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AR057716A1 - Inhibidores de las serina proteasas y composiciones farmaceuticas - Google Patents

Inhibidores de las serina proteasas y composiciones farmaceuticas

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Publication number
AR057716A1
AR057716A1 ARP060103374A ARP060103374A AR057716A1 AR 057716 A1 AR057716 A1 AR 057716A1 AR P060103374 A ARP060103374 A AR P060103374A AR P060103374 A ARP060103374 A AR P060103374A AR 057716 A1 AR057716 A1 AR 057716A1
Authority
AR
Argentina
Prior art keywords
optionally substituted
heterocycloaliphatic
aliphatic
heteroaryl
membered
Prior art date
Application number
ARP060103374A
Other languages
English (en)
Inventor
Robert B Perni
Steve Lyons
Original Assignee
Vertex Pharma
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Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=37654834&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR057716(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Vertex Pharma filed Critical Vertex Pharma
Publication of AR057716A1 publication Critical patent/AR057716A1/es

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/04—Linear peptides containing only normal peptide links
    • C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
    • A01N37/46—N-acyl derivatives
    • 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
    • A61K31/4965—Non-condensed pyrazines
    • A61K31/497—Non-condensed pyrazines 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
    • A61K31/395—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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/005—Enzyme inhibitors
    • 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
    • A61K38/08—Peptides having 5 to 11 amino acids
    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07K5/06139—Dipeptides with the first amino acid being heterocyclic
    • 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
    • C07K5/10—Tetrapeptides
    • C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
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    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
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    • C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
    • C12N9/99—Enzyme inactivation by chemical treatment
    • 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)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Epidemiology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Virology (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Communicable Diseases (AREA)
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  • Microbiology (AREA)
  • Biomedical Technology (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Environmental Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)

Abstract

La presente invencion se refiere a los compuestos de la formula 1: (mezcla de diestereoisomeros) y una composicion farmacéutica en base al compuesto. Reivindicacion 1: Una mezcla de compuestos diastereoisoméricos de la formula (1): o una de sus sales o mezclas farmacéuticamente aceptables, en donde C* representa un átomo de carbono diastereoisomérico; y el isomero R es mayor que el 50% de la mezcla respecto del isomero S en la posicion C*; R1 es RW-, P3- o P4-L2-P3-; R es un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un arilo opcionalmente sustituido o un heteroarilo opcionalmente sustituido; W es un enlace, -NR4-, -O- o -S-; R4 es H, un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un arilo opcionalmente sustituido o un heteroarilo opcionalmente sustituido; P3 es formula (2); T es -C(O)-, -OC(O)-, - NHC(O)-, -C(O)c(O)- o -SO2-; cada R5 y R5' es, de modo independiente, H, un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un fenilo opcionalmente sustituido o un heteroarilo opcionalmente sustituido; R6 es alifático opcionalmente sustituido, un heteroarilo opcionalmente sustituido, un fenilo opcionalmente sustituido; o R5 y R6, junto con los átomos a los que están unidos, pueden formar un heterocicloalifático monocíclico de 5 a 7 miembros opcionalmente sustituido o un heterocicloalifático bicíclico de 6 a 12 miembros opcionalmente sustituido, en donde cada anillo heterocicloalifático contiene opcionalmente un heteroátomo adicional seleccionado de -O-, -S- o -NR50-; R50 es H, un alifático opcionalmente sustituido, un heteroarilo opcionalmente sustituido o un fenilo opcionalmente sustituido; P4-L2-P3 es formula (3); cada R7 y R7' es, de modo independiente, H, un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un fenilo opcionalmente sustituido o un heteroarilo opcionalmente sustituido; o R7 y R7', junto con el átomo al que están unidos, pueden formar un anillo cicloalifático o heterocicloalifático de 3 a 7 miembros; o R7 y R6, junto con los átomos a los que están unidos, pueden formar un heterocicloalifático monocíclico de 5 a 7 miembros opcionalmente sustituido, un heteroarilo monocíclico de 5 a 7 miembros opcionalmente sustituido, un heterocicloalifático bicíclico de 6 a 12 miembros opcionalmente sustituido o un heteroarilo bicíclico de 6 a 12 miembros opcionalmente sustituido, en donde cada anillo heteroalifático o heteroarilo contiene opcionalmente un heteroátomo adicional seleccionado de -O-, -S- o -NR50- o cuando R5 y R6, junto con los átomos a los que están unidos, pueden formar un anillo, R7 y el sistema de anillos formado por R5 y R6 pueden formar un sistema de anillos fusionados opcionalmente sustituidos de 8 a 14 miembros, en donde el sistema de anillos fusionados bicíclicos está además opcionalmente fusionado con un fenilo opcionalmente sustituido para formar un sistema de anillos fusionados tricíclicos de 10 a 16 miembros opcionalmente sustituido; R8 es H o un grupo protector; y R2 es un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un heteroarilo opcionalmente sustituido o un fenilo opcionalmente sustituido; R3 es H, un alifático opcionalmente sustituido, un cicloalifático opcionalmente sustituido, un heterocicloalifático opcionalmente sustituido, un arilo opcionalmente sustituido o un heteroarilo opcionalmente sustituido; L es un enlace, -CF2-, -C(O)- o -SO2-; cada J1, J2, J'2 y J3 es, de modo independiente, halogeno, -OR', _OC(O)N(R')2, -NO2, -CN, CF3-, -OCF3, -R', oxo, tioxo, -N(R')2, -SR', -COR', -SO2R', -SO2N(R')2, -SO3R', - C(O)R', -C(O)C(O)R', -C(O)CH2C(O)R', -C(S)R', -C(O)OR', -OC(O)R', -C(O)N(R')2, -OC(O)N(R')2, -C(S)N(R')2, -(CH2)0-2NHC(O)R', -N(R')N(R')COR', -N(R')N(R')C(O)OR', -N(R')N(R')CON(R')2, -N(R')SO2R', -N(R')SO2N(R')2, N(R')C(O)OR', -N(R')C(O)R', - N(R')C(S)R', -N(R')C(O)N(R')2, -N(R')C(S)N(R')2, -(COR')COR', -N(OR')R', -C(=NH)N(R'), -C(=NH)N(R')2, -C(O)N(OR')R', -C(=NOR')R', -OP(O)(OR')2, -P(O)(R')2, -P(O)(OR')2 o -P(O)(H)(OR') o de J2 y J'2 es H, en donde dos grupos R', junto con los átomos a los que están unidos, pueden formar un sistema de anillos aromáticos o no aromáticos de 3 a 10 miembros con hasta 3 heteroátomos seleccionados de modo independiente de N, O o S, en donde el anillo está opcionalmente fusionado a un arilo C6-10, un heteroarilo C5-10, un cicloalquilo C3-10 o un heterocicloalifático C3-10, y donde cada anillo tiene hasta 3 sustituyentes seleccionados de modo independiente de J2; cada R' está seleccionado, de modo independiente, de H, alifático C1-12, cicloalquilo C3-10 o cicloalquenilo C3-10, cicloalquil C3-10-alifático C1-12, cicloalquenil C3-10-alifático C1-12, arilo C6-10, aril C6-10-alifático C1-12, heterocicloalifático de 3 a 10 miembros, heterocicloalifático de 6 a 10 miembros-alifático C1- 12, heteroarilo de 5 a 10 miembros de heteroaril de 5 a 10 miembros-alifático C1-12, en donde R' tiene hasta 3 sustituyentes seleccionados, cada uno de modo independiente, de J2; o J1 y J2, junto con los átomos a los que están unidos, pueden formar un anillo bicíclico de C8 a C12 opcionalmente sustituido; J1 y J3, junto con los átomos a los que están unidos, pueden formar un anillo bicíclico de C8 a C12 opcionalmente sustituido; J2 y J'2, junto con el átomo de carbono al que están unidos, pueden formar un cicloalifático opcionalmente sustituido de 5-10 miembros o un anillo heterocicloalifático opcionalmente sustituido de 5 a 10 miembros; o J2 y J3, junto con los átomos a los que están unidos, pueden formar un anillo bicíclico de C8 a C12 opcionalmente sustituido. Actividad frente al virus de la hepatitis C.
ARP060103374A 2005-08-02 2006-08-02 Inhibidores de las serina proteasas y composiciones farmaceuticas AR057716A1 (es)

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US (4) US20070105781A1 (es)
EP (3) EP1910341B1 (es)
JP (1) JP2009505966A (es)
KR (1) KR20080033481A (es)
CN (1) CN101277950B (es)
AR (1) AR057716A1 (es)
AU (1) AU2006275413B2 (es)
CA (1) CA2617679A1 (es)
ES (1) ES2401661T3 (es)
IL (1) IL189192A0 (es)
MX (1) MX2008001528A (es)
NO (1) NO20081012L (es)
NZ (1) NZ565540A (es)
RU (2) RU2441020C2 (es)
TW (1) TW200740813A (es)
WO (1) WO2007016589A2 (es)
ZA (1) ZA200801114B (es)

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