ES404252A1 - Benzothiophene derivatives and process for preparing the same - Google Patents
Benzothiophene derivatives and process for preparing the sameInfo
- Publication number
- ES404252A1 ES404252A1 ES404252A ES404252A ES404252A1 ES 404252 A1 ES404252 A1 ES 404252A1 ES 404252 A ES404252 A ES 404252A ES 404252 A ES404252 A ES 404252A ES 404252 A1 ES404252 A1 ES 404252A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- benzo
- thiophene
- general formula
- derivative
- 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 2
- 238000004519 manufacturing process Methods 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical group C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 abstract 2
- 150000004802 benzothiophens Chemical class 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229930192474 thiophene Natural products 0.000 abstract 2
- AWLJKCAIKWWAFR-UHFFFAOYSA-N 1-N,1-N-dibutyl-2-N,2-N-diethyl-3-N,3-N-dimethyl-2-N',2-N'-dipropylpyrrolidine-1,2,2,3-tetramine Chemical compound CCCCN(CCCC)N1CCC(N(C)C)C1(N(CC)CC)N(CCC)CCC AWLJKCAIKWWAFR-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000005605 benzo group Chemical group 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
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
Procedure for the preparation of derivatives of benzo [b] thiophene, of general formula: **(See formula)** and its pharmaceutically acceptable acid addition salts, in which formula R represents hydrogen or a straight or branched chain alkyl group containing 1 to 4 carbon atoms, R'represents hydrogen or methyl, X and X1 being identical, represent each a chlorine, bromine or iodine atom, Am represents a dimethylamino, diethylamino, di-n-propylamino, di-n-butylamino, pyrrolidine, piperidine or perhydroazepine group and n is an integer of the order of 1 to 5 inclusive; characterized in that a properly substituted benzo [b] thiophene derivative of general formula: **(See formula)** in which R, X and X1 have the same meanings as those previously described, it is condensed, in an alkaline medium, with a dibromoalkane of the general formula: **(See formula)** wherein R'and n are defined as above, to form a substituted bromoalkoxy-benzoyl-benzo [b] thiophene of general formula: **(See formula)** wherein R, R', X, X1 and n are defined as above, and said bromoalkoxy-benzoyl-benzo [7] thiophene is further condensed with dimethylamine, diethylamine, di-n-propylamine, di-n-butylamine, pyrrolidine, piperidine or perhydroazepine, to form the required benzo [b] thiophene derivative of formula I which, if desired, is reacted with an appropriate acid to provide a pharmaceutically acceptable acid addition salt of the benzo derivative [b] thiophene of formula I. (Machine-translation by Google Translate, not legally binding)
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 (1)
| Publication Number | Publication Date |
|---|---|
| ES404252A1 true ES404252A1 (en) | 1975-06-01 |
Family
ID=10301169
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES404252A Expired ES404252A1 (en) | 1971-06-25 | 1972-06-24 | Benzothiophene derivatives and process for preparing the 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 SE SE7208187A patent/SE385482B/en unknown
- 1972-06-21 CH CH1795273A patent/CH548409A/en not_active IP Right Cessation
- 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 CA CA145,600A patent/CA959492A/en not_active Expired
- 1972-06-23 SU SU1800666A patent/SU453844A3/ru active
- 1972-06-23 DE DE19722230669 patent/DE2230669A1/en active Pending
- 1972-06-23 SU SU721959344A patent/SU486510A3/en active
- 1972-06-24 ES ES404252A patent/ES404252A1/en not_active Expired
- 1972-06-24 JP JP47063621A patent/JPS4844248A/ja active Pending
- 1972-06-26 OA OA54619A patent/OA04117A/en unknown
- 1972-06-26 AT AT545972A patent/AT312597B/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4844248A (en) | 1973-06-26 |
| GB1357212A (en) | 1974-06-19 |
| BE784260A (en) | 1972-12-01 |
| DE2230669A1 (en) | 1972-12-28 |
| SU486510A3 (en) | 1975-09-30 |
| FI54477C (en) | 1978-12-11 |
| FR2143250A1 (en) | 1973-02-02 |
| AT312597B (en) | 1974-01-10 |
| IE36485B1 (en) | 1976-11-10 |
| CH548409A (en) | 1974-04-30 |
| OA04117A (en) | 1979-11-30 |
| CH549042A (en) | 1974-05-15 |
| CA959492A (en) | 1974-12-17 |
| ZA723868B (en) | 1973-03-28 |
| FR2143250B1 (en) | 1975-06-20 |
| IE36485L (en) | 1972-12-25 |
| SE385482B (en) | 1976-07-05 |
| SU453844A3 (en) | 1974-12-15 |
| AU462617B2 (en) | 1975-06-10 |
| AU4333872A (en) | 1973-12-20 |
| HU166255B (en) | 1975-02-28 |
| NL7208703A (en) | 1972-12-28 |
| FI54477B (en) | 1978-08-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES438303A1 (en) | PROCEDURE FOR PREPARING BENZO (B) THIOPHENE DERIVATIVES. | |
| ES418892A1 (en) | Certain 3-substituted amino alkoxy benzoyl-2-lower alkyl or 2-cycloalkyl benzofurans | |
| ES456610A1 (en) | Therapeutic sulfonamides | |
| ES410731A1 (en) | Alpha-aryl-4-substituted piperidinoalkanol derivatives | |
| ES404252A1 (en) | Benzothiophene derivatives and process for preparing the same | |
| ES369919A1 (en) | N-(morpholino alkyl)-benzo{8 b{9 thiophene-2-carboxamides | |
| GB1318291A (en) | Carboxamide derivatives and fungicidal compositions containing them | |
| DK120483D0 (en) | PHENYL PIPERAZINE DERIVATIVES AND PROCEDURES FOR THEIR PREPARATION | |
| ES437790A1 (en) | PROCEDURE FOR PREPARING PHARMACEUTICAL AND VETERINARY COMPOSITIONS. | |
| ES423958A1 (en) | Process for the manufacture of indole derivatives | |
| ES436883A1 (en) | Alkanolamine derivatives | |
| AU4301189A (en) | New thienyloxy-alkylamine derivates, their process of production and medicaments containing these compounds | |
| ES419142A1 (en) | 2-2-2-methyl-5-nitro-1-imidazolyl-ethyl-2-thiopseudoureas and related compounds | |
| GB1080496A (en) | Improvements in or relating to a new derivatives of 2,4,6-triiodo-3-hydroxy-benzene and process for preparing the same | |
| ES8401957A1 (en) | Preparation of thiophene compounds | |
| GB2012762A (en) | 5,6-dihydro prostacyclin derivatives | |
| US4027030A (en) | Certain thiazole-carboxamides and their pharmaceutical utility | |
| ES432790A1 (en) | A method for producing derivatives of 2-chloropropic acid. (Machine-translation by Google Translate, not legally binding) | |
| KR800000058B1 (en) | Process for preparing benzocycloheptathiphene derivatives | |
| ES459400A1 (en) | 6,11-dihydrodibenzo - thiepin - 11 - ones methods of preparation compositions and uses thereof | |
| ES371236A1 (en) | Procedure for the preparation of new benzofuran derivatives. (Machine-translation by Google Translate, not legally binding) | |
| IE44414L (en) | Furan and thiophene compounds | |
| ES465366A2 (en) | 2-methoxybenzamides | |
| ES411984A1 (en) | Nitrogen containing isoprenoid compounds | |
| ES405913A3 (en) | Procedure for the preparation of derivatives of alcohilxantina basically substituted. (Machine-translation by Google Translate, not legally binding) |