SK642004A3 - Novel indole derivatives - Google Patents

Novel indole derivatives Download PDF

Info

Publication number: SK642004A3
Authority: SK; Slovakia
Prior art keywords: indol; piperazin; ethylsulfanyl; alkyl; ethoxy
Prior art date: 2001-06-29

Application number

SK64-2004A

Other languages

English (en)

Slovak (sk)

Inventor

Mario Rottlander

Ejner Knud Moltzen

Ivan Mikkelsen

Thomas Ruhland

Kim Andersen

Christian Krog-Jensen

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

2002-06-27

Publication date

2004-05-04

2002-06-27 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2004-05-04 Publication of SK642004A3 publication Critical patent/SK642004A3/sk

Links

150000002475 indoles Chemical class 0.000 title claims description 19
229940054051 antipsychotic indole derivative Drugs 0.000 title claims description 16
150000001875 compounds Chemical class 0.000 claims abstract description 64
208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
208000025966 Neurological disease Diseases 0.000 claims abstract description 9
208000028017 Psychotic disease Diseases 0.000 claims abstract description 9
208000019906 panic disease Diseases 0.000 claims abstract description 9
208000019901 Anxiety disease Diseases 0.000 claims abstract description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 8
208000019022 Mood disease Diseases 0.000 claims abstract description 7
206010041250 Social phobia Diseases 0.000 claims abstract description 7
208000030814 Eating disease Diseases 0.000 claims abstract description 6
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 6
235000014632 disordered eating Nutrition 0.000 claims abstract description 6
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 54
-1 hydroxy-C- | 6-alkyl Chemical group 0.000 claims description 31
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 26
102000005962 receptors Human genes 0.000 claims description 26
108020003175 receptors Proteins 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
239000002253 acid Substances 0.000 claims description 16
150000002431 hydrogen Chemical class 0.000 claims description 14
229960003638 dopamine Drugs 0.000 claims description 13
239000003814 drug Substances 0.000 claims description 13
230000009103 reabsorption Effects 0.000 claims description 13
230000005764 inhibitory process Effects 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
201000010099 disease Diseases 0.000 claims description 11
229940076279 serotonin Drugs 0.000 claims description 11
102000017911 HTR1A Human genes 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 10
101150015707 HTR1A gene Proteins 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 8
150000002367 halogens Chemical class 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 6
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 5
230000008485 antagonism Effects 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 claims description 4
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 4
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
239000008194 pharmaceutical composition Substances 0.000 claims description 4
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 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 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 claims description 3
YABMREVHEGXVNR-UHFFFAOYSA-N 2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethoxy]-6-methylpyridine-3-carboxamide Chemical compound CC1=CC=C(C(N)=O)C(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=N1 YABMREVHEGXVNR-UHFFFAOYSA-N 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 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
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 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
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 claims description 3
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 claims description 3
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 claims description 3
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 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
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000004705 ethylthio group Chemical group C(C)S* 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
125000004454 (C1-C6) alkoxycarbonyl 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
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
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
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 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 claims 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 claims description 2
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 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
125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 2
125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 2
PKMSJYPNXSGMBU-UHFFFAOYSA-N 6-cyclopropyl-2-[2-[4-(1h-indol-4-yl)piperazin-1-yl]ethoxy]-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3C=CNC=3C=CC=2)=C(C#N)C(C(F)(F)F)=CC=1C1CC1 PKMSJYPNXSGMBU-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 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
229910052760 oxygen Inorganic materials 0.000 claims description 2
230000000697 serotonin reuptake Effects 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 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 1
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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 1
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 1
208000017194 Affective disease Diseases 0.000 claims 1
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125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims 1
125000001072 heteroaryl group Chemical group 0.000 abstract description 2
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238000010626 work up 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)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Psychiatry (AREA)
Nutrition Science (AREA)
Anesthesiology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

SK64-2004A 2001-06-29 2002-06-27 Novel indole derivatives SK642004A3 (en)

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 (1)

Publication Number	Publication Date
SK642004A3 true SK642004A3 (en)	2004-05-04

Family

ID=8160599

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK64-2004A SK642004A3 (en)	2001-06-29	2002-06-27	Novel indole derivatives

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
CA2451228A1 (en) *	2001-06-29	2003-01-09	H. Lundbeck A/S	Novel heteroaryl derivatives, their preparation and use
US7635696B2 (en)	2004-11-26	2009-12-22	Janssen Pharmaceutica N.V.	Isoxazoline-indole derivatives with an improved antipsychotic and anxiolytic activity
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
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
AR015036A1 (es)	1998-04-29	2001-04-11	American Home Prod	Derivados de indolilo antisicoticos, composicion farmaceutica que los contiene y su uso para la manufactura de un medicamento
AR027134A1 (es) *	1999-12-30	2003-03-12	Lundbeck & Co As H	Derivados de indol.
CA2451228A1 (en)	2001-06-29	2003-01-09	H. Lundbeck A/S	Novel heteroaryl derivatives, their preparation and use

2002
- 2002-06-27 CN CNB028131878A patent/CN100338058C/zh not_active Expired - Fee Related
- 2002-06-27 ES ES02742850T patent/ES2247347T3/es not_active Expired - Lifetime
- 2002-06-27 PL PL02366520A patent/PL366520A1/xx not_active Application Discontinuation
- 2002-06-27 NZ NZ529461A patent/NZ529461A/en unknown
- 2002-06-27 MX MXPA03011766A patent/MXPA03011766A/es active IP Right Grant
- 2002-06-27 WO PCT/DK2002/000436 patent/WO2003002552A1/en not_active Ceased
- 2002-06-27 EA EA200400104A patent/EA006104B1/ru not_active IP Right Cessation
- 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 US US10/482,762 patent/US7342015B2/en not_active Expired - Fee Related
- 2002-06-27 IL IL15883002A patent/IL158830A0/xx unknown
- 2002-06-27 DE DE60206043T patent/DE60206043T2/de not_active Expired - Fee Related
- 2002-06-27 KR KR10-2003-7017127A patent/KR20040019027A/ko not_active Ceased
- 2002-06-27 JP JP2003508933A patent/JP2004535448A/ja active Pending
- 2002-06-27 SK SK64-2004A patent/SK642004A3/sk unknown
- 2002-06-27 UA UA20031211983A patent/UA74651C2/uk unknown
- 2002-06-27 AU AU2002344950A patent/AU2002344950B2/en not_active Ceased
- 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 BR BR0210407-5A patent/BR0210407A/pt not_active IP Right Cessation
- 2002-06-27 CZ CZ2004155A patent/CZ2004155A3/cs unknown
- 2002-06-27 DK DK02742850T patent/DK1399434T3/da active
- 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
EA006104B1 (ru)	2005-08-25
CA2451229A1 (en)	2003-01-09
ES2247347T3 (es)	2006-03-01
HK1069579A1 (zh)	2005-05-27
EP1399434A1 (en)	2004-03-24
IS2431B (is)	2008-10-15
NZ529461A (en)	2005-09-30
NO20035672D0 (no)	2003-12-18
MXPA03011766A (es)	2004-04-02
KR20040019027A (ko)	2004-03-04
EP1399434B1 (en)	2005-09-07
CN100338058C (zh)	2007-09-19
CA2451229C (en)	2009-02-10
ZA200308848B (en)	2006-02-22
DE60206043D1 (de)	2005-10-13
DK1399434T3 (da)	2005-12-12
UA74651C2 (en)	2006-01-16
US20060258678A1 (en)	2006-11-16
IS7022A (is)	2003-11-10
AU2002344950B2 (en)	2008-04-03
BR0210407A (pt)	2004-08-17
PL366520A1 (en)	2005-02-07
CZ2004155A3 (cs)	2004-07-14
AR034658A1 (es)	2004-03-03
NO20035672L (no)	2003-12-18
US7342015B2 (en)	2008-03-11
NO326513B1 (no)	2008-12-22
JP2004535448A (ja)	2004-11-25
BG108538A (bg)	2005-01-31
DE60206043T2 (de)	2006-06-29
WO2003002552A1 (en)	2003-01-09
CN1529703A (zh)	2004-09-15
EA200400104A1 (ru)	2004-04-29
ATE304007T1 (de)	2005-09-15
HUP0400834A2 (hu)	2004-08-30
IL158830A0 (en)	2004-05-12

Legal Events

Date	Code	Title	Description
2010-02-08	FD9A	Suspended procedure due to non-payment of fee

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