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RU98106623A - DITIOLANE DERIVATIVES, THEIR PRODUCTION AND THERAPEUTIC EFFECT - Google Patents

DITIOLANE DERIVATIVES, THEIR PRODUCTION AND THERAPEUTIC EFFECT

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RU98106623A
RU98106623A RU98106623/04A RU98106623A RU98106623A RU 98106623 A RU98106623 A RU 98106623A RU 98106623/04 A RU98106623/04 A RU 98106623/04A RU 98106623 A RU98106623 A RU 98106623A RU 98106623 A RU98106623 A RU 98106623A
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carbon atoms
group containing
group
groups
compound according
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RU98106623/04A
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RU2165932C2 (en
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Фудзита Такаси
Йокояма Томихиса
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Санкио Компани Лимитед
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Claims (23)

1. Соединение формулы (I):
Figure 00000001

в которой: одно из m и n равно 0, а другое равно 0, 1 или 2;
k равно 0 или целому числу 1 - 12;
R1 представляет собой: атом водорода, группу, выбранную из заместителей α, определенных ниже, или алкильную группу, содержащую 1 - 12 атомов углерода, которая является незамещенной или замещена заместителями α и/или заместителями γ в количестве 1 - 3, или такую замещенную или незамещенную алкильную группу, в которой углеродная цепь прерывается атомом кислорода и/или атомом серы;
А представляет собой группу формулы -CON(R2)SO2-, в которой R2 представляет собой атом водорода, алкильную группу, содержащую 1 - 12 атомов углерода, аралкильную группу или аралкильную группу, арильный радикал которой замещен заместителями β в количестве 1 - 3;
B представляет собой одинарную связь или группу формулы
-N(R5)- или -N(R6)N(R5)-,
где R5 и R6 являются одинаковыми или различными, и каждый представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода, или R5, вместе с R1 и атомом азота, к которому они присоединены, могут образовывать гетероциклическое кольцо, содержащее в цикле 5 - 7 атомов, которые могут быть замещены 1 или несколькими группами, выбранными из низших алкильных групп и оксогрупп, и могут далее быть конденсированными с фенильным кольцом; или, когда В представляет собой одинарную связь, R1 может представлять собой гидроксигруппу или группу формулы -OR7 (где R7 представляет собой низшую алкильную группу);
заместители α выбраны из фенильных групп, фенильных групп, замещенных заместителями β в количестве 1 - 3, и гетероциклических групп, которые необязательно могут быть замещены заместителями β в количестве 1 - 3, или конденсированы с фенильньм кольцом, и указанные гетероциклические группы, имеющие 5 или 6 атомов углерода, являются насыщенными, ненасыщенными или ароматическими и содержащими 1 или несколько гетероатомов, выбранных из атомов азота, кислорода и серы;
заместители β выбраны из низших алкильных групп, галогенированных низших алкильных групп, низших алкоксигрупп, гидроксигрупп, карбоксигрупп, карбамоильных групп, атом азота которых может быть замещен, и низших алкоксикарбонильных групп;
заместители γ выбраны из низших алкоксигрупп, аллилоксигрупп, низших алкилтиогрупп, гидроксигрупп, нитроксигрупп, карбоксигрупп, низших алкоксикарбонильных групп, атомов галогена, сульфогрупп, сульфамоильных групп и карбамоильных групп, атом азота которых может быть замещен; и их фармацевтически приемлемые соли.1. The compound of formula (I):
Figure 00000001

in which: one of m and n is 0, and the other is 0, 1 or 2;
k is 0 or an integer of 1 to 12;
R 1 represents: a hydrogen atom, a group selected from substituents α as defined below, or an alkyl group containing 1 to 12 carbon atoms, which is unsubstituted or substituted by substituents α and / or substituents γ in an amount of 1 to 3, or such substituted or an unsubstituted alkyl group in which the carbon chain is interrupted by an oxygen atom and / or a sulfur atom;
A represents a group of the formula —CON (R 2 ) SO 2 -, in which R 2 represents a hydrogen atom, an alkyl group containing 1 to 12 carbon atoms, an aralkyl group or an aralkyl group, the aryl radical of which is substituted with β substituents in an amount of 1 - 3;
B represents a single bond or a group of the formula
—N (R 5 ) - or —N (R 6 ) N (R 5 ) -,
where R 5 and R 6 are the same or different, and each represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms, or R 5 , together with R 1 and the nitrogen atom to which they are attached, can form a heterocyclic ring, containing 5-7 atoms in a cycle which may be substituted by 1 or more groups selected from lower alkyl groups and oxo groups, and may further be fused to a phenyl ring; or, when B is a single bond, R 1 may be a hydroxy group or a group of the formula —OR 7 (where R 7 is a lower alkyl group);
substituents α are selected from phenyl groups, phenyl groups substituted with substituents β in an amount of 1 to 3, and heterocyclic groups that may optionally be substituted with substituents β in an amount of 1 to 3, or fused to a phenyl ring, and said heterocyclic groups having 5 or 6 carbon atoms are saturated, unsaturated or aromatic and containing 1 or more heteroatoms selected from nitrogen, oxygen and sulfur atoms;
substituents β are selected from lower alkyl groups, halogenated lower alkyl groups, lower alkoxy groups, hydroxy groups, carboxy groups, carbamoyl groups the nitrogen atom of which may be substituted, and lower alkoxycarbonyl groups;
substituents γ are selected from lower alkoxy groups, allyloxy groups, lower alkylthio groups, hydroxy groups, nitroxy groups, carboxy groups, lower alkoxycarbonyl groups, halogen atoms, sulfo groups, sulfamoyl groups and carbamoyl groups whose nitrogen atom may be substituted; and their pharmaceutically acceptable salts. 2. Соединение по п.1, представленное формулой (I'):
Figure 00000002

(в которой A, B, R1, k, m и n определены в п.1) и его соли.2. The compound according to claim 1, represented by formula (I '):
Figure 00000002

(in which A, B, R 1 , k, m and n are defined in claim 1) and its salts. 3. Соединение по п.1 или 2, в котором одно из m и n равно 0, а другое равно 0 или 1. 3. The compound according to claim 1 or 2, in which one of m and n is 0, and the other is 0 or 1. 4. Соединение по любому из пп.1-3, в котором k равно 0 или целому числу 1 - 8. 4. The compound according to any one of claims 1 to 3, in which k is 0 or an integer of 1 to 8. 5. Соединение по любому из пп.1-4, в котором R1 представляет собой гетероциклическую группу, алкильную группу, содержащую 1 - 12 атомов углерода, которая является незамещенной или замещена заместителями α и заместителями γ в количестве 1 - 3, или такую замещенную или незамещенную алкильную группу, в которой углеродная цепь прерывается атомом кислорода и/или атомом серы.5. The compound according to any one of claims 1 to 4 , in which R 1 represents a heterocyclic group, an alkyl group containing 1 to 12 carbon atoms, which is unsubstituted or substituted by substituents α and substituents γ in an amount of 1 to 3, or such substituted or an unsubstituted alkyl group in which the carbon chain is interrupted by an oxygen atom and / or a sulfur atom. 6. Соединение по любому из пп. 1-4, в котором R1 представляет собой гидроксигруппу или алкоксигруппу, содержащую 1 - 5 атомов углерода.6. The compound according to any one of paragraphs. 1-4, in which R 1 represents a hydroxy group or an alkoxy group containing 1 to 5 carbon atoms. 7. Соединение по любому из пп.1-6, в котором А представляет собой группу формулы -CON(R2)SO2-, в которой R2 представляет собой атом водорода, алкильную группу, содержащую 1 - 12 атомов углерода, или бензильную группу.7. The compound according to any one of claims 1 to 6, in which A represents a group of the formula —CON (R 2 ) SO 2 -, in which R 2 represents a hydrogen atom, an alkyl group containing 1 to 12 carbon atoms, or benzyl a group. 8. Соединение по любому из пп.1-7, в котором В представляет собой одинарную связь или группу формулы -N(R5)- или -N(R5)N(R6)-, в которых R5 и R6 являются одинаковыми или различными, и каждый из них представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода.8. The compound according to any one of claims 1 to 7, in which B represents a single bond or a group of the formula —N (R 5 ) - or —N (R 5 ) N (R 6 ) -, in which R 5 and R 6 are the same or different, and each of them represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms. 9. Соединение по п.1 или 2, в котором:
одно из m и n равно 0, а другое равно 0 или 1;
k равно 0 или целому числу 1 - 8;
R1 представляет собой гетероциклическую группу, гидроксигруппу, алкоксигруппу, содержащую 1 - 5 атомов углерода, алкильную группу, содержащую 1 - 12 атомов углерода, которая является незамещенной или замещена заместителями α и/или заместителями γ в количестве 1 - 3, или такую замещенную или незамещенную алкильную группу, в которой углеродная цепь прерывается атомом кислорода и/или атомом серы;
А представляет собой группу формулы -CON(R2)SO2-, в которой R2 представляет собой атом водорода, алкильную группу, содержащую 1 - 12 атомов углерода, или бензильную группу; и
B представляет собой одинарную связь или группу формулы -N(R5)- или -N(R5)N(R6)-, в которых R5 и R6 являются одинаковыми или различными, и каждый представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода.9. The compound according to claim 1 or 2, in which:
one of m and n is 0, and the other is 0 or 1;
k is 0 or an integer of 1 to 8;
R 1 represents a heterocyclic group, a hydroxy group, an alkoxy group containing 1 to 5 carbon atoms, an alkyl group containing 1 to 12 carbon atoms, which is unsubstituted or substituted by 1 to 3 substituents α and / or γ substituents, or such substituted or an unsubstituted alkyl group in which the carbon chain is interrupted by an oxygen atom and / or a sulfur atom;
A represents a group of the formula —CON (R 2 ) SO 2 -, in which R 2 represents a hydrogen atom, an alkyl group containing 1 to 12 carbon atoms, or a benzyl group; and
B represents a single bond or a group of the formula —N (R 5 ) - or —N (R 5 ) N (R 6 ) -, in which R 5 and R 6 are the same or different, and each represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms. 10. Соединение по п.1 или 2, в котором оба m и n равны 0. 10. The compound according to claim 1 or 2, in which both m and n are 0. 11. Соединение по любому из пп.1, 2 и 10, в котором k равно целому числу 2 - 6. 11. The compound according to any one of claims 1, 2 and 10, in which k is an integer of 2 to 6. 12. Соединение по любому из пп.1, 2, 10 и 11, в котором R1 представляет собой алкильную группу, содержащую 1 - 5 атомов углерода, алкоксикарбонилалкильную группу, содержащую 3 - 8 атомов углерода, карбоксиалкильную группу, содержащую 2 - 7 атомов углерода, гидроксиалкильную группу, содержащую 2 - 5 атомов углерода, гетероциклическую группу, алкоксигруппу, содержащую 1 - 5 атомов углерода, или гидроксигруппу.12. The compound according to any one of claims 1, 2, 10 and 11, in which R 1 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxycarbonylalkyl group containing 3 to 8 carbon atoms, a carboxyalkyl group containing 2 to 7 atoms carbon, a hydroxyalkyl group containing 2 to 5 carbon atoms, a heterocyclic group, an alkoxy group containing 1 to 5 carbon atoms, or a hydroxy group. 13. Соединение по любому из пп.1, 2, 10-12, в котором А представляет собой группу формулы -CON(R2)SO2-, в которой R2 представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода.13. The compound according to any one of claims 1, 2, 10-12, in which A represents a group of the formula —CON (R 2 ) SO 2 -, in which R 2 represents a hydrogen atom or an alkyl group containing 1 to 12 atoms carbon. 14. Соединение по любому из пп.1, 2, 10-13, в котором В представляет собой одинарную связь или группу формулы -N(R5)- или -N(R5)N(R6)-, в которых R5 и R6 являются одинаковыми или отличными, и каждый представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода.14. The compound according to any one of claims 1, 2, 10-13, in which B represents a single bond or a group of the formula —N (R 5 ) - or —N (R 5 ) N (R 6 ) -, in which R 5 and R 6 are the same or different, and each represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms. 15. Соединение по п.1 или 2, в котором:
оба m и n равны 0;
k равно целому числу от 2 до 6;
R1 представляет собой алкильную группу, содержащую 1 - 5 атомов углерода, алкоксикарбонилалкильную группу, содержащую 3 - 8 атомов углерода, карбоксиалкильную группу, содержащую 2 - 7 атомов углерода, гидроксиалкильную группу, содержащую 2 - 5 атомов углерода, гетероциклическую группу, алкоксигруппу, содержащую 1 - 5 атомов углерода, или гидроксигруппу.15. The compound according to claim 1 or 2, in which:
both m and n are 0;
k is an integer from 2 to 6;
R 1 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxycarbonylalkyl group containing 3 to 8 carbon atoms, a carboxyalkyl group containing 2 to 7 carbon atoms, a hydroxyalkyl group containing 2 to 5 carbon atoms, a heterocyclic group, an alkoxy group containing 1 to 5 carbon atoms, or hydroxy group. А представляет собой группу формулы -CON(R2)SO2-, в которой R2 представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода; и
В представляет собой одинарную связь или группу формулы -N(R5)- или -N(R5)N(R6)-, в которых R5 и R6 являются одинаковыми или отличными, и каждый из них представляет собой атом водорода или алкильную группу, содержащую 1 - 12 атомов углерода.A represents a group of the formula —CON (R 2 ) SO 2 -, in which R 2 represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms; and
B represents a single bond or a group of the formula —N (R 5 ) - or —N (R 5 ) N (R 6 ) -, in which R 5 and R 6 are the same or different, and each of them represents a hydrogen atom or an alkyl group containing 1 to 12 carbon atoms. 16. Соединение по любому из п.1 или 2, в котором k равно 4 или 5. 16. The compound according to any one of claim 1 or 2, in which k is 4 or 5. 17. Соединение по любому из пп.1, 2 и 16, в котором R1 представляет собой алкильную группу, содержащую 1 - 5 атомов углерода, алкоксикарбонилалкильную группу, содержащую 3 - 8 атомов углерода, карбоксиалкильную группу, содержащую 2 - 7 атомов углерода, гидроксиалкильную группу, содержащую 2 - 5 атомов углерода, гетероциклическую группу или алкоксигруппу, содержащую 1 - 5 атомов углерода.17. The compound according to any one of claims 1, 2 and 16, in which R 1 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxycarbonylalkyl group containing 3 to 8 carbon atoms, a carboxyalkyl group containing 2 to 7 carbon atoms, a hydroxyalkyl group containing 2 to 5 carbon atoms, a heterocyclic group or an alkoxy group containing 1 to 5 carbon atoms. 18. Соединение по любому из пп.1, 2, 16 и 17, в котором А представляет собой группу формулы -CONHSO2- или -CONCH3SO2-.18. The compound according to any one of claims 1, 2, 16 and 17, in which a represents a group of the formula —CONHSO 2 - or —CONCH 3 SO 2 -. 19. Соединение по любому из пп.1, 2 и 16-18, в котором В представляет собой одинарную связь или группу формулы -NH-, -NCH3- или -NHNCH3-.19. The compound according to any one of claims 1, 2, and 16-18, wherein B is a single bond or a group of the formula —NH—, —NCH 3 -, or —NHNCH 3 -. 20. Соединение по п.1 или 2, в котором:
оба m и n равны 0;
k равно 4 или 5;
R1 представляет собой алкильную группу, содержащую 1 - 5 атомов углерода, алкоксикарбонилалкильную группу, содержащую 3 - 8 атомов углерода, карбоксиалкильную группу, содержащую 2 - 7 атомов углерода, гидроксиалкильную группу, содержащую 2 - 5 атомов углерода, гетероциклическую группу или алкоксигруппу, содержащую 1 - 5 атомов углерода;
А представляет собой группу формулы -CONHSO2- или -CONCH3SO2-; и
В представляет собой одинарную связь или группу формулы -NH-, -NCH3- или -NHNCH3-.20. The compound according to claim 1 or 2, in which:
both m and n are 0;
k is 4 or 5;
R 1 represents an alkyl group containing 1 to 5 carbon atoms, an alkoxycarbonylalkyl group containing 3 to 8 carbon atoms, a carboxyalkyl group containing 2 to 7 carbon atoms, a hydroxyalkyl group containing 2 to 5 carbon atoms, a heterocyclic group or an alkoxy group containing 1 to 5 carbon atoms;
A represents a group of the formula —CONHSO 2 - or —CONCH 3 SO 2 -; and
B is a single bond or a group of the formula —NH—, —NCH 3 - or —NHNCH 3 -. 21. N-[5-(1,2-Дитиолан-3-ил)пентаноил]метансульфонамид и его фармацевтически приемлемые соли. 21. N- [5- (1,2-Dithiolan-3-yl) pentanoyl] methanesulfonamide and its pharmaceutically acceptable salts. 22. Лекарственное средство общей формулы (I) по любому из пп.1-21 для увеличения активности глутатионредуктазы у млекопитающих. 22. The drug of General formula (I) according to any one of claims 1 to 21 for increasing the activity of glutathione reductase in mammals. 23. Лекарственное средство общей формулы (I) по любому из пп.1-21 для лечения или предупреждения катаракты у млекопитающих. 23. A drug of general formula (I) according to any one of claims 1 to 21 for the treatment or prevention of cataracts in mammals.
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