ZA200502384B - Non-nucleoside reverse transcriptase inhibitors - Google Patents
Non-nucleoside reverse transcriptase inhibitors Download PDFInfo
- Publication number
- ZA200502384B ZA200502384B ZA200502384A ZA200502384A ZA200502384B ZA 200502384 B ZA200502384 B ZA 200502384B ZA 200502384 A ZA200502384 A ZA 200502384A ZA 200502384 A ZA200502384 A ZA 200502384A ZA 200502384 B ZA200502384 B ZA 200502384B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- substituted
- compound
- halogen
- optionally substituted
- Prior art date
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- 239000002726 nonnucleoside reverse transcriptase inhibitor Substances 0.000 title description 5
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4196—1,2,4-Triazoles
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- A—HUMAN NECESSITIES
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- 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
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- 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
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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
- C07D233/66—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 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
- C07D233/84—Sulfur 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
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
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- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- AIDS & HIV (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
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| US7642277B2 (en) * | 2002-12-04 | 2010-01-05 | Boehringer Ingelheim International Gmbh | Non-nucleoside reverse transcriptase inhibitors |
| GB0315111D0 (en) * | 2003-06-27 | 2003-07-30 | Cancer Rec Tech Ltd | Substituted 5-membered ring compounds and their use |
| WO2005087750A1 (en) * | 2004-03-08 | 2005-09-22 | Wyeth | Ion channel modulators |
| WO2005090320A2 (en) * | 2004-03-12 | 2005-09-29 | Wyeth | Triazole derivatives and method of using the same to treat hiv infections |
| WO2005115147A2 (en) * | 2004-05-18 | 2005-12-08 | Merck & Co., Inc. | Hiv reverse transcriptase inhibitors |
| US7517998B2 (en) * | 2004-06-01 | 2009-04-14 | Boehringer Ingelheim International Gmbh | Non nucleoside reverse transcriptase inhibitors |
| EP2433633A1 (en) | 2004-08-25 | 2012-03-28 | Ardea Biosciences, Inc. | Triazolyl alpha -mercaptoacetanildes as inhibitors of HIV reverse transcriptase |
| WO2007050087A1 (en) * | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
| MX2009000871A (es) * | 2006-07-24 | 2009-05-08 | Gilead Sciences Inc | Novedosos inhibidores de transcriptasa inversa de vih. |
| WO2009030996A1 (en) * | 2007-09-05 | 2009-03-12 | Coley Pharmaceutical Group, Inc. | Triazole compounds as toll-like receptor (tlr) agonists |
| DK2217577T3 (da) | 2007-11-27 | 2014-10-20 | Ardea Biosciences Inc | Hidtil ukendte forbindelser og præparater og fremgangsmåder til anvendelse deraf |
| JP2012502050A (ja) * | 2008-09-04 | 2012-01-26 | アルディア バイオサイエンス，インク． | 尿酸値を調節するための化合物、組成物及びそれを使用する方法。 |
| US8242154B2 (en) | 2008-09-04 | 2012-08-14 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| US8173690B2 (en) | 2008-09-04 | 2012-05-08 | Ardea Biosciences, Inc. | Compounds, compositions and methods of using same for modulating uric acid levels |
| CA2760940A1 (en) | 2009-05-20 | 2010-11-25 | Ardea Biosciences, Inc. | Methods of modulating uric acid levels |
| WO2011046646A2 (en) * | 2009-07-10 | 2011-04-21 | Microbiotix, Inc. | Inhibitors of filovirus entry into host cells |
| MX2012015097A (es) * | 2010-07-02 | 2013-05-28 | Gilead Sciences Inc | Derivados de acido naft-2-ilacetico para tratar sida. |
| CN101899013B (zh) * | 2010-07-12 | 2012-07-25 | 山东大学 | 2-(2-取代芳基-2h-1,2,4-三唑-3-巯基)乙酰胺衍生物及其制备方法与应用 |
| US9332757B2 (en) | 2010-10-25 | 2016-05-10 | Vanderbilt University | Composition for inhibition of insect host sensing |
| EP2704575B1 (en) | 2011-05-06 | 2020-06-03 | Vanderbilt University | Composition for inhibition of insect sensing |
| ITMI20120786A1 (it) * | 2012-05-09 | 2013-11-10 | Fond Italiana Sclerosi M Ultipla Fism Onlu | Modulatori del recettore gpr17 |
| AR091651A1 (es) | 2012-07-03 | 2015-02-18 | Ardea Biosciences Inc | Elaboracion de acido 2-(5-bromo-4-(4-ciclopropilnaftalen-1-il)-4h-1,2,4-triazol-3-iltio)acetico |
| RU2626003C2 (ru) * | 2014-04-28 | 2017-07-21 | Общество с ограниченной ответственностью "Квантум Фармасьютикалс" | Амид 1,2,4-триазол-3-илтиогликолевой кислоты, обладающий противовирусной активностью, или его фармацевтически приемлемые соли, фармацевтические композиции и их применение для лечения и профилактики гриппа |
| AU2016238305B2 (en) | 2015-03-25 | 2020-10-08 | Vanderbilt University | Binary compositions as disruptors of ORco-mediated odorant sensing |
| RS60353B1 (sr) | 2015-05-20 | 2020-07-31 | Amgen Inc | Agonisti triazola apj receptora |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| WO2018097944A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
| EP3541805B1 (en) | 2016-11-16 | 2020-10-14 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| WO2018093580A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| MA46824A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole substitués par alkyle en tant qu'agonistes du récepteur apj |
| MA46827A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole à substitution cycloalkyle en tant qu'agonistes du récepteur apj |
| US10906890B2 (en) | 2016-11-16 | 2021-02-02 | Amgen Inc. | Triazole phenyl compounds as agonists of the APJ receptor |
| MA50509A (fr) | 2017-11-03 | 2021-06-02 | Amgen Inc | Agonistes de triazole fusionnés du récepteur apj |
| MA52487A (fr) | 2018-05-01 | 2021-03-10 | Amgen Inc | Pyrimidinones substituées en tant qu'agonistes du récepteur apj |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0759563B2 (ja) * | 1987-01-28 | 1995-06-28 | 大塚化学株式会社 | ピラゾ−ル誘導体、その製造方法及び該誘導体を有効成分とする除草剤 |
| EP0303301A3 (en) * | 1987-08-14 | 1989-05-17 | Fuji Photo Film Co., Ltd. | Silver halide photographic material |
| US6832996B2 (en) * | 1995-06-07 | 2004-12-21 | Arthrocare Corporation | Electrosurgical systems and methods for treating tissue |
| US6245817B1 (en) * | 1997-02-14 | 2001-06-12 | Bayer Corporation | NPY5 receptor antagonists and methods for using same |
| EP0910565A1 (en) * | 1997-02-14 | 1999-04-28 | Bayer Corporation | Amide derivatives as selective neuropeptide y receptor antagonists |
| BRPI9909191B8 (pt) * | 1998-03-27 | 2021-07-06 | Janssen Pharmaceutica Nv | derivados de pirimidina inibidores do hiv, seu uso e composição farmacêutica que os compreende |
| US6414147B1 (en) * | 1998-12-23 | 2002-07-02 | Neurogen Corporation | 2-amino-9-alkylpurines: GABA brain receptor ligands |
| US6593077B2 (en) * | 1999-03-22 | 2003-07-15 | Special Materials Research And Technology, Inc. | Method of making thin films dielectrics using a process for room temperature wet chemical growth of SiO based oxides on a substrate |
| CN1494528A (zh) | 2001-03-02 | 2004-05-05 | ʷ��˿�������ȳ�ķ����˾ | 作为逆转录酶抑制剂的二苯酮 |
| CA2496565C (en) * | 2002-08-23 | 2013-04-02 | Ribapharm Inc. | Non-nucleoside reverse transcriptase inhibitors |
| US7642277B2 (en) * | 2002-12-04 | 2010-01-05 | Boehringer Ingelheim International Gmbh | Non-nucleoside reverse transcriptase inhibitors |
| US20060205026A1 (en) * | 2002-12-19 | 2006-09-14 | Valeant Research & Development | Parallel inducible cell-based kinase screen |
| WO2007050087A1 (en) * | 2004-08-25 | 2007-05-03 | Ardea Biosciences, Inc. | N[S(4-aryl-triazol-3-yl)α -mercaptoacetyl]-p-amino benozoic acids AS HIV REVERSE TRANSCRIPTASE INHIBITORS |
| US8101799B2 (en) * | 2005-07-21 | 2012-01-24 | Ardea Biosciences | Derivatives of N-(arylamino) sulfonamides as inhibitors of MEK |
| WO2007121269A2 (en) * | 2006-04-11 | 2007-10-25 | Ardea Biosciences, Inc. | N-aryl-n'alkyl sulfamides as mek inhibitors |
| ATE483463T1 (de) * | 2006-04-18 | 2010-10-15 | Ardea Biosciences Inc | Pyridonsulfonamide und pyridonsulfamide als mek- hemmer |
| CA2668997C (en) * | 2006-11-09 | 2012-10-09 | Ardea Biosciences, Inc. | 4-cyanophenylamino-substituted bicyclic heterocyclic compounds as hiv inhibitors |
-
2003
- 2003-08-22 CA CA2496565A patent/CA2496565C/en not_active Expired - Fee Related
- 2003-08-22 EA EA200500399A patent/EA009478B1/ru not_active IP Right Cessation
- 2003-08-22 EP EP03786506A patent/EP1545483B1/en not_active Expired - Lifetime
- 2003-08-22 DE DE60336664T patent/DE60336664D1/de not_active Expired - Lifetime
- 2003-08-22 JP JP2004541500A patent/JP4413781B2/ja not_active Expired - Fee Related
- 2003-08-22 CN CN038243377A patent/CN1697650B/zh not_active Expired - Fee Related
- 2003-08-22 WO PCT/US2003/027433 patent/WO2004030611A2/en active Application Filing
- 2003-08-22 EP EP11160994A patent/EP2353593B1/en not_active Expired - Lifetime
- 2003-08-22 AT AT03786506T patent/ATE504294T1/de not_active IP Right Cessation
- 2003-08-22 MX MXPA05002070A patent/MXPA05002070A/es active IP Right Grant
- 2003-08-22 US US10/526,249 patent/US20060135556A1/en not_active Abandoned
- 2003-08-22 BR BR0313747-3A patent/BR0313747A/pt not_active Application Discontinuation
- 2003-08-22 AU AU2003295324A patent/AU2003295324B2/en not_active Ceased
-
2005
- 2005-03-22 ZA ZA200502384A patent/ZA200502384B/en unknown
-
2006
- 2006-05-16 HK HK06105685.3A patent/HK1085667A1/xx not_active IP Right Cessation
-
2008
- 2008-05-02 US US12/114,467 patent/US20080249131A1/en not_active Abandoned
- 2008-11-19 AU AU2008246249A patent/AU2008246249B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003295324A1 (en) | 2004-04-23 |
| EP2353593A1 (en) | 2011-08-10 |
| EA200500399A1 (ru) | 2005-12-29 |
| US20080249131A1 (en) | 2008-10-09 |
| DE60336664D1 (de) | 2011-05-19 |
| WO2004030611A3 (en) | 2004-06-17 |
| EP1545483A2 (en) | 2005-06-29 |
| US20060135556A1 (en) | 2006-06-22 |
| BR0313747A (pt) | 2005-06-21 |
| WO2004030611A2 (en) | 2004-04-15 |
| EP1545483B1 (en) | 2011-04-06 |
| HK1085667A1 (en) | 2006-09-01 |
| CA2496565C (en) | 2013-04-02 |
| ATE504294T1 (de) | 2011-04-15 |
| AU2008246249B2 (en) | 2010-09-30 |
| MXPA05002070A (es) | 2005-07-05 |
| JP2006505543A (ja) | 2006-02-16 |
| EP1545483A4 (en) | 2009-03-25 |
| AU2003295324B2 (en) | 2008-08-28 |
| AU2008246249A1 (en) | 2008-12-11 |
| CN1697650B (zh) | 2010-11-10 |
| EA009478B1 (ru) | 2008-02-28 |
| CA2496565A1 (en) | 2004-04-15 |
| CN1697650A (zh) | 2005-11-16 |
| JP4413781B2 (ja) | 2010-02-10 |
| EP2353593B1 (en) | 2012-08-22 |
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