ES2555209T3 - Inhibidores del citocromo P450 - Google Patents

Inhibidores del citocromo P450 Download PDF

Info

Publication number
ES2555209T3
ES2555209T3 ES08869426.0T ES08869426T ES2555209T3 ES 2555209 T3 ES2555209 T3 ES 2555209T3 ES 08869426 T ES08869426 T ES 08869426T ES 2555209 T3 ES2555209 T3 ES 2555209T3
Authority
ES
Spain
Prior art keywords
alkyl
group
substituted
unsubstituted
haloalkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
ES08869426.0T
Other languages
English (en)
Inventor
Manoj Desai
Hon Chung Hui
Hongtao Liu
Lianhong Xu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Gilead Sciences Inc
Original Assignee
Gilead Sciences Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Gilead Sciences Inc filed Critical Gilead Sciences Inc
Application granted granted Critical
Publication of ES2555209T3 publication Critical patent/ES2555209T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D277/28—Radicals substituted by nitrogen atoms
    • 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
    • A61K31/41—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
    • A61K31/425—Thiazoles
    • A61K31/427—Thiazoles not condensed and containing further heterocyclic 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
    • A61K31/335—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
    • 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
    • A61K31/341—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 not condensed with another ring, e.g. ranitidine, furosemide, bufetolol, muscarine
    • 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-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
    • C07D307/18—Heterocyclic compounds containing five-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
    • C07D307/20—Oxygen atoms
    • 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
    • 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
    • C07D417/14—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 three or more hetero rings
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Molecular Biology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Furan Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Pyridine Compounds (AREA)

Abstract

Un compuesto de Fórmula I,**Fórmula** o una sal, un solvato y/o un éster farmacéuticamente aceptables del mismo, en donde, X1 se selecciona entre el grupo que consiste en -C(O)-O-, -S(O)- y -S(O2)-, -C(O)NR6-; X2 se selecciona entre el grupo que consiste en -O-, -NR6-C(O)-NR6-, -OC(O)NR6-, -NR6- y -NR6C(O)O-; L se selecciona entre el grupo que consiste en un enlace covalente, alquileno y -CHR7-; R1 se selecciona entre el grupo que consiste en fenilo no sustituido, fenilo sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en alquilo, alquilo sustituido, halo, hidroxilo, amino, haloalquilo y ciano, heteroarilalquilo no sustituido, en donde la porción heteroarilo del mismo es tiazolilo y heteroarilalquilo sustituido, en donde la porción heteroarilo del mismo es tiazolilo sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en alquilo, alquilo sustituido, halo, hidroxilo, amino, haloalquilo y ciano; un R2 es bencilo no sustituido y el otro R2 es H o alquilo; R3 se selecciona entre el grupo que consiste en tetrahidro-2H-furo[2,3-b]furanilo no sustituido; tetrahidrofuranilo no sustituido; tiazolilo no sustituido, tiazolilo sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en alquilo, alquilo sustituido, halo, hidroxilo, amino, haloalquilo y ciano; tiazolilmetilo no sustituido y tiazolilmetilo sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en alquilo, alquilo sustituido, halo, hidroxilo, amino, haloalquilo y ciano; R4 es H o alquilo; R5 se selecciona entre el grupo que consiste en H, alquilo y bencilo sustituido con uno o más sustituyentes seleccionados entre el grupo que consiste en alquilo, alquilo sustituido, bencilo, alcoxi, benciloxi, -O-CH2-piridilo, halo, hidroxilo, amino, haloalquilo y ciano; cada R6 se selecciona independientemente entre el grupo que consiste en H, alquilo y cicloalquilo; y R7 se selecciona entre el grupo que consiste en H, alquilo, alquilo sustituido y heterociclilalquilo; en donde cada arilo, heteroarilo, cicloalquilo, heterociclilo, cicloalquilalquilo, heterociclilalquilo, arilalquilo y heteroarilalquilo de R1, R2, R3, R4, R5, R6 y R7 está sin sustituir o sustituido.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
imagen6
imagen7
imagen8
imagen9
imagen10
imagen11
imagen12
imagen13
imagen14
imagen15
imagen16
imagen17
imagen18
imagen19
imagen20
imagen21
imagen22
imagen23
imagen24
imagen25
imagen26
imagen27
imagen28
imagen29
imagen30
imagen31
imagen32
imagen33
imagen34
imagen35
imagen36
imagen37
imagen38
imagen39
imagen40
imagen41
imagen42
imagen43
imagen44
imagen45
imagen46
imagen47
imagen48
imagen49
imagen50
imagen51
imagen52
imagen53
imagen54
imagen55
imagen56
imagen57
imagen58
imagen59
imagen60
imagen61
imagen62
imagen63
imagen64
imagen65
imagen66
2c
imagen67
2d
imagen68
2e
imagen69
2f
imagen70
2g
imagen71
2h
imagen72
2i
imagen73
68 69
2j
imagen74
2k
imagen75
21
imagen76
2m
imagen77
2n
imagen78
2o
imagen79
2p
imagen80
imagen81
imagen82
imagen83
imagen84
imagen85
imagen86
imagen87
imagen88
imagen89
imagen90
imagen91
imagen92
imagen93
imagen94
imagen95
imagen96
imagen97
imagen98
imagen99
imagen100
imagen101
imagen102
imagen103
imagen104
imagen105
imagen106
imagen107
imagen108
imagen109
imagen110
imagen111
imagen112
imagen113
imagen114
imagen115
imagen116
imagen117
imagen118
imagen119
imagen120
imagen121
imagen122
imagen123
imagen124
imagen125
imagen126
imagen127
imagen128
imagen129
imagen130
imagen131
imagen132
imagen133
Bn
bencilo
BnBr
bencilbromuro
BSA
bis(trimetilsilil)acetamida
BzCl
cloruro de benzoílo
CDI
carbonildiimidazol
dba
dibencilidenacetona
DCC
diciclohexilcarbodiimida
DIPEA
di-isopropiletilamina
DMAP
4-dimetilaminopiridina
DMA o DMAC
N,N-dimetilacetamida
DMTCI
cloruro de dimetoxitritilo
DMSO
dimetilsulfóxido
DMF
dimetilformamida
EtOAc
acetato de etilo
IEN
ionización por electronebulización
HMDS
hexametildisilazano
HPLC
cromatografía líquida de alta presión
LDA
diisopropilamida de litio
LRMS
espectro de masas de baja resolución
mCPBA
ácido meta-cloroperbenzoico
MeOH
metanol
m/z o m/e
relación de masa y carga
MH+
masa más 1
MH
masa menos 1
MsOH
ácido metanosulfónico
EM o em
espectro de masas
NBS
N-bromosuccinimida
NMP
N-metilpirrolidinona
ta o t.a.
Temperature ambiente
TMSCl
clorotrimetilsilano
TMSBr
bromotrimetilsilano
TMSI
iodotrimetilsilane
TEA
trietilamina
TBA
tributilamina
TBAP
pirofosfato de tributilamonio
TBSCl
cloruro de t-butildimetilsililo
TEAB
bicarbonato de trietilamonio
TFA
ácido trifluoroacético
123
imagen134
imagen135
imagen136
imagen137
imagen138
imagen139
imagen140
imagen141
imagen142
imagen143
imagen144
imagen145
imagen146
imagen147

Claims (1)

  1. imagen1
    imagen2
    imagen3
    imagen4
    imagen5
ES08869426.0T 2008-01-04 2008-12-19 Inhibidores del citocromo P450 Active ES2555209T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US1907908P 2008-01-04 2008-01-04
US19079P 2008-01-04
PCT/US2008/087821 WO2009088719A1 (en) 2008-01-04 2008-12-19 Inhibitors of cytochrome p450

Publications (1)

Publication Number Publication Date
ES2555209T3 true ES2555209T3 (es) 2015-12-29

Family

ID=40380546

Family Applications (1)

Application Number Title Priority Date Filing Date
ES08869426.0T Active ES2555209T3 (es) 2008-01-04 2008-12-19 Inhibidores del citocromo P450

Country Status (8)

Country Link
US (1) US8759379B2 (es)
EP (1) EP2231628B1 (es)
JP (2) JP5629585B2 (es)
AU (1) AU2008346823B2 (es)
CA (1) CA2710679A1 (es)
ES (1) ES2555209T3 (es)
PT (1) PT2231628E (es)
WO (1) WO2009088719A1 (es)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
UA108738C2 (uk) * 2009-04-03 2015-06-10 Спосіб одержання інгібітора цитохром р450 монооксигенази та залучені проміжні сполуки
PE20121524A1 (es) 2010-01-27 2012-12-03 Viiv Healthcare Co Combinaciones de compuestos que comprenden inhibidores de la integrasa de vih y otros agentes terapeuticos
WO2012088156A1 (en) * 2010-12-21 2012-06-28 Gilead Sciences, Inc. Inhibitors of cytochrome p450
EP4556010A3 (en) 2011-11-30 2025-07-23 Emory University Jak inhibitors for use in the prevention or treatment of a viral disease caused by a coronaviridae
JP2015503624A (ja) * 2012-01-12 2015-02-02 ギリアード サイエンシーズ， インコーポレイテッド 医薬組成物およびその調製方法
CN104540813A (zh) * 2012-06-27 2015-04-22 默沙东公司 磺酰胺衍生物以及使用它们用于改善药物的药物动力学的方法
WO2014000178A1 (en) 2012-06-27 2014-01-03 Merck Sharp & Dohme Corp. Sulfonamide derivatives and methods of use thereof for improving the pharmacokinetics of a drug
CN103694196A (zh) * 2012-09-27 2014-04-02 上海迪赛诺化学制药有限公司 细胞色素p450单加氧酶抑制剂中间体及其制法和用途
JP2016504364A (ja) * 2012-12-26 2016-02-12 アッシア・ケミカル・インダストリーズ・リミテッド コビシスタット塩
WO2014194519A1 (en) 2013-06-07 2014-12-11 Merck Sharp & Dohme Corp. Imidazole derivatives and methods of use thereof for improving pharmacokinetics of drug
JP2016539098A (ja) * 2013-10-25 2016-12-15 チルドレンズ メディカル センター コーポレーション 網膜の血管障害を治療又は予防する方法
WO2015070366A1 (en) 2013-11-12 2015-05-21 Merck Sharp & Dohme Corp. Aryl linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug
WO2015070367A1 (en) 2013-11-12 2015-05-21 Merck Sharp & Dohme Corp. Piperidine or piperazine linked imidazole and triazole derivatives and methods of use thereof for improving the pharmacokinetics of a drug
CN105669749B (zh) * 2014-08-14 2018-03-30 赫斯（西安）生物科技有限公司 抗病毒药物及组合物
CN105884826B (zh) * 2014-08-14 2018-01-19 赫斯（西安）生物科技有限公司 抗病毒药物
DK3236972T3 (en) 2014-12-26 2021-10-04 Univ Emory Antivirale N4-hydroxycytidin-derivativer
JP6804790B1 (ja) 2017-12-07 2020-12-23 エモリー ユニバーシティー Ｎ４−ヒドロキシシチジンおよび誘導体ならびにそれらに関連する抗ウイルス用途
NL2024544B1 (en) * 2018-12-21 2021-03-15 Aim Immunotech Inc Compositions And Methods For Cancer Therapy
WO2022061309A1 (en) * 2020-09-21 2022-03-24 Aim Immunotech Inc. Compositions and methods for treating cancer
CA3200556A1 (en) * 2020-12-01 2021-11-30 David Din Belle 2,3-dihydro-4h-benzo[b][1,4]oxazin-4-yl)(5-(phenyl)-pyridin-3-yl)methanone derivatives and similar compounds as cyp11a1 inhibitors for the treatment of prostate cancer

Family Cites Families (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5142056A (en) * 1989-05-23 1992-08-25 Abbott Laboratories Retroviral protease inhibiting compounds
US5354866A (en) * 1989-05-23 1994-10-11 Abbott Laboratories Retroviral protease inhibiting compounds
US5552558A (en) * 1989-05-23 1996-09-03 Abbott Laboratories Retroviral protease inhibiting compounds
US5362912A (en) * 1989-05-23 1994-11-08 Abbott Laboratories Process for the preparation of a substituted diaminodiol
EP0428849A3 (en) 1989-09-28 1991-07-31 Hoechst Aktiengesellschaft Retroviral protease inhibitors
ATE218541T1 (de) * 1992-08-25 2002-06-15 Searle & Co Hydroxyethylaminosulfonamide verwendbar als inhibitoren retroviraler proteasen
US5968942A (en) * 1992-08-25 1999-10-19 G. D. Searle & Co. α- and β-amino acid hydroxyethylamino sulfonamides useful as retroviral protease inhibitors
EP1302468B1 (en) 1992-12-29 2008-12-17 Abbott Laboratories Processes and intermediates for manufacturing retroviral protease inhibiting compounds
JP3453741B2 (ja) * 1993-07-08 2003-10-06 日本製紙株式会社 感熱記録体
US5628072A (en) * 1994-06-20 1997-05-13 Sharp Plastics Manufacturing Ltd. Eye goggles with laterally adjustable eyepieces within goggles frame
DE4424828A1 (de) * 1994-07-14 1996-01-18 Thomae Gmbh Dr K Neue substituierte Arylsulfonamide, ihre Herstellung und ihre Verwendung als Arzneimittel
US5567823A (en) * 1995-06-06 1996-10-22 Abbott Laboratories Process for the preparation of an HIV protease inhibiting compound
US6037157A (en) 1995-06-29 2000-03-14 Abbott Laboratories Method for improving pharmacokinetics
US5763464A (en) * 1995-11-22 1998-06-09 The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services Retroviral agents containing anthranilamide, substituted benzamide and other subunits, and methods of using same
DE19653427A1 (de) * 1996-12-20 1998-07-02 Siemens Ag Kraftsensor
FR2773994B1 (fr) 1998-01-23 2002-10-11 Univ Nice Sophia Antipolis Prodrogues issues d'anti-proteases inhibitrices du virus de l'immunodeficience humaine (vih) pour l'amelioration de leur biodisponibilite, de leur tropisme vers et/ou de leur delivrance dans le systeme nerveux central
ATE332132T1 (de) 1999-06-04 2006-07-15 Abbott Lab Verbesserte arzneizubereitungen enthaltend ritonavir
EP1222192B8 (en) 1999-10-06 2008-10-01 Tibotec Pharmaceuticals Ltd. Hexahydrofuro¬2,3-b furan-3-yl-n- 3-¬(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino -1-benzyl-2-hydroxypropyl carbamate as retroviral protease inhibitor
AU2001259817A1 (en) * 2000-05-04 2001-11-12 The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services, The National Institutes Of Health Methods of and compounds for inhibiting calpains
US7193065B2 (en) * 2001-07-13 2007-03-20 Roche Diagnostics Operations, Inc. Protease inhibitor conjugates and antibodies useful in immunoassay
UY29101A1 (es) * 2004-09-07 2006-03-31 Smithkline Beecham Corp 1,3-diaminas aceclicas y usos de las mismas
US7786153B2 (en) * 2005-03-02 2010-08-31 Abbott Laboratories Inc. Compounds that are useful for improving pharmacokinetics
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
SG183007A1 (en) 2006-07-07 2012-08-30 Gilead Sciences Inc Modulators of pharmacokinetic properties of therapeutics
PL3150586T3 (pl) * 2007-02-23 2020-06-01 Gilead Sciences, Inc. Modulatory farmakokinetycznych właściwości środków terapeutycznych
EP2170851B1 (en) * 2007-07-06 2013-09-04 Gilead Sciences, Inc. Modulators of pharmacokinetic properties of therapeutics

Also Published As

Publication number Publication date
WO2009088719A1 (en) 2009-07-16
EP2231628B1 (en) 2015-10-28
JP2011508778A (ja) 2011-03-17
EP2231628A1 (en) 2010-09-29
JP2014169338A (ja) 2014-09-18
US8759379B2 (en) 2014-06-24
JP5629585B2 (ja) 2014-11-19
HK1148520A1 (zh) 2011-09-09
US20090175820A1 (en) 2009-07-09
AU2008346823B2 (en) 2015-03-12
CA2710679A1 (en) 2009-07-16
AU2008346823A1 (en) 2009-07-16
PT2231628E (pt) 2015-12-29

Similar Documents

Publication Publication Date Title
ES2555209T3 (es) Inhibidores del citocromo P450
CA2574651C (en) Preparation of alkyl-substituted 2-deoxy-2-fluoro-d-ribofuranosyl pyrimidines and purines and their derivatives
ES2726998T3 (es) Análogos de nucleósidos fluorados modificados
ES2678073T3 (es) Compuestos moduladores de receptores de andrógenos
ES2432590T3 (es) Fenilcarbamatos macrocíclicos inhibidores del VHC
AR062224A1 (es) Tetrazolilos macrociclicos como inhibidores de serina proteasa ns3 del virus de hepatitis c y composiciones farmaceuticas que los comprenden.
WO2010135520A1 (en) Compounds, compositions and methods for treating viral infection
WO2007027248A2 (en) 3', 5' - cyclic nucleoside analogues for treatment of hcv
RU2015148010A (ru) Высокоактивное производное нуклеозида для лечения hcv
CY1112254T1 (el) Αρυλικοι φωσφοραμιδικοι εστερες νουκλεοζιτων και οι χρησεις τους ως αντι-ιικοι παραγοντες για την αντιμετωπιση του ιου της ηπατιτιδας c
KR20170001722A (ko) 1-(2-데옥시-2-플루오로-4-티오-β-D-아라비노푸라노실)시토신의 합성 중간체, 티오뉴클레오시드의 합성 중간체, 및 그들의 제조법
WO2015095305A1 (en) Production of cyclic phosphate, phosphoramidate, thiophosphate, and phosphonate nucleoside compounds
ES2390930T3 (es) Sal de ácido p-toluensulfónico de 5-amino-3-(2'-O-acetil-3'-desoxi-beta-D-ribofuranosil)-3H-tiazolo[4,5-d]pirimidin-2-ona y procedimientos e preparación
JP6175553B2 (ja) チオラン骨格型糖化合物の製造方法およびチオラン骨格型糖化合物
KR20050110611A (ko) 3'-뉴클레오사이드 프로드럭의 생산 방법
HRP20130906T1 (hr) Postupci i intermedijeri za pripravu makrocikliäśkog inhibitora hcv proteaze
PE55298A1 (es) Derivados de pirrolopirrolona
CN117402178B (zh) 作为jak抑制剂和phd抑制剂的嘧啶类化合物
AU2011318241A1 (en) Viral polymerase inhibitors
Guo et al. Discovery of pyrimidine nucleoside dual prodrugs and pyrazine nucleosides as novel anti-HCV agents
JP2014505662A5 (es)
AU2008203443B2 (en) Stereoselective method for the preparation of nucleoside analogues
JPH11140085A5 (es)
FR2900154B1 (fr) Nouveaux composes c-glycosides gem-difluores derives de la podophyllotoxine, leur preparation et leurs applications.
CN102887901A (zh) 无环核苷酸类似物及其制备方法和应用