AR035798A1 - Compuestos inhibidores de aldosa reductasa del grupo de las piridazin-3-onas, composiciones farmaceuticas y metodos de tratamiento de isquemia y enfermedades diabeticas - Google Patents
Compuestos inhibidores de aldosa reductasa del grupo de las piridazin-3-onas, composiciones farmaceuticas y metodos de tratamiento de isquemia y enfermedades diabeticasInfo
- Publication number
- AR035798A1 AR035798A1 ARP020101134A ARP020101134A AR035798A1 AR 035798 A1 AR035798 A1 AR 035798A1 AR P020101134 A ARP020101134 A AR P020101134A AR P020101134 A ARP020101134 A AR P020101134A AR 035798 A1 AR035798 A1 AR 035798A1
- Authority
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- Argentina
- Prior art keywords
- alkyl
- optionally substituted
- substituents
- alkoxy
- hydroxy
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 5
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 3
- 206010012601 diabetes mellitus Diseases 0.000 title abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 230000002401 inhibitory effect Effects 0.000 title 1
- 208000028867 ischemia Diseases 0.000 title 1
- -1 pyrazinopyrazinyl Chemical group 0.000 abstract 35
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 12
- 125000001153 fluoro group Chemical group F* 0.000 abstract 12
- 125000001424 substituent group Chemical group 0.000 abstract 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 8
- 125000002883 imidazolyl group Chemical group 0.000 abstract 8
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 8
- 125000002971 oxazolyl group Chemical group 0.000 abstract 8
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 8
- 125000000335 thiazolyl group Chemical group 0.000 abstract 8
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 6
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 6
- 125000005843 halogen group Chemical group 0.000 abstract 6
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 6
- 125000004076 pyridyl group Chemical group 0.000 abstract 6
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 6
- 125000005493 quinolyl group Chemical group 0.000 abstract 6
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 6
- 125000001544 thienyl group Chemical group 0.000 abstract 6
- 125000001425 triazolyl group Chemical group 0.000 abstract 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 5
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 5
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000002541 furyl group Chemical group 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 4
- 239000003112 inhibitor Substances 0.000 abstract 4
- 125000001624 naphthyl group Chemical group 0.000 abstract 4
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 4
- 125000005554 pyridyloxy group Chemical group 0.000 abstract 4
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 abstract 3
- 229940118148 Aldose reductase inhibitor Drugs 0.000 abstract 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 2
- 208000002249 Diabetes Complications Diseases 0.000 abstract 2
- 206010012655 Diabetic complications Diseases 0.000 abstract 2
- 241000124008 Mammalia Species 0.000 abstract 2
- 239000003288 aldose reductase inhibitor Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000000651 prodrug Substances 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 abstract 1
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 abstract 1
- 102100029077 3-hydroxy-3-methylglutaryl-coenzyme A reductase Human genes 0.000 abstract 1
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 0.000 abstract 1
- 239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 abstract 1
- 102000016912 Aldehyde Reductase Human genes 0.000 abstract 1
- 108010053754 Aldehyde reductase Proteins 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- 208000007342 Diabetic Nephropathies Diseases 0.000 abstract 1
- 208000032131 Diabetic Neuropathies Diseases 0.000 abstract 1
- 208000032781 Diabetic cardiomyopathy Diseases 0.000 abstract 1
- 206010063547 Diabetic macroangiopathy Diseases 0.000 abstract 1
- 206010054044 Diabetic microangiopathy Diseases 0.000 abstract 1
- 206010012689 Diabetic retinopathy Diseases 0.000 abstract 1
- 102100038509 E3 ubiquitin-protein ligase ARIH1 Human genes 0.000 abstract 1
- 229930091371 Fructose Natural products 0.000 abstract 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract 1
- 239000005715 Fructose Substances 0.000 abstract 1
- 102000007390 Glycogen Phosphorylase Human genes 0.000 abstract 1
- 108010046163 Glycogen Phosphorylase Proteins 0.000 abstract 1
- 102100030980 Sodium/hydrogen exchanger 1 Human genes 0.000 abstract 1
- 229940123659 Sorbitol dehydrogenase inhibitor Drugs 0.000 abstract 1
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 229940030600 antihypertensive agent Drugs 0.000 abstract 1
- 239000002220 antihypertensive agent Substances 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 230000005961 cardioprotection Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 abstract 1
- 201000009101 diabetic angiopathy Diseases 0.000 abstract 1
- 208000033679 diabetic kidney disease Diseases 0.000 abstract 1
- 230000010030 glucose lowering effect Effects 0.000 abstract 1
- MNQZXJOMYWMBOU-UHFFFAOYSA-N glyceraldehyde Chemical compound OCC(O)C=O MNQZXJOMYWMBOU-UHFFFAOYSA-N 0.000 abstract 1
- 108010093115 growth factor-activatable Na-H exchanger NHE-1 Proteins 0.000 abstract 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001786 isothiazolyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 239000002590 phosphodiesterase V inhibitor Substances 0.000 abstract 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 abstract 1
- 239000003379 purinergic P1 receptor agonist Substances 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000006085 pyrrolopyridyl group Chemical group 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
- 230000009103 reabsorption Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229940076279 serotonin Drugs 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 abstract 1
Classifications
-
- 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
- C07D409/12—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 linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 hetero ring
-
- 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
- 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
- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Compuestos de piridazin-3-ona, a composiciones farmacéuticas que comprenden esos compuestos y a métodos de utilización de tales compuestos y composiciones para inhibir la aldosa reductasa, disminuir los niveles de sorbitol y, por tanto, hacer descender los niveles de fructosa, y/o tratar o prevenir complicaciones diabéticas tales como neuropatía diabética, retinopatía diabética, nefropatía diabética, cardiomiopatía diabética, microangiopatía diabética y macroangiopatía diabética, en los mamíferos. Se describen también métodos para proporcionar cardioprotección a sujetos no aquejados de diabetes. Se refiere también a composiciones farmacéuticas y a kits que comprenden una combinación de un inhibidor de la aldosa reductasa (ARI), y un inhibidor de la sorbitol deshidrogenasa, y a métodos de utilización de tales composiciones o kits para tratar o prevenir las complicaciones diabéticas anteriores en los mamíferos. Se refiere también a otras combinaciones con los ARIs de la presente, incluyendo combinaciones con agonistas de la adenosina, inhibidores de NHE-1, inhibidores de la glicógeno fosforilasa, inhibidores selectivos de la reabsorción de serotonina, agonistas del GABA, agentes antihipertensivos, inhibidores de la 3-hidroxi-3-metilglutaril coenzima A reductasa, e inhibidores de la fosfodiesterasa-5, y a agentes de disminución de la glucosa. Un compuesto de Fórmula (1), uno de sus profármacos o una sal farmacéuticamente aceptable de dicho compuesto o dicho profármaco, en la que: A es S, SO ó SO2; R1 y R2 son, cada uno independientemente, hidrógeno o metilo; R3 es Het1, -CHR4Het1 ó NR6R7; R4 es hidrógeno o alquilo C1-3; R6 es alquilo C1-6, arilo o Het2; R7 es Het3; Het1 es piridilo, pirimidilo, pirazinilo, piridazinilo, quinolilo, isoquinolilo, quinazolilo, quinoxalilo, ftalazinilo, cinolinilo, naftiridinilo, pteridinilo, pirazinopirazinilo, pirazinopiridazinilo, pirimidopiridazinilo, pirimidopirimidilo, piridopirimidilo, piridopirazinilo, piridopiridazinilo, pirrolilo, furanilo, tienilo, imidazolilo, oxazolilo, tiazolilo, pirazolilo, isoxazolilo, isotiazolilo, triazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, indolilo, benzofuranilo, benzotienilo, bencimidazolilo, benzoxazolilo, benzotiazolilo, indazolilo, bencisoxazolilo, bencisotiazolilo, pirrolopiridilo, furopiridilo, tienopiridilo, imidazolopiridilo, oxazolopiridilo, tiazolopiridilo, pirazolopiridilo, isoxazolopiridilo, isotiazolopiridilo, pirrolopirimidilo, furopirimidilo, tienopirimidilo, imidazolopirimidilo, oxazolopirimidilo, tiazolopirimidilo, pirazolopirimidilo, isoxazolopirimidilo, isotiazolopirimidilo, pirrolopirazinilo, furopirazinilo, tienopirazinilo, imidazolopirazinilo, oxazolopirazinilo, tiazolopirazinilo, pirazolopirazinilo, isoxazolopirazinilo, isotiazolopirazinilo, pirrolopiridazinilo, furopiridazinilo, tienopiridazinilo, imidazolopiridazinilo, oxazolopiridazinilo, tiazolopiridazinilo, pirazolopiridazinilo, isoxazolopiridazinilo o isotiazolopiridazinilo; Het1 está opcionalmente sustituido con hasta un total de cuatro sustituyentes seleccionados independientemente, cada uno de ellos, entre halo, formilo, alcoxi(C1-6)carbonilo, alquenil(C1-6)oxicarbonilo, alcoxi(C1-4)-alquilo (C1-4), C(OH)R12R13, alquil(C1-4)carbonilamido, cicloalquil(C3-7)carbonilamido, fenilcarbonilamido, bencilo, fenilo, naftilo, imidazolilo, piridilo, triazolilo, bencimidazolilo, oxazolilo, isoxazolilo, tiazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, tienilo, benzotiazolilo, pirrolilo, pirazolilo, quinolilo, isoquinolilo, benzoxazolilo, piridazinilo, piridiloxi, piridilsulfonilo, furanilo, fenoxi, tiofenoxi, alquil(C1-4)sulfenilo, alquil(C1-4)sulfonilo, cicloalquilo C3-7, alquilo C1-6 opcionalmente sustituido con hasta tres sustituyentes fluoro, o alcoxi C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro; dichos bencilo, fenilo, naftilo, imidazolilo, piridilo, triazolilo, bencimidazolilo, oxazolilo, isoxazolilo, tiazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, tienilo, benzotiazolilo, pirrolilo, pirazolilo, quinolilo, isoquinolilo, benzoxazolilo, piridazinilo, piridiloxi, piridilsulfonilo, furanilo, fenoxi tiofenoxi, en la definición de sustituyentes para Het1 están opcionalmente sustituidos con hasta tres sustituyentes seleccionados independientemente entre hidroxi, halo, hidroxi-alquilo C1-4, alcoxi(C1-4)-alquilo(C1-4), alquil(C1-6)sulfenilo, alquil(C1-6)sulfinilo, alquil(C1-6)sulfonilo, alquilo C1-6 opcionalmente sustituido con hasta cinco sustituyentes fluoro y alcoxi C1-6 opcionalmente sustituido con hasta cinco sustituyentes fluoro; dichos imidazolilo, oxazolilo, isoxazolilo, tiazolilo y pirazolilo en la definición de sustituyentes para Het1 están opcionalmente sustituidos con hasta dos sustituyentes seleccionados independientemente entre hidroxi, halo, alquilo C1-4, hidroxi-alquilo C1-4, alcoxi(C1-4)-alquilo(C1-4), alquil(C1-4)-fenilo opcionalmente sustituido en la parte de fenilo con un Cl, Br, OMe, Me ó SO2-fenilo en el que dicho SO2-fenilo está opcionalmente sustituido en la parte de fenilo con un Cl, Br, OMe, Me, alquilo C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro, o alcoxi C1-4 opcionalmente sustituido con hasta tres sustituyentes fluoro; R12 y R13 son, cada uno independientemente, hidrógeno o alquilo C1-4; Het2 y Het3 son, cada uno independientemente, imidazolilo, piridilo, triazolilo, bencimidazolilo, oxazolilo, isoxazolilo, tiazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, tienilo, benzotiazolilo, pirrolilo, pirazolilo, quinolilo, isoquinolilo, benzoxazolilo, piridazinilo, piridiloxi, piridilsulfonilo, furanilo, fenoxi y tiofenoxi; Het2 y Het3 están, cada uno independientemente, opcionalmente sustituido con hasta un total de cuatro sustituyentes seleccionados independientemente cada uno de ellos entre halo, formilo, alcoxi(C1-4)carbonilo, alquilenil(C1-6)oxi-carbonilo, alcoxi(C1-4)-alquilo(C1-4), C(OH)R18R19, alquil(C1-4)carbonilamido, cicloalquil(C3-7)carbonilamido, fenilcarbonilamido, fenilo, naftilo, imidazolilo, piridilo, triazolilo, bencimidazolilo, oxazolilo, isoxazolilo, tiazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, tienilo, benzotiazolilo, pirrolilo, pirazolilo, quinolilo, isoquinolilo, benzoxazolilo, piridazinilo, piridiloxi, piridilsulfonilo, furanilo, fenoxi, tiofenoxi, alquil(C1-4)sulfenilo, alquil(C1-4)sulfonilo, cicloalquilo C3-7, alquilo C1-4 opcionalmente sustituido con hasta tres sustituyentes fluoro o alcoxi C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro; dichos fenilo, naftilo, imidazolilo, piridilo, triazolilo, bencimidazolilo, oxazolilo, isoxazolilo, tiazolilo, oxadiazolilo, tiadiazolilo, tetrazolilo, tienilo, benzotiazolilo, pirrolilo, pirazolilo, quinolilo, isoquinolilo, benzoxazolilo, piridazinilo, piridiloxi, piridilsulfonilo, furanilo, fenoxi, tiofenoxi, en la definición de sustituyentes para Het2 y Het3 están opcionalmente sustituidos con hasta tres sustituyentes seleccionados independientemente entre hidroxi, halo, hidroxi-alquilo C1-4, alcoxi(C1-4)-alquilo(C1-4), alquilo C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro y alcoxi C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro; dichos imidazolilo, oxazolilo, isoxazolilo, tiazolilo y pirazolilo en la definición de sustituyentes para Het2 y Het3 están opcionalmente sustituidos con hasta dos sustituyentes seleccionados independientemente entre hidroxi, halo, hidroxi-alquilo C1-4, alcoxi(C1-4)-alquilo(C1-4), alquilo C1-4 opcionalmente sustituido con hasta cinco sustituyentes fluoro y alcoxi C1-4 opcionalmente sustituido con hasta tres sustituyentes fluoro; y R18 y R19 son, cada uno independientemente, hidrógeno o alquilo C1-4; con tal que cuando R3 es NR6R7, entonces A es SO2.
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Families Citing this family (43)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU714980B2 (en) | 1996-07-24 | 2000-01-13 | Warner-Lambert Company Llc | Isobutylgaba and its derivatives for the treatment of pain |
| DE60204611T2 (de) * | 2001-02-28 | 2006-05-11 | Pfizer Products Inc., Groton | Sulfonyl-pyridazinon-derivate zur Verwendung als Aldose-reduktase-inhibitoren |
| PT1373259E (pt) * | 2001-03-30 | 2005-03-31 | Pfizer Prod Inc | Inibidores piridazinona de aldose reductase |
| AU761191B2 (en) * | 2001-05-24 | 2003-05-29 | Pfizer Products Inc. | Therapies for tissue damage resulting from ischemia |
| AU2003200847A1 (en) * | 2002-01-09 | 2003-07-24 | Pfizer Products Inc. | Process and intermediates for pyridazinone antidiabetic agents |
| US20040092522A1 (en) * | 2002-08-15 | 2004-05-13 | Field Mark John | Synergistic combinations |
| US7419981B2 (en) * | 2002-08-15 | 2008-09-02 | Pfizer Inc. | Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor |
| US6872833B2 (en) * | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| US8017634B2 (en) | 2003-12-29 | 2011-09-13 | President And Fellows Of Harvard College | Compositions for treating obesity and insulin resistance disorders |
| US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
| AR049384A1 (es) | 2004-05-24 | 2006-07-26 | Glaxo Group Ltd | Derivados de purina |
| CA2568640C (en) | 2004-06-04 | 2011-08-09 | Teva Pharmaceutical Industries Ltd. | Pharmaceutical composition containing irbesartan |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| US20060035251A1 (en) * | 2004-06-30 | 2006-02-16 | Whitehead Institute For Biomedical Research | Novel methods for high-throughput genome-wide location analysis |
| GB0514809D0 (en) | 2005-07-19 | 2005-08-24 | Glaxo Group Ltd | Compounds |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| AU2007206016A1 (en) * | 2006-01-13 | 2007-07-26 | Wyeth | Sulfonyl substituted 1H-indoles as ligands for the 5-hydroxytryptamine receptors |
| EP2431367A3 (en) | 2006-06-27 | 2012-07-04 | Takeda Pharmaceutical Company Limited | Fused cyclic compounds as GPR40 receptor modulators |
| ATE547394T1 (de) | 2006-12-01 | 2012-03-15 | Bristol Myers Squibb Co | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen |
| WO2008116107A2 (en) * | 2007-03-21 | 2008-09-25 | Takeda San Diego, Inc. | Piperazine derivatives as glucokinase activators |
| JP2010043063A (ja) | 2008-05-09 | 2010-02-25 | Agency For Science Technology & Research | 川崎病の診断及び治療 |
| CA2783699C (en) | 2009-12-08 | 2019-01-15 | Case Western Reserve University | Primary amine compounds for treating ocular disorders |
| US8916563B2 (en) | 2010-07-16 | 2014-12-23 | The Trustees Of Columbia University In The City Of New York | Aldose reductase inhibitors and uses thereof |
| RU2615767C2 (ru) * | 2011-09-15 | 2017-04-11 | Тайпей Медикл Юнивесити | Способ лечения сердечной недостаточности и поражения нервных клеток |
| US9339542B2 (en) * | 2013-04-16 | 2016-05-17 | John L Couvaras | Hypertension reducing composition |
| CA2909442A1 (en) | 2013-04-17 | 2014-10-23 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| CN103739547B (zh) * | 2014-01-03 | 2015-09-02 | 沈阳药科大学 | 2-[6-甲氧基-3-(2,3-二氯苯基)甲基-4-氧代-1,4-二氢-1(4h)-喹啉基]乙酸的合成方法 |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| EP3283074A4 (en) * | 2015-04-14 | 2018-12-05 | Case Western Reserve University | Compositions and methods of modulating short-chain dehydrogenase activity |
| WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
| CN109310674B (zh) | 2016-06-21 | 2022-07-08 | 纽约市哥伦比亚大学理事会 | 醛糖还原酶抑制剂及其使用方法 |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| US10344002B2 (en) | 2016-09-26 | 2019-07-09 | Nusirt Sciences, Inc. | Compositions and methods for treating metabolic disorders |
| EP3548035A4 (en) | 2016-11-30 | 2020-07-22 | Case Western Reserve University | COMBINATIONS OF 15-PGDH INHIBITORS WITH CORCOSTEROIDS AND / OR TNF INHIBITORS AND THEIR USES |
| CN110573154A (zh) | 2017-02-06 | 2019-12-13 | 卡斯西部储备大学 | 调节短链脱氢酶活性的组合物和方法 |
| IL272246B1 (en) | 2017-07-28 | 2025-09-01 | Applied Therapeutics Inc | Derivatives of 2-(4-oxo/thioketone/azo-3-((substituted)benzo[d]thiazol-2-yl)methyl)- 3,4-dihydrothieno[3,4-d]pyridazin-1-yl)acetic acid for use as aldose reductase inhibitors in treating galactosemia or preventing complications associated with galactosemia |
| SG11202105345TA (en) | 2018-11-21 | 2021-06-29 | Univ Case Western Reserve | Compositions and methods of modulating short-chain dehydrogenase activity |
| EP4470609A3 (en) | 2019-01-18 | 2025-03-12 | Astrazeneca AB | Pcsk9 inhibitors and methods of use thereof |
| CN113966396A (zh) | 2019-05-07 | 2022-01-21 | 迈阿密大学 | 遗传性神经病和相关障碍的治疗和检测 |
| MX2021014441A (es) | 2019-05-31 | 2022-01-06 | Ikena Oncology Inc | Inhibidores del dominio asociado mejorador de la transcripcion (tead) y usos de los mismos. |
| WO2020243415A2 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| WO2022120353A1 (en) * | 2020-12-02 | 2022-06-09 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE47592B1 (en) | 1977-12-29 | 1984-05-02 | Ici Ltd | Enzyme inhibitory phthalazin-4-ylacetic acid derivatives, pharmaceutical compositions thereof,and process for their manufacture |
| US4939140A (en) | 1985-11-07 | 1990-07-03 | Pfizer Inc. | Heterocyclic oxophthalazinyl acetic acids |
| US4996204A (en) | 1989-05-11 | 1991-02-26 | Pfizer Inc. | Pyrido[2,3-d]pyridazinones as aldose reductase inhibitors |
| FR2647676A1 (fr) | 1989-06-05 | 1990-12-07 | Union Pharma Scient Appl | Nouveaux derives de pyridazinone, leurs procedes de preparation, medicaments les contenant, utiles notamment comme inhibiteurs de l'aldose reductase |
| KR950001039B1 (ko) * | 1990-11-30 | 1995-02-08 | 가부시끼가이샤 쓰무라 | 크로몬 유도체 및 이 화합물을 유효성분으로 하는 아르도스 리덕타제 저해제 |
| FI934222A7 (fi) | 1991-03-28 | 1993-09-27 | Pfizer | Pyridatsinonietikkahappoja |
| US5834466A (en) | 1994-12-22 | 1998-11-10 | The Regents Of The University Of California | Method for protecting of heart by limiting metabolic and ionic abnormalities developed during ischemia, following ischemia or resulting from ischemia |
| TWI238064B (en) | 1995-06-20 | 2005-08-21 | Takeda Chemical Industries Ltd | A pharmaceutical composition for prophylaxis and treatment of diabetes |
| EE04494B1 (et) * | 1997-09-24 | 2005-06-15 | Orion Corporation | 1-oksa-, asa- ja tianaftaleen-2-oon biseetrid fosfolambaani inhibiitoritena |
| FR2822827B1 (fr) * | 2001-03-28 | 2003-05-16 | Sanofi Synthelabo | Nouveaux derives de n-(arylsulfonyl) beta-aminoacides comportant un groupe aminomethyle substitue, leur procede de preparation et les compositions pharmaceutiques en contenant |
| PT1373259E (pt) * | 2001-03-30 | 2005-03-31 | Pfizer Prod Inc | Inibidores piridazinona de aldose reductase |
| CN1505514A (zh) * | 2001-04-30 | 2004-06-16 | �Ʒ� | 醛糖还原酶抑制剂与环加氧酶-2抑制剂的组合 |
| AU2003200847A1 (en) * | 2002-01-09 | 2003-07-24 | Pfizer Products Inc. | Process and intermediates for pyridazinone antidiabetic agents |
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