KR840002400A - 7-옥사비시클로헵탄 및 7-옥사비시클로헵텐 프로스타글라딘 동족체의 제조방법 - Google Patents
7-옥사비시클로헵탄 및 7-옥사비시클로헵텐 프로스타글라딘 동족체의 제조방법 Download PDFInfo
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- KR840002400A KR840002400A KR1019820005040A KR820005040A KR840002400A KR 840002400 A KR840002400 A KR 840002400A KR 1019820005040 A KR1019820005040 A KR 1019820005040A KR 820005040 A KR820005040 A KR 820005040A KR 840002400 A KR840002400 A KR 840002400A
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- alkyl group
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- 238000000034 method Methods 0.000 title claims 6
- DYWAPFDKPAHSED-UHFFFAOYSA-N 2-cycloheptyloxepane Chemical compound C1CCCCCC1C1OCCCCC1 DYWAPFDKPAHSED-UHFFFAOYSA-N 0.000 title 1
- UHZXPFSCJFEFPS-UHFFFAOYSA-N 7-(cyclohepten-1-yl)-2,3,4,5-tetrahydrooxepine Chemical compound C1CCCCC=C1C1=CCCCCO1 UHZXPFSCJFEFPS-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 31
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 239000002585 base Substances 0.000 claims 7
- -1 silyl ester Chemical class 0.000 claims 5
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 239000012442 inert solvent Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims 2
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 229910052700 potassium Inorganic materials 0.000 claims 2
- 239000011591 potassium Substances 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000001544 thienyl group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 229910010082 LiAlH Inorganic materials 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 241001122767 Theaceae Species 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 150000004982 aromatic amines Chemical class 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- XOGKVJRJHTYDBZ-UHFFFAOYSA-M azanium tetrabutylazanium difluoride Chemical compound [NH4+].[F-].[F-].CCCC[N+](CCCC)(CCCC)CCCC XOGKVJRJHTYDBZ-UHFFFAOYSA-M 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/36—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.4.0) system, e.g. naphols
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4018—Esters of cycloaliphatic acids
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
- C07F9/4059—Compounds containing the structure (RY)2P(=X)-(CH2)n-C(=O)-(CH2)m-Ar, (X, Y = O, S, Se; n>=1, m>=0)
-
- 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)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 다음 일반식(가)의 화합물을 불활성 유기용매 중에서 염기성 조건하에 다음 일반식(나)의 화합물과 반응시켜서 다음 일반식(VIII)의 화합물을 제조하고, X가 CO2R1이고 R1이 저급 알킬기일 때는 전기 일반식(VIII)의 화합물을 환원시킴을 특징으로 하는 다음 일반식(I)의 화합물 및 이들의 모든 입체 이성체를 제조하는 방법.상기 식에서, A 및 B는 같거나 상이하며, A는 CH=CH 또는 (CH2)2이고, B는 CH=CH, C=C 또는 (CH2)2이며, m은 1 내지 8이며, x는 OH,, COR1(여기서, R1은 H 또는 저급 알킬기 임) 또는(여기서, Z는 H, 저급알킬기, 아틸기, SO2=Q(여기서, Q는 저급알킬기 또는 아틸기 임),또는 OR2(여기서, R2는 H임)이며, Y는 알킬기(A와 B중의 적어도 한가지가 CH=CH기가 아니고 X는 CO2R1이 아닐 때), 치환알킬기, 아틸-저급알킬기, 알켄일기, 알킨일기, 아릴기, 피리딜기, 피리딜-저급알킬기, 치환피리딜기, 티에닐기, 티에닐-알킬기, 치환티에닐기, 시클로알킬기, 치환시클로알킬기, 시클로 알킬알킬기 또는 치환시클로알킬알킬기이고, /는 단일 결합 또는 2중 결합을 나타내며, /이 2중 결합을 나타내는 경우에는 A는 CH=CH이고 B는 CH=CH 또는 (CH2)2이고, Y는 알켄일기 또는 알킨일기이며, (상기식(가)에서, R1은 저급알킬기이고, A는 위에서 정의한 것과 같음)(상기식 (나)에서, Y는 위에서 정의한 것과 같음)(상기 식(VIII)에서, A는 (CH2)2또는 -CH=CH-임).
- 제1항에 있어서, 일반식(I)의 화합물을 염기로써 처리한 다음 산으로 처리하여 R1이 수소원자인 일반식(I)의 화합물을 제조하는 방법.
- 제2항에 있어서, R1이 수소원자인 화합물을 커플링제의 존재하에 p-디트로페놀과 반응시킨 다음 이 반응 생성물을 일반식,(여기서, M은 알칼리 금속임)의 화합물과 반응시켜서 X가(여기서, Z는임)인 일반식(I)의 화합물을 제조하는 방법.
- 제1항에 있어서, R1이 저급알킬기인 화합물을 불활성 용매의 존재하에 다음 일반식 (다)의 실릴 보호기와 반응시켜서, 다음 일반식(라)의 보호된 실릴 에스테르를 제조하고 수산화리륨과 같은 염기로 이 실릴에스테르를 처리하여 대응하는 다음 일반식(마)의 화합물로 전환시킨 다음 옥살산 또는 묽은 염산과 같은 산으로 증화시키고 불활성 유기용매 및 염기의 존재하에 술포닐이소시아네이트(O=C=N=SO2Q)와 상기 산을 반응시켜서 다음 일반식(바)의 화합물을 제조하여 테트라부틸 불화암모늄으로써 이 화합물을 처리하여 다음 일반식(사)로 표시되는 일반식(I)의 화합물을 제조하는 방법.(상기 식에서, R3는 저급알킬기 또는 아틸기이고 Y′는 알킬기 또는 아틸기 임)
- 제2항에 있어서, 다음 일반식(아)로 표시되는 화합물을 4-디메틸아미노피리딘과 같은 염기의 촉매적 량과 1당량의 카플링제의 존재하에 p-니트로페놀(PNP)과 반응시켜서 다음 일반식(자)의 대응하는 p-니트로페놀 에스테트로 전환시키고 이 p-니트로페놀 에스테르를 암모니아와 반응시켜서 다음 일반식(차)로 표시되는 일반식(I)의 화합물을 제조하는 방법.
- 제5항에 있어서, p-니트로페놀 에스테트를 알킬아민 또는 아릴아민과 반응시켜서 다음 일반식(XIX)의 화합물을 제조하는 방법.상기 식에서, Z′는 알킬기 또는 아틸기 임.
- 제1항에 있어서, R1가 저급 알킬기인 일반식(I)의 화합물을 불활성 용매중의 강염기의 존재하에 히드록시아민과 반응시킨 다음 중화시켜서 다음 구조식(XX)의 화합물을 제조하는 방법.상기 식에서 X는이고 Z는 OH임.
- 제1항에 있어서, R1이 저급알킬기인 화합물을 불활성 용매의 존재하에 LiAlH4와 반응시켜서 X가 OH인 화합물을 제조하는 방법.
- 제1항에 있어서, 다음 일반식(1)의 화합물을 염기의 존재하에 일반식, (C6H5)3P(CH2)m′CN4HBr(여기서, m′는 1 내지 8임)의 화합물과 반응시켜 다음 일반식(2)의 화합물을 제조한 다음 콜린스 산화(Collins oxidation)시켜서 다음 일반식(3)의 화합물을 제조하고 디알콕시 인산염과 상기 알데히드를 반응시켜서 다음 일반식(4)의 화합물을 제조한 다음 환원시켜서 X가인 다음 일반식(5)의 화합물을 제조하는 방법.
- 제1항에 있어서, 다음 일반식(6)의 화합물을 테트라히드로 푸란 중의 칼륨 t-부록시드 또는 디메틸 술폭시드 중의 수소화나트륨의 존재하에 다음 일반식(7)의 인산염과 반응시킨 다음 이 생성물을 테트라히드로푸란 중의 칼륨 t-부록시드와 같은 염기와 반응시켜 다음 일반식(8)의 화합물을 제조하고 이 안온을 NaBH4-CeCl3로써 환원시켜서 B가 -C=C이고 A가 -(CH2)2- 또는 -CH=CH-인 일반식(I)의 화합물을 제조하는 방법.(상기 식에서 A는 (CH2)2또는 -CH=CH-임)(상기 식에서, X′는 Cl 또는 Br임)(상기 식에서, A는 -(CH2)2- 또는 -CH=CH-임)※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019880015036A KR890000186B1 (ko) | 1981-11-09 | 1988-11-15 | 7-옥사비시클로헵탄 및 7-옥사비시클로헵텐을 함유하는 제약 조성물 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31951181A | 1981-11-09 | 1981-11-09 | |
| US319511 | 1981-11-09 | ||
| US06/378,547 US4537981A (en) | 1981-11-09 | 1982-05-17 | 7-Oxabicycloheptane and 7-oxabicycloheptene compounds |
| US378547 | 1982-05-17 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019880015036A Division KR890000186B1 (ko) | 1981-11-09 | 1988-11-15 | 7-옥사비시클로헵탄 및 7-옥사비시클로헵텐을 함유하는 제약 조성물 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840002400A true KR840002400A (ko) | 1984-07-02 |
| KR890000185B1 KR890000185B1 (ko) | 1989-03-09 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8205040A KR890000185B1 (ko) | 1981-11-09 | 1982-11-08 | 7-옥사비시클로헵탄 및 7-옥사비시클로헵텐 화합물 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4537981A (ko) |
| EP (1) | EP0079694B1 (ko) |
| KR (1) | KR890000185B1 (ko) |
| AU (1) | AU569464B2 (ko) |
| CA (1) | CA1215063A (ko) |
| DE (1) | DE3276317D1 (ko) |
| DK (1) | DK497682A (ko) |
| GR (1) | GR76780B (ko) |
| IE (1) | IE54086B1 (ko) |
| IL (1) | IL66989A0 (ko) |
| NZ (1) | NZ202138A (ko) |
| PH (1) | PH22106A (ko) |
| PT (1) | PT75811B (ko) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4837234A (en) * | 1981-12-23 | 1989-06-06 | National Research Development Corporation | Prostaglandins |
| DE3280020D1 (en) * | 1981-12-23 | 1989-12-21 | Nat Res Dev | Prostaglandins |
| US4614825A (en) * | 1982-05-17 | 1986-09-30 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane and 7-oxabicycloheptene compounds |
| US4474972A (en) * | 1983-03-14 | 1984-10-02 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane prostaglandin intermediates and method for preparing same |
| US4536514A (en) * | 1984-04-06 | 1985-08-20 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted prostaglandin analogs useful in the treatment of thrombolytic disease |
| US4661506A (en) * | 1984-11-30 | 1987-04-28 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted ox prostaglandin analogs |
| US4588743A (en) * | 1985-01-22 | 1986-05-13 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane-substituted oxa prostaglandin analogs and their use in the treatment of thrombolytic disease |
| US4591603A (en) * | 1985-02-25 | 1986-05-27 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted prostaglandin analogs useful in the treatment of thrombotic disease |
| US4611007A (en) * | 1985-04-22 | 1986-09-09 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane substituted prostaglandin analogs useful in the treatment of thrombotic disease |
| US4654366A (en) * | 1986-02-14 | 1987-03-31 | E. R. Squibb & Sons, Inc. | Hydroxamic acids of 7-oxabicyclo[2.2.1]heptane substituted ethers useful as anti-thrombotic agents |
| US4931460A (en) * | 1987-09-17 | 1990-06-05 | E. R. Squibb & Sons, Inc. | Post-ischemic myocardial dysfunction using thromboxane A2 antagonists |
| US4900723A (en) * | 1988-04-29 | 1990-02-13 | E. R. Squibb & Sons, Inc. | Method of preventing or reducing venous thrombosis using a thromboxane A2 receptor antagonist in conjunction with heparin and combination |
| US4925873A (en) * | 1988-09-01 | 1990-05-15 | E. R. Squibb & Sons, Inc. | Method of treating skin injuries using thromboxane A2 receptor antagonists |
| US4839384A (en) * | 1988-10-07 | 1989-06-13 | E. R. Squibb & Sons, Inc. | Method of inhibiting onset of or treating migraine headache using a thromboxane A2 receptor antagonist |
| CA2006086A1 (en) * | 1989-01-17 | 1990-07-17 | A. K. Gunnar Aberg | Method of preventing or treating atherosclerosis using a thromboxane a receptor antagonist |
| CA2007896A1 (en) * | 1989-02-06 | 1990-08-06 | A.K. Gunnar Aberg | Method of treating hypertension using a thromboxane a2 receptor antagonist and new combinations |
| CA2012852A1 (en) * | 1989-05-01 | 1990-11-01 | Miguel A. Ondetti | Method of inhibiting vasospasm and platelet aggregation resulting from angioplasty using thromboxane a receptor antagonists |
| US5093329A (en) * | 1990-03-12 | 1992-03-03 | Allergan, Inc. | Intraocular pressure reducing prostaglandin-like 7-oxabicyclo derivatives |
| ZA911453B (en) * | 1990-03-19 | 1991-11-27 | Squibb & Sons Inc | Method of protecting against and/or treating ulcerative gastrointestinal conditions using a thromoboxane,a2 receptor antagonist and combination useful in preventing and/or treating ulcers and/or inflammation |
| EP1554572B1 (en) | 2001-07-25 | 2009-10-14 | Raptor Pharmaceutical Inc. | Compositions and methods for modulating blood-brain barrier transport |
| EP3827747A1 (en) | 2005-04-28 | 2021-06-02 | Otsuka Pharmaceutical Co., Ltd. | Pharma-informatics system |
| EP2063905B1 (en) | 2006-09-18 | 2014-07-30 | Raptor Pharmaceutical Inc | Treatment of liver disorders by administration of receptor-associated protein (rap)-conjugates |
| NZ616673A (en) | 2009-02-20 | 2014-08-29 | To Bbb Holding B V | Glutathione-based drug delivery system |
| ES2942923T3 (es) | 2009-05-06 | 2023-06-07 | Laboratory Skin Care Inc | Composiciones de administración dérmica que comprenden complejos de agente activo-partículas de fosfato de calcio y métodos de uso de las mismas |
| US20120077778A1 (en) | 2010-09-29 | 2012-03-29 | Andrea Bourdelais | Ladder-Frame Polyether Conjugates |
| DK3142655T3 (da) | 2014-05-16 | 2021-02-01 | Cumberland Pharmaceuticals Inc | Sammensætninger og fremgangsmåder til behandling af hjertefibrose med ifetroban |
| CN107708692A (zh) | 2015-06-30 | 2018-02-16 | 坎伯兰医药品股份有限公司 | Aerd/哮喘中的血栓烷受体拮抗剂 |
| WO2017197107A1 (en) | 2016-05-11 | 2017-11-16 | Cumberland Pharmaceuticals, Inc. | Compositions and methods of treating muscular dystrophy with thromboxane-a2 receptor antagonists |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4088779A (en) * | 1973-05-18 | 1978-05-09 | Ciba-Geigy Corporation | 9-Oxaprostaglandins |
| DE2357953A1 (de) * | 1973-11-21 | 1975-05-28 | Hoechst Ag | Neue, natuerlich nicht vorkommende analoga von prostansaeuren und verfahren zu ihrer herstellung |
| US4254044A (en) * | 1977-11-04 | 1981-03-03 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane- and 7-oxabicycloheptene compounds |
| US4187236A (en) * | 1977-11-04 | 1980-02-05 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane compounds |
| US4220594A (en) * | 1977-11-04 | 1980-09-02 | E. R. Squibb & Sons, Inc. | Hexa- and octahydro-4,7-epoxyisobenzofuran-1-ol and hexa- and octahydro-5,8-epoxy-1H-2-benzopyran-3-ol |
| US4143054A (en) * | 1977-11-04 | 1979-03-06 | E. R. Squibb & Sons, Inc. | 7-oxabicycloheptane- and 7-oxabicycloheptene compounds |
| US4228180A (en) * | 1979-11-01 | 1980-10-14 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane and 7-oxabicycloheptene prostaglandin analogs |
| US4436934A (en) * | 1981-02-05 | 1984-03-13 | Iowa State University Research Foundation, Inc. | Bicyclic prostaglandin analogs and method of synthesis |
| US4416896A (en) * | 1982-05-17 | 1983-11-22 | E. R. Squibb & Sons, Inc. | 7-Oxabicyclopheptane substituted amino prostaglandin analogs useful in the treatment of thrombolytic disease |
| US4456615A (en) * | 1982-10-25 | 1984-06-26 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted amino prostaglandin analogs and their use in inhibiting platelet aggregation and bronchoconstriction |
| US4456616A (en) * | 1982-12-27 | 1984-06-26 | E. R. Squibb & Sons, Inc. | 7-Oxabicycloheptane substituted amino prostaglandin analogs and their use in inhibiting platelet aggregation and bronchoconstriction |
-
1982
- 1982-05-17 US US06/378,547 patent/US4537981A/en not_active Expired - Fee Related
- 1982-10-08 CA CA000413160A patent/CA1215063A/en not_active Expired
- 1982-10-12 NZ NZ202138A patent/NZ202138A/en unknown
- 1982-10-14 PH PH27983A patent/PH22106A/en unknown
- 1982-10-14 AU AU89359/82A patent/AU569464B2/en not_active Ceased
- 1982-10-15 IL IL66989A patent/IL66989A0/xx not_active IP Right Cessation
- 1982-10-22 DE DE8282305634T patent/DE3276317D1/de not_active Expired
- 1982-10-22 EP EP82305634A patent/EP0079694B1/en not_active Expired
- 1982-11-05 IE IE2648/82A patent/IE54086B1/en not_active IP Right Cessation
- 1982-11-08 PT PT75811A patent/PT75811B/pt not_active IP Right Cessation
- 1982-11-08 GR GR69754A patent/GR76780B/el unknown
- 1982-11-08 KR KR8205040A patent/KR890000185B1/ko active
- 1982-11-08 DK DK497682A patent/DK497682A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL66989A0 (en) | 1983-02-23 |
| PT75811B (en) | 1985-07-26 |
| IE822648L (en) | 1983-05-09 |
| EP0079694B1 (en) | 1987-05-13 |
| US4537981A (en) | 1985-08-27 |
| CA1215063A (en) | 1986-12-09 |
| IE54086B1 (en) | 1989-06-07 |
| GR76780B (ko) | 1984-09-04 |
| PH22106A (en) | 1988-06-01 |
| DE3276317D1 (en) | 1987-06-19 |
| KR890000185B1 (ko) | 1989-03-09 |
| AU8935982A (en) | 1983-05-19 |
| NZ202138A (en) | 1986-03-14 |
| DK497682A (da) | 1983-05-10 |
| EP0079694A1 (en) | 1983-05-25 |
| AU569464B2 (en) | 1988-02-04 |
| PT75811A (en) | 1982-12-01 |
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