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Claims for Patent: 5,563,142

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Claims for Patent: 5,563,142

Title: Diaromatic substituted compounds as anti-HIV-1 agents
Abstract:The present invention includes diaromatic substituted heterocyclic compounds (III) ##STR1## which are useful in treating individuals infected with the HIV virus.
Inventor(s): Palmer; John R. (Kalamazoo, MI), Romero; Donna L. (Kalamazoo, MI), Aristoff; Paul A. (Kalamazoo, MI), Thomas; Richard C. (Kalamazoo, MI), Smith; Herman W. (Kalamazoo, MI)
Assignee: The Upjohn Company (Kalamazoo, MI)
Application Number:08/198,428
Patent Claims: 1. A diaromatic substituted compound of formula (III) ##STR31## where R.sub.1 is --CH.sub.2 -- or --CO--; where Z is ##STR32## where n.sub.12 is 1 and n.sub.13 is 1, ##STR33## where Y.sub.3 is --N(Y.sub.3-1)-- where Y.sub.3-1 is C.sub.1 -C.sub.4 alkyl and n.sub.12 and n.sub.13 are as defined above;

where R.sub.6 is --N.dbd.;

where R.sub.7 is --N(R.sub.7-5)(R.sub.7-6) where R.sub.7-5 is

C.sub.1 --C.sub.6 alkyl,

--CH.sub.2 --cyclopropyl,

--CH.sub.2 --CH.sub.2 F, and where R.sub.7-6 is --H;

where R.sub.8 is --CR.sub.8-1 .dbd.where R.sub.8-1 is --H or --F;

where R.sub.9 is --CR.sub.9-1 .dbd.where R.sub.9-1 is --H or --F;

where R.sub.10 is --CR.sub.10-1 .dbd.where R.sub.10-1 is --H or --F;

where Aryl/Heteroaryl is a substituent selected from the group of substituents of formula (7) ##STR34## where . . . . is a double bond; where Q.sub.1 is --NX.sub.11 -- where X.sub.11 is --H;

where X.sub.14 is --H,

--O--CH.sub.2 --.phi.,

--O--CH.sub.2 --COOR.sub.14-10 where R.sub.14-10 is

--H,

C.sub.1 -C.sub.4 alkyl,

--CH.sub.2 --.phi.,

C.sub.1 -C.sub.6 alkyl,

--F, --Cl, Br,

--O--SO.sub.2 --X.sub.14-11 where X.sub.14-11 is C.sub.1 -C.sub.4 alkyl,

--NO.sub.2, --NH.sub.2, --N.sub.3,

--NH--SO.sub.2 --X.sub.14-1 where X.sub.14-1 is C.sub.1 -C.sub.6 alkyl,

--N.dbd.C(X.sub.14-4)--N(X.sub.14-7)(X.sub.14-8) where

(a) X.sub.14-4 is --H or C.sub.1 -C.sub.4 alkyl and where X.sub.14-7 and X.sub.14-8 are the same or different and are C.sub.1 -C.sub.6 alkyl,

--N(X.sub.14-2)--CO--X.sub.14-9 where X.sub.14-2 is --H or C.sub.1 -C.sub.4 alkyl and where X.sub.14-9 is

--H,

C.sub.1 -C.sub.4 alkyl or

--.phi. where X.sub.14-2 is defined above;

where n.sub.7 is 0 or 1;

where X.sub.6 is --H,

--OH,

--O--CH.sub.2 --.phi.,

--CHO,

C.sub.1 -C.sub.3 alkoxy,

--O--SO.sub.2 --X.sub.6-12 where X.sub.6-12 is C.sub.1 -C.sub.4 alkyl,

--C.tbd.N,

--O--(CH.sub.2).sub.n3 --N(X.sub.6-3)(X.sub.6-4) where n.sub.3 is 2 thru 5, where X.sub.6-3 is --H or where X.sub.6-3 and X.sub.6-4 are taken together with the attached nitrogen atom to form a heterocyclic ring selected from the group consisting of 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl, N-morpholinyl or 1-aziridinyl,

--(CH.sub.2).sub.n24 --OH, where n.sub.24 is 1,

--NH--SO.sub.2 --X.sub.6-7 where X.sub.6-7 is C.sub.1 -C.sub.4 alkyl, enantiomers, pharmaceutically acceptable salts, hydrates and solvates thereof.

2. A diaromatic substituted compound (III) according to claim 1 where R.sub.1 is --CO--.

3. A diaromatic substituted compound (III) according to claim 1 where Z is ##STR35##

4. A diaromatic substituted compound (III) according to claim 1 where R.sub.7 is --N(R.sub.7-5)(R.sub.7-6) where R.sub.7-5 is C.sub.1 -C.sub.4 alkyl.

5. A diaromatic substituted compound (III) according to claim 4 where C.sub.1 -C.sub.4 alkyl is --CH.sub.2 --CH.sub.3, --CH(CH.sub.3).sub.2 or --C(CH.sub.3).sub.3.

6. A diaromatic substituted compound (III) according to claim 1 which is

1-[indolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(N,N-diethylamino)-2-pyridinyl]piperazine,

1-[indolyl-2-methyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(propylamino)-2-pyridinyl]piperazine,

1-[5-chloroindoyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piprazine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[5-ethylindolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]-piper azine,

1-[indolyl-2-carbonyl]-4-[3-(cyclopropylmethylamino)-2-pyridinyl]piperazine

1-[5-fluoroindolyl-2-methyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazi ne,

1-[5-benzyloxyindolyl-2-carbonyl]-4-(3-ethylamino-2-pyridinyl)piperazine,

1-[5-benzyloxyindolyl-2-carbonyl]-4-[3-(1-methylethyl)amino-2-pyridinyl]-pi perazine,

1-[indolyl-2-methyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1,1-dimethylethylamino)-2-pyridinyl]piperazine

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(1,1-dimethylethylamino)-2-pyridinyl]pi perazine,

1-[5-(ethoxycarbonylmethoxy)indolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2 -pyridinyl]piperazine,

1-(5-fluoroindolyl-2-carbonyl)-4-[3-methylamino-2-pyridinyl]piperazine,

1-(indolyl-2-carbonyl)-4-[3-(methylamino)-2-pyridinyl]piperazine,

1-[5-(benzyloxycarbonylmethoxy)indolyl-2-carbonyl]-4-[3-(1-methylethylamino )-2-pyridinyl]piperazine,

1-[5-(carboxymethoxy)indolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridi nyl]piperazine,

1-[(5N-(N',N'-dimethylaminomethylene)aminoindolyl)carbonyl]-4-(3-(1-methyle thylamino)-2-pyridinyl)piperazine,

1-[6-methoxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piper azine,

1-[4-methoxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piper azine,

1-[5-methylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]pipera zine,

1-[5-fluoro-6-methoxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridi nyl]piperazine,

1-[5-bromoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperaz ine,

1-[5-bromo-6-methoxyindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridin yl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1-methylpropyl)amino-2-pyridinyl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1-ethylpropyl)amino-2-pyridinyl]piperazine,

1-[5-aminoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperaz ine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(2',2'-dimethylpropylamino)-2-pyridinyl ]piperazine,

1-[5-nitroindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperaz ine,

1-[5-acetamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]pip erazine,

1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyri dinyl]piperazine,

1-[6-formylindoyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperaz ine,

1-[5-azido-2-indolycarbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazi ne,

1-[indolyl-2-carbonyl]-4-[3-(2-fluoroethylamino)-2-pyridinyl]piperazine,

1-[6-hydroxymethylindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl ]piperazine,

1-[6-hydroxymethylindolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperaz ine,

1-(indolyl-2-carbonyl)-4-(N-methyl-N-(3-(1-methylethylamino)-2-pyridinyl)am ino)piperidine,

1-(6-cyanoindolyl-2-carbonyl)-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-(6-cyanoindolyl-2-carbonyl)-4-[3-(1-methylethylamino)-2-pyridinyl]piperaz ine,

1-[5-nitroindolyl-2-carbonyl]-4-[3-(1,1-dimethylethylamino)-2-pyridinyl]pip erazine,

1-[(5-(N',N'-dimethylaminomethylene)aminoindolyl-2-carbonyl]-4-[3-(1,1-dime thylethylamino)-2-pyridinyl]piperazine.

7. A diaromatic substituted compound (III) according to claim 6 which is

1-[indolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(ethylamino)-2-pyridinyl]piperazine,

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]pipera zine,

1-[5-fluoroindolyl-2-methyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazi ne,

1-[indolyl-2-carbonyl]-4-[3-(1,1-dimethylethylamino)-2-pyridinyl]piperazine

1-[5-fluoroindolyl-2-carbonyl]-4-[3-(1,1-dimethylethylamino)-2-pyridinyl]pi perazine,

1-[5-(carboxymethoxy)indolyl-2-carbonyl]-4-[3-(1-methylethyl- amino)-2-pyridinyl]piperazine,

1-[(5N-(N',N'-dimethylaminomethylene)aminoindolyl)carbonyl]-4-(3-(1-methyle thylamino)-2-pyridinyl)piperazine,

1-[indolyl-2-carbonyl]-4-[3-(1-ethylpropyl)amino-2-pyridinyl]piperazine and

1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyri dinyl]piperazine.

8. A diaromatic substituted compound (III) according to claim 6 which is 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyr idinyl]piperazine.

9. A diaromatic substituted compounds (III) according to claim 1 where the pharmaceutically acceptable salt is an acid addition salt.

10. A diaromatic substituted compounds (III) according to claim 9 where the acid addition salt is selected from the group consisting of methanesulfonic, hydrochloric, hydrobromic, sulfuric, phosphoric, nitric, benzoic, citric, tartaric, fumaric, maleic, p-toluenesulfonic, benzenesulfonic, CH.sub.3 --(CH.sub.2).sub.n --COOH where n is 0 thru 4 and HOOC--(CH.sub.2).sub.n --COOH where n is as defined above.

11. A diaromatic substituted compound (III) according to claim 8 which is 1-[5-methanesulfonamidoindolyl-2-carbonyl]-4-[3-(1-methylethylamino)-2-pyr idinyl]piperazine monomethanesulfonate salt.
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