AU2012314943B9 - Benzyl piperidine compounds as lysophosphatidic acid (LPA) receptor antagonist - Google Patents

Benzyl piperidine compounds as lysophosphatidic acid (LPA) receptor antagonist Download PDF

Info

Publication number
AU2012314943B9
AU2012314943B9 AU2012314943A AU2012314943A AU2012314943B9 AU 2012314943 B9 AU2012314943 B9 AU 2012314943B9 AU 2012314943 A AU2012314943 A AU 2012314943A AU 2012314943 A AU2012314943 A AU 2012314943A AU 2012314943 B9 AU2012314943 B9 AU 2012314943B9
Authority
AU
Australia
Prior art keywords
piperidin
benzyl
methyl
subformula
compound
Prior art date
Legal status (The legal status 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 status listed.)
Ceased
Application number
AU2012314943A
Other languages
English (en)
Other versions
AU2012314943A1 (en
AU2012314943B2 (en
Inventor
Christa Burger
Michael Busch
Oliver Poeschke
Kai Schiemann
Wolfgang Staehle
Dirk Wienke
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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 Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of AU2012314943A1 publication Critical patent/AU2012314943A1/en
Publication of AU2012314943B2 publication Critical patent/AU2012314943B2/en
Application granted granted Critical
Publication of AU2012314943B9 publication Critical patent/AU2012314943B9/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4525Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a five-membered ring with oxygen as a ring hetero atom
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4535Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom, e.g. pizotifen
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/454Non 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445Non condensed piperidines, e.g. piperocaine
    • A61K31/4523Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545Non 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/4985Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00Drugs for disorders of the senses
    • A61P27/02Ophthalmic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic 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
    • C07D403/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/02Heterocyclic 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 two hetero rings
    • C07D405/04Heterocyclic 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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic 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
    • C07D405/14Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/02Heterocyclic 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
    • C07D417/04Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Rheumatology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Urology & Nephrology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Immunology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Dermatology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
AU2012314943A 2011-09-26 2012-09-07 Benzyl piperidine compounds as lysophosphatidic acid (LPA) receptor antagonist Ceased AU2012314943B9 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP11007796 2011-09-26
EP11007796.3 2011-09-26
PCT/EP2012/003771 WO2013045028A1 (en) 2011-09-26 2012-09-07 Benzyl piperidine compounds as lysophosphatidic acid (lpa) receptor antagonist

Publications (3)

Publication Number Publication Date
AU2012314943A1 AU2012314943A1 (en) 2014-05-15
AU2012314943B2 AU2012314943B2 (en) 2017-02-02
AU2012314943B9 true AU2012314943B9 (en) 2017-06-08

Family

ID=46845693

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2012314943A Ceased AU2012314943B9 (en) 2011-09-26 2012-09-07 Benzyl piperidine compounds as lysophosphatidic acid (LPA) receptor antagonist

Country Status (9)

Country Link
US (1) US9527850B2 (enExample)
EP (1) EP2844648B1 (enExample)
JP (1) JP6163156B2 (enExample)
CN (1) CN103814024B (enExample)
AU (1) AU2012314943B9 (enExample)
CA (1) CA2849820C (enExample)
ES (1) ES2612934T3 (enExample)
IL (1) IL231699A (enExample)
WO (1) WO2013045028A1 (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2809671B1 (en) * 2012-01-30 2016-01-13 Cephalon, Inc. Imidazo [4, 5 - b]pyridine derivatives as alk and jak modulators for the treatment of proliferative disorders
US10913736B2 (en) * 2014-08-22 2021-02-09 University Of Washington Specific inhibitors of methionyl-tRNA synthetase
JP7054529B2 (ja) 2016-06-21 2022-04-14 エックス4 ファーマシューティカルズ, インコーポレイテッド Cxcr4阻害剤およびその使用
WO2017223243A1 (en) * 2016-06-21 2017-12-28 X4 Pharmaceuticals, Inc. Cxcr4 inhibitors and uses thereof
WO2018016523A1 (ja) * 2016-07-20 2018-01-25 国立大学法人 長崎大学 新規放射線防護剤
WO2020007964A1 (en) * 2018-07-05 2020-01-09 Idorsia Pharmaceuticals Ltd 2-(2-azabicyclo[3.1.0]hexan-1-yl)-1h-benzimidazole derivatives
CN113461640B (zh) * 2021-06-17 2023-08-11 中央民族大学 Lpar1抑制剂、医药用途及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009102574A1 (en) * 2008-02-13 2009-08-20 Merck & Co., Inc. Quinolizidinone m1 receptor positive allosteric modulators

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB804786A (en) * 1955-12-16 1958-11-26 Rhone Poulenc Sa New indole derivatives and process for their preparation
FR2666582B1 (fr) * 1990-09-07 1994-09-02 Synthelabo Derives de benzimidazole, leur preparation et leur application en therapeutique.
ES2048109B1 (es) * 1992-07-20 1994-12-16 Espanola Prod Quimicos Procedimiento de preparacion de nuevos derivados piperidicos del bencimidazol.
EP1695955B1 (en) 2003-12-19 2011-10-12 Ono Pharmaceutical Co., Ltd. Compounds having lysophosphatidic acid receptor antagonism and uses thereof
NZ581889A (en) * 2007-06-29 2011-05-27 Pfizer Benzimidazole derivatives
US20090062268A1 (en) * 2007-08-27 2009-03-05 Lead Therapeutics, Inc. Novel inhibitors of poly(adp-ribose)polymerase (parp)
US8530650B2 (en) * 2008-12-01 2013-09-10 Merck Patent Gmbh 2, 5-diamino-substituted pyrido [4, 3-D] pyrimidines as autotaxin inhibitors against cancer
AU2010234087B2 (en) * 2009-04-02 2016-05-12 Merck Patent Gmbh Piperidine and piperazine derivatives as autotaxin inhibitors

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009102574A1 (en) * 2008-02-13 2009-08-20 Merck & Co., Inc. Quinolizidinone m1 receptor positive allosteric modulators

Also Published As

Publication number Publication date
AU2012314943A1 (en) 2014-05-15
WO2013045028A9 (en) 2014-12-24
IL231699A (en) 2016-09-29
JP6163156B2 (ja) 2017-07-12
AU2012314943B2 (en) 2017-02-02
US9527850B2 (en) 2016-12-27
ES2612934T3 (es) 2017-05-19
WO2013045028A1 (en) 2013-04-04
CA2849820A1 (en) 2013-04-04
EP2844648B1 (en) 2016-11-09
CN103814024A (zh) 2014-05-21
JP2014526526A (ja) 2014-10-06
CN103814024B (zh) 2016-11-23
US20150011557A1 (en) 2015-01-08
CA2849820C (en) 2019-08-27
EP2844648A1 (en) 2015-03-11
IL231699A0 (en) 2014-05-28

Similar Documents

Publication Publication Date Title
AU2013212175B2 (en) Azaheterocyclic compounds
AU2012314943B9 (en) Benzyl piperidine compounds as lysophosphatidic acid (LPA) receptor antagonist
KR102086871B1 (ko) Fgfr 키나제의 억제를 통한 항암 벤조피라진
AU2012280725B2 (en) Substituted azaheterocycles for the treatment of cancer
JP7337951B2 (ja) 癌を治療するための窒素含有芳香族ヘテロ環アミド誘導体
CN103370314B (zh) 作为用于治疗癌症疾病的fgfr激酶抑制剂的取代苯并吡嗪衍生物
RU2625303C2 (ru) Хинолины в качестве модуляторов fgfr киназы
RU2629194C2 (ru) Производные 1,5- и 1,7-нафтиридина, полезные при лечении заболеваний, опосредованных fgfr
JP6549311B2 (ja) インドール誘導体、その調製方法および医薬におけるその使用
AU2012292649B8 (en) N-(Benzimidazol-2-yl)-cyclopropane carboxamides as lysophosphatidic acid antagonists
IL287740B1 (en) Maleate salts of a b-raf kinase inhibitor, crystalline forms, methods of preparation, and uses therefore
WO2019180628A1 (en) Imidazolidin-2-one compounds as prmt5 modulators
WO2014086453A1 (en) Azaheterobicyclic compounds
CN115244048A (zh) 可用于调节AhR信号传导的吡啶并嘧啶衍生物

Legal Events

Date Code Title Description
FGA Letters patent sealed or granted (standard patent)
SREP Specification republished
MK14 Patent ceased section 143(a) (annual fees not paid) or expired