IE33762L - Adamantylcarboxamidophenylacetic acid derivatives - Google Patents
Adamantylcarboxamidophenylacetic acid derivativesInfo
- Publication number
- IE33762L IE33762L IE700375A IE37570A IE33762L IE 33762 L IE33762 L IE 33762L IE 700375 A IE700375 A IE 700375A IE 37570 A IE37570 A IE 37570A IE 33762 L IE33762 L IE 33762L
- Authority
- IE
- Ireland
- Prior art keywords
- nitro
- prepared
- acid
- hydrogen atom
- methyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- -1 1-adamantyl-carbonyl group Chemical group 0.000 abstract 2
- KHMNCHDUSFCTGK-UHFFFAOYSA-N 2-aminophenylacetic acid Chemical compound NC1=CC=CC=C1CC(O)=O KHMNCHDUSFCTGK-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 230000032050 esterification Effects 0.000 abstract 2
- 238000005886 esterification reaction Methods 0.000 abstract 2
- WMUZDBZPDLHUMW-UHFFFAOYSA-N (2-nitrophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC=C1[N+]([O-])=O WMUZDBZPDLHUMW-UHFFFAOYSA-N 0.000 abstract 1
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 abstract 1
- NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- DXXWGXHJDCZCSN-UHFFFAOYSA-N 2-(4-methyl-2-nitrophenyl)acetic acid Chemical compound CC1=CC=C(CC(O)=O)C([N+]([O-])=O)=C1 DXXWGXHJDCZCSN-UHFFFAOYSA-N 0.000 abstract 1
- YETOJTGGLXHUCS-UHFFFAOYSA-N 2-(5-fluoro-2-nitrophenyl)acetonitrile Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1CC#N YETOJTGGLXHUCS-UHFFFAOYSA-N 0.000 abstract 1
- HOWBVGXZCYNPOU-UHFFFAOYSA-N 29640-98-0 Chemical compound OC(=O)CC1=CC(F)=CC=C1[N+]([O-])=O HOWBVGXZCYNPOU-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 abstract 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- WFQOIJIXNFOYCM-UHFFFAOYSA-N methyl 2-[2-nitro-4-(trifluoromethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=C(C(F)(F)F)C=C1[N+]([O-])=O WFQOIJIXNFOYCM-UHFFFAOYSA-N 0.000 abstract 1
- QFRKBSWZBHKADY-UHFFFAOYSA-N methyl 2-[2-nitro-4-(trifluoromethyl)phenyl]hexanoate Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)C(F)(F)F)C(C(=O)OC)CCCC QFRKBSWZBHKADY-UHFFFAOYSA-N 0.000 abstract 1
- HJIWZFAZVDZZNB-UHFFFAOYSA-N methyl 2-[2-nitro-4-(trifluoromethyl)phenyl]propanoate Chemical compound [N+](=O)([O-])C1=C(C=CC(=C1)C(F)(F)F)C(C(=O)OC)C HJIWZFAZVDZZNB-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229960003424 phenylacetic acid Drugs 0.000 abstract 1
- 239000003279 phenylacetic acid Substances 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Rheumatology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (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.
[GB1310606A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81082869A | 1969-03-26 | 1969-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE33762L true IE33762L (en) | 1970-09-26 |
| IE33762B1 IE33762B1 (en) | 1974-10-16 |
Family
ID=25204813
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE375/70A IE33762B1 (en) | 1969-03-26 | 1970-03-25 | New 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 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
- 1970-03-19 SE SE03719/70A patent/SE365507B/xx unknown
- 1970-03-20 DE DE19702014506 patent/DE2014506A1/de active Pending
- 1970-03-25 GB GB1446170A patent/GB1310606A/en not_active Expired
- 1970-03-25 JP JP45024535A patent/JPS4826004B1/ja active Pending
- 1970-03-25 AT AT277570A patent/AT293369B/en not_active IP Right Cessation
- 1970-03-25 CH CH449770A patent/CH529107A/en not_active IP Right Cessation
- 1970-03-25 BG BG014274A patent/BG17524A3/en unknown
- 1970-03-25 BR BR217762/70A patent/BR7017762D0/en unknown
- 1970-03-25 ES ES377921A patent/ES377921A1/en not_active Expired
- 1970-03-25 PL PL1970139589A patent/PL87285B1/pl unknown
- 1970-03-25 IE IE375/70A patent/IE33762B1/en unknown
- 1970-03-25 FR FR7010714A patent/FR2035904B1/fr not_active Expired
- 1970-03-25 BE BE747948D patent/BE747948A/en unknown
- 1970-03-25 IL IL34158A patent/IL34158A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2035904A1 (en) | 1970-12-24 |
| JPS4826004B1 (en) | 1973-08-03 |
| ES377921A1 (en) | 1972-10-16 |
| PL87285B1 (en) | 1976-06-30 |
| CH529107A (en) | 1972-10-15 |
| BR7017762D0 (en) | 1973-02-13 |
| NL7003946A (en) | 1970-09-29 |
| NO129346B (en) | 1974-04-01 |
| IL34158A0 (en) | 1970-05-21 |
| BE747948A (en) | 1970-09-25 |
| AT293369B (en) | 1971-10-11 |
| SE365507B (en) | 1974-03-25 |
| BG17524A3 (en) | 1973-11-10 |
| DK124024B (en) | 1972-09-04 |
| DE2014506A1 (en) | 1970-10-01 |
| FR2035904B1 (en) | 1974-01-11 |
| GB1310606A (en) | 1973-03-21 |
| IE33762B1 (en) | 1974-10-16 |
| IL34158A (en) | 1974-01-14 |
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