JPH0460472B2 - - Google Patents
Info
- Publication number
- JPH0460472B2 JPH0460472B2 JP26705684A JP26705684A JPH0460472B2 JP H0460472 B2 JPH0460472 B2 JP H0460472B2 JP 26705684 A JP26705684 A JP 26705684A JP 26705684 A JP26705684 A JP 26705684A JP H0460472 B2 JPH0460472 B2 JP H0460472B2
- Authority
- JP
- Japan
- Prior art keywords
- camptothecin
- salt
- formula
- tetraalkylammonium
- present
- 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
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 29
- 229940127093 camptothecin Drugs 0.000 claims description 29
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 29
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 12
- -1 camptothecin tetraalkylammonium salt Chemical class 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000005185 salting out Methods 0.000 claims description 3
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000759905 Camptotheca acuminata Species 0.000 description 1
- 239000003390 Chinese drug Substances 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000001668 nucleic acid synthesis Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical class CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 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 |
|---|---|---|---|
| JP26705684A JPS61145184A (ja) | 1984-12-18 | 1984-12-18 | カンプトテシン・テトラアルキルアンモニウム塩およびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26705684A JPS61145184A (ja) | 1984-12-18 | 1984-12-18 | カンプトテシン・テトラアルキルアンモニウム塩およびその製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61145184A JPS61145184A (ja) | 1986-07-02 |
| JPH0460472B2 true JPH0460472B2 (ko) | 1992-09-28 |
Family
ID=17439419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26705684A Granted JPS61145184A (ja) | 1984-12-18 | 1984-12-18 | カンプトテシン・テトラアルキルアンモニウム塩およびその製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61145184A (ko) |
-
1984
- 1984-12-18 JP JP26705684A patent/JPS61145184A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61145184A (ja) | 1986-07-02 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2366106C2 (de) | 2-Amino-6,7-dimethoxy-4-(methoxysubstituierte-lÄ3»4-tetrahydroisochinolin-2-yl)-chinazolinderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| JPS6247195B2 (ko) | ||
| GB2056973A (en) | Camptothecin derivatives useful as antitumour agents | |
| CN102964349A (zh) | 苯并二氮杂*衍生物的托西酸盐及其多晶型、它们的制备方法和用途 | |
| JPH0434999B2 (ko) | ||
| WO1991016337A1 (en) | S-(lower fatty acid)-substituted glutathione derivative | |
| JP2000511556A (ja) | ２０（ｓ）―カンプトテシンの新規な水溶性ｃ―環類似体 | |
| CN111423438B (zh) | 具有抗肿瘤活性的Eudistomins Y类衍生物及其制备方法和应用 | |
| CN111635449B (zh) | 一种羽扇豆醇吡啶季铵盐衍生物及其制备方法与应用 | |
| WO2022017317A1 (zh) | 一种规模化合成河豚毒素的方法 | |
| JPH0160471B2 (ko) | ||
| CN108864089B (zh) | 一种吲哚并吡啶酮药物分子及其制备方法和应用 | |
| CN102241668B (zh) | S-奥美拉唑盐 | |
| CN111362998A (zh) | 氮杂20(r)-人参二醇衍生物及其抗肿瘤应用 | |
| JPH045289A (ja) | アミド化合物 | |
| JPH0460472B2 (ko) | ||
| IL25315A (en) | O-(2-guanidino-ethyl)-oximes | |
| JP3009716B2 (ja) | 新規なカンプトテシン誘導体 | |
| KR950005737B1 (ko) | 징코라이드 혼합물로부터 단성분의 분리방법 | |
| CA1296735C (en) | Platinum(ii) complexes of 2,3-dimercapto-2-butene- dinitrilate(2-)-s,s' derivatives and process for their production | |
| EP0062068B1 (en) | N-phthalidyl-5-fluorouracil derivatives | |
| WO1993020042A1 (en) | Process and intermediate for the purification of oxytetracycline | |
| JPH0370700B2 (ko) | ||
| US4341773A (en) | 2,4-Diamino-5-sulfamoylbenzene sulfonic acids and process for their manufacture | |
| KR100917593B1 (ko) | 덱시부프로펜염의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |