SE7909754L - Forfarande for framstellning av endolderivat - Google Patents
Forfarande for framstellning av endolderivatInfo
- Publication number
- SE7909754L SE7909754L SE7909754A SE7909754A SE7909754L SE 7909754 L SE7909754 L SE 7909754L SE 7909754 A SE7909754 A SE 7909754A SE 7909754 A SE7909754 A SE 7909754A SE 7909754 L SE7909754 L SE 7909754L
- Authority
- SE
- Sweden
- Prior art keywords
- formula
- protected
- amino
- hydroxy
- optionally
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- -1 hydroxychlorophenyl Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims 2
- FZEVMBJWXHDLDB-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-2-en-8-one Chemical compound S1CC=CN2C(=O)C[C@H]21 FZEVMBJWXHDLDB-ZCFIWIBFSA-N 0.000 claims 1
- SXBDXXFTJVHSAF-ZCFIWIBFSA-N (6r)-5-thia-1-azabicyclo[4.2.0]oct-3-en-8-one Chemical class S1C=CCN2C(=O)C[C@H]21 SXBDXXFTJVHSAF-ZCFIWIBFSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 108010010225 RA VII Proteins 0.000 claims 1
- MBQKTLYFUYNAPZ-UHFFFAOYSA-N Rubia akane RA-VII Natural products C1=CC(OC)=CC=C1CC(N(C)C(=O)C(C)NC(=O)C(C)NC(=O)C(N(C1=O)C)C2)C(=O)NC(C)C(=O)N(C)C1CC(C=C1)=CC=C1OC1=CC2=CC=C1OC MBQKTLYFUYNAPZ-UHFFFAOYSA-N 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012530 fluid Substances 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- PFZCOWLKXHIVII-UHFFFAOYSA-N pyridin-1-ium-1-amine Chemical compound N[N+]1=CC=CC=C1 PFZCOWLKXHIVII-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- MBQKTLYFUYNAPZ-FEZMQHRXSA-N ra vii Chemical compound C1=CC(OC)=CC=C1C[C@H](N(C)C(=O)[C@H](C)NC(=O)[C@@H](C)NC(=O)[C@@H](N(C1=O)C)C2)C(=O)N[C@@H](C)C(=O)N(C)[C@H]1CC(C=C1)=CC=C1OC1=CC2=CC=C1OC MBQKTLYFUYNAPZ-FEZMQHRXSA-N 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 238000003797 solvolysis reaction Methods 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
Classifications
-
- 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
- C07D205/095—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 and with a nitrogen atom directly attached in position 3
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (1)
1. Patentkrav satt att framstglla 7p-amin0-3-oefem-3-01karb0nsyraforeningar med formeln NH () Y-O_R(IA) OC— R2 marlbetecknar vate, en acylgrupp med formeln 0 Pa - (X)m - pH - C(B) van i Ra betecknar renal, hydroxifenyl, hydroxi-klorfenyl, tienyl, PYridyl, aminopyridinium, furyl, isotiazyl, tetrazolyl eller 1,4-cyklohexadienyl varvid hydroxisubstituenterna i sAdana grupper ken vane skyddade med acylrester, X beteeknar syre eller svavel, m betecknar 0 eller 1 och Rb betecknar cite eller, om m betecknar 0 eventuellt skyddad amino, karboxi, sulfo eller hydroxi, eller 0-lagalkylfosfono eller 0,0--dilAgalkyl-fosfcno eller, betecknar Nip en 5-amino-5-karboxi-valerylrest van i amino- och karboxigruppen eventuellt Or skyddade, R2 betecknar hydroxi eller bildar tillsammans med karbonylgrupnen -C(=0)- en skyddad karboxylgrupp, 4 och 143 betecknar Irate samt 1-oxiden ay 3-cefemforeningar med fornel IA, motsvarande 2-cefem-fbreningar med formeln 1\ PP 1S (IB) _R3 CR3 van iR, oca 143 har ovan angivna betydelser, eller bland- ningar av 3-cefem- och 2-cefemfbreningar med formeln IA och IS, eller salter an sadana fbreningar med saltbildande grupper, kannetecknat av att manien beefing med formeln hexylamino, N-metyl-cyklohexylamino, dibensylamioo,rr.tyl- bensylamino, N-cyklopropyl-bensylamino, 1-aziridinyl, 1-pyrrelidinyl, 1-piperidyl, 11-2,3,4,5,0,7-hexahydroazepinyl, 4- morfolinyl, 4-tiomorfolinyl, 1-piperazinyl eller 4-meey1-1- piperazinyl genom tillsats an vatten och eventuellt en katalytisk till ekvimolar mangd an en organisk eller ocrganisk s),ra vii temperatmTmellan -° och 01 solvolyserar aminogruppen -N(11) ■Rd till gruppen -0R3:och eventuellt i en erhAllen firening med formeln IA rasp. IB overfbr den fOrestrade karboxylgruppen med formel -C(=0)-4 genom fbrtvalning till den fria karboxylgruppen och eventuellt i en erhAllen fbrening med formeln IA reap. Ii, earl R3 betecknar en acylrest avspaltas dense acylrest gencm behandling med ett iffidhalogenid-hildande medel, omsattning av den erhallna inidhalogeniden med at alkchol till en motsvarande iminoeter ouh solvolysering av den bildade iminoetern, och om sa Onskas, frigbres i en erhAllen fbrening med formeln IA rasp. IB i en hydroxifenylrest Ra eventuellt forevarande skyddad hydroxi och/eller skyddad amino, karboxi, sulfo eller hydroxi Rb och, om sO briskas bverfores en erhAllen fbrening med formeln IA resp, Ii med saltbildande grupp till ett salt eller ett erhallet salt till en fri fOrening och/eller, om sa onskes, separeras en erhallen blandning av isomera fbreningar i de enskilda isomererna. 0—
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH215775A CH626091A5 (en) | 1975-02-20 | 1975-02-20 | Process for preparing enol derivatives |
| CH1096275A CH627759A5 (en) | 1975-08-25 | 1975-08-25 | Process for preparing enol ether compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7909754L true SE7909754L (sv) | 1979-11-26 |
| SE434265B SE434265B (sv) | 1984-07-16 |
Family
ID=25689673
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7601873A SE434951B (sv) | 1975-02-20 | 1976-02-18 | Nytt forfarande for framstellning av 7beta-amino-3-cefem-3-ol-4-karboxylsyraforeningar |
| SE7909754A SE434265B (sv) | 1975-02-20 | 1979-11-26 | Sett att framstella 7beta-amino-3-cefem-3-ol-4-karbonsyraforeningar |
| SE7909753A SE445644B (sv) | 1975-02-20 | 1979-11-26 | 7beta-amino-3-cefem-3-amino-4-karbonsyra-foreningar som mellanprodukter for framstellning av 7beta-amino-3-cefem-3-ol-4-karbonsyra-foreningar |
| SE7909752A SE440349B (sv) | 1975-02-20 | 1979-11-26 | 2-(2-oxoazetidin-1-yl)-krotonsyra-foreningar till anvendning som mellanprodukt vid framstellning av terapeutiskt verdefulla 7beta-amino-3-cefem-foreningar |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7601873A SE434951B (sv) | 1975-02-20 | 1976-02-18 | Nytt forfarande for framstellning av 7beta-amino-3-cefem-3-ol-4-karboxylsyraforeningar |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7909753A SE445644B (sv) | 1975-02-20 | 1979-11-26 | 7beta-amino-3-cefem-3-amino-4-karbonsyra-foreningar som mellanprodukter for framstellning av 7beta-amino-3-cefem-3-ol-4-karbonsyra-foreningar |
| SE7909752A SE440349B (sv) | 1975-02-20 | 1979-11-26 | 2-(2-oxoazetidin-1-yl)-krotonsyra-foreningar till anvendning som mellanprodukt vid framstellning av terapeutiskt verdefulla 7beta-amino-3-cefem-foreningar |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US4110533A (sv) |
| JP (1) | JPS6145627B2 (sv) |
| AT (1) | AT342197B (sv) |
| AU (1) | AU498501B2 (sv) |
| CA (1) | CA1080695A (sv) |
| CS (3) | CS194748B2 (sv) |
| DE (1) | DE2606196A1 (sv) |
| DK (4) | DK157027C (sv) |
| ES (3) | ES445282A1 (sv) |
| FR (1) | FR2301529A1 (sv) |
| GB (1) | GB1530501A (sv) |
| HU (1) | HU174553B (sv) |
| IE (1) | IE43703B1 (sv) |
| IL (2) | IL49064A (sv) |
| MX (1) | MX3311E (sv) |
| NL (1) | NL7601514A (sv) |
| NZ (1) | NZ180049A (sv) |
| PT (1) | PT64823B (sv) |
| SE (4) | SE434951B (sv) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1136132A (en) * | 1975-02-17 | 1982-11-23 | Teruji Tsuji | Cyclization to form cephem ring and intermediates therefor |
| US4579684A (en) * | 1975-02-20 | 1986-04-01 | Ciba-Geigy Corporation | Process for the manufacture of enol derivatives |
| AT342197B (de) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | Neues verfahren zur herstellung von 3-cephemverbindungen |
| US4434287A (en) | 1975-02-20 | 1984-02-28 | Ciba-Geigy Corporation | Cephalosporin derivatives |
| US4013651A (en) * | 1975-05-12 | 1977-03-22 | Eli Lilly And Company | 3-substituted amino-cephalosporins |
| PH17188A (en) * | 1977-03-14 | 1984-06-14 | Fujisawa Pharmaceutical Co | New cephem and cepham compounds and their pharmaceutical compositions and method of use |
| US4301279A (en) | 1979-02-23 | 1981-11-17 | Ciba-Geigy Corporation | Process for the production of 3-hydroxy compounds |
| US4436903A (en) * | 1980-12-22 | 1984-03-13 | Ciba-Geigy Corporation | Process for the production of 7 β-substituted-3-unsubstituted-3-cephem-4-carboxylic acid compounds |
| DE3265390D1 (en) * | 1981-05-19 | 1985-09-19 | Ciba Geigy Ag | Process for the preparation of 4-thio-azetidinone compounds |
| JPS59134779A (ja) * | 1983-01-19 | 1984-08-02 | Otsuka Chem Co Ltd | アゼチジノン誘導体の製造法 |
| JPS60115562A (ja) * | 1983-11-28 | 1985-06-22 | Otsuka Chem Co Ltd | アゼチジノン誘導体の製造法 |
| JPS61178961A (ja) * | 1985-02-01 | 1986-08-11 | Otsuka Chem Co Ltd | アゼチジノン誘導体の製造法 |
| JPH02159453A (ja) * | 1988-12-09 | 1990-06-19 | Miyano:Kk | カム制御装置 |
| JPH04316593A (ja) * | 1991-02-21 | 1992-11-06 | Japan Tobacco Inc | Ｄ−アロサンの製造方法 |
| JP3227497B2 (ja) | 1992-02-18 | 2001-11-12 | 大塚化学株式会社 | β−ラクタム化合物及びその製造法 |
| WO1993016043A1 (en) * | 1992-02-18 | 1993-08-19 | Otsuka Kagaku Kabushiki Kaisha | β-LACTAM COMPOUND AND CEPHEM COMPOUND, AND PRODUCTION THEREOF |
| US5604222A (en) * | 1993-12-27 | 1997-02-18 | Lupin Laboratories, Ltd. | Method for the preparation of 2-chloro sulfinyl azetidinones |
| US5578721A (en) * | 1994-07-11 | 1996-11-26 | Lupin Laboratories Limited | Process for preparation of 3-exomethylene cepham sulfoxide esters |
| US6696594B2 (en) | 2002-05-13 | 2004-02-24 | Saudi Basic Industries Corporation | Process for the conversion of aldehydes to esters |
| US20090324742A1 (en) * | 2006-09-08 | 2009-12-31 | Sonke Svenson | Peham dendrimers as excipients |
| CN113563365B (zh) * | 2021-08-17 | 2024-05-28 | 华中药业股份有限公司 | 一种7-氨基-3-甲氧基-4-头孢烷酸的制备方法 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3518260A (en) * | 1965-03-08 | 1970-06-30 | Lilly Co Eli | Method for preparing aminoacyl cephalosporins |
| BE791160A (fr) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Nouveaux cephemes substitues |
| BE791161A (fr) * | 1972-01-03 | 1973-05-09 | Beecham Group Ltd | Procede pour la preparation d'analogues des cephalosporines |
| US3950352A (en) * | 1972-04-10 | 1976-04-13 | Queen's University | 2,2-Dimethyl-3R-carboxy-6S-phenyl(or phenoxy)acetamido-1-oxa-4-aza-5R-bicyclo[3,2,0]heptan-7-one and processes for their production |
| US3960881A (en) * | 1972-04-24 | 1976-06-01 | Phillips Petroleum Company | Method for preparing 4-carboxythiazolidine-2-thione |
| US3944545A (en) * | 1972-05-10 | 1976-03-16 | Eli Lilly And Company | Process for preparing desacetoxycephalosporins |
| US3960851A (en) * | 1972-05-15 | 1976-06-01 | Eli Lilly And Company | Preparation of desacetoxy-cephalosporin sulfoxides from penicillin sulfoxides |
| AR206201A1 (es) * | 1972-06-29 | 1976-07-07 | Ciba Geigy Ag | Procedimiento para la obtencion de compuestos de acido 7beta-amino-3-cefem-3-01-4-carboxilico0-substituidos |
| GB1431174A (en) * | 1972-06-30 | 1976-04-07 | Clin Midy | Process for the conversion of a penicillin s-oxide into a corresponding desacetoxycephalosporin |
| US3917588A (en) * | 1972-11-28 | 1975-11-04 | Lilly Co Eli | {60 -Aminoacyl cephalosporin ethers |
| AR208068A1 (es) * | 1973-02-23 | 1976-11-30 | Lilly Co Eli | Un procedimiento para preparar derivados de acidos 7-acilamido-3-halo-cefem-4-carboxilico los esteres y las sales farmaceuticamente aceptables de los mismos |
| YU36970B (en) * | 1973-02-23 | 1984-08-31 | Lilly Co Eli | Process for obtaining 7-(amino)-acylamido-3-halocephalosporins |
| AU498131B2 (en) * | 1974-02-26 | 1979-02-15 | Ciba-Geigy Ag | Production of cephems by cyclization |
| US4036835A (en) * | 1974-05-22 | 1977-07-19 | Societa' Farmaceutici Italia | Process for preparing cephalosporins |
| CA1136132A (en) * | 1975-02-17 | 1982-11-23 | Teruji Tsuji | Cyclization to form cephem ring and intermediates therefor |
| AT342197B (de) * | 1975-02-20 | 1978-03-28 | Ciba Geigy Ag | Neues verfahren zur herstellung von 3-cephemverbindungen |
| US4013651A (en) * | 1975-05-12 | 1977-03-22 | Eli Lilly And Company | 3-substituted amino-cephalosporins |
| JPS5214789A (en) * | 1975-07-22 | 1977-02-03 | Shionogi & Co Ltd | Process for preparing 3-substiuted cephem compounds by ring closure |
| US4024152A (en) * | 1975-09-19 | 1977-05-17 | Eli Lilly And Company | 4-Dithio-3-imido-azetidin-2-ones |
| US4008230A (en) * | 1975-10-29 | 1977-02-15 | Eli Lilly And Company | Process for preparing 3-hydroxy cephalosporins |
| US4048162A (en) * | 1975-10-29 | 1977-09-13 | Eli Lilly And Company | Process for preparing 3-hydroxy cephalosporins |
| IE45158B1 (en) * | 1976-08-16 | 1982-06-30 | Lilly Co Eli | 3-chloro-cephem synthesis |
-
1976
- 1976-02-04 AT AT76976A patent/AT342197B/de not_active IP Right Cessation
- 1976-02-10 US US05/671,193 patent/US4110533A/en not_active Expired - Lifetime
- 1976-02-13 NL NL7601514A patent/NL7601514A/xx not_active Application Discontinuation
- 1976-02-17 CS CS775569A patent/CS194748B2/cs unknown
- 1976-02-17 MX MX000002U patent/MX3311E/es unknown
- 1976-02-17 DE DE19762606196 patent/DE2606196A1/de active Granted
- 1976-02-17 CS CS761019A patent/CS194740B2/cs unknown
- 1976-02-17 CS CS775570A patent/CS194749B2/cs unknown
- 1976-02-18 CA CA246,040A patent/CA1080695A/en not_active Expired
- 1976-02-18 ES ES445282A patent/ES445282A1/es not_active Expired
- 1976-02-18 GB GB6363/76A patent/GB1530501A/en not_active Expired
- 1976-02-18 SE SE7601873A patent/SE434951B/sv not_active IP Right Cessation
- 1976-02-19 PT PT64823A patent/PT64823B/pt unknown
- 1976-02-19 DK DK068976A patent/DK157027C/da not_active IP Right Cessation
- 1976-02-19 IE IE322/76A patent/IE43703B1/en unknown
- 1976-02-19 HU HU76CI1643A patent/HU174553B/hu unknown
- 1976-02-19 AU AU11253/76A patent/AU498501B2/en not_active Expired
- 1976-02-19 IL IL49064A patent/IL49064A/xx unknown
- 1976-02-19 NZ NZ180049A patent/NZ180049A/xx unknown
- 1976-02-20 JP JP51017192A patent/JPS6145627B2/ja not_active Expired
- 1976-02-20 FR FR7604723A patent/FR2301529A1/fr active Granted
-
1977
- 1977-06-16 ES ES459827A patent/ES459827A1/es not_active Expired
- 1977-06-16 ES ES459833A patent/ES459833A1/es not_active Expired
-
1979
- 1979-01-08 IL IL56394A patent/IL56394A0/xx unknown
- 1979-05-07 US US06/036,483 patent/US4319027A/en not_active Expired - Lifetime
- 1979-11-26 SE SE7909754A patent/SE434265B/sv not_active IP Right Cessation
- 1979-11-26 SE SE7909753A patent/SE445644B/sv not_active IP Right Cessation
- 1979-11-26 SE SE7909752A patent/SE440349B/sv not_active IP Right Cessation
- 1979-12-10 US US06/102,461 patent/US4293462A/en not_active Expired - Lifetime
-
1987
- 1987-10-16 DK DK543287A patent/DK157080C/da active
- 1987-10-16 DK DK543387A patent/DK167278B1/da active
- 1987-10-16 DK DK543187A patent/DK157079C/da active
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