IE35531B1 - Alpha-phenoxyalkanoic acids and derivatives thereof - Google Patents
Alpha-phenoxyalkanoic acids and derivatives thereofInfo
- Publication number
- IE35531B1 IE35531B1 IE770/71A IE77071A IE35531B1 IE 35531 B1 IE35531 B1 IE 35531B1 IE 770/71 A IE770/71 A IE 770/71A IE 77071 A IE77071 A IE 77071A IE 35531 B1 IE35531 B1 IE 35531B1
- Authority
- IE
- Ireland
- Prior art keywords
- residue
- substituted
- anisole
- carbon atom
- cyclo
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 2
- 150000007513 acids Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001408 amides Chemical group 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical group 0.000 abstract 2
- FLYAGGNZYBWGJK-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclohexan-1-ol Chemical compound C1=CC(OC)=CC=C1C1(O)CCCCC1 FLYAGGNZYBWGJK-UHFFFAOYSA-N 0.000 abstract 1
- ARPAWHNHIRNOOK-UHFFFAOYSA-N 1-(4-methoxyphenyl)cyclooctene Chemical compound C1=CC(OC)=CC=C1C1=CCCCCCC1 ARPAWHNHIRNOOK-UHFFFAOYSA-N 0.000 abstract 1
- UQWCOLCOFGGALX-UHFFFAOYSA-N 1-(cyclohexen-1-yl)-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C1=CCCCC1 UQWCOLCOFGGALX-UHFFFAOYSA-N 0.000 abstract 1
- JWEJZKHMUMYMHS-UHFFFAOYSA-N 2-(cycloocten-1-yl)phenol Chemical compound C1(=CCCCCCC1)C1=C(C=CC=C1)O JWEJZKHMUMYMHS-UHFFFAOYSA-N 0.000 abstract 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 abstract 1
- 238000003747 Grignard reaction Methods 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000003839 salts Chemical class 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Rigid Containers With Two Or More Constituent Elements (AREA)
- Butt Welding And Welding Of Specific Article (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1353362 α-Phenoxyacetic acids CIBAGEIGY AG 17 June 1971 [10 Dec 1970 5 Feb 1971 7 May 1971] 28455/71 Addition to 1332824 Heading C2C Novel α-phenoxyacetic acids in which the α-position is substituted by an alkyl residue having 5 to 12 carbon atoms and the phenyl residue is substituted by a singly unsaturated cycloalkenyl residue the double bond of which extend from the carbon atom adjacent to the phenyl residue to an adjacent carbon atom, or an ester or amide thereof may be prepared by condensation of a phenol that is substituted by a singly unsaturated cycloalkenyl residue the double bond of which extend from the carbon atom adjacent to the phenyl residue to an adjacent carbon atom, with an ester of a glycolic acid that is reactively esterified at the alcoholic hydroxyl group and is substituted in the α- position by a C 5-12 alkyl residue and, if desired, forming a free acid, an amide or a salt thereof or resolving isomers. The intermediates p-(1-cyclohexenyl) and (1- cyclo-octenyl)-phenol may be prepared by forming a Grignard reagent with p-bromo anisole, reacting it with cyclohexanone or cyclo-octanone, followed by dehydration of p-(1-hydroxycyclohexyl) anisole to p-(1-cyclohexenyl)-anisole (p-(1-cyclo-octenyl)-anisole is formed directly as the product of the Grignard reaction), followed by demethylation to form the free phenol. Pharmaceutical compositions of the α-phenoxyacetic acids have a serum-lipid-lowering action when administered orally, parenterally or rectally with the usual excipients.
[GB1353362A]
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1836270A CH563327A5 (en) | 1970-12-10 | 1970-12-10 | Alpha-alkyl-alpha(1-cycloalkenyl)-phenoxy acetic acid derivs - hypoli - intermediates |
| CH173071 | 1971-02-05 | ||
| CH674871A CH575900A5 (en) | 1971-05-07 | 1971-05-07 | Alpha-alkyl-alpha(1-cycloalkenyl)-phenoxy acetic acid derivs - hypoli - intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE35531L IE35531L (en) | 1972-06-10 |
| IE35531B1 true IE35531B1 (en) | 1976-03-18 |
Family
ID=27173204
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE770/71A IE35531B1 (en) | 1970-12-10 | 1971-06-15 | Alpha-phenoxyalkanoic acids and derivatives thereof |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS53130641A (en) |
| AR (6) | AR203613A1 (en) |
| BE (1) | BE768579R (en) |
| CA (1) | CA1008875A (en) |
| CS (4) | CS176197B2 (en) |
| DD (1) | DD99154A6 (en) |
| DE (1) | DE2124796A1 (en) |
| DK (1) | DK133147C (en) |
| FI (1) | FI53811C (en) |
| FR (1) | FR2117832B2 (en) |
| GB (1) | GB1353362A (en) |
| HU (1) | HU168743B (en) |
| IE (1) | IE35531B1 (en) |
| IL (1) | IL37037A (en) |
| NL (1) | NL7107421A (en) |
| NO (1) | NO130642C (en) |
| SE (1) | SE384204B (en) |
-
1971
- 1971-05-14 FI FI1335/71A patent/FI53811C/en active
- 1971-05-14 DK DK235571A patent/DK133147C/en active
- 1971-05-18 SE SE7106434A patent/SE384204B/en unknown
- 1971-05-19 DE DE19712124796 patent/DE2124796A1/en active Pending
- 1971-05-24 DD DD155307A patent/DD99154A6/xx unknown
- 1971-05-24 HU HUCI1115A patent/HU168743B/hu unknown
- 1971-05-28 NL NL7107421A patent/NL7107421A/xx unknown
- 1971-05-31 CS CS3430A patent/CS176197B2/cs unknown
- 1971-05-31 CS CS3428A patent/CS176195B2/cs unknown
- 1971-05-31 CS CS3427A patent/CS176194B2/cs unknown
- 1971-06-02 NO NO2070/71A patent/NO130642C/no unknown
- 1971-06-11 AR AR236137A patent/AR203613A1/en active
- 1971-06-13 IL IL37037A patent/IL37037A/en unknown
- 1971-06-14 CA CA115,513A patent/CA1008875A/en not_active Expired
- 1971-06-15 IE IE770/71A patent/IE35531B1/en unknown
- 1971-06-16 BE BE768579A patent/BE768579R/en active
- 1971-06-17 FR FR7122009A patent/FR2117832B2/fr not_active Expired
- 1971-06-17 GB GB2845571A patent/GB1353362A/en not_active Expired
-
1973
- 1973-01-01 AR AR250398A patent/AR205332A1/en active
- 1973-01-01 AR AR250400A patent/AR205527A1/en active
- 1973-01-01 AR AR250399A patent/AR205526A1/en active
- 1973-10-05 AR AR250396A patent/AR203629A1/en active
- 1973-10-05 AR AR250397A patent/AR209265A1/en active
-
1975
- 1975-05-31 CS CS3426A patent/CS176193B2/cs unknown
-
1978
- 1978-04-12 JP JP4224578A patent/JPS53130641A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CS176195B2 (en) | 1977-06-30 |
| DD99154A6 (en) | 1973-07-20 |
| CA1008875A (en) | 1977-04-19 |
| AR203613A1 (en) | 1975-09-30 |
| AR209265A1 (en) | 1977-04-15 |
| FI53811B (en) | 1978-05-02 |
| NO130642B (en) | 1974-10-07 |
| AR203629A1 (en) | 1975-09-30 |
| SE384204B (en) | 1976-04-26 |
| FR2117832A2 (en) | 1972-07-28 |
| FI53811C (en) | 1978-08-10 |
| IL37037A0 (en) | 1971-08-25 |
| JPS53130641A (en) | 1978-11-14 |
| CS176194B2 (en) | 1977-06-30 |
| AR205332A1 (en) | 1976-04-30 |
| DE2124796A1 (en) | 1972-06-29 |
| AR205526A1 (en) | 1976-05-14 |
| CS176197B2 (en) | 1977-06-30 |
| FR2117832B2 (en) | 1977-02-04 |
| IE35531L (en) | 1972-06-10 |
| BE768579R (en) | 1971-12-16 |
| DK133147B (en) | 1976-03-29 |
| AR205527A1 (en) | 1976-05-14 |
| DK133147C (en) | 1976-08-30 |
| NO130642C (en) | 1975-01-15 |
| HU168743B (en) | 1976-07-28 |
| GB1353362A (en) | 1974-05-15 |
| IL37037A (en) | 1974-06-30 |
| NL7107421A (en) | 1972-06-13 |
| CS176193B2 (en) | 1977-06-30 |
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