CH400177A - Procédé de préparation d'alcaloïdes - Google Patents

Procédé de préparation d'alcaloïdes

Info

Publication number: CH400177A
Authority: CH; Switzerland
Prior art keywords: acid; group; toxiferin; acidic substance; aldehyde
Prior art date: 1958-10-17

Application number

CH7956659A

Other languages

English (en)

French (fr)

Inventor

Rushton Battersby Alan

Francis Hodson Harold

Original Assignee

Nat Res Dev

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.)

1958-10-17

Filing date

1959-10-16

Publication date

1965-10-15

1958-10-17 Priority claimed from GB3329958A external-priority patent/GB938801A/en

1959-10-16 Application filed by Nat Res Dev filed Critical Nat Res Dev

1965-10-15 Publication of CH400177A publication Critical patent/CH400177A/fr

Links

229930013930 alkaloid Natural products 0.000 title claims description 11
238000004519 manufacturing process Methods 0.000 title description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical group CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 11
230000002378 acidificating effect Effects 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
150000001450 anions Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
-1 hydroxyethyl group Chemical group 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical group CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 claims description 2
125000001931 aliphatic group Chemical group 0.000 claims description 2
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
125000005546 pivalic acid group Chemical group 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
UFUDXCDPABDFHK-UHFFFAOYSA-N Wieland - Gumlich aldehyde Natural products C1C2C(C3NC=4C5=CC=CC=4)C(O)OCC=C2CN2C1C35CC2 UFUDXCDPABDFHK-UHFFFAOYSA-N 0.000 description 13
UFUDXCDPABDFHK-SRCYXDNASA-N caracurine VII Chemical compound O[C@@H]([C@H]([C@H]1C2)[C@@H]3NC=4C5=CC=CC=4)OCC=C1CN1[C@@H]2[C@]35CC1 UFUDXCDPABDFHK-SRCYXDNASA-N 0.000 description 11
IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000002253 acid Substances 0.000 description 8
150000003797 alkaloid derivatives Chemical class 0.000 description 8
241001279009 Strychnos toxifera Species 0.000 description 7
239000000203 mixture Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 6
238000005956 quaternization reaction Methods 0.000 description 6
GXFZCDMWGMFGFL-KKXMJGKMSA-N (+)-Tubocurarine chloride hydrochloride Chemical compound [Cl-].[Cl-].C([C@H]1[N+](C)(C)CCC=2C=C(C(=C(OC3=CC=C(C=C3)C[C@H]3C=4C=C(C(=CC=4CC[NH+]3C)OC)O3)C=21)O)OC)C1=CC=C(O)C3=C1 GXFZCDMWGMFGFL-KKXMJGKMSA-N 0.000 description 5
239000008709 Curare Substances 0.000 description 5
238000000862 absorption spectrum Methods 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
229920001429 chelating resin Polymers 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012299 nitrogen atmosphere Substances 0.000 description 4
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
239000002994 raw material Substances 0.000 description 4
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
229940073608 benzyl chloride Drugs 0.000 description 3
238000004821 distillation Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
230000004048 modification Effects 0.000 description 3
238000012986 modification Methods 0.000 description 3
238000004816 paper chromatography Methods 0.000 description 3
229940075930 picrate Drugs 0.000 description 3
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000005406 washing Methods 0.000 description 3
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000003957 anion exchange resin Substances 0.000 description 2
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
210000002196 fr. b Anatomy 0.000 description 2
230000008018 melting Effects 0.000 description 2
238000002844 melting Methods 0.000 description 2
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
229960005453 strychnine Drugs 0.000 description 2
238000002211 ultraviolet spectrum Methods 0.000 description 2
OIKWZAMGBNHJCU-UHFFFAOYSA-N 2,2-dimethylpropanoic acid Chemical compound CC(C)(C)C(O)=O.CC(C)(C)C(O)=O OIKWZAMGBNHJCU-UHFFFAOYSA-N 0.000 description 1
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
230000002921 anti-spasmodic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
150000005524 benzylchlorides Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000007857 degradation product Substances 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
210000003918 fraction a Anatomy 0.000 description 1
210000000540 fraction c Anatomy 0.000 description 1
230000004927 fusion Effects 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000004686 pentahydrates Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
235000019814 powdered cellulose Nutrition 0.000 description 1
229920003124 powdered cellulose Polymers 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
230000003313 weakening effect Effects 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
- C07D471/22—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 systems contains four or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/22—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains four or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH7956659A 1958-10-17 1959-10-16 Procédé de préparation d'alcaloïdes CH400177A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB3329958A GB938801A (en)	1958-10-17	1958-10-17	Production of alkaloids and analogues thereof
GB3633858		1958-11-12

Publications (1)

Publication Number	Publication Date
CH400177A true CH400177A (fr)	1965-10-15

Family

ID=26261809

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7956659A CH400177A (fr)	1958-10-17	1959-10-16	Procédé de préparation d'alcaloïdes

Country Status (3)

Country	Link
BE (1)	BE583711A (da)
CH (1)	CH400177A (da)
DK (1)	DK109390C (da)

1959
- 1959-10-15 DK DK367759A patent/DK109390C/da active
- 1959-10-16 CH CH7956659A patent/CH400177A/fr unknown
- 1959-10-16 BE BE583711A patent/BE583711A/fr unknown

Also Published As

Publication number	Publication date
DK109390C (da)	1968-04-22
BE583711A (fr)	1960-04-19

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EP0022022A1 (fr)	1981-01-07	Nouveaux dérivés acylés de la taurine et leurs sels et procédé pour leur préparation
FR2474494A1 (fr)	1981-07-31	Acides dihydropyrazole carboxyliques
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