ZA200606594B - Tetrazole compounds and their use as metabotropic glutamate receptor antagonists - Google Patents

Tetrazole compounds and their use as metabotropic glutamate receptor antagonists Download PDF

Info

Publication number: ZA200606594B
Authority: ZA; South Africa
Prior art keywords: tetrazol; methyl; triazol; phenyl; ethyl
Prior art date: 2004-02-18

Application number

ZA200606594A

Other languages

English (en)

Inventor

Johansson Martin

Minidis Alexander

Staaf Karin

Wensbo David

Mcleod Donald

Edwards Louise

Isaac Methvin

O'brien Anne

Slassi Abdelmalik

Xin Tao

Original Assignee

Astrazeneca Ab

Nps Pharma Inc

Priority date (The priority date 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 date listed.)

2004-02-18

Filing date

2006-08-08

Publication date

2007-11-28

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=34886129&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ZA200606594(B) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2006-08-08 Application filed by Astrazeneca Ab, Nps Pharma Inc filed Critical Astrazeneca Ab

2007-11-28 Publication of ZA200606594B publication Critical patent/ZA200606594B/en

Links

-1 Tetrazole compounds Chemical class 0.000 title claims description 36
108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims description 32
102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims description 32
239000003825 glutamate receptor antagonist Substances 0.000 title 1
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 41
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 37
125000000217 alkyl group Chemical group 0.000 claims description 28
229910052799 carbon Inorganic materials 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 22
125000003118 aryl group Chemical group 0.000 claims description 20
125000004429 atom Chemical group 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 19
229910052757 nitrogen Inorganic materials 0.000 claims description 19
125000005843 halogen group Chemical group 0.000 claims description 18
125000001072 heteroaryl group Chemical group 0.000 claims description 16
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 15
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 13
150000003852 triazoles Chemical class 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 9
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
125000004193 piperazinyl group Chemical group 0.000 claims description 7
208000002193 Pain Diseases 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 6
230000001404 mediated effect Effects 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
208000020016 psychiatric disease Diseases 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 5
208000012902 Nervous system disease Diseases 0.000 claims description 5
208000025966 Neurological disease Diseases 0.000 claims description 5
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
229920002554 vinyl polymer Polymers 0.000 claims description 5
208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
230000001684 chronic effect Effects 0.000 claims description 4
YKJBTFYGGYMXRG-UHFFFAOYSA-N n-[[2-(3-chlorophenyl)tetrazol-5-yl]methyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(Cl)=C1 YKJBTFYGGYMXRG-UHFFFAOYSA-N 0.000 claims description 4
238000001783 near-resonance Rayleigh scattering spectroscopy Methods 0.000 claims description 4
238000002560 therapeutic procedure Methods 0.000 claims description 4
150000004677 hydrates Chemical class 0.000 claims description 3
DPVHQPGVGADSNV-UHFFFAOYSA-N n,4-dimethyl-n-[[2-(3-methylphenyl)tetrazol-5-yl]methyl]-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(C)=C1 DPVHQPGVGADSNV-UHFFFAOYSA-N 0.000 claims description 3
YXVILKGFMGECJM-UHFFFAOYSA-N n-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 YXVILKGFMGECJM-UHFFFAOYSA-N 0.000 claims description 3
SHJRYGHPCXSPDP-UHFFFAOYSA-N 3-[5-[1-(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)N1CCCN2C1=NN=C2C1=CC=NC=C1 SHJRYGHPCXSPDP-UHFFFAOYSA-N 0.000 claims description 2
GKPBQXKXCXURER-UHFFFAOYSA-N 3-[5-[1-[methyl-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)amino]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 GKPBQXKXCXURER-UHFFFAOYSA-N 0.000 claims description 2
YNYJLGIRFUGDEY-UHFFFAOYSA-N 3-[5-[[methyl-(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)amino]methyl]tetrazol-2-yl]benzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(C#N)=C1 YNYJLGIRFUGDEY-UHFFFAOYSA-N 0.000 claims description 2
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 2
BZTXEMPYJURSGN-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 BZTXEMPYJURSGN-UHFFFAOYSA-N 0.000 claims description 2
ADYINAWGQYFZDK-UHFFFAOYSA-N 4-[4-methyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C)N=N2)=C1 ADYINAWGQYFZDK-UHFFFAOYSA-N 0.000 claims description 2
AVXFPSCDBCQXJF-UHFFFAOYSA-N 4-[5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 AVXFPSCDBCQXJF-UHFFFAOYSA-N 0.000 claims description 2
IUJVCUPZEAGDSU-UHFFFAOYSA-N 4-[5-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 IUJVCUPZEAGDSU-UHFFFAOYSA-N 0.000 claims description 2
ZRPKSYNMJBJRIX-UHFFFAOYSA-N 4-[5-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=C(F)C(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C)N=N2)=C1 ZRPKSYNMJBJRIX-UHFFFAOYSA-N 0.000 claims description 2
NEXXZJKDYDTXEJ-UHFFFAOYSA-N 4-[5-[[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]methylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1SCC(=N1)N=NN1C1=CC(Cl)=CC=C1F NEXXZJKDYDTXEJ-UHFFFAOYSA-N 0.000 claims description 2
BSWZFKOFLUNZSS-UHFFFAOYSA-N 5-[1-[[5-(3,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanyl]ethyl]-2-(3-methylphenyl)tetrazole Chemical compound N=1N=C(C=2C=C(F)C=C(F)C=2)N(CC)C=1SC(C)C(=N1)N=NN1C1=CC=CC(C)=C1 BSWZFKOFLUNZSS-UHFFFAOYSA-N 0.000 claims description 2
XDBPPWPUXFQUBP-UHFFFAOYSA-N 9-[1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)N1CCCCN2C1=NN=C2C1=CC=NC=C1 XDBPPWPUXFQUBP-UHFFFAOYSA-N 0.000 claims description 2
XUNQTJIRDMBDPR-UHFFFAOYSA-N 9-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)N1CCCCN2C1=NN=C2C1=CC=NC=C1 XUNQTJIRDMBDPR-UHFFFAOYSA-N 0.000 claims description 2
DZDODDUVZQOUAR-UHFFFAOYSA-N 9-[[2-(3-chlorophenyl)tetrazol-5-yl]methyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound ClC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCCC3)N=N2)=C1 DZDODDUVZQOUAR-UHFFFAOYSA-N 0.000 claims description 2
208000000094 Chronic Pain Diseases 0.000 claims description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 2
208000005298 acute pain Diseases 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
HOUFSJNBIFUWKT-UHFFFAOYSA-N ethyl 4-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C(=CC=C(C)C=2)F)N=N1 HOUFSJNBIFUWKT-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
OYNCUSOSFPTOOL-UHFFFAOYSA-N n-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C=C(I)C=CC=2)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 OYNCUSOSFPTOOL-UHFFFAOYSA-N 0.000 claims description 2
QNSSPKJKXZTNBR-UHFFFAOYSA-N n-[[2-(3-iodophenyl)tetrazol-5-yl]methyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC=CC(I)=C1 QNSSPKJKXZTNBR-UHFFFAOYSA-N 0.000 claims description 2
125000004043 oxo group Chemical group O=* 0.000 claims description 2
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 4
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
125000001963 4 membered heterocyclic group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
ZQOTYMUJVHFJMO-UHFFFAOYSA-N 1-[2-(3-chlorophenyl)tetrazol-5-yl]-2-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethanol Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(O)CC(N1C2CC2)=NN=C1C1=CC=NC=C1 ZQOTYMUJVHFJMO-UHFFFAOYSA-N 0.000 claims 1
PKDPUENCROCRCH-UHFFFAOYSA-N 1-piperazin-1-ylethanone Chemical compound CC(=O)N1CCNCC1 PKDPUENCROCRCH-UHFFFAOYSA-N 0.000 claims 1
BKKWKXDUSCUVDZ-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-(1-phenylprop-1-en-2-yl)tetrazole Chemical compound N1=NN(C=2C=C(Cl)C=CC=2)N=C1C(C)=CC1=CC=CC=C1 BKKWKXDUSCUVDZ-UHFFFAOYSA-N 0.000 claims 1
BMOGSBKIRGTSIJ-SNVBAGLBSA-N 2-(3-chlorophenyl)-5-[(1r)-1-[[5-(3,5-difluorophenyl)-4-methyl-1,2,4-triazol-3-yl]oxy]ethyl]tetrazole Chemical compound O([C@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C1=CC(F)=CC(F)=C1 BMOGSBKIRGTSIJ-SNVBAGLBSA-N 0.000 claims 1
YRKGWCXYMUDYGM-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)tetrazol-5-yl]-1-(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)ethanol Chemical compound N=1N=C(C=2C=CN=CC=2)N(C2CC2)C=1C(O)CC(=N1)N=NN1C1=CC=CC(Cl)=C1 YRKGWCXYMUDYGM-UHFFFAOYSA-N 0.000 claims 1
SGZLSBWGNCQYJP-UHFFFAOYSA-N 2-[5-(5-methylfuran-2-yl)tetrazol-2-yl]-n-(2-phenylbenzotriazol-5-yl)acetamide Chemical compound O1C(C)=CC=C1C1=NN(CC(=O)NC2=CC3=NN(N=C3C=C2)C=2C=CC=CC=2)N=N1 SGZLSBWGNCQYJP-UHFFFAOYSA-N 0.000 claims 1
ZXCMVOMJHFQABJ-CYBMUJFWSA-N 3-[4-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound C1CN([C@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=NC=CN=C1C#N ZXCMVOMJHFQABJ-CYBMUJFWSA-N 0.000 claims 1
ZXCMVOMJHFQABJ-ZDUSSCGKSA-N 3-[4-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyrazine-2-carbonitrile Chemical compound C1CN([C@@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=NC=CN=C1C#N ZXCMVOMJHFQABJ-ZDUSSCGKSA-N 0.000 claims 1
YKMQYRLZYIFWBU-UHFFFAOYSA-N 3-[5-[(3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepin-9-yl)methyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCCC3)N=N2)=C1 YKMQYRLZYIFWBU-UHFFFAOYSA-N 0.000 claims 1
KNUPDYJEUFQYLB-UHFFFAOYSA-N 3-[5-[(3-pyridin-4-yl-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidin-8-yl)methyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCC3)N=N2)=C1 KNUPDYJEUFQYLB-UHFFFAOYSA-N 0.000 claims 1
QAWNJLHEHASGJD-UHFFFAOYSA-N 3-[5-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)sulfanylmethyl]tetrazol-2-yl]benzonitrile Chemical compound N#CC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 QAWNJLHEHASGJD-UHFFFAOYSA-N 0.000 claims 1
KUWCVGDHTYYBSL-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)SC(N1C2CC2)=NN=C1C1=CC=NC=C1 KUWCVGDHTYYBSL-UHFFFAOYSA-N 0.000 claims 1
HMBGXKUWLFCCOG-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(I)C=CC=2)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 HMBGXKUWLFCCOG-UHFFFAOYSA-N 0.000 claims 1
RLOOOHWJTLPJOK-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-iodophenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound IC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 RLOOOHWJTLPJOK-UHFFFAOYSA-N 0.000 claims 1
OPRJFHQMQBEOEB-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=CC(N2N=C(COC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 OPRJFHQMQBEOEB-UHFFFAOYSA-N 0.000 claims 1
RAYPHVILNUIXPW-UHFFFAOYSA-N 4-[4-cyclopropyl-5-[[2-(3-methylphenyl)tetrazol-5-yl]methylsulfanyl]-1,2,4-triazol-3-yl]pyridine Chemical compound CC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 RAYPHVILNUIXPW-UHFFFAOYSA-N 0.000 claims 1
HBTWXQLKSAOIPA-NSHDSACASA-N 4-[5-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound O([C@@H](C)C1=NN(N=N1)C=1C=C(Cl)C=CC=1)C(N1C)=NN=C1C1=CC=NC=C1 HBTWXQLKSAOIPA-NSHDSACASA-N 0.000 claims 1
ANOCVGIRTXMBMF-UHFFFAOYSA-N 4-[5-[1-[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]ethylsulfanyl]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C(=CC=C(Cl)C=2)F)N=C1C(C)SC(N1C)=NN=C1C1=CC=NC=C1 ANOCVGIRTXMBMF-UHFFFAOYSA-N 0.000 claims 1
JAHBCKUCQCXRRL-UHFFFAOYSA-N 4-[5-[[2-(5-chloro-2-fluorophenyl)tetrazol-5-yl]methylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound FC1=CC=C(Cl)C=C1N1N=C(CSC=2N(C(C=3C=CN=CC=3)=NN=2)C2CC2)N=N1 JAHBCKUCQCXRRL-UHFFFAOYSA-N 0.000 claims 1
ZOMNBCKZYULUDN-CQSZACIVSA-N 6-[4-[(1r)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN([C@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=CC=C(C#N)C=N1 ZOMNBCKZYULUDN-CQSZACIVSA-N 0.000 claims 1
ZOMNBCKZYULUDN-AWEZNQCLSA-N 6-[4-[(1s)-1-[2-(3-chlorophenyl)tetrazol-5-yl]ethyl]piperazin-1-yl]pyridine-3-carbonitrile Chemical compound C1CN([C@@H](C)C2=NN(N=N2)C=2C=C(Cl)C=CC=2)CCN1C1=CC=C(C#N)C=N1 ZOMNBCKZYULUDN-AWEZNQCLSA-N 0.000 claims 1
DIOOLZYLVLEVNL-UHFFFAOYSA-N 8-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethyl]-3-(2-methoxypyridin-4-yl)-6,7-dihydro-5h-[1,2,4]triazolo[4,3-a]pyrimidine Chemical compound C1=NC(OC)=CC(C=2N3CCCN(C3=NN=2)C(C)C2=NN(N=N2)C=2C=C(I)C=CC=2)=C1 DIOOLZYLVLEVNL-UHFFFAOYSA-N 0.000 claims 1
DQZBCKPXVHZVHT-UHFFFAOYSA-N 9-[[2-(3-iodophenyl)tetrazol-5-yl]methyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound IC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCCC3)N=N2)=C1 DQZBCKPXVHZVHT-UHFFFAOYSA-N 0.000 claims 1
MPRZKCDFPSPVSI-UHFFFAOYSA-N 9-[[2-(3-methylphenyl)tetrazol-5-yl]methyl]-3-pyridin-4-yl-5,6,7,8-tetrahydro-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound CC1=CC=CC(N2N=C(CN3C=4N(C(=NN=4)C=4C=CN=CC=4)CCCC3)N=N2)=C1 MPRZKCDFPSPVSI-UHFFFAOYSA-N 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
DOLWUAMIJZGVTC-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]pyrimidine Chemical compound N1=CC=CN2C=NN=C21 DOLWUAMIJZGVTC-UHFFFAOYSA-N 0.000 claims 1
239000004480 active ingredient Substances 0.000 claims 1
239000000969 carrier Substances 0.000 claims 1
PMSVVUSIPKHUMT-UHFFFAOYSA-N cyanopyrazine Chemical compound N#CC1=CN=CC=N1 PMSVVUSIPKHUMT-UHFFFAOYSA-N 0.000 claims 1
VMGBXXDDLLFQDH-UHFFFAOYSA-N ethyl 4-[[2-(3-cyanophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(C=CC=2)C#N)N=N1 VMGBXXDDLLFQDH-UHFFFAOYSA-N 0.000 claims 1
MTGWILXIKBIHEP-UHFFFAOYSA-N n-[1-[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]ethyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N1=NN(C=2C(=CC=C(C)C=2)F)N=C1C(C)N(C)C(N1C)=NN=C1C1=CC=NC=C1 MTGWILXIKBIHEP-UHFFFAOYSA-N 0.000 claims 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
230000004913 activation Effects 0.000 description 14
102000005962 receptors Human genes 0.000 description 12
108020003175 receptors Proteins 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 11
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 8
229930195712 glutamate Natural products 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
125000004076 pyridyl group Chemical group 0.000 description 8
210000003169 central nervous system Anatomy 0.000 description 7
208000021302 gastroesophageal reflux disease Diseases 0.000 description 7
210000000111 lower esophageal sphincter Anatomy 0.000 description 7
210000002569 neuron Anatomy 0.000 description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
230000005284 excitation Effects 0.000 description 6
238000010992 reflux Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
230000000694 effects Effects 0.000 description 4
125000002883 imidazolyl group Chemical group 0.000 description 4
238000000034 method Methods 0.000 description 4
125000002971 oxazolyl group Chemical group 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
230000008569 process Effects 0.000 description 4
125000002098 pyridazinyl group Chemical group 0.000 description 4
125000000335 thiazolyl group Chemical group 0.000 description 4
125000001544 thienyl group Chemical group 0.000 description 4
230000001052 transient effect Effects 0.000 description 4
125000001425 triazolyl group Chemical group 0.000 description 4
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
208000008589 Obesity Diseases 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
208000027520 Somatoform disease Diseases 0.000 description 3
239000000556 agonist Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000002619 bicyclic group Chemical group 0.000 description 3
239000011575 calcium Substances 0.000 description 3
210000004027 cell Anatomy 0.000 description 3
210000003238 esophagus Anatomy 0.000 description 3
125000002541 furyl group Chemical group 0.000 description 3
125000000623 heterocyclic group Chemical group 0.000 description 3
125000000592 heterocycloalkyl group Chemical group 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000003834 intracellular effect Effects 0.000 description 3
125000002757 morpholinyl group Chemical group 0.000 description 3
230000001537 neural effect Effects 0.000 description 3
235000020824 obesity Nutrition 0.000 description 3
208000027753 pain disease Diseases 0.000 description 3
125000004928 piperidonyl group Chemical group 0.000 description 3
230000001242 postsynaptic effect Effects 0.000 description 3
125000003373 pyrazinyl group Chemical group 0.000 description 3
125000003072 pyrazolidinyl group Chemical group 0.000 description 3
125000002755 pyrazolinyl group Chemical group 0.000 description 3
125000000719 pyrrolidinyl group Chemical group 0.000 description 3
125000001422 pyrrolinyl group Chemical group 0.000 description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
125000003831 tetrazolyl group Chemical group 0.000 description 3
125000004568 thiomorpholinyl group Chemical group 0.000 description 3
TYNNZACKVXTHRJ-UHFFFAOYSA-N (2-phenyltetrazol-5-yl)-piperidin-1-ylmethanol Chemical compound N1=NN(C=2C=CC=CC=2)N=C1C(O)N1CCCCC1 TYNNZACKVXTHRJ-UHFFFAOYSA-N 0.000 description 2
JVVUGMRDYFKVPB-UHFFFAOYSA-N 1-[(2-phenyltetrazol-5-yl)methyl]-2h-pyridine Chemical compound N1=NN(C=2C=CC=CC=2)N=C1CN1CC=CC=C1 JVVUGMRDYFKVPB-UHFFFAOYSA-N 0.000 description 2
UOUITGOVEQDAEO-UHFFFAOYSA-N 2,3-dihydro-1h-tetrazolo[1,5-a]azepine Chemical compound C1=CC=CC=C2NNNN21 UOUITGOVEQDAEO-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
101150018425 Cr1l gene Proteins 0.000 description 2
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
102000014384 Type C Phospholipases Human genes 0.000 description 2
108010079194 Type C Phospholipases Proteins 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
125000005213 alkyl heteroaryl group Chemical group 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
125000003725 azepanyl group Chemical group 0.000 description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 2
125000002393 azetidinyl group Chemical group 0.000 description 2
230000004888 barrier function Effects 0.000 description 2
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
125000005872 benzooxazolyl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
ZOOGRGPOEVQQDX-KHLHZJAASA-N cyclic guanosine monophosphate Chemical compound C([C@H]1O2)O[P@](O)(=O)O[C@@H]1[C@H](O)[C@H]2N1C(N=C(NC2=O)N)=C2N=C1 ZOOGRGPOEVQQDX-KHLHZJAASA-N 0.000 description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
230000007423 decrease Effects 0.000 description 2
125000005959 diazepanyl group Chemical group 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000027119 gastric acid secretion Effects 0.000 description 2
125000005945 imidazopyridyl group Chemical group 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
230000000926 neurological effect Effects 0.000 description 2
125000005961 oxazepanyl group Chemical group 0.000 description 2
125000003551 oxepanyl group Chemical group 0.000 description 2
230000036407 pain Effects 0.000 description 2
230000007170 pathology Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
150000003906 phosphoinositides Chemical class 0.000 description 2
125000003386 piperidinyl group Chemical group 0.000 description 2
230000003518 presynaptic effect Effects 0.000 description 2
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 2
125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 2
125000003226 pyrazolyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl group Chemical group 0.000 description 2
125000000168 pyrrolyl group Chemical group 0.000 description 2
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 2
210000002784 stomach Anatomy 0.000 description 2
150000003536 tetrazoles Chemical class 0.000 description 2
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 description 1
125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 description 1
CGSQUVFUQHCEEI-UHFFFAOYSA-N 1-[(2-phenyltetrazol-5-yl)methyl]piperidine Chemical compound N1=NN(C=2C=CC=CC=2)N=C1CN1CCCCC1 CGSQUVFUQHCEEI-UHFFFAOYSA-N 0.000 description 1
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
DUWWRSFBHUBVGQ-UHFFFAOYSA-N 3-[4-methyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethylsulfanyl]-1,2,4-triazol-3-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)SC(N1C)=NN=C1C1=CC=CC(C#N)=C1 DUWWRSFBHUBVGQ-UHFFFAOYSA-N 0.000 description 1
QVHFWIURBFHEIS-UHFFFAOYSA-N 3-[5-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxymethyl]tetrazol-2-yl]benzonitrile Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1OCC(=N1)N=NN1C1=CC=CC(C#N)=C1 QVHFWIURBFHEIS-UHFFFAOYSA-N 0.000 description 1
RRUFGIVOAHHNNN-UHFFFAOYSA-N 3-[5-[1-[(4-cyclopropyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)oxy]ethyl]tetrazol-2-yl]benzonitrile Chemical compound N1=NN(C=2C=C(C=CC=2)C#N)N=C1C(C)OC(N1C2CC2)=NN=C1C1=CC=NC=C1 RRUFGIVOAHHNNN-UHFFFAOYSA-N 0.000 description 1
GFHXCIQYLRWQCU-UHFFFAOYSA-N 3H-[1,2,4]triazolo[4,3-a][1,3]diazepine Chemical compound N1=NCN2C=CC=CN=C12 GFHXCIQYLRWQCU-UHFFFAOYSA-N 0.000 description 1
UWZNWNNKHSVQEC-UHFFFAOYSA-N 4-[4-methyl-5-[1-[2-(3-methylphenyl)tetrazol-5-yl]ethoxy]-1,2,4-triazol-3-yl]pyridine Chemical compound N1=NN(C=2C=C(C)C=CC=2)N=C1C(C)OC(N1C)=NN=C1C1=CC=NC=C1 UWZNWNNKHSVQEC-UHFFFAOYSA-N 0.000 description 1
KQPUIRVPYTXQSS-UHFFFAOYSA-N 4-[5-[1-[2-(3-iodophenyl)tetrazol-5-yl]ethoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine 4-[5-[[2-(3-iodophenyl)tetrazol-5-yl]methoxy]-4-methyl-1,2,4-triazol-3-yl]pyridine Chemical compound IC=1C=C(C=CC1)N1N=C(N=N1)C(C)OC=1N(C(=NN1)C1=CC=NC=C1)C.IC=1C=C(C=CC1)N1N=C(N=N1)COC=1N(C(=NN1)C1=CC=NC=C1)C KQPUIRVPYTXQSS-UHFFFAOYSA-N 0.000 description 1
IIGFWFGPJPEQAS-UHFFFAOYSA-N 4-[5-[[2-(3-chlorophenyl)tetrazol-5-yl]methylsulfanyl]-4-cyclopropyl-1,2,4-triazol-3-yl]pyridine Chemical compound ClC1=CC=CC(N2N=C(CSC=3N(C(C=4C=CN=CC=4)=NN=3)C3CC3)N=N2)=C1 IIGFWFGPJPEQAS-UHFFFAOYSA-N 0.000 description 1
BFTYPTVEAUOSMJ-UHFFFAOYSA-N 5-[[5-(3,5-difluorophenyl)-4-ethyl-1,2,4-triazol-3-yl]sulfanylmethyl]-2-(3-methylphenyl)tetrazole Chemical compound N=1N=C(C=2C=C(F)C=C(F)C=2)N(CC)C=1SCC(=N1)N=NN1C1=CC=CC(C)=C1 BFTYPTVEAUOSMJ-UHFFFAOYSA-N 0.000 description 1
235000014621 Aiphanes minima Nutrition 0.000 description 1
240000000396 Aiphanes minima Species 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
102000000844 Cell Surface Receptors Human genes 0.000 description 1
108010001857 Cell Surface Receptors Proteins 0.000 description 1
208000030814 Eating disease Diseases 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
208000019454 Feeding and Eating disease Diseases 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
108010078321 Guanylate Cyclase Proteins 0.000 description 1
102000014469 Guanylate cyclase Human genes 0.000 description 1
206010019196 Head injury Diseases 0.000 description 1
241000167880 Hirundinidae Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
102000006541 Ionotropic Glutamate Receptors Human genes 0.000 description 1
108010008812 Ionotropic Glutamate Receptors Proteins 0.000 description 1
108090000543 Ligand-Gated Ion Channels Proteins 0.000 description 1
102000004086 Ligand-Gated Ion Channels Human genes 0.000 description 1
102100036834 Metabotropic glutamate receptor 1 Human genes 0.000 description 1
102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 description 1
102000011420 Phospholipase D Human genes 0.000 description 1
108090000553 Phospholipase D Proteins 0.000 description 1
102000015439 Phospholipases Human genes 0.000 description 1
108010064785 Phospholipases Proteins 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
102000030621 adenylate cyclase Human genes 0.000 description 1
108060000200 adenylate cyclase Proteins 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
150000001413 amino acids Chemical group 0.000 description 1
230000036592 analgesia Effects 0.000 description 1
229940035676 analgesics Drugs 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
230000001640 apoptogenic effect Effects 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000001638 cerebellum Anatomy 0.000 description 1
210000003710 cerebral cortex Anatomy 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
238000003745 diagnosis Methods 0.000 description 1
125000006006 difluoroethoxy group Chemical group 0.000 description 1
125000006001 difluoroethyl group Chemical group 0.000 description 1
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 1
125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 description 1
201000010099 disease Diseases 0.000 description 1
235000014632 disordered eating Nutrition 0.000 description 1
239000003596 drug target Substances 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
FLINNCJLYXBVMD-UHFFFAOYSA-N ethyl 4-[[2-(3-chlorophenyl)tetrazol-5-yl]methyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCN1CC1=NN(C=2C=C(Cl)C=CC=2)N=N1 FLINNCJLYXBVMD-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000002964 excitative effect Effects 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
230000037406 food intake Effects 0.000 description 1
235000012631 food intake Nutrition 0.000 description 1
239000012634 fragment Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
230000000971 hippocampal effect Effects 0.000 description 1
210000001320 hippocampus Anatomy 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000002218 hypoglycaemic effect Effects 0.000 description 1
125000002632 imidazolidinyl group Chemical group 0.000 description 1
125000002636 imidazolinyl group Chemical group 0.000 description 1
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
230000006698 induction Effects 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
230000001057 ionotropic effect Effects 0.000 description 1
208000037906 ischaemic injury Diseases 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
230000020796 long term synaptic depression Effects 0.000 description 1
230000027928 long-term synaptic potentiation Effects 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000010369 molecular cloning Methods 0.000 description 1
VLWCHPQMDNHKFE-UHFFFAOYSA-N n-[[2-(2-fluoro-5-methylphenyl)tetrazol-5-yl]methyl]-n,4-dimethyl-5-pyridin-4-yl-1,2,4-triazol-3-amine Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1N(C)CC(=N1)N=NN1C1=CC(C)=CC=C1F VLWCHPQMDNHKFE-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
208000015122 neurodegenerative disease Diseases 0.000 description 1
230000007472 neurodevelopment Effects 0.000 description 1
230000016273 neuron death Effects 0.000 description 1
239000004090 neuroprotective agent Substances 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
230000003957 neurotransmitter release Effects 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
125000001715 oxadiazolyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000001991 pathophysiological effect Effects 0.000 description 1
230000035778 pathophysiological process Effects 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
238000001050 pharmacotherapy Methods 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000005494 pyridonyl group Chemical group 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
230000020341 sensory perception of pain Effects 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
230000003956 synaptic plasticity Effects 0.000 description 1
230000005062 synaptic transmission Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
210000001103 thalamus Anatomy 0.000 description 1
125000001113 thiadiazolyl group Chemical group 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
208000016752 upper digestive tract disease Diseases 0.000 description 1
230000004462 vestibulo-ocular reflex Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
230000031836 visual learning Effects 0.000 description 1
230000002618 waking effect Effects 0.000 description 1

Classifications

- 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
- 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
- A61P1/06—Anti-spasmodics, e.g. drugs for colics, esophagic 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Pain & Pain Management (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

ZA200606594A 2004-02-18 2006-08-08 Tetrazole compounds and their use as metabotropic glutamate receptor antagonists ZA200606594B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US54529104P	2004-02-18	2004-02-18

Publications (1)

Publication Number	Publication Date
ZA200606594B true ZA200606594B (en)	2007-11-28

Family

ID=34886129

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ZA200606594A ZA200606594B (en)	2004-02-18	2006-08-08	Tetrazole compounds and their use as metabotropic glutamate receptor antagonists

Country Status (20)

Country	Link
US (2)	US20070197549A1 (zh)
EP (1)	EP1716125B1 (zh)
JP (1)	JP5084269B2 (zh)
KR (1)	KR20070027504A (zh)
CN (2)	CN1918137B (zh)
AR (1)	AR047812A1 (zh)
AU (1)	AU2005214379B2 (zh)
BR (1)	BRPI0507498A (zh)
CA (1)	CA2556263A1 (zh)
IL (1)	IL177056A0 (zh)
MX (1)	MXPA06009019A (zh)
MY (1)	MY145075A (zh)
NO (1)	NO20063470L (zh)
RU (1)	RU2372347C2 (zh)
SG (1)	SG150539A1 (zh)
TW (1)	TW200533664A (zh)
UA (1)	UA85576C2 (zh)
UY (1)	UY28763A1 (zh)
WO (1)	WO2005080356A1 (zh)
ZA (1)	ZA200606594B (zh)

Families Citing this family (54)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2005214380A1 (en)	2004-02-18	2005-09-01	Astrazeneca Ab	Fused hetrocyclic compounds and their use as metabotropic receptor antagonists for the treatment of gastrointestinal disorders
AU2005214379B2 (en) *	2004-02-18	2012-03-22	Astrazeneca Ab	Tetrazole compounds and their use as metabotropic glutamate receptor antagonits
GB0420722D0 (en)	2004-09-17	2004-10-20	Addex Pharmaceuticals Sa	Novel allosteric modulators
WO2006080533A1 (ja) *	2005-01-31	2006-08-03	Mochida Pharmaceutical Co., Ltd.	３－アミノ－１,２,４－トリアゾール誘導体
US7964619B2 (en)	2005-06-03	2011-06-21	The University Of North Carolina At Chapel Hill	Teraryl components as antiparasitic agents
US8101636B2 (en) *	2005-06-03	2012-01-24	The University Of North Carolina At Chapel Hill	Linear dicationic terphenyls and their aza analogues as antiparasitic agents
UY29796A1 (es)	2005-09-29	2007-04-30	Astrazeneca Ab	Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor
HUP0500921A2 (en) *	2005-10-05	2007-07-30	Richter Gedeon Nyrt	Tetrazole derivatives, process for their preparation and their use
TWI417095B (zh)	2006-03-15	2013-12-01	Janssen Pharmaceuticals Inc	１，４-二取代之３-氰基-吡啶酮衍生物及其作為ｍＧｌｕＲ２-受體之正向異位性調節劑之用途
TW200811179A (en) *	2006-05-05	2008-03-01	Astrazeneca Ab	mGluR5 modulators VI
TW200808800A (en) *	2006-05-05	2008-02-16	Astrazeneca Ab	MGluR5 modulators V
TW200811157A (en)	2006-05-05	2008-03-01	Astrazeneca Ab	mGluR5 modulators I
AR065622A1 (es) *	2007-03-07	2009-06-17	Ortho Mcneil Janssen Pharm	Derivados de 3-ciano -4- (4-fenil- piperidin -1- il) piridin -2- ona
TW200845978A (en) *	2007-03-07	2008-12-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
TW200900065A (en) *	2007-03-07	2009-01-01	Janssen Pharmaceutica Nv	3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
MX2010002537A (es) *	2007-09-14	2010-08-10	Ortho Mcneil Janssen Pharm	4-fenil-1h-piridin-2-onas 1,3-disubstituidas.
DK2203439T3 (da)	2007-09-14	2011-04-18	Ortho Mcneil Janssen Pharm	1',3'-disubstituerede 4-phenyl-3,4,5,6-tetrahydro-2H,1'H-[1,4']-bipyridinyl-2'-oner
PL2200985T3 (pl)	2007-09-14	2011-12-30	Ortho Mcneil Janssen Pharmaceuticals Inc	1,3-Dipodstawione-4-(arylo-X-fenylo)-1H-pirydyn-2-ony
MX2010004272A (es) *	2007-10-19	2010-04-30	Astrazeneca Ab	Derivados de tetrazol como moduladores de receptores de glutamato metabotropicos (mglurs).
WO2009054785A1 (en) *	2007-10-26	2009-04-30	Astrazeneca Ab	1,2,4-triazole ether derivatives as modulators of mglur5
WO2009054794A1 (en) *	2007-10-26	2009-04-30	Astrazeneca Ab	Amino 1,2,4-triazole derivatives as modulators of mglur5
JP5433582B2 (ja)	2007-11-14	2014-03-05	ジャンセンファーマシューティカルズ，インコーポレイテッド．	イミダゾ［１，２−ａ］ピリジン誘導体およびｍＧｌｕＲ２受容体の正のアロステリック調節因子としてのその使用
HUE035295T2 (en)	2008-08-06	2018-05-02	Medivation Technologies Inc	Dihydropyridophthalazinone inhibitors of poly(ADP-ribose)polymerase (PARP)
CA2735764C (en)	2008-09-02	2016-06-14	Ortho-Mcneil-Janssen Pharmaceuticals, Inc.	3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors
CA2738849C (en)	2008-10-16	2016-06-28	Addex Pharma S.A.	Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors
CA2744138C (en)	2008-11-28	2015-08-11	Ortho-Mcneil-Janssen Pharmaceuticals, Inc.	Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors
WO2010068172A1 (en) *	2008-12-12	2010-06-17	Astrazeneca Ab	A new process for preparing 4- [4-methyl-5- (cl- 10alkylthio/c5-10aryl-cl-6alkylthio) -4h-1, 2, 4-triazol-3- yl] pyridines.
US20110306768A1 (en) *	2008-12-18	2011-12-15	Astrazeneca Ab	Processes for the manufacture of 3--pyridine, 4-methyl-3-methylthio-5-(3-pyridyl)-l,2,4-triazole, and (1r)-1-[2-(3-methylphenyl)-2h-tetrazol-5-yl]ethanol
US8349852B2 (en)	2009-01-13	2013-01-08	Novartis Ag	Quinazolinone derivatives useful as vanilloid antagonists
US20100273805A1 (en) *	2009-04-23	2010-10-28	Astrazeneca Ab	Sulphide bridged derivatives as modulators of mglur5 733
MY153913A (en)	2009-05-12	2015-04-15	Janssen Pharmaceuticals Inc	7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
EA020671B1 (ru)	2009-05-12	2014-12-30	Янссен Фармасьютикалз, Инк.	ПРОИЗВОДНЫЕ 1,2,4-ТРИАЗОЛО[4,3-a]ПИРИДИНА И ИХ ПРИМЕНЕНИЕ В КАЧЕСТВЕ ПОЛОЖИТЕЛЬНЫХ АЛЛОСТЕРИЧЕСКИХ МОДУЛЯТОРОВ РЕЦЕПТОРОВ mGluR2
PT2430022E (pt)	2009-05-12	2013-12-26	Janssen Pharmaceuticals Inc	Derivados de 1,2,3-triazolo[4,3-a]piridina e a sua utilização para o tratamento ou prevenção de doenças neurológicas e psiquiátricas
EP2438052A1 (en)	2009-06-05	2012-04-11	Oslo University Hospital HF	Azole derivatives as wtn pathway inhibitors
WO2011082010A1 (en) *	2009-12-29	2011-07-07	Eli Lilly And Company	Tetrahydrotriazolopyridine compounds as selective mglu5 receptor potentiators useful for the treatment of schizophrenia
US20120295942A1 (en)	2010-02-01	2012-11-22	Nicholas James Devereux	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
WO2011095450A1 (en)	2010-02-02	2011-08-11	Novartis Ag	Cyclohexyl amide derivatives as crf receptor antagonists
JP5883397B2 (ja)	2010-02-03	2016-03-15	ビオマリンプハルマセウトイカルインコーポレイテッド	Ｐｔｅｎ欠損に関連した疾患の治療におけるポリ（ａｄｐリボース）ポリメラーゼ（ｐａｒｐ）のジヒドロピリドフタラジノン阻害剤の使用
SI2533640T1 (sl)	2010-02-08	2017-02-28	Medivation Technologies, Inc.	Postopki sinteze derivatov dihidropiridoftalazinona
JP2013540158A (ja)	2010-10-21	2013-10-31	ビオマリンプハルマセウトイカルインコーポレイテッド	結晶性（８Ｓ，９Ｒ）−５−フルオロ−８−（４−フルオロフェニル）−９−（１−メチル−１Ｈ−１，２，４−トリアゾール−５−イル）−８，９−ジヒドロ−２Ｈ−ピリド［４，３，２−ｄｅ］フタラジン−３（７Ｈ）−オントシレート塩
US9271967B2 (en)	2010-11-08	2016-03-01	Janssen Pharmaceuticals, Inc.	1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
ES2536433T3 (es)	2010-11-08	2015-05-25	Janssen Pharmaceuticals, Inc.	Derivados de 1,2,4-triazolo[4,3-a]piridina y su uso como moduladores alostéricos positivos de receptores mGluR2
WO2012062759A1 (en)	2010-11-08	2012-05-18	Janssen Pharmaceuticals, Inc.	1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
CA2820800A1 (en)	2010-12-08	2012-06-14	Oslo University Hospital Hf	Triazole derivatives as wnt signaling pathway inhibitors
KR101235100B1 (ko) *	2010-12-15	2013-02-20	서강대학교산학협력단	트리아졸을 포함하는 삼중연결고리 3차 아민 화합물, 이의 제조방법 및 응용
US9199975B2 (en)	2011-09-30	2015-12-01	Asana Biosciences, Llc	Biaryl imidazole derivatives for regulating CYP17
US8809372B2 (en)	2011-09-30	2014-08-19	Asana Biosciences, Llc	Pyridine derivatives
JO3368B1 (ar)	2013-06-04	2019-03-13	Janssen Pharmaceutica Nv	مركبات 6، 7- ثاني هيدرو بيرازولو [5،1-a] بيرازين- 4 (5 يد)- اون واستخدامها بصفة منظمات تفارغية سلبية لمستقبلات ميجلور 2
JO3367B1 (ar)	2013-09-06	2019-03-13	Janssen Pharmaceutica Nv	مركبات 2،1، 4- ثلاثي زولو [3،4-a] بيريدين واستخدامها بصفة منظمات تفارغية موجبة لمستقبلات ميجلور 2
US20160280691A1 (en)	2013-11-07	2016-09-29	Biomarin Pharmaceutical Inc.	Triazole intermediates useful in the synthesis of protected n-alkyltriazolecarbaldehydes
UA128346C2 (uk)	2014-01-21	2024-06-19	Янссен Фармацевтика Нв	Комбінації, які містять позитивні алостеричні модулятори або ортостеричні агоністи метаботропного глутаматергічного рецептора 2 підтипу, та їх застосування
KR20200036063A (ko)	2014-01-21	2020-04-06	얀센 파마슈티카 엔.브이.	대사 조절형 글루탐산 작동성 수용체 제2아형의 양성 알로스테릭 조절제 또는 오르토스테릭 작동제를 포함하는 조합 및 그 용도
CN111269192A (zh) *	2020-02-25	2020-06-12	成都睿智化学研究有限公司	一种5-羟甲基四氮唑及其衍生物的合成方法

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3509153A (en) *	1967-03-24	1970-04-28	Miles Lab	5-phenyl (or 5-phenylalkyl)-2-(omega-(4-phenyl-1-piperazinyl)alkyl)tetrazoles
US4663332A (en) *	1985-10-10	1987-05-05	Hoffman-La Roche Inc.	5-substituted N-alkylated tetrazoles
AU2363492A (en)	1991-08-03	1993-03-02	Smithkline Beecham Plc	5-ht4 receptor antagonists
DE10023430A1 (de)	2000-05-12	2001-11-15	Bayer Ag	Substituierte N-Benzoyl-N'-(tetrazolylphenyl)-harnstoffe
GB0115862D0 (en)	2001-06-28	2001-08-22	Smithkline Beecham Plc	Compounds
GB0121033D0 (en)	2001-08-30	2001-10-24	Novartis Ag	Organic compounds
CA2462289C (en) *	2001-10-04	2010-02-23	Nicholas D. Cosford	Heteroaryl substituted tetrazole modulators of metabotropic glutamate receptor-5
WO2003051833A2 (en) *	2001-12-18	2003-06-26	Merck & Co., Inc.	Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5
US7592337B2 (en) *	2002-03-12	2009-09-22	Merck & Co., Inc.	Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5
AU2005214379B2 (en) *	2004-02-18	2012-03-22	Astrazeneca Ab	Tetrazole compounds and their use as metabotropic glutamate receptor antagonits

2005
- 2005-02-17 AU AU2005214379A patent/AU2005214379B2/en not_active Expired - Fee Related
- 2005-02-17 EP EP05713793.7A patent/EP1716125B1/en not_active Expired - Lifetime
- 2005-02-17 CN CN2005800043701A patent/CN1918137B/zh not_active Expired - Fee Related
- 2005-02-17 JP JP2006554236A patent/JP5084269B2/ja not_active Expired - Fee Related
- 2005-02-17 US US10/588,756 patent/US20070197549A1/en not_active Abandoned
- 2005-02-17 KR KR1020067015943A patent/KR20070027504A/ko not_active Ceased
- 2005-02-17 MX MXPA06009019A patent/MXPA06009019A/es active IP Right Grant
- 2005-02-17 WO PCT/US2005/005217 patent/WO2005080356A1/en active Application Filing
- 2005-02-17 CA CA002556263A patent/CA2556263A1/en not_active Abandoned
- 2005-02-17 BR BRPI0507498-3A patent/BRPI0507498A/pt not_active IP Right Cessation
- 2005-02-17 MY MYPI20050601A patent/MY145075A/en unknown
- 2005-02-17 RU RU2006127573/04A patent/RU2372347C2/ru not_active IP Right Cessation
- 2005-02-17 UA UAA200608678A patent/UA85576C2/ru unknown
- 2005-02-17 CN CN201010113361A patent/CN101845023A/zh active Pending
- 2005-02-17 SG SG200901214-7A patent/SG150539A1/en unknown
- 2005-02-17 TW TW094104641A patent/TW200533664A/zh unknown
- 2005-02-18 UY UY28763A patent/UY28763A1/es unknown
- 2005-02-18 US US11/060,463 patent/US7691892B2/en not_active Expired - Fee Related
- 2005-02-18 AR ARP050100615A patent/AR047812A1/es unknown
2006
- 2006-07-25 IL IL177056A patent/IL177056A0/en unknown
- 2006-07-28 NO NO20063470A patent/NO20063470L/no not_active Application Discontinuation
- 2006-08-08 ZA ZA200606594A patent/ZA200606594B/en unknown

Also Published As

Publication number	Publication date
CN1918137B (zh)	2012-08-01
AR047812A1 (es)	2006-02-22
US20060004021A1 (en)	2006-01-05
MY145075A (en)	2011-12-15
WO2005080356A1 (en)	2005-09-01
UA85576C2 (ru)	2009-02-10
JP5084269B2 (ja)	2012-11-28
KR20070027504A (ko)	2007-03-09
US7691892B2 (en)	2010-04-06
RU2006127573A (ru)	2008-03-27
CN1918137A (zh)	2007-02-21
JP2007523182A (ja)	2007-08-16
EP1716125A1 (en)	2006-11-02
RU2372347C2 (ru)	2009-11-10
BRPI0507498A (pt)	2007-07-10
AU2005214379B2 (en)	2012-03-22
AU2005214379A1 (en)	2005-09-01
CA2556263A1 (en)	2005-09-01
MXPA06009019A (es)	2007-03-08
CN101845023A (zh)	2010-09-29
NO20063470L (no)	2006-11-17
IL177056A0 (en)	2006-12-10
TW200533664A (en)	2005-10-16
SG150539A1 (en)	2009-03-30
EP1716125B1 (en)	2013-06-19
UY28763A1 (es)	2005-06-30
US20070197549A1 (en)	2007-08-23

Publication	Publication Date	Title
ZA200606594B (en)	2007-11-28	Tetrazole compounds and their use as metabotropic glutamate receptor antagonists
CN105764514B (zh)	2019-07-12	作为tam族激酶抑制剂的氨基吡啶衍生物
US8163756B2 (en)	2012-04-24	Enzyme modulators and treatments
EP2049515B1 (en)	2011-01-26	Triazolyl pyridyl benzenesulfonamides as ccr2 or ccr9 modulators for the treatment of atherosclerosis
CN101208311B (zh)	2013-06-12	作为mGluR5拮抗剂的吡嗪-2-甲酰胺衍生物
JP6346862B2 (ja)	2018-06-20	オレキシンレセプターアンタゴニストとしての置換プロリン／ピペリジン
CN1960984B (zh)	2010-05-12	作为mglu5受体拮抗剂的吡啶-4-基-乙炔基-咪唑和吡唑
KR100742019B1 (ko)	2007-07-23	이미다졸-4-일-에티닐-피리딘 유도체
TW200306824A (en)	2003-12-01	Tachykinin receptor antagonists
AU2008277730A1 (en)	2009-01-22	Pyrazole derivatives as modulators of metabotropic glutamate receptors
WO2012009009A2 (en)	2012-01-19	Novel 2-amino-4-pyrazolyl-thiazole derivatives and their use as allosteric modulators of metabotropic glutamate receptors
EP2376486B1 (en)	2013-11-06	Novel thiazoles derivatives and their use as positive allosteric modulators of metabotropic glutamate receptors
CN100408572C (zh)	2008-08-06	作为谷氨酸受体拮抗剂的咪唑衍生物
US12233065B2 (en)	2025-02-25	Inhibitors of RNA helicase DHX9 and uses thereof
JP5753626B2 (ja)	2015-07-22	ピラゾリジン−３−オン誘導体
AU2011333427A1 (en)	2013-04-11	4- (5-cyano-pyrazol-1-yl) -piperidine derivatives as GPR 119 modulators
US20080064682A1 (en)	2008-03-13	Pyrazole Derivatives
TWI252849B (en)	2006-04-11	Imidazole derivatives III
WO2006043594A1 (ja)	2006-04-27	１，５－ジ複素環－１ｈ－トリアゾール誘導体
ZA200606508B (en)	2007-11-28	Fused heterocyclic compounds and their use as metabotro-pic receptor antagonists for the treatment of gastrointestinal disorders
AU2012247654B2 (en)	2016-05-12	Pyrazolidin-3-one derivatives