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WO2004078731A1 - Acides quinoline-carboxyliques et leurs derives et bibliotheque focalisee - Google Patents

Acides quinoline-carboxyliques et leurs derives et bibliotheque focalisee Download PDF

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Publication number
WO2004078731A1
WO2004078731A1 PCT/RU2004/000081 RU2004000081W WO2004078731A1 WO 2004078731 A1 WO2004078731 A1 WO 2004078731A1 RU 2004000081 W RU2004000081 W RU 2004000081W WO 2004078731 A1 WO2004078731 A1 WO 2004078731A1
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substituted
treatment
optionally substituted
neοbyazaτelnο
group
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Russian (ru)
Inventor
Alexander Vasilievich Ivashchenko
Vladimir Vasilievich Kobak
Volodymyr Mikhailovich Kysil
Yulia Aleksandrovna Kuzovkova
Alexey Petrovich Ilyin
Dmitri Vladimirovich Kravchenko
Sergey Yevgenievich Tkachenko
Alexander Viktorovich Khvat
Ilya Matusovich Okun
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'chemical Diversity Research Institute' Ltd
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'chemical Diversity Research Institute' Ltd
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Priority claimed from RU2003106182/04A external-priority patent/RU2229475C1/ru
Priority claimed from RU2003124470/04A external-priority patent/RU2260002C2/ru
Priority claimed from RU2003125937/04A external-priority patent/RU2257385C2/ru
Application filed by 'chemical Diversity Research Institute' Ltd filed Critical 'chemical Diversity Research Institute' Ltd
Publication of WO2004078731A1 publication Critical patent/WO2004078731A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems

Definitions

  • Acidic acid and their derivatives a specialized library
  • ⁇ ⁇ ezul ⁇ a ⁇ e ⁇ vedenny ⁇ issled ⁇ vany, na ⁇ avlenny ⁇ on ⁇ is ⁇ n ⁇ vy ⁇ bi ⁇ l ⁇ giches ⁇ i a ⁇ ivny ⁇ s ⁇ edineny in ⁇ m including sele ⁇ ivn ⁇ ⁇ davlyayuschi ⁇ ⁇ g ⁇ ammi ⁇ uemuyu ⁇ le ⁇ chnuyu sme ⁇ (a ⁇ z) iz ⁇ b ⁇ e ⁇ a ⁇ eli ⁇ bna ⁇ uzhili n ⁇ vy ⁇ em ⁇ i ⁇ ne ⁇ e ⁇ idny ⁇ ingibi ⁇ v ⁇ as ⁇ az-3.
  • active medicinal substances selectively suppressing programmable cell death (apoptosis); and also to specialized libraries and pharmaceutical companies containing the indicated compounds; as well as the method of their treatment and the method of their use for the treatment and treatment of various diseases, including those associated with increased activation of the disease.
  • ⁇ n ⁇ g ⁇ chislennye issled ⁇ vaniya, ⁇ vedennye in ⁇ slednee v ⁇ emya, ⁇ iveli ⁇ ⁇ y ⁇ iyu vys ⁇ e ⁇ e ⁇ ivny ⁇ ingibi ⁇ v ⁇ as ⁇ azy-3 ⁇ yadu ⁇ e ⁇ idny ⁇ ( ⁇ ags ⁇ a- Sa ⁇ ⁇ .; ⁇ e ⁇ egz ⁇ ⁇ .; e ⁇ ⁇ .; ⁇ ie ⁇ ⁇ .; ⁇ s ⁇ z ⁇ ⁇ .; ⁇ e ⁇ u ⁇ . ⁇ YSh ⁇ ⁇ * sh ⁇ a ⁇ !
  • the following compounds may serve, for example, the following manufactured products that have been developed by the company ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ⁇ ... ( ⁇ tazeSh ⁇ L .; ⁇ a ⁇ z ⁇ e? J corresponding .; ⁇ e ⁇ a ⁇ zku ⁇ . ⁇ ⁇ ⁇ . ⁇ S ⁇ 0,179,162, 2001), ⁇ egsk ⁇ g ⁇ zz ⁇ Sy ⁇ as ⁇ a @ S ⁇ . ( ⁇ réelle ⁇ , ⁇ .; ⁇ technically
  • ⁇ a ⁇ , nedavn ⁇ were ⁇ bna ⁇ uzheny ⁇ as ⁇ aznye ingibi ⁇ y in ⁇ yadu ⁇ inaz ⁇ lin ⁇ v, vesches ⁇ va ⁇ bladayu ⁇ ume ⁇ enn ⁇ y a ⁇ ivn ⁇ s ⁇ yu and sele ⁇ ivn ⁇ s ⁇ yu ( ⁇ s ⁇ C; ⁇ ka ⁇ eg-C; " ⁇ ktz ⁇ .; ⁇ as ⁇ z ⁇ .; ⁇ teg 1; ⁇ ga ⁇ ee ⁇ .; ⁇ a ⁇ ⁇ .; ⁇ a ⁇ ekag 8.
  • chinolin-4 is immune to disease properties.
  • 1,3-dioxo-1,3-dihydrogen-2 [3,4-s] are used chinulin1 (ZY), 4 (5Y) -one and pyrolysis [3,4-s] chinulinZ (1Ya), 4 (5Y) -one-ligand ⁇ réelle réelle réelle ssen ssen ssen.
  • This invention is for substituted chinoline-carboxylic acids and their derivatives 1, 2 and 3
  • ⁇ halogen, an optionally substituted alkyl, an optionally substituted amine group or an optionally substituted hydroxy group;
  • ⁇ Play presents: hydrogen, a halogen atom, an inert substituent, a substituted C-C7 alkyl, a substituted C 2 -C 7 alkenyl, an optionally substituted amine group or an optional non-substituted;
  • Imports water, a large group, or a group-C ( ⁇ ) ⁇ 8 ; or ⁇ 3 and ⁇ 4 instead provide an optionally substituted ample piece - ( ⁇ 2 ) t - 5 where m 3-7; 7
  • ⁇ 5 Delivers: an optionally substituted hydroxy group, a substituted hydroxy group, an optionally substituted amine group, or an optionally substituted or condensed;
  • ⁇ 6 Provides: a hydrogen or inert substituent; ⁇ 7 ⁇ eds ⁇ avlyae ⁇ a ⁇ m v ⁇ d ⁇ da, ine ⁇ ny zames ⁇ i ⁇ el, a ⁇ m gal ⁇ gena, cF 3 S ⁇ , ⁇ 2 ne ⁇ byaza ⁇ eln ⁇ substituted gid ⁇ silnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted ⁇ a ⁇ b ⁇ silnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted amin ⁇ a ⁇ b ⁇ nilnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted al ⁇ ilsul ⁇ nilnuyu g ⁇ u ⁇ u, ne ⁇ byaza
  • ⁇ 8 Provides: an optionally substituted amine group or an optionally substituted hydroxy group
  • ⁇ ⁇ represents acid or ⁇ - ⁇ 9 group
  • ⁇ ⁇ eds ⁇ avlyae ⁇ 9 a ⁇ m v ⁇ d ⁇ da, ine ⁇ ny zames ⁇ i ⁇ el, ne ⁇ byaza ⁇ eln ⁇ substituted amin ⁇ g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted gid ⁇ silnuyu g ⁇ u ⁇ u substituted S ⁇ al ⁇ il C-substituted C 2 -C 7 al ⁇ enil substituted C 2 -C 7 al ⁇ inil substituted in al ⁇ iln ⁇ m or C 7 a ⁇ iln ⁇ m ⁇ agmen ⁇ e - S ⁇ 2 a ⁇ al ⁇ il, zameschennsh in al ⁇ iln ⁇ m or ge ⁇ e ⁇ tsi ⁇ liches ⁇ m ⁇ agmen ⁇ e C - S ⁇ 2 ge ⁇ e ⁇ tsi ⁇ lilal ⁇ il, zameschennsh in al ⁇ iln ⁇ m or a ⁇ iln ⁇ m ⁇ agmen ⁇ e C 7
  • This invention is for the use of substituted chinoline-carboxylic acids and their derivatives of general formula 1, 2 or 3, or both 9
  • “REMOTE” means a series of compounds that are united by a common structure and possesses a shared property, which is, in fact, independent of it. To be honest, for example, the “new potassium channel activity assay”, or the “known inhibitory potency assay”, and so on. Generally, the presence of a common business unit in the compounds in the framework of a single technology is an unavailable and unavailable condition for unavailability. “Scaffold” means the general structured formula or molecular structure or the invariant area of the compounds, which is suitable for all the connections included in the space.
  • Substitute means a chemical radical that is quickly connected to a synthesized process or synthetic product in the process of the synthesis of biological compounds. ⁇
  • a substitute you can serve, for example, a halogen atom, a hydroxyl 10
  • Preferred “inert substitutes” are C ⁇ - C 7 alkyl, C 2 - C 7 alkenyl, C - C 7 alkynyl, C ⁇ - C alkoxy, C - C ⁇ 2 aralkyl, C - C 2 alkaryl, C 3 - Syu cycloalkyl, C 3 - Syu cycloalkenyl, phenyl, substituted phenyl, ( ⁇ 2 ) t- ⁇ - ( ⁇ - ⁇ 7 alkyl), - ( ⁇ 2 ) t - ⁇ ( ⁇ - ⁇ 7 alkyl ) ⁇ , aryl, substituted aryl, heterocyclyl and substituted heterocyclyl.
  • Optionally substituted radical means radical, which has a substituent or radical without a substituent. “Substituted radical” means radical, a substitute is available to someone else. “Uril” means one or several aromatic cycles, each of which includes 5 or 6 carbons. “Err” may be a condensed one, for example, like phthaline or not condensed, such as biphenyl. “Substituted aryl” has one or several “inert substitutes”. “Halogen” means a phthorepus, cold, bromo or iodine.
  • Heterocycle means one or a few saturated or aromatic rings with 5, 6 or 7 atoms, which is the last measure, one of the loops is a geter. The preferred hetero- thems are sulfur, acid and nitrogen. “Heterocycle” can be a condensed or dumb policeman, for example, like benzimidazole, benzene. benzothiazole, quinoline or non-condensed, for example, as bipyridyl and others.
  • “Wetter” means a heterocycle, including, at the very least, one atom of nitrogen, for example, like benzimidazole, benzoxazole. benzothiazole, quinoline, pyrazole, imidazole, oxazole. eleven
  • Substituted heterocycle means a heterocycle having one or more substitutes.
  • This invention is for substituted chinoline-carboxylic acids and their derivatives in general formulas 1, 2 and 3
  • ⁇ 5 Provides: an optionally substituted hydroxy group, a substituted hydroxy group, an optionally substituted amine group or an optionally substituted or condensed azoo; ⁇ Used for: hydrogen or inert substituent; ⁇ 7 ⁇ eds ⁇ avlyae ⁇ a ⁇ m v ⁇ d ⁇ da, ine ⁇ ny zames ⁇ i ⁇ el, a ⁇ m gal ⁇ gena, cF 3 S ⁇ , ⁇ 2 ne ⁇ byaza ⁇ eln ⁇ substituted gid ⁇ silnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted ⁇ a ⁇ b ⁇ silnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted amin ⁇ - ⁇ a ⁇ b ⁇ nilnuyu g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted al ⁇ ilsul ⁇ nilnuyu g ⁇ u ⁇ u, ne ⁇ byaza
  • ⁇ 8 Provides: an optionally substituted amine group or an optionally substituted hydroxy group; ⁇ 'tervicis acid or ⁇ - ⁇ 9 group;
  • ⁇ ⁇ eds ⁇ avlyae ⁇ 9 a ⁇ m v ⁇ d ⁇ da, ine ⁇ ny zames ⁇ i ⁇ el, ne ⁇ byaza ⁇ eln ⁇ substituted amin ⁇ g ⁇ u ⁇ u, ne ⁇ byaza ⁇ eln ⁇ substituted gid ⁇ silnuyu g ⁇ u ⁇ u substituted C 7 S ⁇ al ⁇ il, zameschennsh C 2 -C 7 al ⁇ enil substituted C 2 -C 7 al ⁇ inil substituted in al ⁇ iln ⁇ m a ⁇ iln ⁇ m ⁇ agmen ⁇ e or C 7 - C 12 a ⁇ al ⁇ il substituted in al ⁇ iln ⁇ m or ge ⁇ e ⁇ tsi ⁇ liches ⁇ m ⁇ agmen ⁇ e C 7 - C 12 ge ⁇ e ⁇ tsi ⁇ lilal ⁇ il substituted in al ⁇ iln ⁇ m or a ⁇ iln ⁇ m ⁇ agmen ⁇ e C 7 - C 12 al ⁇ a ⁇ il substituted
  • This invention is a cure for the treatment of or the outcome of amelioration of the disease.
  • se ⁇ y ⁇ uchas ⁇ vuyu ⁇ ⁇ as ⁇ azy, ⁇ u ⁇ em destination ⁇ atsien ⁇ am in need of treatment, e ⁇ e ⁇ ivn ⁇ g ⁇ ⁇ liches ⁇ va ⁇ a ⁇ matsev ⁇ iches ⁇ y ⁇ m ⁇ zitsii, s ⁇ de ⁇ zhaschey in ⁇ aches ⁇ ve a ⁇ ivn ⁇ y subs ⁇ antsii, ⁇ ⁇ ayney me ⁇ e, ⁇ dnu ⁇ in ⁇ lin- ⁇ a ⁇ b ⁇ n ⁇ vuyu ⁇ isl ⁇ y or ⁇ izv ⁇ dn ⁇ e ⁇ bschey ⁇ muly 1, 2 or 3 or i ⁇ ⁇ a ⁇ matsev ⁇ iches ⁇ i ⁇ iemlemuyu s ⁇ l, ⁇ -oxide or hydrate.
  • This invention is not related to the treatment or treatment of diseases
  • This invention is not intended for use with substituted chinoline-carboxylic acids or other general pharmaceutical preparations,
  • the active activity of the compounds of Formula 1. 2 and H is divided into 9 gray compounds (Steps 1-9), which are involved in the regulation of the process ⁇ ivn ⁇ s ⁇ ⁇ as ⁇ az ⁇ edelyalas ⁇ s ⁇ s ⁇ i ⁇ assche ⁇ leniya s ⁇ ve ⁇ s ⁇ vuyuscheg ⁇ subs ⁇ a ⁇ a, ⁇ eds ⁇ avlyayuscheg ⁇ s ⁇ b ⁇ y ⁇ e ⁇ id s ⁇ s ⁇ etsi ⁇ ichn ⁇ y for ⁇ azhd ⁇ y is ⁇ lzuem ⁇ y ⁇ as ⁇ zy ⁇ sled ⁇ va ⁇ eln ⁇ s ⁇ yu amin ⁇ isl ⁇ with ⁇ is ⁇ edinenn ⁇ y ⁇ lu ⁇ estsen ⁇ n ⁇ y g ⁇ u ⁇ y (me ⁇ il ⁇ uma ⁇ in).
  • ⁇ 1 , ⁇ 3 and ⁇ 4 have the above meaning
  • ⁇ 7 has the above meaning
  • ⁇ 7 ⁇ 2
  • ⁇ 2 has the same meaning
  • Disinfectant ⁇ (0.24 g) in water (25 ml) is added while stirring the corresponding amine 8 (0.006 mol) and ethyl 1,2-dihydrogen-2-oxo-6-aminulose-2 The active mass is stirred for 3 hours at room temperature, after which they add another (0.48 g, 0.012 mol), ethanol (25 ml) and 1 hour.
  • Example 7 The general method for the production of ammonium salts of 6- (4-methyl-pyrperidin-1-sulfonyl) -quinoline-4-carboxylic acid 1 (16.17). Scheme 7
  • Example 11 The general method for the production of amides 6- (4-methyl-pyrperidine-1-sulfonyl) - chinulin-4-carboxylic acid 1 (18,19,23,27,30). Scheme 11
  • Example 12 The general method for the production of amides 6- (4-methyl-pyrperidine-1-sulfonyl) - chinulin-4-carboxylic acid 1 26-54). Scheme 12
  • Example 15 The general method for the production of 3,3-dihydro-2-oxo-2,3-dihydrogen-1-indole-5-sulfonylate is 12. Scheme 15
  • Example 16 The general method for the production of amides of 3,3-dichloro-2-oxo-2,3-dihydrogen-Sh-indole-5-sulpho acid 13.
  • Example 18 The general method of obtaining 6-sulfamoyl-quinoline-3,4-wild acid acid formula 1 (Schemes ⁇ , 19).
  • Fresh water (12 g, 0.3 mol) in water (80 ml) is gradually added to the oven at room temperature and stirring 3,3-dil-2-od-2-ind-2-od-2-ind (0.03 mol), keep stirring for 1.5-2 hours, after which they add a methyl compound 6 (0.09 mol). Mix the obtained mass at a constant temperature of 8-12 hours; It is reported that with a yield of 55-87%, 6-sulpho-chinoline-3,4-dicarboxylic acids of formula 1, containing at least IX more than 95% of the basic material (Table 4).
  • Example 24 The general method for the production of 8-sulfamoyl-1,3-dioxo-1,3-dihydride-2 ⁇ - pyro [3,4-sec] chinolens 3.
  • Example 26 4-Methyl-1,3-dioxo-2- (1,3,5-trimethyl-1Ya-pyrazol-4-yl) -2,3-dihydropo- ⁇ -pyruplo [3, 4-s] chinulin -8-armored 3 (452).
  • the resulting mixture is heated by stirring at a temperature of 80 ° C for a complete recovery of the precipitate, after which, for an additional 3 hours.
  • the reaction mixture is cooled, the precipitate is filtered off, washed on the filter with acetic anhydride, anhydrous ethylene, and 6.1 g (56%) of pyridinium 1,3-di-diened Sulphonate 3 (1-11).
  • ⁇ - ⁇ solution in methane
  • ⁇ / ⁇ : 386 [ ⁇ + 1] corresponds to the 2-phenyl-6-sulfonic acid-3, 4-xindiculum acid.
  • Steps 1–9 which are involved in the regulation of pooled mammoth excretion (apoptosis) and inflammatory processes.
  • Combinant diseases were purchased from the company. The efficiency of the distribution was allocated to the speed of the distribution of the corresponding drug, which is a specific drug for the specific 34
  • the cores are pulled out on the microscope in a complete environment and the cell technology is appreciated by the microcircuit system.
  • the processors process 20 days without the use of 24 hours without and in the presence of different concentration of compounds, which have an inhibitory activity in 3.
  • the processing of the car cassette prevents the initiation of the car cassette, which is indicated in the carcass carriage.
  • the effect of the connections in the sale of the appraisal is appreciated in the presence of the cells that have compromised the use of the equipment in the environment.
  • the cells are sown in 96-well plates with a concentrate of cells of 2x10 5 cells / cell and are consumed in a medium that is free of charge.
  • the boards are washed in a Dulbecca factory with a private buffer.
  • the connections are then added to each cell containing 200 ⁇ l of the Dulbecca's physical device with the optional battery and the fee is paid for by the minuscule.
  • the cams are single-ended and opti- mically grow and in the cells they add 200 ⁇ l 10% of the total charge.
  • EXAMPLE 32 illustrating the manufacture of tablets containing 50 mg of active ingredient. Mix, and then mix 800 mg of powder, 800 mg of crushed lactose, 200 mg of talcum powder and 500 mg of the compound of general formulas 1, 2 or 3. The resulting mixture is crushed into granules and mixed. Received granules are tested in the form of tablets weighing 280 mg each. 33.

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

L'invention concerne des compositions, des acides quinoline-carboxyliques substitués et leurs dérivés correspondant à la formule générale 1, 2 et 3 ainsi que leurs sels pharmaceutiquement acceptables, N-oxydes ou hydrates, ainsi que des procédés de fabrication correspondants, une bibliothèque focalisée, des compositions pharmaceutiques et leur utilisation. Les composés de l'invention sont des inhibiteurs d'enzymes de caspase utiles dans la prévention et le traitement de diverses maladies liées à l'activation accentuée de l'apoptose.
PCT/RU2004/000081 2003-03-06 2004-03-03 Acides quinoline-carboxyliques et leurs derives et bibliotheque focalisee Ceased WO2004078731A1 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
RU2003106182 2003-03-06
RU2003106182/04A RU2229475C1 (ru) 2003-03-06 2003-03-06 6-сульфамоилхинолин-4-карбоновые кислоты, их производные и комбинаторная библиотека
RU2003124470 2003-08-08
RU2003124470/04A RU2260002C2 (ru) 2003-08-08 2003-08-08 Замещенные 6-сульфо-2-оксо-1,2-дигидрохинолин 4-карбоновые кислоты и их производные (варианты) и фокусированная библиотека
RU2003125937/04A RU2257385C2 (ru) 2003-08-26 2003-08-26 1,3-диоксо -2,3-дигидро-1h-пирроло[3,4-c]хинолины (варианты), фармацевтические композиции (варианты), способ их получения (варианты) и способы лечения (варианты)
RU2003125937 2003-08-26

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WO2004078731A1 true WO2004078731A1 (fr) 2004-09-16

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GB2450771A (en) * 2007-04-12 2009-01-07 Angeletti P Ist Richerche Bio Heterocyclic compounds and their use as inhibitors of HCV polymersases for the treatment of HCV
WO2010004761A1 (fr) 2008-07-10 2010-01-14 一般社団法人ファルマＩｐ Inhibiteur de stat3 contenant un dérivé de quinoléinecarboxamide en tant que principe actif
US7687666B2 (en) 2006-02-17 2010-03-30 Wyeth Methods for preparing sulfonamide substituted alcohols and intermediates thereof
WO2009155527A3 (fr) * 2008-06-19 2010-06-24 Progenics Pharmaceuticals, Inc. Inhibiteurs de phosphatidylinositol 3 kinase
US7838550B2 (en) 2006-02-17 2010-11-23 Wyeth Llc Selective N-sulfonylation of 2-amino fluoro- and trifluoroalkyl substituted alcohols
EP2465502A1 (fr) * 2010-12-15 2012-06-20 Société Splicos Composés utiles pour traiter le SIDA
US9108919B2 (en) 2009-06-12 2015-08-18 Abivax Compounds useful for treating cancer
KR101564337B1 (ko) 2012-12-10 2015-10-30 주식회사 이큐스앤자루 디하이드로퀴놀린 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 인플루엔자 a형 바이러스에 의한 질환의 예방 또는 치료용 약학적 조성물
US9827237B2 (en) 2013-07-05 2017-11-28 Abivax Compounds useful for treating diseases caused by retroviruses
US10253020B2 (en) 2009-06-12 2019-04-09 Abivax Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging
EP3498701A1 (fr) * 2012-12-21 2019-06-19 Epizyme Inc Inhibiteurs de prmt5 et utilisations associées
CN112358479A (zh) * 2020-12-28 2021-02-12 西北师范大学 一种吡咯并[3,4-c]喹啉-1,3-二酮类化合物的合成方法
US11291705B2 (en) 2016-10-13 2022-04-05 Technion Research & Development Foundation Limited Use of caspase-3 inhibitors and caspase-3 activators in the manufacture of medicament for treating cancer and wound healing
US11426412B2 (en) 2017-10-18 2022-08-30 Jubilant Epipad LLC Imidazo-pyridine compounds as PAD inhibitors
US11441181B2 (en) 2013-01-17 2022-09-13 Abivax miRNA-124 as a biomarker
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
US11629135B2 (en) 2017-11-06 2023-04-18 Jubilant Prodell Llc Pyrimidine derivatives as inhibitors of PD1/PD-L1 activation
US11649211B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US11833156B2 (en) 2017-09-22 2023-12-05 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
US11992499B2 (en) 2018-12-20 2024-05-28 Abivax Quinoline derivatives for use in the treatment of inflammation diseases

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US7687666B2 (en) 2006-02-17 2010-03-30 Wyeth Methods for preparing sulfonamide substituted alcohols and intermediates thereof
US7838550B2 (en) 2006-02-17 2010-11-23 Wyeth Llc Selective N-sulfonylation of 2-amino fluoro- and trifluoroalkyl substituted alcohols
WO2007117778A3 (fr) * 2006-02-24 2008-02-07 Kalypsys Inc Quinolones utiles en tant qu'inhibiteurs de l'oxyde nitrique synthase inductible
GB2450771A (en) * 2007-04-12 2009-01-07 Angeletti P Ist Richerche Bio Heterocyclic compounds and their use as inhibitors of HCV polymersases for the treatment of HCV
WO2009155527A3 (fr) * 2008-06-19 2010-06-24 Progenics Pharmaceuticals, Inc. Inhibiteurs de phosphatidylinositol 3 kinase
US8466290B2 (en) 2008-07-10 2013-06-18 Pharma Ip General Incorporated Association STAT3 inhibitor containing quinolinecarboxamide derivative as active ingredient
WO2010004761A1 (fr) 2008-07-10 2010-01-14 一般社団法人ファルマＩｐ Inhibiteur de stat3 contenant un dérivé de quinoléinecarboxamide en tant que principe actif
KR20110039221A (ko) 2008-07-10 2011-04-15 잇반샤단호우진 파마 아이피 퀴놀린카르복사미드 유도체를 유효 성분으로 하는 ｓｔａｔ３ 저해제
US10975063B2 (en) 2009-06-12 2021-04-13 Abivax Compound, and production method thereof, and methods of treatment using the compound
US9637475B2 (en) 2009-06-12 2017-05-02 Abivax Compounds for treating cancer
US11014918B2 (en) 2009-06-12 2021-05-25 Abivax Compounds and pharmaceutical compositions containing at least one of the compounds
US10683284B2 (en) 2009-06-12 2020-06-16 Abivax Compounds for preventing, inhibiting, or treating cancer, aids and/or premature aging
US9108919B2 (en) 2009-06-12 2015-08-18 Abivax Compounds useful for treating cancer
US9145367B2 (en) 2009-06-12 2015-09-29 Abivax Compounds useful for treating AIDS
US10253020B2 (en) 2009-06-12 2019-04-09 Abivax Compounds for preventing, inhibiting, or treating cancer, AIDS and/or premature aging
US10017498B2 (en) 2009-06-12 2018-07-10 Abivax Compounds useful for treating AIDS
CN103415290A (zh) * 2010-12-15 2013-11-27 斯皮利寇斯公司 用于治疗aids的化合物
WO2012080953A1 (fr) * 2010-12-15 2012-06-21 Splicos Composés utiles pour traiter le sida
RU2598845C2 (ru) * 2010-12-15 2016-09-27 Абивакс ПРОИЗВОДНЫЕ ХИНОЛИН-2-АМИНА, ПРИГОДНЫЕ ДЛЯ ЛЕЧЕНИЯ СПИДа
CN103415290B (zh) * 2010-12-15 2016-09-14 Abivax公司 用于治疗aids的化合物
EP2465502A1 (fr) * 2010-12-15 2012-06-20 Société Splicos Composés utiles pour traiter le SIDA
US9061999B2 (en) 2010-12-15 2015-06-23 Abivax Compounds useful for treating AIDS
KR101564337B1 (ko) 2012-12-10 2015-10-30 주식회사 이큐스앤자루 디하이드로퀴놀린 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 인플루엔자 a형 바이러스에 의한 질환의 예방 또는 치료용 약학적 조성물
EP4219465A3 (fr) * 2012-12-21 2023-09-27 Epizyme, Inc. Inhibiteurs de prmt5 et leurs utilisations
US10980794B2 (en) 2012-12-21 2021-04-20 Epizyme, Inc. PRMT5 inhibitors and uses thereof
EP3498701A1 (fr) * 2012-12-21 2019-06-19 Epizyme Inc Inhibiteurs de prmt5 et utilisations associées
US11441181B2 (en) 2013-01-17 2022-09-13 Abivax miRNA-124 as a biomarker
US9827237B2 (en) 2013-07-05 2017-11-28 Abivax Compounds useful for treating diseases caused by retroviruses
US11649210B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US12202804B2 (en) 2014-07-17 2025-01-21 Abivax In vitro or ex vivo methods for screening a quinoline derivative
US11649211B2 (en) 2014-07-17 2023-05-16 Abivax Use of quinoline derivatives for the treatment of inflammatory diseases
US11291705B2 (en) 2016-10-13 2022-04-05 Technion Research & Development Foundation Limited Use of caspase-3 inhibitors and caspase-3 activators in the manufacture of medicament for treating cancer and wound healing
US12357639B2 (en) 2017-09-22 2025-07-15 Jubilant Epipad LLC Heterocyclic compounds as pad inhibitors
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
US11992499B2 (en) 2018-12-20 2024-05-28 Abivax Quinoline derivatives for use in the treatment of inflammation diseases
CN112358479A (zh) * 2020-12-28 2021-02-12 西北师范大学 一种吡咯并[3,4-c]喹啉-1,3-二酮类化合物的合成方法
CN112358479B (zh) * 2020-12-28 2023-06-16 西北师范大学 一种吡咯并[3,4-c]喹啉-1,3-二酮类化合物的合成方法

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