CA2499134C - Fused azole-pyrimidine derivatives - Google Patents

Fused azole-pyrimidine derivatives Download PDF

Info

Publication number: CA2499134C
Authority: CA; Canada
Prior art keywords: amino; 6alkyl; optionally substituted; hydroxy; quinazolin
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.): Expired - Lifetime

Application number

CA2499134A

Other languages

English (en)

French (fr)

Other versions

CA2499134A1 (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

Bayer Schering Pharma AG

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

2011-12-20

2003-09-18 Application filed by Bayer Schering Pharma AG filed Critical Bayer Schering Pharma AG

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

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DDWJFSYHYPDQEL-UHFFFAOYSA-N pyrimidine;1h-pyrrole Chemical class C=1C=CNC=1.C1=CN=CN=C1 DDWJFSYHYPDQEL-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 109
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
238000011282 treatment Methods 0.000 claims abstract description 21
230000000694 effects Effects 0.000 claims abstract description 18
208000035475 disorder Diseases 0.000 claims abstract description 16
201000010099 disease Diseases 0.000 claims abstract description 12
208000028867 ischemia Diseases 0.000 claims abstract description 11
238000011321 prophylaxis Methods 0.000 claims abstract description 10
206010028980 Neoplasm Diseases 0.000 claims abstract description 9
230000002107 myocardial effect Effects 0.000 claims abstract description 9
206010019280 Heart failures Diseases 0.000 claims abstract description 8
241001465754 Metazoa Species 0.000 claims abstract description 8
201000011510 cancer Diseases 0.000 claims abstract description 8
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 8
230000002757 inflammatory effect Effects 0.000 claims abstract description 8
206010007572 Cardiac hypertrophy Diseases 0.000 claims abstract description 7
208000006029 Cardiomegaly Diseases 0.000 claims abstract description 7
208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 7
208000026935 allergic disease Diseases 0.000 claims abstract description 7
208000006673 asthma Diseases 0.000 claims abstract description 7
201000006370 kidney failure Diseases 0.000 claims abstract description 7
230000007170 pathology Effects 0.000 claims abstract description 7
208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 7
206010039083 rhinitis Diseases 0.000 claims abstract description 7
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 6
208000015023 Graves' disease Diseases 0.000 claims abstract description 5
230000004957 immunoregulator effect Effects 0.000 claims abstract description 5
206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 5
208000024827 Alzheimer disease Diseases 0.000 claims abstract description 4
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 4
-1 methoxyphenyl Chemical group 0.000 claims description 371
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 246
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 134
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 104
229910052736 halogen Inorganic materials 0.000 claims description 81
229910052739 hydrogen Inorganic materials 0.000 claims description 61
239000001257 hydrogen Substances 0.000 claims description 61
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
125000004076 pyridyl group Chemical group 0.000 claims description 52
230000002401 inhibitory effect Effects 0.000 claims description 46
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 45
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
125000001424 substituent group Chemical group 0.000 claims description 43
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
150000002367 halogens Chemical class 0.000 claims description 39
150000003839 salts Chemical class 0.000 claims description 38
125000004193 piperazinyl group Chemical group 0.000 claims description 36
125000003226 pyrazolyl group Chemical group 0.000 claims description 34
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 34
125000002883 imidazolyl group Chemical group 0.000 claims description 32
125000000168 pyrrolyl group Chemical group 0.000 claims description 32
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
239000000126 substance Substances 0.000 claims description 26
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 24
125000000335 thiazolyl group Chemical group 0.000 claims description 23
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
125000004093 cyano group Chemical group *C#N 0.000 claims description 21
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 21
125000001544 thienyl group Chemical group 0.000 claims description 18
125000001153 fluoro group Chemical group F* 0.000 claims description 16
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
239000008194 pharmaceutical composition Substances 0.000 claims description 14
125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
125000000623 heterocyclic group Chemical group 0.000 claims description 12
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
125000003831 tetrazolyl group Chemical group 0.000 claims description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 10
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
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 description 9
125000002098 pyridazinyl group Chemical group 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 claims description 8
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 description 8
125000001041 indolyl group Chemical group 0.000 claims description 8
125000000842 isoxazolyl group Chemical group 0.000 claims description 8
239000000546 pharmaceutical excipient Substances 0.000 claims description 8
125000003386 piperidinyl group Chemical group 0.000 claims description 8
125000003373 pyrazinyl group Chemical group 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
230000001363 autoimmune Effects 0.000 claims description 6
125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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 description 5
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 5
125000005493 quinolyl group Chemical group 0.000 claims description 5
125000005529 alkyleneoxy group Chemical group 0.000 claims description 4
125000002837 carbocyclic group Chemical group 0.000 claims description 4
239000003112 inhibitor Substances 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 claims description 3
125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims description 3
125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 claims description 3
125000004506 1,2,5-oxadiazolyl group Chemical group 0.000 claims description 3
125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims description 3
125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
125000004517 1,2,5-thiadiazolyl group Chemical group 0.000 claims description 2
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 description 2
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 description 2
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 description 2
DVMSOHZFPPOXHJ-UHFFFAOYSA-N 6-acetamido-n-(7,9-dimethoxy-8-methyl-2,3-dihydroimidazo[1,2-c]quinazolin-5-yl)pyridine-3-carboxamide Chemical compound N=1C=2C(OC)=C(C)C(OC)=CC=2C2=NCCN2C=1NC(=O)C1=CC=C(NC(C)=O)N=C1 DVMSOHZFPPOXHJ-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
IKRHMBHZYCZSOX-UHFFFAOYSA-N N=1C2=C(OC)C(OC)=CC=C2C2=NCCN2C=1C=C(O)C1=CC=C(NC(C)=O)N=C1 Chemical compound N=1C2=C(OC)C(OC)=CC=C2C2=NCCN2C=1C=C(O)C1=CC=C(NC(C)=O)N=C1 IKRHMBHZYCZSOX-UHFFFAOYSA-N 0.000 claims description 2
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 description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
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 description 2
208000027866 inflammatory disease Diseases 0.000 claims 6
230000002265 prevention Effects 0.000 claims 5
125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 2
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 2
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
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
125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 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
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Classifications

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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		2002-09-30
EP02021861.6		2002-09-30
PCT/EP2003/010377 WO2004029055A1 (en)	2002-09-30	2003-09-18	Fused azole-pyrimidine derivatives

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Also Published As

Publication number	Publication date
TW200413379A (en)	2004-08-01
EP2042504A1 (en)	2009-04-01
CY1112174T1 (el)	2015-12-09
ES2312843T3 (es)	2009-03-01
PT1549652E (pt)	2008-12-15
HRP20131159B1 (hr)	2019-11-01
KR20050067404A (ko)	2005-07-01
IL166855A (en)	2014-05-28
DK1549652T3 (da)	2009-02-23
NZ539062A (en)	2007-05-31
HRP20050375B1 (hr)	2014-03-14
CA2499134A1 (en)	2004-04-08
PT2042504E (pt)	2011-09-07
NO331457B1 (no)	2012-01-09
AU2003293310A1 (en)	2004-04-19
RU2326881C2 (ru)	2008-06-20
AR041426A1 (es)	2005-05-18
BR0314830A (pt)	2005-08-16
BRPI0314830B1 (pt)	2018-03-27
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