DE1795736C3 - Rifamycin SV derivatives and processes for their preparation - Google Patents
Rifamycin SV derivatives and processes for their preparationInfo
- Publication number
- DE1795736C3 DE1795736C3 DE19651795736 DE1795736A DE1795736C3 DE 1795736 C3 DE1795736 C3 DE 1795736C3 DE 19651795736 DE19651795736 DE 19651795736 DE 1795736 A DE1795736 A DE 1795736A DE 1795736 C3 DE1795736 C3 DE 1795736C3
- Authority
- DE
- Germany
- Prior art keywords
- rifamycin
- preparation
- derivatives
- processes
- formylrifamycin
- 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
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical class OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 description 7
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 description 6
- 229940109171 rifamycin sv Drugs 0.000 description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 4
- BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- BBNQHOMJRFAQBN-UPZFVJMDSA-N 3-formylrifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(C=O)=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BBNQHOMJRFAQBN-UPZFVJMDSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229930189077 Rifamycin Natural products 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- -1 2-morpholinoethyl group Chemical group 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960003292 rifamycin Drugs 0.000 description 2
- 241001468213 Amycolatopsis mediterranei Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- RAFHKEAPVIWLJC-OQQFTUDCSA-N Rifamycin O Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC5(OCC(=O)O5)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C RAFHKEAPVIWLJC-OQQFTUDCSA-N 0.000 description 1
- MTDHGAMVNZGOBI-WYGSVCPZSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21E)-2,15,17,27,29-pentahydroxy-26-[(E)-hydroxyiminomethyl]-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23-dioxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(29),2,4,9,19,21,25,27-octaen-13-yl] acetate Chemical compound CO[C@H]1\C=C\O[C@@]2(C)Oc3c(C2=O)c2c(O)c(\C=N\O)c(NC(=O)\C(C)=C\C=C\[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@@H]1C)c(O)c2c(O)c3C MTDHGAMVNZGOBI-WYGSVCPZSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002365 anti-tubercular Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SQTCRTQCPJICLD-KTQDUKAHSA-N rifamycin B Chemical compound OC1=C(C(O)=C2C)C3=C(OCC(O)=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O SQTCRTQCPJICLD-KTQDUKAHSA-N 0.000 description 1
- BTVYFIMKUHNOBZ-QXMMDKDBSA-N rifamycin s Chemical class O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-QXMMDKDBSA-N 0.000 description 1
- 229940081192 rifamycins Drugs 0.000 description 1
- SQTCRTQCPJICLD-OQQFTUDCSA-N rifomycin-B Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(OCC(=O)O)c4c3C2=O SQTCRTQCPJICLD-OQQFTUDCSA-N 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001429 visible spectrum Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- RAFHKEAPVIWLJC-TWYIRNIGSA-N z67lem9p1w Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)N2)C)OC)C(C(=C3O)C)=C1C1=C3C(=O)C2=C[C@]11OCC(=O)O1 RAFHKEAPVIWLJC-TWYIRNIGSA-N 0.000 description 1
Description
C22H36O5 C 22 H 36 O 5
-CO-CO
(D(D
1515th
CH = NORCH = NOR
in der R Wasserstoff, die Methyl- oder die 2-Morpholinoäthylgruppe darstellt.in which R represents hydrogen, the methyl or the 2-morpholinoethyl group.
2. Verfahren zur Herstellung der Verbindungen nach Anspruch 1, dadurch gekennzeichnet, daß
man 3-Formylrifamycin-SV der Formel Il
C22H311O5 CO2. Process for the preparation of the compounds according to claim 1, characterized in that 3-formylrifamycin SV of the formula II
C 22 H 311 O 5 CO
NHNH
CH = OCH = O
nach an sich bekannten Methoden mit einer Verbindung der allgemeinen Formel IIIby methods known per se with a compound of the general formula III
H2NOR (III)H 2 NOR (III)
umsetzt, in der R die oben angegebene Bedeutung hat.converts, in which R has the meaning given above.
3. Therapeutische Zubereitung, bestehend aus einer oder mehreren Verbindungen nach Anspruch 1 und üblichen Hilfs- und/oder Trägerstoffen. 3. Therapeutic preparation consisting of one or more compounds according to claim 1 and customary auxiliaries and / or carriers.
Gegenstand der Erfindung sind
Derivate der allgemeinen Formel IThe subject of the invention are
Derivatives of the general formula I
Rifamycin-SV- 30 dung der allgemeinen Formel IIIRifamycin-SV- 30 preparation of the general formula III
H1NORH 1 NOR
C22H36O5 C 22 H 36 O 5
COCO
(D(D
CH = NORCH = NOR
in der R Wasserstoff, die Methyl- oder die 2-Morpholino-äthylgruppe darstellt.in which R is hydrogen, the methyl or the 2-morpholino-ethyl group represents.
Die Erfindung betrifft auch ein Verfahren zur Herstellung dieser neuen Antibiotika, das darin besteht, daß man 3-Formylrifamycin-SV der Formel IIThe invention also relates to a process for the preparation of these new antibiotics, which consists in that 3-formylrifamycin-SV of the formula II
C22H36O5 COC 22 H 36 O 5 CO
NHNH
CH = OCH = O
(II)(II)
nach an sich bekannten Methoden mit einer Verbinumsetzt, in der R die oben angegebene Bedeutung hat. In der deutschen Patentschrift 10 89 513 ist diereacted by methods known per se with a compound in which R has the meaning given above. In the German patent 10 89 513 is the
Herstellung des Antibiotikums Rifamycin durch Züchtung von Streptomyces mediterranei ATCC 13 685 beschrieben. In diesem Patent ist auch angegeben, daß Rifamycin aus einem Gemisch antibiotisch wirksamer Substanzen besteht. Eine dieser Substanzen, Rifa-Production of the antibiotic rifamycin by cultivating Streptomyces mediterranei ATCC 13 685 described. This patent also states that rifamycin is more antibiotically effective from a mixture Substances. One of these substances, Rifa-
mycin-B mit der Summenformel C39H49NO14, stellt eine zweibasische Säure (pH l'/2 = 2,8; pH 2'/2 = 6,7) dar, wobei eine der Säuregruppen eine Carboxylgruppe ist. Eine der besonderen Eigenschaften dieses Antibiotikums besteht darin, daß seine Wirksamkeitmycin-B with the empirical formula C 39 H 49 NO 14 , represents a dibasic acid (pH 1 '/ 2 = 2.8; pH 2' / 2 = 6.7), one of the acid groups being a carboxyl group. One of the special properties of this antibiotic is that its effectiveness
zunimmt, wenn es in Wasser gelöst wird, d. h., es wandelt sich in eine andere Substanz mit höherer antibakterieller Wirksamkeit um. Das aktivere, als Rifamycin-S bezeichnete Produkt hat die Summenformel C37H45NO12. Es kann durch milde Reduktion in einincreases when it is dissolved in water, that is, it turns into another substance with higher antibacterial effectiveness. The more active product, known as rifamycin-S, has the empirical formula C 37 H 45 NO 12 . It can be turned into one by mild reduction
weiteres Antibiotikum der Rifamycinklasse, das Rifamycin-SV (C37H47NO12), umgewandelt werden. Das Verfahren zur Herstellung von Rifamycin-SV besteht in der Oxydation von Rifamycin-B zu Rifamycin-O, der Hydrolyse von Rifamycin-0 unter AbspaltungAnother antibiotic of the rifamycin class, the rifamycin-SV (C 37 H 47 NO 12 ), can be converted. The process for the production of rifamycin-SV consists in the oxidation of rifamycin-B to rifamycin-O, the hydrolysis of rifamycin-0 with cleavage
von Glykolsäure zu Rifamycin-S und der Reduktion von Rifamycin-S zu Rifamycin-SV. Sowohl Rifamycin-S als auch Rifamycin-SV weisen keine Carboxylgruppe auf. Sie wird während der Aktivierungsstufe in Form von Glykolsäure abgespalten.from glycolic acid to rifamycin-S and the reduction of rifamycin-S to rifamycin-SV. Both rifamycin-S as well as rifamycin-SV do not have a carboxyl group. It will be used during the activation stage split off in the form of glycolic acid.
Die Struktur der Rifamycine ist in Experientia. Bd. 20 (1964), S. 336,veröffentlicht.The structure of the rifamycins is in experientia. Vol. 20 (1964), p. 336.
Die neuen Derivate des Rifamycins-SV zeichnen sich durch eine ausgeprägte antibakterielle Wirkung in vitro aus, wie aus der nachfolgenden Tabelle 1 hervor-The new derivatives of Rifamycins-SV are characterized by a pronounced antibacterial effect in in vitro, as shown in Table 1 below.
geht, in der die kleinsten Hemmkonzentrationen gegenüber pathogenen Mikroorganismen in ;Vccm angegeben sind. R hat dabei die oben angegebene Bedeutung. in which the smallest inhibitory concentrations against pathogenic microorganisms are given in; Vccm are. R has the meaning given above.
Verbin dung Nr.Connect manure No.
M. aureusM. aureus
S.S.
pyog.pyog.
S.S.
face.face.
B.B.
subt.subt.
Pro- Eicoli Kleb, teus pneuPro-Eicoli adhesive, teus pneu
Pseudom. H37R aereataPseudom. H 37 R aereata
—H
-CH3 -H
-CH 3
0,02 0,01 0,0005 0,010.02 0.01 0.0005 0.01
0,1 0,10.1 0.1
0,005 0,010.005 0.01
-CH2CH2-N O 0,005 0,02 0,05 0,2-CH 2 CH 2 -NO 0.005 0.02 0.05 0.2
10 5
2 510 5
2 5
10 510 5
20
1020th
10
10
1010
10
2020th
5
0,055
0.05
0,50.5
Die ausgezeichnete antibiotische Wirksamkeit der in vitro untersuchten Verbindungen wurde durch In-vivo-Versuche an mit Staphylococcus aureus infkierten Mäusen bestätigt, wobei diese Versuche gemäß dem von Arioli et ai. in Arzneimittel-Forschung Bd. 17, 1967, S. 523, beschriebenen Verfahren durchgeführt wurden. Diese Versuche zeigen, daß die erfindungsgemäßen Verbindungen dem Rifamycin-SV überlegen sind und nur geringe Toxizität besitzen.The excellent antibiotic activity of the compounds examined in vitro was confirmed by in vivo tests on mice infected with Staphylococcus aureus, these experiments according to the method of Arioli et ai. in Arzneimittel -forschung Vol. 17, 1967, p. 523, methods described were carried out. These experiments show that the compounds according to the invention are superior to rifamycin-SV and only have low toxicity.
XI1.connection
XI 1 .
O
y Λ
O
y
Die erfindungsgemäßen Verbindungen haben auch antituberkulöse Wirkung, wie bei Versuchen, die gemäß dem von P a 11 a η g a et al. in Arzneimittel-Forschung, Bd. 17, 1967, S. 529, beschriebenen Verfahren durchgeführt wurden, festgestellt wurde.The compounds according to the invention also have an antitubercular effect, as in experiments according to that of P a 11 a η g a et al. in drug research, Vol. 17, 1967, p. 529, was carried out.
Das folgende Beispiel erläutert das erfindungsgemäße Verfahren.The following example explains the method according to the invention.
45 Beispiel 45 example
3-Formylrifamycin-SV-oxim3-formylrifamycin SV oxime
Ein Gemisch aus 7,3 g 3-Formylrifamycin-SV, 200 ecm Tetrahydrofuran, 27 ecm Pyridin und 0,75 g Hydroxylaminhydrochlorid wird 3 Stunden bei Raumtemperatur gerührt. Dann wird es in etwa 21 Eiswasser gegossen, mit Salzsäure angesäuert und mit Äthylacetat extrahiert. Der organische Extrakt wird auf etwa 50 ecm eingeengt und gekühlt. Die ausgefallenen orangefarbenen Kristalle werden gesammelt und getrocknet. A mixture of 7.3 g of 3-formylrifamycin SV, 200 ecm of tetrahydrofuran, 27 ecm of pyridine and 0.75 g of hydroxylamine hydrochloride are used for 3 hours at room temperature touched. Then it is poured into about 21 ice water, acidified with hydrochloric acid and with ethyl acetate extracted. The organic extract is concentrated to about 50 ecm and cooled. The unusual orange crystals are collected and dried.
Ausbeute 5,7g (76%); F. = 190 bis 1930C. Das UV- und das sichtbare Spektrum zeigen Maxima bei 323ΐημ(Ε!* = 273,9) und 468 πΐμ (E1,* = 179,4).Yield 5.7g (76%); F. = 190 to 193 0 C. The UV and the visible spectrum show maxima at 323ΐημ (Ε! * = 273.9) and 468 πΐμ (E 1 , * = 179.4).
In gleicher Weise wurde das O-Methyloxim erhalten; Fp. = 240bis250°C(Zers.);AmnJt = 325(EJl = 298); 470(Ej* = 198); ferner das O-[2-Morpholinoäthyl]-oxim; Fp. = 157 bis 162° C (Zers.); ληαχ = 325 (EJ* = 253,2); 465 bis 470 (EJ *m = 164,3).The O-methyl oxime was obtained in the same way; Mp = 240-250 ° C (dec.); A mnJt = 325 (EJl = 298); 470 (Ej * = 198); also the O- [2-morpholinoethyl] oxime; M.p. = 157-162 ° C (dec.); λ ηαχ = 325 (EJ * = 253.2); 465 to 470 (EJ * m = 164.3).
Claims (1)
1. Rifamycin-SV-Derivate der allgemeinenPatent claims:
1. Rifamycin SV derivatives of the general
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3032764 | 1964-07-31 | ||
| GB30327/64A GB1109631A (en) | 1964-07-31 | 1964-07-31 | Derivatives of rifamycin sv |
| DE1795567A DE1795567C3 (en) | 1964-07-31 | 1965-07-28 | Rifamycin SV derivatives and processes for their preparation |
| FR63914A FR5518M (en) | 1964-07-31 | 1966-06-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1795736A1 DE1795736A1 (en) | 1974-05-30 |
| DE1795736B2 DE1795736B2 (en) | 1976-04-01 |
| DE1795736C3 true DE1795736C3 (en) | 1976-11-25 |
Family
ID=
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