KR830006158A - 헤테로-프로스타글란딘 유도체의 제조 방법 - Google Patents
헤테로-프로스타글란딘 유도체의 제조 방법 Download PDFInfo
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- KR830006158A KR830006158A KR1019810002839A KR810002839A KR830006158A KR 830006158 A KR830006158 A KR 830006158A KR 1019810002839 A KR1019810002839 A KR 1019810002839A KR 810002839 A KR810002839 A KR 810002839A KR 830006158 A KR830006158 A KR 830006158A
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- hydroxy
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- cyclopentene
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- 238000000034 method Methods 0.000 title claims 7
- 238000002360 preparation method Methods 0.000 title claims 5
- 239000002253 acid Substances 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 11
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 claims 8
- 239000002904 solvent Substances 0.000 claims 8
- -1 alkali metal salt Chemical class 0.000 claims 7
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- 238000004519 manufacturing process Methods 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims 5
- 239000003814 drug Substances 0.000 claims 5
- UQXKQJASJWQKAC-UHFFFAOYSA-N C1=CCCC1.[P] Chemical class C1=CCCC1.[P] UQXKQJASJWQKAC-UHFFFAOYSA-N 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- 239000005977 Ethylene Substances 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- AJYFEARSYOPEAR-FHWLQOOXSA-N (2S)-2-hydroxy-7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid Chemical compound O[C@H](C(=O)O)CCCCC[C@H]1CCC[C@@H]1CCCCCCCC AJYFEARSYOPEAR-FHWLQOOXSA-N 0.000 claims 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 2
- 150000001299 aldehydes Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 229910000085 borane Inorganic materials 0.000 claims 2
- QDPOHAYYMHVFMI-UHFFFAOYSA-N boron;hydrate Chemical compound [B].O QDPOHAYYMHVFMI-UHFFFAOYSA-N 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229910052698 phosphorus Inorganic materials 0.000 claims 2
- 239000011574 phosphorus Substances 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- JUWYRPZTZSWLCY-UHFFFAOYSA-N 5-carboxypentyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCCC(=O)O)C1=CC=CC=C1 JUWYRPZTZSWLCY-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical class CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 1
- OHBTULDTCSOWOY-UHFFFAOYSA-N [C].C=C Chemical compound [C].C=C OHBTULDTCSOWOY-UHFFFAOYSA-N 0.000 claims 1
- 125000004036 acetal group Chemical group 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- MLUCVPSAIODCQM-UHFFFAOYSA-N but-2-enal Chemical group CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- RCTYPNKXASFOBE-UHFFFAOYSA-M chloromercury Chemical compound [Hg]Cl RCTYPNKXASFOBE-UHFFFAOYSA-M 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000000468 ketone group Chemical group 0.000 claims 1
- 229960002523 mercuric chloride Drugs 0.000 claims 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 claims 1
- 150000007523 nucleic acids Chemical class 0.000 claims 1
- 102000039446 nucleic acids Human genes 0.000 claims 1
- 108020004707 nucleic acids Proteins 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 229910052763 palladium Inorganic materials 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 claims 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims 1
- 150000003180 prostaglandins Chemical class 0.000 claims 1
- 230000001681 protective effect Effects 0.000 claims 1
- NCHPDGCQTUJYKK-UHFFFAOYSA-N pyrrolidin-1-ium;acetate Chemical compound CC(O)=O.C1CCNC1 NCHPDGCQTUJYKK-UHFFFAOYSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000004936 stimulating effect Effects 0.000 claims 1
- FQFKTKUFHWNTBN-UHFFFAOYSA-N trifluoro-$l^{3}-bromane Chemical compound FBr(F)F FQFKTKUFHWNTBN-UHFFFAOYSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
- C07C405/0008—Analogues having the carboxyl group in the side-chains replaced by other functional groups
- C07C405/0033—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing sulfur
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/60—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in six-membered rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (18)
- 다음 구조식으로 표현되는 프로스탄산 유도체X는 수소나 하이드록시기이며 X1은 수소인데 X와 X1이 주위의 탄소와 인접할 때는 카르복시기를 나타내며 Z는 수소나 하이드록시기를 나타내는 프로스탄산 유도체와 의약품으로 사용되는 상기 유도체의 알칼리금속염의 제조방법.
- 11(R)-하이드록시-13-옥시-프로스탄산과-의약품으로 사용되는 이 화합물의 알칼리 금속염의 제조방법.
- 11(R)-하이드록시-13-옥시-15(S)-하이드록시-프로스탄산과 의약품으로 사용되는 이 화합물의 알칼리 금속염의 제조방법.
- 9(S)-하이드록시-11(R)-하이도록시-13-옥시-프로스탄산과 의약품으로 사용되는 이 화합물의 알칼리 금속염의 제조방법.
- 9(S)-하이드록시-11(R)-하이도록시-13-옥시-15(S)-하이드록시-프로스탄산과 의약품으로 사용되는 알칼리 금속염의 제조방법.
- 다음 구조식의 프로스탄산 유도체에서R은 구조식-CH2R1의 하이드록시-보호기이며 이 구조식의 R1은 아릴기 또는 아릴킬기이며 D'는기이며 Z'는 수소나 O-R기이고 상기와 같은 뜻을 가지는 R은 실온에서 플레이티늄 차코올 또는 팔라듐 차코올에 의해 가수소화되어 적절한 매질하에서 X가 수소또는 하이드록시기를 나타내는 자유산형의 13-옥시-프로스타글라딘 또는 다음 구조식의 (6-카르복시핵세닐)-3(R)-헵틸록시 유도체가 생성되는데여기서 상기와 같은 뜻인 Z는 적절한 용매와 브론 트리플로라이드 에테레이트의 존재하에서 탈(脫)티오아세탈화 되어 X와 X1주위의 탄소원자와 인접할 때 카르보닐기를 나타내는 13-옥시-프로스타글라딘이 자유산형태로 생성되고 생성된 자유산은 적절한 알칼리 금속 수산화물과 반응하여, 의약품으로 사용되는 이화합물의 아랄리 급속염이 생성되는 특허청구범위 제1항에서 제5항에 따른 프로스탄산 유도체의 제조방법.
- 매질은 아세트산/에탄올 매질이고 용매는 아세톤인 특허청구 범위 제6항에 따른 프로스탄산 유도체의 제조방법.
- 아릴기는 메틸기에 의해 치환되거나 치환되지 않은 페닐이고 아랄킬기는 메틸기에 의해 치환되거나 치환되지 않은 방향족 성분의 벤질인 특허청구 범위 제6항에 따른 프로스탄산 유도체의 제조방법
- 특허청구 범위 제1항에서 제5항에 따른 한개 이상의 프로스탄산 유도체와 이 화합물의 제약학적 전달체나 부형제와 함께 필수 활성용소로 구성되는 의학적, 수의학적 조성물의 제조방법.
- 특허청구 범위 제1항에서 제5항에 따른 한개 이상의 화합물의 유효한 양을 환자에 투약하여 기관지 확장을 자극하거나 혈소판 확장을 억제시키는 방법.
- 다음 구조식으로 표현되는 사이클로펜텐 유도체에서R은 구조식 -CH2R1의 하이드록시-보호기를 나타내며 이 구조식의 R1은 아릴기나 아랄킬기이고 B는일때인 사이클로펜텐 유도체의 제조방법.
- 알릴기는 메틸기에 의해 치환되거나 치환되지 않은 페닐이고 아랄킬기는 메틸기에 의해 치환되거나 치환되지 않은 방향족 성분의 벤질인 특허청구 범위 제11항에 따른 사이클로펜텐 유도체의 제조방법.
- a) 다음 구조식의 핵산디알 유도체에서R은 상기와 같은 뜻이며 D는인데 -10℃에서 실온사이의 온도 및 내부기압에서 적절한 용매의 존재하에 피롤리딘 아세테이트 또는 피페리딘 아세테이트에 의해 고리화되어 B가이고 A가인 사이클로페넨 유도체가 생성되며b) 이 유도체와 실온에서 40℃의 온도 사이에서 p-톨루엔 실폰산의 존재하에 1,3-프로판디올과 반응하며 무수용매의 존재하에 B가인 사이클로펜텐유도체가 생성되며,c) A가인 이 유도체와 순수 디페닐 실렌무수물이 실온에서 적절한 용매하에서 반응하여 B가이며 A가인 사이클로펜텐 유도체가 생성되며d) 이 유도체와 디잇부틸 알루미늄 수화물이 적절한 무수용매의 존재하에서 -10℃와 실온사이의 온도에서 반응하여 B가인 사이클로펜텐 유도체가 생성되는 특허청구 범위 베11항에 따른 사이클로펜텐 유도체의 제조방법.
- 특허청구 범위 제13a항, 제13b항 또는 제13d항의 용매는 벰젠 또는 톨루엔이고 제13d항의 용매는 디클로로메탄인 사이클로펜텐 유도체의 제조방법.
- 구조식(1a)의 화합물의 제조에서 A가또는 신톤 B인 특허청구 범위 제13항에 따른 사이클로펜텐 유도체의 제조방법.
- 구조식(1a)의 화합물의 제조에서 A가또는 신톤 D인 특허청구범위 제13항에 따흔 사이클로펜텐 유도체의 제조방법.
- 구조식(1a)의 화합물의 제조에서 A가또는 신톤 F인 특허청구범위 제13항에 따흔 사이클로펜텐 유도체의 제조방법.
- 다음 구조식의 사이클로펜텐 유도체에서R은 구조식 -CH2R1의 하이드록시-보호기이며 이 구조식에서 R1은 아릴기나 아랄킬기이고 Z'는 수소 또는 -OR기이며 E는이고 R은 상기와 같은 뜻인데 이 유도체의 포밀프로필렌아세탈기가 산매질하에서 가수분해하여 알데하이드가 생성되고 생성된 알데하이드와 (5-카르복시펜틸)-트리페닐포스포늄 브로마이드의 두 음이온은 비티그 반응의 조건하에서 반응하여 에틸렌 카본 사술을 만들고 플레이티늄 차코올 또는 팔라듐 차코올에서 가수소분해되어 에틸렌 사술이 포화되며 하이드록실기의 보호분해 반응이 일너나는데 필요하면 염화수은에 의해 탈티오아세탈화하여 케토기를 형성하여 청구범위 제1항에 따른 화화ㅂ물이 생성되고 구조식(33) 화합물에 신톤 B 또는 신톤 F가 보란의 산화에 의한 보론 수화물과 반응하여 에틸렌 결합의 하이드록시기를 고정시켜서 n-할로게노헵탄 유도체와 반응하여 형성된 하이드록실기를 에테르화하며 에틸렌디티오아세탈기를 라니 니켈과 환원반응시키거나 또는 염화수은과 탈티오 아세탈화반응을 거쳐 케톤기를 형성하고 리튬 트리-세크-부틸보로하이드라이드와 환원반응을 거쳐 하이드록실기를 형성하며 형성된 하이드록실기는 보호되고 신톤 D의 자유하이드록실기를 보호하여 생성된 산고가 보호된-유도체와 보론 수화물이 반응하고 형성된 보란의 산화작용으로 에틸렌 결합의 하이드록실기를 고정하며 n-할로게노헵탄 유도체와 반응하여 형성된 하이드록실기를 에테르화하여 E가인 구조식(33) 화합물이 생성되는 특허청구범위 제1항의 유도체를 제조하기 위한 특허청구 범위 제15항, 제16항, 제17항에 설명된 신톤 B, 신톤 F의 사용방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019840005809A KR850000670B1 (ko) | 1980-08-12 | 1984-09-21 | 사이클로 펜텐 유도체의 제조방법 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB80-26240 | 1980-08-12 | ||
| GB8026240 | 1980-08-12 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840005809A Division KR850000670B1 (ko) | 1980-08-12 | 1984-09-21 | 사이클로 펜텐 유도체의 제조방법 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830006158A true KR830006158A (ko) | 1983-09-17 |
| KR840002175B1 KR840002175B1 (ko) | 1984-11-26 |
Family
ID=10515399
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019810002839A KR840002175B1 (ko) | 1980-08-12 | 1981-08-04 | 사이클로 펜텐유도체의 제조방법 |
| KR1019840005809A KR850000670B1 (ko) | 1980-08-12 | 1984-09-21 | 사이클로 펜텐 유도체의 제조방법 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840005809A KR850000670B1 (ko) | 1980-08-12 | 1984-09-21 | 사이클로 펜텐 유도체의 제조방법 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5754141A (ko) |
| KR (2) | KR840002175B1 (ko) |
| AT (1) | AT378179B (ko) |
| BE (1) | BE889905A (ko) |
| HU (1) | HU185645B (ko) |
| MA (1) | MA19238A1 (ko) |
| SU (1) | SU1145925A3 (ko) |
| ZA (1) | ZA814947B (ko) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3346657C1 (de) * | 1983-12-23 | 1985-01-24 | Braun Ag, 6000 Frankfurt | Schwinghebelantrieb fuer elektrische Kleingeraete |
| DE3346655C1 (de) * | 1983-12-23 | 1985-01-24 | Braun Ag, 6000 Frankfurt | Vorrichtung zur Umwandlung der Drehbewegung eines Exzenters in eine hin- und hergehende Bewegung |
-
1981
- 1981-07-20 ZA ZA814947A patent/ZA814947B/xx unknown
- 1981-08-04 KR KR1019810002839A patent/KR840002175B1/ko active IP Right Grant
- 1981-08-05 MA MA19438A patent/MA19238A1/fr unknown
- 1981-08-10 BE BE0/205621A patent/BE889905A/fr not_active IP Right Cessation
- 1981-08-11 JP JP56126548A patent/JPS5754141A/ja active Pending
- 1981-08-11 HU HU812316A patent/HU185645B/hu unknown
- 1981-08-12 AT AT0354581A patent/AT378179B/de active
- 1981-08-12 SU SU813320103A patent/SU1145925A3/ru active
-
1984
- 1984-09-21 KR KR1019840005809A patent/KR850000670B1/ko active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| SU1145925A3 (ru) | 1985-03-15 |
| KR850000670B1 (ko) | 1985-05-09 |
| HU185645B (en) | 1985-03-28 |
| KR850002757A (ko) | 1985-05-15 |
| BE889905A (fr) | 1982-02-10 |
| ZA814947B (en) | 1982-07-28 |
| MA19238A1 (fr) | 1982-04-01 |
| AT378179B (de) | 1985-06-25 |
| KR840002175B1 (ko) | 1984-11-26 |
| JPS5754141A (ko) | 1982-03-31 |
| ATA354581A (de) | 1984-11-15 |
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