IL28597A - N-trifluoromethyl-n-trihalomethyl-thioamino benzamides and their production - Google Patents
N-trifluoromethyl-n-trihalomethyl-thioamino benzamides and their productionInfo
- Publication number
- IL28597A IL28597A IL2859767A IL2859767A IL28597A IL 28597 A IL28597 A IL 28597A IL 2859767 A IL2859767 A IL 2859767A IL 2859767 A IL2859767 A IL 2859767A IL 28597 A IL28597 A IL 28597A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- hydrogen
- lower alkyl
- formula
- amino benzoic
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
- A61K31/24—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group having an amino or nitro group
- A61K31/245—Amino benzoic acid types, e.g. procaine, novocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C313/08—Sulfenic acids; Derivatives thereof
- C07C313/18—Sulfenamides
- C07C313/20—Sulfenamides having sulfur atoms of sulfenamide groups bound to acyclic carbon atoms
Description
and their production BAYER Certain benzoic acid such as salicylic acid are known as agents for use in It has now been found that new amino benzoic acid amides I hibit very good action both in vitro and in vivo in According to the present the amino benzoic acid amides I are prepared by reacting of the with amines of the wherein and are as above in the presence of an The reaction scheme can be illustrated by the of and butylamine to produce HC1 The used as starting materials are prepared ing to the process of German Patent F 49 313 from and sulphenic acid Suitable inter or or Suitable amines for according to the present inter all aniline and The reaction temperature can be varied fairly wide ranges and such would be known to those skilled in the It is most to operate the tion at a temperature of from to which are suitable for use in the present reaction inter free inert organic such as dloxane or A tertiary base or alkali metal hydroxide is added in order to bind the hydrogen fluoride which is freed during the It is preferred to use twice the quantity of amine required for the following test data illustrates the antimycotic action of the amino benzoic acid Microbiological Experiments The effect of the preparations on the growth of several different test fungi is compiled in the following of Minimum inhibition concentration as of parations nutrient substrate in Microsp I Candida the commune I 40 10 100 100 40 IV 100 20 VI 4 20 20 4 4 100 20 VIII 20 10 10 10 10 IX X 10 20 20 100 100 XI 0 10 10 4 40 40 XVII 10 10 10 with serum without serum The protein binding of the preparations in this test has to be regarded as very The test in vitro was carried out by the series tion and the stab test method on s milieu The preparation shows in the animal in formamide applied locally and once in the therapy a good effect on the course of trichophyty in experiments on guinea and is superior in this test to several commercial preparations with regard to its Salicylic acid anilides in some show similar effect in vitro experiments generally show no effect or an insufficiently weak effect in vivo animal The following examples further trate the present Example 1 Λ 15 Grams are dissolved in 100 ml toluene and solution is mixed dropwise at room temperature with 8 g butylamine in 20 ml The temperature is allowed to rise up to The reaction solution is shaken out with dried and concentrated in a The residue is crystallized from white In an analogous the following compounds were obtained using the following from and from and and from and from and CF3 from and from and cy from and 28597 2 3 from and oromethylthio and 2 Grams are dissolved in 100 ml the solution is mixed with ml aqueous at room while stirring The is allowed to rise up to the two layers are separated and the benzene layer is After from white the reaction product of is In ananalogous the following compounds were obtained using the following 3 from and CI from and from and from and methylamine from and and 16 from 2 j flu from and 3 from and Example 4 18 Grams are dissolved in 100 ml benzene and the solution is mixed with a solution of g butylamine in 200 ml the reaction is the reaction mixture is shaken out with From the benzene solution there is after the reaction product as a crystalline residue of insufficientOCRQuality
Claims (35)
1. Amino benzoic aeid amides of the formulas wherein: R^ is trihalomethyl; Eg is hydrogen, lower alkyl of 1 to 4 carbon atoms, lower alkenyl of 1 to 4 carbon atoms; R^ is hydrogen, lower alkyl, lower alkenyl, cyclo-alkyl, aryl, aodecyl ©r β-hydroxyethyl; or R2 and R^, together with their adjacent nitrogen atom, form a 5 or 6 membered ring which may be interrupted by the additional hateroa oms -0-, -S« or -HRC-, where R_ is hydrogen or lower alkyl; R^ is hydrogen, one or more halogen atoms, lower alkyl, lower alkoxy or trifluoromethyl.
2.,···· · A compound according tc claim 1 wherein ίε tri-chXpromethyl or dichlprofluoromethyl.
3. . The compound
4. , The compound CF.
5. The compound CF.
6. The ccmpcund
7. The compound NHCH SCFC CF„
8. The compound
9. The compound
10. The compound
11. The compound
12. The compound
13. The compound CF.
14. The compound
15. The compound
16. The compound
17. The compound
18. The compound
19. The compound
20. The compound ONHCH. C
21. The compound
22. The compound
23. The compound
24. The compound
25. The compound CF3-N-SCFC12
26. The compound CF3-N-SCFC12
27. The compound
28. The compound
29. The compound CONHC,H
30. 0. The compound
31. 1 The compound
32. 2 The compound
33. The compound CF.
34. The compound
35. A process for the production of amino benzoic acid abides of the formula: CF3 which comprises reacting fluorocarbonyl-N-(trihalomethylthio) N~ trifiuoromethyl-anilines of the formula: 28597/2 32 CP, with amines of the formula. in the presence of an acid-binding agent, wherein in the above formulae R^, ^, and R^ have the same meaning ae in Claim 1, and recovering the amino benzoic acid amide produced. D:BK
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0050207 | 1966-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL28597A true IL28597A (en) | 1971-10-20 |
Family
ID=7103614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL2859767A IL28597A (en) | 1966-09-15 | 1967-09-03 | N-trifluoromethyl-n-trihalomethyl-thioamino benzamides and their production |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT278748B (en) |
| CH (1) | CH487845A (en) |
| DE (1) | DE1543615C3 (en) |
| FR (2) | FR1557674A (en) |
| GB (1) | GB1154870A (en) |
| IL (1) | IL28597A (en) |
-
1966
- 1966-09-15 DE DE19661543615 patent/DE1543615C3/en not_active Expired
-
1967
- 1967-08-11 CH CH1133567A patent/CH487845A/en not_active IP Right Cessation
- 1967-09-03 IL IL2859767A patent/IL28597A/en unknown
- 1967-09-15 FR FR1557674D patent/FR1557674A/fr not_active Expired
- 1967-09-15 AT AT844867A patent/AT278748B/en not_active IP Right Cessation
- 1967-09-15 GB GB42207/67A patent/GB1154870A/en not_active Expired
- 1967-12-14 FR FR132326A patent/FR6979M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1154870A (en) | 1969-06-11 |
| DE1543615A1 (en) | 1969-07-31 |
| FR1557674A (en) | 1969-02-21 |
| DE1543615B2 (en) | 1975-03-13 |
| CH487845A (en) | 1970-03-31 |
| DE1543615C3 (en) | 1975-10-23 |
| FR6979M (en) | 1969-05-27 |
| AT278748B (en) | 1970-02-10 |
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