SE444114B - Forfarande for framstellning av stabila losningar av hydrerade ergotalkaloider - Google Patents

Forfarande for framstellning av stabila losningar av hydrerade ergotalkaloider

Info

Publication number: SE444114B
Authority: SE; Sweden
Prior art keywords: weight; mixture; carbon atoms; propylene glycol; ethanol
Prior art date: 1977-08-06

Application number

SE7808210A

Other languages

English (en)

Swedish (sv)

Other versions

SE7808210L (sv

Inventor

L Ehrhardt

L Patt

V Hartmann

Original Assignee

Sandoz Ag

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.)

1977-08-06

Filing date

1978-07-28

Publication date

1986-03-24

1978-07-28 Application filed by Sandoz Ag filed Critical Sandoz Ag

1979-02-07 Publication of SE7808210L publication Critical patent/SE7808210L/xx

1986-03-24 Publication of SE444114B publication Critical patent/SE444114B/sv

Links

238000000034 method Methods 0.000 title claims description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 34
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 21
239000000203 mixture Substances 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
239000011877 solvent mixture Substances 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 5
150000001298 alcohols Chemical class 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 4
PBUNVLRHZGSROC-VTIMJTGVSA-N dihydro-alpha-ergocryptine Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1 PBUNVLRHZGSROC-VTIMJTGVSA-N 0.000 claims description 3
SEALOBQTUQIVGU-QNIJNHAOSA-N dihydroergocornine Chemical compound C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1 SEALOBQTUQIVGU-QNIJNHAOSA-N 0.000 claims description 3
229960004290 dihydroergocornine Drugs 0.000 claims description 3
LIMAOLZSWRJOMG-HJPBWRTMSA-N dihydroergocristine Chemical compound C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C(C)C)C1=CC=CC=C1 LIMAOLZSWRJOMG-HJPBWRTMSA-N 0.000 claims description 3
229960004318 dihydroergocristine Drugs 0.000 claims description 3
229960002032 dihydroergocryptine Drugs 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims 2
239000001257 hydrogen Substances 0.000 claims 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
125000000217 alkyl group Chemical group 0.000 claims 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
PBKVEOSEPXMKDN-LZHUFOCISA-N chembl2311030 Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)CC)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)N4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(N21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 PBKVEOSEPXMKDN-LZHUFOCISA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
239000000243 solution Substances 0.000 description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
238000003756 stirring Methods 0.000 description 6
150000005846 sugar alcohols Polymers 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000654 additive Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
QHZUABXEBRGBLP-LKWYKXIFSA-N (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-4-benzyl-9b-hydroxy-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,9R,10aR)-N-[(2R,4R,9aS,9bR)-9b-hydroxy-3,5-dioxo-2,4-di(propan-2-yl)-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide (6aR,10aR)-N-[(2S,4S,9bS)-9b-hydroxy-4-(2-methylpropyl)-3,5-dioxo-2-propan-2-yl-3a,4,7,8,9,9a-hexahydrofuro[3,2-g]indolizin-2-yl]-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C1=CC([C@H]2C[C@H](CN(C)[C@@H]2C2)C(=O)N[C@]3(C(=O)C4[C@H](C(N5CCC[C@H]5[C@]4(O)O3)=O)C(C)C)C(C)C)=C3C2=CNC3=C1.C1=CC([C@H]2CC(CN(C)[C@@H]2C2)C(=O)N[C@@]3(C(=O)C4[C@@H](C(N5CCCC5[C@@]4(O)O3)=O)CC(C)C)C(C)C)=C3C2=CNC3=C1.C([C@H]1C(=O)N2CCC[C@H]2[C@]2(O)O[C@](C(C21)=O)(NC(=O)[C@H]1CN(C)[C@H]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C(C)C)C1=CC=CC=C1 QHZUABXEBRGBLP-LKWYKXIFSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
241000221785 Erysiphales Species 0.000 description 2
229930013930 alkaloid Natural products 0.000 description 2
239000012298 atmosphere Substances 0.000 description 2
HESHRHUZIWVEAJ-JGRZULCMSA-N dihydroergotamine 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]2[C@@H](C3=CC=CC4=NC=C([C]34)C2)C1)C)C1=CC=CC=C1 HESHRHUZIWVEAJ-JGRZULCMSA-N 0.000 description 2
229960004704 dihydroergotamine Drugs 0.000 description 2
ADYPXRFPBQGGAH-UMYZUSPBSA-N dihydroergotamine mesylate Chemical compound CS(O)(=O)=O.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]2[C@@H](C=3C=CC=C4NC=C(C=34)C2)C1)C)C1=CC=CC=C1 ADYPXRFPBQGGAH-UMYZUSPBSA-N 0.000 description 2
230000007717 exclusion Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
229960000541 cetyl alcohol Drugs 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
238000002309 gasification Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000000691 measurement method Methods 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
150000002895 organic esters Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
238000011085 pressure filtration Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
230000001225 therapeutic effect Effects 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

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/48—Ergoline derivatives, e.g. lysergic acid, ergotamine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)

SE7808210A 1977-08-06 1978-07-28 Forfarande for framstellning av stabila losningar av hydrerade ergotalkaloider SE444114B (sv)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19772735587 DE2735587A1 (de)	1977-08-06	1977-08-06	Stabile loesungen und verfahren zu deren herstellung

Publications (2)

Publication Number	Publication Date
SE7808210L SE7808210L (sv)	1979-02-07
SE444114B true SE444114B (sv)	1986-03-24

Family

ID=6015843

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SE7808210A SE444114B (sv)	1977-08-06	1978-07-28	Forfarande for framstellning av stabila losningar av hydrerade ergotalkaloider

Country Status (23)

Country	Link
JP (1)	JPS5428811A (de)
AT (1)	AT364463B (de)
AU (1)	AU525725B2 (de)
BE (1)	BE869560R (de)
CA (1)	CA1111348A (de)
CH (1)	CH635347A5 (de)
CS (1)	CS203199B2 (de)
DE (1)	DE2735587A1 (de)
DK (1)	DK337678A (de)
FI (1)	FI782341A7 (de)
FR (1)	FR2399248A2 (de)
GB (1)	GB1596948A (de)
GR (1)	GR72791B (de)
IE (1)	IE47791B1 (de)
IL (1)	IL55285A (de)
IT (1)	IT1202759B (de)
NL (1)	NL7808122A (de)
NO (1)	NO147901C (de)
NZ (1)	NZ188073A (de)
PT (1)	PT68386A (de)
SE (1)	SE444114B (de)
YU (1)	YU188378A (de)
ZA (1)	ZA784435B (de)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2930369A1 (de) *	1979-07-26	1981-02-05	Rentschler Arzneimittel	Arzneimittelloesungen
DE2945636A1 (de) *	1979-11-12	1981-05-21	Sandoz-Patent-GmbH, 7850 Lörrach	Stabile loesungen von hydrierten ergotalkaloiden bzw. ihren salzen und heparin bzw. seinen salzen sowie verfahren zu deren herstellung
DE3227122A1 (de) *	1982-07-20	1984-01-26	Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim	Stabile loesungen von mutterkornalkaloiden
IT1200609B (it) *	1985-04-04	1989-01-27	Poli Ind Chimica Spa	Composizione farmaceutice per il trattamento delle turbe cerebrovascolari e del cervello anziano
AT381232B (de) *	1985-05-13	1986-09-10	Kwizda Fa F Johann	Verfahren zur herstellung stabiler fluessiger loesungen von ergolinderivaten
GB8629781D0 (en) *	1986-12-12	1987-01-21	Glaxo Group Ltd	Pharmaceutical compositions
SK13742001A3 (sk) *	1999-03-26	2002-02-05	Pozen Inc.	Vysokoúčinné dihydroergotamínové prostriedky
DE102007014947B4 (de)	2007-03-23	2010-05-27	Axxonis Pharma Ag	Stabilisierte wässrige Lösungen von Ergolinverbindungen

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3749779A (en) *	1970-08-27	1973-07-31	American Home Prod	Stable solutions of sodium diphenylhydantoin

1977
- 1977-08-06 DE DE19772735587 patent/DE2735587A1/de not_active Withdrawn
1978
- 1978-05-30 GB GB23758/78A patent/GB1596948A/en not_active Expired
- 1978-07-24 CH CH796478A patent/CH635347A5/de not_active IP Right Cessation
- 1978-07-27 FI FI782341A patent/FI782341A7/fi not_active Application Discontinuation
- 1978-07-28 DK DK337678A patent/DK337678A/da not_active Application Discontinuation
- 1978-07-28 NO NO782605A patent/NO147901C/no unknown
- 1978-07-28 SE SE7808210A patent/SE444114B/sv unknown
- 1978-08-02 NL NL787808122A patent/NL7808122A/xx not_active Application Discontinuation
- 1978-08-02 IT IT26407/78A patent/IT1202759B/it active
- 1978-08-03 YU YU01883/78A patent/YU188378A/xx unknown
- 1978-08-04 FR FR7823160A patent/FR2399248A2/fr active Granted
- 1978-08-04 BE BE78189738A patent/BE869560R/xx not_active IP Right Cessation
- 1978-08-04 IL IL55285A patent/IL55285A/xx unknown
- 1978-08-04 GR GR56936A patent/GR72791B/el unknown
- 1978-08-04 AU AU38676/78A patent/AU525725B2/en not_active Expired
- 1978-08-04 AT AT0567378A patent/AT364463B/de not_active IP Right Cessation
- 1978-08-04 CA CA308,775A patent/CA1111348A/en not_active Expired
- 1978-08-04 PT PT68386A patent/PT68386A/pt unknown
- 1978-08-04 ZA ZA784435A patent/ZA784435B/xx unknown
- 1978-08-04 NZ NZ188073A patent/NZ188073A/xx unknown
- 1978-08-04 IE IE1598/78A patent/IE47791B1/en unknown
- 1978-08-04 CS CS785139A patent/CS203199B2/cs unknown
- 1978-08-05 JP JP9576378A patent/JPS5428811A/ja active Pending

Also Published As

Publication number	Publication date
IL55285A (en)	1981-09-13
NZ188073A (en)	1980-12-19
NO782605L (no)	1979-02-07
IE47791B1 (en)	1984-06-27
GB1596948A (en)	1981-09-03
NO147901C (no)	1983-07-06
ZA784435B (en)	1980-03-26
AU3867678A (en)	1980-02-07
NL7808122A (nl)	1979-02-08
YU188378A (en)	1984-02-29
SE7808210L (sv)	1979-02-07
AU525725B2 (en)	1982-11-25
FR2399248B2 (de)	1980-07-18
FI782341A7 (fi)	1979-02-07
DE2735587A1 (de)	1979-02-15
FR2399248A2 (fr)	1979-03-02
ATA567378A (de)	1981-03-15
CS203199B2 (en)	1981-02-27
IL55285A0 (en)	1978-10-31
IE781598L (en)	1979-02-06
GR72791B (de)	1983-12-05
NO147901B (no)	1983-03-28
IT1202759B (it)	1989-02-09
CH635347A5 (en)	1983-03-31
CA1111348A (en)	1981-10-27
DK337678A (da)	1979-02-07
AT364463B (de)	1981-10-27
PT68386A (en)	1978-09-01
JPS5428811A (en)	1979-03-03
IT7826407A0 (it)	1978-08-02
BE869560R (fr)	1979-02-05

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