SK16052003A3 - New indole derivatives with 5-HT6 receptor affinity - Google Patents

New indole derivatives with 5-HT6 receptor affinity Download PDF

Info

Publication number: SK16052003A3
Authority: SK; Slovakia
Prior art keywords: indole; piperazin; methyl; compound; benzenesulfonyl
Prior art date: 2001-06-07

Application number

SK16052003A

Other languages

English (en)

Slovak (sk)

Inventor

Colin Charles Beard

Robin Douglas Clark

Lawrence Emerson Fisher

Ralph New Harris Iii

David Bruce Repke

Original Assignee

Hoffmann La Roche

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.)

2001-06-07

Filing date

2002-05-29

Publication date

2004-10-05

2002-05-29 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2004-10-05 Publication of SK16052003A3 publication Critical patent/SK16052003A3/sk

Links

108091005435 5-HT6 receptors Proteins 0.000 title abstract description 6
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 abstract description 142
239000000203 mixture Substances 0.000 claims abstract description 76
238000002360 preparation method Methods 0.000 claims abstract description 29
238000000034 method Methods 0.000 claims abstract description 27
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 20
239000012453 solvate Substances 0.000 claims abstract description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
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 claims abstract description 9
239000003814 drug Substances 0.000 claims abstract description 7
125000001424 substituent group Chemical group 0.000 claims abstract description 7
-1 C 1-6 -alkoxy Chemical group 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 34
229910052739 hydrogen Inorganic materials 0.000 claims description 28
239000001257 hydrogen Substances 0.000 claims description 27
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 24
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
125000001188 haloalkyl group Chemical group 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000005843 halogen group Chemical group 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
238000006243 chemical reaction Methods 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 19
125000006239 protecting group Chemical group 0.000 claims description 19
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 17
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 17
201000010099 disease Diseases 0.000 claims description 16
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
125000004663 dialkyl amino group Chemical group 0.000 claims description 15
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 15
125000004001 thioalkyl group Chemical group 0.000 claims description 15
125000003282 alkyl amino group Chemical group 0.000 claims description 14
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 13
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 13
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 13
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 13
239000000651 prodrug Substances 0.000 claims description 13
229940002612 prodrug Drugs 0.000 claims description 13
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 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
125000001072 heteroaryl group Chemical group 0.000 claims description 11
GDAVGFZIUMQUFK-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-piperazin-1-yl-1h-indole Chemical compound C=1C=CC=CC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 GDAVGFZIUMQUFK-UHFFFAOYSA-N 0.000 claims description 9
230000002152 alkylating effect Effects 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 8
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 8
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 8
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
URMFOQOYDIKMIK-UHFFFAOYSA-N 1-methyl-7-piperazin-1-yl-3-pyridin-2-ylsulfonylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3N=CC=CC=3)C2=CC=CC=1N1CCNCC1 URMFOQOYDIKMIK-UHFFFAOYSA-N 0.000 claims description 6
AOPYPEADLGTXRA-UHFFFAOYSA-N 3-(benzenesulfonyl)-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC=CC=C1 AOPYPEADLGTXRA-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
HASYOGBGAAQMOE-UHFFFAOYSA-N 2-[(7-piperazin-1-yl-1h-indol-3-yl)sulfonyl]-1,3-benzothiazole Chemical compound N=1C2=CC=CC=C2SC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 HASYOGBGAAQMOE-UHFFFAOYSA-N 0.000 claims description 4
JNFVCANJVNIARP-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfanyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(SC=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1Cl JNFVCANJVNIARP-UHFFFAOYSA-N 0.000 claims description 4
ZWNAAKFEJNASML-UHFFFAOYSA-N 3-(4-methylphenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 ZWNAAKFEJNASML-UHFFFAOYSA-N 0.000 claims description 4
OIXUCVNAHFWIAX-UHFFFAOYSA-N 3-phenylsulfanyl-7-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=CC2=C1NC=C2SC1=CC=CC=C1 OIXUCVNAHFWIAX-UHFFFAOYSA-N 0.000 claims description 4
208000023105 Huntington disease Diseases 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 4
208000028017 Psychotic disease Diseases 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
201000000980 schizophrenia Diseases 0.000 claims description 4
IMQIDUOMANFWEA-UHFFFAOYSA-N 1-methyl-7-piperazin-1-yl-3-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC=CC=1N1CCNCC1 IMQIDUOMANFWEA-UHFFFAOYSA-N 0.000 claims description 3
KSFMHGCCSUWHQR-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C(=C(Cl)C=CC=3)Cl)C2=CC=1N1CCNCC1 KSFMHGCCSUWHQR-UHFFFAOYSA-N 0.000 claims description 3
VNFFUYINJKNKQN-UHFFFAOYSA-N 3-(2,3-dichlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1Cl VNFFUYINJKNKQN-UHFFFAOYSA-N 0.000 claims description 3
MONILMKLUJUPQJ-UHFFFAOYSA-N 3-(2,4-dichlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC=C(Cl)C=C1Cl MONILMKLUJUPQJ-UHFFFAOYSA-N 0.000 claims description 3
PHSSKMCYVXEVGJ-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-1-methyl-7-piperazin-1-ylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C(=CC=CC=3)Cl)C2=CC=CC=1N1CCNCC1 PHSSKMCYVXEVGJ-UHFFFAOYSA-N 0.000 claims description 3
DVMBIRSQFNXXGY-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC=C1S(=O)(=O)C1=CNC2=CC=C(N3CCNCC3)C=C12 DVMBIRSQFNXXGY-UHFFFAOYSA-N 0.000 claims description 3
PNLBETDAZXHYOY-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 PNLBETDAZXHYOY-UHFFFAOYSA-N 0.000 claims description 3
YDNYBANWFSSBCJ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 YDNYBANWFSSBCJ-UHFFFAOYSA-N 0.000 claims description 3
AARLIECDOQZADI-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=C(Cl)C=C(Cl)C=3)C2=CC=1N1CCNCC1 AARLIECDOQZADI-UHFFFAOYSA-N 0.000 claims description 3
ACCRXPJDTORLAF-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)C=2C3=CC(=CC=C3NC=2)N2CCNCC2)=C1 ACCRXPJDTORLAF-UHFFFAOYSA-N 0.000 claims description 3
JPLKRWGVLJIBGH-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC(Cl)=CC(S(=O)(=O)C=2C3=CC=CC(=C3NC=2)N2CCNCC2)=C1 JPLKRWGVLJIBGH-UHFFFAOYSA-N 0.000 claims description 3
ROLMXIQSKFYWJD-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound ClC1=CC=CC(S(=O)(=O)C=2C3=CC=CC(=C3NC=2)N2CCNCC2)=C1 ROLMXIQSKFYWJD-UHFFFAOYSA-N 0.000 claims description 3
DFQRMJUQINQKIV-UHFFFAOYSA-N 3-(4-chlorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CNC2=CC=C(N3CCNCC3)C=C12 DFQRMJUQINQKIV-UHFFFAOYSA-N 0.000 claims description 3
DIUOHDVVFYLFEF-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=CC(F)=CC=3)C2=CC=1N1CCNCC1 DIUOHDVVFYLFEF-UHFFFAOYSA-N 0.000 claims description 3
WMBSYZBDNPJOHN-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-1-methyl-7-piperazin-1-ylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=CC(F)=CC=3)C2=CC=CC=1N1CCNCC1 WMBSYZBDNPJOHN-UHFFFAOYSA-N 0.000 claims description 3
MVASXMIUOMSKSW-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-2-methyl-7-piperazin-1-yl-1h-indole Chemical compound CC=1NC2=C(N3CCNCC3)C=CC=C2C=1S(=O)(=O)C1=CC=C(F)C=C1 MVASXMIUOMSKSW-UHFFFAOYSA-N 0.000 claims description 3
NXWCLGICFPYIQQ-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-5-piperazin-1-yl-1h-indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CNC2=CC=C(N3CCNCC3)C=C12 NXWCLGICFPYIQQ-UHFFFAOYSA-N 0.000 claims description 3
CCIXMBUPVYANKE-UHFFFAOYSA-N 3-(4-fluorophenyl)sulfonyl-7-piperazin-1-yl-1h-indole Chemical compound C1=CC(F)=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 CCIXMBUPVYANKE-UHFFFAOYSA-N 0.000 claims description 3
MUQBBJRTJNEBML-UHFFFAOYSA-N 3-(benzenesulfonyl)-1-methyl-7-piperazin-1-ylindole Chemical compound C=12N(C)C=C(S(=O)(=O)C=3C=CC=CC=3)C2=CC=CC=1N1CCNCC1 MUQBBJRTJNEBML-UHFFFAOYSA-N 0.000 claims description 3
KEBHHQMXRDDUNP-UHFFFAOYSA-N 7-piperazin-1-yl-3-[2-(trifluoromethyl)phenyl]sulfonyl-1h-indole Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)C1=CNC2=C(N3CCNCC3)C=CC=C12 KEBHHQMXRDDUNP-UHFFFAOYSA-N 0.000 claims description 3
CAJWEQVPXOUTIJ-UHFFFAOYSA-N 7-piperazin-1-yl-3-pyridin-2-ylsulfonyl-1h-indole Chemical compound C=1C=CC=NC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 CAJWEQVPXOUTIJ-UHFFFAOYSA-N 0.000 claims description 3
MPOVFRIXKVWYRK-UHFFFAOYSA-N 7-piperazin-1-yl-3-pyridin-4-ylsulfonyl-1h-indole Chemical compound C=1C=NC=CC=1S(=O)(=O)C(C1=CC=C2)=CNC1=C2N1CCNCC1 MPOVFRIXKVWYRK-UHFFFAOYSA-N 0.000 claims description 3
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000020925 Bipolar disease Diseases 0.000 claims description 3
208000008589 Obesity Diseases 0.000 claims description 3
239000000556 agonist Substances 0.000 claims description 3
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
208000028683 bipolar I disease Diseases 0.000 claims description 3
208000015114 central nervous system disease Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
235000020824 obesity Nutrition 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
KZKNUAVJNCEFAG-UHFFFAOYSA-N 1-methyl-5-piperazin-1-yl-3-[3-(trifluoromethyl)phenyl]sulfonylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C=C(C=CC=3)C(F)(F)F)C2=CC=1N1CCNCC1 KZKNUAVJNCEFAG-UHFFFAOYSA-N 0.000 claims description 2
BAHGORPXQDMZAU-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfonyl-1-methyl-5-piperazin-1-ylindole Chemical compound C=1C=C2N(C)C=C(S(=O)(=O)C=3C(=CC=CC=3)Cl)C2=CC=1N1CCNCC1 BAHGORPXQDMZAU-UHFFFAOYSA-N 0.000 claims description 2
XBHZVMURXUWHAP-UHFFFAOYSA-N 3-(3,5-dichlorophenyl)sulfonyl-7-(4-methylpiperazin-1-yl)-1h-indole Chemical compound C1CN(C)CCN1C1=CC=CC2=C1NC=C2S(=O)(=O)C1=CC(Cl)=CC(Cl)=C1 XBHZVMURXUWHAP-UHFFFAOYSA-N 0.000 claims description 2
NCKKZZZBTWJOOL-UHFFFAOYSA-N 3-(4-methoxyphenyl)sulfonyl-2-methyl-7-piperazin-1-yl-1h-indole Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)C1=C(C)NC2=C(N3CCNCC3)C=CC=C12 NCKKZZZBTWJOOL-UHFFFAOYSA-N 0.000 claims description 2
ITWGBNZGHMFGTG-UHFFFAOYSA-N 3-phenylsulfanyl-5-piperazin-1-yl-1h-indole Chemical compound C1CNCCN1C1=CC=C(NC=C2SC=3C=CC=CC=3)C2=C1 ITWGBNZGHMFGTG-UHFFFAOYSA-N 0.000 claims description 2
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
208000012902 Nervous system disease Diseases 0.000 claims description 2
208000025966 Neurological disease Diseases 0.000 claims description 2
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 2
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125000004656 alkyl sulfonylamino group Chemical group 0.000 claims 11
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229940124597 therapeutic agent Drugs 0.000 abstract description 2
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- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Addiction (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Psychology (AREA)
Child & Adolescent Psychology (AREA)
Diabetes (AREA)
Hematology (AREA)
Anesthesiology (AREA)
Hospice & Palliative Care (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Obesity (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK16052003A 2001-06-07 2002-05-29 New indole derivatives with 5-HT6 receptor affinity SK16052003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US29670501P	2001-06-07	2001-06-07
US34021201P	2001-12-13	2001-12-13
PCT/EP2002/005890 WO2002098857A1 (fr)	2001-06-07	2002-05-29	Nouveaux derives de l'indole a affinite pour le recepteur 5-ht6

Publications (1)

Publication Number	Publication Date
SK16052003A3 true SK16052003A3 (en)	2004-10-05

Family

ID=26969776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK16052003A SK16052003A3 (en)	2001-06-07	2002-05-29	New indole derivatives with 5-HT6 receptor affinity

Country Status (32)

Country	Link
US (3)	US6787535B2 (fr)
EP (1)	EP1401813B1 (fr)
JP (1)	JP4187642B2 (fr)
KR (1)	KR100600240B1 (fr)
CN (1)	CN1257892C (fr)
AR (1)	AR036233A1 (fr)
AT (1)	ATE353318T1 (fr)
AU (1)	AU2002310747B2 (fr)
BG (1)	BG108420A (fr)
BR (1)	BR0210929A (fr)
CA (1)	CA2449874C (fr)
CO (1)	CO5630036A2 (fr)
CZ (1)	CZ20033529A3 (fr)
DE (1)	DE60218037T2 (fr)
ES (1)	ES2280546T3 (fr)
HR (1)	HRP20030984A2 (fr)
HU (1)	HUP0401307A2 (fr)
IL (1)	IL158997A0 (fr)
MA (1)	MA27032A1 (fr)
MX (1)	MXPA03011244A (fr)
NO (1)	NO20035359D0 (fr)
NZ (1)	NZ529631A (fr)
PA (1)	PA8546601A1 (fr)
PE (1)	PE20030039A1 (fr)
PL (1)	PL367305A1 (fr)
RU (1)	RU2294932C2 (fr)
SK (1)	SK16052003A3 (fr)
TW (1)	TW591015B (fr)
UY (1)	UY27322A1 (fr)
WO (1)	WO2002098857A1 (fr)
YU (1)	YU96103A (fr)
ZA (1)	ZA200309005B (fr)

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2002
- 2002-05-29 BR BR0210929-8A patent/BR0210929A/pt not_active Application Discontinuation
- 2002-05-29 IL IL15899702A patent/IL158997A0/xx unknown
- 2002-05-29 KR KR1020037016022A patent/KR100600240B1/ko not_active Expired - Fee Related
- 2002-05-29 EP EP02735394A patent/EP1401813B1/fr not_active Expired - Lifetime
- 2002-05-29 CN CNB028115244A patent/CN1257892C/zh not_active Expired - Fee Related
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- 2002-05-29 MX MXPA03011244A patent/MXPA03011244A/es active IP Right Grant
- 2002-05-29 AT AT02735394T patent/ATE353318T1/de not_active IP Right Cessation
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- 2002-05-29 CA CA002449874A patent/CA2449874C/fr not_active Expired - Fee Related
- 2002-05-29 DE DE60218037T patent/DE60218037T2/de not_active Expired - Lifetime
- 2002-05-29 SK SK16052003A patent/SK16052003A3/sk unknown
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- 2002-05-29 PL PL02367305A patent/PL367305A1/xx not_active Application Discontinuation
- 2002-05-29 CZ CZ20033529A patent/CZ20033529A3/cs unknown
- 2002-05-29 WO PCT/EP2002/005890 patent/WO2002098857A1/fr not_active Ceased
- 2002-05-29 AU AU2002310747A patent/AU2002310747B2/en not_active Ceased
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- 2002-05-29 HR HR20030984A patent/HRP20030984A2/hr not_active Application Discontinuation
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- 2002-06-04 AR ARP020102066A patent/AR036233A1/es not_active Application Discontinuation
- 2002-06-06 US US10/164,660 patent/US6787535B2/en not_active Expired - Fee Related
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- 2002-06-07 PE PE2002000481A patent/PE20030039A1/es not_active Application Discontinuation
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- 2003-12-02 NO NO20035359A patent/NO20035359D0/no not_active Application Discontinuation
- 2003-12-03 MA MA27422A patent/MA27032A1/fr unknown
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2004
- 2004-06-25 US US10/876,863 patent/US20040248902A1/en not_active Abandoned
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Publication number	Publication date
MA27032A1 (fr)	2004-12-20
RU2003136731A (ru)	2005-05-20
RU2294932C2 (ru)	2007-03-10
CN1257892C (zh)	2006-05-31
BG108420A (en)	2005-02-28
EP1401813B1 (fr)	2007-02-07
BR0210929A (pt)	2004-06-08
ES2280546T3 (es)	2007-09-16
PL367305A1 (en)	2005-02-21
US20030073700A1 (en)	2003-04-17
CA2449874A1 (fr)	2002-12-12
HRP20030984A2 (en)	2005-10-31
CO5630036A2 (es)	2006-04-28
CN1527816A (zh)	2004-09-08
NO20035359D0 (no)	2003-12-02
HUP0401307A2 (hu)	2004-12-28
CZ20033529A3 (cs)	2004-04-14
MXPA03011244A (es)	2004-02-27
TW591015B (en)	2004-06-11
US20050171118A1 (en)	2005-08-04
AU2002310747B2 (en)	2007-10-11
ZA200309005B (en)	2005-02-21
KR100600240B1 (ko)	2006-07-13
JP4187642B2 (ja)	2008-11-26
UY27322A1 (es)	2003-02-28
EP1401813A1 (fr)	2004-03-31
YU96103A (sh)	2006-08-17
PE20030039A1 (es)	2003-02-13
DE60218037D1 (de)	2007-03-22
PA8546601A1 (es)	2003-01-24
AR036233A1 (es)	2004-08-25
DE60218037T2 (de)	2007-08-23
HK1068610A1 (en)	2005-04-29
WO2002098857A8 (fr)	2004-04-22
US6787535B2 (en)	2004-09-07
US20040248902A1 (en)	2004-12-09
JP2004533460A (ja)	2004-11-04
ATE353318T1 (de)	2007-02-15
NZ529631A (en)	2006-08-31
IL158997A0 (en)	2004-05-12
WO2002098857A1 (fr)	2002-12-12
CA2449874C (fr)	2009-06-23
KR20040004702A (ko)	2004-01-13

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2011-07-06	FD9A	Suspended procedure due to non-payment of fee

Publication	Publication Date	Title
SK16052003A3 (en)	2004-10-05	New indole derivatives with 5-HT6 receptor affinity
EP1401812B1 (fr)	2006-06-28	Derives de 4-piperazinylindole a affinite avec les recepteurs 5-ht6
AU2002310747A1 (en)	2003-05-08	New indole derivatives with 5-HT6 receptor affinity
AU2003283265B2 (en)	2009-03-05	4-piperazinyl benzenesulfonyl indoles with 5-HT6 receptor affinity
EP1335722B1 (fr)	2006-08-30	Derivés indole-sulfoniques pour le traitement de troubles du snc
JP3057109B2 (ja)	2000-06-26	新規インドール誘導体
KR20050057356A (ko)	2005-06-16	2,4-치환된 인돌 및 그의 5-ｈｔ6 조절제로서 용도
JP2006503052A (ja)	2006-01-26	２，７−置換インドール及び５−ｈｔ６モジュレーターとしてのその使用
EP0729958A2 (fr)	1996-09-04	Dérivés antimigraines d'indolylpyridinyl et pyrimidinyl-pipérazinyl-1,2,5-thiadiazoles
CN1321110C (zh)	2007-06-13	具有5－ht6受体亲和力的4－哌嗪基吲哚衍生物
AU2002345587A1 (en)	2003-01-02	4-Piperazinylindole derivatives with 5-HT6 receptor affinity