GB1372541A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1372541A GB1372541A GB3304971A GB5839971A GB1372541A GB 1372541 A GB1372541 A GB 1372541A GB 3304971 A GB3304971 A GB 3304971A GB 5839971 A GB5839971 A GB 5839971A GB 1372541 A GB1372541 A GB 1372541A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- cyclopenta
- prepared
- yloxy
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000001511 cyclopentyl group Chemical class [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 title 1
- -1 di(C 1-3 alkyl)amino radicals Chemical class 0.000 abstract 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 4
- XSDLSEOIVCVTQZ-UHFFFAOYSA-N 2h-cyclopenta[b]furan Chemical class C1=CC2=CCOC2=C1 XSDLSEOIVCVTQZ-UHFFFAOYSA-N 0.000 abstract 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 2
- 150000003180 prostaglandins Chemical class 0.000 abstract 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 abstract 1
- DICZUTMNXOMHQD-UHFFFAOYSA-N 3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one Chemical compound C1CCC2OC(=O)CC21 DICZUTMNXOMHQD-UHFFFAOYSA-N 0.000 abstract 1
- ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 abstract 1
- MLOSJPZSZWUDSK-UHFFFAOYSA-N 4-carboxybutyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCCC(=O)O)C1=CC=CC=C1 MLOSJPZSZWUDSK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000002009 diols Chemical class 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- BVSRWCMAJISCTD-UHFFFAOYSA-N ethyl 2-diethoxyphosphorylpropanoate Chemical compound CCOC(=O)C(C)P(=O)(OCC)OCC BVSRWCMAJISCTD-UHFFFAOYSA-N 0.000 abstract 1
- CJFGCEXKHRHQBH-UHFFFAOYSA-N ethyl 3-(3,4-dichlorophenyl)-2-methylprop-2-enoate Chemical compound ClC=1C=C(C=CC1Cl)C=C(C(=O)OCC)C CJFGCEXKHRHQBH-UHFFFAOYSA-N 0.000 abstract 1
- DZMDXJLJZQUFQB-UHFFFAOYSA-N ethyl 3-(3,4-dichlorophenyl)-2-methylpropanoate Chemical compound CC(C(=O)OCC)CC1=CC(=C(C=C1)Cl)Cl DZMDXJLJZQUFQB-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
- C07D307/935—Not further condensed cyclopenta [b] furans or hydrogenated cyclopenta [b] furans
-
- 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
- C07C405/0016—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
- 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
- C07C405/0025—Analogues having the carboxyl group in the side-chains replaced by other functional groups containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
-
- 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)
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Abstract
1372541 Prostaglandins IMPERIAL CHEMICAL INDUSTRIES Ltd 19 June 1972 [14 July 1971 16 Dec 1971] 33049/71 and 58399/71 Headings C2C and C2P [Also in Divisions C3 and A5] The invention comprises prostaglandins of the formula wherein R<SP>1</SP> is -CH 2 OH, -COOH or alkoxycarbonyl of up to 12 carbon atoms; either R<SP>2</SP> is OH or C 1-4 alkenoyloxy and R<SP>3</SP> is H, or R<SP>2</SP> and R<SP>3</SP> together form = O ; Y is ethylene or vinylene; A is ethylene or trans-vinylene; and R<SP>4</SP> is an aryl radical optionally substituted by halogen atoms, nitro, C 1-3 alkyl, C 1-3 haloalkyl, C 1-3 alkoxy or di(C 1-3 alkyl)amino radicals, and pharmaceutically acceptable salts of those compounds in which R<SP>1</SP> is COOH, and their preparation. They are prepared by hydrolysing compounds of the formula or mixed anhydrates thereof, wherein R<SP>5</SP> and R<SP>6</SP> each or betrahydropyran-2-yloxy or carboxylic acyloxy, followed by, if desired, esterification and reduction of the resulting esters. 16 - Methyl - 9 - oxo - 11α,15 - bis - (tetrahydro pyran - 2 - yloxy) - 17 - (4 - trifluoromethylphenyl) - 18,19,20 - trinor - 5 - cis,13 - transprostadienoic acid is prepared by oxidizing the corresponding 9α-hydroxy compound. Ethyl 2 - methyl - 3 - (3,4 - dichlorophenyl)- propionate is obtained by hydrogenating ethyl 3 - (3,4 - dichlorophenyl) - 2 - methylacrylate resulting from the reaction between ethyl 2-(diethylphosphono)propionate with 3,4-dichlorobenzaldehyde in the presence of butyllithium. Cyclopenta[b]furans of the Formula VI wherein Ac is p-phenylbenzoyl are prepared by reacting 5α - (4 - phenylbenzoylozy) - 4#- formyl - 3,3aα,4,5,6,6aα - hexahydro - 2H- cyclopenta[b]furan-2-one with phosphonates of the formula (MeO) 2 P(O) CH 2 -CO-CH(CH 3 )- OH 2 R<SP>4</SP> in the presence of butyllithium. 9α - Hydroxy - 16 - methyl - 17 - phenyl - 11α, 15 - bis - (tetrahydropyran - 2 - yloxy) - 18,19,20- trinor - 5 - cis, 13 - trans - prostadienoic acid is prepared by reacting (4-carboxybutyl)triphenyl phosphonium bromide with 2-hydroxy-3,3aα,- 4,5,6,6aα - hexahydro - 4# - (4 - methyl - 5 - phenyl- 3 - (tetrahydropyran - 2 - yloxy) - 1 - transpentenyl] - 5α - (tetrahydropyran - 2 - yloxy) - 2H- cyclopenta[b]furan, obtained by reducing the corresponding hexahydro - 2H - cyclopenta[b]- furan-2-one, resulting from the reaction hydropyran on the corresponding diol, which is prepared by hydrolyzing 3,3aα,4,5,5,6aα-hexahydro - 4# - (3 - hydroxy - 4 - methyl - 5 - phenyl- 1 - trans - pentenyl) - 5α - (4 - phenylbenzoyloxy) - 2H - cyclopenta[b]furen - 2 - one, resulting from the reduction of the corresponding cyclopenta- [b]furan of Formula VI above. Phosphonates of the formula are prepared by reacting dimethyl methylphonphosate with esters of the formula R<SP>4</SP>CH 2 CH(CH 3 )COO-alkyl.
Priority Applications (14)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BE786251D BE786251A (en) | 1971-07-14 | NEW DERIVATIVES OF CYCLOPENTANE | |
GB3304971A GB1372541A (en) | 1971-07-14 | 1971-12-16 | Cyclopentane derivatives |
IE876/72A IE36914B1 (en) | 1971-07-14 | 1972-06-22 | Cyclopentane derivatives |
CA145,746A CA986926A (en) | 1971-07-14 | 1972-06-26 | Cyclopentane derivatives |
AU43940/72A AU470384B2 (en) | 1972-06-27 | Cyclopentane derivatives | |
JP6895172A JPS5629665B1 (en) | 1971-07-14 | 1972-07-10 | |
HUIE518A HU166719B (en) | 1971-07-14 | 1972-07-12 | |
CH1046572A CH575902A5 (en) | 1971-07-14 | 1972-07-12 | |
DD164374A DD102141A5 (en) | 1971-07-14 | 1972-07-12 | |
FR7225520A FR2145697B1 (en) | 1971-07-14 | 1972-07-13 | |
SE7209266A SE399706B (en) | 1971-07-14 | 1972-07-13 | PROSTANIC ACID DERIVATIVES USED AS CONTRACTIVE MEANS, FOR TERMINATION OF PREGNANCY AND FOR REGULATION OF THE OSTRUS CYCLE |
NL7209817A NL7209817A (en) | 1971-07-14 | 1972-07-14 | |
DE2234709A DE2234709C2 (en) | 1971-07-14 | 1972-07-14 | Prostanoic acid derivatives and processes for their preparation |
SE7504707A SE7504707L (en) | 1971-07-14 | 1975-04-23 |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3304971 | 1971-07-14 | ||
GB3304971A GB1372541A (en) | 1971-07-14 | 1971-12-16 | Cyclopentane derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1372541A true GB1372541A (en) | 1974-10-30 |
Family
ID=26261688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3304971A Expired GB1372541A (en) | 1971-07-14 | 1971-12-16 | Cyclopentane derivatives |
Country Status (12)
Country | Link |
---|---|
JP (1) | JPS5629665B1 (en) |
BE (1) | BE786251A (en) |
CA (1) | CA986926A (en) |
CH (1) | CH575902A5 (en) |
DD (1) | DD102141A5 (en) |
DE (1) | DE2234709C2 (en) |
FR (1) | FR2145697B1 (en) |
GB (1) | GB1372541A (en) |
HU (1) | HU166719B (en) |
IE (1) | IE36914B1 (en) |
NL (1) | NL7209817A (en) |
SE (2) | SE399706B (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6096902A (en) * | 1996-02-29 | 2000-08-01 | Allergan | Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
EP1551418A1 (en) * | 2002-09-19 | 2005-07-13 | Ilex Oncology Research Sàrl | Substituted ketophosphonate compounds having bone anabolic activity |
US7642370B2 (en) | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2361381A1 (en) * | 1972-07-13 | 1978-03-10 | Pfizer | (15)-(Hetero) aryl prostaglandin analogues - with long-lasting prostaglandin-like activity |
US4113723A (en) | 1972-07-13 | 1978-09-12 | Pfizer Inc. | 15-Substituted-ω-pentanorprostaglandins |
GB1431561A (en) * | 1973-01-31 | 1976-04-07 | Ici Ltd | Cyclopentane derivatives |
US5296504A (en) * | 1988-09-06 | 1994-03-22 | Kabi Pharmacia | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
US6187813B1 (en) | 1990-04-10 | 2001-02-13 | Pharmacia & Upjohn Aktiebolag | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
DE03014533T1 (en) * | 1988-09-06 | 2004-07-15 | Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
US5321128A (en) * | 1988-09-06 | 1994-06-14 | Kabi Pharmacia Ab | Prostaglandin derivatives for the treatment of glaucoma or ocular hypertension |
HU212570B (en) * | 1991-06-24 | 1996-08-29 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 13,14-dihydro-15(r)-17-phenyl-18,19,20-trinor-pgf2alfa-isopropylester |
-
0
- BE BE786251D patent/BE786251A/en unknown
-
1971
- 1971-12-16 GB GB3304971A patent/GB1372541A/en not_active Expired
-
1972
- 1972-06-22 IE IE876/72A patent/IE36914B1/en unknown
- 1972-06-26 CA CA145,746A patent/CA986926A/en not_active Expired
- 1972-07-10 JP JP6895172A patent/JPS5629665B1/ja active Pending
- 1972-07-12 CH CH1046572A patent/CH575902A5/xx not_active IP Right Cessation
- 1972-07-12 HU HUIE518A patent/HU166719B/hu unknown
- 1972-07-12 DD DD164374A patent/DD102141A5/xx unknown
- 1972-07-13 FR FR7225520A patent/FR2145697B1/fr not_active Expired
- 1972-07-13 SE SE7209266A patent/SE399706B/en unknown
- 1972-07-14 NL NL7209817A patent/NL7209817A/xx unknown
- 1972-07-14 DE DE2234709A patent/DE2234709C2/en not_active Expired
-
1975
- 1975-04-23 SE SE7504707A patent/SE7504707L/xx unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6096902A (en) * | 1996-02-29 | 2000-08-01 | Allergan | Cyclopentane heptan(ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
US6573390B2 (en) | 1996-02-29 | 2003-06-03 | Allergan, Inc. | Cyclopentane heptan (ENE)OIC acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
US6680337B2 (en) | 1996-02-29 | 2004-01-20 | Allergan, Inc. | Cyclopentane heptan(ene)oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents |
EP1551418A1 (en) * | 2002-09-19 | 2005-07-13 | Ilex Oncology Research Sàrl | Substituted ketophosphonate compounds having bone anabolic activity |
EP1551418A4 (en) * | 2002-09-19 | 2006-05-03 | Ilex Oncology Res Sarl | Substituted ketophosphonate compounds having bone anabolic activity |
US7642370B2 (en) | 2006-08-07 | 2010-01-05 | Daiichi Fine Chemical Co., Ltd. | Method for preparing prostaglandin derivative |
Also Published As
Publication number | Publication date |
---|---|
DD102141A5 (en) | 1973-12-05 |
CH575902A5 (en) | 1976-05-31 |
BE786251A (en) | 1973-01-15 |
AU4394072A (en) | 1974-01-03 |
DE2234709C2 (en) | 1982-06-03 |
IE36914B1 (en) | 1977-03-30 |
HU166719B (en) | 1975-05-28 |
FR2145697B1 (en) | 1976-04-16 |
JPS5629665B1 (en) | 1981-07-09 |
NL7209817A (en) | 1973-01-16 |
DE2234709A1 (en) | 1973-02-01 |
SE7504707L (en) | 1975-04-23 |
IE36914L (en) | 1973-01-14 |
SE399706B (en) | 1978-02-27 |
FR2145697A1 (en) | 1973-02-23 |
CA986926A (en) | 1976-04-06 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PCNP | Patent ceased through non-payment of renewal fee |