JP2007514790A5 - - Google Patents
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- Publication number
- JP2007514790A5 JP2007514790A5 JP2006545760A JP2006545760A JP2007514790A5 JP 2007514790 A5 JP2007514790 A5 JP 2007514790A5 JP 2006545760 A JP2006545760 A JP 2006545760A JP 2006545760 A JP2006545760 A JP 2006545760A JP 2007514790 A5 JP2007514790 A5 JP 2007514790A5
- Authority
- JP
- Japan
- Prior art keywords
- tetrazol
- alkyl
- fluoro
- compound
- fluoropyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 208000035475 disorder Diseases 0.000 claims 9
- 238000000034 method Methods 0.000 claims 8
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims 5
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims 5
- -1 chloro, bromo, iodo, methoxymethyl Chemical group 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- FBUHFQUZAYMTOM-UHFFFAOYSA-N pyridin-2-ylcyanamide Chemical compound N#CNC1=CC=CC=N1 FBUHFQUZAYMTOM-UHFFFAOYSA-N 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims 3
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- XUICYRFPJOHKGW-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(methoxymethyl)benzonitrile Chemical compound COCC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 XUICYRFPJOHKGW-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 235000010288 sodium nitrite Nutrition 0.000 claims 2
- 239000012453 solvate Substances 0.000 claims 2
- AQGCLHIWIZUYPV-UHFFFAOYSA-N 3-(difluoromethoxy)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound FC(F)OC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 AQGCLHIWIZUYPV-UHFFFAOYSA-N 0.000 claims 1
- RNUMNUGYLBCCEU-UHFFFAOYSA-N 3-(ethylamino)-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound CCNC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 RNUMNUGYLBCCEU-UHFFFAOYSA-N 0.000 claims 1
- GTANSZNHJARZLJ-UHFFFAOYSA-N 3-[2-(5-chloropyridin-2-yl)tetrazol-5-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(Cl)=CC=2)=C1 GTANSZNHJARZLJ-UHFFFAOYSA-N 0.000 claims 1
- SAWSSPISYVVUPP-UHFFFAOYSA-N 3-[5-(5-chloropyridin-2-yl)tetrazol-2-yl]-5-fluorobenzonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(Cl)=CC=2)=C1 SAWSSPISYVVUPP-UHFFFAOYSA-N 0.000 claims 1
- WQWFBZQKKNQGSY-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(2-methoxyethoxy)benzonitrile Chemical compound COCCOC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 WQWFBZQKKNQGSY-UHFFFAOYSA-N 0.000 claims 1
- UYRBZIYJANWFLG-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-(trifluoromethoxy)benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(OC(F)(F)F)C=2)C#N)N=N1 UYRBZIYJANWFLG-UHFFFAOYSA-N 0.000 claims 1
- NDUDAERNMBXBRF-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-iodobenzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(I)C=2)C#N)N=N1 NDUDAERNMBXBRF-UHFFFAOYSA-N 0.000 claims 1
- HVPQJXMCMHHZHI-UHFFFAOYSA-N 3-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]-5-methoxybenzonitrile Chemical compound COC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 HVPQJXMCMHHZHI-UHFFFAOYSA-N 0.000 claims 1
- TUVRMXKPGAJUGF-UHFFFAOYSA-N 3-amino-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound NC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 TUVRMXKPGAJUGF-UHFFFAOYSA-N 0.000 claims 1
- CKISQUUTFPIQAX-UHFFFAOYSA-N 3-fluoro-5-[2-(5-fluoropyridin-2-yl)tetrazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1N1N=C(C=2C=C(C=C(F)C=2)C#N)N=N1 CKISQUUTFPIQAX-UHFFFAOYSA-N 0.000 claims 1
- UQCQFXVIFGQFRL-UHFFFAOYSA-N 3-fluoro-5-[5-(5-fluoropyridin-2-yl)tetrazol-2-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NN(C=2C=C(C=C(F)C=2)C#N)N=N1 UQCQFXVIFGQFRL-UHFFFAOYSA-N 0.000 claims 1
- IFOXWHQFTSCNQB-UHFFFAOYSA-N 5-aminopyridine-2-carbonitrile Chemical group NC1=CC=C(C#N)N=C1 IFOXWHQFTSCNQB-UHFFFAOYSA-N 0.000 claims 1
- QJWNJNTZXKFBKG-UHFFFAOYSA-N 5-fluoro-2-[2-(3-fluoro-5-methoxyphenyl)tetrazol-5-yl]pyridine Chemical compound COC1=CC(F)=CC(N2N=C(N=N2)C=2N=CC(F)=CC=2)=C1 QJWNJNTZXKFBKG-UHFFFAOYSA-N 0.000 claims 1
- BHXHRMVSUUPOLX-UHFFFAOYSA-N 5-fluoropyridine-2-carbonitrile Chemical compound FC1=CC=C(C#N)N=C1 BHXHRMVSUUPOLX-UHFFFAOYSA-N 0.000 claims 1
- RFXRMGATCPIUGX-UHFFFAOYSA-N 6-[2-(3-cyano-5-fluorophenyl)tetrazol-5-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(N2N=C(N=N2)C=2N=CC(=CC=2)C#N)=C1 RFXRMGATCPIUGX-UHFFFAOYSA-N 0.000 claims 1
- WLBDEBUYJGERNR-UHFFFAOYSA-N 6-[5-(3-cyano-5-fluorophenyl)tetrazol-2-yl]pyridine-3-carbonitrile Chemical compound FC1=CC(C#N)=CC(C2=NN(N=N2)C=2N=CC(=CC=2)C#N)=C1 WLBDEBUYJGERNR-UHFFFAOYSA-N 0.000 claims 1
- 208000000094 Chronic Pain Diseases 0.000 claims 1
- 208000018522 Gastrointestinal disease Diseases 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 229910002651 NO3 Inorganic materials 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims 1
- 230000004913 activation Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000005298 acute pain Diseases 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000012295 chemical reaction liquid Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 208000010643 digestive system disease Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 208000018685 gastrointestinal system disease Diseases 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000020016 psychiatric disease Diseases 0.000 claims 1
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 102000005962 receptors Human genes 0.000 claims 1
- 108020003175 receptors Proteins 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53063303P | 2003-12-19 | 2003-12-19 | |
| PCT/US2004/041401 WO2005066155A1 (en) | 2003-12-19 | 2004-12-13 | 5-fluoro-, chloro- and cyano-pyridin-2-yl-tetrazoles as ligands of the metabotropic glutamate receptor-5 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007514790A JP2007514790A (ja) | 2007-06-07 |
| JP2007514790A5 true JP2007514790A5 (https=) | 2008-01-17 |
Family
ID=34748746
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006545760A Pending JP2007514790A (ja) | 2003-12-19 | 2004-12-13 | 代謝共役型グルタミン酸受容体−５のリガンドとしての５−フルオロ−、クロロ−、およびシアノ−ピリジン−２−イル−テトラゾール |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US20070255061A1 (https=) |
| EP (1) | EP1713791B1 (https=) |
| JP (1) | JP2007514790A (https=) |
| KR (1) | KR20060126993A (https=) |
| CN (1) | CN1906187A (https=) |
| AR (1) | AR046768A1 (https=) |
| AT (1) | ATE393767T1 (https=) |
| AU (1) | AU2004312342A1 (https=) |
| BR (1) | BRPI0417308A (https=) |
| CA (1) | CA2548039A1 (https=) |
| DE (1) | DE602004013469T9 (https=) |
| ES (1) | ES2303969T3 (https=) |
| IL (1) | IL175909A0 (https=) |
| MX (1) | MXPA06006674A (https=) |
| NO (1) | NO20062533L (https=) |
| RU (1) | RU2006118021A (https=) |
| TW (1) | TW200524602A (https=) |
| UY (1) | UY28685A1 (https=) |
| WO (1) | WO2005066155A1 (https=) |
| ZA (1) | ZA200604681B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7723362B2 (en) * | 2004-01-08 | 2010-05-25 | Syngenta Crop Protection, Inc. | Pesticidal heterocyclic dihaloallyl compounds |
| AR058807A1 (es) | 2005-09-29 | 2008-02-27 | Astrazeneca Ab | 5-(fenilisoxazoletoxi)-triazol-3-il piridinas sustituidas, para el tratamiento de trastornos mediados por el receptor mglur5 |
| US8349852B2 (en) | 2009-01-13 | 2013-01-08 | Novartis Ag | Quinazolinone derivatives useful as vanilloid antagonists |
| US20120095056A1 (en) * | 2009-03-19 | 2012-04-19 | Neurosearch A/S | 2,5-disubstituted tetrazole derivatives and their use as nicotinic acetylcholine receptor modulators |
| WO2011073298A1 (en) * | 2009-12-18 | 2011-06-23 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor modulators |
| US20120309792A1 (en) * | 2009-12-18 | 2012-12-06 | Neurosearch A/S | Tetrazole derivatives as nicotinic acetylcholine receptor modulators |
| WO2011092290A1 (en) | 2010-02-01 | 2011-08-04 | Novartis Ag | Pyrazolo[5,1b]oxazole derivatives as crf-1 receptor antagonists |
| AR080056A1 (es) | 2010-02-01 | 2012-03-07 | Novartis Ag | Derivados de ciclohexil-amida como antagonistas de los receptores de crf |
| EP2531490B1 (en) | 2010-02-02 | 2014-10-15 | Novartis AG | Cyclohexyl amide derivatives as crf receptor antagonists |
| GB201312800D0 (en) | 2013-07-17 | 2013-08-28 | Heptares Therapeutics Ltd | mGlu5 modulators |
| WO2016001452A1 (en) | 2014-07-04 | 2016-01-07 | Universität Zürich | Compounds, in particular for use in the treatment of a disease or condition for which a bromodomain inhibitor is indicated |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6660753B2 (en) * | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| CN1853630A (zh) * | 2001-02-21 | 2006-11-01 | Nps制药公司 | 杂多环化合物及其在亲代谢的谷氨酸受体拮抗剂中的应用 |
| DE60226756D1 (de) * | 2001-10-04 | 2008-07-03 | Merck & Co Inc | Heteroarylsubstituierte tetrazolmodulatoren des metabotropischen glutamatrezeptors-5 |
-
2004
- 2004-12-13 BR BRPI0417308-2A patent/BRPI0417308A/pt not_active IP Right Cessation
- 2004-12-13 US US10/582,051 patent/US20070255061A1/en not_active Abandoned
- 2004-12-13 AT AT04813689T patent/ATE393767T1/de not_active IP Right Cessation
- 2004-12-13 ES ES04813689T patent/ES2303969T3/es not_active Expired - Lifetime
- 2004-12-13 WO PCT/US2004/041401 patent/WO2005066155A1/en not_active Ceased
- 2004-12-13 CN CNA2004800406448A patent/CN1906187A/zh active Pending
- 2004-12-13 CA CA002548039A patent/CA2548039A1/en not_active Abandoned
- 2004-12-13 RU RU2006118021/04A patent/RU2006118021A/ru not_active Application Discontinuation
- 2004-12-13 DE DE602004013469T patent/DE602004013469T9/de not_active Expired - Fee Related
- 2004-12-13 MX MXPA06006674A patent/MXPA06006674A/es unknown
- 2004-12-13 JP JP2006545760A patent/JP2007514790A/ja active Pending
- 2004-12-13 AU AU2004312342A patent/AU2004312342A1/en not_active Abandoned
- 2004-12-13 KR KR1020067011449A patent/KR20060126993A/ko not_active Withdrawn
- 2004-12-13 EP EP04813689A patent/EP1713791B1/en not_active Expired - Lifetime
- 2004-12-16 TW TW093139143A patent/TW200524602A/zh unknown
- 2004-12-16 AR ARP040104711A patent/AR046768A1/es unknown
- 2004-12-17 UY UY28685A patent/UY28685A1/es unknown
-
2006
- 2006-05-25 IL IL175909A patent/IL175909A0/en unknown
- 2006-06-01 NO NO20062533A patent/NO20062533L/no not_active Application Discontinuation
- 2006-06-07 ZA ZA200604681A patent/ZA200604681B/en unknown
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