KR850002830A - 16-플루오로-16,17-디데하이드로 프로스타노이드의 제조방법 - Google Patents
16-플루오로-16,17-디데하이드로 프로스타노이드의 제조방법 Download PDFInfo
- Publication number
- KR850002830A KR850002830A KR1019840005144A KR840005144A KR850002830A KR 850002830 A KR850002830 A KR 850002830A KR 1019840005144 A KR1019840005144 A KR 1019840005144A KR 840005144 A KR840005144 A KR 840005144A KR 850002830 A KR850002830 A KR 850002830A
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- KR
- South Korea
- Prior art keywords
- hydrogen
- compound
- hydroxy
- alkyl
- formula
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 3
- 229940127293 prostanoid Drugs 0.000 title 1
- 150000003814 prostanoids Chemical class 0.000 title 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 25
- 239000001257 hydrogen Substances 0.000 claims 25
- 150000001875 compounds Chemical class 0.000 claims 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004043 oxo group Chemical group O=* 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- -1 C 1 to C 6 alkyl Chemical group 0.000 claims 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 230000003647 oxidation Effects 0.000 claims 2
- 238000007254 oxidation reaction Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 238000003747 Grignard reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 238000007112 amidation reaction Methods 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000168 pyrrolyl group Chemical group 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004953 trihalomethyl group Chemical group 0.000 claims 1
Classifications
-
- 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
- C07C405/0016—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing only hydroxy, etherified or esterified hydroxy groups
-
- 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
- C07D207/30—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 two double bonds between ring members or between ring members and non-ring members
- C07D207/32—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—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 two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by 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
- 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
- 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
- C07C405/0041—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
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Claims (5)
- 일반식(Ⅱ)의 화합물의 C15카보닐그룹을 환원 또는 그리그나드 반응시키고, 적절한 순서에 따라, 존재가능한 보호그룹을 제거하고, 필요시, 수득된 15S-및 15R-하이드록시 화합물의 에피머성 혼합물을 단일 에피머로 분리하거나; 일반식(Ⅲ)의 화합물을 선택적으로 탈할로겐화 수소화시키고, 존재가능한 보호그룹을 제거하며 A가 -C≡C-인 일반식(Ⅰ)의 화합물을 수득하거나; 일반식(Ⅳ)의 화합물을 산화시키고 보호그룹을 제거하여, 사용된 출발물질에 따라 R1및 R2가 함께 옥소그룹을 형성하는 일반식(Ⅰ)의 화합물, 또는 R3및 R4가 함께 옥소그룹을 형성하는 일반식(Ⅰ)의 화합물 또는 상기의 산화생성물의 혼합물을 수득하고, 혼합물이 수득되는 경우에는 수득된 혼합물을 각각의 산화생성물로 분리시키거나; 일반식(A)의 화합물을 일반식 -(CH2)4-COR(여기에서 R은 하기 정의하는바와 같다)의 그룹을 함유하는 비티히(wittig)시약과 반응시키고, 존재가능한 보호그룹을 제거하여, 기호가시스이중 결합이고,, R1이 하이드록시이며, R2는 수소인 일반식(Ⅰ)의 화합물을 수득하고, 필요시, 수득된 화합물을 R1이 수소이고 R2가 하이드록시인 일반식(Ⅰ)의 상응하는 화합물 또는 R1및 R2가 함께 옥소그룹을 형성하는 일반식(Ⅰ)의 상응하는 화합물로 전환시키고; 필요시, R이 -OH이고 존재하는 하이드록시 그룹이 유리형태이거나 보호된 형태인 일반식(Ⅰ)의 화합물 또는 그의 반응성 유도체를 에스태르화 또는 아미드화 반응에 의해 R이 -OH가 아닌 일반식(Ⅰ)의 화합물로 전환시키고 이어서 존재가능한 보호그룹을 제거하고/하거나 필요시, 일반식(Ⅰ)의 화합물을 염으로 전환시키거나 또는 생성된 염으로부터 일반식(Ⅰ)의 유리화합물을 수득하고/하거나 필요시, 일반식(Ⅰ)의 이성체의 혼합물을 단일 이성체로 분리시킴을 특징으로 하여 일반식(Ⅰ)의 화합물 및 그의약제학적으로 또는 수의학적으로 허용되는 염을 제조하는 방법.상기식에서R은 1) -OH 또는 -OR´(여기에서 R´는 페닐 또는 모노시클로 알킬그룹 또는 O,S 및 N중에서 선택된 적어도 하나의 헤테로 원자를 함유하는 5원 또는 6원헤테로 모노 시클릭환으로 임의로 치환된 C1내지 C6알킬이다);2)(여기에서 R˝및 R´˝는 각각 독립적으로 수소; C1내지 C6알킬; 페닐; 또는 O,S 및 N중에서 선택된 적어도 하나의 헤테로 원자를 함유하는 5원 또는 6원 헤테로 모노시클릭환이거나; 또는 R˝ 및 R´˝는 이들이 결합된 질소원자와 함께, 임의로 O,S 및 N중에서 선택된 추가의 헤테로 원자를 함유하는, 5원 또는 6원 헤테로 모노시클릭환을 형성한다);3) -W-(CH2)n-X(여기에서 W는 -O- 또는 -NH-이고, n은 1내지 4의 정수이며, X는 -OR´그룹 또는그룹인데, 여기에서 R´,R˝ 및 R´˝는 상기와 같다); 또는4) -NHSO2-RIV(여기에서 RIV는 C1내지 C4알킬, 페닐, 또는 C1내지 C4로 치환된 페닐이다)이며; R1및 R2중의 하나는 수소이고 다른 하나는 하이드록시이거나, R1및 R2는 함께 옥소그룹을 형성하고; R3및 R4중의 하나는 수소이고 다른 하나는 하이드록시이거나, R3및 R4는 둘다 수소이거나 또는 함께 옥소그룹을 형성하며; 단 R1및 R2가 옥소그룹을 형성하는 경우에는 R3및 R4는 옥소그룹을 형성하지 않으며; R5및 R6중의 하나는 하이드록시이고 다른 하나는 수소, C1내지 C6알킬, C2내지 C6알케닐, C2내지 C6알키닐 또는 페닐이고; m은 0 또는 1 내지 3의 정수이며;R7은 C1내지 C6알킬; C3내지 C7모노시클로알킬; 비치환된 페닐, 또는 C1내지 C4알킬, C1내지 C4알콕시, 트리-할로 C1내지 C4알킬, 할로겐 및(여기에서 RV및 RVI는 각각 독립적으로 수소, C1내지 C4알킬 또는 페닐이다)중에서 선택된 하나이상의 치환제로 치환된 페닐이거나; 또는 R7은 O,S 및 N중에서 선택된 적어도 하나의 헤테로 원자를 함유하고, 할로겐, C1내지 C4알킬, C1내지 C4알콕시, 페닐 및 펜옥시중에서 선택된 하나이상의 치환제로 임의 치환된 5원 또는 6원 헤테로 모노시클릭환이고; A는트랜스-CH=CH-, -CH2-CH2- 또는 -C≡C-이고 기호는 단일 결합 또는시스이중 결합을 나타내며; Ra는 상기 정의한 바와같은 R 또는 -OQ그룹(여기에서 Q는 카복실산 작용기에 대한 보호그룹이다)이고; R´1및 R´2중의 하나는 수소이고 다른하나는 유리 또는 보호된 하이드록시거나 R´1및 R´2는 함께 보호된 옥소그룹을 형성하며; R´3및 R´4중의 하나는 수소이고 다른 하나는 유리 또는 보호된 하이드록시거나 R´3및 R´4는 둘다 수소이거나 또는 R´3및 R´4는 함께 보호된옥소그룹을 형성하고,R˝1및 R˝2중의 하나는 수소이고 다른하나는 유리 또는 보호된 하이드록시이거나 또는 R˝1및 R˝2는 함께 옥소그룹을 형성하며; R˝3및 R˝4중의 하나는 수소이고 다른하나는 유리 또는 보호된 하이드록시이거나, R˝3및 R˝4는 둘다 수소이거나 또는 함께 옥소그룹을 형성하고; R´5및 R´6중의 하나는 유리 또는 보호된 하이드록시이고 다른 하나는 수소, C1내지 C6알킬, C2내지 C6알케닐, C2내지 C6알키닐 또는 페닐이며; Y는 염소, 브롬 또는 요오드이고; R´˝1,R´˝2,R´˝3및 R´˝4중의 하나는 유리하이드록시그룹이고 R´˝1,R˝´2,R´˝3및 R´˝4중의 나머지는 각기, 옥소를 제외하고는 상기 R˝1,R˝2,R˝3및 R˝4에서 정의된 의미를 나타내며; R˝5및 R˝6중의 하나는 수소, C1내지 C6알킬, C2내지 C6알케닐, C2내지 C6알키닐 또는 페닐이고 다른 하나는 보호된 하이드록시이고; A´는트랜스-CH=CH-, CH2=CH2-, -C≡C- 또는 -CH=CY-(여기에서 Y는 상기와 같다)이다.
- 제1항에 있어서, R이 1) -OH 또는 -OR´(여기에서 R´는 C1내지 C6알킬이다;2)(여기에서 각각의 R˝ 및 R´˝는 독립적으로 수소 또는 C1내지 C6알킬이다); 또는 3) -W-(CH2)n-X(여기에서 W는 -O-이고, n은 2이며, X는 -OR´인데, R´는 C1내지 C6알킬이다)이고; R1및 R2중의 하나는 수소이고 다른 하나는 하이드록시이거나 R1및 R2가 함께 옥소그룹을 형성하며; R3및 R4중의 하나는 수소이고 다른 하나는 하이드록시이거나 R3및 R4는 둘다 수소이고;R5및 R6중의 하나는 수소이고 다른하나는 하이드록시이며; m은 0이고; R7은 C3내지 C5알킬; C5내지 C6시클로알킬; 비치환된 페닐 또는 할로겐또는 트리-할로-메틸로 치환된 페닐; 또는 O,S 및 N중에서 선택된 한개 또는 두개의 헤테로 원자를 함유하는 불포화된 5원 또는 6원 헤테로 모노시클릭 환이며; A는 -CH=CH-트랜스또는 -C≡C-이고; 기호는시스-이중결합 또는 단일결합을 나타내는 일반식(Ⅰ)의 화합물 및 이들의 약제학적으로 또는 수의학적으로 허용되는 염을 제조하는 방법.
- 제1항에 있어서, R7이 m-프로필, m-부틸, m-펠틸, 시클로펜틸, 시클로헥실, 페닐, 클로로-페닐, 트리플루오로메틸페닐, 푸릴, 티에닐, 피롤릴, 이소옥사졸릴, 피리딜 또는 피라지닐인 제2항에서 정의된 일반식(Ⅰ)의 화합물을 제조하는 방법.
- 제1항에 있어서, R이 -OH 또는 -OR´(여기에서 R´는 C1내지 C4알킬이다)이고; R1이 하이드록시이며 R2가 수소이거나 R1및 R2가 함께 옥소그룹을 형성하며; R3가 하이드록시이고 R4가 수소이거나 또는 R3및 R4가 둘다 수소이고; R5및 R6중의 하나가 수소이고 다른 하나는 하이드록시이고; m은 0이며; R7은할로겐원자 또는 트리플루오로메틸 그룹으로 임의로 치환된 페닐이고; A는 -CH=CH-트랜스또는 -C≡C-이고; 기호는시스-이중결합 또는 단일결합인 일반식(Ⅰ)의 화합물 및 이들의 약제학적으로 또는 수의학적으로 허용되는 염을 제조하는 방법.
- 제1항에 있어서, A가 -CH=CH-트랜스</U인 제4항에서 정의된 일반식(Ⅰ)의 화합물을 제조하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8324004 | 1983-09-07 | ||
| GB838324004A GB8324004D0 (en) | 1983-09-07 | 1983-09-07 | 16-fluoro-16 17-didehydro prostanoids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR850002830A true KR850002830A (ko) | 1985-05-20 |
Family
ID=10548451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019840005144A KR850002830A (ko) | 1983-09-07 | 1984-08-24 | 16-플루오로-16,17-디데하이드로 프로스타노이드의 제조방법 |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4626597A (ko) |
| JP (1) | JPS6072859A (ko) |
| KR (1) | KR850002830A (ko) |
| AU (1) | AU562725B2 (ko) |
| BE (1) | BE900414A (ko) |
| CH (1) | CH662114A5 (ko) |
| CS (1) | CS259869B2 (ko) |
| DE (1) | DE3430626A1 (ko) |
| DK (1) | DK406484A (ko) |
| ES (2) | ES8607022A1 (ko) |
| FI (1) | FI843285A (ko) |
| FR (1) | FR2551436B1 (ko) |
| GB (2) | GB8324004D0 (ko) |
| GR (1) | GR80204B (ko) |
| HU (1) | HU192430B (ko) |
| IL (1) | IL72749A (ko) |
| IT (1) | IT1180210B (ko) |
| NL (1) | NL8402666A (ko) |
| NO (1) | NO843355L (ko) |
| NZ (1) | NZ209294A (ko) |
| PT (1) | PT79113B (ko) |
| SE (1) | SE8404334L (ko) |
| SU (1) | SU1442070A3 (ko) |
| ZA (1) | ZA846580B (ko) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8625326D0 (en) * | 1986-10-22 | 1986-11-26 | Glaxo Group Ltd | Medicaments |
| US5317032A (en) * | 1987-10-02 | 1994-05-31 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Prostaglandin cathartic |
| EP0310305B1 (en) * | 1987-10-02 | 1992-07-22 | Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo | Cathartics |
| AU616564B2 (en) * | 1988-09-29 | 1991-10-31 | Sumitomo Chemical Company, Limited | Novel pyrazole compounds, method for production thereof, use thereof and intermediates for production thereof |
| US5099644A (en) * | 1990-04-04 | 1992-03-31 | General Electric Company | Lean staged combustion assembly |
| US6680339B2 (en) | 1996-11-12 | 2004-01-20 | Alcon Manufacturing, Ltd. | 15-fluoro prostaglandins as ocular hypotensives |
| CA2269855A1 (en) * | 1996-11-12 | 1998-05-22 | Alcon Laboratories, Inc. | 15-fluoro prostaglandins as ocular hypotensives |
| CA2477080C (en) * | 2002-03-01 | 2010-09-28 | Allergan, Inc. | Preparation of prostamides |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987087A (en) * | 1971-07-29 | 1976-10-19 | The Upjohn Company | Phenyl-substituted prostaglandin-f type analogs |
| GB1396206A (en) * | 1972-04-27 | 1975-06-04 | Upjohn Co | Prostaglandins and the preparation thereof |
| ZA744581B (en) * | 1973-07-20 | 1975-07-30 | Upjohn Co | Prostoglandin analogs |
| US4059576A (en) * | 1973-08-06 | 1977-11-22 | Hoffmann-La Roche, Inc. | 11-Substituted prostaglandins |
| GB1484591A (en) * | 1974-04-11 | 1977-09-01 | Ono Pharmaceutical Co | Prostaglandin compositions |
| AU501803B2 (en) * | 1975-03-21 | 1979-06-28 | Farmitalia Carlo Erba S.P.A. | Fluoro-prostaglandins |
| US4283417A (en) * | 1976-06-14 | 1981-08-11 | Pfizer Inc. | Bronchodialation with 13,14-dihydro-15-alkenyl prostaglandins |
| US4268522A (en) * | 1976-06-14 | 1981-05-19 | Pfizer Inc. | 13,14-Dihydro-15-alkenyl- and 13,14-dihydro-15-alkynyl prostaglandins and analogs thereof |
-
1983
- 1983-09-07 GB GB838324004A patent/GB8324004D0/en active Pending
-
1984
- 1984-08-01 IT IT22159/84A patent/IT1180210B/it active
- 1984-08-20 FI FI843285A patent/FI843285A/fi not_active Application Discontinuation
- 1984-08-20 DE DE19843430626 patent/DE3430626A1/de not_active Withdrawn
- 1984-08-20 GB GB08421124A patent/GB2146325B/en not_active Expired
- 1984-08-21 NZ NZ209294A patent/NZ209294A/en unknown
- 1984-08-21 AU AU32231/84A patent/AU562725B2/en not_active Ceased
- 1984-08-21 FR FR8413013A patent/FR2551436B1/fr not_active Expired
- 1984-08-22 US US06/643,014 patent/US4626597A/en not_active Expired - Fee Related
- 1984-08-22 CS CS846360A patent/CS259869B2/cs unknown
- 1984-08-22 IL IL72749A patent/IL72749A/xx unknown
- 1984-08-22 PT PT79113A patent/PT79113B/pt unknown
- 1984-08-22 NO NO843355A patent/NO843355L/no unknown
- 1984-08-22 CH CH4020/84A patent/CH662114A5/de not_active IP Right Cessation
- 1984-08-23 ZA ZA846580A patent/ZA846580B/xx unknown
- 1984-08-23 BE BE0/213533A patent/BE900414A/fr not_active IP Right Cessation
- 1984-08-24 KR KR1019840005144A patent/KR850002830A/ko not_active Application Discontinuation
- 1984-08-24 GR GR80204A patent/GR80204B/el unknown
- 1984-08-24 DK DK406484A patent/DK406484A/da not_active Application Discontinuation
- 1984-08-28 JP JP59177631A patent/JPS6072859A/ja active Pending
- 1984-08-30 SE SE8404334A patent/SE8404334L/xx not_active Application Discontinuation
- 1984-08-30 ES ES535551A patent/ES8607022A1/es not_active Expired
- 1984-08-31 NL NL8402666A patent/NL8402666A/nl not_active Application Discontinuation
- 1984-08-31 HU HU843291A patent/HU192430B/hu unknown
-
1985
- 1985-05-31 ES ES543776A patent/ES8604135A1/es not_active Expired
- 1985-10-10 SU SU853961258A patent/SU1442070A3/ru active
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