CH438347A - Procédé de préparation de nouveaux dérivés colchiciques - Google Patents
Procédé de préparation de nouveaux dérivés colchiciquesInfo
- Publication number
- CH438347A CH438347A CH1229863A CH1229863A CH438347A CH 438347 A CH438347 A CH 438347A CH 1229863 A CH1229863 A CH 1229863A CH 1229863 A CH1229863 A CH 1229863A CH 438347 A CH438347 A CH 438347A
- Authority
- CH
- Switzerland
- Prior art keywords
- water
- methylene chloride
- formyl
- carbon atoms
- hydroxymethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- -1 1-hydroxymethyl Chemical class 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 235000020075 ouzo Nutrition 0.000 description 8
- 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 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
- 229960001338 colchicine Drugs 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 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
- 230000015572 biosynthetic process Effects 0.000 description 2
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 2
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 2
- WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CMEGANPVAXDBPL-INIZCTEOSA-N n-[(7s)-1,2,3-trimethoxy-10-methylsulfanyl-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(SC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC CMEGANPVAXDBPL-INIZCTEOSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000408533 Lento Species 0.000 description 1
- 208000020584 Polyploidy Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 229940045695 antineooplastic colchicine derivative Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002886 arachidonoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000004071 biological effect Effects 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- RVOJTCZRIKWHDX-UHFFFAOYSA-N cyclohexanecarbonyl chloride Chemical compound ClC(=O)C1CCCCC1 RVOJTCZRIKWHDX-UHFFFAOYSA-N 0.000 description 1
- AOQONNCNKUWWRI-UHFFFAOYSA-N cyclohexylmethyl carbonochloridate Chemical compound ClC(=O)OCC1CCCCC1 AOQONNCNKUWWRI-UHFFFAOYSA-N 0.000 description 1
- GPTIZNPODRMHFN-UHFFFAOYSA-N cyclohexylmethyl hydrogen carbonate Chemical compound OC(=O)OCC1CCCCC1 GPTIZNPODRMHFN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000403 lignoceroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005645 linoleyl group Chemical group 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
- JWDFWIZNGSOUGC-INIZCTEOSA-N n-[(7s)-10-amino-1,2,3-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(N)=CC=C1C1=C2C=C(OC)C(OC)=C1OC JWDFWIZNGSOUGC-INIZCTEOSA-N 0.000 description 1
- NLBLGIGBTKMQSA-UHFFFAOYSA-N n-[1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5h-benzo[a]heptalen-7-yl]acetamide Chemical compound C1CC(NC(C)=O)C2=CC(=O)C(NC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC NLBLGIGBTKMQSA-UHFFFAOYSA-N 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000007659 semicarbazones Chemical class 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/757—Unsaturated compounds containing a keto groups being part of a ring containing —CHO groups
-
- 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/64—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of functional groups containing oxygen only in singly bound form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups
- C07C49/755—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups a keto group being part of a condensed ring system with two or three rings, at least one ring being a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR911957A FR1359632A (fr) | 1962-10-11 | 1962-10-11 | Dérivés de la colchicine et de la thiocolchicine et procédé de préparation |
| FR914928A FR1359642A (fr) | 1962-10-11 | 1962-11-09 | Dérivés colchiciniques et procédé de préparation |
| FR917511A FR83169E (fr) | 1962-10-11 | 1962-12-04 | Dérivés de la colchicine et de la thiocolchicine et procédé de préparation |
| FR919491A FR1359662A (fr) | 1962-10-11 | 1962-12-21 | Dérivés colchiciques et procédé de préparation |
| FR924190A FR2420M (fr) | 1962-11-09 | 1963-02-08 | Nouveau médicament doué notamment d'activité antimitotique. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH438347A true CH438347A (fr) | 1967-06-30 |
Family
ID=27515140
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1229863A CH438347A (fr) | 1962-10-11 | 1963-10-07 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH1373466A CH444876A (fr) | 1962-10-11 | 1963-10-07 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH1373366A CH444875A (fr) | 1962-10-11 | 1963-10-07 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH25467A CH450401A (fr) | 1962-10-11 | 1963-11-01 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH1345363A CH441292A (fr) | 1962-10-11 | 1963-11-01 | Procédé de préparation de nouveaux dérivés colchiciques |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1373466A CH444876A (fr) | 1962-10-11 | 1963-10-07 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH1373366A CH444875A (fr) | 1962-10-11 | 1963-10-07 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH25467A CH450401A (fr) | 1962-10-11 | 1963-11-01 | Procédé de préparation de nouveaux dérivés colchiciques |
| CH1345363A CH441292A (fr) | 1962-10-11 | 1963-11-01 | Procédé de préparation de nouveaux dérivés colchiciques |
Country Status (9)
| Country | Link |
|---|---|
| US (3) | US3249638A (enExample) |
| BE (1) | BE638469A (enExample) |
| BR (2) | BR6353335D0 (enExample) |
| CH (5) | CH438347A (enExample) |
| DE (3) | DE1795496A1 (enExample) |
| FR (3) | FR1359632A (enExample) |
| GB (2) | GB1027961A (enExample) |
| NL (3) | NL300021A (enExample) |
| SE (5) | SE306089B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE649506A (enExample) * | 1963-06-19 | |||
| US5407536A (en) * | 1994-02-10 | 1995-04-18 | Rhone-Poulenc Inc. | Amphoteric surfactants as glass fiber dispersants for the manufacture of uniform glass fiber mats |
| US5409574A (en) * | 1994-02-10 | 1995-04-25 | Rhone-Poulenc Inc. | Propoxylated fatty amine ethoxylate surfactants as glass fiber dispersants for the manufacture of uniform glass fiber mats |
| US7119229B2 (en) * | 2001-05-28 | 2006-10-10 | Chemtech Research Incorporation | Alkaloid derivative and a pharmaceutical composition containing the same |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2734014A (en) * | 1956-02-07 | Glucoside colchicoside and a method of | ||
| US1915334A (en) * | 1930-10-16 | 1933-06-27 | Du Pont | Fluosilicate of organic heterocyclic bases and process of making it |
| US2075359A (en) * | 1930-10-16 | 1937-03-30 | Du Pont | Insecticide |
| US2141687A (en) * | 1933-08-23 | 1938-12-27 | Firm Soc Of Chemical Ind In Ba | Hydroxyphenylamino-anthracene and process of making same |
| US2128100A (en) * | 1936-06-05 | 1938-08-23 | Du Pont | Preparation of 4, 4'-dialkoxy diphenylamines |
| US2436063A (en) * | 1945-06-20 | 1948-02-17 | American Cyanamid Co | Scarlet fever toxin |
| US2742464A (en) * | 1951-04-25 | 1956-04-17 | Koebner Adolf | Production of capillary active amine-amides |
| US2857422A (en) * | 1956-07-16 | 1958-10-21 | Shell Dev | Production of carbonyl-substituted ethanol esters |
| US2941002A (en) * | 1956-11-06 | 1960-06-14 | Hoechst Ag | Beta-hydroxy carboxylic acid amides substituted at the nitrogen atom |
| US2957022A (en) * | 1957-04-30 | 1960-10-18 | Exxon Research Engineering Co | Esters of cyclopentane-1, 3-dicarboxylic acid |
| US2952585A (en) * | 1957-06-19 | 1960-09-13 | New England Inst For Medical R | Immunizing against and treatment of diseases |
| FR1344157A (fr) * | 1959-05-22 | 1963-11-29 | Roussel Uclaf | Nouvelles colchicines et leur procédé d'obtention |
| US3006812A (en) * | 1960-09-21 | 1961-10-31 | Lab Francais Chimiotherapie | N-desacetyl colchiceine for the treatment of gout |
| US3106514A (en) * | 1961-08-15 | 1963-10-08 | Philips Roxane | Measles virus immunization with gamma globulin administered simultaneously with measles virus vaccine |
| US3105012A (en) * | 1961-10-19 | 1963-09-24 | Parke Davis & Co | Antigen products and means for producing the same |
| NL292766A (enExample) * | 1962-05-18 |
-
0
- NL NL298743D patent/NL298743A/xx unknown
- NL NL299743D patent/NL299743A/xx unknown
- BE BE638469D patent/BE638469A/xx unknown
- NL NL300021D patent/NL300021A/xx unknown
-
1962
- 1962-10-11 FR FR911957A patent/FR1359632A/fr not_active Expired
- 1962-11-09 FR FR914928A patent/FR1359642A/fr not_active Expired
- 1962-12-21 FR FR919491A patent/FR1359662A/fr not_active Expired
-
1963
- 1963-10-01 US US312891A patent/US3249638A/en not_active Expired - Lifetime
- 1963-10-01 US US312890A patent/US3301852A/en not_active Expired - Lifetime
- 1963-10-04 BR BR153335/63A patent/BR6353335D0/pt unknown
- 1963-10-07 CH CH1229863A patent/CH438347A/fr unknown
- 1963-10-07 CH CH1373466A patent/CH444876A/fr unknown
- 1963-10-07 SE SE10968/63A patent/SE306089B/xx unknown
- 1963-10-07 CH CH1373366A patent/CH444875A/fr unknown
- 1963-10-09 DE DE19631795496 patent/DE1795496A1/de active Pending
- 1963-10-09 DE DE19631470196 patent/DE1470196A1/de active Pending
- 1963-10-11 GB GB40287/63A patent/GB1027961A/en not_active Expired
- 1963-10-11 GB GB8455/65A patent/GB1027962A/en not_active Expired
- 1963-10-29 SE SE11913/63A patent/SE306745B/xx unknown
- 1963-10-29 SE SE761/65A patent/SE306090B/xx unknown
- 1963-11-01 CH CH25467A patent/CH450401A/fr unknown
- 1963-11-01 CH CH1345363A patent/CH441292A/fr unknown
- 1963-11-07 US US322039A patent/US3379762A/en not_active Expired - Lifetime
- 1963-11-07 BR BR154414/63A patent/BR6354414D0/pt unknown
- 1963-11-07 DE DE19631470198 patent/DE1470198A1/de active Pending
-
1965
- 1965-01-20 SE SE75965A patent/SE317684B/xx unknown
- 1965-01-20 SE SE76065A patent/SE317980B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3301852A (en) | 1967-01-31 |
| BR6353335D0 (pt) | 1973-07-12 |
| GB1027961A (en) | 1966-05-04 |
| SE306745B (enExample) | 1968-12-09 |
| DE1470196A1 (de) | 1969-09-18 |
| FR1359642A (fr) | 1964-04-30 |
| NL299743A (enExample) | |
| CH441292A (fr) | 1967-08-15 |
| CH444876A (fr) | 1967-10-15 |
| FR1359632A (fr) | 1964-04-30 |
| SE306090B (enExample) | 1968-11-18 |
| DE1470198A1 (de) | 1969-06-12 |
| NL298743A (enExample) | |
| FR1359662A (fr) | 1964-04-30 |
| SE306089B (enExample) | 1968-11-18 |
| US3249638A (en) | 1966-05-03 |
| SE317684B (enExample) | 1969-11-24 |
| NL300021A (enExample) | |
| CH444875A (fr) | 1967-10-15 |
| CH450401A (fr) | 1968-01-31 |
| SE317980B (enExample) | 1969-12-01 |
| BR6354414D0 (pt) | 1973-07-03 |
| BE638469A (enExample) | |
| DE1795496A1 (de) | 1972-01-13 |
| GB1027962A (en) | 1966-05-04 |
| US3379762A (en) | 1968-04-23 |
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