IL128027A - History of benzosulfone, the process for their preparation, pharmaceutical preparations containing them and their use in the preparation of drugs for the treatment of nervous system disorders - Google Patents
History of benzosulfone, the process for their preparation, pharmaceutical preparations containing them and their use in the preparation of drugs for the treatment of nervous system disordersInfo
- Publication number
- IL128027A IL128027A IL12802799A IL12802799A IL128027A IL 128027 A IL128027 A IL 128027A IL 12802799 A IL12802799 A IL 12802799A IL 12802799 A IL12802799 A IL 12802799A IL 128027 A IL128027 A IL 128027A
- Authority
- IL
- Israel
- Prior art keywords
- amino
- lower alkyl
- hydrogen
- pyridine
- phenylamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 239000003814 drug Substances 0.000 title claims description 8
- 208000012902 Nervous system disease Diseases 0.000 title claims description 6
- 208000025966 Neurological disease Diseases 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 80
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
- 239000001257 hydrogen Substances 0.000 claims abstract description 47
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 26
- -1 cyano, amino Chemical group 0.000 claims abstract description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 18
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract description 8
- 125000004193 piperazinyl group Chemical group 0.000 claims abstract description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 8
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract 16
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 7
- 125000001544 thienyl group Chemical group 0.000 claims abstract 7
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims abstract 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- 208000020401 Depressive disease Diseases 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- 208000026139 Memory disease Diseases 0.000 claims description 5
- 208000018737 Parkinson disease Diseases 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- KSMWSYNAJGWNMR-UHFFFAOYSA-N 4-(2-bromo-6-piperazin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(Br)=NC(N2CCNCC2)=C1 KSMWSYNAJGWNMR-UHFFFAOYSA-N 0.000 claims description 4
- KKDCGGDVDFZYTB-UHFFFAOYSA-N 4-(2-chloro-6-pyrrolidin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(Cl)=NC(N2CCCC2)=C1 KKDCGGDVDFZYTB-UHFFFAOYSA-N 0.000 claims description 4
- OEQIXIYYFHPIAA-UHFFFAOYSA-N 4-(2-iodo-6-pyrrolidin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(I)=NC(N2CCCC2)=C1 OEQIXIYYFHPIAA-UHFFFAOYSA-N 0.000 claims description 4
- GTTIHTACBBSWCF-UHFFFAOYSA-N 4-(2-phenyl-6-pyrrolidin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(N2CCCC2)=NC(C=2C=CC=CC=2)=C1 GTTIHTACBBSWCF-UHFFFAOYSA-N 0.000 claims description 4
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
- SGVIRQMTPUPXBQ-UHFFFAOYSA-N 2-(4-aminophenyl)sulfonyl-6-bromo-n-methylpyridin-4-amine Chemical compound CNC1=CC(Br)=NC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 SGVIRQMTPUPXBQ-UHFFFAOYSA-N 0.000 claims description 3
- SRJVAKMYNBMXLD-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonyl-5-bromo-n-methylaniline Chemical compound CNC1=CC(Br)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 SRJVAKMYNBMXLD-UHFFFAOYSA-N 0.000 claims description 3
- FGDYWIYXFCDHOI-UHFFFAOYSA-N 3-[3-(4-aminophenyl)sulfonyl-5-bromoanilino]propan-1-ol Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(Br)=CC(NCCCO)=C1 FGDYWIYXFCDHOI-UHFFFAOYSA-N 0.000 claims description 3
- SBIYLJBIZZNZJV-UHFFFAOYSA-N 4-(3,5-dimethoxyphenyl)sulfonylaniline Chemical compound COC1=CC(OC)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 SBIYLJBIZZNZJV-UHFFFAOYSA-N 0.000 claims description 3
- KSABNQBKVGBSGB-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonyl-6-bromo-n,n-dimethylpyridin-2-amine Chemical compound BrC1=NC(N(C)C)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 KSABNQBKVGBSGB-UHFFFAOYSA-N 0.000 claims description 3
- IXNHUQDFMNQLLU-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonyl-6-bromo-n-methylpyrimidin-2-amine Chemical compound CNC1=NC(Br)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=N1 IXNHUQDFMNQLLU-UHFFFAOYSA-N 0.000 claims description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 3
- YRYVAGQJEFNFOP-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonyl-5-bromo-n,n-dimethylaniline Chemical compound CN(C)C1=CC(Br)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 YRYVAGQJEFNFOP-UHFFFAOYSA-N 0.000 claims description 2
- VBANXLMZDBUBMQ-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonyl-5-bromo-n-ethyl-n-methylaniline Chemical compound CCN(C)C1=CC(Br)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 VBANXLMZDBUBMQ-UHFFFAOYSA-N 0.000 claims description 2
- VQGXDKWYDBXYNK-UHFFFAOYSA-N 4-(4-aminophenyl)sulfonyl-6-bromo-n-methylpyridin-2-amine Chemical compound BrC1=NC(NC)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 VQGXDKWYDBXYNK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 150000002828 nitro derivatives Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 208000020925 Bipolar disease Diseases 0.000 claims 3
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 331
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 191
- 239000002904 solvent Substances 0.000 description 123
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 114
- 239000000243 solution Substances 0.000 description 112
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- 229940093499 ethyl acetate Drugs 0.000 description 110
- 235000019439 ethyl acetate Nutrition 0.000 description 110
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 105
- 239000000203 mixture Substances 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 96
- 239000000741 silica gel Substances 0.000 description 95
- 229910002027 silica gel Inorganic materials 0.000 description 95
- 229960001866 silicon dioxide Drugs 0.000 description 95
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 75
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 68
- 239000013078 crystal Substances 0.000 description 65
- 239000011780 sodium chloride Substances 0.000 description 57
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 54
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 51
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 45
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000012074 organic phase Substances 0.000 description 40
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 36
- 239000011541 reaction mixture Substances 0.000 description 31
- 238000001914 filtration Methods 0.000 description 30
- 229910000029 sodium carbonate Inorganic materials 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 20
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 19
- VVFLAMYJXXXEAN-UHFFFAOYSA-N 4-(2,6-dibromopyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(Br)=NC(Br)=C1 VVFLAMYJXXXEAN-UHFFFAOYSA-N 0.000 description 18
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 18
- 238000003818 flash chromatography Methods 0.000 description 18
- 239000000706 filtrate Substances 0.000 description 17
- 238000010992 reflux Methods 0.000 description 17
- 238000001035 drying Methods 0.000 description 16
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 15
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 15
- 239000000725 suspension Substances 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 13
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 238000002604 ultrasonography Methods 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 229960003390 magnesium sulfate Drugs 0.000 description 10
- 229910000027 potassium carbonate Inorganic materials 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 235000017550 sodium carbonate Nutrition 0.000 description 9
- XIPATZUHJFQGQC-UHFFFAOYSA-N 2,6-dibromo-4-nitropyridine Chemical compound [O-][N+](=O)C1=CC(Br)=NC(Br)=C1 XIPATZUHJFQGQC-UHFFFAOYSA-N 0.000 description 8
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- CMTZTVLAIRCQQM-UHFFFAOYSA-N 4-nitrobenzenethiol;potassium Chemical compound [K].[O-][N+](=O)C1=CC=C(S)C=C1 CMTZTVLAIRCQQM-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000000969 carrier Substances 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- WDFMDNUTOSLOPW-UHFFFAOYSA-N 4-(2-bromo-6-pyrrolidin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(Br)=NC(N2CCCC2)=C1 WDFMDNUTOSLOPW-UHFFFAOYSA-N 0.000 description 6
- 239000012267 brine Substances 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- HCQLFCIOSVENRN-UHFFFAOYSA-N 2,6-dibromo-4-(4-nitrophenyl)sulfonylpyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1=CC(Br)=NC(Br)=C1 HCQLFCIOSVENRN-UHFFFAOYSA-N 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- AQZYJKWPVAMDSM-UHFFFAOYSA-N 2,6-dibromo-4-(4-nitrophenyl)sulfanylpyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=CC(Br)=NC(Br)=C1 AQZYJKWPVAMDSM-UHFFFAOYSA-N 0.000 description 4
- LGRFBXHJZUNVBU-UHFFFAOYSA-N 4-(2-bromo-6-methylpyridin-4-yl)sulfonylaniline Chemical compound BrC1=NC(C)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 LGRFBXHJZUNVBU-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000825 pharmaceutical preparation Substances 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- BOZXAECLDPEYGE-UHFFFAOYSA-N 2,6-dibromo-4-[3-(trifluoromethyl)phenyl]sulfonylpyridine Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)C=2C=C(Br)N=C(Br)C=2)=C1 BOZXAECLDPEYGE-UHFFFAOYSA-N 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 3
- XEPRUPUTKJOFNO-UHFFFAOYSA-N 2-bromo-4-nitro-6-(4-nitrophenyl)sulfonylpyridine Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)C1=CC([N+]([O-])=O)=CC(Br)=N1 XEPRUPUTKJOFNO-UHFFFAOYSA-N 0.000 description 3
- OKZLYPGUZPTKSA-UHFFFAOYSA-N 3-bromo-n-methyl-5-(4-nitrophenyl)sulfanylaniline Chemical compound CNC1=CC(Br)=CC(SC=2C=CC(=CC=2)[N+]([O-])=O)=C1 OKZLYPGUZPTKSA-UHFFFAOYSA-N 0.000 description 3
- IDFJKWVRDKFEID-UHFFFAOYSA-N 4-(2,6-diiodopyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(I)=NC(I)=C1 IDFJKWVRDKFEID-UHFFFAOYSA-N 0.000 description 3
- WRLXFBBQMOJTMH-UHFFFAOYSA-N 4-(2-ethenyl-6-pyrrolidin-1-ylpyridin-4-yl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC(C=C)=NC(N2CCCC2)=C1 WRLXFBBQMOJTMH-UHFFFAOYSA-N 0.000 description 3
- AUXVFTAPQJEIOK-UHFFFAOYSA-N 4-(3,5-dimethoxyphenyl)sulfonyl-2-methylaniline Chemical compound COC1=CC(OC)=CC(S(=O)(=O)C=2C=C(C)C(N)=CC=2)=C1 AUXVFTAPQJEIOK-UHFFFAOYSA-N 0.000 description 3
- NHYXBMSRKCSGSO-UHFFFAOYSA-N 4-(benzenesulfonyl)-2,6-dibromopyridine Chemical compound BrC1=NC(Br)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 NHYXBMSRKCSGSO-UHFFFAOYSA-N 0.000 description 3
- NWRWHCVFPFRWQD-UHFFFAOYSA-N 4-(benzenesulfonyl)-6-bromo-n-methylpyridin-2-amine Chemical compound BrC1=NC(NC)=CC(S(=O)(=O)C=2C=CC=CC=2)=C1 NWRWHCVFPFRWQD-UHFFFAOYSA-N 0.000 description 3
- 108091005435 5-HT6 receptors Proteins 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
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- 239000007916 tablet composition Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QNMBSXGYAQZCTN-UHFFFAOYSA-N thiophen-3-ylboronic acid Chemical compound OB(O)C=1C=CSC=1 QNMBSXGYAQZCTN-UHFFFAOYSA-N 0.000 description 1
- QIWRFOJWQSSRJZ-UHFFFAOYSA-N tributyl(ethenyl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C=C QIWRFOJWQSSRJZ-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/73—Unsubstituted amino or imino radicals
-
- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
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- 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
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- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/32—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C317/34—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring
- C07C317/36—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having sulfone or sulfoxide groups and amino groups bound to carbon atoms of six-membered aromatic rings being part of the same non-condensed ring or of a condensed ring system containing that ring with the nitrogen atoms of the amino groups bound to hydrogen atoms or to carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/84—Nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98100690 | 1998-01-16 |
Publications (2)
| Publication Number | Publication Date |
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| IL128027A0 IL128027A0 (en) | 1999-11-30 |
| IL128027A true IL128027A (en) | 2004-03-28 |
Family
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Family Applications (1)
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| IL12802799A IL128027A (en) | 1998-01-16 | 1999-01-13 | History of benzosulfone, the process for their preparation, pharmaceutical preparations containing them and their use in the preparation of drugs for the treatment of nervous system disorders |
Country Status (33)
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| EP (1) | EP0930302B1 (de) |
| JP (1) | JP3249092B2 (de) |
| KR (1) | KR100319250B1 (de) |
| CN (1) | CN1148356C (de) |
| AR (1) | AR014313A1 (de) |
| AT (1) | ATE236136T1 (de) |
| AU (1) | AU757841B2 (de) |
| BR (1) | BR9900065A (de) |
| CA (1) | CA2258454A1 (de) |
| CO (1) | CO5090847A1 (de) |
| CZ (1) | CZ12099A3 (de) |
| DE (1) | DE69906397T2 (de) |
| DK (1) | DK0930302T3 (de) |
| ES (1) | ES2193607T3 (de) |
| HR (1) | HRP990011B1 (de) |
| HU (1) | HUP9900120A3 (de) |
| ID (1) | ID23234A (de) |
| IL (1) | IL128027A (de) |
| MA (1) | MA26599A1 (de) |
| MY (1) | MY121778A (de) |
| NO (1) | NO312065B1 (de) |
| NZ (1) | NZ333706A (de) |
| PE (1) | PE20000170A1 (de) |
| PL (1) | PL194735B1 (de) |
| PT (1) | PT930302E (de) |
| RU (1) | RU2201922C2 (de) |
| SG (1) | SG71898A1 (de) |
| SI (1) | SI0930302T1 (de) |
| TR (1) | TR199900090A2 (de) |
| TW (1) | TW553938B (de) |
| YU (1) | YU1199A (de) |
| ZA (1) | ZA99254B (de) |
Families Citing this family (36)
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| US7030109B2 (en) | 1999-07-19 | 2006-04-18 | Pharmacia & Upjohn Company | 1,2,3,4,5,6-Hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| MY122278A (en) | 1999-07-19 | 2006-04-29 | Upjohn Co | 1,2,3,4,5,6-hexahydroazepino[4,5-b]indoles containing arylsulfones at the 9-position |
| DE19956791A1 (de) | 1999-11-25 | 2001-05-31 | Merck Patent Gmbh | Neue Sulfonyloxazolamine |
| US7034029B2 (en) | 2000-11-02 | 2006-04-25 | Wyeth | 1-aryl- or 1-alkylsulfonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| NZ525592A (en) * | 2000-11-02 | 2004-07-30 | Wyeth Corp | 1-Aryl- or 1-alkylsufonyl-heterocyclylbenzazoles as 5-hydroxytryptamine-6 ligands |
| HRP20040090A2 (en) | 2001-08-10 | 2004-12-31 | Hoffmann La Roche | Arylsulfonyl derivatives with 5-ht<sub>6</sub> receptor affinity |
| BR0213208A (pt) * | 2001-10-09 | 2004-08-31 | Upjohn Co | Compostos de tetraidro- e hexaidro-carbazóis de arilsulfonila substituìda, suas composições e usos |
| MXPA04009318A (es) * | 2002-03-27 | 2005-01-25 | Glaxo Group Ltd | Derivados de quinolina y su uso como ligados 5-ht6. |
| US6875771B2 (en) | 2002-07-26 | 2005-04-05 | Bristol-Myers Squibb Company | Pyridopyrimidine derivatives as 5-HT6 antagonists |
| EP2316831B1 (de) * | 2002-11-21 | 2013-03-06 | Novartis AG | 2-(morpholin-4-yl)Pyrimidinen als Phosphotidylinositol (PI) 3-Kinase Inhibitoren und deren Verwendung zur Behandlung von Krebs |
| GB0305575D0 (en) | 2003-03-11 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| GB0419192D0 (en) * | 2004-08-27 | 2004-09-29 | Merck Sharp & Dohme | Therapeutic agents |
| ES2337482T3 (es) * | 2004-12-21 | 2010-04-26 | F. Hoffmann-La Roche Ag | Derivados de tetralina y de indano y usos de los mismos. |
| JP2008540438A (ja) * | 2005-05-04 | 2008-11-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャネルのモジュレーターとして有用なピリジン |
| RU2424229C2 (ru) * | 2005-10-06 | 2011-07-20 | Астразенека Аб | Производные бифенилоксиуксусной кислоты, их применение для изготовления лекарственного средства и промежуточные соединения |
| JO2660B1 (en) * | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
| BR122020011920A2 (pt) | 2006-06-16 | 2020-08-25 | Lundbeck & Co As H | composto, composição farmacêutica, método para tratar uma doença, uso de um composto, e processos para a preparação de um composto, e para a fabricação de um composto |
| ATE495153T1 (de) * | 2006-11-09 | 2011-01-15 | Hoffmann La Roche | Arylsulfonylpyrrolidine als 5-ht6-inhibitoren |
| US8173647B2 (en) * | 2007-02-06 | 2012-05-08 | Gordana Atallah | PI 3-kinase inhibitors and methods of their use |
| AU2008315309B2 (en) * | 2007-10-26 | 2011-06-09 | Suven Life Sciences Limited | Amino arylsulfonamide compounds and their use as 5-HT6 ligands |
| EP2288345B1 (de) | 2008-04-18 | 2015-06-10 | University College Dublin National University Of Ireland, Dublin | Psychopharmazeutika |
| UA100192C2 (en) | 2008-11-11 | 2012-11-26 | УАЙТ ЭлЭлСи | 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands |
| RU2443697C1 (ru) | 2010-12-21 | 2012-02-27 | Александр Васильевич Иващенко | Замещенные метил-амины, антагонисты серотониновых 5-ht6 рецепторов, способы получения и применения |
| JP6026544B2 (ja) | 2011-09-27 | 2016-11-16 | ノバルティス アーゲー | 変異体idhの阻害剤としての3−ピリミジン−4−イル−オキサゾリジン−2−オン類 |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| PL2945620T3 (pl) | 2013-01-18 | 2018-03-30 | Cardioxyl Pharmaceuticals, Inc. | Donory nitroksylu o korzystniejszym indeksie terapeutycznym |
| GEP201706699B (en) | 2013-03-14 | 2017-07-10 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant idh |
| EP3083588B1 (de) | 2013-12-20 | 2020-12-09 | Sunshine Lake Pharma Co., Ltd. | Aromatische heterocyclische verbindungen und deren anwendung in pharmazeutika |
| GB201514021D0 (en) | 2015-08-07 | 2015-09-23 | Arner Elias Set Jeno | Novel Pyridines and their use in the treatment of cancer |
| BR112019016233A2 (pt) | 2017-02-07 | 2020-04-07 | Oblique Therapeutics Ab | piridinas substituídas com heterociclilsulfonila e uso das mesmas no tratamento de câncer |
| US11161815B2 (en) | 2017-02-07 | 2021-11-02 | Oblique Therapeutics Ab | Hydrocarbylsulfonyl-substituted pyridines and their use in the treatment of cancer |
| EP3580215A1 (de) | 2017-02-07 | 2019-12-18 | Oblique Therapeutics AB | Heteroarylsulfonylsubstituierte pyridine und deren verwendung zur behandlung von krebs |
| US11208384B2 (en) | 2017-02-07 | 2021-12-28 | Oblique Therapeutics Ab | Sulfinylpyridines and their use in the treatment of cancer |
| IL277071B2 (en) | 2018-03-08 | 2024-07-01 | Incyte Corp | AMINOPYRAZINE DIOL COMPOUNDS AS PI3K-y INHIBITORS |
| US11046658B2 (en) | 2018-07-02 | 2021-06-29 | Incyte Corporation | Aminopyrazine derivatives as PI3K-γ inhibitors |
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| JPS55151560A (en) * | 1979-05-14 | 1980-11-26 | Ishihara Sangyo Kaisha Ltd | Pyridylthioaniline compound |
| JPS60185764A (ja) * | 1984-03-05 | 1985-09-21 | Wako Pure Chem Ind Ltd | ピリジン誘導体の新規な製造法 |
| EP0466096A1 (de) * | 1990-07-12 | 1992-01-15 | Jujo Paper Co., Ltd. | Derivate von 4-Hydroxyphenylsulfonen |
| US5389291A (en) * | 1990-11-27 | 1995-02-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 3,6-disubstituted 2-halopyridines |
| CA2059450A1 (en) * | 1991-01-24 | 1992-07-25 | Nobuyuki Sakashita | Subsituted pyridinesulfonamide compound or its salt, process for preparing the same, and herbicide containing the same |
| GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
| JPH06127956A (ja) * | 1992-10-16 | 1994-05-10 | Copal Co Ltd | ガラスレンズの成形装置 |
| JP3907722B2 (ja) * | 1995-08-23 | 2007-04-18 | 株式会社クラレ | 2−ヒドロキシピリジン類および/または2(1h)−ピリドン類の製造法 |
| JP3907721B2 (ja) * | 1995-08-23 | 2007-04-18 | 株式会社クラレ | 2−アラルキルオキシピリジン類の製造法 |
| WO1997036878A1 (en) * | 1996-03-29 | 1997-10-09 | Ube Industries, Ltd. | Pyrimidine compounds, process for producing the same, and agricultural or horticultural bactericides |
| JP3814885B2 (ja) * | 1996-09-03 | 2006-08-30 | 宇部興産株式会社 | 2−シアノピリミジン誘導体、その製造法及び農園芸用の殺菌剤 |
| WO1998054139A1 (de) * | 1997-05-30 | 1998-12-03 | Basf Aktiengesellschaft | Verfahren zur herstellung substituierter thiopyridine |
| US6197962B1 (en) * | 1998-01-26 | 2001-03-06 | Kuraray Co., Ltd. | Method for producing 2-sulfonylpyridine derivatives and method for producing 2-{[(2-pyridyl)methyl]thio}-1H-benzimidazole derivatives |
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1999
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- 1999-01-08 EP EP99100149A patent/EP0930302B1/de not_active Expired - Lifetime
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