CA2205202A1 - Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents - Google Patents

Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents

Info

Publication number
CA2205202A1
CA2205202A1 CA002205202A CA2205202A CA2205202A1 CA 2205202 A1 CA2205202 A1 CA 2205202A1 CA 002205202 A CA002205202 A CA 002205202A CA 2205202 A CA2205202 A CA 2205202A CA 2205202 A1 CA2205202 A1 CA 2205202A1
Authority
CA
Canada
Prior art keywords
coor6
aryl
lower alkyl
nr6r7
sulfur
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.)
Granted
Application number
CA002205202A
Other languages
French (fr)
Other versions
CA2205202C (en
Inventor
Brian A. Mckittrick
Sundeep Dugar
Duane A. Burnett
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.)
Merck Sharp and Dohme Corp
Original Assignee
Schering Corporation
Brian A. Mckittrick
Sundeep Dugar
Duane A. Burnett
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 claimed from US08/342,197 external-priority patent/US5624920A/en
Application filed by Schering Corporation, Brian A. Mckittrick, Sundeep Dugar, Duane A. Burnett filed Critical Schering Corporation
Publication of CA2205202A1 publication Critical patent/CA2205202A1/en
Application granted granted Critical
Publication of CA2205202C publication Critical patent/CA2205202C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Abstract

Sulfur-substituted azetidinone hypocholesterolemic agents of formula (I), or a pharmaceutically acceptable salt thereof, wherein: Ar1 is aryl, R10-substituted aryl or heteroaryl; Ar2 is aryl or R4-substituted aryl; Ar3 is aryl or R5-substituted aryl; X and Y are -CH2-, -CH(lower alkyl)- or -C(dilower alkyl)-; R is -OR6, -O(CO)R6, -O(CO)OR9 or -O(CO)NR6R7; R1 is hydrogen, lower alkyl or aryl; or R and R1 together are =0; q is 0 or 1; r is 0, 1 or 2; m and n are 0-5; provided that the sum of m, n and q is 1-5; R4 is selected from lower alkyl, -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7, -NR6(CO)R7, -NR6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, -CONR6R7, -COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10CONR6R7, -(lower alkylene)-COOR6 and -CH=CH-COOR6; R5 is selected from -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7 -NR6(CO)R7, -NR6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, -CONR6R7, -COR6, -SO2NR6R7, S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10CONR6R7, -CF3, -CN, -NO2, halogen, -(lower alkylene)COOR6 and -CH=CH-COOR6; R6, R7 and R8 are H, lower alkyl, aryl or aryl-substitued lower alkyl; R9 is lower alkyl, aryl or aryl-sybstituted lower alkyl; and R10 is selected from lower alkyl, -OR6, -O(CO)R6, -O(CO)OR9, -O(CH2)1-5OR6, -O(CO)NR6R7, -NR6R7, -NR6(CO)R7, -NR6(CO)OR9, -NR6(CO)NR7R8, -NR6SO2R9, -COOR6, -CONR6R7, COR6, -SO2NR6R7, -S(O)0-2R9, -O(CH2)1-10-COOR6, -O(CH2)1-10CONR6R7, -CF3, -CN, -NO2 and halogen; are disclosed, as well as pharmaceutical compositions containing them, and a method of lowering serum cholesterol by administering said compounds, alone or in combination with a cholesterol biosynthesis inhibitor.
CA002205202A 1994-11-18 1995-11-15 Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents Expired - Fee Related CA2205202C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US08/342,197 US5624920A (en) 1994-11-18 1994-11-18 Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents
US08/342,197 1994-11-18
US08/463,619 US5633246A (en) 1994-11-18 1995-06-05 Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents
US08/463,619 1995-06-05
PCT/US1995/014134 WO1996016037A1 (en) 1994-11-18 1995-11-15 Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents

Publications (2)

Publication Number Publication Date
CA2205202A1 true CA2205202A1 (en) 1996-05-30
CA2205202C CA2205202C (en) 2002-01-08

Family

ID=26992866

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002205202A Expired - Fee Related CA2205202C (en) 1994-11-18 1995-11-15 Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents

Country Status (25)

Country Link
US (2) US5633246A (en)
EP (1) EP0792264B1 (en)
JP (1) JP2908031B2 (en)
KR (1) KR100235806B1 (en)
CN (1) CN1083833C (en)
AT (1) ATE213726T1 (en)
AU (1) AU698750B2 (en)
BR (1) BR9509669A (en)
CA (1) CA2205202C (en)
CZ (1) CZ289033B6 (en)
DE (1) DE69525643T2 (en)
DK (1) DK0792264T3 (en)
ES (1) ES2169162T3 (en)
FI (1) FI116220B (en)
HK (1) HK1002558A1 (en)
HU (1) HU227672B1 (en)
MX (1) MX9703577A (en)
NO (1) NO308468B1 (en)
NZ (1) NZ296720A (en)
PL (1) PL184310B1 (en)
PT (1) PT792264E (en)
RU (1) RU2159243C2 (en)
SK (1) SK283860B6 (en)
UA (1) UA54381C2 (en)
WO (1) WO1996016037A1 (en)

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Also Published As

Publication number Publication date
BR9509669A (en) 1997-10-28
MX9703577A (en) 1997-08-30
NO308468B1 (en) 2000-09-18
FI972099A (en) 1997-05-16
FI972099A0 (en) 1997-05-16
PT792264E (en) 2002-07-31
AU698750B2 (en) 1998-11-05
UA54381C2 (en) 2003-03-17
NO972272L (en) 1997-05-16
HU227672B1 (en) 2011-11-28
ATE213726T1 (en) 2002-03-15
US5633246A (en) 1997-05-27
JPH09512833A (en) 1997-12-22
DE69525643T2 (en) 2002-09-26
ES2169162T3 (en) 2002-07-01
EP0792264B1 (en) 2002-02-27
DE69525643D1 (en) 2002-04-04
CN1083833C (en) 2002-05-01
FI116220B (en) 2005-10-14
PL184310B1 (en) 2002-09-30
CN1174548A (en) 1998-02-25
DK0792264T3 (en) 2002-04-22
KR100235806B1 (en) 2000-02-01
AU4140196A (en) 1996-06-17
CZ289033B6 (en) 2001-10-17
HUT77088A (en) 1998-03-02
SK283860B6 (en) 2004-03-02
NO972272D0 (en) 1997-05-16
CZ148697A3 (en) 1997-11-12
JP2908031B2 (en) 1999-06-21
HK1002558A1 (en) 1998-09-04
CA2205202C (en) 2002-01-08
NZ296720A (en) 1999-03-29
KR970707092A (en) 1997-12-01
EP0792264A1 (en) 1997-09-03
SK61697A3 (en) 1997-12-10
RU2159243C2 (en) 2000-11-20
US5744467A (en) 1998-04-28
PL320092A1 (en) 1997-09-15
WO1996016037A1 (en) 1996-05-30

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