NO855373L - Fremstilling av dibenz(b,c)-oksepin- og dibenz(b,c)-tiepin-derivater. - Google Patents
Fremstilling av dibenz(b,c)-oksepin- og dibenz(b,c)-tiepin-derivater.Info
- Publication number
- NO855373L NO855373L NO855373A NO855373A NO855373L NO 855373 L NO855373 L NO 855373L NO 855373 A NO855373 A NO 855373A NO 855373 A NO855373 A NO 855373A NO 855373 L NO855373 L NO 855373L
- Authority
- NO
- Norway
- Prior art keywords
- oxepin
- dihydrodibenz
- sup
- general formula
- compound
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 101
- 238000000034 method Methods 0.000 claims abstract description 69
- -1 nitro, hydroxy, cyano, carbamyl Chemical group 0.000 claims abstract description 42
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 239000001257 hydrogen Substances 0.000 claims abstract description 31
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 9
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001424 substituent group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims abstract description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 125000002252 acyl group Chemical group 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 3
- 125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 3
- 125000004103 aminoalkyl group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims abstract 2
- ATYBXHSAIOKLMG-UHFFFAOYSA-N oxepin Chemical compound O1C=CC=CC=C1 ATYBXHSAIOKLMG-UHFFFAOYSA-N 0.000 claims abstract 2
- 150000001412 amines Chemical class 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 125000001246 bromo group Chemical group Br* 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 238000006268 reductive amination reaction Methods 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 150000003551 thiepines Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 150000007522 mineralic acids Chemical class 0.000 abstract description 4
- 150000007524 organic acids Chemical class 0.000 abstract description 4
- 235000005985 organic acids Nutrition 0.000 abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 230000000144 pharmacologic effect Effects 0.000 abstract description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003638 chemical reducing agent Substances 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 10
- 239000007858 starting material Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- IVHAXCDBVWNOJF-UHFFFAOYSA-N 8-chloro-11-(methylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNC)(O)C2=CC=C(Cl)C=C21 IVHAXCDBVWNOJF-UHFFFAOYSA-N 0.000 description 4
- FEEMHGODPIRLAM-UHFFFAOYSA-N 9-chloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=C(Cl)C=C2C(CN(C)C)(O)C2=CC=CC=C21 FEEMHGODPIRLAM-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- BJJXMYXMMQTZCL-UHFFFAOYSA-N 11-(1-aminoethyl)-9-chloro-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=C(Cl)C=C2C(C(N)C)(O)C2=CC=CC=C21 BJJXMYXMMQTZCL-UHFFFAOYSA-N 0.000 description 3
- WOAWMXHGPDJQIR-UHFFFAOYSA-N 11-(methylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNC)(O)C2=CC=CC=C21 WOAWMXHGPDJQIR-UHFFFAOYSA-N 0.000 description 3
- ACYFWWLCJDGKPV-UHFFFAOYSA-N 8-fluoro-11-(methylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNC)(O)C2=CC=C(F)C=C21 ACYFWWLCJDGKPV-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000027939 micturition Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 150000003556 thioamides Chemical group 0.000 description 3
- CUWJWLVZWXASKD-UHFFFAOYSA-N 11-(1-aminoethyl)-2-chloro-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=C(Cl)C=C2C(C(N)C)(O)C2=CC=CC=C21 CUWJWLVZWXASKD-UHFFFAOYSA-N 0.000 description 2
- IQHNPFBZKTVKRF-UHFFFAOYSA-N 11-(1-aminoethyl)-8-chloro-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(C(N)C)(O)C2=CC=C(Cl)C=C21 IQHNPFBZKTVKRF-UHFFFAOYSA-N 0.000 description 2
- HVRIJTZLELFTGU-UHFFFAOYSA-N 11-(aminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CN)(O)C2=CC=CC=C21 HVRIJTZLELFTGU-UHFFFAOYSA-N 0.000 description 2
- UNYXTGALHIZGTG-UHFFFAOYSA-N 11-(ethylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNCC)(O)C2=CC=CC=C21 UNYXTGALHIZGTG-UHFFFAOYSA-N 0.000 description 2
- SWLZSWGYNVRWAG-UHFFFAOYSA-N 11-(methylaminomethyl)-6h-benzo[c][1]benzoxepine-7,8,11-triol Chemical compound C1OC2=CC=CC=C2C(CNC)(O)C2=CC=C(O)C(O)=C21 SWLZSWGYNVRWAG-UHFFFAOYSA-N 0.000 description 2
- GXHSALMACSOSGK-UHFFFAOYSA-N 11-(methylaminomethyl)-9-(trifluoromethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=C(C(F)(F)F)C=C2C(CNC)(O)C2=CC=CC=C21 GXHSALMACSOSGK-UHFFFAOYSA-N 0.000 description 2
- YIIJHCFSXVJWPX-UHFFFAOYSA-N 11-[(dimethylamino)methyl]-2-methylsulfanyl-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=CC=C2C(O)(CN(C)C)C2=CC(SC)=CC=C21 YIIJHCFSXVJWPX-UHFFFAOYSA-N 0.000 description 2
- PFWZBMWLBCWXNT-UHFFFAOYSA-N 11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CN(C)C)(O)C2=CC=CC=C21 PFWZBMWLBCWXNT-UHFFFAOYSA-N 0.000 description 2
- AJVOKWJNZQQNDW-UHFFFAOYSA-N 11-hydroxy-11-[(2-hydroxyethylamino)methyl]-6h-benzo[c][1]benzoxepine-8-carbonitrile Chemical compound C1OC2=CC=CC=C2C(CNCCO)(O)C2=CC=C(C#N)C=C21 AJVOKWJNZQQNDW-UHFFFAOYSA-N 0.000 description 2
- QDAUQDRRVOKUCJ-UHFFFAOYSA-N 2,9-dichloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=C(Cl)C=C2C(CN(C)C)(O)C2=CC(Cl)=CC=C21 QDAUQDRRVOKUCJ-UHFFFAOYSA-N 0.000 description 2
- PTDZMWATFVQSEE-UHFFFAOYSA-N 2-chloro-11-(methylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=C(Cl)C=C2C(CNC)(O)C2=CC=CC=C21 PTDZMWATFVQSEE-UHFFFAOYSA-N 0.000 description 2
- SCPGTZCDEGRQIH-UHFFFAOYSA-N 2-chloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=C(Cl)C=C2C(CN(C)C)(O)C2=CC=CC=C21 SCPGTZCDEGRQIH-UHFFFAOYSA-N 0.000 description 2
- RJKGXKOKUNXLRG-UHFFFAOYSA-N 4-chloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=C(Cl)C=CC=C2C(CN(C)C)(O)C2=CC=CC=C21 RJKGXKOKUNXLRG-UHFFFAOYSA-N 0.000 description 2
- YUSHFLBKQQILNV-UHFFFAOYSA-N 6h-benzo[c][1]benzoxepin-11-one Chemical compound C1OC2=CC=CC=C2C(=O)C2=CC=CC=C21 YUSHFLBKQQILNV-UHFFFAOYSA-N 0.000 description 2
- FEUXUYWHTPCCDS-UHFFFAOYSA-N 8-chloro-11-[(2-hydroxyethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNCCO)(O)C2=CC=C(Cl)C=C21 FEUXUYWHTPCCDS-UHFFFAOYSA-N 0.000 description 2
- PXZMTKDUWDFERO-UHFFFAOYSA-N 8-chloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CN(C)C)(O)C2=CC=C(Cl)C=C21 PXZMTKDUWDFERO-UHFFFAOYSA-N 0.000 description 2
- KHVQSPZIHUOTDU-UHFFFAOYSA-N 9-chloro-11-(methylaminomethyl)-6h-benzo[c][1]benzothiepin-11-ol Chemical compound S1CC2=CC=C(Cl)C=C2C(CNC)(O)C2=CC=CC=C21 KHVQSPZIHUOTDU-UHFFFAOYSA-N 0.000 description 2
- VUUJWQIUVVNLFC-UHFFFAOYSA-N 9-chloro-11-[(2-hydroxyethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=CC=C2C(CNCCO)(O)C2=CC(Cl)=CC=C21 VUUJWQIUVVNLFC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000026723 Urinary tract disease Diseases 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 208000014001 urinary system disease Diseases 0.000 description 2
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
- CZFPEJRJJZKMKF-UHFFFAOYSA-N 1-ethyl-6,11-dihydrobenzo[c][1]benzoxepin-11-ol Chemical compound C(C)C1=CC=CC=2OCC3=C(C(C=21)O)C=CC=C3 CZFPEJRJJZKMKF-UHFFFAOYSA-N 0.000 description 1
- 125000006017 1-propenyl group Chemical group 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- XSRDMTQBWFDBMU-UHFFFAOYSA-N 10-chloro-11-(methylaminomethyl)-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=CC(Cl)=C2C(CNC)(O)C2=CC=CC=C21 XSRDMTQBWFDBMU-UHFFFAOYSA-N 0.000 description 1
- AHLNFPJJOSLGLI-UHFFFAOYSA-N 10-chloro-11-[(2-hydroxyethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=CC(Cl)=C2C(CNCCO)(O)C2=CC=CC=C21 AHLNFPJJOSLGLI-UHFFFAOYSA-N 0.000 description 1
- DFMPSLPGWYYLID-UHFFFAOYSA-N 10-chloro-11-[(dimethylamino)methyl]-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=CC(Cl)=C2C(CN(C)C)(O)C2=CC=CC=C21 DFMPSLPGWYYLID-UHFFFAOYSA-N 0.000 description 1
- VMLZOGDRSJPIJS-UHFFFAOYSA-N 11-(1-aminoethyl)-2-fluoro-6h-benzo[c][1]benzoxepin-11-ol Chemical compound C1OC2=CC=C(F)C=C2C(C(N)C)(O)C2=CC=CC=C21 VMLZOGDRSJPIJS-UHFFFAOYSA-N 0.000 description 1
- XTSZKWLCTFVMDV-UHFFFAOYSA-N 11-(1-aminoethyl)-9-fluoro-6h-benzo[c][1]benzoxepin-11-ol Chemical compound O1CC2=CC=C(F)C=C2C(C(N)C)(O)C2=CC=CC=C21 XTSZKWLCTFVMDV-UHFFFAOYSA-N 0.000 description 1
- BUWSCFBEAQZUOJ-UHFFFAOYSA-N 11-(aminomethyl)-11-hydroxy-6h-benzo[c][1]benzoxepine-4-carbonitrile Chemical compound C1OC2=C(C#N)C=CC=C2C(CN)(O)C2=CC=CC=C21 BUWSCFBEAQZUOJ-UHFFFAOYSA-N 0.000 description 1
- FFBHIDJBYXDDOV-UHFFFAOYSA-N 11-(aminomethyl)-11-hydroxy-6h-benzo[c][1]benzoxepine-7-carbonitrile Chemical compound O1CC2=C(C#N)C=CC=C2C(CN)(O)C2=CC=CC=C21 FFBHIDJBYXDDOV-UHFFFAOYSA-N 0.000 description 1
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- 238000007363 ring formation reaction Methods 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- XHFLOLLMZOTPSM-UHFFFAOYSA-M sodium;hydrogen carbonate;hydrate Chemical compound [OH-].[Na+].OC(O)=O XHFLOLLMZOTPSM-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- 210000003708 urethra Anatomy 0.000 description 1
- 210000003932 urinary bladder Anatomy 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE8500273A SE8500273D0 (sv) | 1985-01-22 | 1985-01-22 | Nya tricykliska foreningar, kompositioner innehallande sadana foreningar, framstellningsforfaranden och behandlingsmetoder |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO855373L true NO855373L (no) | 1986-07-23 |
Family
ID=20358842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO855373A NO855373L (no) | 1985-01-22 | 1985-12-30 | Fremstilling av dibenz(b,c)-oksepin- og dibenz(b,c)-tiepin-derivater. |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4645758A (sv) |
| EP (1) | EP0189078B1 (sv) |
| JP (1) | JPH0798817B2 (sv) |
| AT (1) | ATE44280T1 (sv) |
| AU (1) | AU587597B2 (sv) |
| CA (1) | CA1309409C (sv) |
| DE (1) | DE3664136D1 (sv) |
| DK (1) | DK31486A (sv) |
| FI (1) | FI860199A (sv) |
| IE (1) | IE59600B1 (sv) |
| NO (1) | NO855373L (sv) |
| SE (1) | SE8500273D0 (sv) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0560831B1 (sv) * | 1986-06-17 | 1993-09-03 | Dainippon Pharmaceutical Co | |
| US5340826A (en) * | 1993-02-04 | 1994-08-23 | Pfizer Inc. | Pharmaceutical agents for treatment of urinary incontinence |
| US5574173A (en) * | 1993-12-06 | 1996-11-12 | Schering Corporation | Tricyclic derivatives, compositions and methods of use |
| JP3348230B2 (ja) | 1995-03-03 | 2002-11-20 | アルゴス ファーマシューティカル コーポレーション | 尿失禁の治療用のデキシトルメトルファン又はデキシトルオルファンの使用 |
| US6323206B1 (en) | 1996-07-12 | 2001-11-27 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| KR100447674B1 (ko) * | 1997-04-15 | 2004-09-08 | 교와 핫꼬 고교 가부시끼가이샤 | 삼환식 화합물 |
| US6509346B2 (en) | 1998-01-21 | 2003-01-21 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US6613905B1 (en) | 1998-01-21 | 2003-09-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| CA2319077A1 (en) | 1998-01-21 | 1999-07-29 | Yoshisuke Nakasato | Chemokine receptor antagonists and methods of use therefor |
| US7271176B2 (en) * | 1998-09-04 | 2007-09-18 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use thereof |
| US7541365B2 (en) | 2001-11-21 | 2009-06-02 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists and methods of use therefor |
| US7378408B2 (en) * | 2001-11-30 | 2008-05-27 | Pfizer Inc. | Methods of treatment and formulations of cephalosporin |
| TWI291467B (en) * | 2002-11-13 | 2007-12-21 | Millennium Pharm Inc | CCR1 antagonists and methods of use therefor |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1332145A (sv) * | 1961-06-08 | 1963-12-16 | ||
| NL300844A (sv) * | 1962-11-24 | |||
| NL130988C (sv) * | 1966-07-21 | Boehringer Mannheim Gmbh | ||
| US3876659A (en) * | 1970-09-18 | 1975-04-08 | Sandoz Ag | Spiro tricyclic isoindolines |
| FR2512024A1 (fr) * | 1981-08-27 | 1983-03-04 | Adir | Ethers tricycliques, leur preparation et les compositions pharmaceutiques les contenant |
| JPS6147466A (ja) * | 1984-08-10 | 1986-03-07 | Dainippon Pharmaceut Co Ltd | アミン誘導体 |
-
1985
- 1985-01-22 SE SE8500273A patent/SE8500273D0/sv unknown
- 1985-12-30 NO NO855373A patent/NO855373L/no unknown
- 1985-12-30 IE IE332585A patent/IE59600B1/en not_active IP Right Cessation
-
1986
- 1986-01-10 AU AU52171/86A patent/AU587597B2/en not_active Ceased
- 1986-01-11 DE DE8686100324T patent/DE3664136D1/de not_active Expired
- 1986-01-11 AT AT86100324T patent/ATE44280T1/de not_active IP Right Cessation
- 1986-01-11 EP EP86100324A patent/EP0189078B1/en not_active Expired
- 1986-01-16 FI FI860199A patent/FI860199A/fi not_active Application Discontinuation
- 1986-01-17 US US06/820,428 patent/US4645758A/en not_active Expired - Fee Related
- 1986-01-21 CA CA000500044A patent/CA1309409C/en not_active Expired - Fee Related
- 1986-01-21 JP JP61010959A patent/JPH0798817B2/ja not_active Expired - Lifetime
- 1986-01-21 DK DK31486A patent/DK31486A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| SE8500273D0 (sv) | 1985-01-22 |
| JPH0798817B2 (ja) | 1995-10-25 |
| FI860199A (fi) | 1986-07-23 |
| EP0189078B1 (en) | 1989-06-28 |
| AU587597B2 (en) | 1989-08-24 |
| DK31486A (da) | 1986-07-23 |
| US4645758A (en) | 1987-02-24 |
| IE59600B1 (en) | 1994-03-09 |
| DE3664136D1 (en) | 1989-08-03 |
| ATE44280T1 (de) | 1989-07-15 |
| DK31486D0 (da) | 1986-01-21 |
| CA1309409C (en) | 1992-10-27 |
| AU5217186A (en) | 1986-07-31 |
| EP0189078A1 (en) | 1986-07-30 |
| FI860199A0 (fi) | 1986-01-16 |
| IE853325L (en) | 1986-07-22 |
| JPS61172871A (ja) | 1986-08-04 |
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