DE1595876A1 - Verfahren zur Herstellung von Aminomethylderivaten von Rifamycin SV - Google Patents
Verfahren zur Herstellung von Aminomethylderivaten von Rifamycin SVInfo
- Publication number
- DE1595876A1 DE1595876A1 DE19651595876 DE1595876A DE1595876A1 DE 1595876 A1 DE1595876 A1 DE 1595876A1 DE 19651595876 DE19651595876 DE 19651595876 DE 1595876 A DE1595876 A DE 1595876A DE 1595876 A1 DE1595876 A1 DE 1595876A1
- Authority
- DE
- Germany
- Prior art keywords
- rifamycin
- solution
- lower alkyl
- ecm
- group
- 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.)
- Pending
Links
- 229940109171 rifamycin sv Drugs 0.000 title claims description 13
- 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 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- 230000008569 process Effects 0.000 title claims description 8
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 16
- 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 claims description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 10
- 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 claims description 9
- 235000010323 ascorbic acid Nutrition 0.000 claims description 8
- 239000011668 ascorbic acid Substances 0.000 claims description 8
- 229960005070 ascorbic acid Drugs 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002391 heterocyclic compounds Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- -1 alkyl radical Chemical class 0.000 claims 5
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 19
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound 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 description 15
- 229930189077 Rifamycin Natural products 0.000 description 8
- 229960003292 rifamycin Drugs 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 4
- 239000008098 formaldehyde solution Substances 0.000 description 4
- 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 4
- 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 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000008055 phosphate buffer solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- SDGKUVSVPIIUCF-UHFFFAOYSA-N 2,6-dimethylpiperidine Chemical compound CC1CCCC(C)N1 SDGKUVSVPIIUCF-UHFFFAOYSA-N 0.000 description 1
- MLCFJDJPAIZRMR-WQDCEMHHSA-N 3-dimethylaminomethyl rifamycin sv Chemical compound OC1=C(C(O)=C2C)C3=C(O)C(CN(C)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 MLCFJDJPAIZRMR-WQDCEMHHSA-N 0.000 description 1
- CRQRORLRKWVTQE-DTGFBXAHSA-N 3-pyrrolidino-methyl rifamycin sv 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)NC=2C(O)=C3C(O)=C4C)C)OC)C4=C1C3=C(O)C=2CN1CCCC1 CRQRORLRKWVTQE-DTGFBXAHSA-N 0.000 description 1
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- RICLFGYGYQXUFH-UHFFFAOYSA-N buspirone hydrochloride Chemical compound [H+].[Cl-].C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 RICLFGYGYQXUFH-UHFFFAOYSA-N 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 230000001609 comparable effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- SRJOCJYGOFTFLH-UHFFFAOYSA-N isonipecotic acid Chemical compound OC(=O)C1CCNCC1 SRJOCJYGOFTFLH-UHFFFAOYSA-N 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000002244 precipitate Substances 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/08—Bridged systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13653/64A GB1090115A (en) | 1964-04-02 | 1964-04-02 | Mannich bases of rifamycin sv |
| GB4418064 | 1964-10-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1595876A1 true DE1595876A1 (de) | 1970-03-26 |
Family
ID=26249901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19651595876 Pending DE1595876A1 (de) | 1964-04-02 | 1965-03-25 | Verfahren zur Herstellung von Aminomethylderivaten von Rifamycin SV |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3349082A (en:Method) |
| AT (1) | AT259136B (en:Method) |
| BE (1) | BE661982A (en:Method) |
| BR (1) | BR6568430D0 (en:Method) |
| CH (1) | CH476010A (en:Method) |
| DE (1) | DE1595876A1 (en:Method) |
| DK (1) | DK115992B (en:Method) |
| ES (1) | ES311202A1 (en:Method) |
| FI (1) | FI44399B (en:Method) |
| GB (1) | GB1090115A (en:Method) |
| IL (1) | IL23157A (en:Method) |
| NL (1) | NL6504053A (en:Method) |
| SE (2) | SE313309B (en:Method) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1165179A (en) * | 1966-10-25 | 1969-09-24 | Lepetit Spa | Derivatives of Rifamycin SV |
| CH536851A (de) * | 1966-10-25 | 1973-05-15 | Ciba Geigy Ag | Verfahren zur Herstellung neuer antibiotisch wirksamer Verbindungen der Rifamycinreihen |
| GB1159267A (en) * | 1966-11-03 | 1969-07-23 | Lepetit Spa | Rifamycin Derivatives |
| GB1172155A (en) * | 1967-03-01 | 1969-11-26 | Lepetit Spa | New Rifamycins |
| CH484898A (de) * | 1967-05-29 | 1970-01-31 | Ciba Geigy | Verfahren zur Herstellung von 3-Formylrifamycin SV |
| NL145554B (nl) * | 1967-06-07 | 1975-04-15 | Lepetit Spa | Werkwijze voor het bereiden van een 3-formylrifamycine sv-derivaat |
| FR2059967A1 (en:Method) * | 1969-08-06 | 1971-06-11 | Lepetit Spa | |
| AR207762A1 (es) * | 1973-07-25 | 1976-10-29 | Archifar Ind Chim Trentino | Procedimiento para la preparacion de 3-((4-metil-1-piperazin-1-il)-imino)-metil-rifamicina sv o rifampicina |
| IT1090771B (it) * | 1977-12-20 | 1985-06-26 | Alfa Farmaceutici Spa | Derivati delle 3 carbossirifamicines ed sv e procedimento per la loro preparazione |
| IT1090772B (it) * | 1977-12-20 | 1985-06-26 | Alfa Farmaceutici Spa | Derivati della rifamicina e procedimento per la loro preparazione |
| EP2136626A4 (en) * | 2007-03-19 | 2011-02-23 | Oregon State | Mannich base n-oxide drugs |
| US20100152267A1 (en) * | 2008-12-11 | 2010-06-17 | Macielag Mark J | Novel rifamycin 3,4-(3-substituted aminomethyl) fused pyrrolo derivatives |
-
1964
- 1964-04-02 GB GB13653/64A patent/GB1090115A/en not_active Expired
-
1965
- 1965-03-15 IL IL6523157A patent/IL23157A/xx unknown
- 1965-03-23 US US442166A patent/US3349082A/en not_active Expired - Lifetime
- 1965-03-24 FI FI0715/65A patent/FI44399B/fi active
- 1965-03-25 DE DE19651595876 patent/DE1595876A1/de active Pending
- 1965-03-26 DK DK156965AA patent/DK115992B/da unknown
- 1965-03-29 AT AT283565A patent/AT259136B/de active
- 1965-03-30 ES ES0311202A patent/ES311202A1/es not_active Expired
- 1965-03-31 BR BR168430/65A patent/BR6568430D0/pt unknown
- 1965-03-31 NL NL6504053A patent/NL6504053A/xx unknown
- 1965-04-01 SE SE8164/67A patent/SE313309B/xx unknown
- 1965-04-01 SE SE4216/65A patent/SE316479B/xx unknown
- 1965-04-01 CH CH456365A patent/CH476010A/de not_active IP Right Cessation
- 1965-04-02 BE BE661982D patent/BE661982A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE661982A (en:Method) | 1965-08-02 |
| US3349082A (en) | 1967-10-24 |
| IL23157A (en) | 1969-01-29 |
| GB1090115A (en) | 1967-11-08 |
| DK115992B (da) | 1969-12-01 |
| ES311202A1 (es) | 1965-07-01 |
| FI44399B (en:Method) | 1971-08-02 |
| SE316479B (en:Method) | 1969-10-27 |
| BR6568430D0 (pt) | 1973-08-07 |
| NL6504053A (en:Method) | 1965-10-04 |
| AT259136B (de) | 1967-12-27 |
| SE313309B (en:Method) | 1969-08-11 |
| CH476010A (de) | 1969-07-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| E77 | Valid patent as to the heymanns-index 1977 |