MX2014010684A - Inhibidores de cinasa a base de arileter. - Google Patents
Inhibidores de cinasa a base de arileter.Info
- Publication number
- MX2014010684A MX2014010684A MX2014010684A MX2014010684A MX2014010684A MX 2014010684 A MX2014010684 A MX 2014010684A MX 2014010684 A MX2014010684 A MX 2014010684A MX 2014010684 A MX2014010684 A MX 2014010684A MX 2014010684 A MX2014010684 A MX 2014010684A
- Authority
- MX
- Mexico
- Prior art keywords
- chromene
- pyridin
- amino
- mmol
- methyl
- Prior art date
Links
- 125000003118 aryl group Chemical group 0.000 title claims description 12
- 229940043355 kinase inhibitor Drugs 0.000 title description 2
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 322
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 239000000203 mixture Substances 0.000 claims abstract description 112
- 102100038079 AP2-associated protein kinase 1 Human genes 0.000 claims abstract description 23
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 165
- -1 Ci-C3-amino dialkyl Chemical group 0.000 claims description 161
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 120
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 59
- 150000003839 salts Chemical class 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 38
- 150000002431 hydrogen Chemical group 0.000 claims description 30
- IMFRKJFJCFESDR-UHFFFAOYSA-N 5-methyl-5h-chromene Chemical compound O1C=CC=C2C(C)C=CC=C21 IMFRKJFJCFESDR-UHFFFAOYSA-N 0.000 claims description 27
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 24
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 101000742699 Homo sapiens AP2-associated protein kinase 1 Proteins 0.000 claims description 21
- UUUCLXHMFVIYCF-UHFFFAOYSA-N 1-(5H-chromen-8-yloxy)-4-methylpentan-2-amine Chemical compound CC(C)CC(N)COC1=C2OC=CC=C2CC=C1 UUUCLXHMFVIYCF-UHFFFAOYSA-N 0.000 claims description 20
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 20
- JBOYQZDFEWOILV-UHFFFAOYSA-N 5h-chromene Chemical compound O1C=CC=C2CC=CC=C21 JBOYQZDFEWOILV-UHFFFAOYSA-N 0.000 claims description 19
- IGEIPFLJVCPEKU-UHFFFAOYSA-N pentan-2-amine Chemical compound CCCC(C)N IGEIPFLJVCPEKU-UHFFFAOYSA-N 0.000 claims description 19
- VYRLLMMEJSVJBK-ABLWVSNPSA-N (2S)-4-methyl-1-[(5-methyl-5H-chromen-8-yl)oxy]pentan-2-amine Chemical compound CC(C)C[C@H](N)COC1=C2OC=CC=C2C(C)C=C1 VYRLLMMEJSVJBK-ABLWVSNPSA-N 0.000 claims description 17
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 208000035475 disorder Diseases 0.000 claims description 14
- 208000002193 Pain Diseases 0.000 claims description 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 12
- QZHPTGXQGDFGEN-UHFFFAOYSA-N chromene Chemical compound C1=CC=C2C=C[CH]OC2=C1 QZHPTGXQGDFGEN-UHFFFAOYSA-N 0.000 claims description 11
- 230000000694 effects Effects 0.000 claims description 11
- FTPNVTKAKWPGFX-UHFFFAOYSA-N CCC1C=CC=C2C1=CC=CO2 Chemical compound CCC1C=CC=C2C1=CC=CO2 FTPNVTKAKWPGFX-UHFFFAOYSA-N 0.000 claims description 9
- UUUCLXHMFVIYCF-ZDUSSCGKSA-N N[C@H](COC=1C=CCC2=CC=COC=12)CC(C)C Chemical compound N[C@H](COC=1C=CCC2=CC=COC=12)CC(C)C UUUCLXHMFVIYCF-ZDUSSCGKSA-N 0.000 claims description 9
- 108091000080 Phosphotransferase Proteins 0.000 claims description 9
- 102000020233 phosphotransferase Human genes 0.000 claims description 9
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 claims description 8
- 125000005221 halo alkyl carbonyl amino group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 8
- 125000003003 spiro group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 125000004992 haloalkylamino group Chemical group 0.000 claims description 6
- 208000004296 neuralgia Diseases 0.000 claims description 6
- 208000021722 neuropathic pain Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims description 4
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims description 4
- CFNQLDVKPDTYDD-UHFFFAOYSA-N 5-cyclopropyl-5H-chromene Chemical compound C1(CC1)C1C2=CC=COC2=CC=C1 CFNQLDVKPDTYDD-UHFFFAOYSA-N 0.000 claims description 4
- WCGVKMGRLFGWRU-UHFFFAOYSA-N CC(C)CC(C)(COC1=C2C(=CC=CO2)CC=C1)N Chemical compound CC(C)CC(C)(COC1=C2C(=CC=CO2)CC=C1)N WCGVKMGRLFGWRU-UHFFFAOYSA-N 0.000 claims description 4
- 125000001769 aryl amino group Chemical group 0.000 claims description 4
- 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229960004979 fampridine Drugs 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 3
- SXLUGOSVIYGFMT-UHFFFAOYSA-N 1-[[7-(difluoromethyl)-5H-chromen-8-yl]oxy]-4-methylpentan-2-amine Chemical compound NC(COC=1C(=CCC2=CC=COC12)C(F)F)CC(C)C SXLUGOSVIYGFMT-UHFFFAOYSA-N 0.000 claims description 3
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 3
- 208000020925 Bipolar disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 208000001640 Fibromyalgia Diseases 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 claims description 2
- 208000033808 peripheral neuropathy Diseases 0.000 claims description 2
- OUCYWJAACMAXQD-UHFFFAOYSA-N pyridin-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=N1 OUCYWJAACMAXQD-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 abstract description 4
- 101710148635 AP2-associated protein kinase 1 Proteins 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 320
- 230000014759 maintenance of location Effects 0.000 description 235
- 238000004811 liquid chromatography Methods 0.000 description 156
- 239000000243 solution Substances 0.000 description 156
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 153
- 230000002829 reductive effect Effects 0.000 description 124
- 229910001868 water Inorganic materials 0.000 description 122
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 120
- 235000019439 ethyl acetate Nutrition 0.000 description 113
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- 239000007787 solid Substances 0.000 description 103
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 101
- 239000011541 reaction mixture Substances 0.000 description 101
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- 238000006243 chemical reaction Methods 0.000 description 92
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 91
- 238000004128 high performance liquid chromatography Methods 0.000 description 88
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- 238000005481 NMR spectroscopy Methods 0.000 description 76
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 58
- 229910052938 sodium sulfate Inorganic materials 0.000 description 58
- 235000011152 sodium sulphate Nutrition 0.000 description 58
- 239000012044 organic layer Substances 0.000 description 51
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 50
- 239000012267 brine Substances 0.000 description 48
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 48
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
- 239000003921 oil Substances 0.000 description 41
- 235000019198 oils Nutrition 0.000 description 40
- 239000012071 phase Substances 0.000 description 38
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 37
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 34
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 34
- 238000007792 addition Methods 0.000 description 32
- 238000000746 purification Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- 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 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 25
- NXFFJDQHYLNEJK-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)methyl]-7-fluoro-5-methylsulfonyl-2,3-dihydro-1h-cyclopenta[b]indol-3-yl]acetic acid Chemical compound C1=2C(S(=O)(=O)C)=CC(F)=CC=2C=2CCC(CC(O)=O)C=2N1CC1=CC=C(Cl)C=C1 NXFFJDQHYLNEJK-UHFFFAOYSA-N 0.000 description 24
- BFJMHTOBRRZELQ-UHFFFAOYSA-N 3-iodo-2h-pyrazolo[3,4-c]pyridine Chemical compound N1=CC=C2C(I)=NNC2=C1 BFJMHTOBRRZELQ-UHFFFAOYSA-N 0.000 description 24
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 24
- 239000000284 extract Substances 0.000 description 24
- 125000006239 protecting group Chemical group 0.000 description 24
- 239000000741 silica gel Substances 0.000 description 24
- 229910002027 silica gel Inorganic materials 0.000 description 24
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 23
- 108090000623 proteins and genes Proteins 0.000 description 23
- 229910000024 caesium carbonate Inorganic materials 0.000 description 22
- 238000002953 preparative HPLC Methods 0.000 description 22
- HUAJXUGTDWQYOX-UHFFFAOYSA-N ClC1=C2OC=CC=C2CC=C1 Chemical compound ClC1=C2OC=CC=C2CC=C1 HUAJXUGTDWQYOX-UHFFFAOYSA-N 0.000 description 21
- 238000004587 chromatography analysis Methods 0.000 description 21
- 125000005843 halogen group Chemical group 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 210000004027 cell Anatomy 0.000 description 20
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- 239000000706 filtrate Substances 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 17
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical class C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 229920006395 saturated elastomer Polymers 0.000 description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 238000005859 coupling reaction Methods 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000000725 suspension Substances 0.000 description 15
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 230000000875 corresponding effect Effects 0.000 description 14
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 241000699670 Mus sp. Species 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- 239000003039 volatile agent Substances 0.000 description 12
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 11
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 150000001299 aldehydes Chemical group 0.000 description 11
- 235000019270 ammonium chloride Nutrition 0.000 description 11
- 239000013058 crude material Substances 0.000 description 11
- 238000009472 formulation Methods 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- OBHQDESDGFZAFD-UHFFFAOYSA-N CC(=O)NC1=CC=C2CC=CC=C2O1 Chemical compound CC(=O)NC1=CC=C2CC=CC=C2O1 OBHQDESDGFZAFD-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 10
- XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- ADEKJVNFIQUGRR-UHFFFAOYSA-N 4h-pyridin-3-one Chemical group O=C1CC=CN=C1 ADEKJVNFIQUGRR-UHFFFAOYSA-N 0.000 description 9
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 9
- 101150041968 CDC13 gene Proteins 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 239000004480 active ingredient Substances 0.000 description 9
- 239000000872 buffer Substances 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 230000001225 therapeutic effect Effects 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 8
- 239000005695 Ammonium acetate Substances 0.000 description 8
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 229940043376 ammonium acetate Drugs 0.000 description 8
- 235000019257 ammonium acetate Nutrition 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000003826 tablet Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
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- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
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- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
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- 229960002004 valdecoxib Drugs 0.000 description 1
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- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229940124024 weight reducing agent Drugs 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
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- 229920001285 xanthan gum Polymers 0.000 description 1
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- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/99—Enzyme inactivation by chemical treatment
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/00—Drugs for disorders of the nervous system
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- 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
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- 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
- C07D491/052—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being six-membered
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- 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
- C07D491/20—Spiro-condensed systems
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- Zoology (AREA)
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- Physical Education & Sports Medicine (AREA)
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- Hospice & Palliative Care (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
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| US201261608737P | 2012-03-09 | 2012-03-09 | |
| PCT/US2013/028230 WO2013134036A1 (en) | 2012-03-09 | 2013-02-28 | Aryl ether-base kinase inhibitors |
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| MX2014010684A true MX2014010684A (es) | 2014-10-17 |
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| US8901305B2 (en) | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| US9708337B2 (en) | 2013-02-22 | 2017-07-18 | Bristol-Myers Squibb Company | Aryl amide-based kinase inhibitors |
| US9914740B2 (en) | 2013-07-02 | 2018-03-13 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| EP3016950B1 (en) | 2013-07-02 | 2017-06-07 | Bristol-Myers Squibb Company | Tricyclic pyrido-carboxamide derivatives as rock inhibitors |
| US10253027B2 (en) | 2013-07-08 | 2019-04-09 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| EP3044226B1 (en) * | 2013-09-11 | 2017-09-06 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| WO2015054358A1 (en) | 2013-10-11 | 2015-04-16 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
| JP6276865B2 (ja) * | 2014-01-29 | 2018-02-07 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | アリールラクタムキナーゼ阻害剤 |
| ES2701903T3 (es) * | 2014-01-31 | 2019-02-26 | Bristol Myers Squibb Co | Inhibidores de cinasa a base de quinolina |
| SMT201800665T1 (it) | 2014-04-02 | 2019-01-11 | Bristol Myers Squibb Co | Inibitori biarilici di chinasi |
| ES2740224T3 (es) | 2015-04-10 | 2020-02-05 | Bristol Myers Squibb Co | 6H-isocromeno[3,4-c]piridinas y benzo[c][1,7]naftiridin-6-(5H)-onas como inhibidores de la cinasa asociada a adaptador 1 (AAK1) |
| BR112017019207A2 (pt) * | 2015-05-22 | 2018-04-24 | Dow Agrosciences Llc | recuperação e/ou reutilização de catalisador de paládio após acoplamento de suzuki |
| JP6864674B2 (ja) * | 2015-10-01 | 2021-04-28 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ビアリールキナーゼ阻害剤 |
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| SG10202009148XA (en) | 2016-12-15 | 2020-10-29 | Hoffmann La Roche | Process for preparing btk inhibitors |
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| AU673569B2 (en) | 1992-12-02 | 1996-11-14 | Pfizer Inc. | Catechol diethers as selective PDE-IV inhibitors |
| US5709861A (en) | 1993-04-22 | 1998-01-20 | Emisphere Technologies, Inc. | Compositions for the delivery of antigens |
| US20070060606A1 (en) * | 1999-10-07 | 2007-03-15 | Robertson Harold A | Compounds and methods for modulating phosphodiesterase 10A |
| AU2003230772A1 (en) | 2002-04-05 | 2003-10-27 | Boehringer Ingelheim Pharmaceuticals, Inc. | Cyanamides useful as reversible inhibitors of cysteine proteases |
| WO2004056744A1 (en) | 2002-12-23 | 2004-07-08 | Janssen Pharmaceutica N.V. | Adamantyl acetamides as hydroxysteroid dehydrogenase inhibitors |
| WO2004072018A1 (ja) | 2003-02-12 | 2004-08-26 | Takeda Pharmaceutical Company Limited | アミン誘導体 |
| WO2005000309A2 (en) | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
| US20050288338A1 (en) | 2004-06-24 | 2005-12-29 | Wenqing Yao | Amido compounds and their use as pharmaceuticals |
| CN100494167C (zh) | 2005-08-02 | 2009-06-03 | 天津大学 | 抗乙肝病毒的叔胺氧化物及制备方法和制备药物的应用 |
| JP2007217408A (ja) | 2006-01-19 | 2007-08-30 | Tanabe Seiyaku Co Ltd | 医薬組成物 |
| EP2674428B1 (en) | 2006-04-07 | 2016-04-06 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US20080039535A1 (en) | 2006-08-14 | 2008-02-14 | Wyeth | Methods of identifying agents for treating neurological disorders |
| US20100183514A1 (en) * | 2007-05-29 | 2010-07-22 | President And Fellows Of Harvard College | Molecules involved in regulation of osteoblast activity and osteoclast activity, and methods of use thereof |
| DE102007025717A1 (de) * | 2007-06-01 | 2008-12-11 | Merck Patent Gmbh | Arylether-pyridazinonderivate |
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| US8969564B2 (en) | 2015-03-03 |
| TW201341387A (zh) | 2013-10-16 |
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| US20140179725A1 (en) | 2014-06-26 |
| EP2822952B1 (en) | 2016-04-06 |
| US20130237555A1 (en) | 2013-09-12 |
| CN104144932A (zh) | 2014-11-12 |
| EP2822952A1 (en) | 2015-01-14 |
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| CA2866671A1 (en) | 2013-09-12 |
| EA201491647A1 (ru) | 2014-12-30 |
| UY34666A (es) | 2013-09-30 |
| US8703953B2 (en) | 2014-04-22 |
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