BG61059B2 - Аналози на дономицина - Google Patents
Аналози на дономицина Download PDFInfo
- Publication number
- BG61059B2 BG61059B2 BG098211A BG9821193A BG61059B2 BG 61059 B2 BG61059 B2 BG 61059B2 BG 098211 A BG098211 A BG 098211A BG 9821193 A BG9821193 A BG 9821193A BG 61059 B2 BG61059 B2 BG 61059B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- donosaminylc
- demethoxidonomycinone
- sepimers
- epimers
- compounds
- Prior art date
Links
- STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical class 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 title abstract 2
- 238000000034 method Methods 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 1
- YMMTXWRRJUTBEI-LYTHVRBOSA-N epimer a Chemical compound O=C1NC2=NC=CC=C2[C@@]1(CC1=C2)CC1=CC=C2NC(=O)CN1C(C=CC=C2NC(=O)C3)=C2C3C1 YMMTXWRRJUTBEI-LYTHVRBOSA-N 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 2
- 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 abstract 1
- 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 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 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 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 229940009456 adriamycin Drugs 0.000 description 13
- 206010028980 Neoplasm Diseases 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 229940045799 anthracyclines and related substance Drugs 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000011712 cell development Effects 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 208000032839 leukemia Diseases 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 230000001613 neoplastic effect Effects 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 241000713862 Moloney murine sarcoma virus Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 210000002950 fibroblast Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- NGYIMTKLQULBOO-UHFFFAOYSA-L mercury dibromide Chemical compound Br[Hg]Br NGYIMTKLQULBOO-UHFFFAOYSA-L 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000005748 tumor development 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2608374A GB1467383A (en) | 1974-06-12 | 1974-06-12 | Daunomycin analogues |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61059B2 true BG61059B2 (bg) | 1996-09-30 |
Family
ID=10238087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098211A BG61059B2 (bg) | 1974-06-12 | 1993-11-11 | Аналози на дономицина |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4046878A (xx) |
| JP (1) | JPS5840557B2 (xx) |
| AT (1) | AT337363B (xx) |
| BE (1) | BE830090A (xx) |
| BG (1) | BG61059B2 (xx) |
| CH (1) | CH611317A5 (xx) |
| DE (2) | DE2525633A1 (xx) |
| DK (1) | DK147304C (xx) |
| ES (1) | ES438431A1 (xx) |
| FR (1) | FR2274629A1 (xx) |
| GB (1) | GB1467383A (xx) |
| HK (1) | HK982A (xx) |
| MY (1) | MY103666A (xx) |
| NL (1) | NL173272C (xx) |
| SE (1) | SE423633B (xx) |
| SU (1) | SU645588A3 (xx) |
| ZA (1) | ZA753722B (xx) |
Families Citing this family (44)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1506200A (en) * | 1975-04-30 | 1978-04-05 | Farmaceutici Italia | Glycosides |
| GB1509875A (en) * | 1976-06-14 | 1978-05-04 | Farmaceutici Italia | Optically active anthracyclinones and anthracycline glycosides |
| US4161480A (en) * | 1978-06-05 | 1979-07-17 | G. D. Searle & Co. | Intermediates for the synthesis of 4-demethoxydaunorubicin |
| US4201773A (en) * | 1978-07-26 | 1980-05-06 | The United States Of America As Represented By The Department Of Health, Education And Welfare | 7-O-(2,6-Dideoxy-α-L-lyxo-hexopyranosyl)-daunomycinone, desmethoxy daunomycinone, adriamycinone, and carminomycinone |
| IL55431A (en) * | 1978-08-24 | 1982-07-30 | Yeda Res & Dev | Anthracycline type antibiotics,their preparation and pharmaceutical compositions comprising them |
| NL8001417A (nl) * | 1979-03-17 | 1980-09-19 | Erba Farmitalia | Antitumorglycosiden. |
| JPS5673039A (en) * | 1979-08-20 | 1981-06-17 | Hoffmann La Roche | Naphthacene derivative |
| EP0024727B1 (en) * | 1979-09-01 | 1982-05-26 | FARMITALIA CARLO ERBA S.p.A. | Anthracycline glycosides, processes for their preparation and pharmaceutical composition containing them |
| DE3100968A1 (de) * | 1980-01-16 | 1982-01-14 | Farmitalia Carlo Erba S.p.A., 20159 Milano | Anthracyclinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4348388A (en) * | 1980-04-02 | 1982-09-07 | G.D. Searle & Co. | 11-Amino-11-deoxydaunorubicin and analogs |
| ZA814722B (en) * | 1980-07-18 | 1982-07-28 | Hoffmann La Roche | Novel anthracycline glycosides |
| IT1210476B (it) * | 1981-05-28 | 1989-09-14 | Erba Farmitalia | Antracicline. |
| GB8317037D0 (en) * | 1983-06-23 | 1983-07-27 | Erba Farmitalia | 6-deoxyanthracyclines |
| US5138042A (en) * | 1981-05-28 | 1992-08-11 | Farmitalia Carlo Erba S.P.A. | 6-deoxyanthracyclines |
| US4563444A (en) * | 1982-05-26 | 1986-01-07 | Farmitalia Carlo Erba S.P.A. | Anthracycline glycosides, use and compositions containing same |
| US4604381A (en) * | 1982-07-16 | 1986-08-05 | Farmitalia Carlo Erba S.P.A. | 4-demethoxy-13-dihydrodaunorubicin and use thereof |
| US4562177A (en) * | 1982-08-17 | 1985-12-31 | The Ohio State University Research Foundation | 3'-Amino-2' halo-anthracycline antibiotics |
| US4564674A (en) * | 1983-10-31 | 1986-01-14 | Sagami Chemical Research Center | Process for an anthracycline derivative, and an anthracyclinone derivative useful for the process |
| US4496485A (en) * | 1983-11-25 | 1985-01-29 | G. D. Searle & Co. | Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones |
| US4537882A (en) * | 1984-05-10 | 1985-08-27 | Ohio State University | 4-Demethoxy-3'-desamino-2'-halo-anthracycline and pharmaceutical composition containing same |
| US4697005A (en) * | 1985-03-20 | 1987-09-29 | Ohio State University Research Foundation | 1-fluoro, 4-fluoro, and 1,4-difluoro anthracycline anticancer antibiotics |
| US5124317A (en) * | 1985-08-02 | 1992-06-23 | Farmitalia Carlo Erba S.P.A. | Injectable ready-to-use solutions containing an antitumor anthracycline glycoside |
| NZ224252A (en) * | 1987-04-21 | 1991-09-25 | Erba Carlo Spa | An anthracycline glycoside and its preparation |
| JPS63191263U (xx) * | 1987-05-29 | 1988-12-09 | ||
| GB2212154B (en) * | 1987-11-10 | 1991-03-27 | Erba Carlo Spa | New 4-demethoxy anthracycline derivatives |
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
| GB8808475D0 (en) * | 1988-04-11 | 1988-05-11 | Erba Carlo Spa | Process for preparing 4-demethoxydauno-mycinone |
| GB8818167D0 (en) * | 1988-07-29 | 1988-09-01 | Erba Carlo Spa | Novel 4-substituted anthracyclinones & process for their preparation |
| WO1993018050A1 (en) * | 1992-03-02 | 1993-09-16 | Pfizer Inc. | Sugar derivatives of macrolides |
| US8252520B2 (en) * | 2002-10-11 | 2012-08-28 | Taivex Therapeutics Corporation | Methods and compounds for inhibiting Hec1 activity for the treatment of proliferative diseases |
| US20080161251A1 (en) | 2005-01-21 | 2008-07-03 | Astex Therapeutics Limited | Pharmaceutical Compounds |
| JP5528806B2 (ja) | 2006-10-12 | 2014-06-25 | アステックス、セラピューティックス、リミテッド | 複合薬剤 |
| EP2073807A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US8173621B2 (en) | 2008-06-11 | 2012-05-08 | Gilead Pharmasset Llc | Nucleoside cyclicphosphates |
| NZ593648A (en) * | 2008-12-23 | 2013-09-27 | Gilead Pharmasset Llc | Nucleoside phosphoramidates |
| CL2009002206A1 (es) * | 2008-12-23 | 2011-08-26 | Gilead Pharmasset Llc | Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales. |
| EP2376514A2 (en) * | 2008-12-23 | 2011-10-19 | Pharmasset, Inc. | Nucleoside analogs |
| BR112012012160B1 (pt) | 2009-11-13 | 2022-04-26 | Amgen, Inc. | Material e métodos para tratar ou prevenir doenças associadas ao her-3 |
| KR101715981B1 (ko) | 2010-03-31 | 2017-03-13 | 길리애드 파마셋 엘엘씨 | 뉴클레오사이드 포스포르아미데이트 |
| CA2815154A1 (en) | 2010-08-06 | 2012-02-09 | U3 Pharma Gmbh | Use of her3 binding agents in prostate treatment |
| DE102011113652A1 (de) | 2011-09-19 | 2013-03-21 | Heraeus Precious Metals Gmbh & Co. Kg | Kristallisierung von Idarubicinhydrochlorid |
| EP4176871A1 (en) | 2011-10-03 | 2023-05-10 | Canqura Oncology Ab | Nanoparticles, process for preparation and use thereof as carrier for amphipatic of hydrphobic molecules in fields of medicine including cancer treatment and food related compounds |
| WO2014163558A1 (en) | 2013-04-01 | 2014-10-09 | Moreinx Ab | Nanoparticles, composed of sterol and saponin from quillaja saponaria molina process for preparation and use thereof as carrier for amphipatic of hydrphobic molecules in fields of medicine including cancer treatment and food related compounds |
| EP3669890A1 (en) | 2018-12-18 | 2020-06-24 | Croda International PLC | Filamentous nanoparticles having vaccine adjuvant effect |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3427300A (en) * | 1965-11-12 | 1969-02-11 | Merck & Co Inc | Anti-inflammatory steroid 2'-acetamido-2'-deoxy-glucoside compounds |
| US3803124A (en) * | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
| US3686163A (en) * | 1968-05-14 | 1972-08-22 | Farmaceutici Italia | Dihydrodaunomycin antibiotic and derivatives thereof |
-
1974
- 1974-06-12 GB GB2608374A patent/GB1467383A/en not_active Expired
-
1975
- 1975-05-22 US US05/579,901 patent/US4046878A/en not_active Expired - Lifetime
- 1975-06-06 NL NLAANVRAGE7506745,A patent/NL173272C/xx not_active IP Right Cessation
- 1975-06-09 SE SE7506589A patent/SE423633B/xx not_active IP Right Cessation
- 1975-06-09 FR FR7517881A patent/FR2274629A1/fr active Granted
- 1975-06-09 AT AT437375A patent/AT337363B/de not_active IP Right Cessation
- 1975-06-09 DK DK256875A patent/DK147304C/da not_active IP Right Cessation
- 1975-06-09 DE DE19752525633 patent/DE2525633A1/de active Granted
- 1975-06-09 DE DE1993175027 patent/DE19375027I2/de active Active
- 1975-06-10 JP JP50069250A patent/JPS5840557B2/ja not_active Expired
- 1975-06-10 SU SU752141338A patent/SU645588A3/ru active
- 1975-06-10 ZA ZA00753722A patent/ZA753722B/xx unknown
- 1975-06-11 CH CH756375A patent/CH611317A5/xx not_active IP Right Cessation
- 1975-06-11 BE BE157205A patent/BE830090A/xx not_active IP Right Cessation
- 1975-06-11 ES ES438431A patent/ES438431A1/es not_active Expired
-
1982
- 1982-01-14 HK HK9/82A patent/HK982A/xx unknown
-
1988
- 1988-12-22 MY MYPI88001506A patent/MY103666A/en unknown
-
1993
- 1993-11-11 BG BG098211A patent/BG61059B2/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2274629A1 (fr) | 1976-01-09 |
| DK147304B (da) | 1984-06-12 |
| DE2525633C3 (xx) | 1979-10-18 |
| CH611317A5 (xx) | 1979-05-31 |
| JPS5840557B2 (ja) | 1983-09-06 |
| BE830090A (fr) | 1975-12-11 |
| GB1467383A (en) | 1977-03-16 |
| NL7506745A (nl) | 1975-12-16 |
| ES438431A1 (es) | 1977-02-01 |
| NL173272B (nl) | 1983-08-01 |
| SE7506589L (sv) | 1975-12-15 |
| JPS518260A (xx) | 1976-01-23 |
| SE423633B (sv) | 1982-05-17 |
| SU645588A3 (ru) | 1979-01-30 |
| MY103666A (en) | 1993-08-28 |
| US4046878A (en) | 1977-09-06 |
| DE2525633A1 (de) | 1976-01-02 |
| DE19375027I2 (de) | 2002-06-13 |
| DK256875A (da) | 1975-12-13 |
| AT337363B (de) | 1977-06-27 |
| AU8197975A (en) | 1976-12-16 |
| ZA753722B (en) | 1976-09-29 |
| DE2525633B2 (xx) | 1979-03-01 |
| HK982A (en) | 1982-01-22 |
| DK147304C (da) | 1984-12-17 |
| ATA437375A (de) | 1976-10-15 |
| NL173272C (nl) | 1984-01-02 |
| FR2274629B1 (xx) | 1980-01-11 |
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