ES3001195T3 - Agonistas no peptídicos del receptor de la oxitocina - Google Patents
Agonistas no peptídicos del receptor de la oxitocina Download PDFInfo
- Publication number
- ES3001195T3 ES3001195T3 ES17880082T ES17880082T ES3001195T3 ES 3001195 T3 ES3001195 T3 ES 3001195T3 ES 17880082 T ES17880082 T ES 17880082T ES 17880082 T ES17880082 T ES 17880082T ES 3001195 T3 ES3001195 T3 ES 3001195T3
- Authority
- ES
- Spain
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- alkenyl
- alkynyl
- 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.)
- Active
Links
- 102000004279 Oxytocin receptors Human genes 0.000 title description 17
- 108090000876 Oxytocin receptors Proteins 0.000 title description 17
- 229940127264 non-peptide agonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- 238000011282 treatment Methods 0.000 claims abstract description 68
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 35
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 12
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 12
- 239000003085 diluting agent Substances 0.000 claims abstract description 7
- 239000003937 drug carrier Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 126
- 125000003342 alkenyl group Chemical group 0.000 claims description 110
- 125000000304 alkynyl group Chemical group 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 50
- 125000000623 heterocyclic group Chemical group 0.000 claims description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 33
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 206010041250 Social phobia Diseases 0.000 claims description 15
- 125000004122 cyclic group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 13
- 208000029560 autism spectrum disease Diseases 0.000 claims description 11
- 208000024714 major depressive disease Diseases 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 201000000980 schizophrenia Diseases 0.000 claims description 10
- 206010041243 Social avoidant behaviour Diseases 0.000 claims description 9
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 9
- 230000004064 dysfunction Effects 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000003107 substituted aryl group Chemical group 0.000 claims description 7
- 208000020401 Depressive disease Diseases 0.000 claims description 6
- 230000016571 aggressive behavior Effects 0.000 claims description 6
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 4
- 201000009032 substance abuse Diseases 0.000 claims description 4
- 231100000736 substance abuse Toxicity 0.000 claims description 4
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 3
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 claims description 3
- 229960003920 cocaine Drugs 0.000 claims description 3
- 229960002069 diamorphine Drugs 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 229960002715 nicotine Drugs 0.000 claims description 3
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 3
- 229940127240 opiate Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 3
- 238000000034 method Methods 0.000 abstract description 72
- 239000000203 mixture Substances 0.000 abstract description 47
- 239000003814 drug Substances 0.000 abstract description 9
- 230000000926 neurological effect Effects 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000011273 social behavior Effects 0.000 abstract description 3
- 208000012902 Nervous system disease Diseases 0.000 abstract description 2
- 208000025966 Neurological disease Diseases 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 378
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 108
- 239000011734 sodium Substances 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 64
- 238000005160 1H NMR spectroscopy Methods 0.000 description 63
- 238000000746 purification Methods 0.000 description 59
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 58
- 229910003460 diamond Inorganic materials 0.000 description 58
- 239000010432 diamond Substances 0.000 description 58
- 238000004128 high performance liquid chromatography Methods 0.000 description 56
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 54
- 239000000377 silicon dioxide Substances 0.000 description 52
- 238000003818 flash chromatography Methods 0.000 description 50
- 239000000843 powder Substances 0.000 description 50
- 238000010828 elution Methods 0.000 description 44
- 239000000243 solution Substances 0.000 description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 39
- -1 1,4-disubstituted piperidines Chemical class 0.000 description 38
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 35
- 235000011114 ammonium hydroxide Nutrition 0.000 description 35
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 34
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 32
- 229960001723 oxytocin Drugs 0.000 description 27
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 26
- 101800000989 Oxytocin Proteins 0.000 description 25
- 102400000050 Oxytocin Human genes 0.000 description 25
- 239000002253 acid Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 25
- YGKZUDNKIAQBJC-UHFFFAOYSA-N Cl.Cl.N1C=CC=CC=N1 Chemical compound Cl.Cl.N1C=CC=CC=N1 YGKZUDNKIAQBJC-UHFFFAOYSA-N 0.000 description 24
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000001953 recrystallisation Methods 0.000 description 16
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
- 238000009472 formulation Methods 0.000 description 15
- 238000001665 trituration Methods 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000000725 suspension Substances 0.000 description 14
- 239000007864 aqueous solution Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 239000003995 emulsifying agent Substances 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 239000012267 brine Substances 0.000 description 10
- 150000001721 carbon Chemical group 0.000 description 10
- 239000003086 colorant Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 10
- 239000003755 preservative agent Substances 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 230000001225 therapeutic effect Effects 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000556 agonist Substances 0.000 description 7
- 235000017557 sodium bicarbonate Nutrition 0.000 description 7
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 7
- 230000000699 topical effect Effects 0.000 description 7
- 238000004293 19F NMR spectroscopy Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 239000004909 Moisturizer Substances 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000003974 emollient agent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 230000001333 moisturizer Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003765 sweetening agent Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- QNBTUZONFJXTHH-UHFFFAOYSA-N 1-methyl-5-(4-methyl-2-nitroanilino)pyrazole-4-carbaldehyde Chemical compound CN1N=CC(C=O)=C1NC1=C(C=C(C)C=C1)[N+]([O-])=O QNBTUZONFJXTHH-UHFFFAOYSA-N 0.000 description 5
- UCAXKHVDMCFDKZ-UHFFFAOYSA-N 5-(4-methoxy-2-nitroanilino)-1-methylpyrazole-4-carbaldehyde Chemical compound COC1=CC(=C(C=C1)NC1=C(C=NN1C)C=O)[N+](=O)[O-] UCAXKHVDMCFDKZ-UHFFFAOYSA-N 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical class ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
- 239000007859 condensation product Substances 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 235000013355 food flavoring agent Nutrition 0.000 description 5
- 235000003599 food sweetener Nutrition 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 239000006210 lotion Substances 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 5
- 230000000069 prophylactic effect Effects 0.000 description 5
- 208000024891 symptom Diseases 0.000 description 5
- 229960003726 vasopressin Drugs 0.000 description 5
- VGJDHZBAULCOSN-UHFFFAOYSA-N 1,7-dimethyl-5,10-dihydro-4H-pyrazolo[4,3-c][1,5]benzodiazepine Chemical compound CN1N=CC2=C1NC1=C(NC2)C=C(C=C1)C VGJDHZBAULCOSN-UHFFFAOYSA-N 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 101000986765 Homo sapiens Oxytocin receptor Proteins 0.000 description 4
- 239000004166 Lanolin Substances 0.000 description 4
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 4
- 102100028139 Oxytocin receptor Human genes 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 description 4
- 108010004977 Vasopressins Proteins 0.000 description 4
- 102000002852 Vasopressins Human genes 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000007900 aqueous suspension Substances 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 235000011187 glycerol Nutrition 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 235000019388 lanolin Nutrition 0.000 description 4
- 229940039717 lanolin Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 4
- 229920000053 polysorbate 80 Polymers 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 4
- 230000000717 retained effect Effects 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 239000012049 topical pharmaceutical composition Substances 0.000 description 4
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 3
- RLAVEBYYFYEKAV-UHFFFAOYSA-N 7-methoxy-1-methyl-5,10-dihydro-4H-pyrazolo[4,3-c][1,5]benzodiazepine Chemical compound COC=1C=CC2=C(NCC3=C(N2)N(N=C3)C)C=1 RLAVEBYYFYEKAV-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 235000019483 Peanut oil Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 102000004136 Vasopressin Receptors Human genes 0.000 description 3
- 108090000643 Vasopressin Receptors Proteins 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 230000027455 binding Effects 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000008499 blood brain barrier function Effects 0.000 description 3
- 210000001218 blood-brain barrier Anatomy 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 230000006735 deficit Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000003349 gelling agent Substances 0.000 description 3
- FBPFZTCFMRRESA-UHFFFAOYSA-N hexane-1,2,3,4,5,6-hexol Chemical compound OCC(O)C(O)C(O)C(O)CO FBPFZTCFMRRESA-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002513 implantation Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000004006 olive oil Substances 0.000 description 3
- 235000008390 olive oil Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000312 peanut oil Substances 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- XHRWBYFQXQEVLF-UHFFFAOYSA-N pyrazolo[4,3-e][1,4]diazepine Chemical class C1=NC=CN=C2C=NN=C21 XHRWBYFQXQEVLF-UHFFFAOYSA-N 0.000 description 3
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 238000013268 sustained release Methods 0.000 description 3
- 239000012730 sustained-release form Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- OKQXWBDMQDTLIY-UHFFFAOYSA-N (1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)-(4-methylphenyl)methanone Chemical compound CN1N=CC2=C1NC1=C(N(C2)C(=O)C2=CC=C(C=C2)C)C=CC=C1 OKQXWBDMQDTLIY-UHFFFAOYSA-N 0.000 description 2
- MPMICSFCSQVNFL-UHFFFAOYSA-N (2-methoxyphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound O(C1=C(C(=O)N2CC3=C(NC4=C2C=CC=C4)N(N=C3)C)C=CC=C1)C MPMICSFCSQVNFL-UHFFFAOYSA-N 0.000 description 2
- IXDYONFHOQXWQC-UHFFFAOYSA-N (3,4-dimethylphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound CC=1C=C(C=CC=1C)C(=O)N1C2=C(NC3=C(C1)C=NN3C)C=CC=C2 IXDYONFHOQXWQC-UHFFFAOYSA-N 0.000 description 2
- CDDKMIVDNRINQG-UHFFFAOYSA-N (3,5-dimethoxyphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound COC=1C=C(C=C(C=1)OC)C(=O)N1C2=C(NC3=C(C1)C=NN3C)C=CC=C2 CDDKMIVDNRINQG-UHFFFAOYSA-N 0.000 description 2
- KGAWZUYTLYAFPY-UHFFFAOYSA-N (3-fluorophenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound O=C(N1CC=2C=NN(C=2NC2=C1C=CC=C2)C)C1=CC(F)=CC=C1 KGAWZUYTLYAFPY-UHFFFAOYSA-N 0.000 description 2
- LAFJXJOVJMADRS-UHFFFAOYSA-N (4-bromophenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound BrC1=CC=C(C=C1)C(=O)N1C2=C(NC3=C(C1)C=NN3C)C=CC=C2 LAFJXJOVJMADRS-UHFFFAOYSA-N 0.000 description 2
- KCSXGXAKLOPDLZ-UHFFFAOYSA-N (4-methoxyphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound O=C(N1CC=2C=NN(C=2NC2=C1C=CC=C2)C)C1=CC=C(OC)C=C1 KCSXGXAKLOPDLZ-UHFFFAOYSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- VFZRZRDOXPRTSC-UHFFFAOYSA-N 3,5-Dimethoxybenzaldehyde Chemical compound COC1=CC(OC)=CC(C=O)=C1 VFZRZRDOXPRTSC-UHFFFAOYSA-N 0.000 description 2
- DHQIBPUGSWVDOH-UHFFFAOYSA-N 3,5-bis(phenylmethoxy)benzoic acid Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)O)=CC=1OCC1=CC=CC=C1 DHQIBPUGSWVDOH-UHFFFAOYSA-N 0.000 description 2
- BRTDPKPJDXNQEX-UHFFFAOYSA-N 5-chloro-1-methylpyrazole-4-carbaldehyde Chemical compound CN1N=CC(C=O)=C1Cl BRTDPKPJDXNQEX-UHFFFAOYSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 206010003805 Autism Diseases 0.000 description 2
- 208000020706 Autistic disease Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- JVEJVSBFSJBJNR-UHFFFAOYSA-N C1(=CC=CC=C1)C(=O)N1C2=C(NC=3N(N=CC=3C1)C)C=CC=C2 Chemical compound C1(=CC=CC=C1)C(=O)N1C2=C(NC=3N(N=CC=3C1)C)C=CC=C2 JVEJVSBFSJBJNR-UHFFFAOYSA-N 0.000 description 2
- XHVCVQIHRBNDGP-UHFFFAOYSA-N COc1cc(CN2Cc3cnn(C)c3Nc3ccccc23)cc(OC)c1 Chemical compound COc1cc(CN2Cc3cnn(C)c3Nc3ccccc23)cc(OC)c1 XHVCVQIHRBNDGP-UHFFFAOYSA-N 0.000 description 2
- JDZHDFLDGQNFOE-UHFFFAOYSA-N COc1cccc(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound COc1cccc(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 JDZHDFLDGQNFOE-UHFFFAOYSA-N 0.000 description 2
- IRKHLBUHUZOYKA-UHFFFAOYSA-N Cc1ccc(CN2Cc3cnn(C)c3Nc3ccccc23)cc1C Chemical compound Cc1ccc(CN2Cc3cnn(C)c3Nc3ccccc23)cc1C IRKHLBUHUZOYKA-UHFFFAOYSA-N 0.000 description 2
- DZQMOCCLXKQNJG-UHFFFAOYSA-N Cc1ccc(cc1)S(=O)(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound Cc1ccc(cc1)S(=O)(=O)N1Cc2cnn(C)c2Nc2ccccc12 DZQMOCCLXKQNJG-UHFFFAOYSA-N 0.000 description 2
- WOJAMPWPLGMQIH-UHFFFAOYSA-N Cc1cccc(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound Cc1cccc(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 WOJAMPWPLGMQIH-UHFFFAOYSA-N 0.000 description 2
- YEDMBOPWJLTTPG-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cc(F)cc(F)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cc(F)cc(F)c3)c3ccccc3Nc12 YEDMBOPWJLTTPG-UHFFFAOYSA-N 0.000 description 2
- DSXFKSDXDXBEIY-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cc(O)cc(O)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cc(O)cc(O)c3)c3ccccc3Nc12 DSXFKSDXDXBEIY-UHFFFAOYSA-N 0.000 description 2
- AKMUVHODWMHYBF-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cc(OCc4ccccc4)cc(OCc4ccccc4)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cc(OCc4ccccc4)cc(OCc4ccccc4)c3)c3ccccc3Nc12 AKMUVHODWMHYBF-UHFFFAOYSA-N 0.000 description 2
- BDDFDCMEEVSURJ-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(Cl)c(Cl)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(Cl)c(Cl)c3)c3ccccc3Nc12 BDDFDCMEEVSURJ-UHFFFAOYSA-N 0.000 description 2
- RZDAEOZXDUPTRM-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(cc3)C(F)(F)F)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(cc3)C(F)(F)F)c3ccccc3Nc12 RZDAEOZXDUPTRM-UHFFFAOYSA-N 0.000 description 2
- WZPBDHUDKKREHX-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(cc3)C(O)=O)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(cc3)C(O)=O)c3ccccc3Nc12 WZPBDHUDKKREHX-UHFFFAOYSA-N 0.000 description 2
- ZLNAMKJVXOGZGI-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cccc(Br)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cccc(Br)c3)c3ccccc3Nc12 ZLNAMKJVXOGZGI-UHFFFAOYSA-N 0.000 description 2
- AKVWEHWVMWXOQA-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccccc3Br)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccccc3Br)c3ccccc3Nc12 AKVWEHWVMWXOQA-UHFFFAOYSA-N 0.000 description 2
- WQEWYSPDZBOLGG-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccccn3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccccn3)c3ccccc3Nc12 WQEWYSPDZBOLGG-UHFFFAOYSA-N 0.000 description 2
- NPDHUCSLZCFHQI-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cccnc3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cccnc3)c3ccccc3Nc12 NPDHUCSLZCFHQI-UHFFFAOYSA-N 0.000 description 2
- RVEUGLBBVDZILN-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccncc3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccncc3)c3ccccc3Nc12 RVEUGLBBVDZILN-UHFFFAOYSA-N 0.000 description 2
- OUCHLZVXGIACPT-UHFFFAOYSA-N Cn1ncc2CN(Cc3cc(O)cc(O)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(Cc3cc(O)cc(O)c3)c3ccccc3Nc12 OUCHLZVXGIACPT-UHFFFAOYSA-N 0.000 description 2
- CUBJTZIIQGLGFC-UHFFFAOYSA-N Cn1ncc2CN(c3ccccc3Nc12)S(=O)(=O)c1ccc(Cl)cc1 Chemical compound Cn1ncc2CN(c3ccccc3Nc12)S(=O)(=O)c1ccc(Cl)cc1 CUBJTZIIQGLGFC-UHFFFAOYSA-N 0.000 description 2
- AZMBGVJDCVRVCO-UHFFFAOYSA-N Cn1ncc2CN(c3ccccc3Nc12)S(=O)(=O)c1ccc(cc1)C(F)(F)F Chemical compound Cn1ncc2CN(c3ccccc3Nc12)S(=O)(=O)c1ccc(cc1)C(F)(F)F AZMBGVJDCVRVCO-UHFFFAOYSA-N 0.000 description 2
- 206010012335 Dependence Diseases 0.000 description 2
- 208000012239 Developmental disease Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 208000011688 Generalised anxiety disease Diseases 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000004098 Tetracycline Substances 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000008228 bacteriostatic water for injection Substances 0.000 description 2
- 235000013871 bee wax Nutrition 0.000 description 2
- 239000012166 beeswax Substances 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 230000001055 chewing effect Effects 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 239000010779 crude oil Substances 0.000 description 2
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 2
- 230000001627 detrimental effect Effects 0.000 description 2
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012634 fragment Substances 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 208000029364 generalized anxiety disease Diseases 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 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 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000003340 mental effect Effects 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 239000003094 microcapsule Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000012188 paraffin wax Substances 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 239000011535 reaction buffer Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 2
- 239000003775 serotonin noradrenalin reuptake inhibitor Substances 0.000 description 2
- 150000003384 small molecules Chemical class 0.000 description 2
- 230000003997 social interaction Effects 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 230000008685 targeting Effects 0.000 description 2
- 229930101283 tetracycline Natural products 0.000 description 2
- 229960002180 tetracycline Drugs 0.000 description 2
- 235000019364 tetracycline Nutrition 0.000 description 2
- 150000003522 tetracyclines Chemical class 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000004034 viscosity adjusting agent Substances 0.000 description 2
- HWPGRFRXZNLZEX-UHFFFAOYSA-N way-267,464 Chemical compound CC1=CC(C(=O)N2C3=CC=CC=C3NC=3N(C)N=CC=3C2)=CC=C1CNC(=O)N(CC1)CCN1CC1=CC(O)=CC(O)=C1 HWPGRFRXZNLZEX-UHFFFAOYSA-N 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- RMHKLKFNEPUKRK-UHFFFAOYSA-N (1,7-dimethyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)-phenylmethanone Chemical compound CN1N=CC2=C1NC1=C(N(C2)C(=O)C2=CC=CC=C2)C=C(C=C1)C RMHKLKFNEPUKRK-UHFFFAOYSA-N 0.000 description 1
- SGLYSSXNVWIEGM-UHFFFAOYSA-N (1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)-(4-phenylmethoxyphenyl)methanone Chemical compound Cn1ncc2CN(C(=O)c3ccc(OCc4ccccc4)cc3)c3ccccc3Nc12 SGLYSSXNVWIEGM-UHFFFAOYSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- YQXYQOXRCNEATG-ZAYJLJTISA-N (2s,3s,6r)-3-[[(3r)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2h-pyran-2-carboxylic acid;hydrochloride Chemical compound Cl.O1[C@H](C(O)=O)[C@@H](NC(=O)C[C@H](N)CCN(C)C(N)=N)C=C[C@@H]1N1C(=O)N=C(N)C=C1 YQXYQOXRCNEATG-ZAYJLJTISA-N 0.000 description 1
- HETXLMAPZZPCFC-UHFFFAOYSA-N (3-fluoro-4-methylphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound FC=1C=C(C=CC=1C)C(=O)N1C2=C(NC3=C(C1)C=NN3C)C=CC=C2 HETXLMAPZZPCFC-UHFFFAOYSA-N 0.000 description 1
- PNBMIFBHZLQZOH-UHFFFAOYSA-N (4-hydroxyphenyl)-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound Cn1ncc2CN(C(=O)c3ccc(O)cc3)c3ccccc3Nc12 PNBMIFBHZLQZOH-UHFFFAOYSA-N 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 description 1
- PLXLSEIPPKBORC-UHFFFAOYSA-N 1-bicyclo[2.2.2]octanyl-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepin-5-yl)methanone Chemical compound C12(CCC(CC1)CC2)C(=O)N1C2=C(NC3=C(C1)C=NN3C)C=CC=C2 PLXLSEIPPKBORC-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
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-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
- JSOVGYMVTPPEND-UHFFFAOYSA-N 16-methylheptadecyl 2,2-dimethylpropanoate Chemical compound CC(C)CCCCCCCCCCCCCCCOC(=O)C(C)(C)C JSOVGYMVTPPEND-UHFFFAOYSA-N 0.000 description 1
- ADEJACPCTOIQLO-UHFFFAOYSA-N 1h-pyrazolo[4,3-c]quinoline Chemical compound C1=NC2=CC=CC=C2C2=C1C=NN2 ADEJACPCTOIQLO-UHFFFAOYSA-N 0.000 description 1
- NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-UHFFFAOYSA-N 0.000 description 1
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 1
- MFTLQJWOEXCZHH-UHFFFAOYSA-N 2-(2-fluoroethoxy)benzoic acid Chemical class OC(=O)C1=CC=CC=C1OCCF MFTLQJWOEXCZHH-UHFFFAOYSA-N 0.000 description 1
- FLPJVCMIKUWSDR-UHFFFAOYSA-N 2-(4-formylphenoxy)acetamide Chemical compound NC(=O)COC1=CC=C(C=O)C=C1 FLPJVCMIKUWSDR-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- AMRBZKOCOOPYNY-QXMHVHEDSA-N 2-[dimethyl-[(z)-octadec-9-enyl]azaniumyl]acetate Chemical compound CCCCCCCC\C=C/CCCCCCCC[N+](C)(C)CC([O-])=O AMRBZKOCOOPYNY-QXMHVHEDSA-N 0.000 description 1
- REDSLTKMNCCQBC-UHFFFAOYSA-N 2-fluoro-5-methoxybenzoic acid Chemical class COC1=CC=C(F)C(C(O)=O)=C1 REDSLTKMNCCQBC-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- DLURHXYXQYMPLT-UHFFFAOYSA-N 2-nitro-p-toluidine Chemical compound CC1=CC=C(N)C([N+]([O-])=O)=C1 DLURHXYXQYMPLT-UHFFFAOYSA-N 0.000 description 1
- IWPZKOJSYQZABD-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Natural products COC1=CC(OC)=CC(C(O)=O)=C1 IWPZKOJSYQZABD-UHFFFAOYSA-N 0.000 description 1
- POQJHLBMLVTHAU-UHFFFAOYSA-N 3,4-Dimethylbenzaldehyde Chemical compound CC1=CC=C(C=O)C=C1C POQJHLBMLVTHAU-UHFFFAOYSA-N 0.000 description 1
- OPVAJFQBSDUNQA-UHFFFAOYSA-N 3,4-diMeC6H4COOH Natural products CC1=CC=C(C(O)=O)C=C1C OPVAJFQBSDUNQA-UHFFFAOYSA-N 0.000 description 1
- GZLPFEYTAAXJCP-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-sulfonyl chloride Chemical group CC1=NOC(C)=C1S(Cl)(=O)=O GZLPFEYTAAXJCP-UHFFFAOYSA-N 0.000 description 1
- OTFWXMFLPMUDFP-UHFFFAOYSA-N 4-[(3,5-dihydroxyphenyl)methyl]-N-[[2-methyl-4-(1-methyl-4,10-dihydropyrazolo[4,3-c][1,5]benzodiazepine-5-carbonyl)phenyl]methyl]piperazine-1-carboxamide dihydrochloride Chemical compound Cl.Cl.Cc1cc(ccc1CNC(=O)N1CCN(Cc2cc(O)cc(O)c2)CC1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 OTFWXMFLPMUDFP-UHFFFAOYSA-N 0.000 description 1
- QFMJFXFXQAFGBO-UHFFFAOYSA-N 4-methoxy-2-nitroaniline Chemical compound COC1=CC=C(N)C([N+]([O-])=O)=C1 QFMJFXFXQAFGBO-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- ORILYTVJVMAKLC-UHFFFAOYSA-N Adamantane Natural products C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 1
- 102000009027 Albumins Human genes 0.000 description 1
- 108010088751 Albumins Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 208000000044 Amnesia Diseases 0.000 description 1
- 206010002820 Antisocial behaviour Diseases 0.000 description 1
- 238000006218 Arndt-Eistert homologation reaction Methods 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- DPJPNNDAWCBEBK-UHFFFAOYSA-N CC(C)c1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound CC(C)c1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 DPJPNNDAWCBEBK-UHFFFAOYSA-N 0.000 description 1
- JSTHEPQSHREHEC-UHFFFAOYSA-N CC1CCC(CC1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound CC1CCC(CC1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 JSTHEPQSHREHEC-UHFFFAOYSA-N 0.000 description 1
- JQZGTBWRLVDISM-UHFFFAOYSA-N CCCCCCOc1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound CCCCCCOc1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 JQZGTBWRLVDISM-UHFFFAOYSA-N 0.000 description 1
- QCDZWPOBQMYSBK-UHFFFAOYSA-N CCc1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound CCc1ccc(cc1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 QCDZWPOBQMYSBK-UHFFFAOYSA-N 0.000 description 1
- ZWMMPICZLWDEGJ-UHFFFAOYSA-N COC(=O)C12CCC(CC1)(CC2)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound COC(=O)C12CCC(CC1)(CC2)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 ZWMMPICZLWDEGJ-UHFFFAOYSA-N 0.000 description 1
- JRWLBQZMCNLUOL-UHFFFAOYSA-N COc1ccc(F)c(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 Chemical compound COc1ccc(F)c(c1)C(=O)N1Cc2cnn(C)c2Nc2ccccc12 JRWLBQZMCNLUOL-UHFFFAOYSA-N 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920001661 Chitosan Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEMYAOPFKZMEAX-UHFFFAOYSA-N Cn1ncc2CN(C(=O)C3C(C)(C)C3(C)C)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)C3C(C)(C)C3(C)C)c3ccccc3Nc12 FEMYAOPFKZMEAX-UHFFFAOYSA-N 0.000 description 1
- PBGXKQVMCLFEAS-UHFFFAOYSA-N Cn1ncc2CN(C(=O)C3CC3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)C3CC3)c3ccccc3Nc12 PBGXKQVMCLFEAS-UHFFFAOYSA-N 0.000 description 1
- JPVPHUFAMLJPSB-UHFFFAOYSA-N Cn1ncc2CN(C(=O)C3CCCC3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)C3CCCC3)c3ccccc3Nc12 JPVPHUFAMLJPSB-UHFFFAOYSA-N 0.000 description 1
- RCQQEGIYKIOJNZ-UHFFFAOYSA-N Cn1ncc2CN(C(=O)C3CCCCC3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)C3CCCCC3)c3ccccc3Nc12 RCQQEGIYKIOJNZ-UHFFFAOYSA-N 0.000 description 1
- ZCMVMEBWFDVPOH-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cc(ccc3F)C(F)(F)F)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cc(ccc3F)C(F)(F)F)c3ccccc3Nc12 ZCMVMEBWFDVPOH-UHFFFAOYSA-N 0.000 description 1
- NKMUGCHJVRDNLP-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(F)cc3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(F)cc3)c3ccccc3Nc12 NKMUGCHJVRDNLP-UHFFFAOYSA-N 0.000 description 1
- COJXOOJTVCLXNP-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(OCCF)cc3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(OCCF)cc3)c3ccccc3Nc12 COJXOOJTVCLXNP-UHFFFAOYSA-N 0.000 description 1
- SCVNCOGVYQNEHN-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc(cc3)C(C)(C)C)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc(cc3)C(C)(C)C)c3ccccc3Nc12 SCVNCOGVYQNEHN-UHFFFAOYSA-N 0.000 description 1
- FQBANIKBSATHCP-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc4OCOc4c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc4OCOc4c3)c3ccccc3Nc12 FQBANIKBSATHCP-UHFFFAOYSA-N 0.000 description 1
- AZVIRNJJVKQOQG-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccc4ccccc4c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccc4ccccc4c3)c3ccccc3Nc12 AZVIRNJJVKQOQG-UHFFFAOYSA-N 0.000 description 1
- BZRLDVPASHPBRX-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cccc(OCCF)c3)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cccc(OCCF)c3)c3ccccc3Nc12 BZRLDVPASHPBRX-UHFFFAOYSA-N 0.000 description 1
- TXZIBLADPCMAIH-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cccc4ccccc34)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cccc4ccccc34)c3ccccc3Nc12 TXZIBLADPCMAIH-UHFFFAOYSA-N 0.000 description 1
- ZRNRGMACBOTQDI-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccccc3F)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccccc3F)c3ccccc3Nc12 ZRNRGMACBOTQDI-UHFFFAOYSA-N 0.000 description 1
- BRBXCVIOWOZGAG-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3ccccc3OCCF)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3ccccc3OCCF)c3ccccc3Nc12 BRBXCVIOWOZGAG-UHFFFAOYSA-N 0.000 description 1
- PJPGYFYLKBSVKF-UHFFFAOYSA-N Cn1ncc2CN(C(=O)c3cccnc3F)c3ccccc3Nc12 Chemical compound Cn1ncc2CN(C(=O)c3cccnc3F)c3ccccc3Nc12 PJPGYFYLKBSVKF-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 108010069514 Cyclic Peptides Proteins 0.000 description 1
- 102000001189 Cyclic Peptides Human genes 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- YQYJSBFKSSDGFO-UHFFFAOYSA-N Epihygromycin Natural products OC1C(O)C(C(=O)C)OC1OC(C(=C1)O)=CC=C1C=C(C)C(=O)NC1C(O)C(O)C2OCOC2C1O YQYJSBFKSSDGFO-UHFFFAOYSA-N 0.000 description 1
- 241000283073 Equus caballus Species 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
- 241000282326 Felis catus Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 108091006068 Gq proteins Proteins 0.000 description 1
- 102000052606 Gq-G11 GTP-Binding Protein alpha Subunits Human genes 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000007995 HEPES buffer Substances 0.000 description 1
- 241000208680 Hamamelis mollis Species 0.000 description 1
- 101500028587 Homo sapiens Oxytocin Proteins 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 1
- 208000029726 Neurodevelopmental disease Diseases 0.000 description 1
- 108090000189 Neuropeptides Proteins 0.000 description 1
- 102000003797 Neuropeptides Human genes 0.000 description 1
- 229940122381 Oxytocin receptor agonist Drugs 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
- 241000009328 Perro Species 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 229920002701 Polyoxyl 40 Stearate Polymers 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 229920001219 Polysorbate 40 Polymers 0.000 description 1
- 229920001214 Polysorbate 60 Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010041247 Social fear Diseases 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 208000013200 Stress disease Diseases 0.000 description 1
- 102100037187 Vasopressin V1a receptor Human genes 0.000 description 1
- 101710109831 Vasopressin V1a receptor Proteins 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
- 239000003082 abrasive agent Substances 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
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 238000009825 accumulation 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
- 239000013543 active substance Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N alpha-naphthoic acid Natural products C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 208000024823 antisocial personality disease Diseases 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000003212 astringent agent Substances 0.000 description 1
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- UIAFKZKHHVMJGS-UHFFFAOYSA-N beta-resorcylic acid Natural products OC(=O)C1=CC=C(O)C=C1O UIAFKZKHHVMJGS-UHFFFAOYSA-N 0.000 description 1
- 238000003236 bicinchoninic acid assay Methods 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 229960001631 carbomer Drugs 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 229940073669 ceteareth 20 Drugs 0.000 description 1
- 229940073642 ceteareth-30 Drugs 0.000 description 1
- 229940081733 cetearyl alcohol Drugs 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 229940074979 cetyl palmitate Drugs 0.000 description 1
- 229940119217 chamomile extract Drugs 0.000 description 1
- 235000020221 chamomile extract Nutrition 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- CEZCCHQBSQPRMU-UHFFFAOYSA-L chembl174821 Chemical compound [Na+].[Na+].COC1=CC(S([O-])(=O)=O)=C(C)C=C1N=NC1=C(O)C=CC2=CC(S([O-])(=O)=O)=CC=C12 CEZCCHQBSQPRMU-UHFFFAOYSA-L 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 230000009137 competitive binding Effects 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000013270 controlled release Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- TXWRERCHRDBNLG-UHFFFAOYSA-N cubane Chemical compound C12C3C4C1C1C4C3C12 TXWRERCHRDBNLG-UHFFFAOYSA-N 0.000 description 1
- LTLODARRUYXQKQ-UHFFFAOYSA-N cycloheptyl(4,10-dihydro-1H-pyrrolo[3,2-c][1,5]benzodiazepin-5-yl)methanone Chemical compound O=C(C1CCCCCC1)N1Cc2cc[nH]c2Nc2ccccc12 LTLODARRUYXQKQ-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002327 glycerophospholipids Chemical class 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 229940075529 glyceryl stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 229920000591 gum Polymers 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000012676 herbal extract Substances 0.000 description 1
- UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
- PXDJXZJSCPSGGI-UHFFFAOYSA-N hexadecanoic acid hexadecyl ester Natural products CCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCC PXDJXZJSCPSGGI-UHFFFAOYSA-N 0.000 description 1
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 239000011539 homogenization buffer Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
- 229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000037041 intracellular level Effects 0.000 description 1
- 238000007917 intracranial administration Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000007919 intrasynovial administration Methods 0.000 description 1
- 238000007913 intrathecal administration Methods 0.000 description 1
- 239000002563 ionic surfactant Substances 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Natural products OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose 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
- 150000002632 lipids Chemical class 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 230000029082 maternal behavior Effects 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 230000006984 memory degeneration Effects 0.000 description 1
- 208000023060 memory loss Diseases 0.000 description 1
- 230000004630 mental health Effects 0.000 description 1
- XHQZJYCNDZAGLW-UHFFFAOYSA-N meta-methoxylbenzoic acid Natural products COC1=CC=CC(C(O)=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-N 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- FJQXCDYVZAHXNS-UHFFFAOYSA-N methadone hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 FJQXCDYVZAHXNS-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 239000004200 microcrystalline wax Substances 0.000 description 1
- 235000019808 microcrystalline wax Nutrition 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- BOUCRWJEKAGKKG-UHFFFAOYSA-N n-[3-(diethylaminomethyl)-4-hydroxyphenyl]acetamide Chemical compound CCN(CC)CC1=CC(NC(C)=O)=CC=C1O BOUCRWJEKAGKKG-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
- 239000002088 nanocapsule Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Natural products OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- REIDAMBAPLIATC-UHFFFAOYSA-N p-terephthalic acid monomethyl ester Natural products COC(=O)C1=CC=C(C(O)=O)C=C1 REIDAMBAPLIATC-UHFFFAOYSA-N 0.000 description 1
- CKMXAIVXVKGGFM-UHFFFAOYSA-N para-isopropyl benzoic acid Natural products CC(C)C1=CC=C(C(O)=O)C=C1 CKMXAIVXVKGGFM-UHFFFAOYSA-N 0.000 description 1
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N para-methoxy benzoic acid Natural products COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229940100460 peg-100 stearate Drugs 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 229940049954 penicillin Drugs 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 238000011458 pharmacological treatment Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 229940081066 picolinic acid Drugs 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000729 poly(L-lysine) polymer Polymers 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010483 polyoxyethylene sorbitan monopalmitate Nutrition 0.000 description 1
- 239000000249 polyoxyethylene sorbitan monopalmitate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 229940068977 polysorbate 20 Drugs 0.000 description 1
- 229940101027 polysorbate 40 Drugs 0.000 description 1
- 229940113124 polysorbate 60 Drugs 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000019525 primary metabolic process Effects 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- WWWQQMIEYWZLAF-UHFFFAOYSA-N pyrazolo[3,4-e][1,4]diazepine Chemical compound N1=CC=NC=C2C=NN=C21 WWWQQMIEYWZLAF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000012047 saturated solution Substances 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
- 239000012896 selective serotonin reuptake inhibitor Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 230000009329 sexual behaviour Effects 0.000 description 1
- 239000002210 silicon-based material Substances 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 230000004036 social memory Effects 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 1
- 235000010378 sodium ascorbate Nutrition 0.000 description 1
- 229960005055 sodium ascorbate Drugs 0.000 description 1
- 229910001467 sodium calcium phosphate 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
- 239000001488 sodium phosphate Substances 0.000 description 1
- PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008347 soybean phospholipid Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003408 sphingolipids Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 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
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229940118846 witch hazel Drugs 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
-
- 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
- A61P25/18—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
- A61P25/30—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
- A61P27/00—Drugs for disorders of the senses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2016905126A AU2016905126A0 (en) | 2016-12-12 | Non-peptide oxytocin receptor agonists | |
| PCT/AU2017/051371 WO2018107216A1 (en) | 2016-12-12 | 2017-12-12 | Non-peptide oxytocin receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES3001195T3 true ES3001195T3 (es) | 2025-03-04 |
Family
ID=62557695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES17880082T Active ES3001195T3 (es) | 2016-12-12 | 2017-12-12 | Agonistas no peptídicos del receptor de la oxitocina |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US11491165B2 (https=) |
| EP (2) | EP4494705A3 (https=) |
| JP (3) | JP7089649B2 (https=) |
| KR (1) | KR102561721B1 (https=) |
| CN (1) | CN110248944A (https=) |
| AU (1) | AU2017377653B2 (https=) |
| BR (1) | BR112019012049A2 (https=) |
| CA (1) | CA3046809A1 (https=) |
| DK (1) | DK3551631T3 (https=) |
| ES (1) | ES3001195T3 (https=) |
| FI (1) | FI3551631T3 (https=) |
| HU (1) | HUE070078T2 (https=) |
| IL (1) | IL267276B2 (https=) |
| MX (1) | MX2019006942A (https=) |
| PL (1) | PL3551631T3 (https=) |
| PT (1) | PT3551631T (https=) |
| RU (1) | RU2019120162A (https=) |
| SI (1) | SI3551631T1 (https=) |
| WO (1) | WO2018107216A1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20220079953A1 (en) * | 2018-11-23 | 2022-03-17 | The University Of Sydney | Methods for management of weight |
| KR20220063198A (ko) * | 2019-09-06 | 2022-05-17 | 키녹시스 테라퓨틱스 피티와이 리미티드 | 아편유사제 금단의 치료 |
| JP2022548581A (ja) | 2019-09-13 | 2022-11-21 | オリゲニス ゲーエムベーハー | 例えば自己免疫疾患の処置のための、LRRK2、NUAK1および/またはTYK2キナーゼモジュレータとしての1,4-ジヒドロベンゾ[d]ピラゾロ[3,4-f][1,3]ジアゼピン誘導体および関連する化合物 |
| JP2023552485A (ja) * | 2020-12-14 | 2023-12-15 | キノシス・セラピューティクス・ピーティーワイ・リミテッド | オキシトシン受容体モジュレーター |
| AU2022240104A1 (en) * | 2021-03-18 | 2023-10-05 | Kinoxis Therapeutics Pty Ltd | Methods of treatment |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3770762A (en) * | 1972-08-29 | 1973-11-06 | Parke Davis & Co | Diazepine compounds and methods for their production |
| AR002459A1 (es) | 1995-01-17 | 1998-03-25 | American Cyanamid Co | Antagonistas de vasopresina de benzacepina triciclicos, una composicion farmaceutica que los contiene, un metodo para tratar enfermedades y unprocedimiento para su preparacion. |
| US5536718A (en) * | 1995-01-17 | 1996-07-16 | American Cyanamid Company | Tricyclic benzazepine vasopressin antagonists |
| GB0115515D0 (en) * | 2001-06-25 | 2001-08-15 | Ferring Bv | Oxytocin agonisys |
| GB0120051D0 (en) * | 2001-08-16 | 2001-10-10 | Ferring Bv | Oxytocin agonists |
| EP1449844A1 (en) * | 2003-02-14 | 2004-08-25 | Ferring B.V. | benzamide derivatives as oxytocin agonists and vasopressin antagonists |
| US7342112B2 (en) * | 2003-07-01 | 2008-03-11 | Ppg Industries Ohio, Inc. | Photochromic compounds |
| EP1512687A1 (en) * | 2003-09-05 | 2005-03-09 | Ferring B.V. | Piperazines as oxytocin agonists |
| EP1632494A1 (en) * | 2004-08-24 | 2006-03-08 | Ferring B.V. | Vasopressin v1a antagonists |
| KR100858262B1 (ko) * | 2004-10-13 | 2008-09-11 | 에프. 호프만-라 로슈 아게 | Cdk2 및 혈관신생에 대한 저해제로서 유용하고, 유방암,대장암, 폐암 및 전립선암의 치료용으로 유용한이중치환된 피라졸로벤조디아제핀 |
| CN101203516A (zh) * | 2005-04-05 | 2008-06-18 | 法马科皮亚公司 | 用于免疫抑制的嘌呤及咪唑并吡啶衍生物 |
| AU2006306547A1 (en) | 2005-10-24 | 2007-05-03 | Wyeth | Tricyclic compounds useful as oxytocin receptor agonists |
| WO2008103382A1 (en) * | 2007-02-20 | 2008-08-28 | Sergey Kozmin | Method for assembling high-purity chemical libraries, compounds suppressing acetyl coenzyme a carboxylase activities discovered by same |
| GB0903493D0 (en) * | 2009-02-27 | 2009-04-08 | Vantia Ltd | New compounds |
| US10508108B2 (en) * | 2014-12-05 | 2019-12-17 | Merck Sharp & Dohme Corp. | Tricyclic compounds as inhibitors of mutant IDH enzymes |
| PL3328864T3 (pl) * | 2015-07-06 | 2023-02-27 | Kinoxis Therapeutics Pty Ltd | Związki i kompozycje terapeutyczne do leczenia zaburzeń społecznych i zaburzeń związanych z używaniem substancji psychoaktywnych |
-
2017
- 2017-12-12 CA CA3046809A patent/CA3046809A1/en active Pending
- 2017-12-12 ES ES17880082T patent/ES3001195T3/es active Active
- 2017-12-12 PL PL17880082.7T patent/PL3551631T3/pl unknown
- 2017-12-12 KR KR1020197019977A patent/KR102561721B1/ko active Active
- 2017-12-12 IL IL267276A patent/IL267276B2/en unknown
- 2017-12-12 AU AU2017377653A patent/AU2017377653B2/en active Active
- 2017-12-12 PT PT178800827T patent/PT3551631T/pt unknown
- 2017-12-12 FI FIEP17880082.7T patent/FI3551631T3/fi active
- 2017-12-12 RU RU2019120162A patent/RU2019120162A/ru unknown
- 2017-12-12 CN CN201780085825.XA patent/CN110248944A/zh active Pending
- 2017-12-12 BR BR112019012049-1A patent/BR112019012049A2/pt active Search and Examination
- 2017-12-12 HU HUE17880082A patent/HUE070078T2/hu unknown
- 2017-12-12 JP JP2019531447A patent/JP7089649B2/ja active Active
- 2017-12-12 WO PCT/AU2017/051371 patent/WO2018107216A1/en not_active Ceased
- 2017-12-12 EP EP24212001.2A patent/EP4494705A3/en active Pending
- 2017-12-12 SI SI201731588T patent/SI3551631T1/sl unknown
- 2017-12-12 MX MX2019006942A patent/MX2019006942A/es unknown
- 2017-12-12 EP EP17880082.7A patent/EP3551631B9/en active Active
- 2017-12-12 DK DK17880082.7T patent/DK3551631T3/da active
-
2019
- 2019-06-12 US US16/439,570 patent/US11491165B2/en active Active
-
2022
- 2022-05-11 JP JP2022078250A patent/JP2022097655A/ja active Pending
- 2022-09-16 US US17/932,914 patent/US20230330103A1/en active Pending
-
2024
- 2024-06-05 JP JP2024091625A patent/JP2024107136A/ja active Pending
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES3001195T3 (es) | Agonistas no peptídicos del receptor de la oxitocina | |
| JP6382403B2 (ja) | Lsd1阻害剤としての(ヘテロ)アリールシクロプロピルアミン化合物 | |
| ES2700541T3 (es) | Octahidrociclopentapirroles, su preparación y uso | |
| JP6557674B2 (ja) | 新規クラスのミュー−オピオイド受容体アゴニスト | |
| KR20220092920A (ko) | 헬리오스의 소분자 분해제 및 사용 방법 | |
| KR102204804B1 (ko) | 디히드로피라졸 gpr40 조절제 | |
| BR112015010072B1 (pt) | Compostos, processo para a preparação dos referidos compostos, medicamento comprendendo os mesmos e seu uso relacionado | |
| JP6258867B2 (ja) | 複素環式化合物およびその使用方法 | |
| JP2017514822A (ja) | 置換された4−フェニルピペリジン、その調製及び使用 | |
| MX2013008111A (es) | Derivados de oxazina y su uso en el tratamiento de transtornos neurologicos. | |
| CN107922340B (zh) | 1,2,3,4-四氢异喹啉衍生物、其制备方法和应用 | |
| JP2007538084A (ja) | チエノピリジノン化合物及び治療方法 | |
| ES2250345T3 (es) | Derivados sustituidos de acido 1,2,3,4-tetrahidroquinolin-2-carboxilico. | |
| JP2022540332A (ja) | Bcl-2阻害剤のナノ粒子製剤 | |
| JP2018507897A (ja) | 複素環化合物およびその使用方法 | |
| US20240374737A1 (en) | Erk5 degraders and uses thereof | |
| HK40014275A (en) | Non-peptide oxytocin receptor agonists | |
| WO2026026674A1 (en) | Novel nlrp3 inflammasome inhibitors | |
| CN101534828A (zh) | A1腺苷受体的别构调节物 |