CH648837A5 - Zuckeralkoholderivate, verfahren zu ihrer herstellung, die diese verbindungen enthaltenden pharmazeutischen zubereitungen. - Google Patents
Zuckeralkoholderivate, verfahren zu ihrer herstellung, die diese verbindungen enthaltenden pharmazeutischen zubereitungen. Download PDFInfo
- Publication number
- CH648837A5 CH648837A5 CH6179/80A CH617980A CH648837A5 CH 648837 A5 CH648837 A5 CH 648837A5 CH 6179/80 A CH6179/80 A CH 6179/80A CH 617980 A CH617980 A CH 617980A CH 648837 A5 CH648837 A5 CH 648837A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- dianhydro
- compounds
- compound
- dulcite
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 68
- 238000000034 method Methods 0.000 title claims description 20
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000005846 sugar alcohols Chemical class 0.000 title description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 38
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 23
- -1 acyl anhydride Chemical class 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 239000000811 xylitol Substances 0.000 claims description 11
- 229960002675 xylitol Drugs 0.000 claims description 11
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 239000011230 binding agent Substances 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000011987 methylation Effects 0.000 claims description 8
- 238000007069 methylation reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 5
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 5
- 229930195725 Mannitol Natural products 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000003435 aroyl group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 239000000594 mannitol Substances 0.000 claims description 5
- 235000010355 mannitol Nutrition 0.000 claims description 5
- 239000012022 methylating agents Substances 0.000 claims description 5
- 239000000600 sorbitol Substances 0.000 claims description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
- 239000012312 sodium hydride Substances 0.000 claims description 3
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 3
- IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Inorganic materials [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 claims description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical class CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims description 2
- 229910015900 BF3 Inorganic materials 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 claims description 2
- 229910044991 metal oxide Inorganic materials 0.000 claims description 2
- 150000004706 metal oxides Chemical class 0.000 claims description 2
- 125000001477 organic nitrogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229910001923 silver oxide Inorganic materials 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 4
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000158147 Sator Species 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 150000001266 acyl halides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- 125000005270 trialkylamine group Chemical group 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 84
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 239000011541 reaction mixture Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 31
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000003480 eluent Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 229920006395 saturated elastomer Polymers 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- 239000012230 colorless oil Substances 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- 239000007789 gas Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 229960002920 sorbitol Drugs 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000001085 cytostatic effect Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-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
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- SKCKOFZKJLZSFA-SSGXUJNVSA-N (2R,3S,4S)-hexane-1,2,3,4,5-pentol Chemical compound CC([C@H](O)[C@@H](O)[C@H](O)CO)O SKCKOFZKJLZSFA-SSGXUJNVSA-N 0.000 description 1
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- RILZRCJGXSFXNE-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]ethanol Chemical compound OCCC1=CC=C(OC(F)(F)F)C=C1 RILZRCJGXSFXNE-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 201000000274 Carcinosarcoma Diseases 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 239000000824 cytostatic agent Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Medicinal Preparation (AREA)
- Epoxy Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79VI1266A HU179076B (en) | 1979-08-17 | 1979-08-17 | Process for producing terminal bifunctional xilite-methyl-ethers of citostatic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH648837A5 true CH648837A5 (de) | 1985-04-15 |
Family
ID=11002943
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH6179/80A CH648837A5 (de) | 1979-08-17 | 1980-08-15 | Zuckeralkoholderivate, verfahren zu ihrer herstellung, die diese verbindungen enthaltenden pharmazeutischen zubereitungen. |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5630936A (cs) |
| AT (1) | AT370416B (cs) |
| BE (1) | BE884780A (cs) |
| CA (1) | CA1189525A (cs) |
| CH (1) | CH648837A5 (cs) |
| CS (1) | CS214839B2 (cs) |
| DD (1) | DD153872A5 (cs) |
| DE (1) | DE3030963A1 (cs) |
| DK (1) | DK354980A (cs) |
| FI (1) | FI802551A7 (cs) |
| FR (1) | FR2463762A1 (cs) |
| GB (1) | GB2058760B (cs) |
| HU (1) | HU179076B (cs) |
| NL (1) | NL8004631A (cs) |
| NO (1) | NO152412C (cs) |
| PL (1) | PL130388B1 (cs) |
| SE (1) | SE8005780L (cs) |
| SU (1) | SU1075975A3 (cs) |
-
1979
- 1979-08-17 HU HU79VI1266A patent/HU179076B/hu unknown
-
1980
- 1980-08-13 FI FI802551A patent/FI802551A7/fi not_active Application Discontinuation
- 1980-08-14 DD DD223328A patent/DD153872A5/de unknown
- 1980-08-14 BE BE0/201751A patent/BE884780A/fr not_active IP Right Cessation
- 1980-08-14 AT AT0416180A patent/AT370416B/de not_active IP Right Cessation
- 1980-08-14 FR FR8017974A patent/FR2463762A1/fr active Granted
- 1980-08-15 SU SU802963500A patent/SU1075975A3/ru active
- 1980-08-15 CS CS805630A patent/CS214839B2/cs unknown
- 1980-08-15 DK DK354980A patent/DK354980A/da not_active Application Discontinuation
- 1980-08-15 NO NO802451A patent/NO152412C/no unknown
- 1980-08-15 SE SE8005780A patent/SE8005780L/xx not_active Application Discontinuation
- 1980-08-15 NL NL8004631A patent/NL8004631A/nl not_active Application Discontinuation
- 1980-08-15 CH CH6179/80A patent/CH648837A5/de not_active IP Right Cessation
- 1980-08-15 CA CA000358377A patent/CA1189525A/en not_active Expired
- 1980-08-15 GB GB8026633A patent/GB2058760B/en not_active Expired
- 1980-08-16 PL PL1980226283A patent/PL130388B1/pl unknown
- 1980-08-16 DE DE19803030963 patent/DE3030963A1/de not_active Withdrawn
- 1980-08-18 JP JP11332980A patent/JPS5630936A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| NO802451L (no) | 1981-02-18 |
| FI802551A7 (fi) | 1981-01-01 |
| AT370416B (de) | 1983-03-25 |
| GB2058760A (en) | 1981-04-15 |
| BE884780A (fr) | 1980-12-01 |
| NO152412C (no) | 1985-09-25 |
| PL130388B1 (en) | 1984-08-31 |
| GB2058760B (en) | 1983-07-06 |
| FR2463762A1 (fr) | 1981-02-27 |
| CS214839B2 (en) | 1982-06-25 |
| DD153872A5 (de) | 1982-02-10 |
| DK354980A (da) | 1981-02-18 |
| SU1075975A3 (ru) | 1984-02-23 |
| CA1189525A (en) | 1985-06-25 |
| HU179076B (en) | 1982-08-28 |
| FR2463762B1 (cs) | 1984-10-26 |
| JPS5630936A (en) | 1981-03-28 |
| DE3030963A1 (de) | 1981-03-19 |
| ATA416180A (de) | 1982-08-15 |
| NL8004631A (nl) | 1981-02-19 |
| SE8005780L (sv) | 1981-02-18 |
| PL226283A1 (cs) | 1981-05-22 |
| NO152412B (no) | 1985-06-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD201793A5 (de) | Verfahren zur herstellung von 6-hydroxy-2-(4-hydroxy-phenyl) 3-(4-(2-aminoethoxy)benzoyl)benzo(b)thiophenen | |
| DE2750812C2 (de) | 4-Alkoxy-4-desmethoxydaunomycine und Verfahren zu deren Herstellung | |
| DE2804099A1 (de) | Carminomycinderivate, verfahren zu ihrer herstellung und ihre verwendung | |
| EP0086324B1 (de) | Verfahren zur Herstellung von Ascorbinsäure | |
| EP0004522A2 (de) | Neue dilignolähnliche Verbindungen, dilignolähnliche Verbindungen zur Verwendung bei der Behandlung von Lebererkrankungen sowie diese enthaltende pharmazeutische Präparate | |
| DE3132475A1 (de) | Neue cytostatisch wirksame verbindungen und verfahren zu ihrer herstellung | |
| EP0139859B1 (de) | 1,4-Dihydropyridine, Verfahren zu ihrer Herstellung sowie ihre Verwendung in Arzneimitteln | |
| CH648837A5 (de) | Zuckeralkoholderivate, verfahren zu ihrer herstellung, die diese verbindungen enthaltenden pharmazeutischen zubereitungen. | |
| CH616143A5 (cs) | ||
| DE69229017T2 (de) | Glyceraldehyd-3-pentanid und Verfahren zu ihrer Herstellung | |
| DE2900119C2 (de) | 4''-Desoxy-4''-carbamat- und -dithiocarbamat-Derivate des 11-Acetyl-oleandomycins und deren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE2601333A1 (de) | Neue chemische verbindungen, verfahren zu ihrer herstellung und ihre verwendung als zwischenprodukte | |
| DE3590057C1 (de) | Verfahren zur Herstellung von Diacyldianhydrohexiten | |
| EP0162235B1 (de) | Enantiomerenreine acetalisch mono-geschützte Diole, deren Herstellung und Verwendung | |
| DE3109532C2 (de) | Stereoisomere 1,4;3,6-Dianhydro-2,5-diazido-2,5-didesoxyhexite, Verfahren zur Herstellung derselben und diese Verbindungen enthaltende Arzneimittel | |
| AT381938B (de) | Verfahren zur herstellung von neuen spirobenzofuranonverbindungen | |
| DE2112778A1 (de) | Verfahren zur Herstellung von 2-Cyan-3,4,5,6-tetrahalogenbenzoesaeurealkylestern | |
| CH628634A5 (de) | Verfahren zur herstellung von 2,2'-bis(3,4-epoxy-5-oxotetrahydropyran)aether und produkt. | |
| CH639082A5 (de) | Bicyclische lactol-methyl-aether und ein verfahren zu ihrer herstellung. | |
| DE69909960T2 (de) | Cyclopropylestern von Alfa-Tocopherol, Vitamin E Derivate und Verfahren zu deren Herstellung | |
| CH642975A5 (de) | 4''-deoxy-4''-glyoxamido- und -carbonylthioformamidoderivate von oleandomycin und dessen estern, verfahren zu ihrer herstellung und diese enthaltende arzneimittel. | |
| CH648320A5 (de) | Cytostatische verbindungen, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende arzneimittel. | |
| AT260920B (de) | Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen | |
| AT313913B (de) | Verfahren zur Herstellung von neuen 1.2.3-Trithianverbindungen und deren Salzen | |
| EP0175264B1 (de) | Verfahren zur Herstellung von 2-Amino-3-cyano-5-dialkoxymethyl-pyrazinen und Zwischenprodukte für dieses Verfahren |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |