TW200911806A - Novel compound-827 - Google Patents

Info

Publication number

TW200911806A

TW200911806A TW097123686A TW97123686A TW200911806A TW 200911806 A TW200911806 A TW 200911806A TW 097123686 A TW097123686 A TW 097123686A TW 97123686 A TW97123686 A TW 97123686A TW 200911806 A TW200911806 A TW 200911806A

Authority

TW

Taiwan

Prior art keywords

tetrahydro

cyanocyclopropyl

pyrido

carbonyl

cyclohexanecarboxamide

Prior art date

2007-06-26

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 claims abstract description 159
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
• 108090000625 Cathepsin K Proteins 0.000 claims abstract description 8
• 102000004171 Cathepsin K Human genes 0.000 claims abstract description 8
• 108010005843 Cysteine Proteases Proteins 0.000 claims abstract description 5
• 102000005927 Cysteine Proteases Human genes 0.000 claims abstract description 5
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
• -1 1-cyanocyclopropyl Chemical group 0.000 claims description 111
• PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 claims description 88
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 69
• 150000003839 salts Chemical class 0.000 claims description 64
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 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 36
• 239000002253 acid Substances 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 31
• 238000000034 method Methods 0.000 claims description 30
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 29
• 125000004429 atom Chemical group 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 20
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
• 125000002950 monocyclic group Chemical group 0.000 claims description 18
• 125000005842 heteroatom Chemical group 0.000 claims description 17
• IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 12
• 125000004452 carbocyclyl group Chemical group 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000004434 sulfur atom Chemical group 0.000 claims description 9
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• HVDYERDERUWLKL-UHFFFAOYSA-N 1-(decylamino)cyclopropane-1-carbonitrile Chemical compound C(#N)C1(CC1)NCCCCCCCCCC HVDYERDERUWLKL-UHFFFAOYSA-N 0.000 claims description 7
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
• JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 claims description 7
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000006413 ring segment Chemical group 0.000 claims description 7
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 239000002243 precursor Substances 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• 125000001931 aliphatic group Chemical group 0.000 claims description 5
• 210000000988 bone and bone Anatomy 0.000 claims description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
• NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
• 208000037848 Metastatic bone disease Diseases 0.000 claims description 4
• 208000001132 Osteoporosis Diseases 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000005843 halogen group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 208000004296 neuralgia Diseases 0.000 claims description 4
• 208000021722 neuropathic pain Diseases 0.000 claims description 4
• 201000008482 osteoarthritis Diseases 0.000 claims description 4
• 229910052707 ruthenium Inorganic materials 0.000 claims description 4
• IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
• 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 3
• 125000002837 carbocyclic group Chemical group 0.000 claims description 3
• 125000004122 cyclic group Chemical group 0.000 claims description 3
• NZNMSOFKMUBTKW-UHFFFAOYSA-M cyclohexanecarboxylate Chemical compound [O-]C(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-M 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 230000000010 osteolytic effect Effects 0.000 claims description 3
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 239000003085 diluting agent Substances 0.000 claims description 2
• AEDIXYWIVPYNBI-UHFFFAOYSA-N heptanamide Chemical compound CCCCCCC(N)=O AEDIXYWIVPYNBI-UHFFFAOYSA-N 0.000 claims description 2
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
• 238000006467 substitution reaction Methods 0.000 claims description 2
• 241000124008 Mammalia Species 0.000 claims 2
• 125000004432 carbon atom Chemical group C* 0.000 claims 2
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
• 238000002560 therapeutic procedure Methods 0.000 claims 2
• VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 1
• YPHMISFOHDHNIV-FSZOTQKASA-N Cycloheximide Natural products C1[C@@H](C)C[C@H](C)C(=O)[C@@H]1[C@H](O)CC1CC(=O)NC(=O)C1 YPHMISFOHDHNIV-FSZOTQKASA-N 0.000 claims 1
• 241001122767 Theaceae Species 0.000 claims 1
• 150000005347 biaryls Chemical group 0.000 claims 1
• 235000010290 biphenyl Nutrition 0.000 claims 1
• 150000003857 carboxamides Chemical class 0.000 claims 1
• SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims 1
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexyloxide Natural products O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 56
• 239000003112 inhibitor Substances 0.000 abstract description 33
• 102000005600 Cathepsins Human genes 0.000 abstract description 7
• 108010084457 Cathepsins Proteins 0.000 abstract description 7
• 229910052799 carbon Inorganic materials 0.000 abstract description 7
• 201000010099 disease Diseases 0.000 abstract description 6
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 6
• 229910052731 fluorine Inorganic materials 0.000 abstract description 4
• 230000002441 reversible effect Effects 0.000 abstract description 4
• 230000000694 effects Effects 0.000 abstract description 3
• 229910052700 potassium Inorganic materials 0.000 abstract description 3
• 229910052721 tungsten Inorganic materials 0.000 abstract description 3
• 229910052796 boron Inorganic materials 0.000 abstract description 2
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 180
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
• 239000007787 solid Substances 0.000 description 67
• 238000005481 NMR spectroscopy Methods 0.000 description 60
• 239000000243 solution Substances 0.000 description 53
• 238000006243 chemical reaction Methods 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 43
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 41
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 37
• 239000007858 starting material Substances 0.000 description 35
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 31
• 235000019439 ethyl acetate Nutrition 0.000 description 30
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 28
• 239000003795 chemical substances by application Substances 0.000 description 26
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
• 238000005160 1H NMR spectroscopy Methods 0.000 description 21
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
• 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
• 239000002904 solvent Substances 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 17
• 229910052786 argon Inorganic materials 0.000 description 17
• 239000003814 drug Substances 0.000 description 16
• 150000002148 esters Chemical class 0.000 description 16
• 239000011541 reaction mixture Substances 0.000 description 16
• 238000010438 heat treatment Methods 0.000 description 15
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 14
• 238000003786 synthesis reaction Methods 0.000 description 14
• 238000010992 reflux Methods 0.000 description 13
• 229940079593 drug Drugs 0.000 description 12
• 238000001727 in vivo Methods 0.000 description 12
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
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• 239000005557 antagonist Substances 0.000 description 11
• 239000012267 brine Substances 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
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• BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 10
• 230000015572 biosynthetic process Effects 0.000 description 10
• 239000007789 gas Substances 0.000 description 10
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• 238000012360 testing method Methods 0.000 description 10
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
• FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
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• 125000006239 protecting group Chemical group 0.000 description 8
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• 235000011152 sodium sulphate Nutrition 0.000 description 8
• 244000166102 Eucalyptus leucoxylon Species 0.000 description 7
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• 239000007821 HATU Substances 0.000 description 7
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 7
• 230000000052 comparative effect Effects 0.000 description 7
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• PCEIEQLJYDMRFZ-UHFFFAOYSA-N (1-cyanocyclopropyl)azanium;chloride Chemical compound Cl.N#CC1(N)CC1 PCEIEQLJYDMRFZ-UHFFFAOYSA-N 0.000 description 6
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• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
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• 150000003335 secondary amines Chemical class 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
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• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
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• WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 4
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• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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