IL46790A - Phenoxy(or phenylthio)-cyclohexane(or cyclopentane)carboxylic acid derivatives and their preparation - Google Patents
Phenoxy(or phenylthio)-cyclohexane(or cyclopentane)carboxylic acid derivatives and their preparationInfo
- Publication number
- IL46790A IL46790A IL46790A IL4679075A IL46790A IL 46790 A IL46790 A IL 46790A IL 46790 A IL46790 A IL 46790A IL 4679075 A IL4679075 A IL 4679075A IL 46790 A IL46790 A IL 46790A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- amino
- formula
- compound
- hydrogen
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1364806 Substituted tricyclic furans and thiophenes F HOFFMANN-LA ROCHE & CO AG 24 March 1972 [26 March 1971] 13877/72 Heading C2C Novel compounds of the Formula I wherein R 1 and R 2 are independently hydrogen, halogen, C 1-7 alkyl, C 1-7 alkoxy, C 1-7 alkylthio, trifluoromethyl, cyano, carbamoyl, carboxy, C 1-7 alkoxycarbonyl, nitro, amino, mono-(C 1-7 alkyl) amino, di-(C 1-7 alkyl) amino, acyl, acylamido, sulphamoyl, di-(C 1-7 alkyl) sulphamoyl, or difluoromethylsulphonyl; R 3 is hydrogen, C 1-7 alkyl, amino-C 1-7 alkyl, mono-(C 1-7 alkyl) amino-C 1-7 alkyl, di-(C 1-7 alkyl) amino C 1-7 alkyl; n is 1 or 2 and X is oxygen or sulphur, may be prepared by (a) cyclizing a compound of the formula II wherein at least one position on the phenyl ring ortho to X is unsubstituted, and R<SP>1</SP> 3 is C 1-7 alkyl, (b) treating a compound IIa wherein R<SP>1</SP> 1 and R<SP>1</SP> 2 are independently hydrogen, nitro, trifluoromethyl, C 1-7 alkoxycarbonyl, cyano or acyl (at least one of R<SP>1</SP> 1 and R<SP>1</SP> 2 being other than hydrogen) with an acidic catalyst to yield an appropriate substituted compound I in which X is oxygen, and (c) interconversion of substituents on I by known methods and separation of isomers, i.e. resolution, conversion to a salt with acid or base, saponification of a carboxylic ester group, conversion of a salt of compound I wherein R 3 represents hydrogen into a compound I wherein R 3 represents other than H or alkyl, reduction of a nitro to an amino group, conversion of an amino group into a diazonium salt and thence into hydrogen, halogen, cyano, hydroxy or alkoxy. Compounds of Formula IIa above are prepared by reacting compounds and Cycloalkanes of Formula IV are obtained by halogenating the corresponding halogen free compound. Pharmaceutical compositions having antiinflammatory and anti-rheumatic activity and which are useful for oral, enteral or parenteral administration, contain the above novel compounds I.
[GB1364806A]
Claims (5)
1. Phenoxy (or phenylthio)-cyclohexane (or cyclopentane) carboxy ic acid "derivatives of- he-forinula wherein R^ and independently represent hydrogen, halogen, lower alkyl, lower alkoxy, lower alkanoylamido, provided that at least one of R1 and is other than hydrogen, R'^ represents lower alkyl, n is 1 or 2 and X represents oxygen or sulfur.
2. 3-(3-Chlorophenoxy)-4-oxycyclohexanecarboxylio acid ethyl ester.
3. 3-(4-Chlorophenylthio)-4-oxocyclohexanecarbox lio acid ethyl ester.
4. 3-(1 -Chlorophenoxy)-4-oxocyolopentanecarboxylic acid ethyl ester.
5. Compounds of formula I in Claim 1 , substantially as described herein with reference to the Examples. « 14 ~ 46790/3 6, A process for the preparation of compounds of formula I in Claim 1 wherein a phenol or thiophenol of the formula is reacted with a haloketocycloalkane carboxylic acid ester of the formula in which formulae , R^f E* n and X have the same( meaning as in Claim 1 and Hal is halogen^, 7· A process according to Claim 6, wherein the reaction is carried out in a non-polar or polar solvent. 8· - A process according to Claim 6 or 7> substantiall as described herein with reference to the Examples* PC :mz
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12857071A | 1971-03-26 | 1971-03-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL46790A true IL46790A (en) | 1976-05-31 |
Family
ID=22435954
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39036A IL39036A (en) | 1971-03-26 | 1972-03-20 | Benzofuran and benzothiophene carboxylic acid derivatives,their preparation and compositions containing them |
| IL46790A IL46790A (en) | 1971-03-26 | 1975-03-11 | Phenoxy(or phenylthio)-cyclohexane(or cyclopentane)carboxylic acid derivatives and their preparation |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39036A IL39036A (en) | 1971-03-26 | 1972-03-20 | Benzofuran and benzothiophene carboxylic acid derivatives,their preparation and compositions containing them |
Country Status (17)
| Country | Link |
|---|---|
| AR (3) | AR192514A1 (en) |
| AT (2) | AT319227B (en) |
| AU (1) | AU463471B2 (en) |
| BE (1) | BE781176A (en) |
| CA (1) | CA988529A (en) |
| CH (1) | CH574433A5 (en) |
| DE (1) | DE2214501A1 (en) |
| DK (1) | DK130345B (en) |
| ES (1) | ES401162A1 (en) |
| FR (1) | FR2130655B1 (en) |
| GB (2) | GB1364807A (en) |
| HU (1) | HU164250B (en) |
| IE (2) | IE36187B1 (en) |
| IL (2) | IL39036A (en) |
| NL (1) | NL7203979A (en) |
| SE (2) | SE385704B (en) |
| ZA (1) | ZA721612B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ168896A3 (en) * | 1995-06-27 | 1997-01-15 | Egyt Gyogyszervegyeszeti Gyar | Oxaindene derivatives and process for preparing thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7008628A (en) * | 1969-06-25 | 1970-12-29 |
-
1972
- 1972-03-09 CH CH350472A patent/CH574433A5/xx not_active IP Right Cessation
- 1972-03-09 ZA ZA721612A patent/ZA721612B/en unknown
- 1972-03-20 IL IL39036A patent/IL39036A/en unknown
- 1972-03-20 IE IE2067/74A patent/IE36187B1/en unknown
- 1972-03-20 IE IE354/72A patent/IE36186B1/en unknown
- 1972-03-21 AU AU40245/72A patent/AU463471B2/en not_active Expired
- 1972-03-22 CA CA137,759A patent/CA988529A/en not_active Expired
- 1972-03-23 HU HUHO1463A patent/HU164250B/hu unknown
- 1972-03-24 DK DK145472AA patent/DK130345B/en unknown
- 1972-03-24 AT AT229773A patent/AT319227B/en not_active IP Right Cessation
- 1972-03-24 BE BE781176A patent/BE781176A/en unknown
- 1972-03-24 FR FR7210383A patent/FR2130655B1/fr not_active Expired
- 1972-03-24 GB GB5123373A patent/GB1364807A/en not_active Expired
- 1972-03-24 DE DE19722214501 patent/DE2214501A1/en active Pending
- 1972-03-24 AT AT257972A patent/AT313272B/en not_active IP Right Cessation
- 1972-03-24 GB GB1387772A patent/GB1364806A/en not_active Expired
- 1972-03-24 NL NL7203979A patent/NL7203979A/xx not_active Application Discontinuation
- 1972-03-24 SE SE7203902A patent/SE385704B/en unknown
- 1972-03-25 ES ES401162A patent/ES401162A1/en not_active Expired
- 1972-11-23 AR AR245290A patent/AR192514A1/en active
- 1972-11-24 AR AR245289A patent/AR194407A1/en active
- 1972-11-24 AR AR245291A patent/AR192515A1/en active
-
1974
- 1974-12-27 SE SE7416328A patent/SE7416328L/xx unknown
-
1975
- 1975-03-11 IL IL46790A patent/IL46790A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1364806A (en) | 1974-08-29 |
| FR2130655B1 (en) | 1975-06-20 |
| GB1364807A (en) | 1974-08-29 |
| DK130345C (en) | 1975-07-07 |
| ES401162A1 (en) | 1975-02-01 |
| HU164250B (en) | 1974-01-28 |
| AU463471B2 (en) | 1975-07-08 |
| ZA721612B (en) | 1972-11-29 |
| IE36186L (en) | 1972-09-26 |
| IE36186B1 (en) | 1976-09-01 |
| AT319227B (en) | 1974-12-10 |
| SE7416328L (en) | 1974-12-27 |
| CH574433A5 (en) | 1976-04-15 |
| DE2214501A1 (en) | 1972-10-05 |
| IL39036A0 (en) | 1972-06-28 |
| IL39036A (en) | 1976-05-31 |
| FR2130655A1 (en) | 1972-11-03 |
| AU4024572A (en) | 1972-03-21 |
| AT313272B (en) | 1974-02-11 |
| SE385704B (en) | 1976-07-19 |
| CA988529A (en) | 1976-05-04 |
| AR194407A1 (en) | 1973-07-13 |
| AR192514A1 (en) | 1973-02-21 |
| NL7203979A (en) | 1972-09-28 |
| BE781176A (en) | 1972-09-25 |
| IE36187B1 (en) | 1976-09-01 |
| AR192515A1 (en) | 1973-02-21 |
| DK130345B (en) | 1975-02-10 |
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