WO2013021337A1 - Composés antiviraux à noyau tricyclique condensé - Google Patents

Composés antiviraux à noyau tricyclique condensé Download PDF

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Publication number
WO2013021337A1
WO2013021337A1 PCT/IB2012/054007 IB2012054007W WO2013021337A1 WO 2013021337 A1 WO2013021337 A1 WO 2013021337A1 IB 2012054007 W IB2012054007 W IB 2012054007W WO 2013021337 A1 WO2013021337 A1 WO 2013021337A1
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WO
WIPO (PCT)
Prior art keywords
alkyl
substituted
unsubstituted
compound
analogues
Prior art date
Application number
PCT/IB2012/054007
Other languages
English (en)
Inventor
Vidya Ramdas
Advait Arun JOSHI
Deepak Sahebrao WALKE
Moloy Manoj BANERJEE
Venkata P Palle
Rajender Kumar Kamboj
Original Assignee
Lupin Limited
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 Lupin Limited filed Critical Lupin Limited
Publication of WO2013021337A1 publication Critical patent/WO2013021337A1/fr
Priority to ZA2014/00978A priority Critical patent/ZA201400978B/en

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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
    • C07D491/02—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 two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • 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
    • 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
    • C07D403/14—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 three or more hetero rings

Definitions

  • HCV Persistent hepatitis C virus
  • HCV chronic infection is often asymptomatic with latent periods lasting for decades before manifestation by which time extensive liver damage has occurred.
  • HCV is spread primarily by unscreened blood transfusions and use of contaminated needles and syringes; the highest risk groups are intravenous drug users and people who received blood transfusions (mainly haemophiliacs) before 1990 when screening for HCV was introduced.
  • HCV The sequence diversity of HCV is complex with the virus organized into 6 distinct genotypes and over 100 subtypes. Additionally, HCV exists as many closely related viral sequences, termed as quasi-species, in the infected individual, making specific pharmaceutical targeting of HCV proteins challenging due to the rapid evolution of escape mutants. It is increasingly evident that a broad collection of specific, pan genotypic antiviral drugs targeting multiple essential viral functions, in addition to the current viral therapies will be required for effective global control of HCV.
  • R 1a , R 1 to R 7 , m, n, Y, ring A, ring D and ring E are as defined hereinbelow.
  • Characterization of the replicase machinery required for HCV RNA synthesis has defined the protease/helicase NS3 protein, the NS4A cofactor, the NS4B integral membrane protein, the NS5A protein and the RNA dependent RNA polymerase NS5B as being its essential components.
  • R 3 is selected from O and N(R 11 );
  • R 8b is selected from the group consisting of hydrogen, substituted- or unsubstituted- Ci -6 alkyl, perhaloalkyl, substituted- or unsubstituted- aryl, substituted- or unsubstituted- heteroaryl, substituted- or unsubstituted- cycloalkyl, and substituted- or unsubstituted- heterocyclyl;
  • R 12 is selected from hydrogen and alkyl
  • R 12b is selected from hydrogen, alkyl, perhaloalkyl.
  • Y is particularly selected as
  • ring E is particularly selected as -
  • R 3 is particularly selected as
  • Tricyclic ring systems are also exemplified by a bicyclic ring system in which two non- adjacent carbon atoms of the bicyclic ring are linked by a bond or an alkylene bridge.
  • Representative examples of tricyclic-ring systems include, but are not limited to, tricyclo[3.3.1 .0 3 7 ]nonane and tricyclo[3.3.1 .1 3 7 ]decane (adamantane).
  • cycloalkyi also include spiro systems wherein one of the ring is annulated on a single carbon atom such ring systems are exemplified by spiro[2.5]octane, spiro[4.5]decane, spiro[bicyclo[4.1 .0]heptane-2,1 '-cyclopentane], hexahydro-2'H-spiro[cyclopropane-1 ,1 '- pentalene].
  • aryl refers to a monovalent monocyclic, bicyclic or tricyclic aromatic hydrocarbon ring system.
  • aryl groups include phenyl, naphthyl, anthracenyl, fluorenyl, indenyl, azulenyl, and the like.
  • Aryl group also include partially saturated bicyclic and tricyclic aromatic hydrocarbons such as tetrahydro-naphthalene.
  • heteroaryl refers to a 5-14 membered monocyclic, bicyclic, or tricyclic ring system having 1 -4 ring heteroatoms selected from O, N, or S. and the remainder ring atoms being carbon (with appropriate hydrogen atoms unless otherwise indicated), wherein at least one ring in the ring system is aromatic. Heteroaryl groups may be optionally substituted with one or more substituents. In one embodiment, 0, 1 , 2, 3, or 4 atoms of each ring of a heteroaryl group may be substituted by a substituent.
  • monocyclic heterocycle include, but are not limited to, azetidinyl, azepanyl, aziridinyl, diazepanyl, 1 ,3-dioxanyl, 1 ,3-dioxolanyl, 1 ,3- dithiolanyl, 1 ,3-dithianyl, imidazolinyl, imidazolidinyl, isothiazolinyl, isothiazolidinyl, isoxazolinyl, isoxazolidinyl, morpholinyl, oxadiazolinyl.
  • the compounds of general formula I where all the symbols are as defined earlier can be prepared by methods given in Schemes given below or example. Representative procedures are shown below, however; the disclosure should not be construed to limit the scope of the invention arriving at compound of formula I as disclosed hereinabove.
  • oxime 12 On treatment with isoamyl nitrite in an appropriate solvent, oxime 12 might be generated from 11 which upon reaction with Boc-L-prolinal under basic conditions may lead to formation of 13. Treatment of 13 with triethyl phosphite might lead to the formation of 14.
  • a further embodiment of the present invention is a pharmaceutical composition
  • a pharmaceutical composition comprising any single compound or a combination of two or more compounds delineated herein, or a pharmaceutically acceptable salt thereof, in combination with one or more agents known in the art, with a pharmaceutically acceptable carrier or excipient.
  • compounds of the present invention can be administered as the sole active pharmaceutical agent, or used in combination with one or more agents to treat or prevent hepatitis C infections or the symptoms associated with HCV infection.
  • Other agents to be administered in combination with a compound or combination of compounds of the present invention include therapies for diseases caused by HCV infection that suppresses HCV viral replication by direct or indirect mechanisms.
  • agents include, but not limited to, host immune modulators (for example, interferon-alpha, pegylated interferon-alpha, consensus interferon, interferon-beta, interferon-gamma, CpG oligonucleotides and the like); antiviral compounds that inhibit host cellular functions such as inosine monophosphate dehydrogenase (for example, ribavirin and the like); cytokines that modulate immune function (for example, interleukin 2, interleukin 6, and interleukin 12); a compound that enhances the development of type 1 helper T cell response; interfering RNA; anti-sense RNA; vaccines comprising HCV antigens or antigen adjuvant combinations directed against HCV; agents that interact with host cellular components to block viral protein synthesis by inhibiting the internal ribosome entry site (IRES) initiated translation step of HCV viral replication or to block viral particle maturation and release with agents targeted toward the viroporin family of membrane proteins such as, for example
  • stereoisomers of the compounds of formula I of the present invention may be prepared by stereospecific syntheses or resolution of the achiral compound using an optically active amine, acid or complex forming agent, and separating the diastereomeric salt/complex by fractional crystallization or by column chromatography.
  • cleavable alcohol prodrug moieties include substituted or unsubstituted, branched or unbranched lower alkyl ester moieties, e.g., ethyl esters, di-lower alkylamino lower-alkyl esters, e.g., dimethylaminoethyl ester, acylamino lower alkyl esters, acyloxy lower alkyl esters (e.g., pivaloyloxymethyl ester), aryl esters, e.g., phenyl ester, aryl-lower alkyl esters, e.g., benzyl ester, optionally substituted, e.g., with methyl, halo, or methoxy substituents aryl and aryl- lower alkyl esters, amides, lower-alkyl amides, di-lwer alkyl amides, and hydroxy amides.
  • lower alkyl ester moieties
  • a preferred pharmaceutical carrier is polyethylene glycol, such as PEG 400, and particularly a composition comprising 40% PEG 400 and 60% water or saline. The choice of carrier will be determined in part by the particular compound chosen, as well as by the particular method used to administer the composition. Accordingly, there is a wide variety of suitable formulations of the pharmaceutical composition of the present invention.
  • the parenteral formulations typically will contain from about 0.5% or less to about 25% or more by weight of a compound of the invention in solution. Preservatives and buffers can be used. In order to minimize or eliminate irritation at the site of injection, such compositions can contain one or more nonionic surfactants having a hydrophile-lipophile balance (HLB) of from about 12 to about 17. The quantity of surfactant in such formulations will typically range from about 5% to about 15% by weight. Suitable surfactants include polyethylene sorbitan fatty acid esters, such as sorbitan monooleate and the high molecular weight adducts of ethylene oxide with a hydrophobic base, formed by the condensation of propylene oxide with propylene glycol.
  • HLB hydrophile-lipophile balance
  • Step 4 (S)-tert-butyl 2-(8-(4-(2-((1 S,2R)-2-((tert-butoxycarbonyl)amino)cyclopentyl)-1 H- benzo[d]imidazol-5-yl)phenyl)-4,5-dihydro-3H-benzo[2,3]oxepino[4,5-d]imidazol-2- yl)pyrrolidine-1 -carboxylate (1 d):
  • Example 2 Preparation of methyl ((S)-1-(((1S,2R)-2-(6-(4-(2-((S)-1 -((S)-2- (methoxycarbonyl)amino-3-methylbutanoyl)pyrrolidin-2-yl)-4,5-dihydro-1 H- naphtho[1 ,2-d]imidazol-7-yl)phenyl)-1 H-benzo[d]imidazol-2-yl)cyclopentyl)amino)-3- methyl-1 -oxobutan-2-yl)carbamate (Compound 2): tert-butyl ((1 S,2R)-2-(5-bromo-1 H-benzo[d]imidazol-2-yl)cyclopentyl)carbamate
  • Step 3 (S)-tert-butyl 2-(7-(4-(2-((1 R,2S)-2-((tert-butoxycarbonyl)amino)cyclopentyl)-1 H- benzo[d]imidazol-6-yl)phenyl)-4,5-dihydro-1 H-naphtho[1 ,2-d]imidazol-2-yl)pyrrolidine-1 - carboxylate (2c):
  • Step 1 (S)-tert-butyl 2-(7-bromo-3H-naphtho[1 ,2-d]imidazol-2-yl)pyrrolidine-1 -carboxylate (5a):
  • Step 2 methyl ((S)-1 -(((1 S,2R)-2-(6-(4-(2-((S)-1 -((S)-2-(methoxycarbonyl)amino-3- methylbutanoyl)pyrrolidin-2-yl)-1 H-naphtho[1 ,2-d]imidazol-7-yl)phenyl)-1 H- benzo[d]imidazol-2-yl)cyclopentyl)amino)-3-methyl-1 -oxobutan-2-yl)carbamate (Compound

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne des composés de formule générale I, leurs formes tautomères, leurs stéréo-isomères, leurs analogues, leurs promédicaments, leurs isotopes, leurs N-oxydes, leurs métabolites, leurs sels pharmaceutiquement acceptables, des polymorphes, des solvates, des isomères optiques, des clathrates, des co-cristaux, des combinaisons avec un médicament approprié, des compositions pharmaceutiques les contenant, des procédés de fabrication des composés précités et leur utilisation comme candidats antiviraux, plus spécifiquement comme anti-VHC.
PCT/IB2012/054007 2011-08-08 2012-08-06 Composés antiviraux à noyau tricyclique condensé WO2013021337A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
ZA2014/00978A ZA201400978B (en) 2011-08-08 2014-02-10 Antiviral compounds with a fused tricyclic ring

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1047/KOL/2011 2011-08-08
IN1047KO2011 2011-08-08

Publications (1)

Publication Number Publication Date
WO2013021337A1 true WO2013021337A1 (fr) 2013-02-14

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SG (1) SG10201606446XA (fr)
WO (1) WO2013021337A1 (fr)
ZA (1) ZA201400978B (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9303061B2 (en) 2011-07-09 2016-04-05 Sunshine Luke Pharma Co., Ltd. Spiro compounds as Hepatitis C virus inhibitors
US9309231B2 (en) 2012-08-03 2016-04-12 Sunshine Lake Pharma Co., Ltd. Bridged ring compounds as hepatitis C virus (HCV) inhibitors and pharmaceutical applications thereof
US9326973B2 (en) 2012-01-13 2016-05-03 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US9416139B2 (en) 2012-11-29 2016-08-16 Sunshine Lake Pharma Co., Ltd. Spiro ring compound as hepatitis C virus (HCV) inhibitor and uses thereof
US9717712B2 (en) 2013-07-02 2017-08-01 Bristol-Myers Squibb Company Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus
US9738629B2 (en) 2014-01-23 2017-08-22 Sunshine Lake Pharma Co., Ltd. Bridged ring compounds as Hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof
US9770439B2 (en) 2013-07-02 2017-09-26 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US9775831B2 (en) 2013-07-17 2017-10-03 Bristol-Myers Squibb Company Combinations comprising biphenyl derivatives for use in the treatment of HCV
US9802949B2 (en) 2012-11-29 2017-10-31 Sunshine Lake Pharma Co., Ltd. Fused ring compounds as hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof
US10617675B2 (en) 2015-08-06 2020-04-14 Bristol-Myers Squibb Company Hepatitis C virus inhibitors

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9303061B2 (en) 2011-07-09 2016-04-05 Sunshine Luke Pharma Co., Ltd. Spiro compounds as Hepatitis C virus inhibitors
US9326973B2 (en) 2012-01-13 2016-05-03 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US9309231B2 (en) 2012-08-03 2016-04-12 Sunshine Lake Pharma Co., Ltd. Bridged ring compounds as hepatitis C virus (HCV) inhibitors and pharmaceutical applications thereof
US9416139B2 (en) 2012-11-29 2016-08-16 Sunshine Lake Pharma Co., Ltd. Spiro ring compound as hepatitis C virus (HCV) inhibitor and uses thereof
US9802949B2 (en) 2012-11-29 2017-10-31 Sunshine Lake Pharma Co., Ltd. Fused ring compounds as hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof
US9717712B2 (en) 2013-07-02 2017-08-01 Bristol-Myers Squibb Company Combinations comprising tricyclohexadecahexaene derivatives for use in the treatment of hepatitis C virus
US9770439B2 (en) 2013-07-02 2017-09-26 Bristol-Myers Squibb Company Hepatitis C virus inhibitors
US9775831B2 (en) 2013-07-17 2017-10-03 Bristol-Myers Squibb Company Combinations comprising biphenyl derivatives for use in the treatment of HCV
US9738629B2 (en) 2014-01-23 2017-08-22 Sunshine Lake Pharma Co., Ltd. Bridged ring compounds as Hepatitis C virus inhibitors, pharmaceutical compositions and uses thereof
US10617675B2 (en) 2015-08-06 2020-04-14 Bristol-Myers Squibb Company Hepatitis C virus inhibitors

Also Published As

Publication number Publication date
ZA201400978B (en) 2015-01-28
SG10201606446XA (en) 2016-09-29

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