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AR014974A1 - COMPOUNDS WITH ACTIVITY ON MUSCARINIC RECEPTORS, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND THE USE OF THEM FOR THE MANUFACTURE OF A MEDICINE - Google Patents

COMPOUNDS WITH ACTIVITY ON MUSCARINIC RECEPTORS, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND THE USE OF THEM FOR THE MANUFACTURE OF A MEDICINE

Info

Publication number
AR014974A1
AR014974A1 ARP990101516A ARP990101516A AR014974A1 AR 014974 A1 AR014974 A1 AR 014974A1 AR P990101516 A ARP990101516 A AR P990101516A AR P990101516 A ARP990101516 A AR P990101516A AR 014974 A1 AR014974 A1 AR 014974A1
Authority
AR
Argentina
Prior art keywords
alkyl
nr3r4
aryl
halo
branched
Prior art date
Application number
ARP990101516A
Other languages
Spanish (es)
Original Assignee
Acadia Pharm Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Acadia Pharm Inc filed Critical Acadia Pharm Inc
Publication of AR014974A1 publication Critical patent/AR014974A1/en
Priority to US11/933,177 priority Critical patent/US20080108618A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—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
    • 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
    • C07D207/08—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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings 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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/62—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Hospice & Palliative Care (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Un compuesto con actividad sobre receptores muscarínicos, que comprenden la formula (I) en donde: X1, X2, X3, X4 y X5 se seleccionan entre C, N y O; k es 0o 1; t es 0, 1 o 2; R1 es alquilo C1-8 de cadena ramificada o recta, alquenilo C2-8, alquiniloC1-8, alquilideno C1-8, alcoxi C1-8, heteroalquilo C1-8,aminoalquilo C1-8, haloalquilo C1-8, alcoxicarbonilo C1-8, hidroxialcoxi C1-8, hidroxialquilo C1-8, -SH, alquiltio C1-8, -O-CH2-C5-6 arilo, -C(O)-C5-6 arilosustituido con alquilo C1-3 o halo; arilo C5-6 o cicloalquilo C5-6 que opcionalmente comprende 1 o más heteroátomos seleccionados entre N, S y O; -C(O)NR3R4,-NR3R4, -NR3C(O)NR4R5, -CNR3R4, -OC(O)R3, -(O)(CH2)sNR3R4 o -(CH2)sNR3R4; donde R3, R4 y R5 son iguales o diferentes; cada uno es independientementeseleccionado entre H, alquilo C1-6; arilo C5-6 que opcionalmente comprende 1 o más heteroátomos seleccionados entre N, O y S, y opcionalmente sustituido conhalo o alquilo C1-6; cicloalquilo C3-6; o R3 y R4 junto con el átomo N, cuando está presente, forman una estructura de anillo cíclico que comprende 5-6 átomosseleccionados entre C, N, S y O; y s es un entero de 0 a 8; A es arilo C5-12 o cicloalquilo C5-7; cada uno comprende opcionalmente 1 o más heteroátomosseleccionados entre N, S y O; R2 es H, amino, hidroxilo, halo, o alquilo C1-6 de cadena ramificada o recta, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6,heteroalquilo C1-6, aminoalquilo C1-6, haloalquilo C1-6, alquiltio C1-6, alcoxicarbonilo C1-6, -CN, -CF3, -OR3, -COR3, NO2, -NHR3, -NHC(O)R3, -C(O)NR3R4,-NR3R4, -NR3C(O)NR4R5, -OC(O)R3, -C(O)R3R4, -O(CH2)qNR3, -CNR3R4 o -(CH2)qNR3R4; donde q es un entero desde 1 a 6; n es 0, 1, 2, 3, o 4, los grupos R2, cuandon > 1, son iguales o diferentes; p es 0 o un entero de1 a 5; Y es O, S, CHOH, -NHC(O)-, -C(O)NH-, -C(O)-, -OC(O)-, NR7 o -CH=N-, y R7 es H o alquilo C1-4; oausente; Z es CR8R9 en donde R8 y R9 se seleccionan independientemente entre H y alquilo C1-8 recto o de cadena ramificada; siempre que cuando -(CH2)p-Y- es-(CH2)3-C(O)- o -(CH2)3-S-, y X1 a X5 son C; que -A-(R2)n y R1 no están juntos: o-metil-fenilo y n-butilo, respectivamente; fenilo y n-butilo, respectivamente;A compound with activity on muscarinic receptors, comprising formula (I) wherein: X1, X2, X3, X4 and X5 are selected from C, N and O; k is 0o 1; t is 0, 1 or 2; R1 is branched or straight chain C1-8 alkyl, C2-8 alkenyl, C1-8 alkynyl, C1-8 alkylidene, C1-8 alkoxy, C1-8 heteroalkyl, C1-8 aminoalkyl, C1-8 haloalkyl, C1-8 alkoxycarbonyl , C1-8 hydroxyalkoxy, C1-8 hydroxyalkyl, -SH, C1-8 alkylthio, -O-CH2-C5-6 aryl, -C (O) -C5-6 arylsubstituted with C1-3 alkyl or halo; C5-6 aryl or C5-6 cycloalkyl optionally comprising 1 or more heteroatoms selected from N, S and O; -C (O) NR3R4, -NR3R4, -NR3C (O) NR4R5, -CNR3R4, -OC (O) R3, - (O) (CH2) sNR3R4 or - (CH2) sNR3R4; where R3, R4 and R5 are the same or different; each is independently selected from H, C1-6 alkyl; C5-6 aryl which optionally comprises 1 or more heteroatoms selected from N, O and S, and optionally substituted with halo or C1-6 alkyl; C3-6 cycloalkyl; or R3 and R4 together with the N atom, when present, form a cyclic ring structure comprising 5-6 atoms selected from C, N, S and O; and s is an integer from 0 to 8; A is C5-12 aryl or C5-7 cycloalkyl; each optionally comprises 1 or more heteroatoms selected from N, S and O; R 2 is H, amino, hydroxyl, halo, or straight or branched C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 1-6 alkoxy, C 1-6 heteroalkyl, C 1-6 aminoalkyl, C 1-6 haloalkyl , C1-6 alkylthio, C1-6 alkoxycarbonyl, -CN, -CF3, -OR3, -COR3, NO2, -NHR3, -NHC (O) R3, -C (O) NR3R4, -NR3R4, -NR3C (O) NR4R5, -OC (O) R3, -C (O) R3R4, -O (CH2) qNR3, -CNR3R4 or - (CH2) qNR3R4; where q is an integer from 1 to 6; n is 0, 1, 2, 3, or 4, the groups R2, when> 1, are the same or different; p is 0 or an integer from 1 to 5; Y is O, S, CHOH, -NHC (O) -, -C (O) NH-, -C (O) -, -OC (O) -, NR7 or -CH = N-, and R7 is H or C1-4 alkyl; absent Z is CR8R9 wherein R8 and R9 are independently selected from H and straight or branched C1-8 alkyl; provided that when - (CH2) p-Y- is- (CH2) 3-C (O) - or - (CH2) 3-S-, and X1 to X5 are C; that -A- (R2) n and R1 are not together: o-methyl-phenyl and n-butyl, respectively; phenyl and n-butyl, respectively;

ARP990101516A 1998-03-31 1999-04-05 COMPOUNDS WITH ACTIVITY ON MUSCARINIC RECEPTORS, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND THE USE OF THEM FOR THE MANUFACTURE OF A MEDICINE AR014974A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/933,177 US20080108618A1 (en) 1998-03-31 2007-10-31 Compounds with activity on muscarinic receptors

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US8013398P 1998-03-31 1998-03-31

Publications (1)

Publication Number Publication Date
AR014974A1 true AR014974A1 (en) 2001-04-11

Family

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Application Number Title Priority Date Filing Date
ARP990101516A AR014974A1 (en) 1998-03-31 1999-04-05 COMPOUNDS WITH ACTIVITY ON MUSCARINIC RECEPTORS, A PHARMACEUTICAL COMPOSITION THAT INCLUDES THEM AND THE USE OF THEM FOR THE MANUFACTURE OF A MEDICINE

Country Status (14)

Country Link
EP (1) EP1068185A1 (en)
JP (1) JP2002509918A (en)
KR (2) KR20060120715A (en)
CN (1) CN1303376A (en)
AR (1) AR014974A1 (en)
AU (1) AU762726B2 (en)
BR (1) BR9909277A (en)
CA (1) CA2326804C (en)
MX (1) MXPA00009569A (en)
NO (1) NO319835B1 (en)
NZ (2) NZ525108A (en)
RU (2) RU2230740C2 (en)
WO (1) WO1999050247A1 (en)
ZA (1) ZA200005149B (en)

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