EA016387B1 - 2-(замещенные амино)бензотиазолсульфонамидные ингибиторы вич-протеазы - Google Patents
2-(замещенные амино)бензотиазолсульфонамидные ингибиторы вич-протеазы Download PDFInfo
- Publication number
- EA016387B1 EA016387B1 EA200970052A EA200970052A EA016387B1 EA 016387 B1 EA016387 B1 EA 016387B1 EA 200970052 A EA200970052 A EA 200970052A EA 200970052 A EA200970052 A EA 200970052A EA 016387 B1 EA016387 B1 EA 016387B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- alkyl
- compounds
- formula
- ritonavir
- Prior art date
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- -1 2-(substituted-amino)-benzothiazole sulfonamide Chemical class 0.000 title claims abstract description 46
- 239000004030 hiv protease inhibitor Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 165
- 238000000034 method Methods 0.000 claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- 229940124522 antiretrovirals Drugs 0.000 claims abstract description 5
- 239000003903 antiretrovirus agent Substances 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims description 35
- NCDNCNXCDXHOMX-UHFFFAOYSA-N Ritonavir Natural products C=1C=CC=CC=1CC(NC(=O)OCC=1SC=NC=1)C(O)CC(CC=1C=CC=CC=1)NC(=O)C(C(C)C)NC(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-UHFFFAOYSA-N 0.000 claims description 32
- 229960000311 ritonavir Drugs 0.000 claims description 32
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 claims description 32
- 229940079593 drug Drugs 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 13
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 241001430294 unidentified retrovirus Species 0.000 claims description 10
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
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- 108091005804 Peptidases Proteins 0.000 claims description 6
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
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- 125000000169 tricyclic heterocycle group Chemical group 0.000 claims description 6
- QAGYKUNXZHXKMR-UHFFFAOYSA-N CPD000469186 Natural products CC1=C(O)C=CC=C1C(=O)NC(C(O)CN1C(CC2CCCCC2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-UHFFFAOYSA-N 0.000 claims description 5
- 239000004365 Protease Substances 0.000 claims description 5
- 229960001830 amprenavir Drugs 0.000 claims description 5
- YMARZQAQMVYCKC-OEMFJLHTSA-N amprenavir Chemical compound C([C@@H]([C@H](O)CN(CC(C)C)S(=O)(=O)C=1C=CC(N)=CC=1)NC(=O)O[C@@H]1COCC1)C1=CC=CC=C1 YMARZQAQMVYCKC-OEMFJLHTSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 claims description 5
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- QAGYKUNXZHXKMR-HKWSIXNMSA-N nelfinavir Chemical compound CC1=C(O)C=CC=C1C(=O)N[C@H]([C@H](O)CN1[C@@H](C[C@@H]2CCCC[C@@H]2C1)C(=O)NC(C)(C)C)CSC1=CC=CC=C1 QAGYKUNXZHXKMR-HKWSIXNMSA-N 0.000 claims description 5
- 229960001852 saquinavir Drugs 0.000 claims description 5
- QWAXKHKRTORLEM-UGJKXSETSA-N saquinavir Chemical compound C([C@@H]([C@H](O)CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)C=1N=C2C=CC=CC2=CC=1)C1=CC=CC=C1 QWAXKHKRTORLEM-UGJKXSETSA-N 0.000 claims description 5
- BTZNMODCUKWHLK-UHFFFAOYSA-N C(C1=CC=CC=C1)C(C(CN(CC(C)C)S(=O)(=O)C1=CC2=C(N=C(S2)NC2CCN(CC2)C2CCCC2)C=C1)O)NC(O)=O Chemical compound C(C1=CC=CC=C1)C(C(CN(CC(C)C)S(=O)(=O)C1=CC2=C(N=C(S2)NC2CCN(CC2)C2CCCC2)C=C1)O)NC(O)=O BTZNMODCUKWHLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims description 4
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
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- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000002110 toxicologic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 210000002845 virion Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
-
- 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
-
- 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06116003 | 2006-06-23 | ||
| PCT/EP2007/056235 WO2007147884A1 (en) | 2006-06-23 | 2007-06-22 | 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200970052A1 EA200970052A1 (ru) | 2009-04-28 |
| EA016387B1 true EA016387B1 (ru) | 2012-04-30 |
Family
ID=37596252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA200970052A EA016387B1 (ru) | 2006-06-23 | 2007-06-22 | 2-(замещенные амино)бензотиазолсульфонамидные ингибиторы вич-протеазы |
Country Status (30)
| Country | Link |
|---|---|
| US (1) | US8202887B2 (enExample) |
| EP (1) | EP2035432B1 (enExample) |
| JP (1) | JP5232776B2 (enExample) |
| KR (1) | KR101419320B1 (enExample) |
| CN (1) | CN101479275B (enExample) |
| AP (1) | AP2069A (enExample) |
| AR (1) | AR061619A1 (enExample) |
| AT (1) | ATE544769T1 (enExample) |
| AU (1) | AU2007262943B2 (enExample) |
| BR (1) | BRPI0713487B1 (enExample) |
| CA (1) | CA2653233C (enExample) |
| CL (1) | CL2007001826A1 (enExample) |
| CY (1) | CY1112971T1 (enExample) |
| DK (1) | DK2035432T3 (enExample) |
| EA (1) | EA016387B1 (enExample) |
| ES (1) | ES2381129T3 (enExample) |
| IL (1) | IL195381A (enExample) |
| JO (1) | JO2841B1 (enExample) |
| MX (1) | MX2009000160A (enExample) |
| MY (1) | MY146805A (enExample) |
| NZ (1) | NZ573286A (enExample) |
| PE (1) | PE20080342A1 (enExample) |
| PL (1) | PL2035432T3 (enExample) |
| PT (1) | PT2035432E (enExample) |
| SI (1) | SI2035432T1 (enExample) |
| TW (1) | TWI415851B (enExample) |
| UA (1) | UA96445C2 (enExample) |
| UY (1) | UY30416A1 (enExample) |
| WO (1) | WO2007147884A1 (enExample) |
| ZA (1) | ZA200810350B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JO3090B1 (ar) | 2009-12-11 | 2017-03-15 | Janssen Sciences Ireland Uc | 5- امينو-4- هيدروكسي-بنتويل اميدات |
| EP2588455B1 (en) | 2010-07-02 | 2018-04-04 | Gilead Sciences, Inc. | 2-quinolinyl-acetic acid derivatives as hiv antiviral compounds |
| CN103140474A (zh) | 2010-07-02 | 2013-06-05 | 吉里德科学公司 | 治疗aids的萘-2-基乙酸衍生物 |
| US9024038B2 (en) * | 2010-12-27 | 2015-05-05 | Purdue Research Foundation | Compunds and methods for treating HIV |
| MX2013012266A (es) | 2011-04-21 | 2013-11-22 | Gilead Sciences Inc | Compuestos de benzotiazol y su uso farmaceutico. |
| US9376392B2 (en) | 2012-01-04 | 2016-06-28 | Gilead Sciences, Inc. | 2-(tert-butoxy)-2-(7-methylquinolin-6-yl) acetic acid derivatives for treating AIDS |
| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| 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 |
| WO2021209563A1 (en) | 2020-04-16 | 2021-10-21 | Som Innovation Biotech, S.A. | Compounds for use in the treatment of viral infections by respiratory syndrome-related coronavirus |
| US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083657A2 (en) * | 2001-02-14 | 2002-10-24 | Tibotec Pharmaceuticals Ltd. | Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
| WO2003049746A2 (en) * | 2001-12-12 | 2003-06-19 | Tibotec Pharmaceuticals Ltd. | Combination of cytochome p450 dependent protease inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR0305717A (pt) * | 2002-08-02 | 2004-09-28 | Tibotec Pharm Ltd | Inibidores da protease do hiv 2-amino-benzotiazol sulfonamida de amplo espectro |
| PT1670448E (pt) * | 2003-09-30 | 2008-02-11 | Tibotec Pharm Ltd | Sulfonamidas inibidoras de hcv |
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2007
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- 2007-06-15 UY UY30416A patent/UY30416A1/es not_active Application Discontinuation
- 2007-06-21 CL CL2007001826A patent/CL2007001826A1/es unknown
- 2007-06-22 AR ARP070102776A patent/AR061619A1/es active IP Right Grant
- 2007-06-22 EA EA200970052A patent/EA016387B1/ru not_active IP Right Cessation
- 2007-06-22 PT PT07765554T patent/PT2035432E/pt unknown
- 2007-06-22 TW TW096122406A patent/TWI415851B/zh not_active IP Right Cessation
- 2007-06-22 AT AT07765554T patent/ATE544769T1/de active
- 2007-06-22 AU AU2007262943A patent/AU2007262943B2/en not_active Ceased
- 2007-06-22 UA UAA200813950A patent/UA96445C2/ru unknown
- 2007-06-22 NZ NZ573286A patent/NZ573286A/en not_active IP Right Cessation
- 2007-06-22 WO PCT/EP2007/056235 patent/WO2007147884A1/en not_active Ceased
- 2007-06-22 KR KR1020097000754A patent/KR101419320B1/ko not_active Expired - Fee Related
- 2007-06-22 MY MYPI20085209A patent/MY146805A/en unknown
- 2007-06-22 US US12/304,990 patent/US8202887B2/en not_active Expired - Fee Related
- 2007-06-22 AP AP2008004679A patent/AP2069A/en active
- 2007-06-22 BR BRPI0713487-8A patent/BRPI0713487B1/pt not_active IP Right Cessation
- 2007-06-22 MX MX2009000160A patent/MX2009000160A/es active IP Right Grant
- 2007-06-22 CA CA2653233A patent/CA2653233C/en active Active
- 2007-06-22 PE PE2007000802A patent/PE20080342A1/es active IP Right Grant
- 2007-06-22 CN CN2007800236807A patent/CN101479275B/zh active Active
- 2007-06-22 SI SI200730904T patent/SI2035432T1/sl unknown
- 2007-06-22 PL PL07765554T patent/PL2035432T3/pl unknown
- 2007-06-22 DK DK07765554.6T patent/DK2035432T3/da active
- 2007-06-22 ES ES07765554T patent/ES2381129T3/es active Active
- 2007-06-22 EP EP07765554A patent/EP2035432B1/en active Active
- 2007-06-22 JP JP2009515891A patent/JP5232776B2/ja not_active Expired - Fee Related
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2008
- 2008-11-19 IL IL195381A patent/IL195381A/en active IP Right Grant
- 2008-12-05 ZA ZA200810350A patent/ZA200810350B/xx unknown
-
2012
- 2012-05-08 CY CY20121100429T patent/CY1112971T1/el unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002083657A2 (en) * | 2001-02-14 | 2002-10-24 | Tibotec Pharmaceuticals Ltd. | Broadspectrum 2-(substituted-amino)-benzothiazole sulfonamide hiv protease inhibitors |
| WO2003049746A2 (en) * | 2001-12-12 | 2003-06-19 | Tibotec Pharmaceuticals Ltd. | Combination of cytochome p450 dependent protease inhibitors |
Non-Patent Citations (1)
| Title |
|---|
| D.L.N.G. SURLERAUX ET AL.: "Design of HIV-1 Protease Inhibitors Active on Multidrug-Resistant Virus", JOURNAL OF MEDICINAL CHEMISTRY, vol. 48, no. 6, 2005, pages 1965-1973, XP002414592, scheme 1, compounds 20a-i; tables 2,3 * |
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