NO326513B1 - Nye indolderivater - Google Patents

Nye indolderivater Download PDF

Info

Publication number: NO326513B1
Authority: NO; Norway
Prior art keywords: indol; piperazin; ethylsulfanyl; compound; alkyl
Prior art date: 2001-06-29

Application number

NO20035672A

Other languages

English (en)

Norwegian (no)

Other versions

NO20035672D0 (no

NO20035672L (no

Inventor

Ejner Knud Moltzen

Ivan Mikkelsen

Mario Rottlander

Christian Krog-Jensen

Thomas Ruhland

Kim Andersen

Original Assignee

Lundbeck & Co As H

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-06-29

Filing date

2003-12-18

Publication date

2008-12-22

2003-12-18 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2003-12-18 Publication of NO20035672D0 publication Critical patent/NO20035672D0/no

2003-12-18 Publication of NO20035672L publication Critical patent/NO20035672L/no

2008-12-22 Publication of NO326513B1 publication Critical patent/NO326513B1/no

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
238000000338 in vitro Methods 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
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
208000019901 Anxiety disease Diseases 0.000 description 4
108090000357 Dopamine D4 receptors Proteins 0.000 description 4
102000003962 Dopamine D4 receptors Human genes 0.000 description 4
125000006598 aminocarbonylamino group Chemical group 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
229960003638 dopamine Drugs 0.000 description 4
230000003287 optical effect Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000556 agonist Substances 0.000 description 3
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
210000004556 brain Anatomy 0.000 description 3
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
239000003960 organic solvent Substances 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
201000000980 schizophrenia Diseases 0.000 description 3
239000011734 sodium Substances 0.000 description 3
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208000024891 symptom Diseases 0.000 description 3
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
JZWLOGQTHXRQJD-UHFFFAOYSA-N 2-[4-(1h-indol-4-yl)piperazin-1-yl]ethanethiol Chemical compound C1CN(CCS)CCN1C1=CC=CC2=C1C=CN2 JZWLOGQTHXRQJD-UHFFFAOYSA-N 0.000 description 2
VYKKXFKBCJQVGU-UHFFFAOYSA-N 4,6-dimethyl-2-(2-oxoethylsulfanyl)pyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCC=O)=N1 VYKKXFKBCJQVGU-UHFFFAOYSA-N 0.000 description 2
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 description 2
JGIXDOGIYVLVMD-UHFFFAOYSA-N 4-[4-[2-(2-bromopyridin-3-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound BrC1=NC=CC=C1OCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 JGIXDOGIYVLVMD-UHFFFAOYSA-N 0.000 description 2
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 description 2
NFVXMRGJZGRDTG-UHFFFAOYSA-N 4-[4-[2-(2-methylpyridin-3-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound CC1=NC=CC=C1OCCN1CCN(C=2C=3C=CNC=3C=CC=2)CC1 NFVXMRGJZGRDTG-UHFFFAOYSA-N 0.000 description 2
SULPGVDCLNALLM-UHFFFAOYSA-N 4-[4-[2-(4-methylpyridin-2-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound CC1=CC=NC(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 SULPGVDCLNALLM-UHFFFAOYSA-N 0.000 description 2
XXZYUADVEULHDP-UHFFFAOYSA-N 4-[4-[2-(5-chloropyridin-3-yl)oxyethyl]piperazin-1-yl]-1h-indole Chemical compound ClC1=CN=CC(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C1 XXZYUADVEULHDP-UHFFFAOYSA-N 0.000 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 description 2
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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)

NO20035672A 2001-06-29 2003-12-18 Nye indolderivater NO326513B1 (no)

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 (27)

Country	Link
US (1)	US7342015B2 (cs)
EP (1)	EP1399434B1 (cs)
JP (1)	JP2004535448A (cs)
KR (1)	KR20040019027A (cs)
CN (1)	CN100338058C (cs)
AR (1)	AR034658A1 (cs)
AT (1)	ATE304007T1 (cs)
AU (1)	AU2002344950B2 (cs)
BG (1)	BG108538A (cs)
BR (1)	BR0210407A (cs)
CA (1)	CA2451229C (cs)
CZ (1)	CZ2004155A3 (cs)
DE (1)	DE60206043T2 (cs)
DK (1)	DK1399434T3 (cs)
EA (1)	EA006104B1 (cs)
ES (1)	ES2247347T3 (cs)
HU (1)	HUP0400834A2 (cs)
IL (1)	IL158830A0 (cs)
IS (1)	IS2431B (cs)
MX (1)	MXPA03011766A (cs)
NO (1)	NO326513B1 (cs)
NZ (1)	NZ529461A (cs)
PL (1)	PL366520A1 (cs)
SK (1)	SK642004A3 (cs)
UA (1)	UA74651C2 (cs)
WO (1)	WO2003002552A1 (cs)
ZA (1)	ZA200308848B (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA75407C2 (en) *	2001-06-29	2006-04-17	Lundbeck & Co As H	Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof
ES2331144T3 (es)	2004-11-26	2009-12-22	Janssen Pharmaceutica Nv	Derivados de isoxazolina-indol con actividad antipsicotica y ansiolitica mejorada.
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
CN116554145B (zh) *	2022-01-29	2025-06-03	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)

* Cited by examiner, † Cited by third party
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.
UA75407C2 (en)	2001-06-29	2006-04-17	Lundbeck & Co As H	Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof

2002
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Ceased
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/en not_active Ceased
- 2002-06-27 EP EP02742850A patent/EP1399434B1/en not_active Expired - Lifetime
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 CA CA002451229A patent/CA2451229C/en not_active Expired - Fee Related
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-27 AT AT02742850T patent/ATE304007T1/de not_active IP Right Cessation
- 2002-06-27 HU HU0400834A patent/HUP0400834A2/hu unknown
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 2002-06-27 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 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

Also Published As

Publication number	Publication date
EA200400104A1 (ru)	2004-04-29
NO20035672D0 (no)	2003-12-18
HUP0400834A2 (hu)	2004-08-30
CZ2004155A3 (cs)	2004-07-14
IS2431B (is)	2008-10-15
CN100338058C (zh)	2007-09-19
ES2247347T3 (es)	2006-03-01
BG108538A (bg)	2005-01-31
AR034658A1 (es)	2004-03-03
NZ529461A (en)	2005-09-30
NO20035672L (no)	2003-12-18
MXPA03011766A (es)	2004-04-02
EA006104B1 (ru)	2005-08-25
UA74651C2 (en)	2006-01-16
PL366520A1 (en)	2005-02-07
EP1399434A1 (en)	2004-03-24
HK1069579A1 (zh)	2005-05-27
IS7022A (is)	2003-11-10
DK1399434T3 (da)	2005-12-12
CA2451229A1 (en)	2003-01-09
BR0210407A (pt)	2004-08-17
US20060258678A1 (en)	2006-11-16
JP2004535448A (ja)	2004-11-25
AU2002344950B2 (en)	2008-04-03
CA2451229C (en)	2009-02-10
US7342015B2 (en)	2008-03-11
IL158830A0 (en)	2004-05-12
ZA200308848B (en)	2006-02-22
DE60206043T2 (de)	2006-06-29
KR20040019027A (ko)	2004-03-04
DE60206043D1 (de)	2005-10-13
WO2003002552A1 (en)	2003-01-09
CN1529703A (zh)	2004-09-15
EP1399434B1 (en)	2005-09-07
ATE304007T1 (de)	2005-09-15
SK642004A3 (en)	2004-05-04

Legal Events

Date	Code	Title	Description
2008-07-14	CREP	Change of representative	Representative=s name: PLOUGMANN & VINGTOFT, POSTBOKS 1003 SENTRUM, 0104

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AU2002344949A1 (en)	2003-05-15	Novel heteroaryl derivatives, their preparation and use
CZ20022489A3 (cs)	2002-10-16	Indolová sloučenina a farmaceutický prostředek, který ji obsahuje
AU2002344950B2 (en)	2008-04-03	Novel indole derivatives
WO2001096328A1 (en)	2001-12-20	Indole derivatives useful for the treatment of cns disorders
AU2001273881A1 (en)	2002-03-14	Indole derivatives useful for the treatment of CNS disorders
AU2002344950A1 (en)	2003-05-15	Novel indole derivatives
HK1069579B (en)	2008-07-25	Novel indole derivatives
MXPA02012149A (en)	2008-10-03	Indole derivatives useful for the treatment of cns disorders
IL153234A (en)	2007-12-03	Indole derivatives and pharmaceutical compositions containing them for the treatment of cns disorders
HK1068622B (en)	2007-12-07	Novel heteroaryl derivatives, their preparation and use