CA2207627A1 - 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents - Google Patents
4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agentsInfo
- Publication number
- CA2207627A1 CA2207627A1 CA002207627A CA2207627A CA2207627A1 CA 2207627 A1 CA2207627 A1 CA 2207627A1 CA 002207627 A CA002207627 A CA 002207627A CA 2207627 A CA2207627 A CA 2207627A CA 2207627 A1 CA2207627 A1 CA 2207627A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- optionally substituted
- sum
- heterocycloalkyl
- aryl
- 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
Links
Abstract
4-[(Heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinone hypocholesterolemic agents of formula (I) or a pharmaceutically acceptable salt thereof, wherein: A is optionally substituted heterocycloalkyl, optionally substituted heteroaryl, optionally substituted benzofused heterocycloalkyl, or optionally substituted benzofused heteroaryl; Ar1 is optionally substituted aryl; Ar2 is optionally substituted aryl; Q is a bond or, with the 3-position ring carbon of the azetidinone, forms the spiro group (a); and R1 is selected from the group consisting of -(CH2)9-, wherein q is 2-6 provided that when Q is a spiro ring, q can also be 0 or 1;
-(CH2)e-G-(CH2)r, wherein G is -O-, -C(O)-, phenylene, -NR8- or -S(O)0-2-, e is 0-5 and r is 0-5, provided that the sum of a and r is 1-6; alkenylene; and -(CH2)f-V-(CH2)g-, wherein V is cycloalkylene f is 1-5 and g is 0-5, provided that the sum of f and g is 1-6; R5 is (b), (c), (d), (e), (f), (g) or (h); R6 and R7 are -CH2-, -CH(alkyl)-, -C(dialkyl), -CH=CH- or -C(alkyl)=CH-; or R5 together with an adjacent R6, or R5 together with an adjacent R7, form a -CH=CH- or a -CH=C(alkyl)- group; a and b are independently 0-3, provided both are not zero and when Q is a bond Ri also can be: (i), (j) or (k); M is -O- -S- -S(O)- or -S(O)2-;
X, Y and Z are -CH2-, -CH(alkyl)- or -C(dialkyl); R10 and R12 -OR14, -O(CO)R14, -O(CO)OR16 or -O(CO)NR14R15; R11 and R13 are H, alkyl or aryl; or R10 and R11 together are =O, or R12 and R13 together are =O;
d is 1-3; h is 0-4; s is 0 or 1; t is 0 or 1; m, n and p are independently 0-4; provided that at least one of s and t is 1, and the sum of m, n, p, s and t is 1-6; provided that when p is 0 and t is 1, the sum of m, s and n is 1-5; and provided that when p is 0 and s is 1, the sum of m, t and n is 1-5; v is 0 or 1; j and k are independently I-5 provided that the sum of j, k and v is 1-5; Rs is H, alkyl, arylalkyl, -C(O)RI4 or -COOR14; R9 is H, alkyl, alkoxy, -COON, NO2, -NR14R15, OH or halogeno; R14 and R15 are H, alkyl, aryl and arylalkyl; R16 is alkyl or optionally substituted aryl; and R19 is H, OH or alkoxy are disclosed, as well as a method of lowering serum cholesterol by administering said compounds, pharmaceutical compositions containing them, and the combination of a substituted azetidinone and a cholesterol biosynthesis inhibitor for the treatment and prevention of atherosclerosis.
-(CH2)e-G-(CH2)r, wherein G is -O-, -C(O)-, phenylene, -NR8- or -S(O)0-2-, e is 0-5 and r is 0-5, provided that the sum of a and r is 1-6; alkenylene; and -(CH2)f-V-(CH2)g-, wherein V is cycloalkylene f is 1-5 and g is 0-5, provided that the sum of f and g is 1-6; R5 is (b), (c), (d), (e), (f), (g) or (h); R6 and R7 are -CH2-, -CH(alkyl)-, -C(dialkyl), -CH=CH- or -C(alkyl)=CH-; or R5 together with an adjacent R6, or R5 together with an adjacent R7, form a -CH=CH- or a -CH=C(alkyl)- group; a and b are independently 0-3, provided both are not zero and when Q is a bond Ri also can be: (i), (j) or (k); M is -O- -S- -S(O)- or -S(O)2-;
X, Y and Z are -CH2-, -CH(alkyl)- or -C(dialkyl); R10 and R12 -OR14, -O(CO)R14, -O(CO)OR16 or -O(CO)NR14R15; R11 and R13 are H, alkyl or aryl; or R10 and R11 together are =O, or R12 and R13 together are =O;
d is 1-3; h is 0-4; s is 0 or 1; t is 0 or 1; m, n and p are independently 0-4; provided that at least one of s and t is 1, and the sum of m, n, p, s and t is 1-6; provided that when p is 0 and t is 1, the sum of m, s and n is 1-5; and provided that when p is 0 and s is 1, the sum of m, t and n is 1-5; v is 0 or 1; j and k are independently I-5 provided that the sum of j, k and v is 1-5; Rs is H, alkyl, arylalkyl, -C(O)RI4 or -COOR14; R9 is H, alkyl, alkoxy, -COON, NO2, -NR14R15, OH or halogeno; R14 and R15 are H, alkyl, aryl and arylalkyl; R16 is alkyl or optionally substituted aryl; and R19 is H, OH or alkoxy are disclosed, as well as a method of lowering serum cholesterol by administering said compounds, pharmaceutical compositions containing them, and the combination of a substituted azetidinone and a cholesterol biosynthesis inhibitor for the treatment and prevention of atherosclerosis.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/361,265 US5656624A (en) | 1994-12-21 | 1994-12-21 | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
US08/361,265 | 1994-12-21 | ||
PCT/US1995/016007 WO1996019450A1 (en) | 1994-12-21 | 1995-12-18 | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2207627A1 true CA2207627A1 (en) | 1996-06-27 |
CA2207627C CA2207627C (en) | 2005-11-15 |
Family
ID=35530899
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002207627A Expired - Fee Related CA2207627C (en) | 1994-12-21 | 1995-12-18 | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents |
Country Status (1)
Country | Link |
---|---|
CA (1) | CA2207627C (en) |
-
1995
- 1995-12-18 CA CA002207627A patent/CA2207627C/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
CA2207627C (en) | 2005-11-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU4419896A (en) | 4-{(heterocycloalkyl or heteroaromatic)-substituted phenyphenyl}-2-azetidinones useful as hypolipidemic agents | |
AU669032B2 (en) | New indole, indazole and benzisoxazole compounds, process for preparing them and pharmaceutical compositions containing them | |
HUT69686A (en) | Process for preparing pharmaceutical compositions having serum cholesterol lowering effect | |
EP1036794A4 (en) | 2-aryl-8-oxodihydropurine derivatives, process for producing the same, medicinal compositions containing the same, and intermediates thereof | |
IL102582A0 (en) | Substituted beta-lactam compounds useful as hypocholesterolemic agents and processes for the preparation thereof | |
TW427974B (en) | Hydroxy-substituted azetidinone compounds useful as hypocholesterolemic agents | |
HUT77088A (en) | Sulfur-substituted azetidinone compounds useful as hypocholesterolemic agents and pharmaceutical compositions containing the same | |
CA2235943A1 (en) | Sugar-substituted 2-azetidinones useful as hypocholesterolemic agents | |
AU3464097A (en) | Arylpiperidinol and arylpiperidine derivatives and pharmaceuticals containing the same | |
CA2238845A1 (en) | Novel 2,3,5-trimethyl-4-hydroxy anilide derivatives, preparation thereof and therapeutical use thereof | |
ATE215937T1 (en) | OXAZOLIDINEDIONE DERIVATIVES AND THEIR USE AS HYPOGLYCEMIC AGENTS | |
CA2207627A1 (en) | 4-[(heterocycloalkyl or heteroaromatic)-substituted phenyl]-2-azetidinones useful as hypolipidemic agents | |
NZ334736A (en) | Acylaminoalkenylene-amide derivatives useful in treatments of the respiratory diseases where it is more specific for NK1 than NK2 | |
WO1999025716A3 (en) | Pyranones, method for the production and use thereof | |
PT955286E (en) | D-HYDRO-DERIVATIVES OR TETRA-HYDROFOLANTALINE HAVING AN ESTROGENIC (ANI-) ACTIVITY | |
IL134551A0 (en) | Methods for lowering platelet counts | |
TW333525B (en) | New perhydroisoindole derivatives, their preparation and the pharmaceutical compositions which contain them the invention relates to perhydroisoindole derivatives of general formula (I), and their salts when they exist advantageously as neurokinin A antagonists. | |
ZA200002151B (en) | 1-AZA-2-alkyl-6-aryl-cycloalkane compounds, a process for their preparation and pharmaceutical compositions containing them. | |
KR910007878A (en) | Dihydropyridine Derivatives and Pharmaceutical Compositions | |
KR970042558A (en) | β-methyl carbapenem carboxy ester derivative and preparation method thereof |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKLA | Lapsed |
Effective date: 20121218 |