RU98103460A - DERIVATIVES OF BENZENESULPHONAMIDE, THEIR PRODUCTION AND THERAPEUTIC USE - Google Patents
DERIVATIVES OF BENZENESULPHONAMIDE, THEIR PRODUCTION AND THERAPEUTIC USEInfo
- Publication number
- RU98103460A RU98103460A RU98103460/04A RU98103460A RU98103460A RU 98103460 A RU98103460 A RU 98103460A RU 98103460/04 A RU98103460/04 A RU 98103460/04A RU 98103460 A RU98103460 A RU 98103460A RU 98103460 A RU98103460 A RU 98103460A
- Authority
- RU
- Russia
- Prior art keywords
- hydrogen atom
- pharmaceutically acceptable
- formula
- enantiomers
- branched
- Prior art date
Links
- KHBQMWCZKVMBLN-UHFFFAOYSA-N benzenesulfonimidic acid Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic Effects 0.000 title 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 22
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 10
- 239000011780 sodium chloride Substances 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 8
- 229910052801 chlorine Inorganic materials 0.000 claims 7
- 239000000460 chlorine Substances 0.000 claims 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004122 cyclic group Chemical group 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- YCKRFDGAMUMZLT-UHFFFAOYSA-N fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- DFRHZLORIBBQMD-UHFFFAOYSA-N 3-(2-amino-1-hydroxyethyl)-4-methoxybenzenesulfonamide Chemical compound COC1=CC=C(S(N)(=O)=O)C=C1C(O)CN DFRHZLORIBBQMD-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 150000007513 acids Chemical class 0.000 claims 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 2
- MDYSEIXCBRKUHV-UHFFFAOYSA-N 3-(2-amino-1-hydroxyethyl)-4-chlorobenzenesulfonamide Chemical compound NCC(O)C1=CC(S(N)(=O)=O)=CC=C1Cl MDYSEIXCBRKUHV-UHFFFAOYSA-N 0.000 claims 1
- LVLVILNNIYRTAM-UHFFFAOYSA-N 3-(2-amino-1-hydroxyethyl)-4-fluorobenzenesulfonamide Chemical compound NCC(O)C1=CC(S(N)(=O)=O)=CC=C1F LVLVILNNIYRTAM-UHFFFAOYSA-N 0.000 claims 1
- 239000012448 Lithium borohydride Substances 0.000 claims 1
- IJOOHPMOJXWVHK-UHFFFAOYSA-N Trimethylsilyl chloride Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N Trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims 1
- UAYWVJHJZHQCIE-UHFFFAOYSA-L Zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 150000008331 benzenesulfonamides Chemical class 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- NZTNZPDOBQDOSO-UHFFFAOYSA-N lithium;boron(1-) Chemical compound [Li+].[B-] NZTNZPDOBQDOSO-UHFFFAOYSA-N 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Claims (15)
в которой R1 представляет собой атом водорода, атом галогена, такого как хлор или фтор, или линейную или разветвленную С1-4алкильную или C1-4алкоксильную группу,
R2, R3 и R4 представляют собой, независимо друг от друга, атомы водорода или линейные, разветвленные или циклические С1-4алкильные группы, и
R5 представляет собой атом водорода или С1-2алкильную, C1-2фторалкильную или С1-2перфторалкильную группу, в форме энантиомеров или диастереоизомеров, или смесей этих различных форм, включая рацемические смеси, а также их соли, полученные присоединением фармацевтически приемлемых кислот.1. Benzenesulfonamide compounds of General formula (I)
in which R 1 represents a hydrogen atom, a halogen atom such as chlorine or fluorine, or a linear or branched C 1-4 alkyl or C 1-4 alkoxyl group,
R 2 , R 3 and R 4 are, independently of one another, hydrogen atoms or linear, branched or cyclic C 1-4 alkyl groups, and
R 5 represents a hydrogen atom or a C 1-2 alkyl, C 1-2 fluoroalkyl or C 1-2 perfluoroalkyl group, in the form of enantiomers or diastereoisomers, or mixtures of these various forms, including racemic mixtures, as well as pharmaceutically acceptable salts thereof acceptable acids.
в которой R1 представляет собой линейную или разветвленную С1-4алкоксильную группу, и R2 и R3 представляют собой атомы водорода, R4 представляет собой атом водорода или линейную, разветвленную или циклическую С1-4алкильную группу, и R5 представляет собой атом водорода,
в форме энантиомеров или диастереоизомеров, или смесей этих различных форм, включая рацемические смеси, а также их солей, полученных присоединением фармацевтически приемлемых кислот, при котором
(а) соединение формулы (III)
в которой R1 и R4 такие, как определено выше, подвергают взаимодействию с триметилсилилцианидом в присутствии иодида цинка с получением производного формулы (II)
в которой R1 и R4 такие, как определено выше, (б) восстанавливают полученное производное (II) боргидридом лития в присутствии триметилсилилхлорида с получением соединения формулы (I), (в) возможно превращают это полученное соединение (I) в его энантиомеры или диастереоизомеры, или в его фармацевтически приемлемые соли.14. A method of obtaining compounds of General formula (I)
in which R 1 represents a linear or branched C 1-4 alkoxyl group, and R 2 and R 3 represent hydrogen atoms, R 4 represents a hydrogen atom or a linear, branched or cyclic C 1-4 alkyl group, and R 5 represents a hydrogen atom
in the form of enantiomers or diastereoisomers, or mixtures of these various forms, including racemic mixtures, as well as their salts, obtained by the addition of pharmaceutically acceptable acids, in which
(a) a compound of formula (III)
wherein R 1 and R 4 , as defined above, are reacted with trimethylsilyl cyanide in the presence of zinc iodide to give a derivative of formula (II)
in which R 1 and R 4 are as defined above, (b) reducing the resulting derivative (II) with lithium borohydride in the presence of trimethylsilyl chloride to give a compound of formula (I), (c) possibly converting this obtained compound (I) to its enantiomers or diastereoisomers, or pharmaceutically acceptable salts thereof.
в которой R1 представляет собой атом водорода, атом галогена, такого как хлор или фтор, или линейную или разветвленную С1-4алкильную или C1-4алкоксильную группу, R2, R3 и R4 представляют собой, независимо друг от друга, атомы водорода или линейные, разветвленные или циклические С1-4алкильные группы, и R5 представляет собой атом водорода или С1-2алкильную, C1-2фторалкильную или С1-2перфторалкильную группу, в форме энантиомеров или диастереоизомеров, или смесей этих различных форм, включая рацемические смеси, а также их солей, полученных присоединением фармацевтически приемлемых кислот,
при котором (а) либо производное формулы (VIII)
в которой R4 и R5 такие, как определено выше,
в форме энантиомера или диастереоизомера, или смеси этих различных форм, включая рацемическую смесь, подвергают взаимодействию либо с водородом в присутствии катализатора, такого как палладий на угле, в случае, когда R1 такой, как определено выше, за исключением хлора, либо с трифенилфосфином и затем водным аммиаком в случае, когда R1 представляет собой атом хлора, для получения соединений общей формулы (I), в которой R1, R4 и R5 такие, как определено выше, и R2 и R3 представляют собой атомы водорода, (б) либо производное формулы (VII)
в которой R1, R4 и R5 такие, как определено выше, подвергают взаимодействию с амином формулы R2(R3)NH, в которой R2 представляет собой атом водорода или С1-4алкильную группу, и R3 представляет собой C1-4алкильную группу, с получением соединения общей формулы (I), в которой R2 и R3 такие, как определено выше, или с амином формулы R2(Bn)H, в которой R2 представляет собой алкильную группу, и Вn является бензильной группой, с получением производного формулы (VI), которое затем восстанавливают водородом в присутствии катализатора, такого как палладий на угле, с получением соединения общей формулы (I), в которой R2 представляет собой С1-4алкильную группу, (в) возможно превращают это результирующее соединение (I) в его энантиомеры или диастереоизомеры, или его фармацевтически приемлемые соли.15. The method of obtaining compounds of General formula (I)
in which R 1 represents a hydrogen atom, a halogen atom such as chlorine or fluorine, or a linear or branched C 1-4 alkyl or C 1-4 alkoxyl group, R 2 , R 3 and R 4 represent, independently of each other , hydrogen atoms or linear, branched or cyclic C 1-4 alkyl groups, and R 5 represents a hydrogen atom or a C 1-2 alkyl, C 1-2 fluoroalkyl or C 1-2 perfluoroalkyl group, in the form of enantiomers or diastereoisomers, or mixtures of these various forms, including racemic mixtures, as well as their salts obtained by adjoining insinuation of pharmaceutically acceptable acids
in which (a) either a derivative of the formula (VIII)
in which R 4 and R 5 are as defined above,
in the form of an enantiomer or diastereoisomer, or a mixture of these various forms, including the racemic mixture, is reacted either with hydrogen in the presence of a catalyst, such as palladium on charcoal, in the case where R 1 is as defined above, with the exception of chlorine, or with triphenylphosphine and then aqueous ammonia in the case where R 1 represents a chlorine atom, to obtain compounds of the general formula (I), in which R 1 , R 4 and R 5 are as defined above, and R 2 and R 3 are hydrogen atoms , (b) either a derivative of formula (VII)
in which R 1 , R 4 and R 5 are as defined above, are reacted with an amine of the formula R 2 (R 3 ) NH, in which R 2 represents a hydrogen atom or a C 1-4 alkyl group, and R 3 represents A C 1-4 alkyl group to give a compound of general formula (I) in which R 2 and R 3 are as defined above, or with an amine of formula R 2 (Bn) H in which R 2 is an alkyl group, and Bn is a benzyl group to give a derivative of formula (VI), which is then reduced with hydrogen in the presence of a catalyst, such as palladium on carbon, a compound of general formula (I), wherein R 2 represents a C 1-4 alkyl group, (c) optionally the resulting compound is converted to (I) to its enantiomers or diastereoisomers or its pharmaceutically acceptable salt.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR95/09503 | 1995-08-04 | ||
| FR9509503A FR2737494B1 (en) | 1995-08-04 | 1995-08-04 | BENZENESULFONAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU98103460A true RU98103460A (en) | 2000-01-10 |
| RU2160729C2 RU2160729C2 (en) | 2000-12-20 |
Family
ID=9481713
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU98103460/04A RU2160729C2 (en) | 1995-08-04 | 1996-08-01 | Benzenesulfonamide derivatives, preparation thereof and therapeutic use |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US6214882B1 (en) |
| EP (1) | EP0842148B1 (en) |
| JP (1) | JPH11510175A (en) |
| KR (1) | KR19990029070A (en) |
| CN (1) | CN1198735A (en) |
| AR (1) | AR003972A1 (en) |
| AT (1) | ATE198192T1 (en) |
| AU (1) | AU714948B2 (en) |
| BR (1) | BR9609698A (en) |
| CA (1) | CA2227912A1 (en) |
| CO (1) | CO4750816A1 (en) |
| CZ (1) | CZ30898A3 (en) |
| DE (1) | DE69611303T2 (en) |
| DK (1) | DK0842148T3 (en) |
| ES (1) | ES2154414T3 (en) |
| FR (1) | FR2737494B1 (en) |
| GR (1) | GR3035493T3 (en) |
| HK (1) | HK1010868A1 (en) |
| HU (1) | HUP9900064A3 (en) |
| IL (1) | IL123156A (en) |
| MX (1) | MX9800963A (en) |
| NO (1) | NO309563B1 (en) |
| NZ (1) | NZ315362A (en) |
| PL (1) | PL324778A1 (en) |
| PT (1) | PT842148E (en) |
| RU (1) | RU2160729C2 (en) |
| SK (1) | SK282423B6 (en) |
| TW (1) | TW336929B (en) |
| WO (1) | WO1997006136A1 (en) |
| ZA (1) | ZA966616B (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2761061B1 (en) * | 1997-03-20 | 1999-04-23 | Synthelabo | BENZENESULFONAMIDE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| FR2768055A1 (en) | 1997-09-11 | 1999-03-12 | Synthelabo | USE OF SULFONANILIDE DERIVATIVES FOR OBTAINING A MEDICAMENT FOR THE TREATMENT OF RETROGRADE EJACULATION OR ASPPERMIA |
| FR2768054A1 (en) * | 1997-09-11 | 1999-03-12 | Synthelabo | USE OF BENZENE SULFONAMIDE DERIVATIVES FOR OBTAINING A MEDICAMENT FOR THE TREATMENT OF RETROGRADE EJACULATION OR ASPERMIA |
| WO1999048864A1 (en) * | 1998-03-25 | 1999-09-30 | Godo Shusei Co., Ltd. | Sulfonylurea derivatives and drugs containing the same |
| DE60105020T2 (en) * | 2000-06-07 | 2005-08-18 | Almirall-Prodesfarma S.A. | 6-PHENYLPYRROLOPYRIMIDINDION DERIVATIVES |
| DE10104369A1 (en) * | 2001-02-01 | 2002-08-08 | Boehringer Ingelheim Pharma | Use of 2-amino- (4-hydroxy-2-methanesulfonamidophenyl) ethanol for the treatment of urinary incontinence |
| RU2435778C2 (en) * | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Ruthenium complex ligand, ruthenium complex, ruthenium complex catalyst and synthesis methods and use thereof |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3860647A (en) * | 1973-08-20 | 1975-01-14 | Smithkline Corp | {60 -Aminomethyl-4-hydroxy-3-sulfamyl-benzyl alcohols and 4-hydroxy-3-sulfamyl phenethylamines |
| US3943254A (en) * | 1973-08-20 | 1976-03-09 | Smithkline Corporation | Beta-adrenergic antagonists |
| GB1593651A (en) * | 1977-02-03 | 1981-07-22 | Allen & Hanburys Ltd | Amides |
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| JPS6051106A (en) * | 1983-08-31 | 1985-03-22 | Yamanouchi Pharmaceut Co Ltd | Long acting pharmaceutical preparation of amosulalol hydrochloride |
| FR2581993B1 (en) | 1985-05-14 | 1988-03-18 | Synthelabo | (BENZOYL-4 PIPERIDINO) -2 PHENYL-1 ALCANOLS DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
| ES2078507T3 (en) | 1990-02-07 | 1995-12-16 | Nippon Shinyaku Co Ltd | MEDICINES AND DERIVATIVES OF SULFONANILIDE. |
| GB9020695D0 (en) * | 1990-09-22 | 1990-11-07 | Wellcome Found | Anti-hypertensive tetralins |
| EP0642789B1 (en) * | 1992-05-22 | 1999-09-29 | Senju Pharmaceutical Co., Ltd. | Remedy for glaucoma |
-
1995
- 1995-08-04 FR FR9509503A patent/FR2737494B1/en not_active Expired - Fee Related
-
1996
- 1996-07-31 AR ARP960103821A patent/AR003972A1/en unknown
- 1996-08-01 SK SK146-98A patent/SK282423B6/en unknown
- 1996-08-01 ES ES96927119T patent/ES2154414T3/en not_active Expired - Lifetime
- 1996-08-01 BR BR9609698A patent/BR9609698A/en not_active Application Discontinuation
- 1996-08-01 AT AT96927119T patent/ATE198192T1/en not_active IP Right Cessation
- 1996-08-01 CA CA002227912A patent/CA2227912A1/en not_active Abandoned
- 1996-08-01 PL PL96324778A patent/PL324778A1/en unknown
- 1996-08-01 DK DK96927119T patent/DK0842148T3/en active
- 1996-08-01 AU AU67052/96A patent/AU714948B2/en not_active Ceased
- 1996-08-01 CN CN96197428A patent/CN1198735A/en active Pending
- 1996-08-01 RU RU98103460/04A patent/RU2160729C2/en active
- 1996-08-01 KR KR1019980700374A patent/KR19990029070A/en not_active Application Discontinuation
- 1996-08-01 JP JP9508160A patent/JPH11510175A/en active Pending
- 1996-08-01 DE DE69611303T patent/DE69611303T2/en not_active Expired - Fee Related
- 1996-08-01 IL IL12315696A patent/IL123156A/en not_active IP Right Cessation
- 1996-08-01 MX MX9800963A patent/MX9800963A/en unknown
- 1996-08-01 HU HU9900064A patent/HUP9900064A3/en unknown
- 1996-08-01 US US09/000,336 patent/US6214882B1/en not_active Expired - Fee Related
- 1996-08-01 WO PCT/FR1996/001215 patent/WO1997006136A1/en not_active Application Discontinuation
- 1996-08-01 EP EP96927119A patent/EP0842148B1/en not_active Expired - Lifetime
- 1996-08-01 NZ NZ315362A patent/NZ315362A/en unknown
- 1996-08-01 CZ CZ98308A patent/CZ30898A3/en unknown
- 1996-08-01 PT PT96927119T patent/PT842148E/en unknown
- 1996-08-02 ZA ZA9606616A patent/ZA966616B/en unknown
- 1996-08-02 TW TW085109360A patent/TW336929B/en active
- 1996-08-02 CO CO96041035A patent/CO4750816A1/en unknown
-
1998
- 1998-02-03 NO NO980471A patent/NO309563B1/en not_active IP Right Cessation
- 1998-11-20 HK HK98112150A patent/HK1010868A1/en not_active IP Right Cessation
-
2001
- 2001-02-28 GR GR20010400336T patent/GR3035493T3/en not_active IP Right Cessation
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