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US 8,895,547 B2Granted
Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof
AssigneeSanofi
InventorsThomas Boehme, Christian Engel, Stefan Guessregen, Torsten Haack, Kurt Ritter, Georg Tschank
Life of this patent
Estimating the term…
Abstract
The invention relates to the compounds of formula (I) and to the physiologically acceptable salts thereof. Said compounds are suitable e.g. for the treatment of hyperglycemia.
Claims12
A compound of the formula I
- in which
- L is R1, —CH(R10)(R11);
- R10, R11 are each independently H, F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5, (C1-C6)-alkylene-(R6), (C3-C8)-cycloalkylene-(R6), (C1-C6)-alkylene-(C3-C8)-cycloalkylene-(R6), (C6-C10)-aryl, (C1-C6)-alkylene-((C6-C10)-aryl;
- where the aryl radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5;
- R1 is
- (C6-C10)-aryl, (C3-C8)-cycloalkyl,
- where the
- radical, aryl radical or cycloalkyl radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, —O(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5;
- R2 is H, F, (C1-C3)-alkyl where the alkyl radical may be mono- to trisubstituted by fluorine;
- R3, R4, R5, R13 are each independently
- H, F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, —(C1-C6)-alkylene-(R9), O—(C1-C6)-alkylene-(R9), tert-butyl, isopropylene-(R9), (C═O)—(C1-C6)-alkylene-(R9), (C1-C6)-alkylene-(R9), NH2, NH(C1-C6)-alkylene-(R9), N((C1-C6)-alkylene-R9)2, (C1-C6)-alkylene-NH2, (C1-C6)-alkylene-NH(C1-C6)-alkylene-(R9), (C1-C6)-alkylene-N((C1-C6)-alkylene-R9)2, —O—(C1-C6)-alkylene-NH2, —O—(C1-C6)-alkylene-NH(C1-C6)-alkylene-(R9), —O—(C1-C6)-alkylene-N((C1-C6)-alkylene-R9)2, —NH—(C1-C6)-alkylene-NH2, —NH—(C1-C6)-alkylene-NH(C1-C6)-alkylene-(R9), —NH—(C1-C6)-alkylene-N((C1-C6)-alkylene-R9)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5;
- (C6-C10)-aryl, —(C1-C6)-alkylene-(C6-C10)-aryl,
- where the aryl radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5, (C6-C10)-aryl, (C3-C8)-cycloalkyl, 4- to 12-membered heterocycle;
- where the (C6-C10)-aryl radical, (C3-C8)-cycloalkyl radical, 4- to 12-membered heterocycle radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5;
- 4- to 12-membered heterocycle, —(C1-C6)-alkylene-4- to −12-membered heterocycle,
- where the heterocyclyl radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkylene-(R9), (C1-C6)-alkylene-(R9), NH2, NH(C1-C6)-alkylene-(R9), N((C1-C6)-alkyl)2, SO2—(C1-C6)-alkylene-(R9), SO2—C2H2F3, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkylene-(R9), SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkylene-(R9), CONH2, CONH(C1-C6)-alkylene-(R9), CON((C1-C6)-alkyl)2, SF5, (C6-C10)-aryl, (C3-C8)-cycloalkyl, 4- to 12-membered heterocycle;
- where the (C6-C10)-aryl radical, (C3-C8)-cycloalkyl radical, 4- to 12-membered heterocycle radical may be mono- to trisubstituted by F, Cl, Br, I, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, SF5;
- R6 is H, OH, CF3, CHF2, CH2F, NO2, CN, OCF3, OCHF2, O—(C1-C6)-alkyl, (C1-C6)-alkyl, NH2, NH(C1-C6)-alkyl, N((C1-C6)-alkyl)2, SO2—CH3, SO2—NH2, SO2—NH(C1-C6)-alkyl, SO2—N((C1-C6)-alkyl)2, COOH, COO—(C1-C6)-alkyl, CONH2, CONH(C1-C6)-alkyl, CON((C1-C6)-alkyl)2, O—(CO)—NH2, SF5;
- R7, R8 are each independently H, (C1-C3)-alkyl, where the alkyl radical may be mono- to trisubstituted by fluorine, or R7 and R8 together with the carbon atom to which they are bonded form a 3-8-membered carbocycle or heterocycle;
- R9 is H, OH, OCH3, OCF3, CHF2, CF3;
- and pharmaceutically acceptable salts thereof.
18 more elements
Dependencies are inferred from the claim text.