ES2239226T3 - Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos. - Google Patents
Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos.Info
- Publication number
- ES2239226T3 ES2239226T3 ES02727527T ES02727527T ES2239226T3 ES 2239226 T3 ES2239226 T3 ES 2239226T3 ES 02727527 T ES02727527 T ES 02727527T ES 02727527 T ES02727527 T ES 02727527T ES 2239226 T3 ES2239226 T3 ES 2239226T3
- Authority
- ES
- Spain
- Prior art keywords
- indole
- oxazolo
- formula
- compounds
- cycloalkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000003446 ligand Substances 0.000 title claims description 16
- 230000000862 serotonergic effect Effects 0.000 title claims description 10
- CIACKZWMHRQXBR-UHFFFAOYSA-N 6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical class N1C=CC2=C1C=CC1=C2N=CO1 CIACKZWMHRQXBR-UHFFFAOYSA-N 0.000 title description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 82
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 21
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 125000004429 atom Chemical group 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
- 239000004305 biphenyl Substances 0.000 claims abstract description 5
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 5
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 3
- -1 1-azabicyclo [2.2.2] oct-3-yl Chemical group 0.000 claims description 154
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 13
- 229940079593 drug Drugs 0.000 claims description 10
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 7
- 206010012289 Dementia Diseases 0.000 claims description 7
- 201000000980 schizophrenia Diseases 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 6
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 230000006872 improvement Effects 0.000 claims description 5
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000019901 Anxiety disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 208000028017 Psychotic disease Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 4
- 230000006931 brain damage Effects 0.000 claims description 4
- 231100000874 brain damage Toxicity 0.000 claims description 4
- 208000029028 brain injury Diseases 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- SPFWHUJSJQVRMB-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCN1CCC(O1)=NC2=C1C=CC1=C2C=CN1 SPFWHUJSJQVRMB-UHFFFAOYSA-N 0.000 claims description 3
- AJRVPWOPYOKQDN-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(2-imidazol-1-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CCN1C=CN=C1 AJRVPWOPYOKQDN-UHFFFAOYSA-N 0.000 claims description 3
- FBERXFHTIIVDCZ-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 FBERXFHTIIVDCZ-UHFFFAOYSA-N 0.000 claims description 3
- ZNJKKGYLILLJRG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(5-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC3=CNC4=CC=C(C=C43)OC)=C1C=C2 ZNJKKGYLILLJRG-UHFFFAOYSA-N 0.000 claims description 3
- CHGLCUWMBUYUCI-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound O1C(CCC)=NC(C2=3)=C1C=CC=3NC=C2C1CCN(C)CC1 CHGLCUWMBUYUCI-UHFFFAOYSA-N 0.000 claims description 3
- PXYFHCRZTJGCCR-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC1=CC=CS1 PXYFHCRZTJGCCR-UHFFFAOYSA-N 0.000 claims description 3
- 208000032841 Bulimia Diseases 0.000 claims description 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims description 3
- 208000030814 Eating disease Diseases 0.000 claims description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 3
- 208000023105 Huntington disease Diseases 0.000 claims description 3
- 206010057852 Nicotine dependence Diseases 0.000 claims description 3
- 206010036618 Premenstrual syndrome Diseases 0.000 claims description 3
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 3
- 208000016620 Tourette disease Diseases 0.000 claims description 3
- 235000014632 disordered eating Nutrition 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 230000001590 oxidative effect Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 231100000167 toxic agent Toxicity 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 2
- 108010009685 Cholinergic Receptors Proteins 0.000 claims description 2
- 102000034337 acetylcholine receptors Human genes 0.000 claims description 2
- 125000004197 benzothien-3-yl group Chemical group [H]C1=C(*)C2=C([H])C([H])=C([H])C([H])=C2S1 0.000 claims description 2
- 231100000867 compulsive behavior Toxicity 0.000 claims description 2
- 230000006866 deterioration Effects 0.000 claims description 2
- 210000004558 lewy body Anatomy 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 208000034189 Sclerosis Diseases 0.000 claims 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 110
- 239000000243 solution Substances 0.000 description 61
- 238000001556 precipitation Methods 0.000 description 52
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 208000035475 disorder Diseases 0.000 description 9
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 7
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229940076279 serotonin Drugs 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VOCGEKMEZOPDFP-UHFFFAOYSA-N 2-(6-methoxy-1h-indol-3-yl)ethanamine Chemical compound COC1=CC=C2C(CCN)=CNC2=C1 VOCGEKMEZOPDFP-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 102000005962 receptors Human genes 0.000 description 5
- 108020003175 receptors Proteins 0.000 description 5
- HJORCZCMNWLHMB-UHFFFAOYSA-N 1-(3-aminopropyl)pyrrolidin-2-one Chemical compound NCCCN1CCCC1=O HJORCZCMNWLHMB-UHFFFAOYSA-N 0.000 description 4
- RGUABPVONIGVAT-UHFFFAOYSA-N 3-(4-methylpiperazin-1-yl)propan-1-amine Chemical compound CN1CCN(CCCN)CC1 RGUABPVONIGVAT-UHFFFAOYSA-N 0.000 description 4
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 4
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 4
- 229960003638 dopamine Drugs 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 3
- 108091005477 5-HT3 receptors Proteins 0.000 description 3
- 102000035037 5-HT3 receptors Human genes 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 229960004373 acetylcholine Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 229960000846 camphor Drugs 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 208000013403 hyperactivity Diseases 0.000 description 3
- 238000002483 medication Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002858 neurotransmitter agent Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 235000012222 talc Nutrition 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- WCHWFFFRCUMMIK-UHFFFAOYSA-N 1-[2-(6h-pyrrolo[3,2-e][1,3]benzoxazol-2-yl)ethyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCC(O1)=NC2=C1C=CC1=C2C=CN1 WCHWFFFRCUMMIK-UHFFFAOYSA-N 0.000 description 2
- UTECKXUTRQVEAD-UHFFFAOYSA-N 1-[2-(8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazol-2-yl)ethyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCC(O1)=NC2=C1C=CC1=C2C(C2CCNCC2)=CN1 UTECKXUTRQVEAD-UHFFFAOYSA-N 0.000 description 2
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- FCZRQZWQNZIIAN-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-8-(1-methylpiperidin-4-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(=N3)C=4C5=CC=CC=C5SC=4)C3=C12 FCZRQZWQNZIIAN-UHFFFAOYSA-N 0.000 description 2
- GFCOVMJXZYOTSK-UHFFFAOYSA-N 2-(1-benzothiophen-3-yl)-8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CNCCC1C1=CNC2=CC=C(OC(=N3)C=4C5=CC=CC=C5SC=4)C3=C12 GFCOVMJXZYOTSK-UHFFFAOYSA-N 0.000 description 2
- JKKGNFVYQLLWSC-UHFFFAOYSA-N 2-(2-imidazol-1-ylethyl)-8-(1-methylpiperidin-4-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(CCN3C=NC=C3)=N3)C3=C12 JKKGNFVYQLLWSC-UHFFFAOYSA-N 0.000 description 2
- BIFVEYQXSBFUEN-UHFFFAOYSA-N 2-(2-imidazol-1-ylethyl)-8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CCN1C=CN=C1 BIFVEYQXSBFUEN-UHFFFAOYSA-N 0.000 description 2
- DFXMQXZWIFLTFZ-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C=CNC=2C=C2)=C2OC=1CCN1CCOCC1 DFXMQXZWIFLTFZ-UHFFFAOYSA-N 0.000 description 2
- NNCHTSVVKCAJHC-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)-8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1COCCN1CCC(O1)=NC(C2=3)=C1C=CC=3NC=C2C1CCNCC1 NNCHTSVVKCAJHC-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- HJBSGDXKGYCTOE-UHFFFAOYSA-N 2-[(6-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C=1NC2=CC(OC)=CC=C2C=1CC(O1)=NC2=C1C=CC1=C2C=CN1 HJBSGDXKGYCTOE-UHFFFAOYSA-N 0.000 description 2
- NOEJDLDTBNDVCO-UHFFFAOYSA-N 2-[(6-methoxy-1h-indol-3-yl)methyl]-8-(1-methylpiperidin-4-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C=1NC2=CC(OC)=CC=C2C=1CC(O1)=NC(C2=3)=C1C=CC=3NC=C2C1CCN(C)CC1 NOEJDLDTBNDVCO-UHFFFAOYSA-N 0.000 description 2
- AHFXPSVVYXKVQD-UHFFFAOYSA-N 2-[(6-methoxy-1h-indol-3-yl)methyl]-8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C=1NC2=CC(OC)=CC=C2C=1CC(O1)=NC(C2=3)=C1C=CC=3NC=C2C1CCNCC1 AHFXPSVVYXKVQD-UHFFFAOYSA-N 0.000 description 2
- AWOZFCYHICZPFN-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-8-(1-methylpiperidin-4-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(CCN3CCN(C)CC3)=N3)C3=C12 AWOZFCYHICZPFN-UHFFFAOYSA-N 0.000 description 2
- QGYPYIYNOFCVEG-UHFFFAOYSA-N 2-[2-(4-methylpiperazin-1-yl)ethyl]-8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCN1CCC(O1)=NC2=C1C=CC1=C2C(C2CCNCC2)=CN1 QGYPYIYNOFCVEG-UHFFFAOYSA-N 0.000 description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- WEHXDSNELSUVIT-UHFFFAOYSA-N 2-pyridin-3-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N1C=CC(C=2N=3)=C1C=CC=2OC=3C1=CC=CN=C1 WEHXDSNELSUVIT-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- HVLUYXIJZLDNIS-UHFFFAOYSA-N 2-thiophen-2-ylethanamine Chemical compound NCCC1=CC=CS1 HVLUYXIJZLDNIS-UHFFFAOYSA-N 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 2
- LMIQERWZRIFWNZ-UHFFFAOYSA-N 5-hydroxyindole Chemical compound OC1=CC=C2NC=CC2=C1 LMIQERWZRIFWNZ-UHFFFAOYSA-N 0.000 description 2
- LCNIYPVROPJPML-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(1,3-benzodioxol-5-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)C3=CC=C4OCOC4=C3)=C1C=C2 LCNIYPVROPJPML-UHFFFAOYSA-N 0.000 description 2
- NPNMHINEDFCEKG-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(1-benzothiophen-3-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1=CC=C2C(C=3OC4=CC=C5NC=C(C5=C4N=3)C3C4CCN(C3)CC4)=CSC2=C1 NPNMHINEDFCEKG-UHFFFAOYSA-N 0.000 description 2
- CIPWHMKCOSUIOD-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(2-methoxyphenyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound COC1=CC=CC=C1C(O1)=NC2=C1C=CC1=C2C(C2C3CCN(CC3)C2)=CN1 CIPWHMKCOSUIOD-UHFFFAOYSA-N 0.000 description 2
- PMDZBPHMMDILLL-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(2-morpholin-4-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3C4CCN(CC4)C3)=CNC=2C=C2)=C2OC=1CCN1CCOCC1 PMDZBPHMMDILLL-UHFFFAOYSA-N 0.000 description 2
- PZGFWWZXIZYFCX-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)C3CC4CC(C4(C)C)C3C)=C1C=C2 PZGFWWZXIZYFCX-UHFFFAOYSA-N 0.000 description 2
- GHKTVOSZAVHCFE-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(methoxymethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)COC)=C1C=C2 GHKTVOSZAVHCFE-UHFFFAOYSA-N 0.000 description 2
- CRMBVWUBLDWDMI-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[(6-methoxy-1h-indol-3-yl)methyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CC=3C4=CC=C(C=C4NC=3)OC)=C1C=C2 CRMBVWUBLDWDMI-UHFFFAOYSA-N 0.000 description 2
- UNRZSVCIYDZZBB-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-[2-(4-methylpiperazin-1-yl)ethyl]-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCN1CCC(O1)=NC2=C1C=CC1=C2C(C2C3CCN(CC3)C2)=CN1 UNRZSVCIYDZZBB-UHFFFAOYSA-N 0.000 description 2
- RLTZPWDKZXACDM-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-heptan-3-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)C(CC)CCCC)=C1C=C2 RLTZPWDKZXACDM-UHFFFAOYSA-N 0.000 description 2
- HYFJVIDXXUWFIP-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-methyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)C)=C1C=C2 HYFJVIDXXUWFIP-UHFFFAOYSA-N 0.000 description 2
- DDLZLTSUBGFTSK-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-phenyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C2)CCC1C2C(C1=C2N=3)=CNC1=CC=C2OC=3C1=CC=CC=C1 DDLZLTSUBGFTSK-UHFFFAOYSA-N 0.000 description 2
- IBJQGDWMTAOBCV-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-propan-2-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)C(C)C)=C1C=C2 IBJQGDWMTAOBCV-UHFFFAOYSA-N 0.000 description 2
- FWTRSXHIHAGXMD-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CCC)=C1C=C2 FWTRSXHIHAGXMD-UHFFFAOYSA-N 0.000 description 2
- AZSFJKYHGWDDOZ-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-pyridin-3-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C2)CCC1C2C(C1=C2N=3)=CNC1=CC=C2OC=3C1=CC=CN=C1 AZSFJKYHGWDDOZ-UHFFFAOYSA-N 0.000 description 2
- MLVSNVZZXNMNPV-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1=C2OC=NC2=C2C(C3C4CCN(C3)CC4)=CNC2=C1 MLVSNVZZXNMNPV-UHFFFAOYSA-N 0.000 description 2
- YYYHQTZTMWQEAW-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-(2-morpholin-4-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(CCN3CCOCC3)=N3)C3=C12 YYYHQTZTMWQEAW-UHFFFAOYSA-N 0.000 description 2
- GKAVBMGICVARSX-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-(thiophen-2-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(CC=3SC=CC=3)=N3)C3=C12 GKAVBMGICVARSX-UHFFFAOYSA-N 0.000 description 2
- DGZWCKWDROZSSL-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-phenyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(=N3)C=4C=CC=CC=4)C3=C12 DGZWCKWDROZSSL-UHFFFAOYSA-N 0.000 description 2
- VXKDJWVCROPMLP-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-2-pyridin-3-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC(=N3)C=4C=NC=CC=4)C3=C12 VXKDJWVCROPMLP-UHFFFAOYSA-N 0.000 description 2
- QZDBNUWMCGKKNB-UHFFFAOYSA-N 8-(1-methylpiperidin-4-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(OC=N3)C3=C12 QZDBNUWMCGKKNB-UHFFFAOYSA-N 0.000 description 2
- OQQFWEIPFNFYJY-UHFFFAOYSA-N 8-piperidin-3-yl-2-propyl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound O1C(CCC)=NC(C2=3)=C1C=CC=3NC=C2C1CCCNC1 OQQFWEIPFNFYJY-UHFFFAOYSA-N 0.000 description 2
- URPVAMSEPWRIHO-UHFFFAOYSA-N 8-piperidin-4-yl-2-(thiophen-3-ylmethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C(C3CCNCC3)=CNC=2C=C2)=C2OC=1CC=1C=CSC=1 URPVAMSEPWRIHO-UHFFFAOYSA-N 0.000 description 2
- YJQOINTVKWRPHR-UHFFFAOYSA-N 8-piperidin-4-yl-2-pyridin-3-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CNCCC1C1=CNC2=CC=C(OC(=N3)C=4C=NC=CC=4)C3=C12 YJQOINTVKWRPHR-UHFFFAOYSA-N 0.000 description 2
- ZQQCELRETNKHCX-UHFFFAOYSA-N 8-piperidin-4-yl-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CNCCC1C1=CNC2=CC=C(OC=N3)C3=C12 ZQQCELRETNKHCX-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000723346 Cinnamomum camphora Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 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 2
- 241001465754 Metazoa Species 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000000323 Tourette Syndrome Diseases 0.000 description 2
- 206010047700 Vomiting Diseases 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229930008380 camphor Natural products 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000004064 dysfunction Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N gamma-butyrolactam Natural products O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 206010027175 memory impairment Diseases 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 2
- FLYPBMIJIXGULG-UHFFFAOYSA-N n-methylthiophen-3-amine Chemical compound CNC=1C=CSC=1 FLYPBMIJIXGULG-UHFFFAOYSA-N 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000000626 neurodegenerative effect Effects 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 125000003373 pyrazinyl group Chemical group 0.000 description 2
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 2
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 2
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 2
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- MXYUKLILVYORSK-UHFFFAOYSA-N (+/-)-allo-lobeline Natural products C1CCC(CC(=O)C=2C=CC=CC=2)N(C)C1CC(O)C1=CC=CC=C1 MXYUKLILVYORSK-UHFFFAOYSA-N 0.000 description 1
- MXYUKLILVYORSK-HBMCJLEFSA-N (-)-lobeline Chemical compound C1([C@@H](O)C[C@H]2N([C@H](CCC2)CC(=O)C=2C=CC=CC=2)C)=CC=CC=C1 MXYUKLILVYORSK-HBMCJLEFSA-N 0.000 description 1
- PXJACNDVRNAFHD-UHFFFAOYSA-N (2-methoxyphenyl)methanamine Chemical compound COC1=CC=CC=C1CN PXJACNDVRNAFHD-UHFFFAOYSA-N 0.000 description 1
- 229930007886 (R)-camphor Natural products 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- QLOKJRIVRGCVIM-UHFFFAOYSA-N 1-[(4-methylsulfanylphenyl)methyl]piperazine Chemical compound C1=CC(SC)=CC=C1CN1CCNCC1 QLOKJRIVRGCVIM-UHFFFAOYSA-N 0.000 description 1
- RTJRYCBABFCWOZ-UHFFFAOYSA-N 1-[2-[8-(1-azabicyclo[2.2.2]octan-3-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazol-2-yl]ethyl]pyrrolidin-2-one Chemical compound O=C1CCCN1CCC(O1)=NC2=C1C=CC1=C2C(C2C3CCN(CC3)C2)=CN1 RTJRYCBABFCWOZ-UHFFFAOYSA-N 0.000 description 1
- PZNPLUBHRSSFHT-RRHRGVEJSA-N 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCCCC(=O)O[C@@H](COP([O-])(=O)OCC[N+](C)(C)C)COC(=O)CCCCCCCCCCCCCCC PZNPLUBHRSSFHT-RRHRGVEJSA-N 0.000 description 1
- CMDQAKJECKWECO-UHFFFAOYSA-N 2-(2-imidazol-1-ylethyl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound N=1C(C=2C=CNC=2C=C2)=C2OC=1CCN1C=CN=C1 CMDQAKJECKWECO-UHFFFAOYSA-N 0.000 description 1
- VBZWCSPBGASXRO-UHFFFAOYSA-N 2-[8-(1-azabicyclo[2.2.2]octan-3-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazol-2-yl]-n,n-dimethylethanamine Chemical compound C1N(CC2)CCC2C1C1=CNC2=C1C(N=C(O1)CCN(C)C)=C1C=C2 VBZWCSPBGASXRO-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- ASUDFOJKTJLAIK-UHFFFAOYSA-N 2-methoxyethanamine Chemical compound COCCN ASUDFOJKTJLAIK-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- OANLWIQYRRVBPY-UHFFFAOYSA-N 2-thiophen-3-ylethanamine Chemical compound NCCC=1C=CSC=1 OANLWIQYRRVBPY-UHFFFAOYSA-N 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- RVCMYAWBNRTLIC-UHFFFAOYSA-N 3-(1-azabicyclo[2.2.2]octan-3-yl)-1h-indol-5-ol Chemical compound C1N(CC2)CCC2C1C1=CNC2=CC=C(O)C=C21 RVCMYAWBNRTLIC-UHFFFAOYSA-N 0.000 description 1
- WKNFADCGOAHBPG-UHFFFAOYSA-N 3-(1-methyl-4-piperidinyl)-1H-indol-5-ol Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(O)C=C12 WKNFADCGOAHBPG-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000006306 4-iodophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1I 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
- 108091005435 5-HT6 receptors Proteins 0.000 description 1
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
- UVQXPAXARDATBM-UHFFFAOYSA-N 8-(1-azabicyclo[2.2.2]octan-3-yl)-2-(oxolan-2-yl)-6h-pyrrolo[3,2-e][1,3]benzoxazole Chemical compound C1CCOC1C(O1)=NC2=C1C=CC1=C2C(C2C3CCN(CC3)C2)=CN1 UVQXPAXARDATBM-UHFFFAOYSA-N 0.000 description 1
- 108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 description 1
- 101100283604 Caenorhabditis elegans pigk-1 gene Proteins 0.000 description 1
- 241000557626 Corvus corax Species 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- NLPRAJRHRHZCQQ-UHFFFAOYSA-N Epibatidine Natural products C1=NC(Cl)=CC=C1C1C(N2)CCC2C1 NLPRAJRHRHZCQQ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- 102000004310 Ion Channels Human genes 0.000 description 1
- 108090000862 Ion Channels Proteins 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- HJPOKQICBCJGHE-UHFFFAOYSA-J [C+4].[Cl-].[Cl-].[Cl-].[Cl-] Chemical compound [C+4].[Cl-].[Cl-].[Cl-].[Cl-] HJPOKQICBCJGHE-UHFFFAOYSA-J 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 239000000074 antisense oligonucleotide Substances 0.000 description 1
- 238000012230 antisense oligonucleotides Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019568 aromas Nutrition 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000003693 atypical antipsychotic agent Substances 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 229960004106 citric acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 description 1
- 229960004170 clozapine Drugs 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 210000001947 dentate gyrus Anatomy 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- NLPRAJRHRHZCQQ-IVZWLZJFSA-N epibatidine Chemical compound C1=NC(Cl)=CC=C1[C@@H]1[C@H](N2)CC[C@H]2C1 NLPRAJRHRHZCQQ-IVZWLZJFSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000013773 glyceryl triacetate Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 210000001320 hippocampus Anatomy 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 201000010901 lateral sclerosis Diseases 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
- 125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
- 208000005264 motor neuron disease Diseases 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 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
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- DBGFNLVRAFYZBI-UHFFFAOYSA-N n-methylpyridin-3-amine Chemical compound CNC1=CC=CN=C1 DBGFNLVRAFYZBI-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000002232 neuromuscular Effects 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 210000001009 nucleus accumben Anatomy 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 210000001010 olfactory tubercle Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- CINJIXGRSTYIHP-UHFFFAOYSA-N oxolan-3-ylmethanamine Chemical compound NCC1CCOC1 CINJIXGRSTYIHP-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000004346 phenylpentyl group Chemical group C1(=CC=CC=C1)CCCCC* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- HDOUGSFASVGDCS-UHFFFAOYSA-N pyridin-3-ylmethanamine Chemical compound NCC1=CC=CN=C1 HDOUGSFASVGDCS-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001959 radiotherapy Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 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
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008347 soybean phospholipid 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
- 239000005720 sucrose Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000016978 synaptic transmission, cholinergic Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- DUDAKCCDHRNMDJ-UHFFFAOYSA-N thiophen-3-ylmethanamine Chemical compound NCC=1C=CSC=1 DUDAKCCDHRNMDJ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 229940099259 vaseline Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- 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
- A61P25/14—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Child & Adolescent Psychology (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Reproductive Health (AREA)
- Nutrition Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10121217 | 2001-04-30 | ||
| DE10121217A DE10121217A1 (de) | 2001-04-30 | 2001-04-30 | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2239226T3 true ES2239226T3 (es) | 2005-09-16 |
Family
ID=7683302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES02727527T Expired - Lifetime ES2239226T3 (es) | 2001-04-30 | 2002-04-05 | Derivados de 6h-oxazolo(4,5-e)indol como ligandos de receptores de acetilcolina nicotinicos y/o ligandos serotonergicos. |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US7291633B2 (https=) |
| EP (1) | EP1392699B1 (https=) |
| JP (1) | JP4485746B2 (https=) |
| AR (1) | AR033267A1 (https=) |
| AT (1) | ATE291026T1 (https=) |
| AU (1) | AU2002257752B2 (https=) |
| CA (1) | CA2445835C (https=) |
| CZ (1) | CZ20033194A3 (https=) |
| DE (2) | DE10121217A1 (https=) |
| ES (1) | ES2239226T3 (https=) |
| HU (1) | HUP0304034A2 (https=) |
| SK (1) | SK14482003A3 (https=) |
| WO (1) | WO2002088139A1 (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
| AU2003227522A1 (en) * | 2002-05-30 | 2003-12-19 | Neurosearch A/S | 3-substituted quinuclidines and their use |
| WO2005041957A1 (en) * | 2003-10-29 | 2005-05-12 | Pfizer Products Inc. | Oxindole derivatives and their use as phosphodiesterase type 2 inhibitors |
| US9125900B2 (en) * | 2005-09-14 | 2015-09-08 | University Of The Witwatersrand, Johannesburg | Pharmaceutical composition |
| JP6321662B2 (ja) | 2012-10-12 | 2018-05-09 | ザ ブロード インスティテュート, インコーポレーテッドThe Broad Institute, Inc. | Ｇｓｋ３阻害剤およびその使用の方法 |
| SG11201509371XA (en) * | 2013-05-24 | 2015-12-30 | Nestec Sa | Pathway specific markers for diagnosing irritable bowel syndrome |
| US11203601B2 (en) * | 2017-04-05 | 2021-12-21 | The Broad Institute, Inc. | Tricyclic compounds as glycogen synthase kinase 3 (GSK3) inhibitors and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2073340C (en) | 1990-01-11 | 1997-05-20 | Hakan Vilhelm Wikstrom | Centrally acting 6,7,8,9-tetrahydro-3h-benz(e)indole heterocyclics |
| TW263508B (https=) * | 1991-02-12 | 1995-11-21 | Pfizer | |
| EP0773942A1 (en) | 1994-07-26 | 1997-05-21 | Pfizer Inc. | 4-indole derivatives as serotonin agonists and antagonists |
| US6548530B1 (en) * | 1995-10-03 | 2003-04-15 | The Scripps Research Institute | CBI analogs of CC-1065 and the duocarmycins |
| ES2199553T3 (es) | 1998-03-09 | 2004-02-16 | H.Lundbeck A/S | Indoles sustituidos con 5-heteroarilo. |
| DE10045112A1 (de) | 2000-09-11 | 2002-03-21 | Merck Patent Gmbh | Verwendung von Indolderivaten zur Behandlung von Erkrankungen des zentralen Nervensystems |
| DE10121217A1 (de) * | 2001-04-30 | 2002-10-31 | Merck Patent Gmbh | 6H-Oxazolo[4,5-e]indol-Derivate als nikotinische Acetylcholinrezeptor Liganden und/oder serotonerge Liganden |
-
2001
- 2001-04-30 DE DE10121217A patent/DE10121217A1/de not_active Withdrawn
-
2002
- 2002-04-05 CA CA2445835A patent/CA2445835C/en not_active Expired - Fee Related
- 2002-04-05 DE DE60203283T patent/DE60203283T2/de not_active Expired - Lifetime
- 2002-04-05 ES ES02727527T patent/ES2239226T3/es not_active Expired - Lifetime
- 2002-04-05 AT AT02727527T patent/ATE291026T1/de not_active IP Right Cessation
- 2002-04-05 WO PCT/EP2002/003784 patent/WO2002088139A1/en not_active Ceased
- 2002-04-05 US US10/476,306 patent/US7291633B2/en not_active Expired - Fee Related
- 2002-04-05 HU HU0304034A patent/HUP0304034A2/hu unknown
- 2002-04-05 JP JP2002585437A patent/JP4485746B2/ja not_active Expired - Fee Related
- 2002-04-05 SK SK1448-2003A patent/SK14482003A3/sk unknown
- 2002-04-05 CZ CZ20033194A patent/CZ20033194A3/cs unknown
- 2002-04-05 EP EP02727527A patent/EP1392699B1/en not_active Expired - Lifetime
- 2002-04-05 AU AU2002257752A patent/AU2002257752B2/en not_active Ceased
- 2002-04-26 AR ARP020101530A patent/AR033267A1/es not_active Application Discontinuation
-
2007
- 2007-10-30 US US11/928,961 patent/US7741343B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE60203283T2 (de) | 2006-03-30 |
| DE10121217A1 (de) | 2002-10-31 |
| AR033267A1 (es) | 2003-12-10 |
| HUP0304034A2 (hu) | 2004-04-28 |
| ATE291026T1 (de) | 2005-04-15 |
| DE60203283D1 (de) | 2005-04-21 |
| US20050101649A1 (en) | 2005-05-12 |
| JP2004527562A (ja) | 2004-09-09 |
| SK14482003A3 (sk) | 2004-03-02 |
| WO2002088139A1 (en) | 2002-11-07 |
| EP1392699A1 (en) | 2004-03-03 |
| US20080051394A1 (en) | 2008-02-28 |
| AU2002257752B2 (en) | 2008-02-28 |
| CA2445835A1 (en) | 2002-11-07 |
| EP1392699B1 (en) | 2005-03-16 |
| CA2445835C (en) | 2012-01-03 |
| JP4485746B2 (ja) | 2010-06-23 |
| US7741343B2 (en) | 2010-06-22 |
| US7291633B2 (en) | 2007-11-06 |
| CZ20033194A3 (cs) | 2004-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU211566A9 (en) | New benzimidazoline-2-oxo-1-carboxylic acid derivatives useful as 5-ht receptor antagonists | |
| MX2008015329A (es) | Derivados 1-sulfonilindazolilamina y -amida como ligandos de 5-hidroxitriptamina-6. | |
| JP2025533411A (ja) | Ｋｉｆ１８ａ阻害剤化合物、医薬組成物並びにその製造方法及び応用 | |
| US7741343B2 (en) | 6H-oxazolo[4,5 e]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands | |
| AU700561B2 (en) | Agent for potentiating nerve growth factor activity containing 1,2-ethanediol derivative or salt thereof | |
| JP4593879B2 (ja) | ニコチン性アセチルコリンレセプターリガンドおよび／またはセロトニン作動性リガンドとしてのジヒドロイミダゾ［４，５−ｅ］インドールおよび７Ｈ−ピロロ［３，２−ｆ］キノキサリン誘導体 | |
| EP3820867B1 (en) | Compounds and compositions for the treatment of cystic fibrosis | |
| AU2002310904A1 (en) | Dihydroimidazo[4,5-e]indole and 7H-pyrrolo[3,2-f]quinoxaline derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands | |
| AU2002257752A1 (en) | 6H-OXAZOLO[4,5-E]indole derivatives as nicotinic acetylcholine receptor ligands and/or serotonergic ligands | |
| NZ194245A (en) | 4-phenyl-4,5,6,7-tetrahydropyrrolo(2,3-c)pyridines | |
| JP2004527534A (ja) | ニコチン性アセチルコリン受容体リガンド | |
| GB2225574A (en) | Aryl ureas and carbamates as 5-htä antagonists | |
| JP2006503859A (ja) | 受容体拮抗薬としてのアザ二環式スピロエーテル誘導体 |