ZA200210157B - Tetrazole derivatives. - Google Patents
Tetrazole derivatives. Download PDFInfo
- Publication number
- ZA200210157B ZA200210157B ZA200210157A ZA200210157A ZA200210157B ZA 200210157 B ZA200210157 B ZA 200210157B ZA 200210157 A ZA200210157 A ZA 200210157A ZA 200210157 A ZA200210157 A ZA 200210157A ZA 200210157 B ZA200210157 B ZA 200210157B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- tetrazol
- formula
- accordance
- xanthene
- Prior art date
Links
- 150000003536 tetrazoles Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 107
- 150000003839 salts Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 29
- 239000000203 mixture Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 16
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 230000001154 acute effect Effects 0.000 claims description 13
- 230000002265 prevention Effects 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 10
- 208000027089 Parkinsonian disease Diseases 0.000 claims description 10
- 206010034010 Parkinsonism Diseases 0.000 claims description 10
- 230000001684 chronic effect Effects 0.000 claims description 10
- 208000012902 Nervous system disease Diseases 0.000 claims description 9
- 208000025966 Neurological disease Diseases 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 208000024827 Alzheimer disease Diseases 0.000 claims description 6
- 208000028017 Psychotic disease Diseases 0.000 claims description 6
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 6
- 229930195712 glutamate Natural products 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000030507 AIDS Diseases 0.000 claims description 5
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000000094 Chronic Pain Diseases 0.000 claims description 5
- 206010010904 Convulsion Diseases 0.000 claims description 5
- 206010012289 Dementia Diseases 0.000 claims description 5
- 208000012661 Dyskinesia Diseases 0.000 claims description 5
- 208000020564 Eye injury Diseases 0.000 claims description 5
- 206010019196 Head injury Diseases 0.000 claims description 5
- 208000010496 Heart Arrest Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 208000013016 Hypoglycemia Diseases 0.000 claims description 5
- 206010021143 Hypoxia Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 208000019695 Migraine disease Diseases 0.000 claims description 5
- 208000007101 Muscle Cramp Diseases 0.000 claims description 5
- 206010057852 Nicotine dependence Diseases 0.000 claims description 5
- 208000026251 Opioid-Related disease Diseases 0.000 claims description 5
- 208000017442 Retinal disease Diseases 0.000 claims description 5
- 206010038923 Retinopathy Diseases 0.000 claims description 5
- 208000005392 Spasm Diseases 0.000 claims description 5
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 5
- 206010046543 Urinary incontinence Diseases 0.000 claims description 5
- 206010047700 Vomiting Diseases 0.000 claims description 5
- 208000005298 acute pain Diseases 0.000 claims description 5
- 230000036506 anxiety Effects 0.000 claims description 5
- 230000036770 blood supply Effects 0.000 claims description 5
- 210000004556 brain Anatomy 0.000 claims description 5
- 230000003925 brain function Effects 0.000 claims description 5
- 230000036461 convulsion Effects 0.000 claims description 5
- 230000006870 function Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 230000007954 hypoxia Effects 0.000 claims description 5
- 206010027599 migraine Diseases 0.000 claims description 5
- 201000005040 opiate dependence Diseases 0.000 claims description 5
- 230000035935 pregnancy Effects 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 208000020431 spinal cord injury Diseases 0.000 claims description 5
- 230000008673 vomiting Effects 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 208000010877 cognitive disease Diseases 0.000 claims description 4
- 125000000524 functional group Chemical group 0.000 claims description 4
- 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 3
- 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 3
- 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 3
- 125000003545 alkoxy group Chemical group 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
- 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
- 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 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
- 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
- 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 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
- 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 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
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 2
- 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 2
- 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 2
- 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 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000007812 deficiency Effects 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000007787 solid Substances 0.000 description 40
- 238000007429 general method Methods 0.000 description 34
- 150000002500 ions Chemical class 0.000 description 23
- 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 13
- 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
- JVSMPWHQUPKRNV-UHFFFAOYSA-N 2h-tetrazol-5-amine;hydrate Chemical compound O.NC=1N=NNN=1 JVSMPWHQUPKRNV-UHFFFAOYSA-N 0.000 description 11
- SUEIINDYWPMJEW-UHFFFAOYSA-N 2-ethyltetrazol-5-amine Chemical compound CCN1N=NC(N)=N1 SUEIINDYWPMJEW-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000002775 capsule Substances 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
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 description 7
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- -1 their manufacture Substances 0.000 description 6
- 239000001828 Gelatine Substances 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- SGPSAFCJQSLRDD-UHFFFAOYSA-N 2-(cyclopropylmethyl)tetrazol-5-amine Chemical compound N1=C(N)N=NN1CC1CC1 SGPSAFCJQSLRDD-UHFFFAOYSA-N 0.000 description 4
- AZUKLCJYWVMPML-UHFFFAOYSA-N 2-methyltetrazol-5-amine Chemical compound CN1N=NC(N)=N1 AZUKLCJYWVMPML-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 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 description 3
- CJVLZZSRHIYZJT-UHFFFAOYSA-N 2-(difluoromethyl)tetrazol-5-amine Chemical compound NC=1N=NN(C(F)F)N=1 CJVLZZSRHIYZJT-UHFFFAOYSA-N 0.000 description 3
- WBHVXTQXNWCMJD-UHFFFAOYSA-N 2-propyltetrazol-5-amine Chemical compound CCCN1N=NC(N)=N1 WBHVXTQXNWCMJD-UHFFFAOYSA-N 0.000 description 3
- GTPWIZDTYLYKQB-UHFFFAOYSA-N 2-tert-butyltetrazol-5-amine Chemical compound CC(C)(C)N1N=NC(N)=N1 GTPWIZDTYLYKQB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 229920002261 Corn starch Polymers 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 229940049906 glutamate Drugs 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- VIRGSASWFHWKFL-UHFFFAOYSA-N 1-methoxy-9h-xanthene-9-carbonyl chloride Chemical compound O1C2=CC=CC=C2C(C(Cl)=O)C2=C1C=CC=C2OC VIRGSASWFHWKFL-UHFFFAOYSA-N 0.000 description 2
- MEQTVQVAFGUQRU-UHFFFAOYSA-N 2-(5-aminotetrazol-2-yl)acetonitrile Chemical compound NC=1N=NN(CC#N)N=1 MEQTVQVAFGUQRU-UHFFFAOYSA-N 0.000 description 2
- LNEMRKLKJHWIGK-UHFFFAOYSA-N 2-(methoxymethyl)tetrazol-5-amine Chemical compound COCN1N=NC(N)=N1 LNEMRKLKJHWIGK-UHFFFAOYSA-N 0.000 description 2
- WYNQYSJYBXNFCT-UHFFFAOYSA-N 2-methoxy-9h-xanthene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(Cl)=O)C3=CC(OC)=CC=C3OC2=C1 WYNQYSJYBXNFCT-UHFFFAOYSA-N 0.000 description 2
- NEJVMYROZIQXMS-UHFFFAOYSA-N 2-propan-2-yltetrazol-5-amine Chemical compound CC(C)N1N=NC(N)=N1 NEJVMYROZIQXMS-UHFFFAOYSA-N 0.000 description 2
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 2
- ROKPPCKBNGLANL-UHFFFAOYSA-N 4-methoxy-9h-xanthene-9-carbonyl chloride Chemical compound ClC(=O)C1C2=CC=CC=C2OC2=C1C=CC=C2OC ROKPPCKBNGLANL-UHFFFAOYSA-N 0.000 description 2
- XXOBITQFUQTSKV-UHFFFAOYSA-N 6,11-dihydrobenzo[c][1]benzoxepine-11-carbonyl chloride Chemical compound C1OC2=CC=CC=C2C(C(=O)Cl)C2=CC=CC=C21 XXOBITQFUQTSKV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 239000005557 antagonist Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000008298 dragée Substances 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 239000003823 glutamate receptor agonist Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JHKJQWFHNIOUKY-UHFFFAOYSA-N iodomethylcyclopropane Chemical compound ICC1CC1 JHKJQWFHNIOUKY-UHFFFAOYSA-N 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CPLXDALGPSFXRB-UHFFFAOYSA-N methyl 2-(5-aminotetrazol-2-yl)acetate Chemical compound COC(=O)CN1N=NC(N)=N1 CPLXDALGPSFXRB-UHFFFAOYSA-N 0.000 description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 2
- 239000008108 microcrystalline cellulose Substances 0.000 description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 description 2
- IFILLHOALSZOAY-UHFFFAOYSA-N n-(2-ethyltetrazol-5-yl)-2,2-diphenylacetamide Chemical compound CCN1N=NC(NC(=O)C(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 IFILLHOALSZOAY-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- GFPKAZCCJPBWQO-UHFFFAOYSA-N n-[2-(cyclopropylmethyl)tetrazol-5-yl]-2,2-diphenylacetamide Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)C(=O)NC(=N1)N=NN1CC1CC1 GFPKAZCCJPBWQO-UHFFFAOYSA-N 0.000 description 2
- 239000002858 neurotransmitter agent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- ZXVKXGKPOOIFFF-UHFFFAOYSA-N 1-methoxy-9h-xanthene Chemical compound O1C2=CC=CC=C2CC2=C1C=CC=C2OC ZXVKXGKPOOIFFF-UHFFFAOYSA-N 0.000 description 1
- MKRLJNMGCYBKCR-UHFFFAOYSA-N 1-methoxy-9h-xanthene-9-carboxylic acid Chemical compound O1C2=CC=CC=C2C(C(O)=O)C2=C1C=CC=C2OC MKRLJNMGCYBKCR-UHFFFAOYSA-N 0.000 description 1
- RTMMSCJWQYWMNK-UHFFFAOYSA-N 2,2,2-trifluoroethyl trifluoromethanesulfonate Chemical compound FC(F)(F)COS(=O)(=O)C(F)(F)F RTMMSCJWQYWMNK-UHFFFAOYSA-N 0.000 description 1
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 1
- UEADUMUDFLTHOI-UHFFFAOYSA-N 2-(5-aminotetrazol-2-yl)acetic acid Chemical compound NC=1N=NN(CC(O)=O)N=1 UEADUMUDFLTHOI-UHFFFAOYSA-N 0.000 description 1
- IMWWCJDPYOKKQS-UHFFFAOYSA-N 2-(methoxymethyl)tetrazole Chemical compound COCN1N=CN=N1 IMWWCJDPYOKKQS-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- QZTUHJIPLHLSPP-UHFFFAOYSA-N 2-methoxy-9h-xanthene Chemical compound C1=CC=C2CC3=CC(OC)=CC=C3OC2=C1 QZTUHJIPLHLSPP-UHFFFAOYSA-N 0.000 description 1
- ZLRGGWWZJSJBDR-UHFFFAOYSA-N 2-methoxy-9h-xanthene-9-carboxylic acid Chemical compound C1=CC=C2C(C(O)=O)C3=CC(OC)=CC=C3OC2=C1 ZLRGGWWZJSJBDR-UHFFFAOYSA-N 0.000 description 1
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical class NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- VUFNFAAEMMFBLD-UHFFFAOYSA-N 4-methoxy-9h-xanthene Chemical compound C1C2=CC=CC=C2OC2=C1C=CC=C2OC VUFNFAAEMMFBLD-UHFFFAOYSA-N 0.000 description 1
- UKWRQOKTEGMLMA-UHFFFAOYSA-N 4-methoxy-9h-xanthene-9-carboxylic acid Chemical compound OC(=O)C1C2=CC=CC=C2OC2=C1C=CC=C2OC UKWRQOKTEGMLMA-UHFFFAOYSA-N 0.000 description 1
- OCKABWVMRIIHHE-UHFFFAOYSA-N 9,10-dihydroanthracene-9-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)C3=CC=CC=C3CC2=C1 OCKABWVMRIIHHE-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
- 102100036834 Metabotropic glutamate receptor 1 Human genes 0.000 description 1
- 102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 description 1
- 102100038352 Metabotropic glutamate receptor 3 Human genes 0.000 description 1
- 102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 description 1
- 102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 description 1
- 102100038300 Metabotropic glutamate receptor 6 Human genes 0.000 description 1
- 102100038294 Metabotropic glutamate receptor 7 Human genes 0.000 description 1
- 102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
- AMJRSUWJSRKGNO-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)phenoxy]ethoxy]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O AMJRSUWJSRKGNO-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001270 agonistic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012131 assay buffer Substances 0.000 description 1
- 238000001210 attenuated total reflectance infrared spectroscopy Methods 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229960004903 invert sugar Drugs 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 108010038421 metabotropic glutamate receptor 2 Proteins 0.000 description 1
- 108010038445 metabotropic glutamate receptor 3 Proteins 0.000 description 1
- 108010038422 metabotropic glutamate receptor 4 Proteins 0.000 description 1
- 108010038450 metabotropic glutamate receptor 6 Proteins 0.000 description 1
- 108010038449 metabotropic glutamate receptor 7 Proteins 0.000 description 1
- 108010038448 metabotropic glutamate receptor 8 Proteins 0.000 description 1
- 108010014719 metabotropic glutamate receptor type 1 Proteins 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 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 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 210000002265 sensory receptor cell Anatomy 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- BHEKYOLNRIGGLB-UHFFFAOYSA-N tert-butyl n,n'-dicyclohexylcarbamimidate Chemical compound C1CCCCC1N=C(OC(C)(C)C)NC1CCCCC1 BHEKYOLNRIGGLB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
- Otolaryngology (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 |
|---|---|
| ZA200210157B true ZA200210157B (en) | 2004-03-15 |
Family
ID=8169240
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200210157A ZA200210157B (en) | 2000-07-13 | 2002-12-13 | Tetrazole derivatives. |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US6399641B1 (https=) |
| EP (1) | EP1303499B1 (https=) |
| JP (1) | JP3971298B2 (https=) |
| KR (1) | KR100504292B1 (https=) |
| CN (1) | CN1214017C (https=) |
| AR (1) | AR029706A1 (https=) |
| AT (1) | ATE332895T1 (https=) |
| AU (2) | AU2001278472B2 (https=) |
| BR (1) | BR0112465A (https=) |
| CA (1) | CA2415673A1 (https=) |
| DE (1) | DE60121447T2 (https=) |
| DK (1) | DK1303499T3 (https=) |
| ES (1) | ES2267797T3 (https=) |
| MX (1) | MXPA03000221A (https=) |
| PA (1) | PA8521901A1 (https=) |
| PE (1) | PE20020409A1 (https=) |
| PT (1) | PT1303499E (https=) |
| WO (1) | WO2002006254A1 (https=) |
| ZA (1) | ZA200210157B (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0413347A (pt) | 2003-08-06 | 2006-10-10 | Senomyx Inc | novos sabores, modificadores de sabor, agentes de sabor, realçadores de sabor, agentes de sabor e/ou realçadores umami ou doces, e utilização correspondente |
| WO2005085214A1 (ja) * | 2004-03-05 | 2005-09-15 | Banyu Pharmaceutical Co., Ltd | ジアリール置換複素５員環誘導体 |
| MX2007009388A (es) | 2005-02-04 | 2007-09-25 | Senomyx Inc | Compuestos que comprenden porciones heteroarilo unidas y su uso como modificadores del sabor unami, saborizantes y mejoradores del sabor para composiciones comestibles. |
| TW200715993A (en) | 2005-06-15 | 2007-05-01 | Senomyx Inc | Bis-aromatic amides and their uses as sweet flavor modifiers, tastants, and taste enhancers |
| EP1928437A2 (en) | 2005-08-26 | 2008-06-11 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| US20070112017A1 (en) | 2005-10-31 | 2007-05-17 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| KR101387563B1 (ko) | 2006-04-21 | 2014-04-25 | 세노믹스, 인코포레이티드 | 고효능의 조미용 향료를 포함하는 식품 조성물 및 이의 제조 방법 |
| AU2007249399A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| WO2007134077A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| EP2068872A1 (en) | 2006-09-08 | 2009-06-17 | 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 |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | 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 |
| JP2001525390A (ja) * | 1997-12-10 | 2001-12-11 | エヌピーエス ファーマシューティカルズ インコーポレーテッド | 抗痙攣薬および中枢神経系活性ビス（フルオロフェニル）アルキルアミド類 |
| 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 WO PCT/EP2001/007692 patent/WO2002006254A1/en not_active Ceased
- 2001-07-05 AT AT01956515T patent/ATE332895T1/de not_active IP Right Cessation
- 2001-07-05 EP EP01956515A patent/EP1303499B1/en not_active Expired - Lifetime
- 2001-07-05 JP JP2002512158A patent/JP3971298B2/ja not_active Expired - Fee Related
- 2001-07-05 CN CNB018126987A patent/CN1214017C/zh not_active Expired - Fee Related
- 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 PT PT01956515T patent/PT1303499E/pt unknown
- 2001-07-05 BR BR0112465-0A patent/BR0112465A/pt not_active IP Right Cessation
- 2001-07-05 KR KR10-2003-7000350A patent/KR100504292B1/ko not_active Expired - Fee Related
- 2001-07-05 DK DK01956515T patent/DK1303499T3/da active
- 2001-07-05 ES ES01956515T patent/ES2267797T3/es not_active Expired - Lifetime
- 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 DE DE60121447T patent/DE60121447T2/de not_active Expired - Fee Related
- 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 |
|---|---|
| ES2267797T3 (es) | 2007-03-16 |
| PE20020409A1 (es) | 2002-05-21 |
| PA8521901A1 (es) | 2002-04-25 |
| CN1441791A (zh) | 2003-09-10 |
| CA2415673A1 (en) | 2002-01-24 |
| WO2002006254A1 (en) | 2002-01-24 |
| JP3971298B2 (ja) | 2007-09-05 |
| ATE332895T1 (de) | 2006-08-15 |
| AU7847201A (en) | 2002-01-30 |
| EP1303499B1 (en) | 2006-07-12 |
| EP1303499A1 (en) | 2003-04-23 |
| AR029706A1 (es) | 2003-07-10 |
| DE60121447D1 (de) | 2006-08-24 |
| AU2001278472B2 (en) | 2006-08-03 |
| JP2004504308A (ja) | 2004-02-12 |
| MXPA03000221A (es) | 2003-06-06 |
| CN1214017C (zh) | 2005-08-10 |
| DK1303499T3 (da) | 2006-10-30 |
| KR100504292B1 (ko) | 2005-07-28 |
| BR0112465A (pt) | 2003-07-22 |
| US20020022648A1 (en) | 2002-02-21 |
| KR20030016390A (ko) | 2003-02-26 |
| DE60121447T2 (de) | 2007-02-01 |
| PT1303499E (pt) | 2006-11-30 |
| US6399641B1 (en) | 2002-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP1171423B1 (en) | Carbamic acid derivatives and their use as metabotropic glutamate receptor ligands | |
| AU2001278472B2 (en) | Tetrazole derivatives | |
| AU2001278472A1 (en) | Tetrazole derivatives | |
| HUE026220T2 (en) | Pyridyl derivatives as CFTR modulators | |
| JP5753626B2 (ja) | ピラゾリジン−３−オン誘導体 | |
| CA2388470C (en) | Use of carbonylamino derivatives against cns disorders | |
| CA2914282A1 (en) | Ethynyl derivatives as metabotropic glutamate receptor antagonists | |
| JP6263542B2 (ja) | Ｍｇｌｕｒ５受容体活性のモジュレーターとしてのエチニル誘導体 | |
| AU2004253657B2 (en) | Imidazole derivatives III | |
| CA2511337C (en) | Oxazoles as mglur1 enhancer | |
| US6803381B1 (en) | Carbamic acid derivatives |