AR030302A1 - BISPIDINE COMPOUNDS, PHARMACEUTICAL FORMULATION, USE FOR THE MANUFACTURE OF MEDICINES, PROCESS FOR THE PREPARATION OF THESE INTERMEDIATE COMPOUNDS AND COMPOUNDS - Google Patents

BISPIDINE COMPOUNDS, PHARMACEUTICAL FORMULATION, USE FOR THE MANUFACTURE OF MEDICINES, PROCESS FOR THE PREPARATION OF THESE INTERMEDIATE COMPOUNDS AND COMPOUNDS

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Publication number
AR030302A1
AR030302A1 ARP010103085A ARP010103085A AR030302A1 AR 030302 A1 AR030302 A1 AR 030302A1 AR P010103085 A ARP010103085 A AR P010103085A AR P010103085 A ARP010103085 A AR P010103085A AR 030302 A1 AR030302 A1 AR 030302A1
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Prior art keywords
alkyl
aryl
represent
optionally substituted
terminated
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ARP010103085A
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Spanish (es)
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Astrazeneca Ab
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Priority claimed from SE0002603A external-priority patent/SE0002603D0/en
Priority claimed from SE0002788A external-priority patent/SE0002788D0/en
Application filed by Astrazeneca Ab filed Critical Astrazeneca Ab
Publication of AR030302A1 publication Critical patent/AR030302A1/en

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    • 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
    • C07D471/08—Bridged systems
    • 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
    • A61P9/06—Antiarrhythmics

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Cardiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Compuestos de bispidina que tienen la formula (1), donde R1 representa un fragmento estructural de la formula (2), R4 representa H, halo, alquilo C1-4, -D-OR7, -D-N(R8)R9, o R4, junto con R5, representa =O; R5 representa H, alquilo C1-4, o R5, junto con R4, representa =O; D representa un enlace directo o alquileno C1-4; R7 representa H, alquilo C1-6, -E-arilo, -E-Het1, -C(O)R10a, -C(O)OR10b o -C(O)N(R11a)R11b; R8 representa H, alquilo C1-6, -E-arilo, -E-Het1, -C(O)R10a, -C(O)OR10b, -S(O)2R10c, -[C(O)]nN(R11a)R11b o -C(NH)NH2; R9 representa H, alquilo C1-6, -E-arilo o -C(O)R10d; E representa, cada vez que aparece cuando se utiliza aquí, un enlace directo o alquileno C1-4; R10a a R10d independientemente, representan, cada vez que ocurre cuando se usa aquí, alquilo C1-6 (opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionado de halo, arilo y Het2), arilo, Het3, o R10a y R10d independientemente repesentan H, R11a y R11b independientemente, representa, cada vez que aparece cuando se usa aquí, H, alquilo(C1-6) (opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionado de halo, arilo y Het4), arilo, Het5 o R11a y R11b juntos representan alquileno C3-7, donde el grupo alquileno está opcionalmente interrumpido por un átomo de oxígeno; n representa 1 o 2; A representa -G-, -J-N(R12)-, o -J-O- (donde, en los dos ultimos grupos, J está unido al átomo de nitrogeno de la bispidina); B representa -L-, -L-N(R13)-, -N(R13)-L-, -L-S(O)p- o -L-O- (donde, en estos dos ultimos grupos, L está unido al átomo de carbono que porta R4 y R5); G representa un enlace directo o alquileno C1-6; J representa alquileno C2-6; L representa un enlace directo o alquileno C1-4; p representa 0, 1 o 2; R12 y R13 independientemente representan H o alquilo C1-4; R6 representa arilo, Het6 (ambos grupos están opcionalmente sustituidos y/o terminado (si es apropiado) con uno o más sustituyentes seleccionados de -OH, ciano, halo, nitro, alquilo C1-6 (opcionalmente terminado por -N(H)C(O)OR14a), alcoxi C1-6, arilo, Het7, -N(R15a)R15b, -C(O)R15c, C(O)OR15d, -C(O)N(R15e)R, -N(R15g)C(O)R15h, N(R15i)C(O)N(R15j)R15K, -N(R15m)S(O2)R14b, -S(O)qR14c, -OS(O)2R14d y -S(O)2N(R15n)R15p o cuando R4 y R5 juntos representan = O, R6 puede representar alquilo C1-6; q representa 0, 1 o 2; R2 representa -CN, Het8, -C(O)R16, -C(S)OR17, -C(S)N(R18)R19, -[C(O)]2N(R20a)R20b, -[C(O)]2OR21, -S(O)2R22, -S(O)2N(R23)R24, -C(=N-CN)N(R25)R26, -C(=N-CN)OR27 o alquilo C1-12 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionado de -C(O)R28, -C(O)N(R29a)R29b, -N(R30)R31, -OR32, -S(O)rR33, halogeno, -CN, nitro, arilo y Het9); R16 representa H, arilo, Het10 o alquilo C1-6 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionados de halogeno, -OH, -CN, -N(R34)R35, arilo y Het11); R34 representa H, alquilo C1-6, arilo, Het12, -C(O)R36a o -C(O)OR36b; R18 representa H, arilo, Het13, -C(O)R36a, -C(O)OR36b o alquilo C1-6 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionados de halogeno, - OH, -CN, -C(O)R36a y -C(O)OR36b); R22 representa Het14, arilo, o alquilo C1-6 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionados de halogeno, -OH, -CN, Het15 y arilo); R23 representa H, alquilo C1-6, arilo, Het16, -C(O)R36a, -C(O)OR36b, o -C(O)SR36b; R25 representa H o alquilo C1-6 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionados de halogeno, -OH, -CN, alquilo C1-6 (donde el grupo alquilo está opcionalmente sustituido y/o terminado con uno o más sustituyentes seleccionados de alquilo C1-4 y -OH), alcoxi C1-6 y arilo); R27 representa alquilo C1-6 o arilo; R28 representa H, alquilo C1-6, arilo o Het17; R29a y R29b independientemente representan H, alquilo C1-6, arilo o Het18; R30 representa H, alquilo C1-6, arilo, Het19, -C(O)R37a, -C(O)OR37b o -C(O)N(R37c)R37d; R31 representa H, alquilo C1-6, arilo o Het20; R32 representa H, alquilo C1-6, arilo, Het21, -C(O)R37a, -C(O)OR37b o -C(O)N(R37c)R37d; R3 representa alquilo C1-6, arilo o Het22; r representa 0, 1 o 2; R36a y R36b independientemente representa, cada vez que ocurre cuando se usa aquí, alquilo C1-6, o R36a representa H; R37a a R37d independientemente representan, cada vez que ocurre cuando se utiliza aquí, alquilo C1-6, arilo o Het23, o R37a, R37c y R37d independientemente representan H; Het1 a Het23 independientemente representan, cada vez que ocurre cuando se usa aquí, grupos heterocíclicos con entre cinco y doce miembros que contienen uno o más heteroátomos seleccionados de oxígeno, nitrogeno y/o azufre, R3a y R3b independientemente, representan H, alquilo C1-4, -OR38a, -SR38b, -N(R39)R38c, o R3a y R3b juntos representan alquileno C3-5, -O-Z-O-, -O-Z-S- o -S-Z-S-; R39 representa H, alquilo C1-6 o un fragmento estructural de la formula (2) como definimos anteriormente; Z representa alquileno C2-3 opcionalmente sustituido con uno o más grupos alquilo C1-4; R41 a R46 independientemente representan H o alquilo C1-3; R14a a R14d, R17 y R21 independientemente representan alquilo C1-6; R15a a R15p, R19, R20a, R20b, R24, R26, R35 y R38a a R38c independientemente representan H o alquilo C1-6; donde cada arilo y cada grupo Het (Het1 a Het23), a menos que se especifique de otro modo, está opcionalmente sustituido; o un derivado farmacéuticamente aceptable del mismo; con la condicion de que: (a) cuando R1 representa un fragmento estructura de la formula (2) donde: R4 y R5 juntos representan = O; A representa un enlace directo; entonces B no representa un enlace directo; -N(R13)-L- (donde el grupo -N(R13)- está unido al átomo de carbono que porta R4 y R5), -N(R13)-, -S(O)p- u -O-; (b) cuando R5 representa H o alquilo C1-4; y A representa -J-N(R12)- o -J-O; entonces B no representa -N(R13)-L-, -N(R13)-, -S(O)p- u -O; (c) cuando R4 representa -D-OR7, -D-N(R8)R9 donde D representa un enlace directo entonces: (i) A no representa -J-N(R13)- o -J-O; y (ii) B no representa N-(R13)-L-, -N(R13)-, -S(O)p- u -O-; (d) cuando R3a y R3b ambos representan H; y R1 representa bencilo no sustituido; entonces R2 no representa bencilo no sustituido o benzoilo opcionalmente sustituido; y (e) el compuesto no es: (i) N1-fenil-3-(7-bencil-3,7-diazabiciclo[3.3.1]non-3-il)-propanamida; (ii) 3-bencil-7-[3-(4-cianofenoxi)-2-hidroxipropil]-6,8-dimetil-3,7-diazabiciclo[3.3.1] nonano; (iii) 3-bencil-7-[3-(4-cianofenoxi)-2-hidroxipropil]-6-metil-3,7-diazabiciclo[3.3.1]nonano; (iv) N-{2-(7-bencil-3,7-diazabiciclo[3.3.1]-non-3-il)-1[(4-ciano-fenoxi)metil]etil} metansulfonamida; (v) 3-bencil-7-[3-(2-propil-1,3-dioxolan-2-il)propil]-3,7-diazabiciclo[3.3.1]nonano; o (vi) 7-bencil-3,7-diazabiciclo[3.3.1]nonano-3-etanol; que son utiles para la profilaxis y el tratamiento de las arritmias, en particular, las arritmias atrial y ventricular; formulacion farmacéutica, uso para la fabricacion de medicamentos, proceso para la preparacion de estos compuestos, y compuestos intermediarios.Bispidine compounds having the formula (1), where R1 represents a structural fragment of the formula (2), R4 represents H, halo, C1-4 alkyl, -D-OR7, -DN (R8) R9, or R4, together with R5, represents = O; R5 represents H, C1-4 alkyl, or R5, together with R4, represents = O; D represents a direct bond or C1-4 alkylene; R7 represents H, C1-6 alkyl, -E-aryl, -E-Het1, -C (O) R10a, -C (O) OR10b or -C (O) N (R11a) R11b; R8 represents H, C1-6 alkyl, -E-aryl, -E-Het1, -C (O) R10a, -C (O) OR10b, -S (O) 2R10c, - [C (O)] nN (R11a ) R11b or -C (NH) NH2; R9 represents H, C1-6 alkyl, -E-aryl or -C (O) R10d; E represents, each time it appears when used here, a direct bond or C1-4 alkylene; R10a to R10d independently, represent, whenever it occurs when used herein, C1-6 alkyl (optionally substituted and / or terminated with one or more substituents selected from halo, aryl and Het2), aryl, Het3, or R10a and R10d independently H, R11a and R11b independently represent, each time it appears when used herein, H, (C1-6) alkyl (optionally substituted and / or terminated with one or more substituents selected from halo, aryl and Het4), aryl, Het5 or R11a and R11b together represent C3-7 alkylene, where the alkylene group is optionally interrupted by an oxygen atom; n represents 1 or 2; A represents -G-, -J-N (R12) -, or -J-O- (where, in the last two groups, J is attached to the bispidine nitrogen atom); B represents -L-, -LN (R13) -, -N (R13) -L-, -LS (O) p- or -LO- (where, in these last two groups, L is attached to the carbon atom that R4 and R5); G represents a direct bond or C1-6 alkylene; J represents C2-6 alkylene; L represents a direct bond or C1-4 alkylene; p represents 0, 1 or 2; R12 and R13 independently represent H or C1-4 alkyl; R6 represents aryl, Het6 (both groups are optionally substituted and / or terminated (if appropriate) with one or more substituents selected from -OH, cyano, halo, nitro, C1-6 alkyl (optionally terminated by -N (H) C (O) OR14a), C1-6 alkoxy, aryl, Het7, -N (R15a) R15b, -C (O) R15c, C (O) OR15d, -C (O) N (R15e) R, -N (R15g ) C (O) R15h, N (R15i) C (O) N (R15j) R15K, -N (R15m) S (O2) R14b, -S (O) qR14c, -OS (O) 2R14d and -S (O ) 2N (R15n) R15p or when R4 and R5 together represent = O, R6 may represent C1-6 alkyl; q represents 0, 1 or 2; R2 represents -CN, Het8, -C (O) R16, -C (S ) OR17, -C (S) N (R18) R19, - [C (O)] 2N (R20a) R20b, - [C (O)] 2OR21, -S (O) 2R22, -S (O) 2N ( R23) R24, -C (= N-CN) N (R25) R26, -C (= N-CN) OR27 or C1-12 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected of -C (O) R28, -C (O) N (R29a) R29b, -N (R30) R31, -OR32, -S (O) rR33, halogen, -CN, nitro, aryl and Het9); R16 represents H, aryl, Het10 or C1-6 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected from halogen, -OH, -CN, -N (R34) R35, aryl and Het11); R34 represents H, C1-6 alkyl, aryl, Het12, -C (O) R36a or -C (O) OR36b; R18 represents H, aryl, Het13, -C (O) R36a, -C (O) OR36b or C1-6 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected from halogen, - OH, -CN, -C (O) R36a and -C (O) OR36b); R22 represents Het14, aryl, or C1-6 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected from halogen, -OH, -CN, Het15 and aryl); R23 represents H, C1-6 alkyl, aryl, Het16, -C (O) R36a, -C (O) OR36b, or -C (O) SR36b; R25 represents H or C1-6 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected from halogen, -OH, -CN, C1-6 alkyl (where the alkyl group is optionally substituted and / or terminated with one or more substituents selected from C1-4 alkyl and -OH), C1-6 alkoxy and aryl); R27 represents C1-6 alkyl or aryl; R28 represents H, C1-6 alkyl, aryl or Het17; R29a and R29b independently represent H, C1-6 alkyl, aryl or Het18; R30 represents H, C1-6 alkyl, aryl, Het19, -C (O) R37a, -C (O) OR37b or -C (O) N (R37c) R37d; R31 represents H, C1-6 alkyl, aryl or Het20; R32 represents H, C1-6 alkyl, aryl, Het21, -C (O) R37a, -C (O) OR37b or -C (O) N (R37c) R37d; R3 represents C1-6 alkyl, aryl or Het22; r represents 0, 1 or 2; R36a and R36b independently represents, each time it occurs when used herein, C1-6 alkyl, or R36a represents H; R37a to R37d independently represent, each time it occurs when used herein, C1-6 alkyl, aryl or Het23, or R37a, R37c and R37d independently represent H; Het1 to Het23 independently represent, whenever it occurs when used herein, heterocyclic groups with between five and twelve members containing one or more heteroatoms selected from oxygen, nitrogen and / or sulfur, R3a and R3b independently, represent H, C1- alkyl 4, -OR38a, -SR38b, -N (R39) R38c, or R3a and R3b together represent C3-5 alkylene, -OZO-, -OZS- or -SZS-; R39 represents H, C1-6 alkyl or a structural fragment of the formula (2) as defined above; Z represents C2-3 alkylene optionally substituted with one or more C1-4 alkyl groups; R41 to R46 independently represent H or C1-3 alkyl; R14a to R14d, R17 and R21 independently represent C1-6 alkyl; R15a to R15p, R19, R20a, R20b, R24, R26, R35 and R38a to R38c independently represent H or C1-6 alkyl; where each aryl and each Het group (Het1 to Het23), unless otherwise specified, is optionally substituted; or a pharmaceutically acceptable derivative thereof; with the proviso that: (a) when R1 represents a structure fragment of the formula (2) where: R4 and R5 together represent = O; A represents a direct link; then B does not represent a direct link; -N (R13) -L- (where the group -N (R13) - is attached to the carbon atom carrying R4 and R5), -N (R13) -, -S (O) p- or -O-; (b) when R5 represents H or C1-4 alkyl; and A represents -J-N (R12) - or -J-O; then B does not represent -N (R13) -L-, -N (R13) -, -S (O) p- or -O; (c) when R4 represents -D-OR7, -D-N (R8) R9 where D represents a direct link then: (i) A does not represent -J-N (R13) - or -J-O; and (ii) B does not represent N- (R13) -L-, -N (R13) -, -S (O) p- or -O-; (d) when R3a and R3b both represent H; and R1 represents unsubstituted benzyl; then R2 does not represent unsubstituted benzyl or optionally substituted benzoyl; and (e) the compound is not: (i) N1-phenyl-3- (7-benzyl-3,7-diazabicyclo [3.3.1] non-3-yl) -propanamide; (ii) 3-Benzyl-7- [3- (4-cyanophenoxy) -2-hydroxypropyl] -6,8-dimethyl-3,7-diazabicyclo [3.3.1] nonane; (iii) 3-benzyl-7- [3- (4-cyanophenoxy) -2-hydroxypropyl] -6-methyl-3,7-diazabicyclo [3.3.1] nonane; (iv) N- {2- (7-benzyl-3,7-diazabicyclo [3.3.1] -non-3-yl) -1 [(4-cyano-phenoxy) methyl] ethyl} methanesulfonamide; (v) 3-benzyl-7- [3- (2-propyl-1,3-dioxolan-2-yl) propyl] -3,7-diazabicyclo [3.3.1] nonane; or (vi) 7-benzyl-3,7-diazabicyclo [3.3.1] nonano-3-ethanol; which are useful for the prophylaxis and treatment of arrhythmias, in particular atrial and ventricular arrhythmias; Pharmaceutical formulation, use for the manufacture of medicines, process for the preparation of these compounds, and intermediary compounds.

ARP010103085A 2000-07-07 2001-06-28 BISPIDINE COMPOUNDS, PHARMACEUTICAL FORMULATION, USE FOR THE MANUFACTURE OF MEDICINES, PROCESS FOR THE PREPARATION OF THESE INTERMEDIATE COMPOUNDS AND COMPOUNDS AR030302A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE0002603A SE0002603D0 (en) 2000-07-07 2000-07-07 New compounds
SE0002788A SE0002788D0 (en) 2000-07-27 2000-07-27 New compounds

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AR030302A1 true AR030302A1 (en) 2003-08-20

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US7399765B2 (en) 2003-09-19 2008-07-15 Abbott Laboratories Substituted diazabicycloalkane derivatives
SE0302775D0 (en) * 2003-10-20 2003-10-20 Astrazeneca Ab Chemical compound and assay
RU2472793C1 (en) * 2011-07-20 2013-01-20 Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Московский государственный университет тонких химических технологий имени М.В. Ломоносова" (МИТХТ им.М.В.Ломоносова) 1,5-bis[(tert-butylamino)methyl]-n,n'-di-tert-butylbispidin-9-one and method for production thereof

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CN1440407A (en) 2003-09-03
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AU2001271161A1 (en) 2002-01-21
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PL360474A1 (en) 2004-09-06
CZ200332A3 (en) 2003-04-16
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