NO319835B1 - Forbindelser med innvirkning pa muskarinreseptorer, anvendelser derav og farmasoytiske sammensetninger som innbefatter slike. - Google Patents
Forbindelser med innvirkning pa muskarinreseptorer, anvendelser derav og farmasoytiske sammensetninger som innbefatter slike. Download PDFInfo
- Publication number
- NO319835B1 NO319835B1 NO20004912A NO20004912A NO319835B1 NO 319835 B1 NO319835 B1 NO 319835B1 NO 20004912 A NO20004912 A NO 20004912A NO 20004912 A NO20004912 A NO 20004912A NO 319835 B1 NO319835 B1 NO 319835B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- compound
- butyl
- compound according
- oxo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 129
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 title claims description 31
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 title claims description 31
- 230000000694 effects Effects 0.000 title claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 239000000203 mixture Substances 0.000 claims description 40
- 102000005962 receptors Human genes 0.000 claims description 39
- 108020003175 receptors Proteins 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 201000010099 disease Diseases 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 11
- 230000004410 intraocular pressure Effects 0.000 claims description 11
- -1 o-methylphenyl Chemical group 0.000 claims description 11
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 claims description 9
- 229960004373 acetylcholine Drugs 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 208000024891 symptom Diseases 0.000 claims description 8
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 7
- 208000028698 Cognitive impairment Diseases 0.000 claims description 6
- 208000010877 cognitive disease Diseases 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000003149 muscarinic antagonist Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 206010012289 Dementia Diseases 0.000 claims description 4
- 208000010412 Glaucoma Diseases 0.000 claims description 4
- 230000007000 age related cognitive decline Effects 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000000472 muscarinic agonist Substances 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 230000001270 agonistic effect Effects 0.000 claims description 2
- 229940121743 Muscarinic receptor agonist Drugs 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000001207 fluorophenyl group Chemical group 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 73
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 54
- 239000012074 organic phase Substances 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 210000004027 cell Anatomy 0.000 description 23
- 239000012043 crude product Substances 0.000 description 21
- 239000003480 eluent Substances 0.000 description 21
- 239000000725 suspension Substances 0.000 description 21
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 18
- 239000012298 atmosphere Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
- 238000000605 extraction Methods 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- 239000000872 buffer Substances 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 14
- 239000011777 magnesium Substances 0.000 description 13
- 230000003551 muscarinic effect Effects 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012267 brine Substances 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 11
- 208000024827 Alzheimer disease Diseases 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 229940079593 drug Drugs 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000005557 antagonist Substances 0.000 description 8
- 210000004556 brain Anatomy 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 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 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002609 medium Substances 0.000 description 7
- 238000002953 preparative HPLC Methods 0.000 description 7
- 238000012216 screening Methods 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 239000000556 agonist Substances 0.000 description 6
- 244000309466 calf Species 0.000 description 6
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 6
- 229960004484 carbachol Drugs 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- RINOYHWVBUKAQE-UHFFFAOYSA-N 1-iodo-2-methylbenzene Chemical compound CC1=CC=CC=C1I RINOYHWVBUKAQE-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229930182555 Penicillin Natural products 0.000 description 5
- 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 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000003920 cognitive function Effects 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 230000002496 gastric effect Effects 0.000 description 5
- 229940049954 penicillin Drugs 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 230000000638 stimulation Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229960001685 tacrine Drugs 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CQPGDDAKTTWVDD-UHFFFAOYSA-N 4-bromobutanenitrile Chemical compound BrCCCC#N CQPGDDAKTTWVDD-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 230000002411 adverse Effects 0.000 description 4
- HJJPJSXJAXAIPN-UHFFFAOYSA-N arecoline Chemical compound COC(=O)C1=CCCN(C)C1 HJJPJSXJAXAIPN-UHFFFAOYSA-N 0.000 description 4
- 210000001320 hippocampus Anatomy 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 239000006187 pill Substances 0.000 description 4
- 239000000651 prodrug Substances 0.000 description 4
- 229940002612 prodrug Drugs 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- 229960005322 streptomycin Drugs 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- LAPWDCHUQSJIRB-UHFFFAOYSA-N 1-iodo-2-phenylmethoxybenzene Chemical compound IC1=CC=CC=C1OCC1=CC=CC=C1 LAPWDCHUQSJIRB-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 210000003169 central nervous system Anatomy 0.000 description 3
- 210000003710 cerebral cortex Anatomy 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 210000002569 neuron Anatomy 0.000 description 3
- 230000002093 peripheral effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- NDNUANOUGZGEPO-UHFFFAOYSA-N (s)-2-propylpiperidine Chemical compound CCCC1CCCCN1 NDNUANOUGZGEPO-UHFFFAOYSA-N 0.000 description 2
- HVRUGFJYCAFAAN-UHFFFAOYSA-N 1-bromo-2-ethylbenzene Chemical compound CCC1=CC=CC=C1Br HVRUGFJYCAFAAN-UHFFFAOYSA-N 0.000 description 2
- HQDNDPUCYICAHZ-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2-phenylmethoxyphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 HQDNDPUCYICAHZ-UHFFFAOYSA-N 0.000 description 2
- KKYBXEIOWOSNHO-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)butanenitrile Chemical compound CCCCC1CCN(CCCC#N)CC1 KKYBXEIOWOSNHO-UHFFFAOYSA-N 0.000 description 2
- 102100022738 5-hydroxytryptamine receptor 1A Human genes 0.000 description 2
- 101710138638 5-hydroxytryptamine receptor 1A Proteins 0.000 description 2
- 102100036321 5-hydroxytryptamine receptor 2A Human genes 0.000 description 2
- 101710138091 5-hydroxytryptamine receptor 2A Proteins 0.000 description 2
- 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 2
- 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 2
- 102000012440 Acetylcholinesterase Human genes 0.000 description 2
- 108010022752 Acetylcholinesterase Proteins 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 206010011968 Decreased immune responsiveness Diseases 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 108010008409 Muscarinic M5 Receptor Proteins 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 208000001871 Tachycardia Diseases 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- 102000004142 Trypsin Human genes 0.000 description 2
- 108090000631 Trypsin Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 229940022698 acetylcholinesterase Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000002152 alkylating effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 150000001502 aryl halides Chemical class 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000036471 bradycardia Effects 0.000 description 2
- 208000006218 bradycardia Diseases 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 239000007975 buffered saline Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 238000006555 catalytic reaction Methods 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000001713 cholinergic effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000007370 cognitive improvement Effects 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 230000003111 delayed effect Effects 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 208000037765 diseases and disorders Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- ADEBPBSSDYVVLD-UHFFFAOYSA-N donepezil Chemical compound O=C1C=2C=C(OC)C(OC)=CC=2CC1CC(CC1)CCN1CC1=CC=CC=C1 ADEBPBSSDYVVLD-UHFFFAOYSA-N 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 239000012039 electrophile Substances 0.000 description 2
- 239000012055 enteric layer Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000314 lubricant 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000012730 sustained-release form Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 230000006794 tachycardia Effects 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 239000012588 trypsin Substances 0.000 description 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- CMIBUZBMZCBCAT-HZPDHXFCSA-N (2r,3r)-2,3-bis[(4-methylbenzoyl)oxy]butanedioic acid Chemical compound C1=CC(C)=CC=C1C(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(=O)C1=CC=C(C)C=C1 CMIBUZBMZCBCAT-HZPDHXFCSA-N 0.000 description 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HDPXEBDNEDLBGZ-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(2-propylpiperidin-1-yl)butan-1-one Chemical compound CCCC1CCCCN1CCCC(=O)C1=CC=CC=C1C HDPXEBDNEDLBGZ-UHFFFAOYSA-N 0.000 description 1
- BBVKMUIEPLHMRV-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-methylpiperazin-1-yl)butan-1-one Chemical compound C1CN(C)CCN1CCCC(=O)C1=CC=CC=C1C BBVKMUIEPLHMRV-UHFFFAOYSA-N 0.000 description 1
- NSQIRMKHQBNNBW-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-methylpiperidin-1-yl)butan-1-one Chemical compound C1CC(C)CCN1CCCC(=O)C1=CC=CC=C1C NSQIRMKHQBNNBW-UHFFFAOYSA-N 0.000 description 1
- PTQZZOHGKVJWCQ-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-phenylpiperazin-1-yl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCN(C=2C=CC=CC=2)CC1 PTQZZOHGKVJWCQ-UHFFFAOYSA-N 0.000 description 1
- ORTMSJFXZKVCPW-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-piperidin-1-ylpiperidin-1-yl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCC(N2CCCCC2)CC1 ORTMSJFXZKVCPW-UHFFFAOYSA-N 0.000 description 1
- VZSIPVQQXINEHP-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-propoxy-4-propylpiperidin-1-yl)butan-1-one Chemical compound C1CC(OCCC)(CCC)CCN1CCCC(=O)C1=CC=CC=C1C VZSIPVQQXINEHP-UHFFFAOYSA-N 0.000 description 1
- YACFKGYLJPITOM-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-propoxypiperidin-1-yl)butan-1-one Chemical compound C1CC(OCCC)CCN1CCCC(=O)C1=CC=CC=C1C YACFKGYLJPITOM-UHFFFAOYSA-N 0.000 description 1
- YRELRKHMGKHTBJ-UHFFFAOYSA-N 1-(2-methylphenyl)-4-(4-propylpiperazin-1-yl)butan-1-one Chemical compound C1CN(CCC)CCN1CCCC(=O)C1=CC=CC=C1C YRELRKHMGKHTBJ-UHFFFAOYSA-N 0.000 description 1
- GXIAWAAFIYKHFR-UHFFFAOYSA-N 1-(2-methylphenyl)-4-[4-(propoxymethyl)piperidin-1-yl]butan-1-one Chemical compound C1CC(COCCC)CCN1CCCC(=O)C1=CC=CC=C1C GXIAWAAFIYKHFR-UHFFFAOYSA-N 0.000 description 1
- RSTSINHJHKSVDH-UHFFFAOYSA-N 1-(2-methylphenyl)-4-pyrrolidin-1-ylbutan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCCC1 RSTSINHJHKSVDH-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- FNDJPBCXMYYKSE-UHFFFAOYSA-N 1-benzyl-4-butylidenepiperidine Chemical compound C1CC(=CCCC)CCN1CC1=CC=CC=C1 FNDJPBCXMYYKSE-UHFFFAOYSA-N 0.000 description 1
- SJZKULRDWHPHGG-UHFFFAOYSA-N 1-benzylpiperidin-4-one Chemical compound C1CC(=O)CCN1CC1=CC=CC=C1 SJZKULRDWHPHGG-UHFFFAOYSA-N 0.000 description 1
- YKSVXVKIYYQWBB-UHFFFAOYSA-N 1-butylpiperazine Chemical compound CCCCN1CCNCC1 YKSVXVKIYYQWBB-UHFFFAOYSA-N 0.000 description 1
- JUJREUXKABNEFA-UHFFFAOYSA-N 1-ethoxy-2-iodobenzene Chemical compound CCOC1=CC=CC=C1I JUJREUXKABNEFA-UHFFFAOYSA-N 0.000 description 1
- DANMWBNOPFBJSZ-UHFFFAOYSA-N 1-iodo-2,3-dimethylbenzene Chemical compound CC1=CC=CC(I)=C1C DANMWBNOPFBJSZ-UHFFFAOYSA-N 0.000 description 1
- BUNKQJAMHYKQIM-UHFFFAOYSA-N 1-iodo-2,4-dimethylbenzene Chemical compound CC1=CC=C(I)C(C)=C1 BUNKQJAMHYKQIM-UHFFFAOYSA-N 0.000 description 1
- UNLSSSIQXFBAQU-UHFFFAOYSA-N 1-iodo-2-(methoxymethyl)benzene Chemical compound COCC1=CC=CC=C1I UNLSSSIQXFBAQU-UHFFFAOYSA-N 0.000 description 1
- DVQWNQBEUKXONL-UHFFFAOYSA-N 1-iodo-2-methoxybenzene Chemical compound COC1=CC=CC=C1I DVQWNQBEUKXONL-UHFFFAOYSA-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
- DLFBVCLLSPSHCA-UHFFFAOYSA-N 2-(4-benzylpiperazin-1-yl)-1-(2-methylphenyl)ethanone Chemical compound CC1=CC=CC=C1C(=O)CN1CCN(CC=2C=CC=CC=2)CC1 DLFBVCLLSPSHCA-UHFFFAOYSA-N 0.000 description 1
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
- KQDJTBPASNJQFQ-UHFFFAOYSA-N 2-iodophenol Chemical compound OC1=CC=CC=C1I KQDJTBPASNJQFQ-UHFFFAOYSA-N 0.000 description 1
- AGORNAVFAMJFDX-UHFFFAOYSA-N 3-[(4-butylpiperidin-1-yl)methyl]-1-(2-methylphenyl)hexan-1-one Chemical compound C1CC(CCCC)CCN1CC(CCC)CC(=O)C1=CC=CC=C1C AGORNAVFAMJFDX-UHFFFAOYSA-N 0.000 description 1
- NWOBWLHZNBIKRH-UHFFFAOYSA-N 3-[(4-butylpiperidin-1-yl)methyl]-1-(2-methylphenyl)pentan-1-one Chemical compound C1CC(CCCC)CCN1CC(CC)CC(=O)C1=CC=CC=C1C NWOBWLHZNBIKRH-UHFFFAOYSA-N 0.000 description 1
- WHZJECWQINOKSC-UHFFFAOYSA-N 3-[(4-butylpiperidin-1-yl)methyl]-3-ethyl-1-(2-methylphenyl)pentan-1-one Chemical compound C1CC(CCCC)CCN1CC(CC)(CC)CC(=O)C1=CC=CC=C1C WHZJECWQINOKSC-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-M 3-carboxynaphthalen-2-olate Chemical compound C1=CC=C2C=C(C([O-])=O)C(O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-M 0.000 description 1
- PRQCJPWGCYRMQC-UHFFFAOYSA-N 4-(2,3-dihydroindol-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1C2=CC=CC=C2CC1 PRQCJPWGCYRMQC-UHFFFAOYSA-N 0.000 description 1
- BXNPLRLLZJGIIQ-UHFFFAOYSA-N 4-(2-ethylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound CCC1CCCCN1CCCC(=O)C1=CC=CC=C1C BXNPLRLLZJGIIQ-UHFFFAOYSA-N 0.000 description 1
- GSNZLQKOEZWAFU-UHFFFAOYSA-N 4-(2-propylpiperidin-1-yl)butanenitrile Chemical compound CCCC1CCCCN1CCCC#N GSNZLQKOEZWAFU-UHFFFAOYSA-N 0.000 description 1
- WFTHFMKWIGJXNV-UHFFFAOYSA-N 4-(3,5-dimethylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1C(C)CC(C)CN1CCCC(=O)C1=CC=CC=C1C WFTHFMKWIGJXNV-UHFFFAOYSA-N 0.000 description 1
- XJGZPCDUDPGABB-UHFFFAOYSA-N 4-(3,5-dimethylpiperidin-1-yl)-1-(4-fluoro-2-methylphenyl)butan-1-one Chemical compound C1C(C)CC(C)CN1CCCC(=O)C1=CC=C(F)C=C1C XJGZPCDUDPGABB-UHFFFAOYSA-N 0.000 description 1
- IJUMGEPXHIJRAR-UHFFFAOYSA-N 4-(4-benzylpiperazin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCN(CC=2C=CC=CC=2)CC1 IJUMGEPXHIJRAR-UHFFFAOYSA-N 0.000 description 1
- KVHJLUKJQYDCCZ-UHFFFAOYSA-N 4-(4-benzylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCC(CC=2C=CC=CC=2)CC1 KVHJLUKJQYDCCZ-UHFFFAOYSA-N 0.000 description 1
- FIYXCIBUASFFNF-UHFFFAOYSA-N 4-(4-butoxy-4-butylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OCCCC)(CCCC)CCN1CCCC(=O)C1=CC=CC=C1C FIYXCIBUASFFNF-UHFFFAOYSA-N 0.000 description 1
- CIHXBVUOHPCZAA-UHFFFAOYSA-N 4-(4-butoxy-4-methylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OCCCC)(C)CCN1CCCC(=O)C1=CC=CC=C1C CIHXBVUOHPCZAA-UHFFFAOYSA-N 0.000 description 1
- VJUQSABVBVCILS-UHFFFAOYSA-N 4-(4-butoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OCCCC)CCN1CCCC(=O)C1=CC=CC=C1C VJUQSABVBVCILS-UHFFFAOYSA-N 0.000 description 1
- GYQSOZCXSRLYDP-UHFFFAOYSA-N 4-(4-butyl-4-ethoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCCC)(OCC)CCN1CCCC(=O)C1=CC=CC=C1C GYQSOZCXSRLYDP-UHFFFAOYSA-N 0.000 description 1
- YRRAZZHMHOLJHC-UHFFFAOYSA-N 4-(4-butyl-4-methoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCCC)(OC)CCN1CCCC(=O)C1=CC=CC=C1C YRRAZZHMHOLJHC-UHFFFAOYSA-N 0.000 description 1
- MBSMLILTBZYTAZ-UHFFFAOYSA-N 4-(4-butylpiperazin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CN(CCCC)CCN1CCCC(=O)C1=CC=CC=C1C MBSMLILTBZYTAZ-UHFFFAOYSA-N 0.000 description 1
- NKLPKONKNCTODW-UHFFFAOYSA-N 4-(4-butylpiperazin-1-yl)butanenitrile Chemical compound CCCCN1CCN(CCCC#N)CC1 NKLPKONKNCTODW-UHFFFAOYSA-N 0.000 description 1
- RFXPEERJJDOKGJ-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2,3-dimethylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC(C)=C1C RFXPEERJJDOKGJ-UHFFFAOYSA-N 0.000 description 1
- HBIKLKXKMSHWDH-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2,4-dimethylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=C(C)C=C1C HBIKLKXKMSHWDH-UHFFFAOYSA-N 0.000 description 1
- HWFUOCLGENCVEO-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2,6-dimethylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=C(C)C=CC=C1C HWFUOCLGENCVEO-UHFFFAOYSA-N 0.000 description 1
- OTQXNIUSVXQIPC-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2-chlorophenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1Cl OTQXNIUSVXQIPC-UHFFFAOYSA-N 0.000 description 1
- RZQQFTJRGWURNW-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2-hydroxyphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1O RZQQFTJRGWURNW-UHFFFAOYSA-N 0.000 description 1
- RYTSNOYIEVVNBF-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2-methoxyphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1OC RYTSNOYIEVVNBF-UHFFFAOYSA-N 0.000 description 1
- FQQRDVRVFVHUMV-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-(2-sulfanylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1S FQQRDVRVFVHUMV-UHFFFAOYSA-N 0.000 description 1
- UZAUWJDIFLZVQS-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-1-[2-(2-sulfanylethyl)phenyl]butan-1-one Chemical compound C1CC(CCCC)CCN1CCCC(=O)C1=CC=CC=C1CCS UZAUWJDIFLZVQS-UHFFFAOYSA-N 0.000 description 1
- WYSISLZUNDTUPV-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-3,3-dimethyl-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CC(C)(C)CC(=O)C1=CC=CC=C1C WYSISLZUNDTUPV-UHFFFAOYSA-N 0.000 description 1
- XRBOQJGPCKODHV-UHFFFAOYSA-N 4-(4-butylpiperidin-1-yl)-3-methyl-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCCC)CCN1CC(C)CC(=O)C1=CC=CC=C1C XRBOQJGPCKODHV-UHFFFAOYSA-N 0.000 description 1
- FTPFQMNRBNEBAU-UHFFFAOYSA-N 4-(4-ethoxy-4-methylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OCC)(C)CCN1CCCC(=O)C1=CC=CC=C1C FTPFQMNRBNEBAU-UHFFFAOYSA-N 0.000 description 1
- KOXPNRHLTFCAGW-UHFFFAOYSA-N 4-(4-ethyl-4-methoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CC)(OC)CCN1CCCC(=O)C1=CC=CC=C1C KOXPNRHLTFCAGW-UHFFFAOYSA-N 0.000 description 1
- FLFCGCKXSPACLC-UHFFFAOYSA-N 4-(4-ethyl-4-propoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OCCC)(CC)CCN1CCCC(=O)C1=CC=CC=C1C FLFCGCKXSPACLC-UHFFFAOYSA-N 0.000 description 1
- XDTZKBYNPYRUTN-UHFFFAOYSA-N 4-(4-ethylpiperazin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CN(CC)CCN1CCCC(=O)C1=CC=CC=C1C XDTZKBYNPYRUTN-UHFFFAOYSA-N 0.000 description 1
- NWJBLOOYSAOBIX-UHFFFAOYSA-N 4-(4-hexylpiperazin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CN(CCCCCC)CCN1CCCC(=O)C1=CC=CC=C1C NWJBLOOYSAOBIX-UHFFFAOYSA-N 0.000 description 1
- KXPJTVNXQBWLMV-UHFFFAOYSA-N 4-(4-methoxy-4-methylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OC)(C)CCN1CCCC(=O)C1=CC=CC=C1C KXPJTVNXQBWLMV-UHFFFAOYSA-N 0.000 description 1
- LFVGXASMOOPQCC-UHFFFAOYSA-N 4-(4-methoxy-4-propylpiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCC)(OC)CCN1CCCC(=O)C1=CC=CC=C1C LFVGXASMOOPQCC-UHFFFAOYSA-N 0.000 description 1
- MUZBISUGQWHFDQ-UHFFFAOYSA-N 4-(4-methoxypiperidin-1-yl)-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(OC)CCN1CCCC(=O)C1=CC=CC=C1C MUZBISUGQWHFDQ-UHFFFAOYSA-N 0.000 description 1
- KFHQJFCEGVTMSZ-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)butanenitrile Chemical compound CN1CCN(CCCC#N)CC1 KFHQJFCEGVTMSZ-UHFFFAOYSA-N 0.000 description 1
- JACGFZUFOOVXNN-UHFFFAOYSA-N 4-[3-(hydroxymethyl)piperidin-1-yl]-1-(2-methylphenyl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CC(CO)CCC1 JACGFZUFOOVXNN-UHFFFAOYSA-N 0.000 description 1
- BKUSULJVFWGYTD-UHFFFAOYSA-N 4-[3-(hydroxymethyl)piperidin-1-yl]butanenitrile Chemical compound OCC1CCCN(CCCC#N)C1 BKUSULJVFWGYTD-UHFFFAOYSA-N 0.000 description 1
- UBSBNLBTLFJVOC-UHFFFAOYSA-N 4-[4-(2-ethoxyethyl)piperidin-1-yl]-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(CCOCC)CCN1CCCC(=O)C1=CC=CC=C1C UBSBNLBTLFJVOC-UHFFFAOYSA-N 0.000 description 1
- QTBKOUKLQPVLPE-UHFFFAOYSA-N 4-[4-(2-hydroxyethyl)piperazin-1-yl]-1-(2-methylphenyl)butan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCN1CCN(CCO)CC1 QTBKOUKLQPVLPE-UHFFFAOYSA-N 0.000 description 1
- OHYBAJBLDZUHJW-UHFFFAOYSA-N 4-[4-(ethoxymethyl)piperidin-1-yl]-1-(2-methylphenyl)butan-1-one Chemical compound C1CC(COCC)CCN1CCCC(=O)C1=CC=CC=C1C OHYBAJBLDZUHJW-UHFFFAOYSA-N 0.000 description 1
- GGVGFKIGPQQRFE-UHFFFAOYSA-N 4-bromo-4-chloro-1-phenylbutan-1-one Chemical compound ClC(Br)CCC(=O)C1=CC=CC=C1 GGVGFKIGPQQRFE-UHFFFAOYSA-N 0.000 description 1
- XIQSPCJCAJVNJL-UHFFFAOYSA-N 4-butylpiperidine Chemical compound CCCCC1CCNCC1 XIQSPCJCAJVNJL-UHFFFAOYSA-N 0.000 description 1
- UZOFELREXGAFOI-UHFFFAOYSA-N 4-methylpiperidine Chemical compound CC1CCNCC1 UZOFELREXGAFOI-UHFFFAOYSA-N 0.000 description 1
- CVROVTGNNDIZNS-UHFFFAOYSA-N 4-piperidin-1-ylbutanenitrile Chemical compound N#CCCCN1CCCCC1 CVROVTGNNDIZNS-UHFFFAOYSA-N 0.000 description 1
- OSDDDHPYSNZBPF-UHFFFAOYSA-N 4-pyrrolidin-1-ylbutanenitrile Chemical compound N#CCCCN1CCCC1 OSDDDHPYSNZBPF-UHFFFAOYSA-N 0.000 description 1
- FQZGJACFXHMLGU-UHFFFAOYSA-N 5-(3,5-dimethylpiperidin-1-yl)-1-(2-methylphenyl)pentan-1-one Chemical compound C1C(C)CC(C)CN1CCCCC(=O)C1=CC=CC=C1C FQZGJACFXHMLGU-UHFFFAOYSA-N 0.000 description 1
- COGBRQQLXZQEQC-UHFFFAOYSA-N 5-(4-benzylpiperazin-1-yl)-1-(2-methoxyphenyl)pentan-1-one Chemical compound COC1=CC=CC=C1C(=O)CCCCN1CCN(CC=2C=CC=CC=2)CC1 COGBRQQLXZQEQC-UHFFFAOYSA-N 0.000 description 1
- DOWIQYHHCZFVDA-UHFFFAOYSA-N 5-(4-benzylpiperidin-1-yl)-1-(2-methylphenyl)pentan-1-one Chemical compound CC1=CC=CC=C1C(=O)CCCCN1CCC(CC=2C=CC=CC=2)CC1 DOWIQYHHCZFVDA-UHFFFAOYSA-N 0.000 description 1
- QOFNYGSAVVHOJQ-UHFFFAOYSA-N 5-(4-butylpiperidin-1-yl)-1-(2-methylphenyl)pentan-1-one Chemical compound C1CC(CCCC)CCN1CCCCC(=O)C1=CC=CC=C1C QOFNYGSAVVHOJQ-UHFFFAOYSA-N 0.000 description 1
- FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108060003345 Adrenergic Receptor Proteins 0.000 description 1
- 102000017910 Adrenergic receptor Human genes 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- 206010001488 Aggression Diseases 0.000 description 1
- 206010002942 Apathy Diseases 0.000 description 1
- 241000972773 Aulopiformes Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GUBGYTABKSRVRQ-DCSYEGIMSA-N Beta-Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-DCSYEGIMSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 201000004569 Blindness Diseases 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- QYWRWHSGJDPODU-MARPTJLWSA-N C(C1=CC=CC=C1)N1[C@@H](C[C@H](CC1)C1C(C2=CC(=C(C=C2C1)OC)OC)=O)C Chemical compound C(C1=CC=CC=C1)N1[C@@H](C[C@H](CC1)C1C(C2=CC(=C(C=C2C1)OC)OC)=O)C QYWRWHSGJDPODU-MARPTJLWSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 description 1
- 208000002881 Colic Diseases 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 102000015554 Dopamine receptor Human genes 0.000 description 1
- 108050004812 Dopamine receptor Proteins 0.000 description 1
- 102000034354 Gi proteins Human genes 0.000 description 1
- 108091006101 Gi proteins Proteins 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
- 206010019851 Hepatotoxicity Diseases 0.000 description 1
- 102000000543 Histamine Receptors Human genes 0.000 description 1
- 108010002059 Histamine Receptors Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 206010027940 Mood altered Diseases 0.000 description 1
- 208000021642 Muscular disease Diseases 0.000 description 1
- 201000009623 Myopathy Diseases 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 1
- 208000022873 Ocular disease Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920002253 Tannate Polymers 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 101710120037 Toxin CcdB Proteins 0.000 description 1
- 102000003929 Transaminases Human genes 0.000 description 1
- 108090000340 Transaminases Proteins 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 235000011054 acetic acid Nutrition 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
- 229940081735 acetylcellulose Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 229940072056 alginate Drugs 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 102000030619 alpha-1 Adrenergic Receptor Human genes 0.000 description 1
- 108020004102 alpha-1 Adrenergic Receptor Proteins 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical group 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 210000002159 anterior chamber Anatomy 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- OISFUZRUIGGTSD-LJTMIZJLSA-N azane;(2r,3r,4r,5s)-6-(methylamino)hexane-1,2,3,4,5-pentol Chemical compound N.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO OISFUZRUIGGTSD-LJTMIZJLSA-N 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229960000541 cetyl alcohol Drugs 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 230000006949 cholinergic function Effects 0.000 description 1
- 210000002932 cholinergic neuron Anatomy 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 239000003593 chromogenic compound Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229940090805 clavulanate Drugs 0.000 description 1
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 230000001149 cognitive effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229940126543 compound 14 Drugs 0.000 description 1
- 229940126142 compound 16 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical class CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000007850 degeneration Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 239000007933 dermal patch Substances 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000001177 diphosphate Substances 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates 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
- 208000035475 disorder Diseases 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- 229960003530 donepezil Drugs 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 239000002702 enteric coating Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000003889 eye drop Substances 0.000 description 1
- 229940012356 eye drops Drugs 0.000 description 1
- 230000005669 field effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012054 flavored emulsion Substances 0.000 description 1
- 235000020375 flavoured syrup Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 238000002825 functional assay Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000234 hepatic damage Toxicity 0.000 description 1
- 231100000304 hepatotoxicity Toxicity 0.000 description 1
- 230000007686 hepatotoxicity Effects 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 208000013403 hyperactivity Diseases 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000003907 kidney function Effects 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- JYTUSYBCFIZPBE-AMTLMPIISA-M lactobionate Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O JYTUSYBCFIZPBE-AMTLMPIISA-M 0.000 description 1
- 229940099584 lactobionate Drugs 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 230000008818 liver damage Effects 0.000 description 1
- 230000003908 liver function Effects 0.000 description 1
- 208000018769 loss of vision Diseases 0.000 description 1
- 231100000864 loss of vision Toxicity 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UNKALQOWCZDDGF-UHFFFAOYSA-N methyl 4-(4-butylpiperidin-1-yl)butanoate Chemical compound CCCCC1CCN(CCCC(=O)OC)CC1 UNKALQOWCZDDGF-UHFFFAOYSA-N 0.000 description 1
- QAWFLJGZSZIZHO-UHFFFAOYSA-N methyl 4-bromobutanoate Chemical compound COC(=O)CCCBr QAWFLJGZSZIZHO-UHFFFAOYSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- LRMHVVPPGGOAJQ-UHFFFAOYSA-N methyl nitrate Chemical compound CO[N+]([O-])=O LRMHVVPPGGOAJQ-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000036651 mood Effects 0.000 description 1
- 230000007510 mood change Effects 0.000 description 1
- 230000037023 motor activity Effects 0.000 description 1
- 230000007659 motor function Effects 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- UQLCRQPLVWWHDC-UHFFFAOYSA-N n-phenyloctanamide Chemical compound CCCCCCCC(=O)NC1=CC=CC=C1 UQLCRQPLVWWHDC-UHFFFAOYSA-N 0.000 description 1
- 229920001206 natural gum Polymers 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 210000000478 neocortex Anatomy 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940054534 ophthalmic solution Drugs 0.000 description 1
- 239000002997 ophthalmic solution Substances 0.000 description 1
- 229940100654 ophthalmic suspension Drugs 0.000 description 1
- 210000001328 optic nerve Anatomy 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000013110 organic ligand Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001734 parasympathetic effect Effects 0.000 description 1
- 210000001002 parasympathetic nervous system Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- VUNPWIPIOOMCPT-UHFFFAOYSA-N piperidin-3-ylmethanol Chemical compound OCC1CCCNC1 VUNPWIPIOOMCPT-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 230000001242 postsynaptic effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 210000002442 prefrontal cortex Anatomy 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 235000019515 salmon Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 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
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 230000035900 sweating Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 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
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical class CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 230000004393 visual impairment Effects 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 239000012224 working solution Substances 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
- 229930195724 β-lactose Natural products 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Ophthalmology & Optometry (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US8013398P | 1998-03-31 | 1998-03-31 | |
PCT/US1999/007057 WO1999050247A1 (en) | 1998-03-31 | 1999-03-31 | Compounds with activity on muscarinic receptors |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20004912D0 NO20004912D0 (no) | 2000-09-29 |
NO20004912L NO20004912L (no) | 2000-11-23 |
NO319835B1 true NO319835B1 (no) | 2005-09-19 |
Family
ID=22155464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20004912A NO319835B1 (no) | 1998-03-31 | 2000-09-29 | Forbindelser med innvirkning pa muskarinreseptorer, anvendelser derav og farmasoytiske sammensetninger som innbefatter slike. |
Country Status (14)
Country | Link |
---|---|
EP (1) | EP1068185A1 (ru) |
JP (1) | JP2002509918A (ru) |
KR (2) | KR20060120715A (ru) |
CN (1) | CN1303376A (ru) |
AR (1) | AR014974A1 (ru) |
AU (1) | AU762726B2 (ru) |
BR (1) | BR9909277A (ru) |
CA (1) | CA2326804C (ru) |
MX (1) | MXPA00009569A (ru) |
NO (1) | NO319835B1 (ru) |
NZ (2) | NZ507204A (ru) |
RU (2) | RU2230740C2 (ru) |
WO (1) | WO1999050247A1 (ru) |
ZA (1) | ZA200005149B (ru) |
Families Citing this family (49)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6528529B1 (en) | 1998-03-31 | 2003-03-04 | Acadia Pharmaceuticals Inc. | Compounds with activity on muscarinic receptors |
US6624162B2 (en) | 2001-10-22 | 2003-09-23 | Pfizer Inc. | Imidazopyridine compounds as 5-HT4 receptor modulators |
US7307075B2 (en) | 2001-12-28 | 2007-12-11 | Acadia Pharmaceuticals Inc. | Tetrahydroquinoline analogues as muscarinic agonists |
US7550459B2 (en) | 2001-12-28 | 2009-06-23 | Acadia Pharmaceuticals, Inc. | Tetrahydroquinoline analogues as muscarinic agonists |
MXPA03000145A (es) | 2002-01-07 | 2003-07-15 | Pfizer | Compuestos de oxo u oxi-piridina como moduladores de receptores 5-ht4. |
GB0211230D0 (en) | 2002-05-16 | 2002-06-26 | Medinnova Sf | Treatment of heart failure |
DOP2003000703A (es) | 2002-09-20 | 2004-03-31 | Pfizer | Compuestos de imidazopiradina como agonistas del receptor 5-ht4 |
JP2006502180A (ja) | 2002-09-20 | 2006-01-19 | ファイザー株式会社 | 5−ht4レセプターモジュレーターとしてのn−置換されたピペリジニル−イミダゾピリジン化合物 |
HU227534B1 (en) | 2003-08-04 | 2011-08-29 | Richter Gedeon Nyrt | (thio)carbamoyl-cyclohexane derivatives, process for producing them and pharmaceutical compositions containing them |
EP1651235A4 (en) * | 2003-08-05 | 2008-12-17 | Samaritan Pharmaceuticals Inc | SIGMA-1 RECEPTOR LIGAND WITH ACETYLCHOLINESTERASE-INHIBITORY PROPERTIES |
WO2005033079A1 (ja) | 2003-09-30 | 2005-04-14 | Eisai Co., Ltd. | ヘテロ環化合物を含有する新規な抗真菌剤 |
BRPI0510453A (pt) | 2004-04-30 | 2007-10-30 | Warner Lambert Co | composto substituìdos com morfolina para o tratamento de distúrbios do sistema nervoso central |
KR100875558B1 (ko) | 2004-06-15 | 2008-12-23 | 화이자 인코포레이티드 | 벤즈이미다졸론 카복실산 유도체 |
US7737163B2 (en) | 2004-06-15 | 2010-06-15 | Pfizer Inc. | Benzimidazolone carboxylic acid derivatives |
UA89514C2 (ru) | 2004-12-30 | 2010-02-10 | Janssen Pharmaceutica Nv | Производные фениламидов 4-(бензил)-пиперазин-1-карбоновых кислот и родственные соединения как модуляторы гидролазы амидов жирных кислот для лечения тревоги, боли и других состояний |
EP2395000A1 (en) | 2004-12-30 | 2011-12-14 | Astex Therapeutics Limited | Benzimidazole compounds that modulate the activity of CDK, GSK and aurora kinases |
WO2006106711A1 (ja) | 2005-03-30 | 2006-10-12 | Eisai R & D Management Co., Ltd. | ピリジン誘導体を含有する抗真菌剤 |
US8097610B2 (en) | 2005-08-26 | 2012-01-17 | Shionogi & Co., Ltd. | Derivative having PPAR agonistic activity |
EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
JP2009506069A (ja) | 2005-08-26 | 2009-02-12 | ブレインセルス,インコーポレイティド | ムスカリン性受容体調節による神経発生 |
TWI385169B (zh) | 2005-10-31 | 2013-02-11 | Eisai R&D Man Co Ltd | 經雜環取代之吡啶衍生物及含有彼之抗真菌劑 |
JP5474354B2 (ja) | 2005-12-30 | 2014-04-16 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
US8435970B2 (en) | 2006-06-29 | 2013-05-07 | Astex Therapeutics Limited | Pharmaceutical combinations of 1-cyclopropyl-3-[3-(5-morpholin-4-ylmethyl-1H-benzoimidazol-2-yl)-1H-pyrazol-4-yl]-urea |
CL2008000119A1 (es) | 2007-01-16 | 2008-05-16 | Wyeth Corp | Compuestos derivados de pirazol, antagonistas del receptor nicotinico de acetilcolina; composicion farmaceutica; y uso en el tratamiento de enfermedades tales como demencia senil, alzheimer y esquizofrenia. |
HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
US7875610B2 (en) | 2007-12-03 | 2011-01-25 | Richter Gedeon Nyrt. | Pyrimidinyl-piperazines useful as D3/D2 receptor ligands |
US8513287B2 (en) | 2007-12-27 | 2013-08-20 | Eisai R&D Management Co., Ltd. | Heterocyclic ring and phosphonoxymethyl group substituted pyridine derivatives and antifungal agent containing same |
CN102118970A (zh) | 2008-07-16 | 2011-07-06 | 吉瑞工厂 | 包含多巴胺受体配体的药物制剂 |
HU230067B1 (hu) | 2008-12-17 | 2015-06-29 | Richter Gedeon Nyrt | Új piperazin só és eljárás előállítására |
HUP0800766A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Vegyeszet | Process for the preparation of piperazine derivatives |
HUP0800765A2 (en) | 2008-12-18 | 2010-11-29 | Richter Gedeon Nyrt | A new process for the preparation of piperazine derivatives and their hydrochloric salts |
UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
GB201106817D0 (en) | 2011-04-21 | 2011-06-01 | Astex Therapeutics Ltd | New compound |
CN102558026A (zh) * | 2011-12-27 | 2012-07-11 | 盛世泰科生物医药技术(苏州)有限公司 | 关于4-n-丁基-1-[4-(2-甲基苯基)-4-酮-1-丁基]哌啶的合成及工艺优化 |
US8912197B2 (en) | 2012-08-20 | 2014-12-16 | Forest Laboratories Holdings Ltd. | Crystalline form of carbamoyl-cyclohexane derivatives |
CN102997438A (zh) * | 2012-10-16 | 2013-03-27 | 李誊 | 改善热量利用率的电热水器控制方法 |
GB201218850D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
US9980973B2 (en) | 2012-10-19 | 2018-05-29 | Astex Therapeutics Limited | Bicyclic heterocycle compounds and their uses in therapy |
GB201218862D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
GB201218864D0 (en) | 2012-10-19 | 2012-12-05 | Astex Therapeutics Ltd | Bicyclic heterocycle compounds and their uses in therapy |
PE20161035A1 (es) | 2013-03-15 | 2016-11-13 | Global Blood Therapeutics Inc | Compuestos y usos de estos para la modulacion de la hemoglobina |
EA201992707A1 (ru) | 2013-11-18 | 2020-06-30 | Глобал Блад Терапьютикс, Инк. | Соединения и их применения для модуляции гемоглобина |
RS62301B1 (sr) | 2013-12-20 | 2021-09-30 | Astex Therapeutics Ltd | Biciklična heterociklična jedinjenja i njihove upotrebe u terapiji |
US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
AU2018289303B2 (en) | 2017-06-20 | 2023-12-21 | Imbria Pharmaceuticals, Inc. | Compositions and methods for increasing efficiency of cardiac metabolism |
US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
US11780811B2 (en) | 2020-06-30 | 2023-10-10 | Imbria Pharmaceuticals, Inc. | Methods of synthesizing 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
US11530184B2 (en) | 2020-06-30 | 2022-12-20 | Imbria Pharmaceuticals, Inc. | Crystal forms of 2-[4-[(2,3,4-trimethoxyphenyl)methyl]piperazin-1-yl]ethyl pyridine-3-carboxylate |
US11883396B2 (en) | 2021-05-03 | 2024-01-30 | Imbria Pharmaceuticals, Inc. | Methods of treating kidney conditions using modified forms of trimetazidine |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2695295A (en) * | 1952-12-19 | 1954-11-23 | Mcneilab Inc | Unsymmetrical n, n'-substituted ethylenediamine and piperazine compounds |
GB874206A (en) * | 1956-09-05 | 1961-08-02 | Knoll Ag | Basic derivatives of salicylamide |
NL271658A (ru) * | 1960-12-01 | |||
FR1382425A (fr) * | 1963-01-14 | 1964-12-18 | Ciba Geigy | Procédé de préparation de diaza-cyclo-alcanes, entre autres de la 3-méthyl-4-phényl-1-(2-phénylmercapto-éthyl)-pipérazine |
GB1053301A (ru) * | 1963-01-14 | |||
US3488352A (en) * | 1966-10-11 | 1970-01-06 | Shulton Inc | Basically substituted alkoxy anthranilamides,their corresponding 2-nitro compounds and derivatives thereof |
FR1543944A (fr) * | 1967-03-10 | 1968-10-31 | Bruneau & Cie Lab | Dérivés amidés de l'acide salicylique et leur préparation |
DE2335432A1 (de) * | 1973-07-12 | 1975-01-30 | Boehringer Mannheim Gmbh | 3,4-dihydro-2h-naphthalinon-(1)5-oxy-propyl-piperazin-derivate und verfahren zu ihrer herstellung |
BE792187A (fr) * | 1971-12-03 | 1973-03-30 | Sumitomo Chemical Co | Nouveaux derives d'alkylamines |
GB1459506A (en) * | 1974-02-18 | 1976-12-22 | Wyeth John & Brother Ltd | Piperidine derivatives |
GB1498884A (en) * | 1975-04-15 | 1978-01-25 | Wyeth John & Brother Ltd | Aminoacetamide-pyridyl-tetrahydropyridyl and-piperidyl derivatives |
IL117149A0 (en) * | 1995-02-23 | 1996-06-18 | Schering Corp | Muscarinic antagonists |
US5889006A (en) * | 1995-02-23 | 1999-03-30 | Schering Corporation | Muscarinic antagonists |
PL331536A1 (en) * | 1996-08-15 | 1999-07-19 | Schering Corp | Muscarinic antagonists with an etheric bond |
-
1999
- 1999-03-31 JP JP2000541152A patent/JP2002509918A/ja not_active Withdrawn
- 1999-03-31 EP EP99914306A patent/EP1068185A1/en not_active Withdrawn
- 1999-03-31 MX MXPA00009569A patent/MXPA00009569A/es active IP Right Grant
- 1999-03-31 BR BR9909277-8A patent/BR9909277A/pt not_active Application Discontinuation
- 1999-03-31 CA CA002326804A patent/CA2326804C/en not_active Expired - Fee Related
- 1999-03-31 NZ NZ507204A patent/NZ507204A/en unknown
- 1999-03-31 WO PCT/US1999/007057 patent/WO1999050247A1/en active IP Right Grant
- 1999-03-31 KR KR1020067023572A patent/KR20060120715A/ko not_active Application Discontinuation
- 1999-03-31 CN CN99806618A patent/CN1303376A/zh active Pending
- 1999-03-31 AU AU32187/99A patent/AU762726B2/en not_active Ceased
- 1999-03-31 RU RU2000127105/04A patent/RU2230740C2/ru active
- 1999-03-31 NZ NZ525108A patent/NZ525108A/en unknown
- 1999-03-31 KR KR1020007010780A patent/KR100672186B1/ko not_active IP Right Cessation
- 1999-04-05 AR ARP990101516A patent/AR014974A1/es not_active Application Discontinuation
-
2000
- 2000-09-26 ZA ZA200005149A patent/ZA200005149B/en unknown
- 2000-09-29 NO NO20004912A patent/NO319835B1/no unknown
-
2004
- 2004-03-11 RU RU2004107218/04A patent/RU2278111C2/ru active
Also Published As
Publication number | Publication date |
---|---|
NO20004912D0 (no) | 2000-09-29 |
KR20010042248A (ko) | 2001-05-25 |
EP1068185A1 (en) | 2001-01-17 |
CN1303376A (zh) | 2001-07-11 |
AR014974A1 (es) | 2001-04-11 |
AU762726B2 (en) | 2003-07-03 |
WO1999050247A1 (en) | 1999-10-07 |
CA2326804A1 (en) | 1999-10-07 |
KR100672186B1 (ko) | 2007-01-19 |
RU2278111C2 (ru) | 2006-06-20 |
MXPA00009569A (es) | 2002-08-06 |
KR20060120715A (ko) | 2006-11-27 |
ZA200005149B (en) | 2002-01-08 |
AU3218799A (en) | 1999-10-18 |
NZ525108A (en) | 2005-02-25 |
JP2002509918A (ja) | 2002-04-02 |
BR9909277A (pt) | 2001-10-16 |
RU2004107218A (ru) | 2005-08-20 |
NZ507204A (en) | 2003-12-19 |
RU2230740C2 (ru) | 2004-06-20 |
CA2326804C (en) | 2006-05-02 |
NO20004912L (no) | 2000-11-23 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO319835B1 (no) | Forbindelser med innvirkning pa muskarinreseptorer, anvendelser derav og farmasoytiske sammensetninger som innbefatter slike. | |
US6528529B1 (en) | Compounds with activity on muscarinic receptors | |
EP0496222B1 (de) | Indolderivate | |
CA2621255A1 (en) | Amido compounds and their use as pharmaceuticals | |
NO329065B1 (no) | Derivater av N-[fenyl(piperidin-2yl)metyl]benzamid og anvendelse av de samme i terapeutika | |
NZ547164A (en) | Derivatives of n-[phenyl(piperidine-2-yl)methyl]benzamide, preparation and therapeutic use thereof | |
CA2827567C (en) | Compounds as histamine h3 receptor ligands | |
WO2018071313A1 (en) | N-aryl and n-heteroaryl piperidine derivatives as liver x receptor beta agonists, compositions, and their use | |
DE69031111T2 (de) | Indolderivate | |
IE910747A1 (en) | Derivatives of 4-(aminomethyl)-piperidine, their preparation¹and their therapeutic application | |
NZ243337A (en) | 1-piperidyl substituted quinoline derivatives and pharmaceutical compositions | |
CA3076757C (en) | Heteroaryl compounds as muscarinic m1 receptor positive allosteric modulators | |
US4456604A (en) | 1-(3-Halo-2-pyridinyl) piperazine | |
CA2543133A1 (en) | Compounds with activity on muscarinic receptors | |
NO136841B (no) | Analogifremgangsm}te for fremstilling av terapeutisk aktive fenylimidazolidinoner. | |
NO309037B1 (no) | Substituerte aminoalkylaminopyridiner med virkning ovenfor Helicobacter pylori |