AR076945A1 - Agentes inductores de apoptosis con selectividad por bcl-2 para el tratamiento de cancer y enfermedades inmunes - Google Patents
Agentes inductores de apoptosis con selectividad por bcl-2 para el tratamiento de cancer y enfermedades inmunesInfo
- Publication number
- AR076945A1 AR076945A1 ARP100101935A ARP100101935A AR076945A1 AR 076945 A1 AR076945 A1 AR 076945A1 AR P100101935 A ARP100101935 A AR P100101935A AR P100101935 A ARP100101935 A AR P100101935A AR 076945 A1 AR076945 A1 AR 076945A1
- Authority
- AR
- Argentina
- Prior art keywords
- fused
- heterocycloalkane
- cycloalkane
- heterocycloalkene
- cycloalkene
- Prior art date
Links
- 101000971171 Homo sapiens Apoptosis regulator Bcl-2 Proteins 0.000 title abstract 3
- 102100021569 Apoptosis regulator Bcl-2 Human genes 0.000 title abstract 2
- 206010028980 Neoplasm Diseases 0.000 title 1
- 230000006907 apoptotic process Effects 0.000 title 1
- 201000011510 cancer Diseases 0.000 title 1
- 208000026278 immune system disease Diseases 0.000 title 1
- 230000001939 inductive effect Effects 0.000 title 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 26
- 150000001925 cycloalkenes Chemical class 0.000 abstract 25
- 150000002390 heteroarenes Chemical class 0.000 abstract 24
- 239000004576 sand Substances 0.000 abstract 23
- 229910052717 sulfur Inorganic materials 0.000 abstract 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 11
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 229910052799 carbon Inorganic materials 0.000 abstract 8
- 125000001072 heteroaryl group Chemical group 0.000 abstract 8
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 7
- OTXBWGUYZNKPMG-UHFFFAOYSA-N isofulminic acid Chemical compound O[N+]#[C-] OTXBWGUYZNKPMG-UHFFFAOYSA-N 0.000 abstract 7
- 101150009274 nhr-1 gene Proteins 0.000 abstract 7
- 229910052760 oxygen Inorganic materials 0.000 abstract 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 7
- 125000003342 alkenyl group Chemical group 0.000 abstract 6
- 125000000304 alkynyl group Chemical group 0.000 abstract 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 6
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 abstract 5
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 4
- 125000005842 heteroatom Chemical group 0.000 abstract 4
- 125000001424 substituent group Chemical group 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 abstract 2
- 102220544041 60S ribosomal protein L27_R10A_mutation Human genes 0.000 abstract 2
- 102220542311 60S ribosomal protein L27_R19A_mutation Human genes 0.000 abstract 2
- -1 C (O) N (R1) 2 Proteins 0.000 abstract 2
- 101100240518 Caenorhabditis elegans nhr-12 gene Proteins 0.000 abstract 2
- 101100240527 Caenorhabditis elegans nhr-22 gene Proteins 0.000 abstract 2
- 102220614548 Calmodulin-3_R23A_mutation Human genes 0.000 abstract 2
- 102220614557 Calmodulin-3_R31A_mutation Human genes 0.000 abstract 2
- 102220605470 Coilin_R15A_mutation Human genes 0.000 abstract 2
- 102220605451 Coilin_R36A_mutation Human genes 0.000 abstract 2
- 102220605399 Coilin_R40A_mutation Human genes 0.000 abstract 2
- 102220486696 Cytochrome b-245 chaperone 1_R43G_mutation Human genes 0.000 abstract 2
- 102220486708 Cytochrome b-245 chaperone 1_R44G_mutation Human genes 0.000 abstract 2
- 102220503974 Endogenous retrovirus group K member 6 Rec protein_R13A_mutation Human genes 0.000 abstract 2
- 102220503971 Endogenous retrovirus group K member 6 Rec protein_R14A_mutation Human genes 0.000 abstract 2
- 102220503970 Endogenous retrovirus group K member 6 Rec protein_R18A_mutation Human genes 0.000 abstract 2
- 102220503968 Endogenous retrovirus group K member 6 Rec protein_R20A_mutation Human genes 0.000 abstract 2
- 102220555063 Holliday junction recognition protein_R25A_mutation Human genes 0.000 abstract 2
- 102220595577 Major vault protein_R24A_mutation Human genes 0.000 abstract 2
- 102220544927 Nuclear pore complex protein Nup133_R30A_mutation Human genes 0.000 abstract 2
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 abstract 2
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 abstract 2
- 102220507264 Rab11 family-interacting protein 1_R29A_mutation Human genes 0.000 abstract 2
- 102220507254 Rab11 family-interacting protein 1_R38K_mutation Human genes 0.000 abstract 2
- 102220507255 Rab11 family-interacting protein 1_R39K_mutation Human genes 0.000 abstract 2
- 102220507253 Rab11 family-interacting protein 1_R42A_mutation Human genes 0.000 abstract 2
- 102220470249 Voltage-dependent L-type calcium channel subunit beta-2_R28A_mutation Human genes 0.000 abstract 2
- 102220500097 eIF5-mimic protein 2_R34A_mutation Human genes 0.000 abstract 2
- 239000000651 prodrug Chemical class 0.000 abstract 2
- 229940002612 prodrug Drugs 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 101100294108 Caenorhabditis elegans nhr-41 gene Proteins 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 abstract 1
- 125000004266 aziridin-1-yl group Chemical group [H]C1([H])N(*)C1([H])[H] 0.000 abstract 1
- 108700000711 bcl-X Proteins 0.000 abstract 1
- 102000055104 bcl-X Human genes 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000004366 heterocycloalkenyl group Chemical group 0.000 abstract 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- GCVFCUPRTZORNH-UHFFFAOYSA-N n,n-dimethyl-3-[4-(1,10-phenanthrolin-4-yl)butoxy]aniline;2-pyridin-2-ylpyridine;ruthenium Chemical compound [Ru].N1=CC=CC=C1C1=CC=CC=N1.N1=CC=CC=C1C1=CC=CC=N1.CN(C)C1=CC=CC(OCCCCC=2C3=C(C4=NC=CC=C4C=C3)N=CC=2)=C1 GCVFCUPRTZORNH-UHFFFAOYSA-N 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- 150000003852 triazoles Chemical class 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
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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
- C07D401/12—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
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/407—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
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- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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Abstract
Compuestos que inhiben la actividad de las proteínas anti-apoptoticas Bcl-2 o Bcl-XL, composiciones que contienen dichos compuestos y métodos para tratar enfermedades durante las cuales se expresa la proteína anti-apoptotica Bcl-2. Reivindicacion 1: Un compuesto caracterizado porque tiene la formula (1), o una sal, profármaco o sal de profármaco terapéuticamente aceptable del mismo, A1 es N o C(A2); uno o dos o tres o cada uno de A2, B1, D1 y E1 se seleccionan en forma independiente entre R1, OR1, SR1, S(O)R1, SO2R1, C(O)R1, C(O)OR1, OC(O)R1, NHR1, N(R1)2, C(O)NHR1, C(O)N(R1)2, NHC(O)R1, NHC(O)OR1, NR1C(O)NHR1, NR1C(O)N(R1)2, SO2NHR1, SO2N(R1)2, NHSO2R1, NHSO2NHR1 o N(CH3)SO2N(CH3)R1, y los restantes se seleccionan en forma independiente entre H, F, CI, Br, I, CN, CF3, C(O)OH, C(O)NH2 o C(O)OR1A; Y1 es H, CN, NO2, C(O)OH, F, CI, Br, I, CF3, OCF3, CF2CF3, OCF2CF3, R17, OR17, C(O)R17, C(O)OR17, SR17, NH2, NHR17, N(R17)2, NHC(O)R17, C(O)NH2, C(O)NHR17, C(O)N(R17)2, NHS(O)R17 o NHSO2R17; o B1 y Y1, junto con los átomos a los cuales están unidos , son imidazol o triazol; y uno o dos o cada uno de A2, D1 y E1 se seleccionan en forma independiente entre R1, OR1, SR1, S(O)R1, SO2R1, C(O)R1, C(O)OR1, OC(O)R1, NHR1, N(R1)2, C(O)NHR1, C(O)N(R1)2, NHC(O)R1, NHC(O)OR1, NHC(O)NHR1, N(CH3)C(O)N(CH3)R1, SO2NHR1, SO2N(R1)2, NHSO2R1, NHSO2NHR1 o N(CH3)SO2N(CH3)R1, y los restantes se seleccionan en forma independiente entre H, F, Cl, Br, I, CF3, C(O)OH, C(O)NH2 o C(O)OR1A; R1 es R2, R3, R4 o R5; R1A es alquilo C1-6, alquenilo C3-6 o alquinilo C3-6; R2 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R2A; R2A es cicloalcano o heterocicloalcano; R3 es heteroarilo que no está fusionado o está fusionado con benceno, heteroareno o R3A; R3A es cicloalcano o heterocicloalcano; R4 es cicloalquilo, cicloalquenilo, heterocicloalquilo o heterocicloalquenilo, cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R4A; R4A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R5 es alquilo, alquenilo o alquinilo, cada uno de los cuales no esta sustituido o está sustituido con uno o dos o tres de los siguientes sustituyentes, seleccionados en forma independiente: R6, NC(R6A)(R6B), R7, OR7, SR7, S(O)R7, SO2R7, NHR7, N(R7)2, C(O)R7, C(O)NH2, C(O)NHR7, NHC(O)R7, NHSO2R7, NHC(O)OR7, SO2NH2, SO2NHR7, SO2N(R7)2, NHC(O)NH2, NHC(O)NHR7, NHC(O)CH(CH3)NHC(O)CH(CH3)NH2, NHC(O)CH(CH3)NHC(O)CH(CH3)NHR1, OH, (O), C(O)OH, (O), N3, CN, NH2, CF3, CF2CF3, F, Cl, Br o I; R6 es espiroalquilo C2-5, cada uno de los cuales no esta sustituido o está sustituido con OH, (O), N3, CN, CF3, CF2CF3, F, Cl, Br, I, NH2, NH(CH3) o N(CH3)2; R6A y R6B se seleccionan en forma independiente entre alquilo o, junto con el N al cual están unidos, R6C; R6C es aziridin-1-ilo, azetidin-1-ilo, pirrolidin-1-ilo o piperidin-1-ilo, teniendo cada uno una unidad CH2 no reemplazada o reemplazada con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH; R7 es R8, R9, R10 o R11; R8 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R8A; R8A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R9 es heteroarilo que no está fusionado o está fusionado con areno, heteroareno o R9A; R9A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R10 es cicloalquilo C3-10 o cicloalquenilo C4-10, donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R10A; R10A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R11 es alquilo, alquenilo o alquinilo, cada uno de los cuales no esta sustituido o está sustituido con uno o dos o tres de los siguientes sustituyentes, seleccionados en forma independiente: R12, OR12, NHR12, N(R12)2, C(O)NH2, C(O)NHR12, C(O)N(R12)2, OH, (O), C(O)OH, N3, CN, NH2, CF3, CF2CF3, F, CI, Br o I; R12 es R13, R14, R15 o R16; R13 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R13A; R13A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R14 es heteroarilo, cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R14A; R14A es cicloalcano. cicloalqueno, heterocicloalcano o heterocicloalqueno; R15 es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno, cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R15A; R15A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R16 es alquilo, alquenilo o alquinilo; R17 es R18, R19, R20 o R21; R18 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R18A; R18A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R19 es heteroarilo que no está fusionado o está fusionado con areno, heteroareno o R19A; R19A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R20 es cicloalquilo C3-10 o cicloalquenilo C4-10, donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R20A; R20A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R21 es alquilo, alquenilo o alquinilo, cada uno de los cuales no esta sustituido o está sustituido con uno o dos o tres de los siguientes sustituyentes, seleccionados en forma independiente: R22, OR22, NHR22, N(R22)2, C(O)NH2, C(O)NHR22, C(O)N(R22)2, OH, (O), C(O)OH, N3, CN, NH2, CF3, CF2CF3, F, CI, Br o I; R22 es R23, R24 o R25; R23 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R23A, R23A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R24 es heteroareno que no está fusionado o está fusionado con areno, heteroareno o R24A; R24A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R23 es cicloalquilo C3-6 o cicloalquenilo C4-6, donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R25A; R25A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; Z1 es R26 o R27, cada uno de los cuales está sustituido con R28, R29 o R30, cada uno de los cuales está sustituido con F, Cl, Br, I, CH2R37, CH(R31)(R37), C(R31)(R31A)(R37), C(O)R37, OR37, SR37, S(O)R37, SO2R37, NHR37 o N(R32)R37; R26 es fenilo que no está fusionado o está fusionado con areno o heteroareno; R27 es heteroareno que no está fusionado o está fusionado con areno o heteroareno; R28 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R28A; R28A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno, R29 es heteroarilo o R29A; R29A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R30 es cicloalquilo o cicloalquenilo. donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R30A; R30A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R31 y R31A son en forma independiente F, CI, Br o alquilo o se toman juntos y son espiroalquilo C2-5; R32 es R33, C(O)R33 o C(O)OR33; R33 es R34 o R35; R34 es fenilo que no está fusionado o está fusionado con arilo, heteroarilo o R34A; R34A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R35 es alquilo que no está sustituido o está sustituido con R36; R36 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R36A, R36A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R37 es R38, R39 o R40, cada uno de los cuales está sustituido con F, CI, Br, I, R41, OR41, NHR41, N(R41)2, NHC(O)OR41, SR41, S(O)R41 o SO2R41; R38 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R38A; R38A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R39 es heteroarilo que no está fusionado o está fusionado con areno, heteroareno o R39A; R39A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R40 es cicloalquilo C3-8 o cicloalquenilo C4-8, donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R40A, R40A cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R41 es R42, R43, R44 o R45; R42 es fenilo que no está fusionado o está fusionado con areno, heteroareno o R42A, R42A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R43 es heteroarilo que no está fusionado o está fusionado con areno, heteroareno o R43A; R43A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R44 es cicloalquilo C3-9 o cicloalquenilo C4-7, donde cada uno tiene una o dos unidades CH2 no reemplazadas o reemplazadas en forma independiente con O, C(O), CNOH, CNOCH3, S, S(O), SO2 o NH y una o dos unidades CH no reemplazadas o reemplazadas con N, y cada uno de los cuales no está fusionado o está fusionado con areno, heteroareno o R44A; R44A es cicloalcano, cicloalqueno, heterocicloalcano o heterocicloalqueno; R45 es alquilo, alquenilo o alquinilo, cada uno de los cuales no esta sustituido o está sustituido con uno o dos sustituyentes seleccionados en forma independiente entre: R46, OR46, NHR46, N(R46)2, C(O)NH
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