JP2005532983A - C17,20リアーゼ阻害剤としての3‐ピリジルもしくは4‐イソキノリニルチアゾール - Google Patents
C17,20リアーゼ阻害剤としての3‐ピリジルもしくは4‐イソキノリニルチアゾール Download PDFInfo
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- JP2005532983A JP2005532983A JP2003530675A JP2003530675A JP2005532983A JP 2005532983 A JP2005532983 A JP 2005532983A JP 2003530675 A JP2003530675 A JP 2003530675A JP 2003530675 A JP2003530675 A JP 2003530675A JP 2005532983 A JP2005532983 A JP 2005532983A
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- Prior art keywords
- alkyl
- halogen
- pyridyl
- cycloalkyl
- haloalkyl
- Prior art date
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title claims abstract description 28
- 239000002697 lyase inhibitor Substances 0.000 title description 7
- 229940122014 Lyase inhibitor Drugs 0.000 title description 4
- MOYQLVVBWFGTJI-UHFFFAOYSA-N 4-isoquinolin-1-yl-1,3-thiazole Chemical compound 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 162
- -1 4-isoquinolinyl substituents Chemical group 0.000 claims abstract description 83
- 102000004317 Lyases Human genes 0.000 claims abstract description 70
- 108090000856 Lyases Proteins 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 70
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 29
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 25
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 25
- 201000011510 cancer Diseases 0.000 claims abstract description 22
- 206010006187 Breast cancer Diseases 0.000 claims abstract description 19
- 208000026310 Breast neoplasm Diseases 0.000 claims abstract description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 150000003557 thiazoles Chemical class 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
- 150000002367 halogens Chemical class 0.000 claims description 50
- 239000000126 substance Substances 0.000 claims description 43
- 125000004076 pyridyl group Chemical group 0.000 claims description 35
- 150000001204 N-oxides Chemical class 0.000 claims description 34
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 28
- 125000001188 haloalkyl group Chemical group 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
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- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 12
- 150000001408 amides Chemical class 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 230000036961 partial effect Effects 0.000 claims description 8
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 8
- 150000003852 triazoles Chemical class 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 150000001721 carbon Chemical group 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
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
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- 241000288906 Primates Species 0.000 claims description 3
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- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 229950000244 sulfanilic acid Drugs 0.000 description 1
- 230000019635 sulfation Effects 0.000 description 1
- 238000005670 sulfation reaction Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- CLOXAWYNXXEWBT-UHFFFAOYSA-N tert-butyl n-(3-oxocyclopentyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1CCC(=O)C1 CLOXAWYNXXEWBT-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- PHCBRBWANGJMHS-UHFFFAOYSA-J tetrasodium;disulfate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O PHCBRBWANGJMHS-UHFFFAOYSA-J 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
- 230000004565 tumor cell growth Effects 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 229910052727 yttrium Inorganic materials 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)
- Cardiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Diabetes (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32499301P | 2001-09-26 | 2001-09-26 | |
| PCT/US2002/030483 WO2003027085A2 (en) | 2001-09-26 | 2002-09-26 | 3-pyridyl or 4-isoquinolinyl thiazoles as c17,20 lyase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2005532983A true JP2005532983A (ja) | 2005-11-04 |
Family
ID=23265979
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530675A Withdrawn JP2005532983A (ja) | 2001-09-26 | 2002-09-26 | C17,20リアーゼ阻害剤としての3‐ピリジルもしくは4‐イソキノリニルチアゾール |
| JP2003530682A Withdrawn JP2005528325A (ja) | 2001-09-26 | 2002-09-26 | C17,20リアーゼ阻害剤としての置換3−ピリジルインドール類およびインダゾール類 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003530682A Withdrawn JP2005528325A (ja) | 2001-09-26 | 2002-09-26 | C17,20リアーゼ阻害剤としての置換3−ピリジルインドール類およびインダゾール類 |
Country Status (5)
| Country | Link |
|---|---|
| EP (2) | EP1432706A2 (enExample) |
| JP (2) | JP2005532983A (enExample) |
| AU (2) | AU2002340010A1 (enExample) |
| CA (2) | CA2461360A1 (enExample) |
| WO (8) | WO2003027094A2 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002234843A (ja) * | 2000-12-08 | 2002-08-23 | Takeda Chem Ind Ltd | 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 |
| WO2009099195A1 (ja) | 2008-02-08 | 2009-08-13 | Shiseido Company Ltd. | 美白剤及び皮膚外用剤 |
| JP2011524422A (ja) * | 2008-06-16 | 2011-09-01 | ユニバーシティ オブ テネシー リサーチ ファウンデーション | 癌を処置するための化合物 |
| JP2012500278A (ja) * | 2008-08-20 | 2012-01-05 | シェーリング コーポレイション | 置換ピリジン誘導体および置換ピリミジン誘導体ならびにそれらのウイルス感染の治療における使用 |
| JP2014512411A (ja) * | 2011-04-28 | 2014-05-22 | ノバルティス アーゲー | 17α−ヒドロキシラーゼ/C17,20−リアーゼ阻害剤 |
| JP2018127451A (ja) * | 2017-02-08 | 2018-08-16 | 国立大学法人岐阜大学 | 芳香族アミン化合物の製造方法と新規な芳香族アミン化合物および蛍光発光材料と紫外線吸収剤 |
Families Citing this family (71)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AU2014241816B9 (en) | 2013-03-14 | 2019-02-14 | Pellficure Pharmaceuticals Inc. | Novel therapy for prostate carcinoma |
| EP3191087A1 (en) | 2014-09-12 | 2017-07-19 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| EP3528799A1 (en) | 2016-10-24 | 2019-08-28 | Pellficure Pharmaceuticals, Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| EP4077332A4 (en) * | 2019-12-18 | 2024-05-01 | The Regents of the University of California | LIN28 INHIBITORS AND THEIR METHODS OF USE |
| US20210246109A1 (en) * | 2020-02-11 | 2021-08-12 | University Of Kentucky Research Foundation | Potent and selective inhibitors of cytochrome p450 |
| WO2023049199A1 (en) * | 2021-09-24 | 2023-03-30 | Zeno Management, Inc. | Azole compounds |
| CN117551029A (zh) * | 2023-11-22 | 2024-02-13 | 河南大学 | 一种4-溴-3-氰基吡啶的合成方法 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK150068C (da) * | 1978-06-02 | 1987-06-29 | Pfizer | Analogifremgangsmaade til fremstilling af aminothiazoler |
| JPS55133366A (en) * | 1979-04-05 | 1980-10-17 | Otsuka Pharmaceut Factory Inc | Thiazole derivative |
| US4536505A (en) * | 1983-05-17 | 1985-08-20 | Ciba-Geigy Corporation | Certain N-(pyridyl) indoles |
| DE3940476A1 (de) * | 1989-12-07 | 1991-06-13 | Bayer Ag | Pyridinylpyrimidin-derivate |
| DE3940477A1 (de) * | 1989-12-07 | 1991-06-13 | Bayer Ag | Hetaryl-substituierte pyridinylpyrimidin-derivate |
| JPH04154773A (ja) * | 1990-10-15 | 1992-05-27 | Green Cross Corp:The | チアゾール誘導体 |
| DE4117560A1 (de) * | 1991-05-29 | 1992-12-03 | Bayer Ag | Verwendung von pyridinylpyrimidin-derivaten zum schutz technischer materialien |
| TW223004B (enExample) * | 1991-11-25 | 1994-05-01 | Sumitomo Chemical Co | |
| US5395817A (en) * | 1992-01-22 | 1995-03-07 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| US5599774A (en) * | 1992-01-22 | 1997-02-04 | Imperial Chemical Industries Plc | N-arylindoles and their use as herbicides |
| ATE194332T1 (de) * | 1992-03-09 | 2000-07-15 | Zeneca Ltd | Arylindazoline und ihre anwendung als herbizide |
| US5444038A (en) * | 1992-03-09 | 1995-08-22 | Zeneca Limited | Arylindazoles and their use as herbicides |
| CA2206315A1 (en) * | 1994-11-29 | 1996-06-06 | Hisamitsu Pharmaceutical Co., Inc. | Antibacterial preparation or bactericide comprising 2-aminothiazole derivative and/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 |
| WO1999018099A1 (en) * | 1997-10-03 | 1999-04-15 | Merck Frosst Canada & Co. | Aryl thiophene derivatives as pde iv inhibitors |
| CN1308618A (zh) * | 1998-05-12 | 2001-08-15 | 美国家用产品公司 | 用于治疗胰岛素抗性和高血糖的噁唑芳基-羧酸 |
| WO2000006556A1 (en) * | 1998-07-27 | 2000-02-10 | Abbott Laboratories | Substituted oxazolines as antiproliferative agents |
| DE60136530D1 (de) * | 2000-03-01 | 2008-12-24 | Janssen Pharmaceutica Nv | 2,4-disubstituierte thiazolyl derivate |
-
2002
- 2002-09-26 JP JP2003530675A patent/JP2005532983A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030482 patent/WO2003027094A2/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030834 patent/WO2003027107A1/en not_active Ceased
- 2002-09-26 EP EP02799636A patent/EP1432706A2/en not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030982 patent/WO2003027095A1/en not_active Ceased
- 2002-09-26 CA CA002461360A patent/CA2461360A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030981 patent/WO2003027105A1/en not_active Ceased
- 2002-09-26 EP EP02778338A patent/EP1432698A2/en not_active Withdrawn
- 2002-09-26 AU AU2002340010A patent/AU2002340010A1/en not_active Abandoned
- 2002-09-26 AU AU2002362603A patent/AU2002362603A1/en not_active Abandoned
- 2002-09-26 CA CA002461363A patent/CA2461363A1/en not_active Abandoned
- 2002-09-26 WO PCT/US2002/030924 patent/WO2003027100A1/en not_active Ceased
- 2002-09-26 JP JP2003530682A patent/JP2005528325A/ja not_active Withdrawn
- 2002-09-26 WO PCT/US2002/030983 patent/WO2003027096A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030979 patent/WO2003027101A1/en not_active Ceased
- 2002-09-26 WO PCT/US2002/030483 patent/WO2003027085A2/en not_active Ceased
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002234843A (ja) * | 2000-12-08 | 2002-08-23 | Takeda Chem Ind Ltd | 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 |
| WO2009099195A1 (ja) | 2008-02-08 | 2009-08-13 | Shiseido Company Ltd. | 美白剤及び皮膚外用剤 |
| JP2011524422A (ja) * | 2008-06-16 | 2011-09-01 | ユニバーシティ オブ テネシー リサーチ ファウンデーション | 癌を処置するための化合物 |
| JP2012162541A (ja) * | 2008-06-16 | 2012-08-30 | Univ Of Tennessee Research Foundation | 癌を処置するための化合物 |
| JP2012500278A (ja) * | 2008-08-20 | 2012-01-05 | シェーリング コーポレイション | 置換ピリジン誘導体および置換ピリミジン誘導体ならびにそれらのウイルス感染の治療における使用 |
| JP2014512411A (ja) * | 2011-04-28 | 2014-05-22 | ノバルティス アーゲー | 17α−ヒドロキシラーゼ/C17,20−リアーゼ阻害剤 |
| JP2018127451A (ja) * | 2017-02-08 | 2018-08-16 | 国立大学法人岐阜大学 | 芳香族アミン化合物の製造方法と新規な芳香族アミン化合物および蛍光発光材料と紫外線吸収剤 |
| JP7193071B2 (ja) | 2017-02-08 | 2022-12-20 | 国立大学法人東海国立大学機構 | 蛍光発光材料および紫外線吸収剤 |
Also Published As
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| EP1432706A2 (en) | 2004-06-30 |
| AU2002340010A1 (en) | 2003-04-07 |
| WO2003027101A1 (en) | 2003-04-03 |
| WO2003027100A1 (en) | 2003-04-03 |
| EP1432698A2 (en) | 2004-06-30 |
| AU2002362603A1 (en) | 2003-04-07 |
| WO2003027085A3 (en) | 2003-12-04 |
| JP2005528325A (ja) | 2005-09-22 |
| WO2003027096A1 (en) | 2003-04-03 |
| CA2461363A1 (en) | 2003-04-03 |
| WO2003027105A1 (en) | 2003-04-03 |
| WO2003027107A1 (en) | 2003-04-03 |
| WO2003027095A1 (en) | 2003-04-03 |
| WO2003027094A3 (en) | 2003-10-23 |
| WO2003027094A2 (en) | 2003-04-03 |
| CA2461360A1 (en) | 2003-04-03 |
| WO2003027085A2 (en) | 2003-04-03 |
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