YU7501A - Proces za pripremu zofenopril kalcijumove soli - Google Patents
Proces za pripremu zofenopril kalcijumove soliInfo
- Publication number
- YU7501A YU7501A YU7501A YU7501A YU7501A YU 7501 A YU7501 A YU 7501A YU 7501 A YU7501 A YU 7501A YU 7501 A YU7501 A YU 7501A YU 7501 A YU7501 A YU 7501A
- Authority
- YU
- Yugoslavia
- Prior art keywords
- zofenopril
- potassium salt
- calcium salt
- preparation
- polymorph
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- NSYUKKYYVFVMST-LETVYOFWSA-L zofenopril calcium Chemical class [Ca+2].C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C([O-])=O)SC(=O)C1=CC=CC=C1.C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C([O-])=O)SC(=O)C1=CC=CC=C1 NSYUKKYYVFVMST-LETVYOFWSA-L 0.000 title abstract 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 abstract 3
- IAIDUHCBNLFXEF-MNEFBYGVSA-N zofenopril Chemical compound C([C@@H](C)C(=O)N1[C@@H](C[C@@H](C1)SC=1C=CC=CC=1)C(O)=O)SC(=O)C1=CC=CC=C1 IAIDUHCBNLFXEF-MNEFBYGVSA-N 0.000 abstract 3
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000011084 recovery Methods 0.000 abstract 2
- 229960002769 zofenopril Drugs 0.000 abstract 2
- XXNAGGDFBCTLQA-DHTOPLTISA-N (2r,4r)-4-phenylsulfanylpyrrolidine-2-carboxylic acid;hydrochloride Chemical compound Cl.C1N[C@@H](C(=O)O)C[C@H]1SC1=CC=CC=C1 XXNAGGDFBCTLQA-DHTOPLTISA-N 0.000 abstract 1
- BCAYPPFBOJCRPN-MRVPVSSYSA-N (2s)-3-benzoylsulfanyl-2-methylpropanoic acid Chemical compound OC(=O)[C@H](C)CSC(=O)C1=CC=CC=C1 BCAYPPFBOJCRPN-MRVPVSSYSA-N 0.000 abstract 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 239000001110 calcium chloride Substances 0.000 abstract 1
- 229910001628 calcium chloride Inorganic materials 0.000 abstract 1
- 235000011148 calcium chloride Nutrition 0.000 abstract 1
- 159000000007 calcium salts Chemical class 0.000 abstract 1
- 238000010899 nucleation Methods 0.000 abstract 1
- 238000001556 precipitation Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F11/00—Compounds of calcium, strontium, or barium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Geology (AREA)
- Inorganic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Proces za pripremanje polimorfa A od zofenopril kalcijum soli u gotovo čistoj formi, koja sadrži: a) reakciju S(-)-benzoiltio-2-metilpropanoik acid hlorida sa cis-4-feniltio-L-prolinom u vodi na pH u rasponu od 9.0 do 9.5 i dobijanje zofenoprila u kiseloj formi; b) salifikacija kiselog zofenoprila sa soli kalijuma u alkoholnom rastvoru i dobijanje soli kalijuma; c) pretvaranje soli kalijuma u so kalcijuma putem dodavanja vodenog rastvora zofenopril soli kalijuma u vodeni rastvor CaCl2 na temperaturi od 70-90В°C sa simulatnim zasejavanjem da se obezbedi taloženje polimorfa A.[A process for the preparation of polymorph A of zofenopril calcium salt in substantially pure form, which comprises: a) reaction of S(-)-3-benzoylthio-2-methylpropanoic acid chloride with cis-4-phenylthio-L-proline in water at pH ranging from 9.0 to 9.5 and recovery of zofenopril in the acidic form; b) salification of acid zofenopril with a potassium salt in alcoholic solution, and recovery of the resulting potassium salt; c) conversion of the potassium salt to the calcium salt by addition of a zofenopril potassium salt aqueous solution to a CaCl2 aqueous solution at a temperature of 70-90В°C with simultaneous seeding to promote the precipitation of polymorph A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT1998MI001833A IT1301993B1 (it) | 1998-08-04 | 1998-08-04 | Processo per la preparazione di zofenopril sale di calcio. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU7501A true YU7501A (sh) | 2005-06-10 |
| RS49768B RS49768B (sr) | 2008-06-05 |
Family
ID=11380611
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6521760B1 (sh) |
| EP (1) | EP1102745B1 (sh) |
| JP (1) | JP2002522417A (sh) |
| KR (1) | KR100593428B1 (sh) |
| CN (1) | CN1146538C (sh) |
| AT (1) | ATE266635T1 (sh) |
| AU (1) | AU5372299A (sh) |
| BG (1) | BG65022B1 (sh) |
| BR (1) | BR9912842A (sh) |
| CA (1) | CA2339283C (sh) |
| CU (1) | CU23171A3 (sh) |
| CZ (1) | CZ301908B6 (sh) |
| DE (1) | DE69917282T2 (sh) |
| DK (1) | DK1102745T3 (sh) |
| EA (1) | EA003454B1 (sh) |
| EE (1) | EE04798B1 (sh) |
| ES (1) | ES2221417T3 (sh) |
| HK (1) | HK1039616B (sh) |
| HR (1) | HRP20010083B1 (sh) |
| HU (1) | HU227557B1 (sh) |
| IL (1) | IL141222A0 (sh) |
| IT (1) | IT1301993B1 (sh) |
| NO (1) | NO319773B1 (sh) |
| PL (1) | PL193828B1 (sh) |
| PT (1) | PT1102745E (sh) |
| RS (1) | RS49768B (sh) |
| SI (1) | SI1102745T1 (sh) |
| SK (1) | SK285527B6 (sh) |
| TR (1) | TR200100272T2 (sh) |
| UA (1) | UA65628C2 (sh) |
| WO (1) | WO2000007984A1 (sh) |
| ZA (1) | ZA200100907B (sh) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2006264650B2 (en) * | 2005-07-01 | 2012-08-23 | Generics [Uk] Limited | Zofenopril calcium in polymorph form C |
| EA012845B1 (ru) * | 2005-12-09 | 2009-12-30 | Менарини Интернэшнл Оперейшнс Люксембург С. А. | Фармацевтическая композиция, содержащая зофеноприл и hctz, для лечения гипертензии |
| HRP20150046T1 (xx) * | 2006-05-26 | 2015-03-13 | Generics | Postupci za pripremu zofenopril kalcija |
| GB0715626D0 (en) | 2007-08-10 | 2007-09-19 | Generics Uk Ltd | Crystalline form of zofenopril calcium |
| JP5530369B2 (ja) * | 2008-02-27 | 2014-06-25 | ジェネリクス・［ユーケー］・リミテッド | 新規な結晶形 |
| US8853421B2 (en) | 2008-02-27 | 2014-10-07 | Generics [Uk] Limited | Crystalline forms of zofenopril calcium |
| WO2010084515A2 (en) * | 2009-01-23 | 2010-07-29 | Glenmark Generics Limited | A process for the preparation of zofenopril and its pharmaceutically acceptable salts thereof |
| SI23949A (sl) | 2011-12-19 | 2013-06-28 | Silverstone Pharma | Nove kristalne soli zofenoprila, postopek za njihovo dobivanje in njihova uporaba v terapiji |
| CN104138359B (zh) * | 2013-05-06 | 2016-03-02 | 扬子江药业集团上海海尼药业有限公司 | 佐芬普利钙片的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4105776A (en) * | 1976-06-21 | 1978-08-08 | E. R. Squibb & Sons, Inc. | Proline derivatives and related compounds |
| US4154935A (en) * | 1978-02-21 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Halogen substituted mercaptoacylamino acids |
| US4316906A (en) * | 1978-08-11 | 1982-02-23 | E. R. Squibb & Sons, Inc. | Mercaptoacyl derivatives of substituted prolines |
-
1998
- 1998-08-04 IT IT1998MI001833A patent/IT1301993B1/it active IP Right Grant
-
1999
- 1999-07-30 CZ CZ20010408A patent/CZ301908B6/cs not_active IP Right Cessation
- 1999-07-30 PL PL99345814A patent/PL193828B1/pl unknown
- 1999-07-30 WO PCT/EP1999/005461 patent/WO2000007984A1/en not_active Ceased
- 1999-07-30 EP EP99939416A patent/EP1102745B1/en not_active Expired - Lifetime
- 1999-07-30 CN CNB998105171A patent/CN1146538C/zh not_active Expired - Lifetime
- 1999-07-30 KR KR1020017001379A patent/KR100593428B1/ko not_active Expired - Lifetime
- 1999-07-30 HU HU0103826A patent/HU227557B1/hu unknown
- 1999-07-30 US US09/762,054 patent/US6521760B1/en not_active Expired - Fee Related
- 1999-07-30 TR TR2001/00272T patent/TR200100272T2/xx unknown
- 1999-07-30 SI SI9930575T patent/SI1102745T1/xx unknown
- 1999-07-30 ES ES99939416T patent/ES2221417T3/es not_active Expired - Lifetime
- 1999-07-30 BR BR9912842-0A patent/BR9912842A/pt not_active Application Discontinuation
- 1999-07-30 EA EA200100095A patent/EA003454B1/ru not_active IP Right Cessation
- 1999-07-30 AU AU53722/99A patent/AU5372299A/en not_active Abandoned
- 1999-07-30 DK DK99939416T patent/DK1102745T3/da active
- 1999-07-30 EE EEP200100065A patent/EE04798B1/xx unknown
- 1999-07-30 HK HK02101248.6A patent/HK1039616B/zh not_active IP Right Cessation
- 1999-07-30 PT PT99939416T patent/PT1102745E/pt unknown
- 1999-07-30 UA UA2001010590A patent/UA65628C2/uk unknown
- 1999-07-30 IL IL14122299A patent/IL141222A0/xx not_active IP Right Cessation
- 1999-07-30 JP JP2000563619A patent/JP2002522417A/ja active Pending
- 1999-07-30 CA CA002339283A patent/CA2339283C/en not_active Expired - Lifetime
- 1999-07-30 HR HR20010083A patent/HRP20010083B1/xx not_active IP Right Cessation
- 1999-07-30 DE DE69917282T patent/DE69917282T2/de not_active Expired - Lifetime
- 1999-07-30 SK SK163-2001A patent/SK285527B6/sk not_active IP Right Cessation
- 1999-07-30 RS YUP-75/01A patent/RS49768B/sr unknown
- 1999-07-30 AT AT99939416T patent/ATE266635T1/de active
-
2001
- 2001-01-24 BG BG105176A patent/BG65022B1/bg unknown
- 2001-02-01 NO NO20010552A patent/NO319773B1/no not_active IP Right Cessation
- 2001-02-01 ZA ZA200100907A patent/ZA200100907B/en unknown
- 2001-02-01 CU CU20010032A patent/CU23171A3/es unknown
-
2002
- 2002-05-28 US US10/155,129 patent/US6515012B2/en not_active Expired - Fee Related
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