AR070519A1 - Derivados de piridina como inhibidores de alk-5 y alk-4 - Google Patents
Derivados de piridina como inhibidores de alk-5 y alk-4Info
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- AR070519A1 AR070519A1 ARP090100052A ARP090100052A AR070519A1 AR 070519 A1 AR070519 A1 AR 070519A1 AR P090100052 A ARP090100052 A AR P090100052A AR P090100052 A ARP090100052 A AR P090100052A AR 070519 A1 AR070519 A1 AR 070519A1
- Authority
- AR
- Argentina
- Prior art keywords
- carbon atoms
- alkyl
- halo
- optionally substituted
- hydroxy
- Prior art date
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- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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Abstract
Estos compuestos son utiles para el tratamiento de trastornos inflamatorios u obstructivos de las vías respiratorias, hipertension pulmonar, fibrosis pulmonar, fibrosis hepática, enfermedades musculares y trastornos esqueléticos sistémicos. También se describen composiciones farmacéuticas que contienen los compuestos y procesos para prepararlos. Reivindicacion 1: Un compuesto de formula (1) en forma libre, de sal o de solvato, en donde T1 es un grupo heterocíclico de 4 a 14 miembros o un grupo cicloalquenilo de 4 a 15 átomos de carbono, cada uno, opcionalmente, sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de R1, O-R1, cicloalquilo de 3 a 5 átomos de carbono, alquiltio de 1 a 8 átomos de carbono, halo, halo-alquilo de 1 a 8 átomos de carbono, amino, alquilamino de 1 a 8 átomos de carbono, di(alquil de 1 a 8 átomos de carbono)amino, ciano, oxo, hidroxi, carboxi y nitro; T2 es un grupo heterocíclico de 4 a 14 miembros opcionalmente sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de R1, R2, R5, O-R1, alcoxicarbonilo de 1 a 8 átomos de carbono, alquiltio de 1 a 8 átomos de carbono, halo, halo-alquilo de 1 a 8 átomos de carbono, amino, alquilamino de 1 a 8 átomos de carbono, di(alquil de 1 a 8 átomos de carbono)amino, ciano, oxo, hidroxi, carboxi y nitro; X se selecciona de CRc, N, O y S, con la condicion de que cuando X sea O o S, Ra esté ausente; Ra y Rb cada uno, independientemente, se selecciona de hidrogeno; OH; NHR10; alquilo de 1 a 8 átomos de carbono opcionalmente sustituido en las posiciones uno, dos o tres, con cicloalquilo de 3 a 10 átomos de carbono opcionalmente sustituido en las posiciones uno o dos, con hidroxi, amino, alquilo de 1 a 8 átomos de carbono, alcoxi de 1 a 8 átomos de carbono, halo, ciano, oxo, carboxi o nitro; y arilo de 6 a 15 átomos de carbono opcionalmente sustituido en las posiciones uno, dos o tres, con halo hidroxi, amino, ciano, oxo, carboxi, nitro o R5; o Ra y Rb junto con X, forman un grupo cíclico de 3, 4, 5 o 6 miembros, opcionalmente sustituido con OH, halo, NR6R7 o R1; Rc se selecciona de H, OH, alquilo de 1 a 8 átomos de carbono y NHR10; R1 es un radical alquilo de 1 a 8 átomos de carbono, alquenilo de 2 a 8 átomos de carbono, cicloalquilo de 3 a 8 átomos de carbono o alquinilo de 2 a 8 átomos de carbono, cada uno opcionalmente sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de hidroxi, ciano, amino, halo, R5, -C(=O)-R5, alquilamino de 1 a 8 átomos de carbono, di(alquil de 1 a 8 átomos de carbono)amino, alcanoilamino de 1 a 8 átomos de carbono, alcoxi de 1 a 8 átomos de carbono, -C(=O)NR6R7, -NH(C=O)-alquilo de 1 a 8 átomos de carbono y -SO2NR6R7; R2 es un radical arilo de 6 a 15 átomos de carbono o cicloalquenilo de 4 a 15 átomos de carbono, cada uno opcionalmente sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de halo, hidroxi, R1, R5, alquiltio de 1 a 8 átomos de carbono, ciano, C(=O)H, nitro, -O-arilo de 6 a 15 átomos de carbono, halo-alquilo de 1 a 8 átomos de carbono, -NR6R7, -alquil(de 1 a 8 átomos de carbono)-NR6R7, -alquil(de 1 a 8 átomos de carbono)-R5, -O-R1, opcionalmente sustituido con NR6R7, -O-R5, -C(=O)-R5, -C(=O)NR6R7, -C(=O)O-R1, -OC(=O)-R1, -SO2NH2, -SO2-R1, -NH-SO2-alquilo de 1 a 8 átomos de carbono, -C(=O)-NH-R1, -C(=O)-NH-R5, -SO2-arilo de 6 a 15 átomos de carbono, -SO2R5 y -SO2NR6R7; R4 es hidroxi, alcoxi de 1 a 8 átomos de carbono, alquiltio de 1 a 8 átomos de carbono, halo, halo-alquilo de 1 a 8 átomos de carbono, ciano, carboxi, nitro, -N(H)-C(=NH)-NH2, -N(H)-SO2-R2, -R2, -C(=O)R2, -C(=O)-R5, -O-R2, -O-R5, -N(H)-R5, -N(H)-R2, -NR6R7, -C(=O)-R1, -C(=O)-NH2, -SO2R5, -C(=O)-O-R1, -C(=O)-O-R2, -C(=O)O-R5, -SO2-R2 o -C(=O)-N(H)-alquil(de 1 a 8 átomos de carbono)-C(=O)-N(H)-R2; o R4 es un grupo heterocíclico de 4 a 14 miembros, estando dicho grupo sustituido opcionalmente con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de hidroxi, halo, oxo, ciano, -NR6R7, carboxi, nitro, -N(H)R1, -N(H)-SO2-alquilo de 1 a 8 átomos de carbono, -N(H)-C(=O)-alquil(de 1 a 4 átomos de carbono)-R2, -C(=O)-NH2, -C(=O)-NR6R7, -C(=O)-N(H)-alquil(de 1 a 8 átomos de carbono)-R6, -C(=O)-R2, -C(=O)-R5, alcoxi de 1 a 8 átomos de carbono, alquiltio de 1 a 8 átomos de carbono, cicloalquilo de 3 a 10 átomos de carbono, -C(=O)-R1, halo-alquilo de 1 a 8 átomos de carbono, -R2, -alquil(de 1 a 8 átomos de carbono)R2, -R5, -SO2-alquilo de 1 a 8 átomos de carbono, -SO2-R2, -SO2-R5, -SO2NR6R7 y alquilo de 1 a 8 átomos de carbono opcionalmente sustituido con hidroxi; o R4 es arilo de 6 a 15 átomos de carbono opcionalmente sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de hidroxi, alcoxi de 1 a 8 átomos de carbono, -O-arilo de 6 a 15 átomos de carbono y alquilo de 1 a 8 átomos de carbono opcionalmente sustituido con hidroxi; o R4 es cicloalquilo de 3 a 10 átomos de carbono sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de hidroxi, -NR6R7, halo, ciano, carboxi, nitro y alquilo de 1 a 8átomos de carbono; R5 es un grupo heterocíclico de 4 a 14 miembros opcionalmente sustituido con uno, dos o tres sustituyentes que se seleccionan cada uno independientemente de oxo, halo, -NR6R7, ciano, hidroxi, carboxi, nitro, -R1, alcoxi de 1 a 8 átomos de carbono, alquiltio de 1 a 8 átomos de carbono, halo-alquilo de 1 a 8 átomos de carbono, -C(=O)-NH2, -SO2-NH2, un grupo éter que contiene 2 a 8 átomos de carbono, y uno, dos o tres átomos enlazados con oxígeno, y un grupo heterocíclico de 4 a 10 miembros que contiene uno o más heteroátomos que se seleccionan independientemente de N, O y S, opcionalmente sustituido con uno o más grupos alquilo de 1 a 6 átomos de carbono; R6 y R7 cada uno independientemente, es hidrogeno, -R1, arilo de 6 a 15 átomos de carbono, -alquil(de 1 a 8 átomos de carbono)-arilo de 6 a 15 átomos de carbono, R5 o -alquil(de 1 a 8 átomos de carbono)-R5; o R6 y R7 junto con el átomo de nitrogeno al que están unidos, forman un anillo heterocíclico de 4 a 10 miembros que contiene opcionalmente uno o más heteroátomos adicionales, que se seleccionan independientemente de N, O y S, en donde el anillo heterocíclico está opcionalmente sustituido con uno o más grupos alquilo de 1 a 6 átomos de carbono; R8 y R9, cada uno independientemente es H, halo, OH, R1, O-R1 o CN; y R10 es H, R1, R2, R5, -SO2-R1, -C(=O)-alquil(de 1 a 4 átomos de carbono)-R2, -C(=O)-NR6R7, -C(=O)-R2, -C(=O)-R5, -C(=O)-R1, -alquil(de 1 a 8 átomos de carbono)-R2, -SO2-R1, -SO2-R2, -SO2-R5 o -SO2NR6R7.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP08150187 | 2008-01-11 | ||
EP08168207 | 2008-11-03 |
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AR070519A1 true AR070519A1 (es) | 2010-04-14 |
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ARP090100052A AR070519A1 (es) | 2008-01-11 | 2009-01-08 | Derivados de piridina como inhibidores de alk-5 y alk-4 |
Country Status (22)
Country | Link |
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US (1) | US8343966B2 (es) |
EP (1) | EP2242742B1 (es) |
JP (1) | JP5566909B2 (es) |
KR (1) | KR20100101138A (es) |
CN (1) | CN101918362B (es) |
AR (1) | AR070519A1 (es) |
AU (1) | AU2009203681B2 (es) |
BR (1) | BRPI0907611A2 (es) |
CA (1) | CA2711803A1 (es) |
CL (1) | CL2009000029A1 (es) |
CR (1) | CR11490A (es) |
EA (1) | EA201001127A1 (es) |
EC (1) | ECSP10010336A (es) |
ES (1) | ES2562447T3 (es) |
IL (1) | IL206276A0 (es) |
MA (1) | MA31947B1 (es) |
MX (1) | MX2010007606A (es) |
PE (1) | PE20091316A1 (es) |
TN (1) | TN2010000255A1 (es) |
TW (1) | TW200938536A (es) |
WO (1) | WO2009087212A2 (es) |
ZA (1) | ZA201003929B (es) |
Families Citing this family (22)
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US20110086834A1 (en) * | 2008-06-26 | 2011-04-14 | Amgen Inc. | Alkynyl alcohols as kinase inhibitors |
MX2011012343A (es) * | 2009-05-19 | 2011-12-14 | Dow Agrosciences Llc | Compuestos y metodos para controlar hongos. |
EA201300080A1 (ru) | 2010-07-05 | 2013-06-28 | Мерк Патент Гмбх | Дипиридильные производные, пригодные для лечения заболеваний, индуцированных киназами |
WO2014060381A1 (de) | 2012-10-18 | 2014-04-24 | Bayer Cropscience Ag | Heterocyclische verbindungen als schädlingsbekämpfungsmittel |
US20150284380A1 (en) | 2012-10-31 | 2015-10-08 | Bayer Cropscience Ag | Novel heterocyclic compounds as pest control agents |
EA032458B1 (ru) | 2014-01-14 | 2019-05-31 | Милленниум Фармасьютикалз, Инк. | Гетероарилы и их применение |
EP3094326A4 (en) | 2014-01-14 | 2017-07-26 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
EA201692140A1 (ru) | 2014-04-24 | 2017-04-28 | Новартис Аг | Производные аминопиридина в качестве ингибиторов фосфатидилинозитол 3-киназы |
ES2667424T3 (es) | 2014-04-24 | 2018-05-10 | Novartis Ag | Derivados de pirazina como inhibidores de fosfatidil-inositol-3-quinasa |
CA2945212A1 (en) | 2014-04-24 | 2015-10-29 | Novartis Ag | Amino pyrazine derivatives as phosphatidylinositol 3-kinase inhibitors |
KR20190017030A (ko) | 2016-06-13 | 2019-02-19 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Dnmt1의 억제제로서의 치환된 피리딘 |
US11666555B2 (en) * | 2017-05-17 | 2023-06-06 | Drexel University | RelA inhibitors for biofilm disruption |
US11919902B2 (en) | 2017-12-22 | 2024-03-05 | Hibercell, Inc. | Aryl-bipyridine amine derivatives as phosphatidylinositol phosphate kinase inhibitors |
KR20200128531A (ko) | 2018-01-29 | 2020-11-13 | 카풀루스 테라퓨틱스, 엘엘씨 | 6원 중심 고리를 포함하는 srebp 억제제 |
AU2021307559A1 (en) | 2020-07-15 | 2023-02-16 | Chiesi Farmaceutici S.P.A. | Pyridazinyl amino derivatives as ALK5 inhibitors |
EP4182322B1 (en) | 2020-07-15 | 2024-04-24 | Chiesi Farmaceutici S.p.A. | Pyrido oxazine derivatives as alk5 inhibitors |
CA3185108A1 (en) | 2020-07-15 | 2022-01-20 | Daniele PALA | Pyrido oxazine amino derivatives as alk5 inhibitors |
US20240116948A1 (en) | 2020-12-23 | 2024-04-11 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine derivatives as alk5 inhibitors |
CN112707924A (zh) * | 2020-12-26 | 2021-04-27 | 蚌埠中实化学技术有限公司 | 一种4-胺甲基苯硼酸盐酸盐的合成方法 |
TW202328102A (zh) | 2021-09-21 | 2023-07-16 | 義大利商吉斯藥品公司 | 作為alk5抑制劑之嗒𠯤基胺基衍生物 |
KR102556500B1 (ko) * | 2021-11-19 | 2023-07-19 | 하나제약 주식회사 | 피롤 유도체 또는 이의 약학적 또는 식품학적으로 허용 가능한 염, 및 이를 유효성분으로 포함하는 위장 질환의 예방, 개선 또는 치료용 조성물 |
WO2023208986A1 (en) | 2022-04-27 | 2023-11-02 | Chiesi Farmaceutici S.P.A. | Imidazole derivatives as alk5 inhibitors |
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US2909529A (en) | 1956-07-19 | 1959-10-20 | Merck Ag E | Process for preparing 3, 4-dihydro-1, 2-pyrano-(3, 4-c)-pyridone-(6) |
BE789099A (fr) | 1971-09-22 | 1973-03-21 | Boehringer Sohn Ingelheim | Nouveaux derives de la pyridine et procede pour les fabriquer |
JP4272338B2 (ja) * | 2000-09-22 | 2009-06-03 | バイエル アクチェンゲゼルシャフト | ピリジン誘導体 |
EP1539748A1 (en) | 2002-07-31 | 2005-06-15 | Smithkline Beecham Corporation | 2-phenylpyridin-4-yl derivatives as alk5 inhibitors |
US20040142978A1 (en) * | 2002-12-12 | 2004-07-22 | Pharmacia Corporation | Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase-2 |
RU2005119173A (ru) | 2002-12-20 | 2006-02-27 | Фармация Корпорейшн (Us) | Ациклические пиразольные соединения |
MY145822A (en) | 2004-08-13 | 2012-04-30 | Neurogen Corp | Substituted biaryl piperazinyl-pyridine analogues |
MX2008013430A (es) | 2006-04-19 | 2009-01-26 | Novartis Vaccines & Diagnostic | Compuestos de indazol y metodos para la inhibición de cdc7. |
CN101484449A (zh) | 2006-04-28 | 2009-07-15 | 艾维克有限公司 | 整合酶抑制剂-3 |
WO2007124545A1 (en) | 2006-04-28 | 2007-11-08 | Avexa Limited | Integrase inhibitors - 2 |
WO2007124544A1 (en) | 2006-04-28 | 2007-11-08 | Avexa Limited | Integrase inhibitors - 1 |
NZ580454A (en) | 2007-03-16 | 2011-05-27 | Actelion Pharmaceuticals Ltd | Amino- pyridine derivatives as s1p1 /edg1 receptor agonists |
EP2144877A1 (en) * | 2007-04-04 | 2010-01-20 | UCB Pharma, S.A. | Novel pyridine derivatives, processes for preparing them, pharmaceutical compositions thereof |
NZ581397A (en) | 2007-04-27 | 2012-02-24 | Astrazeneca Ab | Pyrimidine compounds for the inhibition of Eph receptors and for the treatment of cancer |
EA201000615A1 (ru) * | 2007-10-17 | 2010-12-30 | Новартис Аг | Производные имидазо[1,2-а]пиридина, применимые в качестве ингибиторов апк (активиноподобной киназы) |
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2009
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- 2009-01-08 AR ARP090100052A patent/AR070519A1/es not_active Application Discontinuation
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- 2009-01-09 CL CL2009000029A patent/CL2009000029A1/es unknown
- 2009-01-09 PE PE2009000022A patent/PE20091316A1/es not_active Application Discontinuation
- 2009-01-09 CN CN200980102000XA patent/CN101918362B/zh not_active Expired - Fee Related
- 2009-01-09 MX MX2010007606A patent/MX2010007606A/es active IP Right Grant
- 2009-01-09 EP EP09700450.1A patent/EP2242742B1/en active Active
- 2009-01-09 KR KR1020107015161A patent/KR20100101138A/ko not_active Application Discontinuation
- 2009-01-09 AU AU2009203681A patent/AU2009203681B2/en not_active Ceased
- 2009-01-09 ES ES09700450.1T patent/ES2562447T3/es active Active
- 2009-01-09 EA EA201001127A patent/EA201001127A1/ru unknown
- 2009-01-09 CA CA2711803A patent/CA2711803A1/en not_active Abandoned
- 2009-01-09 BR BRPI0907611-5A patent/BRPI0907611A2/pt not_active IP Right Cessation
- 2009-01-09 WO PCT/EP2009/050208 patent/WO2009087212A2/en active Application Filing
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EP2242742A2 (en) | 2010-10-27 |
JP5566909B2 (ja) | 2014-08-06 |
EP2242742B1 (en) | 2015-12-02 |
ES2562447T3 (es) | 2016-03-04 |
US8343966B2 (en) | 2013-01-01 |
US20090215776A1 (en) | 2009-08-27 |
CA2711803A1 (en) | 2009-07-16 |
PE20091316A1 (es) | 2009-09-24 |
TN2010000255A1 (en) | 2011-11-11 |
EA201001127A1 (ru) | 2011-02-28 |
CN101918362A (zh) | 2010-12-15 |
MX2010007606A (es) | 2010-08-23 |
BRPI0907611A2 (pt) | 2015-07-21 |
ZA201003929B (en) | 2011-03-30 |
JP2011509277A (ja) | 2011-03-24 |
AU2009203681A1 (en) | 2009-07-16 |
KR20100101138A (ko) | 2010-09-16 |
CL2009000029A1 (es) | 2009-07-24 |
WO2009087212A2 (en) | 2009-07-16 |
AU2009203681B2 (en) | 2012-08-16 |
CR11490A (es) | 2010-08-11 |
IL206276A0 (en) | 2010-12-30 |
CN101918362B (zh) | 2013-11-27 |
WO2009087212A3 (en) | 2009-09-24 |
MA31947B1 (fr) | 2010-12-01 |
ECSP10010336A (es) | 2010-08-31 |
TW200938536A (en) | 2009-09-16 |
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