GB1398346A - Prostaglandins and the preparation thereof - Google Patents
Prostaglandins and the preparation thereofInfo
- Publication number
- GB1398346A GB1398346A GB1542573A GB1542573A GB1398346A GB 1398346 A GB1398346 A GB 1398346A GB 1542573 A GB1542573 A GB 1542573A GB 1542573 A GB1542573 A GB 1542573A GB 1398346 A GB1398346 A GB 1398346A
- Authority
- GB
- United Kingdom
- Prior art keywords
- cis
- trans
- compounds
- dihydroxy
- hydroxy
- 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
- 229940094443 oxytocics prostaglandins Drugs 0.000 title abstract 5
- 150000003180 prostaglandins Chemical class 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- -1 ethyl-magnesium halide Chemical class 0.000 abstract 4
- 230000001590 oxidative effect Effects 0.000 abstract 3
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 abstract 2
- NKVJKVMGJABKHV-UHFFFAOYSA-N 3-carboxypropyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC(=O)O)C1=CC=CC=C1 NKVJKVMGJABKHV-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical group [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 1
- XOLXDDDYNDJMLN-DSYZDTNSSA-N (Z)-7-[(1R,2R)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-4-enoic acid Chemical class OC1[C@H](CC\C=C/CCC(=O)O)[C@H](C(C1)O)CCC(CCCCC)=O XOLXDDDYNDJMLN-DSYZDTNSSA-N 0.000 abstract 1
- GRHQDJDRGZFIPO-UHFFFAOYSA-N 4-bromobutanoic acid Chemical compound OC(=O)CCCBr GRHQDJDRGZFIPO-UHFFFAOYSA-N 0.000 abstract 1
- NPZIGNRDZFBLQF-UHFFFAOYSA-N [6-(methoxymethylidene)cyclohexa-2,4-dien-1-yl]-diphenylphosphanium;chloride Chemical compound [Cl-].COC=C1C=CC=CC1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 NPZIGNRDZFBLQF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002170 ethers Chemical class 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 230000000699 topical effect Effects 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
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/94—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
-
- 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 System
- 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, i.e. RP(=X)(XH)2 (X = S, 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
-
- 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
1398346 Prostaglandins; 3-carboxypropyltriphenylphosphonium bromide UPJOHN CO 30 March 1973 [27 April 1972] 15425/73 Headings C2C and C2P [Also in Division C3] The invention comprises optically active prostaglandins of the formulae or racemates thereof wherein M is or wherein R 5 is H, CH 3 or CH 2 CH 3 , R 1 is H, C 1-12 alkyl, C 3-10 cycloalkyl, C 7-12 aralkyl, or phenyl optionally substituted by 1 to 3 times by halogen atoms or C 1-4 alkyl radicals, E is trans CH=CH or CH 2 CH 2 , R x is C 2-10 alkyl optionally substituted by 1 or 2 fluorine atoms, provided that R x is not n-pentyl when E is trans- CH=CH-; and D represents one of the four carbocyclic radicals the alkanoate thereof, and the pharmacologically acceptable salts thereof when R 1 is H and processes for their preparation. The 4,5-cisdidehydro-PGFα compounds of the above formula in which R 1 and R 5 are H are prepared by alkylating lactols of the Formulae XXXVIII and LVIII with 3-carboxypropylenetriphenylphosphorane. 4,5-cis-Didehydro-2a-homo-PGF 1 α is obtained by reacting a lactol of the Formula XXXVIII above in which R 2 is n-pentyl with 4-carboxybutylenetriphenylphosphorane. The cis-4,5- didehydro-PGFα compound in which R 5 is CH 3 or CH 2 CH 3 are prepared by reacting methyl- or ethyl-magnesium halide with the 9,11-disilyl ethers of the appropriate 9,11-dihydroxy-15- oxo-cis-4-prostenoic acids or 9,11-dihydroxy-15- oxo-cis-4-trans-13-prostadienoic acids and hydrolysing the resulting product. The cis-4,5- didehydro-PGA, cis-4,5-dedihydro-PGB and cis- 4,5-didehydro-PGF# compounds are obtained by the acidic dehydration of the corresponding PGE compounds by reacting the corresponding PGF compounds with bases whose pH is in aqueous solutions are greater than 10, and reduction of the corresponding PGE compounds respectively. The cis-4,5-didehydro-PGE compounds in which R 5 is H are obtained by oxidizing the corresponding PGF compounds in which the 11- and 15-hydroxy groups are protected with silyl ether groups and removing the protecting groups. The corresponding compounds in which R 6 is CH 3 or CH 2 CH 3 are prepared by oxidizing the corresponding PGF on which the 11-hydroxy group is protected with a silyl ether group and removing the protecting group. 3α,5α - Dihydroxy - 2# - (3 - hydroxy - trans - 1- octenyl) - 1α - cyclopentanepropionaldehyde - 8- lactol is prepared by hydrolysing 2α-(3-methoxy- 2 - propenyl) - 3# - [3 - (tetrahydropyran - 2- yloxy) - trans - 1 - octenyl] - 4α - (tetrahydropyran- 2-yloxy)-1α-cyclopentanol, obtained by reacting 5α - hydroxy - 3α - (tetrahydropyran - 2 - yloxy)- 2# - [3 - (tetrahydropyran - 2 - yloxy) - trans - 1 - octenyl] - 1α - cyclopentaneacetaldehyde γ-lactol with methoxymethylenetriphenylphosphonium chloride and butyllithium in tetrahydrofuran. Methyl - 9α,11α - dihydroxy - 15 - oxo - cis - 4, traps-13-prostadienoate is obtained by oxidizing methyl - 9α,11α,15α - trihydroxy - cis - 4, trans- 13-prostadienoate with 2,3-dichloro-5,6-dicyano- 1,4-benzoquinone. 3α,5α - Dihydroxy - 2# - (3 - hydroxy - 4- methyloctyl) - 1α - cyclopentanepropionaldehyde- #-lactol is obtained by hydrogenating 3α,5α- dihydroxy - 2# - (3 - hydroxy - 4 - methyl - trans- 1 - octenyl) - 1α - cyclopentane - propionaldehyde #-lactol. 3 - Carboxypropyltriphenylphosphonium bromide is prepared by reacting triphenylphosphine with 4-bromobutyric acid. Pharmaceutical compositions, suitable for oral, parenteral, rectal, topical or intravaginal administration, contain the above novel prostaglandins together with pharmaceutically acceptable carriers. The compounds possess similar activities to the naturally occurring prostaglandins.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24799372A | 1972-04-27 | 1972-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1398346A true GB1398346A (en) | 1975-06-18 |
Family
ID=22937208
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1542573A Expired GB1398346A (en) | 1972-04-27 | 1973-03-30 | Prostaglandins and the preparation thereof |
| GB4995074A Expired GB1398347A (en) | 1972-04-27 | 1973-03-30 | Prostaglandin intermediates |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4995074A Expired GB1398347A (en) | 1972-04-27 | 1973-03-30 | Prostaglandin intermediates |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5825668B2 (en) |
| BE (1) | BE798830A (en) |
| CH (1) | CH587811A5 (en) |
| FR (1) | FR2183036B1 (en) |
| GB (2) | GB1398346A (en) |
| NL (1) | NL7305434A (en) |
| ZA (1) | ZA732245B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5563397A (en) * | 1978-10-31 | 1980-05-13 | Mitsubishi Electric Corp | Manufacture of bolling heat transmission surface |
| JPS61144268U (en) * | 1985-02-27 | 1986-09-05 |
-
1973
- 1973-03-30 GB GB1542573A patent/GB1398346A/en not_active Expired
- 1973-03-30 GB GB4995074A patent/GB1398347A/en not_active Expired
- 1973-04-02 ZA ZA732245A patent/ZA732245B/en unknown
- 1973-04-11 CH CH390276A patent/CH587811A5/xx not_active IP Right Cessation
- 1973-04-18 NL NL7305434A patent/NL7305434A/xx not_active Application Discontinuation
- 1973-04-25 JP JP48046326A patent/JPS5825668B2/en not_active Expired
- 1973-04-26 FR FR7315128A patent/FR2183036B1/fr not_active Expired
- 1973-04-27 BE BE130508A patent/BE798830A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL7305434A (en) | 1973-10-30 |
| BE798830A (en) | 1973-10-29 |
| CH587811A5 (en) | 1977-05-13 |
| FR2183036B1 (en) | 1977-11-10 |
| ZA732245B (en) | 1974-03-27 |
| GB1398347A (en) | 1975-06-18 |
| JPS4947350A (en) | 1974-05-08 |
| FR2183036A1 (en) | 1973-12-14 |
| JPS5825668B2 (en) | 1983-05-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |