GB1456323A - Benzothiophenes process for preparing them and pharmaceutical compositions containing the same - Google Patents
Benzothiophenes process for preparing them and pharmaceutical compositions containing the sameInfo
- Publication number
- GB1456323A GB1456323A GB2525674A GB2525674A GB1456323A GB 1456323 A GB1456323 A GB 1456323A GB 2525674 A GB2525674 A GB 2525674A GB 2525674 A GB2525674 A GB 2525674A GB 1456323 A GB1456323 A GB 1456323A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzo
- general formula
- thiophene
- condensing
- prepared
- 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
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical class C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 title abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 4
- -1 dimethylamino, diethylamino, di-n-propylamino Chemical group 0.000 abstract 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001649 bromium compounds Chemical class 0.000 abstract 2
- 150000001805 chlorine compounds Chemical class 0.000 abstract 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- GFNZJAUVJCGWLW-UHFFFAOYSA-N 2-methoxy-1,3-dimethylbenzene Chemical compound COC1=C(C)C=CC=C1C GFNZJAUVJCGWLW-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 abstract 1
- 229910021627 Tin(IV) chloride Inorganic materials 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
- 239000004480 active ingredient Substances 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
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000001575 pathological effect Effects 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 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
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (22)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2525674A GB1456323A (en) | 1974-06-06 | 1974-06-06 | Benzothiophenes process for preparing them and pharmaceutical compositions containing the same |
| AR258913A AR207152A1 (es) | 1974-06-06 | 1975-01-01 | Procedimiento para preparar un nuevo derivado de 2-sustituido-3-(3,5-dimetil-4-dialquilaminoalcoxibenzoil)-benzo(b)-tiofeno |
| US05/569,819 US4007204A (en) | 1974-06-06 | 1975-04-21 | Benzothiophene compounds and the production and use thereof |
| NL7504921A NL7504921A (nl) | 1974-06-06 | 1975-04-25 | Benzo(b)thiofeen-verbindingen en werkwijze voor de bereiding daarvan. |
| ZA00752871A ZA752871B (en) | 1974-06-06 | 1975-05-02 | New heterocyclic compounds, process for preparing them and pharmaceutical compositions containing the same |
| AU81022/75A AU487367B2 (en) | 1974-06-06 | 1975-05-09 | Benzothiophenes, process for preparing them and pharmaceutical compositions containing thesame |
| SE7505482A SE7505482L (sv) | 1974-06-06 | 1975-05-13 | Benso(b)tiofenderivat och sett for framstellning derav |
| IT23297/75A IT1038094B (it) | 1974-06-06 | 1975-05-14 | Composti eterociclici derivati dal benzo b tiofene e composizioni farmaceutiche dello stesso nonche procedimento per la preparazione dei derivati del benzo b tiofene |
| DE19752522655 DE2522655A1 (de) | 1974-06-06 | 1975-05-22 | Benzo(b)thiophenverbindungen verfahren zu deren herstellung sowie diese enthaltende pharmazeutischen zusammensetzungen |
| HU75LA00000867A HU172820B (hu) | 1974-06-06 | 1975-05-30 | Sposob poluchenija proizvodnyih benzotiofena i farmacevticheskikh kompozicijj soderzhahhikh ikh aktivnymi agentami |
| FI751602A FI751602A7 (cg-RX-API-DMAC10.html) | 1974-06-06 | 1975-05-30 | |
| DK251975AA DK135808B (da) | 1974-06-06 | 1975-06-04 | Analogifremgangsmåde til fremstilling af benzo(b)thiophen-derivater eller syreadditionssalte deraf. |
| BE157003A BE829837A (fr) | 1974-06-06 | 1975-06-04 | Nouveaux derives du benzothiophene, leurs procedes de preparation ainsi que les compositions pharmaceutiques les contenant |
| NO751989A NO751989L (cg-RX-API-DMAC10.html) | 1974-06-06 | 1975-06-05 | |
| SU7502143254A SU578002A3 (ru) | 1974-06-06 | 1975-06-05 | Способ получени производных бензо(в)тиофена или их солей |
| OA55520A OA05022A (fr) | 1974-06-06 | 1975-06-06 | Procédé de préparation de nouveaux dérivés de benzothiophène. |
| AT431175A AT341517B (de) | 1974-06-06 | 1975-06-06 | Verfahren zur herstellung von neuen benzo(b)thiophenderivaten und von deren saureadditionssalzen |
| ES438303A ES438303A1 (es) | 1974-06-06 | 1975-06-06 | Procedimiento para preparar derivados de benzo (b) tiofeno. |
| CA228,687A CA1030972A (en) | 1974-06-06 | 1975-06-06 | Pharmacologically active benzo (b) thiophene compounds and process for their preparation |
| JP50069021A JPS516958A (en) | 1974-06-06 | 1975-06-06 | Benzo *b* chiofuenjudotainoseizoho |
| CH730375A CH605910A5 (cg-RX-API-DMAC10.html) | 1974-06-06 | 1975-06-06 | |
| AR261103A AR210265A1 (es) | 1974-06-06 | 1975-11-07 | Procedimiento para preparar un nuevo derivado del 2-sustituido-3-(3,5-dimetil-4dialquilamino propoxibenzoil)-benzo (b)tiofeno |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2525674A GB1456323A (en) | 1974-06-06 | 1974-06-06 | Benzothiophenes process for preparing them and pharmaceutical compositions containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1456323A true GB1456323A (en) | 1976-11-24 |
Family
ID=10224753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2525674A Expired GB1456323A (en) | 1974-06-06 | 1974-06-06 | Benzothiophenes process for preparing them and pharmaceutical compositions containing the same |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4007204A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS516958A (cg-RX-API-DMAC10.html) |
| AR (2) | AR207152A1 (cg-RX-API-DMAC10.html) |
| AT (1) | AT341517B (cg-RX-API-DMAC10.html) |
| BE (1) | BE829837A (cg-RX-API-DMAC10.html) |
| CA (1) | CA1030972A (cg-RX-API-DMAC10.html) |
| CH (1) | CH605910A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE2522655A1 (cg-RX-API-DMAC10.html) |
| DK (1) | DK135808B (cg-RX-API-DMAC10.html) |
| ES (1) | ES438303A1 (cg-RX-API-DMAC10.html) |
| FI (1) | FI751602A7 (cg-RX-API-DMAC10.html) |
| GB (1) | GB1456323A (cg-RX-API-DMAC10.html) |
| HU (1) | HU172820B (cg-RX-API-DMAC10.html) |
| IT (1) | IT1038094B (cg-RX-API-DMAC10.html) |
| NL (1) | NL7504921A (cg-RX-API-DMAC10.html) |
| NO (1) | NO751989L (cg-RX-API-DMAC10.html) |
| OA (1) | OA05022A (cg-RX-API-DMAC10.html) |
| SE (1) | SE7505482L (cg-RX-API-DMAC10.html) |
| SU (1) | SU578002A3 (cg-RX-API-DMAC10.html) |
| ZA (1) | ZA752871B (cg-RX-API-DMAC10.html) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| AU509682B2 (en) * | 1975-10-28 | 1980-05-22 | Eli Lilly And Company | 2-Aroyl-3-Phenylbenzothiophene Derivatives |
| US5175184A (en) * | 1982-10-19 | 1992-12-29 | Kotobuki Seiyaku Company Limited | Benzothiophene derivatives and antihyperuricemia thereof |
| NZ213986A (en) * | 1984-10-30 | 1989-07-27 | Usv Pharma Corp | Heterocyclic or aromatic compounds, and pharmaceutical compositions containing such |
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4912642A (en) * | 1987-09-03 | 1990-03-27 | The Boeing Company | Coordinated engine autothrottle |
| AU2543388A (en) * | 1987-09-30 | 1989-04-18 | University Of Tennessee Research Corporation, The | Certain 3-substituted 2-alkyl benzothiophene derivatives |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| JP3157882B2 (ja) * | 1991-11-15 | 2001-04-16 | 帝国臓器製薬株式会社 | 新規なベンゾチオフエン誘導体 |
| US5789436A (en) * | 1994-04-11 | 1998-08-04 | Chugai Seiyak Kabushiki Kaisha | 4,6 Di-t-butyl-5-hydroxy-2,3-dihydrobenzothiophene |
| CO4410190A1 (es) * | 1994-09-19 | 1997-01-09 | Lilly Co Eli | 3-[4-(2-AMINOETOXI)-BENZOIL]-2-ARIL-6-HIDROXIBENZO [b] TIOFENO CRISTALINO |
| US6653328B1 (en) * | 1995-03-10 | 2003-11-25 | Eli Lilly And Company | 3-benzyl-benzothiophenes |
| US6417199B1 (en) * | 1995-03-10 | 2002-07-09 | Eli Lilly And Company | 3-benzyl-benzothiophenes |
| CA2236007A1 (en) * | 1995-10-31 | 1997-07-17 | Gerald Floyd Smith | Antithrombotic diamines |
| JP2000506885A (ja) * | 1996-03-19 | 2000-06-06 | イーライ・リリー・アンド・カンパニー | ３―［４―（２―アミノエトキシ）ベンゾイル］―２―アリール―６―ヒドロキシベンゾ［ｂ］チオフェンの合成 |
| CA2287993A1 (en) | 1997-04-30 | 1998-11-05 | Mary George Johnson | Antithrombotic agents |
| AU7165398A (en) * | 1997-04-30 | 1998-11-24 | Eli Lilly And Company | A regioselective alkylation process for preparing substituted benzo{b}thiophenes |
| JP2002514217A (ja) | 1997-04-30 | 2002-05-14 | イーライ・リリー・アンド・カンパニー | 抗血栓物質 |
| EP1027051B1 (en) | 1997-04-30 | 2005-01-05 | Eli Lilly And Company | Antithrombotic agents |
| DE69824410T2 (de) | 1997-04-30 | 2005-06-02 | Eli Lilly And Co., Indianapolis | Antithrombosemittel |
| US6284756B1 (en) | 1998-04-30 | 2001-09-04 | Eli Lilly And Company | Antithrombotic agents |
| DE69904427T2 (de) * | 1998-10-28 | 2003-07-17 | Eli Lilly And Co., Indianapolis | Benzothiophenderivate als antithrombotische Mitteln und Zwischenprodukte |
| FR2864536B1 (fr) * | 2003-12-24 | 2006-03-17 | Clariant France Sa | Procede de preparation de n-alkyl-2 (hydroxy-4-benzoyl)-3 benzofurannes et intermediaires pour sa mise en oeuvre |
| NZ606595A (en) * | 2010-08-06 | 2014-08-29 | Tasly Pharmaceutical Group Co | Use of salvia miltiorrhiza composition in preparing drugs for secondary prevention of coronary heart disease |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3514465A (en) * | 1966-12-30 | 1970-05-26 | Degussa | Certain thiazolyl- and pyridinylaminoketones |
| US3706747A (en) * | 1970-06-05 | 1972-12-19 | Pfizer | Benzothieno(3,2-d)- and benzofuro(3,2-d)pyrimidines |
-
1974
- 1974-06-06 GB GB2525674A patent/GB1456323A/en not_active Expired
-
1975
- 1975-01-01 AR AR258913A patent/AR207152A1/es active
- 1975-04-21 US US05/569,819 patent/US4007204A/en not_active Expired - Lifetime
- 1975-04-25 NL NL7504921A patent/NL7504921A/xx not_active Application Discontinuation
- 1975-05-02 ZA ZA00752871A patent/ZA752871B/xx unknown
- 1975-05-13 SE SE7505482A patent/SE7505482L/xx unknown
- 1975-05-14 IT IT23297/75A patent/IT1038094B/it active
- 1975-05-22 DE DE19752522655 patent/DE2522655A1/de active Pending
- 1975-05-30 FI FI751602A patent/FI751602A7/fi not_active Application Discontinuation
- 1975-05-30 HU HU75LA00000867A patent/HU172820B/hu unknown
- 1975-06-04 DK DK251975AA patent/DK135808B/da unknown
- 1975-06-04 BE BE157003A patent/BE829837A/xx unknown
- 1975-06-05 SU SU7502143254A patent/SU578002A3/ru active
- 1975-06-05 NO NO751989A patent/NO751989L/no unknown
- 1975-06-06 ES ES438303A patent/ES438303A1/es not_active Expired
- 1975-06-06 JP JP50069021A patent/JPS516958A/ja active Pending
- 1975-06-06 CH CH730375A patent/CH605910A5/xx not_active IP Right Cessation
- 1975-06-06 AT AT431175A patent/AT341517B/de not_active IP Right Cessation
- 1975-06-06 OA OA55520A patent/OA05022A/xx unknown
- 1975-06-06 CA CA228,687A patent/CA1030972A/en not_active Expired
- 1975-11-07 AR AR261103A patent/AR210265A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| CH605910A5 (cg-RX-API-DMAC10.html) | 1978-10-13 |
| OA05022A (fr) | 1980-12-31 |
| ZA752871B (en) | 1976-04-28 |
| AT341517B (de) | 1978-02-10 |
| DE2522655A1 (de) | 1975-12-18 |
| FI751602A7 (cg-RX-API-DMAC10.html) | 1975-12-07 |
| DK251975A (cg-RX-API-DMAC10.html) | 1975-12-07 |
| AU8102275A (en) | 1976-11-11 |
| ES438303A1 (es) | 1977-01-16 |
| HU172820B (hu) | 1978-12-28 |
| SU578002A3 (ru) | 1977-10-25 |
| CA1030972A (en) | 1978-05-09 |
| IT1038094B (it) | 1979-11-20 |
| BE829837A (fr) | 1975-12-04 |
| US4007204A (en) | 1977-02-08 |
| DK135808C (cg-RX-API-DMAC10.html) | 1977-11-28 |
| AR210265A1 (es) | 1977-07-15 |
| ATA431175A (de) | 1977-06-15 |
| JPS516958A (en) | 1976-01-20 |
| SE7505482L (sv) | 1975-12-08 |
| NL7504921A (nl) | 1975-12-09 |
| AR207152A1 (es) | 1976-09-15 |
| DK135808B (da) | 1977-06-27 |
| NO751989L (cg-RX-API-DMAC10.html) | 1975-12-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] |