NO325513B1 - 8-azabisyklo(3.2.1)okt-2-en-derivater, farmasoytiske preparater som omfatter forbindelsene, anvendelse av forbindelsene til fremstilling av medikamenter for behandling av en sykdom som gir respons pa aktiviteten til nikotin-ACh-reseptormodulatorer, samt fremgangsmate for fremstilling av forbindelsene. - Google Patents
8-azabisyklo(3.2.1)okt-2-en-derivater, farmasoytiske preparater som omfatter forbindelsene, anvendelse av forbindelsene til fremstilling av medikamenter for behandling av en sykdom som gir respons pa aktiviteten til nikotin-ACh-reseptormodulatorer, samt fremgangsmate for fremstilling av forbindelsene. Download PDFInfo
- Publication number
- NO325513B1 NO325513B1 NO19995850A NO995850A NO325513B1 NO 325513 B1 NO325513 B1 NO 325513B1 NO 19995850 A NO19995850 A NO 19995850A NO 995850 A NO995850 A NO 995850A NO 325513 B1 NO325513 B1 NO 325513B1
- Authority
- NO
- Norway
- Prior art keywords
- azabicyclo
- oct
- ene
- methyl
- thienyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 98
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 46
- 201000010099 disease Diseases 0.000 title claims abstract description 31
- 238000011282 treatment Methods 0.000 title claims abstract description 31
- SURHOQQBDZIWSO-UHFFFAOYSA-N 8-azabicyclo[3.2.1]oct-3-ene Chemical class N1C2CCC1C=CC2 SURHOQQBDZIWSO-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 44
- 230000000694 effects Effects 0.000 title claims description 14
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003814 drug Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title description 31
- 108010009685 Cholinergic Receptors Proteins 0.000 title description 22
- 102000034337 acetylcholine receptors Human genes 0.000 title 1
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- -1 2-(3-methoxymethyl) Chemical group 0.000 claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 20
- 208000002193 Pain Diseases 0.000 claims abstract description 17
- 230000036407 pain Effects 0.000 claims abstract description 17
- 201000009032 substance abuse Diseases 0.000 claims abstract description 12
- 230000016160 smooth muscle contraction Effects 0.000 claims abstract description 8
- 208000011117 substance-related disease Diseases 0.000 claims abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 5
- 231100000736 substance abuse Toxicity 0.000 claims abstract description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 3
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 54
- 229960002715 nicotine Drugs 0.000 claims description 32
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 29
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 26
- 208000024827 Alzheimer disease Diseases 0.000 claims description 13
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 12
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 11
- ILPBINAXDRFYPL-UHFFFAOYSA-N 2-octene Chemical compound CCCCCC=CC ILPBINAXDRFYPL-UHFFFAOYSA-N 0.000 claims description 8
- 230000007074 memory dysfunction Effects 0.000 claims description 7
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 208000018737 Parkinson disease Diseases 0.000 claims description 6
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 6
- 230000000391 smoking effect Effects 0.000 claims description 6
- 208000015114 central nervous system disease Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 230000004770 neurodegeneration Effects 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- RPJDXMAIYKVRML-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=C2OC(C3=CC4CCC(C3)N4C)=CC2=C1 RPJDXMAIYKVRML-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- WKIDQHCAQKRASI-UHFFFAOYSA-N 3-[3-(furan-3-yl)thiophen-2-yl]-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C=1SC=CC=1C=1C=COC=1 WKIDQHCAQKRASI-UHFFFAOYSA-N 0.000 claims description 3
- 206010061218 Inflammation Diseases 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- ACDNBQIGAKRKBQ-UHFFFAOYSA-N 1-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)ethanone Chemical compound C1C(C(C)=O)=CC2CCC1N2C ACDNBQIGAKRKBQ-UHFFFAOYSA-N 0.000 claims description 2
- JNTUJVNMCQZBLW-UHFFFAOYSA-N 2-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)-1,3-thiazole Chemical compound CN1C(C2)CCC1C=C2C1=NC=CS1 JNTUJVNMCQZBLW-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- DOXXUIIBFXZGDL-UHFFFAOYSA-N 3-(1-benzofuran-3-yl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=C2C(C3=CC4CCC(C3)N4C)=COC2=C1 DOXXUIIBFXZGDL-UHFFFAOYSA-N 0.000 claims description 2
- VCTUNRRIDDKDLD-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=C2SC(C3=CC4CCC(C3)N4C)=CC2=C1 VCTUNRRIDDKDLD-UHFFFAOYSA-N 0.000 claims description 2
- JEVSFPMGEZIRAQ-UHFFFAOYSA-N 3-(1-benzothiophen-3-yl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=C2C(C3=CC4CCC(C3)N4C)=CSC2=C1 JEVSFPMGEZIRAQ-UHFFFAOYSA-N 0.000 claims description 2
- LNTCLXHNHAMCMH-UHFFFAOYSA-N 3-(2-methoxyphenyl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound COC1=CC=CC=C1C(C1)=CC2N(C)C1CC2 LNTCLXHNHAMCMH-UHFFFAOYSA-N 0.000 claims description 2
- SSHFZBUCQQDHRB-UHFFFAOYSA-N 3-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)aniline Chemical compound CN1C(C2)CCC1C=C2C1=CC=CC(N)=C1 SSHFZBUCQQDHRB-UHFFFAOYSA-N 0.000 claims description 2
- ANCYAZAGAVYFFY-UHFFFAOYSA-N 3-(furan-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C1=CC=CO1 ANCYAZAGAVYFFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- GVAIGIAEFMORID-UHFFFAOYSA-N 8-benzyl-3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C=1C=CC=CC=1CN1C(C2)CCC1C=C2C1=CC=CN=C1 GVAIGIAEFMORID-UHFFFAOYSA-N 0.000 claims description 2
- UYJMAFZVUPEINB-UHFFFAOYSA-N 8-methyl-3-naphthalen-2-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=CC2=CC(C3=CC4CCC(C3)N4C)=CC=C21 UYJMAFZVUPEINB-UHFFFAOYSA-N 0.000 claims description 2
- OZAJXVSFXYHSBL-UHFFFAOYSA-N 8-methyl-3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C1=CC=CN=C1 OZAJXVSFXYHSBL-UHFFFAOYSA-N 0.000 claims description 2
- UIMSGPJIOKWWBP-UHFFFAOYSA-N 8-methyl-3-selenophen-2-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C1=CC=C[se]1 UIMSGPJIOKWWBP-UHFFFAOYSA-N 0.000 claims description 2
- BYFMSWGSOWHDNN-UHFFFAOYSA-N 8-methyl-3-thieno[2,3-b]thiophen-5-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C2CC(C=3SC=4SC=CC=4C=3)=CC1CC2 BYFMSWGSOWHDNN-UHFFFAOYSA-N 0.000 claims description 2
- ZNKDESSNHLUAIY-UHFFFAOYSA-N 8-methyl-3-thieno[3,2-b]thiophen-5-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C2CC(C=3SC=4C=CSC=4C=3)=CC1CC2 ZNKDESSNHLUAIY-UHFFFAOYSA-N 0.000 claims description 2
- UWEJCTMVDPCGSY-UHFFFAOYSA-N 8-methyl-3-thiophen-2-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C1=CC=CS1 UWEJCTMVDPCGSY-UHFFFAOYSA-N 0.000 claims description 2
- DJNFHLLQBYEIJO-UHFFFAOYSA-N 8-methyl-3-thiophen-3-yl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound CN1C(C2)CCC1C=C2C=1C=CSC=1 DJNFHLLQBYEIJO-UHFFFAOYSA-N 0.000 claims description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical group OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 2
- 239000004327 boric acid Chemical group 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- PEZCTSRHKSQSHO-UHFFFAOYSA-N n-[3-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)phenyl]acetamide Chemical compound CN1C(C2)CCC1C=C2C1=CC=CC(NC(C)=O)=C1 PEZCTSRHKSQSHO-UHFFFAOYSA-N 0.000 claims description 2
- CBIVWNSFZSWGPL-UHFFFAOYSA-N 2-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(C3=CC4CCC(C3)N4C)=NC2=C1 CBIVWNSFZSWGPL-UHFFFAOYSA-N 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 208000035475 disorder Diseases 0.000 abstract description 14
- 230000001713 cholinergic effect Effects 0.000 abstract description 9
- 210000003169 central nervous system Anatomy 0.000 abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 208000027866 inflammatory disease Diseases 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 53
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 102000009660 Cholinergic Receptors Human genes 0.000 description 21
- VFWFUHSATLJVSV-WLHGVMLRSA-N (E)-but-2-enedioic acid oct-2-ene Chemical compound CCCCCC=CC.OC(=O)\C=C\C(O)=O VFWFUHSATLJVSV-WLHGVMLRSA-N 0.000 description 19
- 239000004480 active ingredient Substances 0.000 description 18
- 238000004587 chromatography analysis Methods 0.000 description 16
- 239000000843 powder Substances 0.000 description 16
- 230000027455 binding Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000000741 silica gel Substances 0.000 description 14
- 229910002027 silica gel Inorganic materials 0.000 description 14
- 239000002775 capsule Substances 0.000 description 13
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 12
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 description 11
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 description 11
- 239000000872 buffer Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000001530 fumaric acid Substances 0.000 description 10
- 102000005962 receptors Human genes 0.000 description 10
- 108020003175 receptors Proteins 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- QQXLDOJGLXJCSE-KNVOCYPGSA-N tropinone Chemical compound C1C(=O)C[C@H]2CC[C@@H]1N2C QQXLDOJGLXJCSE-KNVOCYPGSA-N 0.000 description 10
- QQXLDOJGLXJCSE-UHFFFAOYSA-N N-methylnortropinone Natural products C1C(=O)CC2CCC1N2C QQXLDOJGLXJCSE-UHFFFAOYSA-N 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 210000004556 brain Anatomy 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 210000001519 tissue Anatomy 0.000 description 8
- 239000002552 dosage form Substances 0.000 description 7
- 208000019901 Anxiety disease Diseases 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 6
- 206010012735 Diarrhoea Diseases 0.000 description 6
- 208000026097 Factitious disease Diseases 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 230000036506 anxiety Effects 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 6
- 230000009871 nonspecific binding Effects 0.000 description 6
- 239000008188 pellet Substances 0.000 description 6
- 230000002265 prevention Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 208000032841 Bulimia Diseases 0.000 description 5
- 206010006550 Bulimia nervosa Diseases 0.000 description 5
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 5
- 206010020651 Hyperkinesia Diseases 0.000 description 5
- 208000000269 Hyperkinesis Diseases 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 208000008589 Obesity Diseases 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 206010043118 Tardive Dyskinesia Diseases 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 206010015037 epilepsy Diseases 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000007937 lozenge Substances 0.000 description 5
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 5
- 230000001537 neural effect Effects 0.000 description 5
- 239000002858 neurotransmitter agent Substances 0.000 description 5
- 235000020824 obesity Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 210000003491 skin Anatomy 0.000 description 5
- 208000000044 Amnesia Diseases 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 208000030814 Eating disease Diseases 0.000 description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 description 4
- 208000019695 Migraine disease Diseases 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- 206010039966 Senile dementia Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960004373 acetylcholine Drugs 0.000 description 4
- 230000000202 analgesic effect Effects 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 4
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 4
- 229940027564 cytisine Drugs 0.000 description 4
- 235000014632 disordered eating Nutrition 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 206010027599 migraine Diseases 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 210000002569 neuron Anatomy 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 201000000980 schizophrenia Diseases 0.000 description 4
- 229940076279 serotonin Drugs 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- KSPVFUJFLJBOLL-UHFFFAOYSA-N (8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl) trifluoromethanesulfonate Chemical compound C1C(OS(=O)(=O)C(F)(F)F)=CC2CCC1N2C KSPVFUJFLJBOLL-UHFFFAOYSA-N 0.000 description 3
- 229930182840 (S)-nicotine Natural products 0.000 description 3
- 208000030507 AIDS Diseases 0.000 description 3
- 206010002383 Angina Pectoris Diseases 0.000 description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 description 3
- 206010003805 Autism Diseases 0.000 description 3
- 208000020706 Autistic disease Diseases 0.000 description 3
- 208000020925 Bipolar disease Diseases 0.000 description 3
- 208000028698 Cognitive impairment Diseases 0.000 description 3
- 206010009900 Colitis ulcerative Diseases 0.000 description 3
- 208000011231 Crohn disease Diseases 0.000 description 3
- 206010012289 Dementia Diseases 0.000 description 3
- NLPRAJRHRHZCQQ-UHFFFAOYSA-N Epibatidine Natural products C1=NC(Cl)=CC=C1C1C(N2)CCC2C1 NLPRAJRHRHZCQQ-UHFFFAOYSA-N 0.000 description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 208000023105 Huntington disease Diseases 0.000 description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 3
- 206010026749 Mania Diseases 0.000 description 3
- 208000026139 Memory disease Diseases 0.000 description 3
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 3
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 3
- 206010028403 Mutism Diseases 0.000 description 3
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 208000004983 Phantom Limb Diseases 0.000 description 3
- 206010056238 Phantom pain Diseases 0.000 description 3
- 208000008348 Post-Concussion Syndrome Diseases 0.000 description 3
- 208000004550 Postoperative Pain Diseases 0.000 description 3
- 208000005107 Premature Birth Diseases 0.000 description 3
- 206010036590 Premature baby Diseases 0.000 description 3
- 206010036618 Premenstrual syndrome Diseases 0.000 description 3
- 206010052276 Pseudodementia Diseases 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 206010041250 Social phobia Diseases 0.000 description 3
- 208000000323 Tourette Syndrome Diseases 0.000 description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 description 3
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 229940049706 benzodiazepine Drugs 0.000 description 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 208000028683 bipolar I disease Diseases 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001684 chronic effect Effects 0.000 description 3
- 208000010877 cognitive disease Diseases 0.000 description 3
- 230000003920 cognitive function Effects 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 230000007850 degeneration Effects 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229960003638 dopamine Drugs 0.000 description 3
- 230000003291 dopaminomimetic effect Effects 0.000 description 3
- 230000004064 dysfunction Effects 0.000 description 3
- 206010013932 dyslexia Diseases 0.000 description 3
- NLPRAJRHRHZCQQ-IVZWLZJFSA-N epibatidine Chemical compound C1=NC(Cl)=CC=C1[C@@H]1[C@H](N2)CC[C@H]2C1 NLPRAJRHRHZCQQ-IVZWLZJFSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 239000008273 gelatin Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 201000001881 impotence Diseases 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- 238000005567 liquid scintillation counting Methods 0.000 description 3
- 230000029849 luteinization Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000006984 memory degeneration Effects 0.000 description 3
- 208000023060 memory loss Diseases 0.000 description 3
- 229960005181 morphine Drugs 0.000 description 3
- 201000003631 narcolepsy Diseases 0.000 description 3
- 208000015122 neurodegenerative disease Diseases 0.000 description 3
- 229940127240 opiate Drugs 0.000 description 3
- 208000033808 peripheral neuropathy Diseases 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 206010036596 premature ejaculation Diseases 0.000 description 3
- 230000000306 recurrent effect Effects 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 208000019116 sleep disease Diseases 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 239000006228 supernatant Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 208000011580 syndromic disease Diseases 0.000 description 3
- 239000012085 test solution Substances 0.000 description 3
- 208000002271 trichotillomania Diseases 0.000 description 3
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 2
- DIOHEXPTUTVCNX-UHFFFAOYSA-N 1,1,1-trifluoro-n-phenyl-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)N(S(=O)(=O)C(F)(F)F)C1=CC=CC=C1 DIOHEXPTUTVCNX-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 2
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- RSUHKGOVXMXCND-UHFFFAOYSA-N 8-benzyl-8-azabicyclo[3.2.1]octan-3-one Chemical compound C1C(=O)CC2CCC1N2CC1=CC=CC=C1 RSUHKGOVXMXCND-UHFFFAOYSA-N 0.000 description 2
- 208000002874 Acne Vulgaris Diseases 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 241000416162 Astragalus gummifer Species 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- GVGLGOZIDCSQPN-PVHGPHFFSA-N Heroin Chemical compound O([C@H]1[C@H](C=C[C@H]23)OC(C)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4OC(C)=O GVGLGOZIDCSQPN-PVHGPHFFSA-N 0.000 description 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 208000016620 Tourette disease Diseases 0.000 description 2
- 229920001615 Tragacanth Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 206010000496 acne Diseases 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 201000007930 alcohol dependence Diseases 0.000 description 2
- 230000037007 arousal Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 210000003710 cerebral cortex Anatomy 0.000 description 2
- 229960003920 cocaine Drugs 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 229960002069 diamorphine Drugs 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 210000005064 dopaminergic neuron Anatomy 0.000 description 2
- 206010013663 drug dependence Diseases 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 229930195712 glutamate Natural products 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 230000004968 inflammatory condition Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 201000003723 learning disability Diseases 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 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
- 238000002844 melting Methods 0.000 description 2
- 206010027175 memory impairment Diseases 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
- 230000003387 muscular Effects 0.000 description 2
- 210000003928 nasal cavity Anatomy 0.000 description 2
- 230000002232 neuromuscular Effects 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 230000002352 nonmutagenic effect Effects 0.000 description 2
- 229960002748 norepinephrine Drugs 0.000 description 2
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 229940005483 opioid analgesics Drugs 0.000 description 2
- 230000037324 pain perception Effects 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 238000000159 protein binding assay Methods 0.000 description 2
- 229940075993 receptor modulator Drugs 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 201000004700 rosacea Diseases 0.000 description 2
- 230000000862 serotonergic effect Effects 0.000 description 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 239000000196 tragacanth Substances 0.000 description 2
- 235000010487 tragacanth Nutrition 0.000 description 2
- 229940116362 tragacanth Drugs 0.000 description 2
- 230000002747 voluntary effect Effects 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- KPWKPGFLZGMMFX-VHSXEESVSA-N (-)-camphanic acid Chemical compound C1C[C@]2(C(O)=O)OC(=O)[C@@]1(C)C2(C)C KPWKPGFLZGMMFX-VHSXEESVSA-N 0.000 description 1
- KPWKPGFLZGMMFX-ZJUUUORDSA-N (1s,4r)-1,7,7-trimethyl-2-oxo-3-oxabicyclo[2.2.1]heptane-4-carboxylic acid Chemical compound C1C[C@@]2(C(O)=O)OC(=O)[C@]1(C)C2(C)C KPWKPGFLZGMMFX-ZJUUUORDSA-N 0.000 description 1
- IBTSWKLSEOGJGJ-UHFFFAOYSA-N (3-acetamidophenyl)boronic acid Chemical compound CC(=O)NC1=CC=CC(B(O)O)=C1 IBTSWKLSEOGJGJ-UHFFFAOYSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- AECUDRROWHBKBX-UHFFFAOYSA-N 1-methoxyethenyl(trimethyl)stannane Chemical group COC(=C)[Sn](C)(C)C AECUDRROWHBKBX-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- RORUEWFPGKJEPN-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-8-ethyl-8-azabicyclo[3.2.1]oct-3-ene Chemical compound C1=CC=C2OC(C3=CC4CCC(C3)N4CC)=CC2=C1 RORUEWFPGKJEPN-UHFFFAOYSA-N 0.000 description 1
- CTIFCRVFVGUGEB-UHFFFAOYSA-N 3-(8-methyl-8-azabicyclo[3.2.1]oct-3-en-3-yl)quinoline Chemical compound C1=CC=CC2=CC(C3=CC4CCC(C3)N4C)=CN=C21 CTIFCRVFVGUGEB-UHFFFAOYSA-N 0.000 description 1
- NYPYPOZNGOXYSU-UHFFFAOYSA-N 3-bromopyridine Chemical compound BrC1=CC=CN=C1 NYPYPOZNGOXYSU-UHFFFAOYSA-N 0.000 description 1
- XCMISAPCWHTVNG-UHFFFAOYSA-N 3-bromothiophene Chemical compound BrC=1C=CSC=1 XCMISAPCWHTVNG-UHFFFAOYSA-N 0.000 description 1
- XADICJHFELMBGX-UHFFFAOYSA-N 5-bromo-2-methoxypyridine Chemical compound COC1=CC=C(Br)C=N1 XADICJHFELMBGX-UHFFFAOYSA-N 0.000 description 1
- VJOWMORERYNYON-UHFFFAOYSA-N 5-ethenyl-2-methylpyridine Chemical compound CC1=CC=C(C=C)C=N1 VJOWMORERYNYON-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 1
- 101710195183 Alpha-bungarotoxin Proteins 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000272079 Bungarus multicinctus Species 0.000 description 1
- 108091006146 Channels Proteins 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000019888 Circadian rhythm sleep disease Diseases 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
- ZGUNAGUHMKGQNY-SSDOTTSWSA-N D-alpha-phenylglycine Chemical compound OC(=O)[C@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-SSDOTTSWSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 241000272060 Elapidae Species 0.000 description 1
- 208000017701 Endocrine disease Diseases 0.000 description 1
- 241000320517 Epipedobates tricolor Species 0.000 description 1
- 241000722985 Fidia Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 102000018997 Growth Hormone Human genes 0.000 description 1
- 108010051696 Growth Hormone Proteins 0.000 description 1
- 241000557766 Guthriea Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010020850 Hyperthyroidism Diseases 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000881 Modified starch Polymers 0.000 description 1
- HSHXDCVZWHOWCS-UHFFFAOYSA-N N'-hexadecylthiophene-2-carbohydrazide Chemical compound CCCCCCCCCCCCCCCCNNC(=O)c1cccs1 HSHXDCVZWHOWCS-UHFFFAOYSA-N 0.000 description 1
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 1
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 206010060860 Neurological symptom Diseases 0.000 description 1
- 241000208125 Nicotiana Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 102000003840 Opioid Receptors Human genes 0.000 description 1
- 108090000137 Opioid Receptors Proteins 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 102100035591 POU domain, class 2, transcription factor 2 Human genes 0.000 description 1
- 101710084411 POU domain, class 2, transcription factor 2 Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000001431 Psychomotor Agitation Diseases 0.000 description 1
- 206010038743 Restlessness Diseases 0.000 description 1
- 206010041349 Somnolence Diseases 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 206010043903 Tobacco abuse Diseases 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- VOXIUXZAOFEFBL-UHFFFAOYSA-N Voacangin Natural products CCC1CC2CN3CC1C(C2)(OC(=O)C)c4[nH]c5ccc(OC)cc5c4C3 VOXIUXZAOFEFBL-UHFFFAOYSA-N 0.000 description 1
- 102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 description 1
- 108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003281 allosteric effect Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000002830 appetite depressant Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 208000013404 behavioral symptom Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 229940050390 benzoate Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 230000006931 brain damage Effects 0.000 description 1
- 231100000874 brain damage Toxicity 0.000 description 1
- 208000029028 brain injury Diseases 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-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
- 230000010221 calcium permeability Effects 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960004424 carbon dioxide Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 210000001638 cerebellum Anatomy 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 1
- 230000006949 cholinergic function Effects 0.000 description 1
- 210000002932 cholinergic neuron Anatomy 0.000 description 1
- 230000009783 cholinergic response Effects 0.000 description 1
- 235000019504 cigarettes Nutrition 0.000 description 1
- 229940114081 cinnamate Drugs 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003166 dihydrofolate reductase inhibitor Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000775 effect on neurotransmitter Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000002615 epidermis Anatomy 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- KHBKYYUHCSVLIX-UHFFFAOYSA-N furan-3-yloxyboronic acid Chemical compound OB(O)OC=1C=COC=1 KHBKYYUHCSVLIX-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000003349 gelling agent Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000000122 growth hormone Substances 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
- HSIBGVUMFOSJPD-CFDPKNGZSA-N ibogaine Chemical compound N1([C@@H]2[C@H]3C[C@H](C1)C[C@@H]2CC)CCC1=C3NC2=CC=C(OC)C=C12 HSIBGVUMFOSJPD-CFDPKNGZSA-N 0.000 description 1
- OLOCMRXSJQJJPL-UHFFFAOYSA-N ibogaine Natural products CCC1CC2CC3C1N(C2)C=Cc4c3[nH]c5ccc(OC)cc45 OLOCMRXSJQJJPL-UHFFFAOYSA-N 0.000 description 1
- AREITJMUSRHSBK-UHFFFAOYSA-N ibogamine Natural products CCC1CC2C3CC1CN2CCc4c3[nH]c5ccccc45 AREITJMUSRHSBK-UHFFFAOYSA-N 0.000 description 1
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 235000001705 insufficient nutrition Nutrition 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 231100000863 loss of memory Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 210000005171 mammalian brain Anatomy 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
- 230000008018 melting Effects 0.000 description 1
- 238000001465 metallisation Methods 0.000 description 1
- XLTANAWLDBYGFU-UHFFFAOYSA-N methyllycaconitine hydrochloride Natural products C1CC(OC)C2(C3C4OC)C5CC(C(C6)OC)C(OC)C5C6(O)C4(O)C2N(CC)CC31COC(=O)C1=CC=CC=C1N1C(=O)CC(C)C1=O XLTANAWLDBYGFU-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- UZHSEJADLWPNLE-GRGSLBFTSA-N naloxone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(O)C2=C5[C@@]13CCN4CC=C UZHSEJADLWPNLE-GRGSLBFTSA-N 0.000 description 1
- 229960004127 naloxone Drugs 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 210000000715 neuromuscular junction Anatomy 0.000 description 1
- 230000000324 neuroprotective effect Effects 0.000 description 1
- 239000003901 neurotransmitter uptake inhibitor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- SXRRGQVUFIKIJD-UHFFFAOYSA-N oct-2-ene;hydrochloride Chemical compound Cl.CCCCCC=CC SXRRGQVUFIKIJD-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 210000000287 oocyte Anatomy 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 208000019906 panic disease Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000004031 partial agonist Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000007310 pathophysiology Effects 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 description 1
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 208000028591 pheochromocytoma Diseases 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
- 150000003053 piperidines Chemical class 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 210000004129 prosencephalon Anatomy 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000241 respiratory effect Effects 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
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 230000005586 smoking cessation Effects 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 210000000278 spinal cord Anatomy 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- WRRVIWDMZZRXRG-UHFFFAOYSA-N tert-butyl 3-pyridin-3-yl-8-azabicyclo[3.2.1]oct-3-ene-8-carboxylate Chemical compound CC(C)(C)OC(=O)N1C(C2)CCC1C=C2C1=CC=CN=C1 WRRVIWDMZZRXRG-UHFFFAOYSA-N 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 208000005057 thyrotoxicosis Diseases 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 208000037820 vascular cognitive impairment Diseases 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- LYTCVQQGCSNFJU-LKGYBJPKSA-N α-bungarotoxin Chemical compound C(/[C@H]1O[C@H]2C[C@H]3O[C@@H](CC(=C)C=O)C[C@H](O)[C@]3(C)O[C@@H]2C[C@@H]1O[C@@H]1C2)=C/C[C@]1(C)O[C@H]1[C@@]2(C)O[C@]2(C)CC[C@@H]3O[C@@H]4C[C@]5(C)O[C@@H]6C(C)=CC(=O)O[C@H]6C[C@H]5O[C@H]4C[C@@H](C)[C@H]3O[C@H]2C1 LYTCVQQGCSNFJU-LKGYBJPKSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/06—Antiabortive agents; Labour repressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Diabetes (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Anesthesiology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Pregnancy & Childbirth (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK62797 | 1997-05-30 | ||
| DK150297 | 1997-12-19 | ||
| DK40898 | 1998-03-24 | ||
| DK53498 | 1998-04-16 | ||
| PCT/DK1998/000225 WO1998054181A1 (en) | 1997-05-30 | 1998-05-29 | 8-azabicyclo(3,2,1)oct-2-ene and octane derivatives as cholinergic ligands at nicotinic ach receptors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO995850L NO995850L (no) | 1999-11-29 |
| NO995850D0 NO995850D0 (no) | 1999-11-29 |
| NO325513B1 true NO325513B1 (no) | 2008-05-26 |
Family
ID=27439314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO19995850A NO325513B1 (no) | 1997-05-30 | 1999-11-29 | 8-azabisyklo(3.2.1)okt-2-en-derivater, farmasoytiske preparater som omfatter forbindelsene, anvendelse av forbindelsene til fremstilling av medikamenter for behandling av en sykdom som gir respons pa aktiviteten til nikotin-ACh-reseptormodulatorer, samt fremgangsmate for fremstilling av forbindelsene. |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US6645977B1 (https=) |
| EP (1) | EP0984965B1 (https=) |
| JP (1) | JP4447663B2 (https=) |
| KR (1) | KR100589872B1 (https=) |
| CN (1) | CN1157392C (https=) |
| AT (1) | ATE267199T1 (https=) |
| AU (1) | AU745964B2 (https=) |
| BR (1) | BR9809697A (https=) |
| CA (1) | CA2289574C (https=) |
| CZ (1) | CZ298824B6 (https=) |
| DE (1) | DE69823994T2 (https=) |
| DK (1) | DK0984965T3 (https=) |
| EE (1) | EE04057B1 (https=) |
| HU (1) | HUP0002713A3 (https=) |
| IL (2) | IL132437A0 (https=) |
| IS (1) | IS2092B (https=) |
| NO (1) | NO325513B1 (https=) |
| NZ (1) | NZ500642A (https=) |
| RU (1) | RU2186780C2 (https=) |
| SK (1) | SK284994B6 (https=) |
| TR (1) | TR199902942T2 (https=) |
| WO (1) | WO1998054181A1 (https=) |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6350758B1 (en) * | 1996-12-02 | 2002-02-26 | Georgetown University | Tropane derivatives and method for their synthesis |
| WO1999065492A1 (en) | 1998-06-19 | 1999-12-23 | Eli Lilly And Company | Inhibition of serotonin reuptake |
| US6218383B1 (en) * | 1998-08-07 | 2001-04-17 | Targacept, Inc. | Pharmaceutical compositions for the prevention and treatment of central nervous system disorders |
| ATE259804T1 (de) * | 1998-11-27 | 2004-03-15 | Neurosearch As | 8-azabicyclo(3.2.1)okt-2-en- und -oktanderivate |
| US6953855B2 (en) | 1998-12-11 | 2005-10-11 | Targacept, Inc. | 3-substituted-2(arylalkyl)-1-azabicycloalkanes and methods of use thereof |
| US6432975B1 (en) * | 1998-12-11 | 2002-08-13 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| AU2278700A (en) | 1999-01-28 | 2000-08-18 | Neurosearch A/S | Novel azabicyclo derivatives and their use |
| US7265115B2 (en) | 1999-01-29 | 2007-09-04 | Abbott Laboratories | Diazabicyclic CNS active agents |
| ES2305373T3 (es) * | 1999-01-29 | 2008-11-01 | Abbott Laboratories | Derivados diazabiciclicos como ligandos del receptor nicotinico de la acetilcolina. |
| NZ513575A (en) | 1999-05-04 | 2003-07-25 | Neurosearch As | Heteroaryl diazabicycloalkanes useful for treating or preventing a disease or a disorder responsive to the activity of nAChR modulators |
| US6890935B2 (en) | 1999-11-01 | 2005-05-10 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| MY145722A (en) * | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| NZ522793A (en) | 2000-07-04 | 2005-02-25 | Neurosearch As | Aryl and heteroaryl diazabicycloalkanes, their preparation and use |
| CN100398103C (zh) * | 2000-10-13 | 2008-07-02 | 神经研究公司 | 通过烟碱性受体激动剂和单胺能物质的联合作用治疗情感性精神障碍 |
| CA2462453C (en) * | 2001-10-02 | 2009-07-28 | Pharmacia & Upjohn Company | Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| CA2476681A1 (en) | 2002-02-19 | 2003-08-28 | Bruce N. Rogers | Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease |
| CN100522976C (zh) * | 2002-05-07 | 2009-08-05 | 神经研究公司 | 氮杂环乙炔基衍生物 |
| GB2398636A (en) * | 2003-02-21 | 2004-08-25 | Ipsen Ltd | Method for determining the quantity of pre-synaptic neuromuscular blocking substance contained in a sample |
| DE602004013427T2 (de) * | 2003-02-28 | 2009-06-04 | Schering Corp. | Biaryltetrahydroisochinolin-piperidine als selektive mch-rezeptor-antagonisten zur behandlung von adipositas und verwandten erkrankungen |
| KR100767854B1 (ko) | 2003-03-12 | 2007-10-17 | 화이자 프로덕츠 인크. | 피리딜옥시메틸 및 벤즈이속사졸 아자비시클릭 유도체 |
| AU2005284908B2 (en) | 2004-09-13 | 2011-12-08 | Morningside Venture Investments Limited | Biosynchronous transdermal drug delivery |
| US20060173037A1 (en) * | 2005-01-10 | 2006-08-03 | Nathalie Schlienger | Aminophenyl derivatives as selective androgen receptor modulators |
| US7662812B2 (en) | 2005-02-16 | 2010-02-16 | Neurosearch A/S | Diazabicyclic aryl derivatives and their use as chinolinergic ligands at nicotinic acetylcholine receptors |
| DE102005007859A1 (de) * | 2005-02-21 | 2006-08-24 | Lts Lohmann Therapie-Systeme Ag | Vefahren für eine medikamentöse Kombinations-Behandlung, sowie hierfür geeignete Arzneimittel-Kombinationen |
| EP1869034A1 (en) * | 2005-04-08 | 2007-12-26 | NeuroSearch A/S | (+) - and (-) -8-alkyl-3-(trifluoralkylsulfonyloxy)-8-azabicycl (3.2.1.)oct-2-ene |
| FR2889701B1 (fr) * | 2005-08-12 | 2007-10-05 | Sanofi Aventis Sa | Derives de 5-pyridinyl-1-azabicyclo[3.2.1]octane, leur preparation en therapeutique. |
| ATE473978T1 (de) | 2005-12-06 | 2010-07-15 | Neurosearch As | Neue diazabicyclische arylderivate und medizinische verwendung dafür |
| US20070134169A1 (en) * | 2005-12-11 | 2007-06-14 | Rabinoff Michael D | Methods for smoking cessation or alcohol cessation or other addiction cessation |
| AU2007213670A1 (en) | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3,9-diazabicyclo[3.3.1]nonane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors |
| WO2007090888A1 (en) | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3-heteroaryl- 3,9-diazabicyclo[3.3.1]nonane derivatives as nicotinic acetylcholine receptor agonists |
| CN101379063A (zh) | 2006-02-10 | 2009-03-04 | 神经研究公司 | 3,9-二氮杂双环[3.3.1]壬烷衍生物及其作为单胺神经递质再摄取抑制剂的用途 |
| MX2008014296A (es) * | 2006-06-12 | 2009-03-06 | Pfizer Prod Inc | Antagonista de ccr5 para mejorar la restitucion inmunitaria y tratar la infeccion oportunista en pacientes con vih. |
| CN103977003A (zh) | 2007-04-02 | 2014-08-13 | 帕金森氏病研究院 | 用于降低治疗的副作用的方法和组合物 |
| TWI415850B (zh) * | 2007-07-20 | 2013-11-21 | Theravance Inc | 製備ｍｕ類鴉片受體拮抗劑之中間物的方法 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| US8697722B2 (en) * | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| ES2439767T3 (es) * | 2008-08-01 | 2014-01-24 | Purdue Pharma Lp | Compuestos de tetrahidropiridinilo y dihidropirrolilo y uso de los mismos |
| AU2009317348A1 (en) * | 2008-11-18 | 2010-05-27 | Neurosearch A/S | 8-azabicyclo [3.2.1]oct-2-ene derivatives and their use as mono-amine neurotransmitter re-uptake inhibitors |
| LT2889033T (lt) | 2008-11-19 | 2018-07-10 | Forum Pharmaceuticals Inc. | Šizofrenijos negatyvių simptomų gydymas (r)-7-chlor-n-(chinuklidin-3-il)benzo[b]tiofen-2-karboksamidu ir jo farmaciniu požiūriu priimtinomis druskomis |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| JP5808319B2 (ja) * | 2009-05-11 | 2015-11-10 | フォルム ファーマシューティカルズ、インコーポレイテッド | アセチルコリンエステラーゼ阻害剤と組み合わせた特定のα７ニコチン酸受容体を用いた認知障害の治療 |
| RU2560729C2 (ru) | 2010-01-11 | 2015-08-20 | АСТРАЕА ТЕРАПЕУТИКС, ЭлЭлСи | Модуляторы никотиновых ацетилхолиновых рецепторов |
| PE20170923A1 (es) | 2010-05-17 | 2017-07-12 | Forum Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida monohidratado |
| EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| WO2014011768A1 (en) * | 2012-07-10 | 2014-01-16 | Adispell, Inc. | Anti-anxiety treatment |
| AU2016211330A1 (en) | 2015-01-28 | 2017-08-03 | Chrono Therapeutics Inc. | Drug delivery methods and systems |
| US9724340B2 (en) | 2015-07-31 | 2017-08-08 | Attenua, Inc. | Antitussive compositions and methods |
| CA3049529A1 (en) | 2017-01-06 | 2018-07-12 | Chrono Therapeutics Inc. | Transdermal drug delivery devices and methods |
| US11596779B2 (en) | 2018-05-29 | 2023-03-07 | Morningside Venture Investments Limited | Drug delivery methods and systems |
| US12397141B2 (en) | 2018-11-16 | 2025-08-26 | Morningside Venture Investments Limited | Thermally regulated transdermal drug delivery system |
| KR102272452B1 (ko) | 2020-12-11 | 2021-07-05 | (주)예광솔라 | 스파이럴 파일 공법 및 이에 적용되는 스파이럴 파일 |
| KR200497569Y1 (ko) | 2021-02-18 | 2023-12-21 | 주식회사 알파인랩 | 지주 기초용 스크루 파일 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133073A (en) * | 1959-12-10 | 1964-05-12 | Sterling Drug Inc | 3-aryl-1, 5-iminocycloalkanes and preparation thereof |
| US3657257A (en) * | 1970-08-31 | 1972-04-18 | Robins Co Inc A H | 3-aryl-8-carbamoyl nortropanes |
| CA1244028A (en) * | 1983-04-14 | 1988-11-01 | Hans Maag | Pyrimidine derivatives |
| GB9019973D0 (en) | 1990-09-12 | 1990-10-24 | Wyeth John & Brother Ltd | Azabicyclic derivatives |
| US5045546A (en) | 1990-10-26 | 1991-09-03 | Hoechst-Roussel Pharmaceuticals Inc. | 8-azabicyclo[3.2.1]octylalkylthiazolidines |
| FI111367B (fi) | 1991-02-04 | 2003-07-15 | Aventis Pharma Inc | Menetelmä terapeuttisesti käyttökelpoisten N-(aryylioksialkyyli)heteroaryyli-8-atsabisyklo[3.2.1]oktaanijohdannaisten valmistamiseksi ja menetelmässä käytetyt välituotteet |
| ES2153360T3 (es) * | 1991-05-29 | 2001-03-01 | Abbott Lab | Compuestos de isoxazol e de isotiazol que mejoran las funciones de razonamiento. |
| US5731317A (en) * | 1995-03-10 | 1998-03-24 | Merck & Co., Inc. | Bridged piperidines promote release of growth hormone |
| GB9507203D0 (en) * | 1995-04-07 | 1995-05-31 | Smithkline Beecham Plc | Novel compounds |
| JPH11512443A (ja) * | 1995-09-22 | 1999-10-26 | ノボ ノルディスク アクティーゼルスカブ | 新規な置換アザ環式またはアザ二環式化合物 |
| DE69637097T2 (de) * | 1995-10-13 | 2007-09-20 | Neurosearch A/S | 8-Azabicyclo(3.2.1)Oct-2-en-Derivate, deren Herstellung und Anwendung |
| GB9706222D0 (en) * | 1997-03-26 | 1997-05-14 | Zeneca Ltd | Bicyclic amine derivatives |
| EP0955301A3 (en) * | 1998-04-27 | 2001-04-18 | Pfizer Products Inc. | 7-aza-bicyclo[2.2.1]-heptane derivatives, their preparation and use according to their affinity for neuronal nicotinic acetylcholine receptors |
| WO1999065492A1 (en) * | 1998-06-19 | 1999-12-23 | Eli Lilly And Company | Inhibition of serotonin reuptake |
-
1998
- 1998-05-29 KR KR1019997011137A patent/KR100589872B1/ko not_active Expired - Fee Related
- 1998-05-29 AT AT98921378T patent/ATE267199T1/de not_active IP Right Cessation
- 1998-05-29 EP EP98921378A patent/EP0984965B1/en not_active Expired - Lifetime
- 1998-05-29 CA CA002289574A patent/CA2289574C/en not_active Expired - Fee Related
- 1998-05-29 WO PCT/DK1998/000225 patent/WO1998054181A1/en not_active Ceased
- 1998-05-29 IL IL13243798A patent/IL132437A0/xx active IP Right Grant
- 1998-05-29 CN CNB988054132A patent/CN1157392C/zh not_active Expired - Fee Related
- 1998-05-29 AU AU74261/98A patent/AU745964B2/en not_active Ceased
- 1998-05-29 NZ NZ500642A patent/NZ500642A/en unknown
- 1998-05-29 DK DK98921378T patent/DK0984965T3/da active
- 1998-05-29 HU HU0002713A patent/HUP0002713A3/hu unknown
- 1998-05-29 JP JP50013099A patent/JP4447663B2/ja not_active Expired - Fee Related
- 1998-05-29 DE DE69823994T patent/DE69823994T2/de not_active Expired - Lifetime
- 1998-05-29 RU RU99128075/04A patent/RU2186780C2/ru not_active IP Right Cessation
- 1998-05-29 BR BR9809697-4A patent/BR9809697A/pt not_active Application Discontinuation
- 1998-05-29 SK SK1626-99A patent/SK284994B6/sk not_active IP Right Cessation
- 1998-05-29 CZ CZ0414799A patent/CZ298824B6/cs not_active IP Right Cessation
- 1998-05-29 TR TR1999/02942T patent/TR199902942T2/xx unknown
- 1998-05-29 EE EEP199900529A patent/EE04057B1/xx not_active IP Right Cessation
-
1999
- 1999-10-17 IL IL132437A patent/IL132437A/en not_active IP Right Cessation
- 1999-11-10 IS IS5243A patent/IS2092B/is unknown
- 1999-11-29 NO NO19995850A patent/NO325513B1/no not_active IP Right Cessation
- 1999-11-29 US US09/450,637 patent/US6645977B1/en not_active Expired - Fee Related
-
2003
- 2003-07-17 US US10/620,559 patent/US6964972B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO325513B1 (no) | 8-azabisyklo(3.2.1)okt-2-en-derivater, farmasoytiske preparater som omfatter forbindelsene, anvendelse av forbindelsene til fremstilling av medikamenter for behandling av en sykdom som gir respons pa aktiviteten til nikotin-ACh-reseptormodulatorer, samt fremgangsmate for fremstilling av forbindelsene. | |
| US6392045B1 (en) | 9-azobicyclo[3.3.1] non-2-ene derivatives as cholinergic ligands at nicotinic ACH receptors | |
| AU744368B2 (en) | Spiro-quinuclidine derivatives, their preparation and use | |
| NO317094B1 (no) | Heteroaryldiazasykloalkaner som kolinerge ligander i nikotinsyreacetylkolinreseptorer | |
| NO309569B1 (no) | Fusjonerte tropanderivater som inhiberer for neurotransmitteropptak | |
| AU747419B2 (en) | Azaring-ether derivatives and their use as nicotinic ACH receptor modulators | |
| AU736547B2 (en) | Azacyclooctane and heptane derivatives, their preparation and use in therapy | |
| MXPA99011081A (en) | 8-azabicyclo(3,2,1)oct-2-ene and octane derivatives as cholinergic ligands at nicotinic ach receptors | |
| PL190567B1 (pl) | Pochodne 8-azabicyklo[3.2.1]okt-2-enowe, preparat farmaceutyczny i zastosowanie pochodnych 8-azabicyklo[3.2.1]okt-2-enowych | |
| UA68347C2 (en) | Derivatives of 8-azabicyclo[3.2.1]oct-2-ene and octane, their synthesis and use | |
| MXPA00004396A (en) | Azaring-ether derivatives and their use as nicotinic ach receptor modulators |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |