Claims for Patent: 8,815,879

Summary for Patent: 8,815,879

Title:	Substituted 4-(selenophen-2(or-3)-ylamino)pyrimidine compounds and methods of use thereof
Abstract:	Selenophene compounds of formula (I) are described herein. In the compounds of Formula (I), ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring; or a mono- or bicyclic saturated heterocyclic fused ring having at least one ring member selected from the group consisting of N, O, S, SO and SO.sub.2; Y in ring B is nitrogen or substituted carbon; X is NR.sup.6, O, S, S(O), or S(O).sub.2. R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.6 are defined in the specification. Selenophene compounds of formula (I) may be used in methods of treating cell proliferative disorders, particularly cancer. Pharmaceutical compositions containing selenophene compounds of formula (I) may be used for treatment, inhibition, or control of cancer. ##STR00001##
Inventor(s):	Kasina; Sudhakar (Mercer Island, WA), Gokaraju; Ganga Raju (Vijayawada, IN), Somepalli; Venkateswarlu (Vijayawada, IN), Gokaraju; Rama Raju (Vijayawada, IN), Gokaraju; Venkata Kanaka Ranga Raju (Vijayawada, IN), Bhupathiraju; Kiran (Vijayawada, IN), Golakoti; Trimurtulu (Vijayawada, IN), Sengupta; Krishanu (Vijayawada, IN), Alluri; Venkata Krishna Raju (Vijayawada, IN)
Assignee:	Kasina Laila Innova Pharmaceuticals Private Limited (Vijayawada, IN)
Application Number:	13/896,538
Patent Claims:	1. A selenophene compound of formula (I), a salt thereof, a solvate or hydrate thereof, or a stereoisomer thereof: ##STR00092## wherein: ring A is a 6-membered aromatic fused ring, optionally containing one, two or three nitrogen atoms; a 5-membered heteroaromatic fused ring containing at least one heteroatom selected from the group consisting of sulfur, oxygen, nitrogen and selenium, with the proviso that no more than one oxygen or sulfur or selenium atom is present; or a mono- or bicyclic saturated heterocyclic fused ring having 3 to 10 carbon atoms and at least one ring member selected from the group consisting of N, O, S, SO and SO.sub.2; wherein ring A is optionally substituted by at least one group independently selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.1-6secondary-alkyl, C.sub.1-6tertiary-alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, C.sub.1-6alkylsulfonyl, and a aryl, heteroaryl and heterocycloalkyl ring; aryl, heteroaryl and heterocycloalkyl ring optionally substituted by halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4-alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, and C.sub.1-6alkylsulfonyl; Y in ring B is N or C--R.sup.5, wherein R.sup.5 is selected from hydrogen, halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.1-6secondary-alkyl, C.sub.1-6tertiary-alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, C.sub.1-6alkylsulfonyl; X is attached to the C2 carbon of the selenophene ring or to the C3 carbon of the seleneophene ring, and X is selected from the group consisting of NR.sup.6, O, S, S(O), and S(O).sub.2; wherein R.sup.6 is selected from hydrogen, amino, C.sub.1-6alkyl, and haloC.sub.1-6alkyl; R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.1-6secondary-alkyl, C.sub.1-6tertiary-alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, amino C.sub.1-6alkoxy, C.sub.1-6alkyl amino C.sub.1-6alkyl, di(C.sub.1-6alkyl)amino C.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, C.sub.1-6alkylsulfonyl, and a aryl, heteroaryl and heterocycloalkyl ring; aryl, heteroaryl and heterocycloalkyl ring optionally substituted by halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, and C.sub.1-6alkylsulfonyl. 2. A selenophene compound of formula (I) as claimed in claim 1, wherein X is attached to the C2 carbon of the seleneophene ring. 3. A selenophene compound of formula (I) as claimed in claim 1, wherein X is attached to the C3 carbon of the seleneophene ring. 4. A selenophene compound of formula (I) as claimed in claim 1, wherein X is NR.sup.6 or O, and wherein R.sup.6 is selected from the group consisting of hydrogen, amino, C-.sub.1-6alkyl, and haloC.sub.1-6alkyl. 5. A selenophene compound of formula (I) as claimed in claim 4, wherein the selenophene compound has a formula selected from the group consisting of Ia, Ib, Ic, and Id: ##STR00093## 6. A selenophene compound of formula (I) as claimed in claim 1, wherein Y is N or CR.sup.5, and wherein the selenophene compound has a formula selected from the group consisting of Ie, If, Ig, and Ih: ##STR00094## 7. A selenophene compound as claimed in claim 1, wherein ring A is a 6-membered aromatic fused ring; said selenophene compound having formula (VI): ##STR00095## wherein: Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, wherein each R.sup.7 is independently selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.1-6secondary-alkyl, C.sub.1-6tertiary-alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, C.sub.1-6alkylsulfonyl, phenyl, benzyl, a five-membered heteroaromatic ring containing at least one heteroatom selected from the group consisting of sulfur, oxygen, nitrogen and selenium, and a group having the following formula: ##STR00096## wherein n is 0 to 5; * indicates a point of attachment to the benzene ring; Z is selected from the group consisting of CH.sub.2, O, S, or NH; and R.sup.11 and R.sup.12 are independently selected from the group consisting of hydrogen, C.sub.1-6alkyl, haloC.sub.1-6alkyl, haloC.sub.1-6alkoxy, and C.sub.3-7cycloalkyl; or R.sup.11 and R.sup.12, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocycloalkyl ring; wherein phenyl and said five-membered heteroaromatic ring are optionally substituted by halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6 alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, or C.sub.1-6alkylsulfonyl; and wherein said five-membered heteroaromatic ring contains no more than one oxygen or sulfur or selenium atom. 8. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are each C--R.sup.7. 9. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, with the proviso that at least one of Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 is N. 10. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, with the proviso that two of Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are N. 11. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, with the proviso that Z.sup.1 and Z.sup.4 are N. 12. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, with the proviso that either Z.sup.1 and Z.sup.3 or Z.sup.2 and Z.sup.4 are N. 13. A selenophene compound of formula (VI) as claimed in claim 7, wherein Z.sup.1, Z.sup.2, Z.sup.3, and Z.sup.4 are independently selected from the group consisting of N and C--R.sup.7, with the proviso that: Z.sup.1 and Z.sup.2 are N; Z.sup.2 and Z.sup.3 are N; or Z.sup.3 and Z.sup.4 are N. 14. A selenophene compound as claimed in claim 1, wherein ring A is a 5-membered heteroaromatic fused ring; said selenophene compound having formula (VII): ##STR00097## wherein: Z.sup.5, Z.sup.6, and Z.sup.7 are independently selected from the group consisting of N, NH, S, Se and C--R.sup.7, wherein each R.sup.7 is independently selected from the group consisting of hydrogen, halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.1-6secondary-alkyl, C.sub.1-6tertiary-alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4-alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6 alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, C.sub.1-6alkylsulfonyl, phenyl, benzyl, a second five-membered heteroaromatic ring containing at least one heteroatom selected from the group consisting of sulfur, oxygen, nitrogen and selenium, and a group having the following formula: ##STR00098## wherein n is 0 to 5; * indicates a point of attachment to the benzene ring; Z is selected from the group consisting of CH.sub.2, O, S, or NH; and R.sup.11 and R.sup.12 are independently selected from the group consisting of hydrogen, C.sub.1-6alkyl, haloC.sub.1-6alkyl, haloC.sub.1-6alkoxy, and C.sub.3-7cycloalkyl; or R.sup.11 and R.sup.12, together with the nitrogen atom to which they are attached, form a 5- to 7-membered heterocycloalkyl ring; wherein phenyl and said second five-membered heteroaromatic ring are optionally substituted by halogen, hydroxy, formyl, carboxylic acid, amino, nitro, cyano, sulfonic acid, thiole, trihalomethyl, sulfonamide, C.sub.1-6alkyl, C.sub.2-6alkenyl, C.sub.2-6alkynyl, C.sub.1-4alkylcarbonyl, C.sub.1-4alkoxycarbonyl, aminocarbonyl, C.sub.1-6alkylaminocarbonyl, di(C.sub.1-6alkyl)aminocarbonyl, haloC.sub.1-6alkyl, hydroxyC.sub.1-6alkyl, C.sub.1-6alkoxy, haloC.sub.1-6alkoxy, hydroxyC.sub.1-6alkoxy, C.sub.3-7cycloalkyl, C.sub.3-7cycloalkoxy, C.sub.1-6alkylamino, di(C.sub.1-6alkyl)amino, aminoC.sub.1-6alkyl, aminoC.sub.1-6alkoxy, C.sub.1-6alkylaminoC.sub.1-6alkyl, di(C.sub.1-6alkyl)aminoC.sub.1-6alkyl, C.sub.1-6alkylsulfinyl, or C.sub.1-6alkylsulfonyl; and wherein said second five-membered heteroaromatic ring contains no more than one oxygen or sulfur or selenium atom. 15. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5, Z.sup.6, and Z.sup.7 are independently selected from the group consisting of S and C--R.sup.7, with the proviso that one of Z.sup.5, Z.sup.6, and Z.sup.7 is S. 16. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5, Z.sup.6, and Z.sup.7 are independently selected from the group consisting of O and C--R.sup.7, with the proviso that one of Z.sup.5, Z.sup.6, and Z.sup.7 is O. 17. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5, Z.sup.6, and Z.sup.7 are independently selected from the group consisting of NH and C--R.sup.7, with the proviso that one of Z.sup.5, Z.sup.6, and Z.sup.7 is NH. 18. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5, Z.sup.6, and Z.sup.7 are independently selected from the group consisting of Se and C--R.sup.7, with the proviso that one of Z.sup.5, Z.sup.6, and Z.sup.7 is Se. 19. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5 is oxygen or nitrogen, Z.sup.6 is C--R.sup.7, and Z.sup.7 is oxygen or nitrogen; wherein Z.sup.5 and Z.sup.7 are not both nitrogen or both oxygen. 20. A selenophene compound of formula (VII) as claimed in claim 14, wherein one of Z.sup.5, Z.sup.6, and Z.sup.7 is O; one of Z.sup.5, Z.sup.6, and Z.sup.7 is N; and one of Z.sup.5, Z.sup.6, and Z.sup.7 is C--R.sup.7, with the proviso that the ring contains an N--O bond. 21. A selenophene compound of formula (VII) as claimed in claim 14, wherein Z.sup.5 is N or NH, Z.sup.6 is C--R.sup.7, and Z.sup.7 is N or NH; wherein Z.sup.5 and Z.sup.7 are not both N or both NH. 22. A selenophene compound of formula (VII) as claimed in claim 14, wherein one of Z.sup.5, Z.sup.6, and Z.sup.7 is N; one of Z.sup.5, Z.sup.6, and Z.sup.7 is NH; and one of Z.sup.5 and Z.sup.7 is C--R.sup.7, with the proviso that the ring contains an N--NH bond. 23. A selenophene compound of formula (VII) as claimed in claim 14, wherein one of Z.sup.5 and Z.sup.7 is N; one of Z.sup.5 and Z.sup.7 is S; and Z.sup.6 is C--R.sup.7, with the proviso that the ring contains both S and N. 24. A selenophene compound of formula (VII) as claimed in claim 14, wherein one of Z.sup.5, Z.sup.6, and Z.sup.7 is S; one of Z.sup.5, Z.sup.6, and Z.sup.7 is N; and one of Z.sup.5 and Z.sup.7 is C--R.sup.7, with the proviso that the ring contains an S--N bond. 25. A selenophene compound selected from the group consisting of: 3-(6,7-Dimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxami- de; 3-(6,7,8-Trimethoxyquinazolin-4-ylamino)-5-tert-butylselenophene-2-car- boxamide; 3-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-tert- -butylselenophene-2-carboxamide; [5-(tert-Butyl)-2-nitroselenophen-3-yl][7-methoxy-6-(3-morpholinopropoxy)- quinazolin-4-yl]amine; 3-(7-(3-Morpholinopropoxy)-6-methoxyquinazolin-4-ylamino)-5-tert-butylsel- enophene-2-carboxamide; 3-(6,7-Bis(2-methoxyethoxy)quinazolin-4-ylamino)-5-tert-butylselenophene-- 2-carboxamide; 3-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-phenyl-seleno- phene-2-carboxamide; 3-(6-Aminoquinazolin-4-ylamino)-5-tert-butylselenophene-2-carboxamide; 3-(6-(2-Chloroacetamido)quinazolin-4-ylamino)-5-tert-butylselenophene-2-c- arboxamide; Methyl 4-(6-(3-morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-methyl-seleno- phene-2-carboxylate; 4-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-ylamino)-5-methylselenop- hene-2-carboxamide; 5-tert-Butyl-3-(pyridino[2,3-d]pyrimidin-4-ylamino)selenophene-2-carboxam- ide; 3-(5-Ethyl-6-methylthiopheno[2,3-d]pyrimidin-4-ylamino)-5-tert-butyls- elenophene-2-carboxamide; 3-(6-(Methylthio)thiopheno[3,2-d]pyrimidin-4-ylamino)-5-tert-butyl-seleno- phene-2-carboxamide; 3-(6-Phenylfuro[2,3-d]pyrimidin-4-ylamino)-5-tert-butylselenophene-2-carb- oxamide; 3-(6-tert-Butylfuro[2,3-d]pyrimidin-4-ylamino)-5-tert-butylseleno- phene-2-carboxamide; Methyl 4-(5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-5-methylselenophene- -2-carboxylate; 3-(6-tert-Butylselenopheno[3,2-d]pyrimidin-4-ylamino)-5-tert-butylselenop- hene-2-carboxamide; 3-(5-Ethyl-6-methylselenopheno[2,3-d]pyrimidin-4-ylamino)-5-tert-butylsel- enophene-2-carboxamide; 3-(2-(Methylthio)thiazolo[4,5-d]pyrimidin-7-ylamino)-5-tert-butylseleno-p- hene-2-carboxamide; 3-(N-(6,7-Dimethoxyquinazolin-4-yl)-N-methylamino)-5-tert-butylseleno-phe- ne-2-carboxamide; 3-(N-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-yl)-N-methylamino)-5-- tert-butylselenophene-2-carboxamide; 3-(N-(6-(3-Morpholinopropoxy)-7-methoxyquinazolin-4-yl)-N-(2-chloroethyl)- amino)-5-tert-butylselenophene-2-carboxamide; 3-(6,7-Dimethoxy-2-methylquinazolin-4-ylamino)-5-tert-butylselenophene-2-- carboxamide; Methyl 4-(6,7-dimethoxy-2-methylquinazolin-4-ylamino)-5-methylselenophene-2-carb- oxylate; 3-(6-(3-Morpholinopropoxy)-7-methoxy-2-methylquinazolin-4-ylamino- )-5-tert-butylselenophene-2-carboxamide; (3-Ethynylphenyl)-5,6,7,8-tetrahydropyrimidino[5',6'-5,4]selenopheno[2,3-- c]pyridin4-ylamine; 3-(2-(4-Chlorophenyl)-6,7-dimethoxyquinazolin-4-ylamino)-5-tert-butylsele- nophene-2-carboxamide; and 3-(6,7-Dimethoxyquinazolin-4-yloxy)-5-tert-butylselenophene-2-carboxamide- . 26. A process for the preparation of a selenophene compound of formula (I) according to claim 1 or a salt thereof; ##STR00099## wherein said process comprises a step selected from the group consisting of: [A] reacting a compound of formula II with a compound of formula III in the presence of a solvent and optionally in the presence of a base selected from the group consisting of organic and inorganic bases; ##STR00100## [B] reacting a compound of formula II with a compound of formula IV in the presence of a solvent and optionally in the presence of a base selected from the group consisting of organic and inorganic bases; ##STR00101## [C] reacting a compound of formula V with dimethylformamide-dimethylacetal or triethylorthoformate or trimethylorthoformate in the presence of a protic solvent; and further reacting with a compound of formula Ma; ##STR00102## [D] reacting a compound of formula V with dimethylformamide-dimethylacetal or triethylorthoformate or trimethylorthoformate in the presence of a protic solvent; and further reacting with a compound of formula IVa; ##STR00103## 27. A process for the preparation of selenophene compound of formula (I) as claimed in claim 26, wherein the selenophene compound of formula (I) is prepared from a compound of formula II, wherein Y in formula II is N or CR.sup.5 and ring A in formula II is selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, thiophene, furan, pyrrole, selenophene, oxazole, isoxazole, imidazole, pyrazole, thiazole, and isothiazole. 28. A process for the preparation of selenophene compound of formula (I) as claimed in claim 26, wherein the selenophene compound of formula (I) is prepared from a compound of formula V, wherein ring A in formula V is selected from the group consisting of benzene, pyridine, pyrazine, pyrimidine, pyridazine, thiophene, furan, pyrrole, selenophene, oxazole, isoxazole, imidazole, pyrazole, thiazole, and isothiazole. 29. A process for the preparation of selenophene compound of formula (I) as claimed in claim 26, wherein the selenophene compound of formula (I) is prepared from a compound of formula II, and wherein X is NH or O. 30. A pharmaceutical composition comprising: at least one selenophene compound of formula (I) according to claim 1, a pharmaceutically acceptable salt thereof, a solvate or hydrate thereof, or a stereoisomer thereof; and at least one additive selected from the group consisting of a pharmaceutically acceptable excipient, a pharmaceutically acceptable diluent, and a pharmaceutically acceptable carrier. 31. The pharmaceutical composition as claimed in claim 30, further comprising at least one anti-tumor agent selected from the group consisting of an Alkylating agent, an Anti-metabolite, a Hormonal therapy agent, a Cytotoxic topoisomerase inhibiting agent, a Anti-angiogenic compound, an Antibody, a VEGF inhibitor, an EGFR (HER1) inhibitor, a HER2 inhibitor, a CDK inhibitor, a Proteasome inhibitor, a Serine/threonine kinase (Raf) inhibitor, a Tyrosine kinase inhibitor, an Androgen receptor antagonist and an Aromatase inhibitor. 32. A pharmaceutical composition as claimed in claim 30, wherein said additive is selected from the group consisting of glucose, fructose, sucrose, maltose, yellow dextrin, white dextrin, aerosol, microcrystalline cellulose, calcium stearate, magnesium stearate, sorbitol, stevioside, corn syrup, lactose, citric acid, tartaric acid, malic acid, succinic acid, lactic acid, L-ascorbic acid, dl-alpha-tocopherol, glycerin, propylene glycol, glycerin fatty ester, poly glycerin fatty ester, sucrose fatty ester, sorbitan fatty ester, propylene glycol fatty ester, acacia, carrageenan, casein, gelatin, pectin, agar, vitamin B group, nicotinamide, calcium pantothenate, amino acids, calcium salts, pigments, flavors, preservatives, distilled water, saline, aqueous glucose solution, alcohol (e.g. ethanol), propylene glycol, polyethylene glycol, animal and vegetable oils, white soft paraffin, paraffin and wax. 33. A pharmaceutical composition as claimed in claim 31, wherein: the Alkylating agent is selected from the group consisting of nitrogen mustard N-oxide, cyclophosphamide, ifosfamide, thiotepa, ranimustine, nimustine, temozolomide, altretamine, apaziquone, brostallicin, bendamustine, carmustine, estramustine, fotemustine, glufosfamide, mafosfamide, bendamustin, mitolactol, cisplatin, carboplatin, eptaplatin, lobaplatin, nedaplatin, oxaliplatin, and satraplatin; the Anti-metabolite is selected from the group consisting of methotrexate, 6-mercaptopurineriboside, mercaptopurine, 5-fluorouracil, tegafur, doxifluridine, carmofur, cytarabine, cytarabine ocfosfate, enocitabine, gemcitabine, fludarabin, 5-azacitidine, capecitabine, cladribine, clofarabine, decitabine, eflornithine, ethynylcytidine, cytosine arabinoside, hydroxyurea, melphalan, nelarabine, nolatrexed, ocfosf[iota]te, disodium premetrexed, pentostatin, pelitrexol, raltitrexed, triapine, trimetrexate, vidarabine, vincristine, and vinorelbine; the Hormonal therapy agent is selected from the group consisting of exemestane, Lupron, anastrozole, doxercalciferol, fadrozole, formestane, abiraterone acetate, finasteride, epristeride, tamoxifen citrate, fulvestrant, Trelstar, toremifene, raloxifene, lasofoxifene, letrozole, sagopilone, ixabepilone, epothilone B, vinblastine, vinflunine, docetaxel, and paclitaxel; the Cytotoxic topoisomerase inhibiting agent is selected from the group consisting of aclarubicin, doxorubicin, amonafide, belotecan, camptothecin, 10-hydroxycamptothecin, 9-aminocamptothecin, diflomotecan, irinotecan, topotecan, edotecarin, epimbicin, etoposide, exatecan, gimatecan, lurtotecan, mitoxantrone, pirambicin, pixantrone, rubitecan, sobuzoxane, tafluposide; the Anti-angiogenic compound is selected from the group consisting of acitretin, aflibercept, angiostatin, aplidine, asentar, axitinib, recentin, bevacizumab, brivanib alaninat, cilengtide, combretastatin, DAST, endostatin, fenretinide, halofuginone, pazopanib, ranibizumab, rebimastat, removab, revlimid, sorafenib, vatalanib, squalamine, sunitinib, telatinib, thalidomide, ukrain, and vitaxin; the Antibody is selected from the group consisting of trastuzumab, cetuximab, bevacizumab, rituximab, ticilimumab, ipilimumab, lumiliximab, catumaxomab, atacicept, oregovomab, and alemtuzumab; the VEGF inhibitor is selected from the group consisting of sorafenib, DAST, bevacizumab, sunitinib, recentin, axitinib, aflibercept, telatinib, brivanib alaninate, vatalanib, pazopanib, and ranibizumab; the EGFR (HER1) inhibitor is selected from the group consisting of cetuximab, panitumumab, vectibix, gefitinib, erlotinib, and Zactima; the HER2 inhibitor is selected from the group consisting of lapatinib, tratuzumab, and pertuzumab; the CDK inhibitor is selected from the group consisting of roscovitine and flavopiridol; the Proteasome inhibitor is selected from the group consisting of bortezomib and carfilzomib; Serine/threonine kinase (Raf) inhibitor is sorafenib; the Tyrosine kinase inhibitor is selected from the group consisting of dasatinib, nilotibib, DAST, bosutinib, sorafenib, bevacizumab, sunitinib, AZD2171, axitinib, aflibercept, telatinib, imatinib mesylate, brivanib alaninate, pazopanib, ranibizumab, vatalanib, cetuximab, panitumumab, vectibix, gefitinib, erlotinib, lapatinib, tratuzumab and pertuzumab; the Androgen receptor antagonist is selected from the group consisting of nandrolone decanoate, fluoxymesterone, Android, Prostaid, andromustine, bicalutamide, flutamide, apocyproterone, apoflutamide, chlormadinone acetate, Androcur, Tabi, cyproterone acetate, and nilutamide; and the Aromatase inhibitor is selected from the group consisting of anastrozole, letrozole, testolactone, exemestane, aminoglutethimide, and formestane. 34. A method of treating or inhibiting, or controlling cell proliferative disorder in a warm blooded animal in need thereof, wherein said method comprises administering to the said warm blooded animal a therapeutically effective amount of at least one selenophene compound of formula (I) as claimed in claim 1. 35. A method of treating or inhibiting, or controlling cell proliferative disorder in a warm blooded animal in need thereof, wherein said method comprises administering to the said warm blooded animal a therapeutically effective amount of at least one composition as claimed in claim 30. 36. A method of treating or inhibiting, or controlling cell proliferative disorder in a warm blooded animal in need thereof, wherein said method comprises administering to the said warm blooded animal a therapeutically effective amount of at least one composition as claimed in claim 31. 37. A method according to claim 34, wherein said cell proliferative disorder is selected from the group consisting of psoriasis, keloids, endometriosis, skeletal disorders, angiogenic or blood vessel proliferative disorders, pulmonary hypertension, fibrotic disorders, mesangial cell proliferative disorders, colonic polyps, polycystic kidney disease, benign prostate hyperplasia (BPH), and solid tumors. 38. A method of treating or controlling tumor or cancer growth by blocking angiogenesis or by inhibiting vascular capillary formation with the administration of at least one selenophene compound of formula (I) as claimed in claim 1, a pharmaceutically acceptable salt thereof, a solvate or hydrate thereof, or a stereoisomer thereof. 39. A method of treating or inhibiting, or controlling cell proliferative disorder as claimed in claim 34, wherein said administering comprises administering by a route selected from the group consisting of intraperitoneal (IP), intravenous (IV), oral (PO), intramuscular (IM), intracutaneous (IC), intradermal (ID), intrauterine, intratumoral and intrarectal.

Details for Patent 8,815,879

Applicant	Tradename	Biologic Ingredient	Dosage Form	BLA	Approval Date	Patent No.	Expiredate
Genentech, Inc.	RITUXAN	rituximab	Injection	103705	11/26/1997		2030-11-18
Idec Pharmaceuticals Corp.	RITUXAN	rituximab	Injection	103737	02/19/2002		2030-11-18
Genentech, Inc.	HERCEPTIN	trastuzumab	For Injection	103792	09/25/1998		2030-11-18
Genentech, Inc.	HERCEPTIN	trastuzumab	For Injection	103792	02/10/2017		2030-11-18