JP2011511810A - インドール化合物およびその使用方法 - Google Patents
インドール化合物およびその使用方法 Download PDFInfo
- Publication number
- JP2011511810A JP2011511810A JP2010546107A JP2010546107A JP2011511810A JP 2011511810 A JP2011511810 A JP 2011511810A JP 2010546107 A JP2010546107 A JP 2010546107A JP 2010546107 A JP2010546107 A JP 2010546107A JP 2011511810 A JP2011511810 A JP 2011511810A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- compound
- substituents
- amino
- compound according
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 190
- 150000002475 indoles Chemical class 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 628
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 1181
- 125000001424 substituent group Chemical group 0.000 claims description 449
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 434
- -1 cyano, hydroxy Chemical group 0.000 claims description 353
- 229910052736 halogen Inorganic materials 0.000 claims description 245
- 125000003545 alkoxy group Chemical group 0.000 claims description 229
- 150000002367 halogens Chemical class 0.000 claims description 225
- 125000003282 alkyl amino group Chemical group 0.000 claims description 216
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 214
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 211
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 196
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 196
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 179
- 239000000203 mixture Substances 0.000 claims description 132
- 229910052799 carbon Inorganic materials 0.000 claims description 125
- 235000019000 fluorine Nutrition 0.000 claims description 124
- 229910052739 hydrogen Inorganic materials 0.000 claims description 101
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
- 239000001257 hydrogen Substances 0.000 claims description 68
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims description 65
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 64
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 63
- 229910052731 fluorine Inorganic materials 0.000 claims description 63
- 239000011737 fluorine Substances 0.000 claims description 63
- 125000001153 fluoro group Chemical group F* 0.000 claims description 60
- 208000015114 central nervous system disease Diseases 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 45
- 208000019901 Anxiety disease Diseases 0.000 claims description 44
- 208000012902 Nervous system disease Diseases 0.000 claims description 42
- 208000028017 Psychotic disease Diseases 0.000 claims description 40
- 201000000980 schizophrenia Diseases 0.000 claims description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 208000008589 Obesity Diseases 0.000 claims description 39
- 239000002552 dosage form Substances 0.000 claims description 39
- 235000020824 obesity Nutrition 0.000 claims description 39
- 230000036506 anxiety Effects 0.000 claims description 38
- 230000036528 appetite Effects 0.000 claims description 37
- 235000019789 appetite Nutrition 0.000 claims description 37
- 206010012601 diabetes mellitus Diseases 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 30
- 201000004624 Dermatitis Diseases 0.000 claims description 30
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 28
- 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 claims description 26
- 208000024827 Alzheimer disease Diseases 0.000 claims description 18
- 201000001880 Sexual dysfunction Diseases 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 231100000872 sexual dysfunction Toxicity 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 16
- 206010012335 Dependence Diseases 0.000 claims description 16
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 16
- 208000016620 Tourette disease Diseases 0.000 claims description 16
- 206010015037 epilepsy Diseases 0.000 claims description 16
- 201000004384 Alopecia Diseases 0.000 claims description 15
- 208000024963 hair loss Diseases 0.000 claims description 15
- 230000003676 hair loss Effects 0.000 claims description 15
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 14
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 14
- 239000006186 oral dosage form Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 12
- 238000006467 substitution reaction Methods 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 150000003840 hydrochlorides Chemical class 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 70
- 150000002222 fluorine compounds Chemical class 0.000 claims 36
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 187
- NLMQHXUGJIAKTH-UHFFFAOYSA-N 4-hydroxyindole Chemical class OC1=CC=CC2=C1C=CN2 NLMQHXUGJIAKTH-UHFFFAOYSA-N 0.000 abstract description 4
- 208000031295 Animal disease Diseases 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 107
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 84
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 78
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 78
- 208000035475 disorder Diseases 0.000 description 72
- 102000005962 receptors Human genes 0.000 description 39
- 108020003175 receptors Proteins 0.000 description 39
- 238000011282 treatment Methods 0.000 description 37
- 230000000694 effects Effects 0.000 description 36
- 125000005843 halogen group Chemical group 0.000 description 23
- 208000019695 Migraine disease Diseases 0.000 description 22
- 206010027599 migraine Diseases 0.000 description 22
- 125000003342 alkenyl group Chemical group 0.000 description 21
- 235000002639 sodium chloride Nutrition 0.000 description 20
- 206010010144 Completed suicide Diseases 0.000 description 17
- 229940079593 drug Drugs 0.000 description 17
- 239000003814 drug Substances 0.000 description 17
- 210000003414 extremity Anatomy 0.000 description 16
- 241000282472 Canis lupus familiaris Species 0.000 description 15
- 230000001965 increasing effect Effects 0.000 description 14
- 239000000556 agonist Substances 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 12
- 230000019771 cognition Effects 0.000 description 12
- 201000010099 disease Diseases 0.000 description 12
- 238000001727 in vivo Methods 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- 229940044601 receptor agonist Drugs 0.000 description 11
- 239000000018 receptor agonist Substances 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 208000020016 psychiatric disease Diseases 0.000 description 10
- 230000001225 therapeutic effect Effects 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 229940076279 serotonin Drugs 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 230000037396 body weight Effects 0.000 description 8
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- 230000002708 enhancing effect Effects 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- 108010072553 5-HT2C Serotonin Receptor Proteins 0.000 description 6
- 102000006902 5-HT2C Serotonin Receptor Human genes 0.000 description 6
- 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 6
- 241000282412 Homo Species 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 239000003937 drug carrier Substances 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- 230000036651 mood Effects 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 230000004584 weight gain Effects 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 5
- 206010012289 Dementia Diseases 0.000 description 5
- 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 5
- 229930006000 Sucrose Natural products 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- 230000003930 cognitive ability Effects 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000005720 sucrose Substances 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 231100000331 toxic Toxicity 0.000 description 5
- 230000002588 toxic effect Effects 0.000 description 5
- 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 4
- 206010006550 Bulimia nervosa Diseases 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 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 4
- 241000124008 Mammalia Species 0.000 description 4
- 206010026749 Mania Diseases 0.000 description 4
- 206010034912 Phobia Diseases 0.000 description 4
- 125000004442 acylamino group Chemical group 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 125000002877 alkyl aryl group Chemical group 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 239000003963 antioxidant agent Substances 0.000 description 4
- 235000006708 antioxidants Nutrition 0.000 description 4
- 230000003542 behavioural effect Effects 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 229960001582 fenfluramine Drugs 0.000 description 4
- 239000000945 filler Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 239000008273 gelatin Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 235000011852 gelatine desserts Nutrition 0.000 description 4
- 230000036541 health Effects 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000008101 lactose 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
- 208000024714 major depressive disease Diseases 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 208000019906 panic disease Diseases 0.000 description 4
- 238000007911 parenteral administration Methods 0.000 description 4
- 230000002093 peripheral effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 208000011117 substance-related disease Diseases 0.000 description 4
- 125000000547 substituted alkyl group Chemical group 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 4
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical class ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000282465 Canis Species 0.000 description 3
- 208000030814 Eating disease Diseases 0.000 description 3
- 208000019454 Feeding and Eating disease Diseases 0.000 description 3
- 206010020772 Hypertension Diseases 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 208000012826 adjustment disease Diseases 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 235000010443 alginic acid Nutrition 0.000 description 3
- 229920000615 alginic acid Polymers 0.000 description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 description 3
- 125000004947 alkyl aryl amino group Chemical group 0.000 description 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 description 3
- 125000004691 alkyl thio carbonyl group Chemical group 0.000 description 3
- 238000010171 animal model Methods 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 239000002830 appetite depressant Substances 0.000 description 3
- 125000001769 aryl amino group Chemical group 0.000 description 3
- 125000004658 aryl carbonyl amino group Chemical group 0.000 description 3
- 125000005199 aryl carbonyloxy group Chemical group 0.000 description 3
- 125000005110 aryl thio group Chemical group 0.000 description 3
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 3
- 201000011510 cancer Diseases 0.000 description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 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
- 230000006378 damage Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 125000004663 dialkyl amino group Chemical group 0.000 description 3
- 125000004986 diarylamino group Chemical group 0.000 description 3
- 235000014632 disordered eating Nutrition 0.000 description 3
- 206010013663 drug dependence Diseases 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 230000003400 hallucinatory effect Effects 0.000 description 3
- 239000000380 hallucinogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 206010027175 memory impairment Diseases 0.000 description 3
- 239000002674 ointment Substances 0.000 description 3
- 201000008482 osteoarthritis Diseases 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000006187 pill Substances 0.000 description 3
- 125000003367 polycyclic group Polymers 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- QVDSEJDULKLHCG-UHFFFAOYSA-N psilocybin Chemical class C1=CC(OP(O)(O)=O)=C2C(CCN(C)C)=CNC2=C1 QVDSEJDULKLHCG-UHFFFAOYSA-N 0.000 description 3
- 201000002859 sleep apnea Diseases 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 2
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- YVLXUPOKFBWUDB-UHFFFAOYSA-N 2-(5-fluoro-4-phenylmethoxy-1h-indol-3-yl)-n,n-dimethylethanamine Chemical compound C=12C(CCN(C)C)=CNC2=CC=C(F)C=1OCC1=CC=CC=C1 YVLXUPOKFBWUDB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 208000008811 Agoraphobia Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 208000020925 Bipolar disease Diseases 0.000 description 2
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
- 208000032928 Dyslipidaemia Diseases 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- 208000027534 Emotional disease Diseases 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 241000287828 Gallus gallus Species 0.000 description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 description 2
- 208000011688 Generalised anxiety disease Diseases 0.000 description 2
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 201000005569 Gout Diseases 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- 101150013372 Htr2c gene Proteins 0.000 description 2
- 206010021030 Hypomania Diseases 0.000 description 2
- 206010022773 Intracranial pressure increased Diseases 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- 229930195725 Mannitol Natural products 0.000 description 2
- 201000009906 Meningitis Diseases 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000027626 Neurocognitive disease Diseases 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 206010033664 Panic attack Diseases 0.000 description 2
- 208000018737 Parkinson disease Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- 241000283984 Rodentia Species 0.000 description 2
- 208000028810 Shared psychotic disease Diseases 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 208000011962 Substance-induced mood disease Diseases 0.000 description 2
- 231100000395 Substance-induced mood disorder Toxicity 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 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 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 description 2
- 102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 description 2
- 208000026345 acute stress disease Diseases 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 230000016571 aggressive behavior Effects 0.000 description 2
- 239000000783 alginic acid Substances 0.000 description 2
- 229960001126 alginic acid Drugs 0.000 description 2
- 150000004781 alginic acids Chemical class 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 125000005200 aryloxy carbonyloxy group Chemical group 0.000 description 2
- 230000006399 behavior Effects 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 208000028683 bipolar I disease Diseases 0.000 description 2
- 208000022257 bipolar II disease Diseases 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 2
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 150000007942 carboxylates Chemical class 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 235000013330 chicken meat Nutrition 0.000 description 2
- 230000001149 cognitive effect Effects 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 201000010064 diabetes insipidus Diseases 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 208000024732 dysthymic disease Diseases 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
- 208000020694 gallbladder disease Diseases 0.000 description 2
- 208000029364 generalized anxiety disease Diseases 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000011283 initial treatment period Methods 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000007913 intrathecal administration Methods 0.000 description 2
- GSEKYIWUAPZIEF-UHFFFAOYSA-N ismine hydrochloride Natural products CNC1=CC=CC=C1C(C(=C1)CO)=CC2=C1OCO2 GSEKYIWUAPZIEF-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- XTTZERNUQAFMOF-QMMMGPOBSA-N lorcaserin Chemical compound C[C@H]1CNCCC2=CC=C(Cl)C=C12 XTTZERNUQAFMOF-QMMMGPOBSA-N 0.000 description 2
- 229960005060 lorcaserin Drugs 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000594 mannitol Substances 0.000 description 2
- 235000010355 mannitol Nutrition 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 2
- 230000004770 neurodegeneration Effects 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 230000009437 off-target effect Effects 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 208000022821 personality disease Diseases 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- 208000019899 phobic disease Diseases 0.000 description 2
- 125000004437 phosphorous atom Chemical group 0.000 description 2
- 208000028173 post-traumatic stress disease Diseases 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 150000003151 propanoic acid esters Chemical class 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 230000000698 schizophrenic effect Effects 0.000 description 2
- 208000019116 sleep disease Diseases 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 201000001716 specific phobia Diseases 0.000 description 2
- 208000020431 spinal cord injury Diseases 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 125000004434 sulfur atom Chemical group 0.000 description 2
- 238000007910 systemic administration Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 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
- QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 1
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- MLBHFBKZUPLWBD-ZETCQYMHSA-N (2S)-1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound C[C@H](N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-ZETCQYMHSA-N 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N (R)-alpha-Tocopherol Natural products OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
- MLBHFBKZUPLWBD-UHFFFAOYSA-N 1-[3-(trifluoromethyl)phenyl]-2-propanamine Chemical compound CC(N)CC1=CC=CC(C(F)(F)F)=C1 MLBHFBKZUPLWBD-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GPOFPOWVZRQGRW-UHFFFAOYSA-N 3-fluoro-2-phenylmethoxybenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1OCC1=CC=CC=C1 GPOFPOWVZRQGRW-UHFFFAOYSA-N 0.000 description 1
- ACMIJDVJWLMBCX-PXAZEXFGSA-N 4-[(3ar,6ar)-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[2,3-c]pyrrol-5-yl]-6-fluoro-n-methyl-2-(2-methylpyrimidin-5-yl)oxy-9h-pyrimido[4,5-b]indol-8-amine Chemical group CNC1=CC(F)=CC(C2=C(N3C[C@@H]4NCC[C@@H]4C3)N=3)=C1NC2=NC=3OC1=CN=C(C)N=C1 ACMIJDVJWLMBCX-PXAZEXFGSA-N 0.000 description 1
- 108091005479 5-HT2 receptors Proteins 0.000 description 1
- 108010072584 5-HT2B Serotonin Receptor Proteins 0.000 description 1
- 102000006969 5-HT2B Serotonin Receptor Human genes 0.000 description 1
- CYEQSOYROKGJDA-UHFFFAOYSA-N 6-methoxy-1h-indazole Chemical class COC1=CC=C2C=NNC2=C1 CYEQSOYROKGJDA-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 208000007848 Alcoholism Diseases 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 101710137189 Amyloid-beta A4 protein Proteins 0.000 description 1
- 101710151993 Amyloid-beta precursor protein Proteins 0.000 description 1
- 102100022704 Amyloid-beta precursor protein Human genes 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 208000015121 Cardiac valve disease Diseases 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- 208000024254 Delusional disease Diseases 0.000 description 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 1
- 206010013654 Drug abuse Diseases 0.000 description 1
- 102100029503 E3 ubiquitin-protein ligase TRIM32 Human genes 0.000 description 1
- 208000037579 Eating reflex epilepsy Diseases 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 206010016717 Fistula Diseases 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 101000634982 Homo sapiens E3 ubiquitin-protein ligase TRIM32 Proteins 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical class ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 201000006347 Intellectual Disability Diseases 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 208000009829 Lewy Body Disease Diseases 0.000 description 1
- 201000002832 Lewy body dementia Diseases 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 239000004909 Moisturizer Substances 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
- 206010029897 Obsessive thoughts Diseases 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 208000027099 Paranoid disease Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000012891 Ringer solution Substances 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 208000000810 Separation Anxiety Diseases 0.000 description 1
- 229940127347 Serotonin 2c Receptor Agonists Drugs 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 206010065604 Suicidal behaviour Diseases 0.000 description 1
- 229920000535 Tan II Polymers 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- BLGXFZZNTVWLAY-CCZXDCJGSA-N Yohimbine Natural products C1=CC=C2C(CCN3C[C@@H]4CC[C@@H](O)[C@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-CCZXDCJGSA-N 0.000 description 1
- DDOSYAJVNWEFNC-VOTSOKGWSA-N [(e)-2-azidoethenyl]benzene Chemical compound [N-]=[N+]=N\C=C\C1=CC=CC=C1 DDOSYAJVNWEFNC-VOTSOKGWSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 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 1
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 201000007930 alcohol dependence Diseases 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 125000004419 alkynylene group Chemical group 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 229940087168 alpha tocopherol Drugs 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- DZHSAHHDTRWUTF-SIQRNXPUSA-N amyloid-beta polypeptide 42 Chemical compound C([C@@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)NCC(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(O)=O)[C@@H](C)CC)C(C)C)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C1=CC=CC=C1 DZHSAHHDTRWUTF-SIQRNXPUSA-N 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 230000007529 anxiety like behavior Effects 0.000 description 1
- 235000021407 appetite control Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical class 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
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 208000025748 atypical depressive disease Diseases 0.000 description 1
- 150000008038 benzoazepines Chemical class 0.000 description 1
- BLGXFZZNTVWLAY-UHFFFAOYSA-N beta-Yohimbin Natural products C1=CC=C2C(CCN3CC4CCC(O)C(C4CC33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-UHFFFAOYSA-N 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 239000004067 bulking agent Substances 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003130 cardiopathic effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 229960001305 cysteine hydrochloride Drugs 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000002716 delivery method Methods 0.000 description 1
- 230000003001 depressive effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229910052805 deuterium Inorganic materials 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- 229910000393 dicalcium diphosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000002651 drug therapy Methods 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000005584 early death Effects 0.000 description 1
- 208000024239 eating seizures Diseases 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000003890 fistula Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 230000005714 functional activity Effects 0.000 description 1
- 230000007160 gastrointestinal dysfunction Effects 0.000 description 1
- 230000005176 gastrointestinal motility Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- YQEMORVAKMFKLG-UHFFFAOYSA-N glycerine monostearate Natural products CCCCCCCCCCCCCCCCCC(=O)OC(CO)CO YQEMORVAKMFKLG-UHFFFAOYSA-N 0.000 description 1
- SVUQHVRAGMNPLW-UHFFFAOYSA-N glycerol monostearate Natural products CCCCCCCCCCCCCCCCC(=O)OCC(O)CO SVUQHVRAGMNPLW-UHFFFAOYSA-N 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 210000003709 heart valve Anatomy 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 101150075901 htr2 gene Proteins 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000000509 infertility Diseases 0.000 description 1
- 230000036512 infertility Effects 0.000 description 1
- 231100000535 infertility Toxicity 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000000266 injurious effect Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- RXYCUKSOYJWGPE-UHFFFAOYSA-N methyl 2-azidoacetate Chemical compound COC(=O)CN=[N+]=[N-] RXYCUKSOYJWGPE-UHFFFAOYSA-N 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- UMLARORAEPLXTC-UHFFFAOYSA-N n-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine;2-methyl-1-phenylpropan-2-amine Chemical compound CC(C)(N)CC1=CC=CC=C1.CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 UMLARORAEPLXTC-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000011623 obesity animal model Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- 208000002851 paranoid schizophrenia Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 238000001050 pharmacotherapy Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 201000000484 premenstrual tension Diseases 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 230000022558 protein metabolic process Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940001470 psychoactive drug Drugs 0.000 description 1
- 238000001671 psychotherapy Methods 0.000 description 1
- 239000004089 psychotropic agent Substances 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 239000003813 safflower oil Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 208000025874 separation anxiety disease Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000000862 serotonergic effect Effects 0.000 description 1
- 239000002485 serotonin 2C agonist Substances 0.000 description 1
- 239000000952 serotonin receptor agonist Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000392 somatic effect Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup 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
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- AOBORMOPSGHCAX-DGHZZKTQSA-N tocofersolan Chemical compound OCCOC(=O)CCC(=O)OC1=C(C)C(C)=C2O[C@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C AOBORMOPSGHCAX-DGHZZKTQSA-N 0.000 description 1
- 229960000984 tocofersolan Drugs 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229910052722 tritium Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- XOSKJKGKWRIMGV-DGCLKSJQSA-N way-163909 Chemical compound C1NCCN2[C@@H]3CCC[C@@H]3C3=CC=CC1=C32 XOSKJKGKWRIMGV-DGCLKSJQSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- BLGXFZZNTVWLAY-SCYLSFHTSA-N yohimbine Chemical compound C1=CC=C2C(CCN3C[C@@H]4CC[C@H](O)[C@@H]([C@H]4C[C@H]33)C(=O)OC)=C3NC2=C1 BLGXFZZNTVWLAY-SCYLSFHTSA-N 0.000 description 1
- 229960000317 yohimbine Drugs 0.000 description 1
- AADVZSXPNRLYLV-UHFFFAOYSA-N yohimbine carboxylic acid Natural products C1=CC=C2C(CCN3CC4CCC(C(C4CC33)C(O)=O)O)=C3NC2=C1 AADVZSXPNRLYLV-UHFFFAOYSA-N 0.000 description 1
- 239000002076 α-tocopherol Substances 0.000 description 1
- 235000004835 α-tocopherol Nutrition 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- 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
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
-
- 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
- A61P25/28—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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Reproductive Health (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2782508P | 2008-02-11 | 2008-02-11 | |
| PCT/US2009/033822 WO2009102805A1 (en) | 2008-02-11 | 2009-02-11 | Indole compounds and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011511810A true JP2011511810A (ja) | 2011-04-14 |
| JP2011511810A5 JP2011511810A5 (https=) | 2012-04-05 |
Family
ID=40445507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010546107A Withdrawn JP2011511810A (ja) | 2008-02-11 | 2009-02-11 | インドール化合物およびその使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20090318527A1 (https=) |
| EP (1) | EP2254865A1 (https=) |
| JP (1) | JP2011511810A (https=) |
| AU (1) | AU2009214724A1 (https=) |
| CA (1) | CA2715282A1 (https=) |
| WO (1) | WO2009102805A1 (https=) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022525036A (ja) * | 2019-03-07 | 2022-05-11 | アーバーメンティス・エルエルシー | 非サイケデリック/精神異常発現性の投与量及び製剤で投与される神経可塑性作用を有する物質を含む組成物並びに使用方法 |
| JP2023513680A (ja) * | 2020-02-04 | 2023-04-03 | マインドセット ファーマ インコーポレイテッド | 中枢神経系障害の治療のためのセロトニン作動性幻覚薬としてのシロシン誘導体 |
| JP2024520485A (ja) * | 2021-05-26 | 2024-05-24 | ブライト マインズ バイオサイエンスィズ インコーポレイテッド | 複素環式化合物及びその調製方法 |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005300045A1 (en) * | 2004-09-27 | 2006-05-04 | Organix, Inc. | Indole compounds useful as serotonin selective agents |
| CN102574787B (zh) * | 2009-07-30 | 2014-12-31 | 新加坡国立大学 | 具有潜在的抗癌活性的小分子异戊二烯基半胱氨酸羧基甲基转移酶抑制剂 |
| EP2464227A4 (en) * | 2009-08-10 | 2013-02-20 | Galenea Corp | COMPOUNDS AND METHODS OF USE |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| WO2018064465A1 (en) * | 2016-09-29 | 2018-04-05 | The Regents Of The University Of California | Compounds for increasing neural plasticity |
| GB2571696B (en) | 2017-10-09 | 2020-05-27 | Compass Pathways Ltd | Large scale method for the preparation of Psilocybin and formulations of Psilocybin so produced |
| US12459965B2 (en) | 2017-10-09 | 2025-11-04 | Compass Pathfinder Limited | Preparation of psilocybin, different polymorphic forms, intermediates, formulations and their use |
| US11485734B2 (en) | 2018-10-02 | 2022-11-01 | Northwestern University | Beta-carbolines as positive allosteric modulators of the human serotonin receptor 2C (5-HT2C) |
| CN113784962B (zh) | 2019-02-27 | 2025-04-25 | 加利福尼亚大学董事会 | 用于治疗脑部疾病的氮杂环庚三烯并-吲哚类和其他杂环 |
| KR20220009954A (ko) | 2019-04-17 | 2022-01-25 | 컴퍼스 패쓰파인더 리미티드 | 신경인지 장애, 만성 통증을 치료하고 염증을 감소시키는 방법 |
| CA3160793A1 (en) * | 2019-12-04 | 2021-06-10 | Neonmind Biosciences Inc. | Use of psilocin, psilocybin or analogs thereof in weight loss, treatment of obesity and compulsive eating disorder |
| KR20240096817A (ko) | 2020-05-19 | 2024-06-26 | 사이빈 아이알엘 리미티드 | 중수소화된 트립타민 유도체 및 사용 방법 |
| US12343328B2 (en) | 2020-12-09 | 2025-07-01 | Caamtech, Inc. | Dialkyl tryptamines and their therapeutic uses |
| JP2025501629A (ja) * | 2021-12-24 | 2025-01-22 | サイロ プロプライエタリ リミテッド | 化合物 |
| US12065404B2 (en) | 2022-03-18 | 2024-08-20 | Enveric Biosciences Canada Inc. | C4-carboxylic acid-substituted tryptamine derivatives and methods of using |
| AU2023307226A1 (en) * | 2022-07-15 | 2025-02-27 | Caamtech, Inc. | Tryptamine derivatives |
| JP2025526785A (ja) * | 2022-08-11 | 2025-08-15 | ギルガメッシュ・ファーマシューティカルズ・インコーポレイテッド | トリプタミン及び気分障害を治療する方法 |
| US20260083759A1 (en) | 2022-09-06 | 2026-03-26 | Hadasit Medical Research Services And Development Ltd | Combinations Comprising Psychedelics for the Treatment of Schizophrenia and Other Neuropsychiatric and Neurologic Disorders |
| AU2024309903A1 (en) | 2023-06-28 | 2026-01-08 | Psylo Pty Ltd | Compounds |
| CN121909189A (zh) | 2023-06-28 | 2026-04-21 | 赛洛私人有限公司 | 用于治疗精神疾病的吡咯并吡啶化合物 |
| WO2025099725A1 (en) | 2023-11-09 | 2025-05-15 | Hadasit Medical Research Services And Development Ltd. | Conjugates and uses thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60222396T2 (de) * | 2001-03-29 | 2008-05-15 | Eli Lilly And Co., Indianapolis | N-(2-arylethyl) benzylamine als 5-ht6 rezeptor-antagoniste |
| AU2005300045A1 (en) * | 2004-09-27 | 2006-05-04 | Organix, Inc. | Indole compounds useful as serotonin selective agents |
-
2009
- 2009-02-11 EP EP09710775A patent/EP2254865A1/en not_active Withdrawn
- 2009-02-11 US US12/369,659 patent/US20090318527A1/en not_active Abandoned
- 2009-02-11 JP JP2010546107A patent/JP2011511810A/ja not_active Withdrawn
- 2009-02-11 AU AU2009214724A patent/AU2009214724A1/en not_active Abandoned
- 2009-02-11 CA CA2715282A patent/CA2715282A1/en not_active Abandoned
- 2009-02-11 WO PCT/US2009/033822 patent/WO2009102805A1/en not_active Ceased
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2022525036A (ja) * | 2019-03-07 | 2022-05-11 | アーバーメンティス・エルエルシー | 非サイケデリック/精神異常発現性の投与量及び製剤で投与される神経可塑性作用を有する物質を含む組成物並びに使用方法 |
| JP7679304B2 (ja) | 2019-03-07 | 2025-05-19 | アーバーメンティス・エルエルシー | 非サイケデリック/精神異常発現性の投与量及び製剤で投与される神経可塑性作用を有する物質を含む組成物並びに使用方法 |
| JP2023513680A (ja) * | 2020-02-04 | 2023-04-03 | マインドセット ファーマ インコーポレイテッド | 中枢神経系障害の治療のためのセロトニン作動性幻覚薬としてのシロシン誘導体 |
| JP2023513679A (ja) * | 2020-02-04 | 2023-04-03 | マインドセット ファーマ インコーポレイテッド | 中枢神経系障害の治療のためのセロトニン作動性幻覚薬としてのシロシン誘導体 |
| JP2024054193A (ja) * | 2020-02-04 | 2024-04-16 | マインドセット ファーマ インコーポレイテッド | 中枢神経系障害の治療のためのセロトニン作動性幻覚薬としてのシロシン誘導体 |
| JP2024520485A (ja) * | 2021-05-26 | 2024-05-24 | ブライト マインズ バイオサイエンスィズ インコーポレイテッド | 複素環式化合物及びその調製方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20090318527A1 (en) | 2009-12-24 |
| AU2009214724A1 (en) | 2009-08-20 |
| EP2254865A1 (en) | 2010-12-01 |
| WO2009102805A1 (en) | 2009-08-20 |
| CA2715282A1 (en) | 2009-08-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2011511810A (ja) | インドール化合物およびその使用方法 | |
| CN113784962B (zh) | 用于治疗脑部疾病的氮杂环庚三烯并-吲哚类和其他杂环 | |
| US8071786B2 (en) | Indole compounds useful as serotonin selective agents | |
| JP4094950B2 (ja) | インドール誘導体および5−ht2bおよび5−ht2c受容体リガンドとしてのそれらの使用 | |
| CA2769474C (fr) | Derives d'acyl-guanidines modulateurs de la voie de signalisation des proteines hedgehog | |
| CN115403570B (zh) | μ-阿片受体激动剂及其制备方法和在医药领域的应用 | |
| FR2903101A1 (fr) | Nouveaux derives naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| JPH08109169A (ja) | 非ペプチドタキキニン受容体拮抗物質 | |
| TW200836743A (en) | Quinazolinone and fused pyrimidinone compounds and their use in treating sodium channel-mediated diseases or conditions | |
| US20150045442A1 (en) | Novel melatonin ligands having antidepressant activity as well as sleep inducing properties | |
| CA2722258C (fr) | N-acylthiourees et n-acylurees inhibiteurs de la voie de signalisation des proteines hedgehog | |
| EP0737670B1 (fr) | Amides tricycliques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent | |
| EA015974B1 (ru) | Производные пирролизина, индолизина и хинолизина, их получение и их применение в терапии | |
| CA3104808A1 (en) | Lactate enhancing compounds and uses thereof | |
| EP0994102B1 (fr) | Dérivés cycliques à chaíne cycloalkylénique, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent | |
| AU2008315309A1 (en) | Amino arylsulfonamide compounds and their use as 5-HT6 ligands | |
| CN110446495A (zh) | 含有7元氮杂杂环的δ阿片受体调节化合物及其使用和制备方法 | |
| WO2009022062A1 (fr) | Nouveaux derives naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| EP2167460A2 (fr) | Nouveaux derives naphtaleniques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| HK40065557A (en) | Azepino-indoles and other heterocycles for treating brain disorders | |
| WO2005012282A1 (fr) | Nouveaux derives du benzothiofene 2-thiosubstitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20120210 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20120210 |
|
| A072 | Dismissal of procedure [no reply to invitation to correct request for examination] |
Free format text: JAPANESE INTERMEDIATE CODE: A073 Effective date: 20130620 |
|
| A300 | Application deemed to be withdrawn because no request for examination was validly filed |
Free format text: JAPANESE INTERMEDIATE CODE: A300 Effective date: 20130702 |