KR20010072171A - 조페노프릴 칼슘염의 제조방법 - Google Patents
조페노프릴 칼슘염의 제조방법 Download PDFInfo
- Publication number
- KR20010072171A KR20010072171A KR1020017001379A KR20017001379A KR20010072171A KR 20010072171 A KR20010072171 A KR 20010072171A KR 1020017001379 A KR1020017001379 A KR 1020017001379A KR 20017001379 A KR20017001379 A KR 20017001379A KR 20010072171 A KR20010072171 A KR 20010072171A
- Authority
- KR
- South Korea
- Prior art keywords
- calcium salt
- zofenopril
- isoform
- potassium salt
- salt
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 23
- 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 claims description 16
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000000243 solution Substances 0.000 claims abstract description 19
- 159000000007 calcium salts Chemical class 0.000 claims abstract description 17
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims abstract description 17
- 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 claims abstract description 17
- 239000007864 aqueous solution Substances 0.000 claims abstract description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims abstract description 8
- 238000001556 precipitation Methods 0.000 claims abstract description 7
- VYXXMAGSIYIYGD-NWAYQTQBSA-N propan-2-yl 2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(pyrimidine-4-carbonylamino)phosphoryl]amino]-2-methylpropanoate Chemical compound CC(C)OC(=O)C(C)(C)NP(=O)(CO[C@H](C)Cn1cnc2c(N)ncnc12)NC(=O)c1ccncn1 VYXXMAGSIYIYGD-NWAYQTQBSA-N 0.000 claims abstract description 7
- 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 claims abstract description 6
- 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 claims abstract description 5
- 229960002769 zofenopril Drugs 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 230000002194 synthesizing effect Effects 0.000 claims abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical group CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 102000001708 Protein Isoforms Human genes 0.000 claims description 14
- 108010029485 Protein Isoforms Proteins 0.000 claims description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 4
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 4
- ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical group [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 229960002429 proline Drugs 0.000 claims description 2
- 208000007530 Essential hypertension Diseases 0.000 claims 3
- 206010000891 acute myocardial infarction Diseases 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 230000004064 dysfunction Effects 0.000 claims 3
- 230000002107 myocardial effect Effects 0.000 claims 3
- 150000007524 organic acids Chemical class 0.000 claims 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- 238000001228 spectrum Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 6
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- -1 benzoylthio Chemical group 0.000 description 3
- 229960005069 calcium Drugs 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229960002713 calcium chloride Drugs 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000004626 scanning electron microscopy Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- LLSDKQJKOVVTOJ-UHFFFAOYSA-L calcium chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Ca+2] LLSDKQJKOVVTOJ-UHFFFAOYSA-L 0.000 description 1
- 229940052299 calcium chloride dihydrate Drugs 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011158 quantitative evaluation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- MJZHAVYNYFDSMZ-QMMMGPOBSA-N s-[(2s)-3-chloro-2-methyl-3-oxopropyl] benzenecarbothioate Chemical compound ClC(=O)[C@@H](C)CSC(=O)C1=CC=CC=C1 MJZHAVYNYFDSMZ-QMMMGPOBSA-N 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 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
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- 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)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (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
Description
Claims (15)
- 실질적으로 순수한 형태의 조페노프릴 칼슘염의 동질 이상체 A를 합성하는 방법에 있어서,a) 염화 S(-)-3-벤조일티오-2-메틸프로파노산을 pH 범위 9.0 내지 9.5에서 물 속에서 시스-4-페닐티오-L-프롤린과 반응시키고 산성 형태로 조페노프릴을 회수하는 단계;b) 산성 조페노프릴을 알코올 용액에서 포타슘염으로 염화시키고, 상기 포타슘염을 회수하는 단계;c) 조페노프릴 포타슘염의 수용액을 70 내지 90℃에서 침전 씨드를 가하면서 CaCl2수용액에 가하여 상기 포타슘염을 칼슘염으로 전환시켜 동질 이상체 A의 침전을 일어나게 하는 단계;를 포함하는 방법.
- 제 1항에 있어서, 단계 a)에서 염화 S(-)-3- 벤조일티오-2-메틸프로파노산을 상응하는 산과 염소화제를 비프로톤 유기용매내에서 -10 내지 50℃의 온도에서 반응시켜 합성하고, 시스-4-페닐티오-L-프롤린과의 반응은 비프로톤 유기 용매내의 상기 산클로라이드 용액을 pH 범위 9.0 내지 9.5, 온도 범위 -10 내지 50℃에서 시스-4-페닐티오-L-프롤린 수용액에 첨가하여 실행되는 것을 특징으로 하는 방법.
- 제 2항에 있어서, pH는 수산화 나트륨을 첨가함으로써 9.0 내지 9.5 사의의 값으로 유지시키는 것을 특징으로 하는 방법.
- 제 2항 또는 3항에 있어서, pH는 9.5로 유지되는 것을 특징으로 하는 방법.
- 제 2항 내지 4항 중 어느 한 항에 있어서, 비프로톤 유기 용매는 에틸 아세테이트, 이소부틸 아세테이트 혹은 메틸렌 클로라이드인 것을 특징으로 하는 방법.
- 제 1항에 있어서, 단계 b)는 알코올 용매내에서 유기산 포타슘염과의 반응에 의하여 수행되는 것을 특징으로 하는 방법.
- 제 6항에 있어서, 상기 유기산 포타슘염은 포타슘 2-에틸 헥사노에이트이고 상기 용매는 이소프로판올인 것을 특징으로 하는 방법.
- 제 1항에 있어서, 단계 c)가 온도 범위 80 내지 85℃에서 실시되는 것을 특징으로 하는 방법.
- 제 1항 내지 8항 중 어느 한 항에 있어서, 7% 미만의 동질 이상체 B가 함유된 조페노프릴 칼슘염의 동질 이상체 A를 얻는 것을 특징으로 하는 방법.
- 실질적으로 순수한 조페노프릴 칼슘염 동질 이상체 A를 활성 성분으로 함유하는 제약학적 조성물.
- 동질 이상체 B의 함유량이 15% 미만인 조페노프릴 칼슘염의 동질 이상체 A를 활성 성분으로 함유하는 제약학적 조성물.
- 동질 이상체 B의 함유량이 7% 미만인 조페노프릴 칼슘염의 동질 이상체 A를 활성 성분으로 함유하는 제약학적 조성물.
- 특발성 고혈압, 심근 기능장애, 급성 심근 경색증을 치료하기 위한 약제를 합성하기 위한 실질적으로 순수한 조페노프릴 칼슘염 동질 이상체 A의 용도.
- 특발성 고혈압, 심근 기능장애, 급성 심근 경색증을 치료하기 위한 약제를 합성하기 위한 동질 이상체 B 함유량이 15% 미만인 실질적으로 순수한 조페노프릴 칼슘염 동질 이상체 A의 용도.
- 특발성 고혈압, 심근 기능장애, 급성 심근 경색증을 치료하기 위한 약제를 합성하기 위한 동질 이상체 B 함유량이 7% 미만인 실질적으로 순수한 조페노프릴 칼슘염 동질 이상체 A의 용도.
Applications Claiming Priority (3)
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. |
ITMI98A001833 | 1998-08-04 | ||
PCT/EP1999/005461 WO2000007984A1 (en) | 1998-08-04 | 1999-07-30 | A process for the preparation of zofenopril calcium salt |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20010072171A true KR20010072171A (ko) | 2001-07-31 |
KR100593428B1 KR100593428B1 (ko) | 2006-06-28 |
Family
ID=11380611
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1020017001379A KR100593428B1 (ko) | 1998-08-04 | 1999-07-30 | 조페노프릴 칼슘염의 제조방법 |
Country Status (32)
Country | Link |
---|---|
US (2) | US6521760B1 (ko) |
EP (1) | EP1102745B1 (ko) |
JP (1) | JP2002522417A (ko) |
KR (1) | KR100593428B1 (ko) |
CN (1) | CN1146538C (ko) |
AT (1) | ATE266635T1 (ko) |
AU (1) | AU5372299A (ko) |
BG (1) | BG65022B1 (ko) |
BR (1) | BR9912842A (ko) |
CA (1) | CA2339283C (ko) |
CU (1) | CU23171A3 (ko) |
CZ (1) | CZ301908B6 (ko) |
DE (1) | DE69917282T2 (ko) |
DK (1) | DK1102745T3 (ko) |
EA (1) | EA003454B1 (ko) |
EE (1) | EE04798B1 (ko) |
ES (1) | ES2221417T3 (ko) |
HK (1) | HK1039616B (ko) |
HR (1) | HRP20010083B1 (ko) |
HU (1) | HU227557B1 (ko) |
IL (1) | IL141222A0 (ko) |
IT (1) | IT1301993B1 (ko) |
NO (1) | NO319773B1 (ko) |
PL (1) | PL193828B1 (ko) |
PT (1) | PT1102745E (ko) |
RS (1) | RS49768B (ko) |
SI (1) | SI1102745T1 (ko) |
SK (1) | SK285527B6 (ko) |
TR (1) | TR200100272T2 (ko) |
UA (1) | UA65628C2 (ko) |
WO (1) | WO2000007984A1 (ko) |
ZA (1) | ZA200100907B (ko) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2007003963A1 (en) * | 2005-07-01 | 2007-01-11 | 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 |
CA2653333C (en) * | 2006-05-26 | 2012-07-31 | Generics (Uk) Limited | Zofenopril calcium |
GB0715626D0 (en) | 2007-08-10 | 2007-09-19 | Generics Uk Ltd | Crystalline form of zofenopril calcium |
CA2864562C (en) * | 2008-02-27 | 2017-05-02 | Generics [Uk] Limited | Novel crystalline forms |
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 |
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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 |
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