CA2672327A1 - Aza-indolyl compounds and methods of use - Google Patents
Aza-indolyl compounds and methods of use Download PDFInfo
- Publication number
- CA2672327A1 CA2672327A1 CA002672327A CA2672327A CA2672327A1 CA 2672327 A1 CA2672327 A1 CA 2672327A1 CA 002672327 A CA002672327 A CA 002672327A CA 2672327 A CA2672327 A CA 2672327A CA 2672327 A1 CA2672327 A1 CA 2672327A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cr19r20
- mmol
- nhc
- cr14r15
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 166
- 125000005334 azaindolyl group Chemical group N1N=C(C2=CC=CC=C12)* 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 282
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 39
- 241000124008 Mammalia Species 0.000 claims abstract description 37
- 230000002159 abnormal effect Effects 0.000 claims abstract description 13
- 230000010261 cell growth Effects 0.000 claims abstract description 11
- 230000003463 hyperproliferative effect Effects 0.000 claims abstract description 10
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 10
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 143
- 125000005843 halogen group Chemical group 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 125000000623 heterocyclic group Chemical group 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 31
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 28
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 13
- 229910006074 SO2NH2 Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 239000002246 antineoplastic agent Substances 0.000 claims description 10
- 229940127089 cytotoxic agent Drugs 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 9
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 5
- 229910004749 OS(O)2 Inorganic materials 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 2
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 127
- 238000011282 treatment Methods 0.000 abstract description 23
- 230000000694 effects Effects 0.000 abstract description 8
- 102000001291 MAP Kinase Kinase Kinase Human genes 0.000 abstract description 5
- 108060006687 MAP kinase kinase kinase Proteins 0.000 abstract description 5
- 238000003745 diagnosis Methods 0.000 abstract description 4
- 238000000338 in vitro Methods 0.000 abstract description 4
- 238000001727 in vivo Methods 0.000 abstract description 4
- 238000011065 in-situ storage Methods 0.000 abstract description 4
- 210000004962 mammalian cell Anatomy 0.000 abstract description 4
- 230000001575 pathological effect Effects 0.000 abstract description 4
- 230000001093 anti-cancer Effects 0.000 abstract description 3
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 295
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 257
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 215
- 239000000243 solution Substances 0.000 description 135
- 239000002904 solvent Substances 0.000 description 127
- -1 hydrocarbon radical Chemical class 0.000 description 111
- 239000007787 solid Substances 0.000 description 111
- 235000019439 ethyl acetate Nutrition 0.000 description 108
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 102
- 229910052740 iodine Inorganic materials 0.000 description 101
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
- 239000011541 reaction mixture Substances 0.000 description 91
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 89
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 84
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 80
- 229940093499 ethyl acetate Drugs 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 70
- 238000003818 flash chromatography Methods 0.000 description 64
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 62
- 239000003921 oil Substances 0.000 description 56
- 235000019198 oils Nutrition 0.000 description 56
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 52
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 239000012044 organic layer Substances 0.000 description 48
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 46
- 239000002585 base Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 43
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 41
- 101150041968 CDC13 gene Proteins 0.000 description 40
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 description 38
- 229910052938 sodium sulfate Inorganic materials 0.000 description 37
- 235000011152 sodium sulphate Nutrition 0.000 description 37
- 210000004027 cell Anatomy 0.000 description 36
- 238000005481 NMR spectroscopy Methods 0.000 description 33
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 239000002253 acid Substances 0.000 description 31
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000012267 brine Substances 0.000 description 29
- 238000010992 reflux Methods 0.000 description 29
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 29
- 238000005160 1H NMR spectroscopy Methods 0.000 description 28
- 239000007832 Na2SO4 Substances 0.000 description 28
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 206010028980 Neoplasm Diseases 0.000 description 26
- 239000000377 silicon dioxide Substances 0.000 description 26
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
- 239000000047 product Substances 0.000 description 23
- WWWTWPXKLJTKPM-UHFFFAOYSA-N 2-aminooxyethanol Chemical compound NOCCO WWWTWPXKLJTKPM-UHFFFAOYSA-N 0.000 description 22
- XZTSFVPMMQNIAJ-UHFFFAOYSA-N o-(2-ethenoxyethyl)hydroxylamine Chemical compound NOCCOC=C XZTSFVPMMQNIAJ-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 21
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 20
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 20
- 108090000744 Mitogen-Activated Protein Kinase Kinases Proteins 0.000 description 20
- 102000004232 Mitogen-Activated Protein Kinase Kinases Human genes 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 19
- 208000035475 disorder Diseases 0.000 description 19
- 239000000758 substrate Substances 0.000 description 19
- 238000003556 assay Methods 0.000 description 18
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 18
- 201000010099 disease Diseases 0.000 description 18
- 238000000746 purification Methods 0.000 description 18
- 239000012453 solvate Substances 0.000 description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 229940002612 prodrug Drugs 0.000 description 17
- 239000000651 prodrug Substances 0.000 description 17
- 239000000706 filtrate Substances 0.000 description 16
- 239000010410 layer Substances 0.000 description 16
- 235000019341 magnesium sulphate Nutrition 0.000 description 16
- 125000001424 substituent group Chemical group 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
- 150000001412 amines Chemical class 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 239000012312 sodium hydride Substances 0.000 description 15
- 229910000104 sodium hydride Inorganic materials 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 125000004043 oxo group Chemical group O=* 0.000 description 14
- 229910000024 caesium carbonate Inorganic materials 0.000 description 13
- 201000011510 cancer Diseases 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 12
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 11
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- 125000004122 cyclic group Chemical group 0.000 description 11
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- 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 10
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- 238000007429 general method Methods 0.000 description 10
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
- PWZIBVWIAKQRMS-UHFFFAOYSA-N (2-fluoro-4-trimethylsilylphenyl) trifluoromethanesulfonate Chemical compound C[Si](C)(C)C1=CC=C(OS(=O)(=O)C(F)(F)F)C(F)=C1 PWZIBVWIAKQRMS-UHFFFAOYSA-N 0.000 description 9
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- 229910052736 halogen Inorganic materials 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- 238000006722 reduction reaction Methods 0.000 description 9
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- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000005859 coupling reaction Methods 0.000 description 6
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- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 6
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- 201000005112 urinary bladder cancer Diseases 0.000 description 1
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- 229960000241 vandetanib Drugs 0.000 description 1
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- 229960002066 vinorelbine Drugs 0.000 description 1
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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
- 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
- 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
- A61P35/00—Antineoplastic agents
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86805506P | 2006-11-30 | 2006-11-30 | |
| US60/868,055 | 2006-11-30 | ||
| US91762007P | 2007-05-11 | 2007-05-11 | |
| US60/917,620 | 2007-05-11 | ||
| US94474307P | 2007-06-18 | 2007-06-18 | |
| US60/944,743 | 2007-06-18 | ||
| PCT/US2007/085962 WO2008067481A1 (en) | 2006-11-30 | 2007-11-29 | Aza-indolyl compounds and methods of use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2672327A1 true CA2672327A1 (en) | 2008-06-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002672327A Abandoned CA2672327A1 (en) | 2006-11-30 | 2007-11-29 | Aza-indolyl compounds and methods of use |
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| EP (1) | EP2099796B1 (enExample) |
| JP (1) | JP5211063B2 (enExample) |
| AR (1) | AR064031A1 (enExample) |
| AT (1) | ATE511509T1 (enExample) |
| AU (1) | AU2007325123B2 (enExample) |
| CA (1) | CA2672327A1 (enExample) |
| CL (1) | CL2007003444A1 (enExample) |
| DK (1) | DK2099796T3 (enExample) |
| PE (1) | PE20081354A1 (enExample) |
| PL (1) | PL2099796T3 (enExample) |
| PT (1) | PT2099796E (enExample) |
| TW (1) | TW200829586A (enExample) |
| WO (1) | WO2008067481A1 (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011526267A (ja) * | 2008-07-03 | 2011-10-06 | バイエル ファーマ アクチエンゲゼルシャフト | 化合物および放射性医薬品の製造方法 |
| US9084781B2 (en) | 2008-12-10 | 2015-07-21 | Novartis Ag | MEK mutations conferring resistance to MEK inhibitors |
| MX360932B (es) | 2010-02-25 | 2018-11-21 | Dana Farber Cancer Inst Inc | Mutaciones del protooncogen de serina/treonina-proteina cinasa b-raf (braf) que confieren resistencia a los inhibidores del protooncogen de serina/treonina-proteina cinasa b-raf. |
| EP2545187B1 (en) | 2010-03-09 | 2018-09-05 | Dana-Farber Cancer Institute, Inc. | Methods of diagnosing and treating cancer in patients having or developing resistance to a first cancer therapy |
| CN103153063B (zh) | 2010-07-30 | 2016-02-17 | 肿瘤疗法科学股份有限公司 | 喹啉衍生物及含有其的melk抑制剂 |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| TW201414734A (zh) | 2012-07-10 | 2014-04-16 | Takeda Pharmaceutical | 氮雜吲哚衍生物 |
| US20150265679A1 (en) | 2012-11-02 | 2015-09-24 | The United States Of America, As Represented By Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undregoing treatment with a mek inhibitor |
| UA111925C2 (uk) | 2012-12-11 | 2016-06-24 | Федора Фармасьютікалз Інк. | БІЦИКЛІЧНІ СПОЛУКИ ТА ЇХ ВИКОРИСТАННЯ ЯК АНТИБАКТЕРІАЛЬНИХ АГЕНТІВ ТА ІНГІБІТОРІВ β-ЛАКТАМАЗИ |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| US20170114323A1 (en) | 2014-06-19 | 2017-04-27 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| WO2017180581A1 (en) | 2016-04-15 | 2017-10-19 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| EP3624795B1 (en) | 2017-05-19 | 2022-04-20 | NFlection Therapeutics, Inc. | Fused heteroaromatic-aniline compounds for treatment of dermal disorders |
| KR102642411B1 (ko) * | 2017-05-19 | 2024-02-28 | 엔플렉션 테라퓨틱스, 인코포레이티드 | 피부병 치료를 위한 피롤로피리딘-아닐린 화합물 |
| CA3073073A1 (en) | 2017-09-08 | 2019-03-14 | F. Hoffmann-La Roche Ag | Diagnostic and therapeutic methods for cancer |
| EP3752200A1 (en) | 2018-02-13 | 2020-12-23 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| JP7406264B2 (ja) | 2018-11-20 | 2023-12-27 | エヌフレクション セラピューティクス インコーポレイテッド | 皮膚障害の処置のためのシアノアリール－アニリン化合物 |
| CN117551073A (zh) | 2018-11-20 | 2024-02-13 | 恩福莱克逊治疗有限公司 | 用于治疗皮肤疾病噻吩基苯胺化合物 |
| US12378240B2 (en) | 2018-11-20 | 2025-08-05 | Nflection Therapeutics, Inc. | Naphthyridinone-aniline compounds for treatment of dermal disorders |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| CA3238962A1 (en) | 2021-11-23 | 2023-06-01 | Nflection Therapeutics, Inc. | Formulations of pyrrolopyridine-aniline compounds |
| CA3247162A1 (en) * | 2022-01-28 | 2023-08-03 | Insilico Medicine Ip Limited | Ectunocleotide pyrophosphatase-phosphodiesterase 1 (ENPP1) inhibitors and their uses |
| JP2025508014A (ja) * | 2022-03-04 | 2025-03-21 | サムジン ファーマシューティカル カンパニー，リミテッド | 新規ヘテロ環化合物およびそれを含む薬学的組成物 |
| WO2024033381A1 (en) | 2022-08-10 | 2024-02-15 | Vib Vzw | Inhibition of tcf4/itf2 in the treatment of cancer |
| WO2025026383A1 (en) * | 2023-08-02 | 2025-02-06 | Insilico Medicine Ip Limited | Crytsalline forms of ectonucleotide pyrophosphatase-phosphodiesterase 1 (enpp1) inhibitors and uses thereof |
| WO2025100940A1 (ko) * | 2023-11-07 | 2025-05-15 | 보로노이 주식회사 | 헤테로아릴 유도체 화합물 및 이의 용도 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235537B2 (en) * | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| AU2003225131A1 (en) | 2002-04-23 | 2003-11-10 | Aventis Pharmaceuticals Inc. | 3-substituted amino-1h-indole-2-carboxylic acid and 3-substituted amino-benzo' b! thiophene-2-carboxylic acid derivatives as interieukin-4 gene expression inhibitors |
| US6929411B2 (en) * | 2003-09-03 | 2005-08-16 | Hewlett-Packard Development Company, L.P. | Selectable control of raster image processor |
| GB0412914D0 (en) * | 2004-06-10 | 2004-07-14 | Oxagen Ltd | Compounds |
| AR049300A1 (es) * | 2004-06-15 | 2006-07-12 | Schering Corp | Compuestos triciclicos antagonistas de mglur1 como agentes terapeuticos |
| US7598259B2 (en) * | 2004-06-15 | 2009-10-06 | Schering Corporation | mGluR1 antagonists as therapeutic agents |
| DE102005013621A1 (de) * | 2005-03-24 | 2006-09-28 | Curacyte Discovery Gmbh | Substituierte 2-Aryl(Hetaryl)-5-aminothieno[2,3-d]pyrimidin-6-carbonsäureamide, Verfahren zu ihrer Herstellung und Verwendung als Pharmazeutika |
| AR070127A1 (es) * | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
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2007
- 2007-11-29 EP EP07854844A patent/EP2099796B1/en active Active
- 2007-11-29 AU AU2007325123A patent/AU2007325123B2/en not_active Ceased
- 2007-11-29 JP JP2009539490A patent/JP5211063B2/ja not_active Expired - Fee Related
- 2007-11-29 CL CL200703444A patent/CL2007003444A1/es unknown
- 2007-11-29 PL PL07854844T patent/PL2099796T3/pl unknown
- 2007-11-29 PE PE2007001679A patent/PE20081354A1/es not_active Application Discontinuation
- 2007-11-29 PT PT07854844T patent/PT2099796E/pt unknown
- 2007-11-29 DK DK07854844.3T patent/DK2099796T3/da active
- 2007-11-29 TW TW096145474A patent/TW200829586A/zh unknown
- 2007-11-29 WO PCT/US2007/085962 patent/WO2008067481A1/en not_active Ceased
- 2007-11-29 AT AT07854844T patent/ATE511509T1/de active
- 2007-11-29 US US11/947,656 patent/US7855216B2/en not_active Expired - Fee Related
- 2007-11-29 CA CA002672327A patent/CA2672327A1/en not_active Abandoned
- 2007-11-29 AR ARP070105307A patent/AR064031A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2099796B1 (en) | 2011-06-01 |
| JP2010511626A (ja) | 2010-04-15 |
| ATE511509T1 (de) | 2011-06-15 |
| TW200829586A (en) | 2008-07-16 |
| DK2099796T3 (da) | 2011-09-05 |
| PT2099796E (pt) | 2011-09-06 |
| AR064031A1 (es) | 2009-03-04 |
| WO2008067481A1 (en) | 2008-06-05 |
| AU2007325123A1 (en) | 2008-06-05 |
| AU2007325123B2 (en) | 2012-12-13 |
| US7855216B2 (en) | 2010-12-21 |
| EP2099796A1 (en) | 2009-09-16 |
| JP5211063B2 (ja) | 2013-06-12 |
| CL2007003444A1 (es) | 2008-06-27 |
| PE20081354A1 (es) | 2008-11-14 |
| HK1135099A1 (en) | 2010-05-28 |
| US20080242655A1 (en) | 2008-10-02 |
| PL2099796T3 (pl) | 2011-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |
Effective date: 20170228 |