SK283621B6 - Deriváty 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridínu, spôsob ich prípravy, farmaceutické kompozície obsahujúce tieto deriváty a ich použitie na výrobu liečiva - Google Patents
Deriváty 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridínu, spôsob ich prípravy, farmaceutické kompozície obsahujúce tieto deriváty a ich použitie na výrobu liečiva Download PDFInfo
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- SK283621B6 SK283621B6 SK287-99A SK28799A SK283621B6 SK 283621 B6 SK283621 B6 SK 283621B6 SK 28799 A SK28799 A SK 28799A SK 283621 B6 SK283621 B6 SK 283621B6
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- OGOWMVYFFWEWQT-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzofuro[3,2-c]pyridine Chemical class O1C2=CC=CC=C2C2=C1CCNC2 OGOWMVYFFWEWQT-UHFFFAOYSA-N 0.000 title claims description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 89
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 34
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 6
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 239000004480 active ingredient Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000005843 halogen group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 4
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 229910052731 fluorine Inorganic materials 0.000 claims 1
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- 125000001424 substituent group Chemical group 0.000 claims 1
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- BQOLKFJNJCOALF-UHFFFAOYSA-N piperidin-1-ium-4,4-diol;chloride Chemical compound Cl.OC1(O)CCNCC1 BQOLKFJNJCOALF-UHFFFAOYSA-N 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
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- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
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- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
- ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
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- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
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- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97201045 | 1997-04-08 | ||
| PCT/EP1998/002136 WO1998045297A1 (en) | 1997-04-08 | 1998-04-02 | 1,2,3,4-TETRAHYDRO-BENZOFURO[3,2-c]PYRIDINE DERIVATIVES__ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK28799A3 SK28799A3 (en) | 2001-03-12 |
| SK283621B6 true SK283621B6 (sk) | 2003-10-07 |
Family
ID=8228191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK287-99A SK283621B6 (sk) | 1997-04-08 | 1998-04-02 | Deriváty 1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridínu, spôsob ich prípravy, farmaceutické kompozície obsahujúce tieto deriváty a ich použitie na výrobu liečiva |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6156757A (ja) |
| EP (1) | EP1019408B1 (ja) |
| JP (1) | JP3287577B2 (ja) |
| KR (1) | KR100315975B1 (ja) |
| CN (1) | CN1097053C (ja) |
| AP (1) | AP1138A (ja) |
| AR (1) | AR012576A1 (ja) |
| AT (1) | ATE270294T1 (ja) |
| AU (1) | AU727599B2 (ja) |
| BG (1) | BG63848B1 (ja) |
| BR (1) | BR9806263A (ja) |
| CA (1) | CA2264598C (ja) |
| CZ (1) | CZ290008B6 (ja) |
| DE (1) | DE69824872T2 (ja) |
| EE (1) | EE03691B1 (ja) |
| ES (1) | ES2224391T3 (ja) |
| GE (1) | GEP20022823B (ja) |
| HU (1) | HUP0003624A3 (ja) |
| ID (1) | ID22131A (ja) |
| IL (1) | IL128701A0 (ja) |
| MY (1) | MY120033A (ja) |
| NO (1) | NO322826B1 (ja) |
| NZ (1) | NZ334501A (ja) |
| PL (1) | PL189549B1 (ja) |
| RU (1) | RU2198175C2 (ja) |
| SK (1) | SK283621B6 (ja) |
| TR (1) | TR199900644T2 (ja) |
| TW (1) | TW589315B (ja) |
| UA (1) | UA52681C2 (ja) |
| WO (1) | WO1998045297A1 (ja) |
| ZA (1) | ZA982969B (ja) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA52681C2 (uk) * | 1997-04-08 | 2003-01-15 | Янссен Фармацевтика Н.В. | Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі |
| UA70334C2 (en) | 1998-10-06 | 2004-10-15 | Janssen Pharmaceutica N V Jans | BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS |
| KR20010071844A (ko) | 1998-10-06 | 2001-07-31 | 디르크 반테 | 의약으로서의 트리사이클릭 δ3-피페리딘 |
| SK285560B6 (sk) * | 1998-12-21 | 2007-03-01 | Janssen Pharmaceutica N. V. | Benzisoxazoly a fenoly ako alfa2-antagonisty, spôsob ich prípravy a farmaceutický prostriedok |
| CA2451606A1 (en) | 2001-07-05 | 2003-01-16 | Pharmacia & Upjohn Company | (hetero) aryl substituted benzofurans as 5-ht ligands |
| ATE521593T1 (de) * | 2002-04-03 | 2011-09-15 | Orion Corp | Verwendung eines alfa2-adrenorezeptorantagonisten bei mit dem zns zusammenhängenden erkrankungen |
| NZ539211A (en) * | 2002-10-04 | 2008-05-30 | Prana Biotechnology Ltd | Neurologically-active compounds |
| MXPA06011777A (es) | 2004-04-12 | 2007-01-16 | Taisho Pharma Co Ltd | Compuesto de amina ciclico. |
| US8470859B2 (en) * | 2006-10-23 | 2013-06-25 | Takeda Pharmaceutical Company Limited | Iminopyridine derivative and use thereof |
| MX2010011652A (es) * | 2008-04-23 | 2010-12-06 | Takeda Pharmaceutical | Derivados de iminopiridina y uso de los mismos. |
| US8481569B2 (en) * | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| US8575186B2 (en) * | 2009-10-05 | 2013-11-05 | Albany Molecular Research, Inc. | Epiminocycloalkyl[b] indole derivatives as serotonin sub-type 6 (5-HT6) modulators and uses thereof |
| US9067949B2 (en) | 2011-01-19 | 2015-06-30 | Albany Molecular Research, Inc. | Benzofuro[3,2-c] pyridines and related analogs as serotonin sub-type 6 (5-HT6) modulators for the treatment of obesity, metabolic syndrome, cognition and schizophrenia |
| GB201704325D0 (en) * | 2017-03-17 | 2017-05-03 | Argonaut Therapeutics Ltd | Compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2570701B1 (fr) * | 1984-09-27 | 1987-05-22 | Synthelabo | Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique |
| US4686226A (en) * | 1985-09-03 | 1987-08-11 | Merck & Co., Inc. | Substituted benzo[b]furo- and benzo[b]thieno quinolizines |
| US4985422A (en) * | 1988-04-27 | 1991-01-15 | Glaxo Group Limited | Lactam derivatives |
| UA52681C2 (uk) * | 1997-04-08 | 2003-01-15 | Янссен Фармацевтика Н.В. | Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі |
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1998
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100402 |