GB1139332A - Substituted phenylacetic acids and processes for their production - Google Patents
Substituted phenylacetic acids and processes for their productionInfo
- Publication number
- GB1139332A GB1139332A GB15497/66A GB1549766A GB1139332A GB 1139332 A GB1139332 A GB 1139332A GB 15497/66 A GB15497/66 A GB 15497/66A GB 1549766 A GB1549766 A GB 1549766A GB 1139332 A GB1139332 A GB 1139332A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- alkyl
- compounds
- radical
- formula
- 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
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 title 1
- -1 alkoxy radical Chemical class 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 3
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical class C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 2
- 150000008061 acetanilides Chemical class 0.000 abstract 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 2
- 239000012346 acetyl chloride Substances 0.000 abstract 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 abstract 2
- ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical class OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 239000012279 sodium borohydride Substances 0.000 abstract 2
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- GRIXINIGTYIHSN-UHFFFAOYSA-N 2-chloro-n,n-diphenylacetamide Chemical class C=1C=CC=CC=1N(C(=O)CCl)C1=CC=CC=C1 GRIXINIGTYIHSN-UHFFFAOYSA-N 0.000 abstract 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 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
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 150000001350 alkyl halides Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001448 anilines Chemical class 0.000 abstract 1
- 239000003125 aqueous solvent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009835 boiling Methods 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 230000000911 decarboxylating effect Effects 0.000 abstract 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 abstract 1
- ZWJINEZUASEZBH-UHFFFAOYSA-N fenamic acid Chemical class OC(=O)C1=CC=CC=C1NC1=CC=CC=C1 ZWJINEZUASEZBH-UHFFFAOYSA-N 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 150000007529 inorganic bases Chemical class 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- FZERHIULMFGESH-UHFFFAOYSA-N methylenecarboxanilide Natural products CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 1
- OSDZHDOKXGSWOD-UHFFFAOYSA-N nitroxyl;hydrochloride Chemical class Cl.O=N OSDZHDOKXGSWOD-UHFFFAOYSA-N 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH496165A CH460804A (de) | 1965-04-08 | 1965-04-08 | Verfahren zur Herstellung von neuen substituierten Phenylessigsäuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1139332A true GB1139332A (en) | 1969-01-08 |
Family
ID=4285534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB15497/66A Expired GB1139332A (en) | 1965-04-08 | 1966-04-07 | Substituted phenylacetic acids and processes for their production |
Country Status (16)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124077A (en) * | 1982-05-11 | 1984-02-15 | Mitsubishi Chem Ind | Immunomodulating agent |
| EP0400558A3 (en) * | 1989-05-29 | 1992-03-04 | Laboratorios Vinas S.A. | Phenylacetic acid derivative |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| US5347036A (en) * | 1985-07-22 | 1994-09-13 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| WO2001003684A3 (en) * | 1999-07-08 | 2002-06-06 | Exocell Inc | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
| US8362294B2 (en) | 2006-06-26 | 2013-01-29 | Novartis Ag | Phenylacetic acid derivatives |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3513199A (en) * | 1967-05-05 | 1970-05-19 | Smithkline Corp | Substituted anilino benzyl alcohols |
| CH506480A (de) * | 1969-02-20 | 1971-04-30 | Ciba Geigy Ag | Verfahren zur Herstellung von neuen, substituierten o-Anilino-phenäthylalkoholen |
| JPS549240A (en) * | 1977-06-23 | 1979-01-24 | Asahi Chem Ind Co Ltd | New derivative of phenylglycolic acid, its preparation and analgesic and antiinflammatory agent contining it as effective component |
| DE3623193A1 (de) * | 1986-07-10 | 1988-01-14 | Gruenenthal Gmbh | Neue verbindungen, diese enthaltende arzneimittel und verfahren zu deren herstellung |
| EP0405602A1 (en) * | 1989-06-30 | 1991-01-02 | Laboratorios Vinas S.A. | New Zinc derivatives of anti-inflammatory drugs having improved therapeutic activity |
| IT1256345B (it) * | 1992-08-20 | 1995-12-01 | Esteri nitrici di derivati dell'acido 2-(2,6-di-alo-fenilammino) fenilacetico e procedimento per la loro preparazione | |
| CN114539086B (zh) | 2022-02-25 | 2023-10-03 | 复旦大学 | 一种双氯芬酸钠的合成方法 |
| CN114516813B (zh) | 2022-02-25 | 2024-05-28 | 复旦大学 | 一种双氯芬酸钠的连续流制备方法 |
-
0
- NL NL133740D patent/NL133740C/xx active
-
1965
- 1965-04-08 CH CH496165A patent/CH460804A/de unknown
- 1965-04-08 FR FR57111A patent/FR1487352A/fr not_active Expired
-
1966
- 1966-04-06 DK DK180566AA patent/DK117639B/da unknown
- 1966-04-06 NO NO162524A patent/NO120793B/no unknown
- 1966-04-06 FI FI660898A patent/FI44619C/fi active
- 1966-04-06 ES ES0325270A patent/ES325270A1/es not_active Expired
- 1966-04-06 ES ES0325271A patent/ES325271A1/es not_active Expired
- 1966-04-07 NL NL6604752A patent/NL6604752A/xx unknown
- 1966-04-07 AT AT619767A patent/AT266096B/de active
- 1966-04-07 AT AT619567A patent/AT262982B/de active
- 1966-04-07 AT AT334966A patent/AT263755B/de active
- 1966-04-07 IL IL25545A patent/IL25545A/en unknown
- 1966-04-07 DE DE1966G0046553 patent/DE1543639B2/de active Granted
- 1966-04-07 AT AT619667A patent/AT262983B/de active
- 1966-04-07 SE SE4833/66A patent/SE322527B/xx unknown
- 1966-04-07 GB GB15497/66A patent/GB1139332A/en not_active Expired
- 1966-04-08 BE BE679315D patent/BE679315A/xx not_active IP Right Cessation
- 1966-07-06 FR FR68443A patent/FR5524M/fr not_active Expired
-
1972
- 1972-04-19 CY CY63772A patent/CY637A/xx unknown
- 1972-12-31 MY MY1972118A patent/MY7200118A/xx unknown
-
1977
- 1977-11-21 DO DO1977002615A patent/DOP1977002615A/es unknown
- 1977-12-09 DO DO1977002614A patent/DOP1977002614A/es unknown
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2124077A (en) * | 1982-05-11 | 1984-02-15 | Mitsubishi Chem Ind | Immunomodulating agent |
| US5237070A (en) * | 1985-07-22 | 1993-08-17 | Riker Laboratories, Inc. | Substituted DI-t-butylphenols |
| US5347036A (en) * | 1985-07-22 | 1994-09-13 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| US5416113A (en) * | 1985-07-22 | 1995-05-16 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| US5495043A (en) * | 1985-07-22 | 1996-02-27 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| US5498745A (en) * | 1985-07-22 | 1996-03-12 | Riker Laboratories, Inc. | Substituted di-t-butylphenols |
| US5527824A (en) * | 1985-07-22 | 1996-06-18 | Riker Laboratories, Inc. | Substituted Di-T-Butlyphenols useful for inhibiting leukotriene synthesis |
| EP0400558A3 (en) * | 1989-05-29 | 1992-03-04 | Laboratorios Vinas S.A. | Phenylacetic acid derivative |
| US6552077B2 (en) | 1996-02-20 | 2003-04-22 | Exocell, Inc. | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
| WO2001003684A3 (en) * | 1999-07-08 | 2002-06-06 | Exocell Inc | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies |
| US8362294B2 (en) | 2006-06-26 | 2013-01-29 | Novartis Ag | Phenylacetic acid derivatives |
| US8586782B2 (en) | 2006-06-26 | 2013-11-19 | Novartis Ag | Phenylacetic acid derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| ES325270A1 (es) | 1967-04-01 |
| BE679315A (enrdf_load_stackoverflow) | 1966-10-10 |
| AT266096B (de) | 1968-11-11 |
| NO120793B (enrdf_load_stackoverflow) | 1970-12-07 |
| DOP1977002614A (es) | 1983-05-27 |
| CH460804A (de) | 1968-08-15 |
| DE1793592B2 (de) | 1977-06-16 |
| IL25545A (en) | 1970-07-19 |
| DE1543639A1 (de) | 1970-02-05 |
| MY7200118A (en) | 1972-12-31 |
| NL6604752A (enrdf_load_stackoverflow) | 1966-10-10 |
| DK117639B (da) | 1970-05-19 |
| FI44619C (fi) | 1971-12-10 |
| AT262983B (de) | 1968-07-10 |
| AT263755B (de) | 1968-08-12 |
| DOP1977002615A (es) | 1983-05-27 |
| FR5524M (enrdf_load_stackoverflow) | 1967-11-06 |
| DE1543639B2 (de) | 1977-02-24 |
| SE322527B (enrdf_load_stackoverflow) | 1970-04-13 |
| FR1487352A (fr) | 1967-07-07 |
| NL133740C (enrdf_load_stackoverflow) | |
| ES325271A1 (es) | 1967-04-01 |
| DE1793592A1 (de) | 1972-04-20 |
| CY637A (en) | 1972-04-19 |
| AT262982B (de) | 1968-07-10 |
| FI44619B (enrdf_load_stackoverflow) | 1971-08-31 |
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