FI76091B - Foerfarande foer framstaellning av antibakteriella 2-(fluoralkyltio)-penem-foereningar. - Google Patents
Foerfarande foer framstaellning av antibakteriella 2-(fluoralkyltio)-penem-foereningar. Download PDFInfo
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- FI76091B FI76091B FI823997A FI823997A FI76091B FI 76091 B FI76091 B FI 76091B FI 823997 A FI823997 A FI 823997A FI 823997 A FI823997 A FI 823997A FI 76091 B FI76091 B FI 76091B
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- Finland
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- formula
- penem
- compound
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- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 239000012442 inert solvent Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004185 ester group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- 241000194017 Streptococcus Species 0.000 description 3
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical compound O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 3
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- 238000013375 chromatographic separation Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 150000002221 fluorine Chemical class 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- CUILPNURFADTPE-UHFFFAOYSA-N hypobromous acid Chemical compound BrO CUILPNURFADTPE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000002941 palladium compounds Chemical class 0.000 description 1
- 125000002217 penem group Chemical group 0.000 description 1
- 229950009506 penicillinase Drugs 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- BLGUIMKBRCQORR-UHFFFAOYSA-M potassium;hexanoate Chemical compound [K+].CCCCCC([O-])=O BLGUIMKBRCQORR-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JMPVZWBJWHQJDD-UHFFFAOYSA-N sulfur tetrachloride Chemical compound ClS(Cl)(Cl)Cl JMPVZWBJWHQJDD-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/28—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with modified 2-carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/09—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a sulfur atom directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Claims (3)
1. FÖrfarande för framställning av antibakteriella 2-fluor-alkyltiopenemföreningar med formeln I OH S H3C " ? S -A H | / (I) ^7 N ^ COOR där A är en rak eller förgrenad C2-C^ fluoralkylgrupp med 1-3 fluoratomer vid samma kolatom, vilken grupp ligger ätminstone pä 2 kolatomers avständ frän
2-S-atomen, R är väte, en farmaceutiskt godtagbar katjon eller en metaboliserbar ester-grupp och stereokemin är 5R,6S,8R, kännetecknat av att framställningen sker genom a) fluorering av en förening med formeln II 0H S H C - C --S' \ (11)
3. I >-s-z J—N—\ o coox där stereokemin är samma som för formeln I, där Z är en rak eller förgrenad alky.lgrupp med 2-4 kolatomer, som substituerats med gruppen Lg, vilken kan ersättas med fluor under reaktions-betingelserna, varvid nämnda grupp Lg liggar ätminstone pä 2 kolatomers avstand frän 2-S-atomen, X är en karboxiskyddsgrupp och hydroxigruppen i 2-ställning i penemen är vid behov skyd-dad, i ett inert lösningsmedel, vid pH 4 - 8 och en tempera-tur melian -70°C - omgivningstemperaturen. 31 76091 b) alkylering av en förening med formeln III ΟΠ s ?H s Η3°ΊΊΐΟ"—>s (III) (f— N-^coox f ^ coox där υ υ stereokemin är samma som för formeln I, X är samma som ovan och hydroxigruppen i 8-ställning i penemen är va.lbart skyddad med en förening med formeln G - Y (IV) där G är en rak eller förgrenad alkylgrupp med 2-4 kolatomer, som substituerats med 1-3 fluoratomer vid samma ko.latom, vilken ligger ätminstone pi en kolatoms avständ frän gruppen Y och Y är en under reaktionsbetingelserna avgäendd grupp, c) ornsättning av en förening med formeln V ς —a ' ?H /sxr/ "3C * f —I-f II <V) H I S J-N\c^° O ' coox där stereokemin är 3S,4R,5R eller 3R,4R,5S, A' är en rak eller förgrenad fluoralkylgrupp med 1-3 fluoratomer vid samma koi-, ' som ligger ätminstone pä en kolatoms avständ frän närliggande svavelatom, X är samma som ovan och vid behov eller om sä önskas är hydroxigruppen i 5-ställning skyddad, med en trevärdig orga-
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32493181 | 1981-11-25 | ||
| US06/324,931 US4411906A (en) | 1981-11-25 | 1981-11-25 | (5R,6S,8R)-6-(1-Hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylates |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI823997A0 FI823997A0 (fi) | 1982-11-22 |
| FI823997L FI823997L (fi) | 1983-05-26 |
| FI76091B true FI76091B (fi) | 1988-05-31 |
| FI76091C FI76091C (sv) | 1988-09-09 |
Family
ID=23265741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI823997A FI76091C (sv) | 1981-11-25 | 1982-11-22 | Förfarande för framställning av antibakteriella 2-(fluoralkyltio)-pene m-föreningar |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US4411906A (sv) |
| EP (1) | EP0080162B1 (sv) |
| JP (1) | JPS5892683A (sv) |
| KR (1) | KR890005148B1 (sv) |
| AT (1) | ATE20666T1 (sv) |
| AU (1) | AU560838B2 (sv) |
| CA (1) | CA1207753A (sv) |
| DE (1) | DE3271955D1 (sv) |
| DK (1) | DK153553C (sv) |
| FI (1) | FI76091C (sv) |
| HK (1) | HK56889A (sv) |
| HU (1) | HU190044B (sv) |
| IE (1) | IE54219B1 (sv) |
| IL (1) | IL67327A0 (sv) |
| MY (1) | MY8700708A (sv) |
| NO (1) | NO159796C (sv) |
| NZ (1) | NZ202574A (sv) |
| OA (1) | OA07255A (sv) |
| PH (1) | PH19647A (sv) |
| PT (1) | PT75878B (sv) |
| SG (1) | SG88388G (sv) |
| ZA (1) | ZA828602B (sv) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5835190A (ja) * | 1981-08-25 | 1983-03-01 | Sankyo Co Ltd | ペネム−３−カルボン酸誘導体 |
| EP0091576B1 (en) * | 1982-03-26 | 1987-07-29 | Hoechst Uk Limited | 7-oxo-4-thia-1-azabicyclo(3,2,0)heptane derivatives |
| EP0110280B1 (en) * | 1982-11-29 | 1994-10-12 | Schering Corporation | Process for the production of penem compounds |
| GB8321677D0 (en) * | 1983-08-11 | 1983-09-14 | Erba Farmitalia | Preparation of penems |
| US5053502A (en) * | 1986-07-21 | 1991-10-01 | Schering Corporation | Anhydro penicillin derivatives |
| US4767853A (en) * | 1986-07-21 | 1988-08-30 | Schering Corporation | Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta-naphthoxythiocarbonylthio-2-azetidinones and hydroxy protected analogs thereof |
| US5075438A (en) * | 1986-07-21 | 1991-12-24 | Schering Corporation | Synthesis of azetidinones |
| US4876338A (en) * | 1986-07-21 | 1989-10-24 | Schering Corporation | Synthesis of azetidinones using CuCl |
| US4948885A (en) * | 1986-07-21 | 1990-08-14 | Schering-Plough Corp. | Synthesis of azetidinones |
| US6365635B1 (en) * | 1998-01-13 | 2002-04-02 | Suntory Limited | Antibacterial composition for topical administration containing antibiotic |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| US4301074A (en) * | 1977-11-17 | 1981-11-17 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid |
| EP0042026B1 (de) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung |
| US4386030A (en) * | 1979-12-31 | 1983-05-31 | Merck & Co., Inc. | Process for preparing 6-(1'-hydroxyethyl)-2-substituted-pen-2-em-3-carboxylic acid |
| DE3169939D1 (en) * | 1980-02-28 | 1985-05-23 | Schering Corp | 2-penem compounds, pharmaceutical compositions containing them and methods for their preparation |
| US4650794A (en) * | 1982-04-29 | 1987-03-17 | Merck & Co., Inc. | 6-(1-hydroxyethyl)-2-carbamimidoyl-pen-2-em-3-carboxylic acids |
| US4614738A (en) * | 1983-03-25 | 1986-09-30 | Schering Corporation | 2-(N-heterocycloaliphaticthio)penems |
| US4587241A (en) * | 1983-11-28 | 1986-05-06 | Schering Corporation | Heterocyclic substituted penems |
-
1981
- 1981-11-25 US US06/324,931 patent/US4411906A/en not_active Expired - Lifetime
-
1982
- 1982-11-18 DE DE8282110612T patent/DE3271955D1/de not_active Expired
- 1982-11-18 EP EP82110612A patent/EP0080162B1/en not_active Expired
- 1982-11-18 AT AT82110612T patent/ATE20666T1/de not_active IP Right Cessation
- 1982-11-22 NZ NZ202574A patent/NZ202574A/en unknown
- 1982-11-22 DK DK519382A patent/DK153553C/da not_active IP Right Cessation
- 1982-11-22 AU AU90787/82A patent/AU560838B2/en not_active Ceased
- 1982-11-22 JP JP57205336A patent/JPS5892683A/ja active Pending
- 1982-11-22 IE IE2765/82A patent/IE54219B1/en not_active IP Right Cessation
- 1982-11-22 PT PT75878A patent/PT75878B/pt not_active IP Right Cessation
- 1982-11-22 PH PH28169A patent/PH19647A/en unknown
- 1982-11-22 FI FI823997A patent/FI76091C/sv not_active IP Right Cessation
- 1982-11-22 ZA ZA828602A patent/ZA828602B/xx unknown
- 1982-11-22 NO NO823903A patent/NO159796C/no unknown
- 1982-11-23 KR KR8205286A patent/KR890005148B1/ko active
- 1982-11-23 OA OA57848A patent/OA07255A/xx unknown
- 1982-11-23 CA CA000416189A patent/CA1207753A/en not_active Expired
- 1982-11-23 IL IL67327A patent/IL67327A0/xx not_active IP Right Cessation
- 1982-11-24 HU HU823777A patent/HU190044B/hu not_active IP Right Cessation
-
1985
- 1985-07-19 US US06/757,047 patent/US4814442A/en not_active Expired - Fee Related
-
1987
- 1987-12-30 MY MY708/87A patent/MY8700708A/xx unknown
-
1988
- 1988-12-24 SG SG883/88A patent/SG88388G/en unknown
-
1989
- 1989-07-13 HK HK568/89A patent/HK56889A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0080162A1 (en) | 1983-06-01 |
| NZ202574A (en) | 1986-06-11 |
| IE822765L (en) | 1983-05-25 |
| NO159796C (no) | 1989-02-08 |
| NO823903L (no) | 1983-05-26 |
| US4814442A (en) | 1989-03-21 |
| HU190044B (en) | 1986-08-28 |
| DK153553C (da) | 1988-12-19 |
| HK56889A (en) | 1989-07-21 |
| AU9078782A (en) | 1983-06-02 |
| JPS5892683A (ja) | 1983-06-02 |
| FI823997L (fi) | 1983-05-26 |
| MY8700708A (en) | 1987-12-31 |
| PT75878B (en) | 1986-01-15 |
| OA07255A (fr) | 1984-04-30 |
| AU560838B2 (en) | 1987-04-16 |
| DK519382A (da) | 1983-05-26 |
| FI823997A0 (fi) | 1982-11-22 |
| ZA828602B (en) | 1983-09-28 |
| IE54219B1 (en) | 1989-07-19 |
| KR840002403A (ko) | 1984-07-02 |
| PH19647A (en) | 1986-06-04 |
| KR890005148B1 (ko) | 1989-12-14 |
| DK153553B (da) | 1988-07-25 |
| CA1207753A (en) | 1986-07-15 |
| PT75878A (en) | 1982-12-01 |
| IL67327A0 (en) | 1983-03-31 |
| NO159796B (no) | 1988-10-31 |
| ATE20666T1 (de) | 1986-07-15 |
| FI76091C (sv) | 1988-09-09 |
| SG88388G (en) | 1989-06-16 |
| DE3271955D1 (en) | 1986-08-14 |
| EP0080162B1 (en) | 1986-07-09 |
| US4411906A (en) | 1983-10-25 |
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