HRP20230518T1 - Heteroarilfenoksibenzamidni opioidni ligandi kapa - Google Patents
Heteroarilfenoksibenzamidni opioidni ligandi kapa Download PDFInfo
- Publication number
- HRP20230518T1 HRP20230518T1 HRP20230518TT HRP20230518T HRP20230518T1 HR P20230518 T1 HRP20230518 T1 HR P20230518T1 HR P20230518T T HRP20230518T T HR P20230518TT HR P20230518 T HRP20230518 T HR P20230518T HR P20230518 T1 HRP20230518 T1 HR P20230518T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- phenoxy
- pyrazol
- benzamide
- pyrrolidin
- Prior art date
Links
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title 2
- 239000003446 ligand Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 14
- 208000035475 disorder Diseases 0.000 claims 12
- 239000001257 hydrogen Substances 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 235000019000 fluorine Nutrition 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- DBYZPAQQFSGNQM-UHFFFAOYSA-N 3-fluoro-4-[4-[[2-(3-methoxy-1-methylpyrazol-4-yl)-4-methylpyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1C(CC(C1)C)C=1C(=NN(C=1)C)OC DBYZPAQQFSGNQM-UHFFFAOYSA-N 0.000 claims 4
- OBDLEFCGVHQDFR-NRFANRHFSA-N 4-[4-[[(2S)-2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound COC1=NN(C=C1[C@H]1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C OBDLEFCGVHQDFR-NRFANRHFSA-N 0.000 claims 4
- 206010012335 Dependence Diseases 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 208000012902 Nervous system disease Diseases 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 4
- 208000011117 substance-related disease Diseases 0.000 claims 4
- IZJXUGBMVIYBBX-UHFFFAOYSA-N 3-fluoro-4-[4-[[2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1C(CCC1)C=1C(=NN(C=1)C)OC IZJXUGBMVIYBBX-UHFFFAOYSA-N 0.000 claims 3
- OTSOROJWPFVWGJ-UHFFFAOYSA-N 4-[4-[[2-(1,3-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]-2-fluorophenoxy]benzamide Chemical compound CN1N=C(C(=C1)C1N(CCC1)CC1=CC(=C(OC2=CC=C(C(=O)N)C=C2)C=C1)F)C OTSOROJWPFVWGJ-UHFFFAOYSA-N 0.000 claims 3
- QUCWSTIZYTWCGA-UHFFFAOYSA-N 4-[4-[[2-(1,3-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]-2-hydroxybenzamide Chemical compound CN1N=C(C(=C1)C1N(CCC1)CC1=CC=C(OC2=CC(=C(C(=O)N)C=C2)O)C=C1)C QUCWSTIZYTWCGA-UHFFFAOYSA-N 0.000 claims 3
- OGMYYCWARGFVKM-UHFFFAOYSA-N 4-[4-[[2-(1,3-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide Chemical compound CN1N=C(C(=C1)C1N(CCC1)CC1=CC=C(OC2=C(C=C(C(=O)N)C=C2)F)C=C1)C OGMYYCWARGFVKM-UHFFFAOYSA-N 0.000 claims 3
- VINQQMQGIRBJBA-UHFFFAOYSA-N 4-[4-[[2-(5-methoxy-1H-pyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound COC1=NNC=C1C1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1 VINQQMQGIRBJBA-UHFFFAOYSA-N 0.000 claims 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 206010013663 drug dependence Diseases 0.000 claims 3
- 229910052731 fluorine Inorganic materials 0.000 claims 3
- 239000011737 fluorine Substances 0.000 claims 3
- FNFXSJQXJIAYOQ-UHFFFAOYSA-N 4-[4-[[2-(1,3-dimethylpyrazol-4-yl)-4-fluoropyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1C=C(C2CC(F)CN2CC2=CC=C(OC3=CC=C(C=C3)C(N)=O)C=C2)C(C)=N1 FNFXSJQXJIAYOQ-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 206010012289 Dementia Diseases 0.000 claims 2
- 206010067889 Dementia with Lewy bodies Diseases 0.000 claims 2
- 208000020401 Depressive disease Diseases 0.000 claims 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 2
- 206010020710 Hyperphagia Diseases 0.000 claims 2
- 201000002832 Lewy body dementia Diseases 0.000 claims 2
- 208000007101 Muscle Cramp Diseases 0.000 claims 2
- 208000025966 Neurological disease Diseases 0.000 claims 2
- 102000003840 Opioid Receptors Human genes 0.000 claims 2
- 108090000137 Opioid Receptors Proteins 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 238000001237 Raman spectrum Methods 0.000 claims 2
- 208000005392 Spasm Diseases 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 208000015114 central nervous system disease Diseases 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 239000010949 copper Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 235000014632 disordered eating Nutrition 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 208000024714 major depressive disease Diseases 0.000 claims 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 230000005855 radiation Effects 0.000 claims 2
- 208000012672 seasonal affective disease Diseases 0.000 claims 2
- 201000009032 substance abuse Diseases 0.000 claims 2
- 231100000736 substance abuse Toxicity 0.000 claims 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- TVPPRAOPQMQEKF-FQEVSTJZSA-N 2-hydroxy-4-[4-[[(2S)-2-(1-methylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1C=CC(=N1)[C@@H]1CCCN1CC1=CC=C(OC2=CC(O)=C(C=C2)C(N)=O)C=C1 TVPPRAOPQMQEKF-FQEVSTJZSA-N 0.000 claims 1
- LCYKHHMTZHLTSV-UHFFFAOYSA-N 2-hydroxy-4-[4-[[2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound OC1=C(C(=O)N)C=CC(=C1)OC1=CC=C(C=C1)CN1C(CCC1)C=1C(=NN(C=1)C)OC LCYKHHMTZHLTSV-UHFFFAOYSA-N 0.000 claims 1
- LPSHPNBSMYEMDL-FQEVSTJZSA-N 3-fluoro-4-[4-[[(2S)-2-(1-methylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1[C@@H](CCC1)C1=NN(C=C1)C LPSHPNBSMYEMDL-FQEVSTJZSA-N 0.000 claims 1
- YRFUMXNASHTPRW-UHFFFAOYSA-N 3-fluoro-4-[4-[[2-(1,3,5-trimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1N=C(C)C(C2CCCN2CC2=CC=C(OC3=C(F)C=C(C=C3)C(N)=O)C=C2)=C1C YRFUMXNASHTPRW-UHFFFAOYSA-N 0.000 claims 1
- XXKKFKGWJDKFRP-UHFFFAOYSA-N 3-fluoro-4-[4-[[2-(3-methyl-1,2-oxazol-5-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1C(CCC1)C1=CC(=NO1)C XXKKFKGWJDKFRP-UHFFFAOYSA-N 0.000 claims 1
- HYJLGFVLYIUNHJ-UHFFFAOYSA-N 3-fluoro-4-[4-[[2-(5-methyl-1,2-oxazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1C(CCC1)C1=NOC(=C1)C HYJLGFVLYIUNHJ-UHFFFAOYSA-N 0.000 claims 1
- JHMYMWMKWFXNSW-UHFFFAOYSA-N 3-fluoro-4-[4-[[3-(3-methoxy-1-methylpyrazol-4-yl)morpholin-4-yl]methyl]phenoxy]benzamide Chemical compound FC=1C=C(C(=O)N)C=CC=1OC1=CC=C(C=C1)CN1C(COCC1)C=1C(=NN(C=1)C)OC JHMYMWMKWFXNSW-UHFFFAOYSA-N 0.000 claims 1
- QHTDNUDQIZQUMY-UHFFFAOYSA-N 4-[2-fluoro-4-[[2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC1=C(OC2=CC=C(C(=O)N)C=C2)C=CC(=C1)CN1C(CCC1)C=1C(=NN(C=1)C)OC QHTDNUDQIZQUMY-UHFFFAOYSA-N 0.000 claims 1
- FALDMHVJQAISEM-UHFFFAOYSA-N 4-[2-fluoro-4-[[3-(3-methoxy-1-methylpyrazol-4-yl)morpholin-4-yl]methyl]phenoxy]benzamide Chemical compound FC1=C(OC2=CC=C(C(=O)N)C=C2)C=CC(=C1)CN1C(COCC1)C=1C(=NN(C=1)C)OC FALDMHVJQAISEM-UHFFFAOYSA-N 0.000 claims 1
- NMUDMWZLQKDPIC-QFIPXVFZSA-N 4-[4-[[(2S)-2-(1,3-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1N=C(C(=C1)[C@H]1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C NMUDMWZLQKDPIC-QFIPXVFZSA-N 0.000 claims 1
- SQTTVJQSZLYRHJ-FQEVSTJZSA-N 4-[4-[[(2S)-2-(2,5-dimethylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]-2-hydroxybenzamide Chemical compound CN1N=C(C=C1[C@H]1N(CCC1)CC1=CC=C(OC2=CC(=C(C(=O)N)C=C2)O)C=C1)C SQTTVJQSZLYRHJ-FQEVSTJZSA-N 0.000 claims 1
- RRRUFRKZUVECCY-FQEVSTJZSA-N 4-[4-[[(2S)-2-(2,5-dimethylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide Chemical compound CN1N=C(C=C1[C@H]1N(CCC1)CC1=CC=C(OC2=C(C=C(C(=O)N)C=C2)F)C=C1)C RRRUFRKZUVECCY-FQEVSTJZSA-N 0.000 claims 1
- XQSMXHCWHFKNBN-IBGZPJMESA-N 4-[4-[[(2S)-2-(5-methyl-1,2,4-thiadiazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CC1=NC(=NS1)[C@H]1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1 XQSMXHCWHFKNBN-IBGZPJMESA-N 0.000 claims 1
- IXMKDJZDFZJLRE-UHFFFAOYSA-N 4-[4-[[2-(1,5-dimethylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide Chemical compound CN1N=C(C=C1C)C1CCCN1CC1=CC=C(OC2=CC=C(C=C2F)C(N)=O)C=C1 IXMKDJZDFZJLRE-UHFFFAOYSA-N 0.000 claims 1
- UJVMLLWLWLEAHP-UHFFFAOYSA-N 4-[4-[[2-(1,5-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide Chemical compound CN1N=CC(=C1C)C1N(CCC1)CC1=CC=C(OC2=C(C=C(C(=O)N)C=C2)F)C=C1 UJVMLLWLWLEAHP-UHFFFAOYSA-N 0.000 claims 1
- ABHDWLWYUHDRCA-UHFFFAOYSA-N 4-[4-[[2-(1,5-dimethylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1N=CC(C2CCCN2CC2=CC=C(OC3=CC=C(C=C3)C(N)=O)C=C2)=C1C ABHDWLWYUHDRCA-UHFFFAOYSA-N 0.000 claims 1
- VKZQFVRJCMCTHK-UHFFFAOYSA-N 4-[4-[[2-(2,4-dimethylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]-3-fluorobenzamide Chemical compound CN1N=CC(C)=C1C1CCCN1CC1=CC=C(OC2=C(F)C=C(C=C2)C(N)=O)C=C1 VKZQFVRJCMCTHK-UHFFFAOYSA-N 0.000 claims 1
- MDEDOMCCHBIFAW-UHFFFAOYSA-N 4-[4-[[2-(2,5-dimethyltriazol-4-yl)pyrrolidin-1-yl]methyl]-2-fluorophenoxy]benzamide Chemical compound CN1N=C(C(=N1)C1N(CCC1)CC1=CC(=C(OC2=CC=C(C(=O)N)C=C2)C=C1)F)C MDEDOMCCHBIFAW-UHFFFAOYSA-N 0.000 claims 1
- CBRKDRSPIIQQRD-UHFFFAOYSA-N 4-[4-[[2-(2,5-dimethyltriazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CN1N=C(C(=N1)C1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C CBRKDRSPIIQQRD-UHFFFAOYSA-N 0.000 claims 1
- RFCFZDKCLQNRIJ-UHFFFAOYSA-N 4-[4-[[2-(3-methoxy-1-methylpyrazol-4-yl)piperidin-1-yl]methyl]phenoxy]benzamide Chemical compound COC1=NN(C=C1C1N(CCCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C RFCFZDKCLQNRIJ-UHFFFAOYSA-N 0.000 claims 1
- OBDLEFCGVHQDFR-UHFFFAOYSA-N 4-[4-[[2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical group COC1=NN(C=C1C1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C OBDLEFCGVHQDFR-UHFFFAOYSA-N 0.000 claims 1
- MOQZUDOEIJJUSZ-UHFFFAOYSA-N 4-[4-[[2-(3-methyl-1,2,4-thiadiazol-5-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound CC1=NSC(=N1)C1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1 MOQZUDOEIJJUSZ-UHFFFAOYSA-N 0.000 claims 1
- HHLDKQWGXRLDLQ-UHFFFAOYSA-N 4-[4-[[2-(5-methoxy-2-methylpyrazol-3-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound COC1=NN(C(=C1)C1N(CCC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C HHLDKQWGXRLDLQ-UHFFFAOYSA-N 0.000 claims 1
- SWSDUMZGZGEFJB-UHFFFAOYSA-N 4-[4-[[3-(3-methoxy-1-methylpyrazol-4-yl)morpholin-4-yl]methyl]phenoxy]benzamide Chemical compound COC1=NN(C=C1C1N(CCOC1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C SWSDUMZGZGEFJB-UHFFFAOYSA-N 0.000 claims 1
- BGOZXSIEXIYHFW-UHFFFAOYSA-N 4-[4-[[4-fluoro-2-(3-methoxy-1-methylpyrazol-4-yl)pyrrolidin-1-yl]methyl]phenoxy]benzamide Chemical compound FC1CC(N(C1)CC1=CC=C(OC2=CC=C(C(=O)N)C=C2)C=C1)C=1C(=NN(C=1)C)OC BGOZXSIEXIYHFW-UHFFFAOYSA-N 0.000 claims 1
- 208000008811 Agoraphobia Diseases 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000029197 Amphetamine-Related disease Diseases 0.000 claims 1
- 102000014461 Ataxins Human genes 0.000 claims 1
- 108010078286 Ataxins Proteins 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 238000012935 Averaging Methods 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 206010006550 Bulimia nervosa Diseases 0.000 claims 1
- 244000025254 Cannabis sativa Species 0.000 claims 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 claims 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 206010008748 Chorea Diseases 0.000 claims 1
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 208000020406 Creutzfeldt Jacob disease Diseases 0.000 claims 1
- 208000003407 Creutzfeldt-Jakob Syndrome Diseases 0.000 claims 1
- 208000010859 Creutzfeldt-Jakob disease Diseases 0.000 claims 1
- 206010012218 Delirium Diseases 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 208000007590 Disorders of Excessive Somnolence Diseases 0.000 claims 1
- 208000026331 Disruptive, Impulse Control, and Conduct disease Diseases 0.000 claims 1
- 208000012661 Dyskinesia Diseases 0.000 claims 1
- 208000014094 Dystonic disease Diseases 0.000 claims 1
- 208000030814 Eating disease Diseases 0.000 claims 1
- 238000005079 FT-Raman Methods 0.000 claims 1
- 208000010235 Food Addiction Diseases 0.000 claims 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims 1
- 201000011240 Frontotemporal dementia Diseases 0.000 claims 1
- 208000011688 Generalised anxiety disease Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 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 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000030990 Impulse-control disease Diseases 0.000 claims 1
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 1
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 1
- 206010026749 Mania Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- 208000010428 Muscle Weakness Diseases 0.000 claims 1
- 206010028372 Muscular weakness Diseases 0.000 claims 1
- 208000002033 Myoclonus Diseases 0.000 claims 1
- 208000027626 Neurocognitive disease Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 1
- 208000026251 Opioid-Related disease Diseases 0.000 claims 1
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims 1
- 208000006199 Parasomnias Diseases 0.000 claims 1
- 206010034158 Pathological gambling Diseases 0.000 claims 1
- 201000009916 Postpartum depression Diseases 0.000 claims 1
- 208000027030 Premenstrual dysphoric disease Diseases 0.000 claims 1
- 206010036618 Premenstrual syndrome Diseases 0.000 claims 1
- 208000029808 Psychomotor disease Diseases 0.000 claims 1
- 238000001069 Raman spectroscopy Methods 0.000 claims 1
- 208000020186 Schizophreniform disease Diseases 0.000 claims 1
- 201000001880 Sexual dysfunction Diseases 0.000 claims 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims 1
- 206010041250 Social phobia Diseases 0.000 claims 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 206010043118 Tardive Dyskinesia Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 208000016620 Tourette disease Diseases 0.000 claims 1
- 208000031674 Traumatic Acute Stress disease Diseases 0.000 claims 1
- 206010044565 Tremor Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 206010048010 Withdrawal syndrome Diseases 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 claims 1
- 208000026345 acute stress disease Diseases 0.000 claims 1
- 201000007930 alcohol dependence Diseases 0.000 claims 1
- 208000022531 anorexia Diseases 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 208000029560 autism spectrum disease Diseases 0.000 claims 1
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims 1
- 230000003542 behavioural effect Effects 0.000 claims 1
- 208000028683 bipolar I disease Diseases 0.000 claims 1
- 208000022257 bipolar II disease Diseases 0.000 claims 1
- 229930003827 cannabinoid Natural products 0.000 claims 1
- 239000003557 cannabinoid Substances 0.000 claims 1
- 208000012601 choreatic disease Diseases 0.000 claims 1
- 201000006145 cocaine dependence Diseases 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 206010061428 decreased appetite Diseases 0.000 claims 1
- 229960002069 diamorphine Drugs 0.000 claims 1
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 208000010118 dystonia Diseases 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 claims 1
- 239000002360 explosive Substances 0.000 claims 1
- 208000029364 generalized anxiety disease Diseases 0.000 claims 1
- 229910052732 germanium Inorganic materials 0.000 claims 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims 1
- LLPOLZWFYMWNKH-CMKMFDCUSA-N hydrocodone Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC LLPOLZWFYMWNKH-CMKMFDCUSA-N 0.000 claims 1
- 229960000240 hydrocodone Drugs 0.000 claims 1
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims 1
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims 1
- 229960001410 hydromorphone Drugs 0.000 claims 1
- 206010020765 hypersomnia Diseases 0.000 claims 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims 1
- 208000014674 injury Diseases 0.000 claims 1
- 206010022437 insomnia Diseases 0.000 claims 1
- 229960004502 levodopa Drugs 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 208000029790 metamphetamine dependence Diseases 0.000 claims 1
- 208000027061 mild cognitive impairment Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 235000020830 overeating Nutrition 0.000 claims 1
- 229960002085 oxycodone Drugs 0.000 claims 1
- 208000019906 panic disease Diseases 0.000 claims 1
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 208000028173 post-traumatic stress disease Diseases 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 206010036596 premature ejaculation Diseases 0.000 claims 1
- 230000033764 rhythmic process Effects 0.000 claims 1
- 208000022610 schizoaffective disease Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 231100000872 sexual dysfunction Toxicity 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 238000000371 solid-state nuclear magnetic resonance spectroscopy Methods 0.000 claims 1
- 238000001228 spectrum Methods 0.000 claims 1
- 230000035882 stress Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- LLPOLZWFYMWNKH-UHFFFAOYSA-N trans-dihydrocodeinone Natural products C1C(N(CCC234)C)C2CCC(=O)C3OC2=C4C1=CC=C2OC LLPOLZWFYMWNKH-UHFFFAOYSA-N 0.000 claims 1
- 230000008733 trauma Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662426980P | 2016-11-28 | 2016-11-28 | |
| US201762576435P | 2017-10-24 | 2017-10-24 | |
| US201762585016P | 2017-11-13 | 2017-11-13 | |
| PCT/IB2017/057418 WO2018096510A1 (en) | 2016-11-28 | 2017-11-27 | Heteroarylphenoxy benzamide kappa opioid ligands |
| EP17818281.2A EP3544972B8 (en) | 2016-11-28 | 2017-11-27 | Heteroarylphenoxy benzamide kappa opioid ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20230518T1 true HRP20230518T1 (hr) | 2023-08-04 |
Family
ID=60782279
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20230518TT HRP20230518T1 (hr) | 2016-11-28 | 2017-11-27 | Heteroarilfenoksibenzamidni opioidni ligandi kapa |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US10316021B2 (enExample) |
| EP (1) | EP3544972B8 (enExample) |
| JP (1) | JP7051853B2 (enExample) |
| CN (1) | CN110234638B (enExample) |
| AU (1) | AU2017365123B2 (enExample) |
| DK (1) | DK3544972T3 (enExample) |
| ES (1) | ES2947293T3 (enExample) |
| FI (1) | FI3544972T3 (enExample) |
| HR (1) | HRP20230518T1 (enExample) |
| HU (1) | HUE061945T2 (enExample) |
| IL (1) | IL266962B (enExample) |
| MX (1) | MX389806B (enExample) |
| PH (1) | PH12019501172A1 (enExample) |
| PL (1) | PL3544972T3 (enExample) |
| PT (1) | PT3544972T (enExample) |
| RS (1) | RS64258B1 (enExample) |
| TW (1) | TWI720272B (enExample) |
| WO (1) | WO2018096510A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3585485A2 (en) * | 2017-02-24 | 2020-01-01 | Xeniopro GmbH | Aromatic compounds which enhance notch signaling, for use in therapy |
| WO2018154118A2 (en) * | 2017-02-24 | 2018-08-30 | Reinmueller Viktoria | Novel aromatic compounds |
| US11266627B1 (en) | 2021-05-04 | 2022-03-08 | Janssen Pharmaceuticals, Inc. | Compositions and methods for the treatment of depression |
| CN111233768B (zh) * | 2020-03-18 | 2021-08-03 | 徐州圣元化工有限公司 | 一种3-(二氟甲基)-1-甲基-1h-吡唑-4-羧酸乙酯的制备方法 |
| AU2021253796B2 (en) * | 2020-04-05 | 2023-06-01 | Pfizer Inc. | Compounds and methods for the treatment of COVID-19 |
| US12161622B2 (en) | 2021-05-04 | 2024-12-10 | Janssen Pharmaceuticals, Inc. | Compositions and methods for the treatment of depression |
| CN119156210A (zh) * | 2022-03-07 | 2024-12-17 | 杨森制药公司 | 纯形式的结晶阿替卡普兰 |
| WO2023170550A1 (en) | 2022-03-07 | 2023-09-14 | Janssen Pharmaceuticals, Inc. | Polymorph forms of aticaprant for use in treating major depressive disorder |
| TW202400135A (zh) | 2022-03-07 | 2024-01-01 | 美商健生醫藥公司 | 包含阿替卡普蘭之組成物 |
| AR130742A1 (es) * | 2022-10-12 | 2025-01-15 | Adama Makhteshim Ltd | Proceso para la preparación de derivados de aminopiridazina |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
| KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
| GB9518953D0 (en) | 1995-09-15 | 1995-11-15 | Pfizer Ltd | Pharmaceutical formulations |
| WO2000035298A1 (en) | 1996-11-27 | 2000-06-22 | Wm. Wrigley Jr. Company | Chewing gum containing medicament active agents |
| GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
| WO2000017162A1 (en) | 1998-09-21 | 2000-03-30 | Takeda Chemical Industries, Ltd. | Novel thiol derivatives, process for producing the same and utilization thereof |
| JP2000159747A (ja) | 1998-09-21 | 2000-06-13 | Takeda Chem Ind Ltd | 新規チオ―ル誘導体、その製造法および用途 |
| IT1303737B1 (it) | 1998-11-11 | 2001-02-23 | Smithkline Beecham Spa | Derivati fenilpiperidinici procedimento per la loro preparazione eloro uso come ligandi del recettore orl-1. |
| MY140236A (en) | 2002-09-19 | 2009-12-31 | Lilly Co Eli | Diarylether compounds useful as opioid receptor antagonists |
| US7365209B2 (en) | 2003-02-11 | 2008-04-29 | Pharmacopeia, Inc. | Nitrogen heterocycle biaryls for osteoporosis and other diseases |
| ATE406360T1 (de) | 2003-03-07 | 2008-09-15 | Lilly Co Eli | Antagonisten der opioidrezeptoren |
| WO2004080966A1 (ja) | 2003-03-14 | 2004-09-23 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| RU2416608C2 (ru) | 2004-08-06 | 2011-04-20 | Оцука Фармасьютикал Ко., Лтд. | Ароматическое соединение |
| JPWO2006088079A1 (ja) | 2005-02-18 | 2008-07-03 | 日本曹達株式会社 | 有機無機複合体 |
| WO2007105637A1 (ja) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | 含窒素複素環誘導体およびそれらを有効成分とする薬剤 |
| DE502007002185D1 (de) | 2006-04-04 | 2010-01-14 | Emodys Gmbh | Verwendung von zusammensetzungen enthaltend kappa-opioidrezeptor-antagonisten zur behandlung von dissoziativen störungen |
| EA017484B1 (ru) | 2008-01-22 | 2012-12-28 | Эли Лилли Энд Компани | Селективный антагонист опиоидных рецепторов каппа |
| EP2257536A4 (en) | 2008-02-14 | 2011-03-23 | Amira Pharmaceuticals Inc | CYCLIC DIARYL ETHERS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS |
| CR11559A (es) | 2008-03-25 | 2010-10-20 | Lilly Co Eli | Antagonista del receptor opioide selectivo kappa |
| US8048895B2 (en) | 2008-04-18 | 2011-11-01 | Research Triangle Institute | Kappa opioid receptor ligands |
| NZ603525A (en) | 2008-06-27 | 2015-02-27 | Celgene Avilomics Res Inc | Pyrimidine based compound and uses thereof |
| EP2379524A1 (en) | 2008-12-18 | 2011-10-26 | Boehringer Ingelheim International GmbH | Serotonin 5-ht2b receptor inhibitors |
| HN2010001319A (es) | 2009-01-26 | 2013-01-15 | Lilly Co Eli | Antagonista del receptor opioide selectivo kappa |
| WO2013059648A1 (en) | 2011-10-21 | 2013-04-25 | Neurotherapeutics Pharma, Inc. | 2,3,5 trisubstituted aryl and heteroaryl amino derivatives, compositions, and methods of use |
| JP2015531382A (ja) | 2012-10-02 | 2015-11-02 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | ピロリジン |
| WO2015109080A1 (en) | 2014-01-15 | 2015-07-23 | Research Triangle Institute | Kappa-opioid receptor selective opioid receptor antagonists |
| WO2016086149A1 (en) | 2014-11-26 | 2016-06-02 | University Of Kansas | Antagonists of the kappa opioid receptor |
-
2017
- 2017-11-22 US US15/820,679 patent/US10316021B2/en active Active
- 2017-11-27 JP JP2019528746A patent/JP7051853B2/ja active Active
- 2017-11-27 DK DK17818281.2T patent/DK3544972T3/da active
- 2017-11-27 ES ES17818281T patent/ES2947293T3/es active Active
- 2017-11-27 FI FIEP17818281.2T patent/FI3544972T3/fi active
- 2017-11-27 MX MX2019006220A patent/MX389806B/es unknown
- 2017-11-27 HR HRP20230518TT patent/HRP20230518T1/hr unknown
- 2017-11-27 HU HUE17818281A patent/HUE061945T2/hu unknown
- 2017-11-27 RS RS20230453A patent/RS64258B1/sr unknown
- 2017-11-27 TW TW106141134A patent/TWI720272B/zh active
- 2017-11-27 PL PL17818281.2T patent/PL3544972T3/pl unknown
- 2017-11-27 WO PCT/IB2017/057418 patent/WO2018096510A1/en not_active Ceased
- 2017-11-27 CN CN201780084763.0A patent/CN110234638B/zh active Active
- 2017-11-27 EP EP17818281.2A patent/EP3544972B8/en active Active
- 2017-11-27 PT PT178182812T patent/PT3544972T/pt unknown
- 2017-11-27 AU AU2017365123A patent/AU2017365123B2/en active Active
-
2019
- 2019-05-28 PH PH12019501172A patent/PH12019501172A1/en unknown
- 2019-05-28 IL IL266962A patent/IL266962B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL3544972T3 (pl) | 2023-07-24 |
| CN110234638A (zh) | 2019-09-13 |
| ES2947293T3 (es) | 2023-08-04 |
| PT3544972T (pt) | 2023-06-20 |
| JP2019535799A (ja) | 2019-12-12 |
| RS64258B1 (sr) | 2023-07-31 |
| HUE061945T2 (hu) | 2023-09-28 |
| PH12019501172A1 (en) | 2019-12-11 |
| NZ754862A (en) | 2024-11-29 |
| EP3544972A1 (en) | 2019-10-02 |
| TW201831460A (zh) | 2018-09-01 |
| DK3544972T3 (da) | 2023-05-30 |
| AU2017365123B2 (en) | 2022-02-17 |
| AU2017365123A1 (en) | 2019-07-11 |
| IL266962A (en) | 2019-07-31 |
| EP3544972B8 (en) | 2023-06-07 |
| FI3544972T3 (fi) | 2023-06-02 |
| JP7051853B2 (ja) | 2022-04-11 |
| EP3544972B1 (en) | 2023-04-26 |
| WO2018096510A1 (en) | 2018-05-31 |
| CN110234638B (zh) | 2022-10-21 |
| IL266962B (en) | 2022-02-01 |
| US20180148432A1 (en) | 2018-05-31 |
| MX2019006220A (es) | 2019-10-07 |
| CA3045242A1 (en) | 2018-05-31 |
| MX389806B (es) | 2025-03-20 |
| US10316021B2 (en) | 2019-06-11 |
| TWI720272B (zh) | 2021-03-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI3544972T3 (fi) | Heteroaryylifenoksibentsamidi-kappa-opioidiligandeja | |
| AU2019230209B2 (en) | Amino acid compounds and methods of use | |
| JP7579805B2 (ja) | アミノ酸化合物の剤形およびレジメン | |
| ES2342675T3 (es) | Ligandos del receptor alfa-7 nicotinico contra enfermedades relacionadas con el snc. | |
| TW202126643A (zh) | 雜環化合物 | |
| RU2008139481A (ru) | Новые 1,4-диаза-бицикло[3.2.2]нонил-оксадиазолильные производные и их медицинское применение | |
| JP5993875B2 (ja) | 縮合アミノジヒドロチアジン誘導体の合成に有用な方法および化合物 | |
| UA128787C2 (uk) | Інгібітори каналів з транзиторним рецепторним потенціалом на основі оксадіазолів | |
| WO2018093946A1 (en) | Magl inhibitors | |
| RU2003130268A (ru) | Производные 4,5-дигидро-1h-пиразола, обладающие сильной cb1-антагонистической активностью | |
| CA3113226A1 (en) | Antibacterial compounds | |
| JP2022153568A (ja) | 化合物、組成物および方法 | |
| WO2019004114A1 (ja) | フロー合成によるジアミン誘導体の製造方法 | |
| IL281634B1 (en) | N-substituted-dioxocyclobutenylamino-3-hydroxy-picolinamides useful as ccr6 inhibitors | |
| JP2023540506A (ja) | 新規の塩、結晶および共結晶 | |
| JP2020520925A (ja) | 化合物、組成物および方法 | |
| JP2023015178A (ja) | インドリノベンゾジアゼピン誘導体の調製方法 | |
| KR102588109B1 (ko) | 암 치료에 유용한 1-(사이클로) 알킬 피리딘-2-온의 트리사이클릭 융합 유도체 | |
| RU2007106970A (ru) | Новые хромен-2-оновые производные и их применение в качестве ингибиторов обратного захвата моноаминовых нейромедиаторов | |
| ES2256506T3 (es) | Agonistas triciclicos del receptor crf. | |
| JP6814470B2 (ja) | モルヒナン誘導体 | |
| JP2026504095A (ja) | ピラゾロキナゾリン類化合物の立体異性体、重水素化誘導体及びその用途 | |
| DE69432259T2 (de) | Verfahren zur herstellung eines oxiranes aziridins oder cyclopropans | |
| ES2313358T3 (es) | Derivados de imidazol tetrasustituidos como moduladores del receptor cannabinoide cb1 con una elevada selectividad de subtipo por el receptor cb1/cb2. | |
| CN108349908B (zh) | 一种取代的苯并咪唑酮化合物及包含该化合物的组合物 |