DK170100B1 - 2'-Substituerede 4-deoxytiazolo(5,4-c)rifamycin SV-derivater, fremgangsmåde til fremstilling heraf, en sådan forbindelse til anvendelse som lægemiddel, anvendelse af forbindelsen til fremstilling af et antibakterielt medikament samt farmaceutisk præparat indeholdende forbindelsen - Google Patents

2'-Substituerede 4-deoxytiazolo(5,4-c)rifamycin SV-derivater, fremgangsmåde til fremstilling heraf, en sådan forbindelse til anvendelse som lægemiddel, anvendelse af forbindelsen til fremstilling af et antibakterielt medikament samt farmaceutisk præparat indeholdende forbindelsen Download PDF

Info

Publication number: DK170100B1
Authority: DK; Denmark
Prior art keywords: compound; rifamycin; alkyl; group; optionally substituted
Prior art date: 1985-12-30

Application number

DK630686A

Other languages

Danish (da)

English (en)

Other versions

DK630686D0 (da

DK630686A (da

Inventor

Bruno Cavalleri

Marco Turconi

Giovanni Tamborini

Original Assignee

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.)

1985-12-30

Filing date

1986-12-29

Publication date

1995-05-22

1986-12-29 Application filed by Lepetit Spa filed Critical Lepetit Spa

1986-12-29 Publication of DK630686D0 publication Critical patent/DK630686D0/da

1987-07-01 Publication of DK630686A publication Critical patent/DK630686A/da

1995-05-22 Application granted granted Critical

1995-05-22 Publication of DK170100B1 publication Critical patent/DK170100B1/da

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 48
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 abstract description 9
238000000034 method Methods 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 6
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
239000003814 drug Substances 0.000 title claims 3
229940124350 antibacterial drug Drugs 0.000 title 1
229940079593 drug Drugs 0.000 title 1
230000000844 anti-bacterial effect Effects 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 10
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 8
125000004193 piperazinyl group Chemical group 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
239000003960 organic solvent Substances 0.000 claims description 5
239000002253 acid Substances 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
150000004885 piperazines Chemical class 0.000 claims description 3
239000003495 polar organic solvent Substances 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
125000002393 azetidinyl group Chemical group 0.000 claims description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims description 2
125000000623 heterocyclic group Chemical group 0.000 claims description 2
125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
125000001984 thiazolidinyl group Chemical group 0.000 claims description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
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 abstract description 5
229940109171 rifamycin sv Drugs 0.000 abstract description 5
238000007385 chemical modification Methods 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
235000019439 ethyl acetate Nutrition 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
XTPGUQSTSWYULT-ZDHWWVNNSA-N Rifamycin P 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)c5scnc5c4c3C2=O XTPGUQSTSWYULT-ZDHWWVNNSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
XTPGUQSTSWYULT-TXXBDZDDSA-N rifamycin p Chemical compound OC1=C(C(O)=C2C)C3=C4N=CSC4=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 XTPGUQSTSWYULT-TXXBDZDDSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 8
239000000047 product Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000003480 eluent Substances 0.000 description 5
239000005457 ice water Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001465754 Metazoa Species 0.000 description 4
-1 aethoxy Chemical group 0.000 description 4
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000012746 preparative thin layer chromatography Methods 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
239000003245 coal Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
235000014347 soups Nutrition 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
JJGDTQXMNCNHNY-RIFCHZFTSA-N 25-desacetylrifamycin p Chemical compound OC1=C(C(O)=C2C)C3=C4N=CSC4=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O JJGDTQXMNCNHNY-RIFCHZFTSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
241000187479 Mycobacterium tuberculosis Species 0.000 description 2
206010040047 Sepsis Diseases 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000001311 chemical methods and process Methods 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
238000011534 incubation Methods 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
208000013223 septicemia Diseases 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
FANCTJAFZSYTIS-IQUVVAJASA-N (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-7a-methyl-1-[(2r)-4-(phenylsulfonimidoyl)butan-2-yl]-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CCCC(/[C@@H]2CC1)=C\C=C\1C([C@@H](O)C[C@H](O)C/1)=C)C)CS(=N)(=O)C1=CC=CC=C1 FANCTJAFZSYTIS-IQUVVAJASA-N 0.000 description 1
ABFQGXBZQWZNKI-UHFFFAOYSA-N 1,1-dimethoxyethanol Chemical compound COC(C)(O)OC ABFQGXBZQWZNKI-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
244000026610 Cynodon dactylon var. affinis Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
241000187654 Nocardia Species 0.000 description 1
241000218657 Picea Species 0.000 description 1
241000295644 Staphylococcaceae Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
CTOUWUYDDUSBQE-UHFFFAOYSA-N benzyl piperazine-1-carboxylate Chemical group C1CNCCN1C(=O)OCC1=CC=CC=C1 CTOUWUYDDUSBQE-UHFFFAOYSA-N 0.000 description 1
238000004166 bioassay Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
OSVHLUXLWQLPIY-KBAYOESNSA-N butyl 2-[(6aR,9R,10aR)-1-hydroxy-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-3-yl]-2-methylpropanoate Chemical compound C(CCC)OC(C(C)(C)C1=CC(=C2[C@H]3[C@H](C(OC2=C1)(C)C)CC[C@H](C3)CO)O)=O OSVHLUXLWQLPIY-KBAYOESNSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical group CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical group C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
239000012071 phase Substances 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
238000000039 preparative column chromatography Methods 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
229960003292 rifamycin Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000007619 statistical method Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 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
- C07D498/10—Spiro-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/18—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Thiazole And Isothizaole Compounds (AREA)

DK630686A 1985-12-30 1986-12-29 2'-Substituerede 4-deoxytiazolo(5,4-c)rifamycin SV-derivater, fremgangsmåde til fremstilling heraf, en sådan forbindelse til anvendelse som lægemiddel, anvendelse af forbindelsen til fremstilling af et antibakterielt medikament samt farmaceutisk præparat indeholdende forbindelsen DK170100B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8531887		1985-12-30
GB858531887A GB8531887D0 (en)	1985-12-30	1985-12-30	Rifamycin sv derivatives

Publications (3)

Publication Number	Publication Date
DK630686D0 DK630686D0 (da)	1986-12-29
DK630686A DK630686A (da)	1987-07-01
DK170100B1 true DK170100B1 (da)	1995-05-22

Family

ID=10590333

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK630686A DK170100B1 (da)	1985-12-30	1986-12-29	2'-Substituerede 4-deoxytiazolo(5,4-c)rifamycin SV-derivater, fremgangsmåde til fremstilling heraf, en sådan forbindelse til anvendelse som lægemiddel, anvendelse af forbindelsen til fremstilling af et antibakterielt medikament samt farmaceutisk præparat indeholdende forbindelsen

Country Status (17)

Country	Link
US (1)	US4880789A (de)
EP (1)	EP0228606B1 (de)
JP (1)	JPH07108909B2 (de)
KR (1)	KR940009795B1 (de)
AT (1)	ATE60772T1 (de)
CA (1)	CA1271472A (de)
DE (1)	DE3677485D1 (de)
DK (1)	DK170100B1 (de)
ES (1)	ES2031815T3 (de)
GB (1)	GB8531887D0 (de)
GR (1)	GR3001543T3 (de)
HK (1)	HK97391A (de)
HU (1)	HU196812B (de)
IE (1)	IE59505B1 (de)
IL (1)	IL80447A (de)
SG (1)	SG67091G (de)
ZA (1)	ZA869453B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL100642A (en) *	1991-01-28	1995-11-27	Lepetit Spa	Process for the preparation of (2-) diethylamino (rifmacin P) AED / P (and its new intermediate
US6375658B1 (en)	2000-04-28	2002-04-23	Smith & Nephew, Inc.	Cartilage grafting
US7256187B2 (en)	2004-03-10	2007-08-14	Cumbre Pharmaceuticals Inc.	Rifamycin C-11 oxime derivatives effective against drug-resistant microbes
US7265107B2 (en)	2004-03-10	2007-09-04	Cumbre Pharmaceuticals Inc.	Rifamycin C-11 oxime cyclo derivatives effective against drug-resistant microbes
US20100125146A1 (en) *	2008-11-19	2010-05-20	Johnson Matthey Public Limited Company	Method for making pharmaceutical compounds

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1470426A (en) *	1974-08-30	1977-04-14	Lepetit Spa	Rifamycins
GB1523199A (en) *	1976-05-28	1978-08-31	Lepetit Spa	Rifamycin sv derivatives
GB1523198A (en) *	1976-05-28	1978-08-31	Lepetit Spa	Thiazolo-rifamycin derivatives
CH629212A5 (it) *	1976-10-18	1982-04-15	Erba Farmitalia	Procedimento per la preparazione di composti di rifamicina.
GB1594134A (en) *	1977-11-25	1981-07-30	Holco Investment Inc	Rifamycins
IT1111173B (it) *	1978-04-27	1986-01-13	Lepetit Spa	Derivati rifamicinici
EP0049683A3 (de) *	1980-09-25	1982-09-01	Ciba-Geigy Ag	Imidazo-Rifamycine, Verfahren zu ihrer Herstellung, diese enthaltende pharmazeutische Präparate sowie ihre Verwendung

1985
- 1985-12-30 GB GB858531887A patent/GB8531887D0/en active Pending
1986
- 1986-10-29 IL IL80447A patent/IL80447A/xx not_active IP Right Cessation
- 1986-12-06 ES ES198686117005T patent/ES2031815T3/es not_active Expired - Lifetime
- 1986-12-06 AT AT86117005T patent/ATE60772T1/de not_active IP Right Cessation
- 1986-12-06 DE DE8686117005T patent/DE3677485D1/de not_active Expired - Lifetime
- 1986-12-06 EP EP19860117005 patent/EP0228606B1/de not_active Expired - Lifetime
- 1986-12-16 IE IE327786A patent/IE59505B1/en not_active IP Right Cessation
- 1986-12-17 ZA ZA869453A patent/ZA869453B/xx unknown
- 1986-12-18 KR KR1019860010871A patent/KR940009795B1/ko not_active Expired - Fee Related
- 1986-12-25 JP JP61308066A patent/JPH07108909B2/ja not_active Expired - Lifetime
- 1986-12-29 DK DK630686A patent/DK170100B1/da not_active IP Right Cessation
- 1986-12-29 HU HU865501A patent/HU196812B/hu not_active IP Right Cessation
- 1986-12-29 CA CA000526359A patent/CA1271472A/en not_active Expired - Lifetime
1988
- 1988-08-24 US US07/238,985 patent/US4880789A/en not_active Expired - Fee Related
1991
- 1991-03-04 GR GR91400257T patent/GR3001543T3/el unknown
- 1991-08-16 SG SG670/91A patent/SG67091G/en unknown
- 1991-12-05 HK HK973/91A patent/HK97391A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
DK630686D0 (da)	1986-12-29
IE863277L (en)	1987-06-30
DK630686A (da)	1987-07-01
IE59505B1 (en)	1994-03-09
HUT45072A (en)	1988-05-30
SG67091G (en)	1991-09-13
HK97391A (en)	1991-12-13
ATE60772T1 (de)	1991-02-15
EP0228606A2 (de)	1987-07-15
HU196812B (en)	1989-01-30
GB8531887D0 (en)	1986-02-05
KR940009795B1 (ko)	1994-10-17
GR3001543T3 (en)	1992-11-23
ZA869453B (en)	1987-09-30
ES2031815T3 (es)	1993-01-01
EP0228606A3 (en)	1989-01-11
IL80447A0 (en)	1987-01-30
EP0228606B1 (de)	1991-02-06
JPH07108909B2 (ja)	1995-11-22
US4880789A (en)	1989-11-14
JPS62158292A (ja)	1987-07-14
IL80447A (en)	1990-09-17
KR870006057A (ko)	1987-07-09
DE3677485D1 (de)	1991-03-14
CA1271472A (en)	1990-07-10

Legal Events

Date	Code	Title	Description
1995-05-22	B1	Patent granted (law 1993)
1999-04-19	PBP	Patent lapsed

Publication	Publication Date	Title
EP0366914B1 (de)	1994-11-30	3'-Hydroxysubstituiertes Benzoxazinorifamycinderivat, Verfahren zu seiner Herstellung und dieses enthaltendes antibakterielles Mittel
SU724087A3 (ru)	1980-03-25	Способ получени гидрохлорида оптически активных дауносаминилпроизводных антрациклинонов
DK149062B (da)	1986-01-06	Analogifremgangsmaade til fremstilling af cefuroximestere
FI60870B (fi)	1981-12-31	Foerfarande foer framstaellning av farmakologiskt vaerdefulla o-substituerade 7beta-amino-3-cefem-3-01-4-karbonsyrafoereningar
SU1586521A3 (ru)	1990-08-15	Способ получени производных гликопептидов
EP0313874B1 (de)	1994-04-13	Dischwefel-Analoge von LL-E33288 Antitumor-Verbindungen
DK170100B1 (da)	1995-05-22	2'-Substituerede 4-deoxytiazolo(5,4-c)rifamycin SV-derivater, fremgangsmåde til fremstilling heraf, en sådan forbindelse til anvendelse som lægemiddel, anvendelse af forbindelsen til fremstilling af et antibakterielt medikament samt farmaceutisk præparat indeholdende forbindelsen
JPS5896097A (ja)	1983-06-07	エリスロマイシンｂ誘導体
ZA200300472B (en)	2003-10-16	Process for the preparation of highly pure crystalline (R,S)-cefuroxime axetil.
EP0333176B1 (de)	1995-11-08	Substituiertes Benzoxazinorifamycinderivat, Verfahren zur Herstellung und dieses Derivat enthaltende Bakterizidmittel
DE69314072T2 (de)	1998-05-07	Cephalosporin-Derivat
AT390956B (de)	1990-07-25	Verfahren zur herstellung von neuen, in 3-stellung substituierten propenylaminothiazolylcephalosporansaeuren und deren estern
US4322412A (en)	1982-03-30	Anthracycline glycosides, their preparation, use and compositions thereof
HUT74883A (en)	1997-02-28	New process and intermediates for preparing naphthyridonecarboxylic acid salts
US4929612A (en)	1990-05-29	Thiadiazolylacetamide cephem derivatives
EP1828206B1 (de)	2009-02-18	Verfahren zur hestellung von cefixim
EP0004270B1 (de)	1981-12-30	Streptovaricin-C-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende antivirale Zubereitungen
FI69079C (fi)	1985-12-10	Foerfarande foer framstaellning av rifamycinderivat med antibakterisk aktivitet
KR950010086B1 (ko)	1995-09-06	신규 2'-치환-4-데옥시-티아졸로[5,4-c]리파마이신 SV 유도체
JP2544488B2 (ja)	1996-10-16	３’―ヒドロキシベンゾキサジノリファマイシン誘導体
JPH02188597A (ja)	1990-07-24	新抗生物質ｎ―アセチルベナノマイシンｂならびにその製造法
US4545936A (en)	1985-10-08	Novel aminonaphthacene derivatives and process for preparation thereof
JPH03101681A (ja)	1991-04-26	５’―（４―プロピルまたは４―イソプロピルピペラジニル）ベンゾキサジノリファマイシン誘導体
CN108101892A (zh)	2018-06-01	一种白杨素非天然氨基酸衍生物及其制备方法和应用
JPH01242589A (ja)	1989-09-27	セフエム化合物