CA2995675C - Heteroaryl compounds and their use as therapeutic drugs - Google Patents

Heteroaryl compounds and their use as therapeutic drugs Download PDF

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Publication number
CA2995675C
CA2995675C CA2995675A CA2995675A CA2995675C CA 2995675 C CA2995675 C CA 2995675C CA 2995675 A CA2995675 A CA 2995675A CA 2995675 A CA2995675 A CA 2995675A CA 2995675 C CA2995675 C CA 2995675C
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CA
Canada
Prior art keywords
amino
pyrazol
methyl
oxy
methy1
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CA2995675A
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English (en)
French (fr)
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CA2995675A1 (en
Inventor
Myeong-Seop Kim
Sumin Kim
Jin Kwan Kim
Hadong Kim
Ki Moon Ryu
Seong Jin Park
Taesun Park
Joon-Ho SHEEN
Taeyoung Yoon
Mi Yeon Jang
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DONG-A SOCIO HOLDINGS Co Ltd
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DONG-A SOCIO HOLDINGS Co Ltd
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Publication of CA2995675A1 publication Critical patent/CA2995675A1/en
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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
    • C07D401/14—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 three or more hetero rings
    • 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
    • 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
    • A61K31/435—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
    • A61K31/435—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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61K31/495—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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines containing further heterocyclic rings
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • 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
    • C07D401/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07D401/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Immunology (AREA)
  • Communicable Diseases (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
CA2995675A 2015-08-31 2016-08-31 Heteroaryl compounds and their use as therapeutic drugs Active CA2995675C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562212520P 2015-08-31 2015-08-31
US62/212,520 2015-08-31
PCT/KR2016/009743 WO2017039331A1 (en) 2015-08-31 2016-08-31 Heteroaryl compounds and their use as therapeutic drugs

Publications (2)

Publication Number Publication Date
CA2995675A1 CA2995675A1 (en) 2017-03-09
CA2995675C true CA2995675C (en) 2023-12-12

Family

ID=58188774

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2995675A Active CA2995675C (en) 2015-08-31 2016-08-31 Heteroaryl compounds and their use as therapeutic drugs

Country Status (21)

Country Link
US (3) US10125118B2 (https=)
EP (1) EP3344613B1 (https=)
JP (2) JP2018528189A (https=)
KR (1) KR102663118B1 (https=)
CN (1) CN108368083B (https=)
AU (1) AU2016317806B2 (https=)
BR (1) BR112018004065B1 (https=)
CA (1) CA2995675C (https=)
CL (1) CL2018000529A1 (https=)
CO (1) CO2018002045A2 (https=)
CR (1) CR20180184A (https=)
ES (1) ES2799300T3 (https=)
IL (1) IL257391B (https=)
MX (1) MX387785B (https=)
MY (1) MY199607A (https=)
PE (1) PE20181017A1 (https=)
PH (1) PH12018500432A1 (https=)
RU (1) RU2723480C2 (https=)
UA (1) UA126372C2 (https=)
WO (1) WO2017039331A1 (https=)
ZA (1) ZA201802033B (https=)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2799300T3 (es) 2015-08-31 2020-12-16 Dong A Socio Holdings Co Ltd Compuestos heteroarilo y su uso como fármacos terapéuticos
US10710980B2 (en) 2016-07-20 2020-07-14 Novartis Ag Aminopyridine derivatives and their use as selective ALK-2 inhibitors
US10913730B2 (en) 2016-10-10 2021-02-09 Dong-A Socio Holdings Co., Ltd. Heteroaryl compounds and their use as Mer inhibitors
GB201820458D0 (en) * 2018-12-14 2019-01-30 Heptares Therapeutics Ltd Ox1 antagonists
GB201901142D0 (en) * 2019-01-28 2019-03-20 Heptares Therapeutics Ltd OX1 Antagonists
GB201905328D0 (en) * 2019-04-15 2019-05-29 Azeria Therapeutics Ltd Inhibitor compounds
JP2023530316A (ja) 2020-06-16 2023-07-14 インサイト・コーポレイション 貧血の治療のためのａｌｋ２阻害剤
WO2022065962A1 (ko) * 2020-09-28 2022-03-31 한국화학연구원 Mlkl 결합 또는 분해용 화합물 및 이들의 의약 용도
TWI893486B (zh) * 2022-10-20 2025-08-11 南韓商東亞Ｓｔ股份有限公司 稠合雙環化合物及其等作為mer及axl抑制劑的用途

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US20020151712A1 (en) 1999-09-14 2002-10-17 Nan-Horng Lin 3-pyrrolidinyloxy-3'-pyridyl ether compounds useful for controlling chemical synaptic transmission
GB0001930D0 (en) 2000-01-27 2000-03-22 Novartis Ag Organic compounds
AR042586A1 (es) 2001-02-15 2005-06-29 Sugen Inc 3-(4-amidopirrol-2-ilmetiliden)-2-indolinona como inhibidores de la protein quinasa; sus composiciones farmaceuticas; un metodo para la modulacion de la actividad catalitica de la proteinquinasa; un metodo para tratar o prevenir una afeccion relacionada con la proteinquinasa
EP1501514B1 (en) * 2002-05-03 2012-12-19 Exelixis, Inc. Protein kinase modulators and methods of use
WO2004054977A1 (en) * 2002-12-13 2004-07-01 Cytopia Pty Ltd Nicotinamide-based kinase inhibitors
SI1569907T1 (sl) 2002-12-13 2016-06-30 Ym Biosciences Australia Pty Ltd Na nikotinamidu osnovani kinazni inhibitorji
CA2517720A1 (en) * 2003-03-11 2004-09-23 Pfizer Products Inc. Pyrazine compounds as transforming growth factor (tgf) inhibitors
US7361764B2 (en) 2004-07-27 2008-04-22 Sgx Pharmaceuticals, Inc. Pyrrolo-pyridine kinase modulators
WO2007011760A2 (en) 2005-07-15 2007-01-25 Kalypsys, Inc. Inhibitors of mitotic kinesin
EP2687533B1 (en) 2006-07-20 2017-07-19 Debiopharm International SA Acrylamide derivatives as FAB I inhibitors
US20140249135A1 (en) 2007-03-01 2014-09-04 Novartis Ag Pim kinase inhibitors and methods of their use
WO2012026712A2 (ko) * 2010-08-23 2012-03-01 주식회사 강스템홀딩스 Ｎｏｄ２의 아고니스트를 처리한 줄기세포 또는 그 배양물을 포함하는 면역질환 또는 염증질환의 예방 또는 치료용 약학조성물
TWI462914B (zh) 2011-09-15 2014-12-01 Hoffmann La Roche 新穎二氫喹啉－２－酮衍生物
ES2799300T3 (es) 2015-08-31 2020-12-16 Dong A Socio Holdings Co Ltd Compuestos heteroarilo y su uso como fármacos terapéuticos

Also Published As

Publication number Publication date
CN108368083A (zh) 2018-08-03
US20230002353A1 (en) 2023-01-05
EP3344613B1 (en) 2020-03-04
CR20180184A (es) 2018-08-23
EP3344613A4 (en) 2019-01-23
JP7208348B2 (ja) 2023-01-18
AU2016317806A1 (en) 2018-02-22
NZ739648A (en) 2024-05-31
PE20181017A1 (es) 2018-06-26
US10947215B2 (en) 2021-03-16
RU2018111072A (ru) 2019-10-04
US20190119252A1 (en) 2019-04-25
US20170355690A9 (en) 2017-12-14
EP3344613A1 (en) 2018-07-11
BR112018004065B1 (pt) 2023-12-12
US12195446B2 (en) 2025-01-14
MX387785B (es) 2025-03-18
US20170066742A1 (en) 2017-03-09
WO2017039331A1 (en) 2017-03-09
ES2799300T3 (es) 2020-12-16
MX2018002574A (es) 2019-02-25
CN108368083B (zh) 2022-02-01
PH12018500432A1 (en) 2018-08-29
JP2022058371A (ja) 2022-04-12
CL2018000529A1 (es) 2018-08-24
BR112018004065A2 (pt) 2018-10-02
IL257391A (en) 2018-04-30
IL257391B (en) 2021-05-31
MY199607A (en) 2023-11-09
KR102663118B1 (ko) 2024-05-03
ZA201802033B (en) 2022-07-27
CO2018002045A2 (es) 2018-05-21
RU2018111072A3 (https=) 2020-01-20
CA2995675A1 (en) 2017-03-09
AU2016317806B2 (en) 2020-11-19
RU2723480C2 (ru) 2020-06-11
US10125118B2 (en) 2018-11-13
JP2018528189A (ja) 2018-09-27
UA126372C2 (uk) 2022-09-28
KR20180044995A (ko) 2018-05-03

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