CA2856386C - Heterocyclic inhibitors of glutaminase - Google Patents

Heterocyclic inhibitors of glutaminase Download PDF

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Publication number
CA2856386C
CA2856386C CA2856386A CA2856386A CA2856386C CA 2856386 C CA2856386 C CA 2856386C CA 2856386 A CA2856386 A CA 2856386A CA 2856386 A CA2856386 A CA 2856386A CA 2856386 C CA2856386 C CA 2856386C
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Prior art keywords
cancer
compound
occurrence
substituted
arylalkyl
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CA2856386A
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English (en)
French (fr)
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CA2856386A1 (en
Inventor
Jim Li
Lijing Chen
Bindu Goyal
Guy Laidig
Timothy Friend Stanton
Eric Brian Sjogren
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Calithera Biosciences Inc
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Calithera Biosciences Inc
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    • 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
    • A61K31/433—Thidiazoles
    • 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
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines 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
    • A61K31/535—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • A61P37/00—Drugs for immunological or allergic disorders
    • 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
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/20—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
    • 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
    • C07D417/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • 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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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurosurgery (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Oncology (AREA)
  • Hospice & Palliative Care (AREA)
  • Immunology (AREA)
  • Pain & Pain Management (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
CA2856386A 2011-11-21 2012-11-19 Heterocyclic inhibitors of glutaminase Active CA2856386C (en)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
US201161562266P 2011-11-21 2011-11-21
US61/562,266 2011-11-21
US201261665370P 2012-06-28 2012-06-28
US61/665,370 2012-06-28
US201261727195P 2012-11-16 2012-11-16
US61/727,195 2012-11-16
PCT/US2012/065816 WO2013078123A1 (en) 2011-11-21 2012-11-19 Heterocyclic inhibitors of glutaminase

Publications (2)

Publication Number Publication Date
CA2856386A1 CA2856386A1 (en) 2013-05-30
CA2856386C true CA2856386C (en) 2022-05-31

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CA2856386A Active CA2856386C (en) 2011-11-21 2012-11-19 Heterocyclic inhibitors of glutaminase

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EP (2) EP2782570B1 (enExample)
JP (3) JP6031527B2 (enExample)
KR (2) KR20190127971A (enExample)
CN (2) CN108785305B (enExample)
AR (1) AR090398A1 (enExample)
AU (1) AU2012340866B2 (enExample)
BR (1) BR112014012129A8 (enExample)
CA (1) CA2856386C (enExample)
CY (1) CY1122707T1 (enExample)
DK (1) DK2782570T3 (enExample)
EA (2) EA026656B1 (enExample)
ES (1) ES2761866T3 (enExample)
HR (1) HRP20192144T1 (enExample)
HU (1) HUE047642T2 (enExample)
IL (2) IL232665A0 (enExample)
LT (1) LT2782570T (enExample)
MX (1) MX362550B (enExample)
PL (1) PL2782570T3 (enExample)
PT (1) PT2782570T (enExample)
RS (1) RS59705B1 (enExample)
SG (2) SG10201607685SA (enExample)
SI (1) SI2782570T1 (enExample)
SM (1) SMT201900738T1 (enExample)
TW (1) TWI585084B (enExample)
WO (1) WO2013078123A1 (enExample)
ZA (2) ZA201404518B (enExample)

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WO2014079011A1 (en) 2012-11-22 2014-05-30 Agios Pharmaceuticals, Inc. Heterocyclic compounds for inhibiting glutaminase and their methods of use
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CN103880777B (zh) * 2014-03-06 2015-12-30 陕西科技大学 一种制备双噻二唑二胺的方法
WO2015138902A1 (en) * 2014-03-14 2015-09-17 Calithera Biosciences, Inc. Combination therapy with glutaminase inhibitors
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SG11201610333VA (en) * 2014-06-13 2017-01-27 Calithera Biosciences Inc Combination therapy with glutaminase inhibitors
PL3164394T3 (pl) 2014-07-03 2020-09-07 Board Of Regents, The University Of Texas System Inhibitory GLS1 do leczenia chorób
WO2016007647A1 (en) 2014-07-09 2016-01-14 The Johns Hopkins University Glutaminase inhibitor discovery and nanoparticle-enhanced delivery for cancer therapy
JP6889101B2 (ja) 2014-08-07 2021-06-18 キャリセラ バイオサイエンシーズ， インコーポレイテッド グルタミナーゼ阻害剤の結晶形態
WO2016054388A1 (en) 2014-10-03 2016-04-07 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Glutaminase inhibitors
JP6768693B2 (ja) * 2015-03-30 2020-10-14 キャリセラ バイオサイエンシーズ， インコーポレイテッド グルタミナーゼ阻害剤を投与する方法
BR112017021312A2 (pt) * 2015-04-06 2018-06-26 Calithera Biosciences Inc tratamento de câncer de pulmão com inibidores de glutaminase
CN107921044B (zh) 2015-06-30 2022-01-21 德州大学系统董事会 用于治疗疾病的gls1抑制剂
SG11201802830QA (en) * 2015-10-05 2018-05-30 Calithera Biosciences Inc Combination therapy with glutaminase inhibitors and immuno-oncology agents
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TW201731511A (zh) * 2015-11-30 2017-09-16 阿斯特捷利康公司 １，３，４-噻二唑化合物及其在治療癌症中之用途
KR102777513B1 (ko) 2015-12-22 2025-03-06 더 보드 오브 리젠츠 오브 더 유니버시티 오브 텍사스 시스템 (ｒ)-1-(4-(6-(2-(4-(3,3-디플루오로시클로부톡시)-6-메틸피리딘-2-일)아세트아미도)피리다진-3-일)-2-플루오로부틸)-ｎ-메틸-1ｈ-1,2,3-트리아졸-4-카르복사미드의 염 형태 및 다형체
WO2018039441A1 (en) 2016-08-25 2018-03-01 Calithera Biosciences, Inc. Combination therapy with glutaminase inhibitors
WO2018039544A1 (en) 2016-08-25 2018-03-01 Calithera Biosciences, Inc. Combination therapy with glutaminase inhibitors
US10786471B2 (en) 2017-02-06 2020-09-29 Massachusetts Institute Of Technology Methods and products related to glutaminase inhibitors
CN107137401A (zh) * 2017-03-28 2017-09-08 刘纪君 一种治疗产后抑郁症的药物组合物
CN106860460B (zh) * 2017-03-29 2019-04-23 上海市第一人民医院 谷氨酰胺酶抑制剂cb-839在制备治疗雌激素敏感型子宫内膜癌的药物中的应用
CN110741003B (zh) * 2017-06-13 2021-07-23 南京明德新药研发有限公司 作为gls1抑制剂的化合物
US10722487B2 (en) 2017-10-18 2020-07-28 Board Of Regents, The University Of Texas System Glutaminase inhibitor therapy
ES2939506T3 (es) * 2018-10-16 2023-04-24 Medshine Discovery Inc Derivado de tiadiazol y usos del mismo como inhibidor de GLS1 para el tratamiento de cáncer
CN110746416A (zh) * 2019-09-05 2020-02-04 中国药科大学 含有三氮唑结构的谷氨酰胺酶gls1抑制剂或其可药用的盐、其制备方法及用途
KR102649592B1 (ko) * 2021-08-18 2024-03-20 한국화학연구원 신규한 마크로사이클 화합물, 이의 제조방법, 이를 유효성분으로 포함하는 암 또는 자가면역질환의 예방 또는 치료용 약학적 조성물
CN116023375A (zh) * 2021-10-25 2023-04-28 成都苑东生物制药股份有限公司 一种杂环类衍生物、其制备方法及用途
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AU2012340866B2 (en) 2017-03-16
CN104220070B (zh) 2020-01-21
EA201692166A1 (ru) 2017-07-31
EP2782570B1 (en) 2019-09-18
KR20190127971A (ko) 2019-11-13
EP2782570A4 (en) 2015-05-27
KR20150000866A (ko) 2015-01-05
CN108785305B (zh) 2021-10-29
AR090398A1 (es) 2014-11-12
CA2856386A1 (en) 2013-05-30
SG11201402305WA (en) 2014-06-27
JP2014533699A (ja) 2014-12-15
MX2014005928A (es) 2014-08-27
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MX362550B (es) 2019-01-24
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CN108785305A (zh) 2018-11-13
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NZ625913A (en) 2015-12-24
CN104220070A (zh) 2014-12-17
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CY1122707T1 (el) 2021-03-12
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