FI68057C - Foerfarande foer framstaellning av antracyklinderivat - Google Patents
Foerfarande foer framstaellning av antracyklinderivat Download PDFInfo
- Publication number
- FI68057C FI68057C FI800298A FI800298A FI68057C FI 68057 C FI68057 C FI 68057C FI 800298 A FI800298 A FI 800298A FI 800298 A FI800298 A FI 800298A FI 68057 C FI68057 C FI 68057C
- Authority
- FI
- Finland
- Prior art keywords
- group
- chloroform
- adriamycin
- derivative
- formula
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- -1 phenylacetyloxy group Chemical group 0.000 claims description 157
- 150000001875 compounds Chemical class 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 44
- 238000002360 preparation method Methods 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 28
- 229940045799 anthracyclines and related substance Drugs 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 13
- 125000004423 acyloxy group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 238000006243 chemical reaction Methods 0.000 claims description 10
- JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims description 9
- 239000003377 acid catalyst Substances 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000000926 separation method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- RHZUVFJBSILHOK-UHFFFAOYSA-N anthracen-1-ylmethanolate Chemical compound C1=CC=C2C=C3C(C[O-])=CC=CC3=CC2=C1 RHZUVFJBSILHOK-UHFFFAOYSA-N 0.000 claims 1
- 239000003830 anthracite Substances 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 100
- 229940009456 adriamycin Drugs 0.000 description 73
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 51
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 44
- AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 41
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 239000000741 silica gel Substances 0.000 description 30
- 229910002027 silica gel Inorganic materials 0.000 description 30
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- 239000000843 powder Substances 0.000 description 19
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
- 239000000047 product Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- 238000004809 thin layer chromatography Methods 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 11
- WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 11
- 230000000259 anti-tumor effect Effects 0.000 description 11
- 238000012746 preparative thin layer chromatography Methods 0.000 description 11
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 11
- 229960000975 daunorubicin Drugs 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- GUGHGUXZJWAIAS-QQYBVWGSSA-N Daunorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 GUGHGUXZJWAIAS-QQYBVWGSSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003776 cleavage reaction Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 230000007017 scission Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 5
- 206010028980 Neoplasm Diseases 0.000 description 5
- 235000011089 carbon dioxide Nutrition 0.000 description 5
- 239000002026 chloroform extract Substances 0.000 description 5
- 229930182470 glycoside Natural products 0.000 description 5
- 150000002338 glycosides Chemical class 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- UOTYVBUEKGMADZ-UHFFFAOYSA-N 1,4-dioxane;4-methylbenzenesulfonic acid Chemical compound C1COCCO1.CC1=CC=C(S(O)(=O)=O)C=C1 UOTYVBUEKGMADZ-UHFFFAOYSA-N 0.000 description 4
- JQCSUVJDBHJKNG-UHFFFAOYSA-N 1-methoxy-ethyl Chemical group C[CH]OC JQCSUVJDBHJKNG-UHFFFAOYSA-N 0.000 description 4
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
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- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- SKYXLDSRLNRAPS-UHFFFAOYSA-N 1,2,4-trifluoro-5-methoxybenzene Chemical compound COC1=CC(F)=C(F)C=C1F SKYXLDSRLNRAPS-UHFFFAOYSA-N 0.000 description 3
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 3
- SHHYVKSJGBTTLX-UHFFFAOYSA-N 1-ethenoxy-6-methylheptane Chemical compound CC(C)CCCCCOC=C SHHYVKSJGBTTLX-UHFFFAOYSA-N 0.000 description 3
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- OHFMYSNQKZBRNM-UHFFFAOYSA-N 1-[2,3-dihydroxy-4-(hydroxymethyl)cyclopentyl]-5-methylpyrimidine-2,4-dione Chemical compound O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)C1 OHFMYSNQKZBRNM-UHFFFAOYSA-N 0.000 description 1
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- CJTTXGOOWXOTSV-UHFFFAOYSA-N methyl 3,4-dihydro-2h-pyran-2-carboxylate Chemical compound COC(=O)C1CCC=CO1 CJTTXGOOWXOTSV-UHFFFAOYSA-N 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- NIXKBAZVOQAHGC-UHFFFAOYSA-N phenylmethanesulfonic acid Chemical compound OS(=O)(=O)CC1=CC=CC=C1 NIXKBAZVOQAHGC-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005708 tetrahydropyranylation reaction Methods 0.000 description 1
- DRTQHJPVMGBUCF-UHFFFAOYSA-N uracil arabinoside Natural products OC1C(O)C(CO)OC1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UHFFFAOYSA-N 0.000 description 1
- 229940045145 uridine Drugs 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1170279 | 1979-02-03 | ||
| JP1170279A JPS55104299A (en) | 1979-02-03 | 1979-02-03 | Anthracycline compounds and their preparation |
| JP11025579A JPS5634695A (en) | 1979-08-31 | 1979-08-31 | Novel anthracycline derivative and its preparation |
| JP11025579 | 1979-08-31 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI800298A7 FI800298A7 (fi) | 1980-08-04 |
| FI68057B FI68057B (fi) | 1985-03-29 |
| FI68057C true FI68057C (fi) | 1985-07-10 |
Family
ID=26347196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI800298A FI68057C (fi) | 1979-02-03 | 1980-02-01 | Foerfarande foer framstaellning av antracyklinderivat |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0014853B1 (de) |
| AR (1) | AR226694A1 (de) |
| AT (1) | AT369384B (de) |
| AU (1) | AU518278B2 (de) |
| CA (1) | CA1136618A (de) |
| DE (1) | DE3063557D1 (de) |
| DK (1) | DK160616C (de) |
| ES (1) | ES8101622A1 (de) |
| FI (1) | FI68057C (de) |
| NZ (1) | NZ192758A (de) |
| PH (1) | PH18200A (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56156300A (en) * | 1980-04-26 | 1981-12-02 | Microbial Chem Res Found | Novel preparative method of anthracyclin derivative |
| JPS6016998A (ja) * | 1983-07-07 | 1985-01-28 | Microbial Chem Res Found | アントラサイクリン誘導体の製造方法 |
| GB2169284A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Epidoxorubicin-14-esters |
| GB2169285A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxydoxorubicin-14-esters |
| GB2169286A (en) * | 1985-01-05 | 1986-07-09 | Erba Farmitalia | 4'-Deoxy-4'-halodoxorubicin-14-esters |
| US4889926A (en) * | 1987-06-12 | 1989-12-26 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Method for the synthesis of (2"R)-4'-O-tetra-hydropyranyladriamycim using 14-chloro-daunomycin as an intermediate |
| US5776458A (en) * | 1990-12-05 | 1998-07-07 | Pharmacia & Upjohn S.P.A. | Anthracycline-conjugates |
| GB9026491D0 (en) * | 1990-12-05 | 1991-01-23 | Erba Carlo Spa | Anthracycline-conjugates |
| IT1282379B1 (it) * | 1996-04-24 | 1998-03-20 | Mini Ricerca Scient Tecnolog | Disaccaridi di antracicline antitumorali. |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| CN102753563A (zh) | 2008-12-23 | 2012-10-24 | 吉利德制药有限责任公司 | 核苷类似物 |
| US8716263B2 (en) | 2008-12-23 | 2014-05-06 | Gilead Pharmasset Llc | Synthesis of purine nucleosides |
| MX2011006891A (es) | 2008-12-23 | 2011-10-06 | Pharmasset Inc | Fosforamidatos de nucleosidos. |
| EA026341B9 (ru) | 2010-03-31 | 2021-12-27 | ГАЙЛИД ФАРМАССЕТ ЭлЭлСи | Кристаллическая форма нуклеозидфосфорамидата |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52148064A (en) * | 1976-05-31 | 1977-12-08 | Microbial Chem Res Found | Antitumors |
| GB1561507A (en) * | 1976-11-17 | 1980-02-20 | Farmaceutici Italia | Snthracycline disaccharides |
| JPS5430146A (en) * | 1977-08-05 | 1979-03-06 | Microbial Chem Res Found | Novel anthracycline derivatives and their preparation |
-
1980
- 1980-01-10 DK DK011480A patent/DK160616C/da not_active IP Right Cessation
- 1980-01-23 EP EP80100352A patent/EP0014853B1/de not_active Expired
- 1980-01-23 DE DE8080100352T patent/DE3063557D1/de not_active Expired
- 1980-01-24 AU AU54895/80A patent/AU518278B2/en not_active Ceased
- 1980-01-24 PH PH23547A patent/PH18200A/en unknown
- 1980-01-30 NZ NZ192758A patent/NZ192758A/xx unknown
- 1980-01-31 AR AR279810A patent/AR226694A1/es active
- 1980-01-31 AT AT0051180A patent/AT369384B/de not_active IP Right Cessation
- 1980-02-01 FI FI800298A patent/FI68057C/fi not_active IP Right Cessation
- 1980-02-01 CA CA000344911A patent/CA1136618A/en not_active Expired
- 1980-02-01 ES ES488209A patent/ES8101622A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE3063557D1 (en) | 1983-07-07 |
| ES488209A0 (es) | 1980-12-16 |
| ATA51180A (de) | 1982-05-15 |
| AR226694A1 (es) | 1982-08-13 |
| DK11480A (da) | 1980-08-04 |
| DK160616C (da) | 1991-09-02 |
| FI68057B (fi) | 1985-03-29 |
| FI800298A7 (fi) | 1980-08-04 |
| PH18200A (en) | 1985-04-25 |
| DK160616B (da) | 1991-04-02 |
| EP0014853A1 (de) | 1980-09-03 |
| AU5489580A (en) | 1980-08-07 |
| NZ192758A (en) | 1982-03-09 |
| EP0014853B1 (de) | 1983-06-01 |
| CA1136618A (en) | 1982-11-30 |
| AT369384B (de) | 1982-12-27 |
| ES8101622A1 (es) | 1980-12-16 |
| AU518278B2 (en) | 1981-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: ZAIDANHOJIN BISEIBUTSU KAGAKU KENKYUKAI |