GB468363A - Manufacture of new organic arsenic compounds - Google Patents
Manufacture of new organic arsenic compoundsInfo
- Publication number
- GB468363A GB468363A GB35995/35A GB3599535A GB468363A GB 468363 A GB468363 A GB 468363A GB 35995/35 A GB35995/35 A GB 35995/35A GB 3599535 A GB3599535 A GB 3599535A GB 468363 A GB468363 A GB 468363A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- sodium
- benzisoxazine
- acetylamino
- hydroxy
- 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
- 150000001495 arsenic compounds Chemical class 0.000 title 1
- 229940093920 gynecological arsenic compound Drugs 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 235000019345 sodium thiosulphate Nutrition 0.000 abstract 4
- 125000003277 amino group Chemical group 0.000 abstract 3
- VYGBQXDNOUHIBZ-UHFFFAOYSA-L sodium formaldehyde sulphoxylate Chemical compound [Na+].[Na+].O=C.[O-]S[O-] VYGBQXDNOUHIBZ-UHFFFAOYSA-L 0.000 abstract 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000004289 sodium hydrogen sulphite Substances 0.000 abstract 2
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 abstract 2
- XUIVKWAWICCWIQ-UHFFFAOYSA-M sodium;formaldehyde;hydrogen sulfite Chemical compound [Na+].O=C.OS([O-])=O XUIVKWAWICCWIQ-UHFFFAOYSA-M 0.000 abstract 2
- KVXDXIPSFOPQTR-UHFFFAOYSA-N (5-acetamido-2-amino-4-hydroxyphenyl)arsonic acid Chemical compound NC1=C(C=C(C(=C1)O)NC(C)=O)[As](O)(=O)O KVXDXIPSFOPQTR-UHFFFAOYSA-N 0.000 abstract 1
- YONQTSYYRBSYHE-UHFFFAOYSA-N (5-amino-2-hydroxyphenyl)arsonic acid Chemical compound NC1=CC=C(O)C([As](O)(O)=O)=C1 YONQTSYYRBSYHE-UHFFFAOYSA-N 0.000 abstract 1
- FNJHGTGVCMYYLD-UHFFFAOYSA-N (dihydroxy-lambda4-sulfanylidene)methanamine Chemical compound NC=S(O)O FNJHGTGVCMYYLD-UHFFFAOYSA-N 0.000 abstract 1
- XJHGBVCKYYNIPE-UHFFFAOYSA-N 2-(4-arsonoanilino)acetic acid Chemical compound OC(=O)CNC1=CC=C([As](O)(O)=O)C=C1 XJHGBVCKYYNIPE-UHFFFAOYSA-N 0.000 abstract 1
- PZHHPNFPPFPNEZ-UHFFFAOYSA-N O-(hydroxy-methylidene-oxo-lambda6-sulfanyl)hydroxylamine Chemical compound C=S(=O)(O)ON PZHHPNFPPFPNEZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- HVALGDAAGKVVSM-UHFFFAOYSA-N dihydroxy(methylidene)-$l^{4}-sulfane Chemical group OS(O)=C HVALGDAAGKVVSM-UHFFFAOYSA-N 0.000 abstract 1
- JWFFTGKETCQJCM-UHFFFAOYSA-N dihydroxy-methylidene-oxo-$l^{6}-sulfane Chemical group OS(O)(=C)=O JWFFTGKETCQJCM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003993 interaction Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
- C07F9/80—Heterocyclic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Abstract
Organo-arseno compounds of the formula <FORM:0468363/IV/1> in which R represents a methylene-bisulphite, methylene-sulphoxylate or methylene-carboxylic acid group and R<1>, whose presence is optional represents one or more substituents or a condensed isoxazine ring, are obtained by (1) reduction of equimolecular proportions of 8-acetylamino-3-hydroxy-1 : 4-benzisoxazine-6-arsonic acid and a phenyl- or benzisoxazinearsonic acid containing a free amino group, and treatment of the product with sodium formaldehyde bisulphite, sodium formaldehyde sulphoxylate or a halogen-acetic acid, (2) interaction in solution of equimolecular proportions of the arseno compound obtained by reduction of 8-acetylamino-3-hydroxy-1 : 4-benzisoazine-6-arsonic acid and the arseno compound obtained by reduction of a phenylor benzisoazine-arsonic acid containing a free amino group, and subsequent treatment of the product with sodium formaldehyde bisulphite, sodium formaldehyde sulphoxylate or a halogen-acetic acid. In either case the subsequent treatment may be dispensed with if a phenyl- or benzisoxazine-arsonic acid is used which contains, instead of the free amino group, an amino-methylene-bisulphite, an amino-methylene-sulphoxylate or an aminomethylene-carboxylic acid group. The products possess therapeutic properties. According to the examples; (1) 8-acetylamino-3-hydroxy - 1 : 4 - benzisoxazine - 6 - arsonic acid and 8-amino-3-hydroxy-1 : 4-benzisoxazine 6-arsonic acid are together reduced with sodium hyposulphite and the product treated with sodium formaldehyde sulphoxylate; (2) a mixture of 8-acetylamino-3-hydroxy-1 : 4-benzisoxazine - 6 - arsonic acid and 5-amino-2-hydroxyphenyl-arsonic acid is reduced with sodium hyposulphite and the resulting arseno compound then treated with formaldehyde and sodium bisulphite; (3) 8-acetylamino-3-hydroxy - 1 : 4 - benzisoxazine - 6 - arsonic acid is reduced with sodium hyposulphite in presence of p-carboxymethylamino-phenylarsonic acid; (4) formaldehyde and sodium bisulphite are added to the arseno compound prepared by reduction with sodium hyposulphite of a mixture of 8-acetylamino-3-hydroxy-1 : 4-benzisoxazine - 6 - arsonic acid and 3 amino - 5 - acetylamino - 4 - hydroxyphenylarsonic acid. Specifications 3615/12, 7865/12, 174,078, 250,577, 278,444, 280,613, and 295,744, [all in Class 2 (iii)], are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35995/35A GB468363A (en) | 1935-12-30 | 1935-12-30 | Manufacture of new organic arsenic compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35995/35A GB468363A (en) | 1935-12-30 | 1935-12-30 | Manufacture of new organic arsenic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB468363A true GB468363A (en) | 1937-06-30 |
Family
ID=10383814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35995/35A Expired GB468363A (en) | 1935-12-30 | 1935-12-30 | Manufacture of new organic arsenic compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB468363A (en) |
-
1935
- 1935-12-30 GB GB35995/35A patent/GB468363A/en not_active Expired
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