ZA200200341B - Substituted isoquinoline derivatives and their use as anticonvulsants. - Google Patents
Substituted isoquinoline derivatives and their use as anticonvulsants. Download PDFInfo
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- ZA200200341B ZA200200341B ZA200200341A ZA200200341A ZA200200341B ZA 200200341 B ZA200200341 B ZA 200200341B ZA 200200341 A ZA200200341 A ZA 200200341A ZA 200200341 A ZA200200341 A ZA 200200341A ZA 200200341 B ZA200200341 B ZA 200200341B
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- ZA
- South Africa
- Prior art keywords
- disorders
- chloro
- compound
- tetrahydroisoquinolin
- disease
- Prior art date
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- 239000001961 anticonvulsive agent Substances 0.000 title claims description 14
- 229940125681 anticonvulsant agent Drugs 0.000 title description 3
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 104
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 208000035475 disorder Diseases 0.000 claims description 19
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 16
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 16
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 16
- 201000006417 multiple sclerosis Diseases 0.000 claims description 16
- 230000001537 neural effect Effects 0.000 claims description 16
- 208000004296 neuralgia Diseases 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 8
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 238000011321 prophylaxis Methods 0.000 claims description 7
- 230000009529 traumatic brain injury Effects 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- QLVXLDYLQRPQFH-UHFFFAOYSA-N 3-acetyl-n-(5,8-dichloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-propan-2-yloxybenzamide Chemical compound C1=C(C(C)=O)C(OC(C)C)=CC=C1C(=O)NC1=CC(Cl)=C(CCNC2)C2=C1Cl QLVXLDYLQRPQFH-UHFFFAOYSA-N 0.000 claims description 4
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- 150000001557 benzodiazepines Chemical class 0.000 claims 3
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
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- 239000000203 mixture Substances 0.000 description 29
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
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- 125000000217 alkyl group Chemical group 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
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- 238000001704 evaporation Methods 0.000 description 7
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
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- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
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- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
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- 125000001424 substituent group Chemical group 0.000 description 4
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- GPVDHNVGGIAOQT-UHFFFAOYSA-N 2,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 2
- CSFDQFSRAYXLLC-UHFFFAOYSA-N 3-acetyl-n-(5,8-dichloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-ethoxybenzamide Chemical compound C1=C(C(C)=O)C(OCC)=CC=C1C(=O)NC1=CC(Cl)=C(CCNC2)C2=C1Cl CSFDQFSRAYXLLC-UHFFFAOYSA-N 0.000 description 2
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- SJSINRIOAOMGCK-UHFFFAOYSA-N 3-bromo-n-(5-chloro-1,2,3,4-tetrahydroisoquinolin-7-yl)-4-methoxybenzamide Chemical compound C1=C(Br)C(OC)=CC=C1C(=O)NC1=CC(Cl)=C(CCNC2)C2=C1 SJSINRIOAOMGCK-UHFFFAOYSA-N 0.000 description 2
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9915589.7A GB9915589D0 (en) | 1999-07-02 | 1999-07-02 | Novel compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200200341B true ZA200200341B (en) | 2004-01-28 |
Family
ID=10856577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200200341A ZA200200341B (en) | 1999-07-02 | 2002-01-15 | Substituted isoquinoline derivatives and their use as anticonvulsants. |
Country Status (30)
| Country | Link |
|---|---|
| US (3) | US6492388B1 (da) |
| EP (2) | EP1367055B1 (da) |
| JP (2) | JP4108977B2 (da) |
| KR (1) | KR20020016879A (da) |
| CN (1) | CN1192022C (da) |
| AR (1) | AR029375A1 (da) |
| AT (2) | ATE260259T1 (da) |
| AU (1) | AU762716B2 (da) |
| BR (1) | BR0011862A (da) |
| CA (2) | CA2376495A1 (da) |
| CO (1) | CO5200763A1 (da) |
| CY (1) | CY1105373T1 (da) |
| CZ (1) | CZ20014721A3 (da) |
| DE (2) | DE60008539T2 (da) |
| DK (2) | DK1367055T3 (da) |
| ES (2) | ES2251665T3 (da) |
| GB (1) | GB9915589D0 (da) |
| GC (1) | GC0000195A (da) |
| HK (2) | HK1062436A1 (da) |
| HU (1) | HUP0203210A3 (da) |
| IL (1) | IL147103A0 (da) |
| MX (1) | MXPA02000064A (da) |
| MY (1) | MY123639A (da) |
| NO (2) | NO20016273D0 (da) |
| NZ (2) | NZ516130A (da) |
| PL (1) | PL355845A1 (da) |
| PT (1) | PT1200409E (da) |
| SI (2) | SI1367055T1 (da) |
| WO (1) | WO2001002366A2 (da) |
| ZA (1) | ZA200200341B (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20010016657A1 (en) * | 1997-03-18 | 2001-08-23 | Smithkline Beecham P.L.C. | Substituted isoquinoline derivatives and their use as anticonvulsants |
| GB9915589D0 (en) * | 1999-07-02 | 1999-09-01 | Smithkline Beecham Plc | Novel compounds |
| CN100341163C (zh) * | 2004-03-29 | 2007-10-03 | 宏齐科技股份有限公司 | 白光发光二极管单元 |
| GB0518237D0 (en) * | 2005-09-07 | 2005-10-19 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| EP2927215A1 (en) | 2014-04-03 | 2015-10-07 | Farma-Derma S.R.L. | Copper chelators |
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-
1999
- 1999-07-02 GB GBGB9915589.7A patent/GB9915589D0/en not_active Ceased
-
2000
- 2000-06-29 AT AT00942223T patent/ATE260259T1/de not_active IP Right Cessation
- 2000-06-29 ES ES03076336T patent/ES2251665T3/es not_active Expired - Lifetime
- 2000-06-29 PL PL00355845A patent/PL355845A1/xx not_active Application Discontinuation
- 2000-06-29 PT PT00942223T patent/PT1200409E/pt unknown
- 2000-06-29 DK DK03076336T patent/DK1367055T3/da active
- 2000-06-29 CZ CZ20014721A patent/CZ20014721A3/cs unknown
- 2000-06-29 HU HU0203210A patent/HUP0203210A3/hu unknown
- 2000-06-29 NZ NZ516130A patent/NZ516130A/en unknown
- 2000-06-29 MX MXPA02000064A patent/MXPA02000064A/es active IP Right Grant
- 2000-06-29 DE DE60008539T patent/DE60008539T2/de not_active Expired - Lifetime
- 2000-06-29 KR KR1020017016975A patent/KR20020016879A/ko not_active Application Discontinuation
- 2000-06-29 EP EP03076336A patent/EP1367055B1/en not_active Expired - Lifetime
- 2000-06-29 EP EP00942223A patent/EP1200409B1/en not_active Expired - Lifetime
- 2000-06-29 CA CA002376495A patent/CA2376495A1/en not_active Abandoned
- 2000-06-29 JP JP2001507806A patent/JP4108977B2/ja not_active Expired - Fee Related
- 2000-06-29 IL IL14710300A patent/IL147103A0/xx unknown
- 2000-06-29 DK DK00942223T patent/DK1200409T3/da active
- 2000-06-29 SI SI200030777T patent/SI1367055T1/sl unknown
- 2000-06-29 DE DE60023362T patent/DE60023362T2/de not_active Expired - Lifetime
- 2000-06-29 WO PCT/GB2000/002500 patent/WO2001002366A2/en active IP Right Grant
- 2000-06-29 US US10/019,104 patent/US6492388B1/en not_active Expired - Fee Related
- 2000-06-29 ES ES00942223T patent/ES2214287T3/es not_active Expired - Lifetime
- 2000-06-29 AU AU56928/00A patent/AU762716B2/en not_active Ceased
- 2000-06-29 SI SI200030374T patent/SI1200409T1/xx unknown
- 2000-06-29 AT AT03076336T patent/ATE307115T1/de not_active IP Right Cessation
- 2000-06-29 NZ NZ534600A patent/NZ534600A/xx unknown
- 2000-06-29 BR BR0011862-1A patent/BR0011862A/pt not_active IP Right Cessation
- 2000-06-29 CA CA002527931A patent/CA2527931A1/en not_active Abandoned
- 2000-06-29 CN CNB008124183A patent/CN1192022C/zh not_active Expired - Fee Related
- 2000-06-30 AR ARP000103344A patent/AR029375A1/es unknown
- 2000-06-30 CO CO00049344A patent/CO5200763A1/es not_active Application Discontinuation
- 2000-06-30 MY MYPI20003014 patent/MY123639A/en unknown
- 2000-07-02 GC GCP2000747 patent/GC0000195A/en active
-
2001
- 2001-12-20 NO NO20016273A patent/NO20016273D0/no not_active Application Discontinuation
-
2002
- 2002-01-15 ZA ZA200200341A patent/ZA200200341B/en unknown
- 2002-09-11 US US10/241,621 patent/US6770657B2/en not_active Expired - Fee Related
- 2002-09-27 HK HK04103853A patent/HK1062436A1/xx not_active IP Right Cessation
- 2002-09-27 HK HK02107175.0A patent/HK1047090B/zh unknown
-
2004
- 2004-01-12 US US10/755,748 patent/US7105536B2/en not_active Expired - Fee Related
-
2006
- 2006-01-10 CY CY20061100021T patent/CY1105373T1/el unknown
- 2006-03-07 NO NO20061099A patent/NO20061099L/no not_active Application Discontinuation
-
2007
- 2007-02-28 JP JP2007049789A patent/JP2007145862A/ja not_active Withdrawn
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