NO312297B1 - Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament - Google Patents
Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament Download PDFInfo
- Publication number
- NO312297B1 NO312297B1 NO19991150A NO991150A NO312297B1 NO 312297 B1 NO312297 B1 NO 312297B1 NO 19991150 A NO19991150 A NO 19991150A NO 991150 A NO991150 A NO 991150A NO 312297 B1 NO312297 B1 NO 312297B1
- Authority
- NO
- Norway
- Prior art keywords
- benzenesulfonyl
- pyrazolo
- methyl
- methylsulfanyl
- pyrimidine
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 10
- 229940079593 drug Drugs 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 8
- APXRHPDHORGIEB-UHFFFAOYSA-N 1H-pyrazolo[4,3-d]pyrimidine Chemical class N1=CN=C2C=NNC2=C1 APXRHPDHORGIEB-UHFFFAOYSA-N 0.000 title description 2
- PEYVWBGHBCDXRT-UHFFFAOYSA-N N1=NNC2=CN=NC2=C1 Chemical class N1=NNC2=CN=NC2=C1 PEYVWBGHBCDXRT-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 64
- -1 di-lower-alkyl-amino Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 208000024827 Alzheimer disease Diseases 0.000 claims description 7
- 208000023105 Huntington disease Diseases 0.000 claims description 7
- 208000026139 Memory disease Diseases 0.000 claims description 7
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 208000025966 Neurological disease Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- MAUMSNABMVEOGP-UHFFFAOYSA-N (methyl-$l^{2}-azanyl)methane Chemical compound C[N]C MAUMSNABMVEOGP-UHFFFAOYSA-N 0.000 claims description 6
- 208000020925 Bipolar disease Diseases 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 208000020401 Depressive disease Diseases 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- VFCWRGUKFKHOAB-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C VFCWRGUKFKHOAB-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- CCEJDZJFMKQICA-UHFFFAOYSA-N 10-(benzenesulfonyl)-11-ethyl-2-piperazin-1-yl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(CC)=NN2C=1N1CCNCC1 CCEJDZJFMKQICA-UHFFFAOYSA-N 0.000 claims description 3
- UDOLYSWYIJXJRX-UHFFFAOYSA-N 10-(benzenesulfonyl)-2-(4-methylpiperazin-1-yl)-11-methylsulfanyl-1,8,12-triazatricyclo[7.3.0.03,7]dodeca-2,7,9,11-tetraene Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCN(C)CC1 UDOLYSWYIJXJRX-UHFFFAOYSA-N 0.000 claims description 3
- WEUOAFDJWUMTLR-UHFFFAOYSA-N 2-[3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-5-yl]oxyethanol Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(OCCO)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WEUOAFDJWUMTLR-UHFFFAOYSA-N 0.000 claims description 3
- LVVLVQQEHHNMTM-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(F)C=C1 LVVLVQQEHHNMTM-UHFFFAOYSA-N 0.000 claims description 3
- IOMUIPHNKVJREA-UHFFFAOYSA-N 3-(4-tert-butylphenyl)sulfonyl-5-methyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)(C)C)C=C1 IOMUIPHNKVJREA-UHFFFAOYSA-N 0.000 claims description 3
- LCERYWUKXGPGNQ-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-5-propan-2-ylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 LCERYWUKXGPGNQ-UHFFFAOYSA-N 0.000 claims description 3
- KDPDMXQMBHTUHG-UHFFFAOYSA-N 3-(benzenesulfonyl)-2-methylsulfanyl-7-piperazin-1-yl-5-propylpyrazolo[1,5-a]pyrimidine Chemical compound N12N=C(SC)C(S(=O)(=O)C=3C=CC=CC=3)=C2N=C(CCC)C=C1N1CCNCC1 KDPDMXQMBHTUHG-UHFFFAOYSA-N 0.000 claims description 3
- WRCGHUOBWDSGJY-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-[(dimethylamino)methyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(CN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 WRCGHUOBWDSGJY-UHFFFAOYSA-N 0.000 claims description 3
- NBTJXYKEPGRADD-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NBTJXYKEPGRADD-UHFFFAOYSA-N 0.000 claims description 3
- SRMFGSKGKUHKCH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 SRMFGSKGKUHKCH-UHFFFAOYSA-N 0.000 claims description 3
- ACAVEAGQNALEAY-UHFFFAOYSA-N 3-benzenesulphonyl-2-methylsulphanyl-6,7-dihydro-5h-cyclopenta[d]pyrazolo[1,5-a]pyrimidin-8-ylamine Chemical compound CSC1=NN2C(N)=C3CCCC3=NC2=C1S(=O)(=O)C1=CC=CC=C1 ACAVEAGQNALEAY-UHFFFAOYSA-N 0.000 claims description 3
- WTLHPKQGVWVPFJ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N)N4N=C3SC)=CC=C21 WTLHPKQGVWVPFJ-UHFFFAOYSA-N 0.000 claims description 3
- HCYCQIRHCHFSLZ-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-7-piperazin-1-yl-3-thiophen-2-ylsulfonylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCNCC3)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CS1 HCYCQIRHCHFSLZ-UHFFFAOYSA-N 0.000 claims description 3
- PNYWTBNVJKJDDI-UHFFFAOYSA-N 8-(benzenesulfonyl)-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound CSC1=NN2C(N)=NC=NC2=C1S(=O)(=O)C1=CC=CC=C1 PNYWTBNVJKJDDI-UHFFFAOYSA-N 0.000 claims description 3
- UJZYDAYPPURDES-UHFFFAOYSA-N C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 Chemical compound C=12CSCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 UJZYDAYPPURDES-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- PPPVADQGCXVIIG-UHFFFAOYSA-N chembl1642114 Chemical compound C=12CCCC2=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 PPPVADQGCXVIIG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- MZHLYLPLUQNPRH-UHFFFAOYSA-N 3-(benzenesulfonyl)-5,6-dimethyl-2-methylsulfanyl-7-piperazin-1-ylpyrazolo[1,5-a]pyrimidine Chemical compound CC=1C(C)=NC2=C(S(=O)(=O)C=3C=CC=CC=3)C(SC)=NN2C=1N1CCNCC1 MZHLYLPLUQNPRH-UHFFFAOYSA-N 0.000 claims description 2
- CJYVLEUNNDIHSZ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-(methoxymethyl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-6-amine Chemical compound CSC1=NN2C=C(N)C(COC)=NC2=C1S(=O)(=O)C1=CC=CC=C1 CJYVLEUNNDIHSZ-UHFFFAOYSA-N 0.000 claims description 2
- KHHFVHLOIOOBGE-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-cyclopropyl-7-(4-methylpiperazin-1-yl)-2-methylsulfanylpyrazolo[1,5-a]pyrimidine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=CC(C3CC3)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KHHFVHLOIOOBGE-UHFFFAOYSA-N 0.000 claims description 2
- GQNCJZJRMRMGDJ-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n,5-n-dimethyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CSC1=NN2C(N)=CC(N(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 GQNCJZJRMRMGDJ-UHFFFAOYSA-N 0.000 claims description 2
- RPYDLZZCQDDXIB-UHFFFAOYSA-N 5-methyl-2-methylsulfanyl-3-(4-propan-2-ylphenyl)sulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C(C)C)C=C1 RPYDLZZCQDDXIB-UHFFFAOYSA-N 0.000 claims description 2
- FBXQGDKVKMTEAF-UHFFFAOYSA-N 5-methyl-3-(2-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1C FBXQGDKVKMTEAF-UHFFFAOYSA-N 0.000 claims description 2
- OWSYFTNTDMXBFQ-UHFFFAOYSA-N 5-methyl-3-(3-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC(C)=C1 OWSYFTNTDMXBFQ-UHFFFAOYSA-N 0.000 claims description 2
- MYJPFAZGUCRKJF-UHFFFAOYSA-N 8-(benzenesulfonyl)-2-methyl-4-(4-methylpiperazin-1-yl)-7-methylsulfanylpyrazolo[1,5-a][1,3,5]triazine Chemical compound CSC1=NN2C(N3CCN(C)CC3)=NC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 MYJPFAZGUCRKJF-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- JXXCBUALBBAQPF-UHFFFAOYSA-N 3-(benzenesulfonyl)-5-n-[2-(dimethylamino)ethyl]-2-methylsulfanylpyrazolo[1,5-a]pyrimidine-5,7-diamine Chemical compound CSC1=NN2C(N)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 JXXCBUALBBAQPF-UHFFFAOYSA-N 0.000 claims 1
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
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- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- SVYCFYNZKMXSEU-UHFFFAOYSA-N n,5-dimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(NC)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 SVYCFYNZKMXSEU-UHFFFAOYSA-N 0.000 description 1
- MCVKRCNWTSRZKG-UHFFFAOYSA-N n,n,5-trimethyl-2-methylsulfanyl-3-naphthalen-2-ylsulfonylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)C3=C4N=C(C)C=C(N4N=C3SC)N(C)C)=CC=C21 MCVKRCNWTSRZKG-UHFFFAOYSA-N 0.000 description 1
- XONFMUICYNIBEQ-UHFFFAOYSA-N n,n,5-trimethyl-3-(4-methylphenyl)sulfonyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-amine Chemical compound CSC1=NN2C(N(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(C)C=C1 XONFMUICYNIBEQ-UHFFFAOYSA-N 0.000 description 1
- SGTHBUSRDBXVCQ-UHFFFAOYSA-N n-[3-(4-bromophenyl)sulfonyl-2-ethyl-5-methylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=C(Br)C=C1 SGTHBUSRDBXVCQ-UHFFFAOYSA-N 0.000 description 1
- NNKXIULLHBGRTD-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-2-ethyl-7-(4-methylpiperazin-1-yl)pyrazolo[1,5-a]pyrimidin-5-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CCC1=NN2C(N3CCN(C)CC3)=CC(NCCN(C)C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 NNKXIULLHBGRTD-UHFFFAOYSA-N 0.000 description 1
- KGSMVKIWXJCCQV-UHFFFAOYSA-N n-[3-(benzenesulfonyl)-5-methyl-2-methylsulfanylpyrazolo[1,5-a]pyrimidin-7-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound CSC1=NN2C(NCCN(C)C)=CC(C)=NC2=C1S(=O)(=O)C1=CC=CC=C1 KGSMVKIWXJCCQV-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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- KCVNFNZJAATRIK-UHFFFAOYSA-M sodium;pyridine-3-sulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CN=C1 KCVNFNZJAATRIK-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 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
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- KQWHKLZRDFJOCN-UHFFFAOYSA-N thieno[3,4-d]pyrimidine Chemical compound N1=CN=CC2=CSC=C21 KQWHKLZRDFJOCN-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- A61P25/14—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
- 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
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D495/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98104346 | 1998-03-11 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO991150D0 NO991150D0 (no) | 1999-03-10 |
| NO991150L NO991150L (no) | 1999-09-13 |
| NO312297B1 true NO312297B1 (no) | 2002-04-22 |
Family
ID=8231568
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19991150A NO312297B1 (no) | 1998-03-11 | 1999-03-10 | Pyrazolopyrimidiner og pyrazolotriaziner, anvendelse og fremgangsmåte for fremstilling derav, samt medikament |
Country Status (34)
| Country | Link |
|---|---|
| US (1) | US6194410B1 (ja) |
| EP (1) | EP0941994B1 (ja) |
| JP (1) | JP3231288B2 (ja) |
| KR (1) | KR100313181B1 (ja) |
| CN (1) | CN1118468C (ja) |
| AR (1) | AR016453A1 (ja) |
| AT (1) | ATE240332T1 (ja) |
| AU (1) | AU752408B2 (ja) |
| BR (1) | BR9901095A (ja) |
| CA (1) | CA2265095C (ja) |
| CZ (1) | CZ291514B6 (ja) |
| DE (1) | DE69907784T2 (ja) |
| DK (1) | DK0941994T3 (ja) |
| ES (1) | ES2198095T3 (ja) |
| HK (1) | HK1023343A1 (ja) |
| HR (1) | HRP990077B1 (ja) |
| HU (1) | HUP9900589A1 (ja) |
| ID (1) | ID23575A (ja) |
| IL (1) | IL128869A (ja) |
| MA (1) | MA26612A1 (ja) |
| MY (1) | MY119536A (ja) |
| NO (1) | NO312297B1 (ja) |
| NZ (1) | NZ334526A (ja) |
| PE (1) | PE20000337A1 (ja) |
| PL (1) | PL331875A1 (ja) |
| PT (1) | PT941994E (ja) |
| RU (1) | RU2218340C2 (ja) |
| SG (1) | SG78336A1 (ja) |
| SI (1) | SI0941994T1 (ja) |
| TR (1) | TR199900531A3 (ja) |
| TW (1) | TW585865B (ja) |
| UY (1) | UY25419A1 (ja) |
| YU (1) | YU12099A (ja) |
| ZA (1) | ZA991946B (ja) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU4331500A (en) | 1999-04-06 | 2000-10-23 | Du Pont Pharmaceuticals Company | Pyrazolotriazines as crf antagonists |
| DE19956791A1 (de) | 1999-11-25 | 2001-05-31 | Merck Patent Gmbh | Neue Sulfonyloxazolamine |
| PE20020394A1 (es) | 2000-08-18 | 2002-06-21 | Agouron Pharma | Compuestos de pirazol y composiciones farmaceuticas que los contienen, que modulan y/o inhiben la actividad de erab/hadh2 |
| BR0208357A (pt) * | 2001-03-13 | 2004-06-29 | Bristol Myers Squibb Pharma Co | Composto, composição farmacêutica, método de antagonização de um receptor de fator de liberação de corticotropina (crf), método de tratamento de disfunção, método de triagem de ligantes, método de detecção de receptores de crf, método de inibição da ligação de crf, artigo industrializado e usos do composto |
| EP1401813B1 (en) | 2001-06-07 | 2007-02-07 | F. Hoffman-la Roche AG | New indole derivatives with 5-ht6 receptor affinity |
| CA2450245A1 (en) | 2001-06-15 | 2002-12-27 | F. Hoffmann-La Roche Ag | 4-piperazinylindole derivatives with 5-ht6 receptor affinity |
| WO2003013510A1 (en) * | 2001-08-07 | 2003-02-20 | Smithkline Beecham P.L.C. | 3-arylsulfonyl-7-piperazinyl- indoles, -benzofurans and -benzothiophenes with 5-ht6 receptor affinity for treating cns disorders |
| RU2309157C2 (ru) * | 2001-12-20 | 2007-10-27 | Уайт | Производные индолилалкиламина в качестве лигандов 5-гидрокситриптамина-6 |
| US6642381B2 (en) * | 2001-12-27 | 2003-11-04 | Hoffman-La Roche Inc. | Pyrimido[5,4-e][1,2,4]triazine-5,7-diamine compounds as protein tyrosine phosphatase inhibitors |
| GB0202679D0 (en) * | 2002-02-05 | 2002-03-20 | Glaxo Group Ltd | Novel compounds |
| UA78999C2 (en) * | 2002-06-04 | 2007-05-10 | Wyeth Corp | 1-(aminoalkyl)-3-sulfonylazaindoles as ligands of 5-hydroxytryptamine-6 |
| US6875771B2 (en) | 2002-07-26 | 2005-04-05 | Bristol-Myers Squibb Company | Pyridopyrimidine derivatives as 5-HT6 antagonists |
| US7329658B2 (en) * | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| EP1592690A1 (en) * | 2003-02-14 | 2005-11-09 | Wyeth | Heterocyclyl-3-sulfonylazaindole or -azaindazole derivatives as 5-hydroxytryptamine-6 ligands |
| KR20050115252A (ko) | 2003-02-28 | 2005-12-07 | 데이진 화-마 가부시키가이샤 | 피라졸로[1,5-ａ]피리미딘 유도체 |
| GB0305559D0 (en) * | 2003-03-11 | 2003-04-16 | Teijin Ltd | Compounds |
| US20080287405A1 (en) * | 2004-05-14 | 2008-11-20 | Thannickal Victor J | Compositions and Methods Relating to Protein Kinase Inhibitors |
| JP5584626B2 (ja) * | 2008-01-24 | 2014-09-03 | アンドレイ・アレクサンドロビッチ・イワシェンコ | ２−アルキルアミノ−３−（アリールスルホニル）−シクロアルキル［ｅ又はｄ］ピラゾロ［１，５−ａ］ピリミジン−セロトニン５−ＨＴ６受容体アンタゴニスト、その調製の方法及び使用 |
| EP2248814A4 (en) | 2008-01-24 | 2011-01-12 | Alla Chem Llc | SUBSTITUTED CYCLOALKAN [E AND D] PYRAZOLO [1,5-A] PYRIMIDINES / ANTAGONISTS OF SEROTONIN 5-HT6 RECEPTORS AND PROCESS FOR THEIR PREPARATION AND THEIR USE |
| RU2369600C1 (ru) | 2008-01-24 | 2009-10-10 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 4-СУЛЬФОНИЛ-ПИРАЗОЛЫ И 3-СУЛЬФОНИЛ-ПИРАЗОЛО[1,5-a]ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ5-HT6 РЕЦЕПТОРОВ, АКТИВНЫЙ КОМПОНЕНТ, ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, ЛЕКАРСТВЕННОЕ СРЕДСТВО И СПОСОБЫ ИХ ПОЛУЧЕНИЯ |
| WO2009093208A2 (ru) | 2008-01-24 | 2009-07-30 | Alla Chem, Llc | ЗАМЕЩЕННЫЕ 2-AMИHO-3-CУЛЬФOHИЛ-ПИPAЗOЛO[1,5-a]ПИPИMИДИHЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| RU2384581C2 (ru) | 2008-05-07 | 2010-03-20 | Андрей Александрович Иващенко | ЗАМЕЩЕННЫЕ 2-АМИНО-3-СУЛЬФОНИЛ-ТЕТРАГИДРО-ПИРАЗОЛО[1,5-a]ПИРИДО-ПИРИМИДИНЫ - АНТАГОНИСТЫ СЕРОТОНИНОВЫХ 5-HT6 РЕЦЕПТОРОВ, СПОСОБЫ ИХ ПОЛУЧЕНИЯ И ПРИМЕНЕНИЯ |
| CA2755968C (en) * | 2008-10-06 | 2019-03-19 | Andrey Alexandrovich Ivashchenko | Substituted 3-arylsulfonyl-pyrazolo[1,5-a]pyrimidines, serotonin 5-ht6 receptor antagonists and methods for the production and use thereof |
| AR074231A1 (es) | 2008-11-27 | 2010-12-29 | Boehringer Ingelheim Int | Derivados de 6, 7, 8, 9-tetrahidro-5h-1, 4, 7, 10a-tetraaza-ciclohept[f]indeno, composiciones farmacéuticas que contienen estos compuestos, su uso en el agonismo del receptor 5-ht2c y procesos para prepararlos. |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| EP2640705A2 (en) | 2010-11-15 | 2013-09-25 | Katholieke Universiteit Leuven | Novel antiviral compounds |
| RU2443697C1 (ru) | 2010-12-21 | 2012-02-27 | Александр Васильевич Иващенко | Замещенные метил-амины, антагонисты серотониновых 5-ht6 рецепторов, способы получения и применения |
| JP6082397B2 (ja) | 2011-09-30 | 2017-02-15 | イプセン ファルマ ソシエテ パール アクシオン サンプリフィエＩｐｓｅｎ Ｐｈａｒｍａ Ｓ．Ａ．Ｓ． | マクロ環状ｌｒｒｋ２キナーゼ阻害剤 |
| NZ630721A (en) * | 2012-03-09 | 2016-12-23 | Lexicon Pharmaceuticals Inc | Pyrazolo[1,5-a]pyrimidine-based compounds, compositions comprising them, and methods of their use |
| TW201542550A (zh) * | 2013-09-06 | 2015-11-16 | Lexicon Pharmaceuticals Inc | 吡唑并［１，５－ａ］嘧啶基化合物、包含彼之組合物以及使用彼之方法 |
| TW201620911A (zh) * | 2014-03-17 | 2016-06-16 | 雷西肯製藥股份有限公司 | 銜接子關聯激酶１之抑制劑、包含其之組成物、及其使用方法 |
| BR112017005299A2 (pt) | 2014-09-17 | 2017-12-12 | Ipsen Pharma Sas | inibidores de lrrk2 cinase macrocíclicos |
| CA2978170C (en) * | 2015-03-09 | 2024-02-27 | Aurigene Discovery Technologies Limited | Pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives as cdk inhibitors |
| WO2017052394A1 (en) * | 2015-09-23 | 2017-03-30 | Uniwersytet Jagielloński | Imidazopyridine compounds and their use as 5-ht6 receptor ligands |
| AU2016348549B2 (en) | 2015-11-02 | 2020-07-23 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidin-7-yl compound |
| EA039102B1 (ru) | 2016-11-02 | 2021-12-03 | Янссен Фармацевтика Нв | Соединения [1,2,4]триазоло[1,5-a]пиримидина в качестве ингибиторов pde2 |
| CA3038913A1 (en) | 2016-11-02 | 2018-05-11 | Janssen Pharmaceutica Nv | [1,2,4]triazolo[1,5-a]pyrimidine compounds as pde2 inhibitors |
| CN109923116B (zh) | 2016-11-02 | 2022-12-06 | 詹森药业有限公司 | 作为pde2抑制剂的[1,2,4]三唑并[1,5-a]嘧啶衍生物 |
| CN112142744A (zh) * | 2019-06-28 | 2020-12-29 | 上海瑛派药业有限公司 | 取代的稠合杂芳双环化合物作为激酶抑制剂及其应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0368897A1 (en) | 1987-07-31 | 1990-05-23 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4921527A (en) * | 1987-07-31 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DE3825043A1 (de) | 1988-07-20 | 1990-02-15 | Schering Ag | 3-methylsulfonyl-pyrazolo(1,5-a)pyrimidin-sulfonsaeureamide, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider, pflanzenwuchsregulierender und fungizider wirkung |
| US5571813A (en) * | 1993-06-10 | 1996-11-05 | Beiersdorf-Lilly Gmbh | Fused pyrimidine compounds and their use as pharmaceuticals |
| AU7001396A (en) | 1995-09-22 | 1997-04-09 | Takeda Chemical Industries Ltd. | Triazole compounds, their production and use |
| DZ2376A1 (fr) | 1996-12-19 | 2002-12-28 | Smithkline Beecham Plc | Dérivés de sulfonamides nouveaux procédé pour leurpréparation et compositions pharmaceutiques les c ontenant. |
| EP0946551A2 (en) | 1996-12-19 | 1999-10-06 | Smithkline Beecham Plc | N-piperazin-1-ylphenyl-benzamide derivatives |
| NZ501258A (en) | 1997-07-11 | 2001-07-27 | Smithkline Beecham P | Benzenesulfonamide compounds with 5HT6 receptor antagonist activity for treating anxiety and/or depression |
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1999
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