GB1026778A - 2-benzyl-2-imidazoline compounds and compositions including them - Google Patents
2-benzyl-2-imidazoline compounds and compositions including themInfo
- Publication number
- GB1026778A GB1026778A GB10585/63A GB1058563A GB1026778A GB 1026778 A GB1026778 A GB 1026778A GB 10585/63 A GB10585/63 A GB 10585/63A GB 1058563 A GB1058563 A GB 1058563A GB 1026778 A GB1026778 A GB 1026778A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- acid
- benzyl
- dimethoxy
- ethylenediamine
- 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
- 239000000203 mixture Substances 0.000 title abstract 4
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical class C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 title abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 8
- 239000002253 acid Substances 0.000 abstract 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Substances OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- -1 cyanide compound Chemical class 0.000 abstract 3
- 235000014113 dietary fatty acids Nutrition 0.000 abstract 3
- 239000000194 fatty acid Substances 0.000 abstract 3
- 229930195729 fatty acid Natural products 0.000 abstract 3
- 150000004665 fatty acids Chemical class 0.000 abstract 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 abstract 2
- PXRKCOCTEMYUEG-UHFFFAOYSA-N 5-aminoisoindole-1,3-dione Chemical compound NC1=CC=C2C(=O)NC(=O)C2=C1 PXRKCOCTEMYUEG-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 abstract 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 abstract 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 abstract 2
- 239000000126 substance Substances 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 abstract 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 abstract 1
- CRIIPKLNFKGQHC-UHFFFAOYSA-N 2,5-dimethoxy-1,3-dimethylbenzene Chemical compound COC1=CC(C)=C(OC)C(C)=C1 CRIIPKLNFKGQHC-UHFFFAOYSA-N 0.000 abstract 1
- YCUYLPMHKQGLSV-UHFFFAOYSA-N 2-(3,6-dimethoxy-2,4-dimethylphenyl)acetonitrile Chemical compound COC1=C(CC#N)C(=C(C(=C1)C)OC)C YCUYLPMHKQGLSV-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 abstract 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 abstract 1
- 241000723346 Cinnamomum camphora Species 0.000 abstract 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 abstract 1
- 241000208690 Hamamelis Species 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 1
- YYVFXSYQSOZCOQ-UHFFFAOYSA-N Oxyquinoline sulfate Chemical compound [O-]S([O-])(=O)=O.C1=C[NH+]=C2C(O)=CC=CC2=C1.C1=C[NH+]=C2C(O)=CC=CC2=C1 YYVFXSYQSOZCOQ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 230000002421 anti-septic effect Effects 0.000 abstract 1
- 229940064004 antiseptic throat preparations Drugs 0.000 abstract 1
- 239000003212 astringent agent Substances 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 150000005524 benzylchlorides Chemical class 0.000 abstract 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000004327 boric acid Substances 0.000 abstract 1
- 229960002645 boric acid Drugs 0.000 abstract 1
- 229960000846 camphor Drugs 0.000 abstract 1
- 229930008380 camphor Natural products 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002462 imidazolines Chemical class 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 229940041616 menthol Drugs 0.000 abstract 1
- QEDKUQXNXOLGMP-UHFFFAOYSA-N n,n-diethyl-2-hydroxypropanamide Chemical compound CCN(CC)C(=O)C(C)O QEDKUQXNXOLGMP-UHFFFAOYSA-N 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 150000002905 orthoesters Chemical class 0.000 abstract 1
- 239000002304 perfume Substances 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q9/00—Preparations for removing hair or for aiding hair removal
- A61Q9/02—Shaving preparations
-
- 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
- C07D233/20—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 substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 2-benzyl-2-imidazoline compounds of the formula <FORM:1026778/C2/1> wherein R1 is methyl, R2 and R3 are independently hydrogen or methyl, and R4 is methyl whenever either or both of R2 and R3 are methyl, but otherwise is hydrogen; and acid addition salts thereof. The imidazolines may be prepared by condensing a compound of the formula <FORM:1026778/C2/2> wherein the symbols R have the meanings stated above, or a suitable functional derivative thereof (e.g. ester, ortho-ester, acid halide, amide or nitrile), with ethylenediamine or a substance or substances which yield ethylenediamine. In an Example 2,5-dimethoxy-4,6-dimethyl - benzyl cyanide is heated with ethylenediamine in the presence of carbon disulphide to form 2-(21,51-dimethoxy-41,61-dimethylbenzyl -2-imidazoline. The initial cyanide compound is obtained by chloromethylating 1,4-dimethoxy-2,6-dimethyl-benzene and reacting the substituted benzyl chloride so obtained with sodium cyanide.ALSO:Pre-shaving compositions comprise emulsions or solutions containing one or more compounds of the formula <FORM:1026778/A5-A6/1> wherein R1 is methyl, R2 and R3 are independently hydrogen or methyl, and R4 is methyl whenever either or both of R2 and R3 are methyl, but otherwise is hydrogen, or their pharmaceutically acceptable acid addition salts together with one or more of the following: alkylene diols or polyols, esters of fatty acids, alkali metal salts of fatty acids (the fatty acids in either case containing 14 to 18 carbon atoms) and polyvinylpyrrolidone. Besides polyvinylpyrrolidone, propylene glycol and isopropyl myristate are exemplified. The acid addition salts may be derived from hydrochloric, hydrobromic, sulphuric, citric or succinic acid. Mixtures of water with ethanol or isopropanol are suitable as vehicles for the compositions which may additionally contain an acid such as adipic, citric or tartaric acid or a hydrolysable salt such as zinc chloride or aluminium chloride. Other optional ingredients include solubilizers such as lactic acid diethylamide, astringents such as hamamelis extract or menthol, antiseptics such as boric acid, camphor, 8-hydroxyquinoline sulphate or p-hydroxybenzoic acid, and perfumes.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEM52484A DE1150180B (en) | 1962-04-12 | 1962-04-12 | Preparations for pre-treating the skin for shaving |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1026778A true GB1026778A (en) | 1966-04-20 |
Family
ID=7307429
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB10585/63A Expired GB1026778A (en) | 1962-04-12 | 1963-03-18 | 2-benzyl-2-imidazoline compounds and compositions including them |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3354175A (en) |
| CH (1) | CH477448A (en) |
| DE (1) | DE1150180B (en) |
| GB (1) | GB1026778A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164406A (en) * | 1988-06-02 | 1992-11-17 | Bristol-Myers Squibb Co. | Method for enhancing transdermal penetration and compositions useful therein |
| GB2249265B (en) * | 1990-10-30 | 1993-04-28 | George Garrett | Shaving lotion |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3846554A (en) * | 1972-12-15 | 1974-11-05 | Cincinnati Milacron Inc | Detergent compositions exhibiting reduced skin irritation and method of reducing detergent irritation |
| US3949067A (en) * | 1974-06-14 | 1976-04-06 | Gibbs Harold E | Shaving lubricant |
| US4185086A (en) * | 1978-05-04 | 1980-01-22 | Johnson & Johnson | Talc compositions |
| US4457912A (en) * | 1982-08-24 | 1984-07-03 | Scodari Nicholas F | Electric razor preshave composition |
| US4540705A (en) * | 1983-03-14 | 1985-09-10 | Sterling Drug Inc. | Antidepressant imidazolines and related compounds |
| US4634705A (en) * | 1984-06-06 | 1987-01-06 | Abbott Laboratories | Adrenergic amidines |
| US6410562B1 (en) | 1998-12-18 | 2002-06-25 | Eli Lilly And Company | Hypoglycemic imidazoline compounds |
| US20040009976A1 (en) * | 2002-04-30 | 2004-01-15 | Kumiko Takeuchi | Hypoglycemic imidazoline compounds |
| AU2007209382A1 (en) * | 2006-01-27 | 2007-08-02 | F. Hoffmann-La Roche Ag | Use of 2-imidazoles for the treatment of CNS disorders |
| EP2076497B1 (en) * | 2006-10-19 | 2012-02-22 | F. Hoffmann-La Roche AG | Aminomethyl-4-imidazoles |
| BRPI0718059A2 (en) * | 2006-10-19 | 2013-11-05 | Holffmann La Roche Ag F | AMINOMETIL-2-IMIDAZOOS WITH AFFINITY WITH AMINE-ASSOCIATED TRACE RECEIVERS |
| WO2008052907A1 (en) * | 2006-11-02 | 2008-05-08 | F. Hoffmann-La Roche Ag | Substituted 2-imidazoles as modulators of the trace amine associated receptors |
| CA2669112A1 (en) * | 2006-11-16 | 2008-05-22 | F. Hoffmann-La Roche Ag | Substituted 4-imidazoles |
| EP2101762B1 (en) * | 2006-12-13 | 2011-05-18 | F. Hoffmann-La Roche AG | Novel 2 -imidazoles as ligands for trace amine associated receptors (taar) |
| US20080146523A1 (en) * | 2006-12-18 | 2008-06-19 | Guido Galley | Imidazole derivatives |
| CA2675221C (en) * | 2007-02-02 | 2016-02-23 | F. Hoffmann-La Roche Ag | Novel 2-aminooxazolines as taar1 ligands |
| EP2121641B1 (en) * | 2007-02-15 | 2014-09-24 | F. Hoffmann-La Roche AG | 2-aminooxazolines as taar1 ligands |
| MX2009013742A (en) | 2007-07-02 | 2010-01-26 | Hoffmann La Roche | 2 -imidazolines having a good affinity to the trace amine associated receptors (taars). |
| WO2009003867A1 (en) * | 2007-07-03 | 2009-01-08 | F. Hoffmann-La Roche Ag | 4-imidazolines and their use as antidepressants |
| WO2009016048A1 (en) * | 2007-07-27 | 2009-02-05 | F. Hoffmann-La Roche Ag | 2-azetidinemethaneamines and 2-pyrrolidinemethaneamines as taar-ligands |
| BRPI0815038A2 (en) * | 2007-08-02 | 2015-03-17 | Hoffmann La Roche | USE OF BENZAMIDE DERIVATIVES FOR TREATMENT OF CNS DISORDERS |
| CA2695331A1 (en) * | 2007-08-03 | 2009-02-12 | F. Hoffmann-La Roche Ag | Pyridinecarboxamide and benzamide derivatives as taar1 ligands |
| US8242153B2 (en) * | 2008-07-24 | 2012-08-14 | Hoffmann-La Roche Inc. | 4,5-dihydro-oxazol-2YL derivatives |
| PE20110215A1 (en) * | 2008-07-24 | 2011-03-31 | Hoffmann La Roche | DERIVATIVES OF 4,5-DIHIDRO-OXAZOL-2-ILO |
| US20100311798A1 (en) * | 2009-06-05 | 2010-12-09 | Decoret Guillaume | 2-aminooxazolines as taar1 ligands |
| US8354441B2 (en) * | 2009-11-11 | 2013-01-15 | Hoffmann-La Roche Inc. | Oxazoline derivatives |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| CN102174316A (en) * | 2011-03-14 | 2011-09-07 | 长江大学 | Method for preparing corrosion inhibitor for resisting carbon dioxide/hydrogen sulfide coexistence corrosion |
| PT3430010T (en) | 2016-03-17 | 2020-09-10 | Hoffmann La Roche | 5-ethyl-4-methyl-pyrazole-3-carboxamide derivative having activity as agonist of taar |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2731471A (en) * | 1956-01-17 | Nxg hi | ||
| CH204728A (en) * | 1935-07-23 | 1939-05-15 | Chem Ind Basel | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. |
| CH204725A (en) * | 1935-07-23 | 1939-05-15 | Chem Ind Basel | Process for the preparation of an imidazole dihydride (4,5) substituted in the 2-position. |
| US2948724A (en) * | 1958-04-21 | 1960-08-09 | Sahyun | Halogenated derivatives of tetrahydro-1-naphthyl cyclic amidines |
-
1962
- 1962-04-12 DE DEM52484A patent/DE1150180B/en active Pending
-
1963
- 1963-03-11 CH CH306463A patent/CH477448A/en not_active IP Right Cessation
- 1963-03-18 GB GB10585/63A patent/GB1026778A/en not_active Expired
- 1963-04-01 US US269729A patent/US3354175A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5164406A (en) * | 1988-06-02 | 1992-11-17 | Bristol-Myers Squibb Co. | Method for enhancing transdermal penetration and compositions useful therein |
| GB2249265B (en) * | 1990-10-30 | 1993-04-28 | George Garrett | Shaving lotion |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1150180B (en) | 1963-06-12 |
| US3354175A (en) | 1967-11-21 |
| CH477448A (en) | 1969-08-31 |
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