FR2446823A1 - 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80) - Google Patents

3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)

Info

Publication number
FR2446823A1
FR2446823A1 FR7900971A FR7900971A FR2446823A1 FR 2446823 A1 FR2446823 A1 FR 2446823A1 FR 7900971 A FR7900971 A FR 7900971A FR 7900971 A FR7900971 A FR 7900971A FR 2446823 A1 FR2446823 A1 FR 2446823A1
Authority
FR
France
Prior art keywords
methoxy
amino
bromophenyl
thenyl
pyrimidine
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
FR7900971A
Other languages
French (fr)
Other versions
FR2446823B1 (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Synthelabo SA
Original Assignee
Delalande SA
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 Delalande SA filed Critical Delalande SA
Priority to FR7900971A priority Critical patent/FR2446823A1/en
Priority to FR7931656A priority patent/FR2476088A2/en
Priority to SE8000068A priority patent/SE444941B/en
Priority to GR60908A priority patent/GR66499B/el
Priority to US06/110,067 priority patent/US4471120A/en
Priority to CH111/80A priority patent/CH647520A5/en
Priority to CA343,219A priority patent/CA1130286A/en
Priority to IT19071/80A priority patent/IT1148801B/en
Priority to ZA00800160A priority patent/ZA80160B/en
Priority to GB8028343A priority patent/GB2055374B/en
Priority to GB8001037A priority patent/GB2042522B/en
Priority to BE0/198955A priority patent/BE881134A/en
Priority to LU82083A priority patent/LU82083A1/en
Priority to MX10153780U priority patent/MX6529E/en
Priority to AU54610/80A priority patent/AU542537B2/en
Priority to ES487721A priority patent/ES487721A1/en
Priority to NL8000277A priority patent/NL8000277A/en
Priority to JP55003433A priority patent/JPS6059915B2/en
Priority to DE3049963A priority patent/DE3049963C2/en
Priority to DE19803001328 priority patent/DE3001328A1/en
Priority to SE8005674A priority patent/SE431984B/en
Publication of FR2446823A1 publication Critical patent/FR2446823A1/en
Priority to CH622080A priority patent/CH646969A5/en
Priority to US06/186,100 priority patent/US4424358A/en
Priority to IT8024713A priority patent/IT1235424B/en
Priority to NL8005774A priority patent/NL8005774A/en
Priority to US06/254,684 priority patent/US4329466A/en
Priority to US06/254,683 priority patent/US4321378A/en
Priority to JP6772381A priority patent/JPS56164187A/en
Priority to US06/399,392 priority patent/US4536580A/en
Priority to CA000409952A priority patent/CA1160227A/en
Priority to JP58122438A priority patent/JPS5976084A/en
Application granted granted Critical
Publication of FR2446823B1 publication Critical patent/FR2446823B1/fr
Granted legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/47One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/02Drugs for disorders of the nervous system for peripheral neuropathies
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D451/00Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C07D451/04Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof with hetero atoms directly attached in position 3 of the 8-azabicyclo [3.2.1] octane or in position 7 of the 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring system

Abstract

Nortropane derivs. of formula (I) and their acid-addn. salts are new. In (I) (a) R is benzyl and A is 2-amino-4-ethoxy-5-pyrimidinyl, 2-methoxyphenyl, 2-methoxy-5-fluorophenyl, 2-methoxy-5-nitrophenyl, 2-methoxy-5-hydroxyphenyl, 2-methoxy-4-amino-5-bromophenyl, 2-methoxy-4-acetamido-5-bromophenyl, 2-methoxy-4-acetamido-5-chlorophenyl, 2-methoxy-4-trifluoroacetamido-5-chlorophenyl, 2-ethoxy-4-amino-5-bromophenyl, 2-methoxy-4-aminophenyl, 2,4,5-trimethoxyphenyl, 2,4-dimethoxyphenyl, 2,3-dimethoxyphenyl, 3,5-dimethoxyphenyl, 2,3,4-trimethoxyphenyl or 2-methoxy-3,5-dibromo-4-aminophenyl; (b) R is m-methy-, m-CF3- or m-halobenzyl and A is 2-methoxy-4-amino-5-bromophenyl; (c) R is p-methyl-, p-methoxy-, p-bromo- or p-chlorobenzyl and A is 2-amino-4-methoxy-5-pyrimidinyl; (d) R is benzyl p-substd. by l lower alkyl, CF3, Cl, Br, or F and A is 2-methoxy-4-amino-5-bromophenyl; (e) R is 3,4-dichlorobenzyl, 2-thenyl or 3-thenyl and A is 2-methoxy-4-amino-5-bromophenyl; (f) R is 2-thenyl, 3-thenyl or 2-furfuryl and A is 2-methoxy-4-amino-5-chlorophenyl; or (g) R is cyclohexylmethyl and A is 2-methoxy-4-amino-5-bromophenyl). Intermediates 2-amino-4-methoxy-5-pyrimidine-carboxylic acid, 2-amino-4-ethoxy-5-pyrimidine-carboxylic acid, methyl 2-amino-4-methoxy-5-pyrimidine-carboxylate and ethyl 2-amino-4-ethoxy-5-pyrimidine-carboxylate are also new. (I) are neuroleptic agents with higher activity and generally lower toxicity than sulpiride.
FR7900971A 1979-01-16 1979-01-16 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80) Granted FR2446823A1 (en)

Priority Applications (31)

Application Number Priority Date Filing Date Title
FR7900971A FR2446823A1 (en) 1979-01-16 1979-01-16 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)
FR7931656A FR2476088A2 (en) 1979-01-16 1979-12-26 NOVEL NOR-TROPANE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION
SE8000068A SE444941B (en) 1979-01-16 1980-01-04 DERIVATIVES OF NORTROPAN AND PHARMACEUTICAL COMPOSITION THEREOF
GR60908A GR66499B (en) 1979-01-16 1980-01-05
US06/110,067 US4471120A (en) 1979-01-16 1980-01-07 Nor-tropane derivatives
CA343,219A CA1130286A (en) 1979-01-16 1980-01-08 Derivates of nor-tropane, a process for preparing same and their application in therapeutics
CH111/80A CH647520A5 (en) 1979-01-16 1980-01-08 NORTROPANE DERIVATIVES, THEIR PREPARATION PROCESS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM.
IT19071/80A IT1148801B (en) 1979-01-16 1980-01-08 NOR-TROPANO DERIVATIVES, THEIR PREPARATION PROCEDURE AND THEIR THERAPEUTIC APPLICATION
ZA00800160A ZA80160B (en) 1979-01-16 1980-01-10 Novel nor-tropane derivatives,a process for preparing same and their application in therapeutics
GB8028343A GB2055374B (en) 1979-01-16 1980-01-11 -amino-3 nor-tropane derivatives
GB8001037A GB2042522B (en) 1979-01-16 1980-01-11 Nor-tropane derivatives a process for preparing same and their application in therapeutics
BE0/198955A BE881134A (en) 1979-01-16 1980-01-14 NEW NOR-TROPANE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION
LU82083A LU82083A1 (en) 1979-01-16 1980-01-14 NEW NOR-TROPANE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION
AU54610/80A AU542537B2 (en) 1979-01-16 1980-01-15 Nor-tropane derivatives
ES487721A ES487721A1 (en) 1979-01-16 1980-01-15 Nor-tropane derivatives
MX10153780U MX6529E (en) 1979-01-16 1980-01-15 PROCEDURE FOR PREPARING DERIVATIVES OF NOR-TROPAN
NL8000277A NL8000277A (en) 1979-01-16 1980-01-16 NEW NOR TROPAN COMPOUNDS, METHOD FOR PREPARING AND THERAPEUTIC USE OF THESE COMPOUNDS.
JP55003433A JPS6059915B2 (en) 1979-01-16 1980-01-16 Novel nortropane derivatives, their production methods and uses
DE3049963A DE3049963C2 (en) 1979-01-16 1980-01-16 3-ß-Amino-nortropan derivatives and process for their preparation
DE19803001328 DE3001328A1 (en) 1979-01-16 1980-01-16 NEW NORTROPAN DERIVATIVES, METHOD FOR THEIR PRODUCTION AND MEDICINAL PRODUCTS CONTAINING THESE DERIVATIVES
SE8005674A SE431984B (en) 1979-01-16 1980-08-12 DERIVATIVES OF 3-BETA AMIRO-NORTROPAN AS INTERMEDIATES FOR THE PREPARATION OF NORTROPANE DERIVATIVES
CH622080A CH646969A5 (en) 1979-01-16 1980-08-18 NOR-TROPANE BETA-AMINO-3 DERIVATIVES.
US06/186,100 US4424358A (en) 1979-01-16 1980-09-11 β-3-Amino nor-tropane compounds
IT8024713A IT1235424B (en) 1979-01-16 1980-09-17 BETA-3-AMINO-NORTROPANE DERIVATIVES
NL8005774A NL8005774A (en) 1979-01-16 1980-10-20 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)
US06/254,684 US4329466A (en) 1979-01-16 1981-04-16 Certain nor-tropan-8-amine-3-aryl or heteroaryl derivatives
US06/254,683 US4321378A (en) 1979-01-16 1981-04-16 8-(5-Pyrimidinecarboxamide)nor-tropane derivatives
JP6772381A JPS56164187A (en) 1979-01-16 1981-05-07 Novel beta-amino-3-nor tropane derivative
US06/399,392 US4536580A (en) 1979-01-16 1982-07-19 4-Amino-5-bromo-2-methoxy-N-[8-(benzyl)]-8-azabicyclo[3.2.1]-3-YL-benzamide or a pharmacologically acceptable acid addition salt thereof
CA000409952A CA1160227A (en) 1979-01-16 1982-08-23 DERIVATIVES OF .beta.-3-AMINO-N-NOR-TROPANES
JP58122438A JPS5976084A (en) 1979-01-16 1983-07-07 Novel nortropane derivative, manufacture and use

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7900971A FR2446823A1 (en) 1979-01-16 1979-01-16 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)

Publications (2)

Publication Number Publication Date
FR2446823A1 true FR2446823A1 (en) 1980-08-14
FR2446823B1 FR2446823B1 (en) 1983-10-21

Family

ID=9220797

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7900971A Granted FR2446823A1 (en) 1979-01-16 1979-01-16 3-Acylamino-8-arylmethyl-nortropane derivs. - useful as neuroleptic agents (NL 18.7.80)

Country Status (3)

Country Link
JP (3) JPS6059915B2 (en)
FR (1) FR2446823A1 (en)
ZA (1) ZA80160B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0067615A1 (en) * 1981-06-17 1982-12-22 Beecham Group Plc Alkylthio derivatives of azabicyclobenzamides, their preparation and pharmaceutical compositions
EP0068700A1 (en) * 1981-06-29 1983-01-05 Beecham Group Plc Azobicycloalkylbenzamides, process for their preparation and pharmaceutical compositions containing them
EP0069482A1 (en) * 1981-06-29 1983-01-12 Beecham Group Plc Azabicycloalkyl benzamides, process for their preparation and pharmaceutical compositions containing them
EP0069481A1 (en) * 1981-06-17 1983-01-12 Beecham Group Plc Azabicycloalkyl benzamides, process for their preparation and pharmaceutical compositions containing them
EP0081054A2 (en) * 1978-12-30 1983-06-15 Beecham Group Plc Azabicyclo alkyl derivatives
WO2009126806A2 (en) 2008-04-11 2009-10-15 Janssen Pharmaceutica Nv Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene a4 hydrolase
WO2010132599A1 (en) 2009-05-14 2010-11-18 Janssen Pharmaceutica Nv Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene a4 hydrolase

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2493848B2 (en) * 1980-11-07 1986-05-16 Delalande Sa NOVEL NOR-TROPANE AND GRANATANE DERIVATIVES, THEIR PREPARATION PROCESS AND THEIR THERAPEUTIC APPLICATION

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1162129A (en) * 1954-10-20 1958-09-09 Sandoz Ag Tropane amide derivatives and their preparation

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5592384A (en) * 1978-12-30 1980-07-12 Beecham Group Ltd Compound having pharmacological activity
JPH01112779A (en) * 1987-10-27 1989-05-01 Oki Electric Ind Co Ltd Voltage reference diode and manufacture thereof

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1162129A (en) * 1954-10-20 1958-09-09 Sandoz Ag Tropane amide derivatives and their preparation

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0081054A3 (en) * 1978-12-30 1983-08-24 Beecham Group Plc Azabicyclo alkyl derivatives
EP0081054A2 (en) * 1978-12-30 1983-06-15 Beecham Group Plc Azabicyclo alkyl derivatives
US4499099A (en) * 1981-06-17 1985-02-12 Beecham Group P.L.C. Nortropane and granatane type compounds useful in treating psychosis
EP0067615A1 (en) * 1981-06-17 1982-12-22 Beecham Group Plc Alkylthio derivatives of azabicyclobenzamides, their preparation and pharmaceutical compositions
EP0069481A1 (en) * 1981-06-17 1983-01-12 Beecham Group Plc Azabicycloalkyl benzamides, process for their preparation and pharmaceutical compositions containing them
US4459300A (en) * 1981-06-29 1984-07-10 Beecham Group P.L.C. Pharmaceutically active aza-bicyclo benzamide derivatives
EP0069482A1 (en) * 1981-06-29 1983-01-12 Beecham Group Plc Azabicycloalkyl benzamides, process for their preparation and pharmaceutical compositions containing them
EP0068700A1 (en) * 1981-06-29 1983-01-05 Beecham Group Plc Azobicycloalkylbenzamides, process for their preparation and pharmaceutical compositions containing them
WO2009126806A2 (en) 2008-04-11 2009-10-15 Janssen Pharmaceutica Nv Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene a4 hydrolase
US7939527B2 (en) 2008-04-11 2011-05-10 Janssen Pharmaceutica Nv Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
EP2336125A1 (en) 2008-04-11 2011-06-22 Janssen Pharmaceutica N.V. Thiazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
US8357684B2 (en) 2008-04-11 2013-01-22 Janssen Pharmaceutica Nv Thyazolopyridin-2-yloxy-phenyl and thiazolopyrazin-2-yloxy-phenyl amines as modulators of leukotriene A4 hydrolase
WO2010132599A1 (en) 2009-05-14 2010-11-18 Janssen Pharmaceutica Nv Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene a4 hydrolase
US8399465B2 (en) 2009-05-14 2013-03-19 Janssen Pharmaceutica Nv Compounds with two fused bicyclic heteroaryl moieties as modulators of leukotriene A4 hydrolase

Also Published As

Publication number Publication date
JPS6059915B2 (en) 1985-12-27
JPS55108871A (en) 1980-08-21
JPS56164187A (en) 1981-12-17
JPS5976084A (en) 1984-04-28
ZA80160B (en) 1981-01-28
FR2446823B1 (en) 1983-10-21

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