BE880020A - Nouveau compose d'imidazole et agent antidepressif contenant ce compose - Google Patents
Nouveau compose d'imidazole et agent antidepressif contenant ce compose Download PDFInfo
- Publication number
- BE880020A BE880020A BE2/58208A BE2058208A BE880020A BE 880020 A BE880020 A BE 880020A BE 2/58208 A BE2/58208 A BE 2/58208A BE 2058208 A BE2058208 A BE 2058208A BE 880020 A BE880020 A BE 880020A
- Authority
- BE
- Belgium
- Prior art keywords
- group
- emi
- lower alkyl
- amino
- compound
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 98
- -1 IMIDAZOLE COMPOUND Chemical class 0.000 title claims description 30
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 30
- 239000000935 antidepressant agent Substances 0.000 title claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 68
- 125000005843 halogen group Chemical group 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 30
- 125000003277 amino group Chemical group 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 230000008569 process Effects 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 5
- LHTWHACIHJYDLR-UHFFFAOYSA-N n-butyl-4-(2-methylimidazol-1-yl)aniline Chemical group C1=CC(NCCCC)=CC=C1N1C(C)=NC=C1 LHTWHACIHJYDLR-UHFFFAOYSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- ZDHNDCMKVXWWLA-UHFFFAOYSA-N 3-(2-methylimidazol-1-yl)aniline Chemical group CC1=NC=CN1C1=CC=CC(N)=C1 ZDHNDCMKVXWWLA-UHFFFAOYSA-N 0.000 claims description 3
- FKHUITJYEBXJCO-UHFFFAOYSA-N 4-(2-methylimidazol-1-yl)-2-(trifluoromethyl)aniline Chemical group CC1=NC=CN1C1=CC=C(N)C(C(F)(F)F)=C1 FKHUITJYEBXJCO-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- RKQGJELNTGGIKM-UHFFFAOYSA-N n,n-dimethyl-4-(2-methylimidazol-1-yl)aniline Chemical group C1=CC(N(C)C)=CC=C1N1C(C)=NC=C1 RKQGJELNTGGIKM-UHFFFAOYSA-N 0.000 claims description 3
- JBCFJMYPJJWIRG-UHFFFAOYSA-N 1,3-oxazole-4-carboxylic acid Chemical compound OC(=O)C1=COC=N1 JBCFJMYPJJWIRG-UHFFFAOYSA-N 0.000 claims description 2
- XNEHDEMADMGKOB-UHFFFAOYSA-N 4-chloro-n-[4-(2-ethylimidazol-1-yl)phenyl]benzamide Chemical group CCC1=NC=CN1C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 XNEHDEMADMGKOB-UHFFFAOYSA-N 0.000 claims description 2
- PTBRBAXSZFTASH-UHFFFAOYSA-N 4-chloro-n-[4-(2-methylimidazol-1-yl)phenyl]benzamide Chemical group CC1=NC=CN1C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 PTBRBAXSZFTASH-UHFFFAOYSA-N 0.000 claims description 2
- LDJUQKDUCNGHHO-UHFFFAOYSA-N 4-fluoro-n-[4-(2-methylimidazol-1-yl)phenyl]benzamide Chemical group CC1=NC=CN1C(C=C1)=CC=C1NC(=O)C1=CC=C(F)C=C1 LDJUQKDUCNGHHO-UHFFFAOYSA-N 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 3
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
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- 239000001257 hydrogen Substances 0.000 claims 1
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
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- 230000000694 effects Effects 0.000 description 6
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- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 6
- 230000004899 motility Effects 0.000 description 6
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- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- XUUHHUAOQCPPLW-UHFFFAOYSA-N 2-methyl-5-(2-methylimidazol-1-yl)aniline Chemical compound CC1=NC=CN1C1=CC=C(C)C(N)=C1 XUUHHUAOQCPPLW-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
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- HJQHINQZCOXIGG-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-2-methylimidazole Chemical compound CC1=NC=CN1C1=CC=C(C)C(C)=C1 HJQHINQZCOXIGG-UHFFFAOYSA-N 0.000 description 3
- HCOWOSINIWWAAE-UHFFFAOYSA-N 4-(2-ethylimidazol-1-yl)aniline Chemical compound CCC1=NC=CN1C1=CC=C(N)C=C1 HCOWOSINIWWAAE-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
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- SIOJLMNJHNNNKW-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-2-ethylimidazole Chemical compound CCC1=NC=CN1C1=CC=C(Cl)C(Cl)=C1 SIOJLMNJHNNNKW-UHFFFAOYSA-N 0.000 description 2
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- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
- A61P25/24—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Engineering & Computer Science (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13932578A JPS5566562A (en) | 1978-11-14 | 1978-11-14 | Novel imidazole derivative and antidepressant containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE880020A true BE880020A (fr) | 1980-03-03 |
Family
ID=15242675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE2/58208A BE880020A (fr) | 1978-11-14 | 1979-11-14 | Nouveau compose d'imidazole et agent antidepressif contenant ce compose |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5566562A (enrdf_load_stackoverflow) |
| BE (1) | BE880020A (enrdf_load_stackoverflow) |
-
1978
- 1978-11-14 JP JP13932578A patent/JPS5566562A/ja active Granted
-
1979
- 1979-11-14 BE BE2/58208A patent/BE880020A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5566562A (en) | 1980-05-20 |
| JPS6140227B2 (enrdf_load_stackoverflow) | 1986-09-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RE | Patent lapsed |
Owner name: EISAI CO. LTD Effective date: 19901130 |