PE20131086A1 - Proceso para preparar compuestos antivirales - Google Patents

Proceso para preparar compuestos antivirales

Info

Publication number
PE20131086A1
PE20131086A1 PE2013000078A PE2013000078A PE20131086A1 PE 20131086 A1 PE20131086 A1 PE 20131086A1 PE 2013000078 A PE2013000078 A PE 2013000078A PE 2013000078 A PE2013000078 A PE 2013000078A PE 20131086 A1 PE20131086 A1 PE 20131086A1
Authority
PE
Peru
Prior art keywords
compound
phosphine
tert
paladium
catalyst precursor
Prior art date
Application number
PE2013000078A
Other languages
English (en)
Inventor
Shashank Shekhar
Thaddeus S Franczyk
David M Barnes
Travis B Dunn
Anthony R Haight
Vincent S Chan
Original Assignee
Abbvie Bahamas Ltd
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=45467152&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20131086(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Abbvie Bahamas Ltd filed Critical Abbvie Bahamas Ltd
Publication of PE20131086A1 publication Critical patent/PE20131086A1/es

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or 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
    • A61K31/495—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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/7056—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing five-membered rings with nitrogen as a ring hetero atom
    • 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]
    • 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
    • A61P31/12—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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B01J31/2419—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member
    • B01J31/2423—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring comprising P as ring member comprising aliphatic or saturated rings
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
    • B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
    • B01J2231/342—Aldol type reactions, i.e. nucleophilic addition of C-H acidic compounds, their R3Si- or metal complex analogues, to aldehydes or ketones
    • B01J2231/344—Boronation, e.g. by adding R-B(OR)2
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
    • B01J2231/4211—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group
    • B01J2231/4227—Suzuki-type, i.e. RY + R'B(OR)2, in which R, R' are optionally substituted alkyl, alkenyl, aryl, acyl and Y is the leaving group with Y= Cl
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4283—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using N nucleophiles, e.g. Buchwald-Hartwig amination
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4288—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using O nucleophiles, e.g. alcohols, carboxylates, esters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
    • B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
    • B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
    • B01J2231/4294—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues using S nucleophiles, e.g. thiols
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/824—Palladium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Zoology (AREA)
  • Immunology (AREA)
  • Inorganic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Peptides Or Proteins (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

REFERIDA A UN PROCEDIMIENTO PARA PREPARAR N-(6-(3-TERT-BUTIL-5-(2,4-DIOXO-3,4-DIHIDROPIRIMIDIN-1(2H)-IL)-2-METOXIFENIL)NAFTALEN-2-IL)METANSULFONAMIDA (COMPUESTO A) O UNA SAL DEL MISMO, QUE COMPRENDE SULFONAMIDAR EL COMPUESTO (5) MEDIANTE UN PRECURSOR DE CATALIZADOR DE METAL DE TRANSICION TAL COMO UN PRECURSOR DE CATALIZADOR DE PALADIO Y UN LIGANDO TAL COMO UNA FOSFINA, EN PRESENCIA DE UNA BASE TAL COMO CARBONATO DE CESIO, CARBONATO DE SODIO, ENTRE OTROS Y UN SOLVENTE TAL COMO TETRAHIDROFURANO, N-METIL-PIRROLIDONA, ENTRE OTROS, DONDE R1a ES FENILO, PERFLUOROBUTILO, ENTRE OTROS Y LA FOSFINA ES 7,7,9,9-TETRAMETIL-8-(2',4',6'-TRIISOPROPILBIFENIL-2-IL)-1,4-DIOXA-8-FOSFAESPIRO[4,5]DECANO, 2,2,6,6-TETRAMETIL.1.(2',4',6'-TRIISOPROPILBIFENIL-2-IL)FOSFINANO, ENTRE OTRAS. EL COMPUESTO (5) SE PREPARA HACIENDO REACCIONAR EL 1-(3-TERT-BUTIL-5-(6-HIDROXINAFTALEN-2-IL)-4-METOXIFENIL)PIRIMIDIN-2,4(1H,3H)-DIONA (COMPUESTO 4) CON FLUORURO DE PERFLUOROBUTANSULFONILO EN PRESENCIA DE UNA BASE Y UN SOLVENTE. EL COMPUESTO 4 SE PREPARA ACOPLANDO EL 1-(3-TERT-BUTIL-5-IODO-4-METOXIFENIL)PIRIMIDIN-2,4(1H,3H)-DIONA CON EL ACIDO 6-HIDROXINAFTALEN-2-ILBORONICO EN PRESENCIA DE UN LIGANDO FOSFINA TAL COMO TRI-T-BUTILFOSFINA, TRIS(2-FURIL)FOSFINA, ENTRE OTROS, UN PRECURSOR DE CATALIZADOR DE METAL DE TRANSICION TAL COMO DIACETATO DE PALADIO (II), TETRAKIS(TRIFENILFOSFIN)PALADIO(0), ENTRE OTROS, UNA BASE TAL COMO CARBONATO DE CESIO, FLUORURO DE CESIO, ENTRE OTROS. DICHOS COMPUESTOS SON INHIBIDORES DEL VHC
PE2013000078A 2010-07-16 2011-07-15 Proceso para preparar compuestos antivirales PE20131086A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US36529310P 2010-07-16 2010-07-16
US201161444475P 2011-02-18 2011-02-18

Publications (1)

Publication Number Publication Date
PE20131086A1 true PE20131086A1 (es) 2013-10-24

Family

ID=45467152

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2013000078A PE20131086A1 (es) 2010-07-16 2011-07-15 Proceso para preparar compuestos antivirales

Country Status (24)

Country Link
US (1) US8895737B2 (es)
EP (3) EP3056486B1 (es)
JP (2) JP5819959B2 (es)
KR (1) KR101893751B1 (es)
CN (2) CN105622525B (es)
AU (1) AU2011278927B2 (es)
BR (1) BR112013001132A2 (es)
CA (1) CA2805748A1 (es)
CL (2) CL2013000159A1 (es)
CO (1) CO6670583A2 (es)
CR (2) CR20180412A (es)
DO (1) DOP2013000017A (es)
EA (2) EA201790723A1 (es)
EC (1) ECSP13012438A (es)
GT (1) GT201300021A (es)
IL (1) IL224222A (es)
MX (2) MX344148B (es)
MY (1) MY167881A (es)
NZ (2) NZ605767A (es)
PE (1) PE20131086A1 (es)
PH (1) PH12013500105A1 (es)
SG (2) SG187102A1 (es)
UA (1) UA115025C2 (es)
WO (1) WO2012009699A2 (es)

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WO2012009699A2 (en) * 2010-07-16 2012-01-19 Abbott Laboratories Process for preparing antiviral compounds
BR112013001138A2 (pt) 2010-07-16 2016-07-05 Abbvie Inc ligantes de fosfina para reações catalíticas
US8975443B2 (en) * 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
US9255074B2 (en) * 2010-07-16 2016-02-09 Abbvie Inc. Process for preparing antiviral compounds
AU2012234259A1 (en) * 2011-03-31 2013-10-03 Libera-Korner, Jeanette Perfluorinated compounds for the non-viral transfer of nucleic acids
CN104884440A (zh) * 2012-08-21 2015-09-02 艾伯维公司 用于制备抗病毒化合物的方法
DK3043803T3 (da) 2013-09-11 2022-08-01 Univ Emory Nukleotid- og nucleosidsammensætninger og deres anvendelse
WO2016054240A1 (en) 2014-09-30 2016-04-07 Sean Dalziel Fixed dose combinations for the treatment of viral diseases
WO2016105547A1 (en) 2014-12-24 2016-06-30 Concert Pharmaceuticals, Inc. Deuterated dasabuvir
JP7129703B2 (ja) 2016-04-28 2022-09-02 エモリー ユニバーシティー アルキン含有ヌクレオチド及びヌクレオシド治療組成物並びにそれらに関連した使用
CN108290844B (zh) * 2016-05-27 2021-04-30 深圳市塔吉瑞生物医药有限公司 一种取代的萘环化合物及药物组合物及其应用
CN110201714B (zh) * 2019-07-04 2022-07-29 蚌埠学院 二氢嘧啶酮类化合物合成方法及催化剂
CN110669006A (zh) * 2019-10-22 2020-01-10 中国科学技术大学 茚并异喹啉类化合物及其制备方法
CN112735799B (zh) * 2020-12-10 2022-12-20 华东理工大学 一种新型磁性材料及其制备方法

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