BG63848B1 - 1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни - Google Patents
1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни Download PDFInfo
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- BG63848B1 BG63848B1 BG103213A BG10321399A BG63848B1 BG 63848 B1 BG63848 B1 BG 63848B1 BG 103213 A BG103213 A BG 103213A BG 10321399 A BG10321399 A BG 10321399A BG 63848 B1 BG63848 B1 BG 63848B1
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- Prior art keywords
- formula
- alkyl
- hydrogen
- radical
- compounds
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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 description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 96
- -1 nitro, hydroxy Chemical group 0.000 claims abstract description 49
- 239000000203 mixture Substances 0.000 claims abstract description 48
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 12
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 12
- 239000003814 drug Substances 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 125000001118 alkylidene group Chemical group 0.000 claims description 6
- 239000003937 drug carrier 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 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 238000007126 N-alkylation reaction Methods 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
- WGSMVIHKBMAWRN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzofuran Chemical compound C1C=CC=C2OCCC21 WGSMVIHKBMAWRN-UHFFFAOYSA-N 0.000 claims description 2
- ZYXHQIPQIKTEDI-UHFFFAOYSA-N 3-[2-(3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridin-2-yl)ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound O1C2=CC=CC=C2C(C2)=C1CCN2CCC(C1=O)=C(C)N=C2N1C=CC=C2 ZYXHQIPQIKTEDI-UHFFFAOYSA-N 0.000 claims description 2
- 208000020401 Depressive disease Diseases 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000005002 aryl methyl group Chemical group 0.000 claims description 2
- 125000000958 aryl methylene group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000008240 homogeneous mixture Substances 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 230000009466 transformation Effects 0.000 claims description 2
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- FPQNWBCHCMEAKI-UHFFFAOYSA-N 3-[2-(3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridin-2-yl)ethyl]-2,7-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound O1C2=CC=CC=C2C(C2)=C1CCN2CCC1=C(C)N=C2C=CC(C)=CN2C1=O FPQNWBCHCMEAKI-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 claims 1
- 230000008685 targeting Effects 0.000 claims 1
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- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- 229910002027 silica gel Inorganic materials 0.000 description 7
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002552 dosage form Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 6
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 6
- 229960001600 xylazine Drugs 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
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- 239000000706 filtrate Substances 0.000 description 5
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- 239000011734 sodium Substances 0.000 description 5
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- 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
- 239000000600 sorbitol Substances 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
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- A—HUMAN NECESSITIES
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P27/06—Antiglaucoma agents or miotics
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Reproductive Health (AREA)
- Psychiatry (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Gynecology & Obstetrics (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 |
|---|---|
| BG103213A BG103213A (en) | 2000-05-31 |
| BG63848B1 true BG63848B1 (bg) | 2003-03-31 |
Family
ID=8228191
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG103213A BG63848B1 (bg) | 1997-04-08 | 1999-02-25 | 1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US6156757A (cs) |
| EP (1) | EP1019408B1 (cs) |
| JP (1) | JP3287577B2 (cs) |
| KR (1) | KR100315975B1 (cs) |
| CN (1) | CN1097053C (cs) |
| AP (1) | AP1138A (cs) |
| AR (1) | AR012576A1 (cs) |
| AT (1) | ATE270294T1 (cs) |
| AU (1) | AU727599B2 (cs) |
| BG (1) | BG63848B1 (cs) |
| BR (1) | BR9806263A (cs) |
| CA (1) | CA2264598C (cs) |
| CZ (1) | CZ290008B6 (cs) |
| DE (1) | DE69824872T2 (cs) |
| EE (1) | EE03691B1 (cs) |
| ES (1) | ES2224391T3 (cs) |
| GE (1) | GEP20022823B (cs) |
| HU (1) | HUP0003624A3 (cs) |
| ID (1) | ID22131A (cs) |
| IL (1) | IL128701A0 (cs) |
| MY (1) | MY120033A (cs) |
| NO (1) | NO322826B1 (cs) |
| NZ (1) | NZ334501A (cs) |
| PL (1) | PL189549B1 (cs) |
| RU (1) | RU2198175C2 (cs) |
| SK (1) | SK283621B6 (cs) |
| TR (1) | TR199900644T2 (cs) |
| TW (1) | TW589315B (cs) |
| UA (1) | UA52681C2 (cs) |
| WO (1) | WO1998045297A1 (cs) |
| ZA (1) | ZA982969B (cs) |
Families Citing this family (15)
| 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 |
| RU2226194C2 (ru) * | 1998-10-06 | 2004-03-27 | Янссен Фармацевтика Н.В. | Трициклические δ3-пиперидины, способы их получения и фармацевтическая композиция на их основе |
| HUP0104812A3 (en) * | 1998-12-21 | 2003-12-29 | Janssen Pharmaceutica Nv | Benzisoxazoles and phenones as alpha2-antagonists, process for their preparation and medicaments containing them |
| WO2003004501A2 (en) * | 2001-07-05 | 2003-01-16 | Pharmacia & Upjohn Company | (hetero) aryl substituted benzofurans as 5-ht ligands |
| JP2005521728A (ja) * | 2002-04-03 | 2005-07-21 | オリオン コーポレーション | ＣＮＳ関連疾患のためのα２−アドレナリン受容体アンタゴニストの使用 |
| ES2440217T3 (es) * | 2002-10-04 | 2014-01-28 | Prana Biotechnology Limited | Compuestos neurológicamente activos |
| BRPI0509893A (pt) | 2004-04-12 | 2007-10-30 | Taisho Pharmaceutical Co Ltd | composto de amina cìclica |
| RU2409582C2 (ru) * | 2004-08-31 | 2011-01-20 | Глэксо Груп Лимитед | Конденсированные трициклические производные для лечения психотических расстройств |
| WO2008050732A1 (fr) * | 2006-10-23 | 2008-05-02 | Takeda Pharmaceutical Company Limited | Dérivé de l'iminopyridine et son utilisation |
| US20110039846A1 (en) * | 2008-04-23 | 2011-02-17 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| US8481569B2 (en) * | 2008-04-23 | 2013-07-09 | Takeda Pharmaceutical Company Limited | Iminopyridine derivatives and use thereof |
| WO2011044134A1 (en) * | 2009-10-05 | 2011-04-14 | Albany Molecular Research, Inc. | Epiminocycloalkyl(b)indole derivatives as serotonin sub-type 6 (5-ht6) modulators and uses thereof |
| WO2012099952A2 (en) * | 2011-01-19 | 2012-07-26 | 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 (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4688803A (en) * | 1984-06-25 | 1987-08-25 | Ollington Robert F | Casino game table and dice |
| 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 |
| RU2045529C1 (ru) * | 1988-04-26 | 1995-10-10 | Ниссан Кемикал Индастриз Лтд. | Способ получения мевалонолактоновых производных |
| US4985422A (en) * | 1988-04-27 | 1991-01-15 | Glaxo Group Limited | Lactam derivatives |
| DE4308451A1 (de) * | 1992-09-10 | 1994-04-14 | Bayer Ag | 3-Aryl-pyron-Derivate |
| 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
- 1998-02-04 UA UA99031180A patent/UA52681C2/uk unknown
- 1998-04-02 GE GEAP19985020A patent/GEP20022823B/en unknown
- 1998-04-02 RU RU99107290/04A patent/RU2198175C2/ru active
- 1998-04-02 AT AT98921458T patent/ATE270294T1/de not_active IP Right Cessation
- 1998-04-02 EE EEP199900114A patent/EE03691B1/xx not_active IP Right Cessation
- 1998-04-02 PL PL98332382A patent/PL189549B1/pl unknown
- 1998-04-02 KR KR1019997002086A patent/KR100315975B1/ko not_active Expired - Fee Related
- 1998-04-02 BR BR9806263-8A patent/BR9806263A/pt not_active Application Discontinuation
- 1998-04-02 IL IL12870198A patent/IL128701A0/xx not_active IP Right Cessation
- 1998-04-02 CN CN98801286A patent/CN1097053C/zh not_active Expired - Lifetime
- 1998-04-02 CA CA002264598A patent/CA2264598C/en not_active Expired - Lifetime
- 1998-04-02 HU HU0003624A patent/HUP0003624A3/hu unknown
- 1998-04-02 AP APAP/P/1999/001650A patent/AP1138A/en active
- 1998-04-02 TR TR1999/00644T patent/TR199900644T2/xx unknown
- 1998-04-02 SK SK287-99A patent/SK283621B6/sk not_active IP Right Cessation
- 1998-04-02 EP EP98921458A patent/EP1019408B1/en not_active Expired - Lifetime
- 1998-04-02 ES ES98921458T patent/ES2224391T3/es not_active Expired - Lifetime
- 1998-04-02 DE DE69824872T patent/DE69824872T2/de not_active Expired - Lifetime
- 1998-04-02 AU AU74307/98A patent/AU727599B2/en not_active Expired
- 1998-04-02 ID IDW990147D patent/ID22131A/id unknown
- 1998-04-02 NZ NZ334501A patent/NZ334501A/en unknown
- 1998-04-02 CZ CZ1999682A patent/CZ290008B6/cs not_active IP Right Cessation
- 1998-04-02 US US09/402,593 patent/US6156757A/en not_active Expired - Lifetime
- 1998-04-02 JP JP54240698A patent/JP3287577B2/ja not_active Expired - Fee Related
- 1998-04-02 WO PCT/EP1998/002136 patent/WO1998045297A1/en not_active Ceased
- 1998-04-03 MY MYPI98001502A patent/MY120033A/en unknown
- 1998-04-07 TW TW087105162A patent/TW589315B/zh not_active IP Right Cessation
- 1998-04-07 AR ARP980101598A patent/AR012576A1/es active IP Right Grant
- 1998-04-07 ZA ZA9802969A patent/ZA982969B/xx unknown
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1999
- 1999-02-23 NO NO19990859A patent/NO322826B1/no not_active IP Right Cessation
- 1999-02-25 BG BG103213A patent/BG63848B1/bg unknown
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