WO2003022821A1 - Heterocycle derivative having 20-hete-producing enzyme inhibitory activity - Google Patents

Heterocycle derivative having 20-hete-producing enzyme inhibitory activity Download PDF

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Publication number
WO2003022821A1
WO2003022821A1 PCT/JP2002/009054 JP0209054W WO03022821A1 WO 2003022821 A1 WO2003022821 A1 WO 2003022821A1 JP 0209054 W JP0209054 W JP 0209054W WO 03022821 A1 WO03022821 A1 WO 03022821A1
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WO
WIPO (PCT)
Prior art keywords
hete
producing enzyme
activity
inhibitory activity
heterocycle derivative
Prior art date
Application number
PCT/JP2002/009054
Other languages
French (fr)
Japanese (ja)
Inventor
Masakazu Sato
Hiroyuki Kakinuma
Hiroki Umemiya
Toshio Nakamura
Original Assignee
Taisho Pharmaceutical Co., Ltd.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Taisho Pharmaceutical Co., Ltd. filed Critical Taisho Pharmaceutical Co., Ltd.
Priority to JP2003526897A priority Critical patent/JPWO2003022821A1/en
Publication of WO2003022821A1 publication Critical patent/WO2003022821A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • 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
    • A61K31/415—1,2-Diazoles
    • A61K31/4155—1,2-Diazoles non condensed 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
    • A61K31/41—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
    • A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
    • 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
    • A61K31/4196—1,2,4-Triazoles
    • 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
    • A61K31/42—Oxazoles
    • 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
    • A61K31/42—Oxazoles
    • A61K31/422—Oxazoles not condensed 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
    • A61K31/41—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
    • A61K31/4245—Oxadiazoles
    • 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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed 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
    • A61K31/435—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
    • A61K31/454—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. pimozide, domperidone
    • 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
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A heterocycle derivative represented by the formula (I) (wherein Y is carbon or nitrogen; R1 is a heterocyclic group; R2 is hydrogen, C1-4 alkyl, C1-4 alkoxy, or halogeno; n is an integer of 1 to 4; and R3 is morpholino, pyrrolidino, 4-C1-6-alkoxycarbonylpiperazin-1-yl-propyl, etc.) or a pharmaceutically acceptable salt of the derivative. Also provided is a medicine which inhibits a 20-HETE-producing enzyme, which participates in microvascular constrictive/dilative activity, cell proliferation activity, and other activity in principal organs such as the kidneys and cerebral blood vessels.
PCT/JP2002/009054 2001-09-06 2002-09-05 Heterocycle derivative having 20-hete-producing enzyme inhibitory activity WO2003022821A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2003526897A JPWO2003022821A1 (en) 2001-09-06 2002-09-05 Heterocyclic derivatives having 20-HETE-producing enzyme inhibitory activity

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2001269896 2001-09-06
JP2001269897 2001-09-06
JP2001-269897 2001-09-06
JP2001-269896 2001-09-06
JP2001-396526 2001-12-27
JP2001396526 2001-12-27

Publications (1)

Publication Number Publication Date
WO2003022821A1 true WO2003022821A1 (en) 2003-03-20

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WO (1) WO2003022821A1 (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003092678A1 (en) * 2002-04-30 2003-11-13 Schering Aktiengesellschaft 1-substituted imidazole derivatives as nos inhibitors
JP2008543958A (en) * 2005-06-28 2008-12-04 サノフィ−アベンティス Heteroaryl-substituted amides containing saturated linker groups and their use as pharmaceuticals
US7576102B2 (en) 2005-12-21 2009-08-18 Decode Genetics Ehf Biaryl substituted nitrogen containing heterocycle inhibitors of LTA4H for treating inflammation
US7652155B2 (en) 2003-04-14 2010-01-26 Nippon Soda Co., Ltd. Diamine derivative, production process therefor and antioxidant
US7674802B2 (en) 2005-12-21 2010-03-09 Decode Genetics, Ehf N-linked aryl heteroaryl inhibitors of LTA4H for treating inflammation
WO2012052412A1 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Novel heterocyclic compounds as pesticides
WO2013100054A1 (en) * 2011-12-27 2013-07-04 大正製薬株式会社 Phenyltriazole derivative
WO2017141927A1 (en) * 2016-02-15 2017-08-24 大正製薬株式会社 Azole-substituted pyridine compound
US9890126B2 (en) * 2012-04-24 2018-02-13 Board Of Trustees Of Northern Illinois University Synthesis of novel inhibitors of isoprenoid biosynthesis (ISPF)
WO2019031618A1 (en) 2017-08-10 2019-02-14 大正製薬株式会社 Pyridine compound substituted with azole
WO2020162612A1 (en) * 2019-02-08 2020-08-13 大正製薬株式会社 Pyridine compound substituted by heteroaryl

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001068610A1 (en) * 2000-03-13 2001-09-20 Taisho Pharmaceutical Co.,Ltd Imidazolylbenzophenone derivatives
WO2001096309A1 (en) * 2000-06-15 2001-12-20 Taisho Pharmaceutical Co., Ltd. Hydroxyformamidine derivatives and medicines containing the same
JP2001354658A (en) * 2000-06-15 2001-12-25 Taisho Pharmaceut Co Ltd Hydroxyformamidine compound and its salt and medicine comprising the same
JP2001354656A (en) * 2000-06-15 2001-12-25 Taisho Pharmaceut Co Ltd Hydroxyformamidine compound and its salt and medicine comprising the same

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2001068610A1 (en) * 2000-03-13 2001-09-20 Taisho Pharmaceutical Co.,Ltd Imidazolylbenzophenone derivatives
WO2001096309A1 (en) * 2000-06-15 2001-12-20 Taisho Pharmaceutical Co., Ltd. Hydroxyformamidine derivatives and medicines containing the same
JP2001354658A (en) * 2000-06-15 2001-12-25 Taisho Pharmaceut Co Ltd Hydroxyformamidine compound and its salt and medicine comprising the same
JP2001354656A (en) * 2000-06-15 2001-12-25 Taisho Pharmaceut Co Ltd Hydroxyformamidine compound and its salt and medicine comprising the same

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2005529138A (en) * 2002-04-30 2005-09-29 シエーリング アクチエンゲゼルシャフト 1-Substituted imidazole derivatives as NOS inhibitors
US6982259B2 (en) 2002-04-30 2006-01-03 Schering Aktiengesellschaft N-heterocyclic derivatives as NOS inhibitors
US7202263B2 (en) 2002-04-30 2007-04-10 Schering Aktiengesellschaft N-heterocyclic derivatives as NOS inhibitors
WO2003092678A1 (en) * 2002-04-30 2003-11-13 Schering Aktiengesellschaft 1-substituted imidazole derivatives as nos inhibitors
US7652155B2 (en) 2003-04-14 2010-01-26 Nippon Soda Co., Ltd. Diamine derivative, production process therefor and antioxidant
US8518976B2 (en) 2005-06-28 2013-08-27 Sanofi Heteroaryl-substituted amides comprising a saturated linker group, and their use as pharmaceuticals
JP2008543958A (en) * 2005-06-28 2008-12-04 サノフィ−アベンティス Heteroaryl-substituted amides containing saturated linker groups and their use as pharmaceuticals
US7576102B2 (en) 2005-12-21 2009-08-18 Decode Genetics Ehf Biaryl substituted nitrogen containing heterocycle inhibitors of LTA4H for treating inflammation
US7674802B2 (en) 2005-12-21 2010-03-09 Decode Genetics, Ehf N-linked aryl heteroaryl inhibitors of LTA4H for treating inflammation
US9173396B2 (en) 2010-10-22 2015-11-03 Bayer Intellectual Property Gmbh Heterocyclic compounds as pesticides
WO2012052412A1 (en) 2010-10-22 2012-04-26 Bayer Cropscience Ag Novel heterocyclic compounds as pesticides
JPWO2013100054A1 (en) * 2011-12-27 2015-05-11 大正製薬株式会社 Phenyltriazole derivatives
WO2013100054A1 (en) * 2011-12-27 2013-07-04 大正製薬株式会社 Phenyltriazole derivative
US9890126B2 (en) * 2012-04-24 2018-02-13 Board Of Trustees Of Northern Illinois University Synthesis of novel inhibitors of isoprenoid biosynthesis (ISPF)
CN108602796A (en) * 2016-02-15 2018-09-28 大正制药株式会社 The pyridine compounds of azole substitution
JPWO2017141927A1 (en) * 2016-02-15 2018-03-01 大正製薬株式会社 Pyridine compounds substituted with azoles
WO2017141927A1 (en) * 2016-02-15 2017-08-24 大正製薬株式会社 Azole-substituted pyridine compound
RU2730498C2 (en) * 2016-02-15 2020-08-24 Тайсо Фармасьютикал Ко., Лтд. Azole-substituted pyridine compound
WO2019031618A1 (en) 2017-08-10 2019-02-14 大正製薬株式会社 Pyridine compound substituted with azole
CN110914254A (en) * 2017-08-10 2020-03-24 大正制药株式会社 Azole-substituted pyridine compound
KR20200038457A (en) 2017-08-10 2020-04-13 다이쇼 세이야꾸 가부시끼가이샤 Pyridine compound substituted with azole
JPWO2019031618A1 (en) * 2017-08-10 2020-07-30 大正製薬株式会社 Pyridine compounds substituted with azoles
JP7052798B2 (en) 2017-08-10 2022-04-12 大正製薬株式会社 Pyridine compound substituted with azole
US11365192B2 (en) 2017-08-10 2022-06-21 Taisho Pharmaceutical Co., Ltd. Pyridine compound substituted with azole
WO2020162612A1 (en) * 2019-02-08 2020-08-13 大正製薬株式会社 Pyridine compound substituted by heteroaryl

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