WO2015009882A3 - Cyano derivatives and their uses - Google Patents

Cyano derivatives and their uses Download PDF

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Publication number
WO2015009882A3
WO2015009882A3 PCT/US2014/046937 US2014046937W WO2015009882A3 WO 2015009882 A3 WO2015009882 A3 WO 2015009882A3 US 2014046937 W US2014046937 W US 2014046937W WO 2015009882 A3 WO2015009882 A3 WO 2015009882A3
Authority
WO
WIPO (PCT)
Prior art keywords
cyano
ethyl
hydrazinecarbonyl
methylguanidine
methylthio
Prior art date
Application number
PCT/US2014/046937
Other languages
French (fr)
Other versions
WO2015009882A2 (en
Inventor
M. Bud Nelson
Dhanalekshmi SAVITHRI
Thiagarajan Balasubramanian
Original Assignee
The Hamner Institutes
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 The Hamner Institutes filed Critical The Hamner Institutes
Publication of WO2015009882A2 publication Critical patent/WO2015009882A2/en
Publication of WO2015009882A3 publication Critical patent/WO2015009882A3/en

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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D233/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54Heterocyclic 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
    • C07D233/66Heterocyclic 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 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
    • C07D233/90Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Compounds inhibit Nrf2 activity for treatment of mycobacterial infection, granulomatous inflammation, tuberculosis, viral infection, or cancer include 5-((2-(2-cyano-3-methylguanidino)ethylthio)methyl)-1 H-imidazole-4carboxamide; 2-cyano-1-(2-( ( 4-hydrazinecarbonyl)-1 H-im idazol-5-yl)methylthio )ethyl-3-methylguanidine; 5-((2-(2-cyano-3-methylguanidino)ethylthio)methyl)-1 H-imidazole-2-carboxamide; 2-cyano-1-(2-((2-hydrazinecarbonyl)-1 H-imidazol-5-yl)methylthio)ethyl-3-methylguanidine; 2-cyano-1-methyl-3-(2-((4- methyl-1 H-imidazol-5-yl)methylamino)ethylguanidine; 3-( ( 2-(2-cyano-3-m ethylg uan idino) ethylth io) m ethyl)pyrazine-2-carboxamide; 6-( ( 2-(2-cyano-3-m ethylg uan idino) ethylth io) m ethyl)pyrazine-2-carboxamide; 2-cyano-1-(2-( ( 4-hydrazinecarbonyl)pyridine-2-yl) methylthio )ethyl-3-methylguanidine; and 2-cyano-1-(2-( ( 4-hydrazinecarbonyl)pyridine-3-yl) methylthio)ethyl-3-methylguanidine; or a pharmaceutically acceptable salt thereof.
PCT/US2014/046937 2013-07-18 2014-07-17 Cyano derivatives and their uses WO2015009882A2 (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
US201361847630P 2013-07-18 2013-07-18
US61/847,630 2013-07-18
US201361891956P 2013-10-17 2013-10-17
US61/891,956 2013-10-17
US201361908215P 2013-11-25 2013-11-25
US61/908,215 2013-11-25
US201462025049P 2014-07-16 2014-07-16
US62/025,049 2014-07-16

Publications (2)

Publication Number Publication Date
WO2015009882A2 WO2015009882A2 (en) 2015-01-22
WO2015009882A3 true WO2015009882A3 (en) 2015-11-12

Family

ID=52346842

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2014/046937 WO2015009882A2 (en) 2013-07-18 2014-07-17 Cyano derivatives and their uses

Country Status (1)

Country Link
WO (1) WO2015009882A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201510077D0 (en) * 2015-06-10 2015-07-22 Novabiotics Ltd Use
CN114394939A (en) * 2022-01-27 2022-04-26 河北科技大学 Synthesis method of cimetidine

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5422350A (en) * 1992-09-10 1995-06-06 Warner-Lambert Company Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use
US5541212A (en) * 1994-01-10 1996-07-30 Metatron, Inc. Use of cimetidine for the control of retrovirus infections
US20020077343A1 (en) * 1998-11-17 2002-06-20 David S. Garvey H2 receptor antagonist compounds in combination with nitric oxide donors, compostions and methods of use
US20070281906A1 (en) * 2001-12-06 2007-12-06 Dalton James T Selective androgen receptor modulators for treating diabetes
US20080274104A1 (en) * 2005-02-10 2008-11-06 Arlinghaus Ralph B Targeting a Secreted Pro-Apoptotic Factor for Cancer Therapeutics

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5422350A (en) * 1992-09-10 1995-06-06 Warner-Lambert Company Nitrogen substituted acridine and cytochrome P450 inhibitors and methods of use
US5541212A (en) * 1994-01-10 1996-07-30 Metatron, Inc. Use of cimetidine for the control of retrovirus infections
US20020077343A1 (en) * 1998-11-17 2002-06-20 David S. Garvey H2 receptor antagonist compounds in combination with nitric oxide donors, compostions and methods of use
US20070281906A1 (en) * 2001-12-06 2007-12-06 Dalton James T Selective androgen receptor modulators for treating diabetes
US20080274104A1 (en) * 2005-02-10 2008-11-06 Arlinghaus Ralph B Targeting a Secreted Pro-Apoptotic Factor for Cancer Therapeutics

Also Published As

Publication number Publication date
WO2015009882A2 (en) 2015-01-22

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