ZA200308848B - Novel indole derivatives. - Google Patents
Novel indole derivatives. Download PDFInfo
- Publication number
- ZA200308848B ZA200308848B ZA200308848A ZA200308848A ZA200308848B ZA 200308848 B ZA200308848 B ZA 200308848B ZA 200308848 A ZA200308848 A ZA 200308848A ZA 200308848 A ZA200308848 A ZA 200308848A ZA 200308848 B ZA200308848 B ZA 200308848B
- Authority
- ZA
- South Africa
- Prior art keywords
- indol
- piperazin
- disorder
- compound
- alkyl
- Prior art date
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- 150000002475 indoles Chemical class 0.000 title description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 55
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 108020003175 receptors Proteins 0.000 claims description 25
- 102000005962 receptors Human genes 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 208000012902 Nervous system disease Diseases 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 229960003638 dopamine Drugs 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 208000019022 Mood disease Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- -1 hydroxy, formyl Chemical group 0.000 claims description 7
- 208000019906 panic disease Diseases 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 208000025966 Neurological disease Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 206010041250 Social phobia Diseases 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
- 230000008485 antagonism Effects 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 208000030814 Eating disease Diseases 0.000 claims description 5
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 5
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 5
- 235000014632 disordered eating Nutrition 0.000 claims description 5
- 230000008517 inhibition of serotonin uptake Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 230000002301 combined effect Effects 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
- YSHMEIYOZBQRJM-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethoxy]pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1OCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 YSHMEIYOZBQRJM-UHFFFAOYSA-N 0.000 claims description 2
- XWIUFAKNWVSOAO-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-6-methylpyridine-3-carboxamide Chemical compound CC1=CC=C(C(N)=O)C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 XWIUFAKNWVSOAO-UHFFFAOYSA-N 0.000 claims description 2
- DWKIKYKSSAQQHN-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-6-thiophen-2-yl-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(C(F)(F)F)=CC=1C1=CC=CS1 DWKIKYKSSAQQHN-UHFFFAOYSA-N 0.000 claims description 2
- QAGOJRNNZJLKQP-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound N#CC1=CC=CN=C1SCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 QAGOJRNNZJLKQP-UHFFFAOYSA-N 0.000 claims description 2
- QJZJMPJNZXUUFJ-UHFFFAOYSA-N 4-[4-[2-(4-methyl-3-methylsulfonyl-6-phenylpyridin-2-yl)sulfanylethyl]piperazin-1-yl]-1h-indole Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(S(C)(=O)=O)C(C)=CC=1C1=CC=CC=C1 QJZJMPJNZXUUFJ-UHFFFAOYSA-N 0.000 claims description 2
- NGNFGVWIOHDMGI-UHFFFAOYSA-N 4-[4-[2-(4-methylpyridin-2-yl)sulfanylethyl]piperazin-1-yl]-1h-indole Chemical compound CC1=CC=NC(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 NGNFGVWIOHDMGI-UHFFFAOYSA-N 0.000 claims description 2
- PUAYMLBANKVXQH-UHFFFAOYSA-N 4-[4-[2-(5-ethylpyrimidin-2-yl)sulfanylethyl]piperazin-1-yl]-1h-indole Chemical compound N1=CC(CC)=CN=C1SCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 PUAYMLBANKVXQH-UHFFFAOYSA-N 0.000 claims description 2
- PPAPPYUTIDDFQT-UHFFFAOYSA-N 4-[4-[2-[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylethyl]piperazin-1-yl]-1h-indole Chemical compound FC(F)(F)C1=CC=NC(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 PPAPPYUTIDDFQT-UHFFFAOYSA-N 0.000 claims description 2
- BLQOIFIWWXIKAF-UHFFFAOYSA-N 4-[4-[3-[5-(trifluoromethyl)pyridin-2-yl]sulfanylpropyl]piperazin-1-yl]-1h-indole Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 BLQOIFIWWXIKAF-UHFFFAOYSA-N 0.000 claims description 2
- 108091005482 5-HT4 receptors Proteins 0.000 claims description 2
- XUWBLHSIWWQLOS-UHFFFAOYSA-N 6-chloro-2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1C#N XUWBLHSIWWQLOS-UHFFFAOYSA-N 0.000 claims description 2
- NLCIDKYYIZFCJL-UHFFFAOYSA-N 6-chloro-5-fluoro-2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound N1=C(Cl)C(F)=CC(C#N)=C1SCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 NLCIDKYYIZFCJL-UHFFFAOYSA-N 0.000 claims description 2
- OVAQVEDYTABUEC-UHFFFAOYSA-N 6-cyclopropyl-2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(C(F)(F)F)=CC=1C1CC1 OVAQVEDYTABUEC-UHFFFAOYSA-N 0.000 claims description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 208000017194 Affective disease Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 2
- NRYAZFRFJWUCIM-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 NRYAZFRFJWUCIM-UHFFFAOYSA-N 0.000 claims 1
- USTKKENSKSSXDS-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 USTKKENSKSSXDS-UHFFFAOYSA-N 0.000 claims 1
- SLTVFVKVICUURL-UHFFFAOYSA-N 2-[3-[4-(1h-indol-4-yl)piperazin-1-yl]propylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 SLTVFVKVICUURL-UHFFFAOYSA-N 0.000 claims 1
- WOHRHCVZHWTOAJ-UHFFFAOYSA-N 4-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-6-methylsulfanyl-2-phenylpyrimidine-5-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(SC)=NC=1C1=CC=CC=C1 WOHRHCVZHWTOAJ-UHFFFAOYSA-N 0.000 claims 1
- INJJXDOOXZYRHI-UHFFFAOYSA-N 4-[4-[2-(2-chloropyridin-3-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound ClC1=NC=CC=C1OCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 INJJXDOOXZYRHI-UHFFFAOYSA-N 0.000 claims 1
- QMNXRSARIFTANN-UHFFFAOYSA-N 4-[4-[2-(4,6-dimethylpyrimidin-2-yl)sulfanylethyl]piperazin-1-yl]-1h-indole Chemical compound CC1=CC(C)=NC(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 QMNXRSARIFTANN-UHFFFAOYSA-N 0.000 claims 1
- KXPVRHGKHAYFOK-UHFFFAOYSA-N 4-[4-[2-(4-methyl-3-methylsulfonyl-6-phenylpyridin-2-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(S(C)(=O)=O)C(C)=CC=1C1=CC=CC=C1 KXPVRHGKHAYFOK-UHFFFAOYSA-N 0.000 claims 1
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-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
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 210000001577 neostriatum Anatomy 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- 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
- A61P25/18—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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DKPA200101037 | 2001-06-29 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200308848B true ZA200308848B (en) | 2006-02-22 |
Family
ID=8160599
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200308848A ZA200308848B (en) | 2001-06-29 | 2003-11-13 | Novel indole derivatives. |
Country Status (28)
Country | Link |
---|---|
US (1) | US7342015B2 (fr) |
EP (1) | EP1399434B1 (fr) |
JP (1) | JP2004535448A (fr) |
KR (1) | KR20040019027A (fr) |
CN (1) | CN100338058C (fr) |
AR (1) | AR034658A1 (fr) |
AT (1) | ATE304007T1 (fr) |
AU (1) | AU2002344950B2 (fr) |
BG (1) | BG108538A (fr) |
BR (1) | BR0210407A (fr) |
CA (1) | CA2451229C (fr) |
CZ (1) | CZ2004155A3 (fr) |
DE (1) | DE60206043T2 (fr) |
DK (1) | DK1399434T3 (fr) |
EA (1) | EA006104B1 (fr) |
ES (1) | ES2247347T3 (fr) |
HK (1) | HK1069579A1 (fr) |
HU (1) | HUP0400834A2 (fr) |
IL (1) | IL158830A0 (fr) |
IS (1) | IS2431B (fr) |
MX (1) | MXPA03011766A (fr) |
NO (1) | NO326513B1 (fr) |
NZ (1) | NZ529461A (fr) |
PL (1) | PL366520A1 (fr) |
SK (1) | SK642004A3 (fr) |
UA (1) | UA74651C2 (fr) |
WO (1) | WO2003002552A1 (fr) |
ZA (1) | ZA200308848B (fr) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2451228A1 (fr) * | 2001-06-29 | 2003-01-09 | H. Lundbeck A/S | Nouveaux derives heteroaryle, preparation et utilisation de ceux-ci |
WO2006056600A1 (fr) | 2004-11-26 | 2006-06-01 | Janssen Pharmaceutica N.V. | Derives d'isoxazoline-indole avec effet antipsychotique et anxiolytique ameliore |
TWI329641B (en) * | 2005-08-31 | 2010-09-01 | Otsuka Pharma Co Ltd | (benzo[b]thiophen-4-yl)piperazine compounds, pharmaceutical compositions comprising the same, uses of the same and processes for preparing the same |
JP4785881B2 (ja) * | 2007-02-27 | 2011-10-05 | 大塚製薬株式会社 | 医薬 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0900792B1 (fr) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Dérivés de pipéridine et de pipérazine comme agonistes du récepteur 5-HT1 |
CN1155567C (zh) * | 1998-04-29 | 2004-06-30 | 惠氏公司 | 抑制精神的吲哚基衍生物 |
AR027134A1 (es) * | 1999-12-30 | 2003-03-12 | Lundbeck & Co As H | Derivados de indol. |
CA2451228A1 (fr) | 2001-06-29 | 2003-01-09 | H. Lundbeck A/S | Nouveaux derives heteroaryle, preparation et utilisation de ceux-ci |
-
2002
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 AT AT02742850T patent/ATE304007T1/de not_active IP Right Cessation
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 2002-06-27 EP EP02742850A patent/EP1399434B1/fr not_active Expired - Lifetime
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Application Discontinuation
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/fr active IP Right Grant
- 2002-06-27 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 HU HU0400834A patent/HUP0400834A2/hu unknown
- 2002-06-27 CA CA002451229A patent/CA2451229C/fr not_active Expired - Fee Related
- 2002-06-28 AR ARP020102449A patent/AR034658A1/es unknown
-
2003
- 2003-11-10 IS IS7022A patent/IS2431B/is unknown
- 2003-11-13 ZA ZA200308848A patent/ZA200308848B/en unknown
- 2003-12-18 NO NO20035672A patent/NO326513B1/no unknown
-
2004
- 2004-01-21 BG BG108538A patent/BG108538A/bg unknown
-
2005
- 2005-03-11 HK HK05102171A patent/HK1069579A1/xx not_active IP Right Cessation
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