NZ581719A - 1-cyanocyclopropyl-derivatives as cathepsin k inhibitors - Google Patents

Info

Publication number

NZ581719A

NZ581719A NZ581719A NZ58171908A NZ581719A NZ 581719 A NZ581719 A NZ 581719A NZ 581719 A NZ581719 A NZ 581719A NZ 58171908 A NZ58171908 A NZ 58171908A NZ 581719 A NZ581719 A NZ 581719A

Authority

NZ

New Zealand

Prior art keywords

pyrido

tetrahydro

carbonyl

cyanocyclopropyl

cyclohexanecarboxamide

Prior art date

2007-06-26

Links

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• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title abstract description 35
• 102000005600 Cathepsins Human genes 0.000 title description 5
• 108010084457 Cathepsins Proteins 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 169
• -1 particular Proteins 0.000 claims abstract description 84
• 238000000034 method Methods 0.000 claims abstract description 14
• 108090000625 Cathepsin K Proteins 0.000 claims abstract description 12
• 102000004171 Cathepsin K Human genes 0.000 claims abstract description 12
• 210000000988 bone and bone Anatomy 0.000 claims abstract description 7
• 230000008569 process Effects 0.000 claims abstract description 7
• 208000037848 Metastatic bone disease Diseases 0.000 claims abstract description 6
• 208000001132 Osteoporosis Diseases 0.000 claims abstract description 6
• 208000004296 neuralgia Diseases 0.000 claims abstract description 6
• 208000021722 neuropathic pain Diseases 0.000 claims abstract description 6
• 201000008482 osteoarthritis Diseases 0.000 claims abstract description 6
• 230000000010 osteolytic effect Effects 0.000 claims abstract description 6
• 238000002360 preparation method Methods 0.000 claims abstract description 6
• 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract description 6
• PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 110
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 109
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 98
• 150000003839 salts Chemical class 0.000 claims description 56
• 125000000217 alkyl group Chemical group 0.000 claims description 32
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 22
• 229910052736 halogen Inorganic materials 0.000 claims description 21
• 125000002950 monocyclic group Chemical group 0.000 claims description 21
• 125000004122 cyclic group Chemical group 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 150000002367 halogens Chemical class 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 17
• 125000000623 heterocyclic group Chemical group 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• UIVATUPCWVUVIM-UHFFFAOYSA-N 1-aminocyclopropane-1-carbonitrile Chemical compound N#CC1(N)CC1 UIVATUPCWVUVIM-UHFFFAOYSA-N 0.000 claims description 14
• 229910052757 nitrogen Inorganic materials 0.000 claims description 14
• 241001465754 Metazoa Species 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 13
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 125000004429 atom Chemical group 0.000 claims description 11
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
• 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 5
• 125000001931 aliphatic group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 208000020084 Bone disease Diseases 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 2
• 102000005927 Cysteine Proteases Human genes 0.000 abstract description 7
• 108010005843 Cysteine Proteases Proteins 0.000 abstract description 7
• 201000010099 disease Diseases 0.000 abstract description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 5
• 230000002441 reversible effect Effects 0.000 abstract description 4
• 206010005949 Bone cancer Diseases 0.000 abstract description 2
• 208000018084 Bone neoplasm Diseases 0.000 abstract description 2
• 208000006673 asthma Diseases 0.000 abstract description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 187
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 141
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 102
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 82
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
• 238000005481 NMR spectroscopy Methods 0.000 description 78
• 239000007787 solid Substances 0.000 description 76
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 51
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 51
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
• 238000006243 chemical reaction Methods 0.000 description 43
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 39
• 239000000203 mixture Substances 0.000 description 33
• 229910001868 water Inorganic materials 0.000 description 32
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• 239000000243 solution Substances 0.000 description 27
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 26
• 239000002904 solvent Substances 0.000 description 22
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 21
• 238000000746 purification Methods 0.000 description 21
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 19
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
• 239000003795 chemical substances by application Substances 0.000 description 18
• 235000019439 ethyl acetate Nutrition 0.000 description 18
• 239000011541 reaction mixture Substances 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 17
• 150000002148 esters Chemical class 0.000 description 17
• 229940093499 ethyl acetate Drugs 0.000 description 15
• AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 14
• 238000010438 heat treatment Methods 0.000 description 14
• RJTZUHVCZIGJMB-UHFFFAOYSA-N hydron;1h-indole;chloride Chemical compound Cl.C1=CC=C2NC=CC2=C1 RJTZUHVCZIGJMB-UHFFFAOYSA-N 0.000 description 14
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 14
• 229940002612 prodrug Drugs 0.000 description 14
• 239000000651 prodrug Substances 0.000 description 14
• 239000000377 silicon dioxide Substances 0.000 description 14
• 229910052786 argon Inorganic materials 0.000 description 13
• 238000010992 reflux Methods 0.000 description 13
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 13
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 12
• 239000002253 acid Substances 0.000 description 12
• 239000012267 brine Substances 0.000 description 12
• 238000001727 in vivo Methods 0.000 description 12
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 12
• 241000282414 Homo sapiens Species 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 229910052938 sodium sulfate Inorganic materials 0.000 description 11
• 235000011152 sodium sulphate Nutrition 0.000 description 11
• 238000013459 approach Methods 0.000 description 10
• 238000003818 flash chromatography Methods 0.000 description 10
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
• 229910000027 potassium carbonate Inorganic materials 0.000 description 10
• 125000004076 pyridyl group Chemical group 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• HCUARRIEZVDMPT-UHFFFAOYSA-M 1h-indole-2-carboxylate Chemical compound C1=CC=C2NC(C(=O)[O-])=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-M 0.000 description 9
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 9
• 235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 9
• 239000007821 HATU Substances 0.000 description 9
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
• 239000005557 antagonist Substances 0.000 description 9
• 239000000047 product Substances 0.000 description 9
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 8
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
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• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 238000007792 addition Methods 0.000 description 7
• 239000006260 foam Substances 0.000 description 7
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• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 7
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 7
• 229910000069 nitrogen hydride Inorganic materials 0.000 description 7
• GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 description 7
• 150000003335 secondary amines Chemical class 0.000 description 7
• 239000007858 starting material Substances 0.000 description 7
• 239000000725 suspension Substances 0.000 description 7
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
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• QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
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• 238000001990 intravenous administration Methods 0.000 description 5
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• 229940124597 therapeutic agent Drugs 0.000 description 5
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• XGALLCVXEZPNRQ-UHFFFAOYSA-N gefitinib Chemical compound C=12C=C(OCCCN3CCOCC3)C(OC)=CC2=NC=NC=1NC1=CC=C(F)C(Cl)=C1 XGALLCVXEZPNRQ-UHFFFAOYSA-N 0.000 description 3
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