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WO2003018013B1 - Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same - Google Patents

Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same

Info

Publication number
WO2003018013B1
WO2003018013B1 PCT/KR2002/000977 KR0200977W WO03018013B1 WO 2003018013 B1 WO2003018013 B1 WO 2003018013B1 KR 0200977 W KR0200977 W KR 0200977W WO 03018013 B1 WO03018013 B1 WO 03018013B1
Authority
WO
WIPO (PCT)
Prior art keywords
chemical formula
stilbene derivative
amended
hydroxy
same
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.)
Ceased
Application number
PCT/KR2002/000977
Other languages
French (fr)
Other versions
WO2003018013A1 (en
Inventor
Sang-Hee Kim
Young-Jin Chun
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.)
Promeditech Inc
Original Assignee
Promeditech Inc
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 Promeditech Inc filed Critical Promeditech Inc
Publication of WO2003018013A1 publication Critical patent/WO2003018013A1/en
Anticipated expiration legal-status Critical
Publication of WO2003018013B1 publication Critical patent/WO2003018013B1/en
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof

Landscapes

  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

A stilbene derivative having cytochrome P450 1B1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same are disclosed. The stilbene derivative is a strong and selective inhibitor of cytochrome P450 1B1, thereby to decrease or prevent chemical carcinogenesis in mammals, in particular the development of a breast cancer, and can be used as a pharmaceutical tool to elucidate the function of cytochrome P450.

Claims

AMENDED CLAIMS
[received by the International Bureau on 24 February 2003 (24.02.03); Original claims 1-3 and 6-8 replaced by amended claim 1-3 and 6-8; claim 9 cancelled
(4 pages)]
1. (amended) A pharmaceutical composition comprising stilbene derivative of the following chemical formula 1 for inhibiting the activity of cytochrome P450 1 B1 enzyme. [Chemical formula 1]
Figure imgf000003_0001
In chemical formula 1 , Ri, R2 and R3 independently represent hydrogen, hydroxy or methoxy group, and
M represents (i) R4-substituted 2-pyridyl, 3-pyridyl or 4-pyridyl group;
(ii) R4-substituted 2-furyl, 3-furyl, 2-pyrrole, 3-pyrrole, 2-thiophenyl, or 3- thiophenyl group; or
(iii) phenyl ring of the following chemical formula I -1 ;
Figure imgf000003_0002
wherein R , R6, R7> and R8 independently represent hydrogen, hydroxy, halogen or C-ι-4 alkoxy group; and at least one of R5 and R9 is hydroxy, halogen or Cι- alkoxy group.
2. (amended) The pharmaceutical composition according to claim 1 , wherein the stilbene derivative is a compound of chemical formula 6. [Chemical formula 6]
Figure imgf000004_0001
In chemical formula 6, Ri represents hydrogen, hydroxy or methoxy group; and Ar represents 2-thiophenyl, 3-thiophenyl, 2-furyl, 3-furyl, 2-pyrrole, 3-pyrrole, 2-pyridyl, 3-pyridyl or 4-pyridyl group.
3.(amended) The pharmaceutical composition according to claim 1 , wherein the stilbene derivative is a compound of chemical formula 7. [Chemical formula 7]
Figure imgf000004_0002
In chemical formula 7, R-i represents hydrogen, hydroxy or methoxy group;
R2 represents hydrogen, hydroxy or Cι-3 alkoxy group; and R3 represents hydroxy or C1.3 alkoxy group.
4. The pharmaceutical composition according to claim 1 , wherein the stilbene derivative is a compound of chemical formula 8. [Chemical formula 8]
Figure imgf000005_0001
5. The pharmaceutical composition according to claim 1 , wherein the stilbene derivative is a compound of chemical formula 17. [Chemical formula 17]
Figure imgf000005_0002
β.(amended) An anticancer or cancer-preventive composition comprising the pharmaceutical composition according to one of claims 1 to 5.
7.(amended) The anticancer or cancer-preventive composition according to claim 6, wherein the cancer is a breast cancer or an ovarian cancer.
8. (amended) A stilbene derivative of the following chemical formula 2 or pharmaceutically acceptable salt thereof. [Chemical formula 2]
Figure imgf000005_0003
In chemical formula 2, M' represents R4-substituted 2-thiophenyl or 3- thiophenyl group; R-t and R3 represent methoxy group; R2 represents hydrogen or methoxy group; and R4 represents hydrogen, hydroxy, halogen or C-i- alkoxy group.
9. (cancelled)
PCT/KR2002/000977 2001-08-31 2002-05-23 Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same Ceased WO2003018013A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR2001/53363 2001-08-31
KR1020010053363A KR20030018800A (en) 2001-08-31 2001-08-31 Phenyl ring derivatives having cytochrome p450 1b1 inhibitory activity and pharmaceutically acceptable salts thereof, preparing process and compositions containing same

Publications (2)

Publication Number Publication Date
WO2003018013A1 WO2003018013A1 (en) 2003-03-06
WO2003018013B1 true WO2003018013B1 (en) 2004-04-08

Family

ID=19713806

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2002/000977 Ceased WO2003018013A1 (en) 2001-08-31 2002-05-23 Stilbene derivative having cytochrome p450 1b1 inhibitory activity, pharmaceutically acceptable salt thereof, method for preparing the same, and composition including the same

Country Status (2)

Country Link
KR (1) KR20030018800A (en)
WO (1) WO2003018013A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1331856C (en) * 2005-08-05 2007-08-15 大连理工大学 Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS
GB2463436A (en) * 2007-06-22 2010-03-17 Univ Aberdeen (11C)methoxy-radiolabelled 2,3',4,5'-tetramethylstilbene (TMS) and its preparation and use
KR101035010B1 (en) * 2009-02-25 2011-05-17 주식회사 엠.에스.라이팅 Air Purification & Lighting Complex
PL223452B1 (en) * 2012-03-30 2016-10-31 Univ Medyczny Im Karola Marcinkowskiego W Poznaniu New trans-stilbene derivatives and their use
WO2015039036A2 (en) * 2013-09-13 2015-03-19 Cortendo Ab(Publ) Novel cytochrome p450 inhibitors and their method of use
JP7679090B2 (en) * 2019-12-23 2025-05-19 カイナン デューク アイピー，エルエルシー Substituted hydroxystilbene compounds and derivatives, synthesis and uses thereof

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0489436A (en) * 1990-07-27 1992-03-23 Ricoh Co Ltd New aromatic compounds and nonlinear optical materials
GB9802522D0 (en) * 1998-02-06 1998-04-01 Montford University De Hydroxylation activated prodrugs
RU2215525C2 (en) * 1998-04-03 2003-11-10 Адзиномото Ко., Инк. Antitumor agent
KR100383366B1 (en) * 2000-12-19 2003-05-12 주식회사 태평양 Novel phenyl derivatives, the process for preparing them and the pharmacological composition and the cosmetic composition containing them

Also Published As

Publication number Publication date
WO2003018013A1 (en) 2003-03-06
KR20030018800A (en) 2003-03-06

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