CH385871A - Verfahren zur Herstellung von Vitamin B12-Derivaten - Google Patents

Verfahren zur Herstellung von Vitamin B12-Derivaten

Info

Publication number: CH385871A
Authority: CH; Switzerland
Prior art keywords: acid; abcdeg; water; dicyanide; hexamide
Prior art date: 1959-07-31

Application number

CH7643559A

Other languages

German (de)

English (en)

Inventor

Bernhauer Konrad Dr Prof

Original Assignee

Hoffmann La Roche

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.)

1959-07-31

Filing date

1959-07-31

Publication date

1964-12-31

1959-07-31 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1959-07-31 Priority to CH7643559A priority Critical patent/CH385871A/de

1960-07-19 Priority to BE593141A priority patent/BE593141A/fr

1964-12-31 Publication of CH385871A publication Critical patent/CH385871A/de

Links

238000000034 method Methods 0.000 title claims description 16
238000004519 manufacturing process Methods 0.000 title claims description 4
150000001867 cobalamins Chemical class 0.000 title claims description 3
150000001412 amines Chemical class 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
150000008064 anhydrides Chemical class 0.000 claims description 4
238000009833 condensation Methods 0.000 claims description 4
230000005494 condensation Effects 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
150000001450 anions Chemical class 0.000 claims description 3
150000001718 carbodiimides Chemical class 0.000 claims description 3
125000004432 carbon atom Chemical group C* 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
239000002253 acid Substances 0.000 description 20
239000000243 solution Substances 0.000 description 19
UFHGABBBZRPRJV-UHFFFAOYSA-N Hydroxysanguinarine Chemical compound C12=CC=C3OCOC3=C2C(=O)N(C)C(C2=C3)=C1C=CC2=CC1=C3OCO1 UFHGABBBZRPRJV-UHFFFAOYSA-N 0.000 description 15
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 12
-1 sodium tetraphenylborate Chemical compound 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
XQRJFEVDQXEIAX-JFYQDRLCSA-M cobinamide Chemical compound [Co]N([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@H](O)C)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O XQRJFEVDQXEIAX-JFYQDRLCSA-M 0.000 description 10
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
239000001913 cellulose Substances 0.000 description 8
229920002678 cellulose Polymers 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000007795 chemical reaction product Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
150000001414 amino alcohols Chemical class 0.000 description 5
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical class CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
239000000047 product Substances 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
229930003779 Vitamin B12 Natural products 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
FDJOLVPMNUYSCM-WZHZPDAFSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+3].N#[C-].N([C@@H]([C@]1(C)[N-]\C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C(\C)/C1=N/C([C@H]([C@@]1(CC(N)=O)C)CCC(N)=O)=C\C1=N\C([C@H](C1(C)C)CCC(N)=O)=C/1C)[C@@H]2CC(N)=O)=C\1[C@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]1[C@@H](O)[C@@H](N2C3=CC(C)=C(C)C=C3N=C2)O[C@@H]1CO FDJOLVPMNUYSCM-WZHZPDAFSA-L 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
ALBYIUDWACNRRB-UHFFFAOYSA-N hexanamide Chemical compound CCCCCC(N)=O ALBYIUDWACNRRB-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
239000011782 vitamin Substances 0.000 description 4
229930003231 vitamin Natural products 0.000 description 4
235000013343 vitamin Nutrition 0.000 description 4
229940088594 vitamin Drugs 0.000 description 4
239000011715 vitamin B12 Substances 0.000 description 4
235000019163 vitamin B12 Nutrition 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
229910000147 aluminium phosphate Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
QTBSBXVTEAMEQO-DYCDLGHISA-N deuterio acetate Chemical compound [2H]OC(C)=O QTBSBXVTEAMEQO-DYCDLGHISA-N 0.000 description 3
238000001962 electrophoresis Methods 0.000 description 3
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
QZXIXSZVEYUCGM-UHFFFAOYSA-N 2-aminopropan-2-ol Chemical compound CC(C)(N)O QZXIXSZVEYUCGM-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical class [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
102000002262 Thromboplastin Human genes 0.000 description 2
108010000499 Thromboplastin Proteins 0.000 description 2
230000001174 ascending effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012535 impurity Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
ANSUDRATXSJBLY-VKHMYHEASA-N methyl (2s)-2-amino-3-hydroxypropanoate Chemical compound COC(=O)[C@@H](N)CO ANSUDRATXSJBLY-VKHMYHEASA-N 0.000 description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000001556 precipitation Methods 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000010802 sludge Substances 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BHOCTMHUVQJYHN-UHFFFAOYSA-N 1-aminoethyl dihydrogen phosphate Chemical compound CC(N)OP(O)(O)=O BHOCTMHUVQJYHN-UHFFFAOYSA-N 0.000 description 1
HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical class O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
MPCRDALPQLDDFX-UHFFFAOYSA-L Magnesium perchlorate Chemical compound [Mg+2].[O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O MPCRDALPQLDDFX-UHFFFAOYSA-L 0.000 description 1
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 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
239000004473 Threonine Substances 0.000 description 1
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
230000003167 anti-vitamin Effects 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
150000004700 cobalt complex Chemical class 0.000 description 1
HFWIMJHBCIGYFH-UHFFFAOYSA-N cyanoform Chemical compound N#CC(C#N)C#N HFWIMJHBCIGYFH-UHFFFAOYSA-N 0.000 description 1
238000006114 decarboxylation reaction Methods 0.000 description 1
238000010612 desalination reaction Methods 0.000 description 1
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
AXZAYXJCENRGIM-UHFFFAOYSA-J dipotassium;tetrabromoplatinum(2-) Chemical compound [K+].[K+].[Br-].[Br-].[Br-].[Br-].[Pt+2] AXZAYXJCENRGIM-UHFFFAOYSA-J 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
GKCXXDSWWDWUHS-BYPYZUCNSA-N ethyl (2s)-2-amino-3-hydroxypropanoate Chemical compound CCOC(=O)[C@@H](N)CO GKCXXDSWWDWUHS-BYPYZUCNSA-N 0.000 description 1
JNTDLWHHJMGLGD-UHNVWZDZSA-N ethyl (2s,3r)-2-amino-3-hydroxybutanoate Chemical compound CCOC(=O)[C@@H](N)[C@@H](C)O JNTDLWHHJMGLGD-UHNVWZDZSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
244000005700 microbiome Species 0.000 description 1
239000011707 mineral Chemical class 0.000 description 1
LPMDNOPQLGRDMA-UHFFFAOYSA-N n'-butylmethanediimine Chemical compound CCCCN=C=N LPMDNOPQLGRDMA-UHFFFAOYSA-N 0.000 description 1
239000002773 nucleotide Substances 0.000 description 1
125000003729 nucleotide group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910001487 potassium perchlorate Inorganic materials 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
150000003722 vitamin derivatives Chemical class 0.000 description 1
238000004065 wastewater treatment Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH7643559A 1959-07-31 1959-07-31 Verfahren zur Herstellung von Vitamin B12-Derivaten CH385871A (de)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH7643559A CH385871A (de)	1959-07-31	1959-07-31	Verfahren zur Herstellung von Vitamin B12-Derivaten
BE593141A BE593141A (fr)	1959-07-31	1960-07-19	Procédé pour la préparation de dérivés de vitamine B12

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH7643559A CH385871A (de)	1959-07-31	1959-07-31	Verfahren zur Herstellung von Vitamin B12-Derivaten

Publications (1)

Publication Number	Publication Date
CH385871A true CH385871A (de)	1964-12-31

Family

ID=4534924

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH7643559A CH385871A (de)	1959-07-31	1959-07-31	Verfahren zur Herstellung von Vitamin B12-Derivaten

Country Status (2)

Country	Link
BE (1)	BE593141A (fr)
CH (1)	CH385871A (fr)

1959
- 1959-07-31 CH CH7643559A patent/CH385871A/de unknown
1960
- 1960-07-19 BE BE593141A patent/BE593141A/fr unknown

Also Published As

Publication number	Publication date
BE593141A (fr)	1961-01-19

Publication	Publication Date	Title
DE1545760C3 (de)	1978-10-05	Vincaleukoblastinderivate
AT399155B (de)	1995-03-27	Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung
AT394853B (de)	1992-07-10	Verfahren zur herstellung von neuen mitosanderivaten
DE1620694B2 (de)	1981-07-16	Verfahren zur Herstellung von 5-Methyl-7-diäthylamino-s-triazolo [1,5-a] pyrimidin und seinen Salzen mit Säuren
CH385871A (de)	1964-12-31	Verfahren zur Herstellung von Vitamin B12-Derivaten
DE1260466B (de)	1968-02-08	Verfahren zur Herstellung von 17-Oxo-D-homo-5alpha- oder 17-Oxo-D-homo-5alpha,13alpha-18-saeuren bzw. von deren Methylestern
DE1163337B (de)	1964-02-20	Verfahren zur Herstellung von Trihydroxamsaeuren
DE2902292C2 (de)	1982-08-05	Verfahren zur Herstellung von 2,4-Diaminobuttersäure oder 4-Amino-2-hydroxybuttersäure
EP0045079A1 (fr)	1982-02-03	Procédé pour la purification de l'amide de l'acide nicotinique I
DE2558507C3 (de)	1979-10-31	Verfahren zur Racemattrennung von dJ-l-Phenyl-2-amino-l-propanol
DE1543811B1 (de)	1971-01-21	Verfahren zur Trennung von racemischem Carnitinnitril in seine optisch aktiven Antipoden
DE3102984A1 (de)	1981-11-26	Verfahren zur herstellung von cysteamin-s-substituierten verbindungen und deren derivaten
DE1545759C3 (de)	1975-10-02	Vincaleukoblastin-derivate und ein Verfahren zu ihrer Herstellung
DE2208631C3 (de)	1978-05-03	N-Isobornyloxycarbonylcephalosporin C, Verfahren zu seiner Herstellung und Verwendung zur Herstellung von Cephalosporin C
DE2723417C3 (de)	1980-08-07	5,6-Epineamin und dessen Verwendung bei der Bekämpfung bakterieller Infektionen
DE1147952B (de)	1963-05-02	Verfahren zur Herstellung von Vitaminen der B-Gruppe und Analogen derselben
AT274249B (de)	1969-09-10	Verfahren zur Herstellung des neuen Scilliglaucosidin-19-ol-α-L-rhamnosids
DE2540134C3 (de)	1978-11-23	L-Phenylalaninderivate, Verfahren zu ihrer Herstellung und ihre Verwendung
AT326839B (de)	1975-12-29	Verfahren zur halbsynthetischen herstellung von vincristin
DE2449942C2 (de)	1982-10-28	2'-Amino-2'-desoxyguanosin und Verfahren zu seiner Herstellung
DE1445831C3 (de)	1976-11-25	7-Phenylacetamido-cephalosporansäurederivate, Verfahren zu deren Herstellung und pharmazeutische Formulierungen
AT258485B (de)	1967-11-27	Verfahren zur Herstellung von neuen Peptiden
CH515274A (de)	1971-11-15	Verfahren zur Herstellung neuer Derivate der 7-Amino-cephalosporansäure mit antibiotischer Wirkung
AT264724B (de)	1968-09-10	Verfahren zur Herstellung von neuen desacetylierten mehrkernigen Indolen
AT288363B (de)	1971-03-10	Verfahren zur Herstellung von neuen β-Aroyl- β-halogenacrylsäuren