FR2477155A1 - Ergocornine, alpha and beta ergocryptine prodn. - by epimerisation of C-8 epimers, ergocornine and ergocryptine(s) with acid in organic solvents - Google Patents

Ergocornine, alpha and beta ergocryptine prodn. - by epimerisation of C-8 epimers, ergocornine and ergocryptine(s) with acid in organic solvents Download PDF

Info

Publication number: FR2477155A1
Authority: FR; France
Prior art keywords: mixture; alkaloids; general formula; salts; compounds
Prior art date: 1980-03-03
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.): Granted

Application number

FR8103916A

Other languages

English (en)

French (fr)

Other versions

FR2477155B1 (2

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Richter Gedeon Vegyeszeti Gyar Nyrt

Original Assignee

Richter Gedeon Vegyeszeti Gyar RT

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.)

1980-03-03

Filing date

1981-02-27

Publication date

1981-09-04

1980-03-03 Priority claimed from HU80697A external-priority patent/HU191022B/hu

1981-02-27 Application filed by Richter Gedeon Vegyeszeti Gyar RT filed Critical Richter Gedeon Vegyeszeti Gyar RT

1981-09-04 Publication of FR2477155A1 publication Critical patent/FR2477155A1/fr

1985-05-17 Application granted granted Critical

1985-05-17 Publication of FR2477155B1 publication Critical patent/FR2477155B1/fr

Status Granted legal-status Critical Current

Links

239000002253 acid Substances 0.000 title claims abstract description 30
239000003960 organic solvent Substances 0.000 title claims abstract description 17
229950001817 alpha-ergocryptine Drugs 0.000 title description 32
UJYGDMFEEDNVBF-UHFFFAOYSA-N Ergocorninine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-UHFFFAOYSA-N 0.000 title description 28
XQUUDUKVJKNJNP-OGGGUQDZSA-N ergocornine Chemical compound C([C@H]1N(C)C2)C([C]34)=CN=C4C=CC=C3C1=C[C@H]2C(=O)N[C@@]1(C(C)C)C(=O)N2[C@@H](C(C)C)C(=O)N3CCC[C@H]3[C@]2(O)O1 XQUUDUKVJKNJNP-OGGGUQDZSA-N 0.000 title description 21
229950010031 beta-ergocryptine Drugs 0.000 title description 10
YYWXOXLDOMRDHW-UHFFFAOYSA-N beta-ergocryptine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)C(C)CC)C(C)C)C2)=C3C2=CNC3=C1 YYWXOXLDOMRDHW-UHFFFAOYSA-N 0.000 title description 10
YYWXOXLDOMRDHW-SGVWFJRMSA-N β-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)[C@@H](C)CC)C(C)C)C2)=C3C2=CNC3=C1 YYWXOXLDOMRDHW-SGVWFJRMSA-N 0.000 title description 10
YDOTUXAWKBPQJW-UHFFFAOYSA-N alpha-Ergocryptinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-UHFFFAOYSA-N 0.000 title description 6
YDOTUXAWKBPQJW-NSLWYYNWSA-N alpha-ergocryptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=CNC3=C1 YDOTUXAWKBPQJW-NSLWYYNWSA-N 0.000 title description 4
229930013930 alkaloid Natural products 0.000 claims abstract description 78
238000006345 epimerization reaction Methods 0.000 claims abstract description 27
238000000034 method Methods 0.000 claims abstract description 17
150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 8
239000000203 mixture Substances 0.000 claims description 131
150000001875 compounds Chemical class 0.000 claims description 47
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 44
150000003839 salts Chemical class 0.000 claims description 42
OFKDAAIKGIBASY-VFGNJEKYSA-N ergotamine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@@](C(N21)=O)(C)NC(=O)[C@H]1CN([C@H]2C(C3=CC=CC4=NC=C([C]34)C2)=C1)C)C1=CC=CC=C1 OFKDAAIKGIBASY-VFGNJEKYSA-N 0.000 claims description 37
229960004943 ergotamine Drugs 0.000 claims description 30
XCGSFFUVFURLIX-UHFFFAOYSA-N ergotaminine Natural products C1=C(C=2C=CC=C3NC=C(C=23)C2)C2N(C)CC1C(=O)NC(C(N12)=O)(C)OC1(O)C1CCCN1C(=O)C2CC1=CC=CC=C1 XCGSFFUVFURLIX-UHFFFAOYSA-N 0.000 claims description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 22
229960003133 ergot alkaloid Drugs 0.000 claims description 22
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238000000926 separation method Methods 0.000 claims description 21
239000011541 reaction mixture Substances 0.000 claims description 20
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 18
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 11
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239000010452 phosphate Substances 0.000 claims description 11
239000002904 solvent Substances 0.000 claims description 11
239000011975 tartaric acid Substances 0.000 claims description 11
235000002906 tartaric acid Nutrition 0.000 claims description 11
239000012535 impurity Substances 0.000 claims description 6
229940095064 tartrate Drugs 0.000 claims description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
239000012452 mother liquor Substances 0.000 claims description 2
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239000000243 solution Substances 0.000 description 17
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 14
150000003013 phosphoric acid derivatives Chemical class 0.000 description 10
XWTYUTWHTOOWSS-WTDBAMAISA-N Ergonine Chemical compound CC[C@@]1(NC(=O)[C@H]2CN(C)C3CC4=CNC5=CC=CC(=C45)C3=C2)O[C@@]2(O)C3CCCN3C(=O)[C@H](C(C)C)N2C1=O XWTYUTWHTOOWSS-WTDBAMAISA-N 0.000 description 9
XWTYUTWHTOOWSS-MWBPXRJMSA-N Ergonine Natural products O=C(N[C@@]1(CC)C(=O)N2[C@H](C(C)C)C(=O)N3[C@@H]([C@]2(O)O1)CCC3)[C@@H]1C=C2[C@H](N(C)C1)Cc1c3c([nH]c1)cccc23 XWTYUTWHTOOWSS-MWBPXRJMSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
208000005223 Alkalosis Diseases 0.000 description 8
239000007858 starting material Substances 0.000 description 8
229960001367 tartaric acid Drugs 0.000 description 8
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XLMJRFCCCWFQRE-SJRQCXNHSA-N ecboline Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)CN2C(=O)[C@]3(C(C)C)NC(=O)[C@@H](CN(C)[C@@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 XLMJRFCCCWFQRE-SJRQCXNHSA-N 0.000 description 7
UJYGDMFEEDNVBF-XJUOHTAZSA-N ergocorninine Chemical compound C1=CC(C=2[C@@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)C(C)C)C(C)C)C2)=C3C2=CNC3=C1 UJYGDMFEEDNVBF-XJUOHTAZSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
JFRCRHHCXKEHBW-UHFFFAOYSA-N Ergoptin Natural products O1C2(O)C3CCCN3C(=O)C(CC(C)C)N2C(=O)C1(CC)NC(=O)C(CN(C)C1C2)C=C1C1=C3C2=CNC3=CC=C1 JFRCRHHCXKEHBW-UHFFFAOYSA-N 0.000 description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
JFRCRHHCXKEHBW-YKAZNSBZSA-N ergoptin Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)[C@@H](CC(C)C)N2C(=O)[C@]3(CC)NC(=O)[C@@H](CN(C)[C@@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 JFRCRHHCXKEHBW-YKAZNSBZSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
XWTYUTWHTOOWSS-FPNLSDLLSA-N 34896-18-9 Chemical compound C([C@H]1[C@]2(O)O3)CCN1C(=O)[C@@H](C(C)C)N2C(=O)[C@]3(CC)NC(=O)[C@@H](CN(C)[C@H]1C2)C=C1C1=C3C2=CNC3=CC=C1 XWTYUTWHTOOWSS-FPNLSDLLSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
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WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
150000001408 amides Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
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-1 ergoptine Natural products 0.000 description 3
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241001136782 Alca Species 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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WVVSZNPYNCNODU-XTQGRXLLSA-N Lysergic acid propanolamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@H](CO)C)C2)=C3C2=CNC3=C1 WVVSZNPYNCNODU-XTQGRXLLSA-N 0.000 description 2
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QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000001476 alcoholic effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
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HEFIYUQVAZFDEE-UHFFFAOYSA-N ergocristinine Natural products N12C(=O)C(C(C)C)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 HEFIYUQVAZFDEE-UHFFFAOYSA-N 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000000463 material Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
150000003892 tartrate salts Chemical class 0.000 description 2
239000003643 water by type Substances 0.000 description 2
NSFIAKFOCAEBER-UHFFFAOYSA-N 2,3-dihydroxy-2,3-bis(4-methylphenyl)butanedioic acid Chemical class C1=CC(C)=CC=C1C(O)(C(O)=O)C(O)(C(O)=O)C1=CC=C(C)C=C1 NSFIAKFOCAEBER-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
241000221751 Claviceps purpurea Species 0.000 description 1
NESVMZOPWPCFAU-UHFFFAOYSA-N Ergoclavinine Natural products C1=CC(C=2C(N(C)CC(C=2)C(=O)NC2(C(=O)N3C(C(N4CCCC4C3(O)O2)=O)CC(C)C)C)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-UHFFFAOYSA-N 0.000 description 1
BOLCFGMGGWCOOE-UHFFFAOYSA-N Ergostine Natural products N12C(=O)C(CC)(NC(=O)C3C=C4C=5C=CC=C6NC=C(C=56)CC4N(C)C3)OC2(O)C2CCCN2C(=O)C1CC1=CC=CC=C1 BOLCFGMGGWCOOE-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
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KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-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
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
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150000001340 alkali metals Chemical class 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical compound [NH4+].OS([O-])(=O)=O BIGPRXCJEDHCLP-UHFFFAOYSA-N 0.000 description 1
LFVGISIMTYGQHF-UHFFFAOYSA-N ammonium dihydrogen phosphate Chemical compound [NH4+].OP(O)([O-])=O LFVGISIMTYGQHF-UHFFFAOYSA-N 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
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239000003054 catalyst Substances 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
229960001270 d- tartaric acid Drugs 0.000 description 1
238000011033 desalting Methods 0.000 description 1
OWEUDBYTKOYTAD-MKTPKCENSA-N ergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@@H]1C=C2C3=CC=CC4=NC=C([C]34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 OWEUDBYTKOYTAD-MKTPKCENSA-N 0.000 description 1
HEFIYUQVAZFDEE-NASJTFDLSA-N ergocristinine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1C=C2C=3C=CC=C4NC=C(C=34)C[C@H]2N(C)C1)C(C)C)C1=CC=CC=C1 HEFIYUQVAZFDEE-NASJTFDLSA-N 0.000 description 1
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FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
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239000011630 iodine Substances 0.000 description 1
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235000019796 monopotassium phosphate Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
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GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
- C07D519/02—Ergot alkaloids of the cyclic peptide type

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

FR8103916A 1980-03-03 1981-02-27 Ergocornine, alpha and beta ergocryptine prodn. - by epimerisation of C-8 epimers, ergocornine and ergocryptine(s) with acid in organic solvents Granted FR2477155A1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU80697A HU191022B (en)	1979-03-26	1980-03-03	Composite tablet

Publications (2)

Publication Number	Publication Date
FR2477155A1 true FR2477155A1 (en)	1981-09-04
FR2477155B1 FR2477155B1 (2)	1985-05-17

Family

ID=10950898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FR8103916A Granted FR2477155A1 (en)	1980-03-03	1981-02-27	Ergocornine, alpha and beta ergocryptine prodn. - by epimerisation of C-8 epimers, ergocornine and ergocryptine(s) with acid in organic solvents

Country Status (6)

Country	Link
BE (1)	BE887712A (2)
CH (1)	CH646707A5 (2)
CS (1)	CS223993B2 (2)
FR (1)	FR2477155A1 (2)
IT (1)	IT1193584B (2)
SU (1)	SU1222198A3 (2)

Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB445325A (en) *	1935-07-29	1936-04-07	Wellcome Found	The manufacture of ergometrine
DE861562C (de) *	1942-09-16	1953-01-05	Sandoz Ag	Verfahren zur Trennung und Reindarstellung von Lysergsaeure- und Isolysergsaeure-Derivaten
DE2805977A1 (de) *	1977-02-22	1978-08-31	Sandoz Ag	Neue ergopeptidalkaloide, ihre herstellung und verwendung
DE2929027A1 (de) *	1978-07-19	1980-01-31	Lek Tovarna Farmacevtskih	Saeureadditionssalze rechtsdrehender ergot-alkaloide, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel
BE880600A (fr) *	1979-12-13	1980-04-01	Richter Gedeon Vegyeszet	Procede d'obtention d'alcaloides peptidiques du type ergol

1981
- 1981-02-11 CH CH89581A patent/CH646707A5/de not_active IP Right Cessation
- 1981-02-18 CS CS811168A patent/CS223993B2/cs unknown
- 1981-02-27 BE BE1/10152A patent/BE887712A/fr not_active IP Right Cessation
- 1981-02-27 FR FR8103916A patent/FR2477155A1/fr active Granted
- 1981-03-02 SU SU813252498A patent/SU1222198A3/ru active
- 1981-03-02 IT IT20088/81A patent/IT1193584B/it active

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB445325A (en) *	1935-07-29	1936-04-07	Wellcome Found	The manufacture of ergometrine
DE861562C (de) *	1942-09-16	1953-01-05	Sandoz Ag	Verfahren zur Trennung und Reindarstellung von Lysergsaeure- und Isolysergsaeure-Derivaten
DE2805977A1 (de) *	1977-02-22	1978-08-31	Sandoz Ag	Neue ergopeptidalkaloide, ihre herstellung und verwendung
DE2929027A1 (de) *	1978-07-19	1980-01-31	Lek Tovarna Farmacevtskih	Saeureadditionssalze rechtsdrehender ergot-alkaloide, verfahren zu deren herstellung sowie ihre verwendung als arzneimittel
BE880600A (fr) *	1979-12-13	1980-04-01	Richter Gedeon Vegyeszet	Procede d'obtention d'alcaloides peptidiques du type ergol

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
HELVETICA CHIMICA ACTA, vol. 26, 1943, Bâle A. STOLL et al. "Die Alkaloide der Ergotoxingruppe: Ergocristin, Ergokryptin und Ergocornin", pages 1570-1601 *

Also Published As

Publication number	Publication date
CS223993B2 (en)	1983-11-25
IT8120088A0 (it)	1981-03-02
FR2477155B1 (2)	1985-05-17
CH646707A5 (en)	1984-12-14
SU1222198A3 (ru)	1986-03-30
BE887712A (fr)	1981-08-27
IT1193584B (it)	1988-07-08

Legal Events

Date	Code	Title	Description
1996-12-27	ST	Notification of lapse

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US20070135638A1 (en)	2007-06-14	Process for the manufacture of lysergic acid
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EP0117861B1 (fr)	1987-12-09	Procédé d'obtention de la vincristine
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HU180056B (hu)	1983-01-28	Üj eljárás ergotoxin-típusú alkaloidok előállítására anyarozsalkaloid keverékekből epimerizáció és/vagy sóképzés útjánn
BE521626A (2)
KR0179369B1 (ko)	1999-05-15	포시노프릴 동질이상체의 선택적 제조 방법
HU183062B (en)	1984-04-28	New process for preparing ergocristine
CH634288A5 (fr)	1983-01-31	Pantoate de guanidine.
CS223994B2 (cs)	1983-11-25	Způsob čištění ergot-alkaloidů
CH625519A5 (2)	1981-09-30