PT1303499E - Derivados de tetrazole - Google Patents
Derivados de tetrazole Download PDFInfo
- Publication number
- PT1303499E PT1303499E PT01956515T PT01956515T PT1303499E PT 1303499 E PT1303499 E PT 1303499E PT 01956515 T PT01956515 T PT 01956515T PT 01956515 T PT01956515 T PT 01956515T PT 1303499 E PT1303499 E PT 1303499E
- Authority
- PT
- Portugal
- Prior art keywords
- tetrazol
- compound
- carboxylic acid
- formula
- xanthene
- Prior art date
Links
- 150000003536 tetrazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 95
- 238000000034 method Methods 0.000 claims description 50
- -1 2-ethyl- N- (2-cyclopropylmethyl-2H-tetrazol-5-yl) -2,2-diphenylacetamide Chemical compound 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 24
- VSBFNCXKYIEYIS-UHFFFAOYSA-N Xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)C3=CC=CC=C3OC2=C1 VSBFNCXKYIEYIS-UHFFFAOYSA-N 0.000 claims description 14
- SUEIINDYWPMJEW-UHFFFAOYSA-N 2-ethyltetrazol-5-amine Chemical compound CCN1N=NC(N)=N1 SUEIINDYWPMJEW-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000001684 chronic effect Effects 0.000 claims description 7
- 208000002193 Pain Diseases 0.000 claims description 6
- 206010034010 Parkinsonism Diseases 0.000 claims description 6
- 230000001154 acute effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 229930195712 glutamate Natural products 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 208000012902 Nervous system disease Diseases 0.000 claims description 5
- 208000025966 Neurological disease Diseases 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 4
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
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- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- AUZWCBORRSXYLV-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)tetrazol-5-amine Chemical compound NC=1N=NN(CC(F)(F)F)N=1 AUZWCBORRSXYLV-UHFFFAOYSA-N 0.000 claims description 3
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- 125000003545 alkoxy group Chemical group 0.000 claims description 3
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- HGGMJOOOHPXAHJ-UHFFFAOYSA-N methyl 2-[5-[(2,2-diphenylacetyl)amino]tetrazol-2-yl]acetate Chemical compound COC(=O)CN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 HGGMJOOOHPXAHJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010027599 migraine Diseases 0.000 claims description 3
- PYVHEKPRGMFMQV-UHFFFAOYSA-N n-[2-(cyanomethyl)tetrazol-5-yl]-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)NC=1N=NN(CC#N)N=1 PYVHEKPRGMFMQV-UHFFFAOYSA-N 0.000 claims description 3
- MGBOODNHQOABEO-UHFFFAOYSA-N n-[2-(difluoromethyl)tetrazol-5-yl]-2,2-diphenylacetamide Chemical compound FC(F)N1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 MGBOODNHQOABEO-UHFFFAOYSA-N 0.000 claims description 3
- 229960002715 nicotine Drugs 0.000 claims description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
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- CMOASNQTFKKHTB-UHFFFAOYSA-N 2,2-diphenyl-n-(2-propan-2-yltetrazol-5-yl)acetamide Chemical compound CC(C)N1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 CMOASNQTFKKHTB-UHFFFAOYSA-N 0.000 claims description 2
- JAQPOQILWCFFDX-UHFFFAOYSA-N 2,2-diphenyl-n-(2-propyltetrazol-5-yl)acetamide Chemical compound CCCN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 JAQPOQILWCFFDX-UHFFFAOYSA-N 0.000 claims description 2
- DLXJVSUNZMABON-UHFFFAOYSA-N 2,2-diphenyl-n-[2-(2,2,2-trifluoroethyl)tetrazol-5-yl]acetamide Chemical compound FC(F)(F)CN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 DLXJVSUNZMABON-UHFFFAOYSA-N 0.000 claims description 2
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PGUUWGJUCVQTIP-UHFFFAOYSA-N n-(2-methyltetrazol-5-yl)-2,2-diphenylacetamide Chemical compound CN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 PGUUWGJUCVQTIP-UHFFFAOYSA-N 0.000 claims description 2
- GTJLDZHHLPYRSM-UHFFFAOYSA-N n-(2-methyltetrazol-5-yl)-9h-xanthene-9-carboxamide Chemical compound CN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 GTJLDZHHLPYRSM-UHFFFAOYSA-N 0.000 claims description 2
- AGMAYJIBVDBMSQ-UHFFFAOYSA-N n-(2-tert-butyltetrazol-5-yl)-2,2-diphenylacetamide Chemical compound CC(C)(C)N1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 AGMAYJIBVDBMSQ-UHFFFAOYSA-N 0.000 claims description 2
- QJGNKJKSZBODQF-UHFFFAOYSA-N n-[2-(cyclopropylmethyl)tetrazol-5-yl]-9h-xanthene-9-carboxamide Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)NC(=N1)N=NN1CC1CC1 QJGNKJKSZBODQF-UHFFFAOYSA-N 0.000 claims description 2
- SYXYWUGTXVQIHA-UHFFFAOYSA-N n-[2-(difluoromethyl)tetrazol-5-yl]-9h-xanthene-9-carboxamide Chemical compound FC(F)N1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 SYXYWUGTXVQIHA-UHFFFAOYSA-N 0.000 claims description 2
- WJHHAVKOLHGCGW-UHFFFAOYSA-N n-[2-(methoxymethyl)tetrazol-5-yl]-2,2-diphenylacetamide Chemical compound COCN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 WJHHAVKOLHGCGW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 206010019233 Headaches Diseases 0.000 claims 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- JZEDQHBBFAIXFW-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-4-methoxy-9h-xanthene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC=CC(OC)=C3OC3=CC=CC=C32)=N1 JZEDQHBBFAIXFW-UHFFFAOYSA-N 0.000 claims 1
- IHRHHDVJXZGGSE-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-9h-thioxanthene-9-carboxamide Chemical group CCN1N=NC(NC(=O)C2C3=CC=CC=C3SC3=CC=CC=C32)=N1 IHRHHDVJXZGGSE-UHFFFAOYSA-N 0.000 claims 1
- BWRVDPZDUPPAHX-UHFFFAOYSA-N n-[2-(methoxymethyl)tetrazol-5-yl]-9h-xanthene-9-carboxamide Chemical compound COCN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 BWRVDPZDUPPAHX-UHFFFAOYSA-N 0.000 claims 1
- 125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 claims 1
- 239000007787 solid Substances 0.000 description 39
- MSYLETHDEIJMAF-UHFFFAOYSA-N 2,2-diphenylacetyl chloride Chemical compound C=1C=CC=CC=1C(C(=O)Cl)C1=CC=CC=C1 MSYLETHDEIJMAF-UHFFFAOYSA-N 0.000 description 11
- JYRSCMLJPXJTLI-UHFFFAOYSA-N 9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3OC2=C1 JYRSCMLJPXJTLI-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- SGPSAFCJQSLRDD-UHFFFAOYSA-N 2-(cyclopropylmethyl)tetrazol-5-amine Chemical compound N1=C(N)N=NN1CC1CC1 SGPSAFCJQSLRDD-UHFFFAOYSA-N 0.000 description 5
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- CJVLZZSRHIYZJT-UHFFFAOYSA-N 2-(difluoromethyl)tetrazol-5-amine Chemical compound NC=1N=NN(C(F)F)N=1 CJVLZZSRHIYZJT-UHFFFAOYSA-N 0.000 description 4
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- LNEMRKLKJHWIGK-UHFFFAOYSA-N 2-(methoxymethyl)tetrazol-5-amine Chemical compound COCN1N=NC(N)=N1 LNEMRKLKJHWIGK-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- Ophthalmology & Optometry (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115170 | 2000-07-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1303499E true PT1303499E (pt) | 2006-11-30 |
Family
ID=8169240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT01956515T PT1303499E (pt) | 2000-07-13 | 2001-07-05 | Derivados de tetrazole |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6399641B1 (enExample) |
| EP (1) | EP1303499B1 (enExample) |
| JP (1) | JP3971298B2 (enExample) |
| KR (1) | KR100504292B1 (enExample) |
| CN (1) | CN1214017C (enExample) |
| AR (1) | AR029706A1 (enExample) |
| AT (1) | ATE332895T1 (enExample) |
| AU (2) | AU2001278472B2 (enExample) |
| BR (1) | BR0112465A (enExample) |
| CA (1) | CA2415673A1 (enExample) |
| DE (1) | DE60121447T2 (enExample) |
| DK (1) | DK1303499T3 (enExample) |
| ES (1) | ES2267797T3 (enExample) |
| MX (1) | MXPA03000221A (enExample) |
| PA (1) | PA8521901A1 (enExample) |
| PE (1) | PE20020409A1 (enExample) |
| PT (1) | PT1303499E (enExample) |
| WO (1) | WO2002006254A1 (enExample) |
| ZA (1) | ZA200210157B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1659881B1 (en) | 2003-08-06 | 2019-04-03 | Senomyx Inc. | Novel flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| AU2005219791B2 (en) * | 2004-03-05 | 2011-06-09 | Msd K.K. | Diaryl-substituted five-membered heterocycle derivative |
| CN101384183B (zh) | 2005-02-04 | 2012-07-04 | 西诺米克斯公司 | 包含连接有杂芳基部分的化合物及其作为用于食物组合物的新型鲜味调节剂、促味剂和味觉增强剂的应用 |
| TW200715993A (en) | 2005-06-15 | 2007-05-01 | Senomyx Inc | Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers |
| EP2258357A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP2275096A3 (en) | 2005-08-26 | 2011-07-13 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
| WO2007047978A2 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| EP2314289A1 (en) | 2005-10-31 | 2011-04-27 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| DK3235811T3 (en) | 2006-04-21 | 2018-11-12 | Senomyx Inc | PROCEDURE FOR THE PREPARATION OF OXALAMIDS |
| US7678808B2 (en) | 2006-05-09 | 2010-03-16 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| EP2021000A2 (en) | 2006-05-09 | 2009-02-11 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2008030651A1 (en) | 2006-09-08 | 2008-03-13 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| EP2093234A1 (en) | 2008-02-08 | 2009-08-26 | Nutrinova Nutrition Specialties & Food Ingredients GmbH | Oligopeptides for use as taste modulators |
| TWI429404B (zh) | 2008-03-03 | 2014-03-11 | Senomyx Inc | 異山梨醇衍生物及彼等作為風味改良劑、促味劑及促味增強劑之用途 |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1343827A (en) * | 1971-06-15 | 1974-01-16 | Science Union & Cie | Acylaminotetrazoles and process for preparing them |
| DE4129742A1 (de) * | 1991-09-06 | 1993-03-11 | Bayer Ag | Heterocyclisch substituierte chinolylmethoxy-phenylacetamide |
| GB9626151D0 (en) * | 1996-12-17 | 1997-02-05 | Lilly Industries Ltd | Pharmaceutical compounds |
| EP1042275B1 (en) * | 1997-12-10 | 2005-11-09 | Nps Pharmaceuticals, Inc. | Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides |
| US6548522B1 (en) * | 1999-10-12 | 2003-04-15 | Hoffmann-La Roche Inc. | Method for treating conditions related to the glutamate receptor using carboxylic acid amide derivatives |
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2001
- 2001-06-27 US US09/892,994 patent/US6399641B1/en not_active Expired - Fee Related
- 2001-07-05 DK DK01956515T patent/DK1303499T3/da active
- 2001-07-05 DE DE60121447T patent/DE60121447T2/de not_active Expired - Fee Related
- 2001-07-05 BR BR0112465-0A patent/BR0112465A/pt not_active IP Right Cessation
- 2001-07-05 JP JP2002512158A patent/JP3971298B2/ja not_active Expired - Fee Related
- 2001-07-05 ES ES01956515T patent/ES2267797T3/es not_active Expired - Lifetime
- 2001-07-05 KR KR10-2003-7000350A patent/KR100504292B1/ko not_active Expired - Fee Related
- 2001-07-05 AU AU2001278472A patent/AU2001278472B2/en not_active Ceased
- 2001-07-05 AU AU7847201A patent/AU7847201A/xx active Pending
- 2001-07-05 CN CNB018126987A patent/CN1214017C/zh not_active Expired - Fee Related
- 2001-07-05 AT AT01956515T patent/ATE332895T1/de not_active IP Right Cessation
- 2001-07-05 CA CA002415673A patent/CA2415673A1/en not_active Abandoned
- 2001-07-05 MX MXPA03000221A patent/MXPA03000221A/es active IP Right Grant
- 2001-07-05 WO PCT/EP2001/007692 patent/WO2002006254A1/en not_active Ceased
- 2001-07-05 PT PT01956515T patent/PT1303499E/pt unknown
- 2001-07-05 EP EP01956515A patent/EP1303499B1/en not_active Expired - Lifetime
- 2001-07-10 PA PA20018521901A patent/PA8521901A1/es unknown
- 2001-07-11 PE PE2001000693A patent/PE20020409A1/es not_active Application Discontinuation
- 2001-07-12 AR ARP010103306A patent/AR029706A1/es unknown
-
2002
- 2002-12-13 ZA ZA200210157A patent/ZA200210157B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03000221A (es) | 2003-06-06 |
| CA2415673A1 (en) | 2002-01-24 |
| EP1303499B1 (en) | 2006-07-12 |
| PE20020409A1 (es) | 2002-05-21 |
| ZA200210157B (en) | 2004-03-15 |
| PA8521901A1 (es) | 2002-04-25 |
| EP1303499A1 (en) | 2003-04-23 |
| CN1214017C (zh) | 2005-08-10 |
| JP3971298B2 (ja) | 2007-09-05 |
| DK1303499T3 (da) | 2006-10-30 |
| AU7847201A (en) | 2002-01-30 |
| DE60121447D1 (de) | 2006-08-24 |
| US20020022648A1 (en) | 2002-02-21 |
| WO2002006254A1 (en) | 2002-01-24 |
| KR100504292B1 (ko) | 2005-07-28 |
| CN1441791A (zh) | 2003-09-10 |
| US6399641B1 (en) | 2002-06-04 |
| KR20030016390A (ko) | 2003-02-26 |
| BR0112465A (pt) | 2003-07-22 |
| ATE332895T1 (de) | 2006-08-15 |
| AU2001278472B2 (en) | 2006-08-03 |
| DE60121447T2 (de) | 2007-02-01 |
| AR029706A1 (es) | 2003-07-10 |
| ES2267797T3 (es) | 2007-03-16 |
| JP2004504308A (ja) | 2004-02-12 |
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