IE37108B1 - Iodo-alkenes - Google Patents
Iodo-alkenesInfo
- Publication number
- IE37108B1 IE37108B1 IE599/76A IE59976A IE37108B1 IE 37108 B1 IE37108 B1 IE 37108B1 IE 599/76 A IE599/76 A IE 599/76A IE 59976 A IE59976 A IE 59976A IE 37108 B1 IE37108 B1 IE 37108B1
- Authority
- IE
- Ireland
- Prior art keywords
- trans
- iodo
- cyclopentene
- och
- cyclohexyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 3
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 2
- 150000003180 prostaglandins Chemical class 0.000 abstract 2
- SJZDDNSUIVLYIN-BQYQJAHWSA-N (e)-1-iodooct-1-ene Chemical compound CCCCCC\C=C\I SJZDDNSUIVLYIN-BQYQJAHWSA-N 0.000 abstract 1
- KTBUGNSRUZRREG-MDZDMXLPSA-N (e)-3-(1-ethoxyethoxy)-1-iodooct-1-ene Chemical compound CCCCCC(\C=C\I)OC(C)OCC KTBUGNSRUZRREG-MDZDMXLPSA-N 0.000 abstract 1
- -1 2-tetrahydropyranyloxy Chemical group 0.000 abstract 1
- BJSLPGNZBIRLNV-UHFFFAOYSA-N C(C)C1=CC(CC1O)=O.OC1C=C(C(C1)=O)CCCCCCC(=O)OCC Chemical compound C(C)C1=CC(CC1O)=O.OC1C=C(C(C1)=O)CCCCCCC(=O)OCC BJSLPGNZBIRLNV-UHFFFAOYSA-N 0.000 abstract 1
- NSMHRVMZHYOGSZ-UHFFFAOYSA-N IC=CCCCCCCCC1=CC=CC=C1 Chemical compound IC=CCCCCCCCC1=CC=CC=C1 NSMHRVMZHYOGSZ-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- IRHYASGSXKKCEL-WEVVVXLNSA-N [(e)-4-iodobut-3-enyl]cyclohexane Chemical compound I\C=C\CCC1CCCCC1 IRHYASGSXKKCEL-WEVVVXLNSA-N 0.000 abstract 1
- BQZXRDJKRSBDST-UXBLZVDNSA-N [(e)-5-iodopent-4-enyl]benzene Chemical compound I\C=C\CCCC1=CC=CC=C1 BQZXRDJKRSBDST-UXBLZVDNSA-N 0.000 abstract 1
- JMVFMMPRPBSDCU-UXBLZVDNSA-N [(e)-5-iodopent-4-enyl]cyclohexane Chemical compound I\C=C\CCCC1CCCCC1 JMVFMMPRPBSDCU-UXBLZVDNSA-N 0.000 abstract 1
- SOHOKGYYESQMHN-YRNVUSSQSA-N [(e)-6-iodohex-5-enyl]benzene Chemical compound I\C=C\CCCCC1=CC=CC=C1 SOHOKGYYESQMHN-YRNVUSSQSA-N 0.000 abstract 1
- ZZMATCATVCPAJU-YRNVUSSQSA-N [(e)-6-iodohex-5-enyl]cyclohexane Chemical compound I\C=C\CCCCC1CCCCC1 ZZMATCATVCPAJU-YRNVUSSQSA-N 0.000 abstract 1
- MCHZXWNMHQWPQP-XYOKQWHBSA-N [(e)-7-iodohept-6-enyl]benzene Chemical compound I\C=C\CCCCCC1=CC=CC=C1 MCHZXWNMHQWPQP-XYOKQWHBSA-N 0.000 abstract 1
- YOMBYYPUZBOVOW-XYOKQWHBSA-N [(e)-7-iodohept-6-enyl]cyclohexane Chemical compound I\C=C\CCCCCC1CCCCC1 YOMBYYPUZBOVOW-XYOKQWHBSA-N 0.000 abstract 1
- AHXDFLPEQWTXGJ-UKTHLTGXSA-N [(e)-8-iodooct-7-enyl]benzene Chemical compound I\C=C\CCCCCCC1=CC=CC=C1 AHXDFLPEQWTXGJ-UKTHLTGXSA-N 0.000 abstract 1
- ZLHUULZTFOPFCM-UKTHLTGXSA-N [(e)-8-iodooct-7-enyl]cyclohexane Chemical compound I\C=C\CCCCCCC1CCCCC1 ZLHUULZTFOPFCM-UKTHLTGXSA-N 0.000 abstract 1
- AGAUJJYFWPKQAT-UHFFFAOYSA-N [Li]C=CC(CCCCC)OC(C)OCC Chemical compound [Li]C=CC(CCCCC)OC(C)OCC AGAUJJYFWPKQAT-UHFFFAOYSA-N 0.000 abstract 1
- PXPDRDIQJMSQFQ-UHFFFAOYSA-N [Li]\C=C\CCCCCC Chemical compound [Li]\C=C\CCCCCC PXPDRDIQJMSQFQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- UOINAUPBIJRWIS-UHFFFAOYSA-N ethyl 7-(3,5-dioxocyclopenten-1-yl)heptanoate Chemical compound CCOC(=O)CCCCCCC1=CC(=O)CC1=O UOINAUPBIJRWIS-UHFFFAOYSA-N 0.000 abstract 1
- NOYKGOKFCDFQJT-UHFFFAOYSA-N ethyl 7-cyclopenta-1,3-dien-1-ylheptanoate Chemical compound CCOC(=O)CCCCCCC1=CC=CC1 NOYKGOKFCDFQJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000006038 hexenyl group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000002900 organolithium compounds Chemical class 0.000 abstract 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- PPTCQVOXIJIQIE-UHFFFAOYSA-N propan-2-yl 7-(3-hydroxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound CC(C)OC(=O)CCCCCCC1=CC(O)CC1=O PPTCQVOXIJIQIE-UHFFFAOYSA-N 0.000 abstract 1
- 230000002997 prostaglandinlike Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
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- 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
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/061—Aluminium compounds with C-aluminium linkage
- C07F5/066—Aluminium compounds with C-aluminium linkage compounds with Al linked to an element other than Al, C, H or halogen (this includes Al-cyanide linkage)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/02—Preparation of halogenated hydrocarbons by addition of halogens to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
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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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl group
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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
- C07C45/56—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
- C07C45/58—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 three-membered rings
-
- 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
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
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- 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
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- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/02—Lithium compounds
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- 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
1419181 Prostaglandins; organolithium compounds WISCONSIN ALUMNI RESEARCH FOUNDATION 24 Jan 1973 [26 Jan 1972 22 May 1972 29 Sept 1972] 3660/73 Headings C2C and C2J The invention comprises a process for preparing prostaglandins of the Formula I wherein R is H, CH 3 or CH 3 CH 2 ; R<SP>1</SP> is H, C 1 -C 9 saturated hydrocarbyl, pentenyl, hexenyl or benzyl; X is H, OH, 2-tetrahydropyranyloxy, OR<SP>11</SP>, wherein R<SP>11</SP> is C 1 -C 5 hydrocarbyl or benzyl, OCOR<SP>111</SP>, wherein R<SP>111</SP> is C 1 -C 8 hydrocarbyl or benzyl, or OCH(R 1 )OR 2 , wherein R 1 and R 2 each are C 1 -C 5 hydrocarbyl; n is 0 to 5; B is -CH 2 CH 2 - or -CH=CH-; Q is OH, OCH 3 or OCH 2 CH 3 ; and the ring A is by reacting compounds of the Formula II wherein B and ring A are as defined above with the proviso that any free hydroxy groups in ring A are protected, and Q is OCH 3 or OCH 2 CH 3 with compounds of the Formula III trans-Li-CH = CH-C(R)(X<SP>1</SP>)(CH 2 ) n R<SP>1</SP> wherein X<SP>1</SP> is H or protected hydroxy as defined above, and if desired removing any protecting groups and/or ester groups, and if desired converting in known manner one ring A to another ring A, and the novel compound of the formula which are obtained by the above process. The following intermediates and starting materials are also prepared: ethyl 1,3-cyclopentadieneheptanoate, ethyl 3-hydroxy-5-oxo- 1 - cyclopentene - 1 - heptanoate ethyl 5- hydroxy - 3 - oxo - 1 - cyclopentene - 1 - heptenoate ethyl 5 - oxo - 3 - (2 - tetrahydropyranyloxy) - 1 - cyclopentene - 1 - heptanoate, ethyl 3,5 - dioxo - 1 - cyclopentene - 1 - heptanoate, isopropyl 3 - hydroxy - 5 - oxo - 1- cyclopentene - 1 - heptanoate, 1 - iodo - 4 - cyclohexyl - 1 - trans - butene, 1 - iodo - 5- cyclohexyl - 1 - trans - pentene, 1 - iodo - 6- cyclohexyl - 1 - trans - hexene, 1 - iodo - 7- cyclohexyl - 1 - trans - heptene, 1 - iodo - 8- cyclohexyl - 1 - trans - octene, 1 - iodo - 5- phenyl - 1 - trans - pentene, 1 - iodo - 6 - phenyl- 1 - trans - hexene, 1 - iodo - 7 - phenyl - 1- trans - heptene, 1 - iodo 8 - phenyl - 1 - transoctene and 1 - iodo - 9 - phenyl - 1 - transnonene. 1 - Lithio - 1 - trans - octene and 1 - lithio- 3 - (1 - ethoxyethoxy) - trans - 1 - octene are obtained by reacting lithium powder in diethyl ether with solutions of 1-iodo-1-trans-octene and the 3 -(1 - ethoxyethoxy) - 1 - iodo - 1- trans-octene respectively. Pharmaceutical compositions contain the above novel compounds and pharmaceutically acceptable carriers or diluents. The compounds possess prostaglandin-like activities. Reference has been directed by the Comptroller to Specification 1,377,258 also Reference has been directed by the Comptroller to Specifications 1,314,292, 1,314,291, 1,282,661 1,198,071, 1,097,533, 1,097,157 and 1,040,544.
[GB1419181A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/221,058 US4031129A (en) | 1972-01-26 | 1972-01-26 | 15-Deoxy-PGE1 and method for preparing same |
| US25572872A | 1972-05-22 | 1972-05-22 | |
| US29344272A | 1972-09-29 | 1972-09-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE37108L IE37108L (en) | 1973-07-26 |
| IE37108B1 true IE37108B1 (en) | 1977-05-11 |
Family
ID=27396893
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE57/73A IE37106B1 (en) | 1972-01-26 | 1973-01-15 | Prostaglandins and method for preparing same |
| IE599/76A IE37108B1 (en) | 1972-01-26 | 1973-01-15 | Iodo-alkenes |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE57/73A IE37106B1 (en) | 1972-01-26 | 1973-01-15 | Prostaglandins and method for preparing same |
Country Status (17)
| Country | Link |
|---|---|
| JP (3) | JPS5333583B2 (en) |
| AR (2) | AR199893A1 (en) |
| AU (1) | AU452896B2 (en) |
| BE (1) | BE794516A (en) |
| BG (3) | BG25206A3 (en) |
| CA (1) | CA1014092A (en) |
| CH (3) | CH580046A5 (en) |
| DD (3) | DD112750A5 (en) |
| DE (2) | DE2365927A1 (en) |
| ES (3) | ES410962A1 (en) |
| FR (3) | FR2181693B1 (en) |
| GB (3) | GB1419181A (en) |
| IE (2) | IE37106B1 (en) |
| IL (5) | IL49286A (en) |
| NL (2) | NL153514B (en) |
| RO (1) | RO71588A (en) |
| SE (3) | SE7600888L (en) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1018970A (en) * | 1972-10-27 | 1977-10-11 | American Home Products Corporation | 15-substituted prostanoic acids |
| JPS5720305B2 (en) * | 1973-02-28 | 1982-04-27 | ||
| US4029693A (en) * | 1975-01-20 | 1977-06-14 | The Upjohn Company | 2A,2B-Dihomo-11-deoxy-17(substituted phenyl)-18,19,20-trinor-PGE2 compounds and their corresponding esters |
| US4032561A (en) * | 1975-05-27 | 1977-06-28 | The Upjohn Company | 17-Phenyl-18,19,20-trinor-cis-4,5-didehydro-PGF1.sub.α compounds |
| US4016184A (en) * | 1975-09-17 | 1977-04-05 | The Upjohn Company | 9-Deoxy-9,10-didehydro-PGD1 compounds |
| US4365075A (en) * | 1975-09-17 | 1982-12-21 | The Upjohn Company | ω-Aryl-PGD compounds |
| US4029814A (en) * | 1975-12-29 | 1977-06-14 | The Upjohn Company | Phenyl-substituted prostaglandin-e type analogs |
| US4219662A (en) * | 1977-02-28 | 1980-08-26 | The Upjohn Company | 11-Deoxy-17-phenyl-PGE1 analogs |
| AU529883B2 (en) * | 1978-09-04 | 1983-06-23 | Australian National University, The | Substituted cyclopentenones |
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0
- BE BE794516D patent/BE794516A/en unknown
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1973
- 1973-01-15 AU AU51081/73A patent/AU452896B2/en not_active Expired
- 1973-01-15 IE IE57/73A patent/IE37106B1/en unknown
- 1973-01-15 CA CA161,270A patent/CA1014092A/en not_active Expired
- 1973-01-15 IE IE599/76A patent/IE37108B1/en unknown
- 1973-01-17 IL IL49286A patent/IL49286A/en unknown
- 1973-01-17 IL IL41305A patent/IL41305A/en unknown
- 1973-01-17 IL IL49285A patent/IL49285A/en unknown
- 1973-01-24 GB GB366073A patent/GB1419181A/en not_active Expired
- 1973-01-24 GB GB4753874A patent/GB1419182A/en not_active Expired
- 1973-01-24 GB GB4753974A patent/GB1419183A/en not_active Expired
- 1973-01-25 NL NL737301094A patent/NL153514B/en unknown
- 1973-01-25 BG BG022528A patent/BG25206A3/en unknown
- 1973-01-25 CH CH270376A patent/CH580046A5/xx not_active IP Right Cessation
- 1973-01-25 ES ES410962A patent/ES410962A1/en not_active Expired
- 1973-01-25 BG BG032229A patent/BG25207A3/en unknown
- 1973-01-25 CH CH105573A patent/CH590834A5/xx not_active IP Right Cessation
- 1973-01-25 JP JP999673A patent/JPS5333583B2/ja not_active Expired
- 1973-01-25 DE DE2365927*A patent/DE2365927A1/en active Pending
- 1973-01-25 CH CH270276A patent/CH578502A5/xx not_active IP Right Cessation
- 1973-01-25 DD DD179628*A patent/DD112750A5/xx unknown
- 1973-01-25 BG BG7300032232A patent/BG25208A3/en unknown
- 1973-01-25 DD DD179629*A patent/DD113214A5/xx unknown
- 1973-01-25 DD DD168453A patent/DD108069A5/xx unknown
- 1973-01-25 AR AR246283A patent/AR199893A1/en active
- 1973-01-25 FR FR7302607A patent/FR2181693B1/fr not_active Expired
- 1973-01-25 RO RO197391055A patent/RO71588A/en unknown
- 1973-01-25 DE DE2365513A patent/DE2365513C3/en not_active Expired
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1974
- 1974-09-18 AR AR255637A patent/AR200537A1/en active
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1975
- 1975-01-17 FR FR7501567A patent/FR2257567B1/fr not_active Expired
- 1975-01-17 FR FR7501566A patent/FR2272642B1/fr not_active Expired
- 1975-06-16 ES ES438595A patent/ES438595A1/en not_active Expired
- 1975-06-16 ES ES438594A patent/ES438594A1/en not_active Expired
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1976
- 1976-01-26 SE SE7600888A patent/SE7600888L/en unknown
- 1976-01-28 SE SE7600889A patent/SE7600889L/en unknown
- 1976-01-28 SE SE7600890A patent/SE7600890L/en unknown
- 1976-03-25 IL IL49286A patent/IL49286A0/en unknown
- 1976-03-25 IL IL49285A patent/IL49285A0/en unknown
- 1976-10-08 JP JP51120458A patent/JPS5253840A/en active Pending
- 1976-10-08 JP JP51120459A patent/JPS5253801A/en active Pending
-
1977
- 1977-07-20 NL NL7708070A patent/NL7708070A/en not_active Application Discontinuation
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