JP2519734B2 - 新規置換ピリド〔２，３−ｂ〕〔１，４〕ベンゾジアゼピン−６−オン，その製法及びその化合物を含む医薬 - Google Patents
新規置換ピリド〔２，３−ｂ〕〔１，４〕ベンゾジアゼピン−６−オン，その製法及びその化合物を含む医薬Info
- Publication number
- JP2519734B2 JP2519734B2 JP62175802A JP17580287A JP2519734B2 JP 2519734 B2 JP2519734 B2 JP 2519734B2 JP 62175802 A JP62175802 A JP 62175802A JP 17580287 A JP17580287 A JP 17580287A JP 2519734 B2 JP2519734 B2 JP 2519734B2
- Authority
- JP
- Japan
- Prior art keywords
- atom
- group
- general formula
- pyrido
- benzodiazepin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 48
- QYETZOYLEWPRIX-UHFFFAOYSA-N pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical class O=C1N=C2C=CC=NC2=NC2=CC=CC=C12 QYETZOYLEWPRIX-UHFFFAOYSA-N 0.000 title claims abstract description 15
- 239000003814 drug Substances 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 32
- 238000002360 preparation method Methods 0.000 title description 11
- 230000008569 process Effects 0.000 title description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 31
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- -1 1,2- ethylene group Chemical group 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 20
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 14
- 150000007524 organic acids Chemical class 0.000 claims abstract description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 11
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 11
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 10
- 239000000460 chlorine Substances 0.000 claims abstract description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 8
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 235000005985 organic acids Nutrition 0.000 claims abstract description 8
- 208000006218 bradycardia Diseases 0.000 claims abstract description 7
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 230000036471 bradycardia Effects 0.000 claims abstract description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 14
- KSSXNHGPIDAUAS-UHFFFAOYSA-N 1,4-benzodiazepin-6-one Chemical compound N1=CC=NC=C2C(=O)C=CC=C21 KSSXNHGPIDAUAS-UHFFFAOYSA-N 0.000 claims description 9
- PGBFOEXPMAAGPS-UHFFFAOYSA-N 9-chloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical group CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 PGBFOEXPMAAGPS-UHFFFAOYSA-N 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 8
- 125000004429 atom Chemical group 0.000 claims 4
- 125000001153 fluoro group Chemical group F* 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 2
- 206010049765 Bradyarrhythmia Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 abstract description 4
- 238000010521 absorption reaction Methods 0.000 abstract description 3
- 230000002349 favourable effect Effects 0.000 abstract description 3
- 230000001515 vagal effect Effects 0.000 abstract description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
- 239000011737 fluorine Substances 0.000 abstract description 2
- 210000004211 gastric acid Anatomy 0.000 abstract description 2
- 230000002911 mydriatic effect Effects 0.000 abstract description 2
- 230000002401 inhibitory effect Effects 0.000 abstract 2
- 206010039424 Salivary hypersecretion Diseases 0.000 abstract 1
- 208000026451 salivation Diseases 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 44
- 230000008018 melting Effects 0.000 description 44
- 239000000203 mixture Substances 0.000 description 41
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 23
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 22
- 239000000126 substance Substances 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000013078 crystal Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 210000000056 organ Anatomy 0.000 description 10
- 239000003826 tablet Substances 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 9
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 5
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 125000004663 dialkyl amino group Chemical group 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- WTIYGHQFUHZRDA-UHFFFAOYSA-N n-ethyl-n-(piperidin-2-ylmethyl)ethanamine Chemical compound CCN(CC)CC1CCCCN1 WTIYGHQFUHZRDA-UHFFFAOYSA-N 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- DHZYXWMZLAKTQV-UHFFFAOYSA-N diazepin-3-one Chemical class O=C1C=CC=CN=N1 DHZYXWMZLAKTQV-UHFFFAOYSA-N 0.000 description 4
- 238000010494 dissociation reaction Methods 0.000 description 4
- 230000005593 dissociations Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
- UZEBJLIOUJPVCE-UHFFFAOYSA-N 9-chloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C12 UZEBJLIOUJPVCE-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 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 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 210000003710 cerebral cortex Anatomy 0.000 description 3
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 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
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 150000004292 cyclic ethers Chemical class 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000003149 muscarinic antagonist Substances 0.000 description 3
- 230000009871 nonspecific binding Effects 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000009518 sodium iodide Nutrition 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- NVSCKPYFRRVVQP-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-2,4,8-trimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC(C)=CC(C)=C2NC(=O)C2=CC(C)=CC=C21 NVSCKPYFRRVVQP-UHFFFAOYSA-N 0.000 description 2
- WLXGYEJLZQXZQC-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-7-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=C(F)C=CC=C21 WLXGYEJLZQXZQC-UHFFFAOYSA-N 0.000 description 2
- VZVIXQWQBRJQTH-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-8-ethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC(CC)=CC=C21 VZVIXQWQBRJQTH-UHFFFAOYSA-N 0.000 description 2
- IKBGLVGRGHQYIH-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-8-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC(F)=CC=C21 IKBGLVGRGHQYIH-UHFFFAOYSA-N 0.000 description 2
- SQVJJPKFSGCJIQ-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-9-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(F)C=C21 SQVJJPKFSGCJIQ-UHFFFAOYSA-N 0.000 description 2
- BKPOKVPVHMZXGY-UHFFFAOYSA-N 2-acetyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C(C)(=O)C=1C=CC2=C(NC3=C(C(N2)=O)C=CC=C3)N=1 BKPOKVPVHMZXGY-UHFFFAOYSA-N 0.000 description 2
- BWEQZMQQWNISED-UHFFFAOYSA-N 2-chloro-11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=C(Cl)N=C2N(C(=O)CCl)C2=CC=CC=C21 BWEQZMQQWNISED-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- XDZVWSDADRXNRD-UHFFFAOYSA-N 4-benzyl-3-(chloromethyl)morpholine;hydrochloride Chemical compound Cl.ClCC1COCCN1CC1=CC=CC=C1 XDZVWSDADRXNRD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NAHUTNUVFDAUFI-UHFFFAOYSA-N 8-bromo-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC(Br)=CC=C21 NAHUTNUVFDAUFI-UHFFFAOYSA-N 0.000 description 2
- KKONBTKPCIKQMC-UHFFFAOYSA-N 9-chloro-11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC(Cl)=CC=C21 KKONBTKPCIKQMC-UHFFFAOYSA-N 0.000 description 2
- KVDBLDYQUSZLDE-KRWDZBQOSA-N 9-chloro-11-[2-[(2s)-2-(diethylaminomethyl)pyrrolidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)C[C@@H]1CCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 KVDBLDYQUSZLDE-KRWDZBQOSA-N 0.000 description 2
- ZAGJGLZECKQXFM-UHFFFAOYSA-N 9-chloro-11-[2-[2-(pyrrolidin-1-ylmethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C=1C(Cl)=CC=C(C(NC2=CC=CN=C22)=O)C=1N2C(=O)CN1CCCCC1CN1CCCC1 ZAGJGLZECKQXFM-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 229920000715 Mucilage Polymers 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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000010617 anise oil Substances 0.000 description 2
- 230000001022 anti-muscarinic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 210000001008 atrial appendage Anatomy 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- 238000010009 beating Methods 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 230000027119 gastric acid secretion Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 210000003405 ileum Anatomy 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000003978 infusion fluid Substances 0.000 description 2
- 150000007529 inorganic bases Chemical group 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000036445 liquid secretion Effects 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 229940041616 menthol Drugs 0.000 description 2
- 229960001383 methylscopolamine Drugs 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- RMHMFHUVIITRHF-UHFFFAOYSA-N pirenzepine Chemical compound C1CN(C)CCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=CC=C21 RMHMFHUVIITRHF-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000002287 radioligand Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 210000001913 submandibular gland Anatomy 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- QCHFTSOMWOSFHM-WPRPVWTQSA-N (+)-Pilocarpine Chemical compound C1OC(=O)[C@@H](CC)[C@H]1CC1=CN=CN1C QCHFTSOMWOSFHM-WPRPVWTQSA-N 0.000 description 1
- PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 1
- CPLXVETYMUMERG-UHFFFAOYSA-N (4-benzylmorpholin-3-yl)methanol Chemical compound OCC1COCCN1CC1=CC=CC=C1 CPLXVETYMUMERG-UHFFFAOYSA-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
- RQXXCWHCUOJQGR-UHFFFAOYSA-N 1,1-dichlorohexane Chemical compound CCCCCC(Cl)Cl RQXXCWHCUOJQGR-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- DHGMDHQNUNRMIN-UHFFFAOYSA-N 1-benzylpyrrolidin-3-one Chemical compound C1C(=O)CCN1CC1=CC=CC=C1 DHGMDHQNUNRMIN-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- WSROIXBCJOAOEP-UHFFFAOYSA-N 10-bromo-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=C(Br)C=CC=C2C(=O)NC2=CC=CN=C21 WSROIXBCJOAOEP-UHFFFAOYSA-N 0.000 description 1
- MEORYRHCRSJSSI-UHFFFAOYSA-N 10-chloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=C1C(Cl)=CC=C2 MEORYRHCRSJSSI-UHFFFAOYSA-N 0.000 description 1
- FBDRPHKCTMUJOS-UHFFFAOYSA-N 10-methyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=C1C(C)=CC=C2 FBDRPHKCTMUJOS-UHFFFAOYSA-N 0.000 description 1
- VRBMHESKIOVTEB-UHFFFAOYSA-N 11-(2-chloroacetyl)-10-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound ClCC(=O)N1C2=NC=CC=C2NC(=O)C2=C1C(C)=CC=C2 VRBMHESKIOVTEB-UHFFFAOYSA-N 0.000 description 1
- WJQAXNZDLDOXHE-UHFFFAOYSA-N 11-(2-chloroacetyl)-2,10-dimethyl-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC(C)=C2N(C(=O)CCl)C2=NC(C)=CC=C21 WJQAXNZDLDOXHE-UHFFFAOYSA-N 0.000 description 1
- DQTLRNOCUWGNDF-UHFFFAOYSA-N 11-(2-chloroacetyl)-2,4,10-trimethyl-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC(C)=C2N(C(=O)CCl)C2=NC(C)=CC(C)=C21 DQTLRNOCUWGNDF-UHFFFAOYSA-N 0.000 description 1
- CNTOLCWONABMRA-UHFFFAOYSA-N 11-(2-chloroacetyl)-2,4,8-trimethyl-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(C)=CC=C2N(C(=O)CCl)C2=NC(C)=CC(C)=C21 CNTOLCWONABMRA-UHFFFAOYSA-N 0.000 description 1
- JOPYPOJILDCDAW-UHFFFAOYSA-N 11-(2-chloroacetyl)-2,4-dimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCl)C2=NC(C)=CC(C)=C21 JOPYPOJILDCDAW-UHFFFAOYSA-N 0.000 description 1
- DHRVNRIWOZQYEX-UHFFFAOYSA-N 11-(2-chloroacetyl)-2-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2N(C(=O)CCl)C2=NC(C)=CC=C21 DHRVNRIWOZQYEX-UHFFFAOYSA-N 0.000 description 1
- JWUPCUAKVPFVHW-UHFFFAOYSA-N 11-(2-chloroacetyl)-7-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound ClCC(=O)N1C2=NC=CC=C2NC(=O)C2=C1C=CC=C2F JWUPCUAKVPFVHW-UHFFFAOYSA-N 0.000 description 1
- VSRVNQSURMOUOQ-UHFFFAOYSA-N 11-(2-chloroacetyl)-8,9-dimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound ClCC(=O)N1C2=NC=CC=C2NC(=O)C2=C1C=C(C)C(C)=C2 VSRVNQSURMOUOQ-UHFFFAOYSA-N 0.000 description 1
- ZQYDGTQJCYLUML-UHFFFAOYSA-N 11-(2-chloroacetyl)-8-ethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(CC)=CC=C2N(C(=O)CCl)C2=NC=CC=C21 ZQYDGTQJCYLUML-UHFFFAOYSA-N 0.000 description 1
- UXJGWMPFGJUCGQ-UHFFFAOYSA-N 11-(2-chloroacetyl)-8-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(F)=CC=C2N(C(=O)CCl)C2=NC=CC=C21 UXJGWMPFGJUCGQ-UHFFFAOYSA-N 0.000 description 1
- ILHQTMDSGUUORN-UHFFFAOYSA-N 11-(2-chloroacetyl)-8-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(C)=CC=C2N(C(=O)CCl)C2=NC=CC=C21 ILHQTMDSGUUORN-UHFFFAOYSA-N 0.000 description 1
- CMOLFOMKSOSXJZ-UHFFFAOYSA-N 11-(2-chloroacetyl)-9-fluoro-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound ClCC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(F)C=C21 CMOLFOMKSOSXJZ-UHFFFAOYSA-N 0.000 description 1
- CCFVQOVADHPHDP-UHFFFAOYSA-N 11-(2-chloroacetyl)-9-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound ClCC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(C)C=C21 CCFVQOVADHPHDP-UHFFFAOYSA-N 0.000 description 1
- PGLRPMLUXKAYPI-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-10-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=C(C)C=CC=C2C(=O)NC2=CC=CN=C21 PGLRPMLUXKAYPI-UHFFFAOYSA-N 0.000 description 1
- XWFJVKJKHJDNTH-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-2,4,10-trimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=C(C)C=CC=C2C(=O)NC2=C(C)C=C(C)N=C21 XWFJVKJKHJDNTH-UHFFFAOYSA-N 0.000 description 1
- BPQQZUFUMPLETQ-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-2,8-dimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC(C)=CC=C2NC(=O)C2=CC(C)=CC=C21 BPQQZUFUMPLETQ-UHFFFAOYSA-N 0.000 description 1
- XFMSBQWSJSQGHB-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-8,9-dimethyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC(C)=C(C)C=C21 XFMSBQWSJSQGHB-UHFFFAOYSA-N 0.000 description 1
- AWNQBPUEPGODQB-UHFFFAOYSA-N 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-9-methyl-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(C)C=C21 AWNQBPUEPGODQB-UHFFFAOYSA-N 0.000 description 1
- IUKZKQYZIDJIRK-UHFFFAOYSA-N 2,10-dichloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=C(Cl)C=CC=C2C(=O)NC2=CC=C(Cl)N=C21 IUKZKQYZIDJIRK-UHFFFAOYSA-N 0.000 description 1
- YQAAWOQXUHEXRZ-UHFFFAOYSA-N 2,10-dimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC(C)=C2NC2=NC(C)=CC=C21 YQAAWOQXUHEXRZ-UHFFFAOYSA-N 0.000 description 1
- NPBWELIVCRAKQA-UHFFFAOYSA-N 2,4,10-trimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC(C)=C2NC2=NC(C)=CC(C)=C21 NPBWELIVCRAKQA-UHFFFAOYSA-N 0.000 description 1
- WTXWEFJAXUDXSO-UHFFFAOYSA-N 2,4,8-trimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(C)=CC=C2NC2=NC(C)=CC(C)=C21 WTXWEFJAXUDXSO-UHFFFAOYSA-N 0.000 description 1
- NEJSZRPFHKBQHV-UHFFFAOYSA-N 2,4-dimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2NC2=NC(C)=CC(C)=C21 NEJSZRPFHKBQHV-UHFFFAOYSA-N 0.000 description 1
- BDKGZSORNOWJNE-UHFFFAOYSA-N 2,8-dimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(C)=CC=C2NC2=NC(C)=CC=C21 BDKGZSORNOWJNE-UHFFFAOYSA-N 0.000 description 1
- HIHBNBWENCCFHS-UHFFFAOYSA-N 2,9-dichloro-11-(2-chloroacetyl)-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=C(Cl)N=C2N(C(=O)CCl)C2=CC(Cl)=CC=C21 HIHBNBWENCCFHS-UHFFFAOYSA-N 0.000 description 1
- JIRMSLCBLMMQQT-UHFFFAOYSA-N 2,9-dichloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC(Cl)=CC=C2NC(=O)C2=CC=C(Cl)C=C21 JIRMSLCBLMMQQT-UHFFFAOYSA-N 0.000 description 1
- AYZHGLAFUOXWLM-UHFFFAOYSA-N 2,9-dichloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC(Cl)=CC=C2NC(=O)C2=CC=C(Cl)C=C12 AYZHGLAFUOXWLM-UHFFFAOYSA-N 0.000 description 1
- NQABIECSSOLVGP-UHFFFAOYSA-N 2-(chloromethyl)piperidin-1-ium;chloride Chemical compound Cl.ClCC1CCCCN1 NQABIECSSOLVGP-UHFFFAOYSA-N 0.000 description 1
- WOXFMYVTSLAQMO-UHFFFAOYSA-N 2-Pyridinemethanamine Chemical group NCC1=CC=CC=N1 WOXFMYVTSLAQMO-UHFFFAOYSA-N 0.000 description 1
- ZQTHSCUBLQNIBW-UHFFFAOYSA-N 2-[2-(diethylaminomethyl)piperidin-1-yl]acetic acid Chemical compound CCN(CC)CC1CCCCN1CC(O)=O ZQTHSCUBLQNIBW-UHFFFAOYSA-N 0.000 description 1
- SVNYLJXNKKKTEF-UHFFFAOYSA-N 2-chloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC(Cl)=CC=C2NC(=O)C2=CC=CC=C21 SVNYLJXNKKKTEF-UHFFFAOYSA-N 0.000 description 1
- YRTRAYRPONISKO-UHFFFAOYSA-N 2-chloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2NC2=NC(Cl)=CC=C21 YRTRAYRPONISKO-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- DBDHTERUDQUZDQ-UHFFFAOYSA-N 2-methyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC=CC=C2NC2=NC(C)=CC=C21 DBDHTERUDQUZDQ-UHFFFAOYSA-N 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- UZGLOGCJCWBBIV-UHFFFAOYSA-N 3-(chloromethyl)pyridin-1-ium;chloride Chemical compound Cl.ClCC1=CC=CN=C1 UZGLOGCJCWBBIV-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- MIRBIZDDMSFTKY-UHFFFAOYSA-N 5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2NC2=CC=CC=C12 MIRBIZDDMSFTKY-UHFFFAOYSA-N 0.000 description 1
- YEGBCTSQUHUAJL-UHFFFAOYSA-N 7-fluoro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=C1C=CC=C2F YEGBCTSQUHUAJL-UHFFFAOYSA-N 0.000 description 1
- JZLRRKBHXWJKSU-UHFFFAOYSA-N 8,9-dimethyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=C1C=C(C)C(C)=C2 JZLRRKBHXWJKSU-UHFFFAOYSA-N 0.000 description 1
- ZUMXXVIKYWNVDD-UHFFFAOYSA-N 8-bromo-11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC=C(Br)C=C21 ZUMXXVIKYWNVDD-UHFFFAOYSA-N 0.000 description 1
- SZMAXCNQRQFOTO-UHFFFAOYSA-N 8-bromo-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(Br)=CC=C2NC2=NC=CC=C21 SZMAXCNQRQFOTO-UHFFFAOYSA-N 0.000 description 1
- VPODJWIJPNXHBC-UHFFFAOYSA-N 8-chloro-11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC=C(Cl)C=C21 VPODJWIJPNXHBC-UHFFFAOYSA-N 0.000 description 1
- NQUYEGAGAHPKQI-UHFFFAOYSA-N 8-chloro-11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC(Cl)=CC=C21 NQUYEGAGAHPKQI-UHFFFAOYSA-N 0.000 description 1
- IHORFTBDOGAILO-UHFFFAOYSA-N 8-chloro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(Cl)=CC=C2NC2=NC=CC=C21 IHORFTBDOGAILO-UHFFFAOYSA-N 0.000 description 1
- JAEZSHWQCLCWMX-UHFFFAOYSA-N 8-fluoro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(F)=CC=C2NC2=NC=CC=C21 JAEZSHWQCLCWMX-UHFFFAOYSA-N 0.000 description 1
- IEZUIQOEMNFOHT-UHFFFAOYSA-N 8-methyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C(=O)C2=CC(C)=CC=C2NC2=NC=CC=C21 IEZUIQOEMNFOHT-UHFFFAOYSA-N 0.000 description 1
- RIIWNTLJRMPXLY-UHFFFAOYSA-N 9-bromo-11-(2-chloroacetyl)-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound O=C1NC2=CC=CN=C2N(C(=O)CCl)C2=CC(Br)=CC=C21 RIIWNTLJRMPXLY-UHFFFAOYSA-N 0.000 description 1
- AJPDHAKCQDVDPA-UHFFFAOYSA-N 9-bromo-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=CC=C(Br)C=C12 AJPDHAKCQDVDPA-UHFFFAOYSA-N 0.000 description 1
- PDHXRRNMYUXODF-UHFFFAOYSA-N 9-chloro-11-[2-[2-(morpholin-4-ylmethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C=1C(Cl)=CC=C(C(NC2=CC=CN=C22)=O)C=1N2C(=O)CN1CCCCC1CN1CCOCC1 PDHXRRNMYUXODF-UHFFFAOYSA-N 0.000 description 1
- YWZDMCIOCCXXQR-UHFFFAOYSA-N 9-chloro-11-[2-[2-[(dimethylamino)methyl]piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CN(C)CC1CCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 YWZDMCIOCCXXQR-UHFFFAOYSA-N 0.000 description 1
- DGRMSRLNUQRVEE-UHFFFAOYSA-N 9-chloro-11-[2-[2-[[ethyl(methyl)amino]methyl]azepan-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(C)CC1CCCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 DGRMSRLNUQRVEE-UHFFFAOYSA-N 0.000 description 1
- SKIYNJKBHVVLBZ-UHFFFAOYSA-N 9-chloro-11-[2-[3-(diethylaminomethyl)morpholin-4-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCN(CC)CC1COCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 SKIYNJKBHVVLBZ-UHFFFAOYSA-N 0.000 description 1
- XEIYMOUVMGIKCJ-UHFFFAOYSA-N 9-chloro-11-[2-[3-(diethylaminomethyl)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C1C(CN(CC)CC)CCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 XEIYMOUVMGIKCJ-UHFFFAOYSA-N 0.000 description 1
- HOIBJQVDHOLEGV-UHFFFAOYSA-N 9-chloro-11-[2-[3-(dimethylamino)piperidin-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound C1C(N(C)C)CCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(Cl)C=C21 HOIBJQVDHOLEGV-UHFFFAOYSA-N 0.000 description 1
- OEDYNQOMETYIAZ-UHFFFAOYSA-N 9-fluoro-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=CC=C(F)C=C12 OEDYNQOMETYIAZ-UHFFFAOYSA-N 0.000 description 1
- DYANXLATMAEUPX-UHFFFAOYSA-N 9-methyl-11-[2-[2-[[methyl(propyl)amino]methyl]azepan-1-yl]acetyl]-5h-pyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound CCCN(C)CC1CCCCCN1CC(=O)N1C2=NC=CC=C2NC(=O)C2=CC=C(C)C=C21 DYANXLATMAEUPX-UHFFFAOYSA-N 0.000 description 1
- GJKMWZLKQRUYQS-UHFFFAOYSA-N 9-methyl-5,11-dihydropyrido[2,3-b][1,4]benzodiazepin-6-one Chemical compound N1C2=NC=CC=C2NC(=O)C2=CC=C(C)C=C12 GJKMWZLKQRUYQS-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- JQGJIGBQKZKRCN-UHFFFAOYSA-N CC1=CC2=C(C(NC3=C(N2C(CN2C(CCCC2)CN(C(C)C)C)=O)N=CC=C3)=O)C=C1 Chemical compound CC1=CC2=C(C(NC3=C(N2C(CN2C(CCCC2)CN(C(C)C)C)=O)N=CC=C3)=O)C=C1 JQGJIGBQKZKRCN-UHFFFAOYSA-N 0.000 description 1
- LYPLZQYCLDUYIB-UHFFFAOYSA-N CCN(CC)CC1CCCCN1CC(=O)N2C3=CC=CC(=C3C(=O)NC4=C2N=CC=C4)C Chemical compound CCN(CC)CC1CCCCN1CC(=O)N2C3=CC=CC(=C3C(=O)NC4=C2N=CC=C4)C LYPLZQYCLDUYIB-UHFFFAOYSA-N 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 235000021538 Chard Nutrition 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- VLJNHYLEOZPXFW-BYPYZUCNSA-N L-prolinamide Chemical compound NC(=O)[C@@H]1CCCN1 VLJNHYLEOZPXFW-BYPYZUCNSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 241001072332 Monia Species 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- ZKDWYGKSIRBBCU-UHFFFAOYSA-N N1C(=O)C2=CC=CC=C2NC2=C1C=CC=[N+]2[O-] Chemical compound N1C(=O)C2=CC=CC=C2NC2=C1C=CC=[N+]2[O-] ZKDWYGKSIRBBCU-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- QCHFTSOMWOSFHM-UHFFFAOYSA-N SJ000285536 Natural products C1OC(=O)C(CC)C1CC1=CN=CN1C QCHFTSOMWOSFHM-UHFFFAOYSA-N 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 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
- 208000001871 Tachycardia Diseases 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910001516 alkali metal iodide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001078 anti-cholinergic effect Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- OPFURXRZISKMJV-UHFFFAOYSA-N azepan-1-ium-2-carboxylate Chemical compound OC(=O)C1CCCCCN1 OPFURXRZISKMJV-UHFFFAOYSA-N 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
- 230000001713 cholinergic effect Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- WVPKAWVFTPWPDB-UHFFFAOYSA-N dichlorophosphinic acid Chemical compound OP(Cl)(Cl)=O WVPKAWVFTPWPDB-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- CNTIXUGILVWVHR-UHFFFAOYSA-N diphosphoryl chloride Chemical compound ClP(Cl)(=O)OP(Cl)(Cl)=O CNTIXUGILVWVHR-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000010575 fractional recrystallization Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000004561 lacrimal apparatus Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
- 229960002329 methacholine Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- JECMDTMOQOVPIU-UHFFFAOYSA-N n-(piperidin-2-ylmethyl)-n-propylpropan-1-amine Chemical compound CCCN(CCC)CC1CCCCN1 JECMDTMOQOVPIU-UHFFFAOYSA-N 0.000 description 1
- RPVZBMVWRRRFHD-UHFFFAOYSA-N n-[(4-benzylmorpholin-3-yl)methyl]-n-ethylethanamine Chemical compound CCN(CC)CC1COCCN1CC1=CC=CC=C1 RPVZBMVWRRRFHD-UHFFFAOYSA-N 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 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
- 239000002245 particle Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229960001416 pilocarpine Drugs 0.000 description 1
- 229960004633 pirenzepine Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002985 plastic film Substances 0.000 description 1
- 239000003880 polar aprotic solvent Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000001747 pupil Anatomy 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 210000005247 right atrial appendage Anatomy 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011182 sodium carbonates Nutrition 0.000 description 1
- 229960001462 sodium cyclamate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- MDDYOVJRBILUNB-UHFFFAOYSA-N xanthanol Natural products CC(O)C=C(OC(=O)C)/C1=CCC2C(CC1C)OC(=O)C2=C MDDYOVJRBILUNB-UHFFFAOYSA-N 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Lubricants (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3626095.9 | 1986-07-31 | ||
| DE19863626095 DE3626095A1 (de) | 1986-07-31 | 1986-07-31 | Neue substituierte pyrido(2,3-b)(1,4)benzodiazepin-6-one, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6335573A JPS6335573A (ja) | 1988-02-16 |
| JP2519734B2 true JP2519734B2 (ja) | 1996-07-31 |
Family
ID=6306503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62175802A Expired - Lifetime JP2519734B2 (ja) | 1986-07-31 | 1987-07-14 | 新規置換ピリド〔２，３−ｂ〕〔１，４〕ベンゾジアゼピン−６−オン，その製法及びその化合物を含む医薬 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4971966A (enExample) |
| EP (1) | EP0254955B1 (enExample) |
| JP (1) | JP2519734B2 (enExample) |
| KR (1) | KR950010073B1 (enExample) |
| AT (1) | ATE76643T1 (enExample) |
| AU (1) | AU594489B2 (enExample) |
| CA (1) | CA1311752C (enExample) |
| DD (1) | DD265146A5 (enExample) |
| DE (2) | DE3626095A1 (enExample) |
| DK (1) | DK169722B1 (enExample) |
| ES (1) | ES2042523T3 (enExample) |
| FI (1) | FI85479C (enExample) |
| GR (1) | GR3005157T3 (enExample) |
| HU (1) | HU197745B (enExample) |
| IE (1) | IE60861B1 (enExample) |
| IL (1) | IL83366A (enExample) |
| NO (1) | NO165345C (enExample) |
| NZ (1) | NZ221278A (enExample) |
| PH (1) | PH26406A (enExample) |
| PT (1) | PT85455B (enExample) |
| ZA (1) | ZA875623B (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3726908A1 (de) * | 1987-08-13 | 1989-02-23 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| DE3820346A1 (de) * | 1988-06-15 | 1989-12-21 | Thomae Gmbh Dr K | Neue kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US5179090A (en) * | 1989-09-11 | 1993-01-12 | Klaus Rudolf | Condensed diazepinones and medicaments containing these compounds |
| US5324832A (en) * | 1991-07-03 | 1994-06-28 | The United States Of America As Represented By The Department Of Health And Human Services | Muscarinic antagonists |
| US5716952A (en) * | 1992-03-18 | 1998-02-10 | Allergan | Method for reducing intraocular pressure in the mammalian eye by administration of muscarinic antagonists |
| US6531502B1 (en) * | 1998-01-21 | 2003-03-11 | Sugen, Inc. | 3-Methylidenyl-2-indolinone modulators of protein kinase |
| CN1241833C (zh) | 2000-10-20 | 2006-02-15 | 昭和电工株式会社 | 生产低碱氧化铝的方法及其设备 |
| GB0428250D0 (en) * | 2004-12-23 | 2005-01-26 | Novartis Ag | Organic compounds |
| JP2007051037A (ja) * | 2005-08-19 | 2007-03-01 | Asahi Kagaku Kogyo Co Ltd | 薄片状αアルミナ粒子の製造方法 |
| JPWO2023190663A1 (enExample) * | 2022-03-30 | 2023-10-05 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1795183B1 (de) * | 1968-08-20 | 1972-07-20 | Thomae Gmbh Dr K | 5,11-Dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-on-derivate und Arzneimittel |
| US4210648A (en) * | 1977-05-31 | 1980-07-01 | Boehringer Ingelheim Gmbh | II-Aminoacyl-5,11-dihydro-6H-pyrido(2,3-B) (1,4)benzodiazepin-6-ones and salts thereof |
| DE3204403A1 (de) * | 1982-02-09 | 1983-08-11 | Dr. Karl Thomae Gmbh, 7950 Biberach | Neue pyridobenzodiazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4558132A (en) * | 1982-07-02 | 1985-12-10 | A. H. Robins Company, Incorporated | Nitro, amino and aroylamino-N-phenylpyridinamines in a process for preparing pyrido[1,4]benzodiazepines |
| DE3409237A1 (de) * | 1984-03-14 | 1985-09-19 | Dr. Karl Thomae Gmbh, 7950 Biberach | Kondensierte diazepinone, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
-
1986
- 1986-07-31 DE DE19863626095 patent/DE3626095A1/de not_active Withdrawn
-
1987
- 1987-07-09 PH PH35517A patent/PH26406A/en unknown
- 1987-07-14 JP JP62175802A patent/JP2519734B2/ja not_active Expired - Lifetime
- 1987-07-15 DE DE8787110190T patent/DE3779369D1/de not_active Expired - Lifetime
- 1987-07-15 AT AT87110190T patent/ATE76643T1/de not_active IP Right Cessation
- 1987-07-15 EP EP87110190A patent/EP0254955B1/de not_active Expired - Lifetime
- 1987-07-15 ES ES87110190T patent/ES2042523T3/es not_active Expired - Lifetime
- 1987-07-29 IL IL83366A patent/IL83366A/xx unknown
- 1987-07-29 DD DD87305486A patent/DD265146A5/de not_active IP Right Cessation
- 1987-07-29 FI FI873297A patent/FI85479C/fi not_active IP Right Cessation
- 1987-07-29 CA CA000543258A patent/CA1311752C/en not_active Expired - Lifetime
- 1987-07-30 HU HU873522A patent/HU197745B/hu not_active IP Right Cessation
- 1987-07-30 NO NO873189A patent/NO165345C/no unknown
- 1987-07-30 NZ NZ221278A patent/NZ221278A/xx unknown
- 1987-07-30 IE IE206287A patent/IE60861B1/en not_active IP Right Cessation
- 1987-07-30 DK DK397687A patent/DK169722B1/da not_active IP Right Cessation
- 1987-07-30 ZA ZA875623A patent/ZA875623B/xx unknown
- 1987-07-30 PT PT85455A patent/PT85455B/pt not_active IP Right Cessation
- 1987-07-31 AU AU76350/87A patent/AU594489B2/en not_active Ceased
- 1987-07-31 KR KR1019870008387A patent/KR950010073B1/ko not_active Expired - Fee Related
- 1987-07-31 US US07/080,716 patent/US4971966A/en not_active Expired - Fee Related
-
1992
- 1992-07-13 GR GR920401502T patent/GR3005157T3/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PT1562946E (pt) | Novos derivados de xantina, sua preparação e sua utilização como produtos farmacêuticos | |
| US7442693B2 (en) | Diazepine compounds as ligands of the melanocortin 1 and/or 4 receptors | |
| JPS60215683A (ja) | 新規縮合ジアゼピノン | |
| JP2519734B2 (ja) | 新規置換ピリド〔２，３−ｂ〕〔１，４〕ベンゾジアゼピン−６−オン，その製法及びその化合物を含む医薬 | |
| CA2354213C (en) | N-triazolylmethyl-piperazine compounds with neurokinin-receptor antagonist activity | |
| CZ2000320A3 (cs) | Deriváty 4-oxo-3,5dihydro-4H-pyridazino[4,5-b]indol-1-acetamidu a farmaceutický prostředek, který je obsahuje | |
| US5175158A (en) | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds | |
| AU608641B2 (en) | Condensed diazepinones | |
| KR100196969B1 (ko) | 축합 디아제피논, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| CS248020B2 (en) | Production method of the (+)-enantiomere or (+-)-racemical 4a,9b-trans-hexahydro-1h-pyridoindole derivatives | |
| JP2574348B2 (ja) | 新規縮合ジアゼピノン、その製造法及びそれを含有する医薬組成物 | |
| US5002943A (en) | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds | |
| WO1998043976A1 (en) | Biphenyl derivatives and medicinal compositions | |
| US4931436A (en) | Condensed diazepinones, processes for preparing them and pharmaceutical compositions containing these compounds | |
| AU622887B2 (en) | Condensed diazepinones | |
| CN101759665B (zh) | 取代苯基哌嗪芳烷醇衍生物及其在制备镇痛药物中的应用 | |
| JPH0232074A (ja) | 新規縮合ジアゼピノン類、それらを製造する方法及びこれらの化合物を含有する医薬組成物 | |
| JPS624288A (ja) | 新規なジアゼピノン化合物 | |
| JPH0240371A (ja) | 新規縮合ジアゼピノン、それらの製造法及びこれらの化合物を含有する医薬的組成物 | |
| CN1950370B (zh) | 对映体纯的六氢吡咯并环戊吡啶-衍生物 | |
| US5610155A (en) | Condensed diazepinones, processes for preparing them and agents containing these compounds for treating diseases of the central nervous system and for promoting cerebral blood circulation |