DE2418127A1 - C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselben - Google Patents
C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselbenInfo
- Publication number
- DE2418127A1 DE2418127A1 DE2418127A DE2418127A DE2418127A1 DE 2418127 A1 DE2418127 A1 DE 2418127A1 DE 2418127 A DE2418127 A DE 2418127A DE 2418127 A DE2418127 A DE 2418127A DE 2418127 A1 DE2418127 A1 DE 2418127A1
- Authority
- DE
- Germany
- Prior art keywords
- digoxin
- alkyl
- methyl
- derivatives
- aprotic solvent
- 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.)
- Withdrawn
Links
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 title claims abstract description 6
- 229960005156 digoxin Drugs 0.000 title abstract description 5
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001351 alkyl iodides Chemical class 0.000 title abstract description 3
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 title abstract 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 title description 5
- 229910000104 sodium hydride Inorganic materials 0.000 title description 5
- 239000012312 sodium hydride Substances 0.000 title description 5
- 239000000010 aprotic solvent Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 7
- 229960003746 metildigoxin Drugs 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- IYJMSDVSVHDVGT-PEQKVOOWSA-N metildigoxin Chemical compound O1[C@H](C)[C@@H](OC)[C@@H](O)C[C@@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O IYJMSDVSVHDVGT-PEQKVOOWSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000009826 distribution Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- -1 methyl halides Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- DMXVDFPEGANQNY-UHFFFAOYSA-N O.OC.ClC(Cl)(Cl)Cl.CCOC(C)=O Chemical compound O.OC.ClC(Cl)(Cl)Cl.CCOC(C)=O DMXVDFPEGANQNY-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229920006158 high molecular weight polymer Polymers 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C07J19/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2418127A DE2418127A1 (de) | 1974-04-13 | 1974-04-13 | C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselben |
| AR260678A AR205139A1 (es) | 1974-04-13 | 1975-01-01 | Procedimiento para la preparacion de nuevos derivados c22-substituidos de la alfa- y betametildigoxina |
| AR20297375D AR202973A1 (es) | 1974-04-13 | 1975-01-01 | Procedimiento para la preparacion de derivados c22-alquilo de la digoxina |
| US05/558,381 US3981862A (en) | 1974-04-13 | 1975-03-14 | Preparation of C22-alkyl derivative of digoxin |
| CA223,698A CA1033714A (en) | 1974-04-13 | 1975-04-02 | Process for the production of c22-alkyl derivatives of digoxin |
| CA223,699A CA1033715A (en) | 1974-04-13 | 1975-04-02 | C-22-SUBSTITUTED DERIVATIVES OF .alpha.-AND .beta.-METHYL-DIGOXIN |
| NL7504090A NL7504090A (nl) | 1974-04-13 | 1975-04-07 | Werkwijzen voor het bereiden en toepassen van c22-gesubstitueerde derivaten van (alpha)- en (beta)-methyl- digoxine. |
| AR258266A AR203906A1 (es) | 1974-04-13 | 1975-04-07 | Procedimiento para la preparacion de nuevos derivados c22 sustituidos de la alfa-y beta-metildigoxina |
| NL7504091A NL7504091A (nl) | 1974-04-13 | 1975-04-07 | Werkwijze voor het bereiden van c22-alkyl-deri- vaten van digoxine. |
| SE7504006A SE7504006L (sv) | 1974-04-13 | 1975-04-08 | Forfarande for framstellning av c22-substituerade derivat av alfa- och beta etyldigoxin. |
| FI751053A FI54317C (fi) | 1974-04-13 | 1975-04-08 | Foerbaettrat foerfarande foer framstaellning av c22-alkylderivat av digoxin |
| SE7504005A SE396392B (sv) | 1974-04-13 | 1975-04-08 | Forfarande for framstellning av c 22-alkyl-derivat av digoxin |
| FI751052A FI751052A7 (enExample) | 1974-04-13 | 1975-04-08 | |
| GB1458275A GB1450014A (en) | 1974-04-13 | 1975-04-09 | C22-substituted derivatives of a-and beta-methyl-digoxin |
| ES436457A ES436457A1 (es) | 1974-04-13 | 1975-04-09 | Procedimiento para la preparacion de nuevos derivados susti-tuidos en posicion c22 de la alfa- y de la beta-metildigoxi-na. |
| CH452975A CH594700A5 (enExample) | 1974-04-13 | 1975-04-09 | |
| CH453075A CH616945A5 (en) | 1974-04-13 | 1975-04-09 | Process for the preparation of C22-substituted derivatives of alpha- and beta-methyldigoxin. |
| GB1459675A GB1449804A (en) | 1974-04-13 | 1975-04-09 | Process for the preparation of digoxin derivatives |
| ES436458A ES436458A1 (es) | 1974-04-13 | 1975-04-09 | Procedimiento para la preparacion de derivados alcohilicos en c22 de la digoxina. |
| AU80044/75A AU483210B2 (en) | 1974-04-13 | 1975-04-10 | New c22-substituted derivatives of - and - methyl digoxin |
| AU80043/75A AU483189B2 (en) | 1974-04-13 | 1975-04-10 | Process forthe preparation of digoxin derivatives |
| AT275175A AT343290B (de) | 1974-04-13 | 1975-04-10 | Verfahren zur herstellung von neuen c22-substituierten derivaten des alfa- und beta-methyldigoxins |
| FR7511369A FR2267109B1 (enExample) | 1974-04-13 | 1975-04-11 | |
| FR7511370A FR2267328B1 (enExample) | 1974-04-13 | 1975-04-11 | |
| JP50045117A JPS5851960B2 (ja) | 1974-04-13 | 1975-04-14 | ジゴキシンノ ｃ２２−アルキル−ユウドウタイノセイホウ |
| JP50045116A JPS50137969A (enExample) | 1974-04-13 | 1975-04-14 | |
| AT330977A AT352908B (de) | 1974-04-13 | 1977-05-09 | Verfahren zur herstellung von neuen c22-substi- tuierten derivaten des alpha - und beta-methyl- digoxins |
| CH369879A CH618444A5 (en) | 1974-04-13 | 1979-04-19 | Process for the preparation of C22-substituted derivatives of alpha- and beta-methyldigoxin. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2418127A DE2418127A1 (de) | 1974-04-13 | 1974-04-13 | C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselben |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2418127A1 true DE2418127A1 (de) | 1975-11-06 |
Family
ID=5912937
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2418127A Withdrawn DE2418127A1 (de) | 1974-04-13 | 1974-04-13 | C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselben |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH594700A5 (enExample) |
| DE (1) | DE2418127A1 (enExample) |
-
1974
- 1974-04-13 DE DE2418127A patent/DE2418127A1/de not_active Withdrawn
-
1975
- 1975-04-09 CH CH452975A patent/CH594700A5/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH594700A5 (enExample) | 1978-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |