AU2018256285B2 - Small molecule inhibitors of Bcl-2-associated death promoter (BAD) phosphorylation - Google Patents

Small molecule inhibitors of Bcl-2-associated death promoter (BAD) phosphorylation Download PDF

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Publication number
AU2018256285B2
AU2018256285B2 AU2018256285A AU2018256285A AU2018256285B2 AU 2018256285 B2 AU2018256285 B2 AU 2018256285B2 AU 2018256285 A AU2018256285 A AU 2018256285A AU 2018256285 A AU2018256285 A AU 2018256285A AU 2018256285 B2 AU2018256285 B2 AU 2018256285B2
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compound
methyl
piperazin
aryl
dichlorophenyl
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AU2018256285A1 (en
Inventor
Mohan CHAKRABHAVI DHANANJAYA
Rangappa Kanchugarakoppal Subbegowda
Peter Edward Lobie
Vijay Kumar Pandey
Shobith Rangappa
Bassappa SALUNDI
Srinivasa VENKATACHALAIAH
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BANGALORE UNIVERSITY
University of Mysore
National University of Singapore
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Bangalore Univ
Of Mysore, University of
University of Mysore
National University of Singapore
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic 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
    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/53—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
    • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
    • C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • 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
    • C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
    • C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/06—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 two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen 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
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/06—Peri-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Furan Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Management, Administration, Business Operations System, And Electronic Commerce (AREA)
  • Professional, Industrial, Or Sporting Protective Garments (AREA)
AU2018256285A 2017-04-19 2018-04-18 Small molecule inhibitors of Bcl-2-associated death promoter (BAD) phosphorylation Active AU2018256285B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB1706162.3 2017-04-19
GBGB1706162.3A GB201706162D0 (en) 2017-04-19 2017-04-19 Compounds
PCT/SG2018/050194 WO2018194520A1 (en) 2017-04-19 2018-04-18 Small molecule inhibitors of bcl-2-associated death promoter (bad) phosphorylation

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AU2018256285A1 AU2018256285A1 (en) 2019-11-07
AU2018256285B2 true AU2018256285B2 (en) 2022-08-04

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US (1) US11292773B2 (https=)
EP (1) EP3612518A4 (https=)
JP (1) JP7423010B2 (https=)
KR (1) KR102753110B1 (https=)
CN (1) CN110719906B (https=)
AU (1) AU2018256285B2 (https=)
CA (1) CA3060939A1 (https=)
GB (1) GB201706162D0 (https=)
IL (1) IL270078B (https=)
MX (1) MX2024000001A (https=)
SG (1) SG11201909418WA (https=)
WO (1) WO2018194520A1 (https=)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201706162D0 (en) * 2017-04-19 2017-05-31 Nat Univ Singapore Compounds
CN112481298A (zh) * 2020-11-11 2021-03-12 清华-伯克利深圳学院筹备办公室 重组质粒及其应用
CN115340527B (zh) * 2021-05-13 2023-09-15 成都先导药物开发股份有限公司 一种bcl-xl抑制剂及其制备方法和用途

Citations (2)

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WO2001007050A1 (en) * 1999-07-26 2001-02-01 Schering Corporation Nociceptin receptor orl-1 agonists for use in treating cough
US20130096133A1 (en) * 2011-10-14 2013-04-18 The Board of Trustees of the University lllinois Procaspase-activating compounds and compositions

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WO2010052448A2 (en) * 2008-11-05 2010-05-14 Ucb Pharma S.A. Fused pyrazine derivatives as kinase inhibitors
JP2017128541A (ja) * 2016-01-21 2017-07-27 学校法人東京女子医科大学 アポトーシス誘導剤
GB201706162D0 (en) * 2017-04-19 2017-05-31 Nat Univ Singapore Compounds

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WO2001007050A1 (en) * 1999-07-26 2001-02-01 Schering Corporation Nociceptin receptor orl-1 agonists for use in treating cough
US20130096133A1 (en) * 2011-10-14 2013-04-18 The Board of Trustees of the University lllinois Procaspase-activating compounds and compositions

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ALAN R. KATRITZKY ET AL, "Amino(hetero)arylmethylation of Phenols with N -[[alpha]-Amino(hetero)arylmethyl]benzotriazoles", JOURNAL OF ORGANIC CHEMISTRY, US, (1999-08-01), vol. 64, no. 16, pages 6071 - 6075 *
CHRISTOV K. et al., "Short-term Modulation of Cell Proliferation and Apoptosis and Preventive/Therapeutic Efficacy of Various Agents in a Mammary Cancer Model", Clin. Cancer Res., vol. 13, no. 18, 2007, pages 5488 - 5496, *
HOSSEINZADEH R. et al., "A green protocol for the one-pot multicomponent Petasis boronic Mannich reaction using ball milling", J. Iran. Chem. Soc., vol. 14, no. 2, (2016-10-04), pages 347 - 355, (2018-06-13) *
KARUBE K. et al., "Comprehensive gene expression profiles of NK cell neoplasms identify vorinostat as an effective drug candidate", Cancer Lett., vol. 333, no. 1, (2013-01-21), pages 47 - 55, (2018-06-13) *
LIN Ho. J.-C. et al., "Induction of apoptosis and cell -cycle arrest in human colon cancer cells by meclizine", Food Chem. Toxicol., vol. 45, no. 6, (2006-12-09), pages 935 - 944, (2018-06-13) *
RICHARD D. J. et al., "Hydroxyquinoline-derived compounds and analoguing of selective Mcl-1 inhibitors using a functional biomarker", Bioorg Med Chem., vol. 21, no. 21, (2013-08-15), pages 6642 - 6649, (2018-06-15) *
S. TABASSUM ET AL, "Sonochemistry - an innovative opportunity towards a one-pot three-component synthesis of novel pyridylpiperazine derivatives ...", NEW JOURNAL OF CHEMISTRY, 2017, vol. 41, no. 9, pages 3515 - 3523 *
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Publication number Publication date
WO2018194520A9 (en) 2019-10-17
IL270078B (en) 2022-09-01
US20200131139A1 (en) 2020-04-30
WO2018194520A1 (en) 2018-10-25
JP2020517745A (ja) 2020-06-18
EP3612518A1 (en) 2020-02-26
GB201706162D0 (en) 2017-05-31
JP7423010B2 (ja) 2024-01-29
CA3060939A1 (en) 2018-10-25
US11292773B2 (en) 2022-04-05
CN110719906A (zh) 2020-01-21
MX2024000001A (es) 2024-02-20
KR102753110B1 (ko) 2025-01-09
KR20200029384A (ko) 2020-03-18
RU2019135562A (ru) 2021-05-19
SG11201909418WA (en) 2019-11-28
AU2018256285A1 (en) 2019-11-07
CN110719906B (zh) 2023-07-28
IL270078A (https=) 2019-12-31
RU2019135562A3 (https=) 2021-07-21
BR112019022015A2 (pt) 2020-05-12
EP3612518A4 (en) 2020-11-25

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