SK652004A3 - Heteroaryl derivatives, pharmaceutical composition with the content thereof and use of the same - Google Patents

Heteroaryl derivatives, pharmaceutical composition with the content thereof and use of the same Download PDF

Info

Publication number: SK652004A3
Authority: SK; Slovakia
Prior art keywords: piperazin; dioxin; dihydrobenzo; ethylsulfanyl; chloro
Prior art date: 2001-06-29

Application number

SK65-2004A

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

2004-09-08

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

2004-09-08 Publication of SK652004A3 publication Critical patent/SK652004A3/sk

Links

125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 28
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
150000001875 compounds Chemical class 0.000 claims abstract description 63
208000019901 Anxiety disease Diseases 0.000 claims abstract description 10
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 8
208000019906 panic disease Diseases 0.000 claims abstract description 8
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 7
206010041250 Social phobia Diseases 0.000 claims abstract description 6
208000030814 Eating disease Diseases 0.000 claims abstract description 5
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
235000014632 disordered eating Nutrition 0.000 claims abstract description 5
-1 hydroxy, formyl Chemical group 0.000 claims description 67
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 49
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 43
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 42
102000005962 receptors Human genes 0.000 claims description 33
108020003175 receptors Proteins 0.000 claims description 33
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 17
239000000203 mixture Substances 0.000 claims description 17
239000002253 acid Substances 0.000 claims description 16
229960003638 dopamine Drugs 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
230000005764 inhibitory process Effects 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 13
150000002367 halogens Chemical class 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
125000002252 acyl group Chemical group 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
208000035475 disorder Diseases 0.000 claims description 10
125000004093 cyano group Chemical group *C#N 0.000 claims description 9
125000004442 acylamino group Chemical group 0.000 claims description 7
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
230000009103 reabsorption Effects 0.000 claims description 7
229940076279 serotonin Drugs 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
ZHIJWZZZCKXDFH-UHFFFAOYSA-N 5-[4-[4-[5-(trifluoromethyl)pyridin-2-yl]sulfanylbutyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 ZHIJWZZZCKXDFH-UHFFFAOYSA-N 0.000 claims description 6
208000027534 Emotional disease Diseases 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
230000008485 antagonism Effects 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
FYEDYNMAOKWPPS-UHFFFAOYSA-N 2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound C=1C(Cl)=CC=2NC(=O)COC=2C=1N(CC1)CCN1CCSC1=NC=CC=C1C#N FYEDYNMAOKWPPS-UHFFFAOYSA-N 0.000 claims description 4
NNPANPCWQVKLQW-UHFFFAOYSA-N 2-[3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 NNPANPCWQVKLQW-UHFFFAOYSA-N 0.000 claims description 4
102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 claims description 4
101710138638 5-hydroxytryptamine receptor 1A Proteins 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
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-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
125000006624 (C1-C6) alkoxycarbonylamino group Chemical group 0.000 claims description 3
XHODGCDQUXRFSU-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[2-(3-piperidin-1-ylsulfonylpyridin-4-yl)sulfanylethyl]piperazine Chemical compound C=1N=CC=C(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)C=1S(=O)(=O)N1CCCCC1 XHODGCDQUXRFSU-UHFFFAOYSA-N 0.000 claims description 3
OXCXPXTYBYSJAV-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[2-(4-methyl-3-methylsulfonyl-6-phenylpyridin-2-yl)oxyethyl]piperazine Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C(S(C)(=O)=O)C(C)=CC=1C1=CC=CC=C1 OXCXPXTYBYSJAV-UHFFFAOYSA-N 0.000 claims description 3
XSJBDYDYBHTSLM-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[3-[5-(trifluoromethyl)pyridin-2-yl]sulfanylpropyl]piperazine Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 XSJBDYDYBHTSLM-UHFFFAOYSA-N 0.000 claims description 3
JQVGSYIWQADKIT-UHFFFAOYSA-N 1-(2,3-dihydro-1,4-benzodioxin-5-yl)-4-[4-[5-(trifluoromethyl)pyridin-2-yl]sulfanylbutyl]piperazine Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 JQVGSYIWQADKIT-UHFFFAOYSA-N 0.000 claims description 3
OZIJHHYSLGLFOL-UHFFFAOYSA-N 1-[2-(5-chloropyridin-3-yl)oxyethyl]-4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazine Chemical compound ClC1=CN=CC(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1 OZIJHHYSLGLFOL-UHFFFAOYSA-N 0.000 claims description 3
WWWCZBWFCQQJBJ-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethoxy]-4-methyl-6-piperidin-1-ylpyridine-3-carbonitrile Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C(C#N)C(C)=CC=1N1CCCCC1 WWWCZBWFCQQJBJ-UHFFFAOYSA-N 0.000 claims description 3
LAZMRPNFYMBBMG-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethoxy]-6-methylpyridine-3-carboxamide Chemical compound CC1=CC=C(C(N)=O)C(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 LAZMRPNFYMBBMG-UHFFFAOYSA-N 0.000 claims description 3
OEPMXIGTJKYHRH-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethoxy]pyridine-4-carbonitrile Chemical compound N#CC1=CC=NC(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1 OEPMXIGTJKYHRH-UHFFFAOYSA-N 0.000 claims description 3
XOEGQEUOVHQEMJ-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-4,6-dimethoxypyrimidine Chemical compound COC1=CC(OC)=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 XOEGQEUOVHQEMJ-UHFFFAOYSA-N 0.000 claims description 3
HONCNXHQIFLUSN-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 HONCNXHQIFLUSN-UHFFFAOYSA-N 0.000 claims description 3
KYGRRDTYQHTEHC-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-4-methoxypyridine-3-carbonitrile Chemical compound COC1=CC=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1C#N KYGRRDTYQHTEHC-UHFFFAOYSA-N 0.000 claims description 3
OLJZTZQWGBMSAW-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-5-ethylpyrimidine Chemical compound N1=CC(CC)=CN=C1SCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 OLJZTZQWGBMSAW-UHFFFAOYSA-N 0.000 claims description 3
DXXQTBBXIMUPBB-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-6-methyl-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound CC1=CC(C(F)(F)F)=C(C#N)C(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 DXXQTBBXIMUPBB-UHFFFAOYSA-N 0.000 claims description 3
IJGINDCKMJEBJO-UHFFFAOYSA-N 2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC=C(C#N)C(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=N1 IJGINDCKMJEBJO-UHFFFAOYSA-N 0.000 claims description 3
NPNDRHCBWAMYKI-UHFFFAOYSA-N 2-[2-[4-(6-chloro-3,4-dihydro-2h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCN2CCN(CC2)C=2C=3OCCNC=3C=C(Cl)C=2)=N1 NPNDRHCBWAMYKI-UHFFFAOYSA-N 0.000 claims description 3
TYTAGQWOOONNBF-UHFFFAOYSA-N 2-[2-[4-(6-chloro-3,4-dihydro-2h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound C=1C(Cl)=CC=2NCCOC=2C=1N(CC1)CCN1CCSC1=NC=CC=C1C#N TYTAGQWOOONNBF-UHFFFAOYSA-N 0.000 claims description 3
USAYJQFCHGXUHD-UHFFFAOYSA-N 2-[3-[4-(8-cyano-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=N1 USAYJQFCHGXUHD-UHFFFAOYSA-N 0.000 claims description 3
NLNBIDZBJUQPLE-UHFFFAOYSA-N 4-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-6-methylsulfanyl-2-phenylpyrimidine-5-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C(C#N)C(SC)=NC=1C1=CC=CC=C1 NLNBIDZBJUQPLE-UHFFFAOYSA-N 0.000 claims description 3
JQQRXUWAYIWOEV-UHFFFAOYSA-N 4-[2-[4-(8-cyano-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-6-methylsulfanyl-2-phenylpyrimidine-5-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=C(C#N)C(SC)=NC=1C1=CC=CC=C1 JQQRXUWAYIWOEV-UHFFFAOYSA-N 0.000 claims description 3
DKXOJCBHCSZEIA-UHFFFAOYSA-N 4-chloro-2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]-6-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=C(C#N)C(SCCN2CCN(CC2)C=2C=3OCC(=O)NC=3C=C(Cl)C=2)=N1 DKXOJCBHCSZEIA-UHFFFAOYSA-N 0.000 claims description 3
DDAYEVUGENSTGN-UHFFFAOYSA-N 5-[4-(2-pyridin-2-ylsulfanylethyl)piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound C1=2OCCOC=2C(C#N)=CC=C1N(CC1)CCN1CCSC1=CC=CC=N1 DDAYEVUGENSTGN-UHFFFAOYSA-N 0.000 claims description 3
JDLVTMNLVDVPNO-UHFFFAOYSA-N 5-[4-[2-(2-bromopyridin-3-yl)oxyethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound BrC1=NC=CC=C1OCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 JDLVTMNLVDVPNO-UHFFFAOYSA-N 0.000 claims description 3
XFQOTMQCDINFLC-UHFFFAOYSA-N 5-[4-[2-(2-chloropyridin-3-yl)oxyethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound ClC1=NC=CC=C1OCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 XFQOTMQCDINFLC-UHFFFAOYSA-N 0.000 claims description 3
FMSXYVSEJHSEAU-UHFFFAOYSA-N 5-[4-[2-(2-methylpyridin-3-yl)oxyethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound CC1=NC=CC=C1OCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 FMSXYVSEJHSEAU-UHFFFAOYSA-N 0.000 claims description 3
PGAQEAAWHSKDOL-UHFFFAOYSA-N 5-[4-[2-(4,6-dimethylpyrimidin-2-yl)sulfanylethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound CC1=CC(C)=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=N1 PGAQEAAWHSKDOL-UHFFFAOYSA-N 0.000 claims description 3
YLTFPHZZKMDBHL-UHFFFAOYSA-N 5-[4-[2-(4-chloro-6-methylpyrimidin-2-yl)sulfanylethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound CC1=CC(Cl)=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=N1 YLTFPHZZKMDBHL-UHFFFAOYSA-N 0.000 claims description 3
JAIGJTNIZZBKMZ-UHFFFAOYSA-N 5-[4-[2-(4-methyl-3-methylsulfonyl-6-phenylpyridin-2-yl)sulfanylethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound N=1C(SCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=C(S(C)(=O)=O)C(C)=CC=1C1=CC=CC=C1 JAIGJTNIZZBKMZ-UHFFFAOYSA-N 0.000 claims description 3
QQBWDPOHBXBFND-UHFFFAOYSA-N 5-[4-[2-(5-chloropyridin-3-yl)oxyethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound ClC1=CN=CC(OCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=C1 QQBWDPOHBXBFND-UHFFFAOYSA-N 0.000 claims description 3
AUVZLNGKOYJJJY-UHFFFAOYSA-N 5-[4-[2-[4-(trifluoromethyl)pyrimidin-2-yl]sulfanylethyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound FC(F)(F)C1=CC=NC(SCCN2CCN(CC2)C=2C=3OCCOC=3C(C#N)=CC=2)=N1 AUVZLNGKOYJJJY-UHFFFAOYSA-N 0.000 claims description 3
KZOWMGNTABUBNR-UHFFFAOYSA-N 5-[4-[3-[5-(trifluoromethyl)pyridin-2-yl]sulfanylpropyl]piperazin-1-yl]-2,3-dihydro-1,4-benzodioxine-8-carbonitrile Chemical compound N1=CC(C(F)(F)F)=CC=C1SCCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 KZOWMGNTABUBNR-UHFFFAOYSA-N 0.000 claims description 3
LOJRBSCDURKAQY-UHFFFAOYSA-N 5-chloro-2-[2-[4-(6-chloro-3,4-dihydro-2h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound N#CC1=CC(Cl)=CN=C1SCCN1CCN(C=2C=3OCCNC=3C=C(Cl)C=2)CC1 LOJRBSCDURKAQY-UHFFFAOYSA-N 0.000 claims description 3
ZMCNHFIEBMXHIO-UHFFFAOYSA-N 5-chloro-2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]-4,6-dimethylpyridine-3-carbonitrile Chemical compound CC1=C(Cl)C(C)=NC(SCCN2CCN(CC2)C=2C=3OCC(=O)NC=3C=C(Cl)C=2)=C1C#N ZMCNHFIEBMXHIO-UHFFFAOYSA-N 0.000 claims description 3
AQKSRIWNBNAASX-UHFFFAOYSA-N 6-chloro-2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-5-fluoropyridine-3-carbonitrile Chemical compound N1=C(Cl)C(F)=CC(C#N)=C1SCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 AQKSRIWNBNAASX-UHFFFAOYSA-N 0.000 claims description 3
MZRSAIHKXIFUGJ-UHFFFAOYSA-N 6-chloro-2-[2-[4-(6-chloro-3,4-dihydro-2h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound C=1C(Cl)=CC=2NCCOC=2C=1N(CC1)CCN1CCSC1=NC(Cl)=CC=C1C#N MZRSAIHKXIFUGJ-UHFFFAOYSA-N 0.000 claims description 3
UXILHMQMVPRBTA-UHFFFAOYSA-N 6-chloro-2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]-4-methylpyridine-3-carbonitrile Chemical compound CC1=CC(Cl)=NC(SCCN2CCN(CC2)C=2C=3OCC(=O)NC=3C=C(Cl)C=2)=C1C#N UXILHMQMVPRBTA-UHFFFAOYSA-N 0.000 claims description 3
PYDFELBOSCSFHP-UHFFFAOYSA-N 6-chloro-2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]-5-fluoropyridine-3-carbonitrile Chemical compound N1=C(Cl)C(F)=CC(C#N)=C1SCCN1CCN(C=2C=3OCC(=O)NC=3C=C(Cl)C=2)CC1 PYDFELBOSCSFHP-UHFFFAOYSA-N 0.000 claims description 3
HJKHPXDIIZPHLJ-UHFFFAOYSA-N 6-chloro-2-[2-[4-(6-chloro-3-oxo-4h-1,4-benzoxazin-8-yl)piperazin-1-yl]ethylsulfanyl]pyridine-3-carbonitrile Chemical compound C=1C(Cl)=CC=2NC(=O)COC=2C=1N(CC1)CCN1CCSC1=NC(Cl)=CC=C1C#N HJKHPXDIIZPHLJ-UHFFFAOYSA-N 0.000 claims description 3
STHVHFHBYSOQLX-UHFFFAOYSA-N 6-chloro-2-[2-[4-(8-cyano-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylsulfanyl]-5-fluoropyridine-3-carbonitrile Chemical compound N1=C(Cl)C(F)=CC(C#N)=C1SCCN1CCN(C=2C=3OCCOC=3C(C#N)=CC=2)CC1 STHVHFHBYSOQLX-UHFFFAOYSA-N 0.000 claims description 3
MSMXELNFSCVCLE-UHFFFAOYSA-N 6-cyclopropyl-2-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethoxy]-4-(trifluoromethyl)pyridine-3-carbonitrile Chemical compound N=1C(OCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C(C#N)C(C(F)(F)F)=CC=1C1CC1 MSMXELNFSCVCLE-UHFFFAOYSA-N 0.000 claims description 3
125000003601 C2-C6 alkynyl 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
239000003937 drug carrier Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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Classifications

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- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
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- 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
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Health & Medical Sciences (AREA)
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Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
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Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
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Heart & Thoracic Surgery (AREA)
Addiction (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SK65-2004A 2001-06-29 2002-06-27 Heteroaryl derivatives, pharmaceutical composition with the content thereof and use of the same SK652004A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200101036		2001-06-29
PCT/DK2002/000435 WO2003002556A1 (en)	2001-06-29	2002-06-27	Novel heteroaryl derivatives, their preparation and use

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SK652004A3 true SK652004A3 (en)	2004-09-08

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US (2)	US20040248883A1 (de)
EP (1)	EP1399438B1 (de)
JP (1)	JP2004535449A (de)
KR (1)	KR20040019026A (de)
CN (1)	CN1310909C (de)
AT (1)	ATE312094T1 (de)
AU (1)	AU2002344949B2 (de)
BG (1)	BG108531A (de)
BR (1)	BR0210401A (de)
CA (1)	CA2451228A1 (de)
CZ (1)	CZ2004156A3 (de)
DE (1)	DE60207857T2 (de)
DK (1)	DK1399438T3 (de)
EA (1)	EA006203B1 (de)
ES (1)	ES2252471T3 (de)
HU (1)	HUP0400344A2 (de)
IL (1)	IL158828A0 (de)
IS (1)	IS2425B (de)
MX (1)	MXPA03011769A (de)
NO (1)	NO326514B1 (de)
NZ (1)	NZ529460A (de)
PL (1)	PL365249A1 (de)
SI (1)	SI1399438T1 (de)
SK (1)	SK652004A3 (de)
UA (1)	UA75407C2 (de)
WO (1)	WO2003002556A1 (de)

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CA2451229C (en) *	2001-06-29	2009-02-10	H. Lundbeck A/S	Indole derivatives
DK1408976T5 (da) *	2001-07-20	2011-01-10	Psychogenics Inc	Behandling af ADHD (Attention deficit hyperactivity disorder)
DE112004001191B4 (de) *	2003-07-02	2017-11-09	Corus Pharma Inc.	Verfahren zur Herstellung des L-Lysin-Salzes von Aztreonam und Verfahren zur Bestimmung des Verunreinigungsgrads in einem amorphen Aztreonam Lysin-Salz
US7160888B2 (en)	2003-08-22	2007-01-09	Warner Lambert Company Llc	[1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia
ES2331144T3 (es)	2004-11-26	2009-12-22	Janssen Pharmaceutica Nv	Derivados de isoxazolina-indol con actividad antipsicotica y ansiolitica mejorada.
CN102822167A (zh)	2010-01-04	2012-12-12	埃南蒂亚有限公司	用于制备利伐沙班的方法及其中间体
JP5546678B2 (ja)	2010-04-12	2014-07-09	ロッテケミカルコーポレーション	チオフェン−縮合環シクロペンタジエニルリガンドを含む遷移金属化合物を使用したポリプロピレンの製造方法
KR100986301B1 (ko)	2010-04-12	2010-10-07	아주대학교산학협력단	테트라하이드로퀴놀린 유도체로부터 유래한 티오펜-축합고리 싸이클로펜타디에닐 4족 금속 화합물 및 이를 이용한 올레핀 중합
JP5567209B2 (ja)	2010-04-12	2014-08-06	ロッテケミカルコーポレーション	オレフィン重合用担持触媒およびこれを用いたポリオレフィンの製造方法
US8916662B2 (en)	2010-04-12	2014-12-23	Lotte Chemical Corporation	Method for preparing olefin-diene copolymer using transition metal compound containing thiophene-fused cyclopentadienyl ligand
JP5567208B2 (ja)	2010-04-12	2014-08-06	ロッテケミカルコーポレーション	オレフィン重合用触媒組成物およびこれを用いたポリオレフィンの製造方法

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FR2667068B1 (fr) *	1990-09-26	1994-09-09	Adir	Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
CA2451229C (en)	2001-06-29	2009-02-10	H. Lundbeck A/S	Indole derivatives

2002
- 2002-06-27 WO PCT/DK2002/000435 patent/WO2003002556A1/en not_active Ceased
- 2002-06-27 MX MXPA03011769A patent/MXPA03011769A/es active IP Right Grant
- 2002-06-27 SI SI200230265T patent/SI1399438T1/sl unknown
- 2002-06-27 US US10/482,764 patent/US20040248883A1/en not_active Abandoned
- 2002-06-27 SK SK65-2004A patent/SK652004A3/sk unknown
- 2002-06-27 NZ NZ529460A patent/NZ529460A/en unknown
- 2002-06-27 CA CA002451228A patent/CA2451228A1/en not_active Abandoned
- 2002-06-27 IL IL15882802A patent/IL158828A0/xx unknown
- 2002-06-27 AT AT02742849T patent/ATE312094T1/de not_active IP Right Cessation
- 2002-06-27 DE DE60207857T patent/DE60207857T2/de not_active Expired - Fee Related
- 2002-06-27 UA UA20031211984A patent/UA75407C2/uk unknown
- 2002-06-27 EP EP02742849A patent/EP1399438B1/de not_active Expired - Lifetime
- 2002-06-27 CN CNB028129946A patent/CN1310909C/zh not_active Expired - Fee Related
- 2002-06-27 JP JP2003508937A patent/JP2004535449A/ja active Pending
- 2002-06-27 BR BR0210401-6A patent/BR0210401A/pt not_active IP Right Cessation
- 2002-06-27 KR KR10-2003-7017125A patent/KR20040019026A/ko not_active Abandoned
- 2002-06-27 PL PL02365249A patent/PL365249A1/xx unknown
- 2002-06-27 DK DK02742849T patent/DK1399438T3/da active
- 2002-06-27 AU AU2002344949A patent/AU2002344949B2/en not_active Ceased
- 2002-06-27 EA EA200400102A patent/EA006203B1/ru not_active IP Right Cessation
- 2002-06-27 HU HU0400344A patent/HUP0400344A2/hu unknown
- 2002-06-27 ES ES02742849T patent/ES2252471T3/es not_active Expired - Lifetime
- 2002-06-27 CZ CZ2004156A patent/CZ2004156A3/cs unknown
2003
- 2003-11-10 IS IS7021A patent/IS2425B/is unknown
- 2003-12-18 NO NO20035673A patent/NO326514B1/no unknown
2004
- 2004-01-14 BG BG108531A patent/BG108531A/bg unknown
2007
- 2007-06-05 US US11/758,511 patent/US7393845B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
JP2004535449A (ja)	2004-11-25
IS2425B (is)	2008-10-15
CN1520410A (zh)	2004-08-11
CN1310909C (zh)	2007-04-18
AU2002344949B2 (en)	2007-05-24
UA75407C2 (en)	2006-04-17
EA200400102A1 (ru)	2004-04-29
US20080027071A1 (en)	2008-01-31
DK1399438T3 (da)	2006-04-18
EA006203B1 (ru)	2005-10-27
NO20035673D0 (no)	2003-12-18
ES2252471T3 (es)	2006-05-16
CZ2004156A3 (cs)	2004-05-12
BG108531A (bg)	2004-08-31
EP1399438A1 (de)	2004-03-24
BR0210401A (pt)	2004-08-17
NO326514B1 (no)	2008-12-22
WO2003002556A1 (en)	2003-01-09
MXPA03011769A (es)	2004-04-02
US7393845B2 (en)	2008-07-01
US20040248883A1 (en)	2004-12-09
EP1399438B1 (de)	2005-12-07
KR20040019026A (ko)	2004-03-04
NZ529460A (en)	2005-09-30
ATE312094T1 (de)	2005-12-15
CA2451228A1 (en)	2003-01-09
HK1068622A1 (en)	2005-04-29
PL365249A1 (en)	2004-12-27
NO20035673L (no)	2003-12-18
IL158828A0 (en)	2004-05-12
IS7021A (is)	2003-11-10
DE60207857D1 (de)	2006-01-12
DE60207857T2 (de)	2006-07-20
HUP0400344A2 (hu)	2004-09-28
SI1399438T1 (sl)	2006-04-30

Legal Events

Date	Code	Title	Description
2012-08-06	FB9A	Suspension of patent application procedure

Publication	Publication Date	Title
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CA2722606A1 (en)	2009-11-12	Urea compounds as gamma secretase modulators
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JP4700614B2 (ja)	2011-06-15	５−ｈｔ１ｆアゴニストとしての置換された２−カルボニルアミノ−６−ピペリジンアミノピリジンおよび置換された１−カルボニルアミノ−３−ピペリジンアミノベンゼン
TW200526630A (en)	2005-08-16	Novel pyridine derivatives
AU2002344949A1 (en)	2003-05-15	Novel heteroaryl derivatives, their preparation and use
JP2006523659A (ja)	2006-10-19	ケモカイン受容体の調節物質としての環式第四級アミノ誘導体
EP1399434B1 (de)	2005-09-07	Neue indolderivate
AU2002344950A1 (en)	2003-05-15	Novel indole derivatives
CZ301114B6 (cs)	2009-11-11	Indolové deriváty