CA2498111A1 - Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors - Google Patents

Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors Download PDF

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Publication number
CA2498111A1
CA2498111A1 CA002498111A CA2498111A CA2498111A1 CA 2498111 A1 CA2498111 A1 CA 2498111A1 CA 002498111 A CA002498111 A CA 002498111A CA 2498111 A CA2498111 A CA 2498111A CA 2498111 A1 CA2498111 A1 CA 2498111A1
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CA
Canada
Prior art keywords
alkyl
haloalkyl
dihydroxy
pyrido
pyrazine
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002498111A
Other languages
English (en)
French (fr)
Inventor
John S. Wai
Boyoung Kim
Thorsten E. Fisher
Linghang Zhuang
Peter D. Williams
Terry A. Lyle
H. Marie Langford
Kyle A. Robinson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2498111A1 publication Critical patent/CA2498111A1/en
Abandoned legal-status Critical Current

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    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/14—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • 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
    • C07D471/04—Ortho-condensed systems

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Virology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA002498111A 2002-09-11 2003-09-10 Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors Abandoned CA2498111A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US40974102P 2002-09-11 2002-09-11
US60/409,741 2002-09-11
PCT/US2003/028366 WO2004024078A2 (en) 2002-09-11 2003-09-10 Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors

Publications (1)

Publication Number Publication Date
CA2498111A1 true CA2498111A1 (en) 2004-03-25

Family

ID=31993997

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002498111A Abandoned CA2498111A1 (en) 2002-09-11 2003-09-10 Dihydroxypyridopyrazine-1,6-dione compounds useful as hiv integrase inhibitors

Country Status (6)

Country Link
US (1) US7517532B2 (cg-RX-API-DMAC7.html)
EP (1) EP1549315A4 (cg-RX-API-DMAC7.html)
JP (1) JP2006506352A (cg-RX-API-DMAC7.html)
AU (1) AU2003267098B2 (cg-RX-API-DMAC7.html)
CA (1) CA2498111A1 (cg-RX-API-DMAC7.html)
WO (1) WO2004024078A2 (cg-RX-API-DMAC7.html)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066414A1 (en) * 2004-12-23 2006-06-29 Virochem Pharma Inc. Hydroxydihydropyridopy razine-1,8-diones and methods for inhibiting hiv integrase
US8410103B2 (en) 2005-04-28 2013-04-02 Shionogi & Co., Ltd. (3S,11aR)-N-[2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide useful as anti-HIV agent

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WO2004047725A2 (en) * 2002-09-11 2004-06-10 Merck & Co. Inc. 8-hydroxy-1-oxo-tetrahydropyrrolopyrazine compounds useful as hiv integrase inhibitors
TW200510425A (en) 2003-08-13 2005-03-16 Japan Tobacco Inc Nitrogen-containing fused ring compound and use thereof as HIV integrase inhibitor
JP2005232103A (ja) * 2004-02-20 2005-09-02 Nagase & Co Ltd 光学活性なビシナルジアミンおよびその製造方法
WO2005120516A2 (en) 2004-06-09 2005-12-22 Merck & Co., Inc. Hiv integrase inhibitors
US7745459B2 (en) 2004-09-21 2010-06-29 Japan Tobacco Inc. Quinolizinone compound and use thereof as HIV integrase inhibitor
JP5317257B2 (ja) * 2005-02-21 2013-10-16 塩野義製薬株式会社 Ｈｉｖインテグラーゼ阻害活性を有する２環性カルバモイルピリドン誘導体
CA2967430C (en) * 2005-03-10 2018-05-08 Gen-Probe Incorporated Systems and methods to perform assays for detecting or quantifying analytes within samples
AU2006244072B2 (en) 2005-05-10 2012-09-20 Intermune, Inc. Pyridone derivatives for modulating stress-activated protein kinase system
US20090312335A1 (en) * 2005-10-27 2009-12-17 John S Wai Hiv Integrase Inhibitors
AU2006307101A1 (en) 2005-10-27 2007-05-03 Shionogi & Co., Ltd. Polycyclic carbamoylpyridone derivative having inhibitory activity on HIV integrase
EP2296653B1 (en) 2008-06-03 2016-01-27 Intermune, Inc. Compounds and methods for treating inflammatory and fibrotic disorders
KR101772610B1 (ko) 2008-07-25 2017-09-12 비이브 헬쓰케어 컴퍼니 화합물
KR101682058B1 (ko) 2008-12-11 2016-12-02 비이브 헬쓰케어 컴퍼니 카르바모일피리돈 ｈｉｖ 인테그라제 억제제를 위한 제조방법 및 중간체
MX383683B (es) 2008-12-11 2025-03-11 Shionogi & Co Sintesis de inhibidores de integrasa de vih de carbamoil-piridona e intermediarios.
TWI518084B (zh) 2009-03-26 2016-01-21 鹽野義製藥股份有限公司 哌喃酮與吡啶酮衍生物之製造方法
JP5737691B2 (ja) * 2009-06-15 2015-06-17 塩野義製薬株式会社 置換された多環性カルバモイルピリドン誘導体
NZ601847A (en) 2010-02-26 2014-03-28 Japan Tobacco Inc 1,3,4,8-tetrahydro-2h-pyrido[1,2-a]pyrazine derivative and use of same as hiv integrase inhibitor
TWI582097B (zh) 2010-03-23 2017-05-11 Ｖｉｉｖ醫療保健公司 製備胺甲醯吡啶酮衍生物及中間體之方法
WO2012039414A1 (ja) 2010-09-24 2012-03-29 塩野義製薬株式会社 置換された多環性カルバモイルピリドン誘導体のプロドラッグ
US9359300B2 (en) 2010-12-06 2016-06-07 Confluence Life Sciences, Inc. Methyl/difluorophenyl-methoxy substituted pyridinone-pyridinyl compounds, methyl-pyridinyl-methoxy substituted pyridinone-pyridinyl compounds, and methyl-pyrimidinyl-methoxy substituted pyridinone-pyridinyl compounds
EP3469907B1 (en) 2010-12-06 2021-03-03 Aclaris Therapeutics, Inc. Substituted pyridinone-pyridinyl compounds
WO2012104866A1 (en) * 2011-01-31 2012-08-09 Council Of Scientific & Industrial Research Chiral 1-(4-methylphenylmethyl)-5-oxo-{n-[(3-t-butoxycarbonyl- aminomethyl)]-piperidin-1-yl}-pyrrolidine-2-carboxamides as inhibitors of collagen induced platelet activation and adhesion
ES2602794T3 (es) 2011-03-31 2017-02-22 Pfizer Inc Piridinonas bicíclicas novedosas
AU2013261023B2 (en) * 2012-05-16 2016-11-24 Cellzome Limited Substituted 3, 4 - dihydro - 2H - pyrido [1, 2 -a] pyrazine - 1, 6 - dione derivatives useful for the treatment of (inter alia) Alzheimer's disease
UA110688C2 (uk) 2012-09-21 2016-01-25 Пфайзер Інк. Біциклічні піридинони
AR092742A1 (es) 2012-10-02 2015-04-29 Intermune Inc Piridinonas antifibroticas
EP2953949B1 (en) 2012-12-20 2016-09-28 Janssen Pharmaceutica NV Novel tricyclic 3,4-dihydro-2h-pyrido[1,2-a]pyrazine-1,6-dione derivatives as gamma secretase modulators
AU2013361401C1 (en) 2012-12-21 2018-08-09 Gilead Sciences, Inc. Polycyclic-carbamoylpyridone compounds and their pharmaceutical use
EP2945944B1 (en) 2013-01-17 2016-11-09 Janssen Pharmaceutica, N.V. Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators
US9493479B2 (en) 2013-04-16 2016-11-15 Merck Sharp & Dohme Corp. Substituted pyrido[1,2-a]pyrazines as HIV integrase inhibitors
RS61724B1 (sr) 2013-06-07 2021-05-31 Aclaris Therapeutics Inc Metil/fluoro-piridinil-metoksi supstituisana piridinon-piridinil jedinjenja i fluoro-pirimidinil-metoksi supstituisana piridinon-piridinil jedinjenja
NO2865735T3 (cg-RX-API-DMAC7.html) 2013-07-12 2018-07-21
EP3019503B1 (en) 2013-07-12 2017-09-06 Gilead Sciences, Inc. Polycyclic-carbamoylpyridone compounds and their use for the treatment of hiv infections
UA117499C2 (uk) * 2013-09-27 2018-08-10 Мерк Шарп Енд Доум Корп. Заміщені похідні хінолізину, які можна використовувати як інгібітори інтегрази віл
US10562897B2 (en) 2014-01-16 2020-02-18 Janssen Pharmaceutica Nv Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators
CN110452216B (zh) 2014-04-02 2022-08-26 英特穆恩公司 抗纤维化吡啶酮类
TW201613936A (en) 2014-06-20 2016-04-16 Gilead Sciences Inc Crystalline forms of(2R,5S,13aR)-8-hydroxy-7,9-dioxo-n-(2,4,6-trifluorobenzyl)-2,3,4,5,7,9,13,13a-octahydro-2,5-methanopyrido[1',2':4,5]pyrazino[2,1-b][1,3]oxazepine-10-carboxamide
NO2717902T3 (cg-RX-API-DMAC7.html) 2014-06-20 2018-06-23
TWI744723B (zh) 2014-06-20 2021-11-01 美商基利科學股份有限公司 多環型胺甲醯基吡啶酮化合物之合成
WO2016005330A1 (en) * 2014-07-07 2016-01-14 F. Hoffmann-La Roche Ag Dihydropyridopyrazine-1,8-diones and their use in the treatment, amelioration or prevention of viral diseases
TWI695003B (zh) 2014-12-23 2020-06-01 美商基利科學股份有限公司 多環胺甲醯基吡啶酮化合物及其醫藥用途
WO2016125048A1 (en) 2015-02-03 2016-08-11 Pfizer Inc. Novel cyclopropabenzofuranyl pyridopyrazinediones
PT3466490T (pt) 2015-04-02 2020-12-24 Gilead Sciences Inc Compostos de carbamoilpiridona policíclicos e sua utilização farmacêutica
JP6621933B2 (ja) 2015-11-09 2019-12-18 ギリアード サイエンシス インコーポレーテッド ヒト免疫不全ウイルスを処置するための治療組成物
KR102741390B1 (ko) 2018-05-31 2024-12-10 시오노기 앤드 컴파니, 리미티드 다환성 카바모일피리돈 유도체
BR112020024098A2 (pt) 2018-05-31 2021-02-17 Shionogi & Co., Ltd. derivado de piridona policíclica
AU2019339777B2 (en) * 2018-09-12 2022-09-01 Novartis Ag Antiviral pyridopyrazinedione compounds
US20230089442A1 (en) * 2019-03-20 2023-03-23 Pachamuthu Kandasamy Technologies useful for oligonucleotide preparation
WO2021195507A1 (en) 2020-03-27 2021-09-30 Aclaris Therapeutics, Inc. Methods and compositions for treating viral infections

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ATE430745T1 (de) 2000-10-12 2009-05-15 Merck & Co Inc Aza- und polyaza naphthalenyl karboxamide als inhibitoren der hiv-integrase
US6841558B2 (en) 2000-10-12 2005-01-11 Merck & Co., Inc. Aza-and polyaza-naphthalenyl carboxamides useful as HIV intergrase inhibitors
CA2463975A1 (en) 2001-10-26 2003-05-01 Maria Emilia Di Francesco Dihydroxypyrimidine carboxamide inhibitors of hiv integrase
DE122008000016I1 (de) 2001-10-26 2011-12-01 Angeletti P Ist Richerche Bio N-substituierte hydroxypyrimidinoncarboxamidhemmerder HIV-integrase.
WO2004047725A2 (en) 2002-09-11 2004-06-10 Merck & Co. Inc. 8-hydroxy-1-oxo-tetrahydropyrrolopyrazine compounds useful as hiv integrase inhibitors
CN1929737A (zh) * 2004-03-09 2007-03-14 默克公司 Hiv整合酶抑制剂

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006066414A1 (en) * 2004-12-23 2006-06-29 Virochem Pharma Inc. Hydroxydihydropyridopy razine-1,8-diones and methods for inhibiting hiv integrase
US8410103B2 (en) 2005-04-28 2013-04-02 Shionogi & Co., Ltd. (3S,11aR)-N-[2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3]oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide useful as anti-HIV agent
US8778943B2 (en) 2005-04-28 2014-07-15 Shionogi & Co., Ltd. Substituted 10-hydroxy-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1h-pyrido[1,2-α]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazine-8-carboxamides
US9051337B2 (en) 2005-04-28 2015-06-09 Shionogi & Co., Ltd. Substituted 10-hydroxy-9,11-dioxo-2,3,4a,5,9,11,13,13a-octahydro-1h-pyrido[1,2-a]pyrrolo[1′,2′:3,4]imidazo[1,2-d]pyrazine-8-carboxamides
US9273065B2 (en) 2005-04-28 2016-03-01 Shionogi & Co., Ltd. Substituted pyrido[1',2':4,5]pyrazino[1,2-a]pyrimidines as HIV integrase inhibitors
US10927129B2 (en) 2005-04-28 2021-02-23 Shinogi & Co., Ltd. N-[(2,4-difluorophenyl)methyl]-6-hydroxy-3-methyl-5,7-dioxo-2,3,5,7,11,11a-hexahydro[1,3] oxazolo[3,2-a]pyrido[1,2-d]pyrazine-8-carboxamide having HIV integrase inhibitory activity
US11267823B2 (en) 2005-04-28 2022-03-08 Shionogi & Co., Ltd. Substituted 1,2,3,3a,4,5,7,9,13,13a-decahydropyrido[1′,2′:4,5]pyrazino[1,2-a]pyrrolo[1,2-c]pyrimidines having HIV integrase inhibitory activity

Also Published As

Publication number Publication date
AU2003267098A1 (en) 2004-04-30
AU2003267098B2 (en) 2008-11-20
WO2004024078A2 (en) 2004-03-25
WO2004024078A3 (en) 2004-05-13
EP1549315A4 (en) 2007-05-23
US7517532B2 (en) 2009-04-14
JP2006506352A (ja) 2006-02-23
EP1549315A2 (en) 2005-07-06
US20060024330A1 (en) 2006-02-02

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Legal Events

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EEER Examination request
FZDE Discontinued