NL8102268A - Germaniumverbindingen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een derglijke germaniumverbinding voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. - Google Patents
Germaniumverbindingen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een derglijke germaniumverbinding voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. Download PDFInfo
- Publication number
- NL8102268A NL8102268A NL8102268A NL8102268A NL8102268A NL 8102268 A NL8102268 A NL 8102268A NL 8102268 A NL8102268 A NL 8102268A NL 8102268 A NL8102268 A NL 8102268A NL 8102268 A NL8102268 A NL 8102268A
- Authority
- NL
- Netherlands
- Prior art keywords
- formula
- germanium compound
- process according
- germanium
- compound
- Prior art date
Links
- 150000002291 germanium compounds Chemical class 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 51
- 206010028980 Neoplasm Diseases 0.000 title claims description 9
- 201000011510 cancer Diseases 0.000 title claims description 9
- 229940126601 medicinal product Drugs 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052732 germanium Inorganic materials 0.000 claims description 5
- 125000000962 organic group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 4
- 125000001905 inorganic group Chemical group 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229940125904 compound 1 Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- 238000009835 boiling Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- YODVNKTXEWISGT-UHFFFAOYSA-N CC[Ge](Cl)(CC)[Ge](Cl)(CC)CC Chemical compound CC[Ge](Cl)(CC)[Ge](Cl)(CC)CC YODVNKTXEWISGT-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- BLABYOVRAXUAJO-UHFFFAOYSA-N CCCCC[Ge](Cl)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC Chemical compound CCCCC[Ge](Cl)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC BLABYOVRAXUAJO-UHFFFAOYSA-N 0.000 description 3
- FRMPNBYQJDBMDW-UHFFFAOYSA-N CC[Ge](CC)(CC)[Ge](C)(Cl)[Ge](CC)(CC)CC Chemical compound CC[Ge](CC)(CC)[Ge](C)(Cl)[Ge](CC)(CC)CC FRMPNBYQJDBMDW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- PFUUQCBAGYSPHY-UHFFFAOYSA-N C=1C=CC=CC=1[Ge](Cl)([Ge](CCCC)(CCCC)CCCC)C1=CC=CC=C1 Chemical compound C=1C=CC=CC=1[Ge](Cl)([Ge](CCCC)(CCCC)CCCC)C1=CC=CC=C1 PFUUQCBAGYSPHY-UHFFFAOYSA-N 0.000 description 2
- HTZWAYCYCLQJRJ-UHFFFAOYSA-N CCCCCCC[Ge](Cl)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC Chemical compound CCCCCCC[Ge](Cl)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC HTZWAYCYCLQJRJ-UHFFFAOYSA-N 0.000 description 2
- FEIALDSSVRCFQO-UHFFFAOYSA-N CCCC[Ge](Cl)(CCCC)[Ge](CCCC)(CCCC)CCCC Chemical compound CCCC[Ge](Cl)(CCCC)[Ge](CCCC)(CCCC)CCCC FEIALDSSVRCFQO-UHFFFAOYSA-N 0.000 description 2
- XJUGQAPJUYJJSI-UHFFFAOYSA-N CCN(CC)[Ge](CC)(CC)[Ge](CC)(CC)N(CC)CC Chemical compound CCN(CC)[Ge](CC)(CC)[Ge](CC)(CC)N(CC)CC XJUGQAPJUYJJSI-UHFFFAOYSA-N 0.000 description 2
- DKLGKJBNHUJHGC-UHFFFAOYSA-N CC[Ge](Cl)(CC)[Ge](CC)(CC)CC Chemical compound CC[Ge](Cl)(CC)[Ge](CC)(CC)CC DKLGKJBNHUJHGC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 208000028018 Lymphocytic leukaemia Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- NEXMICNIHHIZSA-UHFFFAOYSA-N chloro-[4-[chloro(dimethyl)germyl]phenyl]-dimethylgermane Chemical compound C[Ge](C)(Cl)C1=CC=C([Ge](C)(C)Cl)C=C1 NEXMICNIHHIZSA-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- VXGHASBVNMHGDI-UHFFFAOYSA-N digermane Chemical compound [Ge][Ge] VXGHASBVNMHGDI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 208000003747 lymphoid leukemia Diseases 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- NCFSDGWPAKOPOU-UHFFFAOYSA-N n-ethylethanamine;lithium Chemical compound [Li].CCNCC NCFSDGWPAKOPOU-UHFFFAOYSA-N 0.000 description 2
- 231100001095 no nephrotoxicity Toxicity 0.000 description 2
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
- SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- MAMFLTDOXCPOQS-UHFFFAOYSA-N C(C)[GeH]([Ge](CC)(CC)CC)CC Chemical compound C(C)[GeH]([Ge](CC)(CC)CC)CC MAMFLTDOXCPOQS-UHFFFAOYSA-N 0.000 description 1
- FMKIGJPBZATMLZ-UHFFFAOYSA-N CCCCCCC[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC Chemical compound CCCCCCC[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC FMKIGJPBZATMLZ-UHFFFAOYSA-N 0.000 description 1
- XKAWGMJAMUGUSJ-UHFFFAOYSA-N CCCCCCC[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)O[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC Chemical compound CCCCCCC[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)O[Ge](CCCCCCC)(CCCCCCC)[Ge](CCCCCCC)(CCCCCCC)CCCCCCC XKAWGMJAMUGUSJ-UHFFFAOYSA-N 0.000 description 1
- SAWFFIPZFFQIMX-UHFFFAOYSA-N CCCCCC[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC Chemical compound CCCCCC[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC SAWFFIPZFFQIMX-UHFFFAOYSA-N 0.000 description 1
- UPKXRQSCERCRPW-UHFFFAOYSA-N CCCCCC[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)O[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC Chemical compound CCCCCC[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)O[Ge](CCCCCC)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC UPKXRQSCERCRPW-UHFFFAOYSA-N 0.000 description 1
- MHSXRIKWZUHPNW-UHFFFAOYSA-N CCCCCC[Ge](Cl)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC Chemical compound CCCCCC[Ge](Cl)(CCCCCC)[Ge](CCCCCC)(CCCCCC)CCCCCC MHSXRIKWZUHPNW-UHFFFAOYSA-N 0.000 description 1
- MGYBOELVMXPPGM-UHFFFAOYSA-N CCCCC[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC Chemical compound CCCCC[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC MGYBOELVMXPPGM-UHFFFAOYSA-N 0.000 description 1
- XJYUGYZJSCDQQB-UHFFFAOYSA-N CCCCC[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)O[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC Chemical compound CCCCC[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)O[Ge](CCCCC)(CCCCC)[Ge](CCCCC)(CCCCC)CCCCC XJYUGYZJSCDQQB-UHFFFAOYSA-N 0.000 description 1
- INLPFUWSEADOBH-UHFFFAOYSA-N CCCC[Ge](CCCC)(CCCC)[Ge](CCCC)(CCCC)CCCC Chemical compound CCCC[Ge](CCCC)(CCCC)[Ge](CCCC)(CCCC)CCCC INLPFUWSEADOBH-UHFFFAOYSA-N 0.000 description 1
- CQTOWSIAKFFTIU-UHFFFAOYSA-N CCN(CC)[Ge](CC)(CC)[Ge](CC)(CC)CC Chemical compound CCN(CC)[Ge](CC)(CC)[Ge](CC)(CC)CC CQTOWSIAKFFTIU-UHFFFAOYSA-N 0.000 description 1
- MPNSRQWKAXMNPV-UHFFFAOYSA-N CC[Ge](CC)(CC)[Ge](C)(C)[Ge](CC)(CC)CC Chemical compound CC[Ge](CC)(CC)[Ge](C)(C)[Ge](CC)(CC)CC MPNSRQWKAXMNPV-UHFFFAOYSA-N 0.000 description 1
- UOWFWBNGQSNNMQ-UHFFFAOYSA-N CC[Ge](CC)(CC)[Ge](C)([Ge](CC)(CC)CC)O[Ge](C)([Ge](CC)(CC)CC)[Ge](CC)(CC)CC Chemical compound CC[Ge](CC)(CC)[Ge](C)([Ge](CC)(CC)CC)O[Ge](C)([Ge](CC)(CC)CC)[Ge](CC)(CC)CC UOWFWBNGQSNNMQ-UHFFFAOYSA-N 0.000 description 1
- ZJBPDJIPKZEHEY-UHFFFAOYSA-N CC[Ge](Cl)(CC)[Ge](CC)(CC)C1=CC=CC=C1 Chemical compound CC[Ge](Cl)(CC)[Ge](CC)(CC)C1=CC=CC=C1 ZJBPDJIPKZEHEY-UHFFFAOYSA-N 0.000 description 1
- QUGBNCWOXIQULA-UHFFFAOYSA-N C[Ge](C)(C)[Ge](C)(C)Cl Chemical compound C[Ge](C)(C)[Ge](C)(C)Cl QUGBNCWOXIQULA-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005587 carbonate group Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- YQECBLVSMFAWIZ-UHFFFAOYSA-N dichloro(dimethyl)germane Chemical compound C[Ge](C)(Cl)Cl YQECBLVSMFAWIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- IEXRMSFAVATTJX-UHFFFAOYSA-N tetrachlorogermane Chemical compound Cl[Ge](Cl)(Cl)Cl IEXRMSFAVATTJX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- IFUCAAMZMJICIP-UHFFFAOYSA-N triethylgermanium Chemical compound CC[Ge](CC)CC.CC[Ge](CC)CC IFUCAAMZMJICIP-UHFFFAOYSA-N 0.000 description 1
- CKQULDKQRNJABT-UHFFFAOYSA-N trimethylgermanium Chemical compound C[Ge](C)C.C[Ge](C)C CKQULDKQRNJABT-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F7/30—Germanium compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8102268A NL8102268A (nl) | 1980-05-30 | 1981-05-08 | Germaniumverbindingen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een derglijke germaniumverbinding voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
| SE8103403A SE8103403L (sv) | 1980-05-30 | 1981-05-29 | Germaniumforeningar, sett att framstella dem, sett att framstella ett lekemedelspreparat under anvendning av en dylik germaniumforening for behandling av cancer samt det pa sa sett erhallna lekemedelspreparatet |
| GB8116524A GB2077267B (en) | 1980-05-30 | 1981-05-29 | Germanium compounds for the treatment of cancer |
| KR1019810001894A KR830005860A (ko) | 1981-05-08 | 1981-05-29 | 게르마늄 화합물 제조방법 및 암 치료용의 치료의약 제조방법 |
| DE19813121552 DE3121552A1 (de) | 1980-05-30 | 1981-05-29 | Germaniumverbindungen, verfahren zu deren herstellung und dieselben enthaltende arzneimittel zur krebsbehandlung |
| US06/268,139 US4501702A (en) | 1980-05-30 | 1981-05-29 | Germanium compounds |
| YU01374/81A YU137481A (en) | 1980-05-30 | 1981-05-29 | Process for obtaining germanium compounds |
| IL62988A IL62988A0 (en) | 1980-05-30 | 1981-05-29 | Germanium compounds,a process for the preparation thereof,a process for the preparation of a medicine using such a germanium compound for the treatment of cancer,as well as the shaped medicine thus formed and obtained |
| FR8110744A FR2483425A1 (fr) | 1980-05-30 | 1981-05-29 | Composes de germanium, procede d'obtention de medicaments les contenant et medicaments ainsi obtenus |
| AU71150/81A AU7115081A (en) | 1980-05-30 | 1981-05-29 | Germanium compounds |
| IT22035/81A IT1137171B (it) | 1980-05-30 | 1981-05-29 | Composti di germanio, procedimento per la loro preparazione, procedimento per la preparazione di un farmaco mediante tali composti di germanio per il trattamento del cancro,nonche' medicinale finito cosi' ottenuto |
| PT73101A PT73101B (en) | 1980-05-30 | 1981-05-29 | Process for preparing germanium compounds |
| CA000378668A CA1159455A (en) | 1980-05-30 | 1981-05-29 | Germanium compounds, a process for the preparation thereof, a process for the preparation of a medicine using such a germanium compound for the treatment of cancer, as well as the shaped medicine thus formed and obtained |
| YU01350/83A YU135083A (en) | 1980-05-30 | 1983-06-20 | Process for obtaining germanium compounds |
| CA000436138A CA1180275A (en) | 1980-05-30 | 1983-09-06 | Germanium compounds, a process for the preparation thereof, a process for the preparation of a medicine using such a germanium compound for the treatment of cancer, as well as the shaped medicine thus formed and obtained |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL8003159 | 1980-05-30 | ||
| NL8003159 | 1980-05-30 | ||
| NL8102268 | 1981-05-08 | ||
| NL8102268A NL8102268A (nl) | 1980-05-30 | 1981-05-08 | Germaniumverbindingen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een derglijke germaniumverbinding voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8102268A true NL8102268A (nl) | 1981-12-16 |
Family
ID=26645627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8102268A NL8102268A (nl) | 1980-05-30 | 1981-05-08 | Germaniumverbindingen, werkwijze voor het bereiden daarvan, werkwijze voor het bereiden van een geneesmiddel met toepassing van een derglijke germaniumverbinding voor de behandeling van kanker, alsmede aldus verkregen gevormd geneesmiddel. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4501702A (enExample) |
| AU (1) | AU7115081A (enExample) |
| CA (1) | CA1159455A (enExample) |
| DE (1) | DE3121552A1 (enExample) |
| FR (1) | FR2483425A1 (enExample) |
| GB (1) | GB2077267B (enExample) |
| IL (1) | IL62988A0 (enExample) |
| IT (1) | IT1137171B (enExample) |
| NL (1) | NL8102268A (enExample) |
| PT (1) | PT73101B (enExample) |
| SE (1) | SE8103403L (enExample) |
| YU (2) | YU137481A (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE36477E (en) * | 1988-03-29 | 1999-12-28 | Taiho Pharmaceutical Co., Ltd. | Benzoic acid derivatives and process for preparing the same |
| JP2752630B2 (ja) * | 1988-03-29 | 1998-05-18 | 大鵬薬品工業株式会社 | 新規安息香酸誘導体及びその製造方法 |
| JP2652556B2 (ja) * | 1988-08-29 | 1997-09-10 | 株式会社浅井ゲルマニウム研究所 | 有機ゲルマニウム化合物及びその製造方法 |
| DE3844282A1 (de) * | 1988-12-30 | 1990-07-05 | Hoechst Ag | Bisindenyl-derivat und verfahren zu seiner herstellung |
| JP2724397B2 (ja) * | 1989-01-30 | 1998-03-09 | 株式会社浅井ゲルマニウム研究所 | 有機ゲルマニウム化合物及びその製造方法 |
| PL214016B1 (pl) * | 2009-09-11 | 2013-06-28 | Univ Adama Mickiewicza | Nowe winylo-alkinylopodstawione zwiazki germanu oraz sposób otrzymywania winylo-alkinylopodstawionych zwiazków germanu |
-
1981
- 1981-05-08 NL NL8102268A patent/NL8102268A/nl not_active Application Discontinuation
- 1981-05-29 YU YU01374/81A patent/YU137481A/xx unknown
- 1981-05-29 CA CA000378668A patent/CA1159455A/en not_active Expired
- 1981-05-29 IL IL62988A patent/IL62988A0/xx unknown
- 1981-05-29 FR FR8110744A patent/FR2483425A1/fr active Granted
- 1981-05-29 US US06/268,139 patent/US4501702A/en not_active Expired - Fee Related
- 1981-05-29 PT PT73101A patent/PT73101B/pt unknown
- 1981-05-29 IT IT22035/81A patent/IT1137171B/it active
- 1981-05-29 GB GB8116524A patent/GB2077267B/en not_active Expired
- 1981-05-29 DE DE19813121552 patent/DE3121552A1/de not_active Withdrawn
- 1981-05-29 AU AU71150/81A patent/AU7115081A/en not_active Abandoned
- 1981-05-29 SE SE8103403A patent/SE8103403L/ not_active Application Discontinuation
-
1983
- 1983-06-20 YU YU01350/83A patent/YU135083A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2483425A1 (fr) | 1981-12-04 |
| GB2077267A (en) | 1981-12-16 |
| DE3121552A1 (de) | 1982-05-27 |
| US4501702A (en) | 1985-02-26 |
| IT8122035A0 (it) | 1981-05-29 |
| SE8103403L (sv) | 1981-12-01 |
| CA1159455A (en) | 1983-12-27 |
| AU7115081A (en) | 1981-12-03 |
| PT73101B (en) | 1985-01-08 |
| YU135083A (en) | 1983-12-31 |
| IL62988A0 (en) | 1981-07-31 |
| GB2077267B (en) | 1984-06-27 |
| YU137481A (en) | 1983-12-31 |
| IT1137171B (it) | 1986-09-03 |
| FR2483425B1 (enExample) | 1984-10-12 |
| PT73101A (en) | 1981-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1B | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BV | The patent application has lapsed |