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US 6,307,049 B1Granted
Heterocyclic 2-substituted ketoamides
AssigneeThe Procter & Gamble Company
InventorsJohn McMillan McIver, Charles Raymond Degenhardt, David Joseph Eickhoff
Life of this patent
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Abstract
The present disclosure describes novel compounds and compositions which are particularly useful for treating hair loss in mammals, including arresting and/or reversing hair loss and promoting hair growth. The present compounds and compositions may also be useful against a variety of disorders including, for example, multi-drug resistance, human immunodeficiency virus (HIV), cardiac injury, and neurological disorders, and may be useful for controlling parasites and invoking immunosuppression.
Claims11
A compound having a structure:
- and pharmaceutically acceptable salts, hydrates, and biohydrolyzable amides, esters, and imides thereof, wherein:
- (a) V is a heteroatom wherein the heteroatom is nitrogen;
- (b) R1 is selected from the group consisting of alkyl having at least 3 carbon atoms, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, and heteroarylalkenyl;
- (c) Z is a saturated or unsaturated 6-, membered heterocycle that does not contain any heteroatoms other than the V nitrogen;
- (d) K is selected from the group consisting of hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, and heteroarylalkenyl;
- (e) W is selected from the group consisting of nil, hydrogen, and lower alkyl;
- (f) A is selected from the group consisting of nil and alkyl;
- (g) X and Y are each, independently, selected from the group consisting of C(O), P(O), N, O, and S, wherein:
- (i) when X is C(O) then R3 is nil and Y is selected from the group consisting of N, and S;
- (ii) when X is P(O) then R3 is nil and Y is selected from the group consisting of N and O;
- (iii) when X is N then R3 is selected from hydrogen, alkyl, and arylalkyl, Y is selected from the group consisting of C(O) and P(O), and R2 is nil;
- (iv) when X is O then R3 is nil, Y is selected from the group consisting of C(O) and P(O), and R2 is nil;
- and
- (v) when X is S then R3 is nil, Y is C(O), and R2 is nil;
- (h) R2 and R3 are each, independently, selected from the group consisting of nil, hydrogen, alkyl, and arylalkyl;
- (i) R4 is selected from the group consisting of methylene and methyne;
- (j) R5 and R6 are each, independently, selected from the group consisting of nil, hydrogen, alkyl having at least three carbon atoms, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, and heteroarylalkenyl;
- wherein at least one of R5 or R6 is not nil or hydrogen;
- (k) R7, R8, and R9, and R10 are each, independently, selected from the group consisting of nil, hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, heteroarylalkenyl, halo, cyano, hydroxy, oxo, imino, —R14SR15, —R14S(O2)R15, —R14S(O)R15, —R14C(O)R15, —R14C(O)NR15R16, —R14C(O)OR15, —R14OR15, —R14NR15R16, —R14P(O)NR15R16, —R14 P(O)OR15R16, and a spiro moiety, and wherein R7 and R8 may be optionally bonded together to form an aromatic or saturated, carbocyclic or heterocyclic ring wherein the ring is fused to Z;
- wherein when A is nil and X is C(O) at least one of R7, R8, R9, and R10 is not nil or hydrogen;
- (l) R14 is selected from the group consisting of nil, alkyl, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, and heteroarylalkenyl;
- and
- (m) R15 is selected from the group consisting of hydrogen, alkyl, alkenyl, heteroalkyl, heteroalkenyl, cycloalkyl, heterocycloalkyl, aryl, arylalkyl, heteroarylalkyl, arylalkenyl, and heteroarylalkenyl;
- and
- (n) R16 is selected from the group consisting of hydrogen and alkyl.
22 more elements
Dependencies are inferred from the claim text.