IE35123B1 - Phenylalkane derivatives and processes for the preparation thereof - Google Patents
Phenylalkane derivatives and processes for the preparation thereofInfo
- Publication number
- IE35123B1 IE35123B1 IE430/71A IE43071A IE35123B1 IE 35123 B1 IE35123 B1 IE 35123B1 IE 430/71 A IE430/71 A IE 430/71A IE 43071 A IE43071 A IE 43071A IE 35123 B1 IE35123 B1 IE 35123B1
- Authority
- IE
- Ireland
- Prior art keywords
- general formula
- chlorine
- atom
- group
- chlorine atom
- Prior art date
Links
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 5
- 229910052801 chlorine Inorganic materials 0.000 abstract 4
- CWWCQGGNKDBSNT-UHFFFAOYSA-N 2-(2-phenoxyphenyl)acetic acid Chemical class OC(=O)CC1=CC=CC=C1OC1=CC=CC=C1 CWWCQGGNKDBSNT-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- VQJMAIZOEPPELO-KYGIZGOZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-(2-hydroxy-5-methylhexan-2-yl)-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol hydrochloride Chemical compound Cl.CO[C@]12CC[C@@]3(C[C@@H]1C(C)(O)CCC(C)C)[C@H]1Cc4ccc(O)c5O[C@@H]2[C@]3(CCN1CC1CC1)c45 VQJMAIZOEPPELO-KYGIZGOZSA-N 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- KPBCVVSDGJBODL-UHFFFAOYSA-N 1-(2-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OC1=CC=CC=C1 KPBCVVSDGJBODL-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- -1 alkali metal phenolate Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229910052802 copper Inorganic materials 0.000 abstract 1
- 239000010949 copper Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 229910052740 iodine Chemical group 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 229940031826 phenolate Drugs 0.000 abstract 1
- 125000005323 thioketone group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/807—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen all halogen atoms bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1308327 o - Phenoxyphenylacetic acids RECKITT & COLMAN PRODUCTS Ltd 19 April 1971 [14 April 1970] 17832/70 Heading C2C [Also in Division A5] Novel o-phenoxyphenylacetic acids of the general formula wherein R<SP>1</SP> is a hydrogen atom or methyl group, R<SP>2</SP> is a chlorine atom, R<SP>3</SP> is a C 1-6 alkyl group at position 4, a trifluoromethyl group at position 5, a methyl group at position 6 or a chlorine atom at position 4 or 5, and additionally compounds as defined above but wherein R<SP>2</SP> maybe a methoxy group when R<SP>3</SP> is a chlorine atom at position 4; and wherein one or more of the chlorine substituents is/are replaced by a bromine substituent are prepared by hydrolysis of a thioketone of the general formula They may be purified by conversion to the corresponding amide with thionyl chloride and ammonia, followed by alkaline hydrolysis. Thioketones of the second general formula above are prepared by reaction of an alkali metal phenolate and an o-haloacetophenone of the respective general formulµ wherein Y is ONa or OK and X is a chlorine, bromine or iodine atom, at a temperature of at least 120‹ C. in the presence of a copper catalyst and treatment of the resulting o-phenoxyacetophenone of the general formula with sulphur and morpholine.
[GB1308327A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1783270 | 1970-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35123L IE35123L (en) | 1971-10-14 |
| IE35123B1 true IE35123B1 (en) | 1975-11-12 |
Family
ID=10101999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE430/71A IE35123B1 (en) | 1970-04-14 | 1971-04-05 | Phenylalkane derivatives and processes for the preparation thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3766263A (en) |
| JP (1) | JPS536143B1 (en) |
| BE (1) | BE842952Q (en) |
| CA (1) | CA935438A (en) |
| FR (1) | FR2092044B1 (en) |
| GB (1) | GB1308327A (en) |
| HK (1) | HK51576A (en) |
| IE (1) | IE35123B1 (en) |
| KE (1) | KE2633A (en) |
| MY (1) | MY7600176A (en) |
| NL (1) | NL157006B (en) |
| SE (1) | SE372254B (en) |
| ZA (1) | ZA712345B (en) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2451140A1 (en) * | 1973-10-29 | 1975-04-30 | Eisai Co Ltd | M-PHENOXYPHENYLPROPIONIC ACID DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND COMPOUNDS CONTAINING THESE COMPOUNDS |
| CS181686B2 (en) * | 1974-01-14 | 1978-03-31 | Isf Spa | Process for preparing 4-cyclopropylmethylenoxy-3-chlorphenylacetic acid |
| US4065503A (en) * | 1974-09-30 | 1977-12-27 | Sandoz, Inc. | P-Phenoxy-alkylphenones and corresponding alcohols |
| GB2093021B (en) * | 1981-01-24 | 1985-10-02 | Reckitt & Colman Product Ltd | 2-(2,4-dichlorophenoxy) phenylacetic acid |
| US4430510A (en) | 1981-06-18 | 1984-02-07 | Schering Corporation | Process for the preparation of 2-(2,4-dichlorophenoxy)-phenylacetic acid |
| US4468469A (en) * | 1981-11-04 | 1984-08-28 | Miles Laboratories, Inc. | Substituted phenylacetic acids and salts as TBP blocking agents in iodothyronine immunoassays |
| JPS60103906U (en) * | 1983-12-20 | 1985-07-16 | 株式会社ヨコオ | antenna connection device |
| GB8715242D0 (en) * | 1987-06-29 | 1987-08-05 | Wood E M | Fenclofenac as immunosuppressant drug |
| US5145790A (en) * | 1990-05-04 | 1992-09-08 | Abbott Laboratories | Reagents and method for detecting polychlorinated biphenyls |
| AU659106B2 (en) * | 1990-11-06 | 1995-05-11 | Fgn, Inc. | Method for treating colonic polyps by the use of esters and amides of substituted phenyl and pyridyl amino carboxylates |
| US5538852A (en) * | 1992-10-02 | 1996-07-23 | Ecochem Research, Inc. | Immunoassay for polychlorinated biphenyls |
| US6544556B1 (en) | 2000-09-11 | 2003-04-08 | Andrx Corporation | Pharmaceutical formulations containing a non-steroidal antiinflammatory drug and a proton pump inhibitor |
| ITMI20012434A1 (en) * | 2001-11-20 | 2003-05-20 | Dompe Spa | 2-ARYL-PROPIONIC ACIDS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
| ES2418153T3 (en) | 2006-03-08 | 2013-08-12 | Cortria Corporation | Combination therapy with non-selective COX inhibitors to prevent gastric lesions related to COX |
-
1970
- 1970-04-14 GB GB1783270A patent/GB1308327A/en not_active Expired
-
1971
- 1971-04-05 IE IE430/71A patent/IE35123B1/en unknown
- 1971-04-08 CA CA109932A patent/CA935438A/en not_active Expired
- 1971-04-09 US US00132891A patent/US3766263A/en not_active Expired - Lifetime
- 1971-04-13 JP JP2340471A patent/JPS536143B1/ja active Pending
- 1971-04-13 NL NL7104884.A patent/NL157006B/en not_active IP Right Cessation
- 1971-04-13 SE SE7104757A patent/SE372254B/xx unknown
- 1971-04-13 ZA ZA712345A patent/ZA712345B/en unknown
- 1971-04-13 FR FR7112973A patent/FR2092044B1/fr not_active Expired
-
1976
- 1976-05-28 KE KE2633*UA patent/KE2633A/en unknown
- 1976-06-14 BE BE6045556A patent/BE842952Q/en not_active IP Right Cessation
- 1976-08-12 HK HK515/76*UA patent/HK51576A/en unknown
- 1976-12-31 MY MY1976176A patent/MY7600176A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK51576A (en) | 1976-08-20 |
| ZA712345B (en) | 1972-05-31 |
| KE2633A (en) | 1976-06-11 |
| US3766263A (en) | 1973-10-16 |
| DE2117826B2 (en) | 1975-11-20 |
| CA935438A (en) | 1973-10-16 |
| GB1308327A (en) | 1973-02-21 |
| MY7600176A (en) | 1976-12-31 |
| JPS536143B1 (en) | 1978-03-04 |
| NL157006B (en) | 1978-06-15 |
| BE842952Q (en) | 1976-10-01 |
| SE372254B (en) | 1974-12-16 |
| NL7104884A (en) | 1971-10-18 |
| IE35123L (en) | 1971-10-14 |
| FR2092044A1 (en) | 1972-01-21 |
| DE2117826A1 (en) | 1971-10-28 |
| FR2092044B1 (en) | 1975-08-01 |
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