IE36186L - Benzofuran and benzothiophene derivatives. - Google Patents
Benzofuran and benzothiophene derivatives.Info
- Publication number
- IE36186L IE36186L IE720354A IE35472A IE36186L IE 36186 L IE36186 L IE 36186L IE 720354 A IE720354 A IE 720354A IE 35472 A IE35472 A IE 35472A IE 36186 L IE36186 L IE 36186L
- Authority
- IE
- Ireland
- Prior art keywords
- alkyl
- amino
- compound
- hydrogen
- formula
- Prior art date
Links
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 title 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 150000001875 compounds Chemical class 0.000 abstract 10
- -1 cyano, carbamoyl Chemical group 0.000 abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 150000002431 hydrogen Chemical class 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 229910052736 halogen Inorganic materials 0.000 abstract 3
- 150000002367 halogens Chemical class 0.000 abstract 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000003356 anti-rheumatic effect Effects 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 150000002240 furans Chemical class 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
- 150000003577 thiophenes Chemical class 0.000 abstract 1
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]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12857071A | 1971-03-26 | 1971-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36186L true IE36186L (en) | 1972-09-26 |
| IE36186B1 IE36186B1 (en) | 1976-09-01 |
Family
ID=22435954
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE354/72A IE36186B1 (en) | 1971-03-26 | 1972-03-20 | Benzofuran and benzothiphene derivatives |
| IE2067/74A IE36187B1 (en) | 1971-03-26 | 1972-03-20 | Phenoxy and phenylthio compounds |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2067/74A IE36187B1 (en) | 1971-03-26 | 1972-03-20 | Phenoxy and phenylthio compounds |
Country Status (17)
| Country | Link |
|---|---|
| AR (3) | AR192514A1 (en) |
| AT (2) | AT313272B (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) | IE36186B1 (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 ZA ZA721612A patent/ZA721612B/en unknown
- 1972-03-09 CH CH350472A patent/CH574433A5/xx not_active IP Right Cessation
- 1972-03-20 IE IE354/72A patent/IE36186B1/en unknown
- 1972-03-20 IL IL39036A patent/IL39036A/en unknown
- 1972-03-20 IE IE2067/74A patent/IE36187B1/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 GB GB5123373A patent/GB1364807A/en not_active Expired
- 1972-03-24 BE BE781176A patent/BE781176A/en unknown
- 1972-03-24 AT AT257972A patent/AT313272B/en not_active IP Right Cessation
- 1972-03-24 SE SE7203902A patent/SE385704B/en unknown
- 1972-03-24 DK DK145472AA patent/DK130345B/en unknown
- 1972-03-24 DE DE19722214501 patent/DE2214501A1/en active Pending
- 1972-03-24 AT AT229773A patent/AT319227B/en not_active IP Right Cessation
- 1972-03-24 FR FR7210383A patent/FR2130655B1/fr not_active Expired
- 1972-03-24 GB GB1387772A patent/GB1364806A/en not_active Expired
- 1972-03-24 NL NL7203979A patent/NL7203979A/xx not_active Application Discontinuation
- 1972-03-25 ES ES401162A patent/ES401162A1/en not_active Expired
- 1972-11-23 AR AR245290A patent/AR192514A1/en active
- 1972-11-24 AR AR245291A patent/AR192515A1/en active
- 1972-11-24 AR AR245289A patent/AR194407A1/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 |
|---|---|
| CH574433A5 (en) | 1976-04-15 |
| SE7416328L (en) | 1974-12-27 |
| IL39036A0 (en) | 1972-06-28 |
| DK130345B (en) | 1975-02-10 |
| AR194407A1 (en) | 1973-07-13 |
| HU164250B (en) | 1974-01-28 |
| DE2214501A1 (en) | 1972-10-05 |
| CA988529A (en) | 1976-05-04 |
| IE36186B1 (en) | 1976-09-01 |
| NL7203979A (en) | 1972-09-28 |
| FR2130655B1 (en) | 1975-06-20 |
| GB1364806A (en) | 1974-08-29 |
| IL46790A (en) | 1976-05-31 |
| IL39036A (en) | 1976-05-31 |
| GB1364807A (en) | 1974-08-29 |
| AT319227B (en) | 1974-12-10 |
| SE385704B (en) | 1976-07-19 |
| IE36187B1 (en) | 1976-09-01 |
| BE781176A (en) | 1972-09-25 |
| AU4024572A (en) | 1972-03-21 |
| DK130345C (en) | 1975-07-07 |
| ZA721612B (en) | 1972-11-29 |
| FR2130655A1 (en) | 1972-11-03 |
| ES401162A1 (en) | 1975-02-01 |
| AR192515A1 (en) | 1973-02-21 |
| AU463471B2 (en) | 1975-07-08 |
| AR192514A1 (en) | 1973-02-21 |
| AT313272B (en) | 1974-02-11 |
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