AR064370A1 - Nitroderivados de bencenosulfonamidas sustituidas como inhibidores de anhidrasa carbonica composiciones farmaceuticas que los comprenden kits farmaceuticos para su administracion y su uso en la preparacion de un medicamento para el tratamiento del cancer y de trastornos oculares - Google Patents

Nitroderivados de bencenosulfonamidas sustituidas como inhibidores de anhidrasa carbonica composiciones farmaceuticas que los comprenden kits farmaceuticos para su administracion y su uso en la preparacion de un medicamento para el tratamiento del cancer y de trastornos oculares

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Publication number
AR064370A1
AR064370A1 ARP070105642A ARP070105642A AR064370A1 AR 064370 A1 AR064370 A1 AR 064370A1 AR P070105642 A ARP070105642 A AR P070105642A AR P070105642 A ARP070105642 A AR P070105642A AR 064370 A1 AR064370 A1 AR 064370A1
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ono2
alkyl
formula
cancer
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ARP070105642A
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Stefano Biondi
Claudiu Supuran
Francesca Benedini
Ennio Ongini
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Nicox Sa
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/088—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/16—Amides, e.g. hydroxamic acids
    • A61K31/18—Sulfonamides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • 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
    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/51—Y being a hydrogen or a 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
    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
    • C07C311/52—Y being a hetero atom
    • C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C327/00—Thiocarboxylic acids
    • C07C327/20—Esters of monothiocarboxylic acids
    • C07C327/26—Esters of monothiocarboxylic acids having carbon atoms of esterified thiocarboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms

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Abstract

Se describen los nitroderivados que se pueden emplear para el tratamiento de glaucoma, hipertension ocular, degeneracion macular relacionada con la edad, edema macular diabética, retinopatía diabética, retinopatía hipertensiva y vasculopatías retinianas, cáncer, epilepsia, trastorno de altura y enfermedades neuromusculares. Reivindicacion 1: Uso de un inhibidor de anhidrasa carbonica capaz de liberar oxido nítrico para la preparacion de un medicamento para el tratamiento de trastornos oculares y cáncer. Reivindicacion 5: Un compuesto de formula general (1) o una de sus sales aceptables para uso farmacéutico o estereoisomeros: R-(X-Y-ONO2)s, caracterizado porque s es un numero entero igual a 1 o 2; R se selecciona del grupo que consiste en formulas (2a) a (2g), donde n es un numero de 0 a 4; m es un numero entero igual a 0 o 1; R1, R2 y R3 son iguales o diferentes y son H, CI, Br, I, F, CF3, SO2NH2; X1 es -O- o -NH-; N1 es -OH, -COOH, -O-, -C(O)-, -NHR1 o -NR1- donde R1 es H o alquilo C1-6; R' es H o un grupo -(X-Y-ONO2); X es -C(O)-, -O-, -NR1-, -S-, -C(O)O- o -C(O)S-, donde R1 es H o alquilo C1-6; con la condicion de que i) cuando el grupo -(X-Y-ONO2) está unido a N1 entonces: - N1 es -O- o -NR1- y X es -C(O)-, - C(O)O- o -C(O)S-, donde R1 es H o alquilo C1-6; -N1, es -C(O)- y X es -O-, -NR1-, -S-, -C(O)O- o -C(O)S-, donde R1 es H o alquilo C1-6; ii) cuando R' es -(X-Y-ONO2) entonces X es -C(O)-, -C(O)O- o -C(O)S-; iii) cuando s es 2, entonces -X y -Y- de lo dos grupos -(X-Y-ONO2) pueden ser iguales o diferentes; Y es un radical bivalente que tiene el siguiente significado: a) alquileno C1-20 lineal o ramificado; alquileno C1-20 lineal o ramificado sustituido con uno o más de los sustituyentes seleccionados del grupo que consiste en átomos de halogeno, hidroxi, -ONO2 o T, donde T es -OC(O)(alquilo C1-10)-ONO2 u -O(alquilo C1-10)-ONO2; cicloalquileno con 5 a 7 átomos de carbono del anillo cicloalquileno, el anillo está opcionalmente sustituido con cadenas laterales T1, donde T1 es un alquilo C1-10 lineal o ramificado; b) grupo de formula (3); c) grupo de formula (4) donde n0 es un numero de 0 a 20, n1 es un numero de 1 a 20, d) un grupo de formula (5) donde X1 = -OC(O)- o - C(O)O-; n2 es un numero de 0 a 2; R2 es H o CH3; Z es -(CH2)n1- o el radical bivalente definido anteriormente con b), donde n1 es un numero de 1 a 20; e) es un grupo con las formulas (6) y (7) donde Y1 es -CH2-CH2-(CH2)n2a- o -CH=CH-(CH2)n2a- donde n2a es de 0 a 2, X1 es -OC(O)- o -C(O)O-, n2 es un numero de 0 a 2, R2 es H o CH3, Z es -(CH2)n1- o el radical bivalente definido anteriormente en b), donde n1 es un numero de 1 a 20; cuando Y se selecciona de los radicales bivalentes mencionados en b) -e), entonces el grupo terminal -ONO2 está unido a -(CH2)n1; f) grupos (8) y (9) donde: n1'es un numero de 1 a 20, R3 es H, R0 es H o -COCH3; con la condicion de que cuando Y se selecciono entre los radicales bivalentes mencionados en f), entonces el grupo -ONO2 está unido a -(CH2)n1; g) -(CH2-X2)-CH2-CH2- , (g') -(R2)(CH-CH2-X2)n3-CH(R2)CH2- (gö) el grupo de formula (10) donde X2 es -O- o -S-, n3 es un numero de 1 a 6, R2 es H o -CH3 h) un grupo de formula (11) donde: n4 es un numero de 0 a 10; n5 es un numero de 1 a 10; R4, R5, R6, R7 son iguales o diferentes, y son H o alquilo C1-4 lineal o ramificado; donde el grupo -ONO2 está unido a -[C]n5 donde n5 es como se definio anteriormente; Y2 es un anillo heterocíclico saturado, insaturado o aromático de 5 o 6 miembros, que contiene uno o más heteroátomos seleccionados entre nitrogeno, oxígeno, azufre, y se selecciona entre los grupos de formulas (Y1) a (Y13)
ARP070105642A 2006-12-15 2007-12-14 Nitroderivados de bencenosulfonamidas sustituidas como inhibidores de anhidrasa carbonica composiciones farmaceuticas que los comprenden kits farmaceuticos para su administracion y su uso en la preparacion de un medicamento para el tratamiento del cancer y de trastornos oculares AR064370A1 (es)

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CN102203055A (zh) * 2008-09-24 2011-09-28 奈翠根尼斯公司 释放一氧化氮的氨基酸酯化合物、组成物及使用方法
US9085508B2 (en) 2008-09-24 2015-07-21 Oral Delivery Technology Ltd. Nitric oxide releasing amino acid ester compound, composition and method of use
US8062653B2 (en) * 2009-02-18 2011-11-22 Bezwada Biomedical, Llc Controlled release of nitric oxide and drugs from functionalized macromers and oligomers
WO2011098610A1 (en) * 2010-02-12 2011-08-18 Universita Degli Studi Di Firenze Carbonic anhydrase inhibitors
NL1038473C2 (en) 2010-12-24 2012-06-27 Centre Nat Rech Scient Cancer targeting using carbonic anhydrase isoform ix inhibitors.
WO2012175654A1 (en) 2011-06-23 2012-12-27 Facultes Universitaires Notre-Dame De La Paix Tetraline sulfonamide derivatives for use in the treatment of proliferative disorders
CN102675404B (zh) * 2012-05-10 2014-04-09 福建天泉药业股份有限公司 一种甘草次酸硝酸丁酯的制备方法
ITRM20130138A1 (it) 2013-03-07 2014-09-08 Consiglio Nazionale Ricerche Assemblato comprendente un assorbitore della luce nel vicino infrarosso legato covalentemente ad un inibitore dell'anidrasi carbonica
WO2015025283A2 (en) 2013-08-20 2015-02-26 Stichting Maastricht Radiation Oncology "Maastro-Clinic" Dual action carbonic anhydrase inhibitors
CN104478727A (zh) * 2014-12-22 2015-04-01 江西本草天工科技有限责任公司 一种阿魏酸释放一氧化氮的衍生物及其用途
LT6401B (lt) 2015-07-28 2017-06-12 Vilniaus Universitetas Karboanhidrazės selektyvūs inhibitoriai
CN115697981A (zh) 2020-06-02 2023-02-03 耶迪特普大学 作为碳酸酐酶ix的抑制剂用于治疗癌症的2-(3-(2-甲基-6-(对甲苯基)吡啶-3-基)脲基)苯磺酰胺及衍生物

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