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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic 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
- C07D239/28—Heterocyclic 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
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic 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
- C07D451/02—Heterocyclic 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
- C07D451/04—Heterocyclic 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.
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)
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)
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)
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)
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 |
-
1979
- 1979-01-16 FR FR7900971A patent/FR2446823A1/en active Granted
-
1980
- 1980-01-10 ZA ZA00800160A patent/ZA80160B/en unknown
- 1980-01-16 JP JP55003433A patent/JPS6059915B2/en not_active Expired
-
1981
- 1981-05-07 JP JP6772381A patent/JPS56164187A/en active Pending
-
1983
- 1983-07-07 JP JP58122438A patent/JPS5976084A/en active Pending
Patent Citations (1)
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)
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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Legal Events
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TP | Transmission of property |