JPS60152416A - 癌転移抑制剤 - Google Patents
癌転移抑制剤Info
- Publication number
- JPS60152416A JPS60152416A JP774984A JP774984A JPS60152416A JP S60152416 A JPS60152416 A JP S60152416A JP 774984 A JP774984 A JP 774984A JP 774984 A JP774984 A JP 774984A JP S60152416 A JPS60152416 A JP S60152416A
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- metastasis
- agent
- platelet aggregation
- compound
- 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
- 206010028980 Neoplasm Diseases 0.000 title claims abstract description 16
- 201000011510 cancer Diseases 0.000 title claims abstract description 14
- 206010027476 Metastases Diseases 0.000 title abstract description 16
- 230000009401 metastasis Effects 0.000 title abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 239000002257 antimetastatic agent Substances 0.000 claims description 3
- -1 7-(1-piperidinyl)-1,2,8,5-tetrahydroimidazo(2,1-b)quinazolin-2one Chemical compound 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 abstract description 16
- 150000001875 compounds Chemical class 0.000 abstract description 16
- 241001465754 Metazoa Species 0.000 abstract description 11
- 239000003814 drug Substances 0.000 abstract description 11
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 229940079593 drug Drugs 0.000 abstract description 10
- 208000010110 spontaneous platelet aggregation Diseases 0.000 abstract description 10
- 210000004072 lung Anatomy 0.000 abstract description 6
- 230000001394 metastastic effect Effects 0.000 abstract description 6
- 206010061289 metastatic neoplasm Diseases 0.000 abstract description 6
- 230000002401 inhibitory effect Effects 0.000 abstract description 5
- 238000002474 experimental method Methods 0.000 abstract description 4
- FVACZQHQBKPPMX-UHFFFAOYSA-N quinazolin-2-one Chemical compound C1=C[CH]C2=NC(=O)N=CC2=C1 FVACZQHQBKPPMX-UHFFFAOYSA-N 0.000 abstract description 3
- 102000008946 Fibrinogen Human genes 0.000 abstract description 2
- 108010049003 Fibrinogen Proteins 0.000 abstract description 2
- 208000007536 Thrombosis Diseases 0.000 abstract description 2
- 229940012952 fibrinogen Drugs 0.000 abstract description 2
- 210000001772 blood platelet Anatomy 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- MNVCNERGJZWWAO-UHFFFAOYSA-N 7-piperidin-1-yl-5,10-dihydro-3h-imidazo[2,1-b]quinazolin-2-one Chemical compound C=1C=C2NC3=NC(=O)CN3CC2=CC=1N1CCCCC1 MNVCNERGJZWWAO-UHFFFAOYSA-N 0.000 abstract 1
- 208000005189 Embolism Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000006285 cell suspension Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 241000699670 Mus sp. Species 0.000 description 5
- 208000010378 Pulmonary Embolism Diseases 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 238000011081 inoculation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 210000004623 platelet-rich plasma Anatomy 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 208000013210 hematogenous Diseases 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 210000003462 vein Anatomy 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 210000004881 tumor cell Anatomy 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XOOKHQUXRPYSNR-UHFFFAOYSA-N 2,4-dichloro-6-piperidin-1-ylquinazoline Chemical compound C1=CC2=NC(Cl)=NC(Cl)=C2C=C1N1CCCCC1 XOOKHQUXRPYSNR-UHFFFAOYSA-N 0.000 description 1
- PFVGLFKHQGRTRA-UHFFFAOYSA-N 2-amino-5-piperidin-1-ylbenzonitrile Chemical compound C1=C(C#N)C(N)=CC=C1N1CCCCC1 PFVGLFKHQGRTRA-UHFFFAOYSA-N 0.000 description 1
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical class NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 description 1
- HPWJUEZFOUOUEO-UHFFFAOYSA-N 5-chloro-2-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C#N HPWJUEZFOUOUEO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 102000016911 Deoxyribonucleases Human genes 0.000 description 1
- 108010053770 Deoxyribonucleases Proteins 0.000 description 1
- 206010062713 Haemorrhagic diathesis Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000019687 Lamb Nutrition 0.000 description 1
- 208000006552 Lewis Lung Carcinoma Diseases 0.000 description 1
- JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- QHNCOVDGEWMOAM-UHFFFAOYSA-N N=1C=NCC2=CC=CCC=12 Chemical compound N=1C=NCC2=CC=CCC=12 QHNCOVDGEWMOAM-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 230000006502 antiplatelets effects Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000008359 benzonitriles Chemical class 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000012503 blood component Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 229910001424 calcium ion Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003527 fibrinolytic agent Substances 0.000 description 1
- 230000003480 fibrinolytic effect Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000009545 invasion Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910001425 magnesium ion Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP774984A JPS60152416A (ja) | 1984-01-19 | 1984-01-19 | 癌転移抑制剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP774984A JPS60152416A (ja) | 1984-01-19 | 1984-01-19 | 癌転移抑制剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60152416A true JPS60152416A (ja) | 1985-08-10 |
| JPH0374206B2 JPH0374206B2 (enrdf_load_stackoverflow) | 1991-11-26 |
Family
ID=11674341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP774984A Granted JPS60152416A (ja) | 1984-01-19 | 1984-01-19 | 癌転移抑制剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60152416A (enrdf_load_stackoverflow) |
-
1984
- 1984-01-19 JP JP774984A patent/JPS60152416A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0374206B2 (enrdf_load_stackoverflow) | 1991-11-26 |
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