AR049340A1 - 1- heterociclil - l, 5- dihidro- pirido (3,2-b) indol - 2- onas - Google Patents
1- heterociclil - l, 5- dihidro- pirido (3,2-b) indol - 2- onasInfo
- Publication number
- AR049340A1 AR049340A1 ARP050102018A ARP050102018A AR049340A1 AR 049340 A1 AR049340 A1 AR 049340A1 AR P050102018 A ARP050102018 A AR P050102018A AR P050102018 A ARP050102018 A AR P050102018A AR 049340 A1 AR049340 A1 AR 049340A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- 4alkyl
- radical
- hydrogen
- independently
- Prior art date
Links
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title 1
- -1 methanimidamidyl Chemical group 0.000 abstract 36
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 28
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 20
- 125000000217 alkyl group Chemical group 0.000 abstract 19
- 229910052739 hydrogen Inorganic materials 0.000 abstract 16
- 239000001257 hydrogen Substances 0.000 abstract 16
- 125000003118 aryl group Chemical group 0.000 abstract 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 7
- 125000002757 morpholinyl group Chemical group 0.000 abstract 7
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 abstract 6
- 125000003545 alkoxy group Chemical group 0.000 abstract 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 6
- 125000004193 piperazinyl group Chemical group 0.000 abstract 6
- 125000003386 piperidinyl group Chemical group 0.000 abstract 6
- 125000001424 substituent group Chemical group 0.000 abstract 6
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 5
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 abstract 5
- 125000005987 1-oxo-thiomorpholinyl group Chemical group 0.000 abstract 5
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 abstract 5
- 125000001475 halogen functional group Chemical group 0.000 abstract 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 4
- 125000003003 spiro group Chemical group 0.000 abstract 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 2
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 2
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 2
- 125000001786 isothiazolyl group Chemical group 0.000 abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- 125000003373 pyrazinyl group Chemical group 0.000 abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 2
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 2
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 2
- 125000000335 thiazolyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 125000004306 triazinyl group Chemical group 0.000 abstract 2
- 125000001425 triazolyl group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 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
- 125000006700 (C1-C6) alkylthio 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
- 150000001204 N-oxides Chemical class 0.000 abstract 1
- 229910018828 PO3H2 Inorganic materials 0.000 abstract 1
- 229910006069 SO3H Inorganic materials 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 229960005475 antiinfective agent Drugs 0.000 abstract 1
- 239000004599 antimicrobial Substances 0.000 abstract 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000005100 aryl amino carbonyl group Chemical group 0.000 abstract 1
- 125000005129 aryl carbonyl group Chemical group 0.000 abstract 1
- 125000005110 aryl thio group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000002207 metabolite Substances 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 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
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Abstract
La presente se refiere a agentes antiinfecciosos, inhibidores de HIV. Reivindicacion 1: Un compuesto de formula (1), un N-oxido, sal, sal de amonio cuaternario, forma estereoisomera, profármaco, éster o metabolito d dicho compuesto, donde: R1 es hidrogeno, ciano, halo, aminocarbonilo, hidroxicarbonilo, alcoxicarbonilo C1-4, alquilcarbonilo C1-4, mono- o di(alquilo C1-4)aminocarbonilo, arilaminocarbonilo, N-(aril)-N-(alquiloC1-4)aminocarbonilo, metanimidamidilo, N-hidroxi-metanimidamidilo, mono- o di(alquiloC1-4)metanimidamidilo, Het1 o Het2; X es un radical bivalente NR2 O, S, SO, SO2; R2 es: i) hidrogeno, alquilo C1-10, alquenilo C2-10, cicloalquilo C3-7, donde dichos alquilo C1-10, alquenilo C2-10 y cicloalquilo C3-7, cada uno de manera individual e independiente, pueden estar opcionalmente sustituidos con un sustituyente seleccionado del grupo que consiste en ciano, N(R16aR16b), pirrolidinilo, piperidinilo, homopiperidinilo, piperazinilo, 4-(alquiloC1-4)-piperazinilo, morfolinilo, tiomorfolinilo, 1-oxotiomorfolinilo, 1,1-dioxo-tiomorfolinilo, arilo, furanilo, tienilo, pirrolilo, oxazolilo, tiazolilo, imidazolilo, isoxazolilo, isotiazolilo, pirazolilo, oxadiazolilo, tiadiazolilo, triazolilo, tetrazolilo, piridilo, pirimidinilo, pirazinilo, piridazinilo, triazinilo, hidroxicarbonilo, alquilcarbonilo C1-4, N(R16aR16b)carbonilo, alquiloxicarbonilo C1-4, pirrolidin-1-ilcabonilo, piperidin-1-ilcarbonilo, homopiperidin-1-ilcarbonilo, piperazin-1-ilcarbonilo, 4- (alquiloC1-4)-piperazin-1-ilcarbonilo, morfolin-1-ilcarbonilo, tiomorfolin-1-ilcarbonilo, 1-oxotiomorfolin-1-ilcarbonilo y 1,1-dioxo-tiomorfolin-1-ilcarbonilo; o R2 es ii) arilo sustituido con un radical -COOR4; o R2 es iii) alquilo C1-10, alquenilo C2-10, cicloalquilo C3-7, donde dichos alquilo C1-10, alquenilo C2-10 y cicloalquilo C3-7, cada uno de manera individual e independiente, están sustituidos con arilo, donde dicho arilo está sustituido con un radical -COOR4; o R2 es iv) alquilo C1- 10, alquenilo C2-10, cicloalquilo C3-7, donde cada uno de manera individual e independiente está sustituido con un radical seleccionado de -NR5a-C(=NR5b)-NR5cR5d, -NR5a-C(=NR5e)-R5f, -O-NR5a-C(=NR5b)-NR5cR5d, -O-NR5a-C(=NR5e)-R5f, -sulfonil-R6, - NR7R8, -NR9R10, un radical de grupo de formulas (2) a (6), donde cada Q1 es, de manera independiente, un enlace directo, -CH2-, o -CH2-CH2-; cada Q2 es, de manera independiente, O, S, SO o SO2; cada R4 es, de manera independiente, hidrogeno, alquilo C1-4, aril-alquiloC1-4; cada R5a, R5b, R5c, R5d, de manera independiente, es hidrogeno, alquilo C1-4, o aril-alquiloC1-4; cada R5e, R5f es, de manera independiente, hidrogeno, alquilo C1-4, o aril-alquiloC1-4, o R5e y R5f, tomados juntos, pueden formar un radical alcanodiilo bivalente de formula -CH2-CH2- o -CH2-CH2-CH2-; R6 es alquilo C1-4, -N(R5aRb), alquiloxi C1-4, pirrolidin-1-ilo, piperidin-1-ilo, homopiperidin-1-ilo, piperazin-1-ilo, 4-(alquiloC1-4)-piperazin-1-ilo, morfolin-4-ilo, tiomorfolin-4-ilo, 1-oxotiomorfolin-4-ilo y 1,1-dioxotiomorfolin-4-ilo; o R7 es hidrogeno, alquilo C1-4, hidroxi-alquiloC1-4, alcoxiC1-4alquiloC1-4 o alquiloC1-4-carboniloxi-alquiloC1-4; R8 es hidroxi-alquiloC1-4, alcoxiC1-4alquiloC1-4, alquilcarboniloxiC1-4alquiloC1-4, arilo o aril-alquiloC1-4; R9 es hidrogeno o alquilo C1-4; R10 es Het1, Het2, o un radical de formula (7); R11 es arilo, aril-alquiloC1-4, formilo, alquilcarbonilo C1-4, arilcarbonilo, aril-alquilcarboniloC1-4, alquiloxicarbonilo C1-4, aril-alquiloxicarboniloC1-4, R5aR5bN-carbonilo, hidroxi-alquiloC1-4, alquiloxiC1-4alquiloC1-4, aril-alquiloC1-4alquiloC1-4, ariloxi-alquiloC1-4, Het2; cada R12 es, de manera independiente, hidroxi, alquilo C1-4, aril- alquiloC1-4, alquiloxi C1-4, aril-alquiloxiC1-4, oxo, espiro(alcanodioxi C2-4), espiro(di-alquiloxiC1-4), -NR5aR5b; R13 es hidrogeno, hidroxi, alquilo C1-4, alquiloxi C1-4, o aril-alquiloxiC1-4; o R13a es alquilo C1-4, aril-alquiloC1-4, alquiloxicarbonilo C1-4, o aril-alquiloxicarboniloC1-4; cada R13b es hidrogeno o alquilo C1-4; o R2 es iv) un radical grupo de formulas (8) a (12), donde el radical de formula (10), uno de los átomos de hidrogeno en -CpH2p- y uno de los átomos de hidrogeno en -CH(OR14)-CqH2q-, que no es parte de R14, puede estar reemplazado con un enlace directo o un grupo alcanodiilo C1-4; p es 1; 2; o 3; q es 0; 1; 2; o 3; m es 1 a 10; cada R1 es, de manera independiente, hidrogeno, alquilo C1-4, aril- alquiloC1-4, arilo, alquilcarbonilo C1-4, -SO3H, -PO3H2; R15 es un sustituyente seleccionado del grupo que consiste en ciano, NR16aR16b, pirrolidinilo, piperidinilo, homopiperidinilo, piperazinilo, 4-(alquiloC1-4)-piperazinilo, morfolinilo, tiomorfolinilo, 1-oxotiomorfolinilo, 1,1-dioxo-tiomorfolinilo, arilo, furanilo, tienilo, pirrolilo, oxazolilo, tiazolilo, imidazolilo, isoxazolilo, isotiazolilo, pirazolilo, oxadiazolilo, tiadiazolilo, triazolilo, tetrazolilo, piridilo, pirimidinilo, pirazinilo, piridazinilo, triazinilo, hidroxi-carbonilo, alquilcarbonilo C1-4, N(R16aR16b)carbonilo, alquiloxicarbonilo C1-4, pirrolidin-1-ilcabonilo, piperidin-1-ilcarbonilo, homopiperidin-1-ilcarbonilo, piperazin-1-ilcarbonilo, 4- (alquiloC1-4)-piperazin-1-ilcarbonilo, morfolin-1-il-carbonilo, tiomorfolin-1-ilcarbonilo, 1-oxotiomorfolin-1-ilcarbonilo y 1,1-dioxo-tiomorfolin-1-ilcarbonilo; y donde R15 adicionalmente puede ser arilo sustituido con un radical -COOR4, o un radical seleccionado de-NR5a-C(=NR5b)-NR5cR5d, -NR5a-C(=NR5e)-R5f, -O-NR5a-C(=NR5b)-NR5cR5d, -O-NR5a-C(=NR5e)-R5f, -sulfonil-R6, -NR7R8, -NR9R10, un radical de grupo de formulas (2) a (4); donde R4, R5a, R5b, R5c, R5d, R6, R7, R8, R9, R10 y los radicales de formulas (2) a (4) son, de modo independiente, como se describen con anterioridad; R16a es hidrogeno, alquilo C1-4 o alquilo C1-4 sustituido con un sustituyente seleccionado del grupo que consiste en amino, mono- o di(alquiloC1-4)amino, pirrolidinilo, piperidinilo, homopiperidinilo, piperazinilo, 4-(alquiloC1-4)-piperazinilo, morfolinilo, tiomorfolinilo, 1-oxotiomorfolinilo, y 1,1-dioxo-tiomorfolinilo; R16b es hidrogeno, alquilo C1-4 o alquilo C1-4 sustituido con un sustituyente seleccionado del grupo que consiste en amino, mono- o di(alquiloC1-4)amino, pirrolidinilo, piperidinilo, homopiperidinilo, piperazinilo, 4-(alquiloC1-4)-piperazinilo, morfolinilo, tiomorfolinilo, 1-oxotiomorfolinilo, y 1,1-dioxo-tiomorfolinilo; cada R17 es, de manera independiente, hidrogeno, alquilo C1-4 aril-alquiloC1-4; R18 es hidrogeno, hidroxi, alquilo C1-4 o un radical -COOR4; -a1 = a2 - a3 = a4- representa un radical bivalente de la formula (12) a (16), donde uno, dos, tres o cuatro de los átomos de hidrogeno en la formula (12) pueden estar reemplazados con un radical alquilo C1-6, alcoxi C1-4, halo, hidroxi, (R5g)(R5h)N-(alcanodiiloC1-4)-O-, (R7)(R8)N-(alcanodiiloC1-4)-O-, (R8)(R9)N-(alcanodiiloC1-4)-O-, trifluorometilo, ciano, un radical -COOR4, (R5a)(R5b)N-carbonilo, (R5a)(R5b)N-sulfonilo, pirrolidinilsulfonilo, piperidinilsulfonilo, homopiperidinilsulfonilo, formilo, alquilcarbonilo C1-6, nitro, hidroxi-alquiloC1-6, alcoxiC1-4alquiloC1-6, (R4OOC)-alquiloC1-6, un radical -N(R5a)(R5b), -N(R7)(R8), -(R9)(R10), un radical de formula (2), o de formula (17), morfolinilo, tiomorfolinilo, 1-oxotiomorfolinilo, 1,1-dioxo-tiomorfolinilo, (R5g)(R5h)N-(alcanodiiloC1-4)-N(R5c)-, (R7)(R8)N-(alcanodiiloC1-4)-N(R5c)-, (R9)(R10)N- (alcanodiiloC1-4)-N(R5c)-, alquilcarbonilamino C1-6, alquiloxicarbonilamino C1-6, trifluoracetilamino, alquilsulfonilamino C1-6, (R5a)(R5b)N-alquiloC1-4, arilo, Het1 o Het2; R20 es hidrogeno, hidroxi, alquilo C1-4, aril-alquiloC1-4, alquiloxi C1-4, aril-alquiloxiC1-4, oxo, espiro(alquilenodioxiC2-4), espiro(di-alquiloxiC1-4), -NR5gR5h; cada R5g o R5h es, de manera independiente, hidrogeno, alquilo C1-4 o aril-alquiloC1-4, o R5g y R5h junto con el nitrogeno al cual están unidos forman un radical pirrolidinilo, piperidinilo, homopiperidinilo, morfolinilo, piperazinilo o 4-alquilpiperaziniloC1-4; donde cada uno de dichos radicales pirrolidinilo, piperidinilo, homopiperidinilo, morfolinilo, piperazinilo o 4-alquilopiperaziniloC1-4 puede estar opcionalmente sustituido con hidroxi u oxo; o donde uno o más de los átomos de hidrogeno en el grupo de formula de (12) a (16) pueden estar reemplazados por un radical seleccionado de halo y alquilo C1-6; R3 es un sistema de anillo heterocíclico aromático, monocíclico o bicíclico, donde uno, dos tres o cuatro miembros de anillo son heteroátomos, cada uno seleccionado de modo independiente del grupo que consiste en nitrogeno, oxígeno y azufre, y donde los miembros de anillo restantes son átomos de carbono; y donde cada uno de dichos sistemas de anillo heterocíclicos puede estar opcionalmente sustituido con uno, dos, tres, cuatro o cinco sustituyentes, cada uno seleccionado de manera independiente de halo, ciano, nitro, alquilo C1-6, hidroxi-alquiloC1-6, alcoxiC1-4alquiloC1-6, (R5a)(R5b)N-alquiloC1-4, polihalo-alquiloC1-6, cicloalquilo C3-7, aril-alquiloC1-6, formilo, alquilcarbonilo C1-6, un radical -COOR4, (R5a)(R5b)N-carbonilo, (R5a)(R5b)N-sulfonilo, hidroxi, alquiloxi C-16, aril-alquiloxiC1-6, polihalo-alquiloxiC1-6, formiloxi, alquilcarboniloxi C1-6, ariloxi, (R5a)(R5b)N-, formilamino, alquilcarbonilamino C1-6, alquiloxicarbonilamino C1-6, alquilsulfonilamino C1-6, mercapto, alquiltio C1-6, ariltio, aril-alquiltioC1-6, alquilsulfinilo C1-6, alquilsulfonilo C1-6, arilo, -CH(=N-O-R5a), -C(=NH)-NH-R5a; arilo es fenilo opcionalmente sustituido con uno o más sustituyentes, cada uno seleccionado individualmente del grupo que consiste en alquilo C1-6, alcoxi C1-4, halo, hidroxi, amino, trifluorometilo, ciano, nitro, hidroxi-alquiloC1-6, ciano-alquiloC1-6, mono- o di(alquiloC1-4)amino, amino-alquilo1-4, mono- o di(alquiloC1-4)amino-alquiloC1-4; Het1 es un sistema de anillo de 5 miembros, donde uno, dos, tres o cuatro miembros de anillo son heteroátomos seleccionados, cada uno de manera individual e independiente, del grupo que consiste en nitroge
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04102171 | 2004-05-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR049340A1 true AR049340A1 (es) | 2006-07-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP050102018A AR049340A1 (es) | 2004-05-17 | 2005-05-17 | 1- heterociclil - l, 5- dihidro- pirido (3,2-b) indol - 2- onas |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7615639B2 (es) |
| EP (1) | EP1758911A1 (es) |
| JP (1) | JP4898668B2 (es) |
| KR (1) | KR20070015608A (es) |
| CN (1) | CN1953983B (es) |
| AP (1) | AP2006003791A0 (es) |
| AR (1) | AR049340A1 (es) |
| AU (1) | AU2005243439B2 (es) |
| BR (1) | BRPI0511175A (es) |
| CA (1) | CA2564027A1 (es) |
| EA (1) | EA012330B1 (es) |
| IL (1) | IL178555A0 (es) |
| MX (1) | MXPA06013314A (es) |
| NO (1) | NO20065898L (es) |
| TW (1) | TW200607503A (es) |
| WO (1) | WO2005111047A1 (es) |
| ZA (1) | ZA200610587B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA06013312A (es) * | 2004-05-17 | 2007-02-02 | Tibotec Pharm Ltd | 1-fenil-1,5-dihidro-pirido[3,2-b]indol-2-onas 5-sustituidas y analogos como antivirales. |
| CN101305010A (zh) * | 2005-09-01 | 2008-11-12 | 阿雷生物药品公司 | Raf抑制剂化合物及其用法 |
| CN101415708A (zh) | 2006-04-03 | 2009-04-22 | 泰博特克药品有限公司 | 抑制HIV的3,4-二氢-咪唑并[4,5-b]吡啶-5-酮 |
| WO2008037783A1 (en) * | 2006-09-29 | 2008-04-03 | Tibotec Pharmaceuticals Ltd. | Process for preparing 2-oxo-2,5-dihydro-1h-pyrido[3,2-b]indole-3-carbonitriles |
| KR20120034592A (ko) | 2009-04-09 | 2012-04-12 | 베링거 인겔하임 인터내셔날 게엠베하 | Ｈｉｖ 복제의 저해제 |
| CN102858741A (zh) * | 2010-05-14 | 2013-01-02 | 阿费克蒂斯制药股份公司 | 制备p2x7r拮抗剂的新方法 |
| EP3241830A1 (de) | 2016-05-04 | 2017-11-08 | Bayer CropScience Aktiengesellschaft | Kondensierte bicyclische heterocyclen-derivate als schädlingsbekämpfungsmittel |
| CA3031139A1 (en) | 2016-07-19 | 2018-01-25 | Bayer Cropscience Aktiengesellschaft | Condensed bicyclic heterocycle derivatives as pest control agents |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| PH30929A (en) | 1992-09-03 | 1997-12-23 | Janssen Pharmaceutica Nv | Beads having a core coated with an antifungal and a polymer. |
| CZ289214B6 (cs) | 1993-10-01 | 2001-12-12 | Astra Aktiebolag | Způsob zpracování jemně děleného práąkového léčiva, zařízení k provádění tohoto způsobu a aglomeráty vyrobené tímto způsobem |
| US5612330A (en) * | 1994-03-07 | 1997-03-18 | Warner-Lambert Company | Methods for inhibiting and controlling viral growth |
| BR9706897B1 (pt) | 1996-05-20 | 2010-09-21 | forma de dosagem farmacêutica. | |
| ES2201485T3 (es) | 1997-03-26 | 2004-03-16 | Janssen Pharmaceutica N.V. | Palets que tienen un nucleo recubierto con un agente antifungico y un polimero. |
| US6596729B2 (en) | 2000-07-20 | 2003-07-22 | Bristol-Myers Squibb Company | Tricyclic-2-pyridone compounds useful as HIV reverse transcriptase inhibitors |
| US20020182151A1 (en) | 2000-12-18 | 2002-12-05 | The Government Of The U.S.A. As Represented By The Secretary Of The Dept. Of Health & Human Services | Benzoylalkylindolepyridinium componds and pharmaceutical compositions comprising such compounds |
| WO2002059123A2 (en) | 2000-12-18 | 2002-08-01 | The Government Of The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Benzoylalkylindolepyridinium compounds and pharmaceutical compositions comprising such compounds |
| US20030096833A1 (en) * | 2001-08-31 | 2003-05-22 | Jagtap Prakash G. | Substituted ideno[1,2-c]isoquinoline derivatives and methods of use thereof |
| MXPA05005146A (es) * | 2002-11-15 | 2005-07-22 | Tibotec Pharm Ltd | Indolpiridinio sustituido como compuestos antiinfecciosos. |
-
2005
- 2005-05-17 AU AU2005243439A patent/AU2005243439B2/en not_active Ceased
- 2005-05-17 KR KR1020067025910A patent/KR20070015608A/ko not_active Application Discontinuation
- 2005-05-17 AR ARP050102018A patent/AR049340A1/es not_active Application Discontinuation
- 2005-05-17 US US11/568,845 patent/US7615639B2/en not_active Expired - Fee Related
- 2005-05-17 AP AP2006003791A patent/AP2006003791A0/xx unknown
- 2005-05-17 EP EP05749219A patent/EP1758911A1/en not_active Withdrawn
- 2005-05-17 MX MXPA06013314A patent/MXPA06013314A/es active IP Right Grant
- 2005-05-17 TW TW094116037A patent/TW200607503A/zh unknown
- 2005-05-17 JP JP2007517254A patent/JP4898668B2/ja not_active Expired - Fee Related
- 2005-05-17 CN CN200580015818XA patent/CN1953983B/zh not_active Expired - Fee Related
- 2005-05-17 EA EA200602138A patent/EA012330B1/ru not_active IP Right Cessation
- 2005-05-17 CA CA002564027A patent/CA2564027A1/en not_active Abandoned
- 2005-05-17 BR BRPI0511175-7A patent/BRPI0511175A/pt not_active IP Right Cessation
- 2005-05-17 WO PCT/EP2005/052264 patent/WO2005111047A1/en active Application Filing
-
2006
- 2006-10-15 IL IL178555A patent/IL178555A0/en unknown
- 2006-12-15 ZA ZA200610587A patent/ZA200610587B/xx unknown
- 2006-12-18 NO NO20065898A patent/NO20065898L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1953983A (zh) | 2007-04-25 |
| EA012330B1 (ru) | 2009-08-28 |
| BRPI0511175A (pt) | 2007-12-04 |
| JP4898668B2 (ja) | 2012-03-21 |
| CN1953983B (zh) | 2010-05-26 |
| TW200607503A (en) | 2006-03-01 |
| AU2005243439A1 (en) | 2005-11-24 |
| WO2005111047A1 (en) | 2005-11-24 |
| NO20065898L (no) | 2007-02-19 |
| KR20070015608A (ko) | 2007-02-05 |
| AP2006003791A0 (en) | 2006-10-31 |
| AU2005243439B2 (en) | 2011-09-29 |
| US20070265295A1 (en) | 2007-11-15 |
| JP2007538051A (ja) | 2007-12-27 |
| ZA200610587B (en) | 2008-08-27 |
| EA200602138A1 (ru) | 2007-04-27 |
| EP1758911A1 (en) | 2007-03-07 |
| MXPA06013314A (es) | 2007-02-02 |
| CA2564027A1 (en) | 2005-11-24 |
| IL178555A0 (en) | 2007-02-11 |
| US7615639B2 (en) | 2009-11-10 |
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