GB1310606A - Adamantylcarboxamidophenylacetic acid derivatives their preparation and compositions containing them - Google Patents
Adamantylcarboxamidophenylacetic acid derivatives their preparation and compositions containing themInfo
- Publication number
- GB1310606A GB1310606A GB1446170A GB1446170A GB1310606A GB 1310606 A GB1310606 A GB 1310606A GB 1446170 A GB1446170 A GB 1446170A GB 1446170 A GB1446170 A GB 1446170A GB 1310606 A GB1310606 A GB 1310606A
- Authority
- GB
- United Kingdom
- Prior art keywords
- nitro
- prepared
- acid
- hydrogen atom
- methyl
- 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
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Manufacture And Refinement Of Metals (AREA)
Abstract
1310606 2 - (1 - Adamantylcarboxamido)- phenylacetic acids CIBA-GEIGY AG 25 March 1970 [26 March 1969] 14461/70 Heading C2C Novel 2 - (1 - adamantylcarboxamido)- phenylacetic acids of the general formula wherein one of R 1 and R 2 is a hydrogen, fluorine, chlorine or bromine atom or a C 1-4 alkyl, C 1-4 alkoxy or trifluoromethyl group and the other is a hydrogen atom, or both R 1 and R 2 are C 1-4 alkoxy groups, and R 3 and R 4 are each a hydrogen atom or a C 1-4 alkyl group, and, when R 4 is a hydrogen atom in said formula, pharmaceutically acceptable salts thereof with bases are prepared by reaction of a 2-amino-phenylacetic acid of the general formula with an acylating agent containing a 1-adamantyl-carbonyl group and, when in the product R 4 is a hydrogen atom, optional esterification or salification of the product, or, when in the product R 4 is a C 1-4 alkyl group, optional hydrolysis of the product to give the corresponding free acid or a salt thereof, the latter optionally being converted to the free acid. 2 - Amino - phenylacetic acid esters of the second general formula above wherein R 4 is a C 1-4 alkyl group are prepared by esterification of the corresponding 2-nitro-phenylacetic acid and reduction of the resulting 2-nitro-phenylacetic acid ester. Methyl 2-(2-nitro-4-trifluoromethylphenyl)propionate is prepared by reaction of methyl 2-nitro-4-trifluoromethylphenylacetate with methyl iodide in the presence of sodium hydride. Methyl 2-(2-nitro-4-trifluoromethylphenyl)-hexanoate is prepared analogously from 1 - bromo - n - butane. 4 - Methyl - 2 - nitrophenylacetic acid is prepared by reaction of 3- nitro-4-chlorotoluene with diethyl malonate in the presence of sodium, followed by ethanolic potassium hydroxide solution. 5 - Fluoro - 2- nitrophenylacetic acid is prepared by acid hydrolysis of 5-fluoro-2-nitrophenylacetonitrile. Pharmaceutical compositions having antiinflammatory activity comprise, as active ingredient, a 2 - (1 - adamantylcarboxamido)- phenylacetic acid of the first general formula above or, when R 4 is a hydrogen atom in said formula, a pharmaceutically acceptable salt thereof with a base, together with a pharmaceutically acceptable diluent or carrier therefor, and may be administered orally.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US81082869A | 1969-03-26 | 1969-03-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1310606A true GB1310606A (en) | 1973-03-21 |
Family
ID=25204813
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1446170A Expired GB1310606A (en) | 1969-03-26 | 1970-03-25 | Adamantylcarboxamidophenylacetic acid derivatives their preparation and compositions containing them |
Country Status (17)
Country | Link |
---|---|
JP (1) | JPS4826004B1 (en) |
AT (1) | AT293369B (en) |
BE (1) | BE747948A (en) |
BG (1) | BG17524A3 (en) |
BR (1) | BR7017762D0 (en) |
CH (1) | CH529107A (en) |
DE (1) | DE2014506A1 (en) |
DK (1) | DK124024B (en) |
ES (1) | ES377921A1 (en) |
FR (1) | FR2035904B1 (en) |
GB (1) | GB1310606A (en) |
IE (1) | IE33762B1 (en) |
IL (1) | IL34158A (en) |
NL (1) | NL7003946A (en) |
NO (1) | NO129346B (en) |
PL (1) | PL87285B1 (en) |
SE (1) | SE365507B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS60152331U (en) * | 1984-03-14 | 1985-10-09 | レンゴ−株式会社 | desk |
JPS6131224U (en) * | 1984-07-31 | 1986-02-25 | 株式会社 ムラタインテリアデザイン | table |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1113227A (en) * | 1965-06-24 | 1968-05-08 | Searle & Co | Adamantanecarboxylic acid derivatives |
-
1970
- 1970-03-19 SE SE03719/70A patent/SE365507B/xx unknown
- 1970-03-19 NO NO01028/70A patent/NO129346B/no unknown
- 1970-03-19 DK DK137870AA patent/DK124024B/en unknown
- 1970-03-19 NL NL7003946A patent/NL7003946A/xx unknown
- 1970-03-20 DE DE19702014506 patent/DE2014506A1/de active Pending
- 1970-03-25 CH CH449770A patent/CH529107A/en not_active IP Right Cessation
- 1970-03-25 BE BE747948D patent/BE747948A/en unknown
- 1970-03-25 PL PL1970139589A patent/PL87285B1/pl unknown
- 1970-03-25 AT AT277570A patent/AT293369B/en not_active IP Right Cessation
- 1970-03-25 BR BR217762/70A patent/BR7017762D0/en unknown
- 1970-03-25 BG BG014274A patent/BG17524A3/en unknown
- 1970-03-25 IE IE375/70A patent/IE33762B1/en unknown
- 1970-03-25 JP JP45024535A patent/JPS4826004B1/ja active Pending
- 1970-03-25 ES ES377921A patent/ES377921A1/en not_active Expired
- 1970-03-25 IL IL34158A patent/IL34158A/en unknown
- 1970-03-25 FR FR7010714A patent/FR2035904B1/fr not_active Expired
- 1970-03-25 GB GB1446170A patent/GB1310606A/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
PL87285B1 (en) | 1976-06-30 |
DK124024B (en) | 1972-09-04 |
BE747948A (en) | 1970-09-25 |
IL34158A0 (en) | 1970-05-21 |
DE2014506A1 (en) | 1970-10-01 |
CH529107A (en) | 1972-10-15 |
SE365507B (en) | 1974-03-25 |
BR7017762D0 (en) | 1973-02-13 |
IL34158A (en) | 1974-01-14 |
AT293369B (en) | 1971-10-11 |
IE33762L (en) | 1970-09-26 |
FR2035904B1 (en) | 1974-01-11 |
IE33762B1 (en) | 1974-10-16 |
JPS4826004B1 (en) | 1973-08-03 |
ES377921A1 (en) | 1972-10-16 |
NO129346B (en) | 1974-04-01 |
NL7003946A (en) | 1970-09-29 |
BG17524A3 (en) | 1973-11-10 |
FR2035904A1 (en) | 1970-12-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PLNP | Patent lapsed through nonpayment of renewal fees |