CN102267998B - 新型抗寄生虫吡嗪异喹啉衍生物 - Google Patents
新型抗寄生虫吡嗪异喹啉衍生物 Download PDFInfo
- Publication number
- CN102267998B CN102267998B CN201110154047.XA CN201110154047A CN102267998B CN 102267998 B CN102267998 B CN 102267998B CN 201110154047 A CN201110154047 A CN 201110154047A CN 102267998 B CN102267998 B CN 102267998B
- Authority
- CN
- China
- Prior art keywords
- isoquinoline derivative
- pyrazine
- schistosomiasis
- parasitic
- 1mmol
- 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 - Fee Related
Links
- GPBRIMOJKVDGLP-UHFFFAOYSA-N isoquinoline;pyrazine Chemical class C1=CN=CC=N1.C1=NC=CC2=CC=CC=C21 GPBRIMOJKVDGLP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 230000002141 anti-parasite Effects 0.000 title description 2
- 239000003096 antiparasitic agent Substances 0.000 title description 2
- 239000003814 drug Substances 0.000 claims abstract description 11
- 229940079593 drug Drugs 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 241000242677 Schistosoma japonicum Species 0.000 claims abstract description 6
- 230000002147 killing effect Effects 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000004480 active ingredient Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 3
- 201000004409 schistosomiasis Diseases 0.000 description 15
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 6
- 238000003760 magnetic stirring Methods 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 208000030852 Parasitic disease Diseases 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 241001327965 Clonorchis sinensis Species 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 206010033794 paragonimiasis Diseases 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000242678 Schistosoma Species 0.000 description 2
- 238000012258 culturing Methods 0.000 description 2
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- -1 ketone compound Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960002957 praziquantel Drugs 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- RYCFVCRCAQQRQI-UHFFFAOYSA-N O=C(C1CCCC1)N(CC1N2Cc3ccccc13)CC2=O Chemical compound O=C(C1CCCC1)N(CC1N2Cc3ccccc13)CC2=O RYCFVCRCAQQRQI-UHFFFAOYSA-N 0.000 description 1
- RBTHOQPJZQFUPO-UHFFFAOYSA-N O=C(C1CCCCC1)N(CC1)C(c2ccccc2CC2)N2C1=O Chemical compound O=C(C1CCCCC1)N(CC1)C(c2ccccc2CC2)N2C1=O RBTHOQPJZQFUPO-UHFFFAOYSA-N 0.000 description 1
- NTHWGLTXWCGVOW-UHFFFAOYSA-N O=C(CCNC1)N2C1c1ccccc1CC2 Chemical compound O=C(CCNC1)N2C1c1ccccc1CC2 NTHWGLTXWCGVOW-UHFFFAOYSA-N 0.000 description 1
- BOESOANWDKJAPO-UHFFFAOYSA-N O=C(CNC1)N(C2)C1c1c2cccc1 Chemical compound O=C(CNC1)N(C2)C1c1c2cccc1 BOESOANWDKJAPO-UHFFFAOYSA-N 0.000 description 1
- 241000565675 Oncomelania Species 0.000 description 1
- 241000242680 Schistosoma mansoni Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000242541 Trematoda Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000006186 oral dosage form 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
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000007910 systemic administration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 206010048282 zoonosis Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
化合物 | 虫数 | 死亡率等级 | 化合物 | 虫数 | 死亡率等级 |
1 | 20 | A | 35 | 20 | A |
4 | 20 | A | 37 | 20 | A |
7 | 20 | A | 40 | 20 | A |
13 | 20 | A | 43 | 20 | A |
18 | 20 | A | 46 | 20 | A |
19 | 20 | A | 50 | 20 | A |
21 | 20 | A | 54 | 20 | A |
22 | 20 | A | 57 | 20 | A |
24 | 20 | A | 62 | 20 | A |
28 | 20 | A | 64 | 20 | A |
29 | 20 | A | 66 | 20 | A |
30 | 20 | A | 67 | 20 | A |
34 | 20 | A | 69 | 20 | A |
Claims (4)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110154047.XA CN102267998B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117838.3A CN104788457B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117197.1A CN104844606B (zh) | 2011-05-31 | 2011-05-31 | 抗寄生虫吡嗪异喹啉衍生物 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201110154047.XA CN102267998B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201510117838.3A Division CN104788457B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117197.1A Division CN104844606B (zh) | 2011-05-31 | 2011-05-31 | 抗寄生虫吡嗪异喹啉衍生物 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN102267998A CN102267998A (zh) | 2011-12-07 |
CN102267998B true CN102267998B (zh) | 2015-05-13 |
Family
ID=45050475
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
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CN201110154047.XA Expired - Fee Related CN102267998B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117838.3A Expired - Fee Related CN104788457B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117197.1A Expired - Fee Related CN104844606B (zh) | 2011-05-31 | 2011-05-31 | 抗寄生虫吡嗪异喹啉衍生物 |
Family Applications After (2)
Application Number | Title | Priority Date | Filing Date |
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CN201510117838.3A Expired - Fee Related CN104788457B (zh) | 2011-05-31 | 2011-05-31 | 新型抗寄生虫吡嗪异喹啉衍生物 |
CN201510117197.1A Expired - Fee Related CN104844606B (zh) | 2011-05-31 | 2011-05-31 | 抗寄生虫吡嗪异喹啉衍生物 |
Country Status (1)
Country | Link |
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CN (3) | CN102267998B (zh) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102321088A (zh) * | 2011-08-03 | 2012-01-18 | 威海秀水药物研发有限公司 | 一种新型抗血吸虫化合物 |
CN113754666A (zh) * | 2021-09-07 | 2021-12-07 | 凯美克(上海)医药科技有限公司 | 一种苯并吡嗪类化合物及其合成方法 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4661489A (en) * | 1983-07-16 | 1987-04-28 | Beecham Group P.L.C. | Benzazepines, and their use as anthelminthics |
DE3619030A1 (de) * | 1986-06-06 | 1987-12-10 | Bayer Ag | Topisch anwendbare zubereitungen |
CN1683346A (zh) * | 2005-03-01 | 2005-10-19 | 江苏工业学院 | 吡喹酮合成工艺 |
-
2011
- 2011-05-31 CN CN201110154047.XA patent/CN102267998B/zh not_active Expired - Fee Related
- 2011-05-31 CN CN201510117838.3A patent/CN104788457B/zh not_active Expired - Fee Related
- 2011-05-31 CN CN201510117197.1A patent/CN104844606B/zh not_active Expired - Fee Related
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4661489A (en) * | 1983-07-16 | 1987-04-28 | Beecham Group P.L.C. | Benzazepines, and their use as anthelminthics |
DE3619030A1 (de) * | 1986-06-06 | 1987-12-10 | Bayer Ag | Topisch anwendbare zubereitungen |
CN1683346A (zh) * | 2005-03-01 | 2005-10-19 | 江苏工业学院 | 吡喹酮合成工艺 |
Non-Patent Citations (1)
Title |
---|
胡玉琴,等.血吸虫病化学预防药物4H-吡嗪并〔2, 1-a〕异喹啉衍生物的合成.《中国药物化学杂志》.1997,第7卷(第1期),第38页合成路线. * |
Also Published As
Publication number | Publication date |
---|---|
CN104788457A (zh) | 2015-07-22 |
CN104844606B (zh) | 2017-03-01 |
CN104788457B (zh) | 2017-08-25 |
CN102267998A (zh) | 2011-12-07 |
CN104844606A (zh) | 2015-08-19 |
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ASS | Succession or assignment of patent right |
Owner name: SHANDONG UNIVERSITY (WEIHAI) Free format text: FORMER OWNER: SUN DEQUN Effective date: 20150710 |
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Effective date of registration: 20150710 Address after: 264209 Weihai Cultural Road West, Shandong, No. 180 Patentee after: Shandong University, Weihai Address before: 264209 innovation building, hi tech Zone, Shandong, Weihai 507 Patentee before: Sun Dequn |
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