GB1012480A - Anti-inflammatory agents - Google Patents
Anti-inflammatory agentsInfo
- Publication number
- GB1012480A GB1012480A GB2878062A GB2878062A GB1012480A GB 1012480 A GB1012480 A GB 1012480A GB 2878062 A GB2878062 A GB 2878062A GB 2878062 A GB2878062 A GB 2878062A GB 1012480 A GB1012480 A GB 1012480A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- acids
- ethyl
- methyl
- butyl
- 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
- 229940121363 anti-inflammatory agent Drugs 0.000 title 1
- 239000002260 anti-inflammatory agent Substances 0.000 title 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 15
- 239000002253 acid Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004414 alkyl thio group Chemical group 0.000 abstract 4
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 4
- 125000004494 ethyl ester group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- 150000007513 acids Chemical class 0.000 abstract 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 3
- 238000000034 method Methods 0.000 abstract 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-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
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 2
- 125000005108 alkenylthio group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- -1 phenoxy, phenylthio Chemical group 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- JYNKBQIDIFHNCY-UHFFFAOYSA-N 2-(4-cyclopentyloxyphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1OC1CCCC1 JYNKBQIDIFHNCY-UHFFFAOYSA-N 0.000 abstract 1
- ZVLYXVZYZDRFND-UHFFFAOYSA-N 2-(4-ethylsulfanylphenyl)acetic acid Chemical compound CCSC1=CC=C(CC(O)=O)C=C1 ZVLYXVZYZDRFND-UHFFFAOYSA-N 0.000 abstract 1
- KRWRXBILDUJEOP-UHFFFAOYSA-N 2-(4-propylphenyl)propan-1-amine Chemical compound CCCC1=CC=C(C(C)CN)C=C1 KRWRXBILDUJEOP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 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
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000005336 allyloxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000001805 chlorine compounds Chemical class 0.000 abstract 1
- 239000006071 cream Substances 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- AEHWKBXBXYNPCX-UHFFFAOYSA-N ethylsulfanylbenzene Chemical compound CCSC1=CC=CC=C1 AEHWKBXBXYNPCX-UHFFFAOYSA-N 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- PCEBAZIVZVIQEO-UHFFFAOYSA-N iodocyclopentane Chemical compound IC1CCCC1 PCEBAZIVZVIQEO-UHFFFAOYSA-N 0.000 abstract 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000006210 lotion Substances 0.000 abstract 1
- 239000007937 lozenge Substances 0.000 abstract 1
- 150000002691 malonic acids Chemical class 0.000 abstract 1
- CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical class OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 abstract 1
- 239000008247 solid mixture Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 235000020357 syrup Nutrition 0.000 abstract 1
- 239000006188 syrup Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
- C07C29/149—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof with hydrogen or hydrogen-containing gases
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
-
- 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
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/30—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic 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
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The invention comprises compounds of general formula <FORM:1012480/C2/1> wherein R1 represents cycloalkyloxy (C3-C5), cycloalkylthio (C3-C5), alkylthio (C2-C3), when R2 is hydrogen; or R1 represents ethyl, n-propyl, isopropyl, n-butyl, n-pentyl, branched alkyl (C6-C7), cycloalkyl (C3-C5), alkoxy (C3-C4), alkenyloxy (C3-C4), alkylthio (C1-C5), alkenylthio (C3-C5), cycloalkyloxy (C3-C7), cycloalkylthio (C3-C7), phenoxy, phenylthio, alkenyl (C2-C4), when R2 is methyl; X represents CH2OH, COOR3 where R3 is hydrogen or alkyl (C1-C4) or, when R2 is methyl, dialkylamino substituted alkyl (C1-C4), CONH2, CH2NH2; and the non-toxic organic and inorganic salts of the acids, basic esters and amines; provided that X is not CH2OH when R1 is ethyl; and their preparation by methods described, these being analogous to known methods. Processes and intermediate and final compounds in examples are as follows:- 4-Substituted phenyl acetic acids are esterified to form ethyl esters which on treatment with ethyl carbonate yield ethyl 4-substituted phenylmalonates; methyl iodide yields the C-methyl compounds which are hydrolysed to form the malonic acids and these decarboxylated yielding 2-(4-substituted phenyl)-propionic acids. Ethyl esters thereof are obtained and reduced with lithium aluminium hydride to form 2-(4-n-propyl, -n-butyl, and -allyloxy phenyl)-propanols. 2-(4-Propyl and -butyl phenyl)-propionamides are prepared by reacting the acids with thionyl chloride and the acid chlorides with ammonia. 2-(4-Propoxy and -butoxy phenyl)-propionic acids are prepared by hydrogenation of the allyloxy and but-2-enyloxy compounds. 4-Cyclopentyloxyphenyl acetic acid is prepared by hydrolysis of the ethyl ester, obtained from the 4-hydroxy compound by reaction with cyclopentyl iodide. 4-Ethylthioacetophenone, obtained by Friedel-Crafts reaction of thiophenetole and acetyl chloride, yields on reaction with sulphur and morpholine the intermediate thioacetmorpholide which may be hydrolysed to 4-ethylthiophenylacetic acid; 4-n-propyl and -isopropyl thio compounds are similarly obtained. 2-(4-Propylphenyl)-propylamine is obtained by lithium aluminium hydride reduction of the amide.ALSO:Therapeutic compositions comprise compounds of general formula <FORM:1012480/A5-A6/1> wherein R4 represents n-butyl, cycloalkyloxy (C3-C5), cycloalkylthio (C3-C5) or alkylthio (C1-C3) when R2 is hydrogen; or R4 represents n-butyl, n-pentyl, cycloalkyl (C3-C4), alkenyloxy (C4), alkoxy (C4), branched alkyl (C6-C7), alkylthio (C1-C5), alkenylthio (C3-C5), cycloalkyloxy (C3-C7), or cycloalkylthio (C3-C7) when R2 is methyl; and X is CH2OH, COOR3 where R3 is hydrogen or alkyl (C1-C4) or, when R2 is methyl, dialkylamino substituted alkyl (C1-4), CONH2, CH2NH2; and the nontoxic organic and inorganic salts of the acids and amines, in association with a pharmaceutically acceptable diluent or carrier; also solid compositions of 2-41-n-propylphenylpropionic acid its salts and ethyl ester. Forms are described for oral (capsules, tablets, lozenges, granules, mixtures elixirs, syrups, solutions, suspensions), topical (ointments, creams, lotions) and parenteral administration. The compounds have anti-inflammatory, antipyretic and analgesic properties.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2878062A GB1012480A (en) | 1962-07-26 | 1962-07-26 | Anti-inflammatory agents |
| CH932863A CH450382A (en) | 1962-02-02 | 1963-07-26 | Process for the preparation of anti-inflammatory agents |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2878062A GB1012480A (en) | 1962-07-26 | 1962-07-26 | Anti-inflammatory agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1012480A true GB1012480A (en) | 1965-12-08 |
Family
ID=10281041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2878062A Expired GB1012480A (en) | 1962-02-02 | 1962-07-26 | Anti-inflammatory agents |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1012480A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001322A (en) | 1969-05-28 | 1977-01-04 | Eli Lilly And Company | 3-substituted phenylalkyl amines |
| US4335251A (en) | 1976-12-08 | 1982-06-15 | Hisamitsu Pharmaceutical Co. Inc. | Phenyl-i-propionic acid esters and pharmaceutical use thereof |
| EP0057047A1 (en) * | 1981-01-24 | 1982-08-04 | Reckitt And Colman Products Limited | Process for the preparation of 2-(2,4-dichlorophenoxy) phenylacetic acid |
| US4362891A (en) | 1979-06-18 | 1982-12-07 | Glaxo Group Limited | Alkanoic acid derivatives |
| EP0068222A1 (en) * | 1981-06-18 | 1983-01-05 | Technobiotic Ltd. | Process for the preparation of 2-(2,4-dichlorophenoxy)phenylacetic acid |
| EP2129218A4 (en) * | 2007-02-16 | 2011-11-30 | Emisphere Tech Inc | CYCLIC FRACTION COMPOUNDS AND ACTIVE AGENT DELIVERY COMPOSITIONS |
-
1962
- 1962-07-26 GB GB2878062A patent/GB1012480A/en not_active Expired
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4001322A (en) | 1969-05-28 | 1977-01-04 | Eli Lilly And Company | 3-substituted phenylalkyl amines |
| US4335251A (en) | 1976-12-08 | 1982-06-15 | Hisamitsu Pharmaceutical Co. Inc. | Phenyl-i-propionic acid esters and pharmaceutical use thereof |
| US4362891A (en) | 1979-06-18 | 1982-12-07 | Glaxo Group Limited | Alkanoic acid derivatives |
| EP0057047A1 (en) * | 1981-01-24 | 1982-08-04 | Reckitt And Colman Products Limited | Process for the preparation of 2-(2,4-dichlorophenoxy) phenylacetic acid |
| EP0068222A1 (en) * | 1981-06-18 | 1983-01-05 | Technobiotic Ltd. | Process for the preparation of 2-(2,4-dichlorophenoxy)phenylacetic acid |
| EP2129218A4 (en) * | 2007-02-16 | 2011-11-30 | Emisphere Tech Inc | CYCLIC FRACTION COMPOUNDS AND ACTIVE AGENT DELIVERY COMPOSITIONS |
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