CH508621A - Verfahren zur Herstellung neuer Rifamycin-Derivate - Google Patents

Verfahren zur Herstellung neuer Rifamycin-Derivate

Info

Publication number: CH508621A
Authority: CH; Switzerland
Prior art keywords: rifamycin; dependent; deacetyl; quinone; product obtained
Prior art date: 1967-11-24

Application number

CH1652967A

Other languages

German (de)

English (en)

Inventor

Hans Dr Bickel

Wilhelm Dr Kump

Original Assignee

Ciba Geigy Ag

Lepetit Spa

Priority date (The priority date 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 date listed.)

1967-11-24

Filing date

1967-11-24

Publication date

1971-06-15

1967-11-24 Application filed by Ciba Geigy Ag, Lepetit Spa filed Critical Ciba Geigy Ag

1967-11-24 Priority to CH1652967A priority Critical patent/CH508621A/de

1968-11-08 Priority to SE15177/68A priority patent/SE352893B/xx

1968-11-15 Priority to JP43083329A priority patent/JPS4843760B1/ja

1968-11-21 Priority to FR1593300D priority patent/FR1593300A/fr

1968-11-22 Priority to BR204233/68A priority patent/BR6804233D0/pt

1968-11-22 Priority to NL6816746A priority patent/NL6816746A/xx

1968-11-22 Priority to AT581470A priority patent/AT297222B/de

1968-11-22 Priority to AT1137868A priority patent/AT292919B/de

1968-11-23 Priority to ES360632A priority patent/ES360632A1/es

1968-11-25 Priority to CS2176*[A priority patent/CS159753B2/cs

1968-11-25 Priority to CS8019A priority patent/CS159752B2/cs

1971-06-15 Publication of CH508621A publication Critical patent/CH508621A/de

1972-10-13 Priority to JP47101941A priority patent/JPS5025480B1/ja

Links

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 title description 3
230000000844 anti-bacterial effect Effects 0.000 title description 2
229930189077 Rifamycin Natural products 0.000 title 1
229960003292 rifamycin Drugs 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims description 26
150000001875 compounds Chemical class 0.000 claims description 15
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 12
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 10
238000006243 chemical reaction Methods 0.000 claims description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 5
229940109171 rifamycin sv Drugs 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
125000001931 aliphatic group Chemical group 0.000 claims description 3
229910021529 ammonia Inorganic materials 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
150000003335 secondary amines Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 8
125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 claims 2
125000004151 quinonyl group Chemical group 0.000 claims 2
239000003638 chemical reducing agent Substances 0.000 claims 1
238000009833 condensation Methods 0.000 claims 1
230000005494 condensation Effects 0.000 claims 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
238000000746 purification Methods 0.000 claims 1
239000000645 desinfectant Substances 0.000 abstract description 2
239000003755 preservative agent Substances 0.000 abstract description 2
230000000941 anti-staphylcoccal effect Effects 0.000 abstract 1
230000002365 anti-tubercular Effects 0.000 abstract 1
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
239000000243 solution Substances 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
-1 aliphatic amines Chemical class 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 7
239000002253 acid Substances 0.000 description 7
239000002585 base Substances 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
239000000126 substance Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
150000004053 quinones Chemical class 0.000 description 4
150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
229960005070 ascorbic acid Drugs 0.000 description 3
235000010323 ascorbic acid Nutrition 0.000 description 3
239000011668 ascorbic acid Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 2
238000001035 drying Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
150000003460 sulfonic acids Chemical class 0.000 description 2
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
FZKCAHQKNJXICB-UHFFFAOYSA-N 2,1-benzoxazole Chemical compound C1=CC=CC2=CON=C21 FZKCAHQKNJXICB-UHFFFAOYSA-N 0.000 description 1
AFMGWVYWAYHNEH-DRPSXBIXSA-N 25-o-deacetyl-rifamycin Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C\C=C\C(C)C(O)C(C)C(O)C(C)C(O)C(C)C(OC)\C=C\OC1(C)OC2=C3C1=O AFMGWVYWAYHNEH-DRPSXBIXSA-N 0.000 description 1
CJYAFHWRWQLMEB-XOSXFVNUSA-N 3-morpholinorifamycin sv Chemical compound CC1=C(O)C2=C(O)C=3NC(=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\OC(C4=O)(C)OC1=C4C2=C(O)C=3N1CCOCC1 CJYAFHWRWQLMEB-XOSXFVNUSA-N 0.000 description 1
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
241000304886 Bacilli Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
244000248349 Citrus limon Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
239000004264 Petrolatum Substances 0.000 description 1
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 1
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 1
241000295644 Staphylococcaceae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
150000003938 benzyl alcohols Chemical class 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000012876 carrier material Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
230000006196 deacetylation Effects 0.000 description 1
238000003381 deacetylation reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000012530 fluid Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
150000003139 primary aliphatic amines Chemical class 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
150000003242 quaternary ammonium salts Chemical class 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
150000005619 secondary aliphatic amines Chemical class 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 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
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Fodder In General (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH1652967A 1967-11-24 1967-11-24 Verfahren zur Herstellung neuer Rifamycin-Derivate CH508621A (de)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CH1652967A CH508621A (de)	1967-11-24	1967-11-24	Verfahren zur Herstellung neuer Rifamycin-Derivate
SE15177/68A SE352893B (cs)	1967-11-24	1968-11-08
JP43083329A JPS4843760B1 (cs)	1967-11-24	1968-11-15
FR1593300D FR1593300A (cs)	1967-11-24	1968-11-21
NL6816746A NL6816746A (cs)	1967-11-24	1968-11-22
BR204233/68A BR6804233D0 (pt)	1967-11-24	1968-11-22	Processo para a fabricacao de novos derivados de rifamicina
AT581470A AT297222B (de)	1967-11-24	1968-11-22	Verfahren zur Herstellung neuer Rifamycin-Derivate
AT1137868A AT292919B (de)	1967-11-24	1968-11-22	Verfahren zur Herstellung neuer Rifamycin-Derivaten
ES360632A ES360632A1 (es)	1967-11-24	1968-11-23	Procedimiento para la obtencion de derivados de rifamicina.
CS2176*[A CS159753B2 (cs)	1967-11-24	1968-11-25
CS8019A CS159752B2 (cs)	1967-11-24	1968-11-25
JP47101941A JPS5025480B1 (cs)	1967-11-24	1972-10-13

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1652967A CH508621A (de)	1967-11-24	1967-11-24	Verfahren zur Herstellung neuer Rifamycin-Derivate

Publications (1)

Publication Number	Publication Date
CH508621A true CH508621A (de)	1971-06-15

Family

ID=4418148

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1652967A CH508621A (de)	1967-11-24	1967-11-24	Verfahren zur Herstellung neuer Rifamycin-Derivate

Country Status (9)

Country	Link
JP (2)	JPS4843760B1 (cs)
AT (2)	AT297222B (cs)
BR (1)	BR6804233D0 (cs)
CH (1)	CH508621A (cs)
CS (2)	CS159752B2 (cs)
ES (1)	ES360632A1 (cs)
FR (1)	FR1593300A (cs)
NL (1)	NL6816746A (cs)
SE (1)	SE352893B (cs)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5271758U (cs) *	1975-11-21	1977-05-28

1967
- 1967-11-24 CH CH1652967A patent/CH508621A/de not_active IP Right Cessation
1968
- 1968-11-08 SE SE15177/68A patent/SE352893B/xx unknown
- 1968-11-15 JP JP43083329A patent/JPS4843760B1/ja active Pending
- 1968-11-21 FR FR1593300D patent/FR1593300A/fr not_active Expired
- 1968-11-22 AT AT581470A patent/AT297222B/de not_active IP Right Cessation
- 1968-11-22 AT AT1137868A patent/AT292919B/de not_active IP Right Cessation
- 1968-11-22 BR BR204233/68A patent/BR6804233D0/pt unknown
- 1968-11-22 NL NL6816746A patent/NL6816746A/xx unknown
- 1968-11-23 ES ES360632A patent/ES360632A1/es not_active Expired
- 1968-11-25 CS CS8019A patent/CS159752B2/cs unknown
- 1968-11-25 CS CS2176*[A patent/CS159753B2/cs unknown
1972
- 1972-10-13 JP JP47101941A patent/JPS5025480B1/ja active Pending

Also Published As

Publication number	Publication date
FR1593300A (cs)	1970-05-25
CS159753B2 (cs)	1975-01-31
ES360632A1 (es)	1970-07-16
BR6804233D0 (pt)	1973-02-22
SE352893B (cs)	1973-01-15
CS159752B2 (cs)	1975-01-31
NL6816746A (cs)	1969-05-28
JPS4843760B1 (cs)	1973-12-20
AT297222B (de)	1972-03-10
JPS5025480B1 (cs)	1975-08-23
AT292919B (de)	1971-09-10

Legal Events

Date	Code	Title	Description
1976-06-30	PL	Patent ceased

Publication	Publication Date	Title
DE1518002C3 (de)	1975-01-23	Isoflavane und Isoflavene und Verfahren zu Ihrer Herstellung sowie diese enthaltende Arzneimittel
CH504457A (de)	1971-03-15	Verfahren zur Herstellung neuer antibiotisch wirksamer Kondensationsprodukte von Rifamycin S
DE2504045C3 (de)	1978-06-01	16,17 Dihydro-apovincaminsäure-2hydroxypropylester, deren Salze, Verfahren zu ihrer Herstellung und Arzneimittel
CH508621A (de)	1971-06-15	Verfahren zur Herstellung neuer Rifamycin-Derivate
DE1670377C3 (de)	1974-02-28	Verfahren zur Herstellung von Rifamycinderivaten
DE1470285A1 (de)	1970-07-02	Verfahren zur Herstellung des neuen 1-Methyl-N-carbobenzoxy-dihydro-lysergamins
DE1670479A1 (de)	1971-01-28	Verfahren zur Herstellung neuer antibiotisch wirksamer Verbindungen
DE2424540A1 (de)	1974-12-12	Ergolincarbamate
DE2444728A1 (de)	1975-04-10	Verfahren zur herstellung neuer antibiotisch wirksamer verbindungen
CH553211A (de)	1974-08-30	Verfahren zur herstellung neuer rifamycin-derivate.
CH526527A (de)	1972-08-15	Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons
CH594677A5 (en)	1978-01-13	3-(4-Substd.-1-piperazinyl) rifamycin S and SV derivs
CH605974A5 (en)	1978-10-13	3-(4-Substd.-1-piperazinyl) rifamycin S and SV derivs
CH594676A5 (en)	1978-01-13	3-(4-Substd.-1-piperazinyl) rifamycin S and SV derivs
CH550193A (de)	1974-06-14	Verfahren zur herstellung neuer rifamycin-derivate.
DE2047146A1 (de)	1971-04-01	4 Acylamino 1,2,4 tnazol Derivate und Verfahren zu ihrer Herstellung
DE1445626A1 (de)	1968-12-19	Verfahren zur Gewinnung von Alkaloiden
KR790001367B1 (ko)	1979-09-28	리파마이신 s 및 sv 유도체의 제조방법
DE1173093B (de)	1964-07-02	Verfahren zur Herstellung von 3ª-Amino-11-keto-20, 20-bis-hydroxymethyl-5ª-pregnanbzw. von Salzen desselben
CH622797A5 (en)	1981-04-30	Process for the preparation of antibiotically active rifamycin S and SV derivatives
DE1468554B1 (de)	1971-07-15	20beta-tert.-Amino-3alpha-hydroxy-(bzw.-acyloxy)-5beta-pregnane bzw. deren Salze sowie Verfahren zu ihrer Herstellung
DE2004743A1 (de)	1970-09-03	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DE1145175B (de)	1963-03-14	Verfahren zur Gewinnung von Rescidin aus Pflanzen der Rauwolfiaarten und zur Herstellung von dessen Salzen
CH483423A (de)	1969-12-31	Verfahren zur Herstellung einer neuen Indolverbindung
DE2010010A1 (en)	1971-09-23	Bactericidal 6-aminopenicillanic acid deriva - fatty acids.