CA2350899A1 - Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues - Google Patents

Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues Download PDF

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Publication number
CA2350899A1
CA2350899A1 CA002350899A CA2350899A CA2350899A1 CA 2350899 A1 CA2350899 A1 CA 2350899A1 CA 002350899 A CA002350899 A CA 002350899A CA 2350899 A CA2350899 A CA 2350899A CA 2350899 A1 CA2350899 A1 CA 2350899A1
Authority
CA
Canada
Prior art keywords
phenyl
thioureido
carbon atoms
chloro
amide
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002350899A
Other languages
English (en)
Inventor
Stanley Albert Lang
Martin Joseph Digrandi
Jonathan David Bloom
Russell George Dushin
Bryan Mark O'hara
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2350899A1 publication Critical patent/CA2350899A1/fr
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
    • C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/20—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C335/04—Derivatives of thiourea
    • C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C335/22—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/14—Nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/56—Nitrogen atoms
    • C07D211/58—Nitrogen atoms attached in position 4

Abstract

La présente invention concerne des composés représentés par la formule générale (I) ou certains de leurs sels pharmaceutiques. Dans cette formule R¿1?-R¿5? sont indépendamment hydrogène, C¿1?-C¿6? alkyle, C¿2?-C¿6? alcényle, C¿2?-C¿6? alkynyle, C¿1?-C¿6? perhaloalkyle, C¿3?-C¿10? cycloalkyle, hétérocycloalkyle portant 3 à 10 éléments carbonés, aryle, hétéroaryle, halogène, -CN, -NO¿2?, -CO¿2?R¿6?, -COR¿6?, -OR¿6?, -SR¿6?, -SOR¿6?, -SO¿2?R¿6?, -CONR¿7?R¿8?, -NR¿6?N(R¿7?R¿8?), -N(R¿7?R¿8?) ou W-Y-(CH¿2?)¿n?-Z sous la réserve que l'un de R¿1?-R¿5? ne soit pas hydrogène; ou R¿2? et R¿3? ou R¿3? et R¿4?, forment ensemble un hétérocycloalkyle de 3 à 7 segments ou un hétéroaryle de 3 à 7 segments; R¿6? et R¿7? sont indépendamment hydrogène, C¿1?-C¿6? alkyle, C¿1?-C¿6? perhaloalkyle, ou aryle; R¿8? est hydrogène, C¿1?-C¿6? alkyle, C¿1?-C¿6? perhaloalkyle, C¿3?-C¿10? cycloalkyle, hétérocycloalkyle de 3 à 10 segments, aryle ou hétéroaryle, ou R¿7? et R¿8? peuvent former ensemble un hétérocycloalkyle de 3 à 7 segments; R¿9?-R¿12? sont indépendamment hydrogène, C¿1?-C¿4? alkyle, C¿1?-C¿4? perhaloalkyle, halogène, C¿1?-C¿4? alcoxy ou cyano, ou R¿9? et R¿10? ou R¿11? et R¿12? peuvent former ensemble un C¿5?-C¿7? aryle; W est O, NR¿6?, ou est absent; Y est -(CO)- ou -(CO¿2?)-, ou est absent; Z est C¿1?-C¿4? alkyle, -CN, -CO¿2?R¿6?, COR¿6?, -CONR¿7?R¿8?, -OCOR¿6?, -NR¿6?COR¿7?, -OCONR¿6?, -OR¿6?, -SR¿6?, -SOR¿6?, -SO¿2?R¿6?, SR6N(R7R8), -N(R¿7?R¿8?) ou phényle; G est C¿1?-C¿6? alkyle; X est une liaison, -NH, C¿1?-C¿6? alkyle, C¿1?-C¿6? alcényle, C¿1?-C¿6? alcoxy, C¿1?-C¿6? thioalkyle, C¿1?-C¿6? alkylamino, ou (CH)J; J est C¿1?-C¿6? alkyle, C¿3?-C¿7? cycloalkyle, phényle ou benzyle; et n est un entier valant de 1 à 6. Ces composés conviennent au traitement d'affections associées aux virus de l'herpès, y-compris le cytomégalovirus humain, les herpès simplex, le virus d'Epstein-Barr, le virus de la varicelle-zona, les herpèsvirus 6 et 7 humain et l'herpèsvirus de Kaposi.
CA002350899A 1998-12-09 1999-12-06 Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues Abandoned CA2350899A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US20831698A 1998-12-09 1998-12-09
US09/208,316 1998-12-09
PCT/US1999/028844 WO2000034237A2 (fr) 1998-12-09 1999-12-06 Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues

Publications (1)

Publication Number Publication Date
CA2350899A1 true CA2350899A1 (fr) 2000-06-15

Family

ID=22774137

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002350899A Abandoned CA2350899A1 (fr) 1998-12-09 1999-12-06 Inhibiteurs des virus de l'herpes a base de thio-urees contenant des acetamides et des acetamides substitues

Country Status (15)

Country Link
EP (1) EP1137633A2 (fr)
JP (1) JP2002531544A (fr)
KR (1) KR20010087413A (fr)
CN (1) CN1333750A (fr)
AU (1) AU3111200A (fr)
BR (1) BR9916041A (fr)
CA (1) CA2350899A1 (fr)
CZ (1) CZ20012060A3 (fr)
EA (1) EA200100640A1 (fr)
HU (1) HUP0104944A3 (fr)
IL (1) IL143204A0 (fr)
NO (1) NO20012834L (fr)
PL (1) PL349131A1 (fr)
WO (1) WO2000034237A2 (fr)
ZA (1) ZA200104142B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6166028A (en) * 1998-12-09 2000-12-26 American Home Products Corporation Diaminopuridine-containing thiourea inhibitors of herpes viruses
US6844367B1 (en) 1999-09-17 2005-01-18 Millennium Pharmaceuticals, Inc. Benzamides and related inhibitors of factor Xa
WO2001064642A2 (fr) 2000-02-29 2001-09-07 Cor Therapeutics, Inc. Benzamides et inhibiteurs connexes du facteur xa
JP4690889B2 (ja) * 2002-10-24 2011-06-01 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング メチレン尿素誘導体
US7220768B2 (en) * 2003-02-11 2007-05-22 Wyeth Holdings Corp. Isoxazole-containing thiourea inhibitors useful for treatment of varicella zoster virus
EP1660661A2 (fr) 2003-08-08 2006-05-31 Arriva Pharmaceuticals, Inc. Procede de production de proteines dans une levure
CA2772017C (fr) 2003-08-29 2016-05-31 Mitsui Chemicals, Inc. Insecticide s'utilisant en agriculture ou en horticulture et procede d'utilisation correspondant
AU2005221151A1 (en) 2004-03-09 2005-09-22 Arriva Pharmaceuticals, Inc. Treatment of chronic obstructive pulmonary disease by low dose inhalation of protease inhibitor
EP2074085A2 (fr) * 2006-10-13 2009-07-01 Lica Pharmaceuticals A/S Composés de thiocarbamide anti-viraux
ES2382055T3 (es) 2006-11-02 2012-06-04 Millennium Pharmaceuticals, Inc. Métodos para sintetizar sales farmacéuticas de un inhibidor del factor Xa
CN108619123A (zh) * 2018-03-13 2018-10-09 武汉威立得生物医药有限公司 Tenovin-1在制备防治人类疱疹病毒感染药物中的应用
WO2019193541A1 (fr) * 2018-04-06 2019-10-10 Glaxosmithkline Intellectual Property Development Limited Dérivés de cycle aromatiques bicycliques de formule (i) utilisés en tant qu'inhibiteurs d'atf4
CN112807294B (zh) * 2019-11-18 2023-09-05 武汉大学 一种酰基硫脲类化合物在制备治疗或预防单纯疱疹病毒i型感染药物中的应用
WO2022150962A1 (fr) * 2021-01-12 2022-07-21 Westlake Pharmaceutical (Hangzhou) Co., Ltd. Inhibiteurs de protéase, leur préparation et leurs utilisations

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69830751T2 (de) * 1997-04-10 2006-05-18 Pharmacia & Upjohn Co. Llc, Kalamazoo Polyaromatische Verbindungen zur Behandlung von Herpes-Infektionen

Also Published As

Publication number Publication date
NO20012834L (no) 2001-08-07
CZ20012060A3 (cs) 2001-11-14
CN1333750A (zh) 2002-01-30
HUP0104944A2 (hu) 2002-04-29
EA200100640A1 (ru) 2001-12-24
WO2000034237A2 (fr) 2000-06-15
KR20010087413A (ko) 2001-09-15
AU3111200A (en) 2000-06-26
ZA200104142B (en) 2002-10-25
EP1137633A2 (fr) 2001-10-04
NO20012834D0 (no) 2001-06-08
HUP0104944A3 (en) 2003-03-28
BR9916041A (pt) 2001-12-04
JP2002531544A (ja) 2002-09-24
WO2000034237A3 (fr) 2000-11-23
IL143204A0 (en) 2002-04-21
PL349131A1 (en) 2002-07-01

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Legal Events

Date Code Title Description
FZDE Discontinued