HU229224B1 - 2-(substituted-amino)-benzothiazole sulfonamide compounds having broadspectrum hiv protease inhibitor activity and medicaments containing them - Google Patents
2-(substituted-amino)-benzothiazole sulfonamide compounds having broadspectrum hiv protease inhibitor activity and medicaments containing them Download PDFInfo
- Publication number
- HU229224B1 HU229224B1 HU0303257A HUP0303257A HU229224B1 HU 229224 B1 HU229224 B1 HU 229224B1 HU 0303257 A HU0303257 A HU 0303257A HU P0303257 A HUP0303257 A HU P0303257A HU 229224 B1 HU229224 B1 HU 229224B1
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- Prior art keywords
- alkyl
- aryl
- group
- carbon atoms
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- -1 2-(substituted-amino)-benzothiazole sulfonamide compounds Chemical class 0.000 title claims description 90
- 239000003814 drug Substances 0.000 title claims description 30
- 230000000694 effects Effects 0.000 title claims description 17
- 239000004030 hiv protease inhibitor Substances 0.000 title description 2
- 229940122440 HIV protease inhibitor Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 249
- 125000000217 alkyl group Chemical group 0.000 claims description 168
- 239000000543 intermediate Substances 0.000 claims description 120
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 57
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
- 238000002360 preparation method Methods 0.000 claims description 45
- 239000002904 solvent Substances 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
- 125000003277 amino group Chemical group 0.000 claims description 31
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- 150000002431 hydrogen Chemical class 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 24
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- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical class C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 4
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- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
-
- 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
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Communicable Diseases (AREA)
- Tropical Medicine & Parasitology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- AIDS & HIV (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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| PCT/EP2002/001788 WO2002083657A2 (en) | 2001-02-14 | 2002-02-14 | Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
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| Publication Number | Publication Date |
|---|---|
| HUP0303257A2 HUP0303257A2 (hu) | 2004-01-28 |
| HU229224B1 true HU229224B1 (en) | 2013-09-30 |
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| DK (1) | DK1370543T3 (enExample) |
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| EE (1) | EE05385B1 (enExample) |
| ES (1) | ES2275866T3 (enExample) |
| HR (1) | HRP20030735B1 (enExample) |
| HU (1) | HU229224B1 (enExample) |
| IL (2) | IL157171A0 (enExample) |
| MX (1) | MXPA03007236A (enExample) |
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| NZ (1) | NZ527391A (enExample) |
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| SK (1) | SK287582B6 (enExample) |
| WO (1) | WO2002083657A2 (enExample) |
| ZA (1) | ZA200306086B (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| MXPA01012270A (es) | 1999-05-28 | 2003-06-24 | Virco Nv | Nuevos perfiles mutacionales en la transcriptasa reversa de vih-1 correlacionadas con resistencia fenotipica a farmacos. |
| AU2002226316B2 (en) | 2000-10-20 | 2008-06-26 | Virco Bvba | Mutational profiles in HIV-1 reverse transcriptase correlated with phenotypic drug resistance |
| EP1370543B1 (en) | 2001-02-14 | 2006-10-25 | Tibotec Pharmaceuticals Ltd. | Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
| US7109230B2 (en) | 2002-01-07 | 2006-09-19 | Sequoia Pharmaceuticals, Inc. | Resistance-repellent retroviral protease inhibitors |
| US7157489B2 (en) | 2002-03-12 | 2007-01-02 | The Board Of Trustees Of The University Of Illinois | HIV protease inhibitors |
| CA2490764C (en) | 2002-07-01 | 2011-11-22 | Tibotec Pharmaceuticals Ltd. | New mutational profiles in hiv-1 reverse transcriptase correlated with phenotypic drug resistance |
| EP1520247B1 (en) | 2002-07-01 | 2009-05-27 | Tibotec Pharmaceuticals Ltd. | Mutational profiles in hiv-1 protease correlated with phenotypic drug resistance |
| OA12893A (en) * | 2002-08-02 | 2006-10-13 | Tibotec Pharm Ltd | Broadspectrum 2-Amino-Benzothiazole Sulfonamide HIV Protease Inhibitors. |
| BR0305717A (pt) * | 2002-08-02 | 2004-09-28 | Tibotec Pharm Ltd | Inibidores da protease do hiv 2-amino-benzotiazol sulfonamida de amplo espectro |
| WO2005030739A1 (en) * | 2003-09-30 | 2005-04-07 | Tibotec Pharmaceuticals Ltd. | Methods for the preparation of benzoxazole sulfonamide compounds and intermediates thereof |
| DE10360835A1 (de) * | 2003-12-23 | 2005-07-21 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Bicyclische Imidazolverbindungen, deren Herstellung und deren Verwendung als Arzneimittel |
| AU2005244121B2 (en) * | 2004-05-07 | 2012-01-19 | Sequoia Pharmaceuticals, Inc. | Resistance-repellent retroviral protease inhibitors |
| ES2331257T3 (es) | 2005-02-25 | 2009-12-28 | Tibotec Pharmaceuticals | Sintesis de precursores de inhibidores de proteasas. |
| AR053845A1 (es) | 2005-04-15 | 2007-05-23 | Tibotec Pharm Ltd | 5-tiazolilmetil[(1s,2r)-3-[[(2-amino-6-benzoxazolil)sulfonil)](2-metilpropil)amino]-2-hidroxi-1-(fenilmetil)propil]carbamato como mejorador de farmacos metabolizados por el citocromo p450 |
| JO2841B1 (en) * | 2006-06-23 | 2014-09-15 | تيبوتيك فارماسيوتيكالز ليمتد | 2-(substituted-amino) -benzothiazole sulfonamide as protease inhibitors HIV (HIV) |
| WO2011061590A1 (en) | 2009-11-17 | 2011-05-26 | Hetero Research Foundation | Novel carboxamide derivatives as hiv inhibitors |
| JO3090B1 (ar) * | 2009-12-11 | 2017-03-15 | Janssen Sciences Ireland Uc | 5- امينو-4- هيدروكسي-بنتويل اميدات |
| US9024038B2 (en) * | 2010-12-27 | 2015-05-05 | Purdue Research Foundation | Compunds and methods for treating HIV |
| ES2571479T3 (es) | 2012-04-20 | 2016-05-25 | Gilead Sciences Inc | Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH |
| CN104000824B (zh) * | 2014-05-28 | 2016-07-06 | 中山大学 | 苯并五元杂环类化合物在制备抗hiv-1病毒药物中的应用 |
| US11439608B2 (en) | 2017-09-25 | 2022-09-13 | Qun Lu | Roles of modulators of intersectin-CDC42 signaling in Alzheimer's disease |
| CN116354903B (zh) * | 2021-12-28 | 2025-09-09 | 南京药石科技股份有限公司 | 一种6-苯并噻唑磺酰氯的制备方法 |
| WO2024206093A1 (en) * | 2023-03-24 | 2024-10-03 | Purdue Research Foundation | Hiv-1p rotease inhibitors and uses thereof |
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| DE69121436T2 (de) | 1990-03-09 | 1997-01-09 | Milliken Res Corp | Organische Materialien, die sulfonamidogebundene Poly(oxyalkylen)gruppen tragen und ihre Herstellung |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| DE122007000045I2 (de) | 1992-08-25 | 2011-07-21 | Gd Searle Llc Gd Searle Llc | Darunavir oder pharmazeutisch vertragliche Salze, Hydroxyethylaminosulfonamide verwendbar als InhibiEster oder Prodrugs davon. toren retroviraler Proteasen. |
| PH30929A (en) | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| IS2334B (is) * | 1992-09-08 | 2008-02-15 | Vertex Pharmaceuticals Inc., (A Massachusetts Corporation) | Aspartyl próteasi hemjari af nýjum flokki súlfonamíða |
| ES2127938T3 (es) * | 1993-08-24 | 1999-05-01 | Searle & Co | Hidroxietilamino sulfonamidas utiles como inhibidores de proteasas retroviricas. |
| ES2166786T3 (es) | 1993-10-01 | 2002-05-01 | Astrazeneca Ab | Procedimiento i. |
| DE69637380T2 (de) | 1995-01-20 | 2009-09-17 | G.D. Searle Llc, Chicago | Bis-sulfonamid-hydroxyethylamino-derivate als inhibitoren retroviraler proteasen |
| US6140505A (en) * | 1995-03-10 | 2000-10-31 | G. D. Searle & Co. | Synthesis of benzo fused heterocyclic sulfonyl chlorides |
| US5756533A (en) | 1995-03-10 | 1998-05-26 | G.D. Searle & Co. | Amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US6861539B1 (en) * | 1995-03-10 | 2005-03-01 | G. D. Searle & Co. | Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US6150556A (en) * | 1995-03-10 | 2000-11-21 | G. D. Dearle & Co. | Bis-amino acid hydroxyethylamino sulfonamide retroviral protease inhibitors |
| CN1149223C (zh) * | 1995-03-10 | 2004-05-12 | G·D·瑟尔公司 | 杂环羰基氨基酸羟乙氨基磺酰胺逆转录病毒蛋白酶抑制剂 |
| US6143788A (en) * | 1995-03-10 | 2000-11-07 | G.D. Searle & Co. | Bis-amino acid hydroxyethlamino sulfonamide retroviral protease inhibitors |
| US5705500A (en) * | 1995-03-10 | 1998-01-06 | G.D. Searle & Co. | Sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US5753660A (en) * | 1995-11-15 | 1998-05-19 | G. D. Searle & Co. | Substituted sulfonylalkanoylamino hydroxyethylamino sulfonamide retroviral protease inhibitors |
| US6509038B2 (en) | 1996-05-20 | 2003-01-21 | Janssen Pharmaceutica N.V. | Antifungal compositions with improved bioavailability |
| CZ295502B6 (cs) | 1997-03-26 | 2005-08-17 | Janssen Pharmaceutica N. V. | Antifungální peleta, způsob její přípravy a farmaceutická dávková forma s obsahem těchto pelet |
| US6436989B1 (en) | 1997-12-24 | 2002-08-20 | Vertex Pharmaceuticals, Incorporated | Prodrugs of aspartyl protease inhibitors |
| AU2012199A (en) | 1997-12-24 | 1999-07-19 | Vertex Pharmaceuticals Incorporated | Prodrugs of aspartyl protease inhibitors |
| EP1042280A2 (en) | 1997-12-24 | 2000-10-11 | Vertex Pharmaceuticals Incorporated | Prodrugs of aspartyl protease inhibitors |
| AU2010299A (en) | 1997-12-24 | 1999-07-19 | Vertex Pharmaceuticals Incorporated | Prodrugs os aspartyl protease inhibitors |
| BR9912169A (pt) * | 1998-06-19 | 2001-04-10 | Vertex Pharma | Inibidores de sulfonamida de protease de aspartil |
| PT2336134T (pt) * | 1998-06-23 | 2016-10-19 | The Board Of Trustees Of The Univ Of Illionis | Ensaio de aptidão e métodos para reduzir a resistência do hiv à terapia |
| AU4828199A (en) | 1998-06-23 | 2000-01-10 | Board Of Trustees Of The University Of Illinois, The | Multi-drug resistant retroviral protease inhibitors and associated methods |
| AR031520A1 (es) * | 1999-06-11 | 2003-09-24 | Vertex Pharma | Un compuesto inhibidor de aspartilo proteasa, una composicion que lo comprende y un metodo para tratar un paciente con dicha composicion |
| EP1370543B1 (en) | 2001-02-14 | 2006-10-25 | Tibotec Pharmaceuticals Ltd. | Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
-
2002
- 2002-02-14 EP EP02729930A patent/EP1370543B1/en not_active Expired - Lifetime
- 2002-02-14 PT PT02729930T patent/PT1370543E/pt unknown
- 2002-02-14 MX MXPA03007236A patent/MXPA03007236A/es active IP Right Grant
- 2002-02-14 SI SI200230467T patent/SI1370543T1/sl unknown
- 2002-02-14 CA CA2438304A patent/CA2438304C/en not_active Expired - Fee Related
- 2002-02-14 AU AU2002302363A patent/AU2002302363B2/en not_active Ceased
- 2002-02-14 NZ NZ527391A patent/NZ527391A/xx not_active IP Right Cessation
- 2002-02-14 SK SK1102-2003A patent/SK287582B6/sk not_active IP Right Cessation
- 2002-02-14 CZ CZ2003-2415A patent/CZ304273B6/cs not_active IP Right Cessation
- 2002-02-14 CN CNB028049829A patent/CN100369904C/zh not_active Expired - Fee Related
- 2002-02-14 WO PCT/EP2002/001788 patent/WO2002083657A2/en not_active Ceased
- 2002-02-14 IL IL15717102A patent/IL157171A0/xx unknown
- 2002-02-14 DE DE60215623T patent/DE60215623T2/de not_active Expired - Lifetime
- 2002-02-14 AP APAP/P/2003/002856A patent/AP1504A/en active
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- 2003-09-01 BG BG108143A patent/BG66301B1/bg unknown
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2007
- 2007-01-25 CY CY20071100088T patent/CY1108073T1/el unknown
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