PE20170897A1 - Sintesis de copanlisib y su sal diclorhidrato - Google Patents
Sintesis de copanlisib y su sal diclorhidratoInfo
- Publication number
- PE20170897A1 PE20170897A1 PE2017000818A PE2017000818A PE20170897A1 PE 20170897 A1 PE20170897 A1 PE 20170897A1 PE 2017000818 A PE2017000818 A PE 2017000818A PE 2017000818 A PE2017000818 A PE 2017000818A PE 20170897 A1 PE20170897 A1 PE 20170897A1
- Authority
- PE
- Peru
- Prior art keywords
- copanlisib
- optionally
- 2theta
- xrpd
- copper
- Prior art date
Links
- PZBCKZWLPGJMAO-UHFFFAOYSA-N copanlisib Chemical compound C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(N)=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 PZBCKZWLPGJMAO-UHFFFAOYSA-N 0.000 title abstract 2
- 229950002550 copanlisib Drugs 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 239000010949 copper Substances 0.000 abstract 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- STGQPVQAAFJJFX-UHFFFAOYSA-N copanlisib dihydrochloride Chemical compound Cl.Cl.C1=CC=2C3=NCCN3C(NC(=O)C=3C=NC(N)=NC=3)=NC=2C(OC)=C1OCCCN1CCOCC1 STGQPVQAAFJJFX-UHFFFAOYSA-N 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 238000000634 powder X-ray diffraction Methods 0.000 abstract 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 abstract 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 1
- 102000004353 Class I Phosphatidylinositol 3-Kinases Human genes 0.000 abstract 1
- 108010017000 Class I Phosphatidylinositol 3-Kinases Proteins 0.000 abstract 1
- NIQHXSFKSLJILV-UHFFFAOYSA-N NC1N(C=CC=N1)C1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCN2CCOCC2)OC Chemical compound NC1N(C=CC=N1)C1=NC=2C(=C(C=CC2C=2N1CCN2)OCCCN2CCOCC2)OC NIQHXSFKSLJILV-UHFFFAOYSA-N 0.000 abstract 1
- 230000001093 anti-cancer Effects 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007822 coupling agent Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
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- 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
- C07D233/22—Radicals substituted by oxygen atoms
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Se refiere a un metodo para preparar 2-amino-N-[7-metoxi-8-(3-morfolin-4-ilpropoxi)-2,3-dihidroimidazo-[1,2-c]quinazolin-5-il]pirimidin-5-carboxamida (copanlisib) de formula (1), que comprende reaccionar el compuesto a) con b) opcionalmente en presencia de un catalizador, tal como N, N-dimetil-4-aminopiridina, opcionalmente en presencia de un agente de acoplamiento tal como clorhidrato de N- [3-(dimetilamino)propil]-N´-etilcarbodiimida, opcionalmente en un solvente, tal como N, N-dimetilformamida; Son sales de diclorhidrato selectivos: diclorhidrato de copanlisib hidrato I de un pico maximo de XRPD [°2theta] (Cobre (Cu)) de 5,6; diclorhidrato de copanlisib hidrato II de un pico maximo de XRPD [°2theta] (Cobre (Cu)) de 5,7; entre otros. Dicho compuesto inhibe las fosfatidilinositol-3-quinasas de clase I siendo util como anticancerigeno
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14192203.9A EP3018127A1 (en) | 2014-11-07 | 2014-11-07 | Synthesis of copanlisib and its dihydrochloride salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20170897A1 true PE20170897A1 (es) | 2017-07-12 |
Family
ID=51866061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2017000818A PE20170897A1 (es) | 2014-11-07 | 2015-11-05 | Sintesis de copanlisib y su sal diclorhidrato |
Country Status (46)
Families Citing this family (12)
| 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 |
| JP6368353B2 (ja) | 2013-04-08 | 2018-08-01 | バイエル ファーマ アクチエンゲゼルシャフト | 置換された２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン類のリンパ腫治療への使用 |
| WO2016142312A1 (en) | 2015-03-09 | 2016-09-15 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations |
| WO2017153220A1 (en) | 2016-03-08 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | 2—amino—n— [7—methoxy—2, 3-dihydroimidazo-[1, 2-c] quinazolin-5-yl] pyrimidine—5—carboxamides |
| WO2018054782A1 (en) | 2016-09-23 | 2018-03-29 | Bayer Pharma Aktiengesellschaft | Combination of pi3k-inhibitors |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
| US11185549B2 (en) | 2017-06-28 | 2021-11-30 | Bayer Consumer Care Ag | Combination of a PI3K-inhibitor with an androgen receptor antagonist |
| JOP20200053A1 (ar) | 2017-09-08 | 2020-03-08 | Bayer Consumer Care Ag | تركيبات كوبانليسيب |
| EP3498266A1 (en) | 2017-12-15 | 2019-06-19 | Bayer Consumer Care AG | Formulations of copanlisib |
| WO2023139125A1 (en) | 2022-01-18 | 2023-07-27 | Synthon B.V. | Improved process for preparation of copanlisib |
| WO2023218032A1 (en) | 2022-05-13 | 2023-11-16 | Synthon B.V. | Solid forms of copanlisib salts |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1003580A (en) | 1910-08-10 | 1911-09-19 | Remington Typewriter Co | Type-writing machine. |
| US6221877B1 (en) * | 2000-04-12 | 2001-04-24 | Regents Of The University Of California | Substituted 4-phthalimidocarboxanilides as inhibitors of purine salvage phosphoribosyltransferases |
| 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 |
| ES2255624T3 (es) * | 2001-08-15 | 2006-07-01 | E. I. Du Pont De Nemours And Company | Aril amidas sustituidas con grupos orto-heterociclicos para el control de plagas de invertebrados. |
| ATE411996T1 (de) | 2002-09-30 | 2008-11-15 | Bayer Healthcare Ag | Kondensierte azolpyrimidinderivate |
| 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 |
| JP5620275B2 (ja) * | 2008-01-14 | 2014-11-05 | 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Ｂａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | 超増殖性疾患及び脈管形成に関連する疾病を処理するために有用なスルホン置換された２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン誘導体類 |
| 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 |
| JO3733B1 (ar) | 2011-04-05 | 2021-01-31 | Bayer Ip Gmbh | استخدام 3,2-دايهيدروايميدازو[1, 2 -c]كوينازولينات مستبدلة |
| JP6368353B2 (ja) | 2013-04-08 | 2018-08-01 | バイエル ファーマ アクチエンゲゼルシャフト | 置換された２，３−ジヒドロイミダゾ［１，２−ｃ］キナゾリン類のリンパ腫治療への使用 |
| JP6499657B2 (ja) | 2013-12-03 | 2019-04-10 | バイエル ファーマ アクチエンゲゼルシャフト | Ｐｉ３ｋ阻害剤の組み合わせ |
| EP3018131A1 (en) * | 2014-11-07 | 2016-05-11 | Bayer Pharma Aktiengesellschaft | Synthesis of copanlisib and its dihydrochloride salt |
| AU2016231260A1 (en) | 2015-03-09 | 2017-09-21 | Bayer Healthcare Pharmaceuticals Inc. | Use of substituted 2,3-dihydroimidazo[1,2-c]quinazolines |
| WO2016142312A1 (en) | 2015-03-09 | 2016-09-15 | Bayer Pharma Aktiengesellschaft | Substituted 2,3-dihydroimidazo[1,2-c]quinazoline-containing combinations |
| AU2017214230A1 (en) | 2016-02-01 | 2018-08-09 | Bayer Pharma Aktiengesellschaft | Copanlisib biomarkers |
| MA43958A (fr) | 2016-02-01 | 2018-12-12 | Bayer Pharma AG | Biomarqueurs copanlisib |
| WO2017153220A1 (en) | 2016-03-08 | 2017-09-14 | Bayer Pharma Aktiengesellschaft | 2—amino—n— [7—methoxy—2, 3-dihydroimidazo-[1, 2-c] quinazolin-5-yl] pyrimidine—5—carboxamides |
| WO2018054782A1 (en) | 2016-09-23 | 2018-03-29 | Bayer Pharma Aktiengesellschaft | Combination of pi3k-inhibitors |
-
2014
- 2014-11-07 EP EP14192203.9A patent/EP3018127A1/en not_active Withdrawn
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2015
- 2015-11-04 JO JOP/2015/0274A patent/JO3644B1/ar active
- 2015-11-05 KR KR1020177014992A patent/KR102566834B1/ko active Active
- 2015-11-05 CU CU2017000061A patent/CU24489B1/es unknown
- 2015-11-05 US US15/524,581 patent/US10494372B2/en active Active
- 2015-11-05 HR HRP20190720TT patent/HRP20190720T1/hr unknown
- 2015-11-05 DK DK15790150.5T patent/DK3215493T3/da active
- 2015-11-05 MA MA40895A patent/MA40895B1/fr unknown
- 2015-11-05 EA EA201790983A patent/EA035558B1/ru not_active IP Right Cessation
- 2015-11-05 SI SI201530695T patent/SI3215493T1/sl unknown
- 2015-11-05 MX MX2017005893A patent/MX366904B/es active IP Right Grant
- 2015-11-05 PT PT15790150T patent/PT3215493T/pt unknown
- 2015-11-05 NZ NZ731287A patent/NZ731287A/en not_active IP Right Cessation
- 2015-11-05 EP EP15790150.5A patent/EP3215493B1/en active Active
- 2015-11-05 HU HUE15790150A patent/HUE042866T2/hu unknown
- 2015-11-05 TN TN2017000179A patent/TN2017000179A1/en unknown
- 2015-11-05 UY UY0001036392A patent/UY36392A/es not_active Application Discontinuation
- 2015-11-05 CR CR20170184A patent/CR20170184A/es unknown
- 2015-11-05 PE PE2017000818A patent/PE20170897A1/es unknown
- 2015-11-05 MY MYPI2017701550A patent/MY189852A/en unknown
- 2015-11-05 JP JP2017523881A patent/JP6691115B2/ja not_active Expired - Fee Related
- 2015-11-05 CA CA2966800A patent/CA2966800C/en active Active
- 2015-11-05 BR BR112017009470-3A patent/BR112017009470B1/pt not_active IP Right Cessation
- 2015-11-05 TR TR2019/05217T patent/TR201905217T4/tr unknown
- 2015-11-05 ES ES15790150T patent/ES2721778T3/es active Active
- 2015-11-05 RS RS20190453A patent/RS58579B1/sr unknown
- 2015-11-05 SG SG11201703702RA patent/SG11201703702RA/en unknown
- 2015-11-05 ME MEP-2019-107A patent/ME03358B/me unknown
- 2015-11-05 UA UAA201705433A patent/UA122398C2/uk unknown
- 2015-11-05 LT LTEP15790150.5T patent/LT3215493T/lt unknown
- 2015-11-05 WO PCT/EP2015/075789 patent/WO2016071435A2/en not_active Ceased
- 2015-11-05 AU AU2015341788A patent/AU2015341788B2/en not_active Ceased
- 2015-11-05 PL PL15790150T patent/PL3215493T3/pl unknown
- 2015-11-05 CN CN201580072735.8A patent/CN107278204B/zh not_active Expired - Fee Related
- 2015-11-06 AR ARP150103619A patent/AR102570A1/es unknown
- 2015-11-06 TW TW104136742A patent/TWI697495B/zh not_active IP Right Cessation
-
2017
- 2017-04-24 IL IL251874A patent/IL251874A0/en active IP Right Grant
- 2017-05-04 SA SA517381462A patent/SA517381462B1/ar unknown
- 2017-05-04 PH PH12017500833A patent/PH12017500833A1/en unknown
- 2017-05-05 CL CL2017001131A patent/CL2017001131A1/es unknown
- 2017-05-05 EC ECIEPI201727755A patent/ECSP17027755A/es unknown
- 2017-05-05 SV SV2017005433A patent/SV2017005433A/es unknown
- 2017-05-05 DO DO2017000112A patent/DOP2017000112A/es unknown
- 2017-05-05 CO CONC2017/0004532A patent/CO2017004532A2/es unknown
- 2017-05-05 NI NI201700054A patent/NI201700054A/es unknown
- 2017-06-06 ZA ZA2017/03867A patent/ZA201703867B/en unknown
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2019
- 2019-04-23 CY CY20191100444T patent/CY1121602T1/el unknown
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