CS255876B2 - Process for preparing new 10 alpha-methoxy-6-methyl-ergolines - Google Patents

Process for preparing new 10 alpha-methoxy-6-methyl-ergolines Download PDF

Info

Publication number: CS255876B2
Authority: CS; Czechoslovakia
Prior art keywords: methyl; formula; hydrogen; lumilysergol; halo
Prior art date: 1985-06-21

Application number

CS864585A

Other languages

Czech (cs)

English (en)

Inventor

Gabor Megyeri

Tibor Keve

Bela Stefko

Erik Bogsch

Janos Galambos

Anna Kassai

Ferenc Trischler

Eva Palosi

Dora Groo

Egon Karpati

Zsolt Szombathelyi

Laszlo Szporny

Bela Kiss

Istvan Laszlovszky

Erzsebet Lapis

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.)

1985-06-21

Filing date

1986-06-20

Publication date

1988-03-15

1986-06-20 Application filed by Richter Gedeon Vegyeszet filed Critical Richter Gedeon Vegyeszet

1988-03-15 Publication of CS255876B2 publication Critical patent/CS255876B2/cs

Links

238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 21
238000000034 method Methods 0.000 claims abstract description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 15
239000002253 acid Substances 0.000 claims abstract description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 11
229910052794 bromium Inorganic materials 0.000 claims abstract description 10
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
239000000460 chlorine Chemical group 0.000 claims abstract description 10
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 9
229910052740 iodine Chemical group 0.000 claims abstract description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
-1 5-bromo-nicotinoyl group Chemical group 0.000 claims abstract description 6
238000002360 preparation method Methods 0.000 claims abstract description 6
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
150000002148 esters Chemical class 0.000 claims description 9
230000032050 esterification Effects 0.000 claims description 8
238000005886 esterification reaction Methods 0.000 claims description 8
238000006552 photochemical reaction Methods 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
230000015572 biosynthetic process Effects 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
QCCLDOMKAQLVCM-IIWDCPNDSA-N (6aR,10aR)-9-methoxy-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline Chemical class COC1CN([C@@H]2CC3=CNC4=CC=CC([C@H]2C1)=C34)C QCCLDOMKAQLVCM-IIWDCPNDSA-N 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
YSEXMKHXIOCEJA-FVFQAYNVSA-N Nicergoline Chemical compound C([C@@H]1C[C@]2([C@H](N(C)C1)CC=1C3=C2C=CC=C3N(C)C=1)OC)OC(=O)C1=CN=CC(Br)=C1 YSEXMKHXIOCEJA-FVFQAYNVSA-N 0.000 abstract description 11
229960003642 nicergoline Drugs 0.000 abstract description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
230000000903 blocking effect Effects 0.000 abstract description 3
239000011630 iodine Chemical group 0.000 abstract description 3
238000006198 methoxylation reaction Methods 0.000 abstract description 3
239000000543 intermediate Substances 0.000 abstract description 2
239000000810 peripheral vasodilating agent Substances 0.000 abstract description 2
229960002116 peripheral vasodilator Drugs 0.000 abstract description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
101150049660 DRD2 gene Proteins 0.000 abstract 1
230000004048 modification Effects 0.000 abstract 1
238000012986 modification Methods 0.000 abstract 1
230000003389 potentiating effect Effects 0.000 abstract 1
239000000243 solution Substances 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
239000000203 mixture Substances 0.000 description 15
239000000047 product Substances 0.000 description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
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BIXJFIJYBLJTMK-UHFFFAOYSA-N Lysergol Natural products C1=CC(C2=CC(CO)CN(C2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-UHFFFAOYSA-N 0.000 description 7
239000000010 aprotic solvent Substances 0.000 description 7
BIXJFIJYBLJTMK-MEBBXXQBSA-N lysergol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=CNC3=C1 BIXJFIJYBLJTMK-MEBBXXQBSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
238000007069 methylation reaction Methods 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
FQIUCPGDKPXSLL-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid Chemical compound OC(=O)C1=CN=CC(Br)=C1 FQIUCPGDKPXSLL-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
AWFDCTXCTHGORH-HGHGUNKESA-N 6-[4-[(6ar,9r,10ar)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4h-indolo[4,3-fg]quinoline-9-carbonyl]piperazin-1-yl]-1-methylpyridin-2-one Chemical group O=C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4NC(Br)=C(C=34)C2)C1)C)N(CC1)CCN1C1=CC=CC(=O)N1C AWFDCTXCTHGORH-HGHGUNKESA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
229910000147 aluminium phosphate Inorganic materials 0.000 description 4
238000002425 crystallisation Methods 0.000 description 4
230000008025 crystallization Effects 0.000 description 4
239000005457 ice water Substances 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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ZOUBAHRISDTOBN-YMTOWFKASA-N [(6ar,9r)-5-bromo-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=C(Br)NC3=C1 ZOUBAHRISDTOBN-YMTOWFKASA-N 0.000 description 3
UDIJSKHBACNYIE-YMTOWFKASA-N [(6ar,9r)-5-chloro-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methanol Chemical compound C1=CC(C2=C[C@@H](CO)CN([C@@H]2C2)C)=C3C2=C(Cl)NC3=C1 UDIJSKHBACNYIE-YMTOWFKASA-N 0.000 description 3
MOYIIEKIOZCSQI-YMTOWFKASA-N [(6ar,9r)-5-chloro-7-methyl-6,6a,8,9-tetrahydro-4h-indolo[4,3-fg]quinoline-9-yl]methyl dihydrogen phosphate Chemical compound C1=CC(C2=C[C@@H](COP(O)(O)=O)CN([C@@H]2C2)C)=C3C2=C(Cl)NC3=C1 MOYIIEKIOZCSQI-YMTOWFKASA-N 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
230000011987 methylation Effects 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
ZAGRKAFMISFKIO-UHFFFAOYSA-N Isolysergic acid Natural products C1=CC(C2=CC(CN(C2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-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
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
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238000004440 column chromatography Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
238000005695 dehalogenation reaction Methods 0.000 description 2
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 2
230000005496 eutectics Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
238000000605 extraction Methods 0.000 description 2
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125000005843 halogen group Chemical group 0.000 description 2
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ZAGRKAFMISFKIO-QMTHXVAHSA-N lysergic acid Chemical compound C1=CC(C2=C[C@H](CN([C@@H]2C2)C)C(O)=O)=C3C2=CNC3=C1 ZAGRKAFMISFKIO-QMTHXVAHSA-N 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
239000003586 protic polar solvent Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
PUBHWOQIXSNMMN-HIFRSBDPSA-N (6ar,10as)-10a-methoxy-6,6a,7,8,9,10-hexahydro-4h-indolo[4,3-fg]quinoline Chemical class C1=CC([C@]2(OC)[C@H](NCCC2)C2)=C3C2=CNC3=C1 PUBHWOQIXSNMMN-HIFRSBDPSA-N 0.000 description 1
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SVXWLTGAHFBMDF-UHFFFAOYSA-N 1h-imidazole;triphenyl phosphite Chemical compound C1=CNC=N1.C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 SVXWLTGAHFBMDF-UHFFFAOYSA-N 0.000 description 1
CVWMSZOUPMVVRF-UHFFFAOYSA-N 5-bromopyridine-3-carboxylic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound ON1C(=O)CCC1=O.OC(=O)C1=CN=CC(Br)=C1 CVWMSZOUPMVVRF-UHFFFAOYSA-N 0.000 description 1
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VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
102000015554 Dopamine receptor Human genes 0.000 description 1
108050004812 Dopamine receptor Proteins 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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235000019483 Peanut oil Nutrition 0.000 description 1
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YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
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235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000004448 titration Methods 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D457/00—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid
- C07D457/02—Heterocyclic compounds containing indolo [4, 3-f, g] quinoline ring systems, e.g. derivatives of ergoline, of the formula:, e.g. lysergic acid with hydrocarbon or substituted hydrocarbon radicals, attached in position 8

Landscapes

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

CS864585A 1985-06-21 1986-06-20 Process for preparing new 10 alpha-methoxy-6-methyl-ergolines CS255876B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU852446A HU193781B (en)	1985-06-21	1985-06-21	Process for producing 10alpha-methoxy-6-methylergoline derivatives and acid additional salts thereof

Publications (1)

Publication Number	Publication Date
CS255876B2 true CS255876B2 (en)	1988-03-15

Family

ID=10959396

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS864585A CS255876B2 (en)	1985-06-21	1986-06-20	Process for preparing new 10 alpha-methoxy-6-methyl-ergolines

Country Status (14)

Country	Link
BE (1)	BE904956A (de)
CS (1)	CS255876B2 (de)
DD (1)	DD246110A5 (de)
DE (1)	DE3620487A1 (de)
DK (1)	DK291986A (de)
ES (1)	ES8801263A1 (de)
FR (1)	FR2583755B1 (de)
GB (1)	GB2177090B (de)
GR (1)	GR861619B (de)
HU (1)	HU193781B (de)
IT (1)	IT1190135B (de)
LU (1)	LU86486A1 (de)
NL (1)	NL8601584A (de)
PT (1)	PT82807B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU196598B (en) *	1986-04-25	1988-12-28	Richter Gedeon Vegyeszet	Process for producing 1- and/or 8-substituted 2-halogenated ergoline derivatives and pharmaceutics comprising such compounds
GB9603226D0 (en) *	1996-02-15	1996-04-17	Pharmacia Spa	Heterocyclyl-ergoline derivatives

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1094965B (it) *	1978-04-05	1985-08-10	Corvi Mora E	Procedimento di preparazione di derivati del lisergolo
HU193782B (en) *	1985-06-21	1987-11-30	Richter Gedeon Vegyeszet	Process for producing 2-halogeno-nicergoline derivatives and acid additional salts thereof

1985
- 1985-06-21 HU HU852446A patent/HU193781B/hu not_active IP Right Cessation
1986
- 1986-06-19 DE DE19863620487 patent/DE3620487A1/de not_active Withdrawn
- 1986-06-19 NL NL8601584A patent/NL8601584A/nl not_active Application Discontinuation
- 1986-06-19 IT IT20854/86A patent/IT1190135B/it active
- 1986-06-19 FR FR868608869A patent/FR2583755B1/fr not_active Expired - Lifetime
- 1986-06-19 BE BE0/216805A patent/BE904956A/fr not_active IP Right Cessation
- 1986-06-20 GR GR861619A patent/GR861619B/el unknown
- 1986-06-20 DD DD86291508A patent/DD246110A5/de not_active IP Right Cessation
- 1986-06-20 LU LU86486A patent/LU86486A1/de unknown
- 1986-06-20 PT PT82807A patent/PT82807B/pt not_active IP Right Cessation
- 1986-06-20 GB GB8615121A patent/GB2177090B/en not_active Expired
- 1986-06-20 CS CS864585A patent/CS255876B2/cs unknown
- 1986-06-20 DK DK291986A patent/DK291986A/da not_active Application Discontinuation
- 1986-06-20 ES ES556358A patent/ES8801263A1/es not_active Expired

Also Published As

Publication number	Publication date
PT82807A (en)	1986-07-01
GB2177090B (en)	1989-07-12
HUT41023A (en)	1987-03-30
DK291986A (da)	1986-12-22
FR2583755B1 (fr)	1990-06-22
PT82807B (pt)	1988-04-21
GR861619B (en)	1986-10-21
GB8615121D0 (en)	1986-07-23
BE904956A (fr)	1986-12-19
IT8620854A1 (it)	1987-12-19
LU86486A1 (de)	1986-12-02
DE3620487A1 (de)	1987-01-02
FR2583755A1 (fr)	1986-12-26
HU193781B (en)	1987-11-30
NL8601584A (nl)	1987-01-16
DK291986D0 (da)	1986-06-20
DD246110A5 (de)	1987-05-27
IT1190135B (it)	1988-02-10
IT8620854A0 (it)	1986-06-19
ES8801263A1 (es)	1988-01-01
ES556358A0 (es)	1988-01-01
GB2177090A (en)	1987-01-14

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