Patent ID: 6194440
Filing Date: 2001-02-27
Classification: A61K,A61P,A61Q,C07D,Y10S

Abstract:
A method for treating alopecia or promoting hair growth in an animal in need thereof, which comprises administering to said animal an effective amount of a compound of formula I ##STR11##or a pharmaceutically acceptable salt, ester, or solvate thereof, wherein:A is CH.sub.2, O, NH or N--(C.sub.1 -C.sub.4 alkyl);B and D are independently Ar, hydrogen, C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.2 -C.sub.6 straight or branched chain alkenyl or alkynyl, C.sub.5 -C.sub.7 cycloalkyl substituted C.sub.1 -C.sub.6 straight or branched chain alkyl or C.sub.3 -C.sub.6 straight or branched chain alkenyl or alkynyl, C.sub.5 -C.sub.7 cycloalkenyl substituted C.sub.1 -C.sub.6 straight or branched chain alkyl or C.sub.3 -C.sub.6 straight or branched chain alkenyl or alkynyl, Ar substituted C.sub.1 -C.sub.6 straight or branched chain alkyl, or Ar substituted C.sub.3 -C.sub.6 straight or branched chain alkenyl or alkynyl; wherein any carbon atom of said alkyl is optionally replaced by a heteroatom selected from the group consisting of O, S, SO, SO.sub.2 and NR, wherein R is selected from the group consisting of hydrogen, C.sub.1 -C.sub.4 straight or branched chain alkyl, C.sub.3 -C.sub.4 straight or branched chain alkenyl or alkynyl, and C.sub.1 -C.sub.4 bridging alkyl wherein a bridge is formed between the nitrogen and a carbon atom of said heteroatom-containing chain to form a ring, and wherein said ring is optionally fused to an Ar group;J is selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.3 -C.sub.6 straight or branched chain alkenyl, and --CH.sub.2 Ar; K is selected from the group consisting of C.sub.1 -C.sub.4 straight or branched chain alkyl, --CH.sub.2 Ar, and cyclohexylmethyl; or J and K are taken together to form a 5-7 membered heterocyclic ring which is substituted with O, S, SO, or SO.sub.2 ;Z is O or S;Y is O or N, provided thatwhen Y is O, then R.sub.1 is a lone pair of electrons and R.sub.2 is selected from the group consisting of Ar, C.sub.1 -C.sub.6 straight or branched chain alkyl, and C.sub.3 -C.sub.6 straight or branched chain alkenyl or alkynyl; andwhen Y is N, then R.sub.1 and R.sub.2 are independently selected from the group consisting of Ar, C.sub.1 -C.sub.6 straight or branched chain alkyl, and C.sub.3 -C.sub.6 straight or branched chain alkenyl or alkynyl; or R.sub.1 and R.sub.2 are taken together to form a heterocyclic 5-6 membered ring selected from the group consisting of pyrrolidine, imidazolidine, pyrazolidine, piperidine, and piperazine;Ar is a carbocyclic aromatic group selected from the group consisting of phenyl, 1-naphthyl, 2-naphthyl, indenyl, azulenyl, fluorenyl, and anthracenyl; or a heterocyclic aromatic group selected from the group consisting of 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrrolyl, oxazolyl, thiazolyl, imidazolyl, pyraxolyl, 2-pyrazolinyl, pyrazolidinyl, isoxazolyl, isotriazolyl, 1,2,3-oxadiazolyl, 1,2,3-triazolyl, 1,3,4-thiadiazolyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,3,5-trithianyl, indolizinyl, indolyl, isoindolyl, 3H-indolyl, indolinyl, benzo[b]furanyl, benzo[b]thio-phenyl, 1H-indazolyl, benzimidazolyl, benzthiazolyl, purinyl, 4H-quinolizinyl, quinolinyl, 1,2,3,4-tetrahydroquinolinyl, isoquinolinyl, 1,2,3,4-tetrahydroisoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, 1,8-naphthyridinyl, pteridinyl, carbazolyl, acridinyl, phenazinyl, phenothiazinyl, and phenoxazinyl; wherein Ar is unsubstituted or substituted with one or more substituent(s) independently selected from the group consisting of hydrogen, halogen, hydroxy, nitro, --SO.sub.3 H, trifluoromethyl, trifluoromethoxy, C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.2 -C.sub.6 straight or branched chain alkenyl, O-(C.sub.1 -C.sub.6 straight or branched chain alkyl), O-(C.sub.3 -C.sub.4 straight or branched chain alkenyl), O-benzyl, O-phenyl, 1,2-methylenedioxy, --NR.sub.3 R.sub.4, carboxyl, N-(C.sub.1 -C.sub.5 straight or branched chain alkyl or C.sub.3 -C.sub.5 straight or branched chain alkenyl) carboxamides, N,N-di-(C.sub.1 -C.sub.5 straight or branched chain alkyl or C.sub.3 -C.sub.5 straight or branched chain alkenyl) carboxamides, morpholinyl, piperidinyl, O--X, CH.sub.2 --(CH.sub.2).sub.q --X, O--(CH.sub.2).sub.q --X, (CH.sub.2).sub.q --O--X, and CH.dbd.CH--X;R.sub.3 and R.sub.4 are independently selected from the group consisting of C.sub.1 -C.sub.6 straight or branched chain alkyl, C.sub.3 -C.sub.6 straight or branched rain alkenyl, hydrogen, and benzyl; or R.sub.3 and R.sub.4 are taken together to form a 5-6 membered heterocyclic ring;X is selected from the group consisting of 4-methoxyphenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, pyrazyl, quinolyl, 3,5-dimethylisoxazoyl, isoxazoyl, 2-methylthiazoyl, thiazoyl-, 2-thienyl, 3-thienyl, and pyrimidyl;q is 0-2; andn is 0 or 1.