CH290452A - Process for the preparation of a novel derivative of α-naphthylamine-4-sulfonic acid. - Google Patents
Process for the preparation of a novel derivative of α-naphthylamine-4-sulfonic acid.Info
- Publication number
- CH290452A CH290452A CH290452DA CH290452A CH 290452 A CH290452 A CH 290452A CH 290452D A CH290452D A CH 290452DA CH 290452 A CH290452 A CH 290452A
- Authority
- CH
- Switzerland
- Prior art keywords
- naphthylamine
- sub
- preparation
- dehydrating agent
- sulfonic acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- NRZRRZAVMCAKEP-UHFFFAOYSA-N naphthionic acid Chemical class C1=CC=C2C(N)=CC=C(S(O)(=O)=O)C2=C1 NRZRRZAVMCAKEP-UHFFFAOYSA-N 0.000 title description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical group [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000012024 dehydrating agents Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- JWSRMCCRAJUMLX-UHFFFAOYSA-M sodium;4-aminonaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(N)=CC=C(S([O-])(=O)=O)C2=C1 JWSRMCCRAJUMLX-UHFFFAOYSA-M 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical group [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 239000008103 glucose Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical group NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 235000005074 zinc chloride Nutrition 0.000 claims description 2
- 239000011592 zinc chloride Substances 0.000 claims description 2
- 229930182478 glucoside Natural products 0.000 claims 1
- 239000000155 melt Substances 0.000 claims 1
- -1 sodium α-naphthylamine-4-sulfonate glucoside Chemical class 0.000 claims 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 229960001031 glucose Drugs 0.000 description 3
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 208000032843 Hemorrhage Diseases 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 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
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 230000023555 blood coagulation Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 229960003082 galactose Drugs 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 229960003487 xylose Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Procédé de préparation d'un nouveau dérivé de l'acide a-naphthylamine-4-sulfonique. On a trouvé que les nouveaux dérivés de l'acide a-naphthylamine-4-sulfonique, répon dant à la formule donnée ci-dessous, sont doués de propriétés thérapeutiques intéres santes.
EMI0001.0004
Dans cette formule, R est un radical d'hy drate de carbone, par exemple celui d'un monosaccharide, tel que le glucose, 1e galac tose, le xylose, celui d'un polysaccharide, et g est un atome d'hydrogène ou un atome d'un métal monovalent, tel que le sodium, ou un équivalent d'un métal polyvalent, tel que le calcium ou un radical organique ou encore un groupe amino ou amido.
Ces composés sont efficaces dans le traite ment et la prévention des hémorragies, ils augmentent la vitesse de coagulation du sang et réduisent le temps de saignement; de plus, ils sont dépourvus de toxicité.
Le présent brevet a donc pour objet un procédé de préparation d'un de ces nouveaux dérivés, à savoir le glueoside de l'a-naphthyl- amine-4-sulfonate de sodium. Ce procédé est caractérisé en ce que l'on condense du glucose avec de l'a-naphthylamine-4-sulfonate de so dium. Cette condensation peut être effectuée au sein d'un dissolvant, lequel peut être de l'eau ou de préférence un dissolvant anhydre; elle peut aussi être exécutée en l'absence de tout dissolvant ou autre corps.
On peut l'effectuer à l'aide de la chaleur; en présence d'un agent déshydratant, tel que .le chlorure d'ammo nium, le bisulfate de potassium, le chlorure de zinc ou un autre sel de propriétés ana logues. _ Voici, à titre d'exemple, comment le pro cédé du présent brevet peut être exécuté:
On fait réagir 12,26 g d'a-naphthylamine- 4-sulfonate de sodium anhydre avec 10 g de glucose anhydre dans 600 ems d'alcool ab solu en présence d'un gramme de chlorure d'ammonium. On chauffe à ébullition à re flux au bain de vapeur, tout en agitant le mé lange réactionnel continuellement pendant deux heures.
On laisse ensuite refroidir, il se forme une masse cristalline que l'on isole par filtration, on la lave à. l'alcool et l'essore. On obtient une masse cristalline très soluble dans l'eau, peu soluble dans l'alcool et dans l'éther. Ce produit se décompose sans fondre vers 200 C, et son pouvoir rotatoire est de
EMI0001.0035
Ses solutions aqueuses sont stables à la tempé rature ordinaire, même à des pH bas, comme celui du suc gastrique. Il est utilisable en thérapeutique.
Process for the preparation of a novel derivative of α-naphthylamine-4-sulfonic acid. It has been found that the new derivatives of α-naphthylamine-4-sulfonic acid, corresponding to the formula given below, are endowed with valuable therapeutic properties.
EMI0001.0004
In this formula, R is a carbohydrate radical, for example that of a monosaccharide, such as glucose, galac tose, xylose, that of a polysaccharide, and g is a hydrogen atom or an atom of a monovalent metal, such as sodium, or an equivalent of a polyvalent metal, such as calcium or an organic radical or else an amino or amido group.
These compounds are effective in the treatment and prevention of hemorrhages, they increase the rate of blood clotting and reduce the bleeding time; moreover, they are devoid of toxicity.
The subject of the present patent is therefore a process for preparing one of these new derivatives, namely glueoside of sodium α-naphthylamine-4-sulfonate. This process is characterized in that glucose is condensed with sodium α-naphthylamine-4-sulfonate. This condensation can be carried out in a solvent, which can be water or preferably an anhydrous solvent; it can also be performed in the absence of any solvent or other substance.
It can be done using heat; in the presence of a dehydrating agent, such as ammonium chloride, potassium bisulfate, zinc chloride or another salt of similar properties. _ Here is, by way of example, how the process of this patent can be carried out:
12.26 g of anhydrous sodium α-naphthylamine-4-sulfonate are reacted with 10 g of anhydrous glucose in 600 ems of absolute alcohol in the presence of one gram of ammonium chloride. The mixture is heated to a reflux boiling point in a steam bath, while stirring the reaction mixture continuously for two hours.
Then allowed to cool, a crystalline mass is formed which is isolated by filtration and washed with. alcohol and wring it out. A crystalline mass is obtained which is very soluble in water, slightly soluble in alcohol and in ether. This product decomposes without melting at around 200 C, and its rotatory power is
EMI0001.0035
Its aqueous solutions are stable at room temperature, even at low pHs, such as that of gastric juice. It can be used in therapy.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH290452T | 1951-04-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH290452A true CH290452A (en) | 1953-04-30 |
Family
ID=4487075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH290452D CH290452A (en) | 1951-04-20 | 1951-04-20 | Process for the preparation of a novel derivative of α-naphthylamine-4-sulfonic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH290452A (en) |
-
1951
- 1951-04-20 CH CH290452D patent/CH290452A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH290452A (en) | Process for the preparation of a novel derivative of α-naphthylamine-4-sulfonic acid. | |
| CH411363A (en) | Process for the preparation of phosphorus compounds | |
| MC940A1 (en) | Method for preparing n- (1-ethyl-pyrrolidylmethyl) -2-methoxy-5-sulfamidobenzamide | |
| CH401989A (en) | Process for preparing phosphocreatine | |
| US2832719A (en) | Nystatin purification | |
| KR840000766B1 (en) | Process for preparing bismoranolin derivatives | |
| SU609284A1 (en) | Method of preparing 5-nitro-8-oxyquinoline? | |
| US2493645A (en) | Nicotinic acid-beta-picolyl-amide and process for the manufacture thereof | |
| KR910002686B1 (en) | Process for the preparation of 2-diethylamino -1-methyl ethil cis-1-hydroxy-(bicyclohexyl)-2-carboxylate derivatives | |
| US2481597A (en) | Substituted propionic acids and processes of preparing the same | |
| US2715125A (en) | Y-hydroxypropyl theophylline deriva- | |
| Adams et al. | Quinone Imides. XXVI. Adducts of p-Quinonebis-(dimethylaminosulfonimides) and their Hydrolysis Products | |
| JPS58194895A (en) | Improved method for preparing na salt of dbc-amp (n6,2'-o-dibutyryladenosine-3,5'-cyclic phosphate) | |
| BE824491R (en) | PROCESS FOR PREPARING 1,8-NAPHTHYRIDINE DERIVATIVES | |
| CH294177A (en) | Process for the preparation of a new derivative of pyridine. | |
| CH247711A (en) | Process for preparing acetylaminobenzene-sulfonylguanidine. | |
| Tipson et al. | Studies in the Quinoline Series. IX. The Mononitrophenyllepidylcarbinols and Related Compounds | |
| CH370093A (en) | Process for the preparation of diamino-caproic acid derivatives | |
| CH402842A (en) | Process for the preparation of new heparin derivatives | |
| CH216546A (en) | Process for the preparation of 2- (para-amino-benzenesulfamido) -pyridine. | |
| CH341831A (en) | Process for the preparation of condensation products of saccharides with nitrogen of N-desacetyl-alkylthiocolchiceins | |
| CH307324A (en) | A process for preparing amino-2-hydroxy-4- (chloro-4'-phenyl) -5-ethyl-6-pyrimidine. | |
| JPS6111228B2 (en) | ||
| JPS609498B2 (en) | Homoproline production method | |
| CH283239A (en) | Process for preparing a new amide starting from an acid chloride and an amino alcohol. |