SE443787B - Forfarande for framstellning av substituerade kinolizidin- och indolizidinderivat - Google Patents
Forfarande for framstellning av substituerade kinolizidin- och indolizidinderivatInfo
- Publication number
- SE443787B SE443787B SE7805513A SE7805513A SE443787B SE 443787 B SE443787 B SE 443787B SE 7805513 A SE7805513 A SE 7805513A SE 7805513 A SE7805513 A SE 7805513A SE 443787 B SE443787 B SE 443787B
- Authority
- SE
- Sweden
- Prior art keywords
- compound
- calculated
- elemental analysis
- found
- recrystallization
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 10
- HAJKHJOABGFIGP-UHFFFAOYSA-N indolizidine Chemical class C1CCCN2CCCC21 HAJKHJOABGFIGP-UHFFFAOYSA-N 0.000 title claims description 3
- LJPZHJUSICYOIX-UHFFFAOYSA-N quinolizidine Chemical class C1CCCC2CCCCN21 LJPZHJUSICYOIX-UHFFFAOYSA-N 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 53
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 238000000921 elemental analysis Methods 0.000 claims description 30
- 238000002844 melting Methods 0.000 claims description 27
- 230000008018 melting Effects 0.000 claims description 27
- 238000001953 recrystallisation Methods 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 10
- -1 2- (dithen-2-ylmethylene) indolizidine-ethyl bromide Chemical compound 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 101100179824 Caenorhabditis elegans ins-17 gene Proteins 0.000 claims description 2
- 101150089655 Ins2 gene Proteins 0.000 claims description 2
- XQZQHGNNINXNCT-UHFFFAOYSA-N bromomethane;2-(dithiophen-2-ylmethylidene)-3,5,6,7,8,8a-hexahydro-1h-indolizine Chemical compound BrC.C1C2CCCCN2CC1=C(C=1SC=CC=1)C1=CC=CS1 XQZQHGNNINXNCT-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 13
- 239000013078 crystal Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- YECXOZONNKWGKM-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1H-quinolizine bromomethane Chemical compound BrC.C1CCCC2CCCCN21 YECXOZONNKWGKM-UHFFFAOYSA-N 0.000 description 3
- 229930003347 Atropine Natural products 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 3
- 229960000396 atropine Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- 229940102396 methyl bromide Drugs 0.000 description 3
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VFXZIMFKMXRVKV-UHFFFAOYSA-N 8-benzhydrylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine Chemical compound C1C2CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 VFXZIMFKMXRVKV-UHFFFAOYSA-N 0.000 description 2
- MPMXDAWRUSVQSU-UHFFFAOYSA-N 8-benzhydrylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine;hydrochloride Chemical compound Cl.C1C2CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 MPMXDAWRUSVQSU-UHFFFAOYSA-N 0.000 description 2
- JUOLMIOSPHYLRY-UHFFFAOYSA-N 9-benzhydrylidene-1,2,3,4,6,7,8,9a-octahydroquinolizine;bromomethane Chemical compound BrC.C12CCCCN2CCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 JUOLMIOSPHYLRY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- UCGJZJXOPSNTGZ-UHFFFAOYSA-M Prifinium bromide Chemical compound [Br-].CC1[N+](CC)(CC)CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 UCGJZJXOPSNTGZ-UHFFFAOYSA-M 0.000 description 2
- QTSXMEPZSHLZFF-UHFFFAOYSA-M Timepidium bromide Chemical compound [Br-].C1[N+](C)(C)CC(OC)CC1=C(C=1SC=CC=1)C1=CC=CS1 QTSXMEPZSHLZFF-UHFFFAOYSA-M 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- VEQCYNRYAQYICH-UHFFFAOYSA-N bromoethane;9-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,8,9a-octahydroquinolizine Chemical compound CCBr.C12CCCCN2CCCC1=C(C=1SC=CC=1)C1=CC=CS1 VEQCYNRYAQYICH-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229960005275 prifinium bromide Drugs 0.000 description 2
- 230000010344 pupil dilation Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000035922 thirst Effects 0.000 description 2
- 229960003737 timepidium bromide Drugs 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- PCKMKOIOHPIGSJ-UHFFFAOYSA-N 1-benzhydrylidene-3,5,6,7,8,8a-hexahydro-2h-indolizine Chemical compound C12CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 PCKMKOIOHPIGSJ-UHFFFAOYSA-N 0.000 description 1
- UMZOTETUQVFUIS-UHFFFAOYSA-N 1-benzhydrylidene-3,5,6,7,8,8a-hexahydro-2h-indolizine;bromoethane Chemical compound CCBr.C12CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 UMZOTETUQVFUIS-UHFFFAOYSA-N 0.000 description 1
- HDVAWXXJVMJBAR-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-1-ylmethanol Chemical compound C1CCCC2C(CO)CCCN21 HDVAWXXJVMJBAR-UHFFFAOYSA-N 0.000 description 1
- SAGGRGMQWAHRES-UHFFFAOYSA-N 2,3,4,6,7,8,9,9a-octahydro-1h-quinolizin-3-yl(phenyl)methanone Chemical compound C1CC2CCCCN2CC1C(=O)C1=CC=CC=C1 SAGGRGMQWAHRES-UHFFFAOYSA-N 0.000 description 1
- XJWRSCXGDIDATI-UHFFFAOYSA-N 2-(dithiophen-2-ylmethylidene)-3,5,6,7,8,8a-hexahydro-1h-indolizine Chemical compound C1C2CCCCN2CC1=C(C=1SC=CC=1)C1=CC=CS1 XJWRSCXGDIDATI-UHFFFAOYSA-N 0.000 description 1
- FDJHPXXRMFOMJR-UHFFFAOYSA-N 2-benzhydrylidene-3,5,6,7,8,8a-hexahydro-1h-indolizine Chemical compound C1C2CCCCN2CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 FDJHPXXRMFOMJR-UHFFFAOYSA-N 0.000 description 1
- LMLKLKONIPMOSU-UHFFFAOYSA-N 2-benzhydrylidene-3,5,6,7,8,8a-hexahydro-1h-indolizine;bromomethane Chemical compound BrC.C1C2CCCCN2CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 LMLKLKONIPMOSU-UHFFFAOYSA-N 0.000 description 1
- CGUWHYHJOHPWIZ-UHFFFAOYSA-N 2-benzhydrylidene-3,5,6,7,8,8a-hexahydro-1h-indolizine;iodomethane Chemical compound IC.C1C2CCCCN2CC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 CGUWHYHJOHPWIZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- VGRPVFKNUWHHCC-UHFFFAOYSA-N 8-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,9,9a-octahydroquinolizine Chemical compound C1C2CCCCN2CCC1=C(C=1SC=CC=1)C1=CC=CS1 VGRPVFKNUWHHCC-UHFFFAOYSA-N 0.000 description 1
- IXIVMDQLGOHJKM-UHFFFAOYSA-N 8-benzhydrylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine;bromoethane Chemical compound CCBr.C1C2CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 IXIVMDQLGOHJKM-UHFFFAOYSA-N 0.000 description 1
- FXYQSLCDNUQDPV-UHFFFAOYSA-N 8-benzhydrylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine;iodomethane Chemical compound IC.C1C2CCCCN2CCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 FXYQSLCDNUQDPV-UHFFFAOYSA-N 0.000 description 1
- JCNVNRJWEIBDRZ-UHFFFAOYSA-N 9-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,8,9a-octahydroquinolizine Chemical compound C12CCCCN2CCCC1=C(C=1SC=CC=1)C1=CC=CS1 JCNVNRJWEIBDRZ-UHFFFAOYSA-N 0.000 description 1
- SWZBMMCNBDMGKA-UHFFFAOYSA-N 9-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,8,9a-octahydroquinolizine;hydrochloride Chemical compound Cl.C12CCCCN2CCCC1=C(C=1SC=CC=1)C1=CC=CS1 SWZBMMCNBDMGKA-UHFFFAOYSA-N 0.000 description 1
- PAQDLFGONOLCCG-UHFFFAOYSA-N 9-benzhydrylidene-1,2,3,4,6,7,8,9a-octahydroquinolizine Chemical compound C12CCCCN2CCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 PAQDLFGONOLCCG-UHFFFAOYSA-N 0.000 description 1
- ZTGZMMAENJXGBB-UHFFFAOYSA-N 9-benzhydrylidene-1,2,3,4,6,7,8,9a-octahydroquinolizine;iodomethane Chemical compound IC.C12CCCCN2CCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 ZTGZMMAENJXGBB-UHFFFAOYSA-N 0.000 description 1
- DETZBXLXAYCFTM-UHFFFAOYSA-N 9-benzhydrylidene-1,2,3,4,6,7,8,9a-octahydroquinolizine;sulfuric acid Chemical compound OS(O)(=O)=O.C12CCCCN2CCCC1=C(C=1C=CC=CC=1)C1=CC=CC=C1 DETZBXLXAYCFTM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JVODFUNYAOEPHF-UHFFFAOYSA-N CI.C1(=CC=CC=C1)C(=C1CCN2CCCCC12)C1=CC=CC=C1 Chemical compound CI.C1(=CC=CC=C1)C(=C1CCN2CCCCC12)C1=CC=CC=C1 JVODFUNYAOEPHF-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000555745 Sciuridae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 150000001262 acyl bromides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- XTSSLMJWSGLPHX-UHFFFAOYSA-N bromomethane;8-(dithiophen-2-ylmethylidene)-1,2,3,4,6,7,9,9a-octahydroquinolizine Chemical compound BrC.C1C2CCCCN2CCC1=C(C=1SC=CC=1)C1=CC=CS1 XTSSLMJWSGLPHX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- HOZOZZFCZRXYEK-GSWUYBTGSA-M butylscopolamine bromide Chemical compound [Br-].C1([C@@H](CO)C(=O)O[C@H]2C[C@@H]3[N+]([C@H](C2)[C@@H]2[C@H]3O2)(C)CCCC)=CC=CC=C1 HOZOZZFCZRXYEK-GSWUYBTGSA-M 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- IUZPUBPFKPZPON-UHFFFAOYSA-N ethyl 1,2,3,5,6,7,8,8a-octahydroindolizine-1-carboxylate Chemical compound C1CCCC2C(C(=O)OCC)CCN21 IUZPUBPFKPZPON-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000021581 juice product Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D455/00—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine
- C07D455/02—Heterocyclic compounds containing quinolizine ring systems, e.g. emetine alkaloids, protoberberine; Alkylenedioxy derivatives of dibenzo [a, g] quinolizines, e.g. berberine containing not further condensed quinolizine ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pulmonology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Immunology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5526677A JPS53141294A (en) | 1977-05-16 | 1977-05-16 | 22diphenylmethylenequinolitidine and process for preparing same |
| JP10727077A JPS5441892A (en) | 1977-09-08 | 1977-09-08 | Quaternary salt derivative |
| JP13352677A JPS5467020A (en) | 1977-11-09 | 1977-11-09 | 33diphenylmethylenquinolysine quarternary salt derivative |
| JP14661377A JPS5481297A (en) | 1977-12-08 | 1977-12-08 | 11diphenylmethylene quinolitidine tertiary salt derivative |
| JP15284177A JPS5488293A (en) | 1977-12-21 | 1977-12-21 | Quaternary salt derivative |
| JP2153478A JPS54115396A (en) | 1978-02-28 | 1978-02-28 | 22dithienylmethylene quinolitidine quaternary salt derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7805513L SE7805513L (sv) | 1978-11-17 |
| SE443787B true SE443787B (sv) | 1986-03-10 |
Family
ID=27548989
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7805513A SE443787B (sv) | 1977-05-16 | 1978-05-12 | Forfarande for framstellning av substituerade kinolizidin- och indolizidinderivat |
Country Status (24)
| Country | Link |
|---|---|
| AR (1) | AR223814A1 (cs) |
| AT (1) | AT364362B (cs) |
| BE (1) | BE866988A (cs) |
| BG (1) | BG30018A3 (cs) |
| CA (1) | CA1100970A (cs) |
| CH (1) | CH635341A5 (cs) |
| CS (1) | CS211388B2 (cs) |
| DD (1) | DD142447A5 (cs) |
| DE (1) | DE2820687C2 (cs) |
| DK (1) | DK211278A (cs) |
| FI (1) | FI64368C (cs) |
| FR (1) | FR2390956A1 (cs) |
| GB (1) | GB1602927A (cs) |
| GR (1) | GR64422B (cs) |
| HU (1) | HU181441B (cs) |
| IT (1) | IT1113139B (cs) |
| NL (1) | NL186006C (cs) |
| NO (1) | NO149432C (cs) |
| NZ (1) | NZ187258A (cs) |
| PL (1) | PL115343B1 (cs) |
| PT (1) | PT68009B (cs) |
| SE (1) | SE443787B (cs) |
| SU (1) | SU953980A3 (cs) |
| YU (1) | YU40705B (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1994013289A1 (en) * | 1992-12-10 | 1994-06-23 | Tsentr Po Khimii Lekarstvennykh Sredstv | Pharmaceutical compound with anti-ulcer properties |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4089961A (en) * | 1976-11-08 | 1978-05-16 | Smithkline Corporation | Antipsychotically useful quinolizidylidene derivatives of xanthenes, thioxanthenes and dibenzoxepins |
-
1978
- 1978-04-24 BG BG039520A patent/BG30018A3/xx unknown
- 1978-05-03 IT IT7822967A patent/IT1113139B/it active
- 1978-05-08 CA CA302,858A patent/CA1100970A/en not_active Expired
- 1978-05-08 GR GR56170A patent/GR64422B/el unknown
- 1978-05-08 PT PT68009A patent/PT68009B/pt unknown
- 1978-05-11 AT AT0342378A patent/AT364362B/de not_active IP Right Cessation
- 1978-05-11 FR FR7814002A patent/FR2390956A1/fr active Granted
- 1978-05-11 DE DE2820687A patent/DE2820687C2/de not_active Expired
- 1978-05-11 CS CS783027A patent/CS211388B2/cs unknown
- 1978-05-12 SU SU782616071A patent/SU953980A3/ru active
- 1978-05-12 NO NO781693A patent/NO149432C/no unknown
- 1978-05-12 BE BE2056968A patent/BE866988A/xx not_active IP Right Cessation
- 1978-05-12 NZ NZ187258A patent/NZ187258A/xx unknown
- 1978-05-12 DD DD78205365A patent/DD142447A5/de unknown
- 1978-05-12 SE SE7805513A patent/SE443787B/sv not_active IP Right Cessation
- 1978-05-12 DK DK211278A patent/DK211278A/da not_active Application Discontinuation
- 1978-05-15 FI FI781525A patent/FI64368C/fi not_active IP Right Cessation
- 1978-05-15 PL PL1978206809A patent/PL115343B1/pl unknown
- 1978-05-16 YU YU1177/78A patent/YU40705B/xx unknown
- 1978-05-16 GB GB17814/78A patent/GB1602927A/en not_active Expired
- 1978-05-16 HU HU78HO2074A patent/HU181441B/hu not_active IP Right Cessation
- 1978-05-16 NL NLAANVRAGE7805272,A patent/NL186006C/xx not_active IP Right Cessation
- 1978-05-16 CH CH528678A patent/CH635341A5/de not_active IP Right Cessation
- 1978-05-16 AR AR272202A patent/AR223814A1/es active
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| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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