GB1356582A - Process for the manufacture of prostadienoic acid derivatives - Google Patents
Process for the manufacture of prostadienoic acid derivativesInfo
- Publication number
- GB1356582A GB1356582A GB746971A GB746971A GB1356582A GB 1356582 A GB1356582 A GB 1356582A GB 746971 A GB746971 A GB 746971A GB 746971 A GB746971 A GB 746971A GB 1356582 A GB1356582 A GB 1356582A
- Authority
- GB
- United Kingdom
- Prior art keywords
- furan
- epimer
- tetrahydro
- oxo
- trans
- 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
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- POKRQUNDSGAZIA-OALUTQOASA-N 7-[(1r,2s)-2-octylcyclopentyl]hepta-2,4-dienoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCC=CC=CC(O)=O POKRQUNDSGAZIA-OALUTQOASA-N 0.000 title 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 15
- -1 p-phenylbenzoate ester Chemical class 0.000 abstract 6
- CVMKPYXSQWWZFH-UHFFFAOYSA-N 1-dimethoxyphosphorylnonan-2-one Chemical compound CCCCCCCC(=O)CP(=O)(OC)OC CVMKPYXSQWWZFH-UHFFFAOYSA-N 0.000 abstract 3
- 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 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 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
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 abstract 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- VONWDASPFIQPDY-UHFFFAOYSA-N dimethyl methylphosphonate Chemical compound COP(C)(=O)OC VONWDASPFIQPDY-UHFFFAOYSA-N 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002240 furans Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 230000003647 oxidation Effects 0.000 abstract 1
- 238000007254 oxidation reaction Methods 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 150000003180 prostaglandins 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Blinds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1356582 Prostaglandins; dimethyl 2-oxononylphosphonate IMPERIAL CHEMICAL INDUSTRIES Ltd 9 Feb 1972 [22 March 1971] 7469/71 Headings C2C and C2P The invention comprises a process for the manufacture of either C-15 epimer of 20-ethyl- 9α,11α,15 - trihydroxy - cis - 5, trans - 13- prostadienoic acid or an ester thereof with a C 1-6 alkanol which includes the crystallization of a mixture of the epimers of the p-phenylbenzoate ester of the Formula II containing 50% or more of one epimer to give a compound of Formula II enriched in that epimer and containing at least 75% of that epimer, a compound of Formula II above containing at least 75% of one epimer and a mixture of equal parts of the epimers of Formula II above, which is obtained by reducing 2,3,3α#, 6α# - tetrahydro - 2 - oxo - 4# - (3 - oxodec - trans- 1 - enyl) - 5α - (p - phenylbenzoyloxy)cyclopenteno- [b]furan resulting from the reaction between dimethyl 2-oxononylphosphonate, n-butyl lithium and 2,3,3α#,6α# - tetrahydro - 4# -formyl- 2 - oxo - 5α - (p - phenylbenzoyloxy)cyclopenteno- [b]furan, resulting from the oxidation of 2,3,3α#, 6a# - tetrahydro - 4# - hydroxymethyl - 2 - oxo- 5α - (p - phenylbenzoyloxy)cyclopenteno[b]furan, obtained by the demethylation of 2,3,3α#,6α#- tetrahydro - 4# - methoxymethyl - 2 - oxo - 5α - (pphenylbenzoyloxy)cyclopentenu[b]furan, which is prepared by diodinating 2,3,3α#,6α#-tetrahydro- 6# - iodo - 4# - methoxymethyl - 2 - oxo - 5α - (pphenylbenzoyloxy)cyclopenteno[b] furan, obtained by reacting p-phenylbenzoyl chloride with 5α- hydroxy - 6# - iodo - 4# - methoxymethyl - 2- oxo - 2,3,3α#,6α# - tetrahydrocyclopenteno[b]- furan. 20 - Ethyl - 9α,11α,15 - trihydroxy - cis - 5, trans-13-prostadienoic acid (90% of S-epimer) is prepared by hydrolysing the corresponding 11α,15-bis-(tetrahydropyranyl)ether, obtained by adding (4 - carboxybutyl)triphenylphosphonium bromide to a solution of 2,3,3α#,6α#-tetrahydro - 5α - (tetrahydropyran - 2 - yloxy) - 4# - [3S- (tetrahydropyran - 2 - yloxy) - dec - trans - 1- enyl] - 2# - hydroxycyclopenteno[b]furan, resulting from the reduction of the corresponding 2- oxocyclopenteno[b]furan derivative, which is prepared by reacting dihydropyran 2 with 2,3,3α#, 6α# - tetrahydro - 5α - hydroxy - 4# - (3S - hydroxydec - trans - 1 - enyl) - 2 - oxocyclopenteno[b]furan, resulting from the hydrolysis of the 3S-epimer of the compound of Formula II above. Dimethyl 2-oxononylphosphonate is prepared by reacting dimethyl methylphosphonate with nbutyl lithium and ethyl octanoate.
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ZA721159A ZA721159B (en) | 1971-03-22 | 1972-02-21 | Process for the separation of the c-15 epimers of 20-ethyl-9a,11alpha,15-trihydroxy-5-cis-13-trans-prostadienoic acid |
| FR7209844A FR2130503A1 (en) | 1971-03-22 | 1972-03-21 | S-epimer of 20-ethyl-9alpha, 11 alpha, 15-trihydroxy-5-cis-13-trans - prostadienic acid prodn from p-phenylbenzoate esters |
| BE781079A BE781079A (en) | 1971-03-22 | 1972-03-22 | PRODUCTION OF 20-ETHYL-9, 11, 15-TRIHYDROXY-5-CIS-13-TRANS-PROSTADIENOIC ACID EPIMERS AND THEIR |
| NL7203809A NL7203809A (en) | 1971-03-22 | 1972-03-22 | |
| HUIE496A HU163889B (en) | 1971-03-22 | 1972-03-22 | |
| DE19722213907 DE2213907A1 (en) | 1971-03-22 | 1972-03-22 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB749671A GB1395004A (en) | 1971-03-22 | 1971-03-22 | Shower baths |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1356582A true GB1356582A (en) | 1974-06-12 |
Family
ID=9834248
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB749671A Expired GB1395004A (en) | 1971-03-22 | 1971-03-22 | Shower baths |
| GB746971A Expired GB1356582A (en) | 1971-03-22 | 1971-03-22 | Process for the manufacture of prostadienoic acid derivatives |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB749671A Expired GB1395004A (en) | 1971-03-22 | 1971-03-22 | Shower baths |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1395004A (en) |
-
1971
- 1971-03-22 GB GB749671A patent/GB1395004A/en not_active Expired
- 1971-03-22 GB GB746971A patent/GB1356582A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1395004A (en) | 1975-05-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| CSNS | Application of which complete specification have been accepted and published, but patent is not sealed |