TW200911806A - Novel compound-827 - Google Patents
Novel compound-827 Download PDFInfo
- 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
Links
- 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
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- 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 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
- 238000004895 liquid chromatography mass spectrometry Methods 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-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
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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
- 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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- 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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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US94617807P | 2007-06-26 | 2007-06-26 | |
| US4284008P | 2008-04-07 | 2008-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200911806A true TW200911806A (en) | 2009-03-16 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW097123686A TW200911806A (en) | 2007-06-26 | 2008-06-25 | Novel compound-827 |
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| EP (1) | EP2170879B1 (enExample) |
| JP (1) | JP2010531344A (enExample) |
| KR (1) | KR20100039862A (enExample) |
| CN (1) | CN101687864A (enExample) |
| AR (1) | AR067156A1 (enExample) |
| AU (1) | AU2008269513B2 (enExample) |
| BR (1) | BRPI0813306A2 (enExample) |
| CA (1) | CA2689945A1 (enExample) |
| CL (1) | CL2008001899A1 (enExample) |
| CO (1) | CO6251264A2 (enExample) |
| EC (1) | ECSP109882A (enExample) |
| IL (1) | IL202519A0 (enExample) |
| NZ (1) | NZ581719A (enExample) |
| PE (1) | PE20090841A1 (enExample) |
| RU (1) | RU2470023C2 (enExample) |
| TW (1) | TW200911806A (enExample) |
| UY (1) | UY31180A1 (enExample) |
| WO (1) | WO2009001129A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101614723B1 (ko) | 2008-01-11 | 2016-04-22 | 알바니 몰레큘라 리써치, 인크. | Ｍｃｈ 길항물질로서 (1-아지논)-치환된 피리도인돌 |
| RU2544856C2 (ru) | 2008-01-25 | 2015-03-20 | Сергей Олегович Бачурин | НОВЫЕ ПРОИЗВОДНЫЕ 2,3,4,5-ТЕТРАГИДРО-1-ПИРИДО[4,3-b]ИНДОЛА И СПОСОБЫ ИХ ПРИМЕНЕНИЯ |
| JP5666036B2 (ja) * | 2008-01-25 | 2015-02-04 | メディベイション テクノロジーズ， インコーポレイテッド | 新規２，３，４，５−テトラヒドロ−１Ｈ−ピリド［４，３−ｂ］インドール化合物およびその使用方法 |
| WO2010036998A2 (en) | 2008-09-29 | 2010-04-01 | Abbott Laboratories | Indole and indoline derivatives and methods of use thereof |
| US9625475B2 (en) | 2008-09-29 | 2017-04-18 | Abbvie Inc. | Indole and indoline derivatives and methods of use thereof |
| AU2009336040B2 (en) * | 2008-12-18 | 2015-07-16 | Merck Patent Gmbh | Tricyclic azaindoles |
| US7893099B2 (en) * | 2009-06-11 | 2011-02-22 | Hoffman-La Roche Inc. | Cyclopentane derivatives |
| JP2012532144A (ja) * | 2009-07-01 | 2012-12-13 | アルバニー モレキュラー リサーチ， インコーポレイテッド | アジノン置換アゼピノ［ｂ］インドールおよびピリド−ピロロ−アゼピンｍｃｈ−１拮抗薬、ならびにその作製方法および使用 |
| US8618299B2 (en) * | 2009-07-01 | 2013-12-31 | Albany Molecular Research, Inc. | Azinone-substituted azapolycycle MCH-1 antagonists, methods of making, and use thereof |
| WO2011003007A1 (en) * | 2009-07-01 | 2011-01-06 | Albany Molecular Research, Inc. | Azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine mch-1 antagonists, methods of making, and use thereof |
| US9073925B2 (en) * | 2009-07-01 | 2015-07-07 | Albany Molecular Research, Inc. | Azinone-substituted azabicycloalkane-indole and azabicycloalkane-pyrrolo-pyridine MCH-1 antagonists, methods of making, and use thereof |
| PH12012500775A1 (en) | 2009-10-21 | 2012-11-26 | Boehringer Ingelheim Int | Indazole and pyrazolopyridine compounds as ccr1 receptor antagonists |
| US8927550B2 (en) | 2009-10-27 | 2015-01-06 | Boehringer Ingelheim International Gmbh | Heterocyclic compounds as CCR1 receptor antagonists |
| WO2011084433A2 (en) | 2009-12-17 | 2011-07-14 | Abbott Laboratories | Aza-bridged ring-fused indoles and indolines |
| US8524703B2 (en) | 2009-12-17 | 2013-09-03 | Abbvie Inc. | Bridgehead amine ring-fused indoles and indolines |
| US8871786B2 (en) | 2010-04-30 | 2014-10-28 | Boehringer Ingelheim International Gmbh | Azaindazole amide compounds as CCR1 receptor antagonists |
| US8993765B2 (en) | 2010-12-21 | 2015-03-31 | Albany Molecular Research, Inc. | Tetrahydro-azacarboline MCH-1 antagonists, methods of making, and uses thereof |
| US8697700B2 (en) | 2010-12-21 | 2014-04-15 | Albany Molecular Research, Inc. | Piperazinone-substituted tetrahydro-carboline MCH-1 antagonists, methods of making, and uses thereof |
| US8791132B2 (en) | 2011-02-18 | 2014-07-29 | Medivation Technologies, Inc. | Compounds and methods for treatment of hypertension |
| CA2852173A1 (en) * | 2012-01-11 | 2013-07-18 | Lilli Anselm | Macrocyclic amides as protease inhibitors |
| CN103086923B (zh) * | 2013-01-21 | 2014-04-23 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在治疗骨质疏松症方面的应用 |
| CN105593230B (zh) * | 2013-10-08 | 2018-07-06 | 默沙东公司 | 组织蛋白酶半胱氨酸蛋白酶抑制剂 |
| WO2016027285A2 (en) * | 2014-08-22 | 2016-02-25 | Alkem Laboratories Ltd. | Bicyclic heteroaryl amides as cathepsin cysteine protease inhibitors |
| CN105837479B (zh) * | 2016-04-05 | 2017-10-27 | 吉林大学 | 肼腈类组织蛋白酶k抑制剂及其在制备治疗骨关节炎药物中的应用 |
| EP3600451B1 (en) * | 2017-03-29 | 2025-12-24 | Minerva Biotechnologies Corporation | Agents for differentiating stem cells and treating cancer |
| CN118742549A (zh) * | 2022-01-21 | 2024-10-01 | 山东新时代药业有限公司 | 一种组织蛋白酶k抑制剂与其制备方法及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2379747C (en) * | 1999-07-30 | 2008-09-23 | Boehringer Ingelheim Pharmaceuticals, Inc. | Novel succinate derivative compounds useful as cysteine protease inhibitors |
| DE60132975T2 (de) * | 2000-01-06 | 2009-02-26 | Merck Frosst Canada Inc., Kirkland | Neue substanzen und verbindungen als protease-inhibitoren |
| AU2001245764A1 (en) | 2000-03-15 | 2001-09-24 | Axys Pharmaceuticals, Inc. | Novel compounds and compositions as protease inhibitors |
| CA2439415C (en) | 2001-03-02 | 2011-09-20 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| RU2278863C2 (ru) * | 2001-08-10 | 2006-06-27 | Орто-Макнейл Фармасьютикал, Инк. | Замещенные пиразолы, фармацевтическая композиция и способ ингибирования активности катепсина s |
| HUP0402344A2 (hu) * | 2001-12-04 | 2005-02-28 | F. Hoffmann-La Roche Ag | Helyettesített 2-amino-cikloalkán-karboxamidok, felhasználásuk cisztein-proteáz-inhibitorként, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| SE0201977D0 (sv) * | 2002-06-24 | 2002-06-24 | Astrazeneca Ab | Novel compounds |
| SE0203712D0 (sv) | 2002-12-13 | 2002-12-13 | Astrazeneca Ab | Novel compounds |
| WO2004056324A2 (en) | 2002-12-19 | 2004-07-08 | Bristol-Myers Squibb Company | Substituted tricyclic gamma-carbolines as serotonin receptor agonists and antagonists |
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2008
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- 2008-06-24 RU RU2010101279/04A patent/RU2470023C2/ru not_active IP Right Cessation
- 2008-06-24 AU AU2008269513A patent/AU2008269513B2/en not_active Ceased
- 2008-06-24 EP EP08776161A patent/EP2170879B1/en active Active
- 2008-06-24 BR BRPI0813306A patent/BRPI0813306A2/pt not_active IP Right Cessation
- 2008-06-24 CA CA2689945A patent/CA2689945A1/en not_active Abandoned
- 2008-06-24 JP JP2010514135A patent/JP2010531344A/ja active Pending
- 2008-06-24 KR KR1020107001848A patent/KR20100039862A/ko not_active Withdrawn
- 2008-06-24 NZ NZ581719A patent/NZ581719A/en not_active IP Right Cessation
- 2008-06-24 CN CN200880021955A patent/CN101687864A/zh active Pending
- 2008-06-25 US US12/145,855 patent/US8008279B2/en not_active Expired - Fee Related
- 2008-06-25 TW TW097123686A patent/TW200911806A/zh unknown
- 2008-06-25 AR ARP080102722A patent/AR067156A1/es not_active Application Discontinuation
- 2008-06-25 UY UY31180A patent/UY31180A1/es not_active Application Discontinuation
- 2008-06-26 PE PE2008001087A patent/PE20090841A1/es not_active Application Discontinuation
- 2008-06-26 CL CL2008001899A patent/CL2008001899A1/es unknown
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2009
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- 2009-12-22 CO CO09146663A patent/CO6251264A2/es not_active Application Discontinuation
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2010
- 2010-01-15 EC EC2010009882A patent/ECSP109882A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2470023C2 (ru) | 2012-12-20 |
| PE20090841A1 (es) | 2009-08-02 |
| BRPI0813306A2 (pt) | 2017-05-16 |
| ECSP109882A (es) | 2010-02-26 |
| WO2009001129A1 (en) | 2008-12-31 |
| AU2008269513B2 (en) | 2011-06-16 |
| AU2008269513A1 (en) | 2008-12-31 |
| JP2010531344A (ja) | 2010-09-24 |
| IL202519A0 (en) | 2010-06-30 |
| CN101687864A (zh) | 2010-03-31 |
| RU2010101279A (ru) | 2011-08-10 |
| WO2009001129A9 (en) | 2010-02-04 |
| UY31180A1 (es) | 2009-01-30 |
| EP2170879B1 (en) | 2013-01-16 |
| NZ581719A (en) | 2011-08-26 |
| KR20100039862A (ko) | 2010-04-16 |
| CL2008001899A1 (es) | 2009-07-17 |
| EP2170879A1 (en) | 2010-04-07 |
| US20090012077A1 (en) | 2009-01-08 |
| CA2689945A1 (en) | 2008-12-31 |
| AR067156A1 (es) | 2009-09-30 |
| US8008279B2 (en) | 2011-08-30 |
| CO6251264A2 (es) | 2011-02-21 |
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