FR2346003A1 - 9-Oxo-11-alpha methyl prosta-13-enoic acid derivs - as selective anti-ulcer agents without hypotensive or intestinal-contracting side effects - Google Patents
9-Oxo-11-alpha methyl prosta-13-enoic acid derivs - as selective anti-ulcer agents without hypotensive or intestinal-contracting side effectsInfo
- Publication number
- FR2346003A1 FR2346003A1 FR7516321A FR7516321A FR2346003A1 FR 2346003 A1 FR2346003 A1 FR 2346003A1 FR 7516321 A FR7516321 A FR 7516321A FR 7516321 A FR7516321 A FR 7516321A FR 2346003 A1 FR2346003 A1 FR 2346003A1
- Authority
- FR
- France
- Prior art keywords
- oxo
- hypotensive
- intestinal
- side effects
- enoic acid
- 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.)
- Granted
Links
- 208000001953 Hypotension Diseases 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title abstract 2
- 239000003699 antiulcer agent Substances 0.000 title abstract 2
- 230000000694 effects Effects 0.000 title abstract 2
- 208000021822 hypotensive Diseases 0.000 title abstract 2
- 230000001077 hypotensive effect Effects 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- NNOJWZIBHANBJD-OALUTQOASA-N 7-[(1S,2S)-2-octylcyclopentyl]hept-2-enoic acid Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCC=CC(O)=O NNOJWZIBHANBJD-OALUTQOASA-N 0.000 abstract 1
- 208000025865 Ulcer Diseases 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 231100000397 ulcer Toxicity 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Prostenoic acid derivs. of formula (I) and their pharmaceutically acceptable salts are new: (where A = 4-8 C alkylene, esp. hexamethylene; R1 = 1-5C alkyl, esp. n-propyl; R2 and R3 are H or 1-4 C alkyl; R4 = H or 1-4 C alkyl). They are prepd. from corresp. 9-(protected oxo)-15-oxo cpd. by redn. then deprotection. (I) are anti-ulcer agents with little or no hypotensive or intestinal-contracting side effects. Thus, in the rat, 9-oxo-11 alpha 16, 16-trimethyl-15 alpha-hydroxyprost-13-trans-enoic acid has ED50 against indomethacin-(30 mg./kg.) induced ulcer of 0.16 mg./kg. Usual dose is 0.5-100 mg./day for adults e.g., as 3-4 tablets.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7516321A FR2346003A1 (en) | 1975-05-26 | 1975-05-26 | 9-Oxo-11-alpha methyl prosta-13-enoic acid derivs - as selective anti-ulcer agents without hypotensive or intestinal-contracting side effects |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7516321A FR2346003A1 (en) | 1975-05-26 | 1975-05-26 | 9-Oxo-11-alpha methyl prosta-13-enoic acid derivs - as selective anti-ulcer agents without hypotensive or intestinal-contracting side effects |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2346003A1 true FR2346003A1 (en) | 1977-10-28 |
| FR2346003B1 FR2346003B1 (en) | 1978-11-03 |
Family
ID=9155666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7516321A Granted FR2346003A1 (en) | 1975-05-26 | 1975-05-26 | 9-Oxo-11-alpha methyl prosta-13-enoic acid derivs - as selective anti-ulcer agents without hypotensive or intestinal-contracting side effects |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2346003A1 (en) |
-
1975
- 1975-05-26 FR FR7516321A patent/FR2346003A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2346003B1 (en) | 1978-11-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |