CA2461360A1 - Thiazoles 3-pyridyle ou 4-isoquinolinyle utilises comme inhibiteurs de lyase c17,20 - Google Patents
Thiazoles 3-pyridyle ou 4-isoquinolinyle utilises comme inhibiteurs de lyase c17,20 Download PDFInfo
- Publication number
- CA2461360A1 CA2461360A1 CA002461360A CA2461360A CA2461360A1 CA 2461360 A1 CA2461360 A1 CA 2461360A1 CA 002461360 A CA002461360 A CA 002461360A CA 2461360 A CA2461360 A CA 2461360A CA 2461360 A1 CA2461360 A1 CA 2461360A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridyl
- thiazole
- bond
- etoac
- cndot
- 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
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title claims abstract description 75
- 239000002697 lyase inhibitor Substances 0.000 title description 7
- MOYQLVVBWFGTJI-UHFFFAOYSA-N 4-isoquinolin-1-yl-1,3-thiazole Chemical class S1C=NC(C=2C3=CC=CC=C3C=CN=2)=C1 MOYQLVVBWFGTJI-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 238000000034 method Methods 0.000 claims abstract description 93
- 102000004317 Lyases Human genes 0.000 claims abstract description 39
- 108090000856 Lyases Proteins 0.000 claims abstract description 39
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 35
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 28
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 24
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 24
- 201000011510 cancer Diseases 0.000 claims abstract description 21
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 18
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
- -1 4-isoquinolinyl moiety Chemical group 0.000 claims description 107
- 229910052760 oxygen Inorganic materials 0.000 claims description 92
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 74
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 150000002367 halogens Chemical class 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 38
- 150000001204 N-oxides Chemical class 0.000 claims description 32
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 230000002401 inhibitory effect Effects 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 230000036961 partial effect Effects 0.000 claims description 8
- 125000000565 sulfonamide group Chemical group 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 150000003557 thiazoles Chemical class 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 4
- 241000282465 Canis Species 0.000 claims description 3
- 241000283073 Equus caballus Species 0.000 claims description 3
- 241000282324 Felis Species 0.000 claims description 3
- 241000288906 Primates Species 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 16
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 3
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 abstract description 17
- 108090000790 Enzymes Proteins 0.000 abstract description 17
- 125000001424 substituent group Chemical group 0.000 abstract description 12
- 239000003112 inhibitor Substances 0.000 abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 863
- 235000019439 ethyl acetate Nutrition 0.000 description 427
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 225
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 156
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 156
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 151
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 139
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 125
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 121
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 88
- 239000000243 solution Substances 0.000 description 85
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 84
- 239000000543 intermediate Substances 0.000 description 81
- 238000004809 thin layer chromatography Methods 0.000 description 80
- 239000000203 mixture Substances 0.000 description 78
- 229910052757 nitrogen Inorganic materials 0.000 description 77
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 76
- 238000002360 preparation method Methods 0.000 description 75
- 125000001309 chloro group Chemical group Cl* 0.000 description 71
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 67
- 238000006243 chemical reaction Methods 0.000 description 65
- 239000007787 solid Substances 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 49
- 239000002904 solvent Substances 0.000 description 49
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 49
- 229910001868 water Inorganic materials 0.000 description 46
- 239000011541 reaction mixture Substances 0.000 description 43
- 238000007429 general method Methods 0.000 description 41
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 41
- 230000000694 effects Effects 0.000 description 40
- 238000005160 1H NMR spectroscopy Methods 0.000 description 39
- 102000002004 Cytochrome P-450 Enzyme System Human genes 0.000 description 39
- 108010015742 Cytochrome P-450 Enzyme System Proteins 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 37
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 33
- 239000003098 androgen Substances 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 30
- 125000001246 bromo group Chemical group Br* 0.000 description 30
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 29
- 201000010099 disease Diseases 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 26
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 23
- 238000011282 treatment Methods 0.000 description 23
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 22
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000012044 organic layer Substances 0.000 description 21
- 238000010992 reflux Methods 0.000 description 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 20
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 20
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 20
- 239000000725 suspension Substances 0.000 description 20
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 19
- 108010015330 Steroid 17-alpha-Hydroxylase Proteins 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 18
- 102000001854 Steroid 17-alpha-Hydroxylase Human genes 0.000 description 18
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 18
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 18
- 238000010898 silica gel chromatography Methods 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 17
- 101150041968 CDC13 gene Proteins 0.000 description 16
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 16
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 15
- 239000000262 estrogen Substances 0.000 description 15
- 229940011871 estrogen Drugs 0.000 description 15
- 239000000706 filtrate Substances 0.000 description 15
- 238000004128 high performance liquid chromatography Methods 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 14
- MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 14
- 230000001419 dependent effect Effects 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 229940030486 androgens Drugs 0.000 description 13
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
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- 239000012267 brine Substances 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
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- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 229910052720 vanadium Inorganic materials 0.000 description 12
- 229910004373 HOAc Inorganic materials 0.000 description 11
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
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- 239000011593 sulfur Substances 0.000 description 11
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- 125000003118 aryl group Chemical group 0.000 description 10
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- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
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- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
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- 235000011152 sodium sulphate Nutrition 0.000 description 8
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- NRGXDHGSEPOAHR-UHFFFAOYSA-N 2-chloro-1-(4-methylpyridin-3-yl)ethanone Chemical compound CC1=CC=NC=C1C(=O)CCl NRGXDHGSEPOAHR-UHFFFAOYSA-N 0.000 description 7
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 7
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- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
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- 239000002243 precursor Substances 0.000 description 6
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- NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 5
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- 230000009385 viral infection Effects 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/38—Drugs for disorders of the endocrine system of the suprarenal hormones
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (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)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La présente invention concerne de nouveaux thiazoles portant des substituants 3-pyridyle ou 4-isoquinilinyle et des compositions pharmaceutiques de ceux-ci. Cette invention concerne aussi des techniques d'utilisation de ces composés et des compositions pharmaceutiques de cette invention utilisés comme inhibiteurs de lyases, par exemple de l'enzyme 17a-hydroxylase C17,20. Cette invention concerne enfin des techniques de traitement du cancer d'un patient qui consiste à administrer à ce patient un composé de l'invention ou une composition pharmaceutique de ces composés. Il peut s'agir d'un cancer de la prostate ou d'un cancer du sein, par exemple.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32499301P | 2001-09-26 | 2001-09-26 | |
| US60/324,993 | 2001-09-26 | ||
| PCT/US2002/030483 WO2003027085A2 (fr) | 2001-09-26 | 2002-09-26 | Thiazoles 3-pyridyle ou 4-isoquinolinyle utilises comme inhibiteurs de lyase c17,20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2461360A1 true CA2461360A1 (fr) | 2003-04-03 |
Family
ID=23265979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461360A Abandoned CA2461360A1 (fr) | 2001-09-26 | 2002-09-26 | Thiazoles 3-pyridyle ou 4-isoquinolinyle utilises comme inhibiteurs de lyase c17,20 |
| CA002461363A Abandoned CA2461363A1 (fr) | 2001-09-26 | 2002-09-26 | 3-pyridyl indoles et indazoles substitues servant d'inhibiteurs de c17,20 lyase |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002461363A Abandoned CA2461363A1 (fr) | 2001-09-26 | 2002-09-26 | 3-pyridyl indoles et indazoles substitues servant d'inhibiteurs de c17,20 lyase |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1432698A2 (fr) |
| JP (2) | JP2005532983A (fr) |
| AU (2) | AU2002362603A1 (fr) |
| CA (2) | CA2461360A1 (fr) |
| WO (8) | WO2003027101A1 (fr) |
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| JP4160295B2 (ja) * | 2000-12-08 | 2008-10-01 | 武田薬品工業株式会社 | 3−ピリジル基を有する置換チアゾール誘導体、その製造法および用途 |
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| PT630367E (pt) * | 1992-03-09 | 2000-10-31 | Zeneca Ltd | Novos arilindazoles e sua utilizacao como herbicidas |
| KR980700077A (ko) * | 1994-11-29 | 1998-03-30 | 나까토미 히로타카 | 2-아미노티아졸유도체 및 그 염류로 이루어진 항균제 또는 살균제(Antibacterial Prepartion or Bactericide comprising 2-Aminothiazole Derivative or Salt Thereof |
| US6046136A (en) * | 1997-06-24 | 2000-04-04 | Zeneca Limited | Herbicidal heterocyclic N-oxides compounds |
| US5840721A (en) * | 1997-07-09 | 1998-11-24 | Ontogen Corporation | Imidazole derivatives as MDR modulators |
| AU732406B2 (en) * | 1997-10-03 | 2001-04-26 | Merck Frosst Canada & Co. | Aryl thiophene derivatives as PDE IV inhibitors |
| EP1077958A1 (fr) * | 1998-05-12 | 2001-02-28 | American Home Products Corporation | Acides oxazol-aryl-carboxyliques utiles dans le traitement de l'insulinoresistance et de l'hyperglycemie |
| WO2000006556A1 (fr) * | 1998-07-27 | 2000-02-10 | Abbott Laboratories | Antiproliferants a base d'oxazolines substituees |
| WO2001064674A1 (fr) * | 2000-03-01 | 2001-09-07 | Janssen Pharmaceutica N.V. | Derives de thiazolyle 2,4-disubstitue |
-
2002
- 2002-09-26 CA CA002461360A patent/CA2461360A1/fr not_active Abandoned
- 2002-09-26 WO PCT/US2002/030979 patent/WO2003027101A1/fr not_active Ceased
- 2002-09-26 WO PCT/US2002/030981 patent/WO2003027105A1/fr not_active Ceased
- 2002-09-26 EP EP02778338A patent/EP1432698A2/fr not_active Withdrawn
- 2002-09-26 AU AU2002362603A patent/AU2002362603A1/en not_active Abandoned
- 2002-09-26 EP EP02799636A patent/EP1432706A2/fr not_active Withdrawn
- 2002-09-26 AU AU2002340010A patent/AU2002340010A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030482 patent/WO2003027094A2/fr not_active Ceased
- 2002-09-26 WO PCT/US2002/030983 patent/WO2003027096A1/fr not_active Ceased
- 2002-09-26 JP JP2003530675A patent/JP2005532983A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030483 patent/WO2003027085A2/fr not_active Ceased
- 2002-09-26 JP JP2003530682A patent/JP2005528325A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030834 patent/WO2003027107A1/fr not_active Ceased
- 2002-09-26 CA CA002461363A patent/CA2461363A1/fr not_active Abandoned
- 2002-09-26 WO PCT/US2002/030982 patent/WO2003027095A1/fr not_active Ceased
- 2002-09-26 WO PCT/US2002/030924 patent/WO2003027100A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2003027105A1 (fr) | 2003-04-03 |
| AU2002362603A1 (en) | 2003-04-07 |
| CA2461363A1 (fr) | 2003-04-03 |
| WO2003027101A1 (fr) | 2003-04-03 |
| WO2003027085A2 (fr) | 2003-04-03 |
| AU2002340010A1 (en) | 2003-04-07 |
| WO2003027107A1 (fr) | 2003-04-03 |
| WO2003027096A1 (fr) | 2003-04-03 |
| JP2005528325A (ja) | 2005-09-22 |
| WO2003027094A3 (fr) | 2003-10-23 |
| WO2003027085A3 (fr) | 2003-12-04 |
| EP1432698A2 (fr) | 2004-06-30 |
| WO2003027095A1 (fr) | 2003-04-03 |
| EP1432706A2 (fr) | 2004-06-30 |
| WO2003027094A2 (fr) | 2003-04-03 |
| WO2003027100A1 (fr) | 2003-04-03 |
| JP2005532983A (ja) | 2005-11-04 |
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