CA2792598C - Improved cysteine-based prodrugs useful in the treatment of schizophrenia - Google Patents

Improved cysteine-based prodrugs useful in the treatment of schizophrenia Download PDF

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Publication number
CA2792598C
CA2792598C CA2792598A CA2792598A CA2792598C CA 2792598 C CA2792598 C CA 2792598C CA 2792598 A CA2792598 A CA 2792598A CA 2792598 A CA2792598 A CA 2792598A CA 2792598 C CA2792598 C CA 2792598C
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group
acid
compound
compounds
alkyl
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Expired - Fee Related
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CA2792598A
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English (en)
French (fr)
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CA2792598A1 (en
Inventor
Mark A. Wolf
Keith D. Barnes
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Promentis Pharmaceuticals Inc
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Promentis Pharmaceuticals Inc
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    • 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
    • C07D241/06—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members
    • C07D241/08—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having one or two double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/22—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • 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
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/56—Amides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or 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
    • C07D263/44—Two oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members 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
    • 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
    • C07D413/12—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 linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biomedical Technology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Psychiatry (AREA)
  • Public Health (AREA)
  • Neurosurgery (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Addiction (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Saccharide Compounds (AREA)
CA2792598A 2010-03-10 2011-03-08 Improved cysteine-based prodrugs useful in the treatment of schizophrenia Expired - Fee Related CA2792598C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US31262510P 2010-03-10 2010-03-10
US61/312,625 2010-03-10
PCT/US2011/027476 WO2011112535A2 (en) 2010-03-10 2011-03-08 Propionic acids, propionic acid esters, and related compounds

Publications (2)

Publication Number Publication Date
CA2792598A1 CA2792598A1 (en) 2011-09-15
CA2792598C true CA2792598C (en) 2018-06-19

Family

ID=44560545

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2792598A Expired - Fee Related CA2792598C (en) 2010-03-10 2011-03-08 Improved cysteine-based prodrugs useful in the treatment of schizophrenia

Country Status (5)

Country Link
US (1) US8815905B2 (enExample)
EP (2) EP2545033A4 (enExample)
JP (2) JP5978136B2 (enExample)
CA (1) CA2792598C (enExample)
WO (1) WO2011112535A2 (enExample)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5978136B2 (ja) * 2010-03-10 2016-08-24 プロメンテイス・フアーマシユーテイカルズ・インコーポレイテツド プロピオン酸、プロピオン酸エステルおよび関連化合物
AU2014346591B2 (en) 2013-11-08 2018-09-27 Promentis Pharmaceuticals, Inc. Substituted N-acetyl-L-cysteine derivatives and related compounds
US9193681B1 (en) * 2014-05-30 2015-11-24 Promentis Pharmaceuticals, Inc. Propionic acids, propionic acid esters, and related compounds
WO2018174839A1 (en) * 2017-03-18 2018-09-27 Nguyen Mark Quang Cysteine, n-acetylcysteine and penicillamine prodrugs, pharmaceutical compositions thereof, and methods of use
KR102371529B1 (ko) 2020-02-14 2022-03-07 구글 엘엘씨 다수 당사자 도달 및 빈도 추정 보안화

Family Cites Families (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4520028A (en) * 1984-04-06 1985-05-28 Merrell Dow Pharmaceuticals Inc. α-Aminobutyric acid transaminase inhibitors
US6632922B1 (en) * 1998-03-19 2003-10-14 The Regents Of The University Of California Methods and compositions for controlled polypeptide synthesis
JPH11292743A (ja) * 1998-04-03 1999-10-26 Seiwa Kasei Kk パーマネントウェーブ用第１剤
ITMI20011308A1 (it) * 2001-06-21 2002-12-21 Nicox Sa Farmaci per il dolore cronico
ITMI20011307A1 (it) * 2001-06-21 2002-12-21 Nicox Sa Farmaci per l'epilessia
CA2453433A1 (en) * 2001-08-10 2003-02-20 Nitromed, Inc. Methods of use for novel sulfur containing organic nitrate compounds
US6623723B2 (en) * 2001-08-21 2003-09-23 Cellular Sciences Inc. Method for treating bronchial constriction and bronchospasm
JP4927563B2 (ja) * 2003-12-30 2012-05-09 ゼノポート，インコーポレイティド アシルオキシアルキルカルバメートプロドラッグ及び中間体の合成
CN1939912A (zh) * 2005-10-01 2007-04-04 代斌 N－[2－(3－苯基－2－丙烯酰氨基)丙酰基]－噻唑烷酸及其衍生物制备方法
US8138227B2 (en) * 2006-07-06 2012-03-20 Trustees Of Dartmouth College Method for inhibiting or reversing non-enzymatic glycation
WO2008013860A2 (en) * 2006-07-28 2008-01-31 Xenoport, Inc. Acyloxyalkyl carbamate prodrugs of alpha-amino acids, methods of synthesis and use
US7829709B1 (en) * 2007-08-10 2010-11-09 Marquette University Cysteine prodrugs to treat schizophrenia and drug addiction
EP2252596B1 (en) * 2008-02-07 2016-12-28 Marquette University Cysteine and cystine prodrugs to treat schizophrenia and reduce drug cravings
EP2265594A2 (en) * 2008-04-16 2010-12-29 Marquette University Cysteine and cystine bioisosteres to treat schizophrenia and reduce drug cravings
JP5978136B2 (ja) * 2010-03-10 2016-08-24 プロメンテイス・フアーマシユーテイカルズ・インコーポレイテツド プロピオン酸、プロピオン酸エステルおよび関連化合物
US8624052B2 (en) * 2010-11-12 2014-01-07 Promentis Pharmaceuticals, Inc. S-t-butyl protected cysteine di-peptide analogs and related compounds
AU2014346591B2 (en) * 2013-11-08 2018-09-27 Promentis Pharmaceuticals, Inc. Substituted N-acetyl-L-cysteine derivatives and related compounds
US9193681B1 (en) * 2014-05-30 2015-11-24 Promentis Pharmaceuticals, Inc. Propionic acids, propionic acid esters, and related compounds

Also Published As

Publication number Publication date
US8815905B2 (en) 2014-08-26
JP2013522207A (ja) 2013-06-13
CA2792598A1 (en) 2011-09-15
JP5978136B2 (ja) 2016-08-24
JP2016166191A (ja) 2016-09-15
US20110224156A1 (en) 2011-09-15
EP2937334B1 (en) 2017-04-19
EP2937334A1 (en) 2015-10-28
EP2545033A4 (en) 2013-08-21
WO2011112535A3 (en) 2011-12-22
EP2545033A2 (en) 2013-01-16
WO2011112535A2 (en) 2011-09-15

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