NZ579635A - Fused amino pyridine as hsp90 inhibitors - Google Patents

Info

Publication number

NZ579635A

NZ579635A NZ579635A NZ57963508A NZ579635A NZ 579635 A NZ579635 A NZ 579635A NZ 579635 A NZ579635 A NZ 579635A NZ 57963508 A NZ57963508 A NZ 57963508A NZ 579635 A NZ579635 A NZ 579635A

Authority

NZ

New Zealand

Prior art keywords

substituted

compound

mmol

unsubstituted

alkyl

Prior art date

2007-03-20

Links

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• ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 title abstract description 4
• 239000003481 heat shock protein 90 inhibitor Substances 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 598
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 68
• 201000011510 cancer Diseases 0.000 claims abstract description 36
• 238000011282 treatment Methods 0.000 claims abstract description 35
• 150000003839 salts Chemical class 0.000 claims abstract description 30
• 101710113864 Heat shock protein 90 Proteins 0.000 claims abstract description 29
• 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims abstract description 29
• 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 claims abstract description 18
• 239000012453 solvate Substances 0.000 claims abstract description 16
• 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 14
• 230000004770 neurodegeneration Effects 0.000 claims abstract description 8
• 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
• -1 amino, hydroxy Chemical group 0.000 claims description 155
• 125000001072 heteroaryl group Chemical group 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 58
• 125000000623 heterocyclic group Chemical group 0.000 claims description 57
• 229910052739 hydrogen Inorganic materials 0.000 claims description 48
• 239000001257 hydrogen Substances 0.000 claims description 46
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 40
• 125000000217 alkyl group Chemical group 0.000 claims description 39
• 150000002431 hydrogen Chemical group 0.000 claims description 38
• 229910052717 sulfur Inorganic materials 0.000 claims description 37
• 229910052760 oxygen Inorganic materials 0.000 claims description 34
• 210000004027 cell Anatomy 0.000 claims description 32
• 229910052736 halogen Inorganic materials 0.000 claims description 29
• 150000002367 halogens Chemical group 0.000 claims description 29
• 229920006395 saturated elastomer Polymers 0.000 claims description 28
• 239000003814 drug Substances 0.000 claims description 27
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 125000002252 acyl group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
• 125000003282 alkyl amino group Chemical group 0.000 claims description 22
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
• 125000001931 aliphatic group Chemical group 0.000 claims description 20
• 125000003545 alkoxy group Chemical group 0.000 claims description 20
• 208000035475 disorder Diseases 0.000 claims description 20
• 125000004414 alkyl thio group Chemical group 0.000 claims description 19
• 125000003107 substituted aryl group Chemical group 0.000 claims description 19
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 17
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 13
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 10
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
• 230000000750 progressive effect Effects 0.000 claims description 9
• 125000005017 substituted alkenyl group Chemical class 0.000 claims description 9
• 125000004426 substituted alkynyl group Chemical class 0.000 claims description 9
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• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 7
• 125000004122 cyclic group Chemical group 0.000 claims description 7
• 238000004519 manufacturing process Methods 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
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• 239000004480 active ingredient Substances 0.000 claims description 6
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• 208000023105 Huntington disease Diseases 0.000 claims description 5
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• CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 5
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 5
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• 229910020008 S(O) Inorganic materials 0.000 claims description 4
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• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
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• 206010009944 Colon cancer Diseases 0.000 claims description 3
• 206010067889 Dementia with Lewy bodies Diseases 0.000 claims description 3
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• 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims description 3
• 208000001799 Hereditary Optic Atrophies Diseases 0.000 claims description 3
• 208000009829 Lewy Body Disease Diseases 0.000 claims description 3
• 208000000609 Pick Disease of the Brain Diseases 0.000 claims description 3
• 208000032319 Primary lateral sclerosis Diseases 0.000 claims description 3
• 208000009106 Shy-Drager Syndrome Diseases 0.000 claims description 3
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• 208000000323 Tourette Syndrome Diseases 0.000 claims description 3
• 208000016620 Tourette disease Diseases 0.000 claims description 3
• 206010046298 Upper motor neurone lesion Diseases 0.000 claims description 3
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
• 201000006517 essential tremor Diseases 0.000 claims description 3
• 208000014829 head and neck neoplasm Diseases 0.000 claims description 3
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• 230000001969 hypertrophic effect Effects 0.000 claims description 3
• 230000007824 polyneuropathy Effects 0.000 claims description 3
• 230000002062 proliferating effect Effects 0.000 claims description 3
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• 208000003755 striatonigral degeneration Diseases 0.000 claims description 3
• 208000018724 torsion dystonia Diseases 0.000 claims description 3
• 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 2
• 206010003571 Astrocytoma Diseases 0.000 claims description 2
• 206010006187 Breast cancer Diseases 0.000 claims description 2
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• 206010010904 Convulsion Diseases 0.000 claims description 2
• 208000017604 Hodgkin disease Diseases 0.000 claims description 2
• 208000010747 Hodgkins lymphoma Diseases 0.000 claims description 2
• 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
• 206010029260 Neuroblastoma Diseases 0.000 claims description 2
• 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
• 208000006265 Renal cell carcinoma Diseases 0.000 claims description 2
• 208000024770 Thyroid neoplasm Diseases 0.000 claims description 2
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
• 231100000844 hepatocellular carcinoma Toxicity 0.000 claims description 2
• 229910052740 iodine Inorganic materials 0.000 claims description 2
• 201000005202 lung cancer Diseases 0.000 claims description 2
• 208000020816 lung neoplasm Diseases 0.000 claims description 2
• 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
• 201000002528 pancreatic cancer Diseases 0.000 claims description 2
• 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
• 229920000155 polyglutamine Polymers 0.000 claims description 2
• 108010040003 polyglutamine Proteins 0.000 claims description 2
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 2
• 201000002510 thyroid cancer Diseases 0.000 claims description 2
• 125000003396 thiol group Chemical group [H]S* 0.000 claims 9
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• 238000011321 prophylaxis Methods 0.000 claims 2
• 206010005003 Bladder cancer Diseases 0.000 claims 1
• 229910014585 C2-Ce Inorganic materials 0.000 claims 1
• 206010008111 Cerebral haemorrhage Diseases 0.000 claims 1
• 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
• 208000007766 Kaposi sarcoma Diseases 0.000 claims 1
• 206010033128 Ovarian cancer Diseases 0.000 claims 1
• 206010061535 Ovarian neoplasm Diseases 0.000 claims 1
• 206010060862 Prostate cancer Diseases 0.000 claims 1
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
• 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
• 206010047741 Vulval cancer Diseases 0.000 claims 1
• 208000004354 Vulvar Neoplasms Diseases 0.000 claims 1
• 208000029742 colonic neoplasm Diseases 0.000 claims 1
• 208000020658 intracerebral hemorrhage Diseases 0.000 claims 1
• 208000026037 malignant tumor of neck Diseases 0.000 claims 1
• 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 1
• 208000003154 papilloma Diseases 0.000 claims 1
• 206010041823 squamous cell carcinoma Diseases 0.000 claims 1
• 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 1
• 201000005112 urinary bladder cancer Diseases 0.000 claims 1
• 201000005102 vulva cancer Diseases 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 11
• 108090000623 proteins and genes Proteins 0.000 abstract description 9
• 102000004169 proteins and genes Human genes 0.000 abstract description 6
• 108010006519 Molecular Chaperones Proteins 0.000 abstract description 3
• 102000005431 Molecular Chaperones Human genes 0.000 abstract description 3
• 208000037765 diseases and disorders Diseases 0.000 abstract description 2
• 230000012846 protein folding Effects 0.000 abstract description 2
• 230000029983 protein stabilization Effects 0.000 abstract description 2
• 230000022983 regulation of cell cycle Effects 0.000 abstract description 2
• 230000022532 regulation of transcription, DNA-dependent Effects 0.000 abstract description 2
• 230000019491 signal transduction Effects 0.000 abstract description 2
• 238000011105 stabilization Methods 0.000 abstract description 2
• KYAFCVSEPWYUSW-UHFFFAOYSA-N 3h-imidazo[4,5-c]pyridin-2-amine Chemical class C1=NC=C2NC(N)=NC2=C1 KYAFCVSEPWYUSW-UHFFFAOYSA-N 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
• 239000000203 mixture Substances 0.000 description 196
• 239000007787 solid Substances 0.000 description 195
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 167
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 165
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 158
• NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 description 154
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 118
• 238000005481 NMR spectroscopy Methods 0.000 description 106
• 238000000034 method Methods 0.000 description 101
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• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
• 229960004979 fampridine Drugs 0.000 description 77
• 238000004440 column chromatography Methods 0.000 description 71
• 229960001866 silicon dioxide Drugs 0.000 description 68
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• XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 62
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 47
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• 125000004432 carbon atom Chemical group C* 0.000 description 37
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
• 239000003795 chemical substances by application Substances 0.000 description 33
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 33
• MFZBSWSCIWCRKS-UHFFFAOYSA-N 2,9-dimethyl-1,10-phenanthroline;hydrate Chemical compound O.C1=C(C)N=C2C3=NC(C)=CC=C3C=CC2=C1 MFZBSWSCIWCRKS-UHFFFAOYSA-N 0.000 description 30
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• MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 28
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• WNYBGSQHYDNPIE-UHFFFAOYSA-N 4-amino-1-[(4-methoxyphenyl)methyl]-3h-imidazo[4,5-c]pyridine-2-thione Chemical compound C1=CC(OC)=CC=C1CN1C2=CC=NC(N)=C2N=C1S WNYBGSQHYDNPIE-UHFFFAOYSA-N 0.000 description 15
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