FI113370B - Naftylamider som medel för det centrala nervsystemet, förfarande för deras framställning och farmaceutiska kompositioner innehållande dessa - Google Patents

Naftylamider som medel för det centrala nervsystemet, förfarande för deras framställning och farmaceutiska kompositioner innehållande dessa Download PDF

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Publication number
FI113370B
FI113370B FI963294A FI963294A FI113370B FI 113370 B FI113370 B FI 113370B FI 963294 A FI963294 A FI 963294A FI 963294 A FI963294 A FI 963294A FI 113370 B FI113370 B FI 113370B
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ethyl
methoxy
piperazinyl
bromo
naphthalenecarboxamide
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FI963294A
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English (en)
Finnish (fi)
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FI963294A (sv
FI963294A0 (sv
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Lawrence David Wise
Jonathan Wright
Suzanne Ross Kesten
Shelly Ann Glase
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Warner Lambert Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/04—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D275/06—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings condensed with carbocyclic rings or ring systems with hetero atoms directly attached to the ring sulfur atom
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • 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
    • 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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • 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
    • C07D295/12—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 singly or doubly bound nitrogen atoms
    • C07D295/125—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
    • C07D333/66—Nitrogen atoms not forming part of a nitro radical

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Liquid Carbonaceous Fuels (AREA)
  • Chemical And Physical Treatments For Wood And The Like (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Indole Compounds (AREA)

Claims (10)

1. Förening med formeln I
5 OR4 I O H /-y p A ii I / \ s ^—C—N—CHr—CH;—N N—R w 1 *2 io R kännetecknad därav, att R och R1 är lika eller olika och bäda är väte, C^-alkyl, C^-alkoxi, tio-Ci.g-alkoxi, hyd-roxi, amino, Cx_6-alkylamino eller di-C^g-alkylamino, R2 är halogen, nitro, cyano, S02NH-, Cj.g-alkyl eller 15 alkoxi, R3 är väte, hydroxi eller metoxi, R4 är väte eller C^-alkyl, och R5 är fenyl eller fenyl, som är substituerad med 1-3 substituenter, vilka är halogen, hydroxi, C^-alkyl, (ν6-20 alkoxi, tio-C^g-alkoxi eller cyano, eller R5 är 2-, 3- eller 4-pyridinyl, 2-, 3- eller 4-pyridinyl, som är substituerad med halogen, 2-bensotiazolyl, 2-bensoxazolyl, 3-benso[b]tienyl, 7-benso[b]furanyl, 2-, 3-, 4-, 5-, 6- * eller 7-indolyl, 2-, 3-, 4-, 5-, 6-, 7- eller 8-kinolinyl • 25 eller 1-benzisotiazolyl, eller ett farmaceutiskt godtagbart syraadditionssalt därav. t
2. Föreningen enligt patentkravet 1, kännetecknad därav, att R2 är halogen, nitro eller cyano och R4 är metyl eller ,·, 30 etyl. !' 3. Föreningen enligt patentkravet 2, kännetecknad därav, ”· att den är ’4-brom-N- {2- [4-(2,3-diklorfenyl) -1 -piperazinyl] -35 etyl}-1-metoxi-2-naftalenkarboxamid; 4-brom-1-metoxi-N-[2-(4-fenyl-l-piperazinyl)etyl]-2-na fta1enkarboxamid; 113370 4-brom-l-metoxi-N-[2-(4-pyridin-2-yl-l-piperazinyl)-etyl]-2-naftalenkarboxamid; 4-brom-l-metoxi-N-{2-[4-(2-metoxifenyl)-1-piperazi-nyl]etyl}-2-naftalenkarboxamid; 5 4-brom-l-metoxi-N-{2-[4-(2-propylsulfanylfenyl)-1- piperazinyl]etyl}-2-naftalenkarboxamid; 4-brom-l-metoxi-N-[2-(4-o-tolyl-l-piperazinyl)etyl]-2-naftalenkarboxamid; 4-brom-N-(2-[4-(2,3-dimetylfenyl)-1-piperazinyl]-10 etyl}-1-metoxi-2-naftalenkarboxamid; 4-brom-N-{2-[4-(2-klorfenyl)-1-piperazinyl]etyl}-1-metoxi-2-naftalenkarboxamid; 4-brom-N-{2-[4-(3-klorfenyl)-1-piperazinyl]etyl}-1-metoxi-2-naftalenkarboxamid; 15 4-brom-N-{2-[4-(4-klorfenyl)-1-piperazinyl]etyl}-l- metoxi-2-naftalenkarboxamid; 4-brom-N-{2-[4-(3-klor-2-metylfenyl)-1-piperazinyl]-etyl}-l-metoxi-2-naftalenkarboxamid; 4-brom-l-etoxi-N-{2-[4-(2-metoxifenyl)-1-piperazi-20 nyl]etyl}-2-naftalenkarboxamid; 4-brom-l-etoxi-N-[2-(4-pyridin-2-yl-1-piperazinyl)-etyl]-2-naftalenkarboxamid; ; 4-cyano-l-metoxi-N-[2-(4-fenyl-1-piperazinyl)etyl]- * 2-naftalenkarboxamid;
25 N-{2-[4-(1,2-benzisotiazol-3-yl)-1-piperazinyl]- etyl}-4-brom-l-metoxi-2-naftalenkarboxamid; N-{2-[4-(7-bensofuranyl)-1-piperazinyl]etyl}-4-brom-l-metoxi-2-naftalenkarboxamid och N- [2- (4-benso [b] tiofen-3-yl-1-piperazinyl) etyl] -4-30 brom-l-metoxi-2-naftalenkarboxamid. »
4. Användning av en förening med formeln I enligt pa-tentkravet 1 vid framställning av ett farmaceutiskt preparat för behandling av psykoser, psykotisk depres- ’ 35 sion, substansmissbruk och kompulsiva störningar. * » 113370
5. Användning av en förening med formeln I enligt pa-tentkravet 1 vid framställning av ett farmaceutiskt preparat för behandling av schizofreni.
6. Farmaceutisk sammansättning, som lämpar sig för do- sering som medel för behandling av schizofreni och som innehäller en terapeutiskt effektiv mängd av en förening enligt patentkravet 1 i en blandning med ett farmaceutiskt godtagbart fyllmedel, utspädningsmedel eller 10 bärarmedel.
7. Förfarande för framställning av en förening med formeln I OR4
15 OH j-v r il i / \ 5 K2 20 väri R och R1 är lika eller olika och bäda är väte, C^g-alkyl, C^g-alkoxi, tio-C^.g-alkoxi, hydroxi, amino, C1_6- alkylamino eller di-C^g-alkylamino, * R2 är halogen, nitro, cyano, S02NH-, C^g-alkyl eller Cx_6-• · \ · 25 alkoxi, : R3 är väte, hydroxi eller metoxi, R4 är väte eller C^g-alkyl, och . R5 är fenyl eller fenyl, som är substituerad med 1-3 substituenter, vilka är halogen, hydroxi, Cj.g-alkyl, Cx_6-30 alkoxi, tio-C^g-alkoxi eller cyano, eller R5 är 2-, 3-eller 4-pyridinyl, 2-, 3- eller 4-pyridinyl, som är substituerad med halogen, 2-bensotiazolyl, 2-bensoxazo- • lyl, 3-benso[b]tienyl, 7-benso[b]furanyl, 2-, 3-, 4-, 5-, ! 6- eller 7-indolyl, 2-, 3-, 4-, 5-, 6-, 7- eller 8-kino- 35 linyl eller 1-benzisotiazolyl, eller ett farmaceutiskt godtagbart syraadditionssalt därav, kännetecknat därav, att 113370 en förening med formeln II OR4 väri R, R1, R2, R3 och R4 betecknar detsamma som ovan, 10 omsättes med en förening med formeln III H,N CHr—CRr—}/ ^N—R5 III \_/ 15 väri R5 betecknar detsamma som ovan, i närvaro av ett koppiingsmedel och ett lösningsmedel för erhällande av en förening med formeln I och en förening med formeln I omvandlas, om sä önskas, pä sedvanliga sätt tili ett 20 motsvarande farmaceutiskt godtagbart syraadditionssalt och ett motsvarande farmaceutiskt godtagbart syraadditionssalt omvandlas, om sä önskas, pä sedvanliga sätt * tili en förening med formeln I. t » » a t a t
FI963294A 1994-03-24 1996-08-23 Naftylamider som medel för det centrala nervsystemet, förfarande för deras framställning och farmaceutiska kompositioner innehållande dessa FI113370B (sv)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US08/217,395 US5395835A (en) 1994-03-24 1994-03-24 Naphthalamides as central nervous system agents
US21739594 1994-03-24
PCT/US1995/001974 WO1995025727A1 (en) 1994-03-24 1995-02-16 Naphthylamides as central nervous system agents
US9501974 1995-02-16

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FI963294A0 FI963294A0 (sv) 1996-08-23
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US (1) US5395835A (sv)
EP (1) EP0751939B9 (sv)
JP (1) JP3771581B2 (sv)
KR (1) KR100366175B1 (sv)
AT (1) ATE219068T1 (sv)
AU (1) AU683358B2 (sv)
BG (1) BG62887B1 (sv)
CZ (1) CZ284377B6 (sv)
DE (1) DE69527053T2 (sv)
DK (1) DK0751939T5 (sv)
ES (1) ES2178668T4 (sv)
FI (1) FI113370B (sv)
HU (1) HUT76058A (sv)
MX (1) MX9602517A (sv)
NO (1) NO306779B1 (sv)
NZ (1) NZ281824A (sv)
PH (1) PH31335A (sv)
PL (1) PL181270B1 (sv)
PT (1) PT751939E (sv)
RO (1) RO117452B1 (sv)
RU (1) RU2157370C2 (sv)
WO (1) WO1995025727A1 (sv)
ZA (1) ZA952382B (sv)

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DE69527053D1 (de) 2002-07-18
RU2157370C2 (ru) 2000-10-10
NO963996L (no) 1996-09-23
JP3771581B2 (ja) 2006-04-26
JPH09511503A (ja) 1997-11-18
FI963294A (sv) 1996-08-23
EP0751939A1 (en) 1997-01-08
CZ276896A3 (en) 1997-04-16
EP0751939B9 (en) 2003-01-02
ES2178668T3 (es) 2003-01-01
BG100830A (en) 1997-10-31
NO963996D0 (no) 1996-09-23
KR100366175B1 (ko) 2003-04-08
PL316313A1 (en) 1997-01-06
FI963294A0 (sv) 1996-08-23
ATE219068T1 (de) 2002-06-15
PH31335A (en) 1998-07-06
EP0751939B1 (en) 2002-06-12
PT751939E (pt) 2002-11-29
ES2178668T4 (es) 2003-06-16
BG62887B1 (bg) 2000-10-31
AU683358B2 (en) 1997-11-06
AU1877495A (en) 1995-10-09
US5395835A (en) 1995-03-07
DE69527053T2 (de) 2003-01-02
DK0751939T5 (da) 2004-11-08
NZ281824A (en) 1997-10-24
NO306779B1 (no) 1999-12-20
CZ284377B6 (cs) 1998-11-11
PL181270B1 (pl) 2001-07-31
HU9602605D0 (en) 1996-11-28
ZA952382B (en) 1996-01-10
MX9602517A (es) 1997-05-31
RO117452B1 (ro) 2002-03-29
DK0751939T3 (da) 2002-10-07
WO1995025727A1 (en) 1995-09-28
HUT76058A (en) 1997-06-30

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