GB1385828A - Phenoxyacetic acid and cyclopropa-a-naphthoxyacetic acid derivatives - Google Patents
Phenoxyacetic acid and cyclopropa-a-naphthoxyacetic acid derivativesInfo
- Publication number
- GB1385828A GB1385828A GB3831173A GB3831173A GB1385828A GB 1385828 A GB1385828 A GB 1385828A GB 3831173 A GB3831173 A GB 3831173A GB 3831173 A GB3831173 A GB 3831173A GB 1385828 A GB1385828 A GB 1385828A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- hydrogen
- formula
- reacting
- alkyl
- 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
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 abstract 9
- 239000001257 hydrogen Substances 0.000 abstract 9
- 125000000217 alkyl group Chemical group 0.000 abstract 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 4
- 239000000543 intermediate Substances 0.000 abstract 4
- 230000003301 hydrolyzing effect Effects 0.000 abstract 3
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-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
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- FMCAFXHLMUOIGG-IWFBPKFRSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-IWFBPKFRSA-N 0.000 abstract 1
- XCTSGGVBLWBSIJ-UHFFFAOYSA-N 1-methoxy-4-prop-1-en-2-ylbenzene Chemical compound COC1=CC=C(C(C)=C)C=C1 XCTSGGVBLWBSIJ-UHFFFAOYSA-N 0.000 abstract 1
- SFHTZDVXBAOICD-UHFFFAOYSA-N 2-(1H-cyclopropa[a]naphthalen-1-yloxy)acetic acid Chemical class C1(C=2C1=CC=C1C=CC=CC=21)OCC(=O)O SFHTZDVXBAOICD-UHFFFAOYSA-N 0.000 abstract 1
- SUXCRRZYROZECQ-UHFFFAOYSA-N 4-(2,2-dichlorocyclopropyl)aniline Chemical compound C1=CC(N)=CC=C1C1C(Cl)(Cl)C1 SUXCRRZYROZECQ-UHFFFAOYSA-N 0.000 abstract 1
- KPSRODZRAIWAKH-JTQLQIEISA-N Ciprofibrate Natural products C1=CC(OC(C)(C)C(O)=O)=CC=C1[C@H]1C(Cl)(Cl)C1 KPSRODZRAIWAKH-JTQLQIEISA-N 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- KPSRODZRAIWAKH-UHFFFAOYSA-N ciprofibrate Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1C1C(Cl)(Cl)C1 KPSRODZRAIWAKH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 238000005661 deetherification reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 238000006193 diazotization reaction Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002148 esters Chemical class 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
- 230000000871 hypocholesterolemic effect Effects 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- -1 p-(2,2-dichlorocyclopropyl)phenyl Chemical group 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
-
- 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
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/443,418 US3948973A (en) | 1972-08-29 | 1974-02-19 | Halocyclopropyl substituted phenoxyalkanoic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28457772A | 1972-08-29 | 1972-08-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1385828A true GB1385828A (en) | 1975-03-05 |
Family
ID=23090716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3831173A Expired GB1385828A (en) | 1972-08-29 | 1973-08-13 | Phenoxyacetic acid and cyclopropa-a-naphthoxyacetic acid derivatives |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142979A3 (en) * | 1983-11-15 | 1985-12-11 | Sterwin Ag. | Improvements in the production of halocyclopropyl-substituted phenoxyalkanoic acids and esters |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2471364A1 (fr) * | 1979-12-11 | 1981-06-19 | Rhone Poulenc Agrochimie | Nouveaux derives de l'aniline et compositions regulatrices de la croissance des plantes les contenant |
| US4691042A (en) * | 1983-06-24 | 1987-09-01 | The Dow Chemical Company | Preparation of monaoalkylated dihydroxybenzenes and novel compounds prepared thereby |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1121722A (en) * | 1966-03-31 | 1968-07-31 | Ici Ltd | New carboxylic acid derivatives |
| BE754245A (fr) * | 1969-08-01 | 1970-12-31 | Sumitomo Chemical Co | Derives d'acides phenoxy carboxyliques |
-
1973
- 1973-01-01 AR AR249792A patent/AR206596A1/es active
- 1973-08-13 GB GB3831173A patent/GB1385828A/en not_active Expired
- 1973-08-20 IL IL43026A patent/IL43026A/en unknown
- 1973-08-22 AU AU59488/73A patent/AU472631B2/en not_active Expired
- 1973-08-22 ZA ZA735748A patent/ZA735748B/xx unknown
- 1973-08-22 FR FR7330434A patent/FR2197586B1/fr not_active Expired
- 1973-08-23 BE BE1005309A patent/BE803924A/xx not_active IP Right Cessation
- 1973-08-24 PH PH14951A patent/PH10530A/en unknown
- 1973-08-27 CH CH7312272A patent/CH608780A5/xx not_active IP Right Cessation
- 1973-08-27 CH CH959876A patent/CH605584A5/fr not_active IP Right Cessation
- 1973-08-27 AT AT744773A patent/AT331207B/de not_active IP Right Cessation
- 1973-08-28 NO NO3388/73A patent/NO143528C/no unknown
- 1973-08-28 CA CA179,829A patent/CA1023762A/en not_active Expired
- 1973-08-28 SE SE7311687A patent/SE417828B/xx unknown
- 1973-08-28 ES ES418283A patent/ES418283A1/es not_active Expired
- 1973-08-28 DK DK471773AA patent/DK141366B/da not_active IP Right Cessation
- 1973-08-28 FI FI2675/73A patent/FI58629C/fi active
- 1973-08-29 NL NLAANVRAGE7311903,A patent/NL180004C/xx not_active IP Right Cessation
- 1973-08-29 JP JP48096261A patent/JPS585175B2/ja not_active Expired
- 1973-08-29 DE DE2343606A patent/DE2343606C2/de not_active Expired
-
1980
- 1980-02-28 HK HK69/80A patent/HK6980A/xx unknown
-
1982
- 1982-06-02 JP JP57094644A patent/JPS60334B2/ja not_active Expired
- 1982-06-02 JP JP57094645A patent/JPS60335B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0142979A3 (en) * | 1983-11-15 | 1985-12-11 | Sterwin Ag. | Improvements in the production of halocyclopropyl-substituted phenoxyalkanoic acids and esters |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19920813 |