GB1345934A - Cyclopentane derivatives - Google Patents
Cyclopentane derivativesInfo
- Publication number
- GB1345934A GB1345934A GB3304871A GB1345934DA GB1345934A GB 1345934 A GB1345934 A GB 1345934A GB 3304871 A GB3304871 A GB 3304871A GB 1345934D A GB1345934D A GB 1345934DA GB 1345934 A GB1345934 A GB 1345934A
- Authority
- GB
- United Kingdom
- Prior art keywords
- reacting
- furan
- oxo
- hexahydro
- formula
- 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 tetrahydropyran - 2 - yloxy Chemical group 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 6
- 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 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 3
- 229910052708 sodium Inorganic materials 0.000 abstract 3
- 239000011734 sodium Substances 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 abstract 1
- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- SMUSYYONYSPADE-UHFFFAOYSA-N 1-dimethoxyphosphoryl-3-pentoxypropan-2-one Chemical compound CCCCCOCC(=O)CP(=O)(OC)OC SMUSYYONYSPADE-UHFFFAOYSA-N 0.000 abstract 1
- XSDLSEOIVCVTQZ-UHFFFAOYSA-N 2h-cyclopenta[b]furan Chemical compound C1=CC2=CCOC2=C1 XSDLSEOIVCVTQZ-UHFFFAOYSA-N 0.000 abstract 1
- RKSGQXSDRYHVTM-UHFFFAOYSA-N 3-ethoxypropanal Chemical compound CCOCCC=O RKSGQXSDRYHVTM-UHFFFAOYSA-N 0.000 abstract 1
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-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
- IWPPWTPACQFMLJ-UHFFFAOYSA-N 4-propoxybutanoic acid Chemical compound CCCOCCCC(O)=O IWPPWTPACQFMLJ-UHFFFAOYSA-N 0.000 abstract 1
- WUZBGMQIKXKYMX-UHFFFAOYSA-N 6-methoxyhexanoic acid Chemical compound COCCCCCC(O)=O WUZBGMQIKXKYMX-UHFFFAOYSA-N 0.000 abstract 1
- KYTZXOYPYYJVNA-UHFFFAOYSA-N 6-methoxyhexanoyl chloride Chemical compound COCCCCCC(=O)Cl KYTZXOYPYYJVNA-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 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
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 abstract 1
- BMOACRKLCOIODC-UHFFFAOYSA-N butyl 3-butoxypropanoate Chemical compound CCCCOCCC(=O)OCCCC BMOACRKLCOIODC-UHFFFAOYSA-N 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- CURYAPFSRASBCA-UHFFFAOYSA-N ethyl 5-ethoxypent-2-enoate Chemical compound C(C)OCCC=CC(=O)OCC CURYAPFSRASBCA-UHFFFAOYSA-N 0.000 abstract 1
- IGBKIECXPBWKOE-UHFFFAOYSA-N ethyl 5-ethoxypentanoate Chemical compound CCOCCCCC(=O)OCC IGBKIECXPBWKOE-UHFFFAOYSA-N 0.000 abstract 1
- DXBULVYHTICWKT-UHFFFAOYSA-N ethyl 6-bromohexanoate Chemical compound CCOC(=O)CCCCCBr DXBULVYHTICWKT-UHFFFAOYSA-N 0.000 abstract 1
- WEZARSPIKIEHQZ-UHFFFAOYSA-N ethyl 6-methoxyhexanoate Chemical compound CCOC(=O)CCCCCOC WEZARSPIKIEHQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- GAAZBEZRXUMQNY-UHFFFAOYSA-N methyl 4-propoxybutanoate Chemical compound CCCOCCCC(=O)OC GAAZBEZRXUMQNY-UHFFFAOYSA-N 0.000 abstract 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
- C07C51/60—Preparation of carboxylic acid halides by conversion of carboxylic acids or their anhydrides or esters, lactones, salts into halides with the same carboxylic acid part
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1345934 Prosteglandin derivatives; phosphoric acid esters IMPERIAL CHEMICAL INDUSTRIES Ltd 13 June 1972 [14 July 1971] 33048/71 Headings C2C and C2P [Also in Divisions A5 and C3] The invention comprise prosteglandin derivatives of the formula wherein R<SP>1</SP> is hydroxymethyl, carboxyl or alkoxycarbonyl of up to 11 carbon atoms; either R<SP>2</SP> is OH or C 1-4 alkanoyloxy and R<SP>3</SP> is H, or R<SP>2</SP> and R<SP>3</SP> together form an oxo radical; A is -CH 2 CH 2 - or trans-CH=CH-; X is C 1-9 alkylene, and R<SP>4</SP> is C 1-9 alkyl or C 5-7 cycloalkyl provided that X and R<SP>4</SP> together contain not more than 10 carbon atoms, and for those compounds wherein R<SP>1</SP> is carboxy, pharmaceutically acceptable salts. Compounds of the above formula in which R<SP>1</SP> is carboxy are obtained by hydrolysing compounds of the formula or mixed anhydrides thereof, wherein R<SP>5</SP> and R<SP>6</SP> each are a tetrahydropyren-2-yloxy radical. The acids thus obtained may be converted to the corresponding esters by reacting them with diazoalkanes of the formula R<SP>7</SP>.N. 2 , wherein R<SP>7</SP> is C 1-10 alkyl, or reacting salts thereof with C 1-10 alkyl halides, and the esters reduced to compounds of the Formula I above in which R<SP>1</SP> is hydroxymethyl. 9α - Hydroxy - 16 - pentyloxy - 11α,15 - bis- (tetrahydropyran - 2 - yloxy) - 17,18,19,20- tetranor - 5 - cis,13 - trans - prostadienoic acid is prepared by reacting (4-carboxybutyl)triphenylphosphonium bromide with 3,3a#,4,5, 6,6a# - hexahydro - 2 - hydroxy - 4# - [4- pentyloxy - 3 - (tetrahydropyran - 2 - yloxy) - 1 - transbutenyl] - 5α - (tetrahydropyran - 2 - yloxy) 2H - cyclopenta[b]furan, obtained by reducing 3,3a#,4,5,6,6a# - hexahydro - 2 - oxo - 4# - [4- pentyloxy - 3 - (tetrahydropyran - 2 - yloxy) - 1- trans - butenyl] - 5α - (tetrahydropyran - 2 - yloxy)- 2H - cyclopenta[b]furan, resulting from the reaction between dihydropyran and 3,3a#,4,5,6, 6a# - hexahydro - 5α - hydroxy - 2 - oxo - 4#- (4 - pentyloxy - 3 - hydroxy - 1 - trans - butenyl)- 2H-cyclopenta[b]furan, which is made by hydrolysing 3,3a#,4,5,6,6a# - hexahydro - 2 - oxo - 4#- (4 - pentyloxy - 3 - hydroxy - 1 - trans - butenyl)- 5α - (4 - phenylbenzoyloxy) - 2H - cyclopenta[b]- furan obtained by reducing 3,3a,4,5,6,6a#- hexahydro - 2 - oxo - 4# - (3 - oxo - 4 - pentyloxy- 1 - trans - butenyl) - 5α - (4 - phenylbenzoyloxy)- 2H - cyclopenta[b]furan, resulting from the reaction between dimethyl 2-oxo-3-pentyloxypropylphosphonate and 5α - (4 - phenylbenzoyloxy) - 4# - formyl - 3,3a#,4,5,6,6a#- hexahydro - 2H - cyclopenta[b]furan - 2 one. The following compounds are prepared by reacting the appropriate phosphonate with 5α - (4 - phenylbenzoyloxy) - 4# - formyl- 3,3a#,4,5,6,6a# - hexahydrocyclo - 2H - penteno- [b]furan: 3,3a#,4,5,6,6a# - hexahydro - 5α - (4- phenylbenzoyloxy) - 4# - [3 - oxo - 4 - propoxy (or butoxy or isobutoxy, or hexyloxy) - 1 - transbutenyl], 2H-cyclopenteno[b]furan-2-one. 3,3a#,4,5,6,6a# - Hexahydro - 4# - (3 - oxo - 4- pentyloxybutyl) - 5α - (4 - phenylbenzoyloxy) - 2H- cyclopenteno[b]furan-2-one is obtained by hydrogenerating the corresponding unsaturated ketone. Butyl 3-butoxypropionate is prepared by reacting ethyl acrylate with a solution of sodium dissolved in n-butanol. Methyl 4-propoxybutyrate is obtained by esterifying 4-propoxybutyric acid, made by reacting 4- bromobutyric acid with a solution of sodium in n-propanol. Ethyl 5-ethoxypentanoate is made by hydrogenating ethyl 5-ethoxy-2-pentenoate obtained by reacting triethyl phosphonoacetate with 3- ethoxypropionaldehyde resulting from the hydrolysis of the corresponding diethyl acetal 6- methoxyhexanoyl chloride is prepared by reacting thionyl chloride with 6-methoxyhexanoic acid, resulting from the hydrolysis of ethyl 6-methoxyhexanoate, obtained by reacting ethyl 6-bromohexanoate and a solution of sodium in methanol. Phosphonates of the formula are prepared by reacting dimethyl methylphosphonate with compounds of the formula R<SP>4</SP>.O.XCOR<SP>5</SP>, where R<SP>5</SP> is alkoxy or halogen, in the presence of butyl-lithium.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3304871 | 1971-07-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1345934A true GB1345934A (en) | 1974-02-06 |
Family
ID=10347836
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3304871A Expired GB1345934A (en) | 1971-07-14 | 1971-07-14 | Cyclopentane derivatives |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS5617344B1 (en) |
| AU (1) | AU461617B2 (en) |
| BE (1) | BE786250A (en) |
| CA (1) | CA1093069A (en) |
| DD (1) | DD102140A5 (en) |
| DE (1) | DE2234708A1 (en) |
| FR (1) | FR2145696B1 (en) |
| GB (1) | GB1345934A (en) |
| HU (1) | HU166718B (en) |
| IE (1) | IE36421B1 (en) |
| NL (1) | NL7209758A (en) |
| SE (1) | SE7503704L (en) |
| ZA (1) | ZA724234B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4061671A (en) * | 1974-04-03 | 1977-12-06 | Hoechst Aktiengesellschaft | Analogues of prostaglandins |
| US4113766A (en) * | 1973-04-30 | 1978-09-12 | Pfizer Inc. | Oxaprostaglandins |
| US4169895A (en) | 1976-09-28 | 1979-10-02 | Pfizer Inc. | Antisecretory 16,16-dimethyl-17-oxaprostaglandins |
| US4191774A (en) * | 1978-01-18 | 1980-03-04 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | Novel 17-aza-PGF2α derivatives and pharmaceutical compositions containing the same |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4094899A (en) * | 1972-06-02 | 1978-06-13 | Pfizer Inc. | Oxaprostaglandins |
-
0
- BE BE786250D patent/BE786250A/en unknown
-
1971
- 1971-07-14 GB GB3304871A patent/GB1345934A/en not_active Expired
-
1972
- 1972-06-16 IE IE848/72A patent/IE36421B1/en unknown
- 1972-06-20 ZA ZA724234A patent/ZA724234B/en unknown
- 1972-06-21 CA CA145,324A patent/CA1093069A/en not_active Expired
- 1972-06-22 AU AU43766/72A patent/AU461617B2/en not_active Expired
- 1972-07-04 HU HUIE516A patent/HU166718B/hu unknown
- 1972-07-12 DD DD164379A patent/DD102140A5/xx unknown
- 1972-07-13 FR FR7225519A patent/FR2145696B1/fr not_active Expired
- 1972-07-14 NL NL7209758A patent/NL7209758A/xx unknown
- 1972-07-14 DE DE2234708A patent/DE2234708A1/en not_active Ceased
- 1972-07-14 JP JP7067572A patent/JPS5617344B1/ja active Pending
-
1975
- 1975-04-01 SE SE7503704A patent/SE7503704L/xx unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4113766A (en) * | 1973-04-30 | 1978-09-12 | Pfizer Inc. | Oxaprostaglandins |
| US4061671A (en) * | 1974-04-03 | 1977-12-06 | Hoechst Aktiengesellschaft | Analogues of prostaglandins |
| US4169895A (en) | 1976-09-28 | 1979-10-02 | Pfizer Inc. | Antisecretory 16,16-dimethyl-17-oxaprostaglandins |
| US4191774A (en) * | 1978-01-18 | 1980-03-04 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T. | Novel 17-aza-PGF2α derivatives and pharmaceutical compositions containing the same |
Also Published As
| Publication number | Publication date |
|---|---|
| BE786250A (en) | 1973-01-15 |
| ZA724234B (en) | 1973-03-28 |
| CA1093069A (en) | 1981-01-06 |
| NL7209758A (en) | 1973-01-16 |
| IE36421L (en) | 1973-01-14 |
| AU461617B2 (en) | 1975-05-13 |
| JPS5617344B1 (en) | 1981-04-22 |
| AU4376672A (en) | 1974-01-03 |
| SE7503704L (en) | 1975-04-01 |
| FR2145696B1 (en) | 1976-04-16 |
| DE2234708A1 (en) | 1973-02-01 |
| FR2145696A1 (en) | 1973-02-23 |
| HU166718B (en) | 1975-05-28 |
| IE36421B1 (en) | 1976-10-27 |
| DD102140A5 (en) | 1973-12-05 |
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