US4980350A
Expired / Lapsed
US
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Piperazinylalkylpyrimidines as hypoglycemic agents
Assignee: Merck and Co Inc
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Filing: 1989-07-31
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Granted: 1990-12-25
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Expires: 2009-07-31
Abstract
Abstract Novel hypoglycemic agents having the formula (I) are disclosed. <IMAGE> (I)
Inventors
- 👤 Malcolm MacCoss
- 👤 Richard L. Tolman
- 👤 Arthur F. Wagner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 23:12
CPC Classifications
C; C07; C07D; C07D239/00; C07D239/02; C07D239/24; C07D239/28; C07D239/32; C07D239/42; C07D239/46; C07D239/47; C07D251/00; C07D251/02; C07D251/12; C07D251/26; C07D251/40; C07D251/42
Claims Analysis
Total Claims: 24
Claim 1
Independent Claim
191 words
A compound of structural formula I ##STR8## wherein X and Y are independently --N═ and --(C--R 1 )═; provided that at least one of X or Y is --N═ and that when X is --N═, R 1 is other than H, alkyl or alkoxy; R 1 is H, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl or C 1-6 alkoxy; R 2 and R 3 are independently H, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl, or NH 2 , or NR 5 R 6 , or C 1-6 alkoxy; provided that only one of R 2 and R 3 may be H and when R 2 or R 3 is NH 2 or NR 5 R 6 X is --N═; R 4 is H, C 1-6 alkyl, C 6-10 arylC 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl; R 5 and R 6 are independently H, C 1-6 alkyl, or R 5 and R 6 together with the nitrogen atom to which they are attached form a hetero cyclic ring of 5 to 6 atoms; and halo is Br, Cl or F; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
191 words
A compound of structural formula I ##STR8## wherein X and Y are independently --N═ and --(C--R 1 )═; provided that at least one of X or Y is --N═ and that when X is --N═, R 1 is other than H, alkyl or alkoxy; R 1 is H, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl or C 1-6 alkoxy; R 2 and R 3 are independently H, C 1-6 alkyl, haloC 1-6 alkyl, dihaloC 1-6 alkyl, or NH 2 , or NR 5 R 6 , or C 1-6 alkoxy; provided that only one of R 2 and R 3 may be H and when R 2 or R 3 is NH 2 or NR 5 R 6 X is --N═; R 4 is H, C 1-6 alkyl, C 6-10 arylC 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl; R 5 and R 6 are independently H, C 1-6 alkyl, or R 5 and R 6 together with the nitrogen atom to which they are attached form a hetero cyclic ring of 5 to 6 atoms; and halo is Br, Cl or F; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
14 words
A compound of claim 1 wherein: X is --(C--R 1 )═; Y is --N═.
Claim 4
Dependent Claim
74 words
A compound of claim 2 wherein: R 1 is H, C 1-6 alkyl, FC 1-6 alkyl or F 2 C 1-6 alkyl; R 2 is H, C 1-6 alkyl, FC 1-6 alkyl, or F 2 C 1-6 alkyl; R 3 is H, C 1-6 alkyl, FC 1-6 alkyl or F 2 C 1-6 alkyl; provided that only one of R 2 and R 3 is H; R 4 is H or C 1-6 alkyl.
Claim 5
Dependent Claim
27 words
A compound of claim 3 wherein: FC 1-6 alkyl is FCH 2 CH 2 --; and F 2 C 1-6 alkyl is F 2 CHCH 2 --.
Claim 6
Dependent Claim
43 words
A compound of claim 4 wherein: R 1 is H or C 1-6 alkyl; R 2 is H or C 1-6 alkyl; R 3 is H or C 1-6 alkyl; provided that only one of R 2 and R 3 may be H.
Claim 7
Dependent Claim
20 words
A compound of claim 5 wherein: R 1 is H or CH 3 ; R 2 is C 1-6 alkyl.
Claim 8
Dependent Claim
108 words
A compound of claim 6 selected from the group wherein: a. R 1 =H, R 2 =n butyl, R 3 =methyl and R 4 =H; b. R 1 =H, R 2 =sec-butyl, R 3 =H, and R 4 =H; c. R 1 =methyl, R 2 =methyl, R 3 =H, and R 4 =H; d. R 1 =H, R 2 =methyl, R 3 =H, and R 4 =H; e. R 1 =H, R 2 =methyl, R 3 =methyl and R 4 =H; f. R 1 =H, R 2 =methyl, R 3 =H, and R 4 =methyl; g. R 1 =methyl, R 2 =methyl, R 3 =methyl, R 4 =H.
Claim 9
Dependent Claim
14 words
A compound of claim 1 wherein: X is --N═; Y is --(C--R 1 )═.
Claim 10
Dependent Claim
80 words
A compound of claim 8 wherein: R 1 is FC 1-6 alkyl or F 2 C -6 alkyl; R 2 is H or C 1-6 alkyl, FC 1-6 alkyl, F 2 C 1-6 alkyl or NH 2 or NR 5 R 6 ; R 3 is H or C 1-6 alkyl, FC 1-6 alkyl, F 2 C 1-6 alkyl; provided that only one of R 2 and R 3 may be H; R 4 is H or C 1-6 alkyl.
Claim 11
Dependent Claim
31 words
A compound of claim 9 wherein: R 2 is H or C 1-6 alkyl or NH 2 or NR 5 R 6 ; R 3 is H or C 1-6 alkyl.
Claim 12
Dependent Claim
18 words
A compound of claim 10 wherein: R 2 is or NH 2 ; and R 4 is H.
Claim 13
Dependent Claim
12 words
A compound of claim 1 wherein: X is --N═; Y is --N═.
Claim 14
Dependent Claim
49 words
A compound of claim 12 wherein: R 2 is H or C 1-6 alkyl, FC 1-6 alkyl or F 2 C 1-6 alkyl; R 3 is H or C 1-6 alkyl, FC 1-6 alkyl, or F 2 C 1-6 alkyl; and R 4 is H or C 1-6 alkyl.
Claim 15
Dependent Claim
23 words
A compound of claim 13 wherein R 2 is H or C 1-6 alkyl; and R 3 is H or C 1-6 alkyl.
Claim 16
Dependent Claim
18 words
A compound of claim 14 wherein R 2 is methyl, R 3 is H, R 4 is H.
Claim 17
Dependent Claim
30 words
A composition useful for the treatment of diabetes or obesity with associated insulin resistance which consists of an inert carrier and a nontoxic dose of a compound of claim 1.
Claim 18
Dependent Claim
37 words
A method for the treatment of diabetes or obesity with associated insulin resistance which consists of orally administering to a patient in need of such treatment a therapeutically effective nontoxic dose of a compound of claim 1.
Claim 19
Dependent Claim
30 words
A composition useful for the treatment of diabetes or obesity with associated insulin resistance which consists of an inert carrier and a nontoxic dose of a compound of claim 7.
Claim 20
Dependent Claim
37 words
A method for the treatment of diabetes or obesity with associated insulin resistance which consists of orally administering to a patient in need of such treatment a therapeutically effective nontoxic dose of a compound of claim 7.
Claim 21
Dependent Claim
30 words
A composition useful for the treatment of diabetes or obesity with associated insulin resistance which consists of an inert carrier and a nontoxic dose of a compound of claim 11.
Claim 22
Dependent Claim
37 words
A method for the treatment of diabetes or obesity with associated insulin resistance which consists of orally administering to a patient in need of such treatment a therapeutically effective nontoxic dose of a compound of claim 11.
Claim 23
Dependent Claim
30 words
A composition useful for the treatment of diabetes or obesity with associated insulin resistance which consists of an inert carrier and a nontoxic dose of a compound of claim 15.
Claim 24
Dependent Claim
37 words
A method for the treatment of diabetes or obesity with associated insulin resistance which consists of orally administering to a patient in need of such treatment a therapeutically effective nontoxic dose of a compound of claim 15.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-12-24 | 1994-06-25 | 1994-12-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-12-24 | 1998-06-25 | 1998-12-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-12-24 | 2002-06-25 | 2002-12-25 | $7700.00 | Window Closed / Lapsed |