CS258291B1 - Hydrochlorides of (z)-2-alkoxyimino-2-(2/4-aminobenzenesulphonamido/-4-thiazolyl) acetalchlorides - Google Patents
Hydrochlorides of (z)-2-alkoxyimino-2-(2/4-aminobenzenesulphonamido/-4-thiazolyl) acetalchlorides Download PDFInfo
- Publication number
- CS258291B1 CS258291B1 CS871296A CS129687A CS258291B1 CS 258291 B1 CS258291 B1 CS 258291B1 CS 871296 A CS871296 A CS 871296A CS 129687 A CS129687 A CS 129687A CS 258291 B1 CS258291 B1 CS 258291B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- thiazolyl
- alkoxyimino
- aminobenzenesulfonamido
- hydrochlorides
- acetalchlorides
- Prior art date
Links
- 150000003840 hydrochlorides Chemical class 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003782 beta lactam antibiotic agent Substances 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 239000002132 β-lactam antibiotic Substances 0.000 abstract description 2
- 229940124586 β-lactam antibiotics Drugs 0.000 abstract description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 4
- -1 2- [2- (4-Aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-methoxyiminoacetyl chloride hydrochloride Chemical compound 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Landscapes
- Thiazole And Isothizaole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Řešení se týká hydrochloridů (Z)—2— -alkoxyimino-2-j2-(4-aminobenzensulfonamido)-4-thiazolyl] acetylchloridů obecného vzorce I, nových látek, použitelných jako meziprodukty při syntéze nové skupiny antibiotik beta-laktamového typu. Tyto nové látky jsou přístupné reakci (Z)-2- -alkoxyimino-2-f2-(4-aminobenzensulfonamido) -4-thiazolyl (octových kyselin s chloridem fosforečným.The solution relates to hydrochlorides (Z) —2— -alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl chlorides of formula I, new substances useful as intermediates in the synthesis of a novel group beta-lactam antibiotics. These new substances are accessible reaction (Z) -2- -alkoxyimino-2- [2- (4-aminobenzenesulfonamido)] -4-thiazolyl (acetic acid with chloride phosphorous.
Description
Vynález se týká hydrochloridů (Z)-2-alkoxyimino-2-[2-(4-aminobenzensulfonamido)-4-thiazolyl] acetylchloridů obecného vzorce IThe present invention relates to (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl chloride hydrochlorides of the formula I
kde R značí alkylskupinu s 1 až 2 atomy uhlíku. Tyto nové, dosud nepopsané látky jsou základními meziprodukty syntézy nové skupiny polosyntetických antibiotik beta-laktamového typu, jejichž struktura obsahuje (Z)-2-alkoxyimino-2-[2-(4-aminobenzensulfonamido)-4-thiazolyl] acetylskupinu.wherein R is C 1 -C 2 alkyl. These novel, yet undescribed substances are essential intermediates in the synthesis of a new class of semisynthetic beta-lactam antibiotics, the structure of which contains (Z) -2-alkoxyimino-2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetyl.
Látky obecného vzorce I podle vynálezu lze připravovat postupy známými z literatury, například reakcí kyselin (Z)-2-alkoxyimino- [2-(4-aminobenzensulfonamido)-4-thiazolyl]octových s chloridem fosforečným, případně za přítomnosti katalytického množství dimethylformamidu. Jako prostředí se používá s výhodou acetonitril, reakce probíhá při teplotě -40 až 60 °C, s výhodou při teplotě -40 až 0 °C.The compounds of the formula I according to the invention can be prepared by methods known from the literature, for example by reacting (Z) -2-alkoxyimino- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] acetic acids with phosphorus pentachloride, optionally in the presence of a catalytic amount of dimethylformamide. Acetonitrile is preferably used as the medium and the reaction is carried out at a temperature of -40 to 60 ° C, preferably at a temperature of -40 to 0 ° C.
Bližší podrobnosti způsobu přípravy látek podle vynálezu vyplývají z následujících příkladů provedení. Je samozřejmé, žé kromě uvedeného způsobu jsou možné k další alternativy vedoucí k žádaným látkám obecného vzorce I, jež jsou odborníkovi běžné a nemusí být proto výslovně jmenovány.Further details of the preparation of the compounds according to the invention are given in the following examples. It goes without saying that, in addition to the above process, other alternatives leading to the desired compounds of the formula I are possible, which are common to the person skilled in the art and do not have to be explicitly named.
Příklad 1Example 1
Hydrochlorid 2- [2-(4-aminobenzensulfonamido)-4-thiazolyl]-(Z)-2-methoxyiminoacetylchloridu2- [2- (4-Aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-methoxyiminoacetyl chloride hydrochloride
K suspenzi 2 g (0,006 mol) kyseliny 2-[2-(4-aminobenzensulfonamido)-4-thiazolyl]-(Z)-2-methoxyiminooctové v 10 ml bezvodého acetonitrilu se za míchání a chlazení na -25 °C přidá kapka dimethylformamidu a 2,2 g (0,01 mol) chloridu fosforečného. Roztok vzniklý po 15 min míchání bez chlazení se ochladí na -40 °C a vyloučený produkt se po 10 min odsaje a promyje bezvodým benzenem a hexanem. Po vysušení za vakua při 60 °C se získá 1,2 g (52 4) zažloutlého produktu, který se při zahřívání nad 190 °C rozkládá. Obsah chloru (argentometric ky) 104,2 4 vypočteného množství.To a suspension of 2 g (0.006 mol) of 2- [2- (4-aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-methoxyiminoacetic acid in 10 ml of anhydrous acetonitrile was added a drop of dimethylformamide with stirring and cooling to -25 ° C. and 2.2 g (0.01 mol) of phosphorus pentachloride. The solution formed after stirring for 15 minutes without cooling is cooled to -40 ° C and the precipitated product is filtered off with suction after 10 minutes and washed with anhydrous benzene and hexane. After drying under vacuum at 60 ° C, 1.2 g (52%) of a yellowish product are obtained which decomposes when heated above 190 ° C. Chlorine content (argentometric ky) 104.2 4 calculated amount.
Příklad 2Example 2
Hydrochlorid 2-[2-(4-aminobenzensulfonamido)-4-thiazolyl]-(Z)-2-ethoxyiminoacetylchloridu2- [2- (4-Aminobenzenesulfonamido) -4-thiazolyl] - (Z) -2-ethoxyiminoacetyl chloride hydrochloride
Postupem popsaným v příkladu 1 se s použitím ekvivalentního množství ethoxyderivátu s výtěžkem 34,9 % získá titulní sloučenina ve formě nažloutlého produktu, který se při zahřívání nad 180 °C rozkládá. Obsah chloru (argentometricky) 97,6 4 vypočteného množství.Following the procedure described in Example 1, using an equivalent amount of ethoxy derivative in 34.9% yield, the title compound is obtained as a yellowish product which decomposes when heated above 180 ° C. Chlorine content (argentometric) 97.6 4 of the calculated amount.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871296A CS258291B1 (en) | 1987-02-26 | 1987-02-26 | Hydrochlorides of (z)-2-alkoxyimino-2-(2/4-aminobenzenesulphonamido/-4-thiazolyl) acetalchlorides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS871296A CS258291B1 (en) | 1987-02-26 | 1987-02-26 | Hydrochlorides of (z)-2-alkoxyimino-2-(2/4-aminobenzenesulphonamido/-4-thiazolyl) acetalchlorides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS129687A1 CS129687A1 (en) | 1987-11-12 |
| CS258291B1 true CS258291B1 (en) | 1988-08-16 |
Family
ID=5346985
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS871296A CS258291B1 (en) | 1987-02-26 | 1987-02-26 | Hydrochlorides of (z)-2-alkoxyimino-2-(2/4-aminobenzenesulphonamido/-4-thiazolyl) acetalchlorides |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS258291B1 (en) |
-
1987
- 1987-02-26 CS CS871296A patent/CS258291B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS129687A1 (en) | 1987-11-12 |
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