NO312065B1 - Benzosulfon-derivater, anvendelse og fremgangsmåte for fremstilling derav, samt medikament - Google Patents
Benzosulfon-derivater, anvendelse og fremgangsmåte for fremstilling derav, samt medikament Download PDFInfo
- Publication number
- NO312065B1 NO312065B1 NO19990187A NO990187A NO312065B1 NO 312065 B1 NO312065 B1 NO 312065B1 NO 19990187 A NO19990187 A NO 19990187A NO 990187 A NO990187 A NO 990187A NO 312065 B1 NO312065 B1 NO 312065B1
- Authority
- NO
- Norway
- Prior art keywords
- amino
- sulfonyl
- benzenesulfonyl
- phenylamine
- mol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 239000003814 drug Substances 0.000 title claims description 11
- 229940079593 drug Drugs 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 t-butylethynyl Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 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 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 16
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
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- 125000006239 protecting group Chemical group 0.000 claims description 7
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 6
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 201000000980 schizophrenia Diseases 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 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 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
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- 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
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- 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
- 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 3
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- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 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 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
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- 208000028683 bipolar I disease Diseases 0.000 claims description 2
- ZPGINSOGHDYPOS-UHFFFAOYSA-N n'-[3-(4-aminophenyl)sulfonyl-5-bromophenyl]-n-methylpropane-1,3-diamine Chemical compound CNCCCNC1=CC(Br)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 ZPGINSOGHDYPOS-UHFFFAOYSA-N 0.000 claims description 2
- RXRLZOAYLADWKH-UHFFFAOYSA-N n-[4-(4-aminophenyl)sulfonyl-6-bromopyridin-2-yl]-n',n'-dimethylethane-1,2-diamine Chemical compound BrC1=NC(NCCN(C)C)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 RXRLZOAYLADWKH-UHFFFAOYSA-N 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
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 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
- 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 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- VFGHVHYBFRCHNM-UHFFFAOYSA-N n-[4-(4-aminophenyl)sulfonyl-6-bromopyridin-2-yl]-n',n'-dimethylpropane-1,3-diamine Chemical compound BrC1=NC(NCCCN(C)C)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 VFGHVHYBFRCHNM-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HUMMCEUVDBVXTQ-UHFFFAOYSA-N naphthalen-1-ylboronic acid Chemical compound C1=CC=C2C(B(O)O)=CC=CC2=C1 HUMMCEUVDBVXTQ-UHFFFAOYSA-N 0.000 description 1
- KPTRDYONBVUWPD-UHFFFAOYSA-N naphthalen-2-ylboronic acid Chemical compound C1=CC=CC2=CC(B(O)O)=CC=C21 KPTRDYONBVUWPD-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 239000007800 oxidant agent Substances 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
- 229960001779 pargyline Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- HUBMBNGODLWSPA-UHFFFAOYSA-N prop-1-en-2-yloxyboronic acid Chemical compound CC(=C)OB(O)O HUBMBNGODLWSPA-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- CPCFZBOTLAEGND-UHFFFAOYSA-M sodium;4-acetamidobenzenesulfinate Chemical compound [Na+].CC(=O)NC1=CC=C(S([O-])=O)C=C1 CPCFZBOTLAEGND-UHFFFAOYSA-M 0.000 description 1
- UOOVFPYJUPSROO-UHFFFAOYSA-M sodium;naphthalene-1-sulfinate Chemical compound [Na+].C1=CC=C2C(S(=O)[O-])=CC=CC2=C1 UOOVFPYJUPSROO-UHFFFAOYSA-M 0.000 description 1
- JGGFVSGYTHUAOQ-UHFFFAOYSA-M sodium;naphthalene-2-sulfinate Chemical compound [Na+].C1=CC=CC2=CC(S(=O)[O-])=CC=C21 JGGFVSGYTHUAOQ-UHFFFAOYSA-M 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000005062 synaptic transmission Effects 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
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- ZFQWJXFJJZUVPI-UHFFFAOYSA-N tert-butyl n-(4-aminobutyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCCN ZFQWJXFJJZUVPI-UHFFFAOYSA-N 0.000 description 1
- OYCYZDFIPYJLDG-UHFFFAOYSA-N tert-butyl n-[4-[[4-(4-aminophenyl)sulfonyl-6-bromopyridin-2-yl]amino]butyl]carbamate Chemical compound BrC1=NC(NCCCCNC(=O)OC(C)(C)C)=CC(S(=O)(=O)C=2C=CC(N)=CC=2)=C1 OYCYZDFIPYJLDG-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- OBYRCTCRALMZKW-UHFFFAOYSA-N tributyl(cyclohexen-1-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CCCCC1 OBYRCTCRALMZKW-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
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
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- 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
-
- 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
-
- 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
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- 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
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- A61P25/00—Drugs for disorders of the nervous system
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- A61P25/16—Anti-Parkinson drugs
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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
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- A—HUMAN NECESSITIES
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- 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
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- 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 |
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EP98100690 | 1998-01-16 |
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NO990187L NO990187L (no) | 1999-07-19 |
NO312065B1 true NO312065B1 (no) | 2002-03-11 |
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US (1) | US5990105A (cs) |
EP (1) | EP0930302B1 (cs) |
JP (1) | JP3249092B2 (cs) |
KR (1) | KR100319250B1 (cs) |
CN (1) | CN1148356C (cs) |
AR (1) | AR014313A1 (cs) |
AT (1) | ATE236136T1 (cs) |
AU (1) | AU757841B2 (cs) |
BR (1) | BR9900065A (cs) |
CA (1) | CA2258454A1 (cs) |
CO (1) | CO5090847A1 (cs) |
CZ (1) | CZ12099A3 (cs) |
DE (1) | DE69906397T2 (cs) |
DK (1) | DK0930302T3 (cs) |
ES (1) | ES2193607T3 (cs) |
HK (1) | HK1022310A1 (cs) |
HR (1) | HRP990011B1 (cs) |
HU (1) | HUP9900120A3 (cs) |
ID (1) | ID23234A (cs) |
IL (1) | IL128027A (cs) |
MA (1) | MA26599A1 (cs) |
MY (1) | MY121778A (cs) |
NO (1) | NO312065B1 (cs) |
NZ (1) | NZ333706A (cs) |
PE (1) | PE20000170A1 (cs) |
PL (1) | PL194735B1 (cs) |
PT (1) | PT930302E (cs) |
RU (1) | RU2201922C2 (cs) |
SG (1) | SG71898A1 (cs) |
SI (1) | SI0930302T1 (cs) |
TR (1) | TR199900090A3 (cs) |
TW (1) | TW553938B (cs) |
YU (1) | YU1199A (cs) |
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Families Citing this family (35)
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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 |
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 |
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 |
CN1222511C (zh) * | 2000-11-02 | 2005-10-12 | 惠氏公司 | 作为5-羟色胺-6配体的1-芳基-或1-烷基磺酰基-杂环基吲哚 |
KR100608417B1 (ko) | 2001-08-10 | 2006-08-02 | 에프. 호프만-라 로슈 아게 | 5-ht6 수용체 친화성을 갖는 아릴설포닐 유도체 |
WO2003030901A1 (en) * | 2001-10-09 | 2003-04-17 | Pharmacia & Upjohn Company | Arylsulphonyl-substituted tetrahydro- and hexahydro-carbazoles as 5-ht-6 receptor ligands |
BRPI0308696B8 (pt) * | 2002-03-27 | 2021-05-25 | Axovant Sciences Gmbh | composto derivado de quinolina, seu processo de preparação, sua composição farmacêutica e seus usos |
US6875771B2 (en) | 2002-07-26 | 2005-04-05 | Bristol-Myers Squibb Company | Pyridopyrimidine derivatives as 5-HT6 antagonists |
CA2507100C (en) * | 2002-11-21 | 2012-10-09 | Chiron Corporation | 2,4,6-trisubstituted pyrimidines as phosphotidylinositol (pi) 3-kinase inhibitors and their use in the treatment of cancer |
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 |
BRPI0515860B8 (pt) * | 2004-12-21 | 2021-05-25 | Hoffmann La Roche | derivados de tetralin e indano, seus usos, e composição farmacêutica |
WO2006119390A1 (en) * | 2005-05-04 | 2006-11-09 | Vertex Pharmaceuticals Incorporated | Pyridines useful as modulators of ion channels |
JO2660B1 (en) | 2006-01-20 | 2012-06-17 | نوفارتيس ايه جي | Pi-3 inhibitors and methods of use |
PL2044043T5 (pl) | 2006-06-16 | 2022-05-02 | H. Lundbeck A/S | Bromowodorek 1-[2-(2,4-dimetylofenylosulfanylo)fenylo]piperazyny jako związek o połączonym działaniu wychwytu zwrotnego serotoniny i działaniu na 5-ht3 i 5-ht1a do leczenia upośledzenia funckji poznawczych |
MX2009004947A (es) * | 2006-11-09 | 2009-05-19 | Hoffmann La Roche | Arilsulfonil-pirrolidinas como inhibidores 5-hidroxitriptaminas6 (5-ht6). |
US8173647B2 (en) * | 2007-02-06 | 2012-05-08 | Gordana Atallah | PI 3-kinase inhibitors and methods of their use |
BRPI0816571A2 (pt) * | 2007-10-26 | 2015-12-22 | Suven Life Sciences Ltd | "composto, processo para preparação do composto, composição farmacêutica, agente e método para o tratamento de uma doença ou uma desordem do sistema nervoso central relacionada à ou afetada pelo recptor 5-ht6" |
WO2009128058A1 (en) | 2008-04-18 | 2009-10-22 | UNIVERSITY COLLEGE DUBLIN, NATIONAL UNIVERSITY OF IRELAND, DUBLIN et al | Psycho-pharmaceuticals |
UA100192C2 (en) | 2008-11-11 | 2012-11-26 | УАЙТ ЭлЭлСи | 1-(arylsulfonyl)-4-(piperazin-1-yl)-1h-benzimidazoles as 5-hydroxytryptamine-6 ligands |
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JP2020507625A (ja) | 2017-02-07 | 2020-03-12 | オブリーク セラピューティクス アーベー | ヘテロアリールスルホニル置換ピリジンおよび癌の治療におけるそれらの使用 |
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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 |
AU8869091A (en) * | 1990-11-27 | 1992-06-25 | Merck Patent Gesellschaft Mit Beschrankter Haftung | 3,6-disubstituted 2-halopyridines |
GB9214120D0 (en) * | 1991-07-25 | 1992-08-12 | Ici Plc | Therapeutic amides |
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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 |
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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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