UA77462C2 - Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use - Google Patents
Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use Download PDFInfo
- Publication number
- UA77462C2 UA77462C2 UA20040604552A UA20040604552A UA77462C2 UA 77462 C2 UA77462 C2 UA 77462C2 UA 20040604552 A UA20040604552 A UA 20040604552A UA 20040604552 A UA20040604552 A UA 20040604552A UA 77462 C2 UA77462 C2 UA 77462C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methoxy
- morpholin
- isonicotinamide
- ylbenzothiazol
- lower alkyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical class CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims description 4
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- -1 or is acetidinyl Chemical group 0.000 claims abstract description 269
- 150000001875 compounds Chemical class 0.000 claims abstract description 206
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 173
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 23
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract description 22
- 108050000203 Adenosine receptors Proteins 0.000 claims abstract description 20
- 102000009346 Adenosine receptors Human genes 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 9
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 239000011570 nicotinamide Substances 0.000 claims description 20
- 229960003966 nicotinamide Drugs 0.000 claims description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 229940126601 medicinal product Drugs 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- GUPNYUPGXQRCBK-UHFFFAOYSA-N 2-methoxy-3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=2SC(C=3C(=CC=NC=3OC)C(N)=O)=NC=2C(OC)=CC=C1N1CCOCC1 GUPNYUPGXQRCBK-UHFFFAOYSA-N 0.000 claims description 3
- NOXLHSPLCBIZCO-UHFFFAOYSA-N 3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(2-morpholin-4-ylethoxy)pyridine-4-carboxamide Chemical compound COC1=CC=C(C2=C1N=C(S2)C1=C(C(=O)N)C=CN=C1OCCN1CCOCC1)N1CCOCC1 NOXLHSPLCBIZCO-UHFFFAOYSA-N 0.000 claims description 3
- BYYRQHYIVRESLW-UHFFFAOYSA-N 3-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)-2-(4-methyl-3-oxopiperazin-1-yl)pyridine-4-carboxamide Chemical compound C1=2SC(C=3C(=NC=CC=3C(N)=O)N3CC(=O)N(C)CC3)=NC=2C(OC)=CC=C1N1CCOCC1 BYYRQHYIVRESLW-UHFFFAOYSA-N 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 3
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 claims description 2
- VFQXVTODMYMSMJ-UHFFFAOYSA-N isonicotinamide Chemical compound NC(=O)C1=CC=NC=C1 VFQXVTODMYMSMJ-UHFFFAOYSA-N 0.000 claims 2
- KZGJMKPUSWSYIP-UHFFFAOYSA-N 2-(3-methoxyazetidin-1-yl)-n-(4-methoxy-7-morpholin-4-yl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1C(OC)CN1C1=CC(C(=O)NC=2SC3=C(N4CCOCC4)C=CC(OC)=C3N=2)=CC=N1 KZGJMKPUSWSYIP-UHFFFAOYSA-N 0.000 claims 1
- GWSRFTFDSCYSPL-UHFFFAOYSA-N 2-methoxy-n-(4-methoxy-7-phenyl-1,3-benzothiazol-2-yl)pyridine-4-carboxamide Chemical compound C1=NC(OC)=CC(C(=O)NC=2SC3=C(C=4C=CC=CC=4)C=CC(OC)=C3N=2)=C1 GWSRFTFDSCYSPL-UHFFFAOYSA-N 0.000 claims 1
- IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims 1
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- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical class CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Addiction (AREA)
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- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Immunology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01127312 | 2001-11-19 | ||
| PCT/EP2002/012562 WO2003043636A1 (en) | 2001-11-19 | 2002-11-11 | Nicotin-or isonicotin benzothiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA77462C2 true UA77462C2 (en) | 2006-12-15 |
Family
ID=8179263
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UA20040604552A UA77462C2 (en) | 2001-11-19 | 2002-11-11 | Nicotine derivatives of benzothiasol, method for production, pharmaceutical agent and use |
Country Status (38)
| Country | Link |
|---|---|
| US (1) | US6620811B2 (xx) |
| EP (1) | EP1448198B1 (xx) |
| JP (1) | JP4226474B2 (xx) |
| KR (1) | KR100577110B1 (xx) |
| CN (1) | CN100546580C (xx) |
| AR (1) | AR039367A1 (xx) |
| AT (1) | ATE376831T1 (xx) |
| AU (1) | AU2002351955B2 (xx) |
| BR (1) | BR0214245A (xx) |
| CA (1) | CA2467552C (xx) |
| DE (1) | DE60223278T2 (xx) |
| DK (1) | DK1448198T3 (xx) |
| EA (1) | EA007502B1 (xx) |
| EC (1) | ECSP045109A (xx) |
| ES (1) | ES2294187T3 (xx) |
| GT (1) | GT200200232A (xx) |
| HR (1) | HRP20040396A2 (xx) |
| HU (1) | HUP0402161A3 (xx) |
| IL (2) | IL161623A0 (xx) |
| JO (1) | JO2290B1 (xx) |
| MA (1) | MA27083A1 (xx) |
| MX (1) | MXPA04004684A (xx) |
| MY (1) | MY126176A (xx) |
| NO (1) | NO20042576L (xx) |
| NZ (1) | NZ532802A (xx) |
| PA (1) | PA8558001A1 (xx) |
| PE (1) | PE20030713A1 (xx) |
| PL (1) | PL369517A1 (xx) |
| PT (1) | PT1448198E (xx) |
| RS (1) | RS39904A (xx) |
| RU (1) | RU2294933C2 (xx) |
| SI (1) | SI1448198T1 (xx) |
| TN (1) | TNSN04087A1 (xx) |
| TW (1) | TW200407134A (xx) |
| UA (1) | UA77462C2 (xx) |
| UY (1) | UY27542A1 (xx) |
| WO (1) | WO2003043636A1 (xx) |
| ZA (1) | ZA200403817B (xx) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ2003182A3 (cs) * | 2000-06-21 | 2003-06-18 | F. Hoffmann-La Roche Ag | Deriváty benzothiazolu |
| ES2357808T3 (es) * | 2001-06-07 | 2011-04-29 | Christine Dr. Sang | Tratamiento del dolor neuropático con antagonistas del receptor de n-metil-d-aspartato (nmda). |
| US6734179B2 (en) * | 2001-12-12 | 2004-05-11 | Hoffmann-La Roche Inc. | Benzothiazoles |
| US7390813B1 (en) | 2001-12-21 | 2008-06-24 | Xenon Pharmaceuticals Inc. | Pyridylpiperazines and aminonicotinamides and their use as therapeutic agents |
| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| US6872833B2 (en) * | 2003-04-14 | 2005-03-29 | Hoffmann-La Roche Inc. | Adenosine receptor ligands |
| AU2004259347B2 (en) * | 2003-07-23 | 2011-02-24 | Synta Pharmaceuticals, Corp. | Method for modulating calcium ion-release-activated calcium ion channels |
| WO2005011655A2 (en) | 2003-07-30 | 2005-02-10 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives and their use as therapeutic agents |
| JP2007505851A (ja) * | 2003-09-19 | 2007-03-15 | エフ．ホフマン−ラ ロシュ アーゲー | アデノシン受容体リガンドとしてのチアゾピリジン誘導体 |
| EP1677791A4 (en) * | 2003-10-31 | 2007-08-15 | Takeda Pharmaceutical | NITROGENIC CONDENSED HETEROCYCLIC COMPOUNDS |
| HUE025659T2 (en) | 2003-12-26 | 2016-04-28 | Kyowa Hakko Kirin Co Ltd | Thiazole derivatives |
| CN1997371A (zh) * | 2004-07-06 | 2007-07-11 | 泽农医药公司 | 烟酰胺衍生物及其作为治疗剂的用途 |
| JP5202946B2 (ja) * | 2004-07-22 | 2013-06-05 | エフ．ホフマン−ラ ロシュ アーゲー | ベンゾチアゾール誘導体 |
| KR100823799B1 (ko) * | 2004-07-22 | 2008-04-21 | 에프. 호프만-라 로슈 아게 | 벤조티아졸 유도체 |
| JP2008506735A (ja) | 2004-07-22 | 2008-03-06 | エフ．ホフマン−ラ ロシュ アーゲー | 置換されているベンゾチアゾール類 |
| CA2580787A1 (en) | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives for the treatment of diseases mediated by stearoyl-coa desaturase enzymes |
| EP1799668A1 (en) * | 2004-09-20 | 2007-06-27 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as mediators of stearoyl-coa desaturase |
| AR051294A1 (es) * | 2004-09-20 | 2007-01-03 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| US7592343B2 (en) * | 2004-09-20 | 2009-09-22 | Xenon Pharmaceuticals Inc. | Pyridazine-piperazine compounds and their use as stearoyl-CoA desaturase inhibitors |
| BRPI0515488A (pt) * | 2004-09-20 | 2008-07-29 | Xenon Pharmaceuticals Inc | derivados de heterocìclicos e seu uso como agentes terapêuticos |
| WO2006034341A2 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| JP4958786B2 (ja) * | 2004-09-20 | 2012-06-20 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 複素環誘導体および治療薬としてのそれらの使用 |
| US8071603B2 (en) * | 2004-09-20 | 2011-12-06 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
| WO2006048172A1 (en) * | 2004-11-05 | 2006-05-11 | F. Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| JP5066514B2 (ja) * | 2005-03-14 | 2012-11-07 | ハイ ポイント ファーマシューティカルズ，エルエルシー | ベンズアゾール誘導体、組成物及びβ−セクレターゼ阻害剤としての使用方法 |
| BRPI0611187A2 (pt) * | 2005-06-03 | 2010-08-24 | Xenon Pharmaceuticals Inc | derivados aminotiazàis como inibidores da estearoil-coa desaturase humana |
| WO2008059335A1 (en) * | 2006-11-13 | 2008-05-22 | Pfizer Products Inc. | Diaryl, dipyridinyl and aryl-pyridinyl derivatives and uses thereof |
| JP2012525389A (ja) | 2009-04-27 | 2012-10-22 | ハイ ポイント ファーマシューティカルズ，リミティド ライアビリティ カンパニー | 置換イソキノリン誘導体、医薬組成物、及びβ−セクレターゼ阻害剤としての使用方法 |
| TWI548411B (zh) | 2009-04-28 | 2016-09-11 | Kyowa Hakko Kirin Co Ltd | Exercise disorder treatment |
| UA113383C2 (xx) | 2009-09-02 | 2017-01-25 | Терапевтичний агент для лікування тривожних розладів | |
| UA110097C2 (uk) | 2009-09-02 | 2015-11-25 | Терапевтичний агент для лікування розладів настрою | |
| WO2011119465A1 (en) * | 2010-03-23 | 2011-09-29 | High Point Pharmaceuticals, Llc | Substituted imidazo[1,2-b]pyridazine derivatives, pharmaceutical compositions, and methods of use as beta-secretase inhibitors |
| JP5248585B2 (ja) * | 2010-12-15 | 2013-07-31 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | 治療薬としてのニコチンアミド誘導体およびそれらの使用 |
| DE102011005232A1 (de) | 2011-03-08 | 2012-09-13 | AristoCon GmbH & Co. KG | Adenosin und seine Derivate zur Verwendung in der Schmerztherapie |
| PL2903968T3 (pl) | 2012-10-02 | 2017-05-31 | Gilead Sciences, Inc. | Inhibitory demetylaz histonowych |
| WO2020103930A1 (zh) * | 2018-11-22 | 2020-05-28 | 上海科技大学 | 噻唑并环类化合物、其制备方法、中间体和应用 |
| DE102019110904B4 (de) * | 2019-04-26 | 2022-01-20 | Helmholtz-Zentrum Dresden - Rossendorf E. V. | N-(4-methoxy-7-morpholinobenzo[d]thiazol-2-yl)-acetamid-Derivate und deren Verwendung |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0113219B1 (en) | 1982-12-21 | 1987-11-19 | Johnsen & Jorgensen (Plastics) Limited | Dispensing container |
| FI91859C (fi) | 1987-06-17 | 1994-08-25 | Eisai Co Ltd | Analogiamenetelmä antiallergisena aineena aktiivisen bentsotiatsolijohdannaisen valmistamiseksi |
| CZ2003182A3 (cs) * | 2000-06-21 | 2003-06-18 | F. Hoffmann-La Roche Ag | Deriváty benzothiazolu |
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2002
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- 2002-11-11 WO PCT/EP2002/012562 patent/WO2003043636A1/en active IP Right Grant
- 2002-11-11 UA UA20040604552A patent/UA77462C2/uk unknown
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- 2002-11-11 SI SI200230637T patent/SI1448198T1/sl unknown
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- 2004-05-18 MA MA27681A patent/MA27083A1/fr unknown
- 2004-06-18 NO NO20042576A patent/NO20042576L/no not_active Application Discontinuation
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