N-(2-Ethyl-2,3-dihydro-1H-isoindol-5-yl)-4-methyl-benzenesulfonamide | 3606-74-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-Ethyl-2,3-dihydro-1H-isoindol-5-yl)-4-methyl-benzenesulfonamide
• 英文别名: N-(2-ethyl-1,3-dihydroisoindol-5-yl)-4-methylbenzenesulfonamide
• CAS: 3606-74-4
• 化学式: C₁₇H₂₀N₂O₂S
• 分子量: 316.424
• InChiKey: WVRQMBRPNVSPAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

文献信息

• Benzenesulfonamide derivatives
  申请人：Cooper G David

  公开号：US20050085461A1

  公开（公告）日：2005-04-21

  The invention provides compounds of formula (I) wherein A and B represent the groups CH 2 ) m — and CH 2 ) n — respectively; R 1 represents hydrogen or C 1-4 alkyl; R 2 represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC 1-6 alkyl, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, C 1-6 alkoxy, —(CH 2 ) p C 3-6 cycloalkyl, —(CH 2 ) p C 3-6 cycloalkyloxy, —COC 1-6 alkyl, —SO 2 C 1-6 alkyl, —SOC 1-6 alkyl, —S-C 1-6 alkyl, —CO 2 C 1-6 alkyl, —CO 2 NR 7 R 8 , —SO 2 NR 7 R 8 , —(CH 2 ) p NR 7 R 8 , —(CH 2 ) p NR 7 COR 8 , optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R 3 represents hydrogen or C 1-6 alkyl; R 4 represents halogen, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, C 1-6 alkoxy, —(CH 2 ) p C 3-6 cycloalkyl or —(CH 2 ) p C 3-6 cycloalkyloxy; R 5 and R 6 each independently represent hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC 1-6 alkyl, trifluoromethyl, trifluoromethoxy, C 1-6 alkyl, C 1-6 alkoxy, —(CH 2 ) p C 3-6 cycloalkyl, —(CH 2 ) p C 3-6 cycloalkyloxy, —COC 1-6 alkyl, —SO 2 C 1-6 alkyl, —SOC 1-6 alkyl, —S—C 1-6 alkyl, —CO 2 C 1-6 alkyl, —CO 2 NR 7 R 8 , —SO 2 NR 7 R 8 , —(CH 2 ) p NR 7 R 8 , —(CH 2 ) p NR 7 COR 8 , optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R 7 and R 8 each independently represent hydrogen or C 1-6 alkyl; m and n independently represent an integer selected from 1 and 2; p independently represents an integer selected from 0, 1, 2 and 3; or a pharmaceutically acceptable salt or solvate thereof, with the proviso that the compounds 4-methyl-N-(1,2,3,4-tetrahydroisoquinolin-6-yl)-benzenesulfonamide, 7-(4-chlorophenyl)sulfonamido-1,2,3,4-tetrahydroisoquinoline hydrochloride and N-(2-ethyl-5-isoindolinyl)-p-toluenesulfonamide are excluded. The compounds are useful in therapy, in particular as antipsychotic agents.

  该发明提供了式（I）的化合物，其中A和B分别代表基团CH2）m-和 ）n-; R1代表氢或C1-4烷基; R2代表氢，卤素，羟基，氰基，硝基，羟基C1-6烷基，三氟甲基，三氟甲氧基，C1-6烷基，C1-6烷氧基， -（ ）pC3-6环烷基， -（ ）pC3-6环烷氧基， -COC1-6烷基， -SO2C1-6烷基， -SOC1-6烷基， -S-C1-6烷基， -CO2C1-6烷基， -CO2NR7R8， -SO2NR7R8， -（ ）pNR7R8， -（ ）pNR7COR8，可选地取代的芳基，可选地取代的杂环芳基或融合的双环杂环环系; R3代表氢或C1-6烷基; R4代表卤素，三氟甲基，三氟甲氧基，C1-6烷基，C1-6烷氧基， -（ ）pC3-6环烷基或 -（ ）pC3-6环烷氧基; R5和R6各自独立地代表氢，卤素，羟基，氰基，硝基，羟基C1-6烷基，三氟甲基，三氟甲氧基，C1-6烷基，C1-6烷氧基， -（ ）pC3-6环烷基， -（ ）pC3-6环烷氧基， -COC1-6烷基， -SO2C1-6烷基， -SOC1-6烷基， -S-C1-6烷基， -CO2C1-6烷基， -CO2NR7R8， -SO2NR7R8， -（ ）pNR7R8， -（ ）pNR7COR8，可选地取代的芳基，可选地取代的杂环芳基或融合的双环杂环环系; R7和R8各自独立地代表氢或C1-6烷基; m和n各自独立地代表选自1和2的整数; p独立地代表选自0、1、2和3的整数; 或其药学上可接受的盐或溶剂，但不包括4-甲基-N-（1,2,3,4-四氢异喹啉-6-基）-苯磺酰胺，7-（4-氯苯基）磺酰胺-1,2,3,4-四氢异喹啉盐酸盐和N-（2-乙基-5-异吲哚基）-对甲苯磺酰胺。该化合物在治疗中有用，特别是作为抗精神病药物。
• BENZENESULFONAMIDE DERIVATIVES AND THEIR USE AS DOPAMINE D3 AND D2 RECEPTOR LIGANDS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1495004A2

  公开（公告）日：2005-01-12
• [EN] BENZENESULFONAMIDE DERIVATIVES<br/>[FR] DERIVES BENZENESULFONAMIDE
  申请人：GLAXO GROUP LTD

  公开号：WO2003068732A2

  公开（公告）日：2003-08-21

  The invention provides compounds of formula (I) wherein A and B represent the groups -(CH2)m- and -(CH2)n- respectively; R1 represents hydrogen or C1-6alkyl; R2 represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC1-6alkyl, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl, -(CH2)pC3-6cycloalkyloxy, -COC1-6alkyl, -SOC1-6alkyl, -SOC1-6alkyl, -S-C1-6alkyl, -COC1-6alkyl, -CO2NR7R8, -SO2NR7R8, -(CH2)pNR7R8, -(CH2)pNR7COR8, optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R3 represents hydrogen or C1-6alkyl; R4 represents halogen, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl or -(CH2)pC3-6cycloalkyloxy; R5 and R6 each independently represent hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC1-6alkyl, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl, -(CH2)pC3-6cycloalkyloxy, -COC1-6alkyl, -SO2C1-6alkyl, -SOC1-6alkyl, -S-C1-6alkyl, -CO2C1-6alkyl, -CO2NR7R8, -SO2NR7R8, -(CH2)pNR7R8, -(CH2)pNR7COR8, optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R7 and R8 each independently represent hydrogen or C1-6alkyl;m and n independently represent an integer selected from 1 and 2;p independently represents an integer selected from 0, 1, 2 and 3; or a pharmaceutically acceptable salt or solvate thereof,with the proviso that the compounds 4-methyl-N-(1,2,3,4-tetrahydroisoquinolin-6-yl)-benzenesulfonamide, 7-(4-chlorophenyl)sulfonamido-1,2,3,4-tetrahydroisoquinoline hydrochloride and N-(2-ethyl-5-isoindolinyl)-p-toluenesulfonamide are excluded.The compounds are useful in therapy, in particular as antipsychotic agents.
• [EN] BENZENESULFONAMIDE DERIVATIVES AND THEIR USE AS DOPAMINE D3 AND D2 RECEPTOR LIGA DS<br/>[FR] DERIVES BENZENESULFONAMIDE
  申请人：——

  公开号：WO2003068732A3

  公开（公告）日：2004-04-08

  [EN] The invention provides compounds of formula (I) wherein A and B represent the groups -(CH2)m- and -(CH2)n- respectively; R<1> represents hydrogen or C1-6alkyl; R<2> represents hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC1-6alkyl, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl, -(CH2)pC3-6cycloalkyloxy, -COC1-6alkyl, -SOC1-6alkyl, -SOC1-6alkyl, -S-C1-6alkyl, -COC1-6alkyl, -CO2NR<7>R<8>, -SO2NR<7>R<8>, -(CH2)pNR<7>R<8>, -(CH2)pNR<7>COR<8>, optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R<3> represents hydrogen or C1-6alkyl; R<4> represents halogen, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl or -(CH2)pC3-6cycloalkyloxy; R<5> and R<6> each independently represent hydrogen, halogen, hydroxy, cyano, nitro, hydroxyC1-6alkyl, trifluoromethyl, trifluoromethoxy, C1-6alkyl, C1-6alkoxy, -(CH2)pC3-6cycloalkyl, -(CH2)pC3-6cycloalkyloxy, -COC1-6alkyl, -SO2C1-6alkyl, -SOC1-6alkyl, -S-C1-6alkyl, -CO2C1-6alkyl, -CO2NR<7>R<8>, -SO2NR<7>R<8>, -(CH2)pNR<7>R<8>, -(CH2)pNR<7>COR<8>, optionally substituted aryl, optionally substituted heteroaryl or a fused bicyclic heterocyclic ring system; R<7> and R<8> each independently represent hydrogen or C1-6alkyl;m and n independently represent an integer selected from 1 and 2;p independently represents an integer selected from 0, 1, 2 and 3; or a pharmaceutically acceptable salt or solvate thereof,with the proviso that the compounds 4-methyl-N-(1,2,3,4-tetrahydroisoquinolin-6-yl)-benzenesulfonamide, 7-(4-chlorophenyl)sulfonamido-1,2,3,4-tetrahydroisoquinoline hydrochloride and N-(2-ethyl-5-isoindolinyl)-p-toluenesulfonamide are excluded.The compounds are useful in therapy, in particular as antipsychotic agents.
  [FR] La présente invention concerne des composés, ou l'un de leurs sels ou solvats pharmaceutiquement admis, représentés par la formule générale (I) dans laquelle A est un groupe -(CH2)m- et B un groupe -(CH2)n-. Dans cette formule, R<1> est hydrogène ou C1- C 6 alkyle; R<2> est hydrogène, halogène, hydroxy, cyano, nitro, hydroxy C1- C 6 alkyle, trifluorométhyle, trifluorométhoxy, C1-C 6 alkyle, C1-C6 alcoxy, -(CH2)p C3-C6 cycloalkyle, -(CH2)p C3-C6 cycloalkyloxy, -CO C1-C6 alkyle, -SO C1-C6 alkyle, -SO C1-6 alkyle, -S- C1-C6 alkyle, -CO C1-C6 alkyle, -CO2NR<7>R<8>, -SO2NR<7>R<8>, -(CH2)pNR<7>R<8>, -(CH2)pNR<7>COR<8>, aryle éventuellement substitué, hétéroaryle éventuellement substitué, ou un système de noyaux hétérocycliques bicycliques fusionnés; R<3> est hydrogène ou C1-C6 alkyle; R<4> est halogène, trifluorométhyle, trifluorométhoxy, C1-C6 alkyle, C1-C6 alcoxy, -(CH2)p C3-C6 cycloalkyle ou -(CH2)p C3-C6 cycloalkyloxy; R<5> et R<6> sont chacun indépendamment hydrogène, halogène, hydroxy, cyano, nitro, hydroxy C1-C6 alkyle, trifluorométhyle, trifluorométhoxy, C1-C6 alkyle, C1-C6 alcoxy, -(CH2)p C3-C6 cycloalkyle, -(CH2)p C3-C6 cycloalkyloxy, -CO C1-C6 alkyle, -SO2 C1-C6 alkyle, -SO C1-C6 alkyle, -S- C1-C6 alkyle, -CO2 C1-C6 alkyle, -CO2NR<7>R<8>, -SO2NR<7>R<8>, -(CH2)pNR<7>R<8>, -(CH2)pNR<7>COR<8>, aryle éventuellement substitué, hétéroaryle éventuellement substitué, ou un système de noyaux hétérocycliques bicycliques fusionnés; R<7> et R<8> sont chacun indépendamment hydrogène ou C1-C6 alkyle; m et n sont indépendamment un entier valant 1 ou 2; p est indépendamment un entier valant 0, 1, 2 ou 3. Toutefois sont exclus les composés 4-méthyl-N-(1,2,3,4-tétrahydroisoquinolin-6-yl)-benzènesulfonamide, 7-(4-chlorophényl)sulfonamido-1,2,3,4-tétrahydroisoquinoline hydrochlorure et N-(2-éthyl-5-isoindolinyl)-p-toluènesulfonamide. Ces composés convient comme agent thérapeutique, plus particulièrement comme antipsychotiques.