US2462963A - Derivatives of rho-aminobenzenesulfonamides and process of making same - Google Patents
Derivatives of rho-aminobenzenesulfonamides and process of making same Download PDFInfo
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- US2462963A US2462963A US496838A US49683843A US2462963A US 2462963 A US2462963 A US 2462963A US 496838 A US496838 A US 496838A US 49683843 A US49683843 A US 49683843A US 2462963 A US2462963 A US 2462963A
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- US
- United States
- Prior art keywords
- aminobenzenesulphonamido
- derivatives
- salts
- water
- aminobenzenesulfonamides
- 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 - Lifetime
Links
- 238000000034 method Methods 0.000 title description 6
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 13
- 150000003839 salts Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- SOEVVANXSDKPIY-UHFFFAOYSA-M sodium glyoxylate Chemical compound [Na+].[O-]C(=O)C=O SOEVVANXSDKPIY-UHFFFAOYSA-M 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 6
- -1 aminobenzenesulphonamido Chemical group 0.000 description 5
- JNMRHUJNCSQMMB-UHFFFAOYSA-N sulfathiazole Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CS1 JNMRHUJNCSQMMB-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007859 condensation product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- KINFJLYCWPTJRB-UHFFFAOYSA-N 2,2-diacetyloxyacetic acid Chemical compound CC(=O)OC(C(O)=O)OC(C)=O KINFJLYCWPTJRB-UHFFFAOYSA-N 0.000 description 1
- VTSWSQGDJQFXHB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylpyrimidine Chemical compound CC1=C(Cl)N=C(Cl)N=C1Cl VTSWSQGDJQFXHB-UHFFFAOYSA-N 0.000 description 1
- XIJCOJYCASQRKH-UHFFFAOYSA-N 5-ethylsulfanyl-1h-pyrazole Chemical compound CCSC=1C=CNN=1 XIJCOJYCASQRKH-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 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
- WCYIBFCMDXPRJX-UHFFFAOYSA-N N-(4-amino-1,3-dihydropyrazin-2-ylidene)benzenesulfonamide Chemical class NN1CC(=NC=C1)NS(=O)(=O)C1=CC=CC=C1 WCYIBFCMDXPRJX-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960002713 calcium chloride Drugs 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000012535 impurity Substances 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 150000003388 sodium compounds Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/50—Nitrogen atoms bound to hetero atoms
- C07D277/52—Nitrogen atoms bound to hetero atoms to sulfur atoms, e.g. sulfonamides
Definitions
- the salts may contain, in addition, crystal solvents.
- the compounds obtained by the present process dissolve readily in water in the form of their salts.
- the neutral solutions which can be prepared from the salts are therefore particularly suitable for parenteral administration and have the same activity as the parent p-aminobenzenesulphonamides, the latter being presumably reformed in the body.
- Z-(p-aminobenzenesulphonamido) -thiazole is particularly suitan able.
- Other compounds, which are substituted in the sulphonamide group by a polyheteroatomic, heterocyclic radical containing sulphur in the ring, can also be used e. g. Z-(p-aminobenzenesulphonamido) -4,5-dihydrothiazole or 2- (p aminobenzenesulphonamido) thiodiazoles such as 2 (p-aminobenzenesulphonamido) 5 ethyl-thiodiazole.
- Particularly suitable salts of glyoxylic acid are the alkali salts, but the alkaline earth or ammonium salts or the salts with organic bases can also be used for thereaction.
- compounds convertible into glyoxylic acid or its salts may be ne r pl s'lyoxylic. acid esters. rates out in the form oi a white powder. It is glyoxylic acid ester hemiacetals, thioglyoxylic filtered ofl by t washed with alcohol and acid, diacetoxy-acetic acid, 'dihalo-acetic acids, ether and dried at 100 C. etc.
- the corresponding calcium salt can.
- reaction should be advantageously cartained from this compound by reaction with cal-- cium chloride; it is less soluble in cold water than the sodium compound. but fairly soluble zenesizlphonamidobthiazole, are caused to reinwarm water. i
- Example 1 12.5 gm. of sodium glyoxylate are dissolved in com. or water and the solution heated to about 80 C. 25 gm. of 2-(p-aminobenzenesulphonamido)-thiazole are then introduced, stirring continually, and are dissolved completely within a short time. Any impurities can be filtered oil.
- the new compound does not have any real melting point. On heatingit turns dark above 170 C. and decomposition starts at 210-220 C., with frothing. v
- Example 4 25 gm. of 2-(p-aminobenzenesulphonamido)- thlazole are dissolved in 250 com. of hot glacial acetic acid and a warm solution of 15 gm. of glyoiwlic acid ethyl-ester hemi-acetal in 150 com. of glacial acetic acid added. On cooling, a yellowish sticky substance soon begins to separate out, rapidly becoming solid on further cooling. The yield is about 28 gm. The new compound does not melt below 300 0.; above 150 C. it gets darker and darker.
- a process for the manufacture of a derivative of a para-aminobenzenesulplionamide comprising treating 2-(para-aminobenzenesulphonamido) thiazole with sodium glyoxylate in a solvent medium whereby the para-amino group of the 2 (para-aminobenzenesulphonamido) thiazole reacts with the aldehyde group of the sodium glyoxylate.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Description
rled out in such a way that the p-aminobenzenesulphonamides, in particular the 2- (p-aminobenmemo Mar. 1, 1949 UNITED STATES, PATENT orrlca aim,
DERIVATIVES F p-AMINOB FONAMIDES AND PROCESS OF MAKING SAME Ma: Hartmann and Jean Druey. Biehen, Switaorland, 'asaignors to Clba Pharmaceutical Prodgets Ino., Summit, N. 1., a corporation of New erse! No Drawing. Application July so, 1m, sci-m No. 496.838. in Switzerland April 14, ms
2 Claims. (Cl. 260-2395) 2 act with slyoxyiic acid salts, for example with sodium glyoxylate in water. if necessary adding a solvent which is miscible with water, e. g. alcohol. The reaction can also be carried out in the presence of organic solvents, particularly it glyoxylic acid or its esters are used. The compounds obtained in the form; of the free. carboxylic acids. esters, etc. can be converted in a known manner into any water-soluble salt e. g. the sodium, ammonium or calcium salt.
The constitution of the new compounds can not be exactly determined. The analytical results give the following probable formulae:
n-zm-sm-Qraon-ooon a-mn-sm-Q-mr-zn-ooon v I I H a-nn-soQmr-on-mrQswNn-a coon wherein R represents a polyheteroatomic, heterocyclic radical. The salts may contain, in addition, crystal solvents.
The compounds obtained by the present process dissolve readily in water in the form of their salts. The neutral solutions which can be prepared from the salts are therefore particularly suitable for parenteral administration and have the same activity as the parent p-aminobenzenesulphonamides, the latter being presumably reformed in the body.
The appended claims are directed to the preierred form 01. the invention, involving the reaction between sodium glyoxylate and 2-(paminobenzenesulphonamido)-thiazole, and the resulting product.
The suggestion has already been made that chemotherapeuticaily active p-aminobenzenesulphonamides which are only slightly soluble in water should be made water-soluble by the introduction into the amino group of radical 5 containing a salt-forming group. The previous processes or this kind had the disadvantage of being diflicult to carry out, or of giving compounds which are considerably less'active on parenteral administration than the unsubstituted amines. These water-soluble derivatives arepresumably not decomposed rapidly enough, with the result that the parent amines are not able to exert their full eflect. g
It has now been found that derivatives of p-aminobenzenesulphonamides which are watersoluble and at the same time parenterally active can be obtained in a satisfactory way if chemotherapeutically active p-aminobenzenesuiphonamides which are substituted in the sulphonamide 2 group by a polyheteroatomic, heterocyclic radical are caused to react with salts of glyoxylic acid, with this free acid or with compounds convertible into glyoxylic acid or into its salts and, if necessary. converting the compounds obtained into water-soluble salts of the corresponding carboxylic acids.
Amongst the p-aminobenzenesulphonamides mentioned as parent products, Z-(p-aminobenzenesulphonamido) -thiazole is particularly suitan able. Other compounds, which are substituted in the sulphonamide group by a polyheteroatomic, heterocyclic radical containing sulphur in the ring, can also be used e. g. Z-(p-aminobenzenesulphonamido) -4,5-dihydrothiazole or 2- (p aminobenzenesulphonamido) thiodiazoles such as 2 (p-aminobenzenesulphonamido) 5 ethyl-thiodiazole. It is also possible to start from p-amlnobenzenesulphonamido-pyrimidines e. g. fi-(p-aminobenzenesulphonamido) -2,4-di- 4o methyl-pyrimidine or from p-aminobenzenesulphonamido-pyrazines.
Particularly suitable salts of glyoxylic acid are the alkali salts, but the alkaline earth or ammonium salts or the salts with organic bases can also be used for thereaction. As compounds convertible into glyoxylic acid or its salts may be ne r pl s'lyoxylic. acid esters. rates out in the form oi a white powder. It is glyoxylic acid ester hemiacetals, thioglyoxylic filtered ofl by t washed with alcohol and acid, diacetoxy-acetic acid, 'dihalo-acetic acids, ether and dried at 100 C. etc. The corresponding calcium salt can. be ob- The reaction should be advantageously cartained from this compound by reaction with cal-- cium chloride; it is less soluble in cold water than the sodium compound. but fairly soluble zenesizlphonamidobthiazole, are caused to reinwarm water. i
Example 1 12.5 gm. of sodium glyoxylate are dissolved in com. or water and the solution heated to about 80 C. 25 gm. of 2-(p-aminobenzenesulphonamido)-thiazole are then introduced, stirring continually, and are dissolved completely within a short time. Any impurities can be filtered oil.
tinually. when the condensation product sepa- The solution is poured into alcohol, stirring con- 3 Example 2 W I llgmf'of 75 per cent g'lyoxylic acid are dis solved in 80 com." of water andneutralized with Example 3 7.2 gm. of 2-(p-aminobenzenesulphonamido)- thiazole are added to 60 com. of hot absolute alcohol containing 6.2 gm. of 68 per cent glyoxylic acid, a clear solution being obtained after a short time. After cooling, the condensation product is precipitated with ether, filtered off by suction and dried. It is a somewhat yellowish powder which dissolves easily in sodium bicarbonate.
The new compound does not have any real melting point. On heatingit turns dark above 170 C. and decomposition starts at 210-220 C., with frothing. v
In the same way a condensation product, which dissolves readily in bacarbonate to give a clear solution, can be obtained from G-(p-aminobenzenesulphonamido)-2,4-dimethyipyrimidine and glyoxylic acid.
Example 4 25 gm. of 2-(p-aminobenzenesulphonamido)- thlazole are dissolved in 250 com. of hot glacial acetic acid and a warm solution of 15 gm. of glyoiwlic acid ethyl-ester hemi-acetal in 150 com. of glacial acetic acid added. On cooling, a yellowish sticky substance soon begins to separate out, rapidly becoming solid on further cooling. The yield is about 28 gm. The new compound does not melt below 300 0.; above 150 C. it gets darker and darker.
To saponify the ester group, 6 gm. of the substance are dissolved in 30 com. of 2N NaOH and allowed to stand for 20 hours at 20 C. The solution is then neutralized by the addition of 20 com. of 2N HCl and separated from the precipitated amorphous substances. 0n precipitation with alcohol, a compound is obtained, whose properties agree with those of the sodium salt described in Example 1.
What we claim is:
1. A process for the manufacture of a derivative of a para-aminobenzenesulplionamide, comprising treating 2-(para-aminobenzenesulphonamido) thiazole with sodium glyoxylate in a solvent medium whereby the para-amino group of the 2 (para-aminobenzenesulphonamido) thiazole reacts with the aldehyde group of the sodium glyoxylate.
2. The compound obtained by a process consisting in treating 2-(para-aminobenzenesulphonamido) -thiazole with sodium glyoxylate in a solvent medium whereby the para-amino group of the 2-(para-aminobenzenesulphonamidc) -thiazole reacts with the aldehyde group of the sodium glyoxylate.
JEAN DRUEY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Name OTHER REFERENCES Chemical Reviews, vol. 27, pages 107-109 and 127-129 (1940).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH2462963X | 1943-04-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2462963A true US2462963A (en) | 1949-03-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US496838A Expired - Lifetime US2462963A (en) | 1943-04-14 | 1943-07-30 | Derivatives of rho-aminobenzenesulfonamides and process of making same |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2462963A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2566038A (en) * | 1949-03-17 | 1951-08-28 | American Cyanamid Co | Water-soluble sulfonamides |
| US2596950A (en) * | 1947-09-06 | 1952-05-13 | Shell Dev | Method of purifying ammonium sulfate |
| US4052408A (en) * | 1968-07-23 | 1977-10-04 | Ciba-Geigy Corporation | Oxyacetic acid compounds and process for their manufacture |
| US20070052330A1 (en) * | 2005-09-08 | 2007-03-08 | Chien-Kuo Chang | Stackable cabinet structure |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR839711A (en) * | 1937-12-13 | 1939-04-11 | Mouneyrat Et Cie Ets | Preparation of soluble derivatives of 4-amino phenylsulfamide |
| GB517272A (en) * | 1938-06-03 | 1940-01-25 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
| US2303698A (en) * | 1940-06-03 | 1942-12-01 | Lilly Co Eli | Derivatives of p-aminobenzenesulphonylamide (i. e., sulphanilamide) and the process of producing them |
| US2324014A (en) * | 1941-07-31 | 1943-07-13 | Sharp & Dohme Inc | Succinylsulphathiazole |
| US2358031A (en) * | 1944-09-12 | Substituted thiadiazoles |
-
1943
- 1943-07-30 US US496838A patent/US2462963A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2358031A (en) * | 1944-09-12 | Substituted thiadiazoles | ||
| FR839711A (en) * | 1937-12-13 | 1939-04-11 | Mouneyrat Et Cie Ets | Preparation of soluble derivatives of 4-amino phenylsulfamide |
| GB517272A (en) * | 1938-06-03 | 1940-01-25 | May & Baker Ltd | The preparation of new therapeutically useful heterocyclic compounds |
| US2362087A (en) * | 1938-06-03 | 1944-11-07 | May & Baker Ltd | Sulphanilamido-thiazoles |
| US2303698A (en) * | 1940-06-03 | 1942-12-01 | Lilly Co Eli | Derivatives of p-aminobenzenesulphonylamide (i. e., sulphanilamide) and the process of producing them |
| US2324014A (en) * | 1941-07-31 | 1943-07-13 | Sharp & Dohme Inc | Succinylsulphathiazole |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2596950A (en) * | 1947-09-06 | 1952-05-13 | Shell Dev | Method of purifying ammonium sulfate |
| US2566038A (en) * | 1949-03-17 | 1951-08-28 | American Cyanamid Co | Water-soluble sulfonamides |
| US4052408A (en) * | 1968-07-23 | 1977-10-04 | Ciba-Geigy Corporation | Oxyacetic acid compounds and process for their manufacture |
| US20070052330A1 (en) * | 2005-09-08 | 2007-03-08 | Chien-Kuo Chang | Stackable cabinet structure |
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