JPS6158448B2 - - Google Patents
Info
- Publication number
- JPS6158448B2 JPS6158448B2 JP58099609A JP9960983A JPS6158448B2 JP S6158448 B2 JPS6158448 B2 JP S6158448B2 JP 58099609 A JP58099609 A JP 58099609A JP 9960983 A JP9960983 A JP 9960983A JP S6158448 B2 JPS6158448 B2 JP S6158448B2
- Authority
- JP
- Japan
- Prior art keywords
- present
- ceg
- compound
- organic germanium
- antitumor agent
- 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
- 239000002246 antineoplastic agent Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002291 germanium compounds Chemical class 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 7
- 206010028980 Neoplasm Diseases 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- -1 organogermanium compound Chemical class 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 5
- 239000002075 main ingredient Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- MUDDKLJPADVVKF-UHFFFAOYSA-N trichlorogermane Chemical compound Cl[GeH](Cl)Cl MUDDKLJPADVVKF-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZJUHNMADISSFJZ-UHFFFAOYSA-N 2-trichlorogermylpropanoic acid Chemical compound OC(=O)C(C)[Ge](Cl)(Cl)Cl ZJUHNMADISSFJZ-UHFFFAOYSA-N 0.000 description 3
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 201000009030 Carcinoma Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229910052732 germanium Inorganic materials 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CVMBLRBRUFIQFK-UHFFFAOYSA-N 2-trichlorogermylpropanamide Chemical compound NC(=O)C(C)[Ge](Cl)(Cl)Cl CVMBLRBRUFIQFK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000001629 suppression Effects 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910005742 Ge—C Inorganic materials 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003466 anti-cipated effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- PVADDRMAFCOOPC-UHFFFAOYSA-N oxogermanium Chemical group [Ge]=O PVADDRMAFCOOPC-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical group O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
- 230000002100 tumorsuppressive effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58099609A JPS59225117A (ja) | 1983-06-06 | 1983-06-06 | 抗腫瘍剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58099609A JPS59225117A (ja) | 1983-06-06 | 1983-06-06 | 抗腫瘍剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59225117A JPS59225117A (ja) | 1984-12-18 |
| JPS6158448B2 true JPS6158448B2 (enrdf_load_stackoverflow) | 1986-12-11 |
Family
ID=14251833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58099609A Granted JPS59225117A (ja) | 1983-06-06 | 1983-06-06 | 抗腫瘍剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59225117A (enrdf_load_stackoverflow) |
-
1983
- 1983-06-06 JP JP58099609A patent/JPS59225117A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59225117A (ja) | 1984-12-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4299838A (en) | Tryptophan derivatives having an increased effect on the central nervous system | |
| JPS6075454A (ja) | 鎮痛用新規化合物および組成物 | |
| HU197295B (en) | Process for production of new derivatives of n-/2'-aminphenil/-benzamid and medical preparatives containing those as active substance | |
| US20090042838A1 (en) | Phosphaplatins and their use in the treatment of cancers resistant to cisplatin and carboplatin | |
| JPH0261477B2 (enrdf_load_stackoverflow) | ||
| US3676554A (en) | Anti-arthritic compositions comprising phosphine or phosphite gold halide complexes and methods of producing anti-arthritic activity | |
| US5283068A (en) | Procaine double salt complexes | |
| JPS6130560A (ja) | アセチルカルニチンのエステル、その製法およびそれを有効成分とする医薬組成物 | |
| JPS6158449B2 (enrdf_load_stackoverflow) | ||
| US5281588A (en) | Organometallic compounds, methods for their preparation and pharmaceutical compositions containing them | |
| US4748187A (en) | Opioid peptide-degrading enzyme inhibitor with a germanium compound | |
| JPS61145115A (ja) | 塵肺症患者用風邪症候群予防剤 | |
| CA1283904C (en) | Liposoluble platinum (ii) complex and preparation thereof | |
| US4137326A (en) | Use of magnesium monospartate hydrochloride complex | |
| US4973553A (en) | Salt or organogermanium compound and medicine containing the same | |
| JPS6158448B2 (enrdf_load_stackoverflow) | ||
| EP0176005A1 (en) | Novel platinum complexes | |
| US3116312A (en) | Substituted-2-cyanoacetanilides | |
| EP0404062A2 (en) | Organogermanium compound, process for preparation of same as well as use thereof | |
| JPH04211016A (ja) | 抗−ウィルス活性を有する化合物及びそれを含む医薬組成物 | |
| EP0214862B1 (en) | Anti-tumour platinum complexes, their preparation and their use | |
| JPS61145116A (ja) | オステオポロ−ジス治療剤 | |
| KR100249408B1 (ko) | (s)-2,3-디하이드로폴리프레놀,(s)-2,3-디하이드로폴리프레닐모노포스-페이트,이들의제조방법및이들을포함한암의성장또는전이억제용약제 | |
| US3621058A (en) | Novel formamido-cycloalkane derivatives | |
| US5254686A (en) | Procaine double salt complexes |