ZA200405731B - Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands - Google Patents
Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands Download PDFInfo
- Publication number
- ZA200405731B ZA200405731B ZA200405731A ZA200405731A ZA200405731B ZA 200405731 B ZA200405731 B ZA 200405731B ZA 200405731 A ZA200405731 A ZA 200405731A ZA 200405731 A ZA200405731 A ZA 200405731A ZA 200405731 B ZA200405731 B ZA 200405731B
- Authority
- ZA
- South Africa
- Prior art keywords
- sulfonyl
- imidazo
- chloro
- indol
- thiazole
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 96
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- 108091005435 5-HT6 receptors Proteins 0.000 claims description 16
- -1 cycloheteroalkyl Chemical group 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002619 bicyclic group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 208000019901 Anxiety disease Diseases 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N protonated dimethyl amine Natural products CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 3
- 208000019430 Motor disease Diseases 0.000 claims description 3
- 208000018737 Parkinson disease Diseases 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Natural products NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 230000002252 carbamoylating effect Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 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 description 2
- 229940117803 phenethylamine Drugs 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 101500025412 Mus musculus Processed cyclic AMP-responsive element-binding protein 3-like protein 1 Proteins 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 238000010586 diagram Methods 0.000 description 13
- 239000000460 chlorine Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 208000015114 central nervous system disease Diseases 0.000 description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 208000035475 disorder Diseases 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 108020004999 messenger RNA Proteins 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 230000036506 anxiety Effects 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
- 229940076279 serotonin Drugs 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- UGZFQKKKGOPZMG-UHFFFAOYSA-N 2-(2-imino-1,3-thiazol-3-yl)acetic acid Chemical compound OC(=O)CN1C=CSC1=N UGZFQKKKGOPZMG-UHFFFAOYSA-N 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 208000032841 Bulimia Diseases 0.000 description 2
- 206010006550 Bulimia nervosa Diseases 0.000 description 2
- 206010013654 Drug abuse Diseases 0.000 description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 206010019196 Head injury Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000019695 Migraine disease Diseases 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 208000022531 anorexia Diseases 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 125000004438 haloalkoxy group Chemical group 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 206010027599 migraine Diseases 0.000 description 2
- 230000036651 mood Effects 0.000 description 2
- 210000001577 neostriatum Anatomy 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 210000001009 nucleus accumben Anatomy 0.000 description 2
- 210000001010 olfactory tubercle Anatomy 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000008174 sterile solution Substances 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- LTJSKICFXZFBLT-UHFFFAOYSA-N 2-(1-imidazo[2,1-b][1,3]thiazol-5-ylsulfonylindol-3-yl)ethanamine Chemical compound C1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3)C2=C1 LTJSKICFXZFBLT-UHFFFAOYSA-N 0.000 description 1
- YOLHSBHQHDKVKV-UHFFFAOYSA-N 2-[1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]-n,n-dimethylethanamine Chemical compound C1=CC=C2C(CCN(C)C)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 YOLHSBHQHDKVKV-UHFFFAOYSA-N 0.000 description 1
- QNBSNFPYXPFWRW-UHFFFAOYSA-N 2-[1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]ethanamine Chemical compound C1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 QNBSNFPYXPFWRW-UHFFFAOYSA-N 0.000 description 1
- RNYHQAMOZIGXSD-UHFFFAOYSA-N 2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonyl-6-methoxyindol-3-yl]ethanamine Chemical compound COC1=CC=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 RNYHQAMOZIGXSD-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- SBHOLLTVFWOGAI-UHFFFAOYSA-N 2-[5-bromo-1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]ethanamine Chemical compound C1=C(Br)C=C2C(CCN)=CN(S(=O)(=O)C=3N4C=CSC4=NC=3Cl)C2=C1 SBHOLLTVFWOGAI-UHFFFAOYSA-N 0.000 description 1
- MQZGKLOUZNZXFQ-UHFFFAOYSA-N 2-[5-chloro-1-(2,6-dichloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]ethanamine Chemical compound C1=C(Cl)C=C2C(CCN)=CN(S(=O)(=O)C=3N4C=C(Cl)SC4=NC=3Cl)C2=C1 MQZGKLOUZNZXFQ-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 1
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 1
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 1
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 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 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000014630 G protein-coupled serotonin receptor activity proteins Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 238000000636 Northern blotting Methods 0.000 description 1
- 206010033664 Panic attack Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010043903 Tobacco abuse Diseases 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- DXGTUUQHTDOFFQ-UHFFFAOYSA-N [N].C1=CC=C2NC=CC2=C1 Chemical group [N].C1=CC=C2NC=CC2=C1 DXGTUUQHTDOFFQ-UHFFFAOYSA-N 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 210000004727 amygdala Anatomy 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 229940106681 chloroacetic acid Drugs 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229960003920 cocaine Drugs 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000012059 conventional drug carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- 210000001947 dentate gyrus Anatomy 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- ODCCJTMPMUFERV-UHFFFAOYSA-N ditert-butyl carbonate Chemical compound CC(C)(C)OC(=O)OC(C)(C)C ODCCJTMPMUFERV-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- RBQGKSWYSQGVDV-UHFFFAOYSA-N imidazo[2,1-b][1,3]benzothiazole Chemical group C1=CC=C2N3C=CN=C3SC2=C1 RBQGKSWYSQGVDV-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000012948 isocyanate Chemical class 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 150000002540 isothiocyanates Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 230000006993 memory improvement Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000010369 molecular cloning Methods 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- LHCJQTWZVANFIS-UHFFFAOYSA-N n-benzyl-2-[1-(6-chloroimidazo[2,1-b][1,3]thiazol-5-yl)sulfonylindol-3-yl]ethanamine Chemical compound ClC=1N=C2SC=CN2C=1S(=O)(=O)N(C1=CC=CC=C11)C=C1CCNCC1=CC=CC=C1 LHCJQTWZVANFIS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000000626 neurodegenerative effect Effects 0.000 description 1
- 230000000955 neuroendocrine Effects 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- 229940124606 potential therapeutic agent Drugs 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P25/14—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
- A61P25/00—Drugs for disorders of the nervous system
- 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
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Indole Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US34290701P | 2001-12-20 | 2001-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200405731B true ZA200405731B (en) | 2007-02-28 |
Family
ID=23343804
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200405731A ZA200405731B (en) | 2001-12-20 | 2004-07-19 | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
Country Status (30)
Country | Link |
---|---|
US (2) | US6770642B2 (ja) |
EP (1) | EP1455779B1 (ja) |
JP (1) | JP4335684B2 (ja) |
KR (1) | KR100985140B1 (ja) |
CN (1) | CN1309385C (ja) |
AR (1) | AR037906A1 (ja) |
AT (1) | ATE335477T1 (ja) |
AU (1) | AU2002357270B2 (ja) |
BR (1) | BR0215222A (ja) |
CA (1) | CA2470863C (ja) |
CO (1) | CO5590924A2 (ja) |
CY (1) | CY1105705T1 (ja) |
DE (1) | DE60213856T2 (ja) |
DK (1) | DK1455779T3 (ja) |
EC (1) | ECSP045156A (ja) |
ES (1) | ES2269827T3 (ja) |
HK (1) | HK1065949A1 (ja) |
HU (1) | HUP0402640A3 (ja) |
IL (1) | IL162243A0 (ja) |
MX (1) | MXPA04005889A (ja) |
NO (1) | NO330338B1 (ja) |
NZ (1) | NZ533666A (ja) |
PL (1) | PL210413B1 (ja) |
PT (1) | PT1455779E (ja) |
RU (1) | RU2309157C2 (ja) |
SI (1) | SI1455779T1 (ja) |
TW (1) | TWI254705B (ja) |
UA (1) | UA78536C2 (ja) |
WO (1) | WO2003053433A1 (ja) |
ZA (1) | ZA200405731B (ja) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0115262A (pt) * | 2000-11-09 | 2003-08-12 | Mitsui Chemicals Inc | Derivados de amina opticamente ativos e processo de preparação destes |
TW200301251A (en) * | 2001-12-20 | 2003-07-01 | Wyeth Corp | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands |
JP2006528186A (ja) * | 2003-07-23 | 2006-12-14 | ワイス | 5−ヒドロキシトリプタミン−6リガンドとしてのスルホニルジヒドロベンゾイミダゾロン化合物 |
US20050032873A1 (en) * | 2003-07-30 | 2005-02-10 | Wyeth | 3-Amino chroman and 2-amino tetralin derivatives |
JP2007500701A (ja) * | 2003-07-31 | 2007-01-18 | ワイス | 5−ヒドロキシトリプタミン−6リガンドとしてのn−スルホニルヘテロシクロピロリルアルキルアミン化合物 |
AU2004261667A1 (en) * | 2003-08-01 | 2005-02-10 | Genelabs Technologies, Inc. | Bicyclic imidazol derivatives against Flaviviridae |
CA2552106C (en) * | 2004-01-02 | 2011-10-11 | Suven Life Sciences Limited | Novel indeno[2,1a]indenes and isoindol[2,1-a]indoles |
PE20060303A1 (es) * | 2004-06-23 | 2006-05-19 | Wyeth Corp | Metabolitos de indolilalquilamina como ligandos de 5-hidroxitriptamina-6 |
BRPI0519036A2 (pt) * | 2004-12-14 | 2008-12-23 | Wyeth Corp | mÉtodo para o tratamento de um paciente acometido por uma doenÇa neuro-degenerativa; composiÇço farmacÊutica para tratar uma doenÇa neuro-degenerativa; e uso de um agonista 5-ht6 ou de um agonista 5-ht6 |
CN101103026A (zh) * | 2005-01-14 | 2008-01-09 | 健亚生物科技公司 | 用于治疗病毒感染的吲哚衍生物 |
EP1953153A1 (en) * | 2007-01-31 | 2008-08-06 | Laboratorios del Dr. Esteve S.A. | Heterocyclyl-substituted sulfonamides for the treatment of cognitive or food ingestion related disorders |
US20080318941A1 (en) * | 2007-05-24 | 2008-12-25 | Memory Pharmaceuticals Corporation | 4' substituted compounds having 5-ht6 receptor affinity |
DE602007012683D1 (de) * | 2007-07-19 | 2011-04-07 | Esteve Labor Dr | Substituierte Tetrahydro-Chinolinsulfonamidverbindungen, ihre Herstellung und ihre Verwendung als Medikamente |
EP2053052A1 (en) * | 2007-10-23 | 2009-04-29 | Laboratorios del Dr. Esteve S.A. | Process for the preparation of 6-substituted imidazo[2,1-b]thiazole-5-sulfonyl halide |
EP2231160B1 (en) * | 2007-12-04 | 2013-08-14 | Merck Sharp & Dohme Corp. | Tryptamine sulfonamides as 5-ht6 antagonists |
WO2009082268A2 (ru) | 2007-12-21 | 2009-07-02 | Alla Chem, Llc | ЛИГАНДЫ α-АДРЕНОЦЕПТОРОВ, ДОПАМИНОВЫХ, ГИСТАМИНОВЫХ, ИМИДАЗОЛИНОВЫХ И СЕРОТОНИНОВЫХ РЕЦЕПТОРОВ И ИХ ПРИМЕНЕНИЕ |
US20100016297A1 (en) * | 2008-06-24 | 2010-01-21 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
US20100022581A1 (en) * | 2008-07-02 | 2010-01-28 | Memory Pharmaceuticals Corporation | Pyrrolidine-substituted azaindole compounds having 5-ht6 receptor affinity |
US20100029629A1 (en) * | 2008-07-25 | 2010-02-04 | Memory Pharmaceuticals Corporation | Acyclic compounds having 5-ht6 receptor affinity |
US20100056531A1 (en) * | 2008-08-22 | 2010-03-04 | Memory Pharmaceuticals Corporation | Alkyl-substituted 3' compounds having 5-ht6 receptor affinity |
CN104725295B (zh) | 2013-12-20 | 2019-05-24 | 广东东阳光药业有限公司 | 芳杂环类衍生物及其在药物上的应用 |
ES2898965T3 (es) | 2014-08-29 | 2022-03-09 | Chdi Foundation Inc | Sondas de formación de imágenes de la proteína Huntingtina |
US10907197B2 (en) * | 2014-08-29 | 2021-02-02 | Chdi Foundation, Inc. | Probes for imaging huntingtin protein |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5545644A (en) | 1990-10-15 | 1996-08-13 | Pfizer Inc. | Indole derivatives |
US6194410B1 (en) | 1998-03-11 | 2001-02-27 | Hoffman-La Roche Inc. | Pyrazolopyrimidine and pyrazolines and process for preparation thereof |
US6133287A (en) | 1998-03-24 | 2000-10-17 | Allelix Biopharmaceuticals Inc. | Piperidine-indole compounds having 5-HT6 affinity |
GB9820113D0 (en) * | 1998-09-15 | 1998-11-11 | Merck Sharp & Dohme | Therapeutic agents |
US6403808B1 (en) | 1999-12-10 | 2002-06-11 | Virginia Commonwealth University | Selective 5-HT6 receptor ligands |
DK1204662T3 (da) * | 1999-08-12 | 2004-10-04 | Nps Allelix Corp | Azaindoler med serotoninreceptoraffinitet |
WO2001032660A1 (en) * | 1999-11-05 | 2001-05-10 | Nps Allelix Corp. | Compounds having 5-ht6 receptor antagonist activity |
WO2001034146A1 (en) * | 1999-11-08 | 2001-05-17 | Smithkline Beecham Corporation | Novel anti-infectives |
-
2002
- 2002-12-17 EP EP02805601A patent/EP1455779B1/en not_active Expired - Lifetime
- 2002-12-17 BR BR0215222-3A patent/BR0215222A/pt not_active Application Discontinuation
- 2002-12-17 SI SI200230401T patent/SI1455779T1/sl unknown
- 2002-12-17 DK DK02805601T patent/DK1455779T3/da active
- 2002-12-17 WO PCT/US2002/040217 patent/WO2003053433A1/en active IP Right Grant
- 2002-12-17 DE DE60213856T patent/DE60213856T2/de not_active Expired - Lifetime
- 2002-12-17 KR KR1020047009606A patent/KR100985140B1/ko not_active IP Right Cessation
- 2002-12-17 UA UA20040705919A patent/UA78536C2/uk unknown
- 2002-12-17 HU HU0402640A patent/HUP0402640A3/hu unknown
- 2002-12-17 ES ES02805601T patent/ES2269827T3/es not_active Expired - Lifetime
- 2002-12-17 AT AT02805601T patent/ATE335477T1/de active
- 2002-12-17 CA CA2470863A patent/CA2470863C/en not_active Expired - Fee Related
- 2002-12-17 NZ NZ533666A patent/NZ533666A/xx not_active IP Right Cessation
- 2002-12-17 MX MXPA04005889A patent/MXPA04005889A/es active IP Right Grant
- 2002-12-17 CN CNB028281721A patent/CN1309385C/zh not_active Expired - Fee Related
- 2002-12-17 JP JP2003554190A patent/JP4335684B2/ja not_active Expired - Fee Related
- 2002-12-17 AU AU2002357270A patent/AU2002357270B2/en not_active Ceased
- 2002-12-17 PT PT02805601T patent/PT1455779E/pt unknown
- 2002-12-17 PL PL370711A patent/PL210413B1/pl not_active IP Right Cessation
- 2002-12-17 IL IL16224302A patent/IL162243A0/xx unknown
- 2002-12-17 RU RU2004122129/04A patent/RU2309157C2/ru not_active IP Right Cessation
- 2002-12-18 TW TW091136490A patent/TWI254705B/zh active
- 2002-12-18 AR ARP020104951A patent/AR037906A1/es unknown
- 2002-12-19 US US10/323,369 patent/US6770642B2/en not_active Expired - Fee Related
-
2004
- 2004-04-20 US US10/828,014 patent/US7022701B2/en not_active Expired - Fee Related
- 2004-06-15 CO CO04055771A patent/CO5590924A2/es not_active Application Discontinuation
- 2004-06-16 EC EC2004005156A patent/ECSP045156A/es unknown
- 2004-07-19 ZA ZA200405731A patent/ZA200405731B/en unknown
- 2004-07-19 NO NO20043100A patent/NO330338B1/no not_active IP Right Cessation
- 2004-11-10 HK HK04108844A patent/HK1065949A1/xx not_active IP Right Cessation
-
2006
- 2006-10-13 CY CY20061101474T patent/CY1105705T1/el unknown
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200405731B (en) | Indolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands | |
US6767912B2 (en) | Heterocyclylindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands | |
US20040023970A1 (en) | 1-Heterocyclylalkyl-3-sulfonylazaindole or -azaindazole derivatives as 5-hydroxytryptamine-6 ligands | |
ZA200405733B (en) | Azaindolylalkylamine derivatives as 5-hydroxytryptamine-6 ligands. | |
ZA200500021B (en) | 1-(Aminoalkyl)-3-sylfonnylindole and -indazole derivatives as 5-hydroxytryptamine-5 ligands | |
US7608717B2 (en) | Sulfonyldihydroimidazopyridinone compounds as 5-hydroxytryptamine-6 ligands | |
EP1654258A1 (en) | Sulfonyldihydro- benzimidazolone compounds as 5-hydroxytryptamine-6 ligands | |
CA2570818A1 (en) | Indolylalkylamine metabolites as 5-hydroxytrytamine-6 ligands | |
JP6844822B2 (ja) | 疼痛に対して活性を有する置換モルホリン誘導体 | |
EP1803720A1 (en) | Heterocyclindazole and -azaindazole compounds as 5-hydroxytryptamine-6 ligands | |
AU2002236613A1 (en) | Heterocyclindazole and azaindazole compounds as 5-hydroxytryptamine-6 ligands |