AR085280A1 - ACIDOS g-AMINO-BUTIRICO SUSTITUIDOS, PROCESOS E INTERMEDIARIOS PARA SU PREPARACION, UNA COMPOSICION FARMACEUTICA QUE LOS COMPRENDE Y SU USO EN LA TERAPIA DE ENFERMEDADES MEDIADAS POR LA INHIBICION DE NEP - Google Patents
ACIDOS g-AMINO-BUTIRICO SUSTITUIDOS, PROCESOS E INTERMEDIARIOS PARA SU PREPARACION, UNA COMPOSICION FARMACEUTICA QUE LOS COMPRENDE Y SU USO EN LA TERAPIA DE ENFERMEDADES MEDIADAS POR LA INHIBICION DE NEPInfo
- Publication number
- AR085280A1 AR085280A1 ARP120100547A ARP120100547A AR085280A1 AR 085280 A1 AR085280 A1 AR 085280A1 AR P120100547 A ARP120100547 A AR P120100547A AR P120100547 A ARP120100547 A AR P120100547A AR 085280 A1 AR085280 A1 AR 085280A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- cycloalkyl
- phenyl
- halo
- aryl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 3
- 230000005764 inhibitory process Effects 0.000 title abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 238000002560 therapeutic procedure Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title 1
- 150000007513 acids Chemical class 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 230000001404 mediated effect Effects 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 16
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000005843 halogen group Chemical group 0.000 abstract 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 8
- -1 -OH Chemical group 0.000 abstract 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000001072 heteroaryl group Chemical group 0.000 abstract 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 102000003729 Neprilysin Human genes 0.000 abstract 1
- 108090000028 Neprilysin Proteins 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
Classifications
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- A61K31/351—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom not condensed with another ring
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- A61K31/403—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 carbocyclic rings, e.g. carbazole
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Abstract
Estos compuestos tienen actividad de inhibición de neprilisina. Composiciones farmacéuticas que comprenden dichos compuestos; métodos para usar dichos compuestos Usos de los mismos en terapias; y procesos e intermediarios para preparar dichos compuestos.Reivindicación 1: Un compuesto caracterizado porque es de fórmula (1), donde R1 se selecciona entre -OR7 y -NR8R9; R2a se selecciona entre -CH2OH, -CH2OP(O)(OH)2, y -CH2OC(O)CH(R37)NH2; o R2a se toma junto con R7 para formar -CH2O-CR18R19- o se toma junto con R8 para formar -CH2O-C(O)-; R2b se selecciona entre H y -CH3, o se toma junto con R2a para formar -CH2-O-CH2-; Z se selecciona entre -CH- y -N-; X es un heteroarilo C1-9; R3 se encuentra ausente o se selecciona entre H; halo; alquilen C0-5-OH; -NH2; alquilo C1-6; -CF3; cicloalquilo C3-7; alquilen C0-2-O-alquilo C1-6; -C(O)R20; -alquilen C0-1-COOR21; -C(O)NR22R23; -NHC(O)R24; =O; -NO2; -C(CH3)=N(OH); fenilo opcionalmente sustituido con uno o dos grupos seleccionados en forma independiente entre halo, -OH, -CF3, -OCH3, -NHC(O)CH3, y fenilo; naftalenilo; piridinilo; pirazinilo; pirazolilo opcionalmente sustituido con metilo; tiofenilo opcionalmente sustituido con metilo o halo; furanilo; y -CH2-morfolinilo; y R3, cuando está presente, se une a un átomo de carbono; R4 se encuentra ausente o se selecciona entre H; -OH; -alquilo C1-6; alquilen C1-2-COOR35; -CH2OC(O)CH(R36)NH2; -OCH2OC(O)CH(R36)NH2; -OCH2OC(O)CH3; -CH2OP(O)(OH)2; -CH2CH(OH)CH2OH; -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6; piridinilo; y fenilo o bencilo opcionalmente sustituido con uno o más grupos seleccionados entre halo, -COOR35, -OCH3, -OCF3, y -SCF3; y R4, cuando está presente, se une a un átomo de carbono o nitrógeno; o R3 y R4 se toman juntos para formar -fenilen-O-(CH2)1-3- o -fenilen-O-CH2-CHOH-CH2-; a es 0 ó 1; R5 se selecciona entre halo, -CH3, -CF3, y -CN; b es 0 o un entero entre 1 y 3; cada R6 se selecciona en forma independiente entre halo, -OH, -CH3, -OCH3, y -CF3; R7 se selecciona entre H, -alquilo C1-8, -alquilen C1-3-arilo C6-10, -alquilen C1-3-heteroarilo C1-9, cicloalquilo C3-7, -[(CH2)2O]1-3CH3, -alquilen C1-6-OC(O)R10, -alquilen C1-6-NR12R13, -alquilen C1-6-C(O)R31, -alquilen C0-6morfolinilo, -alquilen C1-6-SO2-alquilo C1-6, o un resto seleccionado del grupo de fórmulas (2); R10 se selecciona entre -alquilo C1-6, -O-alquilo C1-6, cicloalquilo C3-7, -O-cicloalquilo C3-7, fenilo, -O-fenilo, -NR12R13, -CH[CH(CH3)2]-NH2, -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6, y -CH(NH2)CH2COOCH3; y R12 y R13 se seleccionan en forma independiente entre H, -alquilo C1-6, y bencilo, o R12 y R13 se toman juntos como -(CH2)3-6-, -C(O)-(CH2)3-, o -(CH2)2O(CH2)2-; R31 se selecciona entre -O-alquilo C1-6, -O-bencilo, y -NR12R13; y R32 es alquilo C1-6 o -alquilen C0-6-arilo C6-10; R8 se selecciona entre H, -OH, -OC(O)R14, -CH2COOH, -O-bencilo, -piridilo, y -OC(S)NR15R16; R14 se selecciona entre H, alquilo C1-6, -arilo C6-10, -OCH2-arilo C6-10, -CH2O-arilo C6-10, y -NR15R16; y R15 y R16 se seleccionan en forma independiente entre H y -alquilo C1-4; R9 se selecciona entre H, alquilo C1-6, y -C(O)-R17; y R17 se selecciona entre H, -alquilo C1-6, cicloalquilo C3-7, -arilo C6-10, y -heteroarilo C1-9; R18 y R19 se seleccionan en forma independiente entre H, -alquilo C1-6, y -O-cicloalquilo C3-7, o R18 y R19 se toman juntos para formar =O; R20 se selecciona entre H y -alquilo C1-6; R21 y R35 se seleccionan en forma independiente entre H, -alquilo C1-6, -alquilen C1-3-arilo C6-10, -alquilen C1-3-heteroarilo C1-9, cicloalquilo C3-7, -[(CH2)2O]1-3CH3, -alquilen C1-6-OC(O)R25, -alquilen C1-6-NR27R28, -alquilen C1-6-C(O)R33, -alquilen C0-6morfolinilo, -alquilen C1-6-SO2-alquilo C1-6, o un resto seleccionado del grupo de fórmulas (3); R25 se selecciona entre alquilo C1-6, -O-alquilo C1-6, cicloalquilo C3-7, -O-cicloalquilo C3-7, fenilo, -O-fenilo, -NR27R28, -CH[CH(CH3)2]-NH2, -CH[CH(CH3)2]-NHC(O)O-alquilo C1-6, y -CH(NH2)CH2COOCH3; R27 y R28 se seleccionan en forma independiente entre H, -alquilo C1-6, y bencilo; o R27 y R28 se toman juntos como -(CH2)3-6-, -C(O)-(CH2)3-, o -(CH2)2O(CH2)2-; R33 se selecciona entre -O-alquilo C1-6, -O-bencilo, y -NR27R28; y R34 es -alquilo C1-6 o -alquilen C0-6-arilo C6-10; R22 y R23 se seleccionan en forma independiente entre H, -alquilo C1-6, -CH2COOH, -(CH2)2OH; -(CH2)2OCH3, -(CH2)2SO2NH2, -(CH2)2N(CH3)2, -alquilen C0-1-cicloalquilo C3-7, y -(CH2)2-imidazolilo; o R22 y R23 se toman juntos para formar un saturado o parcialmente insaturado-heterociclo C3-5 opcionalmente sustituido con halo, -OH, -COOH, o -CONH2; y que contiene opcionalmente un átomo de oxígeno en el anillo; R24 se selecciona entre alquilo C1-6; -alquilen C0-1-O-alquilo C1-6; fenilo opcionalmente sustituido con halo o -OCH3; y -heteroarilo C1-9; R36 se selecciona entre H, -CH(CH3)2, fenilo, y bencilo; y R37 se selecciona entre H, -CH(CH3)2, fenilo, y bencilo; donde cada grupo alquilo en R1, R3, y R4 está opcionalmente sustituido con entre 1 y 8 átomos de flúor; y; donde el ligando metileno en el bifenilo está opcionalmente sustituido con uno o dos grupos alquilo C1-6 o ciclopropilo; o una sal farmacéuticamente aceptable del mismo.
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US201161443827P | 2011-02-17 | 2011-02-17 |
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JP (2) | JP5959065B2 (es) |
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AR (1) | AR085280A1 (es) |
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BR (1) | BR112013020996A8 (es) |
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CO (1) | CO6781518A2 (es) |
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RU (1) | RU2604522C2 (es) |
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2012
- 2012-02-16 WO PCT/US2012/025365 patent/WO2012112742A1/en active Application Filing
- 2012-02-16 US US13/398,015 patent/US8481044B2/en active Active
- 2012-02-16 SG SG2013062401A patent/SG192815A1/en unknown
- 2012-02-16 MY MYPI2013002706A patent/MY163394A/en unknown
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