JP2007500700A

JP2007500700A - 化合物

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Publication number: JP2007500700A
Authority: JP; Japan
Prior art keywords: indazol; compound; propenamide; alkyl; prop
Prior art date: 2003-07-29
Legal status : Pending

Application number

JP2006521933A

Other languages

English (en)

Japanese (ja)

Other versions

JP2007500700A5 (https=

Inventor

ドローリー，デビッド，ハロルド

リン，ジェームズ，アンドリュー

ヴィール，ジェームズ，マーヴィン

Original Assignee

スミスクラインビーチャムコーポレーション

Priority date

2003-07-29

Filing date

2004-07-23

Publication date

2007-01-18

2004-07-23 Application filed by スミスクラインビーチャムコーポレーション filed Critical スミスクラインビーチャムコーポレーション

2007-01-18 Publication of JP2007500700A publication Critical patent/JP2007500700A/ja

2007-09-06 Publication of JP2007500700A5 publication Critical patent/JP2007500700A5/ja

Status Pending legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims description 108
238000000034 method Methods 0.000 claims abstract description 82
101150082971 Sgk1 gene Proteins 0.000 claims abstract description 33
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 33
230000000694 effects Effects 0.000 claims abstract description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
230000001404 mediated effect Effects 0.000 claims abstract description 8
-1 1H-indazol-3-yl Chemical group 0.000 claims description 98
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
150000003839 salts Chemical class 0.000 claims description 38
125000003118 aryl group Chemical group 0.000 claims description 36
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 29
125000001072 heteroaryl group Chemical group 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000012453 solvate Substances 0.000 claims description 24
239000008194 pharmaceutical composition Substances 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
125000003710 aryl alkyl group Chemical group 0.000 claims description 13
125000000753 cycloalkyl group Chemical group 0.000 claims description 13
239000005711 Benzoic acid Substances 0.000 claims description 11
235000010233 benzoic acid Nutrition 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000000732 arylene group Chemical group 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000005549 heteroarylene group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 5
BQQPHEGUYHFUGX-CSKARUKUSA-N (e)-3-(1h-indazol-3-yl)-n-[3-methoxy-4-[2-(2-methoxyethylamino)ethoxy]phenyl]prop-2-enamide Chemical compound C1=C(OC)C(OCCNCCOC)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 BQQPHEGUYHFUGX-CSKARUKUSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
238000002560 therapeutic procedure Methods 0.000 claims description 5
UJFIXTDBQVZLOI-ZHACJKMWSA-N (e)-1-(4-benzylpiperidin-1-yl)-3-(1h-indazol-3-yl)prop-2-en-1-one Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)N(CC1)CCC1CC1=CC=CC=C1 UJFIXTDBQVZLOI-ZHACJKMWSA-N 0.000 claims description 4
PQKCLCOVJGRGEI-AATRIKPKSA-N (e)-3-(1h-indazol-3-yl)-1-(4-pyrazin-2-ylpiperazin-1-yl)prop-2-en-1-one Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)N(CC1)CCN1C1=CN=CC=N1 PQKCLCOVJGRGEI-AATRIKPKSA-N 0.000 claims description 4
NBRMWBYRKNYPOP-BQYQJAHWSA-N (e)-3-(1h-indazol-3-yl)-n-(2-methylpropyl)prop-2-enamide Chemical compound C1=CC=C2C(/C=C/C(=O)NCC(C)C)=NNC2=C1 NBRMWBYRKNYPOP-BQYQJAHWSA-N 0.000 claims description 4
PTIDBCQCYIWPJT-CMDGGOBGSA-N (e)-3-(1h-indazol-3-yl)-n-(3,4,5-trimethoxyphenyl)prop-2-enamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1 PTIDBCQCYIWPJT-CMDGGOBGSA-N 0.000 claims description 4
ZDOKWVCTYKDDIZ-BQYQJAHWSA-N (e)-3-(1h-indazol-3-yl)-n-(6-methoxypyridin-3-yl)prop-2-enamide Chemical compound C1=NC(OC)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 ZDOKWVCTYKDDIZ-BQYQJAHWSA-N 0.000 claims description 4
ZOXOITLUYSGMGB-VQHVLOKHSA-N (e)-3-(1h-indazol-3-yl)-n-[3-methoxy-4-(2-morpholin-4-ylethoxy)phenyl]prop-2-enamide Chemical compound COC1=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=C1OCCN1CCOCC1 ZOXOITLUYSGMGB-VQHVLOKHSA-N 0.000 claims description 4
XDSQLYIXWGORNM-WYMLVPIESA-N (e)-3-(1h-indazol-3-yl)-n-[3-methoxy-4-[2-(2-phenoxyethylamino)ethoxy]phenyl]prop-2-enamide Chemical compound COC1=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=C1OCCNCCOC1=CC=CC=C1 XDSQLYIXWGORNM-WYMLVPIESA-N 0.000 claims description 4
DRASAARUWQATHR-ZRDIBKRKSA-N (e)-3-(1h-indazol-3-yl)-n-[3-methoxy-4-[2-[methyl(propyl)amino]ethoxy]phenyl]prop-2-enamide Chemical compound C1=C(OC)C(OCCN(C)CCC)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 DRASAARUWQATHR-ZRDIBKRKSA-N 0.000 claims description 4
RFMTWNVTCAHWSS-ZHACJKMWSA-N (e)-3-(1h-indazol-3-yl)-n-quinolin-5-ylprop-2-enamide Chemical compound C1=CC=C2C(/C=C/C(NC=3C4=CC=CN=C4C=CC=3)=O)=NNC2=C1 RFMTWNVTCAHWSS-ZHACJKMWSA-N 0.000 claims description 4
CCNBMODZORJIGI-BQYQJAHWSA-N (e)-n-(1,3-benzothiazol-6-yl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound C1=CC=C2C(/C=C/C(NC=3C=C4SC=NC4=CC=3)=O)=NNC2=C1 CCNBMODZORJIGI-BQYQJAHWSA-N 0.000 claims description 4
JXMYVBPMGBOBCY-ZHACJKMWSA-N (e)-n-(2,3-dihydro-1h-inden-5-yl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound C1=CC=C2C(/C=C/C(NC=3C=C4CCCC4=CC=3)=O)=NNC2=C1 JXMYVBPMGBOBCY-ZHACJKMWSA-N 0.000 claims description 4
OAOQRAYQACNNII-BQYQJAHWSA-N (e)-n-(3,4-dimethyl-1,2-oxazol-5-yl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound CC1=NOC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1C OAOQRAYQACNNII-BQYQJAHWSA-N 0.000 claims description 4
JHRAGLLNHTUVQV-MDZDMXLPSA-N (e)-n-(3-acetamidophenyl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound CC(=O)NC1=CC=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1 JHRAGLLNHTUVQV-MDZDMXLPSA-N 0.000 claims description 4
DKXJTYCZBHJPPE-BUHFOSPRSA-N (e)-n-(3-benzoylphenyl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)NC(C=1)=CC=CC=1C(=O)C1=CC=CC=C1 DKXJTYCZBHJPPE-BUHFOSPRSA-N 0.000 claims description 4
VPNUWTCWNUJLCA-SOFGYWHQSA-N (e)-n-(3-chloro-4-morpholin-4-ylphenyl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound ClC1=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=C1N1CCOCC1 VPNUWTCWNUJLCA-SOFGYWHQSA-N 0.000 claims description 4
LZGXLSAUWCEBNP-CMDGGOBGSA-N (e)-n-(3-chlorophenyl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound ClC1=CC=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1 LZGXLSAUWCEBNP-CMDGGOBGSA-N 0.000 claims description 4
ZDUBHWYWPVXMNY-CMDGGOBGSA-N (e)-n-(5-cyclopropyl-2-methylpyrazol-3-yl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound C1=C(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)N(C)N=C1C1CC1 ZDUBHWYWPVXMNY-CMDGGOBGSA-N 0.000 claims description 4
QDZSUIBNZJDUIO-VAWYXSNFSA-N (e)-n-[4-(dimethylamino)phenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 QDZSUIBNZJDUIO-VAWYXSNFSA-N 0.000 claims description 4
XCBCALVDYASWHD-CSKARUKUSA-N (e)-n-[4-[2-(4-acetylpiperazin-1-yl)ethoxy]-3-methoxyphenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound COC1=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=C1OCCN1CCN(C(C)=O)CC1 XCBCALVDYASWHD-CSKARUKUSA-N 0.000 claims description 4
KERQAMZZSOSVKC-ACCUITESSA-N (e)-n-[4-[2-[2-(4-chlorophenyl)ethylamino]ethoxy]-3-methoxyphenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound COC1=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=C1OCCNCCC1=CC=C(Cl)C=C1 KERQAMZZSOSVKC-ACCUITESSA-N 0.000 claims description 4
YBHJVZSUKKHPSA-ACCUITESSA-N (e)-n-[5-(diethylsulfamoyl)-2-methoxyphenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound CCN(CC)S(=O)(=O)C1=CC=C(OC)C(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1 YBHJVZSUKKHPSA-ACCUITESSA-N 0.000 claims description 4
CVJXCMJIXQTKPH-ZHACJKMWSA-N 8-[(e)-3-(1h-indazol-3-yl)prop-2-enoyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)N(CC1)CCC1(C(NC1)=O)N1C1=CC=CC=C1 CVJXCMJIXQTKPH-ZHACJKMWSA-N 0.000 claims description 4
125000004122 cyclic group Chemical group 0.000 claims description 4
VRZSASOIMVAPEE-BQYQJAHWSA-N ethyl 1-[(e)-3-(1h-indazol-3-yl)prop-2-enoyl]piperidine-4-carboxylate Chemical compound C1CC(C(=O)OCC)CCN1C(=O)\C=C\C1=NNC2=CC=CC=C12 VRZSASOIMVAPEE-BQYQJAHWSA-N 0.000 claims description 4
CKXNSRXGWGIMBK-PKNBQFBNSA-N ethyl 4-[2-[4-[[(e)-3-(1h-indazol-3-yl)prop-2-enoyl]amino]-2-methoxyphenoxy]ethylamino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC1NCCOC(C(=C1)OC)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 CKXNSRXGWGIMBK-PKNBQFBNSA-N 0.000 claims description 4
PSJWRNJVSMCGMZ-ZHACJKMWSA-N methyl 4-[[(e)-3-(1h-indazol-3-yl)prop-2-enoyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)\C=C\C1=NNC2=CC=CC=C12 PSJWRNJVSMCGMZ-ZHACJKMWSA-N 0.000 claims description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
GKJUBVWJSMCBNT-MDZDMXLPSA-N (e)-n-(2-cyanophenyl)-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)NC1=CC=CC=C1C#N GKJUBVWJSMCBNT-MDZDMXLPSA-N 0.000 claims description 3
LNRDAZWJQZRGTJ-BUHFOSPRSA-N (e)-n-[3-(4-benzylpiperazine-1-carbonyl)phenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound N=1NC2=CC=CC=C2C=1/C=C/C(=O)NC(C=1)=CC=CC=1C(=O)N(CC1)CCN1CC1=CC=CC=C1 LNRDAZWJQZRGTJ-BUHFOSPRSA-N 0.000 claims description 3
OLRPPNBPIIOXPJ-ACCUITESSA-N (e)-n-[4-[2-[di(propan-2-yl)amino]ethoxy]-3-methoxyphenyl]-3-(1h-indazol-3-yl)prop-2-enamide Chemical compound C1=C(OCCN(C(C)C)C(C)C)C(OC)=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=C1 OLRPPNBPIIOXPJ-ACCUITESSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 2
ONPWQBRKNMHCCG-ZHACJKMWSA-N n-ethyl-3-[[(e)-3-(1h-indazol-3-yl)prop-2-enoyl]amino]-n-(pyridin-4-ylmethyl)benzamide Chemical compound C=1C=CC(NC(=O)\C=C\C=2C3=CC=CC=C3NN=2)=CC=1C(=O)N(CC)CC1=CC=NC=C1 ONPWQBRKNMHCCG-ZHACJKMWSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 3
ZQLCTZDZITZQSH-UHFFFAOYSA-N 2-(1h-indazol-3-yl)prop-2-enamide Chemical class C1=CC=C2C(C(=C)C(=O)N)=NNC2=C1 ZQLCTZDZITZQSH-UHFFFAOYSA-N 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 7
229940126213 SGK1 inhibitor Drugs 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 50
238000001819 mass spectrum Methods 0.000 description 49
239000000203 mixture Substances 0.000 description 46
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 38
238000005481 NMR spectroscopy Methods 0.000 description 37
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 35
235000002639 sodium chloride Nutrition 0.000 description 35
239000007787 solid Substances 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 29
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239000000243 solution Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
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125000005843 halogen group Chemical group 0.000 description 17
239000000543 intermediate Substances 0.000 description 17
239000000843 powder Substances 0.000 description 17
238000009472 formulation Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
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125000004432 carbon atom Chemical group C* 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
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102000001253 Protein Kinase Human genes 0.000 description 13
108060006633 protein kinase Proteins 0.000 description 13
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235000019439 ethyl acetate Nutrition 0.000 description 11
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
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ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 6
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RGBWDPJLJNKEPX-AATRIKPKSA-N (e)-3-(1h-indazol-3-yl)prop-2-enoic acid Chemical compound C1=CC=C2C(/C=C/C(=O)O)=NNC2=C1 RGBWDPJLJNKEPX-AATRIKPKSA-N 0.000 description 5
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
229910052717 sulfur Inorganic materials 0.000 description 5
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
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