NO125675B - - Google Patents
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- Publication number
- NO125675B NO125675B NO4739/68A NO473968A NO125675B NO 125675 B NO125675 B NO 125675B NO 4739/68 A NO4739/68 A NO 4739/68A NO 473968 A NO473968 A NO 473968A NO 125675 B NO125675 B NO 125675B
- Authority
- NO
- Norway
- Prior art keywords
- group
- general formula
- salts
- denotes
- naphthacene
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001935 tetracenyl group Chemical class C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000003876 thiosemicarbazone group Chemical group 0.000 claims description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 12
- DWCNNQOORRREID-UHFFFAOYSA-N 1,2-dichloroethane;methanol Chemical compound OC.ClCCCl DWCNNQOORRREID-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 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 5
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 5
- 229960000975 daunorubicin Drugs 0.000 description 5
- 229960003109 daunorubicin hydrochloride Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 4
- NAALWFYYHHJEFQ-ZASNTINBSA-N (2s,5r,6r)-6-[[(2r)-2-[[6-[4-[bis(2-hydroxyethyl)sulfamoyl]phenyl]-2-oxo-1h-pyridine-3-carbonyl]amino]-2-(4-hydroxyphenyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@@H](C(=O)N[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C=1C=CC(O)=CC=1)C(=O)C(C(N1)=O)=CC=C1C1=CC=C(S(=O)(=O)N(CCO)CCO)C=C1 NAALWFYYHHJEFQ-ZASNTINBSA-N 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 thiocarbamoyl group Chemical group 0.000 description 3
- UHUHDVGYLSYYGD-HSZRJFAPSA-N (2r)-4-methyl-2-(tritylazaniumyl)pentanoate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)([NH2+][C@H](CC(C)C)C([O-])=O)C1=CC=CC=C1 UHUHDVGYLSYYGD-HSZRJFAPSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- 208000007093 Leukemia L1210 Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 230000001093 anti-cancer Effects 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLDAXFJBEVRMHU-SANMLTNESA-N (2s)-3-phenyl-2-(tritylazaniumyl)propanoate Chemical compound C([C@@H](C(=O)[O-])[NH2+]C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 XLDAXFJBEVRMHU-SANMLTNESA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
- ROHFNLRQFUQHCH-RXMQYKEDSA-N D-leucine Chemical compound CC(C)C[C@@H](N)C(O)=O ROHFNLRQFUQHCH-RXMQYKEDSA-N 0.000 description 1
- 229930182819 D-leucine Natural products 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000005452 ethyl sulfates Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- DODCBMODXGJOKD-UHFFFAOYSA-N hydron;methyl 2-amino-4-methylpentanoate;chloride Chemical compound Cl.COC(=O)C(N)CC(C)C DODCBMODXGJOKD-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002485 inorganic esters Chemical class 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR130018 | 1967-11-28 | ||
| DK501468AA DK128113B (da) | 1967-10-18 | 1968-10-17 | Analogifremgangsmåde til fremstilling af napthacenderivater eller disses additionssalte med syrer eller kvaternære ammoniumsalte deraf. |
| DK578468AA DK137193B (da) | 1967-11-28 | 1968-11-27 | Analogifremgangsmåde til fremstilling af naphthacenderivater eller syreadditionssalte eller kvaternære ammoniumsalte deraf. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO125675B true NO125675B (da) | 1972-10-16 |
Family
ID=27222051
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4739/68A NO125675B (da) | 1967-11-28 | 1968-11-27 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3627788A (da) |
| AT (1) | AT287197B (da) |
| BE (1) | BE724531A (da) |
| BR (1) | BR6804207D0 (da) |
| CH (1) | CH493512A (da) |
| DE (1) | DE1811518C3 (da) |
| DK (1) | DK137193B (da) |
| ES (1) | ES360802A1 (da) |
| FI (1) | FI51704C (da) |
| FR (1) | FR1578734A (da) |
| GB (1) | GB1212460A (da) |
| IE (1) | IE32509B1 (da) |
| IL (1) | IL31179A (da) |
| NL (1) | NL157313B (da) |
| NO (1) | NO125675B (da) |
| SE (1) | SE357198B (da) |
| YU (1) | YU33800B (da) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2930637C2 (de) * | 1978-08-03 | 1986-09-25 | Institut International de Pathologie Cellulaire et Moléculaire, Bruxelles | N-(L-Leucyl)-doxorubicin, Verfahren zu dessen Herstellung und dieses enthaltende pharmazeutische Zubereitungen |
| US4296105A (en) * | 1978-08-03 | 1981-10-20 | Institut International De Pathologie Cellulaire Et Moleculaire | Derivatives of doxorubicine, their preparation and use |
| NZ225599A (en) * | 1987-08-04 | 1991-09-25 | Bristol Myers Co | Antibody-enzyme conjugates and combinations with prodrugs for the treatment of tumour cells |
| IL106992A (en) * | 1988-02-11 | 1994-06-24 | Bristol Myers Squibb Co | Noble hydrazonic history of anthracycline and methods for their preparation |
| US5739313A (en) * | 1995-11-13 | 1998-04-14 | Regents Of The University Of Minnesota | Radionuclide labeling of vitamin B12 and coenzymes thereof |
| US6806363B1 (en) | 1999-04-16 | 2004-10-19 | Mayo Foundation For Medical Education & Research | Cobalamin conjugates useful as antitumor agents |
| WO2001028595A1 (en) | 1999-10-15 | 2001-04-26 | Mayo Foundation For Medical Education And Research | Cobalamin conjugates useful as imaging and therapeutic agents |
| US7591995B2 (en) * | 1999-10-15 | 2009-09-22 | Mayo Foundation For Medical Education And Research | Cobalamin conjugates useful as imaging and therapeutic agents |
| TWI228512B (en) | 2000-10-25 | 2005-03-01 | Mayo Foundation | Transcobalamin binding conjugates useful for treating abnormal cellular proliferation |
| JP2005508332A (ja) * | 2001-09-28 | 2005-03-31 | メイオウ・フアウンデーシヨン・フオー・メデイカル・エジユケイシヨン・アンド・リサーチ | 薬剤を送達するための、輸送タンパク質とコンジュゲートコバラミンとの同時投与 |
| US8535750B2 (en) * | 2005-05-17 | 2013-09-17 | Cargill, Incorporated | Granular lecithins, granular lysolecithins, process for their production and compositions containing them |
-
1967
- 1967-11-28 FR FR130018A patent/FR1578734A/fr not_active Expired
-
1968
- 1968-11-13 FI FI683241A patent/FI51704C/fi active
- 1968-11-20 NL NL6816534.A patent/NL157313B/xx not_active IP Right Cessation
- 1968-11-21 BR BR204207/68A patent/BR6804207D0/pt unknown
- 1968-11-27 IE IE1451/68A patent/IE32509B1/xx unknown
- 1968-11-27 BE BE724531D patent/BE724531A/xx not_active IP Right Cessation
- 1968-11-27 GB GB56387/68A patent/GB1212460A/en not_active Expired
- 1968-11-27 NO NO4739/68A patent/NO125675B/no unknown
- 1968-11-27 SE SE16185/68A patent/SE357198B/xx unknown
- 1968-11-27 DK DK578468AA patent/DK137193B/da unknown
- 1968-11-27 IL IL31179A patent/IL31179A/xx unknown
- 1968-11-27 CH CH1768068A patent/CH493512A/fr not_active IP Right Cessation
- 1968-11-27 US US779632A patent/US3627788A/en not_active Expired - Lifetime
- 1968-11-28 ES ES360802A patent/ES360802A1/es not_active Expired
- 1968-11-28 AT AT1157468A patent/AT287197B/de not_active IP Right Cessation
- 1968-11-28 DE DE1811518A patent/DE1811518C3/de not_active Expired
- 1968-11-28 YU YU2814/68A patent/YU33800B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1811518B2 (de) | 1978-09-07 |
| NL157313B (nl) | 1978-07-17 |
| NL6816534A (da) | 1969-05-30 |
| DE1811518C3 (de) | 1979-05-03 |
| FI51704C (fi) | 1977-03-10 |
| IE32509B1 (en) | 1973-08-22 |
| DK137193C (da) | 1978-06-19 |
| YU281468A (en) | 1977-10-31 |
| BE724531A (da) | 1969-05-27 |
| BR6804207D0 (pt) | 1973-02-22 |
| IL31179A (en) | 1972-12-29 |
| IE32509L (en) | 1969-05-28 |
| GB1212460A (en) | 1970-11-18 |
| FR1578734A (da) | 1969-08-22 |
| IL31179A0 (en) | 1969-01-29 |
| DK137193B (da) | 1978-01-30 |
| AT287197B (de) | 1971-01-11 |
| CH493512A (fr) | 1970-07-15 |
| FI51704B (da) | 1976-11-30 |
| SE357198B (da) | 1973-06-18 |
| YU33800B (en) | 1978-05-15 |
| ES360802A1 (es) | 1970-07-16 |
| DE1811518A1 (de) | 1969-07-10 |
| US3627788A (en) | 1971-12-14 |
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