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US 7,001,918 B2Granted
7-pyrrolyl tetracycline compounds and methods of use thereof
AssigneeParatek Pharmaceuticals, Inc.
InventorsSophie Huss, Jose M. Bueno, Jose M. Fiandor, Roger Frechette
Life of this patent
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Abstract
A compound of Formula (I): wherein variables R, R1, R2, R3 and A are as defined in the
Claims17
A compound of formula (I):
- wherein:
- A represents an aromatic, 5-membered heterocycle optionally substituted by one or more groups “R” selected from
- halogen,
- —NRaRb,
- C1-6alkyl,
- C2-6alkenyl,
- C3-6alkynyl,
- aryl,
- heteroaryl,
- hydroxy,
- —OC1-6alkyl,
- formyl,
- cyano,
- trifluoromethyl,
- —CHNOR,
- —CO2Ra,
- —CONRaRb,
- —NRaC(O)Ra,
- —NRaC(O)ORa,
- —OC(O)NRaRb,
- —OC(O)Ra,
- —OC(O)ORa,
- or a C1-6alkyl group substituted by one or more groups selected from hydroxy,
- —NRaRb,
- —OC1-6alkyl,
- —SRa,
- —CHNOR,
- —CO2Ra,
- —CONRaRb,
- —NRaC(O)Ra,
- —NRaC(O)ORa,
- —OC(O)NRaRb,
- —OC(O)Ra,
- —OC(O)ORa
- Ra and Rb independently represent hydrogen or C1-6alkyl;
- R1 represents hydrogen, C1-6alkyl or together R1 and R3 represent a CH2 moiety;
- R2 represents hydrogen, —OC1-6alkyl, —O(O)C1-6alkyl or hydroxy;
- R3 represents hydrogen, hydroxy or together R3 and R1 represent a CH2 moiety, or a pharmaceutically acceptable salt or solvate thereof.
35 more elements
A compound selected from the group consisting of:
- [4(R,S)-(4aα,5aα, 12aα)]-4-(Dimethylamino)-7-(1H-Tetrazol-1-yl)-1,4,4a,5,5a,6, 11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- [4-S-(4aα,5aα, 12aα)]-4-(Dimethylamino)-7-[(4-ethoxycarbonyl)-1H-triazol-1-yl]-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- [4-S-(4aα,5aα, 12aα)]-4-(Dimethylamino)-7-[(5-ethoxycarbonyl)-1H-triazol-1-yl 1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- [4S-(4aα,5aα, 12aα)]-4-(Dimethylamino)-7-(1H-pyrrol-1-yl-3-carboxaldehyde)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- [4S-(4aα,5aαα, 12aα)]-4-(Dimethylamino)-7-(3-((hydroxymino)-methyl)-1H-pyrrol-1-yl)-1,4,4a,5,5a,6,11,12a-octahydro-3, 10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- [4S-(4aα,5aαα, 12aα)]-7-(3-Cyanopyrrol-1-yl)-4-(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3, 10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide;
- and
- [4S-(4aα,5aα, 12aα)]-4-(Dimethylamino)-7-(3-((methyloxymino)methyl)-1H-pyrrol-1-yl)-1,4,4a,5,5a,6,11, 12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide.
5 more elements
Dependencies are inferred from the claim text.