RU2012111695A - Фторзамещенные производные 3,5- дициано-4-(1н-индазол-5-ил) -2, 6-диметил-1,4-дигидропиридина и способы их применения - Google Patents
Фторзамещенные производные 3,5- дициано-4-(1н-индазол-5-ил) -2, 6-диметил-1,4-дигидропиридина и способы их применения Download PDFInfo
- Publication number
- RU2012111695A RU2012111695A RU2012111695/04A RU2012111695A RU2012111695A RU 2012111695 A RU2012111695 A RU 2012111695A RU 2012111695/04 A RU2012111695/04 A RU 2012111695/04A RU 2012111695 A RU2012111695 A RU 2012111695A RU 2012111695 A RU2012111695 A RU 2012111695A
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- formula
- compound
- dicarbonitrile
- dihydropyridin
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- -1 Fluoro-substituted 3,5-dicyano-4- (1H-indazole-5-yl) -2, 6-dimethyl-1,4-dihydropyridine Chemical class 0.000 title claims 4
- 229940085304 dihydropyridine derivative selective calcium channel blockers with mainly vascular effects Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 20
- 239000001257 hydrogen Substances 0.000 claims abstract 20
- 239000012453 solvate Substances 0.000 claims abstract 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract 8
- 229910052731 fluorine Chemical group 0.000 claims abstract 8
- 239000011737 fluorine Chemical group 0.000 claims abstract 8
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract 4
- UYZFYANYSIVDGM-OAHLLOKOSA-N (4r)-2-(difluoromethyl)-4-(6-fluoro-3-methyl-2h-indazol-5-yl)-6-methyl-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC(F)=C1[C@@H]1C(C#N)=C(C)NC(C(F)F)=C1C#N UYZFYANYSIVDGM-OAHLLOKOSA-N 0.000 claims abstract 2
- HWKMGVPKZQVMJQ-OAHLLOKOSA-N (4r)-2-methyl-4-(3-methyl-2h-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC=C1[C@@H]1C(C#N)=C(C)NC(C(F)(F)F)=C1C#N HWKMGVPKZQVMJQ-OAHLLOKOSA-N 0.000 claims abstract 2
- HWKMGVPKZQVMJQ-HNNXBMFYSA-N (4s)-2-methyl-4-(3-methyl-2h-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC=C1[C@H]1C(C#N)=C(C)NC(C(F)(F)F)=C1C#N HWKMGVPKZQVMJQ-HNNXBMFYSA-N 0.000 claims abstract 2
- MCTXOYZRWZOYKI-UHFFFAOYSA-N 2,6-bis(difluoromethyl)-4-(3-methyl-2h-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC=C1C1C(C#N)=C(C(F)F)NC(C(F)F)=C1C#N MCTXOYZRWZOYKI-UHFFFAOYSA-N 0.000 claims abstract 2
- WOWAGKXGSRDYJG-UHFFFAOYSA-N 2,6-bis(difluoromethyl)-4-(6-fluoro-3-methyl-2h-indazol-5-yl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC(F)=C1C1C(C#N)=C(C(F)F)NC(C(F)F)=C1C#N WOWAGKXGSRDYJG-UHFFFAOYSA-N 0.000 claims abstract 2
- UYZFYANYSIVDGM-UHFFFAOYSA-N 2-(difluoromethyl)-4-(6-fluoro-3-methyl-2h-indazol-5-yl)-6-methyl-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC(F)=C1C1C(C#N)=C(C)NC(C(F)F)=C1C#N UYZFYANYSIVDGM-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 230000002062 proliferating effect Effects 0.000 claims 5
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 2
- 241001465754 Metazoa Species 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- UYZFYANYSIVDGM-HNNXBMFYSA-N (4s)-2-(difluoromethyl)-4-(6-fluoro-3-methyl-2h-indazol-5-yl)-6-methyl-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC(F)=C1[C@H]1C(C#N)=C(C)NC(C(F)F)=C1C#N UYZFYANYSIVDGM-HNNXBMFYSA-N 0.000 claims 1
- HWKMGVPKZQVMJQ-UHFFFAOYSA-N 2-methyl-4-(3-methyl-2h-indazol-5-yl)-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound C1=C2C(C)=NNC2=CC=C1C1C(C#N)=C(C)NC(C(F)(F)F)=C1C#N HWKMGVPKZQVMJQ-UHFFFAOYSA-N 0.000 claims 1
- FJWSHEFNTXMEOH-UHFFFAOYSA-N 4-(6-fluoro-1h-indazol-5-yl)-2-methyl-6-(trifluoromethyl)-1,4-dihydropyridine-3,5-dicarbonitrile Chemical compound N#CC1=C(C(F)(F)F)NC(C)=C(C#N)C1C(C(=C1)F)=CC2=C1NN=C2 FJWSHEFNTXMEOH-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 claims 1
- 239000005695 Ammonium acetate Substances 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 206010027476 Metastases Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000005219 aminonitrile group Chemical group 0.000 claims 1
- 229940043376 ammonium acetate Drugs 0.000 claims 1
- 235000019257 ammonium acetate Nutrition 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000001079 digestive effect Effects 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 238000007069 methylation reaction Methods 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 230000000849 parathyroid Effects 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 230000001850 reproductive effect Effects 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- 210000001635 urinary tract Anatomy 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 10
- 125000001153 fluoro group Chemical group F* 0.000 abstract 2
- 0 Cc1c([C@@](C(C#N)=*C(*)(*)*)C(C#N)=C(*)[N-])cc(c(*)n[n]2)c2c1 Chemical compound Cc1c([C@@](C(C#N)=*C(*)(*)*)C(C#N)=C(*)[N-])cc(c(*)n[n]2)c2c1 0.000 description 3
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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/416—1,2-Diazoles condensed with carbocyclic ring systems, e.g. indazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
- A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09172304 | 2009-10-06 | ||
| EP09172304.9 | 2009-10-06 | ||
| PCT/EP2010/064648 WO2011042368A1 (en) | 2009-10-06 | 2010-10-01 | Fluoro-substituted 3,5-dicyano-4-(1h-indazol-5-yl)-2,6-dimethyl-1,4-dihydropyridine derivatives and methods of use thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2012111695A true RU2012111695A (ru) | 2013-10-10 |
Family
ID=43357944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012111695/04A RU2012111695A (ru) | 2009-10-06 | 2010-10-01 | Фторзамещенные производные 3,5- дициано-4-(1н-индазол-5-ил) -2, 6-диметил-1,4-дигидропиридина и способы их применения |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US9422263B2 (esLanguage) |
| EP (1) | EP2485726B1 (esLanguage) |
| JP (1) | JP5753175B2 (esLanguage) |
| KR (1) | KR20120091005A (esLanguage) |
| CN (1) | CN102573838B (esLanguage) |
| AR (1) | AR078486A1 (esLanguage) |
| AU (1) | AU2010305550A1 (esLanguage) |
| BR (1) | BR112012006842A2 (esLanguage) |
| CA (1) | CA2773676C (esLanguage) |
| CL (1) | CL2012000753A1 (esLanguage) |
| CR (1) | CR20120150A (esLanguage) |
| CU (1) | CU20120051A7 (esLanguage) |
| DO (1) | DOP2012000085A (esLanguage) |
| EC (1) | ECSP12011748A (esLanguage) |
| ES (1) | ES2458117T3 (esLanguage) |
| IL (1) | IL218415A0 (esLanguage) |
| IN (1) | IN2012DN02675A (esLanguage) |
| MX (1) | MX2012003603A (esLanguage) |
| NZ (1) | NZ599006A (esLanguage) |
| PE (1) | PE20121392A1 (esLanguage) |
| PH (1) | PH12012500640A1 (esLanguage) |
| RU (1) | RU2012111695A (esLanguage) |
| SG (1) | SG178990A1 (esLanguage) |
| TW (1) | TW201124396A (esLanguage) |
| UY (1) | UY32922A (esLanguage) |
| WO (1) | WO2011042368A1 (esLanguage) |
| ZA (1) | ZA201201524B (esLanguage) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2836662C2 (ru) * | 2019-02-11 | 2025-03-18 | Мерк Патент Гмбх | Индазолилизоксазольные производные для лечения заболеваний, таких как злокачественное новообразование |
| US12486260B2 (en) | 2019-02-11 | 2025-12-02 | Merck Patent Gmbh | Indazolyl-isoxazole derivatives for the treatment of diseases such as cancer |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0650179Y2 (ja) | 1989-06-01 | 1994-12-21 | 株式会社プラコー | ブロー成形機用のダイヘッド |
| JPH0756186Y2 (ja) | 1989-07-24 | 1995-12-25 | 株式会社日本製鋼所 | パリソンの押出成形装置 |
| JP2781376B2 (ja) | 1996-06-17 | 1998-07-30 | エクセル株式会社 | 中空成形品 |
| DE102009056886A1 (de) * | 2009-12-03 | 2011-06-09 | Bayer Schering Pharma Aktiengesellschaft | cMet-Inhibitoren zur Behandlung der Endometriose |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635977A (en) | 1969-11-03 | 1972-01-18 | American Cyanamid Co | Certain 6-trifluoromethylcytosines and thiocytosines their synthesis and their use in the synthesis of uracisls and thiouracil |
| DE59009485D1 (de) | 1989-01-26 | 1995-09-14 | Bayer Ag | Optisch aktive (Meth)Acrylsäure-Derivate, ihre Herstellung, ihre Polymerisation zu optisch aktiven Polymeren und deren Verwendung. |
| DE19546136A1 (de) | 1995-12-11 | 1997-06-12 | Bayer Ag | Chirale stationäre Phasen für die chromatographische Trennung von optischen Isomeren |
| CA2482838A1 (en) | 2002-05-31 | 2003-12-11 | Eisai Co., Ltd. | Pyrazole compounds and pharmaceutical compositions containing the compound |
| WO2005085227A1 (en) | 2004-03-02 | 2005-09-15 | Smithkline Beecham Corporation | Inhibitors of akt activity |
| WO2005084672A1 (de) | 2004-03-03 | 2005-09-15 | Boehringer Ingelheim International Gmbh | Ausgewählte cgrp-antagonisten, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| RU2007126551A (ru) | 2004-12-13 | 2009-01-20 | Айрм Ллк (Bm) | Соединения и композиции, как модуляторы стероидных рецепторов и активности кальциевых каналов |
| AU2006203819A1 (en) | 2005-01-07 | 2006-07-13 | Roskamp Research Llc | Compounds for inhibiting beta-amyloid production and methods of identifying the compounds |
| US7632839B2 (en) * | 2005-01-19 | 2009-12-15 | Merck & Co. Inc. | Mitotic kinesin inhibitors |
| BRPI0719991A2 (pt) * | 2006-12-14 | 2014-03-18 | Bayer Schering Pharma Ag | Derivados de di-hidropiridina úteis como inibidores de proteína cinase |
-
2010
- 2010-09-30 UY UY0001032922A patent/UY32922A/es not_active Application Discontinuation
- 2010-10-01 AU AU2010305550A patent/AU2010305550A1/en not_active Abandoned
- 2010-10-01 KR KR1020127007824A patent/KR20120091005A/ko not_active Withdrawn
- 2010-10-01 WO PCT/EP2010/064648 patent/WO2011042368A1/en not_active Ceased
- 2010-10-01 US US13/496,722 patent/US9422263B2/en not_active Expired - Fee Related
- 2010-10-01 MX MX2012003603A patent/MX2012003603A/es not_active Application Discontinuation
- 2010-10-01 CN CN201080043306.5A patent/CN102573838B/zh not_active Expired - Fee Related
- 2010-10-01 NZ NZ599006A patent/NZ599006A/xx not_active IP Right Cessation
- 2010-10-01 RU RU2012111695/04A patent/RU2012111695A/ru not_active Application Discontinuation
- 2010-10-01 BR BR112012006842A patent/BR112012006842A2/pt not_active Application Discontinuation
- 2010-10-01 JP JP2012532550A patent/JP5753175B2/ja not_active Expired - Fee Related
- 2010-10-01 ES ES10760348.2T patent/ES2458117T3/es active Active
- 2010-10-01 IN IN2675DEN2012 patent/IN2012DN02675A/en unknown
- 2010-10-01 PE PE2012000384A patent/PE20121392A1/es not_active Application Discontinuation
- 2010-10-01 AR ARP100103574A patent/AR078486A1/es unknown
- 2010-10-01 EP EP10760348.2A patent/EP2485726B1/en not_active Not-in-force
- 2010-10-01 SG SG2012015400A patent/SG178990A1/en unknown
- 2010-10-01 PH PH1/2012/500640A patent/PH12012500640A1/en unknown
- 2010-10-01 CA CA2773676A patent/CA2773676C/en not_active Expired - Fee Related
- 2010-10-05 TW TW099133784A patent/TW201124396A/zh unknown
-
2012
- 2012-02-29 ZA ZA2012/01524A patent/ZA201201524B/en unknown
- 2012-03-01 IL IL218415A patent/IL218415A0/en unknown
- 2012-03-26 CU CU20120051A patent/CU20120051A7/es unknown
- 2012-03-26 CL CL2012000753A patent/CL2012000753A1/es unknown
- 2012-03-27 EC ECSP12011748 patent/ECSP12011748A/es unknown
- 2012-03-27 CR CR20120150A patent/CR20120150A/es unknown
- 2012-03-27 DO DO2012000085A patent/DOP2012000085A/es unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2836662C2 (ru) * | 2019-02-11 | 2025-03-18 | Мерк Патент Гмбх | Индазолилизоксазольные производные для лечения заболеваний, таких как злокачественное новообразование |
| US12486260B2 (en) | 2019-02-11 | 2025-12-02 | Merck Patent Gmbh | Indazolyl-isoxazole derivatives for the treatment of diseases such as cancer |
Also Published As
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|---|---|
| US20120264785A1 (en) | 2012-10-18 |
| PH12012500640A1 (en) | 2012-11-12 |
| AU2010305550A1 (en) | 2012-03-29 |
| KR20120091005A (ko) | 2012-08-17 |
| NZ599006A (en) | 2013-11-29 |
| AR078486A1 (es) | 2011-11-09 |
| IN2012DN02675A (esLanguage) | 2015-09-04 |
| UY32922A (es) | 2011-04-29 |
| JP2013506699A (ja) | 2013-02-28 |
| MX2012003603A (es) | 2012-04-20 |
| IL218415A0 (en) | 2012-04-30 |
| BR112012006842A2 (pt) | 2016-06-07 |
| CN102573838B (zh) | 2014-09-24 |
| ZA201201524B (en) | 2013-05-29 |
| TW201124396A (en) | 2011-07-16 |
| SG178990A1 (en) | 2012-04-27 |
| JP5753175B2 (ja) | 2015-07-22 |
| CU20120051A7 (es) | 2012-06-29 |
| CR20120150A (es) | 2012-08-03 |
| HK1172835A1 (en) | 2013-05-03 |
| CN102573838A (zh) | 2012-07-11 |
| DOP2012000085A (es) | 2012-07-15 |
| CA2773676C (en) | 2017-07-04 |
| US9422263B2 (en) | 2016-08-23 |
| EP2485726A1 (en) | 2012-08-15 |
| ES2458117T3 (es) | 2014-04-30 |
| ECSP12011748A (es) | 2012-05-30 |
| CL2012000753A1 (es) | 2012-09-14 |
| WO2011042368A1 (en) | 2011-04-14 |
| CA2773676A1 (en) | 2011-04-14 |
| PE20121392A1 (es) | 2012-10-14 |
| EP2485726B1 (en) | 2014-03-12 |
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