AR055165A1 - Inhibidores ns5b de vhc de indolobenzacepina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de la hepatitis c. - Google Patents
Inhibidores ns5b de vhc de indolobenzacepina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de la hepatitis c.Info
- Publication number
- AR055165A1 AR055165A1 ARP060103983A ARP060103983A AR055165A1 AR 055165 A1 AR055165 A1 AR 055165A1 AR P060103983 A ARP060103983 A AR P060103983A AR P060103983 A ARP060103983 A AR P060103983A AR 055165 A1 AR055165 A1 AR 055165A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cycloalkyl
- amino
- alkoxy
- co2r6
- Prior art date
Links
- 101800001554 RNA-directed RNA polymerase Proteins 0.000 title 1
- 208000006454 hepatitis Diseases 0.000 title 1
- 231100000283 hepatitis Toxicity 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 69
- -1 sulfolanyl Chemical group 0.000 abstract 21
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 11
- 125000003545 alkoxy group Chemical group 0.000 abstract 9
- 125000004193 piperazinyl group Chemical group 0.000 abstract 9
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 8
- 125000003282 alkyl amino group Chemical group 0.000 abstract 7
- 125000001475 halogen functional group Chemical group 0.000 abstract 7
- 125000002757 morpholinyl group Chemical group 0.000 abstract 7
- 125000003386 piperidinyl group Chemical group 0.000 abstract 7
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 7
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 abstract 6
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000001188 haloalkyl group Chemical group 0.000 abstract 5
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 241000711549 Hepacivirus C Species 0.000 abstract 3
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 3
- 125000002393 azetidinyl group Chemical group 0.000 abstract 3
- 125000002541 furyl group Chemical group 0.000 abstract 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 3
- 125000003368 amide group Chemical group 0.000 abstract 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 abstract 2
- 125000005879 dioxolanyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 abstract 2
- 125000005936 piperidyl group Chemical group 0.000 abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 125000001425 triazolyl group Chemical group 0.000 abstract 2
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 241001024304 Mino Species 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 abstract 1
- 125000000335 thiazolyl group Chemical group 0.000 abstract 1
- 125000004306 triazinyl group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed 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
-
- 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
-
- 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
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Virology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compuestos y sales de las formulas (1), (2), (3) y (4) así como composiciones y métodos para usar los compuestos. Los compuestos tienen actividad contra el virus de la hepatitis C (VHC) y son utiles en el tratamiento de aquellos infectados con VHC. Reivindicacion 1: Un compuesto de la formula (1) en donde R1 es CO2R6 o CONR7R8; R2 es CONR9R10, CO2bencilo, NHCO2(alquilo), NHCO2bencilo, NHCO(alquilo), NHCO(cicloalquilo), NHCOR14, NHCO((R15)alquilo), NHCO((R16)alquil0), NHCO(tetrahidropiranilo, NHCO(metoxicicloalquilo), NHCON(R6)2, NHCON(R6)((N(R6)2)alquilo), NHCON(R6)((CO2R6)alquilo), NHCON(R6)((CON(R6)2)alquilo, NHCON(R6) ((COR15)alquilo, NHCON(R6)((tetrahidropiranil)alquilo), o como se muestra en las formulas (5); R3 es H o alquilo; R4 es H, halo, alquilo, alcoxi o benciloxi; R5 es cicloalquilo C5-7; R6 es H, alquilo o cicloalquilo; R7 es H, alquilo, cicloalquilo, alcoxi aminoalquilo, (alquilamino)alquilo, (dialquilamino)alquilo, (CO2R6)alquilo, (CON(R6) (R6))alquilo, (alquilo)CONH, tetrazolilo, tetrahidropiranilo, sulfolanilo, SO2R11, SO2R12, o (R13)alquilo; R8 es hidrogeno, alquilo, o cicloalquilo; o NR7R8 tomado junto es pirrolidinilo, piperidinilo, piperazinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, o tiomorfolinilo, y es substituido con 0-2 substituyentes seleccionados de halo, alquilo, y haloalquilo; R9 es cicloalquilo, dihidroxialquilo, (alcoxi)alquilo, (R12)alquilo, (CHO)alquilo, (CO2R6)alquilo, (CON(R6)2)alquilo, (COR12) alquilo, (COR15) alquilo, ((alcoxialquilo)amido)alquilo, (alquilamido)alquilo, (tetrahidrofuranilo)alquilo, (dioxolanil)alquilo, (alquiloCO)(R6)amino, ((alquiloCO)(R6)amino)alquilo, tetrahidropiranilo, o sulfolanilo; R10 es hidrogeno, alquilo, cicloalquilo, hidroxialquilo, dihidroxialquilo, (alcoxi) alquilo, aminoalquilo, (alquilamino)alquilo, (dialquilamino)alquilo, (R12)alquilo, (CHO)alquilo, (CO2R6)alquilo, (CON(R6)2)alquilo, (COR12)alquilo, (COR15)alquilo, (R16)alquilo, ((alcoxialquilo)amido)alquilo, (alquilamido)alquilo, (tetrahidrofuranilo)alquilo, (dioxolanilo)alquilo, (alquiloCO)(R6) amino, ((alquiloCO(R6)amino)alquilo, tetrahidropiranilo, o sulfalanilo; o NR9R10 tomado junto es azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, o tiomorfolinilo, y es substituido con 0-4 substituyentes seleccionados del grupo que consiste de halo, hidroxi, OPO(OR6)2, alcoxi, alquilo, cicloalquilo, (cicloalquilo)alquilo, haloalquilo, hidroxialquilo, alcoxialquilo, (hidroxi) alcoxialquilo, (alcoxi)alquilo, amino, alquilamino, dialquilamino, (alquiloCO)(R6)amino, (alcoxiCO)(R6)amino, (alcoxialquiloCO)(R6)amino, (alquiloCO)alquiloamino, (cicloalquilo)(PhSO2)amino, CO2R6, CON(R6)2, CONH(alquenilo), (R12)CO, (alquilo)CO, (cicloalquilo)CO, (hidroxialquilo)CO, (hidroxi)cicloalquilo)CO, (aminoalquilo)CO, (acetoxialquilo)CO, PhCO, (furanilo)CO, (benzodioxanil)CO, (alquilo)CO2, SO2R11, SO2R12, (CO2R6)alquilo, (CON(R6)2)alquilo, (COR12)alquilo, (alquiloCO)(R6)aminoalquilo, (PhCONH)alquilo, (R12)alquilo, R12, fenilo, metoxifenilo, pirrolilo, furanilo, tienilo, imidazolilo, isoxazolilo, oxazolilo, tiazolilo, triazolilo, oxadiazolilo, piridinilo, pirimidinilo, pirazinilo, triazinilo, pirazolilo, o como se muestra en as formulas (6) con la condicion de que si NR9R10 es pirrolidinilo, piperidinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, o tiomorfolinilo puede substituirse con 0-2 substituyentes seleccionados de alquilo, hidroxi, amino, alquilamino, dialquilamino, pirrolidinilo, piperidinilo o piridinilo; o NR9R10 tomado junto es como se muestra en las formulas (7) o NR9R10 tomado junto es un amina bicíclica punteada [2.2.1] o [2.2.2] en donde el biciclo contiene 0-1 NR6, NCO2R6, u O; R11es alquilo, haloalquilo, cicloalquilo, alcoxi, amino, alquilamino, dialquilamino, ((R6)(R6)N)alquilamino, (((R6)(R6)N)alquilo)2amino, N,O- dimetilhidroxilamino, o fenilo, en donde el fenilo es substituido con 0-2 substituyentes seleccionados del grupo que consiste de halo, alquilo, haloalquilo y alcoxi; R12 es pirrolidinilo, piperidinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, o tiomorfolinilo, y es substituido con 0-2 substituyentes seleccionados de halo, alquilo, haloalquilo y alcoxi; R13 es pirrolidinilo, piperidinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, tiomorfolinilo, tetrahidrofuranilo, furanilo, tienilo, pirrolilo, pirazolilo, imidazolilo, isoxazolilo, oxazolilo, triazolilo, oxadiazolilo, tetrazolilo, piridinilo, pirazinilo, pirimidinilo, imidazopiridinilo, o benzimidazol y es substituido con 0- 2 substituyentes alquilo; R14 es azetidina, pirrolidinilo, piperidinilo, piperazinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, tiomorfolinilo, o S,S- dioxotiomorfolinilo, y es substituido con 0-3 substituyentes seleccionados de halo, alquilo, hidroxi, alcoxi, aminoalquilo, (alquilamino)alquilo, (dialquilamino)alquilo, (CO2R6)alquilo, (CON(R6)2)alquilo, ((R6CO)(R6)amino)alquilo, (R15)alquilo, (R6CO)(R6)amino, R15, alquiloCO, CF3CO, CO2R6, CON(R6)2, o SO2R6 o R14 es una amina bicíclica ponteada [2.2.1) o [2.2.2] en donde el biciclo contiene 0-1 O; R15 es azetidinilo, pirrolidinilo, piperidinilo, piperazinilo, homomorfolinilo, homopiperidinilo, morfolinilo, o tiomorfolinilo, y es substituido con 0-2 substituyentes halo, alquilo, o alcoxi; y la línea de rayas es ya sea un enlace sencillo o un enlace doble, con la condicion de que si la línea de rayas es un enlace sencillo, el carbono que porta el asterisco está en la configuracion ya sea R, la configuracion S, o una mezcla de R y S; o una sal farmacéuticamente aceptable del mismo.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US71669305P | 2005-09-13 | 2005-09-13 | |
US77150106P | 2006-02-08 | 2006-02-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR055165A1 true AR055165A1 (es) | 2007-08-08 |
Family
ID=37637507
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP060103983A AR055165A1 (es) | 2005-09-13 | 2006-09-12 | Inhibidores ns5b de vhc de indolobenzacepina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de la hepatitis c. |
Country Status (5)
Country | Link |
---|---|
US (1) | US7473688B2 (es) |
AR (1) | AR055165A1 (es) |
PE (1) | PE20070839A1 (es) |
TW (1) | TW200745120A (es) |
WO (1) | WO2007033175A1 (es) |
Families Citing this family (62)
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US7795247B2 (en) | 2004-10-26 | 2010-09-14 | Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa | Tetracyclic indole derivatives as antiviral agents |
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US7456165B2 (en) * | 2006-02-08 | 2008-11-25 | Bristol-Myers Squibb Company | HCV NS5B inhibitors |
GB0608928D0 (en) | 2006-05-08 | 2006-06-14 | Angeletti P Ist Richerche Bio | Therapeutic agents |
US7456166B2 (en) * | 2006-05-17 | 2008-11-25 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
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US7521441B2 (en) * | 2006-05-22 | 2009-04-21 | Bristol-Myers Squibb Company | Cyclopropyl fused indolobenzazepine HCV NS5B inhibitors |
JP5205370B2 (ja) * | 2006-05-25 | 2013-06-05 | ブリストル−マイヤーズ スクイブ カンパニー | シクロプロピル縮合インドロベンゾアゼピンhcvns5b阻害剤 |
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US7541351B2 (en) * | 2007-01-11 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
US7541352B2 (en) * | 2007-02-02 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
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US7541353B2 (en) * | 2007-03-14 | 2009-06-02 | Bristol-Myers Squibb Company | Compounds for the treatment of hepatitis C |
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PT2968316T (pt) | 2013-03-13 | 2019-10-29 | Forma Therapeutics Inc | Derivados de 2-hidroxi-1-{4-[(4-fenilfenil)carbonil]piperazin-1-il}etano-1-ona e compostos relacionados como inibidores da sintase de ácidos gordos (fasn) para o tratamento do cancro |
EP3046924A1 (en) | 2013-09-20 | 2016-07-27 | IDENIX Pharmaceuticals, Inc. | Hepatitis c virus inhibitors |
WO2015103490A1 (en) | 2014-01-03 | 2015-07-09 | Abbvie, Inc. | Solid antiviral dosage forms |
WO2015134560A1 (en) | 2014-03-05 | 2015-09-11 | Idenix Pharmaceuticals, Inc. | Solid forms of a flaviviridae virus inhibitor compound and salts thereof |
US20170135990A1 (en) | 2014-03-05 | 2017-05-18 | Idenix Pharmaceuticals Llc | Pharmaceutical compositions comprising a 5,5-fused heteroarylene flaviviridae inhibitor and their use for treating or preventing flaviviridae infection |
TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
CN113382633A (zh) | 2018-10-29 | 2021-09-10 | 福马治疗股份有限公司 | (4-(2-氟-4-(1-甲基-1H-苯并[d]咪唑-5-基)苯甲酰基)哌嗪-1-基)(1-羟基环丙基)甲酮的固体形式 |
US12083099B2 (en) | 2020-10-28 | 2024-09-10 | Accencio LLC | Methods of treating symptoms of coronavirus infection with viral protease inhibitors |
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TW200400963A (en) * | 2002-05-21 | 2004-01-16 | Wyeth Corp | R-enantiomers of pyranoindole derivatives and the use thereof for the treatment of hepatitis C virus infection or disease |
JP4143669B2 (ja) | 2004-02-24 | 2008-09-03 | 日本たばこ産業株式会社 | 4環縮合複素環化合物及びそのhcvポリメラーゼ阻害剤としての利用 |
US7348425B2 (en) * | 2004-08-09 | 2008-03-25 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
US7153848B2 (en) * | 2004-08-09 | 2006-12-26 | Bristol-Myers Squibb Company | Inhibitors of HCV replication |
CA2585084A1 (en) | 2004-10-26 | 2006-05-04 | Immacolata Conte | Tetracyclic indole derivatives as antiviral agents |
GB0518390D0 (en) | 2005-09-09 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
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- 2006-09-12 WO PCT/US2006/035490 patent/WO2007033175A1/en active Application Filing
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US7473688B2 (en) | 2009-01-06 |
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WO2007033175A1 (en) | 2007-03-22 |
PE20070839A1 (es) | 2007-09-10 |
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