AR070413A1 - Inhibidores macrociclicos de proteasa de serina - Google Patents
Inhibidores macrociclicos de proteasa de serinaInfo
- Publication number
- AR070413A1 AR070413A1 ARP090100353A ARP090100353A AR070413A1 AR 070413 A1 AR070413 A1 AR 070413A1 AR P090100353 A ARP090100353 A AR P090100353A AR P090100353 A ARP090100353 A AR P090100353A AR 070413 A1 AR070413 A1 AR 070413A1
- Authority
- AR
- Argentina
- Prior art keywords
- heterocyclyl
- alkyl
- aryl
- alkynyl
- cycloalkyl
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 21
- 125000001072 heteroaryl group Chemical group 0.000 abstract 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 13
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 abstract 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 abstract 12
- 239000001257 hydrogen Substances 0.000 abstract 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 11
- 125000005915 C6-C14 aryl group Chemical group 0.000 abstract 10
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000004450 alkenylene group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- -1 L is a ligature Chemical group 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 2
- 125000004419 alkynylene group Chemical group 0.000 abstract 2
- 125000004429 atom Chemical group 0.000 abstract 2
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 2
- 125000002993 cycloalkylene group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 abstract 1
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 abstract 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 101150020251 NR13 gene Proteins 0.000 abstract 1
- 102000012479 Serine Proteases Human genes 0.000 abstract 1
- 108010022999 Serine Proteases Proteins 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 208000015181 infectious disease Diseases 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000012453 solvate Substances 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged 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
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Peptides Or Proteins (AREA)
Abstract
En la presente se provee compuestos inhibidores macrocíclicos de proteasa de serina, composiciones farmacéuticas que comprenden los compuestos y su proceso de preparacion. Además se proveen métodos para su uso en el tratamiento de una infeccion por HCV en un huésped que lo necesite. Reivindicacion 1: Un compuesto caracterizado porque tiene la formula (1) o un unico enantiomero, una mezcla racémica, o una mezcla de sus diastereomeros; o su sal, solvato o prodroga farmacéuticamente aceptable; en donde: R5 es -OH, -NR8R9, -NHS(O)2R8, -NHS(O)2NR8R9, -NHC(O)R8, -NHC(O)NR8R9, -C(O)R9, o -C(O)NR8R9, en donde cada R8 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, heterociclilo, aIquiIo C1-6-cicloalquileno C3-7, -CH2NR8aR8b, -CH(R8c)NR8aR8b, -CHR8cCHR8dNR8aR8b, o -CH2CR8cR8dNR8aR8b, en donde: cada R8a, R8c, y R8d es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, heterociclilo, arilo C6-4-alquileno C1-6, y cada R8b es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, heterociclilo, -S(O)kR11, -S(O)kNR11R12, -C(O)R11, -C(O)OR11, -C(O)NR11R12, o -C(=NR13)NR11R12; en donde cada R11, R12, y R13 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, o R11 y R12 junto con el átomo de N al cual están unidos forman heterociclilo; o R8a y R8b junto con el átomo de N al cual están unidos forman heterociclilo; y cada R9 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, o R8 y R9 junto con el átomo de N al cual están unidos forman heterociclilo; R6 es hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, L es una ligadura, alquileno C1-6, cicloalquileno C3-7, alquenileno C2-6, alquinileno C2-6, X, o -(CR6aR6b)pX-; en donde p es un numero entero de 1, 2, o 3; R6a y R6b son cada uno independientemente hidrogeno, halo, ciano, hidroxilo, o alcoxi; y X es -O-, -C(O)-, -C(O)O-, -OC(O)O-, -C(O)NR14-, -NR14-, -NR14C(O)NR15-, -C(=NR14)NR15-, -NR14C(=NR15)NR16-, -S(O)k-, -S(O)kNR14-, -NR14S(O)kNR15-, -P(O)(OR14)-, o -OP(O)(OR14)-, donde cada R14, R15, y R16 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, y cada k es independientemente un numero entero de 1 o 2; Q1 es -O-, -N(R17)-, -C(R18R19)-, o -CR17(NR18R19)-; en donde: cada R17 y R18 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, y cada R19 es independientemente -R20, -C(O)R20, -C(O)OR20, -C(O)NR21R22, -C(=NR20)NR21R22, o -S(O)kR20; donde cada R20, R21, y R22 es independientemente hidrogeno, alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, o R21 y R22 junto con el átomo de N al cual están unidos forman heterociclilo; o R18 y R19 junto con el átomo de C o N al cual están unidos forman cicloalquilo C3-7 o heterociclilo; Q2 es alquileno C3-9, alquenileno C3-9, o alquinileno C3-9, en donde cada uno contiene opcionalmente de uno a tres heteroátomos en la cadena, independientemente seleccionados de O, N, y S; y cada k es independientemente un numero entero de 1 o 2; en donde cada alquilo, alquileno, alquenilo, alquenileno, alquinilo, alquinileno, arilo, cicloalquilo, cicloalquileno, heterociclilo y heteroarilo es opcionalmente sustituido con uno o más grupos, cada uno independientemente seleccionado de ciano, halo, o nitro; alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, cada uno opcionalmente sustituido con uno o más sustituyentes Q; o -C(O)Ra, -C(O)ORa, -C(O)NRbRc, -C(NRa)NRbRc, -ORa, -OC(O)Ra, -OC(O)ORa, -OC(O)NRbRc, -OC(=NRa)NRbRc, -OS(O)Ra, -OS(O)2Ra, -OS(O)NRbRc, -OS(O)2NRbRc, -NRbRc, -NRaC(O)Rb, -NRaC(O)ORb, -NRaC(O)NRbRc, -NRaC(=NRd)NRbRc, -NRaS(O)Rb, -NRaS(O)2Rb, -NRaS(O)NRbRc, -NRaS(O)2NRbRc, -SRa, -S(O)Ra, o -S(O)2Ra; en donde cada Ra, Rb, Rc, y Rd es independientemente hidrogeno; alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, cada uno opcionalmente sustituido con uno o más sustituyentes Q: o Rb y Rc junto con el átomo de N al cual están unidos forman heterociclilo, opcionalmente sustituido con uno o más sustituyentes Q; en donde cada Q es independientemente seleccionado del grupo que consiste en ciano, halo, o nitro; alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, o -C(O)Re, -C(O)ORe, -C(O)NRfRg, -C(NRe)NRfRg, -ORe, -OC(O)Re, -OC(O)ORe, -OC(O)NRfRg, -OC(=NRe)NRfRg, -OS(O)Re, -OS(O)2Re, -OS(O)NRfRg, -OS(O)2NRfRg, -NRfRg, -NReC(O)Rf, -NReC(O)ORf, - NReC(O)NRfRg, -NReC(=NRh)NRfRg, -NReS(O)Rf, -NReS(O)2Rf, -NReS(O)NRfRg, -NReS(O)2NRfRg, -SRe, -S(O)Re, o -S(O)2Re; en donde cada Re, Rf, Rg, y Rh es independientemente hidrogeno; alquilo C1-6, alquenilo C2-6, alquinilo C2-6, cicloalquilo C3-7, arilo C6-14, heteroarilo, o heterociclilo, o Rf y Rg junto con el átomo de N al cual están unidos forman heterociclilo.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2608608P | 2008-02-04 | 2008-02-04 | |
| US8386708P | 2008-07-25 | 2008-07-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR070413A1 true AR070413A1 (es) | 2010-04-07 |
Family
ID=40568607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090100353A AR070413A1 (es) | 2008-02-04 | 2009-02-03 | Inhibidores macrociclicos de proteasa de serina |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US8003659B2 (es) |
| EP (1) | EP2250174B1 (es) |
| JP (1) | JP5574982B2 (es) |
| KR (1) | KR20100118991A (es) |
| CN (1) | CN101977915B (es) |
| AR (1) | AR070413A1 (es) |
| AU (1) | AU2009210789B2 (es) |
| BR (1) | BRPI0908021A2 (es) |
| CA (1) | CA2712971A1 (es) |
| CO (1) | CO6501153A2 (es) |
| CR (1) | CR11618A (es) |
| EC (1) | ECSP10010413A (es) |
| ES (1) | ES2437147T3 (es) |
| IL (1) | IL207333A0 (es) |
| MX (1) | MX2010008523A (es) |
| NI (1) | NI201000136A (es) |
| NZ (1) | NZ587133A (es) |
| RU (1) | RU2490272C2 (es) |
| TW (1) | TW200936131A (es) |
| WO (1) | WO2009099596A2 (es) |
| ZA (1) | ZA201005318B (es) |
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| KR20100027134A (ko) | 2007-05-10 | 2010-03-10 | 인터뮨, 인크. | Ｃ형 간염 바이러스 복제의 신규 펩티드 억제제 |
| WO2009142842A2 (en) | 2008-04-15 | 2009-11-26 | Intermune, Inc. | Novel macrocyclic inhibitors of hepatitis c virus replication |
| UY32099A (es) | 2008-09-11 | 2010-04-30 | Enanta Pharm Inc | Inhibidores macrocíclicos de serina proteasas de hepatitis c |
| KR20110054003A (ko) | 2008-09-17 | 2011-05-24 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｈｃｖ ｎｓ3 프로테아제 억제제와 인터페론 및 리바비린의 병용물 |
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| CN104136453B (zh) | 2012-01-11 | 2018-01-12 | 艾伯维公司 | 用于制备hcv蛋白酶抑制剂的方法 |
| UA119315C2 (uk) | 2012-07-03 | 2019-06-10 | Гіліад Фармассет Елелсі | Інгібітори вірусу гепатиту с |
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- 2009-02-03 AU AU2009210789A patent/AU2009210789B2/en not_active Ceased
- 2009-02-03 NZ NZ587133A patent/NZ587133A/xx not_active IP Right Cessation
- 2009-02-03 CN CN200980109867.8A patent/CN101977915B/zh not_active Expired - Fee Related
- 2009-02-03 CA CA2712971A patent/CA2712971A1/en not_active Abandoned
- 2009-02-03 BR BRPI0908021-0A patent/BRPI0908021A2/pt not_active IP Right Cessation
- 2009-09-18 US US12/563,072 patent/US8093379B2/en active Active
-
2010
- 2010-07-26 ZA ZA2010/05318A patent/ZA201005318B/en unknown
- 2010-08-01 IL IL207333A patent/IL207333A0/en unknown
- 2010-08-03 NI NI201000136A patent/NI201000136A/es unknown
- 2010-08-04 CR CR11618A patent/CR11618A/es not_active Application Discontinuation
- 2010-08-20 EC EC2010010413A patent/ECSP10010413A/es unknown
- 2010-09-06 CO CO10110008A patent/CO6501153A2/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2011520772A (ja) | 2011-07-21 |
| NI201000136A (es) | 2011-03-23 |
| WO2009099596A2 (en) | 2009-08-13 |
| US8093379B2 (en) | 2012-01-10 |
| US20090202480A1 (en) | 2009-08-13 |
| US8003659B2 (en) | 2011-08-23 |
| HK1144198A1 (en) | 2011-02-02 |
| ES2437147T3 (es) | 2014-01-09 |
| RU2490272C2 (ru) | 2013-08-20 |
| CO6501153A2 (es) | 2012-08-15 |
| ECSP10010413A (es) | 2010-11-30 |
| KR20100118991A (ko) | 2010-11-08 |
| IL207333A0 (en) | 2010-12-30 |
| WO2009099596A3 (en) | 2009-12-03 |
| CN101977915A (zh) | 2011-02-16 |
| WO2009099596A4 (en) | 2010-02-04 |
| CR11618A (es) | 2011-01-31 |
| EP2250174B1 (en) | 2013-08-28 |
| ZA201005318B (en) | 2011-10-26 |
| RU2010136973A (ru) | 2012-03-20 |
| AU2009210789A1 (en) | 2009-08-13 |
| TW200936131A (en) | 2009-09-01 |
| CN101977915B (zh) | 2014-08-13 |
| US20100016578A1 (en) | 2010-01-21 |
| MX2010008523A (es) | 2010-08-31 |
| AU2009210789B2 (en) | 2014-01-30 |
| EP2250174A2 (en) | 2010-11-17 |
| BRPI0908021A2 (pt) | 2015-07-21 |
| JP5574982B2 (ja) | 2014-08-20 |
| NZ587133A (en) | 2012-10-26 |
| CA2712971A1 (en) | 2009-08-13 |
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