GB1008649A - New 4,5-dihydro-imidazole derivatives and process for their preparation - Google Patents
New 4,5-dihydro-imidazole derivatives and process for their preparationInfo
- Publication number
- GB1008649A GB1008649A GB1931764A GB1931764A GB1008649A GB 1008649 A GB1008649 A GB 1008649A GB 1931764 A GB1931764 A GB 1931764A GB 1931764 A GB1931764 A GB 1931764A GB 1008649 A GB1008649 A GB 1008649A
- Authority
- GB
- United Kingdom
- Prior art keywords
- general formula
- nitrile
- acid addition
- stands
- prepared
- 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.)
- Expired
Links
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical class C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 abstract 7
- 239000002253 acid Substances 0.000 abstract 5
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 3
- -1 cinnamic acid nitrile Chemical class 0.000 abstract 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 abstract 2
- 229930016911 cinnamic acid Natural products 0.000 abstract 2
- 235000013985 cinnamic acid Nutrition 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 150000002825 nitriles Chemical class 0.000 abstract 2
- 239000000243 solution Substances 0.000 abstract 2
- OOBHFESNSZDWIU-GXSJLCMTSA-N (2s,3s)-3-methyl-2-phenylmorpholine Chemical compound C[C@@H]1NCCO[C@H]1C1=CC=CC=C1 OOBHFESNSZDWIU-GXSJLCMTSA-N 0.000 abstract 1
- 208000010513 Stupor Diseases 0.000 abstract 1
- 150000001555 benzenes Chemical class 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 150000008049 diazo compounds Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 230000004899 motility Effects 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 229960003209 phenmetrazine Drugs 0.000 abstract 1
- 239000006187 pill Substances 0.000 abstract 1
- 230000003389 potentiating effect Effects 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 230000002269 spontaneous effect Effects 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 239000000725 suspension 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:1008649/C2/1> in which A stands for a valency bond or a methylene or ethylene group, X stands for a halogen atom or an alkyl or hydroxyl radical and Y stands for hydrogen atom or ahydroxyl group, and acid addition salts thereof, and the preparation thereof by reacting a nitrile of the general formula <FORM:1008649/C2/2> wherein A, X and Y have the above meanings with a 1:1 mole mixture of ethylene diamine and the di-acid addition salt of ethylene diamine or with a mono-acid addition salt of ethylene diamine, and converting the products thus obtained into their acid addition salts if desired or setting the bases free from their above salts. The nitriles of the second general formula above, wherein X represents an alkyl group are prepared by reacting cinnamic acid nitrile with the appropriate substituted benzene derivative in the presence of aluminium chloride, and those wherein X and Y are hydroxy are prepared by diazotizing the corresponding amino compound and warning the solution of the diazo compound thus obtained. b -Phenyl-b (p-chloro-phenyl)-propio-nitrile is prepared by reacting cinnamic acid nitrile and chlorobenzene in the presence of an anhydrous aluminium chloride. Pharmaceutical compositions, having a sedative effect inhibiting spontaneous motility and also the excitemnt caused by phenmetrazine, and which also potentiate narcosis when administered orally, parenterally or rectally, contain a compound of the first general formula above or an acid additional salt thereof in admixture with appropriate pharmaceutical carriers. Salts specified include ascortates. The compositions may take the form of tablets, coated pills, suspensions, solutions, powders or granules, capsules, emulsions or suppositories.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000444 | 1963-05-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1008649A true GB1008649A (en) | 1965-11-03 |
Family
ID=10994308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1931764A Expired GB1008649A (en) | 1963-05-13 | 1964-05-08 | New 4,5-dihydro-imidazole derivatives and process for their preparation |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB1008649A (en) |
| NL (1) | NL6405247A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0624638A1 (en) * | 1993-05-13 | 1994-11-17 | The Lubrizol Corporation | Compositions useful as additives for lubricants and liquid fuels |
-
1964
- 1964-05-08 GB GB1931764A patent/GB1008649A/en not_active Expired
- 1964-05-12 NL NL6405247A patent/NL6405247A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0624638A1 (en) * | 1993-05-13 | 1994-11-17 | The Lubrizol Corporation | Compositions useful as additives for lubricants and liquid fuels |
| US5458793A (en) * | 1993-05-13 | 1995-10-17 | The Lubrizol Corporation | Compositions useful as additives for lubricants and liquid fuels |
| US5560755A (en) * | 1993-05-13 | 1996-10-01 | The Lubrizol Corporation | Compositions useful as additives for lubricants and liquid fuels |
Also Published As
| Publication number | Publication date |
|---|---|
| NL6405247A (en) | 1964-11-16 |
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