RU2000125690A - Derivatives of benzofurylpyrone - Google Patents
Derivatives of benzofurylpyroneInfo
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- RU2000125690A RU2000125690A RU2000125690/04A RU2000125690A RU2000125690A RU 2000125690 A RU2000125690 A RU 2000125690A RU 2000125690/04 A RU2000125690/04 A RU 2000125690/04A RU 2000125690 A RU2000125690 A RU 2000125690A RU 2000125690 A RU2000125690 A RU 2000125690A
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- carbon atoms
- group containing
- heterocycle
- group
- alkyl group
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- SKPOULXOGAGECM-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)pyran-2-one Chemical class O=C1OC=CC=C1C1=CC2=CC=CC=C2O1 SKPOULXOGAGECM-UHFFFAOYSA-N 0.000 title 1
- 125000004432 carbon atoms Chemical group C* 0.000 claims 176
- 125000000623 heterocyclic group Chemical group 0.000 claims 85
- 229910052739 hydrogen Inorganic materials 0.000 claims 71
- 239000001257 hydrogen Substances 0.000 claims 71
- 125000000217 alkyl group Chemical group 0.000 claims 67
- -1 diethylaminosulfonyl group Chemical group 0.000 claims 63
- 150000002431 hydrogen Chemical class 0.000 claims 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 37
- 150000003839 salts Chemical class 0.000 claims 32
- 239000011780 sodium chloride Substances 0.000 claims 32
- 125000003545 alkoxy group Chemical group 0.000 claims 24
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 19
- 125000003710 aryl alkyl group Chemical group 0.000 claims 14
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 9
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 9
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 239000004480 active ingredient Substances 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 5
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000004429 atoms Chemical group 0.000 claims 4
- 239000003795 chemical substances by application Substances 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 3
- 125000004104 aryloxy group Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000006263 dimethyl aminosulfonyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 3
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N Benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims 2
- YDBQJGWNFSPUNX-UHFFFAOYSA-N [O-][N+](=O)BrC#N Chemical group [O-][N+](=O)BrC#N YDBQJGWNFSPUNX-UHFFFAOYSA-N 0.000 claims 2
- 125000004423 acyloxy group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 201000001320 atherosclerosis Diseases 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims 2
- 150000003626 triacylglycerols Chemical class 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- 125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 claims 1
- 210000004369 Blood Anatomy 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004442 acylamino group Chemical group 0.000 claims 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 1
- 230000037348 biosynthesis Effects 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims 1
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000005842 heteroatoms Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 239000003112 inhibitor Substances 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000037356 lipid metabolism Effects 0.000 claims 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 239000003208 petroleum Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-M phenoxyacetate Chemical compound [O-]C(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-M 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
Claims (32)
где R1 представляет собой водород или алкильную группу, содержащую от 1 до 5 атомов углерода;
R2 представляет собой водород, -CO-R5, где R5 представляет собой водород, алкильную группу, содержащую от 1 до 5 атомов углерода, необязательно содержащую заместители, циклоалкильную группу, содержащую от 3 до 7 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, или гетероцикл или -SO2R6, где R6 представляет собой алкильную группу, содержащую от 1 до 5 атомов углерода, необязательно замещенную галогеном, или арильную группу, содержащую от 6 до 10 атомов углерода;
R3 представляет собой водород, алкильную группу, содержащую от 1 до 5 атомов углерода, алкенильную группу, содержащую от 2 до 5 атомов углерода, алкинильную группу, содержащую от 2 до 5 атомов углерода, циклоалкильную группу, содержащую от 3 до 7 атомов углерода, циклоалкильную группу, содержащую от 3 до 7 атомов углерода - алкильную группу, содержащую от 1 до 5 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, аралкильную группу, содержащую от 1 до 20 атомов углерода, алкокси группу, содержащую от 1 до 5 атомов углерода, или арилокси группу, содержащую от 6 до 10 атомов углерода;
R4 является заместителем в С-4 положении, С-5 положении, С-6 положении или С-7 положении бензофуранового кольца и представляет собой:
R4a, который представляет собой водород, нитро группу, циано группу, атом галогена, гетероцикл, алкенильную группу, содержащую от 2 до 5 атомов углерода, алкинильную группу, содержащую от 2 до 5 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, А= СН(СН2)n-, где А представляет собой алициклический гетероцикл, "= " представляет собой двойную связь и n представляет собой 0, 1 или 2, A= CH(CH2)mO-, где А представляет собой алициклический гетероцикл, "= " представляет собой двойную связь и m представляет собой 1, 2 или 3, A-SO2-(CH2)m-, где А представляет собой алициклический гетероцикл и m представляет собой 1, 2 или 3, -OR7, где R7 представляет собой водород, циклоалкильную группу, содержащую от 3 до 7 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, гетероцикл, или алкилсульфонильную группу, содержащую от 1 до 4 атомов углерода, необязательно замещенную галогеном, или арилсульфонильную группу, содержащую от 6 до 10 атомов углерода, -O-CO-R8, где R8 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, аралкильную группу, содержащую от 7 до 20 атомов углерода, или гетероцикл, -NR9R10 где каждый из R9 и R10 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, аралкильную группу, содержащую от 7 до 20 атомов углерода, гетероцикл, фенильную группу, -SO2-R11, где R11 представляет собой необязательно замещенную галогеном алкильную группу, содержащую от 1 до 12 атомов углерода, замещенную гетероциклом алкильную группу, содержащую от 1 до 6 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, гетероцикл или аралкильную группу, содержащую от 7 до 20 атомов углерода или -CO-R12, где R12 представляет собой водород, алкильную группу, содержащую от 1 до 12 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, аралкильную группу, содержащую от 7 до 20 атомов углерода, гетероцикл, алкокси группу, содержащую от 1 до 10 атомов углерода, замещенную гетероциклом алкильную группу, содержащую от 1 до 6 атомов углерода, арилокси группу, содержащую от 6 до 10 атомов углерода, гетероарилокси группу или аралкилокси группу, содержащую от 7 до 20 атомов углерода, -CO-R13, где R13 представляет собой водород, -ОН, алкильную группу, содержащую от 1 до 4 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, гетероцикл, алкокси группу, содержащую от 1 до 4 атомов углерода, арилокси группу, содержащую от 6 до 10 атомов углерода, или аралкилокси группу, содержащую от 7 до 20 атомов углерода, или -CO-NR14R15, где каждый из R14 и R15 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, циклоалкильную группу, содержащую от 3 до 7 атомов углерода, арильную группу, содержащую от 6 до 10 атомов углерода, аралкильную группу, содержащую от 7 до 20 атомов углерода, гетероцикл или замещенную гетероциклом алкильную группу, содержащую от 1 до 4 атомов углерода;
R4b, который представляет собой насыщенную или ненасыщенную алкокси группу, содержащую от 1 до 6 атомов углерода, необязательно замещенную 1-3 группами, выбранными из группы, состоящей из галогенов, циклоалкильных групп, содержащих от 3 до 7 атомов углерода, фенила, нафтила, гетероциклов, -OR16, где R16 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу или гетероцикл), -O-CO-R16, где R16 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу или гетероцикл, -NR17R18, где каждый из R17 и R18 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, гетероцикл, алкилсульфонильную группу, содержащую от 1 до 4 атомов углерода, фенилсульфонильную группу, -SO2-Het где Het представляет собой гетероцикл, аминосульфонильную группу, метиламиносульфонильную группу, диметиламиносульфонильную группу, диэтиламиносульфонильную группу или алкильную группу, содержащую от 1 до 4 атомов углерода, замещенную одной или двумя группами, выбранными из фенила, гетероциклов, фенокси, -O-Het (где Het представляет собой гетероцикл) и гидроксила, -NH-CO-R19, где R19 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу, гетероцикл, алкокси группу, содержащую от 1 до 4 атомов углерода, или бензилокси группу, -CO-R20 где R20 представляет собой водород, гетероцикл, алкокси группу, содержащую от 1 до 4 атомов углерода, фенокси группу, бензилокси группу или -OR21 (где R21 представляет собой водород или гетероцикл)) и -CO-NR22R23, где каждый из R22 и R23 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, бензильную группу или гетероцикл; или
R4c, который представляет собой алкильную группу, содержащую от 1 до 4 атомов углерода, необязательно замещенную 1-3 группами, выбранными из группы, состоящей из галогенов, циклоалкильных групп, содержащих от 3 до 7 атомов углерода, фенила, нафтила, гетероциклов, -SH, -OR16, где R16 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу или гетероцикл, -O-CO-R16, где R16 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу или гетероцикл, -NR17R18, где каждый из R17 и R18 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, гетероцикл, алкилсульфонильную группу, содержащую от 1 до 4 атомов углерода, фенилсульфонильную группу, -SO2-Het, где Het представляет собой гетероцикл, аминосульфонильную группу, метиламиносульфонильную группу, диметиламиносульфонильную группу, диэтиламиносульфонильную группу или алкильную группу, содержащую от 1 до 4 атомов углерода, замещенную одной или двумя группами, выбранными из фенила, гетероциклов, фенокси, -O-Het, где Het представляет собой гетероцикл и гидроксила, -NH-CO-R19, где R19 представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, фенильную группу, нафтильную группу, бензильную группу, гетероцикл, алкокси группу, содержащую от 1 до 4 атомов углерода, или бензилокси группу, -CO-R20, где R20 представляет собой водород, гетероцикл, алкокси группу, содержащую от 1 до 4 атомов углерода, фенокси группу, бензилокси группу или -OR21, где R21 представляет собой водород или гетероцикл и -CO-NR22R23 где каждый из R22 и R23 независимо представляет собой водород, алкильную группу, содержащую от 1 до 4 атомов углерода, бензильную группу или гетероцикл; и цифры, написанные курсивом, обозначают положения в бензофурановом кольце;
или его соль.1. Derived benzofuryl-α-pyrone represented by the following structural formula (I)
where R 1 represents hydrogen or an alkyl group containing from 1 to 5 carbon atoms;
R 2 is hydrogen, —CO — R 5 , where R 5 is hydrogen, an alkyl group containing from 1 to 5 carbon atoms, optionally containing substituents, a cycloalkyl group containing from 3 to 7 carbon atoms, an aryl group containing from 6 to 10 carbon atoms, or a heterocycle or -SO 2 R 6 , where R 6 represents an alkyl group containing from 1 to 5 carbon atoms, optionally substituted with halogen, or an aryl group containing from 6 to 10 carbon atoms;
R 3 represents hydrogen, an alkyl group containing from 1 to 5 carbon atoms, an alkenyl group containing from 2 to 5 carbon atoms, an alkynyl group containing from 2 to 5 carbon atoms, a cycloalkyl group containing from 3 to 7 carbon atoms, cycloalkyl group containing from 3 to 7 carbon atoms - an alkyl group containing from 1 to 5 carbon atoms, an aryl group containing from 6 to 10 carbon atoms, an aralkyl group containing from 1 to 20 carbon atoms, an alkoxy group containing from 1 up to 5 carbon atoms, or aryloxy a group containing from 6 to 10 carbon atoms;
R 4 is a substituent at the C-4 position, C-5 position, C-6 position or C-7 position of the benzofuran ring and is:
R 4a , which is a hydrogen, nitro group, cyano group, halogen atom, heterocycle, alkenyl group containing from 2 to 5 carbon atoms, an alkynyl group containing from 2 to 5 carbon atoms, an aryl group containing from 6 to 10 atoms carbon, A = CH (CH 2 ) n -, where A represents an alicyclic heterocycle, "=" represents a double bond and n represents 0, 1 or 2, A = CH (CH 2 ) m O-, where A represents is an alicyclic heterocycle, “=” is a double bond and m is 1, 2 or 3, A — SO 2 - (CH 2 ) m -, where A is is an alicyclic heterocycle and m is 1, 2 or 3, -OR 7 where R 7 is hydrogen, a cycloalkyl group containing from 3 to 7 carbon atoms, an aryl group containing from 6 to 10 carbon atoms, a heterocycle, or an alkylsulfonyl group containing from 1 to 4 carbon atoms, optionally substituted with halogen, or an arylsulfonyl group containing from 6 to 10 carbon atoms, —O — CO — R 8 , where R 8 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aryl group containing from 6 to 10 atoms carbon, aralkyl group containing from 7 to 20 carbon atoms, or a heterocycle, —NR 9 R 10 where each of R 9 and R 10 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aralkyl group containing from 7 to 20 carbon atoms, heterocycle, phenyl group, -SO 2 -R 11 , where R 11 is an optionally halogen-substituted alkyl group containing from 1 to 12 carbon atoms, a heterocycle-substituted alkyl group containing from 1 to 6 carbon atoms, an aryl group containing from 6 to 10 carbon atoms , A heterocycle or an aralkyl group having from 7 to 20 carbon atoms or -CO-R 12 where R 12 represents hydrogen, an alkyl group containing from 1 to 12 carbon atoms, an aryl group having from 6 to 10 carbon atoms, an aralkyl a group containing from 7 to 20 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 10 carbon atoms, a heterocycle-substituted alkyl group containing from 1 to 6 carbon atoms, an aryloxy group containing from 6 to 10 carbon atoms, a heteroaryloxy group or aralkyloxy group containing from 7 to 20 carbon atoms, —CO — R 13 , where R 13 is hydrogen, —OH, an alkyl group containing from 1 to 4 carbon atoms, an aryl group containing from 6 to 10 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, aryloxy group containing from 6 to 10 carbon atoms, or aralkyloxy group containing from 7 to 20 carbon atoms, or —CO-NR 14 R 15 , where each of R 14 and R 15 independently represents hydrogen, alkyl a group containing from 1 to 4 carbon atoms, a cycloalkyl group containing from 3 to 7 carbon atoms, aryl g uppu containing from 6 to 10 carbon atoms, an aralkyl group having from 7 to 20 carbon atoms, a heterocycle or a heterocycle-substituted alkyl group having from 1 to 4 carbon atoms;
R 4b , which is a saturated or unsaturated alkoxy group containing from 1 to 6 carbon atoms, optionally substituted with 1-3 groups selected from the group consisting of halogens, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycles, -OR 16 , where R 16 represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a phenyl group, a naphthyl group, a benzyl group or a heterocycle), -O-CO-R 16 , where R 16 represents hydrogen , an alkyl group containing from 1 to 4 carbon atoms , A phenyl group, a naphthyl group, a benzyl group or a heterocycle, -NR 17 R 18, wherein each of R 17 and R 18 independently represents hydrogen, an alkyl group having 1 to 4 carbons, a heterocycle, an alkylsulfonyl group having from 1 up to 4 carbon atoms, phenylsulfonyl group, -SO 2 -Het where Het is a heterocycle, aminosulfonyl group, methylaminosulfonyl group, dimethylaminosulfonyl group, diethylaminosulfonyl group, or an alkyl group containing from 1 to 4 carbon atoms, substituted one oh or two groups selected from phenyl, heterocycles, phenoxy, -O-Het (where Het is a heterocycle) and hydroxyl, -NH-CO-R 19 , where R 19 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a phenyl group, a naphthyl group, a benzyl group, a heterocycle, an alkoxy group having from 1 to 4 carbon atoms, or a benzyloxy group, -CO-R 20 wherein R 20 represents hydrogen, a heterocycle, an alkoxy group having from 1 to 4 carbon atoms, a phenoxy group, a benzyloxy group or -OR 21 (wherein R 21 represents hydrogen yl a heterocycle)) and -CO-NR 22 R 23, wherein each of R 22 and R 23 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a benzyl group or a heterocycle; or
R 4c , which represents an alkyl group containing from 1 to 4 carbon atoms, optionally substituted by 1-3 groups selected from the group consisting of halogens, cycloalkyl groups containing from 3 to 7 carbon atoms, phenyl, naphthyl, heterocycles, - SH, -OR 16 , where R 16 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a phenyl group, a naphthyl group, a benzyl group or a heterocycle, -O-CO-R 16 , where R 16 is hydrogen, alkyl group containing from 1 to 4 carbon atoms, phenyl group, naphtha battening group, a benzyl group or a heterocycle, -NR 17 R 18, wherein each of R 17 and R 18 independently represents hydrogen, an alkyl group having 1 to 4 carbons, a heterocycle, an alkylsulfonyl group having from 1 to 4 carbon atoms , a phenylsulfonyl group, -SO 2 -Het, where Het represents a heterocycle, an aminosulfonyl group, a methylaminosulfonyl group, a dimethylaminosulfonyl group, a diethylaminosulfonyl group, or an alkyl group containing from 1 to 4 carbon atoms substituted with one or two groups, abusive of phenyl, heterocycles, phenoxy, -O-Het, wherein Het represents a heterocycle and hydroxyl, -NH-CO-R 19, where R 19 represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a phenyl group, naphthyl group, benzyl group, heterocycle, alkoxy group containing from 1 to 4 carbon atoms, or benzyloxy group, —CO-R 20 , where R 20 is hydrogen, heterocycle, alkoxy group containing from 1 to 4 carbon atoms, phenoxy group, a benzyloxy group or -OR 21, where R 21 represents hydrogen or a heterocycle, and -CO-NR 22 R 23 de each of R 22 and R 23 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a benzyl group or a heterocycle; and the numbers in italics indicate the positions in the benzofuran ring;
or its salt.
или его соль.4. Derived benzofuryl-α-pyrone according to any one of paragraphs. 1-3, characterized in that R 5 represents (1) an alkyl group containing from 1 to 5 carbon atoms, optionally substituted with 1-4 substituents selected from the group consisting of halogens, —OR 8 , where R 8 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aryl group containing from 6 to 10 carbon atoms, an aralkyl group containing from 7 to 20 carbon atoms, or a heterocycle, -O-CO-R 8 , where R 8 is a hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aryl group containing from 6 to 10 atoms carbon carbon, an aralkyl group containing from 7 to 20 carbon atoms, or a heterocycle, —NR 9 R 10 , where each of R 9 and R 10 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aralkyl group, containing from 7 to 20 carbon atoms, a heterocycle, an optionally halogen-substituted alkylsulfonyl group containing from 1 to 4 carbon atoms, or an arylsulfonyl group containing from 6 to 10 carbon atoms, -NH-CO-R 24 , where R 24 is hydrogen , an alkyl group containing from 1 to 4 carbon atoms, aryl a group containing from 6 to 10 carbon atoms, an aralkyl group containing from 7 to 20 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, or an aralkoxy group containing from 7 to 20 carbon atoms, cycloalkyl groups, containing from 3 to 7 carbon atoms, aryl groups containing from 6 to 10 carbon atoms, heterocycles and -CO-R 25 , where R 25 represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, heterocycle, -OR 8 where R 8 represents hydrogen, an alkyl group containing from 1 to 4 atoms yz Erode, an aryl group having from 6 to 10 carbon atoms, an aralkyl group having from 7 to 20 carbon atoms or a heterocycle, or -NR 26 R 27, wherein each of R 26 and R 27 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, an aralkyl group containing from 7 to 20 carbon atoms or a heterocycle, (2) a hydrogen atom, (3) a cycloalkyl group containing from 3 to 7 carbon atoms, (4) an aryl group containing from 6 to 10 carbon atoms, or (5) a heterocycle;
or its salt.
или его соль.5. Derived benzofuryl-α-pyrone according to any one of paragraphs. 1-3, characterized in that R 5 represents (1) an alkyl group containing from 1 to 5 carbon atoms, optionally substituted with 1-3 substituents selected from the group consisting of —OH, alkoxy groups containing from 1 to 4 carbon atoms, phenoxy, benzyloxy, —O — CO — R 28 , where R 28 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a phenyl group or a heterocycle, —NR 29 R 30 , where each of R 29 and R 30 independently represents hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a benzyl group, a heterocycle or neo an optionally halogen-substituted alkylsulfonyl group containing from 1 to 4 carbon atoms, —NH — CO — R 31 , where R 31 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a heterocycle, an alkoxy group containing from 1 to 4 carbon atoms, or a benzyloxy group, aryl groups containing from 6 to 10 carbon atoms, heterocycles and —CO — R 32 , where R 32 is hydrogen, OR 32 , where R 32 is hydrogen, an alkyl group containing from 1 to 4 carbon atoms, a benzyl group or a heterocycle, -NR 33 R 34, wherein each of R 33 and R 34 Irrespective represents hydrogen, methyl, ethyl, benzyl or a heterocycle or a heterocycle, (2) a cycloalkyl group having from 3 to 7 carbon atoms, (3) an aryl group having from 6 to 10 carbon atoms, or (4) a heterocycle;
or its salt.
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US (2) | US6589984B1 (en) |
EP (1) | EP1063235B1 (en) |
JP (1) | JP3922884B2 (en) |
KR (1) | KR100595332B1 (en) |
CN (1) | CN1170827C (en) |
AT (1) | ATE266659T1 (en) |
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BG (1) | BG104761A (en) |
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HR (1) | HRP20000600A2 (en) |
HU (1) | HUP0101381A3 (en) |
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PL (1) | PL343419A1 (en) |
RU (1) | RU2199536C2 (en) |
SK (1) | SK13412000A3 (en) |
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AU756965B2 (en) * | 1998-03-12 | 2003-01-30 | Microbial Chemistry Research Foundation | Benzofurylpyrone derivatives |
AU2001288432A1 (en) | 2000-09-01 | 2002-03-22 | Icos Corporation | Materials and methods to potentiate cancer treatment |
DE10115408A1 (en) * | 2001-03-29 | 2002-10-02 | Bayer Ag | Benzofuran derivatives |
PL370074A1 (en) * | 2002-02-25 | 2005-05-16 | Kudos Pharmaceuticals Ltd | Pyranones useful as atm inhibitors |
DE10314610A1 (en) | 2003-04-01 | 2004-11-04 | Aventis Pharma Deutschland Gmbh | New diphenylazetidinone with improved physiological properties, process for its preparation, medicaments containing these compounds and its use |
RU2009108280A (en) | 2006-08-08 | 2010-09-20 | Санофи-Авентис (Fr) | Arylamino-arylalkyl-substituted imidazolidine-2,4-dione, methods for their preparation containing these compounds and their use |
EP2025674A1 (en) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituted tetra hydro naphthalines, method for their manufacture and their use as drugs |
DE102007063671A1 (en) | 2007-11-13 | 2009-06-25 | Sanofi-Aventis Deutschland Gmbh | New crystalline diphenylazetidinone hydrates, medicaments containing these compounds and their use |
FR2929276B1 (en) * | 2008-04-01 | 2010-04-23 | Servier Lab | NOVEL DIOSMETIN DERIVATIVES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
AR072707A1 (en) | 2008-07-09 | 2010-09-15 | Sanofi Aventis | HETEROCICLIC COMPOUNDS, PROCESSES FOR THEIR PREPARATION, DRUGS THAT UNDERSTAND THESE COMPOUNDS AND THE USE OF THEM |
WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
EP2470552B1 (en) | 2009-08-26 | 2013-11-13 | Sanofi | Novel crystalline heteroaromatic fluoroglycoside hydrates, pharmaceuticals comprising these compounds and their use |
EP2582709B1 (en) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-one derivatives as inhibitors of lipases and phospholipases |
US8828994B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Di- and tri-substituted oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
EP2683702B1 (en) | 2011-03-08 | 2014-12-24 | Sanofi | New substituted phenyl oxathiazine derivatives, method for their manufacture, medicines containing these compounds and their application |
EP2683703B1 (en) | 2011-03-08 | 2015-05-27 | Sanofi | Novel substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
US8846666B2 (en) | 2011-03-08 | 2014-09-30 | Sanofi | Oxathiazine derivatives which are substituted with benzyl or heteromethylene groups, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
EP2766349B1 (en) | 2011-03-08 | 2016-06-01 | Sanofi | Oxathiazine derivatives substituted with carbocycles or heterocycles, method for producing same, drugs containing said compounds, and use thereof |
EP2683700B1 (en) | 2011-03-08 | 2015-02-18 | Sanofi | Tetra-substituted oxathiazine derivatives, method for their preparation, their usage as medicament and medicament containing same and its use |
US8710050B2 (en) | 2011-03-08 | 2014-04-29 | Sanofi | Di and tri- substituted oxathiazine derivatives, method for the production, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
EP2683698B1 (en) | 2011-03-08 | 2017-10-04 | Sanofi | Benzyl-oxathiazine derivates substituted with adamantane or noradamantane, medicaments containing said compounds and use thereof |
EP2567959B1 (en) | 2011-09-12 | 2014-04-16 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
DE102014214016A1 (en) | 2014-07-18 | 2015-11-05 | Deutsches Zentrum für Luft- und Raumfahrt e.V. | Lightweight structure and method for producing a lightweight structure |
US11433047B2 (en) * | 2015-10-09 | 2022-09-06 | Neurotheryx Canada Ltd. | Pharmaceutical compositions comprising one or more pyrone compounds, and their use for treating inflammatory and neurodegenerative diseases |
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US4668803A (en) | 1984-05-10 | 1987-05-26 | Atlantic Richfield Company | Benzafuran derivatives |
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ZA938019B (en) | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
US6005103A (en) | 1993-11-19 | 1999-12-21 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
AU756965B2 (en) * | 1998-03-12 | 2003-01-30 | Microbial Chemistry Research Foundation | Benzofurylpyrone derivatives |
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