IL91154A - Process for converting daonurovicin to doxorubicin by acid hydrolysis of doxorovicin oxalate extracted from 41-bromo-downorovicin - Google Patents

Process for converting daonurovicin to doxorubicin by acid hydrolysis of doxorovicin oxalate extracted from 41-bromo-downorovicin

Info

Publication number: IL91154A
Authority: IL; Israel
Prior art keywords: doxorubicin; daunorubicin; bromo; hydrolysis; oxalic acid
Prior art date: 1988-10-11

Application number

IL9115489A

Other languages

English (en)

Hebrew (he)

Other versions

IL91154A0 (en

Original Assignee

Sicor Spa

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.)

1988-10-11

Filing date

1989-07-28

Publication date

1994-01-25

1989-07-28 Application filed by Sicor Spa filed Critical Sicor Spa

1990-03-19 Publication of IL91154A0 publication Critical patent/IL91154A0/xx

1994-01-25 Publication of IL91154A publication Critical patent/IL91154A/en

Links

AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 title claims abstract description 67
229960004679 doxorubicin Drugs 0.000 title claims abstract description 36
238000000034 method Methods 0.000 title claims abstract description 18
-1 oxalate ester Chemical class 0.000 title claims abstract description 10
KQRWYZDETCDVGB-TZSSRYMLSA-N (7s,9s)-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9-(2-bromoacetyl)-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CBr)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 KQRWYZDETCDVGB-TZSSRYMLSA-N 0.000 title claims description 17
229960000975 daunorubicin Drugs 0.000 title description 10
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 title description 7
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 title description 6
238000006243 chemical reaction Methods 0.000 title description 4
238000005903 acid hydrolysis reaction Methods 0.000 title description 2
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 14
230000007062 hydrolysis Effects 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 53
235000006408 oxalic acid Nutrition 0.000 claims description 17
150000002148 esters Chemical class 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
239000012736 aqueous medium Substances 0.000 claims 1
239000002609 medium Substances 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
150000003839 salts Chemical class 0.000 description 9
239000000243 solution Substances 0.000 description 9
MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
229960002918 doxorubicin hydrochloride Drugs 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 description 5
229960003109 daunorubicin hydrochloride Drugs 0.000 description 5
238000002955 isolation Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000005904 alkaline hydrolysis reaction Methods 0.000 description 4
230000031709 bromination Effects 0.000 description 4
238000005893 bromination reaction Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000203 mixture Substances 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
125000001475 halogen functional group Chemical group 0.000 description 2
238000005907 ketalization reaction Methods 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000011347 resin Substances 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
238000001179 sorption measurement Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
241000187081 Streptomyces peucetius Species 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001816 cooling Methods 0.000 description 1
150000004292 cyclic ethers Chemical class 0.000 description 1
230000003413 degradative effect Effects 0.000 description 1
238000006567 deketalization reaction Methods 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000001145 hydrido group Chemical group *[H] 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000003901 oxalic acid esters Chemical class 0.000 description 1
239000005011 phenolic resin Substances 0.000 description 1
229920001568 phenolic resin Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000012264 purified product Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins

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)

IL9115489A 1988-10-11 1989-07-28 Process for converting daonurovicin to doxorubicin by acid hydrolysis of doxorovicin oxalate extracted from 41-bromo-downorovicin IL91154A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT8822260A IT1230505B (it)	1988-10-11	1988-10-11	Procedimento per la conversione della daunorubicina in doxorubicina.

Publications (2)

Publication Number	Publication Date
IL91154A0 IL91154A0 (en)	1990-03-19
IL91154A true IL91154A (en)	1994-01-25

Family

ID=11193796

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9115489A IL91154A (en)	1988-10-11	1989-07-28	Process for converting daonurovicin to doxorubicin by acid hydrolysis of doxorovicin oxalate extracted from 41-bromo-downorovicin

Country Status (9)

Country	Link
US (1)	US5008380A (fr)
EP (1)	EP0363604A3 (fr)
JP (1)	JPH02129197A (fr)
KR (1)	KR900006357A (fr)
AU (1)	AU615774B2 (fr)
HU (1)	HUT52516A (fr)
IL (1)	IL91154A (fr)
IT (1)	IT1230505B (fr)
ZA (1)	ZA895727B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5976830A (en) *	1996-05-24	1999-11-02	The Ohio State University Research Foundation	Methods of producing doxorubicin
FR2753703B1 (fr) *	1996-09-20	1998-12-04		Procede de synthese de l'acide mercapto-3-propionique
PT848009E (pt) *	1996-12-16	2000-11-30	Pharmachemie Bv	Processo para a preparacao de epirubicina ou seus sais de adicao de acido a partir de daunorubicina
RU2211842C1 (ru) *	2002-01-31	2003-09-10	Закрытое акционерное общество "Фармсинтез"	Способ получения доксорубицина гидрохлорида
JP2015507019A (ja) *	2012-02-17	2015-03-05	セルシオンコーポレイション	感熱性ナノ粒子製剤およびその製造方法
WO2016159092A1 (fr) *	2015-03-30	2016-10-06	ＭｅｉｊｉＳｅｉｋａファルマ株式会社	Procédé de production d'épirubicine et nouvel intermédiaire de production associé
CN108350015A (zh) *	2015-11-05	2018-07-31	浙江海正药业股份有限公司	一种表柔比星或其盐酸盐的分离纯化方法
EP3509605A4 (fr)	2016-09-09	2020-05-27	Irisys, Inc.	Compositions anticancéreuses liposomales
CN106749447B (zh) *	2017-01-10	2018-02-13	鲁南制药集团股份有限公司	一种盐酸表柔比星中间体化合物
CN108484689B (zh) *	2018-03-06	2020-11-10	道中道（菏泽）制药有限公司	一种戊柔比星合成方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB691364A (en) *	1949-02-18	1953-05-13	Nat Starch Products Inc	Polysaccharide derivatives of substituted dicarboxylic acids
US3803124A (en) *	1968-04-12	1974-04-09	Farmaceutici It Soc	Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives
GB1566330A (en) *	1977-02-16	1980-04-30	Farmaceutici Italia	Anthracycline glycosides
JPS56156300A (en) *	1980-04-26	1981-12-02	Microbial Chem Res Found	Novel preparative method of anthracyclin derivative
GB8413464D0 (en) *	1984-05-25	1984-07-04	Erba Farmitalia	Anthracycline-anionic polymer conjugates
FI860683A7 (fi) *	1984-06-14	1986-02-14	Biogal Gyogyszergyar	Menetelmä adriamysiinin ja sen halidisuolojen valmistamiseksi.
AU3774389A (en) *	1988-06-27	1990-01-23	Board Of Regents, The University Of Texas System	4'-deoxy-2'-halo-anthracycline antibiotics, methods for their use, and intermediates and methods for synthesis thereof

1988
- 1988-10-11 IT IT8822260A patent/IT1230505B/it active
- 1988-11-09 US US07/269,199 patent/US5008380A/en not_active Expired - Lifetime
1989
- 1989-07-20 HU HU893682A patent/HUT52516A/hu unknown
- 1989-07-27 AU AU39011/89A patent/AU615774B2/en not_active Ceased
- 1989-07-27 ZA ZA895727A patent/ZA895727B/xx unknown
- 1989-07-28 IL IL9115489A patent/IL91154A/en not_active IP Right Cessation
- 1989-08-07 JP JP1204524A patent/JPH02129197A/ja active Pending
- 1989-08-13 EP EP89114981A patent/EP0363604A3/fr not_active Ceased
- 1989-08-30 KR KR1019890012408A patent/KR900006357A/ko not_active Withdrawn

Also Published As

Publication number	Publication date
ZA895727B (en)	1990-04-25
AU3901189A (en)	1990-04-26
HUT52516A (en)	1990-07-28
AU615774B2 (en)	1991-10-10
IT1230505B (it)	1991-10-25
IL91154A0 (en)	1990-03-19
IT8822260A0 (it)	1988-10-11
JPH02129197A (ja)	1990-05-17
EP0363604A3 (fr)	1990-07-25
US5008380A (en)	1991-04-16
KR900006357A (ko)	1990-05-08
EP0363604A2 (fr)	1990-04-18

Legal Events

Date	Code	Title	Description
1996-05-14	RH	Patent void

Publication	Publication Date	Title
SU1470197A3 (ru)	1989-03-30	Способ очистки сырого доксорубицина
US4289703A (en)	1981-09-15	Antibiotics
EP0342990B1 (fr)	1995-04-19	Procédé pour la préparation d'érythromcine A-oxime ou d'un sel de ce composé
US4757138A (en)	1988-07-12	Process for producing etoposide
CZ54495A3 (en)	1997-08-13	Process for preparing and/or purification of clavulanic acid
US5008380A (en)	1991-04-16	Process for the conversion of daunorubicin into doxorubicin
US4071536A (en)	1978-01-31	Antibiotics
COXON et al.	1961	Simplified preparation of sophorose (2-O-β-D-glucopyranosyl-D-glucose)
JPH06197782A (ja)	1994-07-19	粗クラブラン酸の精製方法
US3977943A (en)	1976-08-31	Antibiotics
SU993822A3 (ru)	1983-01-30	Способ получени гликозидов антрациклина
US4387232A (en)	1983-06-07	Process for preparing N-acylcarnosine
EP0094632B1 (fr)	1986-02-26	(-)-15-Déoxyspergualin, préparation, et produit pharmaceutique le contenant
EP0517345B1 (fr)	1995-07-19	Intermédiaires du groupe mureidomycine, leur préparation et leur usage
US3860607A (en)	1975-01-14	Process for preparing hydroxy-l-proline or n-acetyl-hydroxy-l-proline from hydrolyzed gelatin
US4495348A (en)	1985-01-22	Derivative of cephamycin C
US5338418A (en)	1994-08-16	Process for production of hydroxocobalamin
US3226305A (en)	1965-12-28	Biological transformation of 1,3,10,11,12-pentahydroxynaphthacene - 2 - carboxamides to tetracycline antibiotics
US4290972A (en)	1981-09-22	Process for the production of 4-aminobutyric acid or its derivatives
US3983109A (en)	1976-09-28	Process for recovering cephalosporin C from A fermentation broth as the N-(p-nitrobenzoyl) derivative
US4204058A (en)	1980-05-20	Process for obtaining cephalosporin C and the salts and derivatives thereof from culture filtrates or culture solutions
KR100274787B1 (ko)	2003-10-22	독소루비신및이의염산염의제조정제방법
JP2512050B2 (ja)	1996-07-03	新規抗かび性抗生物質デキシロシルベナノマイシンｂならびにその製造法
RU2644674C1 (ru)	2018-02-13	Способ получения 3,3',3'',3'''-(3,8,13,17-тетраметилпорфирин-2,7,12,18-тетраил) тетрапропионовой кислоты (копропорфирина)
HU176218B (en)	1981-01-28	Process for preparing apovincamine from vincamine or epivincamine