CA2532078A1 - Naphthylene derivatives as cytochrome p450 inhibitors - Google Patents
Naphthylene derivatives as cytochrome p450 inhibitors Download PDFInfo
- Publication number
- CA2532078A1 CA2532078A1 CA002532078A CA2532078A CA2532078A1 CA 2532078 A1 CA2532078 A1 CA 2532078A1 CA 002532078 A CA002532078 A CA 002532078A CA 2532078 A CA2532078 A CA 2532078A CA 2532078 A1 CA2532078 A1 CA 2532078A1
- Authority
- CA
- Canada
- Prior art keywords
- 10alkyl
- 10alkynyl
- 10alkenyl
- cycloc3
- optionally substituted
- 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
- 208000003311 Cytochrome P-450 Enzyme Inhibitors Diseases 0.000 title description 2
- 125000004957 naphthylene group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 795
- 150000003839 salts Chemical class 0.000 claims abstract description 62
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 201000010099 disease Diseases 0.000 claims abstract description 27
- 102100039282 Cytochrome P450 26A1 Human genes 0.000 claims abstract description 12
- 101710130818 Cytochrome P450 26A1 Proteins 0.000 claims abstract description 8
- 102000004190 Enzymes Human genes 0.000 claims abstract description 8
- 108090000790 Enzymes Proteins 0.000 claims abstract description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 619
- 125000000623 heterocyclic group Chemical group 0.000 claims description 285
- 229920006395 saturated elastomer Polymers 0.000 claims description 282
- 125000001424 substituent group Chemical group 0.000 claims description 252
- 125000005843 halogen group Chemical group 0.000 claims description 251
- 229910052799 carbon Inorganic materials 0.000 claims description 229
- -1 cyano, hydroxy Chemical group 0.000 claims description 225
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 201
- 238000000034 method Methods 0.000 claims description 183
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 165
- 150000001721 carbon Chemical group 0.000 claims description 136
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 88
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 67
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
- 125000002883 imidazolyl group Chemical group 0.000 claims description 46
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 44
- 125000001425 triazolyl group Chemical group 0.000 claims description 42
- 125000005842 heteroatom Chemical group 0.000 claims description 40
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 239000001301 oxygen Substances 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 206010028980 Neoplasm Diseases 0.000 claims description 23
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
- 230000000694 effects Effects 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 16
- 201000011510 cancer Diseases 0.000 claims description 13
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000003937 drug carrier Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 239000000843 powder Substances 0.000 claims description 7
- 150000004492 retinoid derivatives Chemical class 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 206010006187 Breast cancer Diseases 0.000 claims description 5
- 208000026310 Breast neoplasm Diseases 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 208000032839 leukemia Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 4
- 239000002674 ointment Substances 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 239000000829 suppository Substances 0.000 claims description 3
- RRGFPKROLPRMHJ-UHFFFAOYSA-N 1-[(1-methylpyrrolidin-2-yl)-(6-phenylmethoxynaphthalen-2-yl)methyl]imidazole Chemical compound CN1CCCC1C(N1C=NC=C1)C1=CC=C(C=C(OCC=2C=CC=CC=2)C=C2)C2=C1 RRGFPKROLPRMHJ-UHFFFAOYSA-N 0.000 claims description 2
- WNMJTTIGNYLSJY-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]cyclobutane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1(C(O)=O)CCC1 WNMJTTIGNYLSJY-UHFFFAOYSA-N 0.000 claims description 2
- VZAYORFJMPOFKB-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]cyclohexane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1(C(O)=O)CCCCC1 VZAYORFJMPOFKB-UHFFFAOYSA-N 0.000 claims description 2
- JZBAXRLBKQTQQE-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]cyclopentane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1(C(O)=O)CCCC1 JZBAXRLBKQTQQE-UHFFFAOYSA-N 0.000 claims description 2
- PVEQEQGWTRAWFX-UHFFFAOYSA-N 1-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]cyclopropane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1(C(O)=O)CC1 PVEQEQGWTRAWFX-UHFFFAOYSA-N 0.000 claims description 2
- PLXKSCLQIJZCDI-UHFFFAOYSA-N 2-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]-2-ethylbutanoic acid Chemical compound C1=CC2=CC(OCC(CC)(CC)C(O)=O)=CC=C2C=C1C(C(C)N(C)C)N1C=CN=C1 PLXKSCLQIJZCDI-UHFFFAOYSA-N 0.000 claims description 2
- ZCIYBFFBVPVYLH-FGZHOGPDSA-N 3-[6-[(1r,2r)-2-(dimethylamino)-1-imidazol-1-ylbutyl]naphthalen-2-yl]oxy-2,2-dimethylpropanoic acid Chemical compound N1([C@H](C=2C=C3C=CC(OCC(C)(C)C(O)=O)=CC3=CC=2)[C@@H](CC)N(C)C)C=CN=C1 ZCIYBFFBVPVYLH-FGZHOGPDSA-N 0.000 claims description 2
- YLMRCYCGLCIPMC-IERDGZPVSA-N 3-[6-[(1r,2r)-2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-2,2-dimethylpropanoic acid Chemical compound N1([C@H](C=2C=C3C=CC(OCC(C)(C)C(O)=O)=CC3=CC=2)[C@@H](C)N(C)C)C=CN=C1 YLMRCYCGLCIPMC-IERDGZPVSA-N 0.000 claims description 2
- ACFQJABFUNOOOS-UHFFFAOYSA-N 3-[6-[2-(diethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-2,2-dimethylpropanoic acid Chemical compound C=1C=C2C=C(OCC(C)(C)C(O)=O)C=CC2=CC=1C(C(C)N(CC)CC)N1C=CN=C1 ACFQJABFUNOOOS-UHFFFAOYSA-N 0.000 claims description 2
- OZXGHWIQASWJQX-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-2,2-dimethylpropanamide Chemical compound C=1C=C2C=C(OCC(C)(C)C(N)=O)C=CC2=CC=1C(C(C)N(C)C)N1C=CN=C1 OZXGHWIQASWJQX-UHFFFAOYSA-N 0.000 claims description 2
- LEDOEMLBTIQWQV-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-n,2,2-trimethylpropanamide Chemical compound C1=CC2=CC(OCC(C)(C)C(=O)NC)=CC=C2C=C1C(C(C)N(C)C)N1C=CN=C1 LEDOEMLBTIQWQV-UHFFFAOYSA-N 0.000 claims description 2
- RSDPLFJFCIEHAP-UHFFFAOYSA-N 3-[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-n,n,2,2-tetramethylpropanamide Chemical compound C=1C=C2C=C(OCC(C)(C)C(=O)N(C)C)C=CC2=CC=1C(C(C)N(C)C)N1C=CN=C1 RSDPLFJFCIEHAP-UHFFFAOYSA-N 0.000 claims description 2
- LUDUPPNOCMHNSY-UHFFFAOYSA-N 3-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]benzoic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=CC(C(O)=O)=C1 LUDUPPNOCMHNSY-UHFFFAOYSA-N 0.000 claims description 2
- USKWAWWTDNDTTP-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]-n,n-dimethylbenzamide Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=C(C(=O)N(C)C)C=C1 USKWAWWTDNDTTP-UHFFFAOYSA-N 0.000 claims description 2
- QBTDWXVTSLLMNL-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1COC1=CC=C(C=C(C=C2)C(C(C)N(C)C)N3C=NC=C3)C2=C1 QBTDWXVTSLLMNL-UHFFFAOYSA-N 0.000 claims description 2
- XKHSAPXNWDFQIS-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]benzamide Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=C(C(N)=O)C=C1 XKHSAPXNWDFQIS-UHFFFAOYSA-N 0.000 claims description 2
- DMLUZARQJJUBAJ-UHFFFAOYSA-N 4-[[6-[2-(dimethylamino)-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxymethyl]benzoic acid Chemical compound C1=CN=CN1C(C(C)N(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1=CC=C(C(O)=O)C=C1 DMLUZARQJJUBAJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000000443 aerosol Substances 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 238000007911 parenteral administration Methods 0.000 claims description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 40
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 32
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 11
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims 1
- MYLJXYCXVOMQPS-UHFFFAOYSA-N 1-[[6-[1-imidazol-1-yl-2-[methyl(propan-2-yl)amino]propyl]naphthalen-2-yl]oxymethyl]cyclopentane-1-carboxylic acid Chemical compound C1=CN=CN1C(C(C)N(C)C(C)C)C(C=C1C=C2)=CC=C1C=C2OCC1(C(O)=O)CCCC1 MYLJXYCXVOMQPS-UHFFFAOYSA-N 0.000 claims 1
- ZXPSJDOWBKNEAW-UHFFFAOYSA-N 3-[6-[2-[ethyl(methyl)amino]-1-imidazol-1-ylpropyl]naphthalen-2-yl]oxy-2,2-dimethylpropanoic acid Chemical compound C=1C=C2C=C(OCC(C)(C)C(O)=O)C=CC2=CC=1C(C(C)N(C)CC)N1C=CN=C1 ZXPSJDOWBKNEAW-UHFFFAOYSA-N 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- 229930002330 retinoic acid Natural products 0.000 abstract description 39
- 238000011282 treatment Methods 0.000 abstract description 38
- SHGAZHPCJJPHSC-YCNIQYBTSA-N all-trans-retinoic acid Chemical compound OC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C SHGAZHPCJJPHSC-YCNIQYBTSA-N 0.000 abstract description 37
- 229960001727 tretinoin Drugs 0.000 abstract description 35
- 230000002265 prevention Effects 0.000 abstract description 8
- 238000010189 synthetic method Methods 0.000 description 149
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 146
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 128
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 123
- 239000002904 solvent Substances 0.000 description 119
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 116
- 230000008569 process Effects 0.000 description 108
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 85
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 73
- 125000000217 alkyl group Chemical group 0.000 description 68
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 61
- 101150041968 CDC13 gene Proteins 0.000 description 57
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 56
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
- 239000000543 intermediate Substances 0.000 description 51
- 238000005481 NMR spectroscopy Methods 0.000 description 50
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 48
- 238000002360 preparation method Methods 0.000 description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
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- 239000000376 reactant Substances 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- 239000002585 base Substances 0.000 description 35
- 125000001072 heteroaryl group Chemical group 0.000 description 35
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- 229910001868 water Inorganic materials 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
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- 150000002170 ethers Chemical class 0.000 description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 26
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- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 23
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- 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 21
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
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- 239000003112 inhibitor Substances 0.000 description 15
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
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- 238000010898 silica gel chromatography Methods 0.000 description 13
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- 239000012044 organic layer Substances 0.000 description 12
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 description 12
- 229910052727 yttrium Inorganic materials 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- UGFHIPBXIWJXNA-UHFFFAOYSA-N liarozole Chemical compound ClC1=CC=CC(C(C=2C=C3NC=NC3=CC=2)N2C=NC=C2)=C1 UGFHIPBXIWJXNA-UHFFFAOYSA-N 0.000 description 11
- 229950007056 liarozole Drugs 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4192—1,2,3-Triazoles
-
- 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
- A61P17/06—Antipsoriatics
-
- 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
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US48638203P | 2003-07-10 | 2003-07-10 | |
| US60/486,382 | 2003-07-10 | ||
| PCT/US2004/022282 WO2005007631A1 (en) | 2003-07-10 | 2004-07-12 | Naphthylene derivatives as cytochrome p450 inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2532078A1 true CA2532078A1 (en) | 2005-01-27 |
Family
ID=34079229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002532078A Abandoned CA2532078A1 (en) | 2003-07-10 | 2004-07-12 | Naphthylene derivatives as cytochrome p450 inhibitors |
Country Status (15)
| Country | Link |
|---|---|
| EP (1) | EP1654236A1 (ru) |
| JP (1) | JP4832295B2 (ru) |
| KR (1) | KR20060052799A (ru) |
| CN (1) | CN1819996B (ru) |
| AU (1) | AU2004257257B2 (ru) |
| BR (1) | BRPI0412424A (ru) |
| CA (1) | CA2532078A1 (ru) |
| IL (1) | IL172812A0 (ru) |
| IS (1) | IS8223A (ru) |
| MX (1) | MXPA06000401A (ru) |
| NO (1) | NO20060114L (ru) |
| RU (1) | RU2363696C2 (ru) |
| SG (1) | SG144941A1 (ru) |
| UA (1) | UA87822C2 (ru) |
| WO (1) | WO2005007631A1 (ru) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007515433A (ja) * | 2003-12-17 | 2007-06-14 | アラーガン インコーポレイテッド | Ｃｙｐ２６ａおよびｃｙｐ２６ｂの選択的阻害剤を使用するレチノイド反応性障害の処置方法 |
| US7662844B2 (en) | 2004-07-12 | 2010-02-16 | Osi Pharmaceuticals, Inc. | Naphthylene derivatives as cytochrome P450 inhibitors |
| US10414760B2 (en) | 2016-11-29 | 2019-09-17 | Angion Biomedica Corp. | Cytochrome P450 inhibitors and uses thereof |
| JP6088425B2 (ja) | 2010-06-01 | 2017-03-01 | アンジオン バイオメディカ コーポレーション | チトクロームｐ４５０阻害剤およびその使用 |
| KR101848077B1 (ko) * | 2010-11-13 | 2018-04-11 | 이노크린 파마슈티컬즈, 인크. | 금속효소 억제제 화합물 |
| BR112013014484A2 (pt) * | 2010-12-13 | 2016-07-19 | Viamet Pharmaceuticals Inc | compostos inibidores de metaloenzimas |
| CN102586187A (zh) * | 2012-02-23 | 2012-07-18 | 深圳市中美康士生物科技有限公司 | 一种中性粒细胞体外保存方法及培养基 |
| WO2014015137A2 (en) * | 2012-07-18 | 2014-01-23 | Angion Biomedica Corp. | Compositions and methods for treating dysproliferative diseases |
| CA2957785C (en) | 2014-08-11 | 2023-01-03 | Angion Biomedica Corporation | Cytochrome p450 inhibitors and uses thereof |
| CN104523967B (zh) * | 2014-12-12 | 2017-08-01 | 扬子江药业集团北京海燕药业有限公司 | 一种柏艾胶囊作为cyp酶抑制剂的应用 |
| CN107531631B (zh) | 2014-12-31 | 2021-09-03 | 安吉昂生物医药公司 | 用于治疗疾病的方法和药剂 |
| GB201602572D0 (en) * | 2016-02-12 | 2016-03-30 | Eriksson Leif And Strid Ake And Sirsjö Allan | New compound and uses |
| WO2018065288A1 (de) | 2016-10-07 | 2018-04-12 | Bayer Cropscience Aktiengesellschaft | 2-[2-phenyl-1-(sulfonylmethyl)vinyl]-imidazo[4,5-b]pyridin-derivate und verwandte verbindungen als schädlingsbekämpfungsmittel im pflanzenschutz |
| KR102515694B1 (ko) | 2017-01-10 | 2023-03-29 | 바이엘 악티엔게젤샤프트 | 해충 방제제로서의 헤테로사이클 유도체 |
| TW201837026A (zh) | 2017-01-10 | 2018-10-16 | 德商拜耳廠股份有限公司 | 作為除害劑之雜環衍生物（二） |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL291944A (ru) * | 1960-05-04 | |||
| NL131915C (ru) * | 1966-07-27 | |||
| DE3508903A1 (de) * | 1985-03-13 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Neue 3-pyridylmethylnaphtylderivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| DE3628545A1 (de) * | 1985-09-23 | 1987-04-23 | Hoechst Ag | Arylmethylazole und deren salze, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| WO1994008973A1 (en) * | 1992-10-21 | 1994-04-28 | Sankyo Company, Limited | Azole compound |
| JP4546589B2 (ja) * | 1998-04-23 | 2010-09-15 | 武田薬品工業株式会社 | ナフタレン誘導体 |
| ATE293102T1 (de) * | 1998-04-23 | 2005-04-15 | Takeda Pharmaceutical | Naphthalene derivate ,ihre herstellung und verwendung |
| FR2796070B1 (fr) * | 1999-07-06 | 2003-02-21 | Lipha | Derives de benzodiazepines utilisables dans le traitement de dyslipidemies, de l'atherosclerose et du diabete, compositions pharmaceutiques les contenant et procedes de preparation |
| PE20010781A1 (es) * | 1999-10-22 | 2001-08-08 | Takeda Chemical Industries Ltd | Compuestos 1-(1h-imidazol-4-il)-1-(naftil-2-sustituido)etanol, su produccion y utilizacion |
| JP4520012B2 (ja) * | 1999-10-22 | 2010-08-04 | 武田薬品工業株式会社 | １−置換−１−（１ｈ−イミダゾール−４−イル）メタノール類 |
-
2004
- 2004-07-12 JP JP2006518965A patent/JP4832295B2/ja not_active Expired - Fee Related
- 2004-07-12 CN CN200480019732XA patent/CN1819996B/zh not_active Expired - Fee Related
- 2004-07-12 WO PCT/US2004/022282 patent/WO2005007631A1/en active Application Filing
- 2004-07-12 EP EP04756894A patent/EP1654236A1/en not_active Withdrawn
- 2004-07-12 MX MXPA06000401A patent/MXPA06000401A/es active IP Right Grant
- 2004-07-12 SG SG200805435-5A patent/SG144941A1/en unknown
- 2004-07-12 BR BRPI0412424-3A patent/BRPI0412424A/pt not_active IP Right Cessation
- 2004-07-12 CA CA002532078A patent/CA2532078A1/en not_active Abandoned
- 2004-07-12 KR KR1020067000669A patent/KR20060052799A/ko not_active Application Discontinuation
- 2004-07-12 RU RU2006103996/04A patent/RU2363696C2/ru not_active IP Right Cessation
- 2004-07-12 AU AU2004257257A patent/AU2004257257B2/en not_active Expired - Fee Related
- 2004-12-07 UA UAA200601312A patent/UA87822C2/ru unknown
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2005
- 2005-12-26 IL IL172812A patent/IL172812A0/en unknown
-
2006
- 2006-01-06 NO NO20060114A patent/NO20060114L/no not_active Application Discontinuation
- 2006-01-10 IS IS8223A patent/IS8223A/is unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IS8223A (is) | 2006-01-10 |
| IL172812A0 (en) | 2006-06-11 |
| UA87822C2 (ru) | 2009-08-25 |
| AU2004257257A1 (en) | 2005-01-27 |
| RU2363696C2 (ru) | 2009-08-10 |
| CN1819996B (zh) | 2010-10-27 |
| JP2007523866A (ja) | 2007-08-23 |
| NO20060114L (no) | 2006-02-09 |
| WO2005007631A1 (en) | 2005-01-27 |
| JP4832295B2 (ja) | 2011-12-07 |
| SG144941A1 (en) | 2008-08-28 |
| RU2006103996A (ru) | 2006-07-10 |
| KR20060052799A (ko) | 2006-05-19 |
| EP1654236A1 (en) | 2006-05-10 |
| BRPI0412424A (pt) | 2006-09-05 |
| AU2004257257B2 (en) | 2011-05-12 |
| CN1819996A (zh) | 2006-08-16 |
| MXPA06000401A (es) | 2006-03-17 |
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