KR102189562B1 - 아실-하이드라존 및 옥사디아졸 화합물, 이를 포함하는 약학 조성물 및 이의 용도 - Google Patents

아실-하이드라존 및 옥사디아졸 화합물, 이를 포함하는 약학 조성물 및 이의 용도 Download PDF

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KR102189562B1
KR102189562B1 KR1020147017498A KR20147017498A KR102189562B1 KR 102189562 B1 KR102189562 B1 KR 102189562B1 KR 1020147017498 A KR1020147017498 A KR 1020147017498A KR 20147017498 A KR20147017498 A KR 20147017498A KR 102189562 B1 KR102189562 B1 KR 102189562B1
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phenyl
compound
leukemia
compounds
och
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KR20140112489A (ko
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리카르도 호세 누네스
알레산드라 마스카렐로
로센도 아우구스토 유네스
타이사 레지나 슈툼프
파울로 세자르 릴
호세 안드레스 유네스
카롤리나 페레이라 데 수자 멜로
라파엘 레나티노 카네바롤로
루이스 도메네기니 키아라디아
안드레 보톨리니 실베리아
안켈로 브루넬리 알베르토니 라란제이라
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유니베르시다데 페더랄 데 산타 카타리나
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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
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
    • A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
    • 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
    • A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
    • A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered 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
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/72—Hydrazones
    • C07C251/86—Hydrazones having doubly-bound carbon atoms of hydrazone groups bound to carbon atoms of six-membered aromatic rings
    • 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • 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
    • C07D271/107—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with two aryl or substituted aryl radicals attached in positions 2 and 5
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/36—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/42—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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 with nitro or nitroso radicals directly attached to ring carbon atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
KR1020147017498A 2011-11-25 2012-11-26 아실-하이드라존 및 옥사디아졸 화합물, 이를 포함하는 약학 조성물 및 이의 용도 Active KR102189562B1 (ko)

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Application Number Priority Date Filing Date Title
BRPI1107312-8 2011-11-25
BRPI1107312-8A BRPI1107312B1 (pt) 2011-11-25 2011-11-25 Composto de acil-hidrazona
PCT/BR2012/000480 WO2013075199A1 (pt) 2011-11-25 2012-11-26 "compostos acil-hidrazonas e oxadiazóis, composições farmacêuticas compreendendo os mesmos e seus usos

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KR20140112489A KR20140112489A (ko) 2014-09-23
KR102189562B1 true KR102189562B1 (ko) 2020-12-14

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US (1) US20150191445A1 (enExample)
EP (1) EP2784061B1 (enExample)
JP (1) JP2015504432A (enExample)
KR (1) KR102189562B1 (enExample)
CN (1) CN104159887A (enExample)
BR (2) BRPI1107312B1 (enExample)
CA (1) CA2869807C (enExample)
RU (1) RU2664327C2 (enExample)
WO (1) WO2013075199A1 (enExample)

Families Citing this family (5)

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KR101719541B1 (ko) 2015-08-13 2017-03-24 연세대학교 산학협력단 항암용 약학 조성물 및 ano1 활성억제제
KR20170141542A (ko) * 2016-06-15 2017-12-26 국립암센터 위암을 예방 및 치료하는 rhoa 억제제의 약학적 조성물
CN110498809B (zh) * 2018-05-17 2022-04-05 香港科技大学深圳研究院 基于酰腙配体类的有机硼化合物及其制备方法和应用
KR102131331B1 (ko) 2018-09-19 2020-07-07 연세대학교 산학협력단 항암용 신규 약학 조성물 및 ano1 활성억제제
CN113336729B (zh) * 2021-05-31 2022-05-27 四川大学华西医院 硝呋齐特类衍生物及其制备方法和用途

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110189306A1 (en) * 2010-01-13 2011-08-04 Norbert Kartner COMPOUNDS, COMPOSITIONS AND TREATMENTS FOR V-ATPase RELATED DISEASES

Family Cites Families (11)

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Publication number Priority date Publication date Assignee Title
JPS60105621A (ja) * 1983-11-14 1985-06-11 Agency Of Ind Science & Technol 細胞の分化誘導作用を有する生理活性物質およびその製法
IL94389A0 (en) * 1989-06-01 1991-03-10 Health Research Inc Monoclonal antibody reactive to a unique antigen widely present on various human leukemia and lymphoma cells and method of using same for diagnosis and treatment
US5372808A (en) * 1990-10-17 1994-12-13 Amgen Inc. Methods and compositions for the treatment of diseases with consensus interferon while reducing side effect
US6197806B1 (en) * 1995-12-20 2001-03-06 Nippon Zoki Pharmaceutical Co., Ltd. Eliminating agent for activated oxygen and free radicals
CA2400996A1 (en) 2002-09-03 2004-03-03 Lisa Mckerracher 1,4-substituted cyclohexane derivatives
MXPA06007399A (es) 2003-12-23 2007-01-26 Gpc Biotech Inc Inhibidores de quinasas dependientes de ciclina, composiciones y usos relacionados con ellos.
DE102004010207A1 (de) 2004-03-02 2005-09-15 Aventis Pharma S.A. Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate
RU2365589C2 (ru) * 2004-04-01 2009-08-27 Авентис Фармасьютикалз Инк. 1,3,4-оксадиазол-2-оны в качестве модуляторов ppar-дельта, фармацевтические композиции на их основе и способ лечения
AR052559A1 (es) 2005-01-21 2007-03-21 Astex Therapeutics Ltd Derivados de pirazol para inhibir cdk's y gsk's
US7662824B2 (en) 2005-03-18 2010-02-16 Janssen Pharmaceutica Nv Acylhydrazones as kinase modulators
CN1824657A (zh) * 2006-04-05 2006-08-30 贵州大学 3－取代－2－芳基取代－5－(3,4,5－三烷氧基苯基)－1,3,4－噁二唑衍生物及制备方法和用途

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110189306A1 (en) * 2010-01-13 2011-08-04 Norbert Kartner COMPOUNDS, COMPOSITIONS AND TREATMENTS FOR V-ATPase RELATED DISEASES

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
J. Med. Chem. 2010, Vol.53, pp.325-334, 1부.*
Journal of the Brazilian Chemical Society, 2010, Vol.21, No.1, pp.142-150, 1부.*
Journal of the Chinese Chemical Society, 2011, Vol.58, No.1, pp.35-40, 1부.*

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Publication number Publication date
CN104159887A (zh) 2014-11-19
WO2013075199A1 (pt) 2013-05-30
BRPI1107312B1 (pt) 2021-09-08
CA2869807C (en) 2021-03-09
JP2015504432A (ja) 2015-02-12
CA2869807A1 (en) 2013-05-30
KR20140112489A (ko) 2014-09-23
EP2784061A4 (en) 2015-05-27
EP2784061A1 (en) 2014-10-01
EP2784061B1 (en) 2018-11-07
BR112014012582A2 (pt) 2017-06-06
RU2664327C2 (ru) 2018-08-16
US20150191445A1 (en) 2015-07-09
RU2014125519A (ru) 2015-12-27
BRPI1107312A2 (pt) 2016-09-20

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