AU2001282313B2 - Sulphones which modulate the action of gamma secretase - Google Patents

Sulphones which modulate the action of gamma secretase Download PDF

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Publication number
AU2001282313B2
AU2001282313B2 AU2001282313A AU2001282313A AU2001282313B2 AU 2001282313 B2 AU2001282313 B2 AU 2001282313B2 AU 2001282313 A AU2001282313 A AU 2001282313A AU 2001282313 A AU2001282313 A AU 2001282313A AU 2001282313 B2 AU2001282313 B2 AU 2001282313B2
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AU
Australia
Prior art keywords
compound
halogen
compound according
alkyl
disease
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Ceased
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AU2001282313A
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AU2001282313A1 (en
Inventor
Timothy Harrison
Paul Joseph Oakley
Martin Richard Teall
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Organon Pharma UK Ltd
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Merck Sharp and Dohme Ltd
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Publication of AU2001282313A1 publication Critical patent/AU2001282313A1/en
Application granted granted Critical
Publication of AU2001282313B2 publication Critical patent/AU2001282313B2/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • 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
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/14—Sulfones; Sulfoxides having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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
    • C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Control Of El Displays (AREA)
  • Radio Relay Systems (AREA)
  • Control Of Indicators Other Than Cathode Ray Tubes (AREA)
AU2001282313A 2001-04-05 2001-08-21 Sulphones which modulate the action of gamma secretase Ceased AU2001282313B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB0108592.7 2001-04-05
GBGB0108592.7A GB0108592D0 (en) 2001-04-05 2001-04-05 Therapeutic agents
PCT/GB2001/003778 WO2002081433A1 (en) 2001-04-05 2001-08-21 Sulphones which modulate the action of gamma secretase

Publications (2)

Publication Number Publication Date
AU2001282313A1 AU2001282313A1 (en) 2003-04-10
AU2001282313B2 true AU2001282313B2 (en) 2008-01-10

Family

ID=9912330

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2001282313A Ceased AU2001282313B2 (en) 2001-04-05 2001-08-21 Sulphones which modulate the action of gamma secretase

Country Status (9)

Country Link
US (1) US7411004B2 (https=)
EP (1) EP1379496B1 (https=)
JP (1) JP2004531517A (https=)
AT (1) ATE400550T1 (https=)
AU (1) AU2001282313B2 (https=)
CA (1) CA2442885C (https=)
DE (1) DE60134788D1 (https=)
GB (1) GB0108592D0 (https=)
WO (1) WO2002081433A1 (https=)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB0108591D0 (en) * 2001-04-05 2001-05-23 Merck Sharp & Dohme Therapeutic agents
GB0120347D0 (en) * 2001-08-21 2001-10-17 Merck Sharp & Dohme Therapeutic agents
KR100927304B1 (ko) * 2001-12-27 2009-11-18 다이이찌 세이야꾸 가부시기가이샤 β-아밀로이드 단백 생산·분비 저해제
DE10201392A1 (de) * 2002-01-16 2003-07-31 Bayer Ag Phenylsulfoxide und-sulfone
GB0223039D0 (en) 2002-10-04 2002-11-13 Merck Sharp & Dohme Therapeutic compounds
DE10254875A1 (de) * 2002-11-25 2004-06-03 Bayer Healthcare Ag Phenylsulfoxid und -sulfon-Derivate
GB0308318D0 (en) * 2003-04-10 2003-05-14 Merck Sharp & Dohme Therapeutic agents
MXPA05012323A (es) * 2003-05-16 2006-01-30 Merck Sharp & Dohme Sulfonamidas ciclicas para la inhibicion de gama-secretasa.
PL379466A1 (pl) 2003-06-30 2006-09-18 Daiichi Sankyo Company , Limited Heterocykliczne pochodne metylosulfonu
ZA200509613B (en) * 2003-06-30 2007-05-30 Daiichi Seiyaku Co Heterocyclic methyl sulfone derivative
AR047666A1 (es) * 2004-02-20 2006-02-01 Merck Sharp & Dohme Sintesis estereoselectiva del acido ciclohexanopropanoico 4,4-disubstituido
AU2006234441B2 (en) 2005-04-08 2011-07-07 Daiichi Sankyo Company, Limited Pyridylmethylsulfone derivative
ES2382814T3 (es) 2005-05-17 2012-06-13 Merck Sharp & Dohme Ltd. Ácido cis-4-[(4-clorofenil)sulfonil]-4-(2,5-difluorofenil)ciclohexanopropanoico para el tratamiento del cáncer
CA2676715A1 (en) 2007-02-12 2008-08-21 Merck & Co., Inc. Piperazine derivatives for treatment of ad and related conditions
TW200920362A (en) 2007-09-11 2009-05-16 Daiichi Sankyo Co Ltd Alkylsulfone derivatives
EP2222636B1 (en) 2007-12-21 2013-04-10 Ligand Pharmaceuticals Inc. Selective androgen receptor modulators (sarms) and uses thereof
EP2291181B9 (en) 2008-04-18 2013-09-11 University College Dublin National University Of Ireland, Dublin Captodiamine for the treatment of depression symptoms
WO2010114780A1 (en) 2009-04-01 2010-10-07 Merck Sharp & Dohme Corp. Inhibitors of akt activity
PE20121172A1 (es) 2009-10-14 2012-09-05 Merck Sharp & Dohme Piperidinas sustituidas con actividad en la hdm2
WO2011163330A1 (en) 2010-06-24 2011-12-29 Merck Sharp & Dohme Corp. Novel heterocyclic compounds as erk inhibitors
EP3330377A1 (en) 2010-08-02 2018-06-06 Sirna Therapeutics, Inc. Rna interference mediated inhibition of catenin (cadherin-associated protein), beta 1 (ctnnb1) gene expression using short interfering nucleic acid (sina)
US9029341B2 (en) 2010-08-17 2015-05-12 Sirna Therapeutics, Inc. RNA interference mediated inhibition of hepatitis B virus (HBV) gene expression using short interfering nucleic acid (siNA)
EP2613782B1 (en) 2010-09-01 2016-11-02 Merck Sharp & Dohme Corp. Indazole derivatives useful as erk inhibitors
US9242981B2 (en) 2010-09-16 2016-01-26 Merck Sharp & Dohme Corp. Fused pyrazole derivatives as novel ERK inhibitors
WO2012058210A1 (en) 2010-10-29 2012-05-03 Merck Sharp & Dohme Corp. RNA INTERFERENCE MEDIATED INHIBITION OF GENE EXPRESSION USING SHORT INTERFERING NUCLEIC ACIDS (siNA)
WO2012087772A1 (en) 2010-12-21 2012-06-28 Schering Corporation Indazole derivatives useful as erk inhibitors
EP2770987B1 (en) 2011-10-27 2018-04-04 Merck Sharp & Dohme Corp. Novel compounds that are erk inhibitors
US20150299696A1 (en) 2012-05-02 2015-10-22 Sirna Therapeutics, Inc. SHORT INTERFERING NUCLEIC ACID (siNA) COMPOSITIONS
RU2660429C2 (ru) 2012-09-28 2018-07-06 Мерк Шарп И Доум Корп. Новые соединения, которые являются ингибиторами erk
RS56680B1 (sr) 2012-11-28 2018-03-30 Merck Sharp & Dohme Kompozicije i postupci za lečenje kancera
KR102196882B1 (ko) 2012-12-20 2020-12-30 머크 샤프 앤드 돔 코포레이션 Hdm2 억제제로서의 치환된 이미다조피리딘
WO2014120748A1 (en) 2013-01-30 2014-08-07 Merck Sharp & Dohme Corp. 2,6,7,8 substituted purines as hdm2 inhibitors
WO2015034925A1 (en) 2013-09-03 2015-03-12 Moderna Therapeutics, Inc. Circular polynucleotides
US10441567B2 (en) 2014-01-17 2019-10-15 Ligand Pharmaceuticals Incorporated Methods and compositions for modulating hormone levels
EP3525785B1 (en) 2016-10-12 2025-08-27 Merck Sharp & Dohme LLC Kdm5 inhibitors
EP3706747B1 (en) 2017-11-08 2025-09-03 Merck Sharp & Dohme LLC Prmt5 inhibitors
US10947234B2 (en) 2017-11-08 2021-03-16 Merck Sharp & Dohme Corp. PRMT5 inhibitors
US12552826B2 (en) 2018-08-07 2026-02-17 Merck Sharp & Dohme Llc PRMT5 inhibitors
US11981701B2 (en) 2018-08-07 2024-05-14 Merck Sharp & Dohme Llc PRMT5 inhibitors
US12173026B2 (en) 2018-08-07 2024-12-24 Merck Sharp & Dohme Llc PRMT5 inhibitors
EP3833668B1 (en) 2018-08-07 2025-03-19 Merck Sharp & Dohme LLC Prmt5 inhibitors
WO2020214834A1 (en) 2019-04-19 2020-10-22 Ligand Pharmaceuticals Inc. Crystalline forms and methods of producing crystalline forms of a compound
US12595248B2 (en) 2019-12-17 2026-04-07 Merck Sharp & Dohme Llc PRMT5 inhibitors
US12441730B2 (en) 2019-12-17 2025-10-14 Merck Sharp & Dohme Llc PRMT5 inhibitors
BR112022012015A2 (pt) 2019-12-17 2022-08-30 Merck Sharp & Dohme Llc Inibidores de prmt5
WO2021126731A1 (en) 2019-12-17 2021-06-24 Merck Sharp & Dohme Corp. Prmt5 inhibitors
JP7595854B2 (ja) * 2020-05-25 2024-12-09 地方独立行政法人大阪産業技術研究所 ［６，６］メタノフラーレン誘導体の製造方法
US20240116945A1 (en) 2022-09-02 2024-04-11 Merck Sharp & Dohme Llc Exatecan-derived topoisomerase-1 inhibitors pharmaceutical compositions, and uses thereof
WO2024091437A1 (en) 2022-10-25 2024-05-02 Merck Sharp & Dohme Llc Exatecan-derived adc linker-payloads, pharmaceutical compositions, and uses thereof
GEAP202516798A (en) 2022-12-14 2025-10-27 Merck Sharp & Dohme Llc Auristatin linker-payloads, pharmaceutical compositions, and uses thereof

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3016403A (en) * 1955-07-29 1962-01-09 Searle & Co 1-aryl-3-hydroxypropyl sulfones and processes
JPS537691A (en) * 1976-07-09 1978-01-24 Yoshitomi Pharmaceut Ind Ltd Piperazines
DE2735314A1 (de) * 1977-08-05 1979-02-22 Basf Ag Alpha-azolylsulfide und deren derivate
US4675316A (en) * 1978-03-10 1987-06-23 Rohm And Haas Company Substituted azoylmethylarylsulfides and derivatives and pesticidal use thereof
DE2821829A1 (de) * 1978-05-19 1979-11-22 Basf Ag Mittel zur regulierung des pflanzenwachstums
JPS5626847A (en) 1979-08-13 1981-03-16 Sagami Chem Res Center Preparation of substituted salicylic acid derivative
JPS5716840A (en) * 1980-07-03 1982-01-28 Sagami Chem Res Center Phneylacetic acid derivative
US4379921A (en) * 1980-08-21 1983-04-12 Sumitomo Chemical Company, Limited Production of triazolylvinyl ketones
FR2593178B1 (fr) * 1986-01-20 1988-04-29 Esteve Labor Dr Derives de 2-benzimidazolylalkylthio (ou sulfinyle ou sulfonyle) leur preparation et leur application en tant que medicaments.
JPS62181260A (ja) * 1986-02-06 1987-08-08 Nippon Kayaku Co Ltd ピリジン誘導体およびそれを有効成分とする農園芸用殺菌剤
JP3582070B2 (ja) * 1994-08-11 2004-10-27 日本曹達株式会社 フェニルエタン誘導体及びそれを用いた感熱記録材料
JP2001505869A (ja) * 1996-07-22 2001-05-08 モンサント カンパニー チオールスルホン メタロプロテアーゼ阻害剤
US5703129A (en) 1996-09-30 1997-12-30 Bristol-Myers Squibb Company 5-amino-6-cyclohexyl-4-hydroxy-hexanamide derivatives as inhibitors of β-amyloid protein production
NZ514453A (en) 1999-02-26 2003-04-29 Merck & Co Inc Novel sulfonamide compounds and uses thereof
SE9901901D0 (sv) * 1999-05-26 1999-05-26 Astra Ab Compounds
KR100927304B1 (ko) 2001-12-27 2009-11-18 다이이찌 세이야꾸 가부시기가이샤 β-아밀로이드 단백 생산·분비 저해제
DE10201392A1 (de) 2002-01-16 2003-07-31 Bayer Ag Phenylsulfoxide und-sulfone

Also Published As

Publication number Publication date
US7411004B2 (en) 2008-08-12
ATE400550T1 (de) 2008-07-15
US20040082617A1 (en) 2004-04-29
EP1379496A1 (en) 2004-01-14
CA2442885A1 (en) 2002-10-17
EP1379496B1 (en) 2008-07-09
DE60134788D1 (de) 2008-08-21
GB0108592D0 (en) 2001-05-23
WO2002081433A1 (en) 2002-10-17
JP2004531517A (ja) 2004-10-14
CA2442885C (en) 2010-06-29

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