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Patent · US7851479B2 · B2 · US

Use of pyrimidinedione derivative for preventing or treating hepatitis C

(11) Publication number
US7851479B2
(21) Application number
US-27865907-A
(22) Filing date
2007-02-08
(30) Priority date
2006-02-10
(43) Publication date
2010-12-14
(45) Date of grant
2010-12-14
(51) IPC
A61K 31/513; A61K 31/70
(52) CPC
  • A61K Preparations for medical, dental or toiletry purposes: 31/505
  • A61P Specific therapeutic activity of chemical compounds or medicinal preparations: 1/16, 31/12, 31/14
  • B65G Transport or storage devices, e.g. conveyors for loading or tipping, shop conveyor systems or pneumatic tube conveyors: 2201/022, 2249/00, 47/883, 47/912, 49/061, 49/068
(73) Assignee
SAMJIN PHARM CO LTD
(72) Inventors
KWON HO-SEOK; LEE JAE-WOONG; LEE SUN-HWAN; LEE YOUNG-HEE; JOO JEONG-HO; CHUNG SUN-GAN; KIM HYUN-TAE; CHO EUI-HWAN; MYUNG HYUN-NAM
(54) Title
Use of pyrimidinedione derivative for preventing or treating hepatitis C
(57) Abstract

A pyrimidinedione derivative of formula (I) or a pharmaceutically acceptable salt thereof exhibits excellent inhibitory activity against hepatitis C virus.

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Claims (3)

  1. A method for treating hepatitis C in a mammal in need of such treatment, which comprises administering a pyrimidinedione compound of the following formula (I) or a pharmaceutically acceptable salt thereof to the mammal: wherein, R 1 is C 3 ˜C 6 cycloalkyl or C 3 ˜C 6 cycloalkenyl optionally substituted with at least one hydroxyC 1 ˜C 4 alkyl; X is oxygen, sulfur or carbonyl; n is 1 or 2; and R 2, R 3 and R 4 are each independently hydrogen or C 1 ˜C 4 alkyl.
  2. The method of claim 1, wherein R 1 is C 3 ˜C 6 cycloalkyl, cyclopentenyl or hydroxymethylcyclopentenyl.
  3. The method of claim 1, wherein the pyrimidinedione compound is: 1-cyclopropylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopropylmethyl-6-(3,5-dimethyl-phenoxy)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclobutylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopentylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenoxy)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent- 1-enylmethyl-6-(3 5 -dimethyl-benzoyl)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-3-enylmethyl-5-isopropyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione; 1-cyclohexylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopentyl-ethyl)-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-2-enyl-ethyl)-6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-3-enyl-ethyl)-6-(3,5-dimethyl-phenylsulfanyl)-5-ethyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-2-enyl-ethyl)-6-(3,5-dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione; or 6-(3,5-dimethyl-benzoyl)-5-ethyl-1-(4-hydroxymethyl-cyclopent-1-enylmethyl)-1H-pyrimidine-2,4-dione.

Description

This is a National Stage application under 35 U.S.C. §371 of PCT/KR2007/000688 filed on Feb. 8, 2007, which claims priority from Korean patent application 10-2006-0013037 filed Feb. 10, 2006, all of which are incorporated herein by reference.

The present invention relates to a use of a pyrimidinedione derivative or a pharmaceutically acceptable salt thereof for preventing or treating hepatitis C.

Hepatitis C caused by hepatitis C virus (HCV) infection has been extensively studied in the last two decades, but it still remains difficult to treat due to incomplete information on HCV. At present, there is only one drug, Ribavirin, approved by Food and Drug Administration (FDA) for treating hepatitis C (Thomas et al., Hepatology 20(4):440, 1994), which is a purine nucleoside derivative. Interferon-α having antiviral activity against a wide spectrum of DNA and RNA viruses has been suggested as a therapeutic for hepatitis C. However, they are considered to be inappropriate for clinical application due to serious side effects and their low curative effect. Although therapy with Ribavirin-interferon-α combination has shown an improved result, it still exhibits low specificity for hepatitis C virus and low curative effect, besides the accompanying side effects such as anemia and depression. Accordingly, a new therapeutic for hepatitis C having improved curative activity and reduced side effects is required.

Some pyrimidinedione derivatives have been developed for use as an antiviral agent for treating AIDS.

Citations (8)

  • KR20000065885A
  • KR20010006730A
  • US2005009737A1
  • US7429572B2
  • WO0051990A1
  • WO0061563A1
  • WO0061564A1
  • WO9730979A1
Record as JSON
{
  "publication_number": "US7851479B2",
  "country": "US",
  "kind": "B2",
  "title": "Use of pyrimidinedione derivative for preventing or treating hepatitis C",
  "abstract": "A pyrimidinedione derivative of formula (I) or a pharmaceutically acceptable salt thereof exhibits excellent inhibitory activity against hepatitis C virus.",
  "claims": [
    "1. A method for treating hepatitis C in a mammal in need of such treatment, which comprises administering a pyrimidinedione compound of the following formula (I) or a pharmaceutically acceptable salt thereof to the mammal: wherein, R 1 is C 3 ˜C 6 cycloalkyl or C 3 ˜C 6 cycloalkenyl optionally substituted with at least one hydroxyC 1 ˜C 4 alkyl; X is oxygen, sulfur or carbonyl; n is 1 or 2; and R 2, R 3 and R 4 are each independently hydrogen or C 1 ˜C 4 alkyl.",
    "2. The method of claim 1, wherein R 1 is C 3 ˜C 6 cycloalkyl, cyclopentenyl or hydroxymethylcyclopentenyl.",
    "3. The method of claim 1, wherein the pyrimidinedione compound is: 1-cyclopropylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopropylmethyl-6-(3,5-dimethyl-phenoxy)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclobutylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopentylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenoxy)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent- 1-enylmethyl-6-(3 5 -dimethyl-benzoyl)-5-ethyl-1H-pyrimidine-2,4-dione; 1-cyclopent-1-enylmethyl-6-(3,5-dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-cyclopent-3-enylmethyl-5-isopropyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione; 1-cyclohexylmethyl-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopentyl-ethyl)-6-(3,5-dimethyl-phenylsulfanyl)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-2-enyl-ethyl)-6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-3-enyl-ethyl)-6-(3,5-dimethyl-phenylsulfanyl)-5-ethyl-1H-pyrimidine-2,4-dione; 1-(2-cyclopent-2-enyl-ethyl)-6-(3,5-dimethyl-benzoyl)-5-isopropyl-1H-pyrimidine-2,4-dione; or 6-(3,5-dimethyl-benzoyl)-5-ethyl-1-(4-hydroxymethyl-cyclopent-1-enylmethyl)-1H-pyrimidine-2,4-dione."
  ],
  "description_excerpt": "This is a National Stage application under 35 U.S.C. §371 of PCT/KR2007/000688 filed on Feb. 8, 2007, which claims priority from Korean patent application 10-2006-0013037 filed Feb. 10, 2006, all of which are incorporated herein by reference.\n\nThe present invention relates to a use of a pyrimidinedione derivative or a pharmaceutically acceptable salt thereof for preventing or treating hepatitis C.\n\nHepatitis C caused by hepatitis C virus (HCV) infection has been extensively studied in the last two decades, but it still remains difficult to treat due to incomplete information on HCV. At present, there is only one drug, Ribavirin, approved by Food and Drug Administration (FDA) for treating hepatitis C (Thomas et al., Hepatology 20(4):440, 1994), which is a purine nucleoside derivative. Interferon-α having antiviral activity against a wide spectrum of DNA and RNA viruses has been suggested as a therapeutic for hepatitis C. However, they are considered to be inappropriate for clinical application due to serious side effects and their low curative effect. Although therapy with Ribavirin-interferon-α combination has shown an improved result, it still exhibits low specificity for hepatitis C virus and low curative effect, besides the accompanying side effects such as anemia and depression. Accordingly, a new therapeutic for hepatitis C having improved curative activity and reduced side effects is required.\n\nSome pyrimidinedione derivatives have been developed for use as an antiviral agent for treating AIDS.",
  "cpc": [
    "A61K 31/505",
    "A61P 1/16",
    "A61P 31/12",
    "A61P 31/14",
    "B65G 2201/022",
    "B65G 2249/00",
    "B65G 47/883",
    "B65G 47/912",
    "B65G 49/061",
    "B65G 49/068"
  ],
  "ipc": [
    "A61K 31/513",
    "A61K 31/70"
  ],
  "assignees": [
    "SAMJIN PHARM CO LTD"
  ],
  "inventors": [
    "KWON HO-SEOK",
    "LEE JAE-WOONG",
    "LEE SUN-HWAN",
    "LEE YOUNG-HEE",
    "JOO JEONG-HO",
    "CHUNG SUN-GAN",
    "KIM HYUN-TAE",
    "CHO EUI-HWAN",
    "MYUNG HYUN-NAM"
  ],
  "filing_date": "2007-02-08",
  "publication_date": "2010-12-14",
  "grant_date": "2010-12-14",
  "priority_date": "2006-02-10",
  "application_number": "US-27865907-A",
  "family_id": "38345401",
  "citations": [
    "KR20000065885A",
    "KR20010006730A",
    "US2005009737A1",
    "US7429572B2",
    "WO0051990A1",
    "WO0061563A1",
    "WO0061564A1",
    "WO9730979A1"
  ]
}

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