KR860007212A - 유익한 치료학적 특성을 갖는 신규[4.2.0]비시클로옥탄 유도체의 제조방법 - Google Patents
유익한 치료학적 특성을 갖는 신규[4.2.0]비시클로옥탄 유도체의 제조방법 Download PDFInfo
- Publication number
- KR860007212A KR860007212A KR1019860002246A KR860002246A KR860007212A KR 860007212 A KR860007212 A KR 860007212A KR 1019860002246 A KR1019860002246 A KR 1019860002246A KR 860002246 A KR860002246 A KR 860002246A KR 860007212 A KR860007212 A KR 860007212A
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- South Korea
- Prior art keywords
- ynyl
- oct
- ylidene
- hydroxy
- hydroxybicyclo
- Prior art date
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- 238000000034 method Methods 0.000 title claims 5
- 230000009286 beneficial effect Effects 0.000 title 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical class C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 31
- 231100000252 nontoxic Toxicity 0.000 claims abstract 20
- 230000003000 nontoxic effect Effects 0.000 claims abstract 20
- 150000003839 salts Chemical class 0.000 claims abstract 19
- 150000002148 esters Chemical class 0.000 claims abstract 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 15
- 239000001257 hydrogen Substances 0.000 claims abstract 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 52
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 12
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 8
- -1 (Z)-(3'S * Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 4
- 125000006239 protecting group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims 1
- 102100026459 POU domain, class 3, transcription factor 2 Human genes 0.000 claims 1
- 101710133394 POU domain, class 3, transcription factor 2 Proteins 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000006772 olefination reaction Methods 0.000 claims 1
- 150000003018 phosphorus compounds Chemical class 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- 229960000281 trometamol Drugs 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 abstract 1
- 208000024172 Cardiovascular disease Diseases 0.000 abstract 1
- 206010020772 Hypertension Diseases 0.000 abstract 1
- 208000007536 Thrombosis Diseases 0.000 abstract 1
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- H04N9/00—Details of colour television systems
- H04N9/79—Processing of colour television signals in connection with recording
- H04N9/7921—Processing of colour television signals in connection with recording for more than one processing mode
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- 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
- C07C35/31—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 containing eight carbon atoms
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- C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
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- C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
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- C07C403/20—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by carboxyl groups or halides, anhydrides, or (thio)esters thereof
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- C07C45/305—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with halogen containing compounds, e.g. hypohalogenation with halogenochromate reagents, e.g. pyridinium chlorochromate
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- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
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Abstract
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Claims (12)
- 하기 일반식(1),(2) 또는 (3)의 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류를 제조함에 있어서,; 상기식중, n는 2 또는 3이고, R1는 CH2OH,CHO,CO2R [식중, R은기로서, 여기에서 X는기(여기에서, R4는 독립적으로 수소, 또는 탄소 원자수가 1-6개인 알킬기임)], 또는 CO2H기이고, R2는 수소 또는 메틸기이고, R3는 직쇄 또는 측쇄 알킬기(탄소원자수 5-10개),(식중, a는 0.1 또는 2이고, b는 3-7),또는 -(CH2)m-페닐기(여기에서, m는 0,1 또는 2이고, 이 기는 저급 알킬, 저급 알콕시, 트리플루오로메틸기 또는 할로겐으로 임의로 치환됨)임;a) 일반식(식중, R2및 R5는 상기 정의한 바와같음)의 화합물을 적당히 선택된 안정화음이온 또는 일반식(여기에서, P'는 올레핀화반응으로 결합된 통상의 잔기이고, n는 2 또는 3이고, R1는 상기 정의한 바와 같거나, 또는 보호 유도체 또는 그 염임)의 일리드와 반응시켜서 일반식 (1) 화합물과 일반식 (2) 화합물의 혼합물, 또는 화합물(3)과 그의 대응하는 E-화합물의 혼합물을 얻은 후, 혼합물을 분리하거나, 또는(b) 일반식(식중, n,R1,R2및 R3는 상기 정의한 바와같고, Pt는 측쇄의 히드록실 기능기의 보호기임)의 화합물중 보호기를 제거하여 일반식(1),(2) 또는 (3)의 화합물을 얻거나, 또는(c) 일반식(식중, n,R1,R2및 R3는 상기 정의한 바와같고, Pt는 측쇄의 히드록실 작용기의 보호기임)의 화합물중 보호기를 제거하여 일반식(1),(2) 또는 (3)(여기에서, R1는 CH2OH임)의 화합물을 얻은 후, 다음과 같은 임의의 단계, 즉, e) 일반식(1),(2) 또는 (3)의 화합물 중 R1가 CO2H인 화합물을 R1가 CH2OH인 대응하는 화합물로 전환시키거나, 또는 f) R1가 CO2H인 일반식 (1),(2) 또는 (3)의 화합물 중 R1가 CHO인 대응하는 화합물로 전환시키거나, 또는 g) R1가 CO2H인 일반식 (1),(2) 또는 (3)의 화합물 중 R1가 CO2R인 대응하는 화합물로 전환시키고, 또, 다음과 같은 임의의 단계, 즉, h) 일반식 (1),(2) 또는 (3)의 산을 약물학적으로 허용되는 그의 무독성 염으로 전환시키고, i) 일반식 (1),(2) 또는 (3)화합물의 약물학적으로 허용되는 그의 무독성 염을 이에 대응하는 산 또는 에스테르로 전환시키고, j) 일반식 (1),(2) 또는 (3)의 산을 약물학적으로 허용되는 그의 무독성 에스테르로 전환시키고, k) 일반식 (1),(2) 또는 (3)화합물의 약물학적으로 허용되는 그의 무독성 에스테르를 이에 대응하는 산 또는 염으로 전환시키고, I) 일반식 (1),(2) 또는 (3)화합물의 약물학적으로 허용되는 그의 무독성 에스테르를 약물학적으로 허용되는 다른 무독성 에스테르로 전환시키고, m) 일반식 (1),(2) 또는 (3)화합물의 약물학적으로 허용되는 그의 무독성 염을 약물학적으로 허용되는 다른 무독성 염으로 전환시킴을 특징으로 하는 방법.
- 제1항에 있어서, n가 2 또는 3이고, R1가 CO2H,CO2R(식중, R는 제1항에서 정의한 바와같음) 또는 CH2OH이고, R2가 수소 또는 메틸이고, R3가 직쇄 또는 측쇄 알킬기(탄소 원자수 5내지 10개),(식중, a 및 b는 제1항에서 정의한 바와같음), 또는 -(CH2)m-페닐(식중, m는 제1항에서 정의한 바와같음)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류의 제조방법.
- 제2항에 있어서, n가 2 또는 3이고, R1가 CO2R 또는 CO2H이고, R2가 수소 또는 메틸이고, R3가 n-펜틸인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류의 제조방법.
- 제3항에 있어서, n가 2이고, R1가 CO2H이고, R2가 수소이고, R3가 n-펜틸인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시옥트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산, (Z)-(3'S,1R,2R,3S,6R)-4-[2-(3'-히드록시옥트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산 및 (E)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시옥트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산의 제조방법.
- 제2항에 있어서, n가 2 또는 3이고, R1가 CO2R 또는 CO2H이고, R2가 수소 또느 메틸이고, R3가(식중, a는 0 또는 1이고, b는 3-7)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류의 제조방법.
- 제5항에 있어서, n가 2이고, R1가 CH2H이고, R2가 수소이고, R3가(식중, a는 0이고, b는 4임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 (Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-시클로펜틸프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산, (Z)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로펜틸프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산 및 (E)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로펜틸프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산의 제조방법.
- 제5항에 있어서, n가 2이고, R1가 CO2H이고, R2가 수소이고, R3가(식중, a는 0이고, b는 5임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 다음과 같은 화합물의 제조방법.(Z)-(3'S,1R,2R,3S,6R)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;(Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;(E)-(3'S,1S,2S,3R,6S)-4-[2(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;메틸 (Z)-(3'S,1S,2S,3R,6S)-4-[2-3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;(Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-시클로-헥폰프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;(E)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로-헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;(Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-시클로-헥폰프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산;메틸 (Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;메틸 (Z)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;소듐 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;포태슘 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;칼슘 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;마그네슘 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;트로메타민 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트;에틸렌디아민 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트 및 N-메틸-D-글루카민 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트.
- 제5항에 있어서, n가 3이고, R1가 CO2H이고, R2가 수소이고, R3가(식중, a는 0이고,, b는 5임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 다음과 같은 화합물의 제조방법.(Z)-(3'S,1S,2S,3R,6S)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산,(Z)-(3'S,1R,2R,3S,6R)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산,(E)-(3'S,1S,2S,3R,6S)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산,(Z)-(3'S*,1S*,2S*,3R*,6S*)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산,(Z)-(3'S*,1R*,2R*,3S*,6R*)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산 및 (E)-(3'S*,1S*,2S*,3R*,6S*)-5-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]펜탄산.
- 제5항에 있어서, n가 2이고, R1가 CO2R(식중, R는 벤즈아미도페닐 또는 아세틸 아미노페닐임)이고, R2가 수소이고, R3가 (식중, a는 0이고,, b는 5임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 4-벤즈아미도페닐 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트 및 4-아세틸아미도페닐 (Z)-(3'S,1S,2S,3R,6S)-4-[2-(3'-히드록시-3'-시클로헥실프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티레이트의 제조방법.
- 제5항에 있어서, n가 2이고, R1가 CO2H이고, R2가 수소이고, R3가 (식중, a는 1이고, b는 5임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 (Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-시클로헥실부트-1'-이닐,-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산,(Z)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로헥실부트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산 및 (E)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-시클로헥실부트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산의 제조방법.
- 제2항에 있어서, n가 2이고, R1가 CO2H이고, R2가 수소이고, R3가 -CH2)M-페닐(식중, m은 0임)인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류, 즉 (Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-3'-페닐프로프-1'-이닐-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산 및 (Z)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-3'-페닐프로프-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산의 제조방법.
- 제2항에 있어서, n가 2이고, R1가 CO2H이고, R2가 수소이고, R3가인 화합물, 약물학적으로 허용되는 그의 무독성 염 및 그의 에스테르류 즉 (Z)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-4'-엔도-비시클로[3.1.0] 헥스-6-일부트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산,(E)-(3'S*,1S*,2S*,3R*,6S*)-4-[2-(3'-히드록시-4'-엔도-비시클로[3.1.0] 헥스-6-일부트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산 및 (Z)-(3'S*,1R*,2R*,3S*,6R*)-4-[2-(3'-히드록시-4'-엔도-비시클로[3.1.0] 헥스-6-일부트-1'-이닐)-3-히드록시비시클로[4.2.0]옥트-7-일리덴]부티르산의 제조방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US716872 | 1985-03-27 | ||
| US06/716,872 US4608388A (en) | 1985-03-27 | 1985-03-27 | Novel [4,2,0]bicyclooctane derivatives with valuable therapeutic properties |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR860007212A true KR860007212A (ko) | 1986-10-08 |
| KR910000254B1 KR910000254B1 (ko) | 1991-01-23 |
Family
ID=24879801
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019860002246A KR910000254B1 (ko) | 1985-03-27 | 1986-03-26 | 유익한 치료학적 특성을 갖는 신규[4.2.0]비시클로옥탄 유도체의 제조방법 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US4608388A (ko) |
| EP (1) | EP0196617B1 (ko) |
| JP (1) | JPS61227544A (ko) |
| KR (1) | KR910000254B1 (ko) |
| AT (1) | ATE43575T1 (ko) |
| AU (1) | AU599018B2 (ko) |
| CA (1) | CA1284654C (ko) |
| CS (1) | CS257285B2 (ko) |
| DD (1) | DD244132A5 (ko) |
| DE (1) | DE3663660D1 (ko) |
| DK (1) | DK145286A (ko) |
| ES (2) | ES8800146A1 (ko) |
| FI (1) | FI861324A (ko) |
| GR (1) | GR860778B (ko) |
| HU (1) | HU195634B (ko) |
| IL (1) | IL78273A0 (ko) |
| NO (1) | NO164017C (ko) |
| NZ (1) | NZ215610A (ko) |
| PH (1) | PH23489A (ko) |
| PL (5) | PL148469B1 (ko) |
| PT (1) | PT82286B (ko) |
| SU (2) | SU1500153A3 (ko) |
| ZA (1) | ZA862278B (ko) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4678805A (en) * | 1985-03-27 | 1987-07-07 | Syntex (U.S.A.) Inc. | Novel 8-(lower alkyl)bicyclo[4.2.0]octane derivatives with valuable therapeutic properties |
| US4792561A (en) * | 1986-05-29 | 1988-12-20 | Syntex (U.S.A.) Inc. | Carbostyril derivatives as combined thromboxane synthetase and cyclic-AMP phosphodiesterase inhibitors |
| US4735966A (en) * | 1986-08-25 | 1988-04-05 | Syntex (U.S.A.) Inc. | Novel substituted (4.2.0)bicyclooctane derivatives with valuable therapeutic properties |
| US5049497A (en) * | 1986-08-25 | 1991-09-17 | Syntex (U.S.A.) Inc. | Novel process for the synthesis of the enantiomers of bicyclo(4.2.0)oct-2-en-7-one and derivatives |
| US4730078A (en) * | 1987-05-13 | 1988-03-08 | G. D. Searle & Co. | Allenic prostacyclins |
| US4983627A (en) * | 1988-11-10 | 1991-01-08 | Syntex (U.S.A.) Inc. | Novel 6-alkyl and 6.8-dialkylbicyclo(4.2.0)octane derivatives |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4705806A (en) * | 1978-02-13 | 1987-11-10 | Morton Jr Douglas R | Prostacyclin analogs |
| US4288606A (en) * | 1979-06-14 | 1981-09-08 | The Upjohn Company | Esters of prostacyclin-type compounds |
| US4267395A (en) * | 1979-07-05 | 1981-05-12 | The Upjohn Company | 2-Decarboxy-2-hydroxymethyl-19-hydroxy-19-methyl-6A-carba-PGI2 compounds |
| US4420632A (en) * | 1980-04-15 | 1983-12-13 | The Upjohn Company | Composition and process |
| US4306076A (en) * | 1980-04-23 | 1981-12-15 | The Upjohn Company | Inter-phenylene CBA compounds |
-
1985
- 1985-03-27 US US06/716,872 patent/US4608388A/en not_active Expired - Fee Related
-
1986
- 1986-03-26 ES ES553437A patent/ES8800146A1/es not_active Expired
- 1986-03-26 NO NO861244A patent/NO164017C/no unknown
- 1986-03-26 GR GR860778A patent/GR860778B/el unknown
- 1986-03-26 NZ NZ215610A patent/NZ215610A/xx unknown
- 1986-03-26 PL PL1986263593A patent/PL148469B1/pl unknown
- 1986-03-26 HU HU861272A patent/HU195634B/hu not_active IP Right Cessation
- 1986-03-26 EP EP86104158A patent/EP0196617B1/en not_active Expired
- 1986-03-26 DE DE8686104158T patent/DE3663660D1/de not_active Expired
- 1986-03-26 PL PL1986263592A patent/PL263592A1/xx unknown
- 1986-03-26 SU SU864027261A patent/SU1500153A3/ru active
- 1986-03-26 PL PL1986258627A patent/PL148462B1/pl unknown
- 1986-03-26 CA CA000505253A patent/CA1284654C/en not_active Expired - Fee Related
- 1986-03-26 PL PL1986263590A patent/PL148468B1/pl unknown
- 1986-03-26 PH PH33594A patent/PH23489A/en unknown
- 1986-03-26 JP JP61069703A patent/JPS61227544A/ja active Pending
- 1986-03-26 PT PT82286A patent/PT82286B/pt not_active IP Right Cessation
- 1986-03-26 PL PL1986263591A patent/PL263591A1/xx unknown
- 1986-03-26 FI FI861324A patent/FI861324A/fi not_active Application Discontinuation
- 1986-03-26 KR KR1019860002246A patent/KR910000254B1/ko not_active IP Right Cessation
- 1986-03-26 DD DD86288328A patent/DD244132A5/de not_active IP Right Cessation
- 1986-03-26 ZA ZA862278A patent/ZA862278B/xx unknown
- 1986-03-26 DK DK145286A patent/DK145286A/da not_active IP Right Cessation
- 1986-03-26 CS CS862135A patent/CS257285B2/cs unknown
- 1986-03-26 AT AT86104158T patent/ATE43575T1/de active
- 1986-03-26 AU AU55289/86A patent/AU599018B2/en not_active Ceased
- 1986-03-26 IL IL78273A patent/IL78273A0/xx not_active IP Right Cessation
-
1987
- 1987-04-08 SU SU874202298A patent/SU1588275A3/ru active
- 1987-07-30 ES ES557637A patent/ES8802482A1/es not_active Expired
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