CH444144A - Procédé de préparation d'un dérivé de la colchicine - Google Patents

Procédé de préparation d'un dérivé de la colchicine

Info

Publication number: CH444144A
Authority: CH; Switzerland
Prior art keywords: colchicine; demethyl; hydroxymethyl; dimethylaminomethyl; iodide
Prior art date: 1962-11-12

Application number

CH1367563A

Other languages

English (en)

French (fr)

Inventor

Blade Arturo

Muller Georges

Original Assignee

Roussel Uclaf

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.)

1962-11-12

Filing date

1963-11-07

Publication date

1967-09-30

1963-11-07 Application filed by Roussel Uclaf filed Critical Roussel Uclaf

1967-09-30 Publication of CH444144A publication Critical patent/CH444144A/fr

Links

238000000034 method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 7
238000002360 preparation method Methods 0.000 title claims description 4
IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical class C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 title description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
229960001338 colchicine Drugs 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
DPOVAJCRYIUTBD-UHFFFAOYSA-N O2-Demethyl-colchicin Natural products C1CC(NC(C)=O)C2=CC(=O)C(OC)=CC=C2C2=C1C=C(OC)C(O)=C2OC DPOVAJCRYIUTBD-UHFFFAOYSA-N 0.000 claims description 6
230000009471 action Effects 0.000 claims description 6
PRGILOMAMBLWNG-UHFFFAOYSA-N colchicceine Natural products C1CC(NC(C)=O)C2=CC(=O)C(O)=CC=C2C2=C1C=C(OC)C(OC)=C2OC PRGILOMAMBLWNG-UHFFFAOYSA-N 0.000 claims description 6
DPOVAJCRYIUTBD-HNNXBMFYSA-N n-[(7s)-2-hydroxy-1,3,10-trimethoxy-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(O)=C1OC DPOVAJCRYIUTBD-HNNXBMFYSA-N 0.000 claims description 6
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 4
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 claims description 4
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 4
239000000243 solution Substances 0.000 claims description 4
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 3
-1 1-hydroxymethyl Chemical group 0.000 claims description 2
125000005265 dialkylamine group Chemical group 0.000 claims description 2
239000012022 methylating agents‎ Substances 0.000 claims description 2
230000011987 methylation Effects 0.000 claims description 2
238000007069 methylation reaction Methods 0.000 claims description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims 1
150000001350 alkyl halides Chemical class 0.000 claims 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
239000000047 product Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
239000000203 mixture Substances 0.000 description 4
235000020075 ouzo Nutrition 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids 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
238000004458 analytical method Methods 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000010828 elution Methods 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
208000020584 Polyploidy Diseases 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
230000002927 anti-mitotic effect Effects 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
229960004279 formaldehyde Drugs 0.000 description 1
235000019256 formaldehyde Nutrition 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
230000011278 mitosis Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
AAZYNPCMLRQUHI-UHFFFAOYSA-N propan-2-one;2-propan-2-yloxypropane Chemical compound CC(C)=O.CC(C)OC(C)C AAZYNPCMLRQUHI-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N45/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring
- A01N45/02—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds having three or more carbocyclic rings condensed among themselves, at least one ring not being a six-membered ring having three carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1367563A 1962-11-12 1963-11-07 Procédé de préparation d'un dérivé de la colchicine CH444144A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR915142A FR1347137A (fr)	1962-11-12	1962-11-12	Nouveaux dérivés de la colchicine et de la thiocolchicine et procédé de préparation

Publications (1)

Publication Number	Publication Date
CH444144A true CH444144A (fr)	1967-09-30

Family

ID=8790618

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1367563A CH444144A (fr)	1962-11-12	1963-11-07	Procédé de préparation d'un dérivé de la colchicine

Country Status (4)

Country	Link
AT (1)	AT241031B (de)
CH (1)	CH444144A (de)
ES (1)	ES293384A1 (de)
FR (1)	FR1347137A (de)

1962
- 1962-11-12 FR FR915142A patent/FR1347137A/fr not_active Expired
1963
- 1963-11-07 CH CH1367563A patent/CH444144A/fr unknown
- 1963-11-11 ES ES0293384A patent/ES293384A1/es not_active Expired
- 1963-11-12 AT AT903563A patent/AT241031B/de active

Also Published As

Publication number	Publication date
ES293384A1 (es)	1964-01-01
AT241031B (de)	1965-06-25
FR1347137A (fr)	1963-12-27

Publication	Publication Date	Title
EP0051023A1 (de)	1982-05-05	Derivate der Benzoyl- und alpha-Hydroxybenzyl-phenyl-osid-Familie, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung
CH433265A (fr)	1967-04-15	Procédé de préparation de 1,5-dioxo-4-(2'-carboxy- ou carbalcoxy-éthyl)-7aB-méthyl-5,6,7,7a-tétrahydroindanes
CH444144A (fr)	1967-09-30	Procédé de préparation d'un dérivé de la colchicine
CH450401A (fr)	1968-01-31	Procédé de préparation de nouveaux dérivés colchiciques
CH350972A (fr)	1960-12-31	Procédé de préparation de N-désacétyl-N-méthyl-alcoylthiocolchicéines
CH426858A (fr)	1966-12-31	Procédé de préparation de nouveaux dérivés colchiciques
EP0148666B1 (de)	1987-05-20	Verfahren zur Herstellung von Hydroxy-3-methyl-3-glutarsäure
CH368504A (fr)	1963-04-15	Procédé de préparation d'une nouvelle lactone contenant du brome
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BE633582A (de)
CH314548A (fr)	1956-06-15	Procédé de préparation d'un 1-p-nitrophényl-2-acylamido-propanediol-1,3
CN101775055B (zh)	2012-10-24	一种合成4-三氟甲基-4-烯-3-酮甾体化合物的方法
CH404649A (fr)	1965-12-31	Procédé de préparation d'un nouveau dérivé colchicique
CH346890A (fr)	1960-06-15	Procédé pour la préparation de N,N-dibenzyl-x-amino-acides
CH289889A (fr)	1953-03-31	Procédé de préparation d'un acylamidodiol aromatique.
CH316154A (fr)	1956-09-30	Procédé de fabrication de dihydroxy-polyhydrophénanthrènes
BE632523A (de)
CH289890A (fr)	1953-03-31	Procédé de pr<paration d'un acylamidodiol aromatique.
CH421958A (fr)	1966-10-15	Procédé de préparation de nouveaux aminostéroïdes
BE864336A (fr)	1978-06-16	Nouveaux derives d'anthracyclines
CH525206A (fr)	1972-07-15	Procédé de préparation des flavone-7-oxyacétates d'alcoyle inférieur
CH304977A (fr)	1955-01-31	Procédé de préparation d'une oxazoline substituée.
CH404667A (fr)	1965-12-31	Procédé de préparation d'un nouveau dérivé de la pénicilline