WO2000034258A3 - Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group - Google Patents

Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group Download PDF

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Publication number
WO2000034258A3
WO2000034258A3 PCT/US1999/028842 US9928842W WO0034258A3 WO 2000034258 A3 WO2000034258 A3 WO 2000034258A3 US 9928842 W US9928842 W US 9928842W WO 0034258 A3 WO0034258 A3 WO 0034258A3
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WO
WIPO (PCT)
Prior art keywords
carbon atoms
alkyl
hydrogen
heteroaryl
perhaloalkyl
Prior art date
Application number
PCT/US1999/028842
Other languages
French (fr)
Other versions
WO2000034258A2 (en
Inventor
Jonathan David Bloom
Kevin Joseph Curran
Martin Joseph Digrandi
Russell George Dushin
Thomas Richard Jones
Stanley Albert Lang
Adma Antonia Ross
Eugene Anthony Terefenko
Bryan Mark O'hara
Original Assignee
American Home Prod
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
Priority to KR1020017007116A priority Critical patent/KR20010087416A/en
Priority to JP2000586705A priority patent/JP2002531554A/en
Priority to CA002350767A priority patent/CA2350767A1/en
Priority to AU19347/00A priority patent/AU1934700A/en
Application filed by American Home Prod filed Critical American Home Prod
Priority to SK768-2001A priority patent/SK7682001A3/en
Priority to BR9916046-3A priority patent/BR9916046A/en
Priority to IL14318299A priority patent/IL143182A0/en
Priority to PL99349217A priority patent/PL349217A1/en
Priority to EA200100631A priority patent/EA200100631A1/en
Priority to IDW00200101231A priority patent/ID30158A/en
Priority to EP99963023A priority patent/EP1144397A3/en
Publication of WO2000034258A2 publication Critical patent/WO2000034258A2/en
Priority to NO20012832A priority patent/NO20012832L/en
Priority to BG105581A priority patent/BG105581A/en
Publication of WO2000034258A3 publication Critical patent/WO2000034258A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic 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
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two 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
    • C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/06—1,2,3-Thiadiazoles; Hydrogenated 1,2,3-thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Virology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Neurology (AREA)
  • Pulmonology (AREA)
  • AIDS & HIV (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Biotechnology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Furan Compounds (AREA)

Abstract

Compounds having formula (I) wherein R1-R5 are independently selected from hydrogen, alkyl of 1 to 6 carbon atoms, alkenyl of 2 to 6 carbon atoms, alkynyl of 2 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 carbon members, aryl, heteroaryl, halogen, CN, NO2, CO2R6, COR6, OR6, SR6, SOR6, SO2R6, CONR7R8, NR6N(R7R8), N(R7R8) or W-Y-(CH2)n-Z provided that at least one of R1-R5 is not hydrogen; or R2 and R3 or R3 and R4, taken together form a 3 to 7 membered heterocycloalkyl or 3 to 7 membered heteroaryl; R6 and R7 are independently hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, or aryl; R8 is hydrogen, alkyl of 1 to 6 carbon atoms, perhaloalkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 10 carbon atoms, heterocycloalkyl of 3 to 10 members, aryl or heteroaryl, or R7 and R8, taken together may form a 3 to 7 membered heterocycloalkyl; W is O, NR6, or is absent; Y is (CO)- or (CO2)-, or is absent; Z is alkyl of 1 to 4 carbon atoms, CN, CO2R6, COR6, CONR7R8, OCOR6, NR6COR7, OCONR6, OR6, SR6, SOR6, SO2R6, SR6N(R7R8), N(R7R8) or phenyl; G is monocyclic heteroaryl; X is a bond, NH, alkyl of 1 to 6 carbon atoms, alkenyl of 1 to 6 carbon atoms, alkoxy of 1 to 6 carbon atoms, or thioalkyl of 1 to 6 carbon atoms, alkylamino of 1 to 6 carbon atoms, or (CH)J; J is alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or benzyl; and n is an integer from 1 to 6, useful in the treatment of diseases associated with herpes viruses including human cytomegalovirus, herpes simplex viruses, Epstein-Barr virus, varicella-zoster virus, human herpesviruses -6 and -7, and Kaposi herpesvirus.
PCT/US1999/028842 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group WO2000034258A2 (en)

Priority Applications (13)

Application Number Priority Date Filing Date Title
BR9916046-3A BR9916046A (en) 1998-12-09 1999-12-06 Compound, pharmaceutical composition, and processes for inhibiting the replication of a herpes virus and for treating a patient suffering from a herpes virus infection
CA002350767A CA2350767A1 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
AU19347/00A AU1934700A (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
PL99349217A PL349217A1 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
SK768-2001A SK7682001A3 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
JP2000586705A JP2002531554A (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpesvirus, including phenylenediamines
IL14318299A IL143182A0 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
KR1020017007116A KR20010087416A (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
EA200100631A EA200100631A1 (en) 1998-12-09 1999-12-06 INHIBITORS OF HERPES VIRUSES PRESENTING HETEROCYCLIC CARBOXAMIDE-CONTAINING THIOMOCAWN AND HAVING A PHENYLENIA-DIAGROUTE
IDW00200101231A ID30158A (en) 1998-12-09 1999-12-06 THIOUREA THAT CONTAIN HETEROSICLIC OF CARBOXAMIDE, PREVENTION OF HERPES VIRUSES CONTAINING PHENILENADIAMINE CLUSTERS
EP99963023A EP1144397A3 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group
NO20012832A NO20012832L (en) 1998-12-09 2001-06-08 Heterocyclic carboxamide-containing thiourea inhibitors of herpesvirus containing phenylenediamine group
BG105581A BG105581A (en) 1998-12-09 2001-06-08 Heterocyclic carboxamide-containing thiurea inhibitor of herpes viruses containing phenylenediamine group

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US20855998A 1998-12-09 1998-12-09
US09/208,559 1999-12-09

Publications (2)

Publication Number Publication Date
WO2000034258A2 WO2000034258A2 (en) 2000-06-15
WO2000034258A3 true WO2000034258A3 (en) 2001-11-29

Family

ID=22775044

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1999/028842 WO2000034258A2 (en) 1998-12-09 1999-12-06 Heterocyclic carboxamide-containing thiourea inhibitors of herpes viruses containing phenylenediamine group

Country Status (18)

Country Link
EP (1) EP1144397A3 (en)
JP (1) JP2002531554A (en)
CN (1) CN1348446A (en)
AU (1) AU1934700A (en)
BG (1) BG105581A (en)
BR (1) BR9916046A (en)
CA (1) CA2350767A1 (en)
CZ (1) CZ20011956A3 (en)
EA (1) EA200100631A1 (en)
HU (1) HUP0200232A2 (en)
ID (1) ID30158A (en)
IL (1) IL143182A0 (en)
NO (1) NO20012832L (en)
PL (1) PL349217A1 (en)
SK (1) SK7682001A3 (en)
TR (1) TR200101664T2 (en)
WO (1) WO2000034258A2 (en)
ZA (1) ZA200104377B (en)

Families Citing this family (12)

* 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
DK1259485T3 (en) 2000-02-29 2006-04-10 Millennium Pharm Inc Benzamides and related inhibitors of factor Xa
US7220768B2 (en) * 2003-02-11 2007-05-22 Wyeth Holdings Corp. Isoxazole-containing thiourea inhibitors useful for treatment of varicella zoster virus
WO2008057972A1 (en) 2006-11-02 2008-05-15 Millennium Pharmaceuticals, Inc. Methods of synthesizing pharmaceutical salts of a factor xa inhibitor
EP2914592B1 (en) 2012-11-03 2017-10-11 Boehringer Ingelheim International GmbH Inhibitors of cytomegalovirus
US9284310B2 (en) 2012-11-03 2016-03-15 Boehringer Ingelheim International Gmbh Inhibitors of cytomegalovirus
CN110565100B (en) * 2019-07-12 2021-05-07 西北工业大学 Cobaltocene cation-based corrosion inhibitor and preparation method and use method thereof
CN117769548A (en) 2021-08-05 2024-03-26 浙江海正药业股份有限公司 Aromatic acetylene derivative and preparation method and application thereof
WO2023088718A1 (en) 2021-11-19 2023-05-25 Basf Se Bicyclic compounds for the control of invertebrate pests
CN115433093A (en) * 2022-09-26 2022-12-06 无锡双启科技有限公司 Preparation method of 3-chloro-4-trifluoromethylaniline
CN115710190A (en) * 2022-11-16 2023-02-24 常州佳德医药科技有限公司 4-methoxy-2-amino-N, N-dimethylaniline, preparation method and application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998045259A2 (en) * 1997-04-10 1998-10-15 Pharmacia & Upjohn Company Polyaromatic antiviral compositions

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998045259A2 (en) * 1997-04-10 1998-10-15 Pharmacia & Upjohn Company Polyaromatic antiviral compositions

Also Published As

Publication number Publication date
TR200101664T2 (en) 2002-03-21
EA200100631A1 (en) 2002-02-28
BG105581A (en) 2001-12-31
WO2000034258A2 (en) 2000-06-15
CA2350767A1 (en) 2000-06-15
EP1144397A3 (en) 2002-09-11
JP2002531554A (en) 2002-09-24
ID30158A (en) 2001-11-08
CN1348446A (en) 2002-05-08
HUP0200232A2 (en) 2002-05-29
BR9916046A (en) 2001-10-02
PL349217A1 (en) 2002-07-01
EP1144397A2 (en) 2001-10-17
CZ20011956A3 (en) 2001-10-17
AU1934700A (en) 2000-06-26
ZA200104377B (en) 2002-12-20
NO20012832D0 (en) 2001-06-08
IL143182A0 (en) 2002-04-21
NO20012832L (en) 2001-08-07
SK7682001A3 (en) 2002-07-02

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