NO742545L - - Google Patents

Info

Publication number: NO742545L
Authority: NO; Norway
Prior art keywords: cyanocobalamin; methylcobalamin; solution; water; oxalic acid
Prior art date: 1973-08-08

Application number

NO742545A

Other languages

English (en)

Norwegian (no)

Inventor

J Boige

Original Assignee

Opochimie L

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.)

1973-08-08

Filing date

1974-07-12

Publication date

1975-03-10

1973-08-08 Priority claimed from FR7328998A external-priority patent/FR2240232A1/fr

1973-12-28 Priority claimed from FR7346829A external-priority patent/FR2256174A2/fr

1974-07-12 Application filed by Opochimie L filed Critical Opochimie L

1975-03-10 Publication of NO742545L publication Critical patent/NO742545L/no

Links

RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=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 RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 claims description 77
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
235000000639 cyanocobalamin Nutrition 0.000 claims description 38
239000011666 cyanocobalamin Substances 0.000 claims description 38
229960002104 cyanocobalamin Drugs 0.000 claims description 38
235000007672 methylcobalamin Nutrition 0.000 claims description 34
239000011585 methylcobalamin Substances 0.000 claims description 34
JEWJRMKHSMTXPP-BYFNXCQMSA-M methylcobalamin Chemical compound C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=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 JEWJRMKHSMTXPP-BYFNXCQMSA-M 0.000 claims description 34
ASARMUCNOOHMLO-WLORSUFZSA-L cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2s)-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+2].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\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 ASARMUCNOOHMLO-WLORSUFZSA-L 0.000 claims description 22
238000000034 method Methods 0.000 claims description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 18
CPKISUMKCULUNR-UHFFFAOYSA-N 2-methoxy-2-oxoacetic acid Chemical compound COC(=O)C(O)=O CPKISUMKCULUNR-UHFFFAOYSA-N 0.000 claims description 15
238000007069 methylation reaction Methods 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
239000002184 metal Substances 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 11
239000000843 powder Substances 0.000 claims description 11
239000012429 reaction media Substances 0.000 claims description 10
230000011987 methylation Effects 0.000 claims description 9
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
150000001868 cobalt Chemical class 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
229910002651 NO3 Inorganic materials 0.000 claims 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
238000006722 reduction reaction Methods 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
229920005989 resin Polymers 0.000 description 8
239000011347 resin Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 4
125000004093 cyano group Chemical group *C#N 0.000 description 4
239000000047 product Substances 0.000 description 4
150000001768 cations Chemical class 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
238000000746 purification Methods 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
239000011701 zinc Substances 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
241001070941 Castanea Species 0.000 description 2
235000014036 Castanea Nutrition 0.000 description 2
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001450 anions Chemical class 0.000 description 2
239000011324 bead Substances 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
229940010007 cobalamins Drugs 0.000 description 2
150000001867 cobalamins Chemical class 0.000 description 2
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 2
229910001429 cobalt ion Inorganic materials 0.000 description 2
229910001981 cobalt nitrate Inorganic materials 0.000 description 2
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 2
MULYSYXKGICWJF-UHFFFAOYSA-L cobalt(2+);oxalate Chemical compound [Co+2].[O-]C(=O)C([O-])=O MULYSYXKGICWJF-UHFFFAOYSA-L 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
YOZNUFWCRFCGIH-BYFNXCQMSA-L hydroxocobalamin Chemical compound O[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=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 YOZNUFWCRFCGIH-BYFNXCQMSA-L 0.000 description 2
-1 methyl- Chemical group 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
230000007017 scission Effects 0.000 description 2
150000003751 zinc Chemical class 0.000 description 2
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 1
229930003270 Vitamin B Natural products 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003957 anion exchange resin Substances 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
239000003729 cation exchange resin Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
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 1
239000002131 composite material Substances 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
235000004867 hydroxocobalamin Nutrition 0.000 description 1
239000011704 hydroxocobalamin Substances 0.000 description 1
229960001103 hydroxocobalamin Drugs 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000011282 treatment Methods 0.000 description 1
235000019156 vitamin B Nutrition 0.000 description 1
239000011720 vitamin B Substances 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)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO742545A 1973-08-08 1974-07-12 NO742545L (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7328998A FR2240232A1 (en)	1973-08-08	1973-08-08	Methylcobalamine prepn from cyanocobalamine - by reduction and methylation using methyl acid oxalate and a metal
FR7346829A FR2256174A2 (en)	1973-12-28	1973-12-28	Methylcobalamine prepn from cyanocobalamine - by reduction and methylation using methyl acid oxalate and a metal

Publications (1)

Publication Number	Publication Date
NO742545L true NO742545L (de)	1975-03-10

Family

ID=26217885

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO742545A NO742545L (de)	1973-08-08	1974-07-12

Country Status (16)

Country	Link
JP (1)	JPS5727119B2 (de)
AR (1)	AR199756A1 (de)
CA (1)	CA1019726A (de)
CH (1)	CH583744A5 (de)
DE (1)	DE2434967A1 (de)
DK (1)	DK136775B (de)
ES (1)	ES428798A1 (de)
GB (1)	GB1419933A (de)
IE (1)	IE41823B1 (de)
IL (1)	IL45384A (de)
IN (1)	IN139935B (de)
LU (1)	LU70582A1 (de)
NL (1)	NL7410061A (de)
NO (1)	NO742545L (de)
OA (1)	OA04753A (de)
SE (1)	SE412589B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
RU2151773C1 (ru) *	1999-03-10	2000-06-27	Казанский государственный университет им. В.И. Ульянова-Ленина	ТЕТРАКИС-(L-ГИСТИДИНАТО)-μ-ПЕРОКСИДИКОБАЛЬТА (III) ГЕПТАГИДРАТ, ПРОЯВЛЯЮЩИЙ АНТИАНЕМИЧЕСКУЮ, РАДИОПРОТЕКТОРНУЮ И АНТИАРИТМИЧЕСКУЮ АКТИВНОСТЬ
WO2002098896A1 (en)	2001-06-05	2002-12-12	Eisai Co., Ltd.	Process for producing methylcobalamin
CN102391340A (zh) *	2011-10-31	2012-03-28	河北玉星生物工程有限公司	一种甲钴胺的制备方法
HUE063127T2 (hu) *	2016-07-08	2024-01-28	Healthtech Bio Actives S L U	Eljárás metilkobalamin tisztítására
CN114874276B (zh) *	2022-04-21	2024-06-21	南京工业大学	一种改进的合成甲钴胺的方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE789252A (fr) *	1971-11-10	1973-03-26	Boige Jean	Procede de fabrication de la methylcobalamine

1974
- 1974-07-12 NO NO742545A patent/NO742545L/no unknown
- 1974-07-17 DK DK386274AA patent/DK136775B/da unknown
- 1974-07-19 DE DE2434967A patent/DE2434967A1/de active Pending
- 1974-07-22 LU LU70582A patent/LU70582A1/xx unknown
- 1974-07-23 CA CA205,451A patent/CA1019726A/en not_active Expired
- 1974-07-24 IN IN1642/CAL/74A patent/IN139935B/en unknown
- 1974-07-25 NL NL7410061A patent/NL7410061A/xx unknown
- 1974-07-26 OA OA55258A patent/OA04753A/xx unknown
- 1974-07-26 AR AR254903A patent/AR199756A1/es active
- 1974-07-29 CH CH1040374A patent/CH583744A5/xx not_active IP Right Cessation
- 1974-07-31 ES ES428798A patent/ES428798A1/es not_active Expired
- 1974-08-01 GB GB3400874A patent/GB1419933A/en not_active Expired
- 1974-08-02 SE SE7410005A patent/SE412589B/xx unknown
- 1974-08-02 IL IL45384A patent/IL45384A/xx unknown
- 1974-08-06 IE IE1654/74A patent/IE41823B1/en unknown
- 1974-08-07 JP JP8995074A patent/JPS5727119B2/ja not_active Expired

Also Published As

Publication number	Publication date
DK136775C (de)	1978-05-08
LU70582A1 (de)	1976-05-31
SE7410005L (de)	1975-02-10
NL7410061A (nl)	1975-02-11
SE412589B (sv)	1980-03-10
IE41823B1 (en)	1980-04-09
DK136775B (da)	1977-11-21
AU7188674A (en)	1976-02-05
OA04753A (fr)	1980-08-31
JPS5041900A (de)	1975-04-16
CH583744A5 (de)	1977-01-14
CA1019726A (en)	1977-10-25
ES428798A1 (es)	1976-09-16
IE41823L (en)	1975-02-08
JPS5727119B2 (de)	1982-06-08
DK386274A (de)	1975-04-01
IL45384A (en)	1976-09-30
IL45384A0 (en)	1974-11-29
IN139935B (de)	1976-08-21
AR199756A1 (es)	1974-09-23
DE2434967A1 (de)	1975-02-20
GB1419933A (en)	1975-12-31

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Williams et al.	1959	The Stereochemistry of Complex Inorganic Compounds. XXIV. Cobalt Stibenediamine Complexes1
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