AR083052A1 - Inhibidores de las proteasas de serina del vhc derivados de prolinas macrociclicas - Google Patents

Inhibidores de las proteasas de serina del vhc derivados de prolinas macrociclicas

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Publication number
AR083052A1
AR083052A1 ARP110103420A ARP110103420A AR083052A1 AR 083052 A1 AR083052 A1 AR 083052A1 AR P110103420 A ARP110103420 A AR P110103420A AR P110103420 A ARP110103420 A AR P110103420A AR 083052 A1 AR083052 A1 AR 083052A1
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AR
Argentina
Prior art keywords
substituted
cycloalkenyl
cycloalkyl
heteroaryl
heteroatoms selected
Prior art date
Application number
ARP110103420A
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English (en)
Inventor
Jiang Long
Yat Sun Or
Jun Ma
Guoqiang Wang
Bin Wang
Original Assignee
Enanta Pharm Inc
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Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=45817947&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR083052(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Enanta Pharm Inc filed Critical Enanta Pharm Inc
Publication of AR083052A1 publication Critical patent/AR083052A1/es

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    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/12—Cyclic peptides with only normal peptide bonds in the ring
    • C07K5/123—Tripeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/19—Cytokines; Lymphokines; Interferons
    • A61K38/21—Interferons [IFN]
    • A61K38/212—IFN-alpha
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more 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
    • 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
    • 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
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/19—Cytokines; Lymphokines; Interferons
    • A61K38/21—Interferons [IFN]
    • A61K38/215—IFN-beta
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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
    • A61P31/04—Antibacterial agents
    • 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
    • A61P31/10—Antimycotics
    • 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
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    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • 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
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D498/18—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/81—Protease inhibitors
    • C07K14/8107—Endopeptidase (E.C. 3.4.21-99) inhibitors
    • C07K14/811—Serine protease (E.C. 3.4.21) inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
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    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
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    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0821—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp
    • C07K5/0823—Tripeptides with the first amino acid being heterocyclic, e.g. His, Pro, Trp and Pro-amino acid; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
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    • C07K5/08—Tripeptides
    • C07K5/0827—Tripeptides containing heteroatoms different from O, S, or N
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

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  • Health & Medical Sciences (AREA)
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  • Medicinal Chemistry (AREA)
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  • Animal Behavior & Ethology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Estos compuestos inhiben la actividad de las proteasas de serina, en particular la actividad de la proteasa NS3-NS4A del virus de la hepatitis C (VHC). En consecuencia, los compuestos de la presente solicitud interfieren con el ciclo de vida del virus de la hepatitis C y también son útiles como agentes antivirales. Composiciones farmacéuticas que comprenden los compuestos mencionados para su administración a un sujeto que sufre de una infección por VHC.Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1) donde A es nulo, -(C=O)-, -S(O)2, -C(=N-OR1)- o -C(=N-CN)-; B se selecciona entre cicloalquilo C3-12, cicloalquilo C3-12 sustituido; cicloalquenilo C3-12, cicloalquenilo C3-12 sustituido; heterocicloalquilo C3-12 y heterocicloalquilo C3-12 sustituido; o B es un resto de fórmula (2), donde R7 y R8 son en forma independiente entre sí alquilo C1-8 o alquenilo C2-8 y están opcionalmente sustituidos en forma independiente entre sí con uno o más halo; M1 y M2 se seleccionan en forma independiente entre sí entre O ó NR1; cada R1 se selecciona en forma independiente en cada caso entre el grupo que consiste en: (i) hidrógeno; (ii) arilo; arilo sustituido; heteroarilo; o heteroarilo sustituido; (iii) heterocicloalquilo o heterocicloalquilo sustituido; y (iv) alquilo C1-8, alquenilo C2-8, alquinilo C2-8 donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S, o N; -alquilo C1-8 sustituido, alquenilo C2-8 sustituido, o alquinilo C2-8 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; -cicloalquilo C3-12, cicloalquilo C3-12 sustituido; cicloalquenilo C3-12 o cicloalquenilo C3-12 sustituido; L1 y L2 se seleccionan en forma independiente entre sí entre alquileno C1-8, alquenileno C2-8, o alquinileno C2-8 donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S, o N; alquileno C1-8 sustituido, alquenileno C2-8 sustituido, o alquinileno C2-8 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; cicloalquileno C3-12, o cicloalquileno C3-12 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; cicloalquenileno C3-12, y -cicloalquenileno C3-12 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N;. W es nulo, -O-, -S-, -NH-, -N(Me)-, -C(O)NH-, o -C(O)N(Me)-; X e Y tomados junto con los átomos de carbono a los cuales se encuentran unidos para formar una porción cíclica que se selecciona entre arilo, arilo sustituido, heteroarilo, heteroarilo sustituido, heterociclo, heterociclo sustituido, carbociclo, y carbociclo sustituido; X’ es N o -C(R2)-, donde R2 se selecciona entre el grupo que consiste en: (i) hidrógeno, halógeno, CN, CF3, NO2, OR3, SR3, -NHS(O)2-R3, -NH(SO2)NR4R5, NR4R5, CO2R3, COR3, CONR4R5, N(R1)COR3; arilo; arilo sustituido; heteroarilo; o heteroarilo sustituido; (ii) heterocicloalquilo o heterocicloalquilo sustituido; y (iii) alquilo C1-8, alquenilo C2-8, o alquinilo C2-8 donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S, o N; alquilo C1-8 sustituido, alquenilo C2-8 sustituido, o -alquinilo C2-8 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; cicloalquilo C3-12, cicloalquilo C3-12 sustituido; cicloalquenilo C3-12, o cicloalquenilo C3-12 sustituido; cada R3 se selecciona en forma independiente entre alquilo C1-8, alquenilo C2-8, o alquinilo C2-8 donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S, o N; alquilo C1-8 sustituido, alquenilo C2-8 sustituido, o alquinilo C2-8 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; cicloalquilo C3-12, cicloalquilo C3-12 sustituido; cicloalquenilo C3-12, o cicloalquenilo C3-12 sustituido; heterociclo; heterociclo sustituido; arilo; arilo sustituido; heteroarilo; o heteroarilo sustituido; cada uno de R4 y R5 se selecciona en forma independiente entre H y R3, o R4 y R5 combinados junto con el N se unen para formar un anillo heterocíclico; R y R’ se seleccionan en forma independiente entre sí entre el grupo que consiste en: (i) alquilo C1-8, alquenilo C2-8, o alquinilo C2-8 donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S, o N; alquilo C1-8 sustituido, alquenilo C2-8 sustituido, o alquinilo C2-8 sustituido donde cada uno contiene 0, 1, 2 ó 3 heteroátomos seleccionados entre O, S o N; cicloalquilo C3-12, cicloalquilo C3-12 sustituido; alquilcicloalquilo C4-12, alquilcicloalquilo C4-12 sustituido, cicloalquenilo C3-12, cicloalquenilo C3-12 sustituido; alquilcicloalquenilo C4-12, o alquilcicloalquenilo C4-12 sustituido; (ii) arilo; arilo sustituido; heteroarilo; o heteroarilo sustituido; (iii) heterocicloalquilo o heterocicloalquilo sustituido; y (iv) hidrógeno o deuterio; G se selecciona entre -OH, -NHS(O)2-R3, -NH(SO2)NR4R5, y NR4R5; y R’’ se selecciona entre hidrógeno, metilo, etilo, y alilo.
ARP110103420A 2010-09-21 2011-09-20 Inhibidores de las proteasas de serina del vhc derivados de prolinas macrociclicas AR083052A1 (es)

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US38505810P 2010-09-21 2010-09-21
US201161499994P 2011-06-22 2011-06-22
US201161504616P 2011-07-05 2011-07-05

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WO2010132163A1 (en) * 2009-05-13 2010-11-18 Enanta Pharmaceuticals, Inc. Macrocyclic compounds as hepatitis c virus inhibitors
WO2011049908A2 (en) * 2009-10-19 2011-04-28 Enanta Pharmaceuticals, Inc. Bismacrokyclic compounds as hepatitis c virus inhibitors
NZ608720A (en) 2010-09-21 2015-03-27 Enanta Pharm Inc Macrocyclic proline derived hcv serine protease inhibitors
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