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US 6,191,161 B1Granted
Prolylendopeptidase inhibitors
AssigneeChinoin Gyogyszer es Vegyeszeti
InventorsKároly Kánai, Sándor Erdö, Andrea Szappanos, Judit Bence, István Hermecz, Györgyné Szvoboda, Sándor Bátori, Gergely Héja, Mariá Balogh, Ágnes Horváth, Judit Sipos, Bodor Veronika Bártáne, Zsolt Párkányi, Viktor Lakics, Péter Molnár
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Abstract
The present invention relates to new prolylendopeptidase inhibitors of general formula (I).
Claims9
A compound of formula (I)
- A—B—C—D—L (I)
- wherein:
- A is formula (I),
- wherein:
- R1, R2, R3 and R4 each is a hydrogen atom, halogen atom, hydroxyl group, straight chain or branched chain alkyl or alkenyl- or alkinyl or alkoxy- or alkenyloxy- or alkinyloxy group consisting of 1-6 carbon atoms, nitro-group, amino group, monoalkylamino or monoacylamino group of 1-12 carbon atoms, or dialkylamino- or diacylamino group of 2-24 carbon atoms, where the acyl group is an alkyl, aralkyl, cycloalkyl or aryl type-, cyano group, mercapto group, carboxyl group, esterified carboxyl group of 2-7 carbon atoms, hydroxyalkyl group of 1-6 carbon atoms, acyl group of 1-7 carbon atoms, acyloxy group of 1-7 carbon atoms, phenyl or benzyl group, anilino group, benzoyl group, phenoxy group, benzyloxy group, isocyanato group, isothiocyanato group, alkylthio group of 1-6 carbon atoms, sulfamino or sulfamoyl group, thiocyanato or cyanato group;
- R and R6 each is a hydrogen atom, hydroxyl group, phenyl group or alkyl group of 1-4 carbon atoms or R5 and R6 together is an oxo group;
- B is a —(CH2)m—C(═O)— group, wherein m is an integer of 1 to 21;
- —O—(CH2)p—C(═O)— group wherein p is an integer of 1 to 3;
- or a
- and R14 each is a hydrogen alkyl or alkoxy group of 1-6 carbon atoms, halogen, amino group optionally substituted with one or two alkyl groups of 1-6 carbon atoms, or
- phenyl, phenoxy, aryl-alkyl group of 7-12 carbon atoms or aryl-alkoxy group of 7-12 carbon atoms, each of them optionally are 1, 2 or 3 same or different substituents identical to R1, R2, R3 or R4;
- or
- two of R9, R10, R11, R12, R13 and R14 together is an oxo or epoxy group or further chemical bond or four of them together have two further chemical bonds and the remaining groups are hydrogen atoms;
- or
- R9, R10, R11, R12, R13 and R14 together with the chain carbon atoms is a saturated or unsaturated homocycle of 3-8 carbon atoms or a saturated or unsaturated heterocycle of 2-7 carbon atoms and a nitrogen or sulfur or oxygen atom, to which optionally an aromatic ring of 6-10 carbon atoms is condensed;
- and
- w is zero or 1;
- C is a prolyl group of formula (37), (39), or (40),
- wherein:
- Hlg is a fluorine, chlorine, bromine, or iodine atom;
- R5 and R6 are, independently from each other, a hydrogen atom, hydroxyl group, phenyl group or alkyl group of 1-4 carbon atoms;
- or
- R5 and R6 together are an oxo-group;
- R16 is an alkoxy group of 1-4 carbon atoms, or an —NH—CH2—CN group, or an —NH—CH2—CO2R7 group, where R7 is defined as above;
- or a D structural unit or an L structural unit;
- or a group of the formula (44),
- wherein:
- R15 is a hydrogen atom, alkyl group of 1-6 carbon atoms, phenyl or naphthyl group;
- D is a covalent chemical bond;
- and
- L is a pyrrolidino or 2-cyanopyrrolidino group wherein the pyrrolidino or 2-cyanopyrolidino group is optionally substituted by one halogen atom or geminally by two halogen atoms;
- and optical, cis-trans, geometric isomers, epimers, tautomers or salts thereof.
29 more elements
Dependencies are inferred from the claim text.