AU2003256003A1 - Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors - Google Patents
Novel oxazole and thiazole compounds as transforming growth factor (TGF) inhibitors Download PDFInfo
- Publication number
- AU2003256003A1 AU2003256003A1 AU2003256003A AU2003256003A AU2003256003A1 AU 2003256003 A1 AU2003256003 A1 AU 2003256003A1 AU 2003256003 A AU2003256003 A AU 2003256003A AU 2003256003 A AU2003256003 A AU 2003256003A AU 2003256003 A1 AU2003256003 A1 AU 2003256003A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- cio
- compound
- phenyl
- methyl
- 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
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- 102000009618 Transforming Growth Factors Human genes 0.000 title description 18
- 108010009583 Transforming Growth Factors Proteins 0.000 title description 18
- 239000003112 inhibitor Substances 0.000 title description 10
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 title description 5
- 150000003557 thiazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 176
- 125000000217 alkyl group Chemical group 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 75
- -1 hydroxy, oxo, mercapto Chemical class 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000003545 alkoxy group Chemical group 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 239000000651 prodrug Substances 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- 125000004122 cyclic group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 241001465754 Metazoa Species 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
- 125000003368 amide group Chemical group 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000003367 polycyclic group Chemical group 0.000 claims description 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims description 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 2
- 206010019668 Hepatic fibrosis Diseases 0.000 claims description 2
- 206010039710 Scleroderma Diseases 0.000 claims description 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims description 2
- 230000002500 effect on skin Effects 0.000 claims description 2
- 206010020718 hyperplasia Diseases 0.000 claims description 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 230000037390 scarring Effects 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- CCPHAMSKHBDMDS-UHFFFAOYSA-N Chetoseminudin B Natural products C=1NC2=CC=CC=C2C=1CC1(SC)NC(=O)C(CO)(SC)N(C)C1=O CCPHAMSKHBDMDS-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 40
- 239000000243 solution Substances 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 28
- 239000002585 base Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 239000002253 acid Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
- 239000002904 solvent Substances 0.000 description 17
- 125000005843 halogen group Chemical group 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000003814 drug Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000443 aerosol Substances 0.000 description 9
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 239000002798 polar solvent Substances 0.000 description 6
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 5
- 231100000252 nontoxic Toxicity 0.000 description 5
- 230000003000 nontoxic effect Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000003880 polar aprotic solvent Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 230000019491 signal transduction Effects 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- KISWVXRQTGLFGD-UHFFFAOYSA-N 2-[[2-[[6-amino-2-[[2-[[2-[[5-amino-2-[[2-[[1-[2-[[6-amino-2-[(2,5-diamino-5-oxopentanoyl)amino]hexanoyl]amino]-5-(diaminomethylideneamino)pentanoyl]pyrrolidine-2-carbonyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-(diaminomethylideneamino)p Chemical compound C1CCN(C(=O)C(CCCN=C(N)N)NC(=O)C(CCCCN)NC(=O)C(N)CCC(N)=O)C1C(=O)NC(CO)C(=O)NC(CCC(N)=O)C(=O)NC(CCCN=C(N)N)C(=O)NC(CO)C(=O)NC(CCCCN)C(=O)NC(C(=O)NC(CC(C)C)C(O)=O)CC1=CC=C(O)C=C1 KISWVXRQTGLFGD-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical group [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- 108091000080 Phosphotransferase Proteins 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000000021 kinase assay Methods 0.000 description 4
- BDGDWWGTAFXEEW-UHFFFAOYSA-N methylsulfinylmethane;oxalyl dichloride Chemical compound CS(C)=O.ClC(=O)C(Cl)=O BDGDWWGTAFXEEW-UHFFFAOYSA-N 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
- 239000010452 phosphate Substances 0.000 description 4
- 102000020233 phosphotransferase Human genes 0.000 description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 4
- 239000003586 protic polar solvent Substances 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- HFHZWWWPYIYROW-UHFFFAOYSA-N 2-bromo-1-(6-methylpyridin-2-yl)-2-quinolin-6-ylethanone;hydrobromide Chemical compound Br.CC1=CC=CC(C(=O)C(Br)C=2C=C3C=CC=NC3=CC=2)=N1 HFHZWWWPYIYROW-UHFFFAOYSA-N 0.000 description 3
- KMDJYIUSRDMDMW-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-4-bromo-1,3-oxazole Chemical compound N1=COC(C=2C=C3OCOC3=CC=2)=C1Br KMDJYIUSRDMDMW-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
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- 239000005695 Ammonium acetate Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 102000047918 Myelin Basic Human genes 0.000 description 3
- 101710107068 Myelin basic protein Proteins 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 125000000539 amino acid group Chemical group 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
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- 238000003556 assay Methods 0.000 description 3
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- 238000001704 evaporation Methods 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 150000002367 halogens Chemical group 0.000 description 3
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- 229960004592 isopropanol Drugs 0.000 description 3
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- 229940011051 isopropyl acetate Drugs 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- 239000000843 powder Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
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- 239000003826 tablet Substances 0.000 description 3
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- UIIOVRFUJRDPLJ-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(6-methylpyridin-2-yl)ethanone Chemical compound CC1=CC=CC(CC(=O)C=2C=C3OCOC3=CC=2)=N1 UIIOVRFUJRDPLJ-UHFFFAOYSA-N 0.000 description 2
- NIYRQWLFSCORML-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-bromo-2-(6-methylpyridin-1-ium-2-yl)ethanone;bromide Chemical compound [Br-].CC1=CC=CC(C(Br)C(=O)C=2C=C3OCOC3=CC=2)=[NH+]1 NIYRQWLFSCORML-UHFFFAOYSA-N 0.000 description 2
- UFHMNJKABGHUOC-UHFFFAOYSA-N 1-(6-methylpyridin-2-yl)-2-quinolin-6-ylethanone Chemical compound CC1=CC=CC(C(=O)CC=2C=C3C=CC=NC3=CC=2)=N1 UFHMNJKABGHUOC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZEMZPXWZVTUONV-UHFFFAOYSA-N 2-(2-dicyclohexylphosphanylphenyl)-n,n-dimethylaniline Chemical group CN(C)C1=CC=CC=C1C1=CC=CC=C1P(C1CCCCC1)C1CCCCC1 ZEMZPXWZVTUONV-UHFFFAOYSA-N 0.000 description 2
- FPQMUQPPAYCAME-UHFFFAOYSA-N 2-Acetyl-6-methylpyridine Chemical compound CC(=O)C1=CC=CC(C)=N1 FPQMUQPPAYCAME-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41212002P | 2002-09-18 | 2002-09-18 | |
| US60/412,120 | 2002-09-18 | ||
| US47126503P | 2003-05-16 | 2003-05-16 | |
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| PCT/IB2003/003823 WO2004026863A1 (en) | 2002-09-18 | 2003-09-08 | Novel oxazole and thiazole compounds as transforming growth factor (tgf) inhibitors |
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| DE60330362D1 (de) * | 2002-09-18 | 2010-01-14 | Pfizer Prod Inc | Neue pyrazol-verbindungen als hemmer des transformierenden wachstumsfaktors (tgf) |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
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| US7410988B2 (en) * | 2004-08-13 | 2008-08-12 | Genentech, Inc. | 2-Amido-thiazole-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| EP1798229A4 (en) * | 2004-09-07 | 2009-07-29 | Sankyo Co | SUBSTITUTED BIPHENYL DERIVATIVE |
| AU2005286728A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-CoA desaturase |
| CA2580855A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| WO2006034441A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| JP4958785B2 (ja) | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼインヒビターとしてのそれらの使用 |
| BRPI0515483A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos para o tratamento de doenças mediadas por enzimas estearoil-coa desaturase |
| TW200626155A (en) | 2004-09-20 | 2006-08-01 | Xenon Pharmaceuticals Inc | Heterocyclic derivatives and their use as therapeutic agents |
| CN101084211A (zh) | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为治疗剂的用途 |
| WO2007130075A1 (en) | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| BRPI0619966A2 (pt) * | 2005-12-16 | 2011-10-25 | Alcon Inc | controle de pressão intra-ocular usando agentes de modulação de alk5 |
| WO2008150827A1 (en) * | 2007-05-29 | 2008-12-11 | Smithkline Beecham Corporation | Naphthyridine, derivatives as p13 kinase inhibitors |
| US8268874B2 (en) | 2008-03-03 | 2012-09-18 | University Of Notre Dame Du Lac | Anti-cancer compounds, synthesis thereof, and methods of using same |
| US8865732B2 (en) | 2008-03-21 | 2014-10-21 | Novartis Ag | Heterocyclic compounds and uses thereof |
| AU2012203026B2 (en) * | 2008-03-21 | 2014-06-12 | Novartis Ag | Novel heterocyclic compounds and uses thereof |
| WO2009155388A1 (en) | 2008-06-20 | 2009-12-23 | Bristol-Myers Squibb Company | Imidazopyridine and imidazopyrazine compounds useful as kinase inhibitors |
| US9242969B2 (en) | 2013-03-14 | 2016-01-26 | Novartis Ag | Biaryl amide compounds as kinase inhibitors |
| WO2015103355A1 (en) | 2014-01-01 | 2015-07-09 | Medivation Technologies, Inc. | Compounds and methods of use |
| UY36294A (es) | 2014-09-12 | 2016-04-29 | Novartis Ag | Compuestos y composiciones como inhibidores de quinasa |
| CN105585565B (zh) * | 2014-10-23 | 2019-10-01 | 中国医学科学院药物研究所 | 含2-苯胺基-4-噻唑基吡啶衍生物及其制法和药物组合物与用途 |
| CN106243012A (zh) * | 2016-08-02 | 2016-12-21 | 北方民族大学 | 新型吲哚类衍生物及其制备方法 |
| EP3515446B1 (en) | 2016-09-19 | 2023-12-20 | Novartis AG | Therapeutic combinations comprising a raf inhibitor and a erk inhibitor |
| CN110494166B (zh) | 2017-05-02 | 2022-11-08 | 诺华股份有限公司 | 组合疗法 |
| IL271149B2 (en) * | 2017-06-14 | 2024-05-01 | Trevena Inc | Compounds for modulating s1p1 activity and methods of using the same |
| KR102881316B1 (ko) | 2019-05-13 | 2025-11-05 | 노파르티스 아게 | 암 치료를 위한 raf 억제제로서의 n-(3-(2-(2-하이드록시에톡시)-6-모르폴리노피리딘-4-일)-4-메틸페닐)-2 (트리플루오로메틸)이소니코틴아미드의 새로운 결정질 형태 |
| CN112694477B (zh) * | 2019-10-22 | 2024-02-06 | 四川科伦博泰生物医药股份有限公司 | 吡唑并环类化合物，包含其的药物组合物，其制备方法及其用途 |
| CN114727977A (zh) | 2019-11-19 | 2022-07-08 | 特维娜有限公司 | 化合物和化合物s1p1调节剂的制备方法 |
| CN115466260B (zh) * | 2022-09-06 | 2023-10-13 | 延边大学 | 含氨基酸结构的咪唑和噻唑类衍生物及其制备方法和应用 |
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| EP0149884B1 (en) | 1983-09-09 | 1992-12-16 | Takeda Chemical Industries, Ltd. | 5-pyridyl-1,3-thiazole derivatives, their production and use |
| GB9201692D0 (en) | 1992-01-27 | 1992-03-11 | Smithkline Beecham Intercredit | Compounds |
| CA2288741A1 (en) | 1997-05-22 | 1998-11-26 | G.D. Searle And Co. | 4-aryl-3(5)-heteroaryl substituted pyrazoles as p38 kinase inhibitors |
| AU7726898A (en) | 1997-05-22 | 1998-12-11 | G.D. Searle & Co. | Pyrazole derivatives as p38 kinase inhibitors |
| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
| WO1999021555A2 (en) | 1997-10-27 | 1999-05-06 | Takeda Chemical Industries, Ltd. | Adenosine a3 receptor antagonists |
| WO2000061576A1 (en) * | 1999-04-09 | 2000-10-19 | Smithkline Beecham Corporation | Triarylimidazoles |
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| PE20020506A1 (es) | 2000-08-22 | 2002-07-09 | Glaxo Group Ltd | Derivados de pirazol fusionados como inhibidores de la proteina cinasa |
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| US20040077697A1 (en) | 2001-02-02 | 2004-04-22 | Hiroyuki Koshio | 2-Acylaminothiazole derivative or its salt |
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| CA2450400A1 (en) | 2001-06-11 | 2002-12-19 | Takeda Chemical Industries, Ltd. | Medicinal compositions |
| AR039241A1 (es) | 2002-04-04 | 2005-02-16 | Biogen Inc | Heteroarilos trisustituidos y metodos para su produccion y uso de los mismos |
| JP2005539000A (ja) | 2002-07-31 | 2005-12-22 | スミスクライン・ビーチャム・コーポレイション | Ａｌｋ５阻害剤としての２−フェニルピリジン−４−イル誘導体 |
| GB0217787D0 (en) | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | C ompounds |
| DE60330362D1 (de) | 2002-09-18 | 2010-01-14 | Pfizer Prod Inc | Neue pyrazol-verbindungen als hemmer des transformierenden wachstumsfaktors (tgf) |
| HRP20050251A2 (en) | 2002-09-18 | 2005-10-31 | Pfizer Products Inc. | Triazole derivatives as transforming growth factor (tfg) inhibitors |
| AP2005003262A0 (en) | 2002-09-18 | 2005-03-31 | Pfizer Prod Inc | Novel isothiazole and isoxazole compounds as tranforming growth factor (TGF) inhibitors. |
| ES2325687T3 (es) | 2002-09-18 | 2009-09-14 | Pfizer Products Inc. | Compuestos de imidazol novedosos como inhibidores del factor de crecimiento transformante (tgf). |
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2003
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- 2003-09-08 CA CA2499429A patent/CA2499429C/en not_active Expired - Fee Related
- 2003-09-08 JP JP2004568899A patent/JP4518956B2/ja not_active Expired - Fee Related
- 2003-09-08 AU AU2003256003A patent/AU2003256003A1/en not_active Abandoned
- 2003-09-08 EA EA200500354A patent/EA200500354A1/ru unknown
- 2003-09-08 HR HR20050250A patent/HRP20050250A2/xx not_active Application Discontinuation
- 2003-09-08 AP AP2005003261A patent/AP2005003261A0/xx unknown
- 2003-09-08 DE DE60327443T patent/DE60327443D1/de not_active Expired - Lifetime
- 2003-09-08 AT AT03797426T patent/ATE430147T1/de not_active IP Right Cessation
- 2003-09-08 OA OA1200500075A patent/OA12926A/en unknown
- 2003-09-08 KR KR1020057004611A patent/KR20050057415A/ko not_active Ceased
- 2003-09-08 PL PL03375975A patent/PL375975A1/xx not_active Application Discontinuation
- 2003-09-08 CN CNA038222205A patent/CN1681810A/zh active Pending
- 2003-09-08 BR BR0314383-0A patent/BR0314383A/pt not_active IP Right Cessation
- 2003-09-08 MX MXPA05002332A patent/MXPA05002332A/es active IP Right Grant
- 2003-09-08 EP EP03797426A patent/EP1542994B1/en not_active Expired - Lifetime
- 2003-09-08 ES ES03797426T patent/ES2323421T3/es not_active Expired - Lifetime
- 2003-09-15 UY UY27978A patent/UY27978A1/es not_active Application Discontinuation
- 2003-09-15 PA PA20038582701A patent/PA8582701A1/es unknown
- 2003-09-15 PE PE2003000939A patent/PE20040987A1/es not_active Application Discontinuation
- 2003-09-16 AR ARP030103357A patent/AR041273A1/es unknown
- 2003-09-17 TW TW092125637A patent/TW200413362A/zh unknown
- 2003-09-17 US US10/667,187 patent/US7273936B2/en not_active Expired - Fee Related
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2005
- 2005-02-24 IS IS7711A patent/IS7711A/is unknown
- 2005-03-15 CR CR7743A patent/CR7743A/es not_active Application Discontinuation
- 2005-03-16 CO CO05024531A patent/CO5550473A2/es not_active Application Discontinuation
- 2005-03-18 MA MA28157A patent/MA27443A1/fr unknown
- 2005-04-15 NO NO20051838A patent/NO20051838L/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20040110797A1 (en) | 2004-06-10 |
| CR7743A (es) | 2005-06-15 |
| EA200500354A1 (ru) | 2005-10-27 |
| US7273936B2 (en) | 2007-09-25 |
| MXPA05002332A (es) | 2005-06-08 |
| HRP20050250A2 (en) | 2005-10-31 |
| CA2499429A1 (en) | 2004-04-01 |
| UY27978A1 (es) | 2004-04-30 |
| IS7711A (is) | 2005-02-24 |
| JP2006502235A (ja) | 2006-01-19 |
| ES2323421T3 (es) | 2009-07-15 |
| DE60327443D1 (de) | 2009-06-10 |
| OA12926A (en) | 2006-10-13 |
| CO5550473A2 (es) | 2005-08-31 |
| TW200413362A (en) | 2004-08-01 |
| AP2005003261A0 (en) | 2005-03-31 |
| WO2004026863A8 (en) | 2005-04-21 |
| NO20051838L (no) | 2005-04-15 |
| ATE430147T1 (de) | 2009-05-15 |
| KR20050057415A (ko) | 2005-06-16 |
| WO2004026863A1 (en) | 2004-04-01 |
| MA27443A1 (fr) | 2005-07-01 |
| PE20040987A1 (es) | 2004-12-27 |
| CA2499429C (en) | 2010-09-21 |
| EP1542994A1 (en) | 2005-06-22 |
| PL375975A1 (en) | 2005-12-12 |
| JP4518956B2 (ja) | 2010-08-04 |
| PA8582701A1 (es) | 2004-04-23 |
| CN1681810A (zh) | 2005-10-12 |
| BR0314383A (pt) | 2005-07-19 |
| EP1542994B1 (en) | 2009-04-29 |
| AR041273A1 (es) | 2005-05-11 |
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| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |