NO118262B - - Google Patents

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Info

Publication number: NO118262B
Authority: NO; Norway
Prior art keywords: parts; volume; methanol; deserpidine; acid
Prior art date: 1966-02-07

Application number

NO166289A

Other languages

English (en)

Norwegian (no)

Inventor

Artur Fischer

Original Assignee

Artur Fischer

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1966-02-07

Filing date

1967-01-06

Publication date

1969-12-01

1967-01-06 Application filed by Artur Fischer filed Critical Artur Fischer

1969-12-01 Publication of NO118262B publication Critical patent/NO118262B/no

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 180
CVBMAZKKCSYWQR-BPJCFPRXSA-N Deserpidine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cccc3 CVBMAZKKCSYWQR-BPJCFPRXSA-N 0.000 claims description 42
229960001993 deserpidine Drugs 0.000 claims description 42
ISMCNVNDWFIXLM-WCGOZPBSSA-N deserpidine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ISMCNVNDWFIXLM-WCGOZPBSSA-N 0.000 claims description 42
238000002844 melting Methods 0.000 claims description 22
230000008018 melting Effects 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
238000002425 crystallisation Methods 0.000 claims description 16
230000008025 crystallization Effects 0.000 claims description 16
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 claims description 13
241000208332 Rauvolfia Species 0.000 claims description 13
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 claims description 13
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 claims description 13
238000000034 method Methods 0.000 claims description 13
229960003147 reserpine Drugs 0.000 claims description 13
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 claims description 13
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 claims description 13
241000196324 Embryophyta Species 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
229930013930 alkaloid Natural products 0.000 claims description 9
150000007513 acids Chemical class 0.000 claims description 7
150000003797 alkaloid derivatives Chemical class 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 5
238000000926 separation method Methods 0.000 claims description 5
230000015572 biosynthetic process Effects 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
238000000909 electrodialysis Methods 0.000 claims description 4
238000001179 sorption measurement Methods 0.000 claims description 3
239000002585 base Substances 0.000 claims 1
239000012458 free base Substances 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 57
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 55
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
239000000243 solution Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
239000000284 extract Substances 0.000 description 25
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000000463 material Substances 0.000 description 22
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
235000011054 acetic acid Nutrition 0.000 description 19
239000013078 crystal Substances 0.000 description 16
241000147497 Rauvolfia tetraphylla Species 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
238000009835 boiling Methods 0.000 description 10
239000012452 mother liquor Substances 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 9
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
235000011114 ammonium hydroxide Nutrition 0.000 description 8
239000002904 solvent Substances 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000005406 washing Methods 0.000 description 7
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 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
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
239000000287 crude extract Substances 0.000 description 6
238000000605 extraction Methods 0.000 description 6
235000011007 phosphoric acid Nutrition 0.000 description 6
239000000932 sedative agent Substances 0.000 description 6
230000001624 sedative effect Effects 0.000 description 6
229910002651 NO3 Inorganic materials 0.000 description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 5
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910017604 nitric acid Inorganic materials 0.000 description 5
-1 picronolates Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
239000003463 adsorbent Substances 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
239000002198 insoluble material Substances 0.000 description 4
239000000155 melt Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012454 non-polar solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000002798 polar solvent Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CJDRUOGAGYHKKD-UHFFFAOYSA-N Iso-ajmalin Natural products CN1C2=CC=CC=C2C2(C(C34)O)C1C1CC3C(CC)C(O)N1C4C2 CJDRUOGAGYHKKD-UHFFFAOYSA-N 0.000 description 3
OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 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
150000001875 compounds Chemical class 0.000 description 3
238000009826 distribution Methods 0.000 description 3
239000002035 hexane extract Substances 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical class OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
239000011347 resin Substances 0.000 description 3
229920005989 resin Polymers 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
CJDRUOGAGYHKKD-RQBLFBSQSA-N 1pon08459r Chemical compound CN([C@H]1[C@@]2(C[C@@]3([H])[C@@H]([C@@H](O)N42)CC)[H])C2=CC=CC=C2[C@]11C[C@@]4([H])[C@H]3[C@H]1O CJDRUOGAGYHKKD-RQBLFBSQSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
241001270428 Rauvolfia cubana Species 0.000 description 2
244000061121 Rauvolfia serpentina Species 0.000 description 2
241000610007 Rauvolfia vomitoria Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229960004332 ajmaline Drugs 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000000502 dialysis Methods 0.000 description 2
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
208000021822 hypotensive Diseases 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
238000002329 infrared spectrum Methods 0.000 description 2
238000002955 isolation Methods 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
150000002823 nitrates Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
239000000843 powder Substances 0.000 description 2
235000019260 propionic acid Nutrition 0.000 description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical class O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000008259 solid foam Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 description 2
UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
CZJDUZOWQVAEEV-XIEZEKGWSA-N (+)-19-epi-Ajmalicine Natural products O=C(OC)C=1[C@@H]2[C@@H]([C@@H](C)OC=1)C[N+]1[C@H](c3[nH]c4c(c3CC1)cccc4)C2 CZJDUZOWQVAEEV-XIEZEKGWSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
BIJIGLRLIDSMCO-UHFFFAOYSA-N Deserpidinsaeure-methylester Natural products C1=CC=C2C(CCN3CC4CC(O)C(C(C4CC33)C(=O)OC)OC)=C3NC2=C1 BIJIGLRLIDSMCO-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
CJDRUOGAGYHKKD-JZQIZOIBSA-N Isoajmaline Chemical compound CN1C2=CC=CC=C2[C@@]2([C@@H](C34)O)[C@@H]1[C@@H]1C[C@H]3[C@@H](CC)[C@H](O)N1[C@H]4C2 CJDRUOGAGYHKKD-JZQIZOIBSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
GRTOGORTSDXSFK-XJTZBENFSA-N ajmalicine Chemical compound C1=CC=C2C(CCN3C[C@@H]4[C@H](C)OC=C([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 GRTOGORTSDXSFK-XJTZBENFSA-N 0.000 description 1
229940007897 ajmalicine Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000012675 alcoholic extract Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
WYTGDNHDOZPMIW-RCBQFDQVSA-N alstonine Natural products C1=CC2=C3C=CC=CC3=NC2=C2N1C[C@H]1[C@H](C)OC=C(C(=O)OC)[C@H]1C2 WYTGDNHDOZPMIW-RCBQFDQVSA-N 0.000 description 1
229960004909 aminosalicylic acid Drugs 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
229960004365 benzoic acid Drugs 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000004531 blood pressure lowering effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
150000004862 dioxolanes Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000013505 freshwater Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
ICIWUVCWSCSTAQ-UHFFFAOYSA-N iodic acid Chemical class OI(=O)=O ICIWUVCWSCSTAQ-UHFFFAOYSA-N 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
230000005923 long-lasting effect Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000012528 membrane Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
239000008601 oleoresin Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
ZLQMRLSBXKQKMG-UHFFFAOYSA-N rauniticine Natural products COC(=O)C1=CC2CC3N(CCc4c3[nH]c5ccccc45)CC2C(C)O1 ZLQMRLSBXKQKMG-UHFFFAOYSA-N 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
QWAUBSSAJRGKPX-ZXKDJJQISA-O serpentinine Chemical compound N1C2=CC=CC=C2C(CCN2C\C3=C/C)=C1C2CC3C(C(=O)OC)CC(C=1C2=CC=CC=C2NC=11)=C[N+]2=C1CC1C(C(=O)OC)=COC(C)C1C2 QWAUBSSAJRGKPX-ZXKDJJQISA-O 0.000 description 1
QWAUBSSAJRGKPX-ZRJGMHBZSA-N serpentinine Natural products COC(=O)C(Cc1c[n+]2CC3C(C)OC=C(C3Cc2c4[n-]c5ccccc5c14)C(=O)OC)C6CC7N(CCc8c7[nH]c9ccccc89)C/C/6=C/C QWAUBSSAJRGKPX-ZRJGMHBZSA-N 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A63—SPORTS; GAMES; AMUSEMENTS
- A63H—TOYS, e.g. TOPS, DOLLS, HOOPS OR BUILDING BLOCKS
- A63H33/00—Other toys
- A63H33/04—Building blocks, strips, or similar building parts
- A63H33/042—Mechanical, electrical, optical, pneumatic or hydraulic arrangements; Motors

Landscapes

Toys (AREA)
Quick-Acting Or Multi-Walled Pipe Joints (AREA)
Actuator (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO166289A 1966-02-07 1967-01-06 NO118262B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DEF0048366		1966-02-07

Publications (1)

Publication Number	Publication Date
NO118262B true NO118262B (da)	1969-12-01

Family

ID=7102199

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO166289A NO118262B (da)	1966-02-07	1967-01-06

Country Status (13)

Country	Link
US (1)	US3475849A (da)
AT (1)	AT276175B (da)
BE (1)	BE691227A (da)
CH (1)	CH443096A (da)
DE (1)	DE1603294A1 (da)
ES (1)	ES336081A1 (da)
FI (1)	FI49777C (da)
FR (1)	FR1510464A (da)
GB (1)	GB1140795A (da)
IL (1)	IL27301A (da)
NL (1)	NL6618093A (da)
NO (1)	NO118262B (da)
SE (1)	SE368909B (da)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2441858C2 (de) *	1974-08-31	1985-05-09	Festo-Maschinenfabrik Gottlieb Stoll, 7300 Esslingen	Spiel- und Lehrbaukasten zur Darstellung von pneumatischen Bewegungsabläufen
DK138205B (da) *	1976-07-30	1978-07-31	Lego As	Plejlstangsled til legetøjsbyggesæt.
DK167379B1 (da) *	1990-12-04	1993-10-25	Lego As	Legetoejsbyggeelement med affjedringsmekanisme
US6893316B2 (en) *	2003-05-08	2005-05-17	Mattel, Inc.	Toys with mechanical interaction and method of using the same
US10695686B2 (en) *	2013-09-27	2020-06-30	Innovation First, Inc.	Mechanical spinning robot toy
CN112530239B (zh) *	2020-12-09	2022-06-24	杭州超乎智能科技有限公司	一种便于组装的控制板

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1060619A (en) *	1911-08-25	1913-05-06	Pinafour Toy Mfg Company	Toy.
US2451593A (en) *	1945-10-11	1948-10-19	Jr George Washington	Suction gun
GB616778A (en) *	1946-12-30	1949-01-26	Alfred James Watkins	Toy steam engine
US3076286A (en) *	1955-07-15	1963-02-05	Stephen J Czecholinski	Building blocks
US3193149A (en) *	1963-09-03	1965-07-06	Everett E Beaubien	Toy liquid dispenser

1966
- 1966-02-07 DE DE19661603294 patent/DE1603294A1/de active Pending
- 1966-12-12 AT AT1142966A patent/AT276175B/de active
- 1966-12-14 BE BE691227D patent/BE691227A/xx unknown
- 1966-12-23 NL NL6618093A patent/NL6618093A/xx unknown
- 1966-12-28 SE SE17779/66A patent/SE368909B/xx unknown
1967
- 1967-01-06 NO NO166289A patent/NO118262B/no unknown
- 1967-01-23 IL IL27301A patent/IL27301A/xx unknown
- 1967-01-26 CH CH129967A patent/CH443096A/de unknown
- 1967-01-26 ES ES0336081A patent/ES336081A1/es not_active Expired
- 1967-02-01 US US613299A patent/US3475849A/en not_active Expired - Lifetime
- 1967-02-02 FI FI670298A patent/FI49777C/fi active
- 1967-02-03 GB GB5405/67A patent/GB1140795A/en not_active Expired
- 1967-02-06 FR FR93793A patent/FR1510464A/fr not_active Expired

Also Published As

Publication number	Publication date
NL6618093A (da)	1967-08-08
SE368909B (da)	1974-07-29
FR1510464A (fr)	1968-01-19
IL27301A (en)	1970-09-17
GB1140795A (en)	1969-01-22
BE691227A (da)	1967-05-16
FI49777B (da)	1975-06-30
FI49777C (fi)	1975-10-10
US3475849A (en)	1969-11-04
ES336081A1 (es)	1967-12-16
AT276175B (de)	1969-11-10
DE1603294A1 (de)	1970-08-13
CH443096A (de)	1967-08-31

Publication	Publication Date	Title
EP0036087B1 (en)	1983-05-25	Process for isolating rosmarinic acid from plants
NO143347B (no)	1980-10-13	Utgangsmateriale for fremstilling av benzodiazepinderivater
US2752351A (en)	1956-06-26	Crystalline reserpine, salts and compositions thereof
NO118262B (da)	1969-12-01
US2824874A (en)	1958-02-25	Reserpic acid and derivatives
DE2823461A1 (de)	1978-12-14	Verfahren zur gewinnung der alkaloid- komponenten der pflanze vinca rosea l.
US4198344A (en)	1980-04-15	Process for the preparation of polyhydroxylated steroids, lysergol and ergolinic alkaloids
US6147228A (en)	2000-11-14	Convenient method for the large scale isolation of garcinia acid
FI56968B (fi)	1980-01-31	Foerfarande foer framstaellning av hoegren kristallisk kenodesoxicholsyra
US3033877A (en)	1962-05-08	Process of preparing same
Manske	1943	THE ALKALOIDS OF FUMARIACEOUS PLANTS: XXXVI. CORYDALIS THALICTRIFOLIA FRANCH. AND THE CONSTITUTION OF A NEW ALKALOID, THALICTRIFOLINE
US2866784A (en)	1958-12-30	Process for obtaining voacanga alkaloids
Saito et al.	1934	On the alkaloids of white hellebore. I. Isolation of constituent alkaloids
US2252709A (en)	1941-08-19	Erythramine and process for its production
US3008954A (en)	1961-11-14	Process for obtaining an koquinuclt
US2982769A (en)	1961-05-02	Active substance and process for
US2876228A (en)	1959-03-03	Recovery of rescinnamine
SU700130A1 (ru)	1979-11-30	Способ получени строфантидина
US2945851A (en)	1960-07-19	Process for obtaining an active substance with action on the heart from plants of the voacanga genus
SU912034A3 (ru)	1982-03-07	Способ разделени алкалоидов дииндола
US2963475A (en)	1960-12-06	Process for extraction of alkaloidal substance from plants of the apocynaceae family
SU613757A1 (ru)	1978-07-05	Способ получени аймалина
US2346753A (en)	1944-04-18	Process for the preparation of cardiac glucoside
SU435825A1 (ru)	1974-07-15	Способ получения олеандрина
RU2157204C1 (ru)	2000-10-10	Способ получения платифиллина гидротартрата