IL24221A - Chromones and processes for the preparation thereof - Google Patents
Chromones and processes for the preparation thereofInfo
- Publication number
- IL24221A IL24221A IL2422165A IL2422165A IL24221A IL 24221 A IL24221 A IL 24221A IL 2422165 A IL2422165 A IL 2422165A IL 2422165 A IL2422165 A IL 2422165A IL 24221 A IL24221 A IL 24221A
- Authority
- IL
- Israel
- Prior art keywords
- carried out
- actual
- molar ratio
- starting
- chromones
- Prior art date
Links
- 150000004777 chromones Chemical class 0.000 title 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 claims 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000029058 respiratory gaseous exchange Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 230000004936 stimulating effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CBQYNPHHHJTCJS-UHFFFAOYSA-N Alline Chemical compound C1=CC=C2C3(O)CCN(C)C3NC2=C1 CBQYNPHHHJTCJS-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003555 analeptic effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 1
- 229940005991 chloric acid Drugs 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- JQAPAVKJKVLDNR-UHFFFAOYSA-N n-ethylethanamine;piperidine Chemical compound CCNCC.C1CCNCC1 JQAPAVKJKVLDNR-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Registered Patent Attorneys Tel Aviv CE FOR on Israeli tovontin the nature of this invention and in what nanner to he as DO by S A a ie B d C r ti convenient such as ethyl alcohol and condensed with a secondary such as diethylamine piperidine or in a molar ratio boiling under reflux or by heating in an for a convenient period of the mixture is then cooled and and if is concentrated until dry under the residue is taken up again in a little water and the undissolved portion is extracted with a solvent such as The layer is peatedly washed with a satured aqueous solution of and thereafter dried over and admixed with alcoholic chloric acid in a slight The mixture is concentrated til dry under and the residue is from a convenient solvent such as alcohol In order that the invention may be readily carried it is described in greater detail in the following which are by way of illustration Example 1 HOI A mixture of 1 of 400 of absolute 45 of a alcoholic solution of dimethylamine was heated in an autoclave at a temperature of After removing the the resultant I residue was taken up in water and that part of the residue which insoluble in water was taken up in The chloroformic layer was washed 3 times with saturated solution of NaCl dried over anhydrous sodium filtered and acidified with a slight excess of alcoholic hydrochloric residue left after removing the solvent and recrystallizing from an solution gave of a i js alline product having a melting point Calculated for actual Example 2 The operatio was carried out as in example starting with chloromethyl and in a molar ratio of The yield was and a product obtained with a melting of for actual N CI Example The operation was carried out in example 1 starting with romone and piperidine i a molar ratio of The yield was and a product was obtained having a melting point of for actual CI Example 4 HC1 The operation was carried out as in example starting and line in a molar ratio of having a melting nylchromone HCl The operation was carried out as in example starting with and dimethylamine in molar ratio of The yield was and a product was obtained having a melting point of for actual N CI Example 6 HCl The operation was carried out as in starting with and diethylamine in a molar ratio of The yield was and a product was obtained having a melting point of for actual N CI Example i HCl The operation was carried out as in starting with and having poin of for actual CI Example HCl operation was carried out as in starting with and morpholin in a molar ratio of The yield was 6 and a product was obtained having a melting point of J for C 0 NCI actual N CI Example 2 HCl The operation was carried out as example starting with and piperidine in a molar ratio of The yield and a product was obtained having a meltin point of for actual Example 2 The was carried out as in example starting with and morpholine in a molar ratio of The and was obtained having a mel ing poin of for C actual N CI I order better to illustrate the value of the rementioned dat of the pharmacological tests which were carried out are hereafter set These compounds relate to some of the products subjected to a closer study relation to other central nervous known to the medical profession such as metrazol and these substances when in high doses cause and excitation central ervous Hence the dose in which caused convulsions in of the treated animals referred to as be considered an optimum rence to calculate the exciting power of the various drugs in relation to metrazol which was taken as a In the class examined drugs were found which were even more acti ve than which was up to as one of most active amongst the stimulating substances of the nervous The value of the lethal dose in the dose which caused convulsions and the relative power or the ratio between the of metrazol and the of the compound according to the invention are set out in the from the foregoing table that of the compounds in this invention are capable of antagonizing the lethal effects of acid more readily than the most active substances so far employed in this Two of the aforementioned compounds namely example and example 1 being the two most active from the analeptic point of view were tested with regard to their breathing stimulating The breathing stimulating activity was on rabbits and on rabbits whose respiration was depressed by of The obtained are set out in the following Table TABLE III Index Activity In table III the values are given index and of the specific activity the latter in relation to metrazol which was as a insufficientOCRQuality
Claims (1)
1. ia or and is chloride chloride drochloride hydroch ride hydrochlor hydrochlor insufficientOCRQuality
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2422165A IL24221A (en) | 1965-08-24 | 1965-08-24 | Chromones and processes for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL2422165A IL24221A (en) | 1965-08-24 | 1965-08-24 | Chromones and processes for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL24221A true IL24221A (en) | 1969-03-27 |
Family
ID=11043702
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2422165A IL24221A (en) | 1965-08-24 | 1965-08-24 | Chromones and processes for the preparation thereof |
Country Status (1)
| Country | Link |
|---|---|
| IL (1) | IL24221A (en) |
-
1965
- 1965-08-24 IL IL2422165A patent/IL24221A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Beltrami et al. | Some Methylhydrazonium Salts; An Improved Synthesis of Tetramethylhydrazine1 | |
| Stevens et al. | Isolation of an Epoxyether from the Reaction of an α-Haloketone with Base1 | |
| DK162992B (en) | METHOD OF ANALOGY FOR THE PREPARATION OF 1-PIPERAZINYL-3-PHENYL-INDANDER DERIVATIVES OR ACID ADDITION SALTS. | |
| DK150502B (en) | METHOD OF ANALOGUE FOR THE PREPARATION OF AMINOPHENYLETHANOLAMINES AND THEIR OXAZOLIDINES AND ACID ADDITION SALTS THEREOF | |
| Lancaster et al. | An Improved Synthesis of 3-Methylpyrrole | |
| IL24221A (en) | Chromones and processes for the preparation thereof | |
| NO132093B (en) | ||
| US3742074A (en) | Process for the preparation of aromatic trifluoromethyl compounds of the benzene series | |
| US2960507A (en) | Piperidine compounds | |
| NO135248B (en) | ||
| US2143491A (en) | Diphenylacetic acid esters | |
| JPH01308251A (en) | Production of bis(2, 2, 6, 6-tetramethyl-4- pyperidinyl)amine | |
| Asahina et al. | CCXX.—A synthesis of rutæcarpine | |
| US3544623A (en) | 3-isopropyltyrosine | |
| US2721203A (en) | Chloral nicotinamide and method for preparing the same | |
| Walker et al. | Limitations in Ring Rearrangement of Fused γ-Lactams Imposed by a Quaternary Carbon Atom. Cyclization of Acid Lactams to Spiro Keto Lactams | |
| SU480216A3 (en) | The method of obtaining - (aminophenyl) aliphatic derivatives of carboxylic acids or their salts, or their oxides | |
| Alt et al. | Reactions of Enamines. VIII. The Reaction of Eniminium Salts with Trichloroacetate1 | |
| Feuer et al. | Michael-type Reactions with α, α, ι, ι-Tetranitroalkanes1 | |
| US3665032A (en) | Resolution of l-dopa intermediate | |
| Fuson et al. | An Abnormal Reaction in the Sommelet Aldehyde Synthesis | |
| SU61643A1 (en) | The method of obtaining highly concentrated formic acid | |
| SU122745A3 (en) | The method of obtaining the acid chlorides of one- or polybasic aryl carboxylic acids | |
| SU368223A1 (en) | METHOD OF OBTAINING SUBSTITUTED AROMATIC KETONES | |
| SU561563A1 (en) | The method of obtaining anesthetics-spatial isomeric benzoic esters of 1-alkyl (alkenyl) -2-methyl4-oxydecahydroquinoline |