GB1384024A - Process for the preparation of 3-hydroxy-2-3-hydroxy-1-octenyl- 5-oxocyclopentane-heptanoic acid and derivatives thereof - Google Patents
Process for the preparation of 3-hydroxy-2-3-hydroxy-1-octenyl- 5-oxocyclopentane-heptanoic acid and derivatives thereofInfo
- Publication number
- GB1384024A GB1384024A GB1415273A GB1415273A GB1384024A GB 1384024 A GB1384024 A GB 1384024A GB 1415273 A GB1415273 A GB 1415273A GB 1415273 A GB1415273 A GB 1415273A GB 1384024 A GB1384024 A GB 1384024A
- Authority
- GB
- United Kingdom
- Prior art keywords
- tetrahydropyran
- oxy
- hydroxy
- octenyl
- heptanoate
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000005749 Copper compound Substances 0.000 abstract 2
- -1 alkenyl copper compound Chemical class 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- VSMOENVRRABVKN-UHFFFAOYSA-N (+/-)-matsutakeol Natural products CCCCCC(O)C=C VSMOENVRRABVKN-UHFFFAOYSA-N 0.000 abstract 1
- VSMOENVRRABVKN-MRVPVSSYSA-N 1-Octen-3-ol Natural products CCCCC[C@H](O)C=C VSMOENVRRABVKN-MRVPVSSYSA-N 0.000 abstract 1
- ZIQZDBIMVJFVBY-UHFFFAOYSA-N 2-(1,2-dibromooctan-3-yloxy)oxane Chemical compound BrCC(C(CCCCC)OC1OCCCC1)Br ZIQZDBIMVJFVBY-UHFFFAOYSA-N 0.000 abstract 1
- IKSVRFLFLHXCFK-UHFFFAOYSA-N 2-oct-1-yn-3-yloxyoxane Chemical compound CCCCCC(C#C)OC1CCCCO1 IKSVRFLFLHXCFK-UHFFFAOYSA-N 0.000 abstract 1
- YDXQPTHHAPCTPP-UHFFFAOYSA-N 3-Octen-1-ol Natural products CCCCC=CCCO YDXQPTHHAPCTPP-UHFFFAOYSA-N 0.000 abstract 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 abstract 1
- 125000001475 halogen functional group Chemical group 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229960002523 mercuric chloride Drugs 0.000 abstract 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 abstract 1
- PQKUWAVOSCVDCT-UHFFFAOYSA-N methyl 7-(3-hydroxy-5-oxocyclopenten-1-yl)heptanoate Chemical compound COC(=O)CCCCCCC1=CC(O)CC1=O PQKUWAVOSCVDCT-UHFFFAOYSA-N 0.000 abstract 1
- RMSROFOPTSOXCN-UHFFFAOYSA-N methyl 7-[3-(oxan-2-yloxy)-5-oxocyclopenten-1-yl]heptanoate Chemical compound C1C(=O)C(CCCCCCC(=O)OC)=CC1OC1OCCCC1 RMSROFOPTSOXCN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
Classifications
-
- 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 System
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
-
- 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
- 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
-
- 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
Abstract
1384024 Prostaglandins; organocopper compounds G D SEARLE & CO 23 March 1973 [14 April 1972] 14152/73 Headings C2J and C2C [Also in Division C3] Compounds of Formula I in which X=-CH 2 -, -CH(OH)-, -CH(OSiAlk 3 )- or -CH(OCOY)-, Alk being C 1-7 alkyl, THP being tetrahydropyran-2-yl and Y being H or C 1-6 alkyl, R=H or Alk, R<SP>1</SP>=H or C 1-4 alkyl, R<SP>11</SP>=OH, OTHP, OAlkOAlk or OSiAlk 3 , Z=-CH=CH- or -CH 2 -CH 2 -, m=3 or 4, n=2-8 and the wavy lines represent the alternative α or # configuration or the epimeric mixture, are prepared by reacting a compound of Formula II with an alkenyl copper compound of Formula III, IV or V optionally followed by hydrolysis of the protecting groups if desired. The following intermediates are prepared in the examples: methyl 3(RS) - hydroxy - 5 - oxo - 1- cyclopentene - 1 - heptanoate, methyl 3(RS)- (tetrahydropyran - 2 - yl)oxy - 5 - oxo - 1 - cyclopentene - 1 - heptanoate, methyl 3(R or S)- hydroxy - 5.- [(1 - carboxyisoamyl) - oxyimino]- 1 - cyclopentene - 1 - heptanoate, methyl 3(R or S) - hydroxy - 5 - oxo - 1 - cyclopentene - 1 - heptanoate, 3(RS) - (tetrahydropyran - 2 - yl) oxy - 1 - octyne, 3(RS) - (tetrahydropyran - 2 -yl) oxy - 1 - trans - octenyl iodide, 3(RS) - 1 - octen- 3 - ol, 3(RS) - (tetrahydropyran - 2 - yl)oxy - 1- octene, 1,2 - dibromo - 3(RS) - (tetrahydropyran- 2 - yl)oxy - octane, 3(RS) - (tetrahydropyran - 2- yl) - oxy - 1 - trans - octenyl bromide, 3(RS)- hydroxy - 1 - cis - octenyl iodide and 3(RS)- tetrahydropyran-2-yl)oxy-1-cis-octenyl iodide. 3 - (Tetrahydropyran - 2 - yl)oxy - 1 - alkenyl copper compounds are prepared by reaction of a 1 - halo - 3 - (tetrahydropyran - 2 - yl)oxy - 1- alkene with magnesium metal activated with mercuric chloride, followed by treatment with cuprous iodide. 3(RS)-(tetrahydropyran-2-yl) oxy-1-octenyl copper is prepared in Example 3A.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24423872A | 1972-04-14 | 1972-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1384024A true GB1384024A (en) | 1974-02-12 |
Family
ID=22921943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1415273A Expired GB1384024A (en) | 1972-04-14 | 1973-03-23 | Process for the preparation of 3-hydroxy-2-3-hydroxy-1-octenyl- 5-oxocyclopentane-heptanoic acid and derivatives thereof |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4914444A (en) |
| AU (1) | AU468029B2 (en) |
| CH (1) | CH584687A5 (en) |
| DE (1) | DE2315312A1 (en) |
| FR (1) | FR2180099B1 (en) |
| GB (1) | GB1384024A (en) |
| HU (1) | HU168106B (en) |
| NL (1) | NL7305303A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7897795B2 (en) | 2008-04-09 | 2011-03-01 | Scinopharm Taiwan Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010041632A (en) * | 1998-03-06 | 2001-05-25 | 아스트라제네카 악티에볼라그 | Novel Process |
-
1973
- 1973-03-23 GB GB1415273A patent/GB1384024A/en not_active Expired
- 1973-03-27 DE DE2315312A patent/DE2315312A1/en not_active Withdrawn
- 1973-04-13 JP JP48042071A patent/JPS4914444A/ja active Pending
- 1973-04-13 AU AU54472/73A patent/AU468029B2/en not_active Expired
- 1973-04-13 HU HUSE1670A patent/HU168106B/hu unknown
- 1973-04-13 FR FR7313540A patent/FR2180099B1/fr not_active Expired
- 1973-04-16 CH CH540573A patent/CH584687A5/xx not_active IP Right Cessation
- 1973-04-16 NL NL7305303A patent/NL7305303A/xx not_active Application Discontinuation
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7897795B2 (en) | 2008-04-09 | 2011-03-01 | Scinopharm Taiwan Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
| US8436194B2 (en) | 2008-04-09 | 2013-05-07 | Scinopharm Taiwan, Ltd. | Process for the preparation of prostaglandin analogues and intermediates thereof |
| US8742143B2 (en) | 2008-04-09 | 2014-06-03 | Scinopharm Taiwan, Ltd. | Process for the preparation of prostaglandin analogues |
Also Published As
| Publication number | Publication date |
|---|---|
| HU168106B (en) | 1976-02-28 |
| JPS4914444A (en) | 1974-02-07 |
| FR2180099B1 (en) | 1977-12-30 |
| NL7305303A (en) | 1973-10-16 |
| AU5447273A (en) | 1974-10-17 |
| DE2315312A1 (en) | 1973-10-25 |
| FR2180099A1 (en) | 1973-11-23 |
| CH584687A5 (en) | 1977-02-15 |
| AU468029B2 (en) | 1975-12-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |