UA72538C2 - Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents - Google Patents
Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents Download PDFInfo
- Publication number
- UA72538C2 UA72538C2 UA2002031948A UA2002031948A UA72538C2 UA 72538 C2 UA72538 C2 UA 72538C2 UA 2002031948 A UA2002031948 A UA 2002031948A UA 2002031948 A UA2002031948 A UA 2002031948A UA 72538 C2 UA72538 C2 UA 72538C2
- Authority
- UA
- Ukraine
- Prior art keywords
- thiazol
- isopropyl
- amino
- oxoethyl
- acetamide
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 title 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
- 201000011510 cancer Diseases 0.000 claims abstract description 11
- 208000035475 disorder Diseases 0.000 claims abstract description 11
- 230000002062 proliferating effect Effects 0.000 claims abstract description 11
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 4
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 4
- 208000036142 Viral infection Diseases 0.000 claims abstract description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 4
- 230000009385 viral infection Effects 0.000 claims abstract description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 273
- -1 pyrrolidino, morpholino, piperazino Chemical group 0.000 claims description 188
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 120
- 150000001875 compounds Chemical class 0.000 claims description 119
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 49
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- 125000003282 alkyl amino group Chemical group 0.000 claims description 20
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 16
- 125000003277 amino group Chemical group 0.000 claims description 14
- 102000016736 Cyclin Human genes 0.000 claims description 13
- 108050006400 Cyclin Proteins 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 12
- 230000000694 effects Effects 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 230000005764 inhibitory process Effects 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 10
- 108091000080 Phosphotransferase Proteins 0.000 claims description 9
- 125000001769 aryl amino group Chemical group 0.000 claims description 9
- 125000005110 aryl thio group Chemical group 0.000 claims description 9
- 102000020233 phosphotransferase Human genes 0.000 claims description 9
- 125000003386 piperidinyl group Chemical group 0.000 claims description 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- 208000031481 Pathologic Constriction Diseases 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- SNCZNSNPXMPCGN-UHFFFAOYSA-N butanediamide Chemical compound NC(=O)CCC(N)=O SNCZNSNPXMPCGN-UHFFFAOYSA-N 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 6
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002883 imidazolyl group Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 208000037804 stenosis Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 241000124008 Mammalia Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 5
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 5
- 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 230000022131 cell cycle Effects 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
- 230000036262 stenosis Effects 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 201000009030 Carcinoma Diseases 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 201000005787 hematologic cancer Diseases 0.000 claims description 4
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 229960003966 nicotinamide Drugs 0.000 claims description 4
- 235000005152 nicotinamide Nutrition 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- 230000002980 postoperative effect Effects 0.000 claims description 4
- 210000001685 thyroid gland Anatomy 0.000 claims description 4
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 3
- 201000006107 Familial adenomatous polyposis Diseases 0.000 claims description 3
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 3
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- 206010027476 Metastases Diseases 0.000 claims description 3
- 208000009905 Neurofibromatoses Diseases 0.000 claims description 3
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
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- 230000003325 follicular Effects 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims description 2
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- 230000001085 cytostatic effect Effects 0.000 claims description 2
- 239000002254 cytotoxic agent Substances 0.000 claims description 2
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 230000014399 negative regulation of angiogenesis Effects 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
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- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000000049 pigment Substances 0.000 claims 1
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pulmonology (AREA)
- Hospice & Palliative Care (AREA)
- Oncology (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/372,832 US6114365A (en) | 1999-08-12 | 1999-08-12 | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| PCT/IB2000/001423 WO2001014353A1 (en) | 1999-08-12 | 2000-08-11 | Arylmethyl-carbonylamino-thiazole derivatives and their use as antitumor agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA72538C2 true UA72538C2 (en) | 2005-03-15 |
Family
ID=23469806
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA2002031948A UA72538C2 (en) | 1999-08-12 | 2000-11-08 | Arylmethylcarbonylaminothiazole derivatives and use thereof as antitumoral agents |
Country Status (36)
| Country | Link |
|---|---|
| US (3) | US6114365A (pt) |
| EP (1) | EP1204649B1 (pt) |
| JP (1) | JP4864260B2 (pt) |
| KR (2) | KR100773709B1 (pt) |
| CN (1) | CN100410245C (pt) |
| AP (1) | AP1853A (pt) |
| AT (1) | ATE375987T1 (pt) |
| AU (1) | AU782882B2 (pt) |
| BG (1) | BG65484B1 (pt) |
| BR (1) | BR0013281A (pt) |
| CA (1) | CA2381097C (pt) |
| CY (1) | CY1107108T1 (pt) |
| CZ (1) | CZ303138B6 (pt) |
| DE (1) | DE60036803T2 (pt) |
| DK (1) | DK1204649T3 (pt) |
| EA (1) | EA005375B1 (pt) |
| EE (1) | EE04939B1 (pt) |
| ES (1) | ES2295056T3 (pt) |
| GE (1) | GEP20053475B (pt) |
| HK (1) | HK1054233B (pt) |
| HR (1) | HRP20020127B1 (pt) |
| HU (1) | HUP0202492A3 (pt) |
| IL (2) | IL147924A0 (pt) |
| IS (1) | IS2594B (pt) |
| MA (1) | MA25433A1 (pt) |
| MX (1) | MXPA02001508A (pt) |
| NO (1) | NO323576B1 (pt) |
| NZ (1) | NZ517236A (pt) |
| OA (1) | OA12047A (pt) |
| PT (1) | PT1204649E (pt) |
| RS (1) | RS50300B (pt) |
| SI (1) | SI1204649T1 (pt) |
| SK (1) | SK287373B6 (pt) |
| UA (1) | UA72538C2 (pt) |
| WO (1) | WO2001014353A1 (pt) |
| ZA (1) | ZA200201117B (pt) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA024672B1 (ru) * | 2009-03-20 | 2016-10-31 | Оникс Терапьютикс, Инк. | Кристаллические трипептидные ингибиторы эпоксикетон-протеазы |
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| US20020150921A1 (en) * | 1996-02-09 | 2002-10-17 | Francis Barany | Detection of nucleic acid sequence differences using the ligase detection reaction with addressable arrays |
| US6407103B2 (en) | 1998-04-21 | 2002-06-18 | Bristol-Myers Squibb Pharma Company | Indeno [1,2-c] pyrazol-4-ones and their uses |
| US6320050B1 (en) * | 1999-03-29 | 2001-11-20 | Hoffmann-La Roche Inc. | Heteroaromatic glucokinase activators |
| US6610846B1 (en) * | 1999-03-29 | 2003-08-26 | Hoffman-La Roche Inc. | Heteroaromatic glucokinase activators |
| DK1169038T3 (da) | 1999-04-15 | 2012-11-26 | Bristol Myers Squibb Co | Cykliske proteintyrosinkinaseinhibitorer |
| US7125875B2 (en) * | 1999-04-15 | 2006-10-24 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| US6114365A (en) * | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| JP4776843B2 (ja) | 1999-10-01 | 2011-09-21 | イムノゲン インコーポレーティッド | 免疫複合体及び化学療法剤を用いる癌治療用組成物及び方法 |
| US20040048844A1 (en) * | 1999-10-20 | 2004-03-11 | Bristol-Myers Squibb Pharma Company | Acylsemicarbazides as cyclin dependent kinase inhibitors useful as anti-cancer and anti-proliferative agents |
| US6291504B1 (en) | 1999-10-20 | 2001-09-18 | Dupont Pharmaceuticals Company | Acylsemicarbazides and their uses |
| JP2004517840A (ja) * | 2000-11-27 | 2004-06-17 | フアルマシア・イタリア・エツセ・ピー・アー | フェニルアセトアミド−ピラゾール誘導体およびそれの抗腫瘍薬としての使用 |
| WO2002044174A2 (en) * | 2000-12-01 | 2002-06-06 | Bristol-Myers Squibb Pharma Company | 3-(2,4-dimethylthiazol-5-yl) indeno[1,2-c]pyrazol-4-one derivatives as cdk inhibitors |
| WO2002046182A1 (en) | 2000-12-08 | 2002-06-13 | Bristol-Myers Squibb Pharma Company | Semicarbazides and their uses as cyclin dependent kinase inhibitors |
| DK1347971T3 (da) | 2000-12-21 | 2006-05-15 | Bristol Myers Squibb Co | Thiazolylinhibitorer af tyrosinkinaser fra Tec-familien |
| EP1256578B1 (en) | 2001-05-11 | 2006-01-11 | Pfizer Products Inc. | Thiazole derivatives and their use as cdk inhibitors |
| EP1724270A3 (en) | 2001-07-19 | 2007-01-03 | Pfizer Italia S.r.l. | Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents |
| GEP20105095B (en) * | 2001-07-19 | 2010-10-25 | Pfizer Italia Srl | Phenylacetamido-thiazole derivatives, process for their preparation and their use as antitumor agents |
| US7087768B2 (en) * | 2001-09-27 | 2006-08-08 | Equispharm Co., Ltd. | Fumagillol derivatives and preparing method thereof |
| EP2305648A1 (en) * | 2001-12-21 | 2011-04-06 | Novo Nordisk A/S | Amide derivatives useful as glucokinase activators |
| BR0312023A (pt) * | 2002-06-27 | 2005-03-22 | Novo Nordisk As | Composto, composto ativador da glicose cinase, método para evitar a hipoglicemia, uso de um composto, e, composição farmacêutica |
| CA2515728A1 (en) * | 2003-02-12 | 2004-08-26 | Pfizer Inc. | Antiproliferative 2-(sulfo-phenyl)-aminothiazole derivatives |
| CA2516234A1 (en) * | 2003-02-21 | 2004-09-02 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
| JP4758337B2 (ja) * | 2003-03-31 | 2011-08-24 | 株式会社アールテック・ウエノ | 血管透過性亢進疾患を治療する方法 |
| WO2005014591A1 (en) * | 2003-07-15 | 2005-02-17 | L'oreal | 2-acylamino or 2-sulfonylamino-1, 3-thiazoles as couplers for the oxidation dyeing of keratin fibres |
| FR2857664B1 (fr) * | 2003-07-15 | 2007-12-14 | Oreal | Nouveaux derives thiazoles et utilisation de ces derives pour la teinture des fibres keratiniques |
| US7351727B2 (en) * | 2003-09-02 | 2008-04-01 | Bristol-Myers Squibb Company | Inhibitors of 15-lipoxygenase |
| US20050074424A1 (en) * | 2003-10-03 | 2005-04-07 | Lev Salnikov | Using polyion polymers with glucose infusion for a cancer selective chemotherapy compound and method |
| US20070196395A1 (en) * | 2003-12-12 | 2007-08-23 | Mackerell Alexander | Immunomodulatory compounds that target and inhibit the py'binding site of tyrosene kinase p56 lck sh2 domain |
| PT1723128E (pt) * | 2004-01-06 | 2013-02-27 | Novo Nordisk As | Heteroaril-ureias e o seu uso como activadores da glicoquinase |
| CA2584493A1 (en) | 2004-06-18 | 2006-01-05 | Gpc Biotech, Inc. | Kinase inhibitors for treating cancers |
| EP1621536A1 (en) * | 2004-07-27 | 2006-02-01 | Aventis Pharma S.A. | Amino cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors |
| EP1621539A1 (en) * | 2004-07-27 | 2006-02-01 | Aventis Pharma S.A. | Heterocycle -substituted cyclic urea derivatives, preparation thereof and pharmaceutical use thereof as kinase inhibitors |
| EP1781287A4 (en) * | 2004-08-13 | 2008-02-27 | Genentech Inc | THIAZOLE-BASED COMPOUNDS HAVING ENZYMATIC INHIBITORY ACTIVITY USING ADENOSINE TRIPHOSPHATE (ATP) |
| ATE432921T1 (de) | 2004-12-23 | 2009-06-15 | Gpc Biotech Ag | Quadratsäurederivate mit antiproliferativer wirkung |
| WO2007130075A1 (en) * | 2005-06-03 | 2007-11-15 | Xenon Pharmaceuticals Inc. | Aminothiazole derivatives as human stearoyl-coa desaturase inhibitors |
| US7999114B2 (en) * | 2005-07-08 | 2011-08-16 | Novo Nordisk A/S | Dicycloalkylcarbamoyl ureas as glucokinase activators |
| RU2443691C2 (ru) | 2005-07-14 | 2012-02-27 | Транстех Фарма, Инк. | Мочевинные активаторы глюкокиназы |
| EP1914234A1 (en) * | 2006-10-16 | 2008-04-23 | GPC Biotech Inc. | Pyrido[2,3-d]pyrimidines and their use as kinase inhibitors |
| WO2008084043A1 (en) * | 2007-01-09 | 2008-07-17 | Novo Nordisk A/S | Urea glucokinase activators |
| WO2008084044A1 (en) | 2007-01-11 | 2008-07-17 | Novo Nordisk A/S | Urea glucokinase activators |
| JP5568312B2 (ja) * | 2007-02-13 | 2014-08-06 | アーべー・シオンス | キナーゼ阻害剤としての２−アミノチアゾール化合物の合成方法 |
| US8450348B2 (en) * | 2007-02-21 | 2013-05-28 | Forma Tm, Llc | Derivatives of squaric acid with anti-proliferative activity |
| TWI437986B (zh) * | 2008-01-31 | 2014-05-21 | R Tech Ueno Ltd | 噻唑衍生物及使用該衍生物作為ｖａｐ－１抑制劑之用途 |
| US8232402B2 (en) | 2008-03-12 | 2012-07-31 | Link Medicine Corporation | Quinolinone farnesyl transferase inhibitors for the treatment of synucleinopathies and other indications |
| EP2112150B1 (en) | 2008-04-22 | 2013-10-16 | Forma Therapeutics, Inc. | Improved raf inhibitors |
| EP2112152A1 (en) | 2008-04-22 | 2009-10-28 | GPC Biotech AG | Dihydropteridinones as Plk Inhibitors |
| BRPI0920927A2 (pt) | 2008-11-13 | 2019-09-24 | Link Medicine Corp | derivados de azaquinolinona e usos dos mesmos |
| UA103918C2 (en) * | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| EP2440556A1 (en) * | 2009-06-10 | 2012-04-18 | Vertex Pharmaceuticals Incorporated | Inhibitors of phosphatidylinositol 3-kinase |
| DE102009043260A1 (de) * | 2009-09-28 | 2011-04-28 | Merck Patent Gmbh | Pyridinyl-imidazolonderivate |
| EP2325185A1 (en) | 2009-10-28 | 2011-05-25 | GPC Biotech AG | Plk inhibitor |
| HU0900798D0 (en) | 2009-12-21 | 2010-03-01 | Vichem Chemie Kutato Kft | 4-phenylamino-pyrimidine derivatives having protein kinase inhibitor activity |
| WO2012092471A2 (en) * | 2010-12-29 | 2012-07-05 | Development Center For Biotechnology | Novel tubulin inhibitors and methods of using the same |
| RU2011122942A (ru) | 2011-06-08 | 2012-12-20 | Общество С Ограниченной Ответственностью "Асинэкс Медхим" | Новые ингибиторы киназ |
| CN103387551B (zh) * | 2012-05-11 | 2015-05-20 | 中国人民解放军军事医学科学院毒物药物研究所 | 噻唑类化合物及其用途 |
| US9617225B2 (en) | 2012-08-23 | 2017-04-11 | Virostatics Srl | 4,6-disubstituted aminopyrimidine derivatives have anti-HIV activity |
| HUE060671T2 (hu) | 2016-04-11 | 2023-04-28 | Genfit | Eljárás fibrotikus betegségek kezelésére |
| TWI828644B (zh) | 2017-12-06 | 2024-01-11 | 仁新醫藥股份有限公司 | 微管蛋白抑制劑 |
| AU2019215799B2 (en) * | 2018-02-01 | 2022-04-14 | The University Of Sydney | Anti-cancer compounds |
| JP2021526130A (ja) | 2018-06-12 | 2021-09-30 | ブイティーブイ・セラピューティクス・エルエルシー | インスリンまたはインスリン類似体と組み合わせたグルコキナーゼ活性化薬の治療的使用 |
| EP3712127A1 (en) | 2019-03-22 | 2020-09-23 | Deutsches Krebsforschungszentrum | Novel inhibitors of histone deacetylase 10 |
| US20220151962A1 (en) | 2019-03-22 | 2022-05-19 | Deutsches Krebsforschungszentrum | Novel inhibitors of histone deacetylase 10 |
| JPWO2021162054A1 (pt) * | 2020-02-10 | 2021-08-19 | ||
| CN115322208B (zh) * | 2021-05-10 | 2023-04-11 | 中国药科大学 | 2-氨基噻唑类衍生物及其制备方法和医药用途 |
| WO2023182780A1 (ko) * | 2022-03-22 | 2023-09-28 | 오토텔릭바이오 주식회사 | 티아졸 유도체 화합물 및 이의 용도 |
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| NL125062C (pt) * | 1960-04-20 | |||
| TW513418B (en) * | 1996-07-31 | 2002-12-11 | Otsuka Pharma Co Ltd | Thiazole derivatives, their production and use |
| JPH1095777A (ja) * | 1996-07-31 | 1998-04-14 | Otsuka Pharmaceut Co Ltd | チアゾール誘導体 |
| US6794392B1 (en) * | 1996-09-30 | 2004-09-21 | Schering Aktiengesellschaft | Cell differentiation inducer |
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| US6040321A (en) * | 1997-11-12 | 2000-03-21 | Bristol-Myers Squibb Company | Aminothiazole inhibitors of cyclin dependent kinases |
| JP2002518380A (ja) * | 1998-06-18 | 2002-06-25 | ブリストル−マイヤーズ スクイブ カンパニー | サイクリン依存キナーゼの炭素置換アミノチアゾール抑制剤 |
| GB9823871D0 (en) * | 1998-10-30 | 1998-12-23 | Pharmacia & Upjohn Spa | 2-Amino-thiazole derivatives, process for their preparation, and their use as antitumour agents |
| DK1169038T3 (da) * | 1999-04-15 | 2012-11-26 | Bristol Myers Squibb Co | Cykliske proteintyrosinkinaseinhibitorer |
| US6114365A (en) | 1999-08-12 | 2000-09-05 | Pharmacia & Upjohn S.P.A. | Arylmethyl-carbonylamino-thiazole derivatives, process for their preparation, and their use as antitumor agents |
| US6992081B2 (en) * | 2000-03-23 | 2006-01-31 | Elan Pharmaceuticals, Inc. | Compounds to treat Alzheimer's disease |
| SE0102440D0 (sv) * | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compound |
| US6936629B2 (en) * | 2001-12-21 | 2005-08-30 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of flavivirus infections |
| AR042941A1 (es) * | 2003-01-27 | 2005-07-06 | Fujisawa Pharmaceutical Co | Derivados de tiazol, su preparacion, composiciones farmaceuticas que los contienen y su uso en la fabricacion de medicamentos inhibidores de la proteina-1 de adhesion vascular (vap-1) |
-
1999
- 1999-08-12 US US09/372,832 patent/US6114365A/en not_active Expired - Lifetime
-
2000
- 2000-08-11 KR KR1020027001844A patent/KR100773709B1/ko not_active IP Right Cessation
- 2000-08-11 DE DE60036803T patent/DE60036803T2/de not_active Expired - Lifetime
- 2000-08-11 WO PCT/IB2000/001423 patent/WO2001014353A1/en active IP Right Grant
- 2000-08-11 EA EA200200247A patent/EA005375B1/ru not_active IP Right Cessation
- 2000-08-11 SK SK180-2002A patent/SK287373B6/sk not_active IP Right Cessation
- 2000-08-11 JP JP2001518441A patent/JP4864260B2/ja not_active Expired - Fee Related
- 2000-08-11 DK DK00962760T patent/DK1204649T3/da active
- 2000-08-11 NZ NZ517236A patent/NZ517236A/en not_active IP Right Cessation
- 2000-08-11 GE GE4757A patent/GEP20053475B/en unknown
- 2000-08-11 RS YUP-97/02A patent/RS50300B/sr unknown
- 2000-08-11 OA OA1200200052A patent/OA12047A/en unknown
- 2000-08-11 CZ CZ20020486A patent/CZ303138B6/cs not_active IP Right Cessation
- 2000-08-11 SI SI200030974T patent/SI1204649T1/sl unknown
- 2000-08-11 BR BR0013281-0A patent/BR0013281A/pt not_active IP Right Cessation
- 2000-08-11 AT AT00962760T patent/ATE375987T1/de active
- 2000-08-11 EE EEP200200064A patent/EE04939B1/xx not_active IP Right Cessation
- 2000-08-11 KR KR1020077014635A patent/KR100827563B1/ko not_active IP Right Cessation
- 2000-08-11 AU AU74400/00A patent/AU782882B2/en not_active Ceased
- 2000-08-11 EP EP00962760A patent/EP1204649B1/en not_active Expired - Lifetime
- 2000-08-11 CA CA002381097A patent/CA2381097C/en not_active Expired - Fee Related
- 2000-08-11 IL IL14792400A patent/IL147924A0/xx active IP Right Grant
- 2000-08-11 CN CNB008127336A patent/CN100410245C/zh not_active Expired - Fee Related
- 2000-08-11 US US10/048,474 patent/US6784198B1/en not_active Expired - Fee Related
- 2000-08-11 HU HU0202492A patent/HUP0202492A3/hu unknown
- 2000-08-11 MX MXPA02001508A patent/MXPA02001508A/es active IP Right Grant
- 2000-08-11 PT PT00962760T patent/PT1204649E/pt unknown
- 2000-08-11 ES ES00962760T patent/ES2295056T3/es not_active Expired - Lifetime
- 2000-08-11 AP APAP/P/2002/002441A patent/AP1853A/en active
- 2000-11-08 UA UA2002031948A patent/UA72538C2/uk unknown
-
2002
- 2002-01-31 IL IL147924A patent/IL147924A/en not_active IP Right Cessation
- 2002-02-08 ZA ZA200201117A patent/ZA200201117B/en unknown
- 2002-02-11 NO NO20020683A patent/NO323576B1/no not_active IP Right Cessation
- 2002-02-11 IS IS6264A patent/IS2594B/is unknown
- 2002-02-12 HR HR20020127A patent/HRP20020127B1/xx not_active IP Right Cessation
- 2002-03-05 BG BG106481A patent/BG65484B1/bg unknown
- 2002-03-11 MA MA26547A patent/MA25433A1/fr unknown
-
2003
- 2003-09-11 HK HK03106484.7A patent/HK1054233B/zh not_active IP Right Cessation
-
2004
- 2004-07-29 US US10/902,326 patent/US20050004120A1/en not_active Abandoned
-
2007
- 2007-12-20 CY CY20071101629T patent/CY1107108T1/el unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA024672B1 (ru) * | 2009-03-20 | 2016-10-31 | Оникс Терапьютикс, Инк. | Кристаллические трипептидные ингибиторы эпоксикетон-протеазы |
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