DE3619665A1 - Quaternaere ammoniumsalze von furosemid, diese enthaltende arzneimittel und verfahren zu ihrer herstellung - Google Patents
Quaternaere ammoniumsalze von furosemid, diese enthaltende arzneimittel und verfahren zu ihrer herstellungInfo
- Publication number
- DE3619665A1 DE3619665A1 DE19863619665 DE3619665A DE3619665A1 DE 3619665 A1 DE3619665 A1 DE 3619665A1 DE 19863619665 DE19863619665 DE 19863619665 DE 3619665 A DE3619665 A DE 3619665A DE 3619665 A1 DE3619665 A1 DE 3619665A1
- Authority
- DE
- Germany
- Prior art keywords
- furosemide
- quaternary ammonium
- betaine
- choline
- hydroxide
- Prior art date
- 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.)
- Withdrawn
Links
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical class C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 title claims description 45
- 229960003883 furosemide Drugs 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 10
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 150000003863 ammonium salts Chemical class 0.000 title 1
- 239000000376 reactant Substances 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 8
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229960003237 betaine Drugs 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229960001231 choline Drugs 0.000 claims description 4
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 claims description 3
- 235000019743 Choline chloride Nutrition 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 claims description 3
- 229960003178 choline chloride Drugs 0.000 claims description 3
- 150000004820 halides Chemical group 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000005207 tetraalkylammonium group Chemical group 0.000 claims description 3
- 150000004679 hydroxides Chemical class 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 4
- -1 furosemide choline salt Chemical class 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000004381 Choline salt Substances 0.000 description 10
- 235000019417 choline salt Nutrition 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M potassium chloride Inorganic materials [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000003868 ammonium compounds Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000002934 diuretic Substances 0.000 description 2
- 230000001882 diuretic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000008215 water for injection Substances 0.000 description 2
- MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- 208000037147 Hypercalcaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000013736 caramel Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- LQJVOKWHGUAUHK-UHFFFAOYSA-L disodium 5-amino-4-hydroxy-3-phenyldiazenylnaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].OC1=C2C(N)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 LQJVOKWHGUAUHK-UHFFFAOYSA-L 0.000 description 1
- WZRZTHMJPHPAMU-UHFFFAOYSA-L disodium;(3e)-3-[(4-amino-3-sulfonatophenyl)-(4-amino-3-sulfophenyl)methylidene]-6-imino-5-methylcyclohexa-1,4-diene-1-sulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(=N)C(C)=CC1=C(C=1C=C(C(N)=CC=1)S([O-])(=O)=O)C1=CC=C(N)C(S(O)(=O)=O)=C1 WZRZTHMJPHPAMU-UHFFFAOYSA-L 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229940046250 furosemide injection Drugs 0.000 description 1
- 230000000148 hypercalcaemia Effects 0.000 description 1
- 208000030915 hypercalcemia disease Diseases 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000014666 liquid concentrate Nutrition 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000007967 peppermint flavor Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 239000001508 potassium citrate Substances 0.000 description 1
- 229960002635 potassium citrate Drugs 0.000 description 1
- QEEAPRPFLLJWCF-UHFFFAOYSA-K potassium citrate (anhydrous) Chemical compound [K+].[K+].[K+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O QEEAPRPFLLJWCF-UHFFFAOYSA-K 0.000 description 1
- 235000011082 potassium citrates Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000009419 refurbishment Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/10—Antioedematous agents; Diuretics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/751,763 US4663348A (en) | 1985-07-02 | 1985-07-02 | Furosemide salts and pharmaceutical preparations thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3619665A1 true DE3619665A1 (de) | 1987-01-08 |
Family
ID=25023379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19863619665 Withdrawn DE3619665A1 (de) | 1985-07-02 | 1986-06-11 | Quaternaere ammoniumsalze von furosemid, diese enthaltende arzneimittel und verfahren zu ihrer herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4663348A (en, 2012) |
| JP (1) | JPS625975A (en, 2012) |
| AU (1) | AU599034B2 (en, 2012) |
| BE (1) | BE904986A (en, 2012) |
| CH (1) | CH670448A5 (en, 2012) |
| DE (1) | DE3619665A1 (en, 2012) |
| DK (1) | DK312586A (en, 2012) |
| FR (1) | FR2584405B1 (en, 2012) |
| GB (1) | GB2189239B (en, 2012) |
| IT (1) | IT1191972B (en, 2012) |
| LU (1) | LU86484A1 (en, 2012) |
| NL (1) | NL8601519A (en, 2012) |
| SE (1) | SE8602917L (en, 2012) |
| ZA (1) | ZA864207B (en, 2012) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4920145A (en) * | 1988-02-29 | 1990-04-24 | Gaf Chemical Corporation | Water-soluble complexes of water-insoluble pharmaceutical compounds and preparation thereof |
| IT1237115B (it) * | 1989-10-24 | 1993-05-18 | Sali della furosemide, procedimento per la loro preparazione e composizionni farmaceutiche che li contengono | |
| DE69118716T2 (de) * | 1991-12-03 | 1996-12-19 | Kokuyo Kk | Beidseitig zu öffnende/verschliessende vorrichtung zum ordnen |
| US8008283B2 (en) * | 1998-12-23 | 2011-08-30 | Neurotherapeutics Pharma, Inc. | Methods and compositions for the treatment of neuropsychiatric disorders |
| US8722668B2 (en) * | 1998-12-23 | 2014-05-13 | Daryl W. Hochman | Methods and compositions for the treatment of neuropathic pain and neuropsychiatric disorders |
| US7214711B2 (en) * | 1998-12-23 | 2007-05-08 | Neurotherapeutics Pharma Llc | Method of treating migraine headache without aura |
| FI114538B (fi) * | 2001-01-12 | 2004-11-15 | Finnfeeds Finland Ltd | Glysiinibetaiinin käyttö verenpainetta alentavan tuotteen valmistukseen |
| US6989386B2 (en) * | 2002-04-30 | 2006-01-24 | Dana-Farber Cancer Institute | Pharmaceutically active ornithine derivatives, ammonium salts thereof and methods of making same |
| RU2416404C1 (ru) * | 2009-10-05 | 2011-04-20 | Государственное образовательное учреждение высшего профессионального образования "Алтайский государственный медицинский университет Федерального агентства по здравоохранению и социальному развитию" | Средство, обладающее мочегонным действием |
| EP2535342B1 (en) * | 2010-02-10 | 2014-08-06 | Kissei Pharmaceutical Co., Ltd. | Salt of fused heterocyclic derivative and crystal thereof |
| SG11201508251RA (en) * | 2013-04-05 | 2015-11-27 | Scpharmaceuticals Llc | Pharmaceutical formulations for subcutaneous administration of furosemide |
| US11246851B2 (en) | 2019-01-04 | 2022-02-15 | Sq Innovation Ag | Pharmaceutical compositions of furosemide and uses thereof |
| CA3128033A1 (en) | 2019-01-31 | 2020-08-06 | Scpharmaceuticals Inc. | Concentrated liquid pharmaceutical formulations of furosemide and methods of administering the same |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3058882A (en) * | 1959-12-28 | 1962-10-16 | Hoechst Ag | N'-substituted-3-carboxy-6-halo-sulfanilamide and derivatives thereof |
| US3565920A (en) * | 1966-12-29 | 1971-02-23 | Ciba Geigy Corp | 5-sulfamyl-anthranilic acids |
| DK138322B (da) * | 1970-07-13 | 1978-08-14 | Dumex Ltd As | Fremgangsmåde til fremstilling af N-substituered antranilsyrederivater. |
| FR2210607A1 (en) * | 1972-12-20 | 1974-07-12 | Aries Robert | 4-Chloro-5-sulphamoyl-N-furfuryl-anthranilic acid prepn. - from furfural and 4-chloro-5-sulphamoyl anthranilic acid |
| DE2343218C2 (de) * | 1973-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Furosemid enthaltende Pellets |
| LU74319A1 (en, 2012) * | 1976-02-09 | 1977-08-19 | ||
| DE3025367A1 (de) * | 1980-07-04 | 1982-01-28 | Hoechst Ag, 6000 Frankfurt | Salz aus furosemid oder piretanid als saeurekomponente und penbutolol oder (-)-3-(4- (3-(3,4-dimethoxyphenylaethylamino)-2-hydroxy-propoxy) -phenyl ) -crotonsaeurenitril als basenkomponente, verfahren zu seiner herstellung, dieses enthaltendes mittel und dessen verwendung |
-
1985
- 1985-07-02 US US06/751,763 patent/US4663348A/en not_active Expired - Fee Related
-
1986
- 1986-06-05 ZA ZA864207A patent/ZA864207B/xx unknown
- 1986-06-11 NL NL8601519A patent/NL8601519A/nl unknown
- 1986-06-11 DE DE19863619665 patent/DE3619665A1/de not_active Withdrawn
- 1986-06-16 AU AU58890/86A patent/AU599034B2/en not_active Ceased
- 1986-06-20 LU LU86484A patent/LU86484A1/fr unknown
- 1986-06-23 FR FR868609017A patent/FR2584405B1/fr not_active Expired
- 1986-06-23 GB GB08615275A patent/GB2189239B/en not_active Expired
- 1986-06-24 BE BE6/48235A patent/BE904986A/fr not_active IP Right Cessation
- 1986-06-25 IT IT48183/86A patent/IT1191972B/it active
- 1986-06-30 JP JP61151855A patent/JPS625975A/ja active Pending
- 1986-07-01 CH CH2639/86A patent/CH670448A5/fr not_active IP Right Cessation
- 1986-07-01 DK DK312586A patent/DK312586A/da not_active Application Discontinuation
- 1986-07-01 SE SE8602917A patent/SE8602917L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| GB2189239A (en) | 1987-10-21 |
| AU5889086A (en) | 1987-01-08 |
| NL8601519A (nl) | 1987-02-02 |
| DK312586A (da) | 1987-01-03 |
| IT1191972B (it) | 1988-03-31 |
| GB8615275D0 (en) | 1986-07-30 |
| GB2189239B (en) | 1989-02-01 |
| FR2584405B1 (fr) | 1989-02-24 |
| FR2584405A1 (fr) | 1987-01-09 |
| IT8648183A0 (it) | 1986-06-25 |
| US4663348A (en) | 1987-05-05 |
| ZA864207B (en) | 1987-02-25 |
| AU599034B2 (en) | 1990-07-12 |
| SE8602917L (sv) | 1987-01-03 |
| BE904986A (fr) | 1986-12-24 |
| SE8602917D0 (sv) | 1986-07-01 |
| JPS625975A (ja) | 1987-01-12 |
| LU86484A1 (fr) | 1986-12-02 |
| DK312586D0 (da) | 1986-07-01 |
| CH670448A5 (en, 2012) | 1989-06-15 |
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