CA2966796A1 - Synthesis of copanlisib and its dihydrochloride salt - Google Patents

Synthesis of copanlisib and its dihydrochloride salt Download PDF

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Publication number
CA2966796A1
CA2966796A1 CA2966796A CA2966796A CA2966796A1 CA 2966796 A1 CA2966796 A1 CA 2966796A1 CA 2966796 A CA2966796 A CA 2966796A CA 2966796 A CA2966796 A CA 2966796A CA 2966796 A1 CA2966796 A1 CA 2966796A1
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CA
Canada
Prior art keywords
formula
compound
optionally
copanlisib
solvent
Prior art date
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
CA2966796A
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English (en)
French (fr)
Other versions
CA2966796C (en
Inventor
Jan-Georg Peters
Jurgen Stiehl
Kai Lovis
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 Pharma AG
Original Assignee
Bayer 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.)
Filing date
Publication date
Application filed by Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of CA2966796A1 publication Critical patent/CA2966796A1/en
Application granted granted Critical
Publication of CA2966796C publication Critical patent/CA2966796C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D233/24—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
CA2966796A 2014-11-07 2015-11-05 Synthesis of copanlisib and its dihydrochloride salt Active CA2966796C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP14192202.1A EP3018131A1 (en) 2014-11-07 2014-11-07 Synthesis of copanlisib and its dihydrochloride salt
EP14192202.1 2014-11-07
PCT/EP2015/075765 WO2016071426A1 (en) 2014-11-07 2015-11-05 Synthesis of copanlisib and its dihydrochloride salt

Publications (2)

Publication Number Publication Date
CA2966796A1 true CA2966796A1 (en) 2016-05-12
CA2966796C CA2966796C (en) 2022-12-06

Family

ID=51866060

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2966796A Active CA2966796C (en) 2014-11-07 2015-11-05 Synthesis of copanlisib and its dihydrochloride salt

Country Status (34)

Country Link
US (1) US10035803B2 (und)
EP (2) EP3018131A1 (und)
JP (1) JP6691114B2 (und)
KR (1) KR102562286B1 (und)
CN (1) CN107074776B (und)
AR (1) AR102568A1 (und)
AU (1) AU2015341779B2 (und)
BR (1) BR112017009471B1 (und)
CA (1) CA2966796C (und)
CL (1) CL2017001130A1 (und)
CO (1) CO2017004533A2 (und)
DK (1) DK3215507T3 (und)
EA (1) EA031248B1 (und)
ES (1) ES2716730T3 (und)
HR (1) HRP20190527T8 (und)
HU (1) HUE042794T2 (und)
IL (1) IL251586B (und)
JO (1) JO3487B1 (und)
LT (1) LT3215507T (und)
MX (1) MX365111B (und)
MY (1) MY183123A (und)
NZ (1) NZ730843A (und)
PE (1) PE20170951A1 (und)
PL (1) PL3215507T3 (und)
PT (1) PT3215507T (und)
RS (1) RS58494B1 (und)
SG (1) SG11201702999XA (und)
SI (1) SI3215507T1 (und)
TR (1) TR201904346T4 (und)
TW (1) TWI697494B (und)
UA (1) UA118999C2 (und)
UY (1) UY36396A (und)
WO (1) WO2016071426A1 (und)
ZA (1) ZA201703866B (und)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
EP2508525A1 (en) 2011-04-05 2012-10-10 Bayer Pharma Aktiengesellschaft Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts
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
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
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
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
US11185549B2 (en) 2017-06-28 2021-11-30 Bayer Consumer Care Ag Combination of a PI3K-inhibitor with an androgen receptor antagonist

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1319674B1 (it) * 2000-12-01 2003-10-23 Erregierre Spa Processo per la preparazione dell'acido1-(aminometil)cicloesanacetico.
TW565582B (en) * 2001-04-13 2003-12-11 Kaneka Corp Diamine, acid dianhydride, and reactive group containing polyimide composition prepared therefrom and preparing them
US7375232B2 (en) * 2001-08-15 2008-05-20 E.I. Du Pont De Nemours And Company Ortho-heterocyclic substituted aryl amides for controlling invertebrate pests
KR101059652B1 (ko) 2002-09-30 2011-08-25 바이엘 파마 악티엔게젤샤프트 접합 아졸-피리미딘 유도체
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
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
MY156209A (en) 2009-11-04 2016-01-29 Novartis Ag Heterocyclic sulfonamide derivatives useful mek inhibitors
EP2508525A1 (en) * 2011-04-05 2012-10-10 Bayer Pharma Aktiengesellschaft Substituted 2,3-dihydroimidazo[1,2-c]quinazoline salts

Also Published As

Publication number Publication date
ZA201703866B (en) 2019-06-26
EP3215507B1 (en) 2018-12-26
CN107074776A (zh) 2017-08-18
RS58494B1 (sr) 2019-04-30
MX365111B (es) 2019-05-23
WO2016071426A1 (en) 2016-05-12
EA201790982A1 (ru) 2017-10-31
BR112017009471B1 (pt) 2023-02-28
TW201625633A (zh) 2016-07-16
EP3018131A1 (en) 2016-05-11
AU2015341779A1 (en) 2017-05-11
ES2716730T3 (es) 2019-06-14
MY183123A (en) 2021-02-15
SI3215507T1 (sl) 2019-04-30
JO3487B1 (ar) 2020-07-05
CO2017004533A2 (es) 2017-07-19
NZ730843A (en) 2022-12-23
IL251586A0 (en) 2017-06-29
MX2017005891A (es) 2017-06-30
CA2966796C (en) 2022-12-06
UY36396A (es) 2016-06-30
UA118999C2 (uk) 2019-04-10
TWI697494B (zh) 2020-07-01
CN107074776B (zh) 2021-02-02
PT3215507T (pt) 2019-03-29
IL251586B (en) 2019-05-30
AR102568A1 (es) 2017-03-08
KR102562286B1 (ko) 2023-08-02
US10035803B2 (en) 2018-07-31
EA031248B1 (ru) 2018-12-28
BR112017009471A2 (pt) 2018-01-02
JP6691114B2 (ja) 2020-04-28
PE20170951A1 (es) 2017-07-13
AU2015341779B2 (en) 2020-02-27
DK3215507T3 (en) 2019-04-15
HRP20190527T1 (hr) 2019-05-17
JP2017536352A (ja) 2017-12-07
HRP20190527T8 (hr) 2020-02-21
HUE042794T2 (hu) 2019-07-29
LT3215507T (lt) 2019-04-10
US20170327505A1 (en) 2017-11-16
KR20170078654A (ko) 2017-07-07
EP3215507A1 (en) 2017-09-13
PL3215507T3 (pl) 2019-08-30
CL2017001130A1 (es) 2018-01-19
TR201904346T4 (tr) 2019-04-22
SG11201702999XA (en) 2017-05-30

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