DK2142499T3 - Substituerede sulfonamider, fremgangsmåde til deres fremstilling, farmaceutisk præparat bestående deraf og deres anvendelse til behandling af glaukom - Google Patents

Substituerede sulfonamider, fremgangsmåde til deres fremstilling, farmaceutisk præparat bestående deraf og deres anvendelse til behandling af glaukom Download PDF

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DK2142499T3
DK2142499T3 DK08741979.2T DK08741979T DK2142499T3 DK 2142499 T3 DK2142499 T3 DK 2142499T3 DK 08741979 T DK08741979 T DK 08741979T DK 2142499 T3 DK2142499 T3 DK 2142499T3
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benzene
bis
sulfonamide
sulfamoyl
benzamide
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Fridrich Gregan
Milan Remko
Elena Sluciakova
Jarmila Knapikova
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Unimed Pharma Spol Sro
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    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/17—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
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    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

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Claims (11)

1. Anvendelse af substituerede sulfonamider med den almene formel (I)
(l) hvori hvis R1 er CO, så er R2 NH eller O, og hvis R1 er S02, så er R2 NH; og R omfatter tertiær diCi-4alkylaminogrupper, hvor alkylenhederne er de samme eller forskellige, eller aminogrupper, hvor alkylenhederne tilsammen danner 5, 6 eller 7-ledede mættede ringe eller deres ender er forbundne via heteroatomet O, eller R er 4-(N,N-diethylaminoethoxy)benzyl når R1 er S02 og R2 er NH; eller R er 4[N-(morpholinopropyl)sulfamoyl]phenyl når R1 er CO og R2 er NH; og n er antallet af carbonatomer i den forbindende alifatiske kæde, hvor n er 0, 2 eller 3, og/eller fysiologisk acceptable salte, hydrater eller solvater deraf, til fremstilling af et lægemiddel til behandling af glaukom.
2. Anvendelse af substituerede sulfonamider med den almene formel (I) ifølge krav 1, hvori når R1 er CO, så er R2, R og n som vist i nedenstående tabel:
og/eller fysiologisk acceptable salte, hydrater eller solvater deraf, til fremstilling af et lægemiddel til behandling af glaukom.
3. Anvendelse af substituerede sulfonamider med den almene formel (I) ifølge krav 1,
(O hvori R1 er S02, R2 er NH, og R og n er som vist i nedenstående tabel:
og/eller fysiologisk acceptable salte, hydrater eller solvater deraf, til fremstilling af et lægemiddel til behandling af glaukom.
4. Anvendelse af substituerede sulfonamider ifølge et af de foregående krav hvilke har den almene formel (I) ifølge krav 1, og som er valgt blandt: N-(N,N-Diethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-1), N-(N,N-Diethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-2), N-(Pyrrolidinoethyl)benzen-l,4-bis(sulfonamid); (1-3), N-(Pyrrolidinopropyl)benzen-l,4-bis(sulfonamid); (1-4), N-(Morpholinoethyl)benzen-l,4-bis(sulfonamid); (1-5), N-(Morpholinopropyl)benzen-l,4-bis(sulfonamid); (1-6), N-(4-Diethylaminoethoxybenzyl)benzen-l,4-bis(sulfonamid); (1-7), N-(Dimethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-8), N-(Dimethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-9), N-(N,N-Dipropylaminoethyl)benzen-l,4-bis(sulfonamid); (I-10), N-(N,N-Dipropylaminopropyl)benzen-l,4-bis(sulfonamid); (I-11), N-(N,N-Dibutylaminoethyl)benzen-l,4-bis(sulfonamid); (1-12), N-(N,N-Dibutylaminopropyl)benzen-l,4-bis(sulfonamid); (1-13), N-(N-Methyl-N-ethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-14), N-(N-Methyl-N-ethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-15), N-(N-Ethyl-N-propylaminoethyl)benzen-l,4-bis(sulfonamid); (1-16), N-(N-Ethyl-N-propylaminopropyl)benzen-l,4-bis(sulfonamid); (1-17), N-(N-Ethyl-N-butylaminoethyl)benzen-l,4-bis(sulfonamid); (1-18), N-(N-Ethyl-N-butylaminopropyl)benzen-l,4-bis(sulfonamid); (1-19), N-(n-Propyl-N-butylaminoethyl)benzen-l,4-bis(sulfonamid); (1-20), N-(n-Propyl-N-butylaminopropyl)benzen-l,4-bis(sulfonamid); (1-21), N-(Piperidinoethyl)benzen-l,4-bis(sulfonamid); (1-22), N-(Piperidinopropyl)benzen-l,4-bis(sulfonamid); (1-23), 4-Sulfamoyl-N-(N,N-dimethylaminoethyl)benzamid; (II-1), 4-Sulfamoyl-N-(N,N-dimethylaminopropyl)benzamid; (II-2), 4-Sulfamoyl-N-(N,N-diethylaminoethyl)benzamid; (II-3), 4-Sulfamoyl-N-(N,N-diethylaminopropyl)benzamid; (II-4), 4-Sulfamoyl-N-(morpholinoethyl)benzamid; (II-5), 4-Sulfamoyl-N-(morpholinopropyl)benzamid; (II-6), 4-[N-(Morpholinopropyl)sulfamoyl]phenylsulfamoylbenzamid; (II-7), (N,N-Diethylaminoethyl)-4-sulfamoylbenzoat; (II-8), (N,N-Diethylaminopropyl)-4-sulfamoylbenzoat; (II-9), (N,N-Dipropylaminoethyl)-4-sulfamoylbenzoat; (II-10), (N,N-Dipropylaminopropyl)-4-sulfamoylbenzoat; (II-11), 4-Sulfamoyl-N-(N,N-dipropylaminoethyl)benzamid; (11-12), 4-Sulfamoyl-N-(N,N-dipropylaminopropyl)benzamid; (11-13), (N,N-Dibutylaminoethyl)-4-sulfamoylbenzoat; (11-14), (N,N-Dibutylaminopropyl)-4-sulfamoylbenzoat; (11-15), 4-Sulfamoyl-N-(N,N-dibutylaminoethyl)benzamid; (11-16),
4-Sulfamoyl-N-(N,N-dibutylaminopropyl)benzamid; (II-17), (N-Methyl-N-ethylaminoethyl)-4-sulfamoylbenzoat; (11-18), (N-Methyl-N-ethylaminopropyl)-4-sulfamoylbenzoat; (11-19), 4-Sulfamoyl-N-(N-methyl-N-ethylaminoethyl)benzamid; (11-20), 4-Sulfamoyl-N-(N-methyl-N-ethylaminopropyl)benzamid; (11-21), (N-Ethyl-N-propylaminoethyl)-4-sulfamoylbenzoat; (11-22), (N-Ethyl-N-propylaminopropyl)-4-sulfamoylbenzoat; (11-23), 4-Sulfamoyl-N-(N-ethyl-N-propylaminoethyl)benzamid; (11-24), 4-Sulfamoyl-N-(N-ethyl-N-propylaminopropyl)benzamid; (11-25), (N-Propyl-N-butylaminoethyl)-4-sulfamoylbenzoat; (11-26), (N-Propyl-N-butylaminopropyl)-4-sulfamoylbenzoat; (11-27), 4-Sulfamoyl-N-(N-propyl-N-butylaminoethyl)benzamid; (11-28), 4-Sulfamoyl-N-(N-propyl-N-butylaminopropyl)benzamid; (11-29), (N-Ethyl-N-butylaminoethyl)-4-sulfamoylbenzoat; (11-30), (N-Ethyl-N-butylaminopropyl)-4-sulfamoylbenzoat; (11-31), 4-Sulfamoyl-N-(N-ethyl-N-butylaminoethyl)benzamid; (11-32), 4-Sulfamoyl-N-(N-ethyl-N-butylaminopropyl)benzamid; (11-33), (Pyrrolidinoethyl)-4-sulfamoylbenzoat; (11-34), (Pyrrolidinopropyl)-4-sulfamoylbenzoat; (11-35), 4-Sulfamoyl-N-(pyrrolidinoethyl)benzamid; (11-36), 4-Sulfamoyl-N-(pyrrolidinopropyl)benzamid; (11-37), (Piperidinoethyl)-4-sulfamoylbenzoat; (11-38), (Piperidinopropyl)4-sulfamoylbenzoat; (11-39), 4-Sulfamoyl-N-(piperidinoethyl)benzamid; (11-40), og 4-Sulfamoyl-N-(piperidinopropyl)benzamid; (11-41).
5. Substituerede sulfonamider med den almene formel (I)
O) hvori R1 er S02, R2 NH; og R og n er som vist i nedenstående tabel:
og fysiologisk acceptable salte, hydrater eller solvater deraf.
6. Substituerede sulfonamider med den almene formel (I) ifølge krav 5, som er N-(N,N-Diethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-1), N-(N,N-Diethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-2), N-(Pyrrolidinoethyl)benzen-l,4-bis(sulfonamid); (1-3), N-(Pyrrolidinopropyl)benzen-l,4-bis(sulfonamid); (1-4), N-(Morpholinoethyl)benzen-l,4-bis(sulfonamid); (1-5), N-(Morpholinopropyl)benzen-l,4-bis(sulfonamid); (1-6), N-(4-Diethylaminoethoxybenzyl)benzen-l,4-bis(sulfonamid); (1-7), N-(Dimethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-8), N-(Dimethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-9), N-(N,N-Dipropylaminoethyl)benzen-l,4-bis(sulfonamid); (I-10), N-(N,N-Dipropylaminopropyl)benzen-l,4-bis(sulfonamid); (I-11), N-(N,N-Dibutylaminoethyl)benzen-l,4-bis(sulfonamid); (1-12), N-(N,N-Dibutylaminopropyl)benzen-l,4-bis(sulfonamid); (1-13), N-(N-Methyl-N-ethylaminoethyl)benzen-l,4-bis(sulfonamid); (1-14), N-(N-Methyl-N-ethylaminopropyl)benzen-l,4-bis(sulfonamid); (1-15), N-(N-Ethyl-N-propylaminoethyl)benzen-l,4-bis(sulfonamid); (1-16), N-(N-Ethyl-N-propylaminopropyl)benzen-l,4-bis(sulfonamid); (1-17), N-(N-Ethyl-N-butylaminoethyl)benzen-l,4-bis(sulfonamid); (1-18), N-(N-Ethyl-N-butylaminopropyl)benzen-l,4-bis(sulfonamid); (1-19), N-(n-Propyl-N-butylaminoethyl)benzen-l,4-bis(sulfonamid); (1-20), N-(n-Propyl-N-butylaminopropyl)benzen-l,4-bis(sulfonamid); (1-21), N-(Piperidinoethyl)benzen-l,4-bis(sulfonamid); (1-22), og N-(Piperidinopropyl)benzen-l,4-bis(sulfonamid); (1-23).
7. Substituerede sulfonamider med den almene formel (I) ifølge krav 5 eller 6, og/eller fysiologisk acceptable salte, hydrater eller solvater deraf, til anvendelse som carboanhydrase-inhibitorer, såsom antiglaucoma-midler.
8. Farmaceutisk præparat til anvendelse ved profylakse og ved behandling af sygdomme, kendetegnet ved, at det omfatter et substitueret sulfonamid med den almene formel (I) ifølge krav 5 eller 6 og/eller fysiologiske acceptable salte, hydrater eller solvater deraf som den aktive forbindelse og en farmaceutiske bærer.
9. Farmaceutisk præparat ifølge krav 8, kendetegnet ved, at det omfatter et yderligere aktivt middel til profylakse eller behandling af sygdomme, især til behandling af øjensygdomme, valgt fra gruppen bestående af sympatomimetika såsom brimonidin, clonidin, apraclonidin; parasympatomimetika såsom pilocarpin, carbachole; betablokkere såsom timolol, betaxolol, levobunolol; og prostagladinanaloger såsom latanoprost, bimaprost, travaprost; og andre antiglaucoma-midler såsom guanethidin eller dapiprazol.
10. Fremgangsmåde til fremstilling af forbindelser med den almene formel (I) ifølge krav 5, kendetegnet ved at aminen med den almene formel (IV)
(IV) hvor R er som defineret i krav 5, behandles med 4-sulfamoybenzensulfonylchlorid med formel (V)
(V) i et organisk opløsningsmiddel i nærvær af overskud af base ved en temperatur på 0 til 20 °C, hvorved en nukleofil reaktion giver det substituerede 1,4-bissulfonamid.
11. Fremgangsmåden ifølge krav 10, kendetegnet ved at tetrahyd rof uran eller ether anvendes som organisk opløsningsmiddel, og triethylamin anvendes som base.
DK08741979.2T 2007-04-20 2008-04-18 Substituerede sulfonamider, fremgangsmåde til deres fremstilling, farmaceutisk præparat bestående deraf og deres anvendelse til behandling af glaukom DK2142499T3 (da)

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SK54-2007A SK542007A3 (sk) 2007-04-20 2007-04-20 Substituované sulfónamidy, spôsob ich prípravy, farmaceutický prostriedok s ich obsahom a ich použitie
PCT/SK2008/050005 WO2008130332A1 (en) 2007-04-20 2008-04-18 Subsituted sulphonamides, process for their preparation, pharmaceutical composition comprising thereof and their use

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AU2008241590B2 (en) 2012-06-21
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CA2684591A1 (en) 2008-10-30
AR065966A1 (es) 2009-07-15
PE20090807A1 (es) 2009-07-20
NZ581302A (en) 2012-03-30
UY31028A1 (es) 2008-11-28
RU2009134079A (ru) 2011-05-27
US20100125076A1 (en) 2010-05-20
TWI392492B (zh) 2013-04-11
PL2142499T3 (pl) 2015-05-29
US8193184B2 (en) 2012-06-05
WO2008130332A1 (en) 2008-10-30
UA99279C2 (ru) 2012-08-10
HUE024552T2 (hu) 2016-02-29
JO3206B1 (ar) 2018-03-08
BRPI0809728A2 (pt) 2016-10-18
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PT2142499E (pt) 2015-02-09
EP2142499B1 (en) 2014-12-10
CL2008001109A1 (es) 2008-11-03
ES2528284T3 (es) 2015-02-06
SK542007A3 (sk) 2008-11-06
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