FI58635C - Foerfarande foer framstaellning av nya antimikrobiska pleuromutiliner - Google Patents
Foerfarande foer framstaellning av nya antimikrobiska pleuromutiliner Download PDFInfo
- Publication number
- FI58635C FI58635C FI2645/72A FI264572A FI58635C FI 58635 C FI58635 C FI 58635C FI 2645/72 A FI2645/72 A FI 2645/72A FI 264572 A FI264572 A FI 264572A FI 58635 C FI58635 C FI 58635C
- Authority
- FI
- Finland
- Prior art keywords
- carbon atoms
- deoxy
- alkyl
- solution
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 239000002253 acid Substances 0.000 claims abstract description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 3
- ZRZNJUXESFHSIO-UHFFFAOYSA-N Pleuromutilin Natural products CC1C(O)C(C)(C=C)CC(OC(=O)CO)C2(C)C(C)CCC31C2C(=O)CC3 ZRZNJUXESFHSIO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- ZRZNJUXESFHSIO-VYTKZBNOSA-N pleuromutilin Chemical compound C([C@H]([C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CO)C)C[C@]32[C@H]1C(=O)CC3 ZRZNJUXESFHSIO-VYTKZBNOSA-N 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 14
- 238000000034 method Methods 0.000 abstract description 11
- 239000001257 hydrogen Substances 0.000 abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 2
- 229940088710 antibiotic agent Drugs 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Substances 0.000 abstract 4
- 125000004423 acyloxy group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 abstract 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000005977 Ethylene Substances 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229920002554 vinyl polymer Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 239000000243 solution Substances 0.000 description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 26
- 229960002771 retapamulin Drugs 0.000 description 23
- -1 piperidino, perhydroazepinyl Chemical group 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 239000011734 sodium Substances 0.000 description 15
- 229910052708 sodium Inorganic materials 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- OBUUFWIMEGVAQS-UHFFFAOYSA-N Pleuromutenol Natural products CC1C(O)C(C)(C=C)CC(O)C2(C)C(C)CCC31C2C(=O)CC3 OBUUFWIMEGVAQS-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical compound C([C@H]([C@@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)OC(=O)CS[C@@H]3C[C@H]4CC[C@H](N4C)C3)C)C[C@]32[C@H]1C(=O)CC3 STZYTFJPGGDRJD-NHUWBDDWSA-N 0.000 description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000001035 drying Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 5
- CURCMGVZNYCRNY-UHFFFAOYSA-N trimethylazanium;iodide Chemical compound I.CN(C)C CURCMGVZNYCRNY-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- CMBJWSUWPPPZTH-UHFFFAOYSA-N 1-(diethylamino)ethanethiol;hydrochloride Chemical compound Cl.CCN(CC)C(C)S CMBJWSUWPPPZTH-UHFFFAOYSA-N 0.000 description 3
- MPNXSZJPSVBLHP-UHFFFAOYSA-N 2-chloro-n-phenylpyridine-3-carboxamide Chemical compound ClC1=NC=CC=C1C(=O)NC1=CC=CC=C1 MPNXSZJPSVBLHP-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000000845 anti-microbial effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- BTRRKMZXZMBFJK-UHFFFAOYSA-N 5-(dimethylamino)pentane-1-thiol Chemical compound CN(C)CCCCCS BTRRKMZXZMBFJK-UHFFFAOYSA-N 0.000 description 2
- 241000203022 Acholeplasma laidlawii Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XMBZUNHETOKKBH-UHFFFAOYSA-N Dihydro-Mutilin Natural products CC1C(O)C(CC)(C)CC(O)C2(C)C(C)CCC31CCC(=O)C32 XMBZUNHETOKKBH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JHPVVOXKINUOSC-UHFFFAOYSA-N diethyl(methyl)azanium;iodide Chemical compound [I-].CC[NH+](C)CC JHPVVOXKINUOSC-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000005342 ion exchange Methods 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- IGZUNAJRZXRCSF-UHFFFAOYSA-N 1-(dibutylamino)ethanethiol Chemical compound CCCCN(C(C)S)CCCC IGZUNAJRZXRCSF-UHFFFAOYSA-N 0.000 description 1
- IZWSBHCOPASJIU-UHFFFAOYSA-N 1-morpholin-4-ylethanethiol;hydrochloride Chemical compound Cl.CC(S)N1CCOCC1 IZWSBHCOPASJIU-UHFFFAOYSA-N 0.000 description 1
- VLMKESHEPNXNIN-UHFFFAOYSA-N 1-piperidin-1-ylethanethiol;hydrochloride Chemical compound Cl.CC(S)N1CCCCC1 VLMKESHEPNXNIN-UHFFFAOYSA-N 0.000 description 1
- CYUWFRRFLRNCHI-UHFFFAOYSA-N 1-pyrrolidin-1-ylethanethiol Chemical compound CC(S)N1CCCC1 CYUWFRRFLRNCHI-UHFFFAOYSA-N 0.000 description 1
- OSBBLAPMQVESCS-UHFFFAOYSA-N 1-thiomorpholin-4-ylethanethiol Chemical compound S1CCN(CC1)C(C)S OSBBLAPMQVESCS-UHFFFAOYSA-N 0.000 description 1
- YBGNWNAEGNRKLO-UHFFFAOYSA-N 2-(azepan-1-yl)ethanethiol Chemical compound SCCN1CCCCCC1 YBGNWNAEGNRKLO-UHFFFAOYSA-N 0.000 description 1
- HFLIHGJYVCGOEH-UHFFFAOYSA-N 5-(dimethylamino)pentan-1-ol Chemical compound CN(C)CCCCCO HFLIHGJYVCGOEH-UHFFFAOYSA-N 0.000 description 1
- IPBUERDNRWYKON-UHFFFAOYSA-N 5-chloro-n,n-dimethylpentan-1-amine;hydrochloride Chemical compound Cl.CN(C)CCCCCCl IPBUERDNRWYKON-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241000202955 Mycoplasma bovigenitalium Species 0.000 description 1
- 241000204048 Mycoplasma hominis Species 0.000 description 1
- 241001127548 Mycoplasma hyorhinis ATCC 17981 Species 0.000 description 1
- 241001148555 Mycoplasma meleagridis Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- DSVGQVZAZSZEEX-UHFFFAOYSA-N [C].[Pt] Chemical compound [C].[Pt] DSVGQVZAZSZEEX-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 239000003957 anion exchange resin Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004820 blood count Methods 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- XMEVHPAGJVLHIG-FMZCEJRJSA-N chembl454950 Chemical compound [Cl-].C1=CC=C2[C@](O)(C)[C@H]3C[C@H]4[C@H]([NH+](C)C)C(O)=C(C(N)=O)C(=O)[C@@]4(O)C(O)=C3C(=O)C2=C1O XMEVHPAGJVLHIG-FMZCEJRJSA-N 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- RTOIPDPHQXGIRG-JKZASVEESA-N dihydropleuromutilin Chemical compound C[C@H]1[C@H](O)[C@@](CC)(C)C[C@@H](OC(=O)CO)C2(C)[C@H](C)CCC31CCC(=O)[C@H]32 RTOIPDPHQXGIRG-JKZASVEESA-N 0.000 description 1
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NRVFDGZJTPCULU-UHFFFAOYSA-N meda Chemical compound Cl.CN(C)CCS NRVFDGZJTPCULU-UHFFFAOYSA-N 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 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 description 1
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI794061A FI60204C (fi) | 1971-10-05 | 1979-12-27 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pleuromutiliner |
| FI794060A FI60198C (fi) | 1971-10-05 | 1979-12-27 | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pleuromutiliner |
Applications Claiming Priority (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1445071A CH560180A5 (en) | 1971-10-05 | 1971-10-05 | Pleuromutilin derivs - with antibacterial activity |
| CH1445171 | 1971-10-05 | ||
| CH1445071 | 1971-10-05 | ||
| CH1445171A CH559719A5 (en) | 1971-10-05 | 1971-10-05 | Pleuromutilin derivs - with antibacterial activity |
| CH773972 | 1972-05-25 | ||
| CH774072 | 1972-05-25 | ||
| CH773872 | 1972-05-25 | ||
| CH774072A CH575375A5 (en, 2012) | 1972-05-25 | 1972-05-25 | |
| CH773872A CH572893A5 (en) | 1972-05-25 | 1972-05-25 | Pleuromutilin derivs - with antibacterial activity |
| CH773972A CH568272A5 (en) | 1972-05-25 | 1972-05-25 | (Para-substd phenoxy- or phenylthio-acetoxy)-pleuromutilin deriv - prepd by reacting para-hydroxy or-mercapto cpds with e.g. aminoalkyl halides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58635B FI58635B (fi) | 1980-11-28 |
| FI58635C true FI58635C (fi) | 1981-03-10 |
Family
ID=27509313
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI2645/72A FI58635C (fi) | 1971-10-05 | 1972-09-26 | Foerfarande foer framstaellning av nya antimikrobiska pleuromutiliner |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4278674A (en, 2012) |
| JP (1) | JPS577147B2 (en, 2012) |
| BE (1) | BE789629A (en, 2012) |
| BG (2) | BG21386A3 (en, 2012) |
| CA (1) | CA979447A (en, 2012) |
| DD (1) | DD100706A5 (en, 2012) |
| DE (2) | DE2248237C2 (en, 2012) |
| DK (1) | DK139720B (en, 2012) |
| FI (1) | FI58635C (en, 2012) |
| FR (1) | FR2157828B1 (en, 2012) |
| GB (1) | GB1410505A (en, 2012) |
| HU (1) | HU168436B (en, 2012) |
| IE (1) | IE37699B1 (en, 2012) |
| IL (1) | IL40494A (en, 2012) |
| NL (1) | NL177403C (en, 2012) |
| NO (3) | NO136459C (en, 2012) |
| OA (1) | OA04192A (en, 2012) |
| PH (1) | PH11870A (en, 2012) |
| RO (2) | RO67478A (en, 2012) |
| SE (3) | SE398348B (en, 2012) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987194A (en) * | 1975-05-12 | 1976-10-19 | E. R. Squibb & Sons, Inc. | Use of pleuromutilin derivatives for the treatment of swine dysentery |
| DE2823712C2 (de) | 1978-05-31 | 1987-04-09 | Sandoz-Patent-GmbH, 7850 Lörrach | Verfahren zur Herstellung von Pleuromutilin-Derivaten |
| FR2428030A1 (fr) * | 1978-06-06 | 1980-01-04 | Sandoz Sa | Procede de preparation de derives de la pleuromutiline |
| JPS56168463A (en) * | 1980-05-30 | 1981-12-24 | Iwao Koyama | Telephone set |
| LU82738A1 (fr) * | 1980-08-29 | 1982-05-10 | Continental Pharma | Derives d'aminothiols,leur preparation et utilisation ainsi que compositions contenant ces derives |
| JPS60121870A (ja) * | 1983-12-06 | 1985-06-29 | Matsushita Electric Ind Co Ltd | インタ−ホン装置 |
| JPS62137952A (ja) * | 1985-12-12 | 1987-06-20 | Sakuragi Kunio | 電話機 |
| JPH01105238U (en, 2012) * | 1988-01-05 | 1989-07-14 | ||
| CA2240467A1 (en) * | 1996-01-03 | 1997-07-17 | Smithkline Beecham P.L.C. | Carbamoyloxy derivatives of mutiline and their use as antibacterials |
| FR2746012B1 (fr) * | 1996-03-13 | 1998-05-22 | Utilisation de la tiamuline pour la preparation d'un medicament comme agent de reversion de la multichimioresistance cancereuse | |
| UY25225A1 (es) * | 1997-10-29 | 2000-12-29 | Smithkline Beecham Plc | Derivados de pleuromutilina utiles como agentes antimicrobianos |
| WO2000027790A1 (en) * | 1998-11-11 | 2000-05-18 | Smithkline Beecham P.L.C. | Mutilin compounds |
| AU3036200A (en) * | 1998-12-18 | 2000-07-12 | Smithkline Beecham Plc | Mutilin 14-ester derivatives having antibacterial activity |
| GB9912657D0 (en) * | 1999-06-01 | 1999-07-28 | Smithkline Beecham Plc | Novel compounds |
| GB9918037D0 (en) * | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| GB0017031D0 (en) * | 2000-07-11 | 2000-08-30 | Biochemie Gmbh | Antimicrobials |
| PE20020676A1 (es) * | 2000-09-13 | 2002-08-27 | Biochemie Gmbh | Compuestos de mutilina como antibacterianos |
| GB0207495D0 (en) * | 2002-03-28 | 2002-05-08 | Biochemie Gmbh | Organic compounds |
| GB0308114D0 (en) * | 2003-04-08 | 2003-05-14 | Glaxo Group Ltd | Novel compounds |
| ATE450535T1 (de) * | 2003-09-03 | 2009-12-15 | Glaxo Group Ltd | Neues verfahren zur herstellung von pleuromutilinderivaten |
| GB0504314D0 (en) * | 2005-03-02 | 2005-04-06 | Glaxo Group Ltd | Novel polymorph |
| WO2006104667A2 (en) * | 2005-03-10 | 2006-10-05 | Smithkline Beecham Corporation | Novel method |
| GB0513058D0 (en) * | 2005-06-27 | 2005-08-03 | Sandoz Ag | Organic compounds |
| EP1808431A1 (en) * | 2006-01-16 | 2007-07-18 | Nabriva Therapeutics Forschungs GmbH | Mutilin derivatives and their use as pharmaceutical |
| WO2008117796A1 (ja) * | 2007-03-28 | 2008-10-02 | Dainippon Sumitomo Pharma Co., Ltd. | 新規ムチリン誘導体 |
| CN101434567B (zh) * | 2008-12-19 | 2012-10-24 | 李扬 | 一种二乙氨基乙硫醇的制备方法 |
| CN103709115A (zh) * | 2012-10-09 | 2014-04-09 | 山东亨利医药科技有限责任公司 | 截短侧耳素类抗生素衍生物 |
| MY176727A (en) | 2012-12-03 | 2020-08-20 | Pfizer | Selective androgen receptor modulators |
| CN104447449B (zh) * | 2014-12-30 | 2016-06-15 | 陕西师范大学 | 一锅法合成泰妙菌素的方法 |
| CN110981769B (zh) * | 2019-12-19 | 2022-02-18 | 江苏威凌生化科技有限公司 | 一种制备泰秒菌素的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT301753B (de) * | 1969-07-25 | 1972-09-25 | Biochemie Gmbh | Verfahren zur Herstellung neuer Pleuromutilin-Derivate |
| US3919290A (en) * | 1972-10-03 | 1975-11-11 | Sandoz Ltd | Substituted 14-desoxy-mutilins |
| US4107164A (en) * | 1971-10-05 | 1978-08-15 | Sandoz Ltd. | Certain pleuromulilin ester derivatives |
| US4032530A (en) * | 1971-10-05 | 1977-06-28 | Sandoz Ltd. | Certain pleuromutilins |
-
0
- BE BE789629D patent/BE789629A/xx not_active IP Right Cessation
-
1972
- 1972-09-26 SE SE7212374A patent/SE398348B/xx unknown
- 1972-09-26 DK DK475372AA patent/DK139720B/da not_active IP Right Cessation
- 1972-09-26 FI FI2645/72A patent/FI58635C/fi active
- 1972-09-27 NO NO3453/72A patent/NO136459C/no unknown
- 1972-09-29 NL NLAANVRAGE7213254,A patent/NL177403C/xx not_active IP Right Cessation
- 1972-09-29 PH PH13949A patent/PH11870A/en unknown
- 1972-10-02 GB GB4525972A patent/GB1410505A/en not_active Expired
- 1972-10-02 DE DE2248237A patent/DE2248237C2/de not_active Expired
- 1972-10-02 DE DE2265666A patent/DE2265666C2/de not_active Expired
- 1972-10-03 HU HUSA2407A patent/HU168436B/hu unknown
- 1972-10-03 CA CA153,116A patent/CA979447A/en not_active Expired
- 1972-10-03 IE IE1339/72A patent/IE37699B1/xx unknown
- 1972-10-03 RO RO7281505A patent/RO67478A/ro unknown
- 1972-10-03 RO RO7281506A patent/RO67479A/ro unknown
- 1972-10-04 JP JP9913872A patent/JPS577147B2/ja not_active Expired
- 1972-10-04 BG BG023481A patent/BG21386A3/xx unknown
- 1972-10-04 BG BG023482A patent/BG20773A3/xx unknown
- 1972-10-04 IL IL40494A patent/IL40494A/en unknown
- 1972-10-04 OA OA54711A patent/OA04192A/xx unknown
- 1972-10-05 DD DD166051A patent/DD100706A5/xx unknown
- 1972-10-05 FR FR7235340A patent/FR2157828B1/fr not_active Expired
-
1973
- 1973-12-04 NO NO4618/73A patent/NO137440C/no unknown
- 1973-12-04 NO NO4617/73A patent/NO136837C/no unknown
-
1975
- 1975-08-26 SE SE7509456A patent/SE424074B/xx unknown
- 1975-08-26 SE SE7509457A patent/SE419984B/xx unknown
-
1979
- 1979-11-29 US US06/098,333 patent/US4278674A/en not_active Expired - Lifetime
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