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US 6,638,925 B2Granted
Benzazepine derivatives, medicaments containing the same and their use to prepare medicaments
AssigneeSanochemia Ltd.
InventorsLaszlo Czollner, Johannes Frohlich, Ulrich Jordis, Bernhard Kuenburg
Life of this patent
Estimating the term…
Abstract
New derivatives of benzazepine, particularly of benzofuro[3a,3,2,ef][2]benzazepin of the general formula (I) and new compounds of the general formula (III) Drugs, containing compounds of formulas (I) and/or (III), which can be used successfully for the treatment of Alzheimer's disease and related dementia conditions, as well as for the treatment of Langdon-Down syndrome, are also described.
Claims3
A compound of formula (1)
- in which R1, R2 either are the same or different and represent
- hydrogen, F, Cl, Br, I, CN, NC, OH, SH, NO2, SO3H, NH2, CF3, or
- straight or branched lower (C1-C6) alkyl or alkoxy or
- an amino group substituted by one or more straight or branched lower (C1-C6) alkyl or alkyl carbonyl or alkoxy carbonyl group or
- a COOH, COO alkyl, CONH2, CON(alkyl)2 group or
- R1-R2 may together form —CH═CH—CH═CH—, —O—(CH2)n—O—,
- with n=1 to 3;
- R3 is the same as R1, or
- R2-R3 can jointly form:
- —O—(CH2)n—O—, with n=1 to 3;
- R4, R5:
- are each independently hydrogen or an alkyl, alkenyl, alkinyl, or
- S—R8, wherein R8 is hydrogen or a straight or branched lower (C1-C10) alkyl group
- SO—R8, SO2R8
- OH, or OH substituted for H with an O-protective group
- O—CS—N—R8
- O—CO—N—R9, wherein R9 has the following meaning:
- O—CO—R8, or
- R4, R5 may jointly be ═N—NH—R10, ═N—NR10R11, or ═N—O—R11, wherein R10 is hydrogen, straight or branched lower (C1-C6) alkyl or alkyl carbonyl or alkyl carbonyloxy group or —SO3H, and R11 is hydrogen, straight or branched lower (C1-C6) alkyl or alkyl carbonyl group, or —SO3H;
- R4 and R5 may also be:
- wherein Y1 is O, S, NH or N—R10 and Y2 is —OH, —SH, —NH2 or —NHR10
- G1, G2:
- jointly or separately have the meaning:
- —C(R13, R14)—, wherein R13, R14 can be hydrogen, OH, a straight or branched lower alkyl, aryl, alkoxy or aryloxy group or jointly as an alkyl spiro system (C3 to C7 spiro ring)
- G1 and G2 may jointly represent
- with m=1 to 7
- G3:
- represents CH2 or ═CO
- R6 represents a group —(G4)p—(G5)q—G6 with p, q=0-1, in which G4 satisfies the following definition
- —(CH2)r—, —C(R15R16)—(CR2)r—, with r=1 to 6 and R15, R16=hydrogen, or straight or branched lower alkyl, cycloalkyl, or aryl groups
- —O— or —NR15
- wherein s=1-4, and t=0-4
- wherein G7═NR15, O or S,
- G5 can be identical with or different from G4 and, in the event that p=1, additionally represents —S—,
- G6 fulfills the following definition:
- wherein
- R17, R18, R19 and R20 individually or jointly are the same or different, and are hydrogen, straight or branched lower alkyl, cycloalkyl or aryl groups, where R17 and R18 and R19 and R20 can jointly form a cycloalkyl group (with a ring size of 3-8)
- G8═O, S, NH, NR21—(CH2)n—,
- R21═CHO, COOR17 or a heteroaryl group selected from the group consisting of 2-pyridyl, 4-pyridyl, and 2-pyrimidinyl, which is unsubstituted or substituted identically or differently by one or several F, Cl, Br, I, NO2, OH, alkyl, alkyloxy, CN, NC or CF3, CHO, COOH, COO alkyl, SO3H, SH or S-alkyl groups, or
- a methyl group, which is substituted by 1-3 phenyl groups, which are unsubstituted or substituted identically or differently by one or more F, Cl, Br, I, NO2 alkyl, alkyloxy, CN, NC or CF3 groups,
- wherein G8 can also be:
- —CHO, COOR17, —CONR17
- a straight or branched lower arylalkyl, arylalkenyl, arylalkinyl, cycloalkyl or aryl groups,
- —O—R17, —NR17R18, phthalamid o, —CN or —NC;
- R7 is identical with R6 or represents —O—(−) (N-oxide) or a free electron pair (e-pair), wherein R6 and R7 can also form a common ring, 3 to 8 carbon atoms in size and
- X exists only if, and represents an ion of a pharmacologically unstable inorganic or organic acid, where R6 and R7 are present and the nitrogen atom thus carries a positive charge;
- and
- Z═N or N+ in the event that R6 and R7 are present jointly and R7 is not O−.
45 more elements
Dependencies are inferred from the claim text.