CA1159455A - 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 - Google Patents
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 obtainedInfo
- Publication number
- CA1159455A CA1159455A CA000378668A CA378668A CA1159455A CA 1159455 A CA1159455 A CA 1159455A CA 000378668 A CA000378668 A CA 000378668A CA 378668 A CA378668 A CA 378668A CA 1159455 A CA1159455 A CA 1159455A
- Authority
- CA
- Canada
- Prior art keywords
- group
- chloro
- germanium compound
- administrable
- purifying
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 53
- 150000002291 germanium compounds Chemical class 0.000 title claims abstract description 13
- 238000002360 preparation method Methods 0.000 title abstract description 11
- 206010028980 Neoplasm Diseases 0.000 title abstract description 10
- 201000011510 cancer Diseases 0.000 title abstract description 9
- 239000003814 drug Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 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 claims description 5
- 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 claims description 5
- 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 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 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 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 229910052732 germanium Inorganic materials 0.000 claims description 4
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims description 3
- 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 claims 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 claims description 3
- 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 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000005587 carbonate group Chemical group 0.000 claims description 3
- 150000007942 carboxylates Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 3
- 125000005544 phthalimido group Chemical group 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical group Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 claims description 2
- 238000009877 rendering Methods 0.000 claims 12
- 239000000126 substance Substances 0.000 claims 12
- -1 tri-germanium Chemical compound 0.000 claims 9
- YGNUJFPXSWTBJX-UHFFFAOYSA-N [GeH4+][GeH3] Chemical compound [GeH4+][GeH3] YGNUJFPXSWTBJX-UHFFFAOYSA-N 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 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 claims 2
- CUJGQPNITCDMRZ-UHFFFAOYSA-N Cl[GeH2+]([GeH3])Cl Chemical compound Cl[GeH2+]([GeH3])Cl CUJGQPNITCDMRZ-UHFFFAOYSA-N 0.000 claims 2
- 239000012380 dealkylating agent Substances 0.000 claims 2
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical group [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 claims 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 15
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 238000009835 boiling Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- 238000004821 distillation Methods 0.000 description 7
- 239000007788 liquid Substances 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
- 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
- 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
- 229960004132 diethyl ether Drugs 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 125000000962 organic group Chemical group 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 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
- 125000001931 aliphatic group Chemical group 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
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 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
- NCFSDGWPAKOPOU-UHFFFAOYSA-N n-ethylethanamine;lithium Chemical compound [Li].CCNCC NCFSDGWPAKOPOU-UHFFFAOYSA-N 0.000 description 2
- 231100000417 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-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
- 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 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
- 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 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
- QWDAZKFGHRLROA-UHFFFAOYSA-N CC[Ge](CC)(CC)[Ge](CC)(CC)O[Ge](CC)(CC)[Ge](CC)(CC)CC Chemical compound CC[Ge](CC)(CC)[Ge](CC)(CC)O[Ge](CC)(CC)[Ge](CC)(CC)CC QWDAZKFGHRLROA-UHFFFAOYSA-N 0.000 description 1
- 241000088885 Chlorops Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000428533 Rhis Species 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
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- BDMFYHHLDXQFQD-UHFFFAOYSA-N butyl(trichloro)germane Chemical compound CCCC[Ge](Cl)(Cl)Cl BDMFYHHLDXQFQD-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 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
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000001905 inorganic group Chemical group 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 229940091250 magnesium supplement Drugs 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
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000003058 platinum compounds Chemical class 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000004083 survival effect Effects 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
- 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
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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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. |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000436138A Division 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1159455A true CA1159455A (en) | 1983-12-27 |
Family
ID=26645627
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000378668A Expired 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 |
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 |
| NL8102268A (nl) | 1981-12-16 |
| SE8103403L (sv) | 1981-12-01 |
| 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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