IL31390A - Nitrofuran derivatives,their preparation,and pharmaceutical and veterinary compositions containing them - Google Patents
Nitrofuran derivatives,their preparation,and pharmaceutical and veterinary compositions containing themInfo
- Publication number
- IL31390A IL31390A IL31390A IL3139069A IL31390A IL 31390 A IL31390 A IL 31390A IL 31390 A IL31390 A IL 31390A IL 3139069 A IL3139069 A IL 3139069A IL 31390 A IL31390 A IL 31390A
- Authority
- IL
- Israel
- Prior art keywords
- pharmaceutical
- carboxylic acid
- reaction mixture
- veterinary compositions
- radical
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 6
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 title description 5
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 title description 2
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 10
- 229910017604 nitric acid Inorganic materials 0.000 claims description 10
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 239000000047 product Substances 0.000 claims description 5
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 2
- VYOBETUUXYCOLS-UHFFFAOYSA-N (2-formyl-5-nitro-2H-furan-5-yl) propanoate propanoic acid Chemical compound C(CC)(=O)O.C(CC)(=O)O.[N+](=O)([O-])C1(C=CC(O1)C=O)OC(CC)=O VYOBETUUXYCOLS-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000000802 nitrating effect Effects 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 241000588722 Escherichia Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960001907 nitrofurazone Drugs 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
-
- 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
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
A process preparation of nitrofuran derivatives and pharmaceutical and veterinary compositions containing such derivatives ns a process for the preparation of acylated nitrofuran derivatives and pharmaceutical and veterinary compositions containing and their The invention provides a new process for preparing diacyl compounds of the general formula this the present invention provides a process for the preparation of compounds of formula wherein furfural and nitric acid are continuously fed at about to a prepared mixture of oulphuric and nitric acids and the anhydride the carboxylic acid whose radical to be introduced into the prepared and the reaction product is recovered from the reaction mixture without the addition of water and This process avoids any danger of which exists in known processes for the nitration of furfural The anhydride of the aliphatic acid is preferably in the stochiometrical amount equivalent to the In the the precipitation of crystals begins when the mixture of furfural and nitric acid is being introduced into the mixture The crystals are by The reaction product thus recovered is pre erably subjected to by treatment with an preferably a straight or branched lower aliphatic alcohol containing carbon with The stabilised compounds are readily and suitable for therapeutical The invention provides pharmaceutical and veterinar compositions comprising as active ingredient at least one compound of the formula The compositions may be in solid powder ointments and or liquid form suitable for or parenteral They may in admixture with the active inert or anic or inoranic ha a The pharmaceutical and veterinary compositions according to the present invention can be prepared by conventional by admixing the active ingredient with the desired diluents The invention is illustrated by the following Examples to which it is not Example 1 204 g of acetic anhydride are introduced into an 1 litre flask equipped with a stirrer and a and cooled to then g of concentrated sulphuric acid are The mixture stirred for 10 then 5 of nitric acid and g of water are This initial mixture is kept at 68 g of nitric acid and 96 g of freshly destillated furfural are added continuously and concurrently to the nitrating mixture with stirring and external cooling at The rate of addition of the two components is preferably proportional and should completed at the same After the addition of about part of the furfural the precipitation of the it becomes more and more When complete amount of nitric acid and furfural has been added the mixture is stirred at a temperature between and until a thick crystalline mass has The is covered with cold methanol and filtered with The product is dissolved in double its amount of hot the solution is clarified with activated charcoal and and the filtrate is crystallised by cooling in an The precipitated crystals are filtered and dried in vacuo at J The activity of the product has been determined by in vitro The following results have been Escherichia coli flavus The above values are expressed in The infrared spectrum of tho compound contains the following characteristic 1202 Example 2 330 g of propionic anhydride are introduced into an 1 litre flask equipped with a stirrer and a and cooled to then 1 g of sulphuric acid is mixture is stirred at for 10 minutes and 48 g of nitric acid are 54 g of nitric acid and g of freshly distilled furfural are added concurrently and continuously to the nitrating mixture aforesaid with stirrin and external cooling at at such a rate that the addition of both components is completed at the same The precipitation of the begins already during the After the addition the reaction mixture is stirred at a temperature between until a thick crystalline mass formed and the crystallization has become The precipitate is covered with cooled methanol and filtered The precipitated crystals are filtered and dried in vacuo at Thus 62 g of are molecular weight The activity of the product has been determined by in vitro tests and the following results have been obtained Escherichia The above values are expressed in The infrared spectrum of the compound contains the following characteristic 1514 New nitrofuran their and pharmaceutical and veterinary compositions containing them GXARA C This invention concerns new acylated nitrofuran pharmaceutical and veterinary compositions containing and their The invention provides new compounds of the general formula new compounds of the formula I can he used for huma and veterinar purposes as and may bo the radical a straight or branched chained aliphatic carboxyllc acid haying preferably not more than 8 carbon Particularly suitable are the compounds in which R is the acetyl or radicals the compounds are stabilised by contact with an organic solvent such as a lower aliphatic alcohol or It is known that by the nitration of furfural with nitric acid in anhydride formed Farmacie and that this compound can be converted into which is an important starting material used for the preparation of a number of valuable 7 insufficientOCRQuality
Claims (6)
1. 5-Iii ro-5-acyl-2 , 5-dihydro-furan-2-al diacyl compounds of the general formula H H wherein R stands for the acyl-radical of ah aliphatic carboxylic acid.
2. 5-Nitro-5-propionoxy-2 , 5-dihydro-furan-2-al- dipropionate,
3. 5-J¾itro-5-acetoxy-2 , 5-dihydro-furan-2-al-diacetate·
4. A process for the preparation of compounds according to Claims 1, 2 or 3 , wherein furfural and nitric acid are continuously fed at about 0 G to a prepared mixture of sulphuric and nitric acids and the anhydride of the carboxylic acid whose radical R is to be introduced into the prepared molecule, and the reaction product is recovered from the reaction mixture without the addition of water and alkali*
5. process according to Claim 4 » wherein the product recovered from the reaction mixture is 3 tabilized by contact with an organic solvent such as a lower aliphatic alcohol or acetone.
6. Pharmaceutical and veterinary compositions comprising ae aotive ingredient at least one oompound according to Claims 1, 2 or 3 , optionally stabilized by the process according to Claim 5 ·
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI000768 | 1968-01-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL31390A0 IL31390A0 (en) | 1969-03-27 |
| IL31390A true IL31390A (en) | 1972-09-28 |
Family
ID=10994345
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL31390A IL31390A (en) | 1968-01-09 | 1969-01-09 | Nitrofuran derivatives,their preparation,and pharmaceutical and veterinary compositions containing them |
Country Status (8)
| Country | Link |
|---|---|
| CA (1) | CA948645A (en) |
| DE (1) | DE1900711A1 (en) |
| DK (1) | DK123478B (en) |
| FR (1) | FR2000089A1 (en) |
| GB (1) | GB1250992A (en) |
| IL (1) | IL31390A (en) |
| NL (1) | NL157800B (en) |
| SE (1) | SE357965B (en) |
-
1969
- 1969-01-03 SE SE00080/69A patent/SE357965B/xx unknown
- 1969-01-07 GB GB1250992D patent/GB1250992A/en not_active Expired
- 1969-01-08 DE DE19691900711 patent/DE1900711A1/en active Pending
- 1969-01-08 NL NL6900306.A patent/NL157800B/en unknown
- 1969-01-09 DK DK11769AA patent/DK123478B/en unknown
- 1969-01-09 FR FR6900166A patent/FR2000089A1/fr not_active Withdrawn
- 1969-01-09 CA CA039,641A patent/CA948645A/en not_active Expired
- 1969-01-09 IL IL31390A patent/IL31390A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE357965B (en) | 1973-07-16 |
| NL157800B (en) | 1978-09-15 |
| DK123478B (en) | 1972-06-26 |
| GB1250992A (en) | 1971-10-27 |
| NL6900306A (en) | 1969-07-11 |
| IL31390A0 (en) | 1969-03-27 |
| FR2000089A1 (en) | 1969-08-29 |
| DE1900711A1 (en) | 1969-07-31 |
| CA948645A (en) | 1974-06-04 |
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