DE3464488D1 - Conjugate addition of organocuprates generated from copper (i) cyanide and vinyl stannanes useful in prostaglandin analog synthesis - Google Patents
Conjugate addition of organocuprates generated from copper (i) cyanide and vinyl stannanes useful in prostaglandin analog synthesisInfo
- Publication number
- DE3464488D1 DE3464488D1 DE8484104827T DE3464488T DE3464488D1 DE 3464488 D1 DE3464488 D1 DE 3464488D1 DE 8484104827 T DE8484104827 T DE 8484104827T DE 3464488 T DE3464488 T DE 3464488T DE 3464488 D1 DE3464488 D1 DE 3464488D1
- Authority
- DE
- Germany
- Prior art keywords
- copper
- reagent
- cyanide
- organocuprates
- useful
- 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
- 150000003180 prostaglandins Chemical class 0.000 title abstract 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 title 1
- 229920002554 vinyl polymer Polymers 0.000 title 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 6
- 238000000034 method Methods 0.000 abstract 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052802 copper Inorganic materials 0.000 abstract 2
- 239000010949 copper Substances 0.000 abstract 2
- -1 alkenyl lithium Chemical compound 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000000010 aprotic solvent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 231100001261 hazardous Toxicity 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 238000010791 quenching Methods 0.000 abstract 1
- 230000000171 quenching effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 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
-
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2208—Compounds having tin linked only to carbon, hydrogen and/or halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Manufacture And Refinement Of Metals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/493,709 US4543421A (en) | 1983-05-11 | 1983-05-11 | Conjugate addition of organocuprates generated from copper (I) cyanide and vinyl stannanes useful in prostaglandin analog synthesis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3464488D1 true DE3464488D1 (en) | 1987-08-06 |
Family
ID=23961378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8484104827T Expired DE3464488D1 (en) | 1983-05-11 | 1984-04-30 | Conjugate addition of organocuprates generated from copper (i) cyanide and vinyl stannanes useful in prostaglandin analog synthesis |
Country Status (7)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178139B1 (en) * | 1984-10-08 | 1989-07-05 | Teijin Limited | Process for producing 2,3-disubstituted -4-substituted cyclopentanones, enantiomorphs, or mixtures thereof |
| US4785124A (en) * | 1987-06-08 | 1988-11-15 | G. D. Searle & Co. | Process for preparing higher order cuprate complexes |
| US4777275A (en) * | 1987-06-09 | 1988-10-11 | G. D. Searle & Co. | Process of preparing higher order cuprate complexes |
| US5233059A (en) * | 1991-07-25 | 1993-08-03 | Iowa State University Research Foundation, Inc. | Synthesis of benzoprostacyclins using palladium catalysis |
| US5618959A (en) * | 1995-03-10 | 1997-04-08 | Vivus Incorporated | Process for preparing prostaglandin E1, E2 and analogs thereof using furylcopper reagents |
| JP4153998B2 (ja) | 1996-11-14 | 2008-09-24 | 第一ファインケミカル株式会社 | プロスタグランジン類の製造方法 |
| WO1999009992A1 (fr) | 1997-08-27 | 1999-03-04 | Yoshitomi Pharmaceutical Industries, Ltd. | Promoteurs de neovascularisation |
| WO2006134201A1 (en) | 2005-06-17 | 2006-12-21 | Suomen Ympäristökeskus | Method and device for collecting oil from the surface of water by using a wave damping space |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238623A (en) * | 1976-03-29 | 1980-12-09 | Miles Laboratories, Inc. | 5,6-Benzo analogues of prostaglandin |
| US4170709A (en) * | 1977-10-03 | 1979-10-09 | American Home Products Corporation | 16-Keto PGE2 methyl esters |
| US4127612A (en) * | 1978-03-17 | 1978-11-28 | Miles Laboratories, Inc. | 19-Hydroxy PGE1 carbinol analogues |
| US4171331A (en) * | 1978-06-05 | 1979-10-16 | Miles Laboratories, Inc. | 1 And 2-substituted analogues of certain prostaglandins |
| US4363817A (en) * | 1981-08-27 | 1982-12-14 | Miles Laboratories, Inc. | Enol acylate analogs of E1 and E2 prostaglandins |
-
1983
- 1983-05-11 US US06/493,709 patent/US4543421A/en not_active Expired - Fee Related
-
1984
- 1984-01-09 CA CA000444952A patent/CA1201118A/en not_active Expired
- 1984-03-28 JP JP59058523A patent/JPS59210065A/ja active Granted
- 1984-04-30 EP EP84104827A patent/EP0133450B1/en not_active Expired
- 1984-04-30 DE DE8484104827T patent/DE3464488D1/de not_active Expired
- 1984-04-30 AT AT84104827T patent/ATE28075T1/de not_active IP Right Cessation
- 1984-05-10 AU AU27905/84A patent/AU544962B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| EP0133450B1 (en) | 1987-07-01 |
| EP0133450A3 (en) | 1985-04-03 |
| AU2790584A (en) | 1984-11-15 |
| US4543421A (en) | 1985-09-24 |
| JPS59210065A (ja) | 1984-11-28 |
| JPS6344743B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-09-06 |
| CA1201118A (en) | 1986-02-25 |
| AU544962B2 (en) | 1985-06-27 |
| ATE28075T1 (de) | 1987-07-15 |
| EP0133450A2 (en) | 1985-02-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |