DK167360B1 - Fremgangsmaade til fremstilling af pristinamycin iib-derivater - Google Patents

Fremgangsmaade til fremstilling af pristinamycin iib-derivater Download PDF

Info

Publication number: DK167360B1
Authority: DK; Denmark
Prior art keywords: alkyl; compound; nitrogen; isomer; ruthenium
Prior art date: 1986-07-09

Application number

DK349887A

Other languages

Danish (da)

English (en)

Other versions

DK349887A (da

DK349887D0 (da

Inventor

Devnandan Chatterjee

Neil Victor Harris

Trevor Parker

Christopher Smith

Peter James Warren

Original Assignee

May & Baker Ltd

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.)

1986-07-09

Filing date

1987-07-07

Publication date

1993-10-18

1987-07-07 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1987-07-07 Publication of DK349887D0 publication Critical patent/DK349887D0/da

1988-01-10 Publication of DK349887A publication Critical patent/DK349887A/da

1993-10-18 Application granted granted Critical

1993-10-18 Publication of DK167360B1 publication Critical patent/DK167360B1/da

Links

238000000034 method Methods 0.000 title claims abstract description 23
JOOMGSFOCRDAHL-XKCHLWDXSA-N pristinamycin-IIB Natural products CC(C)[C@@H]1OC(=O)[C@H]2CCCN2C(=O)c3coc(CC(=O)C[C@@H](O)C=C(C)C=CCNC(=O)C=C[C@H]1C)n3 JOOMGSFOCRDAHL-XKCHLWDXSA-N 0.000 title claims abstract description 7
238000002360 preparation method Methods 0.000 title abstract description 7
108010015791 Streptogramin A Proteins 0.000 title abstract description 5
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 20
238000007254 oxidation reaction Methods 0.000 claims abstract description 15
230000003647 oxidation Effects 0.000 claims abstract description 14
KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical class OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 claims abstract description 14
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract description 13
239000002253 acid Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 9
230000003197 catalytic effect Effects 0.000 claims abstract description 8
229910052707 ruthenium Inorganic materials 0.000 claims abstract description 8
229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 6
238000011065 in-situ storage Methods 0.000 claims abstract description 4
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
150000003304 ruthenium compounds Chemical class 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 10
125000004432 carbon atom Chemical group C* 0.000 claims abstract 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 6
125000005842 heteroatom Chemical group 0.000 claims abstract 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 6
229910052760 oxygen Inorganic materials 0.000 claims abstract 6
239000001301 oxygen Substances 0.000 claims abstract 6
125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract 5
125000006413 ring segment Chemical group 0.000 claims abstract 4
125000003282 alkyl amino group Chemical group 0.000 claims abstract 2
229910052799 carbon Inorganic materials 0.000 claims abstract 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 117
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 42
229910052717 sulfur Chemical group 0.000 claims description 21
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 claims description 14
229960003961 pristinamycin Drugs 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
150000003457 sulfones Chemical class 0.000 claims description 4
150000003462 sulfoxides Chemical class 0.000 claims description 4
YVMBAUWDIGJRNY-BESUKNQGSA-N 4o8o7q7iu4 Chemical compound C1C(=O)C[C@H](O)\C=C(/C)\C=C\CNC(=O)\C=C\[C@@H](C)[C@@H](C(C)C)OC(=O)C2=CCCN2C(=O)C2=COC1=N2.N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YVMBAUWDIGJRNY-BESUKNQGSA-N 0.000 claims description 3
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 2
RLNUPSVMIYRZSM-UHFFFAOYSA-N Pristinamycin Natural products CC1OC(=O)C(C=2C=CC=CC=2)NC(=O)C2CC(=O)CCN2C(=O)C(CC=2C=CC(=CC=2)N(C)C)CCN(C)C(=O)C2CCCN2C(=O)C(CC)NC(=O)C1NC(=O)C1=NC=CC=C1O RLNUPSVMIYRZSM-UHFFFAOYSA-N 0.000 claims description 2
108010079780 Pristinamycin Proteins 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
DAIKHDNSXMZDCU-OUDXUNEISA-N pristinamycin-IIA Natural products CC(C)[C@H]1OC(=O)C2=CCCN2C(=O)c3coc(CC(=O)C[C@H](O)C=C(C)C=CCNC(=O)C=C[C@@H]1C)n3 DAIKHDNSXMZDCU-OUDXUNEISA-N 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims 3
238000004519 manufacturing process Methods 0.000 claims 1
150000004684 trihydrates Chemical class 0.000 claims 1
-1 [(S)-1-methyl-2-pyrrolidinyl]methyl group Chemical group 0.000 abstract description 94
150000001875 compounds Chemical class 0.000 abstract description 52
239000000203 mixture Substances 0.000 abstract description 28
125000001174 sulfone group Chemical group 0.000 abstract 4
ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 3
239000005864 Sulphur Substances 0.000 abstract 3
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical class C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 78
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 42
239000000243 solution Substances 0.000 description 38
239000007787 solid Substances 0.000 description 32
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
229910052739 hydrogen Inorganic materials 0.000 description 24
239000000843 powder Substances 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
238000003756 stirring Methods 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 15
229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
238000004458 analytical method Methods 0.000 description 14
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 13
239000000706 filtrate Substances 0.000 description 13
239000008346 aqueous phase Substances 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000010410 layer Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
239000000284 extract Substances 0.000 description 10
239000000463 material Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000003818 flash chromatography Methods 0.000 description 8
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 7
239000000047 product Substances 0.000 description 7
239000005909 Kieselgur Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
GJFJJZHAMZHQMO-UHFFFAOYSA-N dioxoruthenium dihydrate Chemical compound O.O.O=[Ru]=O GJFJJZHAMZHQMO-UHFFFAOYSA-N 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000007853 buffer solution Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
239000006071 cream Substances 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
239000002027 dichloromethane extract Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
239000007979 citrate buffer Substances 0.000 description 2
WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 2
JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
DZKRDHLYQRTDBU-UPHRSURJSA-N (z)-but-2-enediperoxoic acid Chemical compound OOC(=O)\C=C/C(=O)OO DZKRDHLYQRTDBU-UPHRSURJSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 4-nitrobenzenecarboperoxoic acid Chemical compound OOC(=O)C1=CC=C([N+]([O-])=O)C=C1 ZJAFQAPHWPSKRZ-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000006229 carbon black Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960002887 deanol Drugs 0.000 description 1
125000005117 dialkylcarbamoyl group Chemical group 0.000 description 1
239000012972 dimethylethanolamine Substances 0.000 description 1
FGEKTVAHFDQHBU-UHFFFAOYSA-N dioxoruthenium;hydrate Chemical compound O.O=[Ru]=O FGEKTVAHFDQHBU-UHFFFAOYSA-N 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229920001971 elastomer Polymers 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
150000004966 inorganic peroxy acids Chemical class 0.000 description 1
125000005956 isoquinolyl group Chemical group 0.000 description 1
239000002609 medium Substances 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
150000004967 organic peroxy acids Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
150000004968 peroxymonosulfuric acids Chemical class 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical group C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 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
- C07D498/12—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
- C07D498/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06139—Dipeptides with the first amino acid being heterocyclic
- C07K5/06182—Dipeptides with the first amino acid being heterocyclic and Pristinamycin II; Derivatives thereof

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Biophysics (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)

DK349887A 1986-07-09 1987-07-07 Fremgangsmaade til fremstilling af pristinamycin iib-derivater DK167360B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB868616768A GB8616768D0 (en)	1986-07-09	1986-07-09	Process
GB8616768		1986-07-09

Publications (3)

Publication Number	Publication Date
DK349887D0 DK349887D0 (da)	1987-07-07
DK349887A DK349887A (da)	1988-01-10
DK167360B1 true DK167360B1 (da)	1993-10-18

Family

ID=10600806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK349887A DK167360B1 (da)	1986-07-09	1987-07-07	Fremgangsmaade til fremstilling af pristinamycin iib-derivater

Country Status (19)

Country	Link
US (1)	US4866172A (de)
EP (1)	EP0252720B1 (de)
JP (1)	JPS6323885A (de)
KR (1)	KR880001645A (de)
AT (1)	ATE67506T1 (de)
AU (1)	AU601445B2 (de)
CA (1)	CA1314878C (de)
DE (1)	DE3773066D1 (de)
DK (1)	DK167360B1 (de)
ES (1)	ES2029836T3 (de)
FI (1)	FI86303C (de)
GB (1)	GB8616768D0 (de)
GR (1)	GR3003048T3 (de)
IE (1)	IE60744B1 (de)
IL (1)	IL83116A (de)
NZ (1)	NZ220984A (de)
PT (1)	PT85274B (de)
SU (1)	SU1639429A3 (de)
ZA (1)	ZA874937B (de)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3778359D1 (de) *	1987-07-07	1992-05-21	Rhone Poulenc Sante	Verfahren zur herstellung von derivaten von pristinamycin iib.
FR2664598A1 (fr) *	1990-07-16	1992-01-17	Rhone Poulenc Rorer Sa	Procede de preparation de sulfinyl pristinamycine iib.
FR2664597B1 (fr) *	1990-07-16	1994-09-02	Rhone Poulenc Sante	Procede de preparation de sulfonylpristinamycine iib.
FR2664599B1 (fr) *	1990-07-16	1993-06-18	Rhone Poulenc Sante	Vinylsulfonyl pristinamycine et sa preparation.
FR2664600B1 (fr) *	1990-07-16	1994-09-02	Rhone Poulenc Sante	Nouveau sel derive de la dialcoylaminoalcoyl-sulfonyl-26 pristinamycine iib.
US5242938A (en) *	1992-08-27	1993-09-07	Merck & Co., Inc.	Derivatives of virginiamycin M1
US5689173A (en) *	1995-02-07	1997-11-18	Sanyo Electric Co., Ltd.	Battery pack
FR2766489B1 (fr)	1997-07-28	1999-08-27	Rhone Poulenc Rorer Sa	Derives de streptogramines, leur preparation et les compositions qui les contiennent
FR2818644B1 (fr) *	2000-12-21	2004-10-22	Aventis Pharma Sa	Derives de streptogramines, leur preparation et les compositions qui les contiennent

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2549064B1 (fr) *	1983-07-13	1985-10-25	Rhone Poulenc Sante	Nouveaux derives de synergistines utiles pour la preparation de nouveaux medicaments antimicrobiens et leur preparation
FR2549065B1 (fr) *	1983-07-13	1985-10-25	Rhone Poulenc Sante	Nouveaux derives de synergistines, leur preparation et les compositions pharmaceutiques qui les contiennent
FR2576022B1 (fr) *	1985-01-11	1987-09-11	Rhone Poulenc Sante	Nouveaux derives de la pristinamycine ii b, leur preparation et les compositions pharmaceutiques qui les contiennent

1986
- 1986-07-09 GB GB868616768A patent/GB8616768D0/en active Pending
1987
- 1987-07-07 AT AT87306001T patent/ATE67506T1/de not_active IP Right Cessation
- 1987-07-07 CA CA000541447A patent/CA1314878C/en not_active Expired - Fee Related
- 1987-07-07 IL IL83116A patent/IL83116A/xx not_active IP Right Cessation
- 1987-07-07 NZ NZ220984A patent/NZ220984A/xx unknown
- 1987-07-07 SU SU874202981A patent/SU1639429A3/ru active
- 1987-07-07 JP JP62167959A patent/JPS6323885A/ja active Pending
- 1987-07-07 IE IE180987A patent/IE60744B1/en not_active IP Right Cessation
- 1987-07-07 ZA ZA874937A patent/ZA874937B/xx unknown
- 1987-07-07 PT PT85274A patent/PT85274B/pt not_active IP Right Cessation
- 1987-07-07 ES ES198787306001T patent/ES2029836T3/es not_active Expired - Lifetime
- 1987-07-07 FI FI873015A patent/FI86303C/fi not_active IP Right Cessation
- 1987-07-07 AU AU75292/87A patent/AU601445B2/en not_active Ceased
- 1987-07-07 EP EP87306001A patent/EP0252720B1/de not_active Expired - Lifetime
- 1987-07-07 DK DK349887A patent/DK167360B1/da not_active IP Right Cessation
- 1987-07-07 DE DE8787306001T patent/DE3773066D1/de not_active Expired - Fee Related
- 1987-07-07 KR KR1019870007266A patent/KR880001645A/ko not_active Ceased
1988
- 1988-04-12 US US07/183,310 patent/US4866172A/en not_active Expired - Fee Related
1991
- 1991-10-31 GR GR91401641T patent/GR3003048T3/el unknown

Also Published As

Publication number	Publication date
IL83116A0 (en)	1987-12-31
FI873015A0 (fi)	1987-07-07
ATE67506T1 (de)	1991-10-15
DE3773066D1 (de)	1991-10-24
AU7529287A (en)	1988-01-14
IL83116A (en)	1993-02-21
NZ220984A (en)	1989-12-21
GR3003048T3 (en)	1993-02-17
DK349887A (da)	1988-01-10
ZA874937B (en)	1988-03-30
EP0252720B1 (de)	1991-09-18
FI873015A7 (fi)	1988-01-10
AU601445B2 (en)	1990-09-13
ES2029836T3 (es)	1992-10-01
GB8616768D0 (en)	1986-08-13
US4866172A (en)	1989-09-12
IE871809L (en)	1988-01-09
IE60744B1 (en)	1994-08-10
JPS6323885A (ja)	1988-02-01
PT85274B (pt)	1990-03-30
FI86303C (fi)	1992-08-10
KR880001645A (ko)	1988-04-25
DK349887D0 (da)	1987-07-07
FI86303B (fi)	1992-04-30
PT85274A (en)	1987-08-01
EP0252720A2 (de)	1988-01-13
CA1314878C (en)	1993-03-23
SU1639429A3 (ru)	1991-03-30
EP0252720A3 (en)	1988-06-29

Legal Events

Date	Code	Title	Description
1993-10-18	B1	Patent granted (law 1993)
1996-03-25	PBP	Patent lapsed

Publication	Publication Date	Title
JP2730612B2 (ja)	1998-03-25	８‐クロロ‐１１‐〔１‐〔（５‐メチル‐３‐ピリジル）メチル〕‐４‐ピペリジリデン〕‐６，１１‐ジヒドロ‐５Ｈ‐ベンゾ〔５，６〕シクロヘプタ〔１，２‐ｂ〕ピリジン
PT98011B (pt)	1997-04-30	Processo para a preparacao de pirazolopirimidinonas uteis como agentes antianginosos
DK167360B1 (da)	1993-10-18	Fremgangsmaade til fremstilling af pristinamycin iib-derivater
ZA200405175B (en)	2005-06-21	Coumarines useful as biomarkers.
IE55055B1 (en)	1990-05-09	Esters of phosphinylalkanoyl substituted prolines
EP0222413A2 (de)	1987-05-20	Forskolinderivate
CS276785B6 (en)	1992-08-12	PROCESS FOR PREPARING NOVEL DERIVATIVES OF 1H,3H-PYRROLO-(1,2-c)THIAZOLE-7-CARBOXAMIDE
PL161369B1 (en)	1993-06-30	Method of obtaining novel derivatives of 2-iminobenzothiazoline
PT1732929E (pt)	2010-12-21	Composto de benzopirano tricíclico enquanto agentes antiarrítmicos
JPH0249788A (ja)	1990-02-20	ピラノベンゾオキサジアゾール誘導体
FI89267B (fi)	1993-05-31	Foerfarande foer framstaellning av terapeutiskt aktiva 4,5-dihydro-oxazoler
US3506646A (en)	1970-04-14	Process for the preparation of 7h-pyrido (1,2-b)(1,2,5)benzothiadiazepine 5,5 - dioxides and pyrrolo(1,2-b)(1,2,5)benzothiadiazepine 5,5-dioxides
DK154083B (da)	1988-10-10	Analogifremgangsmaade til fremstilling af halogenvincamonderivater eller optisk aktive isomere eller syreadditionssalte deraf
GB2206577A (en)	1989-01-11	New process for the preparation of therapeutically useful pristinamycin IIB sulphone derivatives
DK153487B (da)	1988-07-18	Analogifremgangsmaade til fremstilling af 2-(perhydro-1,4-diazino)-pyrimidooe5,4-daapyrimidinderivater
US4138489A (en)	1979-02-06	Vasodilating octahydro-1,12-methano-oxymethano[2,3-a]-indoloquinolizines
FI71733B (fi)	1986-10-31	Foerfarande foer framstaellning av farmaceutiskt aktiva 3,6-substituerade 2-vinyl-kromoner
JPH0140033B2 (de)	1989-08-24
JPS62145083A (ja)	1987-06-29	縮合イミダゾ−ル誘導体
US3697523A (en)	1972-10-10	2-substituted-11-(4-methyl-1-piperizinyl)-dibenzo {8 b,f{9 -1,4-oxazepin-(4-oxide)
DK169681B1 (da)	1995-01-09	Fremgangsmåde til fremstilling af pristinamycin IIB-derivater
US3803149A (en)	1974-04-09	5-piperazinyl-10-dioxo-dibenzo(c,f)thiazepines and process for making them
KR950013565B1 (ko)	1995-11-09	시네르지스틴 및 이를 포함하는 제약학적 조성물
JPH03200764A (ja)	1991-09-02	新規グアニジノ安息香酸誘導体及びその酸付加塩
FI81580B (fi)	1990-07-31	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pyridazopyridazinderivat och nya mellanprodukter.