IE36485B1 - Benzothiophene derivatives and process for preparing same - Google Patents
Benzothiophene derivatives and process for preparing sameInfo
- Publication number
- IE36485B1 IE36485B1 IE790/72A IE79072A IE36485B1 IE 36485 B1 IE36485 B1 IE 36485B1 IE 790/72 A IE790/72 A IE 790/72A IE 79072 A IE79072 A IE 79072A IE 36485 B1 IE36485 B1 IE 36485B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- reaction
- compound
- june
- prepared
- Prior art date
Links
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 abstract 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- -1 dimethylamino, diethylamino, di - n - propylamino, di - n - butylamino, pyrrolidino, piperidino Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 abstract 1
Classifications
-
- 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
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
1357212 Benzothiapine derivatives LABAZ 16 June 1972 [25 June 1971] 30032/71 Heading C2C Novel compounds of Formula I and the pharmaceutically acceptable acid addition salts thereof, for example the oxalate or hydrochloride, wherein R represents hydrogen or a branched or straight-chain alkyl group containing from 1 to 4 carbon atoms, R<SP>1</SP> represents hydrogen or methyl, X and X 1 , which are identical, each represent an atom of chlorine, bromine or iodine, Am represents a dimethylamino, diethylamino, di - n - propylamino, di - n - butylamino, pyrrolidino, piperidino or perhydroazepino group, and n is an integer in the range of from I to 5 inclusive are prepared by reaction of HAm with a compound of Formula IV or in the case where n is 1 or 2 by reaction of a compound II with (Z is halogen or tosyloxy). Intermediates of Formula IV above are prepared by reaction of with an intermediate of Formula II above obtained by the demethylation of the corresponding methyl ether starting material followed by halogenation. Pharmaceutical compositions in conventional forms for oral or rectal administration comprise an above novel compound and a carrier or diluent. The compositions are of use in the treatment of heart conditions.
[GB1357212A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3003271A GB1357212A (en) | 1971-06-25 | 1971-06-25 | Benzothiophene derivatives and process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36485L IE36485L (en) | 1972-12-25 |
| IE36485B1 true IE36485B1 (en) | 1976-11-10 |
Family
ID=10301169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE790/72A IE36485B1 (en) | 1971-06-25 | 1972-06-07 | Benzothiophene derivatives and process for preparing same |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS4844248A (en) |
| AT (1) | AT312597B (en) |
| AU (1) | AU462617B2 (en) |
| BE (1) | BE784260A (en) |
| CA (1) | CA959492A (en) |
| CH (2) | CH549042A (en) |
| DE (1) | DE2230669A1 (en) |
| ES (1) | ES404252A1 (en) |
| FI (1) | FI54477C (en) |
| FR (1) | FR2143250B1 (en) |
| GB (1) | GB1357212A (en) |
| HU (1) | HU166255B (en) |
| IE (1) | IE36485B1 (en) |
| NL (1) | NL7208703A (en) |
| OA (1) | OA04117A (en) |
| SE (1) | SE385482B (en) |
| SU (2) | SU453844A3 (en) |
| ZA (1) | ZA723868B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3947470A (en) * | 1974-06-20 | 1976-03-30 | Smithkline Corporation | Substituted benzofurans and benzothiophenes |
| JPS5973579A (en) * | 1982-10-19 | 1984-04-25 | Kotobuki Seiyaku Kk | Benzofuran or benzothiophene derivative, diuretic agent containing said compound as active constituent and preparation thereof |
| NO174506B (en) * | 1984-10-30 | 1994-02-07 | Usv Pharma Corp | Analogous procedure for the preparation of therapeutically active compounds |
| CA2145614A1 (en) * | 1994-03-31 | 1995-10-01 | Jeffrey A. Dodge | Intermediates and processes for preparing benzothiophene compounds |
| CA2231013A1 (en) * | 1997-04-30 | 1998-10-30 | Eli Lilly And Company | Process for preparing benzoic acid derivative intermediates and benzothiophene pharmaceuticals |
-
1971
- 1971-06-25 GB GB3003271A patent/GB1357212A/en not_active Expired
-
1972
- 1972-06-01 BE BE784260A patent/BE784260A/en unknown
- 1972-06-05 FI FI1578/72A patent/FI54477C/en active
- 1972-06-06 ZA ZA723868A patent/ZA723868B/en unknown
- 1972-06-07 IE IE790/72A patent/IE36485B1/en unknown
- 1972-06-13 HU HULA799A patent/HU166255B/hu unknown
- 1972-06-13 AU AU43338/72A patent/AU462617B2/en not_active Expired
- 1972-06-21 CH CH930272A patent/CH549042A/en not_active IP Right Cessation
- 1972-06-21 CH CH1795273A patent/CH548409A/en not_active IP Right Cessation
- 1972-06-21 SE SE7208187A patent/SE385482B/en unknown
- 1972-06-22 FR FR7222480A patent/FR2143250B1/fr not_active Expired
- 1972-06-23 NL NL7208703A patent/NL7208703A/xx not_active Application Discontinuation
- 1972-06-23 DE DE19722230669 patent/DE2230669A1/en active Pending
- 1972-06-23 SU SU1800666A patent/SU453844A3/ru active
- 1972-06-23 CA CA145,600A patent/CA959492A/en not_active Expired
- 1972-06-23 SU SU721959344A patent/SU486510A3/en active
- 1972-06-24 JP JP47063621A patent/JPS4844248A/ja active Pending
- 1972-06-24 ES ES404252A patent/ES404252A1/en not_active Expired
- 1972-06-26 AT AT545972A patent/AT312597B/en not_active IP Right Cessation
- 1972-06-26 OA OA54619A patent/OA04117A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE385482B (en) | 1976-07-05 |
| SU453844A3 (en) | 1974-12-15 |
| CH548409A (en) | 1974-04-30 |
| BE784260A (en) | 1972-12-01 |
| FR2143250B1 (en) | 1975-06-20 |
| FI54477B (en) | 1978-08-31 |
| NL7208703A (en) | 1972-12-28 |
| GB1357212A (en) | 1974-06-19 |
| AU4333872A (en) | 1973-12-20 |
| SU486510A3 (en) | 1975-09-30 |
| JPS4844248A (en) | 1973-06-26 |
| AU462617B2 (en) | 1975-06-10 |
| CH549042A (en) | 1974-05-15 |
| FI54477C (en) | 1978-12-11 |
| IE36485L (en) | 1972-12-25 |
| FR2143250A1 (en) | 1973-02-02 |
| CA959492A (en) | 1974-12-17 |
| ES404252A1 (en) | 1975-06-01 |
| HU166255B (en) | 1975-02-28 |
| DE2230669A1 (en) | 1972-12-28 |
| AT312597B (en) | 1974-01-10 |
| OA04117A (en) | 1979-11-30 |
| ZA723868B (en) | 1973-03-28 |
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