JP2003510319A5 - - Google Patents
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- Publication number
- JP2003510319A5 JP2003510319A5 JP2001526530A JP2001526530A JP2003510319A5 JP 2003510319 A5 JP2003510319 A5 JP 2003510319A5 JP 2001526530 A JP2001526530 A JP 2001526530A JP 2001526530 A JP2001526530 A JP 2001526530A JP 2003510319 A5 JP2003510319 A5 JP 2003510319A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonyl
- methyl
- thien
- piperidin
- benzamide
- 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.)
- Granted
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- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 377
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 183
- -1 piperazino group Chemical group 0.000 description 139
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 111
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 101
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 45
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 11
- 229910052757 nitrogen Inorganic materials 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 4
- 229940124530 sulfonamide Drugs 0.000 description 4
- 150000003456 sulfonamides Chemical class 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 3
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000005605 benzo group Chemical group 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- KVVBPLSURQZWBX-UHFFFAOYSA-N n-[[5-[[3-benzyl-7-cyano-1-(1h-imidazol-5-ylmethyl)-3,5-dihydro-2h-1,4-benzodiazepin-4-yl]sulfonyl]thiophen-2-yl]methyl]benzamide Chemical compound C=1C=CC=CC=1C(=O)NCC(S1)=CC=C1S(=O)(=O)N(C(C1)CC=2C=CC=CC=2)CC2=CC(C#N)=CC=C2N1CC1=CNC=N1 KVVBPLSURQZWBX-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- VPKKBWBYGRMALQ-UHFFFAOYSA-N 1-$l^{1}-azanylpyrrolidine Chemical compound [N]N1CCCC1 VPKKBWBYGRMALQ-UHFFFAOYSA-N 0.000 description 2
- 125000006334 2,4-difluoro benzoyl group Chemical group [H]C1=C([H])C(C(*)=O)=C(F)C([H])=C1F 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- PTRWZUIFMORETL-UHFFFAOYSA-N 4-azatricyclo[9.4.0.03,8]pentadeca-1(15),2,5,7,9,11,13-heptaene Chemical compound C1=CC2=CC=CC=C2C=C2NC=CC=C21 PTRWZUIFMORETL-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 125000001072 heteroaryl group Chemical group 0.000 description 2
- 229940095102 methyl benzoate Drugs 0.000 description 2
- QFFCMSVSOLNBCG-UHFFFAOYSA-N n-[[5-(4-heptanoylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]-3-methoxybenzamide Chemical compound C1CC(C(=O)CCCCCC)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=CC(OC)=C1 QFFCMSVSOLNBCG-UHFFFAOYSA-N 0.000 description 2
- ZPJQMHGRPIUNAQ-UHFFFAOYSA-N n-[[5-[4-(2,4-difluorobenzoyl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)C(=O)C=2C(=CC(F)=CC=2)F)S1 ZPJQMHGRPIUNAQ-UHFFFAOYSA-N 0.000 description 2
- IWZGGZOMLSVQHZ-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-3-nitrobenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)=C1 IWZGGZOMLSVQHZ-UHFFFAOYSA-N 0.000 description 2
- QDHJPQKWODVHIM-UHFFFAOYSA-N n-[[5-[4-(benzotriazol-1-yl)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]-4-nitrobenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=CC=CC=C3N=N2)S1 QDHJPQKWODVHIM-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004193 piperazinyl group Chemical group 0.000 description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- QUOOJHOUWWKDLC-UHFFFAOYSA-N 1-[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]benzotriazole-5-carboxylic acid Chemical compound N1=NC2=CC(C(=O)O)=CC=C2N1C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 QUOOJHOUWWKDLC-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004098 2,6-dichlorobenzoyl group Chemical group O=C([*])C1=C(Cl)C([H])=C([H])C([H])=C1Cl 0.000 description 1
- NITIZPRHXHKHKE-UHFFFAOYSA-N 2-[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]benzotriazole-5-carboxylic acid Chemical compound N1=C2C=C(C(=O)O)C=CC2=NN1C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 NITIZPRHXHKHKE-UHFFFAOYSA-N 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- XXUNIGZDNWWYED-UHFFFAOYSA-N 2-methylbenzamide Chemical compound CC1=CC=CC=C1C(N)=O XXUNIGZDNWWYED-UHFFFAOYSA-N 0.000 description 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- PABNZKZLNDPPRJ-UHFFFAOYSA-N 2h-isoindol-5-amine Chemical compound C1=C(N)C=CC2=CNC=C21 PABNZKZLNDPPRJ-UHFFFAOYSA-N 0.000 description 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- ZEMKFYWBBJQTTO-UHFFFAOYSA-N 3-[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]benzotriazole-5-carboxylic acid Chemical compound C12=CC(C(=O)O)=CC=C2N=NN1C(CC1)CCN1S(=O)(=O)C(S1)=CC=C1CNC(=O)C1=CC=C(Cl)C=C1 ZEMKFYWBBJQTTO-UHFFFAOYSA-N 0.000 description 1
- NPJZEZNSWGSLMI-UHFFFAOYSA-N 3-[[1-[5-[[(3-methoxybenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C(N)=O)=C1 NPJZEZNSWGSLMI-UHFFFAOYSA-N 0.000 description 1
- ZTLOSGSELOXHON-UHFFFAOYSA-N 3-[[1-[5-[[(3-nitrobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound NC(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 ZTLOSGSELOXHON-UHFFFAOYSA-N 0.000 description 1
- QQQGBUXUGKEYGK-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(2-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CC=2)[N+]([O-])=O)=C1 QQQGBUXUGKEYGK-UHFFFAOYSA-N 0.000 description 1
- PVGNZTSNAGJCPB-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-nitroanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)[N+]([O-])=O)=C1 PVGNZTSNAGJCPB-UHFFFAOYSA-N 0.000 description 1
- LVRMUVFFBUDIAS-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-phenylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 LVRMUVFFBUDIAS-UHFFFAOYSA-N 0.000 description 1
- FGVUIHFBKUSHJC-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)S(N)(=O)=O)=C1 FGVUIHFBKUSHJC-UHFFFAOYSA-N 0.000 description 1
- ISABLLPEAKALNX-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[(3-nitropyridin-2-yl)amino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC=CN=2)[N+]([O-])=O)=C1 ISABLLPEAKALNX-UHFFFAOYSA-N 0.000 description 1
- UWQRKPXBKSKMQC-UHFFFAOYSA-N 3-methoxy-n-[[5-[4-[2-nitro-4-(trifluoromethylsulfonyl)anilino]piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound COC1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C(=CC(=CC=2)S(=O)(=O)C(F)(F)F)[N+]([O-])=O)=C1 UWQRKPXBKSKMQC-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- CABYWBAUQVRJRM-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-phenylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NCC=2SC(=CC=2)S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 CABYWBAUQVRJRM-UHFFFAOYSA-N 0.000 description 1
- JOPXXSDRUTXQOU-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-propylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound CCCC1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 JOPXXSDRUTXQOU-UHFFFAOYSA-N 0.000 description 1
- BSLBMLQMHLDZMK-UHFFFAOYSA-N 3-nitro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=C(C=CC=3)[N+]([O-])=O)=CC=2)=C1 BSLBMLQMHLDZMK-UHFFFAOYSA-N 0.000 description 1
- MMROKRYETKOHRY-UHFFFAOYSA-N 4-[[1-[5-[[(4-chlorobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)CC1 MMROKRYETKOHRY-UHFFFAOYSA-N 0.000 description 1
- BHKRSZFGOWKFIT-UHFFFAOYSA-N 4-[[1-[5-[[(4-nitrobenzoyl)amino]methyl]thiophen-2-yl]sulfonylpiperidin-4-yl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC1CCN(S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)CC1 BHKRSZFGOWKFIT-UHFFFAOYSA-N 0.000 description 1
- HRENJJAUOQBRJD-UHFFFAOYSA-N 4-chloro-n-[(5-piperazin-1-ylsulfonylthiophen-2-yl)methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCNCC2)S1 HRENJJAUOQBRJD-UHFFFAOYSA-N 0.000 description 1
- YMMNSNFRGFKVMR-UHFFFAOYSA-N 4-chloro-n-[[5-(3-oxopyrrolidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CC(=O)CC2)S1 YMMNSNFRGFKVMR-UHFFFAOYSA-N 0.000 description 1
- XYFOIXJKYRPEFX-UHFFFAOYSA-N 4-chloro-n-[[5-(4-imidazo[4,5-b]pyridin-3-ylpiperidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)N2C3=NC=CC=C3N=C2)S1 XYFOIXJKYRPEFX-UHFFFAOYSA-N 0.000 description 1
- UDTUQGKGRIJGDJ-UHFFFAOYSA-N 4-chloro-n-[[5-(4-phenylmethoxypiperidin-1-yl)sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)OCC=2C=CC=CC=2)S1 UDTUQGKGRIJGDJ-UHFFFAOYSA-N 0.000 description 1
- DJUDYCQCDKMWKD-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-phenylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCC(CC2)NC=2C=C(C=CC=2)C=2C=CC=CC=2)S1 DJUDYCQCDKMWKD-UHFFFAOYSA-N 0.000 description 1
- IYZRWZSWTUOPRF-UHFFFAOYSA-N 4-chloro-n-[[5-[4-(3-sulfamoylanilino)piperidin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound NS(=O)(=O)C1=CC=CC(NC2CCN(CC2)S(=O)(=O)C=2SC(CNC(=O)C=3C=CC(Cl)=CC=3)=CC=2)=C1 IYZRWZSWTUOPRF-UHFFFAOYSA-N 0.000 description 1
- CXODZXYALWYOJQ-WUXMJOGZSA-N 4-chloro-n-[[5-[4-[(e)-3-phenylprop-2-enoyl]piperazin-1-yl]sulfonylthiophen-2-yl]methyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC1=CC=C(S(=O)(=O)N2CCN(CC2)C(=O)\C=C\C=2C=CC=CC=2)S1 CXODZXYALWYOJQ-WUXMJOGZSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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| EP1193267A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active hydrophilic sulfonamide derivatives as inhibitors of protein JunKinases |
| EP1193268A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
| EP1193256A1 (en) * | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active benzsulfonamide derivatives as inhibitors of JNK proteins |
| ATE330950T1 (de) | 2000-12-13 | 2006-07-15 | Wyeth Corp | Heterocyclische sulfonamide als inhibitoren der beta-amyloid-produktion |
| US6657070B2 (en) | 2000-12-13 | 2003-12-02 | Wyeth | Production of chirally pure α-amino acids and N-sulfonyl α-amino acids |
| WO2002083648A1 (fr) | 2001-04-16 | 2002-10-24 | Eisai Co., Ltd. | Nouveau compose a base de 1h-indazole |
| CA2452259A1 (en) * | 2001-07-23 | 2003-02-06 | Applied Research Systems Ars Holding N.V. | Arylsulfonamide derivatives as c-jun-n-terminal kinases (jnk's) inhibitors |
| PA8557501A1 (es) | 2001-11-12 | 2003-06-30 | Pfizer Prod Inc | Benzamida, heteroarilamida y amidas inversas |
| WO2003042190A1 (en) | 2001-11-12 | 2003-05-22 | Pfizer Products Inc. | N-alkyl-adamantyl derivatives as p2x7-receptor antagonists |
| AU2003241925A1 (en) | 2002-05-31 | 2003-12-19 | Eisai R&D Management Co., Ltd. | Pyrazole compound and medicinal composition containing the same |
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| US7071223B1 (en) | 2002-12-31 | 2006-07-04 | Pfizer, Inc. | Benzamide inhibitors of the P2X7 receptor |
| PA8591801A1 (es) | 2002-12-31 | 2004-07-26 | Pfizer Prod Inc | Inhibidores benzamidicos del receptor p2x7. |
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-
1999
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2000
- 2000-09-26 AR ARP000105044A patent/AR031531A1/es active IP Right Grant
- 2000-09-28 WO PCT/IB2000/001380 patent/WO2001023378A1/en not_active Ceased
- 2000-09-28 PL PL354169A patent/PL212237B1/pl not_active IP Right Cessation
- 2000-09-28 US US10/070,954 patent/US8012995B1/en not_active Expired - Fee Related
- 2000-09-28 JP JP2001526530A patent/JP5015397B2/ja not_active Expired - Fee Related
- 2000-09-28 DK DK00960921T patent/DK1218374T3/da active
- 2000-09-28 BR BR0014641-2A patent/BR0014641A/pt not_active IP Right Cessation
- 2000-09-28 EP EP00960921A patent/EP1218374B1/en not_active Expired - Lifetime
- 2000-09-28 SK SK580-2002A patent/SK287058B6/sk not_active IP Right Cessation
- 2000-09-28 TR TR2002/00789T patent/TR200200789T2/xx unknown
- 2000-09-28 AT AT00960921T patent/ATE309998T1/de active
- 2000-09-28 MX MXPA02003199A patent/MXPA02003199A/es active IP Right Grant
- 2000-09-28 DE DE60024115T patent/DE60024115T2/de not_active Expired - Lifetime
- 2000-09-28 EA EA200200417A patent/EA005368B1/ru not_active IP Right Cessation
- 2000-09-28 ES ES00960921T patent/ES2248114T3/es not_active Expired - Lifetime
- 2000-09-28 UA UA2002032472A patent/UA74796C2/uk unknown
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- 2000-09-28 CN CNB008135681A patent/CN1189467C/zh not_active Expired - Fee Related
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- 2000-09-28 EE EEP200200165A patent/EE05109B1/xx not_active IP Right Cessation
- 2000-09-28 KR KR1020027003983A patent/KR100827533B1/ko not_active Expired - Fee Related
- 2000-09-28 HK HK03100202.1A patent/HK1048306B/zh not_active IP Right Cessation
- 2000-09-28 NZ NZ517424A patent/NZ517424A/en not_active IP Right Cessation
- 2000-09-28 SI SI200030771T patent/SI1218374T1/sl unknown
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- 2002-03-26 NO NO20021530A patent/NO324792B1/no not_active IP Right Cessation
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