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Heterocyclic Compounds, Method For Production And Uses Thereof

Abstract: The present disclosure described heterocyclic compounds of Formula I or, its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof and pharmaceutical compositions containing them as the active ingredient. The present disclosure also describes the synthesis and characterization of aforementioned compounds to exhibit high antimicrobial activity. The compounds of the present disclosure are useful as medicaments and their use in the manufacture of medicaments for treatment, prevention or suppression of diseases, and conditions mediated by microbes.

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Notices, Deadlines & Correspondence

Patent Information

Application #
Filing Date
20 March 2015
Publication Number
41/2016
Publication Type
INA
Invention Field
BIOTECHNOLOGY
Status
Email
lsmds@lakshmisri.com
Parent Application

Applicants

BUGWORKS RESEARCH INDIA PVT LTD
Suite 105, 88, Borewell Road, Whitefield, Bangalore - 560 066

Inventors

1. PEER MOHAMED, Shahul Hameed
Suite 105, 88, Borewell, Road, Whitefield, Bangalore -560 066
2. BHARATHAM, Nagakumar
Suite 105, 88, Borewell, Road, Whitefield, Bangalore - 560 066
3. KATAGIHALLIMATH, Nainesh
Suite 105, 88, Borewell, Road, Whitefield, Bangalore - 560 066
4. VENKATARAMAN, Bala Subramaniam
Suite 105, 88, Borewell, Road, Whitefield, Bangalore - 560 066
5. DATTA, Santanu
Suite 105, 88, Borewell, Road, Whitefield, Bangalore - 560 066

Specification

DESC:HETEROCYCLIC COMPOUNDS, METHOD FOR PRODUCTION AND USES THEREOF ,CLAIMS:1. A compound of Formula I


Formula I
or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof, wherein Q is selected from the group consisting of CO, SO2, COCH2 and CONH; ring A, and B are independently represents a 5-8 membered substituted or unsubstituted heteroaryl ring system; ring C represents a 5-8 membered substituted or unsubstituted ring which is unsaturated or partially unsaturated optionally having up to three heteroatom independently selected from O, N or S; R1 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, NO2, NH2, SO2NH2, CF3, CN, halo, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R2 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, CF3, halo, OCH3, OCH2CH3, OCF3, CN, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R3 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, CF3, halo, OCH3, OCH2CH3, OCF3, CN, SO2CH3, and C3-C5 alkoxy alkyl; R4 is independently selected from the group consisting of H, halo, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, CF3, OCF3, OCH3, OCH2CH3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; R5 is independently selected from the group consisting of H, halo, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, alkoxy, CF3, OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2.
2. A compound as claimed in claim 1, or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof,
wherein Q is selected from the group consisting of CO, SO2, COCH2 and CONH; ring A, and B are independently represents a 5-8 membered substituted or unsubstituted heteroaryl ring system; ring C represents a 5-8 membered substituted or unsubstituted ring which is unsaturated or partially unsaturated optionally having up to three heteroatom independently selected from O, N or S; R1 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, or heteroarylalkyl, NO2, NH2 SO2NH2, CF3, CN, halo, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R2 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, CF3, OCH3, halo, OCF3, CN, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R3 is independently selected from the group consisting of H, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, and C3-C5 alkoxy alkyl; R4 is independently selected from the group consisting of H, halo, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, alkoxy,CF3, OCF3, OCH3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; R5 is independently selected from the group consisting of H, halo, C1 16 alkyl, aryl, alkenyl, alkynyl, heteroaryl, C3-C8 cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclyl, heterocyclylalkyl, heteroarylalkyl, CF3, OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2.
3. A compound of Formula II as claimed in claim 1,

Formula II
or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof,
wherein, Q is selected from the group consisting of CO, SO2, COCH2 and CONH; ring A is selected from a 5-6 membered heteroaryl ring system; R1 is independently selected from the group consisting of C1 6 alkyl, aryl, heteroaryl, NO2, NH2, SO2NH2, CF3, CN, halo, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R2 is independently selected from the group consisting of H, C1 6 alkyl, aryl, heteroaryl, C3-C8 cycloalkyl , CF3, OCH3, OCH2CH3, OCF3, CN, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R3 is independently selected from the group consisting of H, C1 6 alkyl, aryl, heteroaryl, CF3, halo, OCH3, OCH2CH3, OCF3, CN, SO2CH3, and C3-C5 alkoxy alkyl; R4 is independently selected from the group consisting of H, halo, C1 6 alkyl, C3-C5 cycloalkyl, aryl, heteroaryl, CF3, OCH3, OCH2CH3, OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; R5 is independently selected from the group consisting of H, halo, C1 6 alkyl, C3-C5 cycloalkyl, aryl, heteroaryl, CF3, alkoxy, OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; Y and Z are independently selected from N, C-R6 or C-R7; R6 is independently selected from the group consisting of H, C1 6 alkyl, C3-C5 cycloalkyl, CN, CF3, CH2OCH3, CH2OCF3, CH2N(CH3)2, COOH, CONH2, CONHCH3 ; X1, Y1, Z1, and W1 are independently selected from N or C-R7 ; R7 is independently selected from the group consisting of H, halo, C1-C6 alkyl, aryl, heteroaryl, CF3, OCH3, CN, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2.
4. A compound of Formula II as claimed in claim 1, or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof,
wherein, Q is selected from the group consisting of CO, SO2, COCH2 and CONH; ring A is selected from a 5-6 membered heteroaryl ring system; R1 is independently selected from the group consisting of C1 6 alkyl, aryl, heteroaryl, NO2, SO2NH2, CF3, CN, halo, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R2 is independently selected from the group consisting of H, C1 6 alkyl, aryl, heteroaryl, C3-C8 cycloalkyl , CF3, OCH3, OCF3, CN, NHSO2CH3, NHSO2CF3, COOH, NHCOCF3 and SO2CH3; R3 is independently selected from the group consisting of H, C1 6 alkyl, aryl, heteroaryl, and C3-C5 alkoxy alkyl; R4 is independently selected from the group consisting of H, halo, C1 6 alkyl, C3-C5 cycloalkyl, aryl, heteroaryl, CF3, OCH3, OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; R5 is independently selected from the group consisting of H, halo, C1 6 alkyl, C3-C5 cycloalkyl, aryl, heteroaryl, CF3, , OCF3, OCHF2, CN, NO2, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2; Y and Z are independently selected from N, C-R6 or C-R7; R6 is independently selected from the group consisting of H, C1 6 alkyl, C3-C5 cycloalkyl, CN, CF3, CH2OCH3, CH2OCF3, CH2N(CH3)2, COOH, CONH2, CONHCH3 ; X1, Y1, Z1, and W1 are independently selected from N or C-R7 ; R7 is independently selected from the group consisting of H, halo, C1-C6 alkyl, aryl, heteroaryl, CF3, OCH3, CN, COOH, CONH2, CONHCH3, SO2CH3 and SO2NH2.
5. A compound of Formula II as claimed in claim 1, or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof, wherein, ring A is selected from the group consisting of

6. A compound of Formula II or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof, which is selected from a group consisting of:
N-(5-methyl-4-phenylthiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-fluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-cyanophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(3-cyano-4-fluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide); ;
N-(4-(4-fluorophenyl)thiazol-2-yl)-5-(trifluoromethyl)thiophene-2-carboxamide;
N-(4-(4-fluorophenyl)thiazol-2-yl)-5-nitrothiophene-3-carboxamide;
N-(4-(3,4-difluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(2,4-difluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-(methylsulfonyl)phenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(6-methoxypyridin-3-yl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-fluoro-2-methoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(3-fluoro-4-methylphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-fluoro-3-methoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-chloro-3-fluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
5-Nitro-N-(4-(4-(trifluoromethoxy)phenyl)thiazol-2-yl)thiophene-2-carboxamide;
N-(4-(2,5-difluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(3,5-difluorophenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(3,4-difluoro-5-methoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4,5-difluoro-2-methylphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-fluoro-2-methylphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(5-fluoropyridin-2-yl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(2,4-difluoro-5-methoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-chloro-3-methoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(4-chloro-3-ethoxyphenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide;
N-(4-(3-methoxy-4-(trifluoromethyl)phenyl)thiazol-2-yl)-5-nitrothiophene-2-carboxamide; and
5-Amino-N-(4-(4-chloro-3-methoxyphenyl)thiazol-2-yl)thiophene-2-carboxamide.

7. A process of preparation of compound of Formula I or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof.
8. A composition comprising a compound of Formula (I) or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof together with a carrier.
9. A process of preparation of a composition comprising a compound of Formula (I) or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof together with a carrier.
10. The present disclosure further relates to a compound of Formula I or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof, for use in killing or inhibiting the growth of a microorganism selected from the group consisting of bacteria, virus, fungi and protozoa.
11. The present disclosure further relates to use of a compound of Formula I or its stereoisomers, pharmaceutically acceptable salts, complexes, hydrates, solvates, tautomers, polymorphs, racemic mixtures, optically active forms and pharmaceutically active derivative thereof, in killing or inhibiting the growth of a microorganism selected from the group consisting of bacteria, virus, fungi and protozoa.

Documents

Application Documents

# Name Date
1 PD015196IN-SC SPEC FOR FILING.pdf 2015-03-28
2 PD015196IN-SC FORM 3.pdf 2015-03-28
3 1426-CHE-2015-Power of Attorney-010915.pdf 2015-11-07
4 1426-CHE-2015-Form 1-010915.pdf 2015-11-07
5 1426-CHE-2015-Correspondence-010915.pdf 2015-11-07
6 OTHERS [18-03-2016(online)].pdf 2016-03-18
7 Description(Complete) [18-03-2016(online)].pdf 2016-03-18
8 abstract-1426-CHE-2015-jpeg.jpg 2016-09-13
9 OTHERS [16-05-2017(online)].pdf 2017-05-16