JP2006516626A

JP2006516626A - 化学的化合物

化学的化合物 Download PDF

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Publication number: JP2006516626A
Authority: JP; Japan
Prior art keywords: alkyl; pyridin; amino; compound according; benzimidazol
Prior art date: 2003-01-28
Legal status : Pending

Application number

JP2006503012A

Other languages

English (en)

Japanese (ja)

Other versions

JP2006516626A5 (enExample

Inventor

ドリューリー，デイビッド，ハロルド

サードハンター，ロバート，ニール，ザ

Original Assignee

スミスクラインビーチャムコーポレーション

Priority date

2003-01-28

Filing date

2004-01-27

Publication date

2006-07-06

2004-01-27 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

2006-07-06 Publication of JP2006516626A publication Critical patent/JP2006516626A/ja

2007-03-08 Publication of JP2006516626A5 publication Critical patent/JP2006516626A5/ja

Status Pending legal-status Critical Current

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150000001875 compounds Chemical class 0.000 title claims description 103
238000000034 method Methods 0.000 claims abstract description 42
230000000694 effects Effects 0.000 claims abstract description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
238000002360 preparation method Methods 0.000 claims abstract description 17
230000001404 mediated effect Effects 0.000 claims abstract description 8
101150082971 Sgk1 gene Proteins 0.000 claims abstract 4
HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract 4
-1 C 1 -C 6 alkyl Chemical group 0.000 claims description 54
150000003839 salts Chemical class 0.000 claims description 42
125000003118 aryl group Chemical group 0.000 claims description 38
125000005843 halogen group Chemical group 0.000 claims description 29
239000012453 solvate Substances 0.000 claims description 28
125000001072 heteroaryl group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
239000008194 pharmaceutical composition Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 17
229910052799 carbon Inorganic materials 0.000 claims description 16
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000000623 heterocyclic group Chemical group 0.000 claims description 16
208000035475 disorder Diseases 0.000 claims description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
241000124008 Mammalia Species 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000006273 (C1-C3) alkyl 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
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
FUSVWYRZUBCJBA-UHFFFAOYSA-N 2-[2-amino-5-(3-cyanophenyl)pyridin-3-yl]-3h-benzimidazole-5-sulfonamide Chemical compound C1=C(C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)C(N)=NC=C1C1=CC=CC(C#N)=C1 FUSVWYRZUBCJBA-UHFFFAOYSA-N 0.000 claims description 4
HJOBCAIXQIZFSY-UHFFFAOYSA-N 2-[2-amino-5-(4-methoxyphenyl)pyridin-3-yl]-3h-benzimidazole-5-sulfonamide Chemical compound C1=CC(OC)=CC=C1C1=CN=C(N)C(C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)=C1 HJOBCAIXQIZFSY-UHFFFAOYSA-N 0.000 claims description 4
HIPALRDMCQACSM-UHFFFAOYSA-N 3-(6-fluoro-1h-benzimidazol-2-yl)-5-(4-fluorophenyl)pyridin-2-amine Chemical compound C1=C(C=2NC3=CC(F)=CC=C3N=2)C(N)=NC=C1C1=CC=C(F)C=C1 HIPALRDMCQACSM-UHFFFAOYSA-N 0.000 claims description 4
BIXLAMXENIEOHK-UHFFFAOYSA-N 5-(4-fluorophenyl)-3-(4-methyl-1h-benzimidazol-2-yl)pyridin-2-amine Chemical compound N=1C=2C(C)=CC=CC=2NC=1C(C(=NC=1)N)=CC=1C1=CC=C(F)C=C1 BIXLAMXENIEOHK-UHFFFAOYSA-N 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 4
IVPCWDBJWBWWLM-UHFFFAOYSA-N 2-[2-amino-5-(3,4,5-trimethoxyphenyl)pyridin-3-yl]-3h-benzimidazole-5-sulfonamide Chemical compound COC1=C(OC)C(OC)=CC(C=2C=C(C(N)=NC=2)C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)=C1 IVPCWDBJWBWWLM-UHFFFAOYSA-N 0.000 claims description 3
WMQSQHURLVYITM-UHFFFAOYSA-N 2-[2-amino-5-(3-methoxyphenyl)pyridin-3-yl]-3h-benzimidazole-5-sulfonamide Chemical compound COC1=CC=CC(C=2C=C(C(N)=NC=2)C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)=C1 WMQSQHURLVYITM-UHFFFAOYSA-N 0.000 claims description 3
MEJJEZUUIVPVSS-UHFFFAOYSA-N 2-[2-amino-5-(4-fluorophenyl)pyridin-3-yl]-3h-benzimidazole-5-sulfonamide Chemical compound C1=C(C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)C(N)=NC=C1C1=CC=C(F)C=C1 MEJJEZUUIVPVSS-UHFFFAOYSA-N 0.000 claims description 3
CLRWMPFUTCKUQH-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-5-phenylpyridin-2-amine Chemical compound C1=C(C=2NC3=CC=CC=C3N=2)C(N)=NC=C1C1=CC=CC=C1 CLRWMPFUTCKUQH-UHFFFAOYSA-N 0.000 claims description 3
230000035790 physiological processes and functions Effects 0.000 claims description 3
LPDYFVZTFPDLJH-UHFFFAOYSA-N 2-(2-amino-5-phenylpyridin-3-yl)-3h-benzimidazole-5-sulfonamide Chemical compound C1=C(C=2NC3=CC(=CC=C3N=2)S(N)(=O)=O)C(N)=NC=C1C1=CC=CC=C1 LPDYFVZTFPDLJH-UHFFFAOYSA-N 0.000 claims description 2
LWCDOVGPENQJFK-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-5-(3-methoxyphenyl)pyridin-2-amine Chemical compound COC1=CC=CC(C=2C=C(C(N)=NC=2)C=2NC3=CC=CC=C3N=2)=C1 LWCDOVGPENQJFK-UHFFFAOYSA-N 0.000 claims description 2
YROZFOKSWZOYMK-UHFFFAOYSA-N 3-(4-methyl-1h-benzimidazol-2-yl)-5-phenylpyridin-2-amine Chemical compound N=1C=2C(C)=CC=CC=2NC=1C(C(=NC=1)N)=CC=1C1=CC=CC=C1 YROZFOKSWZOYMK-UHFFFAOYSA-N 0.000 claims description 2
TWWBQGYWZTWEHB-UHFFFAOYSA-N 3-(5-chloro-6-fluoro-1h-benzimidazol-2-yl)-5-(3-methoxyphenyl)pyridin-2-amine Chemical compound COC1=CC=CC(C=2C=C(C(N)=NC=2)C=2NC3=CC(F)=C(Cl)C=C3N=2)=C1 TWWBQGYWZTWEHB-UHFFFAOYSA-N 0.000 claims description 2
KMQXMUPSJARRJE-UHFFFAOYSA-N 3-(6-fluoro-1h-benzimidazol-2-yl)-5-phenylpyridin-2-amine Chemical compound C1=C(C=2NC3=CC(F)=CC=C3N=2)C(N)=NC=C1C1=CC=CC=C1 KMQXMUPSJARRJE-UHFFFAOYSA-N 0.000 claims description 2
SPFWTUFOLVVHTC-UHFFFAOYSA-N 3-(6-methoxy-1h-benzimidazol-2-yl)-5-phenylpyridin-2-amine Chemical compound N1C2=CC(OC)=CC=C2N=C1C(C(=NC=1)N)=CC=1C1=CC=CC=C1 SPFWTUFOLVVHTC-UHFFFAOYSA-N 0.000 claims description 2
ASAPGNUILRWSGQ-UHFFFAOYSA-N 5-(3-methoxyphenyl)-3-(4-methyl-1h-benzimidazol-2-yl)pyridin-2-amine Chemical compound COC1=CC=CC(C=2C=C(C(N)=NC=2)C=2NC3=CC=CC(C)=C3N=2)=C1 ASAPGNUILRWSGQ-UHFFFAOYSA-N 0.000 claims description 2
CINKOKVGIIGBBG-UHFFFAOYSA-N methyl 2-(2-amino-5-phenylpyridin-3-yl)-3h-benzimidazole-5-carboxylate Chemical compound N1C2=CC(C(=O)OC)=CC=C2N=C1C(C(=NC=1)N)=CC=1C1=CC=CC=C1 CINKOKVGIIGBBG-UHFFFAOYSA-N 0.000 claims description 2
IAZXOXWJANJRDV-UHFFFAOYSA-N methyl 2-[2-amino-5-(3-methoxyphenyl)pyridin-3-yl]-3h-benzimidazole-5-carboxylate Chemical compound N1C2=CC(C(=O)OC)=CC=C2N=C1C(C(=NC=1)N)=CC=1C1=CC=CC(OC)=C1 IAZXOXWJANJRDV-UHFFFAOYSA-N 0.000 claims description 2
201000010099 disease Diseases 0.000 abstract description 7
YNFBMDWHEHETJW-UHFFFAOYSA-N 2-pyridin-2-yl-1h-benzimidazole Chemical class N1=CC=CC=C1C1=NC2=CC=CC=C2N1 YNFBMDWHEHETJW-UHFFFAOYSA-N 0.000 abstract description 5
229940126213 SGK1 inhibitor Drugs 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
235000002639 sodium chloride Nutrition 0.000 description 36
238000001819 mass spectrum Methods 0.000 description 29
239000000203 mixture Substances 0.000 description 29
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
238000005160 1H NMR spectroscopy Methods 0.000 description 25
239000002904 solvent Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
235000019439 ethyl acetate Nutrition 0.000 description 15
125000004432 carbon atom Chemical group C* 0.000 description 14
238000003786 synthesis reaction Methods 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
239000000243 solution Substances 0.000 description 13
238000006467 substitution reaction Methods 0.000 description 13
102000001253 Protein Kinase Human genes 0.000 description 12
230000015572 biosynthetic process Effects 0.000 description 12
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239000000843 powder Substances 0.000 description 12
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
108091000080 Phosphotransferase Proteins 0.000 description 10
239000004480 active ingredient Substances 0.000 description 10
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 10
UWCJRCQDXPHJOC-UHFFFAOYSA-N n-[3-formyl-5-(3-methoxyphenyl)pyridin-2-yl]-2,2-dimethylpropanamide Chemical compound COC1=CC=CC(C=2C=C(C=O)C(NC(=O)C(C)(C)C)=NC=2)=C1 UWCJRCQDXPHJOC-UHFFFAOYSA-N 0.000 description 10
102000020233 phosphotransferase Human genes 0.000 description 10
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125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 9
125000000753 cycloalkyl group Chemical group 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
239000003826 tablet Substances 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
102000004190 Enzymes Human genes 0.000 description 8
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125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 8
239000002585 base Substances 0.000 description 8
229940088598 enzyme Drugs 0.000 description 8
QLIOMYUFKLGBFE-UHFFFAOYSA-N n-(3-formyl-5-phenylpyridin-2-yl)-2,2-dimethylpropanamide Chemical compound C1=C(C=O)C(NC(=O)C(C)(C)C)=NC=C1C1=CC=CC=C1 QLIOMYUFKLGBFE-UHFFFAOYSA-N 0.000 description 8
125000004043 oxo group Chemical group O=* 0.000 description 8
KDOAJEVCIZYWDI-UHFFFAOYSA-N 2-amino-5-bromopyridine-3-carbaldehyde Chemical compound NC1=NC=C(Br)C=C1C=O KDOAJEVCIZYWDI-UHFFFAOYSA-N 0.000 description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 7
239000011734 sodium Substances 0.000 description 7
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 6
YMOGCAWTVPTVDP-UHFFFAOYSA-N 2-amino-5-(4-fluorophenyl)pyridine-3-carbaldehyde Chemical compound C1=C(C=O)C(N)=NC=C1C1=CC=C(F)C=C1 YMOGCAWTVPTVDP-UHFFFAOYSA-N 0.000 description 6
QULXUUQWVHVHSM-UHFFFAOYSA-N 3,4-diaminobenzenesulfonamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1N QULXUUQWVHVHSM-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
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CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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239000007788 liquid Substances 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
NLLGFYPSWCMUIV-UHFFFAOYSA-N (3-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC(B(O)O)=C1 NLLGFYPSWCMUIV-UHFFFAOYSA-N 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
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125000005842 heteroatom Chemical group 0.000 description 5
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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DCJFTQZBLWOVSO-UHFFFAOYSA-N n-[3-(1h-benzimidazol-2-yl)-5-phenylpyridin-2-yl]-2,2-dimethylpropanamide Chemical compound C1=C(C=2NC3=CC=CC=C3N=2)C(NC(=O)C(C)(C)C)=NC=C1C1=CC=CC=C1 DCJFTQZBLWOVSO-UHFFFAOYSA-N 0.000 description 4
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HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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JGQISMMUWYTUGM-UHFFFAOYSA-N 3-(1h-benzimidazol-2-yl)-5-phenylpyridin-2-amine;hydrochloride Chemical compound Cl.C1=C(C=2NC3=CC=CC=C3N=2)C(N)=NC=C1C1=CC=CC=C1 JGQISMMUWYTUGM-UHFFFAOYSA-N 0.000 description 3
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OAPVIBHQRYFYSE-UHFFFAOYSA-N 5-Phenyl-2-pyridinamine Chemical compound C1=NC(N)=CC=C1C1=CC=CC=C1 OAPVIBHQRYFYSE-UHFFFAOYSA-N 0.000 description 3
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