NO326513B1 - Nye indolderivater - Google Patents
Nye indolderivater Download PDFInfo
- Publication number
- NO326513B1 NO326513B1 NO20035672A NO20035672A NO326513B1 NO 326513 B1 NO326513 B1 NO 326513B1 NO 20035672 A NO20035672 A NO 20035672A NO 20035672 A NO20035672 A NO 20035672A NO 326513 B1 NO326513 B1 NO 326513B1
- Authority
- NO
- Norway
- Prior art keywords
- indol
- piperazin
- ethylsulfanyl
- compound
- alkyl
- Prior art date
Links
- 150000002475 indoles Chemical class 0.000 title description 4
- 229940054051 antipsychotic indole derivative Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 63
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- -1 hydroxy, formyl Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 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 8
- 208000012902 Nervous system disease Diseases 0.000 claims description 7
- 208000025966 Neurological disease Diseases 0.000 claims description 7
- 208000028017 Psychotic disease Diseases 0.000 claims description 7
- 208000019906 panic disease Diseases 0.000 claims description 7
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 206010041250 Social phobia Diseases 0.000 claims description 5
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 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 description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 208000011688 Generalised anxiety disease Diseases 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- 208000029364 generalized anxiety disease Diseases 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 3
- SZBBEHRNLFGLKC-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]-4-methyl-6-piperidin-1-ylpyridine-3-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(C)=CC=1N1CCCCC1 SZBBEHRNLFGLKC-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- RKXVPUIGCFWIHZ-UHFFFAOYSA-N 2-[4-[4-(1h-indol-4-yl)piperazin-1-yl]butylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 RKXVPUIGCFWIHZ-UHFFFAOYSA-N 0.000 claims description 3
- RAZMCGBENHHDPP-UHFFFAOYSA-N 4-[4-(2-pyridin-2-ylsulfanylethyl)piperazin-1-yl]-1h-indole Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CCSC1=CC=CC=N1 RAZMCGBENHHDPP-UHFFFAOYSA-N 0.000 claims description 3
- DHWOSAMCWVMMBK-UHFFFAOYSA-N 4-[4-(2-pyrimidin-2-ylsulfanylethyl)piperazin-1-yl]-1h-indole Chemical compound C1CN(C=2C=3C=CNC=3C=CC=2)CCN1CCSC1=NC=CC=N1 DHWOSAMCWVMMBK-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- 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 3
- 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 3
- VYGJIHASCBYTCH-UHFFFAOYSA-N 4-[4-[4-[5-(trifluoromethyl)pyridin-2-yl]sulfanylbutyl]piperazin-1-yl]-1h-indole Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 VYGJIHASCBYTCH-UHFFFAOYSA-N 0.000 claims description 3
- 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 3
- 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 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 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
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 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 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
- RJTYGMQZTXZJCF-UHFFFAOYSA-N 4-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethylsulfanyl]pyrimidine-5-carbonitrile Chemical compound N#CC1=CN=CN=C1SCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 RJTYGMQZTXZJCF-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 32
- 102000005962 receptors Human genes 0.000 description 20
- 108020003175 receptors Proteins 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 11
- 229940079593 drug Drugs 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 208000020016 psychiatric disease Diseases 0.000 description 10
- 230000000697 serotonin reuptake Effects 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 208000020401 Depressive disease Diseases 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 230000027455 binding Effects 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 230000003042 antagnostic effect Effects 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
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- 239000003446 ligand Substances 0.000 description 5
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N 5-methoxy-N,N-dimethyltryptamine Chemical compound COC1=CC=C2NC=C(CCN(C)C)C2=C1 ZSTKHSQDNIGFLM-UHFFFAOYSA-N 0.000 description 4
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- 125000006598 aminocarbonylamino group Chemical group 0.000 description 4
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- 229910002027 silica gel Inorganic materials 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000024827 Alzheimer disease Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000000561 anti-psychotic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
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- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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- DVCRWPDKYSPKQX-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethoxy]-4-methyl-6-piperidin-1-ylpyridine-3-carbonitrile Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(C)=CC=1N1CCCCC1 DVCRWPDKYSPKQX-UHFFFAOYSA-N 0.000 description 2
- 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 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 description 2
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- WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
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- 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
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- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
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- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
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- VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
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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)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DKPA200101037 | 2001-06-29 | ||
| PCT/DK2002/000436 WO2003002552A1 (en) | 2001-06-29 | 2002-06-27 | Novel indole derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20035672D0 NO20035672D0 (no) | 2003-12-18 |
| NO20035672L NO20035672L (no) | 2003-12-18 |
| NO326513B1 true NO326513B1 (no) | 2008-12-22 |
Family
ID=8160599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20035672A NO326513B1 (no) | 2001-06-29 | 2003-12-18 | Nye indolderivater |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US7342015B2 (uk) |
| EP (1) | EP1399434B1 (uk) |
| JP (1) | JP2004535448A (uk) |
| KR (1) | KR20040019027A (uk) |
| CN (1) | CN100338058C (uk) |
| AR (1) | AR034658A1 (uk) |
| AT (1) | ATE304007T1 (uk) |
| AU (1) | AU2002344950B2 (uk) |
| BG (1) | BG108538A (uk) |
| BR (1) | BR0210407A (uk) |
| CA (1) | CA2451229C (uk) |
| CZ (1) | CZ2004155A3 (uk) |
| DE (1) | DE60206043T2 (uk) |
| DK (1) | DK1399434T3 (uk) |
| EA (1) | EA006104B1 (uk) |
| ES (1) | ES2247347T3 (uk) |
| HK (1) | HK1069579A1 (uk) |
| HU (1) | HUP0400834A2 (uk) |
| IL (1) | IL158830A0 (uk) |
| IS (1) | IS2431B (uk) |
| MX (1) | MXPA03011766A (uk) |
| NO (1) | NO326513B1 (uk) |
| NZ (1) | NZ529461A (uk) |
| PL (1) | PL366520A1 (uk) |
| SK (1) | SK642004A3 (uk) |
| UA (1) | UA74651C2 (uk) |
| WO (1) | WO2003002552A1 (uk) |
| ZA (1) | ZA200308848B (uk) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK1399438T3 (da) * | 2001-06-29 | 2006-04-18 | Lundbeck & Co As H | Hidtil ukendte heteroarylderivater samt fremstilling og anvendelse heraf |
| DE602005016836D1 (de) | 2004-11-26 | 2009-11-05 | Janssen Pharmaceutica Nv | Chotischer und anxiolytischer aktivität |
| AR055203A1 (es) * | 2005-08-31 | 2007-08-08 | Otsuka Pharma Co Ltd | Derivados de benzotiofeno con propiedades antipsicoticas |
| JP4785881B2 (ja) * | 2007-02-27 | 2011-10-05 | 大塚製薬株式会社 | 医薬 |
| CN116554145A (zh) * | 2022-01-29 | 2023-08-08 | 江苏恩华药业股份有限公司 | 芳烷基-4-(1h)吲哚基哌嗪衍生物、其制备方法和应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0900792B1 (en) * | 1997-09-02 | 2003-10-29 | Duphar International Research B.V | Piperazine and piperidine derivatives as 5-HT1A and dopamine D2-receptor (ant)agonists |
| WO1999055672A2 (en) * | 1998-04-29 | 1999-11-04 | American Home Products Corporation | Antipsychotic indolyl derivatives |
| AR027134A1 (es) * | 1999-12-30 | 2003-03-12 | Lundbeck & Co As H | Derivados de indol. |
| DK1399438T3 (da) * | 2001-06-29 | 2006-04-18 | Lundbeck & Co As H | Hidtil ukendte heteroarylderivater samt fremstilling og anvendelse heraf |
-
2002
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 HU HU0400834A patent/HUP0400834A2/hu unknown
- 2002-06-27 AT AT02742850T patent/ATE304007T1/de not_active IP Right Cessation
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 CA CA002451229A patent/CA2451229C/en not_active Expired - Fee Related
- 2002-06-27 EP EP02742850A patent/EP1399434B1/en not_active Expired - Lifetime
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Application Discontinuation
- 2002-06-27 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/en active IP Right Grant
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-28 AR ARP020102449A patent/AR034658A1/es unknown
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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
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2004
- 2004-01-21 BG BG108538A patent/BG108538A/bg unknown
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2005
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