CA2499134A1 - Fused azole-pyrimidine derivatives - Google Patents

Fused azole-pyrimidine derivatives Download PDF

Info

Publication number: CA2499134A1
Authority: CA; Canada
Prior art keywords: amino; 6alkyl; optionally substituted; hydroxy; alkyl
Prior art date: 2002-09-30
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Granted

Application number

CA002499134A

Other languages

English (en)

French (fr)

Other versions

CA2499134C (en

Inventor

Mitsuyuki Shimada

Toshiki Murata

Kinji Fuchikami

Hideki Tsujishita

Naoki Omori

Issei Kato

Mami Miura

Klaus Urbahns

Florian Gantner

Kevin Bacon

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bayer Intellectual Property GmbH

Original Assignee

Individual

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-09-30

Filing date

2003-09-18

Publication date

2004-04-08

2003-09-18 Application filed by Individual filed Critical Individual

2004-04-08 Publication of CA2499134A1 publication Critical patent/CA2499134A1/en

2011-12-20 Application granted granted Critical

2011-12-20 Publication of CA2499134C publication Critical patent/CA2499134C/en

2023-09-18 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

DDWJFSYHYPDQEL-UHFFFAOYSA-N pyrimidine;1h-pyrrole Chemical class C=1C=CNC=1.C1=CN=CN=C1 DDWJFSYHYPDQEL-UHFFFAOYSA-N 0.000 title 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 13
238000011282 treatment Methods 0.000 claims abstract 11
208000035475 disorder Diseases 0.000 claims abstract 8
150000001875 compounds Chemical class 0.000 claims abstract 6
208000028867 ischemia Diseases 0.000 claims abstract 6
238000011321 prophylaxis Methods 0.000 claims abstract 6
241001465754 Metazoa Species 0.000 claims abstract 5
201000010099 disease Diseases 0.000 claims abstract 5
238000000034 method Methods 0.000 claims abstract 5
206010007572 Cardiac hypertrophy Diseases 0.000 claims abstract 4
208000006029 Cardiomegaly Diseases 0.000 claims abstract 4
206010019280 Heart failures Diseases 0.000 claims abstract 4
206010028980 Neoplasm Diseases 0.000 claims abstract 4
208000001647 Renal Insufficiency Diseases 0.000 claims abstract 4
208000026935 allergic disease Diseases 0.000 claims abstract 4
208000006673 asthma Diseases 0.000 claims abstract 4
201000011510 cancer Diseases 0.000 claims abstract 4
206010012601 diabetes mellitus Diseases 0.000 claims abstract 4
230000000694 effects Effects 0.000 claims abstract 4
201000006370 kidney failure Diseases 0.000 claims abstract 4
230000002107 myocardial effect Effects 0.000 claims abstract 4
230000007170 pathology Effects 0.000 claims abstract 4
208000002815 pulmonary hypertension Diseases 0.000 claims abstract 4
206010039083 rhinitis Diseases 0.000 claims abstract 4
208000024827 Alzheimer disease Diseases 0.000 claims abstract 2
201000001320 Atherosclerosis Diseases 0.000 claims abstract 2
208000015023 Graves' disease Diseases 0.000 claims abstract 2
230000004957 immunoregulator effect Effects 0.000 claims abstract 2
230000002757 inflammatory effect Effects 0.000 claims abstract 2
208000015122 neurodegenerative disease Diseases 0.000 claims abstract 2
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract 2
-1 carboxy, amino Chemical group 0.000 claims 145
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 99
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 90
229910052736 halogen Inorganic materials 0.000 claims 35
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 34
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 32
229910052739 hydrogen Inorganic materials 0.000 claims 32
239000001257 hydrogen Substances 0.000 claims 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 21
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 19
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
125000004193 piperazinyl group Chemical group 0.000 claims 16
150000003839 salts Chemical class 0.000 claims 16
125000004093 cyano group Chemical group *C#N 0.000 claims 15
150000002367 halogens Chemical class 0.000 claims 14
239000003814 drug Substances 0.000 claims 13
125000004076 pyridyl group Chemical group 0.000 claims 13
125000000719 pyrrolidinyl group Chemical group 0.000 claims 13
125000001424 substituent group Chemical group 0.000 claims 13
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 12
125000003226 pyrazolyl group Chemical group 0.000 claims 12
125000000168 pyrrolyl group Chemical group 0.000 claims 11
125000001544 thienyl group Chemical group 0.000 claims 11
125000002883 imidazolyl group Chemical group 0.000 claims 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 10
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 9
125000001412 tetrahydropyranyl group Chemical group 0.000 claims 9
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 8
125000001153 fluoro group Chemical group F* 0.000 claims 8
125000000623 heterocyclic group Chemical group 0.000 claims 8
229910052757 nitrogen Inorganic materials 0.000 claims 8
125000002252 acyl group Chemical group 0.000 claims 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 7
239000000126 substance Substances 0.000 claims 7
125000003831 tetrazolyl group Chemical group 0.000 claims 7
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 6
125000001309 chloro group Chemical group Cl* 0.000 claims 6
208000027866 inflammatory disease Diseases 0.000 claims 6
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims 5
125000003545 alkoxy group Chemical group 0.000 claims 5
125000000217 alkyl group Chemical group 0.000 claims 5
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
125000005842 heteroatom Chemical group 0.000 claims 5
125000001041 indolyl group Chemical group 0.000 claims 5
125000000842 isoxazolyl group Chemical group 0.000 claims 5
238000004519 manufacturing process Methods 0.000 claims 5
229910052760 oxygen Inorganic materials 0.000 claims 5
125000003386 piperidinyl group Chemical group 0.000 claims 5
230000002265 prevention Effects 0.000 claims 5
125000003373 pyrazinyl group Chemical group 0.000 claims 5
125000002098 pyridazinyl group Chemical group 0.000 claims 5
125000000714 pyrimidinyl group Chemical group 0.000 claims 5
229920006395 saturated elastomer Polymers 0.000 claims 5
229910052717 sulfur Inorganic materials 0.000 claims 5
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 4
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 4
125000002837 carbocyclic group Chemical group 0.000 claims 4
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
125000002541 furyl group Chemical group 0.000 claims 4
230000002401 inhibitory effect Effects 0.000 claims 4
125000004043 oxo group Chemical group O=* 0.000 claims 4
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 4
125000000335 thiazolyl group Chemical group 0.000 claims 4
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
125000004423 acyloxy group Chemical group 0.000 claims 3
125000005529 alkyleneoxy group Chemical group 0.000 claims 3
125000005466 alkylenyl group Chemical group 0.000 claims 3
125000003118 aryl group Chemical group 0.000 claims 3
230000001363 autoimmune Effects 0.000 claims 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 3
150000002431 hydrogen Chemical group 0.000 claims 3
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 3
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 3
125000005493 quinolyl group Chemical group 0.000 claims 3
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims 2
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims 2
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims 2
125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims 2
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 2
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims 2
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical group C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims 2
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
108091007960 PI3Ks Proteins 0.000 claims 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 2
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
125000005843 halogen group Chemical group 0.000 claims 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
125000001786 isothiazolyl group Chemical group 0.000 claims 2
229960003966 nicotinamide Drugs 0.000 claims 2
235000005152 nicotinamide Nutrition 0.000 claims 2
239000011570 nicotinamide Substances 0.000 claims 2
125000002971 oxazolyl group Chemical group 0.000 claims 2
125000005545 phthalimidyl group Chemical group 0.000 claims 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 2
229940124530 sulfonamide Drugs 0.000 claims 2
150000003456 sulfonamides Chemical class 0.000 claims 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
OFLWXVAVEUGESJ-UHFFFAOYSA-N 5-hydroxy-n-(7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=CC=CC=2C2=NCCN2C=1NC(=O)C1=CN=CC(O)=C1 OFLWXVAVEUGESJ-UHFFFAOYSA-N 0.000 claims 1
WDUOOUHHGZTOGS-UHFFFAOYSA-N 5-hydroxy-n-[8-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]pyridine-3-carboxamide Chemical compound OC1=CN=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)C(F)(F)F)=C1 WDUOOUHHGZTOGS-UHFFFAOYSA-N 0.000 claims 1
NLNPBNLAWKRRHD-UHFFFAOYSA-N 6-acetamido-n-(7,8-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C2=C(OC)C(OC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=C(NC(C)=O)N=C1 NLNPBNLAWKRRHD-UHFFFAOYSA-N 0.000 claims 1
FVDOKSHTMIWXIT-UHFFFAOYSA-N 6-acetamido-n-(8-morpholin-4-yl-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound C1=NC(NC(=O)C)=CC=C1C(=O)NC1=NC2=CC(N3CCOCC3)=CC=C2C2=NCCN12 FVDOKSHTMIWXIT-UHFFFAOYSA-N 0.000 claims 1
NNPVFUBXJDNKEQ-UHFFFAOYSA-N 6-amino-n-(8-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C2=CC(OC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=C(N)N=C1 NNPVFUBXJDNKEQ-UHFFFAOYSA-N 0.000 claims 1
UZUHFERMDRXBBY-UHFFFAOYSA-N 6-methyl-n-(8-morpholin-4-yl-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound C1=NC(C)=CC=C1C(=O)NC1=NC2=CC(N3CCOCC3)=CC=C2C2=NCCN12 UZUHFERMDRXBBY-UHFFFAOYSA-N 0.000 claims 1
URQZZWTWWDIILI-UHFFFAOYSA-N C1=NC(NC(=O)C)=CC=C1C(O)=CC1=NC2=C(Br)C=C(C)C=C2C2=NCCN12 Chemical compound C1=NC(NC(=O)C)=CC=C1C(O)=CC1=NC2=C(Br)C=C(C)C=C2C2=NCCN12 URQZZWTWWDIILI-UHFFFAOYSA-N 0.000 claims 1
ZFBKAFXRMLXDRD-UHFFFAOYSA-N C1=NC(NC(=O)C)=CC=C1C(O)=CC1=NC2=CC(N3CCOCC3)=CC=C2C2=NCCN12 Chemical compound C1=NC(NC(=O)C)=CC=C1C(O)=CC1=NC2=CC(N3CCOCC3)=CC=C2C2=NCCN12 ZFBKAFXRMLXDRD-UHFFFAOYSA-N 0.000 claims 1
HELQRUXEULFFET-UHFFFAOYSA-N C=1N=CC(O)=CC=1C(O)=CC(N1CCN=C1C1=CC=2)=NC1=CC=2N1CCOCC1 Chemical compound C=1N=CC(O)=CC=1C(O)=CC(N1CCN=C1C1=CC=2)=NC1=CC=2N1CCOCC1 HELQRUXEULFFET-UHFFFAOYSA-N 0.000 claims 1
208000003807 Graves Disease Diseases 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
FCKJZIRDZMVDEM-UHFFFAOYSA-N N-(7,8-dimethoxy-2,3-dihydro-1H-imidazo[1,2-c]quinazolin-5-ylidene)pyridine-3-carboxamide Chemical compound COC1=C(C2=NC(=NC(=O)C3=CN=CC=C3)N4CCNC4=C2C=C1)OC FCKJZIRDZMVDEM-UHFFFAOYSA-N 0.000 claims 1
ZZKWRRWQJBSIDH-UHFFFAOYSA-N N=1C=2C(OC)=C(C)C(OC)=CC=2C2=NCCN2C=1C=C(O)C1=CC=C(NC(C)=O)N=C1 Chemical compound N=1C=2C(OC)=C(C)C(OC)=CC=2C2=NCCN2C=1C=C(O)C1=CC=C(NC(C)=O)N=C1 ZZKWRRWQJBSIDH-UHFFFAOYSA-N 0.000 claims 1
XNBBGYUSKXEZLX-UHFFFAOYSA-N N=1C=2C(OC)=C(OCC(=O)N(C)C)C=CC=2C2=NCCN2C=1C=C(O)C1=CC=CN=C1 Chemical compound N=1C=2C(OC)=C(OCC(=O)N(C)C)C=CC=2C2=NCCN2C=1C=C(O)C1=CC=CN=C1 XNBBGYUSKXEZLX-UHFFFAOYSA-N 0.000 claims 1
IGBOWGRCZADSFI-UHFFFAOYSA-N N=1C=2C(OC)=C(OCCCC(O)=O)C=CC=2C2=NCCN2C=1C=C(O)C1=CC=CN=C1 Chemical compound N=1C=2C(OC)=C(OCCCC(O)=O)C=CC=2C2=NCCN2C=1C=C(O)C1=CC=CN=C1 IGBOWGRCZADSFI-UHFFFAOYSA-N 0.000 claims 1
239000012828 PI3K inhibitor Substances 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
239000003112 inhibitor Substances 0.000 claims 1
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims 1
DDCLADNGPFQZSB-UHFFFAOYSA-N n-(2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-1h-imidazo[4,5-b]pyridine-6-carboxamide Chemical compound N1=C2NC=NC2=CC(C(NC=2N3CCN=C3C3=CC=CC=C3N=2)=O)=C1 DDCLADNGPFQZSB-UHFFFAOYSA-N 0.000 claims 1
WJODTNOONJXHKU-UHFFFAOYSA-N n-(2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-5-hydroxypyridine-3-carboxamide Chemical compound OC1=CN=CC(C(=O)NC=2N3CCN=C3C3=CC=CC=C3N=2)=C1 WJODTNOONJXHKU-UHFFFAOYSA-N 0.000 claims 1
WLMLINJCJZLAOS-UHFFFAOYSA-N n-(7,8-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-1h-imidazo[4,5-b]pyridine-6-carboxamide Chemical compound N1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C(=C3N=2)OC)OC)=C1 WLMLINJCJZLAOS-UHFFFAOYSA-N 0.000 claims 1
XGHJTEVSDNRYAR-UHFFFAOYSA-N n-(7,8-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C(=C3N=2)OC)OC)=C1 XGHJTEVSDNRYAR-UHFFFAOYSA-N 0.000 claims 1
INHNAKDFTXZXEM-UHFFFAOYSA-N n-(7,8-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-5-[(4-methoxyphenyl)methoxy]pyridine-3-carboxamide Chemical compound C1=CC(OC)=CC=C1COC1=CN=CC(C(=O)NC=2N3CCN=C3C3=CC=C(OC)C(OC)=C3N=2)=C1 INHNAKDFTXZXEM-UHFFFAOYSA-N 0.000 claims 1
HVKVBUYYHADEHA-UHFFFAOYSA-N n-(7,8-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-5-hydroxypyridine-3-carboxamide Chemical compound N=1C2=C(OC)C(OC)=CC=C2C2=NCCN2C=1NC(=O)C1=CN=CC(O)=C1 HVKVBUYYHADEHA-UHFFFAOYSA-N 0.000 claims 1
OYLANDUSDVCRTH-UHFFFAOYSA-N n-(7,9-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC2=NC3=C(OC)C=C(C=C3C3=NCCN32)OC)=C1 OYLANDUSDVCRTH-UHFFFAOYSA-N 0.000 claims 1
LUNNURQBAPDEMI-UHFFFAOYSA-N n-(7-bromo-8-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C2=C(Br)C(OC)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 LUNNURQBAPDEMI-UHFFFAOYSA-N 0.000 claims 1
KYCQJNMAGGBSJJ-UHFFFAOYSA-N n-(7-fluoro-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C=3C=CC=C(C=3N=2)F)=C1 KYCQJNMAGGBSJJ-UHFFFAOYSA-N 0.000 claims 1
OHJFOHABJNLWCY-UHFFFAOYSA-N n-(7-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=CC=CC=2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 OHJFOHABJNLWCY-UHFFFAOYSA-N 0.000 claims 1
IJIDTQVVHSOPAF-UHFFFAOYSA-N n-(8,9-dimethoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-5-hydroxypyridine-3-carboxamide Chemical compound N12CCN=C2C=2C=C(OC)C(OC)=CC=2N=C1NC(=O)C1=CN=CC(O)=C1 IJIDTQVVHSOPAF-UHFFFAOYSA-N 0.000 claims 1
IHPWQNLIEKSOJQ-UHFFFAOYSA-N n-(8-bromo-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)Br)=C1 IHPWQNLIEKSOJQ-UHFFFAOYSA-N 0.000 claims 1
UJEYTQLWSQINEE-UHFFFAOYSA-N n-(8-bromo-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C2=CC(Br)=CC=C2C2=NCCN2C=1NC(=O)C1=CC=CN=C1 UJEYTQLWSQINEE-UHFFFAOYSA-N 0.000 claims 1
SEVAILJEPMRNGP-UHFFFAOYSA-N n-(8-chloro-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)Cl)=C1 SEVAILJEPMRNGP-UHFFFAOYSA-N 0.000 claims 1
SZYHENGDPQTFHO-UHFFFAOYSA-N n-(8-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)OC)=C1 SZYHENGDPQTFHO-UHFFFAOYSA-N 0.000 claims 1
WXXASWRNPCIELK-UHFFFAOYSA-N n-(8-methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)C)=C1 WXXASWRNPCIELK-UHFFFAOYSA-N 0.000 claims 1
ATMSVZNHDIDXSD-UHFFFAOYSA-N n-(9-methoxy-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC2=NC3=CC=C(C=C3C3=NCCN32)OC)=C1 ATMSVZNHDIDXSD-UHFFFAOYSA-N 0.000 claims 1
VHWOLZRKGYCAEL-UHFFFAOYSA-N n-[7-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C=3C=CC=C(C=3N=2)C(F)(F)F)=C1 VHWOLZRKGYCAEL-UHFFFAOYSA-N 0.000 claims 1
MWFQXOPXRILSJE-UHFFFAOYSA-N n-[8-(trifluoromethyl)-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl]-3h-benzimidazole-5-carboxamide Chemical compound C1=C2NC=NC2=CC(C(=O)NC=2N3CCN=C3C3=CC=C(C=C3N=2)C(F)(F)F)=C1 MWFQXOPXRILSJE-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
230000005764 inhibitory process Effects 0.000 abstract 2
208000023328 Basedow disease Diseases 0.000 abstract 1
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 abstract 1
206010012438 Dermatitis atopic Diseases 0.000 abstract 1
208000005189 Embolism Diseases 0.000 abstract 1
208000012659 Joint disease Diseases 0.000 abstract 1
208000018737 Parkinson disease Diseases 0.000 abstract 1
206010040070 Septic Shock Diseases 0.000 abstract 1
208000001435 Thromboembolism Diseases 0.000 abstract 1
201000008937 atopic dermatitis Diseases 0.000 abstract 1
150000007980 azole derivatives Chemical class 0.000 abstract 1
239000000825 pharmaceutical preparation Substances 0.000 abstract 1
230000036303 septic shock Effects 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

CA2499134A 2002-09-30 2003-09-18 Fused azole-pyrimidine derivatives Expired - Lifetime CA2499134C (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP02021861.6		2002-09-30
EP02021861		2002-09-30
PCT/EP2003/010377 WO2004029055A1 (en)	2002-09-30	2003-09-18	Fused azole-pyrimidine derivatives

Publications (2)

Publication Number	Publication Date
CA2499134A1 true CA2499134A1 (en)	2004-04-08
CA2499134C CA2499134C (en)	2011-12-20

Family

ID=32039115

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2499134A Expired - Lifetime CA2499134C (en)	2002-09-30	2003-09-18	Fused azole-pyrimidine derivatives

Country Status (33)

Country	Link
US (2)	US7511041B2 (und)
EP (2)	EP1549652B1 (und)
JP (1)	JP4790266B2 (und)
KR (1)	KR101059652B1 (und)
CN (1)	CN100384846C (und)
AR (2)	AR041426A1 (und)
AT (2)	ATE411996T1 (und)
AU (1)	AU2003293310B2 (und)
BR (1)	BRPI0314830B8 (und)
CA (1)	CA2499134C (und)
CY (2)	CY1109790T1 (und)
DE (1)	DE60324296D1 (und)
DK (2)	DK2042504T3 (und)
EC (2)	ECSP055768A (und)
ES (2)	ES2312843T3 (und)
HK (1)	HK1084393A1 (und)
HR (2)	HRP20050375B1 (und)
IL (1)	IL166855A (und)
MA (1)	MA27483A1 (und)
MX (1)	MXPA05001808A (und)
MY (1)	MY140756A (und)
NO (1)	NO331457B1 (und)
NZ (1)	NZ539062A (und)
PE (1)	PE20050089A1 (und)
PL (1)	PL226562B1 (und)
PT (2)	PT1549652E (und)
RU (1)	RU2326881C9 (und)
SI (2)	SI2042504T1 (und)
TW (1)	TWI327570B (und)
UA (1)	UA82205C2 (und)
UY (1)	UY28001A1 (und)
WO (1)	WO2004029055A1 (und)
ZA (1)	ZA200503306B (und)

Families Citing this family (81)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6667300B2 (en)	2000-04-25	2003-12-23	Icos Corporation	Inhibitors of human phosphatidylinositol 3-kinase delta
NZ545547A (en)	2003-08-29	2009-07-31	Mitsui Chemicals Inc	Insecticide for agricultural or horticultural use and method of use thereof
ES2607804T3 (es)	2004-05-13	2017-04-04	Icos Corporation	Quinazolinones como inhibidores de la fosfatidilinositol humana 3-quinasa delta
US20060106013A1 (en)	2004-10-07	2006-05-18	Boehringer Ingelheim International Gmbh	PI3-kinases
WO2006040645A1 (en) *	2004-10-11	2006-04-20	Ranbaxy Laboratories Limited	N-(3,5-dichloropyridin-4-yl)-2,4,5-alkoxy and 2,3,4-alkoxy benzamide derivatives as pde-iv (phophodiesterase type-iv) inhibitors for the treatment of inflammatory diseases such as asthma
CA2605158A1 (en)	2005-04-14	2006-10-26	The Trustees Of Boston University	Diagnostic for lung disorders using class prediction
SG172738A1 (en) *	2005-07-29	2011-07-28	4Sc Ag	Novel heterocyclic nf-kb inhibitors
US7517995B2 (en)	2006-04-06	2009-04-14	Boehringer Ingelheim International Gmbh	Thiazolyl-dihydro-cyclopentapyrazole
US7691868B2 (en)	2006-04-06	2010-04-06	Boehringer Ingelheim International Gmbh	Thiazolyl-dihydro-quinazoline
WO2007127175A2 (en) *	2006-04-26	2007-11-08	F. Hoffmann-La Roche Ag	Pharmaceutical compounds
WO2008064244A2 (en) *	2006-11-20	2008-05-29	The Trustees Of Columbia University In The City Of New York	Phosphoinositide modulation for the treatment of neurodegenerative diseases
AR064106A1 (es) *	2006-12-05	2009-03-11	Bayer Schering Pharma Ag	Derivados de 2,3-dihidroimidazo [1,2-c] quinazolina sustituida utiles para el tratamiento de enfermedades y trastornos hiper-proliferativos asociados con la angiogenesis
EP1953163A1 (en) *	2007-02-01	2008-08-06	Boehringer Ingelheim Pharma GmbH & Co. KG	Pteridinone derivatives as PI3-kinases inhibitors
WO2008148023A2 (en) *	2007-05-23	2008-12-04	Medical College Of Georgia Research Institute, Inc.	Compositions and methods for treating neurological disorders
JP2010539239A (ja) *	2007-09-17	2010-12-16	グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー	Ｐｉ３キナーゼ阻害剤としてのピリドピリミジン誘導体
US20090186951A1 (en)	2007-09-19	2009-07-23	Brody Jerome S	Identification of novel pathways for drug development for lung disease
WO2009091550A2 (en) *	2008-01-14	2009-07-23	Bayer Healthcare Llc	Sulfone substituted 2,3-dihydroimidazo [1,2-c] quinazoline derivatives useful for treating hyper-proliferative disorders and diseases with angiogenesis
EP2250160B1 (en)	2008-01-25	2015-11-11	Millennium Pharmaceuticals, Inc.	Thiophenes and their use as phosphatidylinositol 3-kinase (pi3k) inhibitors
US20090227575A1 (en) *	2008-03-04	2009-09-10	Wyeth	7H-PYRROLO[2,3-H]QUINAZOLINE COMPOUNDS, THEIR USE AS mTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESIS
WO2009128520A1 (ja) *	2008-04-18	2009-10-22	塩野義製薬株式会社	Ｐ１３ｋ阻害活性を有する複素環化合物
WO2009155527A2 (en) *	2008-06-19	2009-12-23	Progenics Pharmaceuticals, Inc.	Phosphatidylinositol 3 kinase inhibitors
EP2168582A1 (en)	2008-09-24	2010-03-31	Bayer Schering Pharma Aktiengesellschaft	Combinations of substituted 2,3-dihydroimidazo[1,2-c]quinazolines
EP2168583A1 (en)	2008-09-24	2010-03-31	Bayer Schering Pharma Aktiengesellschaft	Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines for the treatment of myeloma
WO2010038165A1 (en) *	2008-09-30	2010-04-08	Pfizer Inc.	Imidazo[1,5]naphthyridine compounds, their pharmaceutical use and compositions
ES2443127T3 (es) *	2008-11-11	2014-02-17	Jeil Pharmaceutical Co., Ltd.	Nuevos derivados tricíclicos o sales de éstos farmacéuticamente aceptables, su procedimiento de fabricación y composiciones farmacéuticas que los contienen
WO2010057048A1 (en)	2008-11-13	2010-05-20	Calistoga Pharmaceuticals Inc.	Therapies for hematologic malignancies
US9492449B2 (en)	2008-11-13	2016-11-15	Gilead Calistoga Llc	Therapies for hematologic malignancies
US9495515B1 (en)	2009-12-09	2016-11-15	Veracyte, Inc.	Algorithms for disease diagnostics
EP2391619A1 (en)	2009-01-30	2011-12-07	Millennium Pharmaceuticals, Inc.	Heteroaryls and their use as pi3k inhibitors
US9090601B2 (en)	2009-01-30	2015-07-28	Millennium Pharmaceuticals, Inc.	Thiazole derivatives
EP2411391A1 (en)	2009-03-24	2012-02-01	Gilead Calistoga LLC	Atropisomers of2-purinyl-3-tolyl-quinazolinone derivatives and methods of use
WO2010123931A1 (en)	2009-04-20	2010-10-28	Calistoga Pharmaceuticals Inc.	Methods of treatment for solid tumors
CA2759476C (en) *	2009-04-30	2018-10-09	Julie Nicole Hamblin	Novel compounds
EP2456443A1 (en)	2009-07-21	2012-05-30	Gilead Calistoga LLC	Treatment of liver disorders with pi3k inhibitors
WO2011031896A2 (en) *	2009-09-09	2011-03-17	Avila Therapeutics, Inc.	Pi3 kinase inhibitors and uses thereof
EA201201414A8 (ru) *	2010-04-16	2013-12-30	Байер Интеллектчуал Проперти Гмбх	КОМБИНАЦИИ, СОДЕРЖАЩИЕ ЗАМЕЩЕННЫЕ 2,3-ДИГИДРОИМИДАЗО[1,2-c]ХИНАЗОЛИНЫ
US9062038B2 (en)	2010-08-11	2015-06-23	Millennium Pharmaceuticals, Inc.	Heteroaryls and uses thereof
EP2621486A1 (en)	2010-10-01	2013-08-07	Bayer Intellectual Property GmbH	Substituted n-(2-arylamino)aryl sulfonamide-containing combinations
CN103339133B (zh) *	2010-11-11	2016-06-15	拜耳知识产权有限责任公司	烷氧基取代的2,3-二氢咪唑并[1,2-c]喹唑啉
JP5940078B2 (ja) *	2010-11-11	2016-06-29	バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒＩｎｔｅｌｌｅｃｔｕａｌＰｒｏｐｅｒｔｙＧｍｂＨ	アリールアミノアルコール−置換２，３−ジヒドロイミダゾ［１，２−ｃ］キノリン
UA113280C2 (xx) *	2010-11-11	2017-01-10		АМІНОСПИРТЗАМІЩЕНІ ПОХІДНІ 2,3-ДИГІДРОІМІДАЗО$1,2-c]ХІНАЗОЛІНУ, ПРИДАТНІ ДЛЯ ЛІКУВАННЯ ГІПЕРПРОЛІФЕРАТИВНИХ ПОРУШЕНЬ І ЗАХВОРЮВАНЬ, ПОВ'ЯЗАНИХ З АНГІОГЕНЕЗОМ
JO3733B1 (ar)	2011-04-05	2021-01-31	Bayer Ip Gmbh	استخدام 3,2-دايهيدروايميدازو[1, 2 -c]كوينازولينات مستبدلة
EP2508525A1 (en)	2011-04-05	2012-10-10	Bayer Pharma Aktiengesellschaft	Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts
EA201690461A1 (ru)	2012-03-05	2016-11-30	Джилид Калистога Ллс	Полиморфные формы (s)-2-(1-(9h-пурин-6-иламино)пропил)-5-фтор-3-фенилхиназолин-4(3h)-она
WO2014186036A1 (en)	2013-03-14	2014-11-20	Allegro Diagnostics Corp.	Methods for evaluating copd status
MX2015011899A (es)	2013-03-15	2016-05-05	Genentech Inc	Metodos para el tratamiento de cáncer y prevención de resistencia a los fármacos para el cáncer.
ES2708350T3 (es)	2013-04-08	2019-04-09	Bayer Pharma AG	Uso de 2,3-dihidroimidazo[1,2-c]quinazolinas para el tratamiento de linfomas
EA029568B8 (ru)	2013-05-01	2018-08-31	Ф.Хоффманн-Ля Рош Аг	Бигетероарильные соединения и их применения
WO2015027431A1 (en)	2013-08-29	2015-03-05	Merck Sharp & Dohme Corp.	2,2-difluorodioxolo a2a receptor antagonists
JP2017500319A (ja)	2013-12-20	2017-01-05	ギリアードカリストガエルエルシー	（ｓ）−２−（１−（９ｈ−プリン−６−イルアミノ）プロピル）−５−フルオロ−３−フェニルキナゾリン−４（３ｈ）−オンの塩酸塩の多形形態
AU2014364410B2 (en)	2013-12-20	2017-11-16	Gilead Calistoga Llc	Process methods for phosphatidylinositol 3-kinase inhibitors
MX2016016530A (es)	2014-06-13	2017-03-27	Gilead Sciences Inc	Inhibidores de fosfatidilinositol 3-quinasa.
CN114606309A (zh)	2014-11-05	2022-06-10	威拉赛特公司	使用机器学习和高维转录数据的诊断系统和方法
EP3018131A1 (en)	2014-11-07	2016-05-11	Bayer Pharma Aktiengesellschaft	Synthesis of copanlisib and its dihydrochloride salt
EP3018127A1 (en)	2014-11-07	2016-05-11	Bayer Pharma Aktiengesellschaft	Synthesis of copanlisib and its dihydrochloride salt
CA2978830A1 (en)	2015-03-09	2016-09-15	Bayer Pharma Aktiengesellschaft	Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations
CN105130998B (zh) *	2015-09-25	2017-07-28	苏州立新制药有限公司	库潘尼西的制备方法
CN105130997B (zh) *	2015-09-25	2017-12-05	苏州明锐医药科技有限公司	一种库潘尼西的制备方法
CN108884098B (zh) *	2016-03-08	2021-09-14	拜耳制药股份公司	2-氨基-N-[7-甲氧基-2,3-二氢咪唑并[1,2-c]喹唑啉-5-基]嘧啶-5-甲酰胺类
EP3219329A1 (en)	2016-03-17	2017-09-20	Bayer Pharma Aktiengesellschaft	Combinations of copanlisib
WO2018009915A1 (en)	2016-07-08	2018-01-11	Trustees Of Boston University	Gene expression-based biomarker for the detection and monitoring of bronchial premalignant lesions
CN109729716B (zh)	2016-09-23	2022-03-15	拜耳制药股份公司	Pi3k-抑制剂的组合产品
JP2020503289A (ja)	2016-12-14	2020-01-30	ターベダセラピューティクスインコーポレイテッドＴａｒｖｅｄａＴｈｅｒａｐｅｕｔｉｃｓ，Ｉｎｃ．	Ｈｓｐ９０標的化コンジュゲート及びその製剤
CA3054249A1 (en)	2017-02-24	2018-08-30	Bayer Pharma Aktiengesellschaft	Combinations of copanlisib with anti-pd-1 antibody
US11185549B2 (en)	2017-06-28	2021-11-30	Bayer Consumer Care Ag	Combination of a PI3K-inhibitor with an androgen receptor antagonist
MX2020002633A (es)	2017-09-08	2020-07-13	Bayer Consumer Care Ag	Formulaciones de copanlisib.
EP3498266A1 (en)	2017-12-15	2019-06-19	Bayer Consumer Care AG	Formulations of copanlisib
BR112020005455A2 (pt) *	2017-09-20	2020-09-24	Abm Therapeutics Corporation	derivados de iminopirimidina cíclica como inibidores de cinase
EP3694511A1 (en)	2017-10-13	2020-08-19	INSERM (Institut National de la Santé et de la Recherche Médicale)	Combination treatment of pancreatic cancer
US20200355693A1 (en)	2017-11-23	2020-11-12	Inserm (Institut National De La Sante Et De La Recherche Medicale)	A new marker for predicting the sensitivity to pi3k inhibitors
WO2019105734A1 (en)	2017-11-28	2019-06-06	Bayer Consumer Care Ag	Combinations of copanlisib
WO2019105835A1 (en)	2017-11-29	2019-06-06	Bayer Consumer Care Ag	Combinations of copanlisib and anetumab ravtansine
WO2019197269A1 (en)	2018-04-11	2019-10-17	Bayer Aktiengesellschaft	Combinations of copanlisib with triazolone derivatives and their use in the treatment of cancer
WO2020020385A1 (zh) *	2018-07-27	2020-01-30	上海翰森生物医药科技有限公司	含三并环类衍生物抑制剂、其制备方法和应用
CN109053554B (zh) *	2018-08-01	2020-07-28	江苏八巨药业有限公司	一种使用催化剂合成3-乙酰吡啶的方法
US20210187134A1 (en)	2018-08-28	2021-06-24	Bayer As	Combination of pi3k-inhibitors and targeted thorium conjugates
US20210369724A1 (en)	2018-10-16	2021-12-02	Bayer Aktiengesellschaft	Combination of atr kinase inhibitors with 2,3-dihydroimidazo[1,2-c]quinazoline compounds
WO2020096927A1 (en)	2018-11-05	2020-05-14	Iovance Biotherapeutics, Inc.	Expansion of tils utilizing akt pathway inhibitors
CN113195000A (zh)	2018-12-21	2021-07-30	第一三共株式会社	抗体-药物缀合物和激酶抑制剂的组合
WO2020164997A1 (en)	2019-02-12	2020-08-20	Bayer Aktiengesellschaft	Combination of pi3k-inhibitors
CN114621236A (zh) *	2022-04-25	2022-06-14	河南湾流生物科技有限公司	一种喹啉类饲料添加剂的制备方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3644354A (en) *	1968-09-16	1972-02-22	Sandoz Ag	5-substituted-2 3-dihydroimidazo(1 2-c)quinazolines
US4287341A (en)	1979-11-01	1981-09-01	Pfizer Inc.	Alkoxy-substituted-6-chloro-quinazoline-2,4-diones
CN1033644C (zh) *	1993-01-02	1996-12-25	瑞安大药厂股份有限公司	3-取代甲基-2，3-二氢咪唑并[1，2-c]喹唑啉衍生物，其制备与用途
RU2203669C2 (ru)	1994-08-12	2003-05-10	Про-Нейрон Инк.	Способы лечения сепсиса и воспалений с помощью оксипуриновых нуклеозидов
EP2311806A3 (en) *	1996-01-29	2011-08-10	The United States of America, Represented by the Secretary, Department of Health and Human Services	Dihydropyridine-, pyridine-, benzopyranone- and triazoloquinazoline derivatives, their preparation and their use as adenosine receptor antagonists
US5932584A (en) *	1997-05-06	1999-08-03	National Science Council	Optically active 2,3-dihydroimidazo(1,2-C) quinazoline derivatives, the preparation and antihypertensive use thereof
SI3029041T1 (sl)	2000-04-25	2020-08-31	Icos Corporation	Inhibitorji humane delta fosfatidil-inozitol 3-kinaze
CA2407593C (en) *	2000-04-27	2011-01-11	Yamanouchi Pharmaceutical Co. Ltd.	Fused heteroaryl derivatives

2003
- 2003-09-18 KR KR1020057005434A patent/KR101059652B1/ko active IP Right Grant
- 2003-09-18 SI SI200332036T patent/SI2042504T1/sl unknown
- 2003-09-18 EP EP03788908A patent/EP1549652B1/en not_active Expired - Lifetime
- 2003-09-18 WO PCT/EP2003/010377 patent/WO2004029055A1/en active Application Filing
- 2003-09-18 MX MXPA05001808A patent/MXPA05001808A/es active IP Right Grant
- 2003-09-18 UA UAA200504176A patent/UA82205C2/uk unknown
- 2003-09-18 PT PT03788908T patent/PT1549652E/pt unknown
- 2003-09-18 EP EP08075839A patent/EP2042504B1/en not_active Expired - Lifetime
- 2003-09-18 ES ES03788908T patent/ES2312843T3/es not_active Expired - Lifetime
- 2003-09-18 PL PL375935A patent/PL226562B1/pl unknown
- 2003-09-18 JP JP2004538935A patent/JP4790266B2/ja not_active Expired - Lifetime
- 2003-09-18 CA CA2499134A patent/CA2499134C/en not_active Expired - Lifetime
- 2003-09-18 DK DK08075839.4T patent/DK2042504T3/da active
- 2003-09-18 AU AU2003293310A patent/AU2003293310B2/en not_active Expired
- 2003-09-18 SI SI200331490T patent/SI1549652T1/sl unknown
- 2003-09-18 NZ NZ539062A patent/NZ539062A/en not_active IP Right Cessation
- 2003-09-18 PT PT08075839T patent/PT2042504E/pt unknown
- 2003-09-18 DE DE60324296T patent/DE60324296D1/de not_active Expired - Lifetime
- 2003-09-18 RU RU2005113165/04A patent/RU2326881C9/ru active
- 2003-09-18 AT AT03788908T patent/ATE411996T1/de active
- 2003-09-18 DK DK03788908T patent/DK1549652T3/da active
- 2003-09-18 BR BRPI0314830A patent/BRPI0314830B8/pt active IP Right Grant
- 2003-09-18 AT AT08075839T patent/ATE511510T1/de active
- 2003-09-18 CN CNB038233673A patent/CN100384846C/zh not_active Expired - Lifetime
- 2003-09-18 ES ES08075839T patent/ES2367141T3/es not_active Expired - Lifetime
- 2003-09-18 US US10/527,376 patent/US7511041B2/en active Active
- 2003-09-29 UY UY28001A patent/UY28001A1/es active IP Right Grant
- 2003-09-29 AR ARP030103542A patent/AR041426A1/es active IP Right Grant
- 2003-09-29 TW TW092126767A patent/TWI327570B/zh not_active IP Right Cessation
- 2003-09-29 PE PE2003000986A patent/PE20050089A1/es active IP Right Grant
- 2003-09-29 MY MYPI20033701A patent/MY140756A/en unknown
2005
- 2005-02-14 IL IL166855A patent/IL166855A/en active IP Right Grant
- 2005-04-25 ZA ZA200503306A patent/ZA200503306B/en unknown
- 2005-04-27 HR HRP20050375AA patent/HRP20050375B1/hr not_active IP Right Cessation
- 2005-04-27 NO NO20052076A patent/NO331457B1/no not_active IP Right Cessation
- 2005-04-28 EC EC2005005768A patent/ECSP055768A/es unknown
- 2005-04-29 MA MA28247A patent/MA27483A1/fr unknown
2006
- 2006-04-19 HK HK06104675.8A patent/HK1084393A1/xx not_active IP Right Cessation
2009
- 2009-01-09 CY CY20091100017T patent/CY1109790T1/el unknown
- 2009-03-30 US US12/414,257 patent/US8129386B2/en not_active Expired - Lifetime
- 2009-07-01 AR ARP090102458A patent/AR072458A2/es not_active Application Discontinuation
2011
- 2011-02-07 EC EC2011005768A patent/ECSP11005768A/es unknown
- 2011-08-10 CY CY20111100771T patent/CY1112174T1/el unknown
2013
- 2013-12-04 HR HRP20131159A patent/HRP20131159B1/hr not_active IP Right Cessation

Also Published As

Publication number	Publication date
UY28001A1 (es)	2004-04-30
HRP20131159B1 (hr)	2019-11-01
ATE511510T1 (de)	2011-06-15
CY1112174T1 (el)	2015-12-09
BRPI0314830B8 (pt)	2021-05-25
US20090270388A1 (en)	2009-10-29
TWI327570B (en)	2010-07-21
PT1549652E (pt)	2008-12-15
CN1688582A (zh)	2005-10-26
ES2367141T3 (es)	2011-10-28
UA82205C2 (en)	2008-03-25
HK1084393A1 (en)	2006-07-28
HRP20050375A2 (en)	2006-05-31
ECSP11005768A (es)	2011-03-31
HRP20050375B1 (hr)	2014-03-14
DK1549652T3 (da)	2009-02-23
NO20052076L (no)	2005-04-27
AR041426A1 (es)	2005-05-18
US8129386B2 (en)	2012-03-06
AU2003293310B2 (en)	2010-04-01
IL166855A (en)	2014-05-28
MY140756A (en)	2010-01-15
EP1549652A1 (en)	2005-07-06
CA2499134C (en)	2011-12-20
RU2326881C9 (ru)	2009-04-10
TW200413379A (en)	2004-08-01
WO2004029055A1 (en)	2004-04-08
NZ539062A (en)	2007-05-31
KR20050067404A (ko)	2005-07-01
PE20050089A1 (es)	2005-04-20
BR0314830A (pt)	2005-08-16
ZA200503306B (en)	2006-07-26
PT2042504E (pt)	2011-09-07
US20060128732A1 (en)	2006-06-15
JP2006508063A (ja)	2006-03-09
US7511041B2 (en)	2009-03-31
EP1549652B1 (en)	2008-10-22
NO331457B1 (no)	2012-01-09
ECSP055768A (es)	2005-08-11
HRP20131159A2 (hr)	2014-05-23
EP2042504A1 (en)	2009-04-01
CY1109790T1 (el)	2014-09-10
MA27483A1 (fr)	2005-08-01
DE60324296D1 (de)	2008-12-04
ATE411996T1 (de)	2008-11-15
CN100384846C (zh)	2008-04-30
KR101059652B1 (ko)	2011-08-25
MXPA05001808A (es)	2005-08-16
RU2005113165A (ru)	2005-10-10
PL226562B1 (pl)	2017-08-31
ES2312843T3 (es)	2009-03-01
SI2042504T1 (sl)	2011-10-28
RU2326881C2 (ru)	2008-06-20
SI1549652T1 (sl)	2009-04-30
DK2042504T3 (da)	2011-09-19
BRPI0314830B1 (pt)	2018-03-27
EP2042504B1 (en)	2011-06-01
PL375935A1 (en)	2005-12-12
AR072458A2 (es)	2010-09-01
AU2003293310A1 (en)	2004-04-19
JP4790266B2 (ja)	2011-10-12

Legal Events

Date	Code	Title	Description
2008-09-17	EEER	Examination request
2023-11-20	MKEX	Expiry	Effective date: 20230918

Publication	Publication Date	Title
CA2499134A1 (en)	2004-04-08	Fused azole-pyrimidine derivatives
JP5911638B2 (ja)	2016-04-27	ベンゾチアゾール−６−イル酢酸誘導体およびｈｉｖ感染を処置するためのそれらの使用
JP5878546B2 (ja)	2016-03-08	ｓＧＣ刺激剤
JP2020504136A5 (und)	2021-02-04
US10130629B2 (en)	2018-11-20	Pharmaceutical combinations
ES2697051T3 (es)	2019-01-21	Actividad antiviral de heterociclos bicíclicos
AU2012345557A1 (en)	2014-06-26	Novel trifluoromethyl-oxadiazole derivatives and their use in the treatment of disease
RU2006136881A (ru)	2008-04-27	Фармацевтическая композиция, содержащая производное бензодиазепина и ингибитор белка слияния rsv
WO2001097849A1 (fr)	2001-12-27	Potentialisateurs d'effet antitumoral
JP2017512794A5 (und)	2018-05-10
JP2012532931A5 (und)	2014-10-09
JP2007518809A5 (und)	2008-01-31
JP2017508766A5 (und)	2018-05-10
KR20060110006A (ko)	2006-10-23	비전형 항정신병제와 코르티코트로핀 방출 인자 길항제의치료적 조합물
JP2013505930A5 (und)	2013-08-08
RU2016141646A (ru)	2018-04-27	Ингибиторы trka киназы, основанные на них композиции и способы
RU2016141645A (ru)	2018-04-27	ИНГИБИТОРЫ TrkA КИНАЗЫ, ОСНОВАННЫЕ НА НИХ КОМПОЗИЦИИ И СПОСОБЫ
JP2013515032A5 (und)	2014-01-30
JP2013519724A5 (und)	2014-04-03
RU2012139828A (ru)	2014-03-27	Производные пиразолопиперидина в качестве ингибиторов nadph-оксидазы
CA2587026A1 (en)	2006-05-04	Use of dipyridamole in combination with antithrombotics for treatment and prevention of thromboembolic diseases
RU2011105059A (ru)	2012-08-20	Применение производных пиримидиламинобензамида для лечения фиброза
KR20110097966A (ko)	2011-08-31	백혈병의 치료를 위한, 피리미딜아미노벤즈아미드 화합물과 조합된 ｃ-ｓｒｃ 억제제의 용도
JP2009532438A5 (und)	2010-05-20
AU2005205914A1 (en)	2005-08-04	Combination of organic compounds