AR067762A1 - Proceso para preparar 5-fluoro-1h-pirazolo (3,4-b) piridin-3-amina y derivados de la misma - Google Patents
Proceso para preparar 5-fluoro-1h-pirazolo (3,4-b) piridin-3-amina y derivados de la mismaInfo
- Publication number
- AR067762A1 AR067762A1 ARP080103330A ARP080103330A AR067762A1 AR 067762 A1 AR067762 A1 AR 067762A1 AR P080103330 A ARP080103330 A AR P080103330A AR P080103330 A ARP080103330 A AR P080103330A AR 067762 A1 AR067762 A1 AR 067762A1
- Authority
- AR
- Argentina
- Prior art keywords
- ring
- aliphatic
- optionally substituted
- con
- heterocyclyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 125000001931 aliphatic group Chemical group 0.000 abstract 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 13
- 125000000623 heterocyclic group Chemical group 0.000 abstract 13
- 229910052757 nitrogen Inorganic materials 0.000 abstract 11
- 125000001072 heteroaryl group Chemical group 0.000 abstract 10
- 150000001875 compounds Chemical class 0.000 abstract 9
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 8
- 125000004429 atom Chemical group 0.000 abstract 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 7
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 229910052760 oxygen Inorganic materials 0.000 abstract 5
- 125000001475 halogen functional group Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 3
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 3
- 239000001301 oxygen Substances 0.000 abstract 3
- UFONWAPOQPJJLL-UHFFFAOYSA-N 5-fluoro-2h-pyrazolo[3,4-b]pyridin-3-amine Chemical compound C1=C(F)C=C2C(N)=NNC2=N1 UFONWAPOQPJJLL-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- -1 TV-R6 Chemical group 0.000 abstract 2
- 125000001118 alkylidene group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- 238000003786 synthesis reaction Methods 0.000 abstract 2
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- 125000000041 C6-C10 aryl group Chemical group 0.000 abstract 1
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 abstract 1
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 abstract 1
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000000382 dechlorinating effect Effects 0.000 abstract 1
- 238000006298 dechlorination reaction Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000006574 non-aromatic ring group Chemical group 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
Abstract
Un proceso para la síntesis de 5-fluoro-1H-pirazolo[3,4-b]piridin-3-amina a elevado rendimiento y pureza. También se refiere a procesos para la síntesis de derivados de 5-fluoro-1H pirazolo[3,4-b]piridin-3-amina Estos procesos son utiles para preparar compuestos biologicamente activos, particularmente, ciertos inhibidores GSK-3 o derivados de los mismos. Reivindicacion 1: Un proceso pata preparar un compuesto de la formula 5, caracterizado porque comprende el paso de declorar selectivamente un compuesto de la formula 1, en condiciones de decloracion adecuadas para formar un compuesto de la formula 2. Reivindicacion 17: Un proceso para preparar un compuestote la formula (1) caracterizado porque: Z2 es N o CRZ; Rx es T1-R3; Ry es T2-R10, o Rx y Ry se toman junto con los átomos intervinientes para formar un anillo aromático o no aromático, fusionado de 5-8 miembros que tiene 0-3 heteroátomos en el anillo, seleccionados entre oxígeno, azufre o nitrogeno, donde cualquier carbono sustituible en dicho anillo fusionado formado por Rx y Ry está sustituido por T-R3, y cualquier nitrogeno sustituible en dicho anillo formado por Rx y Ry está sustituido con R4; Rz es H, halo, o grupo alifático C1-6, donde el grupo alifático está opcionalmente sustituido con 1-5 grupos seleccionados entre halo, -CN, y -OR; cada T y T1 es, independientemente, un enlace o una cadena de alquilideno C1-4; T2 es, independientemente, un enlace o una cadena de alquilideno C1-4 donde, hasta tres unidades de metileno de la cadena de alquilideno, están opcionalmente reemplazadas por y -O-, -C(=O)-, -S(O)-, -S(O)2, -S-, o -N(R4)-; Anillo D es un anillo monociclico de 4-7 miembros o anillo bicíclico de 8-10 miembros seleccionados entre un anillo heterociclilo, arilo, heteroarilo, o carbociclilo; dicho anillo heterociclilo o heteroarilo tiene 1-4 heteroátomos seleccionados entre nitrogeno, oxígeno o azufre, donde cada carbono del anillo sustituible del Anillo D está independientemente sustituido con oxo, R1, o -R5 y cualquier nitrogeno sustituible del anillo está independientemente sustituido con -R4; R1 se selecciona entre -halo, -CN, -NO2, T-V-R6, fenilo, un anillo heteroarilo de 5-6 miembros, un anillo heterociclilo de 5-6 miembros, o un grupo alifático C1-6, dichos anillos de fenilo, heteroarilo, y heterociclilo están, opcionalmente, sustituidos con hasta tres grupos independientemente seleccionados entre halo, oxo, o -R8, dicho grupo alifático C1-6 está opcionalmente sustituido con halo, ciano, nitro, u oxígeno, o R1 y un sustituyente adyacente tomados junto con los átomos intervinientes, forman dicho anillo fusionado al Anillo D; V es -O-, -S-, -SO-, -SO2-, -N(R6)SO2-, -SO2N(R6)-, -N(R6)-, -CO-, -CO2-, -N(R6)CO-, -N(R6)C(O)O-, -N(R6)CON(R6)-, -N(R6)SO2N(R6)-, -N(R6)N(R6)-, -C(O)N(R6)-, -OC(O)N(R6)-, -C(R6)2O-, -C(R6)2S-, -C(R6)2SO-, -C(R6)2SO2-, -C(R6)2SO2N(R6)-, -C(R6)2N(R6)-, -C(R6)2N(R6)C(O)-, -C(R6)2N(R6)C(O)O-, -C(R6)=NN(R6)-, -C(R6)=N-O-, -C(R6)2N(R6)N(R6)-, -C(R6)2N(R6)SO2N(R6)-, o -C(R6)2N(R6)CON(R6)-; cada R3 y R10 se selecciona independientemente entre -R, -halo, -OR, -C(=O)R, -CO2R, -COCOR, -COCH2COR, -NO2, -CN, -S(O)R, -S(O)2R, -SR, -N(R4)2, -CON(R7)2, -SO2N(R7)2, -OC(=O)R, -N(R7)COR, -N(R7)CO2Rö, -N(R4)N(R4)2, -N(R7)CON(R7)2, -N(R7)SO2N(R7)2, -N(R4)SO2R, o -OC(=O)N(R7)2; cada R se selecciona independientemente entre hidrogeno o un grupo opcionalmente sustituido seleccionado entre un grupo alifático C1-6, arilo C6-10, un anillo heteroarilo que tiene 5-10 átomos en el anillo, o un anillo heterociclilo que tiene 4-10 átomos en el anillo; cada R está opcionalmente sustituida con 0-5 R9 o J; cada R4 se selecciona independientemente entre -R7, -COR7, -CO2Rö, -CON(R7)2, o -SO2R7, o dos R4 en el mismo nitrogeno se toman juntas para formar un anillo heterociclilo o heteroarilo de 3-8 miembros; donde dicho anillo heterociclilo o heteroarilo está opcionalmente sustituido con 0-3 J4; cada R5 se selecciona independientemente entre -R, halo, -OR, -C(=O)R -CO2R, -COCOR, -NO2, -CN, -S(O)R, -SO2R, -SR, -N(R4)2, -CON(R4)2, -SO2N(R4)2, -OC(=O)R, -N(R4)COR, -N(R4)CO2Rö, -N(R4)N(R4)2, -C(=NH)N(R4)2, -C(=NH)OR, -N(R4)CON(R4)2, -N(R4)SO2N(R4)2, -N(R4)SO2R, o -OC(=O)N(R4)2; cada R6 se selecciona independientemente entre hidrogeno o un grupo alifático C1-4 opcionalmente sustituido con 0-3 J6; o dos grupos R6 en el mismo átomo de nitrogeno se toman junto con el átomo de nitrogeno para formar un anillo heterociclilo o heteroarilo de 5-6 miembros, donde dicho anillo heterociclilo o heteroarilo está opcionalmente sustituido con 0-4 J6; cada R7 se selecciona independientemente entre hidrogeno o Rö; o dos R7 en el mismo nitrogeno se toman junto con el nitrogeno para formar un anillo heterociclilo o heteroarilo de 5-8 miembros, donde dicho anillo heterociclilo o heteroarilo está opcionalmente sustituido con 0-4 Jö; cada R8 se selecciona independientemente entre -OR6, -SR6, -COR6, -SO2R6, -N(R6)2, -N(R6)N(R6)2, -CN, -NO2, -CON(R6)2, -CO2R6, o un grupo alifático C1-4, donde dicho grupo alifático C1-4 está opcionalmente sustituido con 0-3 J8; cada R9 es -R', -halo, -OR', -C(O)R', -CO2R', -COCOR', COCH2COR', -NO2, -CN, -S(O)R', -S(O)2R', -SR', -N(R')2, -CON(R')2, -SO2N(R')2, -OC(=O)R', -N(R')COR', -N(R')CO2-alifático C1-6, -N(R')N(R')2, -N(R')CON(R')2, -N(R')SO2N(R')2, -N(R')SO2R', -OC(=O)N(R')2, =NN(R')2, =N-OR', o =O; cada R' es independientemente hidrogeno o un grupo alifático C1-6 opcionalmente sustituido con 0-4 J'; o dos R', junto con el(los) átomo(s) al que están ligados, forman un anillo carbociclilo o heterociclilo de 3-6 miembros donde dicho carbociclilo está opcionalmente sustituido con 0-4 J' y donde dicho heterociclilo contiene 1-2 heteroátomos seleccionados entre O, N, o S; cada Rö es independientemente un grupo alifático C1-6 opcionalmente sustituido con 0-4 Jö; y cada J4, J', y Jö es independientemente NH2, NH-alifático C1-4, N(alifático C1-4)2, halogeno, alifático C1-4, OH, O-alifático C1-4, NO2, CN, CO2H, CO2-alifático C1-4, O-haloalifático C1-4, o halo alifático C1-4 cada J es halo, OH, o alifático C1-6; cada J6 y J8 es independientemente -halo, -OR, oxo, alifático C1-6, -C(=O)R, -CO2R, -COCOR, COCH2COR, -NO2, -CN, -S(O)R, -S(O)2R, -SR, -N(R4)2, -CON(R7)2, -SO2N(R7)2, -OC(=O)R, -N(R7)COR, -N(R7)CO2-alifático C1-6, -N(R4)N(R4)2, =NN(R4)2, =N-OR, -N(R7)CON(R7)2, -N(R7)SO2N(R7)2, -N(R4)SO2R, o -OC(=O)N(R7)2; o 2 grupos J6 o J8, en el mismo átomo o en átomos diferentes, junto con el(los) átomo(s) a los que están ligados, forman un anillo de 3-8 miembros saturado, parcialmente saturado o insaturado que tiene 0-2 heteroátomos seleccionados entre O, N, o S; que comprende el paso de sintetizar un compuesto de la formula 5, de acuerdo con el proceso de cualquiera de las reivindicaciones 1-16; y combinar dicho compuesto con un compuesto de la formula 6, donde LG es un grupo saliente adecuado; y Rx, Ry, Z2, y el Anillo D son como definimos aquí para los compuestos de la formula 1; en condiciones de reaccion adecuadas para formar un compuesto de la formula 1.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US95301907P | 2007-07-31 | 2007-07-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR067762A1 true AR067762A1 (es) | 2009-10-21 |
Family
ID=39884162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080103330A AR067762A1 (es) | 2007-07-31 | 2008-07-31 | Proceso para preparar 5-fluoro-1h-pirazolo (3,4-b) piridin-3-amina y derivados de la misma |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US8242272B2 (es) |
| EP (1) | EP2176261B1 (es) |
| JP (2) | JP5553751B2 (es) |
| CN (1) | CN101790532B (es) |
| AR (1) | AR067762A1 (es) |
| AU (1) | AU2008282156B2 (es) |
| CA (1) | CA2694499A1 (es) |
| ES (1) | ES2400104T3 (es) |
| HK (1) | HK1141806A1 (es) |
| MX (1) | MX2010001137A (es) |
| NZ (1) | NZ582879A (es) |
| TW (1) | TW200916468A (es) |
| WO (1) | WO2009018415A1 (es) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2435997T3 (es) * | 2007-03-09 | 2013-12-26 | Vertex Pharmaceuticals, Inc. | Aminopirimidinas útiles como inhibidores de las proteínas cinasas |
| RU2010129928A (ru) | 2007-12-19 | 2012-01-27 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Пиразоло[1, 5-а]пиримидины, используемые в качестве ингибиторов jak2 |
| JP2011513483A (ja) * | 2008-03-10 | 2011-04-28 | バーテックス ファーマシューティカルズ インコーポレイテッド | タンパク質キナーゼの阻害剤として有用なピリミジンおよびピリジン |
| CA2789427A1 (en) * | 2010-02-11 | 2011-08-18 | Vanderbilt University | Pyrazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolothiophene and pyrazolothiazole compounds as mglur4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| DE102010021637A1 (de) | 2010-05-26 | 2011-12-01 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 5-Fluor-1H-Pyrazolopyridine und ihre Verwendung |
| PE20130781A1 (es) | 2010-07-06 | 2013-07-20 | Astrazeneca Ab | Agentes terapeuticos 976 |
| DE102011007891A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| DE102011003315A1 (de) | 2011-01-28 | 2012-08-02 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimindine und Triazine und ihre Verwendung |
| CN103180327B (zh) | 2010-07-09 | 2016-08-10 | 拜耳知识产权有限责任公司 | 稠环的4-氨基嘧啶及其作为可溶性鸟甘酸环化酶的刺激物的用途 |
| DE102010031148A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Ag | Annellierte 4-Aminopyrimidine und ihre Verwendung |
| DE102010031149A1 (de) | 2010-07-09 | 2012-01-12 | Bayer Schering Pharma Aktiengesellschaft | Annellierte Pyrimidine und Triazine und ihre Verwendung |
| AU2011275825A1 (en) | 2010-07-09 | 2013-02-07 | Bayer Intellectual Property Gmbh | Ring-fused pyrimidines and triazines and use thereof for the treatment and/or prophylaxis of cardiovascular diseases |
| DE102010031666A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Carbamat-substituierte Diaminopyrimidine und ihre Verwendung |
| DE102010031667A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Methyl-pyrimidin-5-ylcarbamate und ihre Verwendung |
| DE102010031665A1 (de) | 2010-07-22 | 2012-01-26 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Oxazolidinone und Oxazinanone und ihre Verwendung |
| DE102010040234A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Verfahren zur Herstellung von 5-Flour-1H-pyrazolo[3,4-b]pyridin-3-carbonitril |
| DE102010040233A1 (de) | 2010-09-03 | 2012-03-08 | Bayer Schering Pharma Aktiengesellschaft | Bicyclische Aza-Heterocyclen und ihre Verwendung |
| DE102010043379A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Substituierte 6-Fluor-1H-Pyrazolo[4,3-b]pyridine und ihre Verwendung |
| DE102010043380A1 (de) | 2010-11-04 | 2012-05-10 | Bayer Schering Pharma Aktiengesellschaft | Benzyl-substituierte Carbamate und ihre Verwendung |
| DE102012200357A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102011007890A1 (de) | 2011-04-21 | 2012-10-25 | Bayer Pharma Aktiengesellschaft | Fluoralkyl-substituierte Pyrazolopyridine und ihre Verwendung |
| CN103619845B (zh) | 2011-04-21 | 2016-08-17 | 拜耳知识产权有限责任公司 | 氟烷基取代的吡唑并吡啶及其用途 |
| DE102011078715A1 (de) | 2011-07-06 | 2013-01-10 | Bayer Pharma AG | Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung |
| DE102012200354A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Heteroaryl-substituierte Pyrazolopyridine und ihre Verwendung |
| AU2012280246A1 (en) | 2011-07-06 | 2014-01-23 | Bayer Intellectual Property Gmbh | Heteroaryl-substituted pyrazolopyridines and use thereof as soluble guanylate cyclase stimulators |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| CN104039784B (zh) | 2011-09-02 | 2017-08-22 | 拜耳知识产权有限责任公司 | 取代的增环嘧啶及其用途 |
| DE102011082041A1 (de) | 2011-09-02 | 2013-03-07 | Bayer Pharma AG | Substituierte annellierte Pyrimidine und ihre Verwendung |
| DE102012200351A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Pharma Aktiengesellschaft | Substituierte annellierte Pyrimidine und ihre Verwendung |
| MY168412A (en) * | 2011-11-25 | 2018-11-09 | Adverio Pharma Gmbh | Method for producing substituted 5-fluoro-1h-pyrazolopyridines |
| DE102012200360A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte Triazine und ihre Verwendung |
| DE102012200352A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte, annellierte Imidazole und Pyrazole und ihre Verwendung |
| DE102012200349A1 (de) | 2012-01-11 | 2013-07-11 | Bayer Intellectual Property Gmbh | Substituierte annellierte Pyrimidine und Triazine und ihre Verwendung |
| CA2866213A1 (en) | 2012-03-06 | 2013-09-12 | Bayer Intellectual Property Gmbh | Substituted azabicycles and use thereof |
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-
2008
- 2008-07-31 CA CA2694499A patent/CA2694499A1/en not_active Abandoned
- 2008-07-31 TW TW097129121A patent/TW200916468A/zh unknown
- 2008-07-31 MX MX2010001137A patent/MX2010001137A/es not_active Application Discontinuation
- 2008-07-31 JP JP2010520181A patent/JP5553751B2/ja not_active Expired - Fee Related
- 2008-07-31 CN CN2008801048142A patent/CN101790532B/zh not_active Expired - Fee Related
- 2008-07-31 AU AU2008282156A patent/AU2008282156B2/en not_active Ceased
- 2008-07-31 EP EP08796922A patent/EP2176261B1/en not_active Not-in-force
- 2008-07-31 NZ NZ582879A patent/NZ582879A/en not_active IP Right Cessation
- 2008-07-31 WO PCT/US2008/071714 patent/WO2009018415A1/en active Application Filing
- 2008-07-31 AR ARP080103330A patent/AR067762A1/es unknown
- 2008-07-31 ES ES08796922T patent/ES2400104T3/es active Active
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2010
- 2010-01-28 US US12/695,292 patent/US8242272B2/en not_active Expired - Fee Related
- 2010-09-02 HK HK10108334.6A patent/HK1141806A1/xx not_active IP Right Cessation
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2012
- 2012-01-11 US US13/347,926 patent/US8598361B2/en not_active Expired - Fee Related
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2013
- 2013-11-12 JP JP2013233687A patent/JP2014055160A/ja active Pending
Also Published As
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| US8242272B2 (en) | 2012-08-14 |
| EP2176261A1 (en) | 2010-04-21 |
| US8598361B2 (en) | 2013-12-03 |
| CN101790532B (zh) | 2013-11-20 |
| AU2008282156A1 (en) | 2009-02-05 |
| JP2010535241A (ja) | 2010-11-18 |
| CN101790532A (zh) | 2010-07-28 |
| AU2008282156B2 (en) | 2014-07-17 |
| MX2010001137A (es) | 2010-03-31 |
| HK1141806A1 (en) | 2010-11-19 |
| NZ582879A (en) | 2012-03-30 |
| TW200916468A (en) | 2009-04-16 |
| JP2014055160A (ja) | 2014-03-27 |
| US20100184980A1 (en) | 2010-07-22 |
| US20120232275A1 (en) | 2012-09-13 |
| ES2400104T3 (es) | 2013-04-05 |
| CA2694499A1 (en) | 2009-02-05 |
| EP2176261B1 (en) | 2012-12-19 |
| WO2009018415A1 (en) | 2009-02-05 |
| JP5553751B2 (ja) | 2014-07-16 |
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