AR084389A1 - Compuestos de nucleosidos 1’-carba sustituidos para tratamiento antiviral - Google Patents
Compuestos de nucleosidos 1’-carba sustituidos para tratamiento antiviralInfo
- Publication number
- AR084389A1 AR084389A1 ARP110101821A ARP110101821A AR084389A1 AR 084389 A1 AR084389 A1 AR 084389A1 AR P110101821 A ARP110101821 A AR P110101821A AR P110101821 A ARP110101821 A AR P110101821A AR 084389 A1 AR084389 A1 AR 084389A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- aryl
- heterocyclyl
- carbocyclyl
- alkynyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 5
- VZQXUWKZDSEQRR-UHFFFAOYSA-N Nucleosid Natural products C12=NC(SC)=NC(NCC=C(C)C)=C2N=CN1C1OC(CO)C(O)C1O VZQXUWKZDSEQRR-UHFFFAOYSA-N 0.000 title 1
- 230000000840 anti-viral effect Effects 0.000 title 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 8
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 7
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000005884 carbocyclylalkyl group Chemical group 0.000 abstract 6
- 125000001072 heteroaryl group Chemical group 0.000 abstract 6
- 125000004452 carbocyclyl group Chemical group 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 239000002777 nucleoside Substances 0.000 abstract 2
- -1 C2- heterocyclyl 20 Chemical group 0.000 abstract 1
- 208000005176 Hepatitis C Diseases 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 208000010710 hepatitis C virus infection Diseases 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003835 nucleoside group Chemical group 0.000 abstract 1
- 239000010452 phosphate Substances 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
-
- 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no 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
- C07D309/10—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Oncology (AREA)
- Virology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Saccharide Compounds (AREA)
Abstract
Se proporcionan profármacos de nucleósidos fosfato de pirrolo[1,2-f][1,2,4]triazin-7-ilo en donde la posición 1’ del azúcar del nucleósido está sustituida con CN. Los compuestos, las composiciones y los usos provistos son eficaces para el tratamiento de infecciones de Hepatitis C.Reivindicación 1: Un compuesto de fórmula (1) o una sal o éster farmacéuticamente aceptable del mismo; en donde: R1 es un H, alquilo C1-8, alquenilo C2-8, o alquinilo C2-8; R2 es OH o -OC(O)R3; cada R3 es independiente del H, OR4, NH(R4), N(R4)2, SR4, alquilo C2-8, alquenilo C2-8, alquinilo C2-8, carbociclilo C3-8, carbociclilalquilo C4-8, arilo-alquilo C1-8, heterociclilo-alquilo C1-8, arilo, heterociclilo o heteroarilo; cada Ra, R4 o R6 es independiente del alquilo C1-8, alquenilo C2-8, alquinilo C2-8, carbociclilo C3-8, carbociclilalquilo C4-8, arilo-alquilo C1-8, heterociclilo-alquilo C1-8, arilo C6-20, heterociclilo C2-20 o heteroarilo; uno de los W1 o W2 es un compuesto de fórmula (2) y el otro de los W1 o W2 es OR4 o el compuesto de formula (2); cada Rc, Rd o R5 es independiente del H, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, carbociclilo C3-8, carbociclilalquilo C4-8, arilo-alquilo C1-8, heterociclilo-alquilo C1-8, arilo C6-20, heterociclilo C2-20 o heteroarilo; cada R8 es un halógeno, NR11R12, N(R11)OR11, NR11NR11R12, N3, NO, NO2, CHO, CN, -CH(=NR11), CH=NNHR11, CH=N(OR11), CH(OR11)2, C(=O)NR11R12, C(=S)NR11R12, C(=O)OR11, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, carbociclilalquilo C4-8, arilo C6-20, heterociclilo C2-20, heteroarilo, -C(=O)alquilo C1-8, -S(O)n-alquilo C1-8, arilo-alquilo C1-8, OR11 o SR11; cada n es independientemente 0, 1 ó 2; cada R9 o R10 es independiente del H, halógeno, NR11R12, N(R11)OR11, NR11NR11R12, N3, NO, NO2, CHO, CN, -CH(=NR11), -CH=NHNR11, -CH=N(OR11), -CH(OR11)2, -C(=O)NR11R12, -C(=S)NR11R12, -C(=O)OR11, R11, OR11 o SR11; cada R11 o R12 es independiente del H, alquilo C1-8, alquenilo C2-8, alquinilo C2-8, carbociclilo C3-8, carbociclilalquilo C4-8, arilo-alquilo C1-8, heterociclilo-alquilo C1-8, arilo C6-20, heterociclilo C2-20, heteroarilo, -C(=O)alquilo C1-8, -S(O)n-alquilo C1-8 o R11 y R12 junto con un nitrógeno al cual están unidos forman un anillo heterocíclico de 3 a 7 miembros en donde cualquiera de los átomos de carbono de dicho anillo heterocíclico puede reemplazarse opcionalmente con -O-, -S(O)n- o -NRa-; en donde cada alquilo C1-8, alquenilo C2-8, alquinilo C2-8, carbociclilo C3-8, carbociclilalquilo C4-8, arilo-alquilo C1-8, heterociclilo-alquilo C1-8, arilo C6-20, heterociclilo C2-20, heteroarilo de Rc, Rd, R1, R2, R3, R4, R5, R6, R8, R11 o R12 está, independientemente, sustituido, de manera opcional, con uno o más halo, hidroxi, CN, N3, N(Ra)2 NH(Ra), NH2, C(O)N(Ra)2, C(O)NH(Ra), C(O)NH2, OC(O)N(Ra)2, OC(O)NH(Ra), OC(O)NH2, C(O)ORa, OC(O)ORa, C(O)Ra, OC(O)Ra, S(O)nRa, S(O)2N(Ra)2, S(O)2NH(Ra), S(O)2NH2, ORa o Ra.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34959710P | 2010-05-28 | 2010-05-28 | |
| US35335110P | 2010-06-10 | 2010-06-10 | |
| US36604110P | 2010-07-20 | 2010-07-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR084389A1 true AR084389A1 (es) | 2013-05-15 |
Family
ID=45375840
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110101821A AR084389A1 (es) | 2010-05-28 | 2011-05-27 | Compuestos de nucleosidos 1’-carba sustituidos para tratamiento antiviral |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8415308B2 (es) |
| EP (1) | EP2576534B1 (es) |
| JP (4) | JP5837577B2 (es) |
| AR (1) | AR084389A1 (es) |
| CY (1) | CY1115479T1 (es) |
| DK (1) | DK2576534T3 (es) |
| ES (1) | ES2465265T3 (es) |
| HK (1) | HK1182387A1 (es) |
| HR (1) | HRP20140370T1 (es) |
| ME (1) | ME01882B (es) |
| PL (1) | PL2576534T3 (es) |
| PT (1) | PT2576534E (es) |
| RS (1) | RS53244B (es) |
| SI (1) | SI2576534T1 (es) |
| SM (1) | SMT201400048B (es) |
| TW (1) | TW201201815A (es) |
| UY (1) | UY33414A (es) |
| WO (1) | WO2011150288A1 (es) |
Families Citing this family (69)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY164523A (en) | 2000-05-23 | 2017-12-29 | Univ Degli Studi Cagliari | Methods and compositions for treating hepatitis c virus |
| AU2003298658A1 (en) | 2002-11-15 | 2004-06-15 | Idenix (Cayman) Limited | 2'-branched nucleosides and flaviviridae mutation |
| HUE025528T2 (en) | 2008-04-23 | 2016-05-30 | Gilead Sciences Inc | 1'-substituted carba-nucleoside analogs for antiviral treatment |
| EP2480559B1 (en) | 2009-09-21 | 2013-07-03 | Gilead Sciences, Inc. | Processes and intermediates for the preparation of 1'-cyano-carbanucleoside analogs |
| TW201201815A (en) * | 2010-05-28 | 2012-01-16 | Gilead Sciences Inc | 1'-substituted-carba-nucleoside prodrugs for antiviral treatment |
| KR20200052384A (ko) | 2010-07-19 | 2020-05-14 | 길리애드 사이언시즈, 인코포레이티드 | 부분입체 이성질성으로 순수한 포스포라미데이트 전구약물의 제조 방법 |
| EP2595980B1 (en) | 2010-07-22 | 2014-09-03 | Gilead Sciences, Inc. | Methods and compounds for treating paramyxoviridae virus infections |
| CA2822037A1 (en) * | 2010-12-20 | 2012-06-28 | Gilead Sciences, Inc. | Methods for treating hcv |
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| NZ623396A (en) | 2011-09-16 | 2016-07-29 | Gilead Pharmasset Llc | Methods for treating hcv |
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| UA119050C2 (uk) | 2013-11-11 | 2019-04-25 | Ґілеад Саєнсиз, Інк. | ПІРОЛО[1.2-f][1.2.4]ТРИАЗИНИ, ЯКІ ВИКОРИСТОВУЮТЬСЯ ДЛЯ ЛІКУВАННЯ РЕСПІРАТОРНО-СИНЦИТІАЛЬНИХ ВІРУСНИХ ІНФЕКЦІЙ |
| EP3131914B1 (en) | 2014-04-16 | 2023-05-10 | Idenix Pharmaceuticals LLC | 3'-substituted methyl or alkynyl nucleosides for the treatment of hcv |
| EP3137454A1 (en) | 2014-04-28 | 2017-03-08 | Pfizer Inc. | Heteroaromatic compounds and their use as dopamine d1 ligands |
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| US20120020921A1 (en) | 2012-01-26 |
| JP2016094404A (ja) | 2016-05-26 |
| JP2013528184A (ja) | 2013-07-08 |
| SMT201400048B (it) | 2014-05-07 |
| US8415308B2 (en) | 2013-04-09 |
| HK1182387A1 (en) | 2013-11-29 |
| ES2465265T3 (es) | 2014-06-05 |
| WO2011150288A1 (en) | 2011-12-01 |
| PL2576534T3 (pl) | 2014-07-31 |
| HRP20140370T1 (hr) | 2014-05-23 |
| JP5837577B2 (ja) | 2015-12-24 |
| EP2576534B1 (en) | 2014-03-19 |
| UY33414A (es) | 2011-12-30 |
| TW201201815A (en) | 2012-01-16 |
| PT2576534E (pt) | 2014-05-29 |
| CY1115479T1 (el) | 2017-01-04 |
| SI2576534T1 (sl) | 2014-06-30 |
| JP2018162268A (ja) | 2018-10-18 |
| JP6193332B2 (ja) | 2017-09-06 |
| EP2576534A1 (en) | 2013-04-10 |
| DK2576534T3 (da) | 2014-04-22 |
| RS53244B (en) | 2014-08-29 |
| ME01882B (me) | 2014-12-20 |
| JP2018012706A (ja) | 2018-01-25 |
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