JPS5569567A - Novel imidazole compound, and antidepressant containing the same - Google Patents
Novel imidazole compound, and antidepressant containing the sameInfo
- Publication number
- JPS5569567A JPS5569567A JP14281378A JP14281378A JPS5569567A JP S5569567 A JPS5569567 A JP S5569567A JP 14281378 A JP14281378 A JP 14281378A JP 14281378 A JP14281378 A JP 14281378A JP S5569567 A JPS5569567 A JP S5569567A
- Authority
- JP
- Japan
- Prior art keywords
- lower alkyl
- phenyl
- imidazole compound
- novel imidazole
- compound
- 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
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title abstract 4
- -1 imidazole compound Chemical class 0.000 title abstract 3
- 230000001430 anti-depressive effect Effects 0.000 title abstract 2
- 239000000935 antidepressant agent Substances 0.000 title abstract 2
- 229940005513 antidepressants Drugs 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- XNEHDEMADMGKOB-UHFFFAOYSA-N 4-chloro-n-[4-(2-ethylimidazol-1-yl)phenyl]benzamide Chemical compound CCC1=NC=CN1C(C=C1)=CC=C1NC(=O)C1=CC=C(Cl)C=C1 XNEHDEMADMGKOB-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000002535 acidifier Substances 0.000 abstract 1
- 229960000836 amitriptyline Drugs 0.000 abstract 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 229960004801 imipramine Drugs 0.000 abstract 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 abstract 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
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
NEW MATERIAL:A novel imidazole compound of formula I and its pharmacologically permissible acid addition salt [R1,2 are H or lower alkyl; R3 is lower alkyl, phenyl, etc.; R4 is H, lower alkyl, etc.; R5 is H, -CF3, etc.; A is carbonyl or sulfonyl; the positions of R5 and -N(R4)-A-R3 groups on the phenyl nucleus are arbitrary.]. EXAMPLE:1-[4-(4-Chlorobenzoylamino)phenyl]-2-ethylimidazole. USE:A low-toxic antidepressant having non-specific anti-reserpic activity in contrast with conventional tri-cyclic antidepressants such as imipramine and amitriptyline. PROCESS:The objective compound I is prepared, e.g. by reacting a primary amino compound II with a carboxylic acid, sulfonic acid, or their reactive derivative (R3A- OH), in an inert solvent such as chloroform, optionally in the presence of a de- acidifying agent such as potassium carbonate, at room temp. to 150 deg.C.
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14281378A JPS5569567A (en) | 1978-11-21 | 1978-11-21 | Novel imidazole compound, and antidepressant containing the same |
| US06/093,469 US4301169A (en) | 1978-11-14 | 1979-11-13 | Novel imidazole compound and anti-depressing agent containing the same |
| SE7909371A SE447653B (en) | 1978-11-14 | 1979-11-13 | IMIDAZOLD DERIVATIVES AND PHARMACEUTICAL COMPOSITION CONTAINING SUCH DERIVATIVES |
| GB7939283A GB2044754B (en) | 1978-11-14 | 1979-11-13 | Imidazoles |
| NL7908331A NL7908331A (en) | 1978-11-14 | 1979-11-14 | IMIDA SOLE DERIVATIVES WITH ANTI-DEPRESSIVE EFFECT. |
| CH1014979A CH642635A5 (en) | 1978-11-14 | 1979-11-14 | IMIDAZOLE DERIVATIVES, PROCESSES FOR THEIR PREPARATION AND MEDICINAL COMPOSITIONS CONTAINING THESE DERIVATIVES. |
| CA339,861A CA1126272A (en) | 1978-11-14 | 1979-11-14 | Imidazole compound and anti-depressing agent containing the same |
| IT27268/79A IT1127223B (en) | 1978-11-14 | 1979-11-14 | IMIDAZOLE COMPOUND AND MEDICATION AGAINST THE DEPRESSIVE STATES CONTAINING THIS COMPOUND |
| FR7928099A FR2441616B1 (en) | 1978-11-14 | 1979-11-14 | NOVEL IMIDAZOLE, PROCESS FOR ITS PREPARATION AND THERAPEUTIC APPLICATION |
| DE19792946020 DE2946020A1 (en) | 1978-11-14 | 1979-11-14 | IMIDAZOLE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| US06/252,674 US4402966A (en) | 1978-11-14 | 1981-04-09 | Acylaminophenyl imidazoles and anti-depressing agent containing the same |
| US06/469,548 US4533669A (en) | 1978-11-14 | 1983-02-25 | Anti-depressant imidazoles |
| US06/741,935 US4602031A (en) | 1978-11-14 | 1985-06-06 | Anti-depressant imidazoles, compositions and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP14281378A JPS5569567A (en) | 1978-11-21 | 1978-11-21 | Novel imidazole compound, and antidepressant containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5569567A true JPS5569567A (en) | 1980-05-26 |
| JPS6241224B2 JPS6241224B2 (en) | 1987-09-02 |
Family
ID=15324215
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP14281378A Granted JPS5569567A (en) | 1978-11-14 | 1978-11-21 | Novel imidazole compound, and antidepressant containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5569567A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029163A1 (en) * | 1994-04-27 | 1995-11-02 | Nippon Soda Co., Ltd. | Imidazole derivative and process for producing the same |
| US7553837B2 (en) | 2003-08-01 | 2009-06-30 | Nippon Soda Co., Ltd. | Phenylazole compounds production process and antioxidants |
| US7652155B2 (en) | 2003-04-14 | 2010-01-26 | Nippon Soda Co., Ltd. | Diamine derivative, production process therefor and antioxidant |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5387398A (en) * | 1977-01-07 | 1978-08-01 | Bristol Myers Co | 44substituted imidazo*1*22a* quinoxalines intermediates thereof and process for preparing same |
-
1978
- 1978-11-21 JP JP14281378A patent/JPS5569567A/en active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5387398A (en) * | 1977-01-07 | 1978-08-01 | Bristol Myers Co | 44substituted imidazo*1*22a* quinoxalines intermediates thereof and process for preparing same |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029163A1 (en) * | 1994-04-27 | 1995-11-02 | Nippon Soda Co., Ltd. | Imidazole derivative and process for producing the same |
| US5965743A (en) * | 1994-04-27 | 1999-10-12 | Nippon Soda Co., Ltd. | N-substituted imidazol derivative |
| US7652155B2 (en) | 2003-04-14 | 2010-01-26 | Nippon Soda Co., Ltd. | Diamine derivative, production process therefor and antioxidant |
| US7553837B2 (en) | 2003-08-01 | 2009-06-30 | Nippon Soda Co., Ltd. | Phenylazole compounds production process and antioxidants |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6241224B2 (en) | 1987-09-02 |
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