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

Info

Publication number
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
Authority
RU
Russia
Prior art keywords
substituted
possibly
amino
phenyl
carboxamides
Prior art date
Application number
RU2008102156/04A
Other languages
Russian (ru)
Other versions
RU2008102156A (en
Inventor
Александр Васильевич Иващенко (US)
Александр Васильевич Иващенко
Андрей Александрович Иващенко (RU)
Андрей Александрович Иващенко
Дмитрий Владимирович Кравченко (RU)
Дмитрий Владимирович Кравченко
Original Assignee
Андрей Александрович Иващенко
Алла Хем, Ллс
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Андрей Александрович Иващенко, Алла Хем, Ллс filed Critical Андрей Александрович Иващенко
Priority to RU2008102156/04A priority Critical patent/RU2371444C1/en
Publication of RU2008102156A publication Critical patent/RU2008102156A/en
Application granted granted Critical
Publication of RU2371444C1 publication Critical patent/RU2371444C1/en

Links

Images

Landscapes

  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

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.

Figure 00000001
Figure 00000002
Figure 00000003
Figure 00000004
Figure 00000005
Figure 00000006
Figure 00000007
Figure 00000008
Figure 00000009
Figure 00000010
Figure 00000011
Figure 00000012
Figure 00000013
Figure 00000014
Figure 00000015
Figure 00000016
Figure 00000017
Figure 00000018
Figure 00000019
Figure 00000020
Figure 00000021
Figure 00000022
Figure 00000023
Figure 00000024
Figure 00000025
Figure 00000026
Figure 00000027
Figure 00000028
Figure 00000029
Figure 00000030
Figure 00000031
Figure 00000032
Figure 00000033
Figure 00000034
Figure 00000035
Figure 00000036
Figure 00000037
Figure 00000038
Figure 00000039
Figure 00000040
Figure 00000041
Figure 00000042
Figure 00000043
Figure 00000044
Figure 00000045
Figure 00000046
Figure 00000047
Figure 00000048
Figure 00000049
Figure 00000050
Figure 00000051
Figure 00000052
Figure 00000053
Figure 00000054
Figure 00000055
Figure 00000056
Figure 00000057
Figure 00000058
Figure 00000059
Figure 00000060
Figure 00000061
Figure 00000062
Figure 00000063
Figure 00000064
Figure 00000065
Figure 00000066
Figure 00000067
Figure 00000068
Figure 00000069
Figure 00000070
Figure 00000071
Figure 00000072
Figure 00000073
Figure 00000074
The text of the description is given in facsimile form.
Figure 00000001
Figure 00000002
Figure 00000003
Figure 00000004
Figure 00000005
Figure 00000006
Figure 00000007
Figure 00000008
Figure 00000009
Figure 00000010
Figure 00000011
Figure 00000012
Figure 00000013
Figure 00000014
Figure 00000015
Figure 00000016
Figure 00000017
Figure 00000018
Figure 00000019
Figure 00000020
Figure 00000021
Figure 00000022
Figure 00000023
Figure 00000024
Figure 00000025
Figure 00000026
Figure 00000027
Figure 00000028
Figure 00000029
Figure 00000030
Figure 00000031
Figure 00000032
Figure 00000033
Figure 00000034
Figure 00000035
Figure 00000036
Figure 00000037
Figure 00000038
Figure 00000039
Figure 00000040
Figure 00000041
Figure 00000042
Figure 00000043
Figure 00000044
Figure 00000045
Figure 00000046
Figure 00000047
Figure 00000048
Figure 00000049
Figure 00000050
Figure 00000051
Figure 00000052
Figure 00000053
Figure 00000054
Figure 00000055
Figure 00000056
Figure 00000057
Figure 00000058
Figure 00000059
Figure 00000060
Figure 00000061
Figure 00000062
Figure 00000063
Figure 00000064
Figure 00000065
Figure 00000066
Figure 00000067
Figure 00000068
Figure 00000069
Figure 00000070
Figure 00000071
Figure 00000072
Figure 00000073
Figure 00000074

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.
RU2008102156/04A 2008-01-24 2008-01-24 FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY RU2371444C1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
RU2008102156/04A RU2371444C1 (en) 2008-01-24 2008-01-24 FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
RU2008102156/04A RU2371444C1 (en) 2008-01-24 2008-01-24 FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY

Publications (2)

Publication Number Publication Date
RU2008102156A RU2008102156A (en) 2009-07-27
RU2371444C1 true RU2371444C1 (en) 2009-10-27

Family

ID=41047995

Family Applications (1)

Application Number Title Priority Date Filing Date
RU2008102156/04A RU2371444C1 (en) 2008-01-24 2008-01-24 FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY

Country Status (1)

Country Link
RU (1) RU2371444C1 (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014207213A1 (en) 2013-06-28 2014-12-31 Medizinische Universität Innsbruck Novel inhibitors of protein kinase c epsilon signaling
CN109096292A (en) * 2018-08-24 2018-12-28 河南大学 A kind of small organic molecule probe, preparation method and application
EP3498701A1 (en) * 2012-12-21 2019-06-19 Epizyme Inc Prmt5 inhibitors and uses thereof
CN112480134A (en) * 2020-12-17 2021-03-12 河南大学 Pair of isomers, preparation method and application thereof
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11459338B2 (en) 2017-11-24 2022-10-04 Jubilant Episcribe Llc Heterocyclic compounds as PRMT5 inhibitors
CN115197240A (en) * 2021-07-08 2022-10-18 江南大学 Quinoline compound, synthesis method, pharmaceutical composition and application
US11529341B2 (en) 2018-03-13 2022-12-20 Jubilant Prodel LLC Bicyclic compounds as inhibitors of PD1/PD-L1 interaction/activation
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CIUSTEA MIHAI et al. Identification of Non-Nucleoside DNA Synthesis Inhibitors of Vaccinia Virus by High-Throughput Screening. Journal of Medicinal Chemistry. 2008, 51(20), 6563-6570. RAGHAVENDRA M. et al. Microwave-assisted one-pot synthesis of some new furo[2,3-b]quinolines using potassium carbonate under solvent-free conditions. Canadian Journal of Chemistry, 2007, 85(12), 1041-1044. ВАСHIТЕ, ETIFY ABDEL-GHAFAR. Synthesis of new pyrazolo[3,4-b]quinolines, thieno[2,3-b]quinolines, and related condensed heterocyclic systems. Journal of the Chinese Chemical Society, 2001, 48(6B), 1175-1183. MEKHEIMER, RAMADAN A. et al. Fused quinoline heterocycles IV. First synthesis of four heterocyclic ring systems of 1H-5-thia-1,2,3,6-tetraazaacephenanthrylenes and 1H-5-thia-1,3,6-triazaacephenanthrylenes. Phosphorus, Sulfur and Silicon and the Related Elements, 2001, 175, 49-63. FATHY N.M. Synthesis of some thienoquinoline derivatives with expected pharmacological activity. Communications de la Fac *

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
CN109096292A (en) * 2018-08-24 2018-12-28 河南大学 A kind of small organic molecule probe, preparation method and application
CN112480134A (en) * 2020-12-17 2021-03-12 河南大学 Pair of isomers, preparation method and application thereof
CN115197240A (en) * 2021-07-08 2022-10-18 江南大学 Quinoline compound, synthesis method, pharmaceutical composition and application
CN115197240B (en) * 2021-07-08 2024-03-26 江南大学 Quinoline compound, synthesis method, pharmaceutical composition and application

Also Published As

Publication number Publication date
RU2008102156A (en) 2009-07-27

Similar Documents

Publication Publication Date Title
RU2371444C1 (en) FURO- AND THIENO[2,3-b]-QUINOLINE-2-CARBOXAMIDES, METHOD OF PRODUCTION AND ANTITUBERCULOUS ACTIVITY
RU2345996C1 (en) Annelated azaheterocyclic amides, which include pyrimidine fragment, method of obtaining and their application
RU2395506C2 (en) Chemokine receptor antagonists
RU2424240C2 (en) Antibacterial piperidine derivatives
RU2388750C2 (en) Inhibitors of phosphodiesterase 4 containing n-substituted diarylamine analogues
RU2321579C2 (en) Substituted derivatives of cyclohexan-1,4-diamine, method for their preparing and drug
RU2007128085A (en) QUALITY AMMONIUM SALTS AS AN M3 ANTAGONISTS
CA3085590A1 (en) Substituted indole compounds useful as tlr inhibitors
MX2007007428A (en) Heterocyclic compounds as ccr2b antagonists.
PE20060609A1 (en) DERIVATIVES OF QUINUCLIDINES AS ANTAGONISTS OF THE MUSCARINAL RECEPTOR (M3)
KR20040043197A (en) Aminoalkyl-substituted aromatic bicyclic compounds, method for the production thereof and their use as medicaments
UY29421A1 (en) NEW COMPOUNDS OF N- (N-SULFONYLAMINOARILMETIL) CYCLOPROPANOCARBOXANIDA SUBSTITUTED, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM TO APPLICATIONS.
AR067475A1 (en) NON BASIC S ANTAGONISTS OF THE RECEIVER OF THE CONCENTRATING HORMONE OF MELANINA 1
RU2007101685A (en) MODULATORS OF NICOTINE ACETYLCHOLINE ALPHA 7 RECEPTORS AND THEIR THERAPEUTIC APPLICATIONS
RU2009143926A (en) PYRIDINE DERIVATIVES REPLACED BY A HETEROCYCLIC CYCLE AND PHOSPHONOAMINO GROUP, AND CONTAINING THEIR ANTIFUNGIC AGENT
RU2007128080A (en) Pyrrolidinium derivatives as muscarinic receptors of the Ministry of Health
RU2015156524A (en) NEW CONDENSED PYRIMIDINE COMPOUND OR ITS SALT
RU2006138426A (en) Thiazolopyridine derivatives containing their pharmaceutical compositions and methods for treating conditions mediated by glucokinase
PE20080371A1 (en) N-BENZOIL-Y-N-BENZYLPYRROLIDIN-3-ILAMINES AS HISTAMINE-3 ANTAGONISTS
WO2006088193A1 (en) Anti-tumor agent
RU2004121688A (en) 7-AMINOBENZENESIAZOLE DERIVATIVES AS LIGANDS OF THE Adenosine Receptor
RU2009146124A (en) DIHYDROCHINOIN AND DYHIDRONAFTHYRIDINE JNK KINASE INHIBITORS
RU2348628C2 (en) Oxazolidinone antibiotics substituted by cyclopropyl group, and their derivatives
MXPA05009660A (en) Pyridyloxymethyl and benzisoxazole azabicyclic derivatives.
JP7086608B2 (en) Voltage-gated T-type calcium channel inhibitor

Legal Events

Date Code Title Description
MM4A The patent is invalid due to non-payment of fees

Effective date: 20120125

NF4A Reinstatement of patent

Effective date: 20121210

MM4A The patent is invalid due to non-payment of fees

Effective date: 20160125