ES2475206T3 - Derivados de oxima como inhibidores de HSP90 - Google Patents
Derivados de oxima como inhibidores de HSP90 Download PDFInfo
- Publication number
- ES2475206T3 ES2475206T3 ES09706850.6T ES09706850T ES2475206T3 ES 2475206 T3 ES2475206 T3 ES 2475206T3 ES 09706850 T ES09706850 T ES 09706850T ES 2475206 T3 ES2475206 T3 ES 2475206T3
- Authority
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- Spain
- Prior art keywords
- methyl
- amino
- pyrimidin
- fluoro
- phenyl
- Prior art date
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- 150000002923 oximes Chemical class 0.000 title claims description 22
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 title description 54
- -1 amino, carbonylamino, aminocarbonyl Chemical group 0.000 claims abstract description 523
- 150000001875 compounds Chemical class 0.000 claims abstract description 274
- 125000001424 substituent group Chemical group 0.000 claims abstract description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 57
- 125000003118 aryl group Chemical group 0.000 claims abstract description 56
- 239000001257 hydrogen Substances 0.000 claims abstract description 56
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 53
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 50
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 38
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 21
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 19
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 18
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 16
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 14
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 12
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 150000002367 halogens Chemical class 0.000 claims abstract description 7
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 4
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 160
- BDTRIDKONHOQQN-UHFFFAOYSA-N 4h-pyrimidin-5-one Chemical compound O=C1CN=CN=C1 BDTRIDKONHOQQN-UHFFFAOYSA-N 0.000 claims description 100
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 58
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- 201000011510 cancer Diseases 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 22
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 10
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
- IWTFOFMTUOBLHG-UHFFFAOYSA-N 2-methoxypyridine Chemical compound COC1=CC=CC=N1 IWTFOFMTUOBLHG-UHFFFAOYSA-N 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 8
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000004963 sulfonylalkyl group Chemical group 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 206010003246 arthritis Diseases 0.000 claims description 6
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 6
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- NCBQCQLKWVEYDM-UHFFFAOYSA-N 4-methyl-7,8-dihydro-6H-pyrido[4,3-d]pyrimidin-5-one Chemical compound CC=1C2=C(N=CN=1)CCNC2=O NCBQCQLKWVEYDM-UHFFFAOYSA-N 0.000 claims description 3
- DRQRNJQGXVDZBU-TZIWHRDSSA-N (2r)-2-[[(7r)-2-amino-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-yl]amino]oxy-4-hydroxy-n,n-dimethylbutanamide Chemical compound COC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(/C3=C(C)N=C(N)N=C3C2)=N\O[C@H](CCO)C(=O)N(C)C)=N1 DRQRNJQGXVDZBU-TZIWHRDSSA-N 0.000 claims description 2
- BHFXPKPIPBNKFI-UHFFFAOYSA-N 2,3,4,7,8,8a-hexahydro-1h-pyrrolo[1,2-a]pyrazin-6-one Chemical compound C1NCCN2C(=O)CCC21 BHFXPKPIPBNKFI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000979 2-amino-2-oxoethyl group Chemical group [H]C([*])([H])C(=O)N([H])[H] 0.000 claims description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 206010052779 Transplant rejections Diseases 0.000 claims description 2
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 claims description 2
- DRQRNJQGXVDZBU-CTNGQTDRSA-N (2s)-2-[[(7r)-2-amino-7-[4-fluoro-2-(6-methoxypyridin-2-yl)phenyl]-4-methyl-7,8-dihydropyrido[4,3-d]pyrimidin-5-yl]amino]oxy-4-hydroxy-n,n-dimethylbutanamide Chemical compound COC1=CC=CC(C=2C(=CC=C(F)C=2)[C@@H]2NC(/C3=C(C)N=C(N)N=C3C2)=N\O[C@@H](CCO)C(=O)N(C)C)=N1 DRQRNJQGXVDZBU-CTNGQTDRSA-N 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 125000004103 aminoalkyl group Chemical group 0.000 abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 95
- 238000000034 method Methods 0.000 description 75
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- 239000000243 solution Substances 0.000 description 54
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- 230000015572 biosynthetic process Effects 0.000 description 47
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- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 description 45
- 101710113864 Heat shock protein 90 Proteins 0.000 description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 44
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- 229910001868 water Inorganic materials 0.000 description 34
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| US10159508P | 2008-09-30 | 2008-09-30 | |
| US101595P | 2008-09-30 | ||
| PCT/US2009/032728 WO2009097578A1 (en) | 2008-02-01 | 2009-01-30 | Oxim derivatives as hsp90 inhibitors |
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| ES2475206T3 true ES2475206T3 (es) | 2014-07-10 |
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