DK142700B - Analogifremgangsmåde til fremstilling af pleuromutiliner. - Google Patents
Analogifremgangsmåde til fremstilling af pleuromutiliner. Download PDFInfo
- Publication number
- DK142700B DK142700B DK498176A DK498176A DK142700B DK 142700 B DK142700 B DK 142700B DK 498176 A DK498176 A DK 498176A DK 498176 A DK498176 A DK 498176A DK 142700 B DK142700 B DK 142700B
- Authority
- DK
- Denmark
- Prior art keywords
- general formula
- deoxy
- compound
- piperazino
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- -1 ethylmercaptoacetoxy Chemical group 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OBUUFWIMEGVAQS-KWMSOUESSA-N (1S,2R,3S,4S,6R,7R,8S,14R)-4-ethenyl-3,6-dihydroxy-2,4,7,14-tetramethyltricyclo[5.4.3.01,8]tetradecan-9-one Chemical class C([C@H]([C@@]1(C)[C@H](O)C[C@@](C)(C=C)[C@@H](O)[C@@H]2C)C)C[C@]32[C@@H]1C(=O)CC3 OBUUFWIMEGVAQS-KWMSOUESSA-N 0.000 description 7
- STZYTFJPGGDRJD-NHUWBDDWSA-N retapamulin Chemical class 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 7
- 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 6
- 239000000047 product Substances 0.000 description 6
- 229960002771 retapamulin Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 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 4
- 239000012442 inert solvent Substances 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229960004989 tetracycline hydrochloride Drugs 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEPLMSNXIMBXSO-UHFFFAOYSA-N 2-[4-(1-sulfanylethyl)piperazin-1-yl]ethanol Chemical compound CC(S)N1CCN(CCO)CC1 WEPLMSNXIMBXSO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000009835 boiling Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- WFCSWCVEJLETKA-UHFFFAOYSA-N 2-piperazin-1-ylethanol Chemical compound OCCN1CCNCC1 WFCSWCVEJLETKA-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 description 1
- 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 1
- 206010023567 Labyrinthitis Diseases 0.000 description 1
- 241001430197 Mollicutes Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000202955 Mycoplasma bovigenitalium Species 0.000 description 1
- 241000204022 Mycoplasma gallisepticum Species 0.000 description 1
- 241000204048 Mycoplasma hominis Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 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
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK498176A DK142700B (da) | 1971-10-05 | 1976-11-03 | Analogifremgangsmåde til fremstilling af pleuromutiliner. |
Applications Claiming Priority (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1445071 | 1971-10-05 | ||
| CH1445171 | 1971-10-05 | ||
| CH1445171A CH559719A5 (en) | 1971-10-05 | 1971-10-05 | Pleuromutilin derivs - with antibacterial activity |
| CH1445071A CH560180A5 (en) | 1971-10-05 | 1971-10-05 | Pleuromutilin derivs - with antibacterial activity |
| CH774072A CH575375A5 (cs) | 1972-05-25 | 1972-05-25 | |
| 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 |
| CH773972 | 1972-05-25 | ||
| CH773872A CH572893A5 (en) | 1972-05-25 | 1972-05-25 | Pleuromutilin derivs - with antibacterial activity |
| CH774072 | 1972-05-25 | ||
| CH773872 | 1972-05-25 | ||
| DK475372 | 1972-09-26 | ||
| DK475372AA DK139720B (da) | 1971-10-05 | 1972-09-26 | Analogifremgangsmåde til fremstilling af pleuromutiliner. |
| DK498176 | 1976-11-03 | ||
| DK498176A DK142700B (da) | 1971-10-05 | 1976-11-03 | Analogifremgangsmåde til fremstilling af pleuromutiliner. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK498176A DK498176A (cs) | 1976-11-03 |
| DK142700B true DK142700B (da) | 1980-12-22 |
| DK142700C DK142700C (cs) | 1981-09-28 |
Family
ID=27561129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK498176A DK142700B (da) | 1971-10-05 | 1976-11-03 | Analogifremgangsmåde til fremstilling af pleuromutiliner. |
Country Status (1)
| Country | Link |
|---|---|
| DK (1) | DK142700B (cs) |
-
1976
- 1976-11-03 DK DK498176A patent/DK142700B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK498176A (cs) | 1976-11-03 |
| DK142700C (cs) | 1981-09-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1194875A (fr) | Procede pour la preparation de derive de la thieno [3,2-c] pyridine et les derives ainsi obtenus | |
| GB2143528A (en) | Salts of 2-(2,6-dichloroanilino)-phenyl acetic acid | |
| FI69839C (fi) | Foerfarande foer framstaellning av terapeutiskt aktiva difenylmetoxialkylpiperazinderivat | |
| FI63244C (fi) | Foerfarande foer framstaellning av antibakteriska erytromysinderivater | |
| NO137440B (no) | Analogifremgangsm}te for fremstilling av terapeutisk aktive pleuromutiliner | |
| FR2471968A1 (fr) | Ethers basiques, leur procede de preparation et compositions pharmaceutiques les contenant | |
| FR2581993A1 (fr) | Derives de (benzoyl-4 piperidino)-2 phenyl-1 alcanols, leur preparation et leur application en therapeutique | |
| CH644348A5 (fr) | Amino-ethers oxydes, leur procede de preparation et medicament les contenant. | |
| SK106595A3 (en) | Substituted derivatives of 4-phenyl-6-amino-nicotinic acid, mnufacturing process thereof, drugs containing these substances and their use | |
| EP0579681A1 (en) | Crystalline tiagabine hydrochloride monohydrate, its preparation and use | |
| KR880002273B1 (ko) | 아미디노 피페리딘 유도체의 제조방법 | |
| FR2704224A1 (fr) | Nouveaux acides et esters phénoxy isobutyriques substitués. | |
| US4886835A (en) | Alkadiene derivatives, their preparation, and pharmaceutical compositions containing them | |
| US6136852A (en) | 3,4-disubstituted phenylethanolaminotetralincarboxylic acid derivatives | |
| FR2549059A1 (fr) | Procede de preparation de 1-pyridyl-alkyl-4-aryl-piperazines, leur separation en les antipodes optiques (enantiomorphes) respectifs et les stereo-isomeres ainsi obtenus | |
| HU211579A9 (en) | 2-amino-5-cyano-1,4-dihydropyridines, and their use in medicaments | |
| US4285935A (en) | Dehydropeptide compounds, their production and their medical use | |
| EP0146392A1 (en) | B-phenethanolamine antiobesity agents | |
| FR2549058A1 (fr) | Nouveaux derives de la 1,4-dihydropyridine, leur preparation et leur utilisation comme medicaments | |
| DK142700B (da) | Analogifremgangsmåde til fremstilling af pleuromutiliner. | |
| FR2753970A1 (fr) | Derives de n-(benzothiazol-2-yl) piperidine-1-ethanamine, leur preparation et leur application en therapeutique | |
| DE3625738A1 (de) | 2-acyloxypropylamin-derivate, verfahren zu deren herstellung und deren verwendung | |
| US4275068A (en) | Lipid lowering alkylene glycols and ester derivatives thereof | |
| FR2555580A1 (fr) | Nouveaux composes azabicycliques, procede pour les preparer et medicaments les contenant | |
| FI60204B (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara pleuromutiliner |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |