AR093364A1 - Imidazo[1,2-a]piridincarboxamidas aminosustituidas y su uso - Google Patents

Imidazo[1,2-a]piridincarboxamidas aminosustituidas y su uso

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Publication number
AR093364A1
AR093364A1 ARP130104043A ARP130104043A AR093364A1 AR 093364 A1 AR093364 A1 AR 093364A1 AR P130104043 A ARP130104043 A AR P130104043A AR P130104043 A ARP130104043 A AR P130104043A AR 093364 A1 AR093364 A1 AR 093364A1
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AR
Argentina
Prior art keywords
alkyl
substituted
alkoxy
group
trifluoromethyl
Prior art date
Application number
ARP130104043A
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English (en)
Inventor
Dr Vakalopoulos Alexandros
Dr Follmann Markus
Dr Hartung Ingo
Dr Buchgraber Philipp
Dr Jautelat Rolf
Dr Hafeld Jorma
Lindner Niels
Dr Gromov Alexey
Dr Wunder Frank
Prof Dr Stasch Johannes
Peter - Dr Redlich Gorden
Min Dr Li Volkhart
Maria Jian - Dr Becker-Pelster Eva
Dr Knorr Andreas
Original Assignee
Bayer Pharma AG
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Priority claimed from US13/789,655 external-priority patent/US9126998B2/en
Application filed by Bayer Pharma AG filed Critical Bayer Pharma AG
Publication of AR093364A1 publication Critical patent/AR093364A1/es

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Abstract

La presente se refiere a imidazo[1,2-a]piridin-3-carboxamidas sustituidas, a procedimientos para su preparación, a su uso solas o en combinaciones 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 especial para el tratamiento y/o la prevención de enfermedades cardiovasculares. Reivindicación 1: Compuesto de la fórmula (1), en donde A representa CH₂, CD₂ o CH(CH₃); R¹ representa alquilo C₄₋₆, cicloalquilo C₃₋₇ o fenilo, en donde alquilo C₄₋₆ puede estar sustituido hasta seis veces con flúor, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 a 4 sustituyentes seleccionados, de modo independiente entre si del grupo de flúor, trifluorometilo y alquilo C₁₋₄, y en donde fenilo puede estar sustituido con 1 a 4 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, monofluorometilo, difluorometilo, trifluorometilo, alquil C₁₋₄, cicloalquilo C₃₋₆, alcoxi C₁₋₄, difluorometoxi y trifluorometoxi; R² representa hidrógeno, alquilo C₁₋₄, ciclopropilo, monofluorometilo, difluorometilo o trifluorometilo; R³ representa un grupo de la fórmula (2) ó (3) en donde * representa el sitio de unión con el grupo carbonilo; L¹A representa un enlace o alcan C₁₋₄-diílo, en donde alcan C₁₋₄-diílo puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, hidroxi y alcoxi C₁₋₄; L¹B representa un enlace o alcan C₁₋₄-diílo; L¹C representa un enlace o alcan C₁₋₄-diilo, en donde alcan C₁₋₄-diílo puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, hidroxi y alcoxi C₁₋₄; R⁷ representa hidrógeno, alquilo C₁₋₆, alquenilo C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, ciano, heteroalquilo de 5 a 10 miembros, naftilo o fenilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, difluorometoxi, trifluorometoxi, hidroxi, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo, alquil C₁₋₄-sulfonilo, fenilo, fenoxi y benciloxi, en donde fenilo, fenoxi y benciloxi, a su vez, pueden estar sustituidos con 1 a 3 sustituyentes halógeno o alcoxi C₁₋₄, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄ y alcoxi C₁₋₄, y en donde fenilo y heteroarilo de 5 a 10 miembros pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, nitro, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, -NH(CO)CH₃, alquilo C₁₋₄, cicloalquilo C₁₋₄, alquenilo C₁₋₄, alquil C₁₋₄-sulfonilo, alcoxi C₁₋₄-carbonil y alcoxi C₁₋₄, en donde alcoxi C₁₋₄ puede estar sustituido con hidroxi, y en donde el fenilo puede estar sustituido en 2 átomos de carbono adyacentes con un puente de difluorometilendioxi; R⁸ representa hidrógeno o alquilo C₁₋₄, o R⁷ y R⁸ junto con el átomo de carbono al que están unidos, forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros o el heterociclo de 4 a 7 miembros, a su vez, pueden estar sustituidos con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor y alquilo C₁₋₄; R⁹ representa hidrógeno, ciano, alquilo C₁₋₆, alquenil C₂₋₆, alquinilo C₂₋₆, cicloalquilo C₃₋₇, heteroarilo de 5 a 10 miembros o fenilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, hidroxi, ciano, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo, alquil C₁₋₄-sulfonilo, heteroarilo de 5 ó 6 miembros, fenilo, fenoxi y benciloxi, en donde fenilo, fenoxi y benciloxi, a su vez, pueden estar sustituidos con 1 a 3 sustituyentes halógeno o alcoxi C₁₋₄, en donde heteroarilo de 5 ó 6 miembros puede estar benzocondensado o sustituido con un heteroarilo de 5 ó 6 miembros, en donde heteroarilo de 5 ó 6 miembros puede estar sustituido con alquilo C₁₋₄ o trifluorometilo, en donde cicloalquilo C₃₋₇ puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄ y alcoxi C₁₋₄, y en donde fenilo y heteroarilo de 5 a 10 miembros pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno, ciano, difluorometilo, trifluorometilo, difluorometoxi, trifluorometoxi, alquilo C₁₋₄, cicloalquilo C₁₋₄, alcoxi C₁₋₄, alcoxi C₁₋₄-carbonilo y alquil C₁₋₄-sulfonilo, en donde alcoxi C₁₋₄ puede estar sustituido con hidroxi, y en donde puede estar sustituido en 2 átomos de carbono adyacentes del fenilo con un puente de difluorometilendioxi; R¹⁰ representa hidrógeno o alquilo C₁₋₄, o R⁹ y R¹⁰ junto con el átomo de carbono al que están unidos, forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros o el heterociclo de 4 a 7 miembros, a su vez, pueden estar sustituidos con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, bencilo y alquilo C₁₋₄, siempre que los radicales R⁷ y R⁹ no representen al mismo tiempo fenilo, o R⁷ y R⁹ junto con los átomos de carbono a los que están unidos, así como el grupo L¹B forman un carbociclo de 3 a 7 miembros o un heterociclo de 4 a 7 miembros, en donde el carbociclo de 3 a 7 miembros puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de alquilo C₁₋₄, flúor, hidroxi y alcoxi C₁₋₄, siempre que, al mismo tiempo, no más que uno de los pares de radicales R⁷ y R⁸, R⁹ y R¹⁰ o bien R⁷ y R⁹ forme un carbo- o heterociclo; R¹¹ representa hidrógeno o alquilo C₁₋₄, en donde alquilo C₁₋₄ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, hidroxi y alcoxi C₁₋₄; R¹² representa hidrógeno, alquilo C₁₋₆, cicloalquil C₃₋₇, fenilo o bencilo, en donde alquilo C₁₋₆ puede estar sustituido con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, hidroxi, alcoxi C₁₋₄ y fenoxi, y en donde fenilo y bencilo pueden estar sustituidos con 1 a 3 sustituyentes seleccionados, de modo independiente entre sí, del grupo de halógeno y trifluorometilo, o R¹¹ y R¹² junto con el átomo de nitrógeno al que están unidos, forman un aza-heterociclo de 4 a 7 miembros, en donde el aza-heterociclo de 4 a 7 miembros puede estar sustituido con 1 ó 2 sustituyentes seleccionados, de modo independiente entre sí, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquil C₃₋₇, hidroxi, alcoxi C₁₋₄ y heterociclilo de 4 a 7 miembros; y L² representa un enlace o alcan C₁₋₄-diílo; R¹³ representa un aza-heterociclilo de 5 a 9 miembros, unido a través de un átomo de carbono del anillo, en donde el aza-heterociclilo de 5 a 9 miembros puede estar sustituido con 1 a 5 sustituyentes seleccionados, de modo independiente, del grupo de flúor, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇ y bencilo, y en donde el aza-heterociclilo de 5 a 9 miembros puede estar fusionado con un anillo fenilo que, a su vez, puede estar sustituido con 1 ó 2 sustituyentes seleccionados de halógeno, alquilo C₁₋₄, alcoxi C₁₋₄ y trifluorometilo, o representa adamantilo; R⁴ representa hidrógeno; R⁵ representa hidrógeno, halógeno, ciano, monofluorometilo, difluorometilo, trifluorometilo, alquilo C₁₋₄, cicloalquilo C₃₋₇, alquenil C₂₋₄, alquinilo C₂₋₄, difluorometoxi, trifluorometoxi, alcoxi C₁₋₄, amino, heterociclilo de 4 a 7 miembros o heteroarilo de 5 ó 6 miembros; R⁶ representa hidrógeno, ciano o halógeno; así como sus N-óxidos, sales, solvatos, sales de los N-óxidos y solvatos de los N-óxidos y sales.
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Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9126998B2 (en) 2012-11-05 2015-09-08 Bayer Pharma AG Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US8778964B2 (en) * 2012-11-05 2014-07-15 Bayer Pharma Aktiengesellschaft Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use
US9624214B2 (en) 2012-11-05 2017-04-18 Bayer Pharma Aktiengesellschaft Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US9776997B2 (en) 2013-06-04 2017-10-03 Bayer Pharma Aktiengesellschaft 3-aryl-substituted imidazo[1,2-A]pyridines and their use
EP3094327A1 (en) 2014-01-13 2016-11-23 Ironwood Pharmaceuticals, Inc. USE OF sGC STIMULATORS FOR THE TREATMENT OF NEUROMUSCULAR DISORDERS
US9688699B2 (en) 2014-02-19 2017-06-27 Bayer Pharma Aktiengesellschaft 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines
CN106715426A (zh) * 2014-03-21 2017-05-24 拜耳医药股份有限公司 氰基取代的咪唑并[1,2‑a]吡啶甲酰胺及其用途
CN106470995A (zh) * 2014-05-02 2017-03-01 拜耳医药股份有限公司 用于治疗心血管疾病的作为可溶性鸟苷酸环化酶刺激物的咪唑并[1,2‑a]吡啶类
WO2015165970A1 (de) * 2014-05-02 2015-11-05 Bayer Pharma Aktiengesellschaft 6-chlor-substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung als stimulatoren der löslichen guanylatcyclase
CA2969265A1 (en) * 2014-12-02 2016-06-09 Bayer Pharma Aktiengesellschaft Substituted pyrazolo[1,5-a]pyridines and imidazo[1,2-a]pyrazines and their use
EP3227287B1 (de) * 2014-12-02 2019-08-07 Bayer Pharma Aktiengesellschaft Heteroaryl-substituierte imidazo[1,2-a]pyridine und ihre verwendung
JP2018505886A (ja) * 2015-02-05 2018-03-01 バイエル・ファルマ・アクティエンゲゼルシャフト 心血管疾患を治療するための可溶性グアニル酸シクラーゼ（ＳＧＣ）の刺激物質としてのＮ−置換８−［（２，６−ジフルオロベンジル）オキシ］−２，６−ジメチルイミダゾ［１，２−ａ］ピラジン−３−カルボキサミド誘導体
EP3286185A1 (de) * 2015-02-05 2018-02-28 Bayer Pharma Aktiengesellschaft Substituierte pyrazolo[1,5-a]pyridin-3-carboxamide und ihre verwendung
MX2017014057A (es) 2015-05-06 2018-04-10 Bayer Pharma AG El uso de estimuladores sgc, activadores gc, solos y combinaciones con inhibidores pde5 para el tratamiento de ulceras digitales (du) concomitante con esclerosis sistemica (ssc).
CN107709314A (zh) 2015-06-11 2018-02-16 巴斯利尔药物国际股份公司 外排泵抑制剂及其治疗性用途
JP6849618B2 (ja) 2015-07-23 2021-03-24 バイエル・ファルマ・アクティエンゲゼルシャフト 中性エンドペプチダーゼの阻害剤（ＮＥＰ阻害剤）および／またはアンジオテンシンＩＩ拮抗薬と組み合わせた可溶性グアニル酸シクラーゼ（ｓＧＣ）の刺激薬および／または活性化薬ならびにその使用
US20180344735A1 (en) 2015-12-14 2018-12-06 Ironwood Pharmaceuticals, Inc. USE OF sGC STIMULATORS FOR THE TREATMENT OF GASTROINTESTINAL SPHINCTER DYSFUNCTION
JOP20170113B1 (ar) * 2016-05-09 2023-03-28 Bayer Pharma AG مركبات 5، 6، 7، 8-رباعي هيدرو [1، 2، 4] تريازولو [4، 3-أ] بيريدين 3(2h)-ون مستبدلة ومركبات 2، 5، 6، 7-رباعي هيدرو-3h-بيرولو [2، 1-ج] [1، 2، 4] تريازول-3-ون واستخداماتها
SI3507291T1 (sl) 2016-09-02 2021-11-30 Cyclerion Therapeutics, Inc. Kondenzirani biciklični SGS stimulatorji
CN109890379A (zh) 2016-10-11 2019-06-14 拜耳制药股份公司 包含sGC活化剂和盐皮质激素受体拮抗剂的组合产品
EP3525779B1 (de) 2016-10-11 2024-06-05 Bayer Pharma Aktiengesellschaft Kombination enthaltend den sgc stimulator vericuguat und den mineralcorticoid-rezeptor-antagonist finerenone
EP3554488A2 (en) 2016-12-13 2019-10-23 Cyclerion Therapeutics, Inc. Use of sgc stimulators for the treatment of esophageal motility disorders
WO2018153899A1 (de) 2017-02-22 2018-08-30 Bayer Pharma Aktiengesellschaft Selektive partielle adenosin a1 rezeptor-agonisten in kombination mit stimulatoren und/oder aktivatoren der löslichen guanylatcyclase (sgc)
WO2018184976A1 (de) 2017-04-05 2018-10-11 Bayer Pharma Aktiengesellschaft Substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung
WO2019081353A1 (de) 2017-10-24 2019-05-02 Bayer Aktiengesellschaft Substituierte imidazopyridinamide und ihre verwendung
EP3787610A1 (en) * 2018-04-30 2021-03-10 Bayer Aktiengesellschaft The use of sgc activators and sgc stimulators for the treatment of cognitive impairment
EP3566704A1 (en) 2018-05-11 2019-11-13 Bayer Aktiengesellschaft The use of non-steroidal mineralocorticoid receptor antagonists alone or in combination for the treatment of muscular or neuromuscular diseases
EP3793553A1 (en) 2018-05-15 2021-03-24 Bayer Aktiengesellschaft 1,3-thiazol-2-yl substituted benzamides for the treatment of diseases associated with nerve fiber sensitization
EP3574905A1 (en) 2018-05-30 2019-12-04 Adverio Pharma GmbH Method of identifying a subgroup of patients suffering from dcssc which benefits from a treatment with sgc stimulators and sgc activators in a higher degree than a control group
KR20250141845A (ko) 2018-07-11 2025-09-29 티센토 쎄라퓨틱스 인크. 미토콘드리아 장애의 치료를 위한 sGC 자극제의 용도
WO2020164008A1 (en) 2019-02-13 2020-08-20 Bayer Aktiengesellschaft Process for the preparation of porous microparticles
WO2020216669A1 (de) 2019-04-23 2020-10-29 Bayer Aktiengesellschaft Phenylsubstituierte imidazopyridinamide und ihre verwendung
EP3822265A1 (en) 2019-11-15 2021-05-19 Bayer AG Substituted hydantoinamides as adamts7 antagonists
EP3822268A1 (en) 2019-11-15 2021-05-19 Bayer Aktiengesellschaft Substituted hydantoinamides as adamts7 antagonists
JP2023035862A (ja) * 2021-08-30 2023-03-13 Jnc株式会社 シクロブタン環を有するジアミン誘導体、およびその塩
EP4456896A1 (en) 2021-12-29 2024-11-06 Bayer Aktiengesellschaft Treatment of cardiopulmonary disorders
KR20240144177A (ko) 2021-12-29 2024-10-02 바이엘 악티엔게젤샤프트 (5s)-{[2-(4-카르복시페닐)에틸][2-(2-{[3-클로로-4'-(트리플루오로메틸)비페닐-4-일]메톡시}페닐)에틸]아미노}-5,6,7,8-테트라히드로퀴놀린-2-카르복실산및 약학적 활성 화합물로서 사용하기 위한 이의 결정질 형태를 제조하는 방법
AU2022427770A1 (en) 2021-12-29 2024-07-04 Bayer Aktiengesellschaft Pharmaceutical dry powder inhalation formulation
WO2024102699A1 (en) * 2022-11-07 2024-05-16 ELANCO US, Inc. Guanylate cyclase (gc) stimulator formulations and uses thereof

Family Cites Families (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0266890A1 (en) 1986-10-07 1988-05-11 Yamanouchi Pharmaceutical Co. Ltd. Imidazopyridine derivatives, their production, and pharmaceutical compositions containing them
SE8704248D0 (sv) 1987-10-30 1987-10-30 Haessle Ab Medical use
JP2643274B2 (ja) 1988-04-08 1997-08-20 三菱化学株式会社 イミダゾ〔１，２−ａ〕ピリジン誘導体
US5593993A (en) 1991-08-02 1997-01-14 Medivir Ab Method for inhibition of HIV related viruses
FR2714907B1 (fr) 1994-01-07 1996-03-29 Union Pharma Scient Appl Nouveaux dérivés de l'Adénosine, leurs procédés de préparation, compositions pharmaceutiques les contenant.
IL112778A0 (en) 1994-03-04 1995-05-26 Merck & Co Inc Substituted heterocycles, their preparation and pharmaceutical compositions containing them
JPH11505524A (ja) 1995-05-01 1999-05-21 藤沢薬品工業株式会社 イミダゾ１，２−ａピリジンおよびイミダゾ１，２−ａピリデジン誘導体、および骨吸収阻害剤としてのその用途
CA2196263C (en) 1996-02-09 2004-10-26 Barry Jackson Process for the preparation of 4-oxoimidazolinium salts
EP0802192A1 (de) 1996-04-17 1997-10-22 Bayer Ag Heterocyclisch-substituierte Phenylglycinolamide mit antiatherosklerotischer Wirkung und Verfahren zu ihrer Herstellung
DE19642255A1 (de) * 1996-10-14 1998-04-16 Bayer Ag Verwendung von 1-Benzyl-3-(substituierten-hetaryl) -kondensierten Pyrazol-Derivaten
US6403588B1 (en) 2000-04-27 2002-06-11 Yamanouchi Pharmaceutical Co., Ltd. Imidazopyridine derivatives
CN1173975C (zh) 2000-04-27 2004-11-03 山之内制药株式会社 咪唑并吡啶衍生物
EP1537214B1 (en) * 2002-09-01 2006-03-01 Washington University Regulated bacterial lysis for gene vaccine vector delivery and antigen release
US7135575B2 (en) 2003-03-03 2006-11-14 Array Biopharma, Inc. P38 inhibitors and methods of use thereof
EP1778685B1 (de) 2004-08-02 2008-03-26 Schwarz Pharma Ag Carboxamide des indolizins und seiner aza- und diazaderivate
GB0508992D0 (en) 2005-05-03 2005-06-08 Novartis Ag Organic compounds
CA2612723A1 (en) 2005-06-24 2007-01-04 Eli Lilly And Company Tetrahydrocarbazole derivatives useful as androgen receptor modulators
GB0514203D0 (en) 2005-07-11 2005-08-17 Novartis Ag Organic compounds
PE20080403A1 (es) 2006-07-14 2008-04-25 Amgen Inc Derivados heterociclicos fusionados y metodos de uso
CN101553474B (zh) 2006-10-19 2013-02-27 霍夫曼-拉罗奇有限公司 作为糖尿病用11b-HSD1抑制剂的咪唑啉酮和咪唑烷酮衍生物
DE102006054562A1 (de) 2006-11-20 2008-05-21 Bayer Healthcare Ag Verfahren zum Nachweis von Pyrophosphat mit Biolumineszenz Detektion
CN101631786A (zh) 2006-12-20 2010-01-20 先灵公司 新颖的jnk抑制剂
WO2008134553A1 (en) 2007-04-26 2008-11-06 Xenon Pharmaceuticals Inc. Methods of using bicyclic compounds in treating sodium channel-mediated diseases
US8198449B2 (en) 2008-09-11 2012-06-12 Bristol-Myers Squibb Company Compounds for the treatment of hepatitis C
CA2793086C (en) 2010-03-18 2018-08-21 Institut Pasteur Korea Substituted imidazo[1,2-a]pyridine compounds and their use in the treatment of bacterial infections
DE102010020553A1 (de) 2010-05-14 2011-11-17 Bayer Schering Pharma Aktiengesellschaft Substituierte 8-Alkoxy-2-aminotetralin-Derivate und ihre Verwendung
KR20140019004A (ko) 2010-05-27 2014-02-13 머크 샤프 앤드 돔 코포레이션 가용성 구아닐레이트 시클라제 활성화제
EP2687210A1 (de) 2010-06-25 2014-01-22 Bayer Intellectual Property GmbH Verwendung von Stimulatoren und Aktivatoren der löslichen Guanylatzyklase zur Behandlung von Sichelzellanämie und Konservierung von Blutersatzstoffen
KR102104125B1 (ko) 2011-04-21 2020-05-29 재단법인 한국파스퇴르연구소 소염 화합물
AR086589A1 (es) 2011-05-30 2014-01-08 Astellas Pharma Inc Compuestos imidazopiridina
US9126998B2 (en) * 2012-11-05 2015-09-08 Bayer Pharma AG Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US8778964B2 (en) * 2012-11-05 2014-07-15 Bayer Pharma Aktiengesellschaft Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use
US8796305B2 (en) * 2012-11-05 2014-08-05 Bayer Pharma Aktiengesellschaft Carboxy-substituted imidazo[1,2-a]pyridinecarboxamides and their use
US9624214B2 (en) 2012-11-05 2017-04-18 Bayer Pharma Aktiengesellschaft Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use
EA027909B1 (ru) 2012-11-30 2017-09-29 Астеллас Фарма Инк. Имидазопиридиновые соединения
US9776997B2 (en) 2013-06-04 2017-10-03 Bayer Pharma Aktiengesellschaft 3-aryl-substituted imidazo[1,2-A]pyridines and their use
CA2920559A1 (en) 2013-08-08 2015-02-12 Bayer Pharma Aktiengesellschaft Substituted imidazo[1,2-a]pyrazinecarboxamides and use thereof
CA2920565A1 (en) 2013-08-08 2015-02-12 Bayer Pharma Aktiengesellschaft Substituted pyrazolo[1,5-a]pyridine-3-carboxamides and use thereof
WO2015082411A1 (de) 2013-12-05 2015-06-11 Bayer Pharma Aktiengesellschaft Aryl- und hetaryl-substituierte imidazo[1,2-a]pyridin-3-carboxamide und ihre verwendung
US9688699B2 (en) 2014-02-19 2017-06-27 Bayer Pharma Aktiengesellschaft 3-(pyrimidine-2-yl)imidazo[1,2-a]pyridines
WO2015140254A1 (de) 2014-03-21 2015-09-24 Bayer Pharma Aktiengesellschaft Substituierte imidazo[1,2-a]pyridincarboxamide und ihre verwendung
CN106715426A (zh) 2014-03-21 2017-05-24 拜耳医药股份有限公司 氰基取代的咪唑并[1,2‑a]吡啶甲酰胺及其用途
US20170050962A1 (en) 2014-05-02 2017-02-23 Bayer Pharma Aktiengesellschaft Imidazo[1,2-a]pyridines as stimulators of soluble guanylate cyclase for treating cardiovascular diseases
CN106470995A (zh) 2014-05-02 2017-03-01 拜耳医药股份有限公司 用于治疗心血管疾病的作为可溶性鸟苷酸环化酶刺激物的咪唑并[1,2‑a]吡啶类

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