ES2430821T3 - Compuestos de N-arilpirazol para usar contra la diabetes - Google Patents
Compuestos de N-arilpirazol para usar contra la diabetes Download PDFInfo
- Publication number
- ES2430821T3 ES2430821T3 ES07839443T ES07839443T ES2430821T3 ES 2430821 T3 ES2430821 T3 ES 2430821T3 ES 07839443 T ES07839443 T ES 07839443T ES 07839443 T ES07839443 T ES 07839443T ES 2430821 T3 ES2430821 T3 ES 2430821T3
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- Prior art keywords
- methyl
- alkyl
- aryl
- pyrimidin
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 156
- 206010012601 diabetes mellitus Diseases 0.000 title description 23
- -1 halo (C1-C6) alkyl Chemical group 0.000 claims abstract description 169
- 125000003118 aryl group Chemical group 0.000 claims abstract description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 50
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 29
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 24
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 19
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims abstract description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- 125000004450 alkenylene group Chemical group 0.000 claims abstract description 8
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims abstract description 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract description 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims abstract description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 5
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims abstract description 3
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 3
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 58
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 47
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 36
- 201000010099 disease Diseases 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 31
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- 239000003814 drug Substances 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 208000024891 symptom Diseases 0.000 claims description 15
- 201000001421 hyperglycemia Diseases 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 12
- 206010028980 Neoplasm Diseases 0.000 claims description 11
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- 206010061218 Inflammation Diseases 0.000 claims description 10
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- 208000006673 asthma Diseases 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
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- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 230000028327 secretion Effects 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 230000003914 insulin secretion Effects 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 claims description 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
- 229910052710 silicon Inorganic materials 0.000 claims description 5
- 125000000335 thiazolyl group Chemical group 0.000 claims description 5
- 125000006530 (C4-C6) alkyl group Chemical group 0.000 claims description 4
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 229910052731 fluorine Chemical group 0.000 claims description 4
- 239000011737 fluorine Chemical group 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 claims description 3
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 claims description 3
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
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- 229960002632 acarbose Drugs 0.000 claims description 2
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 229960003105 metformin Drugs 0.000 claims description 2
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
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- 210000002237 B-cell of pancreatic islet Anatomy 0.000 claims 2
- 210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims 1
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 131
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 129
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 112
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 50
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
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- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
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| US851083P | 2006-10-10 | ||
| PCT/US2007/021678 WO2008045484A1 (en) | 2006-10-10 | 2007-10-09 | N-aryl pyrazole compounds for use against diabetes |
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| ES2430821T3 true ES2430821T3 (es) | 2013-11-21 |
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| EP (1) | EP2079728B1 (enExample) |
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| TW (1) | TW200831491A (enExample) |
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| ES2551095T3 (es) * | 2007-07-19 | 2015-11-16 | Lundbeck, H., A/S | Amidas heterocíclicas de 5 miembros y compuestos relacionados |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| BRPI0816382A2 (pt) | 2007-09-06 | 2015-02-24 | Merck Sharp & Dohme | Composto, composição, e, métodos para ativar a guanilato ciclase solúvel e para tratar ou previnir doenças |
| AU2010218224B2 (en) | 2009-02-26 | 2013-06-27 | Merck Sharp & Dohme Corp. | Soluble guanylate cyclase activators |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2571359A4 (en) * | 2010-05-20 | 2013-10-23 | Merck Sharp & Dohme | NOVEL PROLYLCARBOXYPEPTIDASE HEMMER |
| EA023254B1 (ru) | 2010-05-27 | 2016-05-31 | Мерк Шарп Энд Домэ Корп. | Активаторы растворимой гуанилатциклазы |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| JP5605104B2 (ja) * | 2010-09-10 | 2014-10-15 | セントラル硝子株式会社 | ピラゾール化合物の製造方法 |
| AR087701A1 (es) * | 2011-08-31 | 2014-04-09 | Japan Tobacco Inc | Derivados de pirazol con actividad inhibidora de sglt1 |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| EP2760862B1 (en) | 2011-09-27 | 2015-10-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| ES2707323T3 (es) | 2012-12-07 | 2019-04-03 | Chemocentryx Inc | Diazol lactamas |
| ES2648994T3 (es) * | 2012-12-21 | 2018-01-09 | Chemocentryx, Inc. | Diazolamidas como antagonistas del receptor CCR1 |
| CN103772282B (zh) * | 2014-02-26 | 2015-09-23 | 上海毕得医药科技有限公司 | 一种3-叔丁基-1h-吡唑-4-甲醛的制备方法 |
| WO2016138631A1 (en) | 2015-03-03 | 2016-09-09 | Eli Lilly And Company | Imidazo benzamide compounds |
| CN118994191A (zh) * | 2016-02-05 | 2024-11-22 | 戴纳立制药公司 | 受体相互作用蛋白激酶1的抑制剂 |
| WO2017176965A1 (en) | 2016-04-07 | 2017-10-12 | Chemocentryx, Inc. | Reducing tumor burden by administering ccr1 antagonists in combination with pd-1 inhibitors or pd-l1 inhibitors |
| HRP20220636T1 (hr) | 2016-12-09 | 2022-07-22 | Denali Therapeutics Inc. | Spojevi korisni kao inhibitori ripk1 |
| SG11202009179TA (en) * | 2018-04-04 | 2020-10-29 | Japan Tobacco Inc | Pyrazole compounds substituted with heteroaryl and pharmaceutical use thereof |
| WO2020007729A1 (en) | 2018-07-04 | 2020-01-09 | Boehringer Ingelheim International Gmbh | Triazole benzamide derivatives as gpr142 agonists |
| US11034669B2 (en) | 2018-11-30 | 2021-06-15 | Nuvation Bio Inc. | Pyrrole and pyrazole compounds and methods of use thereof |
| AU2023206890A1 (en) | 2022-01-12 | 2024-08-22 | Denali Therapeutics Inc. | Crystalline forms of (s)-5-benzyl-n-(5-methyl-4-oxo-2, 3,4,5- tetrahydropyrido [3,2-b] [l,4]oxazepin-3-yl)-4h-l,2,4-triazole-3-carboxamide |
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| US4265874A (en) | 1980-04-25 | 1981-05-05 | Alza Corporation | Method of delivering drug with aid of effervescent activity generated in environment of use |
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| TW312694B (enExample) | 1994-09-26 | 1997-08-11 | Daiichi Seiyaku Co | |
| US5883105A (en) * | 1996-04-03 | 1999-03-16 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| AR038955A1 (es) | 1996-12-05 | 2005-02-02 | Amgen Inc | Compuestos de pirimidinona y piridona sustituidos y metodos para su uso |
| US6169086B1 (en) * | 1997-01-27 | 2001-01-02 | Daiichi Pharmaceutical Co., Ltd. | Pyrazole derivatives |
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| JP4960565B2 (ja) | 2000-05-12 | 2012-06-27 | ジェンザイム コーポレーション | ＴＮＦαシグナル伝達のモジュレータ |
| WO2002023986A1 (en) | 2000-08-25 | 2002-03-28 | Sankyo Company, Limited | 4-acylaminopyrazole derivatives |
| US20040198758A1 (en) * | 2001-08-17 | 2004-10-07 | Rapado Liliana Parra | N-heterocyclyl substituted thienyloxy-pyrimidines used as herbicides |
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| CA2564325A1 (en) | 2004-04-30 | 2005-11-24 | Bayer Pharmaceuticals Corporation | Substituted pyrazolyl urea derivatives useful in the treatment of cancer |
| WO2007008541A2 (en) | 2005-07-08 | 2007-01-18 | Kalypsys, Inc. | Cellular cholesterol absorption modifiers |
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-
2007
- 2007-10-09 EP EP07839443.4A patent/EP2079728B1/en active Active
- 2007-10-09 WO PCT/US2007/021678 patent/WO2008045484A1/en not_active Ceased
- 2007-10-09 CA CA002675511A patent/CA2675511A1/en not_active Abandoned
- 2007-10-09 ES ES07839443T patent/ES2430821T3/es active Active
- 2007-10-09 JP JP2009532398A patent/JP2010505957A/ja not_active Withdrawn
- 2007-10-09 US US11/973,900 patent/US8022061B2/en not_active Expired - Fee Related
- 2007-10-09 CL CL200702904A patent/CL2007002904A1/es unknown
- 2007-10-09 MX MX2009003821A patent/MX2009003821A/es unknown
- 2007-10-09 AU AU2007308154A patent/AU2007308154A1/en not_active Abandoned
- 2007-10-09 TW TW096137866A patent/TW200831491A/zh unknown
- 2007-10-10 AR ARP070104489A patent/AR063240A1/es unknown
- 2007-10-10 PE PE2007001365A patent/PE20080858A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2675511A1 (en) | 2008-04-17 |
| MX2009003821A (es) | 2009-05-25 |
| PE20080858A1 (es) | 2008-08-06 |
| AR063240A1 (es) | 2009-01-14 |
| CL2007002904A1 (es) | 2008-06-06 |
| EP2079728B1 (en) | 2013-09-25 |
| TW200831491A (en) | 2008-08-01 |
| US8022061B2 (en) | 2011-09-20 |
| US20080153778A1 (en) | 2008-06-26 |
| AU2007308154A1 (en) | 2008-04-17 |
| JP2010505957A (ja) | 2010-02-25 |
| WO2008045484A1 (en) | 2008-04-17 |
| EP2079728A1 (en) | 2009-07-22 |
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