RU99109459A - MONOCYCLIC L-NUCLEOSIDS, THEIR ANALOGUES AND APPLICATIONS - Google Patents

MONOCYCLIC L-NUCLEOSIDS, THEIR ANALOGUES AND APPLICATIONS

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RU99109459A
RU99109459A RU99109459/04A RU99109459A RU99109459A RU 99109459 A RU99109459 A RU 99109459A RU 99109459/04 A RU99109459/04 A RU 99109459/04A RU 99109459 A RU99109459 A RU 99109459A RU 99109459 A RU99109459 A RU 99109459A
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lower alkyl
independently selected
compound
alkylamines
independently
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RU99109459/04A
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RU2188828C2 (en
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Кандасейми РАМАСЕЙМИ
Роберт Тэм
Деврон Эверетт
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Ай-Си-Эн Фармасьютикалз, Инк.
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Claims (16)

1. Соединение, имеющее структуру в соответствии с формулой I, в которой сахар находится в L - конформации
Figure 00000001

где A нeзaвиcимo выбрано из N или С;
В, С, Е, F независимо выбраны из СН, СО, N, S, Se, О, NR1, CCONH2, ССН3, C-R2 или Р; R1 независимо представляет собой Н, низший алкил, низшие алкиламины, СОСН3, низший алкилалкенил, низший алкилвинил или низшие алкиларилы; R2 независимо представляет собой Н, ОН, галогены, CN, N3, NH2, C(= O)NH2, C(=S)NH2, C(=NH)NH2 • HCI, C(=NOH)NH2, C(=NH)OMe, низший алкил, низшие алкиламины, низший алкилалкенил, низший алкилвинил, низшие алкиларилы или замещенные гетероциклы;
D независимо выбрано из СН, СО, N, S, Se, О, NR1, CCONH2, ССН3, С-R2, Р или отсутствия: где R1 независимо представляет собой Н, О, низший алкил, низшие алкиламины, СОСН3, низший алкилалкенил, низший алкилвинил или низшие алкиларилы, a R2 независимо представляет собой Н, ОН, галогены, CN, N3, NH2, низший алкил, низшие алкиламины, низший алкилалкенил, низший алкилвинил, низшие алкиларилы или замещенные гетероциклы;
X независимо представляет собой О, S, СН2 или NR, где R представляет собой СОСН3;
R1 и R4 независимо выбраны из Н, CN, N3, СН2ОН, низшего алкила и низших алкиламинов;
R2, R3, R5, R6, R7 и R8 независимо выбраны из Н, ОН, CN, N3, галогенов, СН2ОН, NH2, ОСН3, NНСН3, ОNНСН3, SСН3, SPh, алкенила, низшего алкила, низших алкиламинов и замещенных гетероциклов; и
R1, R2, R3, R4, R5, R6, R7 и R8 не все замещены одновременно, так что
когда R2= R3= Н, то тогда R7 и R8 представляют собой водороды или отсутствуют;
когда R1, R4 или R5 замещены, то тогда R7= R8=H и R2=R3=ОН:
когда R2 или R3 замещены, то тогда R7 и R8 представляют собой Н или ОН;
когда R7 или R8 замещены, то тогда R2 и R3 представляют собой Н или ОН;
когда R7 и R8 представляют собой гидроксил, то тогда R2 и R3 не представляют собой ОН;
когда А=N, В=СО, C=N или NH, D=CO или C-NH2, Е представляет собой СН или имеет заместитель по С; F=CH, Х=O, S или СН2, то тогда R2 не будет представлять собой Н, ОН, СН3, галогены, N3, CN, SH, SPh, СН2OН, СН2OСН3, CH2SH, CH2F, СН2N3, арил, арилокси или гетероциклы;
когда А= N, В=СО, C=N или NH, D=CO или C-NH2, Е представляет собой СН, С-СН3 или галоген, F=CH, Х=N-СОСН3, то тогда R2 не будет представлять собой Н или ОН;
когда A=N, В=СН, С=СН или СН3, D=CH или С-СН3, Е представляет собой СН, С-СН3 или C-CONH2, F= CH, Х=O или СН2, то тогда R2 не будет представлять собой Н или ОН;
когда A= N; B= N, СО или СН, С=СН, С-Сl или С-ОСН3, D=CH или C-Ph, Е представляет собой СН, С-Сl или C-Ph, F=N или СО; Х=O, то тогда R2 не будет представлять собой Н или ОН;
когда A=N, В=СО или CS, C=N или NH, D=CO или C-NH2, Е представляет собой СН или N, F=N или СН, X=O, то тогда R2 не будет представлять собой Н или ОН, и
когда A= C, B=CH, C=NH, D=CO, CS или C-NH2, E представляет собой N или NH, F=CO или CH, X=O, то тогда R2 не будет представлять собой Н или ОН.1. A compound having a structure in accordance with formula I, in which sugar is in the L - conformation
Figure 00000001

where A is indelibly selected from N or C;
B, C, E, F are independently selected from CH, CO, N, S, Se, O, NR 1 , CCONH 2 , CCH 3 , CR 2 or P; R 1 independently represents H, lower alkyl, lower alkylamines, COCH 3 , lower alkylalkenyl, lower alkylvinyl or lower alkylaryls; R 2 independently represents H, OH, halogen, CN, N 3 , NH 2 , C (= O) NH 2 , C (= S) NH 2 , C (= NH) NH 2 • HCl, C (= NOH) NH 2 , C (= NH) OMe, lower alkyl, lower alkylamines, lower alkyl alkenyl, lower alkyl vinyl, lower alkylaryls, or substituted heterocycles;
D is independently selected from CH, CO, N, S, Se, O, NR 1 , CCONH 2 , CCH 3 , C-R 2 , P or unavailable: where R 1 is independently H, O, lower alkyl, lower alkyl amines, COCH 3 , lower alkyl alkenyl, lower alkyl vinyl or lower alkylaryls, a R 2 independently represents H, OH, halogens, CN, N 3 , NH 2 , lower alkyl, lower alkyl amines, lower alkyl alkenyl, lower alkyl vinyl, lower alkylaryls or substituted heterocycles;
X is independently O, S, CH 2 or NR, where R is COCH 3 ;
R 1 and R 4 are independently selected from H, CN, N 3 , CH 2 OH, lower alkyl and lower alkylamines;
R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are independently selected from H, OH, CN, N 3 , halogen, CH 2 OH, NH 2 , OCH 3 , NHCH 3 , ONHCH 3 , SCCH 3 , SPh, alkenyl, lower alkyl, lower alkylamines and substituted heterocycles; and
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are not all substituted at the same time, so
when R 2 = R 3 = H, then R 7 and R 8 are hydrogens or absent;
when R 1 , R 4 or R 5 are substituted, then R 7 = R 8 = H and R 2 = R 3 = OH:
when R 2 or R 3 is substituted, then R 7 and R 8 are H or OH;
when R 7 or R 8 is substituted, then R 2 and R 3 are H or OH;
when R 7 and R 8 are hydroxyl, then R 2 and R 3 are not OH;
when A = N, B = CO, C = N or NH, D = CO or C-NH 2 , E is CH or has a substituent on C; F = CH, X = O, S or CH 2, then R 2 does not represent H, OH, CH3, halogens, N 3, CN, SH, SPh, CH 2 OH, CH 2 OCH 3, CH 2 SH, CH 2 F, CH 2 N 3 , aryl, aryloxy or heterocycles;
when A = N, B = CO, C = N or NH, D = CO or C-NH 2 , E is CH, C — CH 3 or halogen, F = CH, X = N-COCH 3 , then R 2 will not be H or OH;
when A = N, B = CH, C = CH or CH 3 , D = CH or C-CH 3 , E is CH, C-CH 3 or C-CONH 2 , F = CH, X = O or CH 2 then R 2 will not be H or OH;
when A = N; B = N, CO or CH, C = CH, C-Cl or C-OCH 3 , D = CH or C-Ph, E is CH, C-Cl or C-Ph, F = N or CO; X = O, then R 2 will not be H or OH;
when A = N, B = CO or CS, C = N or NH, D = CO or C-NH 2 , E is CH or N, F = N or CH, X = O, then R 2 will not be are H or OH, and
when A = C, B = CH, C = NH, D = CO, CS or C-NH 2 , E is N or NH, F = CO or CH, X = O, then R 2 will not be H or he. 2. Соединение по п.1, далее имеющее структуру в соответствии с формулой III
Figure 00000002

где Х независимо представляет собой О, S, CH2 и NR, где R представляет собой СОСН3;
R' и R" независимо выбраны из Н, СN, C(=O)NH2, NH2, C(=S)NH2, C(=NH)NH2 • HCI, C(= NOH)NH2, C(=NH)OMe, гетероциклов, галогенов, низшего алкила или низшего алкиларила;
R1 и R4 независимо выбраны из Н, CN, N3, СН2ОН, низшего алкила или низших алкиламинов; и
R2, R3, R5, R6, R7 и R8 независимо выбраны из Н, ОН, CN, N3, галогенов, СН2OН, NH2, ОСН3, NHCH3, ONHCH3, SСН3, SPh, алкенила, низшего алкила, низших алкиламинов или замещенных гетероциклов так, что,
когда R2= R3= Н, то тогда R7 и R8 представляют собой водороды или отсутствуют;
в соединениях формулы III R' предпочтительно представляет собой карбоксамид или CN, а R" представляет собой водород или галогены; R1=R4=R5=R7= R8=H и R2=R3=ОН, а Х предпочтительно представляет собой кислород.2. The compound according to claim 1, further having a structure in accordance with formula III
Figure 00000002

where X independently represents O, S, CH 2 and NR, where R represents COCH 3 ;
R 'and R "are independently selected from H, CN, C (= O) NH 2 , NH 2 , C (= S) NH 2 , C (= NH) NH 2 • HCl, C (= NOH) NH 2 , C (= NH) OMe, heterocycles, halogens, lower alkyl or lower alkylaryl;
R 1 and R 4 are independently selected from H, CN, N 3 , CH 2 OH, lower alkyl or lower alkylamines; and
R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are independently selected from H, OH, CN, N 3 , halogens, CH 2 OH, NH 2 , OCH 3 , NHCH 3 , ONHCH 3 , SCH 3 , SPh, alkenyl, lower alkyl, lower alkylamines or substituted heterocycles such that,
when R 2 = R 3 = H, then R 7 and R 8 are hydrogens or absent;
in compounds of formula III, R 'is preferably carboxamide or CN, and R "is hydrogen or halogen; R 1 = R 4 = R 5 = R 7 = R 8 = H and R 2 = R 3 = OH, and X is preferably is oxygen. 3. Соединение по п.1, далее имеющее структуру в соответствии с формулой IV
Figure 00000003

где А независимо выбрано из N или С;
В, С, Е и F независимо выбраны из СН, СО, N, S, Se, О, NR1, CCONH2, ССН3, C-R2 или Р; R1 независимо представляет собой Н, низший алкил, низшие алкиламины, СОСН3, низший алкилалкенил, низший алкилвинил или низшие алкиларилы; R2 независимо представляет собой Н, ОН, галогены, CN, N3, NH2, C(= O)NH2, C(=S)NH2, C(=NH)NH2 • HCI, C(=NOH)NH2, C(=NH)OMe, низший алкил, низшие алкиламины, низший алкилалкенил, низший алкилвинил, низшие алкиларилы или замещенные гетероциклы;
Х независимо представляет собой О, S, СН2 или NR, где R представляет собой СОСН3;
R1 и R4 независимо выбраны из Н, CN, N3, СН2OН, низшего алкила или низших алкиламинов и
R2, R3, R5, R6, R7 и R8 независимо выбраны из Н, ОН, CN, N3, галогенов, NH2, СН2OН, ОСН3, NНСН3, ОNНСН3, SСН3, SPh, алкенила, аллила, низшего алкила, низших алкиламинов или замещенных гетероциклов так, что,
когда R2= R3= H, то тогда R7 и R8 представляют собой водороды или отсутствуют;
когда А представляет собой углерод, B=E=N, С представляет собой N-Ph, то тогда F не представляет собой СН;
когда A= N, С представляет собой СН, В=Е=С-СН3, то тогда F не является азотом, и
когда А представляет собой углерод, B=N, C=C-CONH2, Е=СН; F=S, то тогда Х не представляет собой СН2;
в соединениях формулы IV R1 предпочтительно представляет собой Н, низший алкил или аллил; R2 предпочтительно представляет собой Н, ОН, галогены, СN, N3, NH2, C(= O)NH2, C(=S)NH2, C(=NH)NH2 • HCI, C(=NOH)NH2 или C(=NH)OMe; и когда R1= R4= R5=R7=R8=H, то тогда предпочтительно R2=R3=ОН, а Х предпочтительно представляет собой кислород.3. The compound according to claim 1, further having a structure in accordance with formula IV
Figure 00000003

where a is independently selected from N or C;
B, C, E and F are independently selected from CH, CO, N, S, Se, O, NR 1 , CCONH 2 , CCH 3 , CR 2 or P; R 1 independently represents H, lower alkyl, lower alkylamines, COCH 3 , lower alkylalkenyl, lower alkylvinyl or lower alkylaryls; R 2 independently represents H, OH, halogen, CN, N 3 , NH 2 , C (= O) NH 2 , C (= S) NH 2 , C (= NH) NH 2 • HCl, C (= NOH) NH 2 , C (= NH) OMe, lower alkyl, lower alkylamines, lower alkyl alkenyl, lower alkyl vinyl, lower alkylaryls, or substituted heterocycles;
X independently represents O, S, CH 2 or NR, where R is COCH 3 ;
R 1 and R 4 are independently selected from H, CN, N 3 , CH 2 OH, lower alkyl or lower alkylamines, and
R 2 , R 3 , R 5 , R 6 , R 7 and R 8 are independently selected from H, OH, CN, N 3 , halogens, NH 2 , CH 2 OH, OCH 3 , NHCH 3 , ONHCH 3 , SCCH 3 , SPh, alkenyl, allyl, lower alkyl, lower alkylamines or substituted heterocycles so that,
when R 2 = R 3 = H, then R 7 and R 8 are hydrogens or absent;
when A is carbon, B = E = N, C is N-Ph, then F is not CH;
when A = N, C is CH, B = E = C — CH 3 , then F is not nitrogen, and
when A is carbon, B = N, C = C-CONH 2 , E = CH; F = S, then X does not represent CH 2 ;
in compounds of formula IV, R 1 is preferably H, lower alkyl or allyl; R 2 is preferably H, OH, halogen, CN, N 3 , NH 2 , C (= O) NH 2 , C (= S) NH 2 , C (= NH) NH 2 • HCl, C (= NOH) NH 2 or C (= NH) OMe; and when R 1 = R 4 = R 5 = R 7 = R 8 = H, then preferably R 2 = R 3 = OH, and X is preferably oxygen. 4. Соединение по 1, далее имеющее структуру в соответствии с формулой V
Figure 00000004

где А независимо выбрано из N или С;
В, С, Е, F независимо выбраны из СН, СО, N, S, Se, О, NR1 CCONH2, ССН3, C-R2 или Р; R1 представляет собой независимо Н, низший алкил, низшие алкиламины, СОСН3, низший алкилалкенил, низший алкилвинил или низшие алкиларилы; R2 представляет собой независимо Н, ОН, галогены, CN, N3, NH2, C(=O)NH2, C(= S)NH2, C(= NH)NH2 • HCI, C(=NOH)NH2, C(=NH)OMe, низший алкил, низшие алкиламины, низший алкилалкенил, низший алкилвинил, низшие алкиларилы или замещенные гетероциклы;
D независимо выбрано из СН, СО, N, S, Se, О, NR1, CCONH2, ССН3, С-R2, Р или отсутствия; R1 независимо представляет собой Н, О, низший алкил, низшие алкиламины, СОСН3, низший алкилалкенил, низший алкилвинил или низшие алкиларилы; R2 независимо представляет собой Н, ОН, галогены, CN, N3, NH2, низший алкил, низшие алкиламины, низший алкилалкенил, низший алкилвинил, низшие алкиларилы или замещенные гетероциклы;
Х представляет собой независимо О, S, СН2 или NR, где R представляет собой СОСН3;
R1 и R4 независимо выбраны из Н, CN, N3, СН2ОН, низшего алкила или низших алкиламинов; и
R2, R3, R5, R6, R7, и R8 независимо выбраны из Н, ОН, CN, N3, галогенов, СН2OН, NH2, ОСН3, NHCH3, ONHCH3, SСН3, SPh, алкенила, низшего алкила, низших алкиламинов и замещенных гетероциклов так, что,
когда R2= R3= Н, то тогда R7 и R8 представляют собой водороды или отсутствуют;
когда A=N, В=СО, C=N или NH, D=CO или C-NH2, E представляет собой СН или замещен по С, F=CH, Х=O, S или СН2, то тогда R2 не будет представлять собой Н, ОН, СН3, галогены, N3, CN, SH, SPh, СН2OН, СН2OСН3, CH2SH, CH2F, CH2N3, арил, арилокси или гетероциклы;
когда A= N, В=СО, C=N или NH, D=CO или C-NH2, Е представляет собой СН, С-СН3 или галоген, F=CH, X=N-COCH3, то тогда R2 не будет представлять собой Н или ОН;
когда A=N, В=СН, С=СН или СН3, D=CH или С-СН3, Е представляет собой СН, С-СН3 или C-CONH2, F=CH, Х=O или СН2, то тогда R2 не будет представлять собой Н или ОН;
когда A= N, B= N, СО или СН, С=СН, С-Сl или С-ОСН3, D=CH или C-Ph, Е представляет собой СН, С-Сl или C-Ph, F=N или СО, Х=O, то тогда R2 не будет представлять собой Н или ОН;
когда A=N, B=CO или CS, C=N или NH, D=CO или C-NH2, E представляет собой СН или N, F=N или СН; Х=O, то тогда R2 не будет представлять собой Н или ОН, и
когда А= С, В=СН, C=NH, D=CO, CS или C-NH2, Е представляет собой N или NH, F=CO или СН, Х=O, то тогда R2 не будет представлять собой Н или ОН.4. The compound of 1, then having a structure in accordance with formula V
Figure 00000004

where a is independently selected from N or C;
B, C, E, F are independently selected from CH, CO, N, S, Se, O, NR 1 CCONH 2 , CCH 3 , CR 2, or P; R 1 is independently H, lower alkyl, lower alkylamines, COCH 3 , lower alkyl alkenyl, lower alkyl vinyl or lower alkylaryls; R 2 is independently H, OH, halogen, CN, N 3 , NH 2 , C (= O) NH 2 , C (= S) NH 2 , C (= NH) NH 2 • HCl, C (= NOH) NH 2 , C (= NH) OMe, lower alkyl, lower alkylamines, lower alkyl alkenyl, lower alkyl vinyl, lower alkylaryls, or substituted heterocycles;
D is independently selected from CH, CO, N, S, Se, O, NR 1 , CCONH 2 , CCH 3 , C-R 2 , P or absence; R 1 independently represents H, O, lower alkyl, lower alkylamines, COCH 3 , lower alkylalkenyl, lower alkylvinyl or lower alkylaryls; R 2 is independently H, OH, halogen, CN, N 3 , NH 2 , lower alkyl, lower alkyl amines, lower alkyl alkenyl, lower alkyl vinyl, lower alkylaryls, or substituted heterocycles;
X is independently O, S, CH 2 or NR, where R is COCH 3 ;
R 1 and R 4 are independently selected from H, CN, N 3 , CH 2 OH, lower alkyl or lower alkylamines; and
R 2 , R 3 , R 5 , R 6 , R 7 , and R 8 are independently selected from H, OH, CN, N 3 , halogens, CH 2 OH, NH 2 , OCH 3 , NHCH 3 , ONHCH 3 , SCH 3 , SPh, alkenyl, lower alkyl, lower alkylamines and substituted heterocycles so that,
when R 2 = R 3 = H, then R 7 and R 8 are hydrogens or absent;
when A = N, B = CO, C = N or NH, D = CO or C-NH 2 , E is CH or is substituted by C, F = CH, X = O, S or CH 2 , then R 2 will not be H, OH, CH 3 , halogen, N 3 , CN, SH, SPh, CH 2 OH, CH 2 OCH 3 , CH 2 SH, CH 2 F, CH 2 N 3 , aryl, aryloxy or heterocycles;
when A = N, B = CO, C = N or NH, D = CO or C-NH 2 , E is CH, C — CH 3 or halogen, F = CH, X = N-COCH 3 , then R 2 will not be H or OH;
when A = N, B = CH, C = CH or CH 3 , D = CH or C-CH 3 , E is CH, C-CH 3 or C-CONH 2 , F = CH, X = O or CH 2 then R 2 will not be H or OH;
when A = N, B = N, CO or CH, C = CH, C-Cl or C-OCH 3 , D = CH or C-Ph, E is CH, C-Cl or C-Ph, F = N or CO, X = O, then R 2 will not be H or OH;
when A = N, B = CO or CS, C = N or NH, D = CO or C-NH 2 , E is CH or N, F = N or CH; X = O, then R 2 will not represent H or OH, and
when A = C, B = CH, C = NH, D = CO, CS or C-NH 2 , E is N or NH, F = CO or CH, X = O, then R 2 will not be H or he. 5. Соединение по п.1,
где А, В и Е представляют собой азот;
С представляет собой C-C(O)NH2;
D отсутствует;
F представляет собой СН;
X представляет собой кислород;
R1, R4, R5, R7 и R8 представляют собой водороды:
a R2, R3 и R6 представляют собой гидроксил.5. The compound according to claim 1,
where a, b and E are nitrogen;
C is CC (O) NH 2 ;
D is absent;
F is CH;
X is oxygen;
R 1 , R 4 , R 5 , R 7 and R 8 are hydrogens:
a R 2 , R 3 and R 6 are hydroxyl. 6. Соединение по п.1, включая L-Рибавирин,
где R2 и R3 представляют собой ОН, один из R5 и R6 представляет собой Н, а другой представляет собой ОН;
А, С и F представляют собой N,
D отсутствует,
а Е представляет собой C-CO-NH2.6. The compound according to claim 1, including L-Ribavirin,
wherein R 2 and R 3 are OH, one of R 5 and R 6 is H, and the other is OH;
A, C and F are N,
D is missing,
and E is C — CO — NH 2 . 7. Соединение по любому из пп. 1 - 6, где это соединение является α-нуклеозидом. 7. The compound according to any one of paragraphs. 1 - 6, where this compound is α-nucleoside. 8. Соединение по любому из пп. 1 - 6, где это соединение является β-нуклеозидом. 8. The compound according to any one of paragraphs. 1 - 6, where this compound is β-nucleoside. 9. Фармацевтическое соединение, включающее в себя соединение по любому из пп.1 - 6, или его фармацевтически приемлемый эфир или соль, в смеси с по меньшей мере одним фармацевтически приемлемым носителем. 9. A pharmaceutical compound comprising a compound according to any one of claims 1 to 6, or a pharmaceutically acceptable ester or salt thereof, in a mixture with at least one pharmaceutically acceptable carrier. 10. Способ лечения пациента, имеющего воспалительное медицинское состояние, которое положительно реагирует на введение соединения по любому из пп.1 - 6, при котором предоставляют это соединение; вводят дозу этого соединения пациенту; и наблюдают пациента в отношении эффективности и побочных эффектов. 10. A method of treating a patient having an inflammatory medical condition that responds positively to the administration of a compound according to any one of claims 1 to 6, wherein this compound is provided; administered a dose of this compound to the patient; and the patient is observed for efficacy and side effects. 11. Способ по п.10, где медицинское состояние является инфекцией. 11. The method according to claim 10, where the medical condition is an infection. 12. Способ по п.10, где медицинское состояние является инвазией. 12. The method according to claim 10, where the medical condition is invasion. 13. Способ по п.10, где медицинское состояние является неоплазмой. 13. The method according to claim 10, where the medical condition is neoplasm. 14. Способ по п.10, где медицинское состояние является аутоиммунным заболеванием. 14. The method of claim 10, where the medical condition is an autoimmune disease. 15. Способ по п.10, где стадия введения соединения пациенту включает в себя введение терапевтического количества этого соединения. 15. The method of claim 10, wherein the step of administering the compound to the patient comprises administering a therapeutic amount of the compound. 16. Способ противоположной модуляции Th1- и Тh2-активностей у пациента, при котором предоставляют соединение по одному из пп.1 - 6 и вводят дозу этого соединения пациенту. 16. A method of the opposite modulation of the Th1- and Th2-activities in a patient, in which they provide a compound in accordance with one of claims 1-6, and a dose of this compound is administered to the patient.
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