KR910014389A - 포스핀산 에스테르의 부분 입체 이성질체의 선택적 제조 방법 - Google Patents
포스핀산 에스테르의 부분 입체 이성질체의 선택적 제조 방법 Download PDFInfo
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- KR910014389A KR910014389A KR1019910000782A KR910000782A KR910014389A KR 910014389 A KR910014389 A KR 910014389A KR 1019910000782 A KR1019910000782 A KR 1019910000782A KR 910000782 A KR910000782 A KR 910000782A KR 910014389 A KR910014389 A KR 910014389A
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- isomers
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- lower alkyl
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- 238000000034 method Methods 0.000 title claims abstract 11
- 150000002148 esters Chemical class 0.000 title 1
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims abstract 10
- 238000006243 chemical reaction Methods 0.000 claims abstract 7
- -1 phosphinic acid ester Chemical class 0.000 claims abstract 7
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 claims abstract 3
- 239000012973 diazabicyclooctane Substances 0.000 claims abstract 3
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims abstract 3
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 238000005984 hydrogenation reaction Methods 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000002994 raw material Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229910001415 sodium ion Inorganic materials 0.000 claims 2
- XRZWVSXEDRYQGC-ZJUUUORDSA-N (2s,4s)-4-cyclohexylpyrrolidin-1-ium-2-carboxylate Chemical compound C1N[C@H](C(=O)O)C[C@H]1C1CCCCC1 XRZWVSXEDRYQGC-ZJUUUORDSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- LKHYFCSSVZVVNF-UHFFFAOYSA-N ethyl hexanoate;sodium Chemical compound [Na].CCCCCC(=O)OCC LKHYFCSSVZVVNF-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 abstract 1
- 102000004270 Peptidyl-Dipeptidase A Human genes 0.000 abstract 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- KMPWYEUPVWOPIM-KODHJQJWSA-N cinchonidine Chemical compound C1=CC=C2C([C@H]([C@H]3[N@]4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-KODHJQJWSA-N 0.000 abstract 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229960001880 fosinopril sodium Drugs 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- TVTJZMHAIQQZTL-WATAJHSMSA-M sodium;(2s,4s)-4-cyclohexyl-1-[2-[[(1s)-2-methyl-1-propanoyloxypropoxy]-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate Chemical compound [Na+].C([P@@](=O)(O[C@H](OC(=O)CC)C(C)C)CC(=O)N1[C@@H](C[C@H](C1)C1CCCCC1)C([O-])=O)CCCC1=CC=CC=C1 TVTJZMHAIQQZTL-WATAJHSMSA-M 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3258—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3264—Esters with hydroxyalkyl compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Cosmetics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (11)
- a) 하기 구조식(Ⅰ)의 포스핀산 에스테르를 유기 용매 중의 4-메틸모르폴린, 디아자비시클로옥탄, 퀴누클리딘, 1-메틸피롤리딘 또는 신코니딘의 존재 하에, 약40℃내지 138℃의 온도에서 하기 구조식(Ⅱ)의 할로 에스테르와 반응시켜서 4개의 이성체질의 혼합물로 이루어진 중간체를 얻고, b) a)단계에서 얻은 4개의 이성질체의 혼합물을 수소 첨가 반응시켜서, R3에스테르기를 제거하여, 목적하지 않은 부분 입체 이성질체 쌍으로부터 목적하는 부분 입체 이성질체 쌍을 증가된 수율로 얻는 단계로 이루어진 것이 특징인 하기 구조식(Ⅲ C)및 (Ⅲ D)이 이성질체를 포함하는 목적하지 않은 부분 입체 이성질체 쌍에 비하여 하기 구조식(Ⅲ A)및 (Ⅲ B)의 이성질체를 포함하는 목적하는 부분 입체 이성질체쌍을 증가된 수율로 제조하는 방법.상기 각 식에서 R1은 저급 알킬, 시클로알킬, 아릴, 아릴-저급 알킬 또는 시클로알킬-저급 알킬기이고, n은 0또는 1이며, R2은 수소 원자, 저급 알킬 또는 아릴-저급 알킬기이고, R3은 이고, R4은 저급 알킬, 저급 알콕시, 페닐,, 또는 디(저급 알킬) 아미노기이고, Hal은 Br또는 Cl이고, X는 수소 원자, 저급 알킬, 또는 페닐기이고, Y는 수소 원자, 저급 알킬, 저급 알콕시 또는 페닐기이다.
- 제1항에 있어서, R1이고이고, n이 0이며, R2가 수소 원자이고, Hal이 Cl이며, R3이-CH2- 이고, X가 -CH(CH3)2이며, Y가 C2H5인 것이 특징인 방법.
- 제2항에 있어서, (a) 단계의 반응을 4-메틸모르폴린의 존재 항에 수행하고, 목적하지 않은 부분 입체 이성질체 쌍에 대한 목적하는 부분 입체 이성질체 쌍의 비율이 약 1.5인 것이 특징인 방법.
- 제3항에 있어서, (a) 단계의 반응을 톨루엔 중에서 약 95℃의 온도에서 약 18내지 19시간 동안 수행하고, (b)단계의 수소 첨가 반응을 탄소 상의 팔라듐의 존재 하에 1psi에서 수소 기포 발생기킴으로서 수행하는 것이 특징인 방법.
- (a) 하기 구조식의 포스핀산 에스테르를유기 용매 중의 4-메틸모르폴린, 디아자비시클로옥탄, 퀴누클리딘, 1-메틸피톨리딘 또는 신코니딘의 존재하에, 약 40℃내지 약 138℃의 온도에서 하기 구조식의 할로 에스테르와반응시켜서 4개의 이성질체의 혼합물로 이루어진 중간체를 얻고, b) a) 단계에서 얻은 4개의 이성질체 혼합물을 수소 첨가 반응시켜서, 하기 구조식(Ⅲ C)및 (Ⅲ D)의 이성질체를 포함하는 목적하지 않은 부분 입체 이성질체 쌍에 비하여 하기 구조식(Ⅲ A)및 (Ⅲ B)의 이성질체를 포함하는 목적하는 부분 입체 이성질체쌍을 증가된 수율로 얻고,c) 목적하는 부분 입체 이성질체 쌍을 메틸이소부틸 케톤을 사용하여 추출시킴으로서 상기 b) 단계에서 얻은 목적하지 않은 부분 입체 이성질체로부터 분리시키고, d) 상기(c)단계에서 얻은 목적하는 부분 입체 이성질체쌍을 광학적으로 활성인 아민으로 처리하여 염을 형성시키고 목적하는 이성질체의 염을 강산 또는 산염으로 처리함으로써 분할시켜 하기 구조식(Ⅲ A)의 부분 입체 이성질체를 얻고,e) 상기(d) 단계에서 얻은 분할된 상 생성물을 (트랜스)-4-시클로헥실-L-프롤린, 일염산염과 커플링시키고, 이어서 나트륨 이온 원료로 처리하여 포시노프릴 나트륨을 얻는 단계로 이루어진 것이 특징인 포시노프릴 나트륨을 증가된 수율로 제조하는 방법.
- 제5항에 있어서, (a) 단계의 반응을 4-메틸모르폴린의 존재 하에서 수행하고, 목적하지 않은 부분 입체 이성질체 쌍에 대한 목적하는 부분 입체 이성질체 쌍의 비율이 약 1.5인 것이 특징인 방법.
- 제6항에 있어서, 상기(a) 단계에서의 반응을 톨루엔 중에서 약 95℃의 온도에서 약 18-19시간동안 수행하고, 상기(b) 단계에서의 수소 첨가 반응을 탄소 상의 팔라듐의 존재 하에 1psi에서 수소 기포 발생시킴으로서 수행하는 것이 특징인 방법.
- 제7항에 있어서, 상기 (d) 단계에서의 분할제가-신코니딘인 것이 특징인 방법.
- 제8항에 있어서, 상기 (e) 단계에서의 커플링 반응을 커플링제의 존재 하에서 수행하는 것이 특징인 방법.
- 제9항에 있어서, 상기 (e) 단계에서의 커플링제가 N,N′-디시클로헥실카르보디이미드이고, 나트륨 이온의 원료가 2-에틸 헥산산 나트륨염인 것이 특징인 방법.
- 제8항에 있어서, 상기 (d) 단계에서의 분할된 산 생성물을 상기 (e) 단계에서의 커플링 반응을 수행하기 전에 활성화 형태로 전환시키는 것이 특징인 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019980040259A KR0179470B1 (ko) | 1990-01-19 | 1998-09-28 | 포시노프릴 나트륨의 선택적 제조 방법 |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US467,451 | 1990-01-19 | ||
| US07/467,451 US5008399A (en) | 1990-01-19 | 1990-01-19 | Diastereoselective preparation of phosphinate esters |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980040259A Division KR0179470B1 (ko) | 1990-01-19 | 1998-09-28 | 포시노프릴 나트륨의 선택적 제조 방법 |
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| Publication Number | Publication Date |
|---|---|
| KR910014389A true KR910014389A (ko) | 1991-08-31 |
| KR0179368B1 KR0179368B1 (ko) | 1999-05-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019910000782A KR0179368B1 (ko) | 1990-01-19 | 1991-01-18 | 포스핀산 에스테르의 부분 입체 이성질체의 선택적 제조방법 |
| KR1019980040259A KR0179470B1 (ko) | 1990-01-19 | 1998-09-28 | 포시노프릴 나트륨의 선택적 제조 방법 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019980040259A KR0179470B1 (ko) | 1990-01-19 | 1998-09-28 | 포시노프릴 나트륨의 선택적 제조 방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US5008399A (ko) |
| EP (1) | EP0437799B1 (ko) |
| JP (1) | JP2846484B2 (ko) |
| KR (2) | KR0179368B1 (ko) |
| CN (1) | CN1026791C (ko) |
| AT (1) | ATE118779T1 (ko) |
| AU (1) | AU623562B2 (ko) |
| CA (1) | CA2032900C (ko) |
| DE (1) | DE69017183T2 (ko) |
| DK (1) | DK0437799T3 (ko) |
| ES (1) | ES2068321T3 (ko) |
| FI (1) | FI101539B1 (ko) |
| HU (1) | HU208142B (ko) |
| IE (1) | IE67354B1 (ko) |
| IL (1) | IL96838A (ko) |
| NO (1) | NO179915C (ko) |
| PT (1) | PT96519B (ko) |
| RU (1) | RU2044740C1 (ko) |
| ZA (1) | ZA9196B (ko) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9304619D0 (en) * | 1993-03-06 | 1993-04-21 | Ciba Geigy Ag | Esters |
| US6555139B2 (en) | 1999-06-28 | 2003-04-29 | Wockhardt Europe Limited | Preparation of micron-size pharmaceutical particles by microfluidization |
| JP2004520440A (ja) * | 2001-04-30 | 2004-07-08 | ルピン ラボラトリーズ リミティド | フォシノプリルナトリウムの製造方法 |
| CN100497335C (zh) * | 2005-10-27 | 2009-06-10 | 上海医药工业研究院 | 取代氧膦基乙酸的光学拆分方法 |
| CN100488969C (zh) * | 2005-10-27 | 2009-05-20 | 上海医药工业研究院 | 光学活性的取代氧膦基乙酸盐及其用途 |
| IT1394407B1 (it) | 2009-05-25 | 2012-06-15 | Dipharma Francis Srl | Procedimento per la preparazione di fosinopril e suoi intermedi |
| IT1406151B1 (it) | 2010-12-06 | 2014-02-14 | Dipharma Francis Srl | Procedimento per la preparazione di fosinopril e suoi intermedi |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4337201A (en) * | 1980-12-04 | 1982-06-29 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
| US4384123A (en) * | 1980-12-04 | 1983-05-17 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl substituted prolines |
| US4873356A (en) * | 1987-09-30 | 1989-10-10 | E. R. Squibb & Sons, Inc. | Method for preparing phosphinic acids used in preparing ace inhibitors and intermediates produced thereby |
-
1990
- 1990-01-19 US US07/467,451 patent/US5008399A/en not_active Expired - Lifetime
- 1990-12-20 AU AU68319/90A patent/AU623562B2/en not_active Expired
- 1990-12-20 CA CA002032900A patent/CA2032900C/en not_active Expired - Lifetime
- 1990-12-21 ES ES90125061T patent/ES2068321T3/es not_active Expired - Lifetime
- 1990-12-21 EP EP90125061A patent/EP0437799B1/en not_active Expired - Lifetime
- 1990-12-21 DK DK90125061.3T patent/DK0437799T3/da active
- 1990-12-21 AT AT90125061T patent/ATE118779T1/de not_active IP Right Cessation
- 1990-12-21 DE DE69017183T patent/DE69017183T2/de not_active Expired - Lifetime
- 1990-12-31 IL IL9683890A patent/IL96838A/en not_active IP Right Cessation
-
1991
- 1991-01-04 ZA ZA9196A patent/ZA9196B/xx unknown
- 1991-01-07 IE IE4791A patent/IE67354B1/en not_active IP Right Cessation
- 1991-01-16 FI FI910231A patent/FI101539B1/fi active
- 1991-01-18 NO NO910214A patent/NO179915C/no not_active IP Right Cessation
- 1991-01-18 PT PT96519A patent/PT96519B/pt not_active IP Right Cessation
- 1991-01-18 JP JP3019468A patent/JP2846484B2/ja not_active Expired - Lifetime
- 1991-01-18 HU HU91179A patent/HU208142B/hu unknown
- 1991-01-18 RU SU914894275A patent/RU2044740C1/ru active
- 1991-01-18 KR KR1019910000782A patent/KR0179368B1/ko not_active IP Right Cessation
- 1991-01-19 CN CN91100404A patent/CN1026791C/zh not_active Expired - Lifetime
-
1998
- 1998-09-28 KR KR1019980040259A patent/KR0179470B1/ko not_active IP Right Cessation
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