IE34820B1 - Alpha-phenoxyacetic acids and derivatives thereof - Google Patents
Alpha-phenoxyacetic acids and derivatives thereofInfo
- Publication number
- IE34820B1 IE34820B1 IE160770A IE160770A IE34820B1 IE 34820 B1 IE34820 B1 IE 34820B1 IE 160770 A IE160770 A IE 160770A IE 160770 A IE160770 A IE 160770A IE 34820 B1 IE34820 B1 IE 34820B1
- Authority
- IE
- Ireland
- Prior art keywords
- cycloalkenyl
- residue
- substituted
- reacting
- polycyclic
- Prior art date
Links
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000002148 esters Chemical group 0.000 abstract 3
- 125000003367 polycyclic group Chemical group 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-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
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002950 monocyclic group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- HTDQSWDEWGSAMN-UHFFFAOYSA-N 1-bromo-2-methoxybenzene Chemical compound COC1=CC=CC=C1Br HTDQSWDEWGSAMN-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001299 aldehydes Chemical class 0.000 abstract 1
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 125000002843 carboxylic acid group Chemical group 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000001335 demethylating effect Effects 0.000 abstract 1
- 238000004821 distillation Methods 0.000 abstract 1
- 150000004795 grignard reagents Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 150000002632 lipids Chemical class 0.000 abstract 1
- 210000004185 liver Anatomy 0.000 abstract 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 210000002966 serum Anatomy 0.000 abstract 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-
- 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
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (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)
Abstract
1332824 α-Phenoxyacetic acids and derivatives thereof CIBA-GEIGY AG 17 Dec 1970 [18 Dec 1969 30 Oct 1970] 59975/70 Heading C2C Novel α-phenoxyacetic acids in which the α position is substituted by one or two C 1-4 alkyl or -alkenyl residues and the phenyl residue is substituted by a lower alkylated 5- or 6- membered monocyclic or polycyclic 1-cycloalkenyl residue, an unsubstituted 5- or 6- membered polycyclic 1-cycloalkenyl residue or an unsubstituted or lower alkylated 7- to 12- membered monocyclic or polycyclic 1-cycloalkenyl residue, wherein 1-cycloalkenyl means a singly unsaturated cycloalkenyl residue, the double bond of which extends from the carbon atom which is adjacent to the phenyl residue to an adjacent carbon atom, and ester and amides thereof may be prepared by (a) condensing a phenol which is substituted by an appropriate 1-cycloalkenyl residue with an α-halogenoacetic acid ester which is further substituted in the α- position by one or two C 1-4 alkyl or -alkenyl residues; (b) reacting a phenol as in (a) with an aldehyde or ketone derived from a C 1-4 alkane or -alkene in the presence of a tri- or tetrahalogenated methane derivative and a strong base or (c) forming a carboxylic acid or ester or amide thereof by reacting a corresponding compound having a modified carboxylic acid group with water, an alcohol, ammonia or an amine and thereafter optionally inter-converting the compounds of the invention by known methods. The intermediate p-(1-cycloalkenyl)phenols may be prepared by forming the Grignard reagent of a bromoanisole and reacting it with a cycloalkanone and dehydrating the hydrolysis product if dehydration does not occur on distillation followed by demethylating the obtained anisole. Pharmaceutical compositions of the compounds of the invention show a serum triglyceride lowering action, serum cholesterol lowering action and bring about a lowering of liver lipids when administered orally or parenterally with the usual excipients.
[GB1332824A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1899069 | 1969-12-18 | ||
| CH1607770 | 1970-10-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE34820L IE34820L (en) | 1971-06-18 |
| IE34820B1 true IE34820B1 (en) | 1975-08-20 |
Family
ID=25717373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE160770A IE34820B1 (en) | 1969-12-18 | 1970-12-15 | Alpha-phenoxyacetic acids and derivatives thereof |
Country Status (8)
| Country | Link |
|---|---|
| AR (2) | AR192704A1 (en) |
| BE (1) | BE760449A (en) |
| CA (1) | CA987337A (en) |
| DE (1) | DE2060573A1 (en) |
| FR (1) | FR2081376B1 (en) |
| GB (1) | GB1332824A (en) |
| IE (1) | IE34820B1 (en) |
| NL (1) | NL7018444A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2598146B1 (en) * | 1986-04-30 | 1989-01-20 | Rech Ind | NEW PROCESS FOR THE PREPARATION OF FIBRATES. |
-
1970
- 1970-12-09 DE DE19702060573 patent/DE2060573A1/en active Pending
- 1970-12-10 CA CA100,255A patent/CA987337A/en not_active Expired
- 1970-12-15 IE IE160770A patent/IE34820B1/en unknown
- 1970-12-15 FR FR7045165A patent/FR2081376B1/fr not_active Expired
- 1970-12-17 BE BE760449A patent/BE760449A/en unknown
- 1970-12-17 GB GB5997570A patent/GB1332824A/en not_active Expired
- 1970-12-17 NL NL7018444A patent/NL7018444A/xx unknown
- 1970-12-18 AR AR23305970A patent/AR192704A1/en active
-
1971
- 1971-09-24 AR AR23816371A patent/AR192896A1/en active
Also Published As
| Publication number | Publication date |
|---|---|
| AR192704A1 (en) | 1973-03-14 |
| CA987337A (en) | 1976-04-13 |
| NL7018444A (en) | 1971-06-22 |
| DE2060573A1 (en) | 1971-06-24 |
| AR192896A1 (en) | 1973-03-21 |
| GB1332824A (en) | 1973-10-03 |
| BE760449A (en) | 1971-06-17 |
| FR2081376A1 (en) | 1971-12-03 |
| FR2081376B1 (en) | 1975-12-26 |
| IE34820L (en) | 1971-06-18 |
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