JP2006513202A - 血管形成インヒビターとしてのピペリジニル−チアゾールカルボン酸誘導体 - Google Patents
血管形成インヒビターとしてのピペリジニル−チアゾールカルボン酸誘導体 Download PDFInfo
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- JP2006513202A JP2006513202A JP2004563361A JP2004563361A JP2006513202A JP 2006513202 A JP2006513202 A JP 2006513202A JP 2004563361 A JP2004563361 A JP 2004563361A JP 2004563361 A JP2004563361 A JP 2004563361A JP 2006513202 A JP2006513202 A JP 2006513202A
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- piperidinyl
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- LTADQRWAAWTFQF-UHFFFAOYSA-N 4-piperidin-1-yl-1,3-thiazole-2-carboxylic acid Chemical class S1C(C(=O)O)=NC(N2CCCCC2)=C1 LTADQRWAAWTFQF-UHFFFAOYSA-N 0.000 title 1
- 229940121369 angiogenesis inhibitor Drugs 0.000 title 1
- 239000004037 angiogenesis inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 37
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims abstract description 32
- 239000002525 vasculotropin inhibitor Substances 0.000 claims abstract description 21
- 201000009273 Endometriosis Diseases 0.000 claims abstract description 18
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 208000002780 macular degeneration Diseases 0.000 claims abstract description 12
- 230000001154 acute effect Effects 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 60
- -1 aralkoxy group Chemical group 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 20
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 20
- 201000011510 cancer Diseases 0.000 claims description 17
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 125000004104 aryloxy group Chemical group 0.000 claims description 12
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 125000001544 thienyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000002541 furyl group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 6
- 238000011200 topical administration Methods 0.000 claims description 6
- HKZCWJKZGLEYBZ-UHFFFAOYSA-N n-(5-carbamoyl-2-methoxyphenyl)-2-[1-[[4-(dimethylamino)phenyl]carbamothioyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC(=O)C1=CSC(C2CCN(CC2)C(=S)NC=2C=CC(=CC=2)N(C)C)=N1 HKZCWJKZGLEYBZ-UHFFFAOYSA-N 0.000 claims description 5
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Chemical group N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- ZQGVXCZSHVLLNA-UHFFFAOYSA-N 2-[1-(1-benzofuran-2-carbonyl)piperidin-4-yl]-n-(5-carbamoyl-2-methoxyphenyl)-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC(=O)C1=CSC(C2CCN(CC2)C(=O)C=2OC3=CC=CC=C3C=2)=N1 ZQGVXCZSHVLLNA-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- RKRNGWLHGHJULB-UHFFFAOYSA-N n-(5-carbamoyl-2-methoxyphenyl)-2-[1-(4,7-dimethylpyrazolo[5,1-c][1,2,4]triazine-3-carbonyl)piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC(=O)C1=CSC(C2CCN(CC2)C(=O)C2=C(N3N=C(C)C=C3N=N2)C)=N1 RKRNGWLHGHJULB-UHFFFAOYSA-N 0.000 claims description 3
- GNYSPFJSQCPIQD-UHFFFAOYSA-N n-(5-carbamoyl-2-methoxyphenyl)-2-[1-[2-(2-chlorophenyl)acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC(=O)C1=CSC(C2CCN(CC2)C(=O)CC=2C(=CC=CC=2)Cl)=N1 GNYSPFJSQCPIQD-UHFFFAOYSA-N 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- JITDERODDZHJOA-UHFFFAOYSA-N n-(5-carbamoyl-2-methoxyphenyl)-2-[1-[2-(3,4-dimethylphenoxy)acetyl]piperidin-4-yl]-1,3-thiazole-4-carboxamide Chemical compound COC1=CC=C(C(N)=O)C=C1NC(=O)C1=CSC(C2CCN(CC2)C(=O)COC=2C=C(C)C(C)=CC=2)=N1 JITDERODDZHJOA-UHFFFAOYSA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 abstract description 33
- 230000000699 topical effect Effects 0.000 abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 41
- 125000001424 substituent group Chemical group 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
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- 239000000203 mixture Substances 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 19
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 229910052736 halogen Inorganic materials 0.000 description 17
- 150000002367 halogens Chemical class 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 125000002971 oxazolyl group Chemical group 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 239000003921 oil Substances 0.000 description 13
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- 239000011541 reaction mixture Substances 0.000 description 13
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- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 125000004953 trihalomethyl group Chemical group 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 230000033115 angiogenesis Effects 0.000 description 9
- 238000003556 assay Methods 0.000 description 9
- 125000005438 isoindazolyl group Chemical group 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- LHNMNSLNPGLLEM-UHFFFAOYSA-N ethyl 2-piperidin-4-yl-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2CCNCC2)=N1 LHNMNSLNPGLLEM-UHFFFAOYSA-N 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 125000002636 imidazolinyl group Chemical group 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 239000002674 ointment Substances 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical group N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 101000742346 Crotalus durissus collilineatus Zinc metalloproteinase/disintegrin Proteins 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 101000872559 Hediste diversicolor Hemerythrin Proteins 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 125000002015 acyclic group Chemical group 0.000 description 6
- 239000007900 aqueous suspension Substances 0.000 description 6
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 description 6
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- 239000011616 biotin Substances 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
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- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 6
- 125000003373 pyrazinyl group Chemical group 0.000 description 6
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 6
- 125000003226 pyrazolyl group Chemical group 0.000 description 6
- 125000002098 pyridazinyl group Chemical group 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 6
- 125000000168 pyrrolyl group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
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- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 6
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- BBQVCBKOBKHCKH-UHFFFAOYSA-N 2-[1-[[4-(dimethylamino)phenyl]carbamothioyl]piperidin-4-yl]-1,3-thiazole-4-carboxylic acid Chemical compound C1=CC(N(C)C)=CC=C1NC(=S)N1CCC(C=2SC=C(N=2)C(O)=O)CC1 BBQVCBKOBKHCKH-UHFFFAOYSA-N 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
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- DBMJEISEWDBAPA-UHFFFAOYSA-N ethyl 2-[1-[[4-(dimethylamino)phenyl]carbamothioyl]piperidin-4-yl]-1,3-thiazole-4-carboxylate Chemical compound CCOC(=O)C1=CSC(C2CCN(CC2)C(=S)NC=2C=CC(=CC=2)N(C)C)=N1 DBMJEISEWDBAPA-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- 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
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Ophthalmology & Optometry (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0230162.0A GB0230162D0 (en) | 2002-12-24 | 2002-12-24 | Compounds useful in inhibiting angiogenesis |
| PCT/GB2003/005651 WO2004058750A1 (en) | 2002-12-24 | 2003-12-24 | Piperidinyl-thiazole carboxylic acid derivatives as angiogenesis inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006513202A true JP2006513202A (ja) | 2006-04-20 |
| JP2006513202A5 JP2006513202A5 (enExample) | 2007-02-08 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004563361A Pending JP2006513202A (ja) | 2002-12-24 | 2003-12-24 | 血管形成インヒビターとしてのピペリジニル−チアゾールカルボン酸誘導体 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20060135501A1 (enExample) |
| EP (1) | EP1581528B1 (enExample) |
| JP (1) | JP2006513202A (enExample) |
| AT (1) | ATE368662T1 (enExample) |
| AU (2) | AU2003290335A1 (enExample) |
| CA (1) | CA2511506A1 (enExample) |
| DE (1) | DE60315355T2 (enExample) |
| GB (1) | GB0230162D0 (enExample) |
| WO (2) | WO2004058750A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007506651A (ja) * | 2003-06-25 | 2007-03-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ｍｔｐ阻害剤としてのチアゾリルピペリジン誘導体 |
| JP2007532135A (ja) * | 2004-04-13 | 2007-11-15 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 高血糖症および関連障害の処置のための、ヒトｇタンパク質共役レセプターおよびそのモジュレーター |
| JP2010516765A (ja) * | 2007-01-25 | 2010-05-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性アミド |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1637529A1 (en) * | 2004-09-20 | 2006-03-22 | 4Sc Ag | Novel piperidin-4-yl-thiazole-carboxamide analogues as inhibitors of T-cell proliferation and uses thereof |
| WO2006032322A1 (en) * | 2004-09-20 | 2006-03-30 | 4Sc Ag | NOVEL HETEROCYCLIC NF-κB INHIBITORS |
| US7601745B2 (en) | 2004-09-27 | 2009-10-13 | 4Sc Ag | Heterocyclic NF-kB inhibitors |
| TW200738701A (en) | 2005-07-26 | 2007-10-16 | Du Pont | Fungicidal carboxamides |
| AU2006278998A1 (en) * | 2005-07-29 | 2007-02-15 | 4Sc Ag | Novel heterocyclic NF-kB inhibitors |
| GB0518494D0 (en) * | 2005-09-09 | 2005-10-19 | Argenta Discovery Ltd | Thiazole compounds |
| EP1832585A1 (en) * | 2006-03-10 | 2007-09-12 | ORIDIS BIOMED Forschungs- und Entwicklungs GmbH | Thiazole-piperidine derivatives for treatment of hyperproliferative diseases |
| EP1832586A1 (en) * | 2006-03-10 | 2007-09-12 | Oridis Biomed Forschungs- und Entwicklungs GmbH | Thiazole-piperidine derivatives in treatment of diseases of liver and the pancreas |
| WO2007104557A2 (en) * | 2006-03-15 | 2007-09-20 | 4Sc Ag | Novel heterocyclic nf-kb inhibitors |
| EP1834954A1 (en) * | 2006-03-15 | 2007-09-19 | 4Sc Ag | Thiazoles as NF-kB Inhibitors (proteasome inhibitors) |
| JP2009529555A (ja) * | 2006-03-15 | 2009-08-20 | ４エスツェー アクチェンゲゼルシャフト | 新規複素環式ＮＦ−κＢ阻害薬 |
| WO2008013622A2 (en) * | 2006-07-27 | 2008-01-31 | E. I. Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| US9090604B2 (en) | 2006-07-27 | 2015-07-28 | E I Du Pont De Nemours And Company | Fungicidal azocyclic amides |
| US7638541B2 (en) | 2006-12-28 | 2009-12-29 | Metabolex Inc. | 5-ethyl-2-{4-[4-(4-tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidine |
| CN101754962B (zh) | 2007-07-19 | 2013-12-25 | 赛马拜制药公司 | 作为rup3或gpr119受体的激动剂治疗糖尿病和代谢性病症的n-氮杂环状经取代吡咯、吡唑、咪唑、三唑和四唑衍生物 |
| WO2009018844A1 (en) * | 2007-08-09 | 2009-02-12 | Oridis Biomed Forschungs- Und Entwicklungs Gmbh | Thiazole-piperidine derivatives for treatment of hyperproliferative diseases |
| DE102007047735A1 (de) | 2007-10-05 | 2009-04-09 | Merck Patent Gmbh | Thiazolderivate |
| TWI428091B (zh) | 2007-10-23 | 2014-03-01 | Du Pont | 殺真菌劑混合物 |
| EP2070925A1 (de) * | 2007-12-10 | 2009-06-17 | Bayer Schering Pharma Aktiengesellschaft | Neue 2-substituierte Tiazol-4-carbonsäureamid-Derivative deren Herstellung und Verwendung als Arzneimittel |
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- 2003-12-24 CA CA002511506A patent/CA2511506A1/en not_active Abandoned
- 2003-12-24 EP EP03789563A patent/EP1581528B1/en not_active Expired - Lifetime
- 2003-12-24 AT AT03789563T patent/ATE368662T1/de not_active IP Right Cessation
- 2003-12-24 AU AU2003290335A patent/AU2003290335A1/en not_active Abandoned
- 2003-12-24 US US10/540,645 patent/US20060135501A1/en not_active Abandoned
- 2003-12-24 WO PCT/GB2003/005654 patent/WO2004058751A1/en not_active Ceased
- 2003-12-24 DE DE60315355T patent/DE60315355T2/de not_active Expired - Fee Related
- 2003-12-24 JP JP2004563361A patent/JP2006513202A/ja active Pending
- 2003-12-24 AU AU2003294143A patent/AU2003294143A1/en not_active Abandoned
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| JPH11513382A (ja) * | 1995-10-20 | 1999-11-16 | ドクトル カルル トーマエ ゲゼルシャフト ミット ベシュレンクテル ハフツング | ５員複素環化合物、これらの化合物を含む医薬品、それらの使用及びそれらの調製方法 |
| WO1998046599A1 (en) * | 1997-04-16 | 1998-10-22 | J. Uriach & Cia. S.A. | Novel carboxamides as platelet aggregation inhibitors |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007506651A (ja) * | 2003-06-25 | 2007-03-22 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ｍｔｐ阻害剤としてのチアゾリルピペリジン誘導体 |
| JP2007532135A (ja) * | 2004-04-13 | 2007-11-15 | アリーナ ファーマシューティカルズ， インコーポレイテッド | 高血糖症および関連障害の処置のための、ヒトｇタンパク質共役レセプターおよびそのモジュレーター |
| JP2008263979A (ja) * | 2004-04-13 | 2008-11-06 | Arena Pharmaceuticals Inc | 高血糖症および関連障害の処置のための、ヒトｇタンパク質共役レセプターおよびそのモジュレーター |
| JP2010516765A (ja) * | 2007-01-25 | 2010-05-20 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 殺菌性アミド |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1581528B1 (en) | 2007-08-01 |
| US20060135501A1 (en) | 2006-06-22 |
| WO2004058751A1 (en) | 2004-07-15 |
| GB0230162D0 (en) | 2003-02-05 |
| CA2511506A1 (en) | 2004-07-15 |
| WO2004058750A1 (en) | 2004-07-15 |
| AU2003290335A1 (en) | 2004-07-22 |
| EP1581528A1 (en) | 2005-10-05 |
| DE60315355D1 (de) | 2007-09-13 |
| AU2003294143A1 (en) | 2004-07-22 |
| ATE368662T1 (de) | 2007-08-15 |
| DE60315355T2 (de) | 2008-05-08 |
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