ZA200610162B - 2-(1H-indolylsulfanyl)-aryl amine derivatives for use in the treatment of affective disorders, pain, ADHD and stress urinary incontinence - Google Patents
2-(1H-indolylsulfanyl)-aryl amine derivatives for use in the treatment of affective disorders, pain, ADHD and stress urinary incontinence Download PDFInfo
- Publication number
- ZA200610162B ZA200610162B ZA200610162A ZA200610162A ZA200610162B ZA 200610162 B ZA200610162 B ZA 200610162B ZA 200610162 A ZA200610162 A ZA 200610162A ZA 200610162 A ZA200610162 A ZA 200610162A ZA 200610162 B ZA200610162 B ZA 200610162B
- Authority
- ZA
- South Africa
- Prior art keywords
- alk
- indole
- phenylsulfanyl
- methyl
- piperazin
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 29
- 208000002193 Pain Diseases 0.000 title claims description 12
- 208000019022 Mood disease Diseases 0.000 title claims description 11
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 title claims description 9
- 206010066218 Stress Urinary Incontinence Diseases 0.000 title claims description 9
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 95
- 239000001257 hydrogen Substances 0.000 claims description 95
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 50
- 229910052736 halogen Inorganic materials 0.000 claims description 46
- 150000002367 halogens Chemical class 0.000 claims description 44
- 150000002431 hydrogen Chemical class 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 claims description 17
- 239000003772 serotonin uptake inhibitor Substances 0.000 claims description 17
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229960002748 norepinephrine Drugs 0.000 claims description 13
- 208000020401 Depressive disease Diseases 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 239000000221 dopamine uptake inhibitor Substances 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 239000002767 noradrenalin uptake inhibitor Substances 0.000 claims description 11
- 229940076279 serotonin Drugs 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 230000009286 beneficial effect Effects 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 208000027520 Somatoform disease Diseases 0.000 claims description 7
- 208000027753 pain disease Diseases 0.000 claims description 7
- 229940094659 Dopamine reuptake inhibitor Drugs 0.000 claims description 6
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 229940127221 norepinephrine reuptake inhibitor Drugs 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 208000008035 Back Pain Diseases 0.000 claims description 3
- 208000001640 Fibromyalgia Diseases 0.000 claims description 3
- 206010019233 Headaches Diseases 0.000 claims description 3
- 206010028391 Musculoskeletal Pain Diseases 0.000 claims description 3
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 claims description 3
- 208000007613 Shoulder Pain Diseases 0.000 claims description 3
- 231100000869 headache Toxicity 0.000 claims description 3
- JQMCYPJXSAJJFZ-UHFFFAOYSA-N 1-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanylindole Chemical compound C=1C(C)=CC=C(SC=2C3=CC=CC=C3N(C)C=2)C=1N1CCNCC1 JQMCYPJXSAJJFZ-UHFFFAOYSA-N 0.000 claims description 2
- FQLZUIWSGITTEM-UHFFFAOYSA-N 4-chloro-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=C(Cl)C=CC=C3NC=2)C=1N1CCNCC1 FQLZUIWSGITTEM-UHFFFAOYSA-N 0.000 claims description 2
- GUSQZTYAJURGEX-UHFFFAOYSA-N 4-fluoro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(F)=CC=CC=2NC=C1SC1=CC=CC=C1N1CCNCC1 GUSQZTYAJURGEX-UHFFFAOYSA-N 0.000 claims description 2
- TVCLCRSWLWCSEA-UHFFFAOYSA-N 4-methoxy-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(OC)=CC=CC=2NC=C1SC1=CC=CC=C1N1CCNCC1 TVCLCRSWLWCSEA-UHFFFAOYSA-N 0.000 claims description 2
- AESFNTUSMPVBGB-UHFFFAOYSA-N 4-methoxy-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1H-indole 7-methoxy-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1H-indole Chemical compound COC1=C2C(=CNC2=CC=C1)SC1=C(C=C(C=C1)C)N1CCNCC1.COC=1C=CC=C2C(=CNC12)SC1=C(C=C(C=C1)C)N1CCNCC1 AESFNTUSMPVBGB-UHFFFAOYSA-N 0.000 claims description 2
- MYRKXONYFQHLOS-UHFFFAOYSA-N 4-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=C(C)C=CC=C3NC=2)C=1N1CCNCC1 MYRKXONYFQHLOS-UHFFFAOYSA-N 0.000 claims description 2
- NZJWUKVJFVXMQI-UHFFFAOYSA-N 5-fluoro-2-methyl-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound CC=1NC2=CC=C(F)C=C2C=1SC1=CC=CC=C1N1CCNCC1 NZJWUKVJFVXMQI-UHFFFAOYSA-N 0.000 claims description 2
- POCSMPIABSLFOC-UHFFFAOYSA-N 5-fluoro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1SC1=CC=CC=C1N1CCNCC1 POCSMPIABSLFOC-UHFFFAOYSA-N 0.000 claims description 2
- QHMPNDIYNSKRRX-UHFFFAOYSA-N 5-methoxy-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1SC1=CC=CC=C1N1CCNCC1 QHMPNDIYNSKRRX-UHFFFAOYSA-N 0.000 claims description 2
- AZCRTFQDUUEFBW-UHFFFAOYSA-N 5-methoxy-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1SC1=CC=C(C)C=C1N1CCNCC1 AZCRTFQDUUEFBW-UHFFFAOYSA-N 0.000 claims description 2
- RJIGKGWKBHXRHU-UHFFFAOYSA-N 5-methoxy-4-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=C(C)C(OC)=CC=C2NC=C1SC1=CC=C(C)C=C1N1CCNCC1 RJIGKGWKBHXRHU-UHFFFAOYSA-N 0.000 claims description 2
- UHGMRJVWQKZFML-UHFFFAOYSA-N 5-methyl-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(C)=CC=C2NC=C1SC1=CC=CC=C1N1CCNCC1 UHGMRJVWQKZFML-UHFFFAOYSA-N 0.000 claims description 2
- DJRBTFYASKGZGB-UHFFFAOYSA-N 6-fluoro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(F)=CC=C2C=1SC1=CC=CC=C1N1CCNCC1 DJRBTFYASKGZGB-UHFFFAOYSA-N 0.000 claims description 2
- MLGUXRHUCVQCNY-UHFFFAOYSA-N 6-methoxy-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(OC)=CC=C2C=1SC1=CC=CC=C1N1CCNCC1 MLGUXRHUCVQCNY-UHFFFAOYSA-N 0.000 claims description 2
- VVLWVGJUPRLFRN-UHFFFAOYSA-N 7-chloro-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=CC=CC(Cl)=C3NC=2)C=1N1CCNCC1 VVLWVGJUPRLFRN-UHFFFAOYSA-N 0.000 claims description 2
- YIQAGFJDCVIBGK-UHFFFAOYSA-N 7-fluoro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(F)=CC=CC=2C=1SC1=CC=CC=C1N1CCNCC1 YIQAGFJDCVIBGK-UHFFFAOYSA-N 0.000 claims description 2
- PQHUAEQWPBDFRI-UHFFFAOYSA-N 7-fluoro-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=CC=CC(F)=C3NC=2)C=1N1CCNCC1 PQHUAEQWPBDFRI-UHFFFAOYSA-N 0.000 claims description 2
- NMTHUYDZODRYQT-UHFFFAOYSA-N 7-methoxy-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(OC)=CC=CC=2C=1SC1=CC=CC=C1N1CCNCC1 NMTHUYDZODRYQT-UHFFFAOYSA-N 0.000 claims description 2
- PTXMMZMMRJNMIQ-UHFFFAOYSA-N 7-methyl-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(C)=CC=CC=2C=1SC1=CC=CC=C1N1CCNCC1 PTXMMZMMRJNMIQ-UHFFFAOYSA-N 0.000 claims description 2
- GZZQNQVEVIAZPG-UHFFFAOYSA-N CC=1NC2=CC=CC=C2C1SC1=C(C=CC=C1)N1CCNCC1.CC1=C(NC2=CC=CC=C12)SC1=C(C=C(C=C1)C)N1CCNCC1 Chemical compound CC=1NC2=CC=CC=C2C1SC1=C(C=CC=C1)N1CCNCC1.CC1=C(NC2=CC=CC=C12)SC1=C(C=C(C=C1)C)N1CCNCC1 GZZQNQVEVIAZPG-UHFFFAOYSA-N 0.000 claims description 2
- WZTZUBGPTVEELA-UHFFFAOYSA-N COC=1C(=C2C(=CNC2=CC1)SC1=C(C=CC=C1)N1CCNCC1)C.C(C)C=1C=CC=C2C(=CNC12)SC1=C(C=CC=C1)N1CCNCC1 Chemical compound COC=1C(=C2C(=CNC2=CC1)SC1=C(C=CC=C1)N1CCNCC1)C.C(C)C=1C=CC=C2C(=CNC12)SC1=C(C=CC=C1)N1CCNCC1 WZTZUBGPTVEELA-UHFFFAOYSA-N 0.000 claims description 2
- BRIYECQXNNLHCU-UHFFFAOYSA-N FC1=C2C(=CNC2=CC=C1)SC1=C(C=C(C=C1)C)N1CCNCC1.FC1=CC=C2C(=CNC2=C1)SC1=C(C=C(C=C1)C)N1CCNCC1 Chemical compound FC1=C2C(=CNC2=CC=C1)SC1=C(C=C(C=C1)C)N1CCNCC1.FC1=CC=C2C(=CNC2=C1)SC1=C(C=C(C=C1)C)N1CCNCC1 BRIYECQXNNLHCU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 102000019208 Serotonin Plasma Membrane Transport Proteins Human genes 0.000 claims 8
- 108010012996 Serotonin Plasma Membrane Transport Proteins Proteins 0.000 claims 8
- 230000002401 inhibitory effect Effects 0.000 claims 8
- 208000017194 Affective disease Diseases 0.000 claims 6
- 229940126570 serotonin reuptake inhibitor Drugs 0.000 claims 6
- 102000006441 Dopamine Plasma Membrane Transport Proteins Human genes 0.000 claims 4
- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 claims 4
- 102000008092 Norepinephrine Plasma Membrane Transport Proteins Human genes 0.000 claims 4
- 108010049586 Norepinephrine Plasma Membrane Transport Proteins Proteins 0.000 claims 4
- 206010041250 Social phobia Diseases 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- 208000019906 panic disease Diseases 0.000 claims 4
- 208000008811 Agoraphobia Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010033664 Panic attack Diseases 0.000 claims 2
- 206010034912 Phobia Diseases 0.000 claims 2
- 201000009916 Postpartum depression Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000024732 dysthymic disease Diseases 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 2
- 201000001716 specific phobia Diseases 0.000 claims 2
- PRTHIFIPLRRXMA-UHFFFAOYSA-N 1-methyl-3-(2-piperazin-1-ylphenyl)sulfanylindole Chemical compound C12=CC=CC=C2N(C)C=C1SC1=CC=CC=C1N1CCNCC1 PRTHIFIPLRRXMA-UHFFFAOYSA-N 0.000 claims 1
- UGWLGFOHUSKMML-UHFFFAOYSA-N 1-methyl-3-(2-piperidin-4-ylphenyl)sulfanylindole Chemical compound C12=CC=CC=C2N(C)C=C1SC1=CC=CC=C1C1CCNCC1 UGWLGFOHUSKMML-UHFFFAOYSA-N 0.000 claims 1
- WJIGJEIWGBVZBV-UHFFFAOYSA-N 2-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound CC=1NC2=CC=CC=C2C=1SC1=CC=CC=C1C1CCNCC1 WJIGJEIWGBVZBV-UHFFFAOYSA-N 0.000 claims 1
- QPGJQAGXCOBJOO-UHFFFAOYSA-N 2-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound CC=1NC2=CC=CC=C2C=1SC1=CC=C(C)C=C1N1CCNCC1 QPGJQAGXCOBJOO-UHFFFAOYSA-N 0.000 claims 1
- ALJGPJHSMRDUKY-UHFFFAOYSA-N 3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C1CNCCC1C1=CC=CC=C1SC1=CNC2=CC=CC=C12 ALJGPJHSMRDUKY-UHFFFAOYSA-N 0.000 claims 1
- DWVXSNHKYWOBSG-UHFFFAOYSA-N 3-methyl-2-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound N1C2=CC=CC=C2C(C)=C1SC1=CC=CC=C1N1CCNCC1 DWVXSNHKYWOBSG-UHFFFAOYSA-N 0.000 claims 1
- AIUQVJNKEUGLJG-UHFFFAOYSA-N 3-methyl-2-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound N1C2=CC=CC=C2C(C)=C1SC1=CC=CC=C1C1CCNCC1 AIUQVJNKEUGLJG-UHFFFAOYSA-N 0.000 claims 1
- ZGIQIRWWZCMKHD-UHFFFAOYSA-N 4-chloro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2NC=C1SC1=CC=CC=C1N1CCNCC1 ZGIQIRWWZCMKHD-UHFFFAOYSA-N 0.000 claims 1
- RNZQXBXMXKGZIB-UHFFFAOYSA-N 4-chloro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(Cl)=CC=CC=2NC=C1SC1=CC=CC=C1C1CCNCC1 RNZQXBXMXKGZIB-UHFFFAOYSA-N 0.000 claims 1
- JNBKXDHDXQLHKA-UHFFFAOYSA-N 4-fluoro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(F)=CC=CC=2NC=C1SC1=CC=CC=C1C1CCNCC1 JNBKXDHDXQLHKA-UHFFFAOYSA-N 0.000 claims 1
- DQJUMWVFXTZNPY-UHFFFAOYSA-N 4-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(C)=CC=CC=2NC=C1SC1=CC=CC=C1C1CCNCC1 DQJUMWVFXTZNPY-UHFFFAOYSA-N 0.000 claims 1
- UVXXNTANIZOHPH-UHFFFAOYSA-N 5-chloro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1SC1=CC=CC=C1C1CCNCC1 UVXXNTANIZOHPH-UHFFFAOYSA-N 0.000 claims 1
- WZZWFVWYBKLFLZ-UHFFFAOYSA-N 5-fluoro-2-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound CC=1NC2=CC=C(F)C=C2C=1SC1=CC=CC=C1C1CCNCC1 WZZWFVWYBKLFLZ-UHFFFAOYSA-N 0.000 claims 1
- YBGIZCWAFAVFAY-UHFFFAOYSA-N 5-fluoro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(F)=CC=C2NC=C1SC1=CC=CC=C1C1CCNCC1 YBGIZCWAFAVFAY-UHFFFAOYSA-N 0.000 claims 1
- XRZSNJZPPHPJGP-UHFFFAOYSA-N 5-methoxy-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(OC)=CC=C2NC=C1SC1=CC=CC=C1C1CCNCC1 XRZSNJZPPHPJGP-UHFFFAOYSA-N 0.000 claims 1
- JBOKSQDDINDANG-UHFFFAOYSA-N 5-methoxy-4-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C12=C(C)C(OC)=CC=C2NC=C1SC1=CC=CC=C1C1CCNCC1 JBOKSQDDINDANG-UHFFFAOYSA-N 0.000 claims 1
- ZUHIJCHAKDJTBI-UHFFFAOYSA-N 5-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(C)=CC=C2NC=C1SC1=CC=CC=C1C1CCNCC1 ZUHIJCHAKDJTBI-UHFFFAOYSA-N 0.000 claims 1
- WSADGSSRENSOCF-UHFFFAOYSA-N 5-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=CC(C)=CC=C3NC=2)C=1N1CCNCC1 WSADGSSRENSOCF-UHFFFAOYSA-N 0.000 claims 1
- KDPAAQBLSUPSNY-UHFFFAOYSA-N 6-chloro-3-(2-piperazin-1-ylphenyl)sulfanyl-1H-indole 5-nitro-3-(2-piperazin-1-ylphenyl)sulfanyl-1H-indole Chemical compound ClC1=CC=C2C(=CNC2=C1)SC1=C(C=CC=C1)N1CCNCC1.[N+](=O)([O-])C=1C=C2C(=CNC2=CC1)SC1=C(C=CC=C1)N1CCNCC1 KDPAAQBLSUPSNY-UHFFFAOYSA-N 0.000 claims 1
- HNUGGGPVQAQVAN-UHFFFAOYSA-N 6-chloro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1SC1=CC=CC=C1C1CCNCC1 HNUGGGPVQAQVAN-UHFFFAOYSA-N 0.000 claims 1
- BZLPFKGSRPYQPS-UHFFFAOYSA-N 6-fluoro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(F)=CC=C2C=1SC1=CC=CC=C1C1CCNCC1 BZLPFKGSRPYQPS-UHFFFAOYSA-N 0.000 claims 1
- VBABWFAGNZJZCC-UHFFFAOYSA-N 6-methyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(C)=CC=C2C=1SC1=CC=CC=C1C1CCNCC1 VBABWFAGNZJZCC-UHFFFAOYSA-N 0.000 claims 1
- KNODMQDBBJCTOS-UHFFFAOYSA-N 6-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=CC=C(C)C=C3NC=2)C=1N1CCNCC1 KNODMQDBBJCTOS-UHFFFAOYSA-N 0.000 claims 1
- UOBKUGGEWHYZLY-UHFFFAOYSA-N 7-chloro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(Cl)=CC=CC=2C=1SC1=CC=CC=C1N1CCNCC1 UOBKUGGEWHYZLY-UHFFFAOYSA-N 0.000 claims 1
- XTCOOZWBTCPMKS-UHFFFAOYSA-N 7-chloro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(Cl)=CC=CC=2C=1SC1=CC=CC=C1C1CCNCC1 XTCOOZWBTCPMKS-UHFFFAOYSA-N 0.000 claims 1
- ZOAUPABXLUBSQV-UHFFFAOYSA-N 7-ethyl-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(CC)=CC=CC=2C=1SC1=CC=CC=C1C1CCNCC1 ZOAUPABXLUBSQV-UHFFFAOYSA-N 0.000 claims 1
- JUIHNTDYPZSBRT-UHFFFAOYSA-N 7-fluoro-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(F)=CC=CC=2C=1SC1=CC=CC=C1C1CCNCC1 JUIHNTDYPZSBRT-UHFFFAOYSA-N 0.000 claims 1
- WVJBRPSNOBQYEW-UHFFFAOYSA-N 7-methoxy-3-(2-piperidin-4-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC=2C(OC)=CC=CC=2C=1SC1=CC=CC=C1C1CCNCC1 WVJBRPSNOBQYEW-UHFFFAOYSA-N 0.000 claims 1
- GWEWYMSDIPLHDE-UHFFFAOYSA-N 7-methyl-3-(4-methyl-2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1C(C)=CC=C(SC=2C3=CC=CC(C)=C3NC=2)C=1N1CCNCC1 GWEWYMSDIPLHDE-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000935 antidepressant agent Substances 0.000 description 10
- 229940005513 antidepressants Drugs 0.000 description 9
- 125000001153 fluoro group Chemical group F* 0.000 description 9
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- 229960003638 dopamine Drugs 0.000 description 7
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 7
- -1 1H-INDOLYLSULFANYL Chemical class 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- ZEUITGRIYCTCEM-KRWDZBQOSA-N (S)-duloxetine Chemical compound C1([C@@H](OC=2C3=CC=CC=C3C=CC=2)CCNC)=CC=CS1 ZEUITGRIYCTCEM-KRWDZBQOSA-N 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 description 4
- 229960002866 duloxetine Drugs 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 4
- 230000000697 serotonin reuptake Effects 0.000 description 4
- 229960004688 venlafaxine Drugs 0.000 description 4
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 4
- 201000001880 Sexual dysfunction Diseases 0.000 description 3
- 230000002301 combined effect Effects 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000001041 indolyl group Chemical group 0.000 description 3
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 3
- 231100000872 sexual dysfunction Toxicity 0.000 description 3
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical compound C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940123685 Monoamine oxidase inhibitor Drugs 0.000 description 2
- AHOUBRCZNHFOSL-UHFFFAOYSA-N Paroxetine hydrochloride Natural products C1=CC(F)=CC=C1C1C(COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000009977 dual effect Effects 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000002899 monoamine oxidase inhibitor Substances 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 229960002296 paroxetine Drugs 0.000 description 2
- 230000013275 serotonin uptake Effects 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000003568 thioethers Chemical class 0.000 description 2
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 description 1
- IEASOXWLILLCAI-UHFFFAOYSA-N 3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C1CNCCN1C1=CC=CC=C1SC1=CNC2=CC=CC=C12 IEASOXWLILLCAI-UHFFFAOYSA-N 0.000 description 1
- PLNNSZMFMTXIRE-UHFFFAOYSA-N 4-methyl-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C1=2C(C)=CC=CC=2NC=C1SC1=CC=CC=C1N1CCNCC1 PLNNSZMFMTXIRE-UHFFFAOYSA-N 0.000 description 1
- LTLJPVDBVOPOIJ-UHFFFAOYSA-N 5-chloro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C12=CC(Cl)=CC=C2NC=C1SC1=CC=CC=C1N1CCNCC1 LTLJPVDBVOPOIJ-UHFFFAOYSA-N 0.000 description 1
- 210000002348 5-ht neuron Anatomy 0.000 description 1
- PQEOCODGDJLYFY-UHFFFAOYSA-N 6-chloro-3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole Chemical compound C=1NC2=CC(Cl)=CC=C2C=1SC1=CC=CC=C1N1CCNCC1 PQEOCODGDJLYFY-UHFFFAOYSA-N 0.000 description 1
- LSYZPUPHIYWFAS-UHFFFAOYSA-N 6-methyl-3-(2-piperazin-1-ylphenyl)sulfanyl-1H-indole 3-[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]sulfanyl-1H-indole Chemical compound CC1=CC=C2C(=CNC2=C1)SC1=C(C=CC=C1)N1CCNCC1.N1CCC(=CC1)C1=C(C=CC=C1)SC1=CNC2=CC=CC=C12 LSYZPUPHIYWFAS-UHFFFAOYSA-N 0.000 description 1
- 208000007415 Anhedonia Diseases 0.000 description 1
- 241001272567 Hominoidea Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229960001058 bupropion Drugs 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 229960001653 citalopram Drugs 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 230000002825 dopamine reuptake Effects 0.000 description 1
- 229940000406 drug candidate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- HXOXWUZERSKAAF-UHFFFAOYSA-N methyl 3-(2-piperazin-1-ylphenyl)sulfanyl-1h-indole-7-carboxylate Chemical compound C=1NC=2C(C(=O)OC)=CC=CC=2C=1SC1=CC=CC=C1N1CCNCC1 HXOXWUZERSKAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 230000000966 norepinephrine reuptake Effects 0.000 description 1
- 230000012154 norepinephrine uptake Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 229960003770 reboxetine Drugs 0.000 description 1
- CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229940009065 wellbutrin Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
- A61P25/22—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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58855504P | 2004-07-16 | 2004-07-16 | |
| DKPA200401121 | 2004-07-16 | ||
| US69173605P | 2005-06-17 | 2005-06-17 | |
| DKPA200500893 | 2005-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200610162B true ZA200610162B (en) | 2008-06-25 |
Family
ID=39243745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200610162A ZA200610162B (en) | 2004-07-16 | 2005-07-13 | 2-(1H-indolylsulfanyl)-aryl amine derivatives for use in the treatment of affective disorders, pain, ADHD and stress urinary incontinence |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US7678800B2 (uk) |
| EP (1) | EP1771415B1 (uk) |
| JP (1) | JP4865710B2 (uk) |
| KR (1) | KR20070036061A (uk) |
| CN (1) | CN1972911A (uk) |
| AR (1) | AR052308A1 (uk) |
| AT (1) | ATE420071T1 (uk) |
| AU (1) | AU2005263324A1 (uk) |
| BR (1) | BRPI0512073A (uk) |
| CA (1) | CA2570805C (uk) |
| CY (1) | CY1108942T1 (uk) |
| DE (1) | DE602005012272D1 (uk) |
| DK (1) | DK1771415T3 (uk) |
| EA (1) | EA011418B1 (uk) |
| ES (1) | ES2317266T3 (uk) |
| HR (1) | HRP20090112T3 (uk) |
| IL (1) | IL179924A0 (uk) |
| MX (1) | MXPA06015201A (uk) |
| NO (1) | NO20066010L (uk) |
| PL (1) | PL1771415T3 (uk) |
| PT (1) | PT1771415E (uk) |
| RS (1) | RS50804B (uk) |
| SI (1) | SI1771415T1 (uk) |
| UA (1) | UA82610C2 (uk) |
| WO (1) | WO2006007843A1 (uk) |
| ZA (1) | ZA200610162B (uk) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR054394A1 (es) * | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de 2- (1h-indolilsulfanil)-aril amina |
| AR054393A1 (es) | 2005-06-17 | 2007-06-20 | Lundbeck & Co As H | Derivados de benzo(b)furano y benzo(b)tiofeno, composiciones farmaceuticas que los contienen y su uso en la fabricacion de un medicamento para el tratamiento de enfermedades mediadas por la inhibicion de la reabsorcion de neurotransmisores de amina biogenicos. |
| US7629473B2 (en) | 2005-06-17 | 2009-12-08 | H. Lundbeck A/S | 2-(1H-indolylsulfanyl)-aryl amine derivatives |
| EA016054B1 (ru) * | 2006-06-16 | 2012-01-30 | Х. Лундбекк А/С | Кристаллические формы 4-[2-(4-метилфенилсульфанил)фенил] пиперидина с объединенным ингибированием повторного поглощения серотонина и норадреналина для лечения невропатической боли |
| TWI432194B (zh) * | 2007-03-20 | 2014-04-01 | Lundbeck & Co As H | ４-〔２-（４-甲基苯硫基）苯基〕哌啶之新穎治療用途 |
| EP2297070A2 (en) * | 2008-07-03 | 2011-03-23 | Bayer Schering Pharma Aktiengesellschaft | Compounds and processes for production of radiopharmaceuticals |
| RU2015145162A (ru) * | 2013-11-14 | 2017-12-19 | Кэлифорниа Инститьют Оф Текнолоджи | Аккомодирующая интраокулярная линза |
| EP3083588B1 (en) | 2013-12-20 | 2020-12-09 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic compounds and their application in pharmaceuticals |
| US9974785B2 (en) | 2014-07-08 | 2018-05-22 | Sunshine Lake Pharma Co., Ltd. | Aromatic heterocyclic derivatives and pharmaceutical applications thereof |
| CN108536644B (zh) * | 2015-12-04 | 2022-04-12 | 格兰菲智能科技有限公司 | 由装置端推核心入队列的装置 |
Family Cites Families (79)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803143A (en) | 1969-09-08 | 1974-04-09 | Eisai Co Ltd | 6-amino alkylene 6,7-dihydro-5h-dibenzo (b,g),(1,5)thiazocines |
| US4018830A (en) | 1969-09-22 | 1977-04-19 | Merck & Co., Inc. | Phenylthioaralkylamines |
| US4055665A (en) | 1974-11-25 | 1977-10-25 | Merck & Co., Inc. | Treating arrythmia with phenylthioaralkylamines |
| US4056632A (en) | 1975-07-21 | 1977-11-01 | Burroughs Wellcome Co. | 2-Hydroxymethyl-2'-aminomethyl-diphenylsulfides and method of use |
| US4241071A (en) | 1977-01-27 | 1980-12-23 | American Hoechst Corporation | Antidepressant (α-phenyl-2-tolyl)azacycloalkanes |
| US4198417A (en) | 1979-01-10 | 1980-04-15 | American Hoechst Corporation | Phenoxyphenylpiperidines |
| DE3640475A1 (de) | 1986-11-27 | 1988-06-09 | Hoechst Sa Lab | Arzneimittel auf basis von derivaten des 3,4-diphenylpiperidins, die verwendung der derivate als arzneimittel sowie neue 3,4-diphenylpiperidinderivate und verfahren zu ihrer herstellung |
| EP0396827A1 (en) | 1989-05-09 | 1990-11-14 | SPOFA Spojené Podniky Pro Zdravotnickou Vyrobu | 2-Phenylthiobenzylamine dervivatives and acid addition salts thereof |
| GB8912971D0 (en) | 1989-06-06 | 1989-07-26 | Wellcome Found | Halogen substituted diphenylsulfides |
| US6645969B1 (en) | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
| HUT69705A (en) | 1991-11-25 | 1995-09-28 | Pfizer | Indole derivatives |
| GB9126311D0 (en) | 1991-12-11 | 1992-02-12 | Wellcome Found | Substituted diphenylsulfides |
| GB9226532D0 (en) | 1992-12-21 | 1993-02-17 | Smithkline Beecham Plc | Compounds |
| US5945425A (en) | 1994-04-29 | 1999-08-31 | G.D. Searle & Co. | Method of using (H+ /K+)ATPase inhibitors as antiviral agents |
| ES2239766T3 (es) | 1995-01-23 | 2005-10-01 | Daiichi Suntory Pharma Co., Ltd. | Alivio o remedio para sintomas causados por enfermedades isquemicas y compuestos de fenilpiperidina utilizados para ello. |
| ES2128281T1 (es) | 1995-11-06 | 1999-05-16 | Gist Brocades Bv | Proceso de desesterificacion. |
| CZ293595A3 (cs) | 1995-11-09 | 1999-12-15 | Farmak A. S. | Deriváty N,N-dimethyl-2-(arylthio)benzylaminu, jejich soli, způsoby jejich přípravy a jejich použití v léčivých přípravcích |
| US5912256A (en) | 1996-06-20 | 1999-06-15 | Eli Lilly And Company | Compounds having effects on serotonin-related systems |
| EP0923548B1 (en) | 1996-08-27 | 2003-03-12 | Wyeth | 4-aminoethoxy indoles as dopamin d2 agonists and as 5ht 1a ligands |
| GB9725953D0 (en) | 1997-12-08 | 1998-02-04 | Pfizer Ltd | Compounds useful in therapy |
| DE19756036A1 (de) | 1997-12-17 | 1999-06-24 | Merck Patent Gmbh | Amid- und Harnstoffderivate |
| US6333146B1 (en) | 1999-03-10 | 2001-12-25 | Fuji Photo Film Co., Ltd. | Methine compound and silver halide photographic material containing the same |
| IL145528A0 (en) | 1999-04-02 | 2002-06-30 | Icos Corp | INHIBITORS OF LFA-1 BINDING TO ICAMs AND USES THEREOF |
| CA2372481A1 (en) | 1999-04-30 | 2000-11-09 | The Trustees Of The University Of Pennsylvania | Spect imaging agents for serotonin transporters |
| BR0012984A (pt) | 1999-08-04 | 2002-07-16 | Millennium Pharm Inc | Método para tratar um estado associado com o mc4-r em um mamìfero, composto de ligação ao mc4-r, e, composição farmacêutica |
| US6410736B1 (en) | 1999-11-29 | 2002-06-25 | Pfizer Inc. | Biaryl ether derivatives useful as monoamine reuptake inhibitors |
| TR200201004T2 (tr) | 1999-10-13 | 2002-11-21 | Pfizer Products Inc. | Monoamin reuptake önleyicileri olarak biaril eter türevleri |
| IL150337A0 (en) | 1999-12-30 | 2002-12-01 | Lundbeck & Co As H | Phenylpiperazinyl derivatives |
| UA72948C2 (uk) | 1999-12-30 | 2005-05-16 | Х. Луннбек А/С | Заміщені похідні фенілпіперазину, фармацевтична композиція та спосіб лікування афективних або неврологічних захворювань і розладів |
| UA73756C2 (en) | 1999-12-30 | 2005-09-15 | Lundbeck & Co As H | HALOGEN-SUBSTITUTED 4-PHENYL-1-PIPERAZIN, PIPERIDIN AND TETRAHYDROPIRIDINE û DERIVATIVES A PHARMACEUTICAL COMPOSITION BASED THEREON, THEIR APPLICATION FOR PRODUCING MEDICAMENT, AND A METHOD FOR THE TREATMENT OF PSYCHOSIS |
| AU2001243334A1 (en) | 2000-02-29 | 2001-09-12 | Integriderm, Inc. | Inhibitors of melanocyte tyrosinase as topical skin lighteners |
| AU2001258771A1 (en) | 2000-05-19 | 2001-11-26 | Takeda Chemical Industries Ltd. | -secretase inhibitors |
| US6455738B1 (en) | 2000-07-13 | 2002-09-24 | Rhodia Chimie | Process for the sulfonation of an aromatic compound |
| CA2416384A1 (en) | 2000-07-17 | 2003-01-16 | Takeda Chemical Industries, Ltd. | Sulfone derivatives, their production and use |
| AU2001279955A1 (en) | 2000-08-18 | 2002-03-04 | Sterix Limited | 2-substituted estradiol derivative for inhibiting superoxid dismutase |
| CZ2003493A3 (cs) | 2000-09-01 | 2003-08-13 | Fmc Corporation | Disubstituované benzeny jakožto insekticidy |
| AU2001288623A1 (en) | 2000-09-05 | 2002-03-22 | Tularik, Inc. | Fxr modulators |
| EP1193268A1 (en) | 2000-09-27 | 2002-04-03 | Applied Research Systems ARS Holding N.V. | Pharmaceutically active sulfonamide derivatives bearing both lipophilic and ionisable moieties as inhibitors of protein Junkinases |
| US6852816B2 (en) | 2000-10-06 | 2005-02-08 | Biocompatibles Uk Limited | Zwitterionic polymers |
| CA2425259A1 (en) | 2000-10-11 | 2002-04-18 | Tularik, Inc. | Modulation of ccr4 function |
| WO2002040024A1 (en) | 2000-11-14 | 2002-05-23 | Merck Patent Gmbh | Novel uses of combined 5-ht1a agonists and serotonin reuptake inhibitors |
| AR035521A1 (es) * | 2000-12-22 | 2004-06-02 | Lundbeck & Co As H | Derivados de 3-indolina y composicion farmaceutica que los comprende |
| US6436938B1 (en) | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
| WO2002062766A2 (en) | 2001-02-07 | 2002-08-15 | Millennium Pharmaceuticals, Inc. | Melanocortin-4 receptor binding compounds and methods of use thereof |
| CA2449874C (en) * | 2001-06-07 | 2009-06-23 | F. Hoffmann-La Roche Ag | New indole derivatives with 5-ht6 receptor affinity |
| US7199147B2 (en) | 2001-06-12 | 2007-04-03 | Dainippon Sumitomo Pharma Co., Ltd. | Rho kinase inhibitors |
| UA81749C2 (uk) * | 2001-10-04 | 2008-02-11 | Х. Луннбек А/С | Фенілпіперазинові похідні як інгібітори зворотного захоплення серотоніну |
| US7064139B2 (en) | 2001-10-29 | 2006-06-20 | Uniroyal Chemical Company, Inc. | Method for treating retroviral infections |
| MXPA04004674A (es) | 2001-11-14 | 2004-08-12 | Schering Corp | Ligados de los receptors de los canabinodies. |
| HUP0402319A2 (hu) | 2001-12-21 | 2005-02-28 | H. Lundbeck A/S | Szerotonin és norepinefrin felvételt gátló aminoindán-származékok |
| US8048408B2 (en) | 2002-01-16 | 2011-11-01 | Biocompatibles Uk Limited | Polymer conjugates |
| US20050261298A1 (en) | 2002-01-18 | 2005-11-24 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| RU2314314C2 (ru) | 2002-03-04 | 2008-01-10 | Джапан Сайенс Энд Текнолоджи Эйдженси | Новые фосфонамиды, способ их получения и их применение |
| AU2003218452C1 (en) | 2002-03-29 | 2009-07-23 | Massachusetts Institute Of Technology | Light emitting device including semiconductor nanocrystals |
| DE10217006A1 (de) | 2002-04-16 | 2003-11-06 | Merck Patent Gmbh | Substituierte Indole |
| US7217732B2 (en) | 2002-06-19 | 2007-05-15 | Schering Corporation | Cannabinoid receptor agonists |
| TW200401641A (en) | 2002-07-18 | 2004-02-01 | Wyeth Corp | 1-Heterocyclylalkyl-3-sulfonylindole or-indazole derivatives as 5-hydroxytryptamine-6 ligands |
| KR100686758B1 (ko) | 2002-09-17 | 2007-02-26 | 에프. 호프만-라 로슈 아게 | 2,7-치환된 인돌 및 5-ｈｔ6 조절 인자로서의 그 용도 |
| MXPA05002836A (es) | 2002-09-17 | 2005-05-27 | Hoffmann La Roche | Indoles 2,4-sustituidos y su uso como moduladores 5-ht6. |
| EP1402888A1 (en) | 2002-09-18 | 2004-03-31 | Jerini AG | The use of substituted carbocyclic compounds as rotamases inhibitors |
| US20040266732A1 (en) | 2002-09-20 | 2004-12-30 | Jorge Galvez | Therapeutic agents, methods, and treatments |
| MXPA05004128A (es) * | 2002-10-18 | 2005-06-22 | Hoffmann La Roche | 4-piperazinil bencenosulfonil indoles con afinidad al receptor 5-hidroxitriptamina 6 (5-ht6). |
| US20040137389A1 (en) | 2002-12-19 | 2004-07-15 | Kouta Fukui | Heat-developable light-sensitive material |
| CA2511214C (en) | 2002-12-20 | 2012-12-18 | Tularik, Inc. | Asthma and allergic inflammation modulators |
| US7189501B2 (en) | 2002-12-27 | 2007-03-13 | Fuji Photo Film Co., Ltd. | Silver halide color photographic photosensitive material |
| DE10300098A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Ag | Kupfer-Carben-Komplexe und ihre Verwendung |
| WO2004069888A2 (en) | 2003-02-05 | 2004-08-19 | Biocompatibles Uk Limited | Block copolymers |
| TW200505902A (en) | 2003-03-20 | 2005-02-16 | Schering Corp | Cannabinoid receptor ligands |
| US7893096B2 (en) | 2003-03-28 | 2011-02-22 | Novartis Vaccines And Diagnostics, Inc. | Use of small molecule compounds for immunopotentiation |
| US7244763B2 (en) | 2003-04-17 | 2007-07-17 | Warner Lambert Company Llc | Compounds that modulate PPAR activity and methods of preparation |
| WO2005035516A1 (ja) | 2003-10-10 | 2005-04-21 | Ono Pharmaceutical Co., Ltd. | 新規縮合複素環化合物およびその用途 |
| US7229751B2 (en) | 2003-11-20 | 2007-06-12 | Konica Minolta Medical & Graphic, Inc. | Silver salt photothermographic dry imaging material and image forming method using the same |
| CA2550091A1 (en) | 2003-12-19 | 2005-07-07 | Elixir Pharmaceuticals, Inc. | Methods of treating a disorder |
| BRPI0417858B1 (pt) | 2003-12-23 | 2017-10-10 | H. Lundbeck A/S | Derivative compounds of aniline and pharmaceutical composition that understand it |
| SE528250C2 (sv) | 2004-02-27 | 2006-10-03 | Calignum Technologies Ab | Komposition innefattande en initiator och ett förfarande för att behandla trä med kompositionen |
| JP4569142B2 (ja) | 2004-03-22 | 2010-10-27 | コニカミノルタホールディングス株式会社 | 表示素子 |
| JP4448730B2 (ja) | 2004-04-20 | 2010-04-14 | 富士フイルム株式会社 | 感光性組成物、該感光性組成物に用いられる化合物及び該感光性組成物を用いたパターン形成方法 |
| WO2006006172A2 (en) | 2004-07-15 | 2006-01-19 | Ramot At Tel Aviv University Ltd. | Use of anti-amyloid agents for treating and typing pathogen infections |
| WO2006098380A1 (ja) | 2005-03-15 | 2006-09-21 | Fujifilm Corporation | 円盤状化合物を用いた表面処理法、表面処理用（潤滑）組成物及び表面処理された物品 |
-
2005
- 2005-07-12 AR ARP050102877A patent/AR052308A1/es not_active Application Discontinuation
- 2005-07-13 PL PL05759183T patent/PL1771415T3/pl unknown
- 2005-07-13 WO PCT/DK2005/000491 patent/WO2006007843A1/en active Application Filing
- 2005-07-13 KR KR1020067025769A patent/KR20070036061A/ko not_active Application Discontinuation
- 2005-07-13 EA EA200602180A patent/EA011418B1/ru not_active IP Right Cessation
- 2005-07-13 BR BRPI0512073-0A patent/BRPI0512073A/pt not_active IP Right Cessation
- 2005-07-13 AU AU2005263324A patent/AU2005263324A1/en not_active Abandoned
- 2005-07-13 SI SI200530606T patent/SI1771415T1/sl unknown
- 2005-07-13 PT PT05759183T patent/PT1771415E/pt unknown
- 2005-07-13 DE DE602005012272T patent/DE602005012272D1/de active Active
- 2005-07-13 JP JP2007520664A patent/JP4865710B2/ja not_active Expired - Fee Related
- 2005-07-13 UA UAA200612493A patent/UA82610C2/uk unknown
- 2005-07-13 ZA ZA200610162A patent/ZA200610162B/en unknown
- 2005-07-13 AT AT05759183T patent/ATE420071T1/de active
- 2005-07-13 RS RSP-2009/0070A patent/RS50804B/sr unknown
- 2005-07-13 DK DK05759183T patent/DK1771415T3/da active
- 2005-07-13 CA CA2570805A patent/CA2570805C/en not_active Expired - Fee Related
- 2005-07-13 US US11/629,043 patent/US7678800B2/en not_active Expired - Fee Related
- 2005-07-13 EP EP05759183A patent/EP1771415B1/en active Active
- 2005-07-13 CN CNA200580020862XA patent/CN1972911A/zh active Pending
- 2005-07-13 ES ES05759183T patent/ES2317266T3/es active Active
- 2005-07-13 MX MXPA06015201A patent/MXPA06015201A/es not_active Application Discontinuation
-
2006
- 2006-12-07 IL IL179924A patent/IL179924A0/en unknown
- 2006-12-27 NO NO20066010A patent/NO20066010L/no not_active Application Discontinuation
-
2009
- 2009-02-23 HR HR20090112T patent/HRP20090112T3/xx unknown
- 2009-03-31 CY CY20091100373T patent/CY1108942T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS50804B (sr) | 2010-08-31 |
| AU2005263324A1 (en) | 2006-01-26 |
| DK1771415T3 (da) | 2009-02-23 |
| ES2317266T3 (es) | 2009-04-16 |
| JP2008506640A (ja) | 2008-03-06 |
| CN1972911A (zh) | 2007-05-30 |
| BRPI0512073A (pt) | 2008-02-06 |
| CA2570805A1 (en) | 2006-01-26 |
| CY1108942T1 (el) | 2014-07-02 |
| KR20070036061A (ko) | 2007-04-02 |
| EA011418B1 (ru) | 2009-02-27 |
| DE602005012272D1 (de) | 2009-02-26 |
| AR052308A1 (es) | 2007-03-14 |
| US7678800B2 (en) | 2010-03-16 |
| ATE420071T1 (de) | 2009-01-15 |
| PT1771415E (pt) | 2009-03-16 |
| MXPA06015201A (es) | 2007-03-15 |
| SI1771415T1 (sl) | 2009-04-30 |
| EA200602180A1 (ru) | 2007-04-27 |
| JP4865710B2 (ja) | 2012-02-01 |
| HRP20090112T3 (en) | 2009-03-31 |
| IL179924A0 (en) | 2007-05-15 |
| NO20066010L (no) | 2006-12-27 |
| US20080027074A1 (en) | 2008-01-31 |
| EP1771415A1 (en) | 2007-04-11 |
| EP1771415B1 (en) | 2009-01-07 |
| PL1771415T3 (pl) | 2009-06-30 |
| UA82610C2 (uk) | 2008-04-25 |
| CA2570805C (en) | 2010-08-24 |
| WO2006007843A1 (en) | 2006-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ZA200610162B (en) | 2-(1H-indolylsulfanyl)-aryl amine derivatives for use in the treatment of affective disorders, pain, ADHD and stress urinary incontinence | |
| Mauri et al. | A risk-benefit assessment of sulpiride in the treatment of schizophrenia | |
| Taciak et al. | Drugs which influence serotonin transporter and serotonergic receptors: pharmacological and clinical properties in the treatment of depression | |
| Tarazi et al. | Iloperidone, asenapine and lurasidone: a primer on their current status | |
| CA2567249A1 (en) | Lithium combinations, and uses related thereto | |
| JP2008538577A (ja) | ジヒドロベンゾフラン誘導体およびその使用 | |
| JP2008536946A (ja) | うつ病の処置または予防のための新規の治療的組み合わせ | |
| JP2008542378A (ja) | 精神病性障害を管理する方法および組成物 | |
| Bymaster et al. | New approaches to developing antidepressants by enhancing monoaminergic neurotransmission | |
| UA96447C2 (uk) | Поліморфні форми (2s)-(4e)-n-метил-5-[3-(5-ізопропоксипіридин)іл]-4-пентен-2-аміну для лікування розладів центральної нервової системи | |
| ZA200006817B (en) | Combination therapy for treatment of Bipolar Disorders. | |
| Smeraldi et al. | Agomelatine in depression | |
| AU2004303461B2 (en) | 2-(1H-indolylsulfanyl)-benzyl amine derivatives as SSRI | |
| RU2011146032A (ru) | Соединения-агонисты рецептора 5-ht4 для лечения расстройств познавательной способности | |
| CN104955483A (zh) | 用低剂量药剂治疗抑郁症和其它疾病 | |
| CN115734785A (zh) | (S)-(4,5-二氢-7H-噻吩并[2,3-c]吡喃-7-基)-N-甲基甲胺用于治疗神经和精神方面的病症 | |
| Kintscher | Reuptake inhibitors of dopamine, noradrenaline, and serotonin | |
| Phillips | Treating body dysmorphic disorder using medication | |
| ZA200605058B (en) | 2-(1H-indolylsulfanyl)-benzyl amine derivatives as SSRI | |
| Gaszner et al. | Major depression and the synthetic enhancer substances,(−)-deprenyl and R-(−)-1-(benzofuran-2-yl)-2-propylaminopentane | |
| CN101189215A (zh) | 苯并氧氮辛因及其治疗用途 | |
| Behere et al. | Antidepressants | |
| Stevens et al. | Psychopharmacology in the medical setting | |
| Mody et al. | In search of novel and therapeutically significant melatoninergic ligands | |
| US20060217394A1 (en) | Treatment of anhedonia |