NO761705L - - Google Patents

Info

Publication number: NO761705L
Authority: NO; Norway
Prior art keywords: formula; compound; filtered; less; rifamycin
Prior art date: 1975-05-20

Application number

NO761705A

Other languages

English (en)

Norwegian (no)

Inventor

L Marsili

V Rossetti

C Pasqualucci

Original Assignee

Archifar Ind Chim Trentino

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.)

1975-05-20

Filing date

1976-05-19

Publication date

1976-11-23

1976-05-19 Application filed by Archifar Ind Chim Trentino filed Critical Archifar Ind Chim Trentino

1976-11-23 Publication of NO761705L publication Critical patent/NO761705L/no

Links

QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 108
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 59
239000011701 zinc Substances 0.000 claims description 59
229910052725 zinc Inorganic materials 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 47
-1 nitro, amino Chemical group 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 13
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
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 claims description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
229910052742 iron Inorganic materials 0.000 claims description 4
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
229930189077 Rifamycin Natural products 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
150000002170 ethers Chemical class 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229960003292 rifamycin Drugs 0.000 claims description 3
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 2
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
229910017604 nitric acid Inorganic materials 0.000 claims description 2
239000007800 oxidant agent Substances 0.000 claims description 2
USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 2
150000002366 halogen compounds Chemical class 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
239000000243 solution Substances 0.000 description 62
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 48
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
239000002244 precipitate Substances 0.000 description 28
235000010265 sodium sulphite Nutrition 0.000 description 24
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
QBRFPWPICDILII-WVKYYCEASA-N 3-amino-4-iminorifamycin-s Chemical compound O=C1C(C(O)=C2C)=C3C(N)=C(N)C1=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](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O QBRFPWPICDILII-WVKYYCEASA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 19
238000000862 absorption spectrum Methods 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 11
239000008346 aqueous phase Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
239000008055 phosphate buffer solution Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 8
235000011152 sodium sulphate Nutrition 0.000 description 8
239000000203 mixture Substances 0.000 description 7
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
235000010378 sodium ascorbate Nutrition 0.000 description 5
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 5
229960005055 sodium ascorbate Drugs 0.000 description 5
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 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 description 4
241000786363 Rhampholeon spectrum Species 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
UNNGUFMVYQJGTD-UHFFFAOYSA-N 2-Ethylbutanal Chemical compound CCC(CC)C=O UNNGUFMVYQJGTD-UHFFFAOYSA-N 0.000 description 2
BYGQBDHUGHBGMD-UHFFFAOYSA-N 2-methylbutanal Chemical compound CCC(C)C=O BYGQBDHUGHBGMD-UHFFFAOYSA-N 0.000 description 2
OPHQOIGEOHXOGX-UHFFFAOYSA-N 3,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1OC OPHQOIGEOHXOGX-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000005864 Sulphur Substances 0.000 description 2
SMPJCQGFZSDIHE-GVDHMVJUSA-N [(7S,9E,11S,12R,13S,14R,15R,16R,17S,18S,19E,21Z)-26-amino-2,15,17-trihydroxy-11-methoxy-3,7,12,14,16,18,22-heptamethyl-6,23,27,29-tetraoxo-8,30-dioxa-24-azatetracyclo[23.3.1.14,7.05,28]triaconta-1(28),2,4,9,19,21,25-heptaen-13-yl] acetate Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C(N)=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 SMPJCQGFZSDIHE-GVDHMVJUSA-N 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
235000010323 ascorbic acid Nutrition 0.000 description 2
239000011668 ascorbic acid Substances 0.000 description 2
229960005070 ascorbic acid Drugs 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
WTWBUQJHJGUZCY-UHFFFAOYSA-N cuminaldehyde Chemical compound CC(C)C1=CC=C(C=O)C=C1 WTWBUQJHJGUZCY-UHFFFAOYSA-N 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
229910052760 oxygen Inorganic materials 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical group OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 2
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
239000001893 (2R)-2-methylbutanal Substances 0.000 description 1
ZYECOAILUNWEAL-NUDFZHEQSA-N (4z)-4-[[2-methoxy-5-(phenylcarbamoyl)phenyl]hydrazinylidene]-n-(3-nitrophenyl)-3-oxonaphthalene-2-carboxamide Chemical compound COC1=CC=C(C(=O)NC=2C=CC=CC=2)C=C1N\N=C(C1=CC=CC=C1C=1)/C(=O)C=1C(=O)NC1=CC=CC([N+]([O-])=O)=C1 ZYECOAILUNWEAL-NUDFZHEQSA-N 0.000 description 1
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical group C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
JMPVYNJKWJGXEY-UHFFFAOYSA-N 1-phenyltetrazole-5-carbaldehyde Chemical compound O=CC1=NN=NN1C1=CC=CC=C1 JMPVYNJKWJGXEY-UHFFFAOYSA-N 0.000 description 1
ANWMNLAAFDCKMT-UHFFFAOYSA-N 2-(2-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC=C1C=O ANWMNLAAFDCKMT-UHFFFAOYSA-N 0.000 description 1
OACPOWYLLGHGCR-UHFFFAOYSA-N 2-chloro-6-fluorobenzaldehyde Chemical compound FC1=CC=CC(Cl)=C1C=O OACPOWYLLGHGCR-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
ZWDVQMVZZYIAHO-UHFFFAOYSA-N 2-fluorobenzaldehyde Chemical compound FC1=CC=CC=C1C=O ZWDVQMVZZYIAHO-UHFFFAOYSA-N 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
IQAIPUWCYPGRQL-UHFFFAOYSA-N 2-hydroxyacetic acid;hydrate Chemical compound O.OCC(O)=O IQAIPUWCYPGRQL-UHFFFAOYSA-N 0.000 description 1
AEHWVNPVEUVPMT-UHFFFAOYSA-N 2-methyl-1,3-thiazole-4-carbaldehyde Chemical compound CC1=NC(C=O)=CS1 AEHWVNPVEUVPMT-UHFFFAOYSA-N 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
241000187479 Mycobacterium tuberculosis Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
DCFDVJPDXYGCOK-UHFFFAOYSA-N cyclohex-3-ene-1-carbaldehyde Chemical compound O=CC1CCC=CC1 DCFDVJPDXYGCOK-UHFFFAOYSA-N 0.000 description 1
KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
IDXVHCVIZRQSRA-UHFFFAOYSA-N ethyl 3-formylcyclohexane-1-carboxylate Chemical compound CCOC(=O)C1CCCC(C=O)C1 IDXVHCVIZRQSRA-UHFFFAOYSA-N 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
238000000643 oven drying Methods 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
125000003831 tetrazolyl group Chemical group 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- 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
- A61P31/06—Antibacterial agents for tuberculosis
- 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
- C07D498/12—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 three hetero rings
- C07D498/20—Spiro-condensed systems

Landscapes

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

NO761705A 1975-05-20 1976-05-19 NO761705L (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT05157/75A IT1056271B (it)	1975-05-20	1975-05-20	Prodotti derivati dalle amine aromatiche

Publications (1)

Publication Number	Publication Date
NO761705L true NO761705L (de)	1976-11-23

Family

ID=11118558

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO761705A NO761705L (de)	1975-05-20	1976-05-19

Country Status (27)

Country	Link
US (1)	US4226765A (de)
JP (1)	JPS5248698A (de)
AR (1)	AR213175A1 (de)
AT (1)	AT344897B (de)
AU (1)	AU497327B2 (de)
BE (1)	BE842036A (de)
CA (1)	CA1053667A (de)
CH (1)	CH625804A5 (de)
CS (1)	CS194763B2 (de)
DE (1)	DE2622638C2 (de)
DK (1)	DK143852C (de)
FI (1)	FI60207C (de)
FR (1)	FR2311778A1 (de)
GB (1)	GB1546954A (de)
HU (1)	HU172924B (de)
IE (1)	IE42997B1 (de)
IL (1)	IL49606A (de)
IN (1)	IN142992B (de)
IT (1)	IT1056271B (de)
NL (1)	NL180478C (de)
NO (1)	NO761705L (de)
PL (1)	PL101470B1 (de)
PT (1)	PT65113B (de)
SE (1)	SE443142B (de)
SU (1)	SU686620A3 (de)
YU (1)	YU39965B (de)
ZA (1)	ZA762989B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK345977A (da) *	1976-09-30	1978-03-31	Archifar Ind Chim Trentino	G rifamycinforbindelser og fremgangsmaade til deres fremstillin
GB1576886A (en) *	1977-04-20	1980-10-15	Lepetit Spa	Rifamycin derivatives
CH633014A5 (en) *	1978-06-09	1982-11-15	Erba Farmitalia	Rifamycin compounds
BE886395A (fr) *	1980-02-13	1981-03-16	Erba Farmitalia	Derives de rifamycine
IT1201963B (it) *	1983-03-24	1989-02-02	Prodotti Antibiotici Spa	Derivati delle rifamicine e procedimento per la loro preparazione
JPS61197941U (de) *	1985-05-30	1986-12-10
WO2003045319A2 (en) *	2001-11-21	2003-06-05	Activbiotics, Inc.	Targeted therapeutics and uses thereof
US7820652B2 (en) *	2003-09-24	2010-10-26	Activbiotics Pharma, Llc	Regimen for the administration of rifamycin-class antibiotics

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL130099C (de) *	1963-10-11
FR208F (de) *	1964-07-31
CA930734A (en) *	1969-08-11	1973-07-24	Bickel Hans	Antibiotically active rifamycin compounds and processes for their manufacture

1975
- 1975-05-20 IT IT05157/75A patent/IT1056271B/it active
1976
- 1976-05-07 CH CH574076A patent/CH625804A5/it not_active IP Right Cessation
- 1976-05-10 IE IE999/76A patent/IE42997B1/en unknown
- 1976-05-11 AT AT343076A patent/AT344897B/de not_active IP Right Cessation
- 1976-05-11 SE SE7605341A patent/SE443142B/xx not_active IP Right Cessation
- 1976-05-12 GB GB19508/76A patent/GB1546954A/en not_active Expired
- 1976-05-12 US US05/685,624 patent/US4226765A/en not_active Expired - Lifetime
- 1976-05-13 CS CS763210A patent/CS194763B2/cs unknown
- 1976-05-14 YU YU1211/76A patent/YU39965B/xx unknown
- 1976-05-17 FR FR7614749A patent/FR2311778A1/fr active Granted
- 1976-05-17 CA CA252,701A patent/CA1053667A/en not_active Expired
- 1976-05-18 IN IN866/CAL/76A patent/IN142992B/en unknown
- 1976-05-18 FI FI761392A patent/FI60207C/fi not_active IP Right Cessation
- 1976-05-18 AU AU14047/76A patent/AU497327B2/en not_active Expired
- 1976-05-19 DK DK220276A patent/DK143852C/da not_active IP Right Cessation
- 1976-05-19 PT PT65113A patent/PT65113B/pt unknown
- 1976-05-19 NO NO761705A patent/NO761705L/no unknown
- 1976-05-19 NL NLAANVRAGE7605355,A patent/NL180478C/xx not_active IP Right Cessation
- 1976-05-19 HU HU76AI00000257A patent/HU172924B/hu unknown
- 1976-05-19 IL IL49606A patent/IL49606A/xx unknown
- 1976-05-19 AR AR263326A patent/AR213175A1/es active
- 1976-05-19 ZA ZA762989A patent/ZA762989B/xx unknown
- 1976-05-20 PL PL1976189732A patent/PL101470B1/pl unknown
- 1976-05-20 JP JP51058495A patent/JPS5248698A/ja active Granted
- 1976-05-20 SU SU762360101A patent/SU686620A3/ru active
- 1976-05-20 DE DE2622638A patent/DE2622638C2/de not_active Expired
- 1976-05-20 BE BE167191A patent/BE842036A/xx unknown

Also Published As

Publication number	Publication date
DE2622638C2 (de)	1986-11-13
CH625804A5 (de)	1981-10-15
FI761392A (de)	1976-11-21
CA1053667A (en)	1979-05-01
FR2311778B1 (de)	1979-06-15
CS194763B2 (en)	1979-12-31
US4226765A (en)	1980-10-07
NL7605355A (nl)	1976-11-23
DK220276A (da)	1976-11-21
YU121176A (en)	1982-08-31
AU497327B2 (en)	1978-12-07
BE842036A (fr)	1976-09-16
DE2622638A1 (de)	1976-12-09
SU686620A3 (ru)	1979-09-15
NL180478C (nl)	1987-03-02
IE42997L (en)	1976-11-20
AR213175A1 (es)	1978-12-29
PT65113A (en)	1976-06-01
FR2311778A1 (fr)	1976-12-17
DK143852B (da)	1981-10-19
JPS554756B2 (de)	1980-01-31
SE443142B (sv)	1986-02-17
GB1546954A (en)	1979-05-31
IL49606A0 (en)	1976-07-30
IN142992B (de)	1977-09-17
AU1404776A (en)	1977-11-24
PT65113B (en)	1977-10-10
PL101470B1 (pl)	1978-12-30
YU39965B (en)	1985-06-30
IT1056271B (it)	1982-01-30
HU172924B (hu)	1979-01-28
IL49606A (en)	1979-11-30
FI60207B (fi)	1981-08-31
AT344897B (de)	1978-08-10
FI60207C (fi)	1981-12-10
ATA343076A (de)	1977-12-15
IE42997B1 (en)	1980-12-03
NL180478B (nl)	1986-10-01
SE7605341L (sv)	1976-11-21
ZA762989B (en)	1977-04-27
DK143852C (da)	1982-03-15
JPS5248698A (en)	1977-04-18

Publication	Publication Date	Title
Yalpani et al.	1971	1, 2, 3-Selenadiazole and its derivatives
NO136947B (no)	1977-08-22	Bredb}ndsrundstr}leantenne.
US4219478A (en)	1980-08-26	Rifamycin compounds
NO761705L (de)	1976-11-23
US4013680A (en)	1977-03-22	Process for the preparation of aromatic α-keto carboxylic acids
NO763846L (de)	1977-05-13
Reeve et al.	1975	New syntheses of thiadiazinones, thiazolidinedione hydrazones, and hydroxythiazoles from phenyl (trichloromethyl) carbinols
KR810000103B1 (ko)	1981-02-14	리파마이신 화합물의 제조방법
FI62098C (fi)	1982-11-10	Foerfarande foer framstaellning av tiazolo(5,4-c)rifamycin sv och dess derivat
US3678051A (en)	1972-07-18	Derivatives of 1,6-phenazinediol 5,10-dioxide
US4351942A (en)	1982-09-28	Isochromans
CA1262732A (en)	1989-11-07	Preparation of 1,3-dihydro-4-pyridoyl-2h-imidazol-2- ones
NO159658B (no)	1988-10-17	Mellomprodukt for fremstilling av 1,1-diokso-penicillanoyloksymetyl-6-(2-amino-2-fenyl-acetamido)penicillanat-antibiotika.
US3966720A (en)	1976-06-29	Process for producing desacetoxy cephalosporanic acid compound
SU429062A1 (ru)	1974-05-25	СПОСОБ ПОЛУЧЕНИЯ ПИРИДО[2,3-Ь] [1,5]ТИАЗЕПИНОНОВПредлагаетс способ получени пиридо [2,3-й] [!1,5]тиазепиионов, которые могут найти применение в качестве биологически активных веществ.В литературе нет сведений о получении производных указанной гетероциклической сисге- мы. Известны лишь производные пиримидо [i2,5-&] ['1,5]тиазепинона, способ получени которых основан на реакции 5-амино-6-меркапто- пиримидинов с хлорангидридом р-бромпропио- новой кислоты с последующей циклизацией образующихс при этом 5-(р-бромпропионил) амино-6-меркаптопиримидинов и пиримидоти- азепины.Оказалось, что этим методом нельз получить пиридотиазепиноны, так как реакци 2-меркапто-З-аминопиридинов с хлорангидридом р-бромн\|ропионовой кислоты протекает одновременно по амино- и меркаптогруппе, в результате чего образуютс соединени , от которых не удаетс перейти к пиридотиазепино- нам.Предлагаетс способ получени ииридо [2,3-6] [1,5]тиазепинонов общей формулы 1Ri , , I ^',N—<где R — водород, алкоксил или галоид;RI — водород или алкил. Способ заключаетс в том, что 2-меркапто- 3-аминопиридин общей формулы 2IN'H,SH1015где R имеет указанные значени , нодвер- гают взаимодействию с р-галогеналкановой кислотой в среде растворител , например спирта, в присутствии гидроокисей щелочных металлов, полученный при этом 2-(\|р-карбо- кснэтил)тио-3-аминопиридин общей формулы 320иf^^^^-I II г- СООНV-s-^2530где R имеет указанные значени , цикли- зуют под действием дициклогексилкарбоди- имида в среде растворител и образовавшиес целевые соединени формулы 1, где Ri — водород, или выдел ют обычными нриемами или, если это необходимо, далее перевод т в целевые соединени общей формулы 1, где Ri •— алкил, действием галоидалкилов, например
US3210337A (en)	1965-10-05	6-(benzofurylcarboxamido)- and 6-(thianaphthenylcarboxamido)-penicillanic acid derivatives
KR790001261B1 (ko)	1979-09-18	리파 마이신 화합물의 제조방법
Girges et al.	1988	Synthesis of some new 3-substituted-4-hydroxy-1-methyl-quinolin-2-one derivatives as potential antibacterial and antifungal agents
Albert et al.	1973	1, 2, 3-Triazoles. Part I. Some 4-aminotriazole-5-carbaldehydes
US3941781A (en)	1976-03-02	Preparation of 3-alkylthiomethyl cephalosporins
FJELDSTAD et al.	1973	IV-Quaternary Compounds
KR790001528B1 (ko)	1979-10-26	리파마이신 화합물의 제조방법
SU578889A3 (ru)	1977-10-30	Способ получени производных пенициллинов или цефалоспоринов, или их солей или их эфиров
KR820000498B1 (ko)	1982-04-08	리파마이신 화합물의 제조방법
FI82692B (fi)	1990-12-31	Foerfarande foer framstaellning av 1,3-dihydro-4-pyridinyl-2h-imidazol-2-oner.