GB1111361A - 4-phenoxyalkanoic acids and derivatives thereof - Google Patents
4-phenoxyalkanoic acids and derivatives thereofInfo
- Publication number
- GB1111361A GB1111361A GB2338666A GB2338666A GB1111361A GB 1111361 A GB1111361 A GB 1111361A GB 2338666 A GB2338666 A GB 2338666A GB 2338666 A GB2338666 A GB 2338666A GB 1111361 A GB1111361 A GB 1111361A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- alkyl
- radical
- carbon atoms
- reacting
- 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
- 239000002253 acid Substances 0.000 title abstract 9
- 150000007513 acids Chemical class 0.000 title 1
- 150000002148 esters Chemical class 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 150000001408 amides Chemical class 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000004820 halides Chemical class 0.000 abstract 3
- 231100000252 nontoxic Toxicity 0.000 abstract 3
- 230000003000 nontoxic effect Effects 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000004104 aryloxy group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000743 hydrocarbylene group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 230000000871 hypocholesterolemic effect Effects 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000050 nutritive effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
- C07C59/64—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Novel compounds of formula <FORM:1111361/C2/1> where R is a hydrogen atom or a C1- 5 alkyl radical; each of R1 and R2 is a C1- 5 alky radical; X is a halogen atom or a C1- 5 alkyl, C1- 5 haloalkyl, cycloalkyl, C1- 5 alkoxy, C1- 5 alkylthio, aryl, aralkyl, aryloxy or aralkoxy radical, or, taken together, two X radicals on adjacent carbon atoms of the benzene ring may be combined to form a hydrocarbylene chain containing 3 or 4 carbon atoms between its points of attachment; and n is 0, 1, 2 or 3, and the non-toxic pharmacologically acceptable salts, esters or amides thereof, are prepared by treating a compound of Formula II <FORM:1111361/C2/2> wherein R3 is an alkyl radical, with a reducing agent, and, if desired, hydrolysing the 4-phenoxy-alkanoic acid ester obtained. The salts are produced by reacting the acid with a base having a non-toxic pharmacologically acceptable cation. Esters may be obtained from the corresponding acid, e.g. by reacting the acid with an alcohol, or by converting the acid to its halide, and reacting the halide with an alcohol. Amides may aso be prepared from the acid or acid halide or from the ester. The 4 - phenoxy - 2 - alkenoic acid ester starting materials may be prepared by treating a 2-phenoxyalkanal with an alkoxycarbonyl-alkylidene - triarylphosphorane or an alkyl dialkoxyphosphinylalkanoate.ALSO:Therapeutic compositions having hypocholesterolemic activity and which can be administered orally or parenterally, contain as active ingredient a compound of formula <FORM:1111361/A5-A6/1> where R is a hydrogen atom or C1-5 alkyl group, each of R1 and R2 is a C1-5 alkyl radical; X is a halogen atom, or a C1-5 alkyl, C1-5 haloalkyl, cycloalkyl, C1-5 alkoxy, C1-5 alkylthio, aryl, aralkyl, aryloxy or aralkoxy radical, or taken together, two X radicals on adjacent carbon atoms may be combined to form a hydrocarbylene chain containing 3 or 4 carbon atoms between its points of attachment, and n is 0, 1, 2 or 3, or non-toxic pharmaceutically acceptable salt, ester or amide thereof, if desired, in association with a further pharmaceutically active compound, e.g. a known hypocholesterolemic or nutritive agent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45943665A | 1965-05-27 | 1965-05-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1111361A true GB1111361A (en) | 1968-04-24 |
Family
ID=23824762
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2338666A Expired GB1111361A (en) | 1965-05-27 | 1966-05-25 | 4-phenoxyalkanoic acids and derivatives thereof |
Country Status (6)
| Country | Link |
|---|---|
| BR (1) | BR6679625D0 (en) |
| CH (1) | CH471063A (en) |
| DE (1) | DE1543764A1 (en) |
| FR (1) | FR5865M (en) |
| GB (1) | GB1111361A (en) |
| NL (1) | NL6607056A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132367A3 (en) * | 1983-07-18 | 1985-05-15 | Eli Lilly And Company | Leukotriene antagonists |
| US4764521A (en) * | 1983-07-18 | 1988-08-16 | Eli Lilly And Company | Leukotriene antagonists and a method of use there as |
| US5462954A (en) * | 1991-11-25 | 1995-10-31 | Eli Lilly And Company | Substituted phenyl phenol leukotriene antagonists |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3674836A (en) * | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
| US4172146A (en) * | 1973-05-08 | 1979-10-23 | Ciba-Geigy Corporation | Substituted phenyl derivatives |
| US4416687A (en) * | 1982-02-01 | 1983-11-22 | Monsanto Company | 3,5-Bis (trifluoromethyl)phenoxy carboxylic acids and derivatives thereof |
-
1966
- 1966-05-18 BR BR17962566A patent/BR6679625D0/en unknown
- 1966-05-23 NL NL6607056A patent/NL6607056A/xx unknown
- 1966-05-24 CH CH744666A patent/CH471063A/en not_active IP Right Cessation
- 1966-05-25 GB GB2338666A patent/GB1111361A/en not_active Expired
- 1966-05-25 DE DE19661543764 patent/DE1543764A1/en active Pending
- 1966-08-12 FR FR73054A patent/FR5865M/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0132367A3 (en) * | 1983-07-18 | 1985-05-15 | Eli Lilly And Company | Leukotriene antagonists |
| US4764521A (en) * | 1983-07-18 | 1988-08-16 | Eli Lilly And Company | Leukotriene antagonists and a method of use there as |
| US5462954A (en) * | 1991-11-25 | 1995-10-31 | Eli Lilly And Company | Substituted phenyl phenol leukotriene antagonists |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6679625D0 (en) | 1973-10-23 |
| NL6607056A (en) | 1966-11-28 |
| CH471063A (en) | 1969-04-15 |
| FR5865M (en) | 1968-03-11 |
| DE1543764A1 (en) | 1970-01-02 |
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