SU578002A3 - Способ получени производных бензо(в)тиофена или их солей - Google Patents
Способ получени производных бензо(в)тиофена или их солейInfo
- Publication number
- SU578002A3 SU578002A3 SU7502143254A SU2143254A SU578002A3 SU 578002 A3 SU578002 A3 SU 578002A3 SU 7502143254 A SU7502143254 A SU 7502143254A SU 2143254 A SU2143254 A SU 2143254A SU 578002 A3 SU578002 A3 SU 578002A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzo
- thiophene
- ethyl
- salts
- benzene
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 7
- 150000003839 salts Chemical class 0.000 title description 2
- 150000004802 benzothiophens Chemical class 0.000 title 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 26
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 18
- 229930192474 thiophene Natural products 0.000 description 13
- 125000005605 benzo group Chemical group 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 4
- 235000006408 oxalic acid Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 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 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- DWQVMSLZCNGRDU-UHFFFAOYSA-N oxalic acid;thiophene Chemical compound C=1C=CSC=1.OC(=O)C(O)=O DWQVMSLZCNGRDU-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- BUNROVZNGITPIX-UHFFFAOYSA-N zinc;benzene Chemical compound [Zn+2].C1=CC=[C-]C=C1.C1=CC=[C-]C=C1 BUNROVZNGITPIX-UHFFFAOYSA-N 0.000 description 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
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 |
|---|---|
| SU578002A3 true SU578002A3 (ru) | 1977-10-25 |
Family
ID=10224753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502143254A SU578002A3 (ru) | 1974-06-06 | 1975-06-05 | Способ получени производных бензо(в)тиофена или их солей |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4007204A (OSRAM) |
| JP (1) | JPS516958A (OSRAM) |
| AR (2) | AR207152A1 (OSRAM) |
| AT (1) | AT341517B (OSRAM) |
| BE (1) | BE829837A (OSRAM) |
| CA (1) | CA1030972A (OSRAM) |
| CH (1) | CH605910A5 (OSRAM) |
| DE (1) | DE2522655A1 (OSRAM) |
| DK (1) | DK135808B (OSRAM) |
| ES (1) | ES438303A1 (OSRAM) |
| FI (1) | FI751602A7 (OSRAM) |
| GB (1) | GB1456323A (OSRAM) |
| HU (1) | HU172820B (OSRAM) |
| IT (1) | IT1038094B (OSRAM) |
| NL (1) | NL7504921A (OSRAM) |
| NO (1) | NO751989L (OSRAM) |
| OA (1) | OA05022A (OSRAM) |
| SE (1) | SE7505482L (OSRAM) |
| SU (1) | SU578002A3 (OSRAM) |
| ZA (1) | ZA752871B (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU509682B2 (en) * | 1975-10-28 | 1980-05-22 | Eli Lilly And Company | 2-Aroyl-3-Phenylbenzothiophene Derivatives |
| US4133814A (en) * | 1975-10-28 | 1979-01-09 | Eli Lilly And Company | 2-Phenyl-3-aroylbenzothiophenes useful as antifertility agents |
| 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 |
| US4851554A (en) * | 1987-04-06 | 1989-07-25 | University Of Tennessee Research Corporation | Certain 3-substituted 2-alkyl benzofuran derivatives |
| US4806663A (en) * | 1987-04-06 | 1989-02-21 | The 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 |
| US4831156A (en) * | 1987-09-30 | 1989-05-16 | The University Of Tennessee Research Corp. | 3-substituted 2-alkyl indole derivatives |
| AU2543388A (en) * | 1987-09-30 | 1989-04-18 | University Of Tennessee Research Corporation, The | Certain 3-substituted 2-alkyl benzothiophene 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 |
| ES2173182T3 (es) * | 1994-04-11 | 2002-10-16 | Chugai Pharmaceutical Co Ltd | Derivado de 4,6-dl-butil-2,3-dihidrobenzotiofenos como antioxidantes de ldl. |
| CO4410191A1 (es) * | 1994-09-19 | 1997-01-09 | Lilly Co Eli | SINTESIS DE 3-[4-(2-AMINOETOXI)BENZOIL]-2-ARIL-6- HIDROXIBENZO [b] TIOFENOS |
| US6417199B1 (en) * | 1995-03-10 | 2002-07-09 | Eli Lilly And Company | 3-benzyl-benzothiophenes |
| US6653328B1 (en) * | 1995-03-10 | 2003-11-25 | 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 |
| EP0980367A4 (en) | 1997-04-30 | 2003-03-19 | Lilly Co Eli | ANTITHROMBOTIC AGENTS |
| 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 |
| KR20010020379A (ko) * | 1997-04-30 | 2001-03-15 | 피터 지. 스트링거 | 치환된 벤조[ｂ]티오펜을 제조하기 위한 레지오선택적 알킬화 방법 |
| DE69824410T2 (de) | 1997-04-30 | 2005-06-02 | Eli Lilly And Co., Indianapolis | Antithrombosemittel |
| JP2002501503A (ja) | 1997-04-30 | 2002-01-15 | イーライ・リリー・アンド・カンパニー | 抗血栓症剤 |
| US6284756B1 (en) | 1998-04-30 | 2001-09-04 | Eli Lilly And Company | Antithrombotic agents |
| DK0997460T3 (da) * | 1998-10-28 | 2003-03-31 | Lilly Co Eli | Benzothiophenforbindelser som antithrombotiske midler og mellemprodukter |
| 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 |
| EP2601958B1 (en) * | 2010-08-06 | 2017-03-29 | Tasly Pharmaceutical Group Co., Ltd. | 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 HU HU75LA00000867A patent/HU172820B/hu unknown
- 1975-05-30 FI FI751602A patent/FI751602A7/fi not_active Application Discontinuation
- 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 AT AT431175A patent/AT341517B/de not_active IP Right Cessation
- 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 OA OA55520A patent/OA05022A/xx unknown
- 1975-06-06 CA CA228,687A patent/CA1030972A/en not_active Expired
- 1975-06-06 ES ES438303A patent/ES438303A1/es not_active Expired
- 1975-11-07 AR AR261103A patent/AR210265A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| CA1030972A (en) | 1978-05-09 |
| DE2522655A1 (de) | 1975-12-18 |
| BE829837A (fr) | 1975-12-04 |
| AR210265A1 (es) | 1977-07-15 |
| US4007204A (en) | 1977-02-08 |
| AU8102275A (en) | 1976-11-11 |
| AR207152A1 (es) | 1976-09-15 |
| DK135808B (da) | 1977-06-27 |
| SE7505482L (sv) | 1975-12-08 |
| ES438303A1 (es) | 1977-01-16 |
| DK135808C (OSRAM) | 1977-11-28 |
| CH605910A5 (OSRAM) | 1978-10-13 |
| GB1456323A (en) | 1976-11-24 |
| IT1038094B (it) | 1979-11-20 |
| HU172820B (hu) | 1978-12-28 |
| ATA431175A (de) | 1977-06-15 |
| FI751602A7 (OSRAM) | 1975-12-07 |
| NO751989L (OSRAM) | 1975-12-09 |
| OA05022A (fr) | 1980-12-31 |
| NL7504921A (nl) | 1975-12-09 |
| AT341517B (de) | 1978-02-10 |
| DK251975A (OSRAM) | 1975-12-07 |
| JPS516958A (en) | 1976-01-20 |
| ZA752871B (en) | 1976-04-28 |
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