CS223993B2 - Method of making the ergot-alcaloid - Google Patents

Method of making the ergot-alcaloid Download PDF

Info

Publication number: CS223993B2
Authority: CS; Czechoslovakia
Prior art keywords: alkaloids; formula; salts; mixture; ergotamine
Prior art date: 1980-03-03

Application number

CS811168A

Other languages

Czech (cs)

English (en)

Inventor

Laszlo Terdy

Janos Kiss

Arpad Trompler

Istvan Zambo

Zsuzsana Foeldesi

Lajos Dancsi

Anna Kassai

Maria Gazdag

Original Assignee

Richter Gedeon Vegyeszet

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

1981-02-18

Publication date

1983-11-25

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

1981-02-18 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1982-01-12 Priority to CS82247A priority Critical patent/CS223994B2/cs

1983-11-25 Publication of CS223993B2 publication Critical patent/CS223993B2/cs

Links

238000004519 manufacturing process Methods 0.000 title description 2
229930013930 alkaloid Natural products 0.000 claims abstract description 65
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 36
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 abstract description 27
229960004943 ergotamine Drugs 0.000 claims abstract description 22
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 abstract description 22
238000000034 method Methods 0.000 claims abstract description 22
239000002585 base Substances 0.000 claims abstract description 20
229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 19
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims abstract description 18
239000012452 mother liquor Substances 0.000 claims abstract description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract 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 abstract description 17
239000011975 tartaric acid Substances 0.000 claims abstract description 17
235000002906 tartaric acid Nutrition 0.000 claims abstract description 17
239000002253 acid Substances 0.000 claims abstract description 16
239000003960 organic solvent Substances 0.000 claims abstract description 16
239000002904 solvent Substances 0.000 claims abstract description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 76
150000001875 compounds Chemical class 0.000 claims description 42
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
239000011541 reaction mixture Substances 0.000 claims description 17
238000006345 epimerization reaction Methods 0.000 claims description 10
150000007513 acids Chemical class 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
238000000926 separation method Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 4
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
239000003513 alkali Chemical class 0.000 claims 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical class [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims 1
229910000397 disodium phosphate Inorganic materials 0.000 claims 1
235000019800 disodium phosphate Nutrition 0.000 claims 1
239000001488 sodium phosphate Substances 0.000 claims 1
229960003133 ergot alkaloid Drugs 0.000 abstract description 21
229910019142 PO4 Inorganic materials 0.000 abstract description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 abstract description 6
239000010452 phosphate Substances 0.000 abstract description 6
238000006243 chemical reaction Methods 0.000 abstract description 5
229940095064 tartrate Drugs 0.000 abstract description 2
239000012458 free base Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
235000021317 phosphate Nutrition 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
150000003797 alkaloid derivatives Chemical class 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
-1 alkaloid tartrates Chemical class 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
NESVMZOPWPCFAU-ZPRCMDFASA-N ergosine 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)C2)=C3C2=CNC3=C1 NESVMZOPWPCFAU-ZPRCMDFASA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
150000003013 phosphoric acid derivatives Chemical class 0.000 description 5
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
XWTYUTWHTOOWSS-UHFFFAOYSA-N Ergonin Natural products O1C2(O)C3CCCN3C(=O)C(C(C)C)N2C(=O)C1(CC)NC(=O)C(CN(C)C1C2)C=C1C1=C3C2=CNC3=CC=C1 XWTYUTWHTOOWSS-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000013078 crystal Substances 0.000 description 3
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 3
239000002609 medium Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
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 description 2
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 description 2
229950001817 alpha-ergocryptine Drugs 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
UJYGDMFEEDNVBF-UHFFFAOYSA-N ergocornin Chemical compound 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 description 2
238000000855 fermentation Methods 0.000 description 2
230000004151 fermentation Effects 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
239000005556 hormone Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
LQIAZOCLNBBZQK-UHFFFAOYSA-N 1-(1,2-Diphosphanylethyl)pyrrolidin-2-one Chemical compound PCC(P)N1CCCC1=O LQIAZOCLNBBZQK-UHFFFAOYSA-N 0.000 description 1
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
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 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
241000282994 Cervidae 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
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 1
206010019233 Headaches Diseases 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
230000001476 alcoholic effect Effects 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
BIGPRXCJEDHCLP-UHFFFAOYSA-N ammonium bisulfate Chemical class [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
229910000387 ammonium dihydrogen phosphate Inorganic materials 0.000 description 1
229940125684 antimigraine agent Drugs 0.000 description 1
239000002282 antimigraine agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
229950010031 beta-ergocryptine Drugs 0.000 description 1
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 description 1
229960003237 betaine Drugs 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
239000012267 brine Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
238000001514 detection method Methods 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002118 epoxides Chemical class 0.000 description 1
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 1
150000002148 esters Chemical class 0.000 description 1
PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000000605 extraction Methods 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
238000001640 fractional crystallisation Methods 0.000 description 1
239000003502 gasoline Substances 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
231100000869 headache Toxicity 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
235000019837 monoammonium phosphate Nutrition 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000004880 oxines Chemical class 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
238000012018 process simulation test Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical group CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000008096 xylene Substances 0.000 description 1
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 description 1

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

Landscapes

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)

CS811168A 1980-03-03 1981-02-18 Method of making the ergot-alcaloid CS223993B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CS82247A CS223994B2 (cs)	1980-03-03	1982-01-12	Způsob čištění ergot-alkaloidů

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CS223993B2 true CS223993B2 (en)	1983-11-25

Family

ID=10950898

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS811168A CS223993B2 (en)	1980-03-03	1981-02-18	Method of making the ergot-alcaloid

Country Status (6)

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

Family Cites Families (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
CH626373A5 (fr) *	1977-02-22	1981-11-13	Sandoz Ag
YU41110B (en) *	1978-07-19	1986-12-31	Lek Tovarna Farmacevtskih	Process for preparing dextrorotatory ergot alcaloids acid addition salts
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 FR FR8103916A patent/FR2477155A1/fr active Granted
- 1981-02-27 BE BE1/10152A patent/BE887712A/fr not_active IP Right Cessation
- 1981-03-02 IT IT20088/81A patent/IT1193584B/it active
- 1981-03-02 SU SU813252498A patent/SU1222198A3/ru active

Also Published As

Publication number	Publication date
BE887712A (fr)	1981-08-27
CH646707A5 (en)	1984-12-14
SU1222198A3 (ru)	1986-03-30
IT8120088A0 (it)	1981-03-02
FR2477155A1 (en)	1981-09-04
IT1193584B (it)	1988-07-08
FR2477155B1 (fr)	1985-05-17

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