NZ587207A - Oxim derivatives as hsp90 inhibitors - Google Patents

Info

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

2008-02-01

Links

• Espacenet
• Global Dossier
• Discuss

• 239000003481 heat shock protein 90 inhibitor Substances 0.000 title description 26
• 150000001875 compounds Chemical class 0.000 claims abstract description 218
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 44
• 239000000203 mixture Substances 0.000 claims abstract description 39
• 201000011510 cancer Diseases 0.000 claims abstract description 26
• 206010061218 Inflammation Diseases 0.000 claims abstract description 7
• 206010003246 arthritis Diseases 0.000 claims abstract description 7
• 230000004054 inflammatory process Effects 0.000 claims abstract description 7
• 238000002360 preparation method Methods 0.000 claims abstract description 7
• 208000022559 Inflammatory bowel disease Diseases 0.000 claims abstract description 5
• 201000004681 Psoriasis Diseases 0.000 claims abstract description 4
• 206010052779 Transplant rejections Diseases 0.000 claims abstract description 3
• 125000000217 alkyl group Chemical group 0.000 claims description 1559
• 125000005842 heteroatom Chemical group 0.000 claims description 874
• 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
• 150000002431 hydrogen Chemical class 0.000 claims description 121
• 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
• 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 53
• 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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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
• 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 claims description 24
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• 125000002947 alkylene group Chemical group 0.000 claims description 16
• 125000001118 alkylidene group Chemical group 0.000 claims description 16
• 125000000304 alkynyl group Chemical group 0.000 claims description 16
• 150000002367 halogens Chemical class 0.000 claims description 16
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
• 125000001153 fluoro group Chemical group F* 0.000 claims description 13
• 125000004043 oxo group Chemical group O=* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 11
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• 125000002723 alicyclic group Chemical group 0.000 claims description 6
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• 125000001931 aliphatic group Chemical group 0.000 claims description 5
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• 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
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
• 239000003814 drug Substances 0.000 claims description 4
• 150000002576 ketones Chemical group 0.000 claims description 4
• 125000005188 oxoalkyl group Chemical group 0.000 claims description 4
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 3
• 125000001188 haloalkyl group Chemical group 0.000 claims description 3
• 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
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• 101710113864 Heat shock protein 90 Proteins 0.000 abstract description 65
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• 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
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• 108010006519 Molecular Chaperones Proteins 0.000 description 17
• 125000004093 cyano group Chemical group *C#N 0.000 description 17
• 229920006395 saturated elastomer Polymers 0.000 description 17
• 125000002619 bicyclic group Chemical group 0.000 description 16
• 230000002401 inhibitory effect Effects 0.000 description 16
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• 229940002612 prodrug Drugs 0.000 description 15
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• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
• 235000018102 proteins Nutrition 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 12
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• 125000004419 alkynylene group Chemical group 0.000 description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 12
• 150000001721 carbon Chemical group 0.000 description 12
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 12
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
• 230000007170 pathology Effects 0.000 description 12
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 11
• ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 11
• 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
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
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• 125000003367 polycyclic group Chemical group 0.000 description 9
• 125000006413 ring segment Chemical group 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 108091006112 ATPases Proteins 0.000 description 8
• 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
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
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• QTQAWLPCGQOSGP-GBTDJJJQSA-N geldanamycin Chemical group N1C(=O)\C(C)=C/C=C\[C@@H](OC)[C@H](OC(N)=O)\C(C)=C/[C@@H](C)[C@@H](O)[C@H](OC)C[C@@H](C)CC2=C(OC)C(=O)C=C1C2=O QTQAWLPCGQOSGP-GBTDJJJQSA-N 0.000 description 8
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• 125000004404 heteroalkyl group Chemical group 0.000 description 7
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