CA1180275A - Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode - Google Patents

Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode

Info

Publication number: CA1180275A
Authority: CA; Canada
Prior art keywords: group; formula; treatment; pharmaceutically acceptable; acceptable carrier
Prior art date: 1980-05-30
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

Application number

CA000436138A

Other languages

English (en)

Inventor

Eric J. Bulten

Antonius M.J. Liebregts

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

Original Assignee

Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

Priority date (The priority date 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 date listed.)

1980-05-30

Filing date

1983-09-06

Publication date

1985-01-02

1981-05-08 Priority claimed from NL8102268A external-priority patent/NL8102268A/nl

1983-09-06 Application filed by Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO filed Critical Nederlandse Organisatie voor Toegepast Natuurwetenschappelijk Onderzoek TNO

1983-09-06 Priority to CA000436138A priority Critical patent/CA1180275A/fr

1985-01-02 Application granted granted Critical

1985-01-02 Publication of CA1180275A publication Critical patent/CA1180275A/fr

Status Expired legal-status Critical Current

Links

150000002291 germanium compounds Chemical class 0.000 title claims abstract description 23
206010028980 Neoplasm Diseases 0.000 title claims description 29
201000011510 cancer Diseases 0.000 title claims description 19
238000000034 method Methods 0.000 title abstract description 16
238000002360 preparation method Methods 0.000 title abstract description 11
239000003814 drug Substances 0.000 title abstract description 10
125000003118 aryl group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 28
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000005587 carbonate group Chemical group 0.000 claims description 2
150000007942 carboxylates Chemical group 0.000 claims description 2
125000004185 ester group Chemical group 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate group Chemical group [N+](=O)([O-])[O-] NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 2
125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims description 2
125000005544 phthalimido group Chemical group 0.000 claims description 2
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
125000004001 thioalkyl group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
125000000962 organic group Chemical group 0.000 abstract description 5
230000000259 anti-tumor effect Effects 0.000 abstract description 4
229910052732 germanium Inorganic materials 0.000 abstract description 4
GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract description 4
229910052799 carbon Inorganic materials 0.000 abstract description 2
125000005842 heteroatom Chemical group 0.000 abstract description 2
125000000129 anionic group Chemical group 0.000 abstract 2
230000000694 effects Effects 0.000 abstract 1
210000003734 kidney Anatomy 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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
239000000243 solution Substances 0.000 description 11
238000009835 boiling Methods 0.000 description 10
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 7
239000007788 liquid Substances 0.000 description 7
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
238000004821 distillation Methods 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
229960004132 diethyl ether Drugs 0.000 description 4
230000007717 exclusion Effects 0.000 description 4
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 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 3
VXGHASBVNMHGDI-UHFFFAOYSA-N digermane Chemical compound [Ge][Ge] VXGHASBVNMHGDI-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
239000003208 petroleum Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
WUQCDHQMKUEOLZ-UHFFFAOYSA-N C(CCCCCC)[GeH]([Ge](CCCCCCC)(CCCCCCC)CCCCCCC)CCCCCCC Chemical compound C(CCCCCC)[GeH]([Ge](CCCCCCC)(CCCCCCC)CCCCCCC)CCCCCCC WUQCDHQMKUEOLZ-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
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 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
238000005481 NMR spectroscopy Methods 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
125000001905 inorganic group Chemical group 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
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
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
SWJPEBQEEAHIGZ-UHFFFAOYSA-N 1,4-dibromobenzene Chemical compound BrC1=CC=C(Br)C=C1 SWJPEBQEEAHIGZ-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
UCDVYLIJVWBEDI-UHFFFAOYSA-N C(C)[GeH2][GeH3] Chemical compound C(C)[GeH2][GeH3] UCDVYLIJVWBEDI-UHFFFAOYSA-N 0.000 description 1
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 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
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
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
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 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
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
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 1
LZFYUKGXWJPWJP-UHFFFAOYSA-N C[GeH2][GeH2][GeH3] Chemical compound C[GeH2][GeH2][GeH3] LZFYUKGXWJPWJP-UHFFFAOYSA-N 0.000 description 1
241000088885 Chlorops Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
-1 XIX Chloro- Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
235000019270 ammonium chloride Nutrition 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
125000001309 chloro group Chemical group Cl* 0.000 description 1
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 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
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004817 gas chromatography Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 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
NCFSDGWPAKOPOU-UHFFFAOYSA-N n-ethylethanamine;lithium Chemical compound [Li].CCNCC NCFSDGWPAKOPOU-UHFFFAOYSA-N 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
ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
150000003058 platinum compounds Chemical class 0.000 description 1
238000001953 recrystallisation 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
229910052727 yttrium Inorganic materials 0.000 description 1

CA000436138A 1980-05-30 1983-09-06 Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode Expired CA1180275A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000436138A CA1180275A (fr)	1980-05-30	1983-09-06	Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
NL8003159		1980-05-30
NL8003159		1980-05-30
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.
NL8102268		1981-05-08
CA000378668A CA1159455A (fr)	1980-05-30	1981-05-29	Composes de germanium, procede de preparation et preparation d'un medicament le contenant qui peut etre utilise pour le traitement du cancer. medicament moule le contenant
CA000436138A CA1180275A (fr)	1980-05-30	1983-09-06	Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000378668A Division CA1159455A (fr)	1980-05-30	1981-05-29	Composes de germanium, procede de preparation et preparation d'un medicament le contenant qui peut etre utilise pour le traitement du cancer. medicament moule le contenant

Publications (1)

Publication Number	Publication Date
CA1180275A true CA1180275A (fr)	1985-01-02

Family

ID=27426307

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000436138A Expired CA1180275A (fr)	1980-05-30	1983-09-06	Composes de germanium, procede de preparation et preparation d'un medicament le contenant utilise pour le traitement du cancer ainsi que le produit moule obtenu par cette methode

Country Status (1)

Country	Link
CA (1)	CA1180275A (fr)

1983
- 1983-09-06 CA CA000436138A patent/CA1180275A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2002-01-02	MKEX	Expiry

Publication	Publication Date	Title
SU514569A3 (ru)	1976-05-15	Способ получени производных пиридазина
US3095434A (en)	1963-06-25	Organotin sulfonates
US3256290A (en)	1966-06-14	4-methoxypolychloropyridines
Considine et al.	1963	Organotin Chemistry: II. The Reaction of Diorganotin Oxides with Phenols
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US3734925A (en)	1973-05-22	N-amino-3,4-dimethyl-6-isobutyl-phthalimides
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US5047526A (en)	1991-09-10	Dehydrogenative silylation process of organic compounds having active hydrogen
Ishihara et al.	1990	A Facile Synthesis of β‐Selenolactams
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US3674789A (en)	1972-07-04	Tricyclohexyltin esters