GB1423664A - Prostaglandin compounds - Google Patents
Prostaglandin compoundsInfo
- Publication number
- GB1423664A GB1423664A GB4324173A GB4324173A GB1423664A GB 1423664 A GB1423664 A GB 1423664A GB 4324173 A GB4324173 A GB 4324173A GB 4324173 A GB4324173 A GB 4324173A GB 1423664 A GB1423664 A GB 1423664A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- pgf
- pge
- formulμ
- 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
- -1 Prostaglandin compounds Chemical class 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 3
- 150000003180 prostaglandins Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002170 ethers Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 229920000858 Cyclodextrin Polymers 0.000 abstract 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008016 pharmaceutical coating Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1423664 3,16-Dimethylprostaglandins ONO PHARMACEUTICAL CO Ltd 14 Sept 1973 [16 Sept 1972] 43241/73 Heading C2C [Also in Division C3] The invention comprises 3,16-dimethylprostaglandins of the Formulµ V and XVIII wherein A represents a grouping of the formula X is -CH 2 CH 2 - or cis -CH=CH-, Y is trans -CH=CH- or, when X is -CH 2 CH 2 -, Y may be -CH 2 CH 2 -, and the esters thereof, and cyclodextrin clathrates of such acids and esters, and non-toxic salts of such acids and prostaglandins of the formulµ wherein THP is 2-tetrahydropyranyl optionally substituted by at least one alkyl radical, and their preparation. 3,16-Dimethyl-PGA 2 and 3,16-dimethyl-PGA 1 are prepared by the acidic dehydration of 3,16-dimethyl-PGE 2 and 3,16- dimethyl-PGE 1 respectively, which are obtained by hydrolysing 3,16-dimethyl-PGE 2 11,15-bistetrahydro pyranyl ether and 3,16-dimethyl- PGE 1 11,15 - bis - tetrahydropyranyl ether, obtained by oxidizing the corresponding 3,16- dimethyl-PGF 2α and 3,16-dimethyl-PGF 1α bistetrahydropyranyl ethers, resulting from the reaction of 2 - hydroxy - 4# - (4 - methyl - 3- tetrahydropyran - 2<SP>1 </SP>- yloxy trans - 1 - octenyl)- 5α - (tetrahydropyran - 2 - yloxy) - 3,3a,4,5,6,6ahexahydro - 2H - cyclopenta[b]furan with a phosphorone of the formula (Ph), P = CH-CH 2 -CH(CH 3 )-CH 2 -COOH, followed by, if desired, hydrogenation of the 5,6-double bond. 3,16-Dimethyl-PGF 2α and 3,16-dimethyl-PGF 1α are prepared by hydrolysing the corresponding 11,15-bis(tetrahydropyronyl) ethers. Compounds of the above formula in which X and Y both are -CH 2 CH 2 - are obtained by hydrogenating the corresponding compounds wherein X is -CH 2 CH 2 - or cis -CH=CH- and Y is trans -CH=CH-. The prostaglandin alcohols of the above formula are made by reducing the corresponding methyl esters, in which any carbonyl group present in in the cyclopentane ring is protected as an oximo group. Pharmaceutical compositions, suitable for oral, parenteral, rectal or vaginal administration, contain the novel prostaglandins of Formulµ V and XVIII together with pharmaceutical carriers or coatings. The compounds possess similar activities to the corresponding natural prostaglandins. Reference has been directed by the Comptroller to Specifications 1,198,071 and 1,282,661.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47093012A JPS4949963A (en) | 1972-09-16 | 1972-09-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1423664A true GB1423664A (en) | 1976-02-04 |
Family
ID=14070503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4324173A Expired GB1423664A (en) | 1972-09-16 | 1973-09-14 | Prostaglandin compounds |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4949963A (en) |
| AU (1) | AU6034273A (en) |
| BE (1) | BE804898A (en) |
| DE (1) | DE2346664A1 (en) |
| FR (1) | FR2199981B1 (en) |
| GB (1) | GB1423664A (en) |
| ZA (1) | ZA737328B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4026927A (en) * | 1973-09-25 | 1977-05-31 | Yamanouchi Pharmaceutical Co., Ltd. | Novel prostaglandin derivatives |
| US4058665A (en) * | 1975-11-06 | 1977-11-15 | Yamanouchi Pharmaceutical Co., Ltd. | Novel 3,15-dilower alkyl PGE2 derivatives |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA72713B (en) * | 1971-02-26 | 1972-10-25 | Ici Ltd | Cyclopentane derivatives |
| FR2134673A1 (en) * | 1971-04-30 | 1972-12-08 | Ono Pharmaceutical Co | Novel optically active isomers of prostaglandin analoguesof natural configuration useful as hypotensive agents, diuretics,contraceptives, for treating gastric ulcer and asthma, and forinhibiting platelet aggregation |
| JPS4864073A (en) * | 1971-04-30 | 1973-09-05 |
-
1972
- 1972-09-16 JP JP47093012A patent/JPS4949963A/ja active Pending
-
1973
- 1973-09-14 FR FR7333077A patent/FR2199981B1/fr not_active Expired
- 1973-09-14 GB GB4324173A patent/GB1423664A/en not_active Expired
- 1973-09-14 BE BE135690A patent/BE804898A/en unknown
- 1973-09-14 ZA ZA737328*A patent/ZA737328B/en unknown
- 1973-09-14 AU AU60342/73A patent/AU6034273A/en not_active Expired
- 1973-09-17 DE DE19732346664 patent/DE2346664A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2199981A1 (en) | 1974-04-19 |
| ZA737328B (en) | 1974-08-28 |
| JPS4949963A (en) | 1974-05-15 |
| AU6034273A (en) | 1975-03-20 |
| FR2199981B1 (en) | 1977-07-15 |
| DE2346664A1 (en) | 1974-04-11 |
| BE804898A (en) | 1974-03-14 |
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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 |