DD143774A5 - Verfahren zur herstellung von zwischenprodukten zur synthese von 1,9-dihydroxy-hexahydrodibenzopyranen - Google Patents
Verfahren zur herstellung von zwischenprodukten zur synthese von 1,9-dihydroxy-hexahydrodibenzopyranen Download PDFInfo
- Publication number
- DD143774A5 DD143774A5 DD76213370A DD21337076A DD143774A5 DD 143774 A5 DD143774 A5 DD 143774A5 DD 76213370 A DD76213370 A DD 76213370A DD 21337076 A DD21337076 A DD 21337076A DD 143774 A5 DD143774 A5 DD 143774A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- methyl
- dimethyl
- hydroxy
- aromatic
- radical
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 238000003786 synthesis reaction Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000013067 intermediate product Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000012312 sodium hydride Substances 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 4
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 description 35
- 239000003921 oil Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- -1 butoxy, pentoxy Chemical group 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 150000002500 ions Chemical class 0.000 description 11
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 7
- 239000005977 Ethylene Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000730 antalgic agent Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- HLAUCEOFCOXKNF-UHFFFAOYSA-N 2-bromoheptane Chemical compound CCCCCC(C)Br HLAUCEOFCOXKNF-UHFFFAOYSA-N 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 229940035676 analgesics Drugs 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 229960004242 dronabinol Drugs 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000002348 vinylic group Chemical group 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 2
- JFWGYKRUMPKNKF-UHFFFAOYSA-N 5,7-dihydroxy-2,2-dimethyl-3h-chromen-4-one Chemical compound C1=C(O)C=C2OC(C)(C)CC(=O)C2=C1O JFWGYKRUMPKNKF-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000001953 Hypotension Diseases 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 208000021822 hypotensive Diseases 0.000 description 2
- 230000001077 hypotensive effect Effects 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004309 pyranyl group Chemical class O1C(C=CC=C1)* 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YULFFYZCWUUTNC-YWPNNVDBSA-N (1r)-1-[(4r,4ar,8as)-2,6-bis(4-chlorophenyl)-4-methyl-8,8a-dihydro-4ah-[1,3]dioxino[5,4-d][1,3]dioxin-4-yl]ethane-1,2-diol Chemical compound C([C@@H]1OC(O[C@]([C@@H]1O1)(C)[C@H](O)CO)C=2C=CC(Cl)=CC=2)OC1C1=CC=C(Cl)C=C1 YULFFYZCWUUTNC-YWPNNVDBSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- OXTCFQFUNXTODT-UHFFFAOYSA-N 2-heptan-2-yloxy-2,3-dihydrochromen-4-one Chemical compound CC(CCCCC)OC1OC2=CC=CC=C2C(C1)=O OXTCFQFUNXTODT-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000005975 2-phenylethyloxy group Chemical group 0.000 description 1
- BVPCLVMIRNEUBW-UHFFFAOYSA-N 3-bromobutylbenzene Chemical compound CC(Br)CCC1=CC=CC=C1 BVPCLVMIRNEUBW-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- PCGYMVLAXCQBPQ-UHFFFAOYSA-N 4-bromopentylbenzene Chemical compound CC(Br)CCCC1=CC=CC=C1 PCGYMVLAXCQBPQ-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- BCWZCKDYMFWZLB-UHFFFAOYSA-N 5-(4-phenoxybutan-2-yl)benzene-1,3-diol Chemical compound C=1C(O)=CC(O)=CC=1C(C)CCOC1=CC=CC=C1 BCWZCKDYMFWZLB-UHFFFAOYSA-N 0.000 description 1
- DJNQFKJTTYUIFP-UHFFFAOYSA-N 5-(5-phenylpentan-2-yl)benzene-1,3-diol Chemical compound C=1C(O)=CC(O)=CC=1C(C)CCCC1=CC=CC=C1 DJNQFKJTTYUIFP-UHFFFAOYSA-N 0.000 description 1
- NPZVOFWVJHAEDH-UHFFFAOYSA-N 5-(5-pyridin-4-ylpentan-2-yl)benzene-1,3-diol Chemical compound C=1C(O)=CC(O)=CC=1C(C)CCCC1=CC=NC=C1 NPZVOFWVJHAEDH-UHFFFAOYSA-N 0.000 description 1
- CCECWYOKGVHLKC-UHFFFAOYSA-N 5-(6-phenylhexan-2-yl)benzene-1,3-diol Chemical compound C=1C(O)=CC(O)=CC=1C(C)CCCCC1=CC=CC=C1 CCECWYOKGVHLKC-UHFFFAOYSA-N 0.000 description 1
- BSBJNWAFSRQOGN-UHFFFAOYSA-N 5-hydroxy-2,2-dimethyl-7-sulfanyl-3h-chromen-4-one Chemical compound C1=C(S)C=C2OC(C)(C)CC(=O)C2=C1O BSBJNWAFSRQOGN-UHFFFAOYSA-N 0.000 description 1
- COAQQDPZYRYYOP-UHFFFAOYSA-N 5-hydroxy-3-(hydroxymethylidene)-2,2-dimethyl-7-(2-phenylethyl)chromen-4-one Chemical compound C=1C(O)=C2C(=O)C(=CO)C(C)(C)OC2=CC=1CCC1=CC=CC=C1 COAQQDPZYRYYOP-UHFFFAOYSA-N 0.000 description 1
- ZFVFQRLBTBBQSK-UHFFFAOYSA-N 5-phenylpentan-2-ol Chemical compound CC(O)CCCC1=CC=CC=C1 ZFVFQRLBTBBQSK-UHFFFAOYSA-N 0.000 description 1
- XWGCUHKGFJCGQA-UHFFFAOYSA-N 5-phenylpentan-2-yl methanesulfonate Chemical compound CS(=O)(=O)OC(C)CCCC1=CC=CC=C1 XWGCUHKGFJCGQA-UHFFFAOYSA-N 0.000 description 1
- AAIHVZNCFQTVCA-UHFFFAOYSA-N 9-nor-9β-hydroxyhexahydrocannabinol Chemical group C1C(O)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 AAIHVZNCFQTVCA-UHFFFAOYSA-N 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241001432959 Chernes Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 101000873676 Homo sapiens Secretogranin-2 Proteins 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 101100232411 Mus musculus Clns1a gene Proteins 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100035835 Secretogranin-2 Human genes 0.000 description 1
- 238000007239 Wittig reaction Methods 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000002456 anti-arthritic effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 125000001743 benzylic group Chemical group 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 0.000 description 1
- 239000003557 cannabinoid Chemical group 0.000 description 1
- 229930003827 cannabinoid Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004126 codeine Drugs 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000003533 narcotic effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- GZQUFIUZBLOTMM-UHFFFAOYSA-N pentyl methanesulfonate Chemical compound CCCCCOS(C)(=O)=O GZQUFIUZBLOTMM-UHFFFAOYSA-N 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
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- 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
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/20—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 hydrogenated in the hetero ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
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- Chemical & Material Sciences (AREA)
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- Veterinary Medicine (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Transplantation (AREA)
- Heart & Thoracic Surgery (AREA)
- Anesthesiology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US62821075A | 1975-11-03 | 1975-11-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD143774A5 true DD143774A5 (de) | 1980-09-10 |
Family
ID=24517939
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD76213370A DD143774A5 (de) | 1975-11-03 | 1976-11-01 | Verfahren zur herstellung von zwischenprodukten zur synthese von 1,9-dihydroxy-hexahydrodibenzopyranen |
| DD76203283A DD137837A5 (de) | 1975-11-03 | 1976-11-01 | Verfahren zur herstellung von zwischenprodukten fuer die synthese von 1,9-dihydroxy-hexahydro-dibenzopyranen |
| DD7600195548A DD129214A5 (de) | 1975-11-03 | 1976-11-01 | Verfahren zur herstellung von neuen 1,9-dihydroxy-hexahydrodibenzopyranen |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD76203283A DD137837A5 (de) | 1975-11-03 | 1976-11-01 | Verfahren zur herstellung von zwischenprodukten fuer die synthese von 1,9-dihydroxy-hexahydro-dibenzopyranen |
| DD7600195548A DD129214A5 (de) | 1975-11-03 | 1976-11-01 | Verfahren zur herstellung von neuen 1,9-dihydroxy-hexahydrodibenzopyranen |
Country Status (25)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0765890A (ja) * | 1993-08-26 | 1995-03-10 | Sumitomo Wiring Syst Ltd | コネクタ |
| JP2988237B2 (ja) * | 1994-01-31 | 1999-12-13 | 住友電装株式会社 | 簡易防水コネクタ |
| JP5037799B2 (ja) * | 2005-06-30 | 2012-10-03 | パナソニック株式会社 | テレビコンセント |
| JP7516898B2 (ja) | 2020-06-16 | 2024-07-17 | 株式会社アイシン | シフト装置 |
-
1976
- 1976-08-19 IE IE1842/76A patent/IE43700B1/en unknown
- 1976-10-11 SE SE7611275A patent/SE432251B/xx unknown
- 1976-10-18 GR GR51965A patent/GR65202B/el unknown
- 1976-10-19 IL IL50717A patent/IL50717A/xx unknown
- 1976-10-19 CA CA263,717A patent/CA1099269A/en not_active Expired
- 1976-10-19 NZ NZ182368A patent/NZ182368A/xx unknown
- 1976-10-21 ZA ZA766281A patent/ZA766281B/xx unknown
- 1976-10-22 PH PH19046A patent/PH14811A/en unknown
- 1976-10-27 ES ES452772A patent/ES452772A1/es not_active Expired
- 1976-11-01 DD DD76213370A patent/DD143774A5/de unknown
- 1976-11-01 RO RO7688274A patent/RO71411A/ro unknown
- 1976-11-01 YU YU02681/76A patent/YU268176A/xx unknown
- 1976-11-01 DD DD76203283A patent/DD137837A5/xx unknown
- 1976-11-01 RO RO7695638A patent/RO76124A/ro unknown
- 1976-11-01 DD DD7600195548A patent/DD129214A5/xx unknown
- 1976-11-01 RO RO7695637A patent/RO76006A/ro unknown
- 1976-11-01 RO RO7695639A patent/RO75876A/ro unknown
- 1976-11-02 PT PT65781A patent/PT65781B/pt unknown
- 1976-11-02 DK DK495876A patent/DK495876A/da not_active Application Discontinuation
- 1976-11-02 JP JP51132264A patent/JPS5277065A/ja active Granted
- 1976-11-02 FI FI763131A patent/FI763131A7/fi not_active Application Discontinuation
- 1976-11-02 NO NO763725A patent/NO148745C/no unknown
- 1976-11-02 HU HU76PI550A patent/HU178321B/hu unknown
- 1976-11-02 CS CS767070A patent/CS207571B2/cs unknown
- 1976-11-03 BG BG036486A patent/BG28057A4/xx unknown
- 1976-11-03 EG EG680/76A patent/EG12648A/xx active
- 1976-11-03 PL PL1976193435A patent/PL125297B1/pl not_active IP Right Cessation
- 1976-11-03 SU SU762416855A patent/SU843748A3/ru active
- 1976-11-03 BG BG034599A patent/BG27552A3/xx unknown
- 1976-11-03 BG BG036485A patent/BG28058A4/xx unknown
-
1977
- 1977-07-14 AR AR268433A patent/AR220521A1/es active
- 1977-07-19 PH PH20008A patent/PH14383A/en unknown
- 1977-07-26 SU SU772506503A patent/SU677661A3/ru active
- 1977-07-29 SU SU772505754A patent/SU677660A3/ru active
- 1977-09-29 ES ES462783A patent/ES462783A1/es not_active Expired
- 1977-09-29 ES ES462784A patent/ES462784A1/es not_active Expired
-
1978
- 1978-02-16 SU SU782579903A patent/SU784772A4/ru active
-
1979
- 1979-09-21 CH CH852079A patent/CH622790A5/fr not_active IP Right Cessation
- 1979-11-15 JP JP54148293A patent/JPS5943958B2/ja not_active Expired
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1980
- 1980-05-29 PH PH24092A patent/PH16788A/en unknown
- 1980-12-16 JP JP55177955A patent/JPS5943955B2/ja not_active Expired
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