AR089788A1 - Fenilimidazopirazoles sustituidos y su uso - Google Patents
Fenilimidazopirazoles sustituidos y su usoInfo
- Publication number
- AR089788A1 AR089788A1 ARP130100206A ARP130100206A AR089788A1 AR 089788 A1 AR089788 A1 AR 089788A1 AR P130100206 A ARP130100206 A AR P130100206A AR P130100206 A ARP130100206 A AR P130100206A AR 089788 A1 AR089788 A1 AR 089788A1
- Authority
- AR
- Argentina
- Prior art keywords
- fluorine
- hydroxy
- hydrogen
- alkyl
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 229910052731 fluorine Chemical group 0.000 abstract 14
- 239000011737 fluorine Chemical group 0.000 abstract 14
- 229910052739 hydrogen Inorganic materials 0.000 abstract 13
- 239000001257 hydrogen Substances 0.000 abstract 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 10
- 150000002431 hydrogen Chemical class 0.000 abstract 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 7
- 229910052801 chlorine Inorganic materials 0.000 abstract 7
- 239000000460 chlorine Substances 0.000 abstract 7
- -1 hydroxy, methoxy Chemical group 0.000 abstract 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 4
- 150000002221 fluorine Chemical class 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 238000011282 treatment Methods 0.000 abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 102220495208 NAD(P)H pyrophosphatase NUDT13, mitochondrial_R12A_mutation Human genes 0.000 abstract 2
- 102220495705 NAD(P)H pyrophosphatase NUDT13, mitochondrial_R13A_mutation Human genes 0.000 abstract 2
- 206010028980 Neoplasm Diseases 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 201000010099 disease Diseases 0.000 abstract 2
- 230000006806 disease prevention Effects 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000003566 oxetanyl group Chemical group 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000012453 solvate Substances 0.000 abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- NITZQUOSJIYMRX-UHFFFAOYSA-N 1-phenylimidazo[1,2-b]pyrazole Chemical class C1=CN2N=CC=C2N1C1=CC=CC=C1 NITZQUOSJIYMRX-UHFFFAOYSA-N 0.000 abstract 1
- 206010029113 Neovascularisation Diseases 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000002491 angiogenic effect Effects 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 230000003463 hyperproliferative effect Effects 0.000 abstract 1
- CYCBAKHQLAYYHQ-UHFFFAOYSA-N imidazo[4,5-c]pyrazole Chemical group N1=NC2=NC=NC2=C1 CYCBAKHQLAYYHQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000002483 medication Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004043 oxo group Chemical class O=* 0.000 abstract 1
- 238000009097 single-agent therapy Methods 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
La presente se refiere a derivados de 1-fenil-1H-imidazo[1,2-b]pirazol, a procedimientos para su preparación, a su uso para el tratamiento y/o la prevención de enfermedades así como a su uso para la preparación de medicamentos para el tratamiento y/o la prevención de enfermedades, en particular de enfermedades angiogénicas y de enfermedades hiperproliferativas en las que es importante la neovascularización, como por ejemplo, enfermedades cancerosas y tumorales. Tales tratamientos pueden realizarse como monoterapia o también en combinación con otros medicamentos u otras medidas terapéuticas. Reivindicación 1: Compuesto de la fórmula (1) en la que ArN representa un aza-heteroarilo de 5 ó 6 miembros, que está seleccionado del grupo de formulas (2), donde * marca el enlace con el grupo imidazopirazol e Y significa O, S o NH; R¹ representa hidrógeno o flúor; R² representa hidrógeno o alquilo C₁₋₄; R³ representa hidrógeno; R⁴A y R⁴B independientemente entre sí representan hidrógeno, flúor, cloro, metilo, fluorometilo, difluorometilo, trifluorometilo, hidroximetilo, metoximetilo, etilo, hidroxi, metoxi o trifluorometoxi; R⁵ representa hidrógeno, flúor, cloro o metilo; R⁶ representa hidrógeno, flúor, metilo o hidroxi; Z¹ representa C-R⁷A o N; Z² representa C-R⁷B o N; Z³ representa C-R⁸ o N; Z⁴ representa C-R⁹ o N; y Z⁵ representa C-R¹⁰ o N; donde en total como máximo uno de los miembros de anillo Z¹, Z², Z³, Z⁴ y Z⁵ representa N, y donde R⁷A y R⁷B independientemente entre sí significan hidrógeno, flúor, cloro, metilo, hidroxi o metoxi; R⁸ significa hidrógeno, flúor, cloro o metilo; R⁹ significa hidrógeno, pentafluorosulfanilo, (trifluorometil)sulfanilo, trimetilsililo, alquilo C₁₋₆, alcoxi C₁₋₆, cicloalquilo C₃₋₆, oxetanilo o tetrahidropiranilo, donde alquilo C₁₋₆ y alcoxi C₁₋₆ pueden estar sustituidos hasta seis veces con flúor, y cicloalquilo C₃₋₆, oxetanilo y tetrahidropiranilo pueden estar sustituidos hasta dos veces, de manera igual o diferente, con un resto seleccionado de la serie de flúor, metilo, trifluorometilo e hidroxi; y R¹⁰ significa hidrógeno, flúor, cloro, bromo, ciano, alquilo C₁₋₆, hidroxi, alcoxi C₁₋₆, alquilsulfonilo C₁₋₄, cicloalquilo C₃₋₆, fenilo, heteroarilo de 5 ó 6 miembros o un grupo de la fórmula -L¹-C(=O)-OR¹¹, L¹-NR¹²AR¹²B, -L¹-C(=O)NR¹³AR¹³B, L²-S(=O)₂NR¹³AR¹³B o -L³-R¹⁴, donde alquilo C₁₋₆ y alcoxi C₁₋₆ pueden estar sustituidos con un resto seleccionado de la serie de hidroxi, metoxi, etoxi, 2-hidroxietoxi, 2-metoxietoxi, 2-etoxietoxi, amino, metilamino y dimetilamino o pueden estar sustituidos hasta seis veces con flúor, y cicloalquilo C₃₋₆ puede estar sustituido hasta dos veces, de manera igual o diferente, con un resto seleccionado de la serie de metilo, hidroxi, metoxi, etoxi, amino, metilamino y dimetilamino, y fenilo y heteroarilo de 5 ó 6 miembros pueden estar hasta sustituidos hasta dos veces, de manera igual o diferente, con un resto seleccionado de la serie de flúor, cloro, ciano, metilo y trifluorometilo; y donde L¹ constituye un enlace o -CH₂-; L² constituye un enlace o -CH₂-; L³ constituye un enlace u -O-; R¹¹ constituye hidrógeno o alquilo C₁₋₄; R¹²A, R¹²B, R¹³A y R¹³B independientemente entre sí constituyen hidrógeno o alquilo C₁₋₄, donde alquilo C₁₋₄ puede estar sustituido respectivamente con un resto seleccionado de la serie de hidroxi, metoxi, etoxi, amino, metilamino y dimetilamino, o R¹²A y R¹²B o bien R¹³A y R¹³B están enlazados entre sí y junto con el átomo de nitrógeno al que están unidos, respectivamente forman un heterociclo de 4 a 6 miembros, que puede contener un heteroátomo del anillo de la serie de N, O ó S y que puede estar sustituido hasta dos veces, de manera igual o diferente, con un resto seleccionado de la serie de flúor, ciano, alquilo C₁₋₄, hidroxi, alcoxi C₁₋₄ y oxo; y R¹⁴ constituye un heterociclo de 4 a 6 miembros unido mediante un átomo de carbono del anillo, que contiene un heteroátomo del anillo de la serie de N, O ó S y que puede estar sustituido hasta dos veces, de manera igual o diferente, con un resto seleccionado de la serie de flúor, ciano, alquilo C₁₋₄, hidroxi, alcoxi C₁₋₄ y oxo; donde R¹⁰ no significa hidrógeno, flúor, cloro o bromo, cuando Z⁴ representa CH o N, y Z⁵ no representa N, cuando Z⁴ representa CH; como también sus sales sus solvatos y solvatos de las sales.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12152515 | 2012-01-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR089788A1 true AR089788A1 (es) | 2014-09-17 |
Family
ID=47594775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP130100206A Pending AR089788A1 (es) | 2012-01-25 | 2013-01-23 | Fenilimidazopirazoles sustituidos y su uso |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US20150005288A1 (es) |
| EP (1) | EP2807162B1 (es) |
| JP (1) | JP6101290B2 (es) |
| KR (1) | KR20140117582A (es) |
| CN (1) | CN104411707B (es) |
| AP (1) | AP2014007869A0 (es) |
| AR (1) | AR089788A1 (es) |
| AU (1) | AU2013211707A1 (es) |
| BR (1) | BR112014018450A8 (es) |
| CA (1) | CA2862163A1 (es) |
| CL (1) | CL2014001959A1 (es) |
| CO (1) | CO7101244A2 (es) |
| CR (1) | CR20140362A (es) |
| CU (1) | CU20140096A7 (es) |
| DO (1) | DOP2014000173A (es) |
| EA (1) | EA201491427A1 (es) |
| EC (1) | ECSP14010868A (es) |
| ES (1) | ES2639338T3 (es) |
| GT (1) | GT201400161A (es) |
| HK (1) | HK1203198A1 (es) |
| IL (1) | IL233652A0 (es) |
| MA (1) | MA35877B1 (es) |
| MX (1) | MX2014008893A (es) |
| PE (1) | PE20142421A1 (es) |
| PH (1) | PH12014501687A1 (es) |
| SG (1) | SG11201404118XA (es) |
| TN (1) | TN2014000320A1 (es) |
| TW (1) | TW201343649A (es) |
| UY (1) | UY34590A (es) |
| WO (1) | WO2013110590A1 (es) |
| ZA (1) | ZA201405392B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104411707B (zh) * | 2012-01-25 | 2017-03-01 | 拜耳药业股份公司 | 取代的苯基咪唑并吡唑及其用途 |
| EP3027026A4 (en) | 2013-07-31 | 2017-05-03 | Windward Pharma, Inc. | Aerosol tyrosine kinase inhibitor compounds and uses thereof |
| EP3214936A1 (en) | 2014-11-06 | 2017-09-13 | Basf Se | 3-pyridyl heterobicyclic compound for controlling invertebrate pests |
| KR20180057716A (ko) * | 2015-10-08 | 2018-05-30 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 헤테로사이클-치환된 비시클릭 아졸 살충제 |
| UY38366A (es) * | 2018-09-13 | 2020-04-30 | Syngenta Participations Ag | Compuestos de azol-amida pesticidamente activos |
| CN109096195A (zh) * | 2018-09-27 | 2018-12-28 | 上海雅本化学有限公司 | 一种艾曲波帕的制备方法 |
| EP4045482A1 (de) * | 2019-10-16 | 2022-08-24 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 1,1'-disulfandiylbis(4-fluor-2-methyl-5-nitrobenzol) |
| US20230145003A1 (en) * | 2020-01-29 | 2023-05-11 | Foghorn Therapeutics Inc. | Compounds and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0753730B2 (ja) * | 1988-07-26 | 1995-06-07 | 三共株式会社 | イミダゾピラゾール誘導体 |
| UA80171C2 (en) * | 2002-12-19 | 2007-08-27 | Pfizer Prod Inc | Pyrrolopyrimidine derivatives |
| US7419978B2 (en) * | 2003-10-22 | 2008-09-02 | Bristol-Myers Squibb Company | Phenyl-aniline substituted bicyclic compounds useful as kinase inhibitors |
| KR101061599B1 (ko) * | 2008-12-05 | 2011-09-02 | 한국과학기술연구원 | 비정상 세포 성장 질환의 치료를 위한 단백질 키나아제 저해제인 신규 인다졸 유도체, 이의 약학적으로 허용가능한염 및 이를 유효성분으로 함유하는 약학적 조성물 |
| WO2010147898A2 (en) * | 2009-06-15 | 2010-12-23 | Rigel Pharmaceuticals, Inc. | Small molecule inhibitors of spleen tyrosine kinase (syk) |
| KR101116756B1 (ko) * | 2009-10-27 | 2012-03-13 | 한국과학기술연구원 | 단백질 키나아제 저해활성을 갖는 신규의 1,6-치환된 인돌 화합물 |
| CN104411707B (zh) * | 2012-01-25 | 2017-03-01 | 拜耳药业股份公司 | 取代的苯基咪唑并吡唑及其用途 |
-
2013
- 2013-01-22 CN CN201380016585.XA patent/CN104411707B/zh not_active Expired - Fee Related
- 2013-01-22 SG SG11201404118XA patent/SG11201404118XA/en unknown
- 2013-01-22 ES ES13700765.4T patent/ES2639338T3/es active Active
- 2013-01-22 KR KR1020147023244A patent/KR20140117582A/ko not_active Application Discontinuation
- 2013-01-22 US US14/372,917 patent/US20150005288A1/en not_active Abandoned
- 2013-01-22 AP AP2014007869A patent/AP2014007869A0/xx unknown
- 2013-01-22 AU AU2013211707A patent/AU2013211707A1/en not_active Abandoned
- 2013-01-22 EP EP13700765.4A patent/EP2807162B1/de active Active
- 2013-01-22 PE PE2014001145A patent/PE20142421A1/es not_active Application Discontinuation
- 2013-01-22 EA EA201491427A patent/EA201491427A1/ru unknown
- 2013-01-22 BR BR112014018450A patent/BR112014018450A8/pt not_active IP Right Cessation
- 2013-01-22 WO PCT/EP2013/051106 patent/WO2013110590A1/de active Application Filing
- 2013-01-22 CA CA2862163A patent/CA2862163A1/en not_active Abandoned
- 2013-01-22 JP JP2014553682A patent/JP6101290B2/ja not_active Expired - Fee Related
- 2013-01-22 MX MX2014008893A patent/MX2014008893A/es unknown
- 2013-01-23 AR ARP130100206A patent/AR089788A1/es active Pending
- 2013-01-23 US US13/748,043 patent/US9394309B2/en not_active Expired - Fee Related
- 2013-01-23 UY UY0001034590A patent/UY34590A/es not_active Application Discontinuation
- 2013-01-24 TW TW102102567A patent/TW201343649A/zh unknown
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2014
- 2014-07-15 IL IL233652A patent/IL233652A0/en unknown
- 2014-07-21 MA MA37230A patent/MA35877B1/fr unknown
- 2014-07-22 ZA ZA2014/05392A patent/ZA201405392B/en unknown
- 2014-07-24 PH PH12014501687A patent/PH12014501687A1/en unknown
- 2014-07-24 GT GT201400161A patent/GT201400161A/es unknown
- 2014-07-24 CL CL2014001959A patent/CL2014001959A1/es unknown
- 2014-07-24 DO DO2014000173A patent/DOP2014000173A/es unknown
- 2014-07-24 TN TNP2014000320A patent/TN2014000320A1/fr unknown
- 2014-07-25 CO CO14162331A patent/CO7101244A2/es unknown
- 2014-07-25 EC ECIEPI201410868A patent/ECSP14010868A/es unknown
- 2014-07-28 CR CR20140362A patent/CR20140362A/es unknown
- 2014-07-28 CU CU2014000096A patent/CU20140096A7/es unknown
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2015
- 2015-04-17 HK HK15103743.7A patent/HK1203198A1/xx not_active IP Right Cessation
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