JPH07504192A - ５−ｈｔ３受容体拮抗剤としての２，６‐メタノ‐２ｈ‐キノリジン誘導体 - Google Patents

５−ｈｔ３受容体拮抗剤としての２，６‐メタノ‐２ｈ‐キノリジン誘導体

Info

Publication number: JPH07504192A
Authority: JP; Japan
Prior art keywords: treatment; treat; compound; formulas; nausea
Prior art date: 1992-02-24
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP5514868A

Other languages

English (en)

Japanese (ja)

Inventor

ジットス，モーリス　ダブリュー．

Original Assignee

メレルダウファーマス−ティカルズ　インコーポレイテッド

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-02-24

Filing date

1993-02-03

Publication date

1995-05-11

1993-02-03 Application filed by メレルダウファーマス−ティカルズ　インコーポレイテッド filed Critical メレルダウファーマス−ティカルズ　インコーポレイテッド

1995-05-11 Publication of JPH07504192A publication Critical patent/JPH07504192A/ja

Status Pending legal-status Critical Current

Links

102000035037 5-HT3 receptors Human genes 0.000 title description 4
108091005477 5-HT3 receptors Proteins 0.000 title description 4
229940044551 receptor antagonist Drugs 0.000 title description 4
239000002464 receptor antagonist Substances 0.000 title description 4
238000011282 treatment Methods 0.000 claims description 37
150000001875 compounds Chemical class 0.000 claims description 33
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 13
238000000034 method Methods 0.000 claims description 8
208000010877 cognitive disease Diseases 0.000 claims description 7
208000019695 Migraine disease Diseases 0.000 claims description 6
206010047700 Vomiting Diseases 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
201000000980 schizophrenia Diseases 0.000 claims description 6
208000011117 substance-related disease Diseases 0.000 claims description 6
206010013654 Drug abuse Diseases 0.000 claims description 5
206010026749 Mania Diseases 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 3
230000002757 inflammatory effect Effects 0.000 claims 4
239000000126 substance Substances 0.000 claims 4
208000011580 syndromic disease Diseases 0.000 claims 4
239000008194 pharmaceutical composition Substances 0.000 claims 3
239000003638 chemical reducing agent Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000013543 active substance Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
230000000694 effects Effects 0.000 description 5
208000024891 symptom Diseases 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
-1 hydrogen Chemical class 0.000 description 4
210000004379 membrane Anatomy 0.000 description 4
239000012528 membrane Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
239000000758 substrate Substances 0.000 description 4
229940113081 5 Hydroxytryptamine 3 receptor antagonist Drugs 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
208000028017 Psychotic disease Diseases 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000012790 adhesive layer Substances 0.000 description 3
230000008485 antagonism Effects 0.000 description 3
239000007864 aqueous solution Substances 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
208000035475 disorder Diseases 0.000 description 3
238000005516 engineering process Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
239000003369 serotonin 5-HT3 receptor antagonist Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
239000005973 Carvone Substances 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-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
241001465754 Metazoa Species 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000006399 behavior Effects 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
235000009508 confectionery Nutrition 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug 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
230000003400 hallucinatory effect Effects 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000010410 layer 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
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
239000003094 microcapsule Substances 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000007911 parenteral administration Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
238000001959 radiotherapy Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
238000010561 standard procedure Methods 0.000 description 2
239000004094 surface-active agent Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
102000004217 thyroid hormone receptors Human genes 0.000 description 2
108090000721 thyroid hormone receptors Proteins 0.000 description 2
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
QXHUQQSVSDVEBE-UHFFFAOYSA-N 5-chloro-2,2-dimethyl-3h-1-benzofuran-7-carboxylic acid Chemical compound ClC1=CC(C(O)=O)=C2OC(C)(C)CC2=C1 QXHUQQSVSDVEBE-UHFFFAOYSA-N 0.000 description 1
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 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
241000218645 Cedrus Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
206010012335 Dependence Diseases 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
229930091371 Fructose Natural products 0.000 description 1
239000005715 Fructose Substances 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
208000010412 Glaucoma Diseases 0.000 description 1
241000282412 Homo Species 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
206010062717 Increased upper airway secretion Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
SNIXRMIHFOIVBB-UHFFFAOYSA-N N-Hydroxyl-tryptamine Chemical compound C1=CC=C2C(CCNO)=CNC2=C1 SNIXRMIHFOIVBB-UHFFFAOYSA-N 0.000 description 1
208000026344 Nasal disease Diseases 0.000 description 1
206010028813 Nausea Diseases 0.000 description 1
206010028980 Neoplasm Diseases 0.000 description 1
208000030880 Nose disease Diseases 0.000 description 1
208000021384 Obsessive-Compulsive disease Diseases 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
206010034912 Phobia Diseases 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
208000010378 Pulmonary Embolism Diseases 0.000 description 1
241000700159 Rattus Species 0.000 description 1
101710084593 Sensory histidine kinase/phosphatase NtrB Proteins 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
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 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
240000008042 Zea mays Species 0.000 description 1
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000037374 absorbed through the skin Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
150000001495 arsenic compounds Chemical class 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
230000036471 bradycardia Effects 0.000 description 1
208000006218 bradycardia Diseases 0.000 description 1
230000007885 bronchoconstriction Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 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
235000015165 citric acid Nutrition 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000009792 diffusion process Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
230000006870 function Effects 0.000 description 1
230000030135 gastric motility Effects 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
230000000622 irritating effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
235000009973 maize Nutrition 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
239000011976 maleic acid Substances 0.000 description 1
230000007257 malfunction Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
239000011259 mixed solution Substances 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
230000002107 myocardial effect Effects 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
230000008693 nausea Effects 0.000 description 1
208000004296 neuralgia Diseases 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
229960002715 nicotine Drugs 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
208000019906 panic disease Diseases 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
208000026435 phlegm Diseases 0.000 description 1
208000019899 phobic disease Diseases 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
JWHOQZUREKYPBY-UHFFFAOYSA-N rubonic acid Natural products CC1(C)CCC2(CCC3(C)C(=CCC4C5(C)CCC(=O)C(C)(C)C5CC(=O)C34C)C2C1)C(=O)O JWHOQZUREKYPBY-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
210000001044 sensory neuron Anatomy 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000000935 solvent evaporation Methods 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004575 stone Substances 0.000 description 1
239000010902 straw Substances 0.000 description 1
201000006152 substance dependence Diseases 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/18—Bridged systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- 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
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
- 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
- A61P25/18—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
- A61P25/24—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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP5514868A 1992-02-24 1993-02-03 ５−ｈｔ３受容体拮抗剤としての２，６‐メタノ‐２ｈ‐キノリジン誘導体 Pending JPH07504192A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP92400474		1992-02-24
EP92400474.0		1992-02-24
PCT/US1993/000880 WO1993017019A1 (en)	1992-02-24	1993-02-03	2,6-methano-2h-quinolizin derivative as 5-ht3-receptor antagonist

Publications (1)

Publication Number	Publication Date
JPH07504192A true JPH07504192A (ja)	1995-05-11

Family

ID=8211614

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5514868A Pending JPH07504192A (ja)	1992-02-24	1993-02-03	５−ｈｔ３受容体拮抗剤としての２，６‐メタノ‐２ｈ‐キノリジン誘導体

Country Status (14)

Country	Link
EP (1)	EP0628043A1 (2)
JP (1)	JPH07504192A (2)
KR (1)	KR100287933B1 (2)
AU (1)	AU675060B2 (2)
CA (1)	CA2130563C (2)
FI (1)	FI105917B (2)
HU (1)	HU216831B (2)
IL (1)	IL104821A (2)
MX (1)	MX9300948A (2)
NO (1)	NO943101D0 (2)
NZ (1)	NZ249346A (2)
TW (1)	TW226374B (2)
WO (1)	WO1993017019A1 (2)
ZA (1)	ZA931146B (2)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU2672500A (en)	1999-02-18	2000-09-04	Novartis Ag	Systemic use of 5-ht3 receptor antagonists against rheumatic inflammatory processes
US8524731B2 (en)	2005-03-07	2013-09-03	The University Of Chicago	Use of opioid antagonists to attenuate endothelial cell proliferation and migration
CN101171010B (zh)	2005-03-07	2014-09-17	芝加哥大学	阿片样物质拮抗剂用于减少内皮细胞增殖和迁移的用途
US9662325B2 (en)	2005-03-07	2017-05-30	The University Of Chicago	Use of opioid antagonists to attenuate endothelial cell proliferation and migration
US8518962B2 (en)	2005-03-07	2013-08-27	The University Of Chicago	Use of opioid antagonists

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE68924545T2 (de) *	1988-02-23	1996-03-21	Merrell Dow Pharma	Verwendung von Chinolizin- und Chinolizinon-Derivaten zur Herstellung von Arzneimitteln.
EP0517984A1 (en) *	1991-06-11	1992-12-16	Merrell Dow Pharmaceuticals Inc.	Derivatives of amide analogs of certain methano bridged quinolizines

1993
- 1993-02-03 EP EP93904797A patent/EP0628043A1/en not_active Withdrawn
- 1993-02-03 WO PCT/US1993/000880 patent/WO1993017019A1/en not_active Ceased
- 1993-02-03 HU HU9402436A patent/HU216831B/hu unknown
- 1993-02-03 AU AU36034/93A patent/AU675060B2/en not_active Expired
- 1993-02-03 KR KR1019940702945A patent/KR100287933B1/ko not_active Expired - Lifetime
- 1993-02-03 CA CA002130563A patent/CA2130563C/en not_active Expired - Lifetime
- 1993-02-03 JP JP5514868A patent/JPH07504192A/ja active Pending
- 1993-02-03 NZ NZ249346A patent/NZ249346A/en not_active IP Right Cessation
- 1993-02-18 ZA ZA931146A patent/ZA931146B/xx unknown
- 1993-02-19 TW TW082101189A patent/TW226374B/zh not_active IP Right Cessation
- 1993-02-22 MX MX9300948A patent/MX9300948A/es unknown
- 1993-02-22 IL IL10482193A patent/IL104821A/xx not_active IP Right Cessation
1994
- 1994-08-23 NO NO943101A patent/NO943101D0/no unknown
- 1994-08-23 FI FI943872A patent/FI105917B/fi not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0628043A1 (en)	1994-12-14
NO943101L (no)	1994-08-23
NZ249346A (en)	1995-10-26
IL104821A0 (en)	1993-06-10
AU3603493A (en)	1993-09-13
HU216831B (hu)	1999-09-28
CA2130563C (en)	1997-11-11
ZA931146B (en)	1993-09-14
WO1993017019A1 (en)	1993-09-02
AU675060B2 (en)	1997-01-23
NO943101D0 (no)	1994-08-23
HUT68249A (en)	1995-06-28
FI105917B (fi)	2000-10-31
CA2130563A1 (en)	1993-09-02
TW226374B (2)	1994-07-11
MX9300948A (es)	1993-08-01
KR950700297A (ko)	1995-01-16
FI943872L (fi)	1994-08-23
IL104821A (en)	1997-01-10
FI943872A0 (fi)	1994-08-23
KR100287933B1 (ko)	2001-05-02
HU9402436D0 (en)	1994-10-28

Publication	Publication Date	Title
JP2000512623A (ja)	2000-09-26	ドーパミンｄ▲下４▼レセプターアンタゴニストとしての２，４―ジアミノピリミジン誘導体
JPH054983A (ja)	1993-01-14	イソキノリノン誘導体、その製造方法およびその誘導体を有効成分として含有する５−ｈｔ３レセプター拮抗剤
PT98168B (pt)	1998-12-31	Processo para a preparacao de novos derivados do indole e de composicoes farmaceuticas que os contem
GB2292143A (en)	1996-02-14	Pyrrolo-pyridine derivatives
JPH06509574A (ja)	1994-10-27	５−ｈｔ↓４レセプターアンタゴニスト
JPH08512299A (ja)	1996-12-24	５ｈｔ▲下２ｃ▼アンタゴニストとしてのインドリン誘導体
DE69111816T4 (de)	1996-08-01	Indolederivate und ihre verwendung als serotonin-antagoniste.
ES2246918T3 (es)	2006-03-01	2-(1h-indol-3-yl)-2-oxo-acetamidas con actividad antitumoral.
JPH06511261A (ja)	1994-12-15	新規なインドール誘導体
JPS63258476A (ja)	1988-10-25	ヘキサヒドロ−８−ヒドロキシ−２，６−メタノ−２ｈ−キノリジン−３（４ｈ）−オンのエステル類及び関連化合物類
RU2132683C1 (ru)	1999-07-10	Применение производных индола в качестве 5hti агонистов
JP3377227B2 (ja)	2003-02-17	あるメタノ架橋キノリジン類のアミド類似体類の誘導体類
IE83573B1 (en)		Derivatives of amide analogs of certain methano bridged quinolizines
CA2216701A1 (en)	1996-10-03	Piperidine derivatives
JPWO1996030367A1 (ja)	1998-05-26	ピペリジン誘導体
KR100287933B1 (ko)	2001-05-02	5-ht3-수용체 길항제로서의 2,6-메타노-2h-퀴놀리진 유도체,이의 제조방법 및 이를 포함하는 약제학적 조성물
CN1582282B (zh)	2012-06-06	取代的四环系四氢呋喃衍生物的扁桃酸盐化合物
CN101242819A (zh)	2008-08-13	催眠药以及取代的双芳基和杂芳基化合物的组合产品及其治疗应用
CN1455770A (zh)	2003-11-12	(2－氮杂二环[2.2.1]庚烷－7－基)甲醇衍生物作为烟碱类乙酰胆碱受体激动剂
US5508287A (en)	1996-04-16	2,6-methano-2H-quinolizin derivative as 5-HT3 -receptor antagonist
ES2218582T3 (es)	2004-11-16	2,3-dihidro-1,4-dioxinopiridinas sustituidas vasoconstrictoras.
DK175643B1 (da)	2005-01-03	Anvendelse af quinolizin- og quinolizinon-derivater ved fremstilling af lægemidler
JP2838282B2 (ja)	1998-12-16	血管攣縮治療剤
JP2002517392A (ja)	2002-06-18	５ｈｔレセプターに対して親和性を有するｎ−ベンゾジオキサニルメチル−１−ピペリジル−メチルアミン化合物
JPH05230057A (ja)	1993-09-07	光学活性インダゾール―３―カルボキサミド誘導体及びそれを有効成分とする制吐剤