Aryl and heteroaryl[7-(aryl and heteroaryl)-pyrazolo-[1,5-a]-pyrimidin-3-yl]methanones

Claim 2

A compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C 1 -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C l -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C l -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or alkyl(Cl-C3); R 2 , R 4 and R 5 are each hydrogen or alkyl(C l -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C l -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C l -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide.

Claim 3

A compound according to Claim 1 wherein R 1 is 2-furanyl; R 2 , R 4 and R S are each hydrogen; and R 3 is 3-(trifluoromethyl)phenyl, 3-pyridinyl or 4-pyridinyl.

Claim 4

A compound according to Claim 1, wherein R 1 is unsubstituted phenyl; phenyl substituted by 4-methyl, 4-ethyl, 4-methoxy, 3,4-dimethoxy or 4-dimethylamino; 2-furanyl; 2-thienyl; 2-pyridinyl; or 4-pyridinyl; R 2 , R 4 and R 5 are each hydrogen; and R 3 is 3-(trifluoromethyl)phenyl; 3-pyridinyl; 4-pyridinyl; 3-[N-alkyl(C l -C 6 )alkanoylamino-(C 1 -C 6 )]phenyl; or 3-[alkylamino(C l -C 6 )].

Claim 5

The compound according to Claim 1, phenyl-[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; (4-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimi- din-3-yl]-methanone; phenyl[7-(4-pyridinyl)pyrazolo[l,S--a]pyrimidin-3-yl]methanone; phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; (4-methoxyphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone; (3-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]-pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo[1,5-a]-pyrimidin-3-yl][3-(trifluoromethyl)phenyl]methanone; 2-thienyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyri- midin-3-yl]methanone; 2-furanyl[7-[3-(trifluoromethyl)phenyll- pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-furanyl[7-(3--pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [2-methyl-7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenyl- methanone; (4-methylphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; phenyl[7-(4-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]methanone, pyridine-1-oxide; 2-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl)methanone; 2-pyridinyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl-2-thiazolyl-methanone; 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone; 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]-pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-(3--pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin--3-yl]methanone; (2-fluorophenyl)[7-(3-pyridinyl)pyrazolo-[l,S-a]pyrimidin-3-yl]methanone; (2-fluorophenyl)[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-2--furanylmethanone; or [7-[3-(ethylamino)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl]phenylmethanone.

Claim 8

The method according to Claim 5, wherein the compound is phenyl [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin--3-yl]methanone; (4-fluorophenyl)[7-(4-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]-methanone; phenyl[7-(4-pyridinyl)-pyrazolo[l,5-a]pyrimidin-3-yl]methanone; phenyl[7-[3-(t r i-fluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; (4-methoxyphenyl)(7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin--3-yl]methanone; (3-fluorophenyl)[7-(4-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl][3-(trifluoromethyl)phenyl]methanone; 2-thienyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyri- midin-3-yl]methanone; 2-furanyl[7-[3-(trifluoromethyl)phenyl]-pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-furanyl[7-(3--pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl)methanone; [2-methyl-7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]phenyl- methanone; (4-methylphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; phenyl[7-(4-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]methanone, pyridine-I-oxide; 2-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl]methanone; 2-pyridinyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl-2-thiazolyl-methanone; 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone; 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]-pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-(3--pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-(3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin--3-yl]methanone; (2-fluorophenyl)[7-(3-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]methanone; (2-fluorophenyl)[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-2--furanylmethanone; or [7-[3-(ethylamino)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl]phenylmethanone.

Claim 9

A composition of matter in dosage unit form comprising from 2-750 mg of a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C l -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C l -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C l -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or al ky l( C l - C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C l -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C l -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-I-oxide; in association with a pharmaceutically acceptable carrier.

Claim 10

A composition of matter in dosage unit form comprising from 2-750 mg of a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C l -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C l -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C l -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or al ky l( C l - C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C l -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C l -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-I-oxide; in association with a pharmaceutically acceptable carrier.

Claim 11

The composition of matter according to Claim 7, wherein the compound is phenyl[7-(3-pyridinyl)pyrazolo-. [1,5-a]pyrimidin-3-yl]methanone; (4-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-methanone; phenyl-[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; phenyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]py- rimidin-3-yl]methanone; (4-methoxyphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; (3-fluorophenyl)[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-[3-(trifluoromethyl)phenyl]methanone; 2-thienyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-furanyl[7-[3-(trifluoromethyl)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl]methanone; 2-furanyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [2-methyl-7--(3-pyridinyl)pycazolo[4,5-a]pyrimidin-3-yl]phenylmeth- anone; (4-methylphenyl)[7-(3-pyridinyl)pyrazolo[1,5-a]-pyrimidin-3-yl]methanone; phenyl[7-(4-pyridinyl)pyrazolo-[1,5-a]pyrimidin-3-yl]methanone, pyridine-1-oxide; 2-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 2-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo-[1,5-a]pyrimidin-3-yl]methanone; 2-pyridinyl[7-(4-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; [7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]-2-thiazolyl-methanone; 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyri- midin)-3-yl]methanone; 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-(3-pyridinyl)pyrazolo[1,5-a]pyrimidin-3-yl]methanone; 4-pyridinyl[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]py- rimidin-3-yl]methanone; (2-fluorophenyl)[7-(3-pyridinyl)py- razolo [1,5-a]pyrimidin-3-yl]methanone; (2-fluorophenyl)[7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-methanone; [7-[3-(ethylamino)phenyl]pyrazolo[1,5-a]pyrimidin--3-yl]-2-furanylmethanone; or [7-[3-(ethylamino)phenyl]-pyrazolo[1,5-a]pyrimidin-3-yl]phenylmethanone.

Claim 12

A process of preparing a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C l -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C 1 -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C l -C 3 ) or alkyl(Cl-C3); R 2 , R 4 and R 5 are each hydrogen or alkyl(C 1 -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C l -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide, which comprises reacting a compound of the formula: with a compound of the formula: wherein X is 0, S or NR 6 when Y is or C≡CH when X is 0 and X is when Y is chloro, bromo or Z; R 6 is alkyl (C 1 -C 6 ), cyclohexyl, cyclopentyl, phenyl or (CH 2 ) m -phenyl, where m is an integer 1-3; L and M are each -OR 7 or -SR 7 or when L and M are taken together, they form where n is an integer 2 or 3 and L and M are 0 or S; R 7 is alkyl (C 1 -C 6 ); Z is -SR 7 , ORg, NR 9 R 10 or NHR 6 ; R 8 is hydrogen, alkyl (C 1 -C 10 ), -(CH 2 ) m -phenyl where m 'is an integer 1-3, alkanoyl (C 2 -C 10 ), benzoyl or carboalkoxy (C 2 -C 10 ); R 9 and R 10 are each hydrogen, alkyl (C 1 -C 10 ) or phenyl or when R 9 and R 10 are taken together with the nitrogen atom to which they are attached, they form where p is an integer 4-6, or where G is 0, or N-D where D is alkyl (Ci-C 6 ), benzyl, benzoyl, or alkanoyl(C 2 -C 7 ); under neutral or acidic conditions at 20-150°C for 1-10 hours.

Claim 13

A process of preparing a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C l -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C 1 -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C l -C 3 ) or alkyl(Cl-C3); R 2 , R 4 and R 5 are each hydrogen or alkyl(C 1 -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C l -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide, which comprises reacting a compound of the formula: with a compound of the formula: wherein X is 0, S or NR 6 when Y is or C≡CH when X is 0 and X is when Y is chloro, bromo or Z; R 6 is alkyl (C 1 -C 6 ), cyclohexyl, cyclopentyl, phenyl or (CH 2 ) m -phenyl, where m is an integer 1-3; L and M are each -OR 7 or -SR 7 or when L and M are taken together, they form where n is an integer 2 or 3 and L and M are 0 or S; R 7 is alkyl (C 1 -C 6 ); Z is -SR 7 , ORg, NR 9 R 10 or NHR 6 ; R 8 is hydrogen, alkyl (C 1 -C 10 ), -(CH 2 ) m -phenyl where m 'is an integer 1-3, alkanoyl (C 2 -C 10 ), benzoyl or carboalkoxy (C 2 -C 10 ); R 9 and R 10 are each hydrogen, alkyl (C 1 -C 10 ) or phenyl or when R 9 and R 10 are taken together with the nitrogen atom to which they are attached, they form where p is an integer 4-6, or where G is 0, or N-D where D is alkyl (Ci-C 6 ), benzyl, benzoyl, or alkanoyl(C 2 -C 7 ); under neutral or acidic conditions at 20-150°C for 1-10 hours.

Claim 14

We claim:

Claim 15

A process of preparing a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C l -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), al- k y lamino(C l -C 3 ), dialkylamino(C l -C 3 ), methylenedioxy, alkylsulfonyl(C l -C 3 ) or alkanoylamino(Cl-C3); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or alkyl(C 1 -C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C 1 -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C l -C 3 ), alkanoylamino(C l -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide, which comprises reacting a compound of the formula: with a compound of the formula: wherein X is 0, S or NR 6 when Y is or C≡CH when X is 0 and X is when Y is chloro, bromo or Z; R 6 is alkyl (C 1 -C 6 ), cyclohexyl, cyclopentyl, phenyl or (CH 2 ) m -phenyl, where m is an integer 1-3; L and M are each -OR 7 or -SR 7 or when L and M are taken together, they form where n is an integer 2 or 3 and L and M are 0 or S; R 7 is alkyl (C 1 -C 6 ); Z is -SR 7 , OR 8 , NRgR l o or NHR 6 ; R 8 is hydrogen, alkyl (C 1 -C 10 ), -(CH 2 ) m -phenyl where m is an integer 1-3, alkanoyl (C 2 -C 10 ) benzoyl or carboalkoxy (C 2 -C 10 ); Rg and R 10 are each hydro- g en, alkyl (C 1 -C 10 ) or phenyl or when Rg and R 10 are taken together with the nitrogen atom to which they are attached, they form where p is an integer 4-6, or where G is 0, or N-D where D is alkyl (C 1 -C 6 ), benzyl, benzoyl, or alkanoyl (C 2 -C 7 ); under neutral or acidic conditions at 20-150°C for 1-10 hours.

Claim 16

A process of preparing a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C l -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), al- k y lamino(C l -C 3 ), dialkylamino(C l -C 3 ), methylenedioxy, alkylsulfonyl(C l -C 3 ) or alkanoylamino(Cl-C3); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or alkyl(C 1 -C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C 1 -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C 1 -C 6 ), dialkylamino(C l -C 3 ), alkanoylamino(C l -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide, which comprises reacting a compound of the formula: with a compound of the formula: wherein X is 0, S or NR 6 when Y is or C≡CH when X is 0 and X is when Y is chloro, bromo or Z; R 6 is alkyl (C 1 -C 6 ), cyclohexyl, cyclopentyl, phenyl or (CH 2 ) m -phenyl, where m is an integer 1-3; L and M are each -OR 7 or -SR 7 or when L and M are taken together, they form where n is an integer 2 or 3 and L and M are 0 or S; R 7 is alkyl (C 1 -C 6 ); Z is -SR 7 , OR 8 , NRgR l o or NHR 6 ; R 8 is hydrogen, alkyl (C 1 -C 10 ), -(CH 2 ) m -phenyl where m is an integer 1-3, alkanoyl (C 2 -C 10 ) benzoyl or carboalkoxy (C 2 -C 10 ); Rg and R 10 are each hydro- g en, alkyl (C 1 -C 10 ) or phenyl or when Rg and R 10 are taken together with the nitrogen atom to which they are attached, they form where p is an integer 4-6, or where G is 0, or N-D where D is alkyl (C 1 -C 6 ), benzyl, benzoyl, or alkanoyl (C 2 -C 7 ); under neutral or acidic conditions at 20-150°C for 1-10 hours.

Claim 17

A composition of matter in dosage unit form comprising from 2-750 mg of a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C l -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or alkyl(C l -C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C l -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C l -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide ; in association with a pharmaceutically acceptable carrier.

Claim 18

A composition of matter in dosage unit form comprising from 2-750 mg of a compound of the formula: wherein R 1 is unsubstituted phenyl; phenyl mono- or di-substituted by halogen, alkoxy(C l -C 3 ) or alkyl(C 1 -C 3 ); phenyl mono-substituted by trifluoromethyl, alkylthio(C 1 -C 3 ), alkylamino(C 1 -C 3 ), dialkylamino(C 1 -C 3 ), methylenedioxy, alkylsulfonyl(C 1 -C 3 ) or alkanoylamino(C l -C 3 ); naphthalenyl; thiazolyl; biphenyl; thienyl; furanyl; pyridinyl; substituted thiazolyl; substituted biphenyl; substituted thienyl; or substituted pyridinyl wherein the substituents are one or two of halogen, alkoxy(C 1 -C 3 ) or alkyl(C l -C 3 ); R 2 , R 4 and R 5 are each hydrogen or alkyl(C l -C 3 ); and R 3 is unsubstituted phenyl, phenyl mono-substituted by halogen, trifluoromethyl, alkoxy(C 1 -C 3 ), amino, alkyl(C 1 -C 3 ), alkylamino(C l -C 6 ), dialkylamino(C 1 -C 3 ), alkanoylamino(C 1 -C 6 ), N-alkyl(C 1 -C 6 )alkanoylamino(C 1 -C 6 ), cyano or alkylthio-(C 1 -C 3 ); furanyl; thienyl; pyridinyl; or pyridine-1-oxide ; in association with a pharmaceutically acceptable carrier.