AR054191A1 - Compuestos de 3 aminopirrolidina sustituidos utiles como inhibidores de la recaptacion de monoamina - Google Patents
Compuestos de 3 aminopirrolidina sustituidos utiles como inhibidores de la recaptacion de monoaminaInfo
- Publication number
- AR054191A1 AR054191A1 ARP060101917A ARP060101917A AR054191A1 AR 054191 A1 AR054191 A1 AR 054191A1 AR P060101917 A ARP060101917 A AR P060101917A AR P060101917 A ARP060101917 A AR P060101917A AR 054191 A1 AR054191 A1 AR 054191A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- lower alkyl
- groups
- substituted
- optionally substituted
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 238000011084 recovery Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 47
- -1 pyrrolidine compound Chemical class 0.000 abstract 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 11
- 125000004414 alkyl thio group Chemical group 0.000 abstract 9
- 125000003545 alkoxy group Chemical group 0.000 abstract 8
- 125000005843 halogen group Chemical group 0.000 abstract 7
- 125000003277 amino group Chemical group 0.000 abstract 6
- 125000000623 heterocyclic group Chemical group 0.000 abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- 125000004076 pyridyl group Chemical group 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 4
- 125000002252 acyl group Chemical group 0.000 abstract 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 125000000335 thiazolyl group Chemical group 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004043 oxo group Chemical group O=* 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 2
- 230000001225 therapeutic effect Effects 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000005157 alkyl carboxy group Chemical group 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 125000005037 alkyl phenyl group Chemical group 0.000 abstract 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005366 cycloalkylthio group Chemical group 0.000 abstract 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract 1
- 230000001747 exhibiting effect Effects 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 abstract 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 125000001041 indolyl group Chemical group 0.000 abstract 1
- 125000005956 isoquinolyl group Chemical group 0.000 abstract 1
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 abstract 1
- 125000005029 naphthylthio group Chemical group C1(=CC=CC2=CC=CC=C12)S* 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002971 oxazolyl group Chemical group 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000005936 piperidyl group Chemical group 0.000 abstract 1
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 1
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 1
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 1
- 125000005554 pyridyloxy group Chemical group 0.000 abstract 1
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 1
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 abstract 1
- 238000001228 spectrum Methods 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical group C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 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 ring carbon atoms
- C07D207/14—Nitrogen atoms not forming part of a nitro radical
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Abstract
El compuesto de pirrolidina o una sal del mismo de la presente puede usarse para producir una preparacion farmacéutica de espectro terapéutico más amplio y capaz de exhibir suficientes efectos terapéuticos luego de un corto término de administracion. Reivindicacion 1: Un compuesto de pirrolidina de formula general (1), o una sal del mismo, caracterizado porque cada uno de R101 y R102 es independientemente uno de los siguientes grupos (1) a (86): (1) un grupo fenilo , (2) un grupo piridilo; (3) a un grupo benzotienilo; (4) un grupo indolilo; (5) un grupo 2, 3-dihidro-lH-indenilo; (6) un grupo naftilo; (7) un grupo benzofurilo; (8) un grupo quinolilo;(9) un grupo tiazolilo; (10) un grupo pirimidinilo; (11) un grupo pirazinilo; (12) un grupo benzotiazolilo; (13) un grupo tieno[3, 2-b]piridilo; (14) un grupo tienilo; (15) un grupo cicloalquilo; (16) un grupo tetrahidropiranilo; (17) un grupo pirrolilo; (18) un grupo 2, 4-dihidro-l, 3-benzodioxinilo; (19) un grupo 2, 3-dihidrobenzofurilo; (20) un grupo 9H-fluorenilo; (21) un grupo pirazolilo; (22) un grupo piridazinilo; (23) un grupo indolinilo; (24) un grupo tieno[2, 3-b]piridilo; (25) un grupo tieno[3, 2-d]pirimidinio; (26) un grupo tieno [3, 2- e]pirimidinilo; (27) un grupo lH-pirazolo[3, 4-b]piridilo; (28) un grupo isoquinolilo; (29) un grupo 2,3-dihidro-l,4-benzoxadinilo; (30) un grupo quinoxalinilo; (31) un grupo quinazolinilo; (32) un grupo 1,2,3,4-tetrahidroquinolilo; (33) un grupo cicloalquilo alquilo inferior; (34) un grupo alquilo inferior alquiltio inferior; (35) un grupo alquilo inferior amino-sustituido opcionalmente sustituido por uno o dos grupos alquilo inferior en el grupo amino; (36) un grupo fenoxi alquilo inferior; (37) un grupo piridiloxi alquilo inferior; (38) un grupo alquinilo inferior; (39) un grupo fenilo alquenilo inferior; (40) un grupo 1, 3-benzodioxolilo; (41) un grupo 2,3-dihidro-l, -benzodioxinilo; (42) un grupo 3,4-dihidro-l,5- benzodioxepinilo; (43) un grupo dihidropiridilo; (44) un grupo 1, 2-dihidroquinolilo; (45) un grupo 1,2,3,4-tetrahidroisoquinolilo; (46) un grupo benzoxazolilo; (47) un grupo benzoisotiazolilo; (48) un grupo indazolilo; (49) un grupo benzoimidazolilo; (50) un grupo imidazolilo; (51) un grupo 1,2,3,4-tetrahidronaftilo alquilo inferior; (52) un grupo imidazo[1,2-a]piridilo alquilo inferior; (53) un grupo tiazolilo alquilo inferior; (54) un grupo tetrahidropiranilo alquilo inferior; (55) un grupo piperidilo alquilo inferior; (56) un grupo difenilo alcoxi inferior-sustituido alquilo inferior; (57) un grupo alcoxicarbonilo inferior-sustituido alquilo inferior; (58) un grupo fenilo alcoxicarbonilo inferior-sustituido alquilo inferior; (59) un grupo hidroxi-sustituido alquilo inferior; (60) un grupo alcoxi inferior alquilo inferior; (61) un grupo carboxi alquilo inferior; (62) un grupo carbamoilo-sustituido alquilo inferior opcionalmente sustituido con uno o dos grupos alquilo inferior en el grupo carbamoilo; (63) un grupo alquenilo inferior; (64) un grupo morfolinilocarbonilo alquilo inferior; (65) un grupo benzoílo alquilo inferior; (66) un grupo feniltio alquilo inferior; (67) un grupo naftiltio alquilo inferior; (68) un grupo cicloalquiltio alquilo inferior; (69) un grupo piridiltio alquilo inferior; (70) un grupo pirimidiniltio alquilo inferior; (71) un grupo furiltio alquilo inferior; (72) un grupo tieniltio alquilo inferior; (73) un grupo 1,3,4- tiadiazoliltio alquilo inferior; (74) un grupo benzimidazoliltio alquilo inferior; (75) un grupo benzotiazoliltio alquilo inferior; (76) un grupo tetrazoliltio alquilo inferior; (77) un grupo benzoxazoliltio alquilo inferior; (78) un grupo tiazoliltio alquilo inferior; (79) un grupo imidazoliltio alquilo inferior; (80) un grupo amino-sustituido alquilo inferior alquiltio inferior opcionalmente sustituido con uno o dos grupos alquilo inferior en el grupo amino; (81) un grupo fenilo- sustituido alquilo inferior alquiltio inferior; (82) un grupo furilo-sustituido alquilo inferior alquiltio inferior; (83) un grupo piridilo-sustituido alquilo inferior alquiltio inferior; (84) un grupo hidroxi-sustituido alquilo inferior alquiltio inferior; (85) un grupo fenoxi-sustituido alquilo inferior alquiltio inferior; y (86) un grupo alcoxicarbonilo inferior-sustituido alquilo inferior alquiltio inferior; y cada uno de los grupos (1) a (32), (37), (39) a (56), (64) a (79), (81) a (83) y (85) pueden tener uno o más sustituyentes seleccionados entre los siguientes (1-1) a (1-37) en el anillo cicloalquilo, aromático o heterocíclico; (1-1) átomos de halogeno; (1-2) grupos alquiltio inferior opcionalmente sustituidos con uno o más átomos de halogeno; (1-3) grupos alquilo inferior opcionalmente sustituidos con uno o más átomos de halogeno; (1-4) grupos alcoxi inferior opcionalmente sustituidos con uno o más átomos de halogeno; (1-5) un grupo nitro; (1-6) grupos alcoxi inferior carbonilo; (1-7) grupos amino opcionalmente sustituidos con uno o dos grupos alquilo inferior; (1-8) grupos alquilo inferior sulfonilo; (1-9) un grupo ciano; (1-10) un grupo carboxi; (1-11) un grupo hidroxi; (1-12) grupos tienilo; (1-13) grupos oxazolilo; (1-14) grupos naftilo; (1-15) un grupo benzoílo; (1-16) grupos fenoxi opcionalmente sustituidos con uno a tres átomos de halogeno en el anillo fenilo; (1-17) grupos fenilo alcoxi inferior; (1-18) grupos alcanoilo inferior; (1-19) grupos fenilo opcionalmente sustituidos en el anillo fenilo con uno a cinco sustituyentes seleccionados dentro del grupo consistente en átomos de halogeno, grupos alcoxi inferior, un grupo ciano, grupos alcanoilo inferior y grupos alquilo inferior; (1-20) grupos fenilo alquilo inferior; (1-21) grupos ciano alquilo inferior; (1-22) grupos de 5 a 7 miembros saturados sulfonilo sustituido por un grupo heterocíclico, el grupo heterocíclico contiene en el anillo heterocíclico uno o dos heteroátomos seleccionados dentro del grupo consistente en nitrogeno, oxígeno y azufre; (1-23) grupos tiazolilo opcionalmente sustituidos con uno o dos grupos alquilo inferior en el anillo tiazol; (1-24) grupos imidazolilo; (1-25) grupos amino alquilo inferior opcionalmente sustituidos con uno o dos grupos alquilo inferior en el grupo amino; (1-26) grupos pirrolidinilo alcoxi inferior; (1-27) grupos isoxazolilo; (1-28) grupos cicloalquilocarbonilo; (1-29) grupos naftiloxi; (1-30) grupos piridilo; (1-31) grupos furilo; (1-32) grupos feniltio; (1-33) grupo oxo; (1-34) grupo carbamoilo; (1-35) grupos heterocíclico saturados de 5 a 7 miembros que contienen uno o dos heteroátomos seleccionados dentro del grupo consistente en nitrogeno, oxígeno y azufre, estando el grupo heterocíclico opcionalmente sustituido por uno a tres sustituyentes seleccionados dentro del grupo consistente en el grupo oxo; grupos alquilo inferior; grupos alcanoilo inferior; grupos fenilo alquilo inferior; grupos fenilo opcionalmente sustituidos en el anillo fenilo por uno a tres miembros seleccionados dentro del grupos consistente en átomos de halogeno y grupos alcoxi inferior; y grupos piridilo; (1-36) grupo oxido; y (1-37) grupos alcoxido inferior; siempre que R101 y R102 no sean simultáneamente fenilo insustituido.
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