FR2718M - - Google Patents
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- Publication number
- FR2718M FR2718M FR934782A FR934782A FR2718M FR 2718 M FR2718 M FR 2718M FR 934782 A FR934782 A FR 934782A FR 934782 A FR934782 A FR 934782A FR 2718 M FR2718 M FR 2718M
- Authority
- FR
- France
- Prior art keywords
- deacetylamino
- colchiceinamide
- methyl
- antimitotic
- dose
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 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 claims description 10
- 230000002927 anti-mitotic effect Effects 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 6
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 3
- 201000009030 Carcinoma Diseases 0.000 claims description 2
- 208000002699 Digestive System Neoplasms Diseases 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000002547 new drug Substances 0.000 claims description 2
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims 10
- 229960001338 colchicine Drugs 0.000 claims 5
- 231100000636 lethal dose Toxicity 0.000 claims 4
- 230000000394 mitotic effect Effects 0.000 claims 4
- 239000002674 ointment Substances 0.000 claims 3
- 239000000843 powder Substances 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- 239000003826 tablet Substances 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 2
- 241000699670 Mus sp. Species 0.000 claims 2
- 241000700159 Rattus Species 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 230000011278 mitosis Effects 0.000 claims 2
- 230000000144 pharmacologic effect Effects 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 238000010254 subcutaneous injection Methods 0.000 claims 2
- 239000007929 subcutaneous injection Substances 0.000 claims 2
- 239000011260 aqueous acid Substances 0.000 claims 1
- 239000007900 aqueous suspension Substances 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 210000001185 bone marrow Anatomy 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 230000002349 favourable effect Effects 0.000 claims 1
- 238000002347 injection Methods 0.000 claims 1
- 239000007924 injection Substances 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- 238000010186 staining Methods 0.000 claims 1
- 238000010561 standard procedure Methods 0.000 claims 1
- 230000000298 stathmokinetic effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 231100000816 toxic dose Toxicity 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 231100000820 toxicity test Toxicity 0.000 claims 1
- 238000005303 weighing Methods 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- IPDJRYUVROTJTO-UHFFFAOYSA-N 1,2,3,10-tetramethoxy-6,7-dihydro-5h-benzo[a]heptalen-9-one Chemical compound C1CCC2=CC(=O)C(OC)=CC=C2C2=C1C=C(OC)C(OC)=C2OC IPDJRYUVROTJTO-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PRGILOMAMBLWNG-HNNXBMFYSA-N Colchiceine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(O)=CC=C1C1=C2C=C(OC)C(OC)=C1OC PRGILOMAMBLWNG-HNNXBMFYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 206010028980 Neoplasm Diseases 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 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 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 208000025113 myeloid leukemia Diseases 0.000 description 1
- 230000009826 neoplastic cell growth Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
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
- C07C49/753—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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA724233A CA724233A (en) | 1962-12-21 | Desacetylamino n-methyl colchiceinamide et son procede de preparation | |
| FR934782A FR2718M (enrdf_load_stackoverflow) | 1963-05-14 | 1963-05-14 | |
| GB3861463A GB991153A (en) | 1962-10-11 | 1963-10-01 | Colchiceine derivative |
| CH1235463A CH404649A (fr) | 1962-10-11 | 1963-10-08 | Procédé de préparation d'un nouveau dérivé colchicique |
| DK472863AA DK103833C (da) | 1962-12-21 | 1963-10-09 | Fremgangsmåde til fremstilling af desacetylamino-N-methylcolchiceinamid. |
| BE638665A BE638665A (fr) | 1962-12-21 | 1963-10-15 | Nouveau derive colchicique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR934782A FR2718M (enrdf_load_stackoverflow) | 1963-05-14 | 1963-05-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| FR2718M true FR2718M (enrdf_load_stackoverflow) | 1964-09-11 |
Family
ID=8585988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR934782A Expired FR2718M (enrdf_load_stackoverflow) | 1962-10-11 | 1963-05-14 |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2718M (enrdf_load_stackoverflow) |
-
1963
- 1963-05-14 FR FR934782A patent/FR2718M/fr not_active Expired
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