NZ587207A - Oxim derivatives as hsp90 inhibitors - Google Patents
Oxim derivatives as hsp90 inhibitorsInfo
- Publication number
- NZ587207A NZ587207A NZ587207A NZ58720709A NZ587207A NZ 587207 A NZ587207 A NZ 587207A NZ 587207 A NZ587207 A NZ 587207A NZ 58720709 A NZ58720709 A NZ 58720709A NZ 587207 A NZ587207 A NZ 587207A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alkyl
- methyl
- amino
- hetero
- fluoro
- Prior art date
Links
- 239000003481 heat shock protein 90 inhibitor Substances 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 218
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- 239000000203 mixture Substances 0.000 claims abstract description 39
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- 206010003246 arthritis Diseases 0.000 claims abstract description 7
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- 238000002360 preparation method Methods 0.000 claims abstract description 7
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- 125000000217 alkyl group Chemical group 0.000 claims description 1559
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- 125000003118 aryl group Chemical group 0.000 claims description 483
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 464
- -1 (C9_i2)bicycloaryl Chemical group 0.000 claims description 386
- 229910052739 hydrogen Inorganic materials 0.000 claims description 197
- 239000001257 hydrogen Substances 0.000 claims description 196
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 185
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 159
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 148
- 125000005843 halogen group Chemical group 0.000 claims description 137
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 136
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 119
- 125000001424 substituent group Chemical group 0.000 claims description 112
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000003545 alkoxy group Chemical group 0.000 claims description 75
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 75
- 125000004104 aryloxy group Chemical group 0.000 claims description 72
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 66
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 63
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 60
- 201000010099 disease Diseases 0.000 claims description 59
- 125000003282 alkyl amino group Chemical group 0.000 claims description 58
- 150000002923 oximes Chemical class 0.000 claims description 58
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- 150000003839 salts Chemical class 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 39
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- 125000002993 cycloalkylene group Chemical group 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims description 5
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 4
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- 125000005188 oxoalkyl group Chemical group 0.000 claims description 4
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- VGPBPWRBXBKGRE-UHFFFAOYSA-N n-(oxomethylidene)hydroxylamine Chemical group ON=C=O VGPBPWRBXBKGRE-UHFFFAOYSA-N 0.000 claims description 2
- AKCMCFPQVUTWFW-UHFFFAOYSA-N pyrrolidin-3-yl acetate Chemical compound CC(=O)OC1CCNC1 AKCMCFPQVUTWFW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
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- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 101710113864 Heat shock protein 90 Proteins 0.000 abstract description 65
- 238000000034 method Methods 0.000 abstract description 56
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- 230000008569 process Effects 0.000 abstract description 12
- 238000011282 treatment Methods 0.000 abstract description 9
- JGINAUIHQNPWRY-UHFFFAOYSA-N 7,8-dihydropyrido[4,3-d]pyrimidine Chemical class C1=NC=C2C=NCCC2=N1 JGINAUIHQNPWRY-UHFFFAOYSA-N 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 description 52
- 125000004429 atom Chemical group 0.000 description 43
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- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 238000001727 in vivo Methods 0.000 description 24
- 230000000694 effects Effects 0.000 description 23
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- 125000004093 cyano group Chemical group *C#N 0.000 description 17
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
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- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 12
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- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 12
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- 125000004433 nitrogen atom Chemical group N* 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 11
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- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 8
- JRZJKWGQFNTSRN-UHFFFAOYSA-N Geldanamycin Natural products C1C(C)CC(OC)C(O)C(C)C=C(C)C(OC(N)=O)C(OC)CCC=C(C)C(=O)NC2=CC(=O)C(OC)=C1C2=O JRZJKWGQFNTSRN-UHFFFAOYSA-N 0.000 description 8
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 8
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Landscapes
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| WO2009097578A1 (en) * | 2008-02-01 | 2009-08-06 | Takeda Pharmaceutical Company Limited | Oxim derivatives as hsp90 inhibitors |
| US8637504B2 (en) | 2008-06-13 | 2014-01-28 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta secretase inhibitory activity |
| WO2010047372A1 (ja) | 2008-10-22 | 2010-04-29 | 塩野義製薬株式会社 | Ｂａｃｅ１阻害活性を有する２－アミノピリミジン－４－オンおよび２－アミノピリジン誘導体 |
| RU2012129168A (ru) | 2009-12-11 | 2014-01-20 | Сионоги Энд Ко. Лтд. | Производные оксазина |
| CA2816285A1 (en) | 2010-10-29 | 2012-05-03 | Shionogi & Co., Ltd. | Naphthyridine derivative |
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| WO2012147763A1 (ja) | 2011-04-26 | 2012-11-01 | 塩野義製薬株式会社 | オキサジン誘導体およびそれを含有するｂａｃｅ１阻害剤 |
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| CN121889155A (zh) | 2023-08-07 | 2026-04-17 | 锐新医药公司 | 用于治疗ras蛋白相关疾病或病症的rmc-6291 |
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