RU2371444C1 - FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY - Google Patents

FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY Download PDF

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RU2371444C1
RU2371444C1 RU2008102156/04A RU2008102156A RU2371444C1 RU 2371444 C1 RU2371444 C1 RU 2371444C1 RU 2008102156/04 A RU2008102156/04 A RU 2008102156/04A RU 2008102156 A RU2008102156 A RU 2008102156A RU 2371444 C1 RU2371444 C1 RU 2371444C1
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Александр Васильевич Иващенко (US)
Александр Васильевич Иващенко
Андрей Александрович Иващенко (RU)
Андрей Александрович Иващенко
Дмитрий Владимирович Кравченко (RU)
Дмитрий Владимирович Кравченко
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Андрей Александрович Иващенко
Алла Хем, Ллс
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Abstract

FIELD: chemistry.
SUBSTANCE: in formula
Figure 00000081
compounds, each of R1, R2, R3, R4 is a substitute for a cyclic system, chosen from hydrogen, halogen, C1-C6-alkyl; C1-C6-alkoxy group; X is a heteroatom, chosen from oxygen or sulphur; R5 and R6 independently represent amino group substitutes, chosen from hydrogen, possibly substituted C1-C6-alkyl; possibly substituted C3-C6-cycloalkyl, which can be annealed with a benzene ring; possibly substituted phenyl, which can be annealed with dioxole, dioxine, -(CH2)n group, where n=4 to 6, or with a 5 or 6-member possibly substituted and possibly condensed azaheterocyclyl; possibly substituted saturated or unsaturated 5-6-member heterocyclyl, containing 1-2 heteroatoms, chosen form nitrogen, oxygen, sulphur and possibly condensed with a benzene ring, or R5 and R6 together with the nitrogen atom to which they are bonded, form an optionally substituted 5 or 6-member azahetero ring, possibly containing an additional heteroatom, chosen from nitrogen, and possibly annealed with a benzene ring or spiro-condensed with dioxole, where substitutes in the said alkyl, cycloalkyl, phenyl and heterocyclyl are chosen from halogen atoms, possibly substituted C1-C6-alkyl, CF3, possibly substituted C3-C6-cycloalkyl, possibly substituted phenyl, 5 or 6-member heterocyclyl, nitro group, substituted amino group, alkyloxycarbonyl, substituted carbonyl, aminocarbonyl, alkylsulphanyl.
EFFECT: design of an efficient method of producing new substituted furo[2,3-b]quinoline-2-carboxamides and substituted thieno[2,3-b]quinoline-2-carboxamides or their racemates, or their optical isomers, as well as their pharmaceutically acceptable salts and/or hydrates of general formula (I), which have antituberculous activity.
9 cl, 1 dwg, 7 tbl, 5 ex

Description

Текст описания приведен в факсимильном виде.

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The text of the description is given in facsimile form.
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Claims (9)

1. Азагетероциклические соединения, представляющие собой замещенные фуро[2,3-b]хинолин-2-карбоксамиды и замещенные тиено[2,3-b]хинолин-2-карбоксамиды, или их рацематы, или их оптические изомеры, а также их фармацевтически приемлемые соли и/или гидраты общей формулы (I)
Figure 00000075

где каждый из R1, R2, R3, R4 представляет собой заместитель циклической системы, выбранный из водорода, галогена, C1-С6-алкила; C1-С6-алкоксигруппы;
Х представляет собой гетероатом, выбранный из кислорода или серы;
R5 и R6 независимо друг от друга представляют собой заместители аминогруппы, выбранные из водорода, возможно замещенного C1-С6-алкила;
возможно замещенного С3-С6-циклоалкила, который может быть аннелирован с бензольным кольцом;
возможно замещенного фенила, который может быть аннелирован с диоксолом, диоксином, с группой -(СН2)n, где n=4-6, или с 5-6-членным возможно замещенным и возможно конденсированным азагетероциклилом;
возможно замещенного насыщенного или ненасыщенного 5-6-членного гетероциклила, содержащего 1-2 гетероатома, выбранных из азота, кислорода, серы и возможно конденсированного с бензольным кольцом,
или R5 и R6 вместе с атомом азота, с которым они связаны, образуют необязательно замещенный 5-6-членный азагетероцикл, возможно содержащий дополнительно гетероатом, выбранный из азота, и возможно аннелированный с бензольным кольцом или спироконденсированный с диоксолом,
при этом заместители в указанном алкиле, циклоалкиле, фениле и гетероциклиле выбираются из атомов галогена, возможно замещенного C1-С6-алкила, CF3, возможно замещенного С3-С6-циклоалкила, возможно замещенного фенила, 5-6-членного гетероциклила, нитрогруппы, замещенной аминогруппы, алкилоксикарбонила, замещенного карбонила, аминокарбонила, алкилсульфанила; исключая:
соединения, в которых Х=O, R1=R2=R4=R5=R6=H, R3=H, СН3, ОСН3;
соединения, в которых X=S, R1=R2=R3=R4=R5=H, R6=H, 1-азабицикло[2.2.2]окт-3-ил;
соединения, в которых X=S, R1=R3=R4=R5=H, R2=CH3, R6=H, СН3, 2,5-диоксопирролидин-1-ил, 1,3-диоксоизоиндолин-2-ил, или R5 и R6 вместе с атомом азота, с которым они связаны, образуют 3,5-диметил-4,5-дигидро-1Н-пиразол-1-ил, 5-метил-1Н-пиразол-3(2Н)-оксо-2-ил;
соединения, в которых X=S, R1=R2=R4=R5=H, R3=трет-бутил, R6=H, (CH2)2NHBoc, (CH2)2NH2, (CH2)2NHCH3, (СН2)2N(СН3)2, (CH2)2CN, CH2CN, [1-(2,4-диметоксибензил)-2-оксо-азетидин-3-ил], 2-оксо-азетидин-3-ил, 2-амино-1-(S)-фенил-этил, 2(S)-амино-1-(3-аминофенил)этил, 2-амино-1(S)-{3-[(пиразин-2-карбонил)амино]фенил}этил, 2-амино-1(S)-{3-[(3-аминопиразин-2-карбонил)амино]фенил}этил, 2-амино-1(S)-{3-[(5-метил-изоксазол-3-карбонил)амино]фенил}этил;
и соединения, в которых X=S, R1=R2=R4=R5=H, R3=1-метил-циклопентил, R6=2-амино-1-(S)-{3-[(фуран-2-карбонил)амино]фенил}этил, 2-амино-1(S)-{3-[(1-метил-1Н-пиразол-3-карбонил)-амино]фенил}этил.1. Azaheterocyclic compounds, which are substituted furo [2,3-b] quinoline-2-carboxamides and substituted thieno [2,3-b] quinoline-2-carboxamides, or their racemates, or their optical isomers, and also their pharmaceutically acceptable salts and / or hydrates of the general formula (I)
Figure 00000075

where each of R 1 , R 2 , R 3 , R 4 represents a Deputy of the cyclic system selected from hydrogen, halogen, C 1 -C 6 -alkyl; C 1 -C 6 alkoxy groups;
X represents a heteroatom selected from oxygen or sulfur;
R 5 and R 6, independently of one another, are amino substituents selected from hydrogen, optionally substituted C 1 -C 6 alkyl;
optionally substituted C 3 -C 6 cycloalkyl which can be annelated with a benzene ring;
possibly substituted phenyl, which can be annelated with dioxol, dioxin, with the group - (CH 2 ) n , where n = 4-6, or with a 5-6 membered possibly substituted and possibly fused azaheterocyclyl;
possibly substituted saturated or unsaturated 5-6 membered heterocyclyl containing 1-2 heteroatoms selected from nitrogen, oxygen, sulfur and possibly fused to a benzene ring,
or R 5 and R 6, together with the nitrogen atom to which they are bonded, form an optionally substituted 5-6 membered azaheterocycle, optionally further containing a heteroatom selected from nitrogen, and possibly annelated with a benzene ring or spirocondensed with dioxole,
while the substituents in said alkyl, cycloalkyl, phenyl and heterocyclyl are selected from halogen atoms, possibly substituted C 1 -C 6 alkyl, CF 3 , optionally substituted C 3 -C 6 cycloalkyl, optionally substituted phenyl, 5-6 membered heterocyclyl a nitro group, a substituted amino group, alkyloxycarbonyl, substituted carbonyl, aminocarbonyl, alkylsulfanyl; excluding:
compounds in which X = O, R 1 = R 2 = R 4 = R 5 = R 6 = H, R 3 = H, CH 3 , OCH 3 ;
compounds in which X = S, R 1 = R 2 = R 3 = R 4 = R 5 = H, R 6 = H, 1-azabicyclo [2.2.2] oct-3-yl;
compounds in which X = S, R 1 = R 3 = R 4 = R 5 = H, R 2 = CH 3 , R 6 = H, CH 3 , 2,5-dioxopyrrolidin-1-yl, 1,3- dioxoisoindolin-2-yl, or R 5 and R 6 together with the nitrogen atom to which they are attached form 3,5-dimethyl-4,5-dihydro-1H-pyrazol-1-yl, 5-methyl-1H-pyrazole -3 (2H) -oxo-2-yl;
compounds in which X = S, R 1 = R 2 = R 4 = R 5 = H, R 3 = tert-butyl, R 6 = H, (CH 2 ) 2 NHBoc, (CH 2 ) 2 NH 2 , ( CH 2 ) 2 NHCH 3 , (CH 2 ) 2 N (CH 3 ) 2 , (CH 2 ) 2 CN, CH 2 CN, [1- (2,4-dimethoxybenzyl) -2-oxo-azetidin-3-yl ], 2-oxo-azetidin-3-yl, 2-amino-1- (S) -phenyl-ethyl, 2 (S) -amino-1- (3-aminophenyl) ethyl, 2-amino-1 (S) - {3 - [(pyrazine-2-carbonyl) amino] phenyl} ethyl, 2-amino-1 (S) - {3 - [(3-aminopyrazine-2-carbonyl) amino] phenyl} ethyl, 2-amino 1 (S) - {3 - [(5-methyl-isoxazole-3-carbonyl) amino] phenyl} ethyl;
and compounds in which X = S, R 1 = R 2 = R 4 = R 5 = H, R 3 = 1-methyl-cyclopentyl, R 6 = 2-amino-1- (S) - {3 - [( furan-2-carbonyl) amino] phenyl} ethyl, 2-amino-1 (S) - {3 - [(1-methyl-1H-pyrazole-3-carbonyl) amino] phenyl} ethyl. 2. Соединения по п.1, представляющие собой замещенные фуро[2,3-b]хинолин-2-карбоксамиды и тиено[2,3-b]хинолин-2-карбоксамиды, содержащие пиперидиновый, пиперазиновый или пирролидиновый фрагмент, общей формулы II
Figure 00000076

Figure 00000077
Figure 00000078

где R1, R2, R3, R4 и Х имеют вышеуказанное значение; W представляет собой замещенные пиперидин, пиперазин или пирролидин;
R6, R7, R8, R9 и R10 независимо друг от друга представляют собой водород, возможно замещенные C1-С6-алкил, С3-С6-циклоалкил, возможно замещенные фенил, этоксикарбонил, карбамоил, оксогруппу;
n - означает число -C(R11R12)- групп и принимает значения от 0 до 3;
R11, R12 представляют собой водород;
Y - представляет собой углерод или азот.2. The compounds according to claim 1, which are substituted furo [2,3-b] quinoline-2-carboxamides and thieno [2,3-b] quinoline-2-carboxamides containing a piperidine, piperazine or pyrrolidine fragment of the general formula II
Figure 00000076

Figure 00000077
Figure 00000078

where R 1 , R 2 , R 3 , R 4 and X have the above meaning; W represents substituted piperidine, piperazine or pyrrolidine;
R 6 , R 7 , R 8 , R 9 and R 10 independently represent hydrogen, optionally substituted C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, optionally substituted phenyl, ethoxycarbonyl, carbamoyl, oxo;
n - means the number of -C (R 11 R 12 ) - groups and takes values from 0 to 3;
R 11 , R 12 represent hydrogen;
Y - represents carbon or nitrogen. 3. Соединения по п.1 или 2, представляющие собой замещенные N-((пиперидин-4-ил)метил)фуро[2,3-b]хинолин-2-карбоксамиды и замещенные N-((пиперидин-4-ил)метил)тиено[2,3-b]хинолин-2-карбоксамиды общей формулы III
Figure 00000079

где R1, R2, R10 и Х имеют вышеуказанное значение.3. The compounds according to claim 1 or 2, which are substituted N - ((piperidin-4-yl) methyl) furo [2,3-b] quinoline-2-carboxamides and substituted N - ((piperidin-4-yl) methyl) thieno [2,3-b] quinoline-2-carboxamides of the general formula III
Figure 00000079

where R 1 , R 2 , R 10 and X have the above meaning. 4. Способ получения фуро[2,3-b]хинолин-2-карбоксамидов (Х=O) 3 и тиено[2,3-b]хинолин-2-карбоксамидов (X=S) 4 по любому из пп.1-3 взаимодействием замещенных карбоновых кислот 1 с подходящими аминами 2 в присутствии 1,1'-карбонилдиимидазола (КДИ) в среде органического растворителя
Figure 00000080
4. The method of obtaining furo [2,3-b] quinoline-2-carboxamides (X = O) 3 and thieno [2,3-b] quinoline-2-carboxamides (X = S) 4 according to any one of claims 1- 3 by reacting substituted carboxylic acids 1 with suitable amines 2 in the presence of 1,1'-carbonyldiimidazole (CDI) in an organic solvent
Figure 00000080
 5. Активное начало для фармацевтических композиций и лекарственных средств, обладающее противотуберкулезной активностью и представляющее собой соединения общей формулы I по любому из пп.1, 2 или 3.5. The active principle for pharmaceutical compositions and medicines, having anti-tuberculosis activity and representing compounds of general formula I according to any one of claims 1, 2 or 3. 6. Фармацевтическая композиция, обладающая противотуберкулезной активностью, содержащая фармацевтически эффективное количество активного начала по п.5.6. A pharmaceutical composition having anti-tuberculosis activity, comprising a pharmaceutically effective amount of an active principle according to claim 5. 7. Способ получения фармацевтической композиции по п.6 смешением эффективного количества активного начала по п.5 с инертным наполнителем и/или растворителем.7. The method of obtaining the pharmaceutical composition according to claim 6 by mixing an effective amount of the active principle according to claim 5 with an inert filler and / or solvent. 8. Лекарственное средство в форме таблеток, капсул или инъекций, помещенных в фармацевтически приемлемую упаковку, для профилактики и лечения туберкулеза, включающее в свой состав активное начало по п.5 или фармацевтическую композицию по п.7.8. A medicine in the form of tablets, capsules or injections in a pharmaceutically acceptable package for the prevention and treatment of tuberculosis, comprising the active principle according to claim 5 or the pharmaceutical composition according to claim 7. 9. Способ профилактики и лечения туберкулеза путем введения лекарственного средства по п.8. 9. A method for the prevention and treatment of tuberculosis by administering the drug of claim 8.
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EP3498701A1 (en) * 2012-12-21 2019-06-19 Epizyme Inc Prmt5 inhibitors and uses thereof
EP4219465A3 (en) * 2012-12-21 2023-09-27 Epizyme, Inc. Prmt5 inhibitors and uses thereof
US10980794B2 (en) 2012-12-21 2021-04-20 Epizyme, Inc. PRMT5 inhibitors and uses thereof
WO2014207213A1 (en) 2013-06-28 2014-12-31 Medizinische Universität Innsbruck Novel inhibitors of protein kinase c epsilon signaling
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
CN109096292B (en) * 2018-08-24 2019-09-10 河南大学 A kind of small organic molecule probe, preparation method and application
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