CA2415673A1 - Tetrazole derivatives - Google Patents
Tetrazole derivatives Download PDFInfo
- Publication number
- CA2415673A1 CA2415673A1 CA002415673A CA2415673A CA2415673A1 CA 2415673 A1 CA2415673 A1 CA 2415673A1 CA 002415673 A CA002415673 A CA 002415673A CA 2415673 A CA2415673 A CA 2415673A CA 2415673 A1 CA2415673 A1 CA 2415673A1
- Authority
- CA
- Canada
- Prior art keywords
- tetrazol
- compound
- formula
- xanthene
- amide
- 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.)
- Abandoned
Links
- 150000003536 tetrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 150000002367 halogens Chemical class 0.000 claims abstract description 3
- -1 N-(2-methyl-2H-tetrazol-5-yl)-2,2-Biphenyl-acetamide Chemical compound 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 230000001154 acute effect Effects 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
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- UZYUNDIGZSPOII-UHFFFAOYSA-N methyl 2-[5-(9h-xanthene-9-carbonylamino)tetrazol-2-yl]acetate Chemical compound COC(=O)CN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 UZYUNDIGZSPOII-UHFFFAOYSA-N 0.000 claims description 3
- 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
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- JAJWUYHPUGNXLE-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-1-methoxy-9h-xanthene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=C(OC)C=CC=C3OC3=CC=CC=C32)=N1 JAJWUYHPUGNXLE-UHFFFAOYSA-N 0.000 claims description 3
- XUKOQYVNKXGVFG-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-2-methoxy-9h-xanthene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC(OC)=CC=C3OC3=CC=CC=C32)=N1 XUKOQYVNKXGVFG-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- JOJJBQXFMKAOGS-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-9,10-dihydroanthracene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC=CC=C3CC3=CC=CC=C32)=N1 JOJJBQXFMKAOGS-UHFFFAOYSA-N 0.000 claims description 3
- IHRHHDVJXZGGSE-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-9h-thioxanthene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC=CC=C3SC3=CC=CC=C32)=N1 IHRHHDVJXZGGSE-UHFFFAOYSA-N 0.000 claims description 3
- HVTLYEBQNBWUIT-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-9h-xanthene-9-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 HVTLYEBQNBWUIT-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- RSZVCJLSWBLJAI-UHFFFAOYSA-N n-(2-propan-2-yltetrazol-5-yl)-9h-xanthene-9-carboxamide Chemical compound CC(C)N1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 RSZVCJLSWBLJAI-UHFFFAOYSA-N 0.000 claims description 3
- GTJYBDRTHSQVNP-UHFFFAOYSA-N n-(2-propyltetrazol-5-yl)-9h-xanthene-9-carboxamide Chemical compound CCCN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 GTJYBDRTHSQVNP-UHFFFAOYSA-N 0.000 claims description 3
- JLLYZLQGZOZUKO-UHFFFAOYSA-N n-(2-tert-butyltetrazol-5-yl)-9h-xanthene-9-carboxamide Chemical compound CC(C)(C)N1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 JLLYZLQGZOZUKO-UHFFFAOYSA-N 0.000 claims description 3
- RXVNIYXUWPHADG-UHFFFAOYSA-N n-[2-(2,2,2-trifluoroethyl)tetrazol-5-yl]-9h-xanthene-9-carboxamide Chemical compound FC(F)(F)CN1N=NC(NC(=O)C2C3=CC=CC=C3OC3=CC=CC=C32)=N1 RXVNIYXUWPHADG-UHFFFAOYSA-N 0.000 claims description 3
- PGRRUUBSWSDXKO-UHFFFAOYSA-N n-[2-(cyanomethyl)tetrazol-5-yl]-9h-xanthene-9-carboxamide Chemical compound C12=CC=CC=C2OC2=CC=CC=C2C1C(=O)NC=1N=NN(CC#N)N=1 PGRRUUBSWSDXKO-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 description 3
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- JWWLKNIUYMQZLO-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-6,11-dihydrobenzo[c][1]benzoxepine-11-carboxamide Chemical compound CCN1N=NC(NC(=O)C2C3=CC=CC=C3OCC3=CC=CC=C32)=N1 JWWLKNIUYMQZLO-UHFFFAOYSA-N 0.000 claims description 2
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- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical class NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 abstract description 2
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- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Otolaryngology (AREA)
- Urology & Nephrology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00115170.3 | 2000-07-13 | ||
| EP00115170 | 2000-07-13 | ||
| PCT/EP2001/007692 WO2002006254A1 (en) | 2000-07-13 | 2001-07-05 | Tetrazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2415673A1 true CA2415673A1 (en) | 2002-01-24 |
Family
ID=8169240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002415673A Abandoned CA2415673A1 (en) | 2000-07-13 | 2001-07-05 | Tetrazole derivatives |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6399641B1 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1303499B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP3971298B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR100504292B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1214017C (cg-RX-API-DMAC7.html) |
| AR (1) | AR029706A1 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE332895T1 (cg-RX-API-DMAC7.html) |
| AU (2) | AU7847201A (cg-RX-API-DMAC7.html) |
| BR (1) | BR0112465A (cg-RX-API-DMAC7.html) |
| CA (1) | CA2415673A1 (cg-RX-API-DMAC7.html) |
| DE (1) | DE60121447T2 (cg-RX-API-DMAC7.html) |
| DK (1) | DK1303499T3 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2267797T3 (cg-RX-API-DMAC7.html) |
| MX (1) | MXPA03000221A (cg-RX-API-DMAC7.html) |
| PA (1) | PA8521901A1 (cg-RX-API-DMAC7.html) |
| PE (1) | PE20020409A1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT1303499E (cg-RX-API-DMAC7.html) |
| WO (1) | WO2002006254A1 (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA200210157B (cg-RX-API-DMAC7.html) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7476399B2 (en) | 2003-08-06 | 2009-01-13 | Senomyx Inc. | Flavors, flavor modifiers, tastants, taste enhancers, umami or sweet tastants, and/or enhancers and use thereof |
| CA2558278A1 (en) * | 2004-03-05 | 2005-09-15 | Banyu Pharmaceutical Co., Ltd. | Diaryl-substituted five-membered heterocycle derivative |
| EP1850681B1 (en) | 2005-02-04 | 2019-12-18 | Firmenich Incorporated | Compounds comprising linked hetero aryl moieties and their use as novel umami flavor modifiers, tastants and taste enhancers for comestible compositions |
| AR055329A1 (es) | 2005-06-15 | 2007-08-15 | Senomyx Inc | Amidas bis-aromaticas y sus usos como modificadores de sabor dulce, saborizantes, y realzadores de sabor |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP2275096A3 (en) | 2005-08-26 | 2011-07-13 | Braincells, Inc. | Neurogenesis via modulation of the muscarinic receptors |
| AU2006304787A1 (en) | 2005-10-21 | 2007-04-26 | Braincells, Inc. | Modulation of neurogenesis by PDE inhibition |
| CA2625210A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| EP3398452B1 (en) | 2006-04-21 | 2024-10-02 | Firmenich Incorporated | Comestible compositions comprising high potency savory flavorants |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| AU2007249435A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 HT receptor mediated neurogenesis |
| BRPI0716604A2 (pt) | 2006-09-08 | 2013-04-09 | Braincells Inc | combinaÇÕes contendo um derivado de 4-acilaminopiridina |
| 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 |
| CA2313236A1 (en) * | 1997-12-10 | 1999-06-17 | Nps Pharmaceuticals, Inc. | Anticonvulsant and central nervous system-active bis(fluorophenyl)alkylamides, corresponding acids, and uses |
| 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 |
-
2001
- 2001-06-27 US US09/892,994 patent/US6399641B1/en not_active Expired - Fee Related
- 2001-07-05 MX MXPA03000221A patent/MXPA03000221A/es active IP Right Grant
- 2001-07-05 AU AU7847201A patent/AU7847201A/xx active Pending
- 2001-07-05 EP EP01956515A patent/EP1303499B1/en not_active Expired - Lifetime
- 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 AU AU2001278472A patent/AU2001278472B2/en not_active Ceased
- 2001-07-05 WO PCT/EP2001/007692 patent/WO2002006254A1/en not_active Ceased
- 2001-07-05 DE DE60121447T patent/DE60121447T2/de not_active Expired - Fee Related
- 2001-07-05 KR KR10-2003-7000350A patent/KR100504292B1/ko not_active Expired - Fee Related
- 2001-07-05 JP JP2002512158A patent/JP3971298B2/ja not_active Expired - Fee Related
- 2001-07-05 PT PT01956515T patent/PT1303499E/pt unknown
- 2001-07-05 CN CNB018126987A patent/CN1214017C/zh not_active Expired - Fee Related
- 2001-07-05 BR BR0112465-0A patent/BR0112465A/pt not_active IP Right Cessation
- 2001-07-05 ES ES01956515T patent/ES2267797T3/es not_active Expired - Lifetime
- 2001-07-05 DK DK01956515T patent/DK1303499T3/da active
- 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 |
|---|---|
| AU7847201A (en) | 2002-01-30 |
| PE20020409A1 (es) | 2002-05-21 |
| DE60121447T2 (de) | 2007-02-01 |
| BR0112465A (pt) | 2003-07-22 |
| US20020022648A1 (en) | 2002-02-21 |
| AR029706A1 (es) | 2003-07-10 |
| KR20030016390A (ko) | 2003-02-26 |
| JP2004504308A (ja) | 2004-02-12 |
| US6399641B1 (en) | 2002-06-04 |
| DK1303499T3 (da) | 2006-10-30 |
| EP1303499B1 (en) | 2006-07-12 |
| MXPA03000221A (es) | 2003-06-06 |
| DE60121447D1 (de) | 2006-08-24 |
| PT1303499E (pt) | 2006-11-30 |
| JP3971298B2 (ja) | 2007-09-05 |
| ES2267797T3 (es) | 2007-03-16 |
| ZA200210157B (en) | 2004-03-15 |
| CN1214017C (zh) | 2005-08-10 |
| EP1303499A1 (en) | 2003-04-23 |
| AU2001278472B2 (en) | 2006-08-03 |
| CN1441791A (zh) | 2003-09-10 |
| KR100504292B1 (ko) | 2005-07-28 |
| WO2002006254A1 (en) | 2002-01-24 |
| ATE332895T1 (de) | 2006-08-15 |
| PA8521901A1 (es) | 2002-04-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |