JPS61267591A - 有機ゲルマニウム化合物 - Google Patents
有機ゲルマニウム化合物Info
- Publication number
- JPS61267591A JPS61267591A JP27175085A JP27175085A JPS61267591A JP S61267591 A JPS61267591 A JP S61267591A JP 27175085 A JP27175085 A JP 27175085A JP 27175085 A JP27175085 A JP 27175085A JP S61267591 A JPS61267591 A JP S61267591A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- give
- present
- germanium
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title abstract description 42
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 2
- 150000002291 germanium compounds Chemical class 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 8
- 108090000790 Enzymes Proteins 0.000 abstract description 8
- 102000004190 Enzymes Human genes 0.000 abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract description 6
- 239000013078 crystal Substances 0.000 abstract description 5
- 229910052732 germanium Inorganic materials 0.000 abstract description 5
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 abstract description 5
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 4
- 150000004795 grignard reagents Chemical class 0.000 abstract description 3
- 239000007818 Grignard reagent Substances 0.000 abstract description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052794 bromium Inorganic materials 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 7
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- -1 organogermanium compound Chemical class 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 102000001490 Opioid Peptides Human genes 0.000 description 3
- 108010093625 Opioid Peptides Proteins 0.000 description 3
- 230000000593 degrading effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003399 opiate peptide Substances 0.000 description 3
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 3
- 102000004400 Aminopeptidases Human genes 0.000 description 2
- 108090000915 Aminopeptidases Proteins 0.000 description 2
- 102100030988 Angiotensin-converting enzyme Human genes 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000000259 anti-tumor effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 1
- NLIJOIUVZBYQRS-UHFFFAOYSA-N 3-trichlorogermylpropanoic acid Chemical compound OC(=O)CC[Ge](Cl)(Cl)Cl NLIJOIUVZBYQRS-UHFFFAOYSA-N 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- WOPFYEBXNBBNKV-UHFFFAOYSA-N O[GeH2]C(C)C(O)=O Chemical class O[GeH2]C(C)C(O)=O WOPFYEBXNBBNKV-UHFFFAOYSA-N 0.000 description 1
- 108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HCXOEFUEXIXLCL-UHFFFAOYSA-N [Br].[Ge] Chemical compound [Br].[Ge] HCXOEFUEXIXLCL-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 229940125532 enzyme inhibitor Drugs 0.000 description 1
- 239000002532 enzyme inhibitor Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000007769 metal material Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 229940005483 opioid analgesics Drugs 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59-281002 | 1984-12-29 | ||
| JP28100284 | 1984-12-29 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33503592A Division JPH0699312B2 (ja) | 1984-12-29 | 1992-11-19 | オピオイド分解酵素阻害剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61267591A true JPS61267591A (ja) | 1986-11-27 |
| JPH0583558B2 JPH0583558B2 (enrdf_load_stackoverflow) | 1993-11-26 |
Family
ID=17632898
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP27175085A Granted JPS61267591A (ja) | 1984-12-29 | 1985-12-03 | 有機ゲルマニウム化合物 |
| JP33503592A Expired - Lifetime JPH0699312B2 (ja) | 1984-12-29 | 1992-11-19 | オピオイド分解酵素阻害剤 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP33503592A Expired - Lifetime JPH0699312B2 (ja) | 1984-12-29 | 1992-11-19 | オピオイド分解酵素阻害剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (2) | JPS61267591A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4002651A1 (de) * | 1989-01-30 | 1990-08-02 | Asai Germanium Res Inst | Organogermaniumverbindungen, verfahren zum herstellen derselben und mittel zum inhibieren der aktivitaet eines opioidpeptiddegradierenden enzyms |
-
1985
- 1985-12-03 JP JP27175085A patent/JPS61267591A/ja active Granted
-
1992
- 1992-11-19 JP JP33503592A patent/JPH0699312B2/ja not_active Expired - Lifetime
Non-Patent Citations (2)
| Title |
|---|
| CHEMICAL ABSTRACTS=1972 * |
| J.HETEROCYCL.CHEM=1974 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4002651A1 (de) * | 1989-01-30 | 1990-08-02 | Asai Germanium Res Inst | Organogermaniumverbindungen, verfahren zum herstellen derselben und mittel zum inhibieren der aktivitaet eines opioidpeptiddegradierenden enzyms |
| FR2642426A1 (fr) * | 1989-01-30 | 1990-08-03 | Asai Germanium Res Inst | Compose d'organogermanium, procedes pour leur fabrication et agent inhibiteur des enzymes de degradation des peptides opioides |
| US5041577A (en) * | 1989-01-30 | 1991-08-20 | Asai Germanium Research Institute Co., Ltd. | Organogermanium compounds, processes for producing the same, and agent for inhibiting the activity of opioid peptide-degrading enzyme |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH05238935A (ja) | 1993-09-17 |
| JPH0699312B2 (ja) | 1994-12-07 |
| JPH0583558B2 (enrdf_load_stackoverflow) | 1993-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |