CN101676287A - 用作抗癫痫药的6-(取代苯氧基)-四唑并[5,1-a]酞嗪衍生物及其可药用盐 - Google Patents
用作抗癫痫药的6-(取代苯氧基)-四唑并[5,1-a]酞嗪衍生物及其可药用盐 Download PDFInfo
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- CN101676287A CN101676287A CN200810165734A CN200810165734A CN101676287A CN 101676287 A CN101676287 A CN 101676287A CN 200810165734 A CN200810165734 A CN 200810165734A CN 200810165734 A CN200810165734 A CN 200810165734A CN 101676287 A CN101676287 A CN 101676287A
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- tetrazolo
- phthalazines
- pharmaceutically acceptable
- compound
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- 150000003839 salts Chemical class 0.000 title claims abstract description 11
- -1 6-(substituted phenoxy)-tetrazolo[5,1-a] phthalazine Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000001961 anticonvulsive agent Substances 0.000 claims description 11
- 229960003965 antiepileptics Drugs 0.000 claims description 9
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- KADJHMQFWKPVKP-UHFFFAOYSA-N 6-(4-chlorophenoxy)tetrazolo[5,1-a]phthalazine Chemical class C1=CC(Cl)=CC=C1OC(C1=CC=CC=C11)=NN2C1=NN=N2 KADJHMQFWKPVKP-UHFFFAOYSA-N 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 238000007259 addition reaction Methods 0.000 abstract 2
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract 1
- 206010029350 Neurotoxicity Diseases 0.000 description 10
- 206010044221 Toxic encephalopathy Diseases 0.000 description 10
- 230000007135 neurotoxicity Effects 0.000 description 10
- 231100000228 neurotoxicity Toxicity 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940125904 compound 1 Drugs 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002082 anti-convulsion Effects 0.000 description 3
- 206010015037 epilepsy Diseases 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 2
- 238000011047 acute toxicity test Methods 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000003556 anti-epileptic effect Effects 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001037 epileptic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 1
- 206010003591 Ataxia Diseases 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000007972 injectable composition Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- FJPYVLNWWICYDW-UHFFFAOYSA-M sodium;5,5-diphenylimidazolidin-1-ide-2,4-dione Chemical class [Na+].O=C1[N-]C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FJPYVLNWWICYDW-UHFFFAOYSA-M 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 1
- 229960000604 valproic acid Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Claims (6)
Priority Applications (1)
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CN200810165734XA CN101676287B (zh) | 2008-09-19 | 2008-09-19 | 用作抗癫痫药的6-(取代苯氧基)-四唑并[5,1-a]酞嗪衍生物及其可药用盐 |
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CN200810165734XA CN101676287B (zh) | 2008-09-19 | 2008-09-19 | 用作抗癫痫药的6-(取代苯氧基)-四唑并[5,1-a]酞嗪衍生物及其可药用盐 |
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CN101676287A true CN101676287A (zh) | 2010-03-24 |
CN101676287B CN101676287B (zh) | 2012-05-23 |
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Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102824342A (zh) * | 2011-06-17 | 2012-12-19 | 全哲山 | 一类用作抗癫痫药的化合物及其可药用盐 |
CN102887910A (zh) * | 2012-08-27 | 2013-01-23 | 全哲山 | 用作抗癫痫药的7-烷氧基-[1,2,4]三唑并[3,4-b]苯并噻唑-3(2H)-酮衍生物及其制备方法 |
CN103214488A (zh) * | 2012-01-21 | 2013-07-24 | 内蒙古民族大学 | 喹啉酮衍生物和以该化合物为活性成份的药物组合物及其制备方法 |
CN103816133A (zh) * | 2014-02-25 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | 一种用于抗癫痫病药物的q808固体分散体及其制备方法 |
CN103819477A (zh) * | 2014-02-21 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | 一种6-(4-氯苯氧基)-四唑并[5,1-a]酞嗪的多晶型制备方法及其应用 |
CN105456269A (zh) * | 2015-12-03 | 2016-04-06 | 青岛市市立医院 | 一种治疗前列腺增生的药物组合物及其应用 |
-
2008
- 2008-09-19 CN CN200810165734XA patent/CN101676287B/zh active Active
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102824342A (zh) * | 2011-06-17 | 2012-12-19 | 全哲山 | 一类用作抗癫痫药的化合物及其可药用盐 |
CN103214488A (zh) * | 2012-01-21 | 2013-07-24 | 内蒙古民族大学 | 喹啉酮衍生物和以该化合物为活性成份的药物组合物及其制备方法 |
CN102887910A (zh) * | 2012-08-27 | 2013-01-23 | 全哲山 | 用作抗癫痫药的7-烷氧基-[1,2,4]三唑并[3,4-b]苯并噻唑-3(2H)-酮衍生物及其制备方法 |
CN102887910B (zh) * | 2012-08-27 | 2016-08-24 | 全哲山 | 用作抗癫痫药的7-烷氧基-[1,2,4]三唑并[3,4-b]苯并噻唑-3(2H)-酮衍生物及其制备方法 |
CN103819477A (zh) * | 2014-02-21 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | 一种6-(4-氯苯氧基)-四唑并[5,1-a]酞嗪的多晶型制备方法及其应用 |
WO2015123801A1 (zh) * | 2014-02-21 | 2015-08-27 | 吉林英联尚德科技开发有限公司 | 一种6-(4-氯苯氧基)-四唑并[5,1-a]酞嗪的多晶型制备方法及其应用 |
CN103816133A (zh) * | 2014-02-25 | 2014-05-28 | 吉林英联尚德科技开发有限公司 | 一种用于抗癫痫病药物的q808固体分散体及其制备方法 |
CN103816133B (zh) * | 2014-02-25 | 2016-07-06 | 吉林英联尚德科技开发有限公司 | 一种用于抗癫痫病药物的q808固体分散体及其制备方法 |
CN105456269A (zh) * | 2015-12-03 | 2016-04-06 | 青岛市市立医院 | 一种治疗前列腺增生的药物组合物及其应用 |
CN105456269B (zh) * | 2015-12-03 | 2018-12-25 | 青岛市市立医院 | 一种治疗前列腺增生的药物组合物及其应用 |
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CN101676287B (zh) | 2012-05-23 |
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Owner name: JILIN ACTIS SUNTECH TECHNOLOGY DEVELOPMENT CO., LT Free format text: FORMER OWNER: QUAN ZHESHAN Effective date: 20110805 |
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Free format text: CORRECT: ADDRESS; FROM: 133000 YANBIAN KOREAN AUTONOMOUS PREFECTURE, JILIN PROVINCE TO: 130033 CHANGCHUN, JILIN PROVINCE |
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Effective date of registration: 20110805 Address after: 130033 No. 1433, Zhanjiang Road, Changchun economic and Technological Development Zone, Jilin, China Applicant after: JILIN YINGLIANSHANGDE TECHNOLOGY DEVELOPMENT CO., LTD. Address before: Yanji City, Jilin province 133000 Station Street No. 121 Applicant before: Quan Zheshan |
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