GB1506755A - Pharmaceutically useful prostenoic acid derivatives - Google Patents
Pharmaceutically useful prostenoic acid derivativesInfo
- Publication number
- GB1506755A GB1506755A GB21845/75A GB2184575A GB1506755A GB 1506755 A GB1506755 A GB 1506755A GB 21845/75 A GB21845/75 A GB 21845/75A GB 2184575 A GB2184575 A GB 2184575A GB 1506755 A GB1506755 A GB 1506755A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- hydroxymethyl
- oxo
- reacting
- ethyl
- 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
- NNOJWZIBHANBJD-OALUTQOASA-N 7-[(1S,2S)-2-octylcyclopentyl]hept-2-enoic acid Chemical class CCCCCCCC[C@H]1CCC[C@@H]1CCCCC=CC(O)=O NNOJWZIBHANBJD-OALUTQOASA-N 0.000 title 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 6
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 4
- 150000003180 prostaglandins Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- -1 5,5 - ethylenedioxy Chemical group 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentane carboxylic acid Natural products OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 230000000026 anti-ulcerogenic effect Effects 0.000 abstract 1
- 125000006243 carbonyl protecting group Chemical group 0.000 abstract 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical class O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- VMIBXGDYRRTQMO-UHFFFAOYSA-N ethyl 7-iodoheptanoate Chemical compound CCOC(=O)CCCCCCI VMIBXGDYRRTQMO-UHFFFAOYSA-N 0.000 abstract 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 150000002596 lactones Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1506755 Prostaglandins SANKYO CO Ltd 21 May 1975 21845/75 Heading C2C The invention comprises prostaglandins of the Formula I wherein R<SP>2</SP> and R<SP>3</SP> each are C 1-4 alkyl and R<SP>4</SP> is H or C 1-4 alkyl and pharmaceutically acceptable salts thereof where R<SP>4</SP> is H, and their preparation. The prostaglandins are obtained by removing the carbonyl protecting groups from compounds of the Formula II which are made by reducing the corresponding 15-oxo compounds, resulting from the reaction between compounds of the formula with the appropriate cyclopentanecarboxaldehydes. Methyl 7-(5,5 - ethylenedioxy - 2# - formyl - 3α- methyl - 1α - cyclopentyl)heptanoate is prepared by oxidizing methyl 7 - (5,5 - ethylenedioxy - 2#- hydroxymethyl - 3α - methyl - 1α - cyclopentyl) heptanoate, resulting from the reaction between ethylene glycol and methyl 7 - (2# - hydroxymethyl - 3α - methyl - 5 - oxo - 1α - cyclopentyl) heptanoate, which is obtained by treating 2# - hydroxymethyl - 1α - (6 - methoxycarbonylhexyl) - 3α - methyl - 5 - oxo - 1# - cyclopentanecarboxylic acid γ-lactone with bases, the lactone being obtained by reacting ethyl 7-iodoheptanoate with 2# - hydroxymethyl - 3α - methyl - 5- oxo - 1# - cyclopentanecarboxylic acid γ-lactone, resulting from reacting potassium t-butoxide with 3# - ethoxycarbonyloxymethyl - 4α - methylcyclopentan - 1 - one, which is prepared by hydrolysing 3# - ethoxycarbonyloxymethyl - 4α- methylcyclopentan - 1 - one ethylene acetal, obtained by reacting ethyl chloroformate with 3# - hydroxymethyl - 4α - methylcyclopentan- 1 - one ethylene acetal, the latter being obtained by reducing ethyl 8α-methyl-1,4-dioxaspiro[4,4]nonane - 7# - carboxylate, which is prepared by reacting sodium ethoxide with ethyl 8α - methyl - 1,4 - dioxospiro[4,4]nonone - 7α- carboxylate, obtained by reacting ethylene glycol with ethyl 2α - methyl - 4 - oxo - 1α - cyolopentanecarboxylate, which is prepared by treating 2#- methoxycarbonyl - 3α - methyl - 4α - ethoxycarbonylcyclopentanone with sodium iodide and glacial acetic acid. Pharmaceutical compositions, suitable for oral and parenteral administration, contain the above prostaglandins or salts thereof together with pharmaceutical carriers or diluents. The compounds possess anti-ulcerogenic activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21845/75A GB1506755A (en) | 1975-05-21 | 1975-05-21 | Pharmaceutically useful prostenoic acid derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB21845/75A GB1506755A (en) | 1975-05-21 | 1975-05-21 | Pharmaceutically useful prostenoic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1506755A true GB1506755A (en) | 1978-04-12 |
Family
ID=10169784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB21845/75A Expired GB1506755A (en) | 1975-05-21 | 1975-05-21 | Pharmaceutically useful prostenoic acid derivatives |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1506755A (en) |
-
1975
- 1975-05-21 GB GB21845/75A patent/GB1506755A/en not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 49R | Reference inserted (sect. 9/1949) | ||
| PS | Patent sealed | ||
| SP | Amendment (slips) printed | ||
| PCNP | Patent ceased through non-payment of renewal fee |