CH616647A5 - - Google Patents
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- Publication number
- CH616647A5 CH616647A5 CH968376A CH968376A CH616647A5 CH 616647 A5 CH616647 A5 CH 616647A5 CH 968376 A CH968376 A CH 968376A CH 968376 A CH968376 A CH 968376A CH 616647 A5 CH616647 A5 CH 616647A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- derivatives
- benzocycloheptene
- radical
- carbon atoms
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 104
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 69
- -1 alkyl radical Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 38
- 239000000460 chlorine Substances 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 26
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000011707 mineral Substances 0.000 claims description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
- 150000007522 mineralic acids Chemical class 0.000 claims description 16
- 150000007524 organic acids Chemical class 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 12
- 235000005985 organic acids Nutrition 0.000 claims description 12
- SRGHTELVPDTMSI-UHFFFAOYSA-N 1h-benzo[7]annulen-1-amine Chemical class C1=CC=CC=C2C(N)C=CC=C21 SRGHTELVPDTMSI-UHFFFAOYSA-N 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 230000018044 dehydration Effects 0.000 claims description 4
- 238000006297 dehydration reaction Methods 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000011734 sodium Substances 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 3
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 3
- JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 141
- 239000000047 product Substances 0.000 description 118
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- 239000000203 mixture Substances 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 25
- 239000000243 solution Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000012074 organic phase Substances 0.000 description 16
- 239000000377 silicon dioxide Substances 0.000 description 15
- 239000012047 saturated solution Substances 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 229910021529 ammonia Inorganic materials 0.000 description 12
- 239000000284 extract Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
- HEOQXHNKRXRCTO-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulene Chemical compound C1CCCCC2=CC=CC=C21 HEOQXHNKRXRCTO-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- PATXNKIMSPSHMM-UHFFFAOYSA-N 3-chloro-7-(methylamino)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol Chemical compound OC1CC(NC)CCC2=CC=C(Cl)C=C21 PATXNKIMSPSHMM-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 6
- 229940087646 methanolamine Drugs 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- JNRKVVIKJKHAJM-UHFFFAOYSA-N 8,9-dihydrobenzo[7]annulen-5-one Chemical compound O=C1C=CCCC2=CC=CC=C12 JNRKVVIKJKHAJM-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 235000011087 fumaric acid Nutrition 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- QYQCHWFJKODOFG-UHFFFAOYSA-N 7-(dimethylamino)-5-phenyl-6,7,8,9-tetrahydrobenzo[7]annulen-5-ol Chemical compound C1C(N(C)C)CCC2=CC=CC=C2C1(O)C1=CC=CC=C1 QYQCHWFJKODOFG-UHFFFAOYSA-N 0.000 description 4
- JGRYPYKKMJFLEY-UHFFFAOYSA-N 7-(methylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound OC1CC(NC)CCC2=CC=CC=C21 JGRYPYKKMJFLEY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- SCEZBURBUAIBOK-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound C1CN(C)CCN1C1CC(O)C2=CC=CC=C2CC1 SCEZBURBUAIBOK-UHFFFAOYSA-N 0.000 description 3
- BHLSVSQLUQODGS-UHFFFAOYSA-N 7-(dimethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound OC1CC(N(C)C)CCC2=CC=CC=C21 BHLSVSQLUQODGS-UHFFFAOYSA-N 0.000 description 3
- XFZBLULZQHTDLF-UHFFFAOYSA-N 7-(dimethylamino)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CC(N(C)C)CCC2=CC=CC=C21 XFZBLULZQHTDLF-UHFFFAOYSA-N 0.000 description 3
- HKRWEBFHMZGMCB-UHFFFAOYSA-N 7-(methylamino)-5-phenyl-6,7,8,9-tetrahydrobenzo[7]annulen-5-ol Chemical compound C1C(NC)CCC2=CC=CC=C2C1(O)C1=CC=CC=C1 HKRWEBFHMZGMCB-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 3
- 208000020401 Depressive disease Diseases 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
- 229910052808 lithium carbonate Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- OQKZSMVOTBJSST-WLHGVMLRSA-N (E)-but-2-enedioic acid 3-chloro-N,N-dimethyl-8,9-dihydro-7H-benzo[7]annulen-7-amine Chemical compound OC(=O)\C=C\C(O)=O.C1=CC(N(C)C)CCC2=CC=C(Cl)C=C21 OQKZSMVOTBJSST-WLHGVMLRSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XIENOGULFMYIGZ-UHFFFAOYSA-N 1-chloro-7-(methylamino)-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-ol Chemical compound OC1CC(NC)CCC2=C(Cl)C=CC=C21 XIENOGULFMYIGZ-UHFFFAOYSA-N 0.000 description 2
- VZCJWRGSPOJGLH-UHFFFAOYSA-N 3-chloro-8,9-dihydrobenzo[7]annulen-5-one Chemical class C1CC=CC(=O)C2=CC(Cl)=CC=C21 VZCJWRGSPOJGLH-UHFFFAOYSA-N 0.000 description 2
- LOISBKFXIXXAAL-UHFFFAOYSA-N 7-(4-methylpiperazin-1-yl)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound C1CN(C)CCN1C1CC(=O)C2=CC=CC=C2CC1 LOISBKFXIXXAAL-UHFFFAOYSA-N 0.000 description 2
- JMSFIVQQLBAFGW-UHFFFAOYSA-N 7-(methylamino)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CC(NC)CCC2=CC=CC=C21 JMSFIVQQLBAFGW-UHFFFAOYSA-N 0.000 description 2
- OXKKEVFCGNOTNQ-UHFFFAOYSA-N 7-pyrrolidin-1-yl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound C1CC2=CC=CC=C2C(O)CC1N1CCCC1 OXKKEVFCGNOTNQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- WWVMUMHYOWBHQS-UHFFFAOYSA-N n-methyl-8,9-dihydro-7h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C1=CC(NC)CCC2=CC=CC=C21 WWVMUMHYOWBHQS-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000002524 organometallic group Chemical group 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- BYENNPOSPUZKMQ-UHFFFAOYSA-N 1-chloro-n-methyl-8,9-dihydro-7h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C1=CC(NC)CCC2=C(Cl)C=CC=C21 BYENNPOSPUZKMQ-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZVCPCZRXWGOICC-UHFFFAOYSA-N 1h-benzo[7]annulene Chemical class C1=CC=CC=C2CC=CC=C21 ZVCPCZRXWGOICC-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 description 1
- QADMFWJCWPCSSH-UHFFFAOYSA-N 3-chloro-7-(methylamino)-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CC(NC)CCC2=CC=C(Cl)C=C21 QADMFWJCWPCSSH-UHFFFAOYSA-N 0.000 description 1
- JPULZQMYPMQECI-UHFFFAOYSA-N 3-chloro-n,n-dimethyl-8,9-dihydro-7h-benzo[7]annulen-7-amine Chemical compound C1=CC(N(C)C)CCC2=CC=C(Cl)C=C21 JPULZQMYPMQECI-UHFFFAOYSA-N 0.000 description 1
- MRUWMQFQMKVFJJ-UHFFFAOYSA-N 3-chloro-n-methyl-8,9-dihydro-7h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C1=CC(NC)CCC2=CC=C(Cl)C=C21 MRUWMQFQMKVFJJ-UHFFFAOYSA-N 0.000 description 1
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- XHVULKQHRQZNMW-UHFFFAOYSA-N 5H-benzocycloheptene Chemical compound C1C=CC=CC2=CC=CC=C12 XHVULKQHRQZNMW-UHFFFAOYSA-N 0.000 description 1
- RTSRUUJKIOUOCT-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulen-4-amine Chemical group C1CCCCC2=C1C=CC=C2N RTSRUUJKIOUOCT-UHFFFAOYSA-N 0.000 description 1
- ZBNIQZCMPPVSKL-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound OC1CCCCC2=CC=CC=C12 ZBNIQZCMPPVSKL-UHFFFAOYSA-N 0.000 description 1
- KWHUHTFXMNQHAA-UHFFFAOYSA-N 6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound O=C1CCCCC2=CC=CC=C12 KWHUHTFXMNQHAA-UHFFFAOYSA-N 0.000 description 1
- WKJSBFXJGZJVET-UHFFFAOYSA-N 7,8-dihydrobenzo[7]annulen-9-one Chemical compound O=C1CCC=CC2=CC=CC=C12 WKJSBFXJGZJVET-UHFFFAOYSA-N 0.000 description 1
- JHZUHZOUGFWUEQ-UHFFFAOYSA-N 7-(ethylamino)-6,7,8,9-tetrahydro-5h-benzo[7]annulen-5-ol Chemical compound OC1CC(NCC)CCC2=CC=CC=C21 JHZUHZOUGFWUEQ-UHFFFAOYSA-N 0.000 description 1
- ORQONBDVGHVCKP-UHFFFAOYSA-N 7-pyrrolidin-1-yl-6,7,8,9-tetrahydrobenzo[7]annulen-5-one Chemical compound C1CC2=CC=CC=C2C(=O)CC1N1CCCC1 ORQONBDVGHVCKP-UHFFFAOYSA-N 0.000 description 1
- DTRRHWQMEXXDFE-UHFFFAOYSA-N 8,9-dihydro-7h-benzo[7]annulene Chemical compound C1CCC=CC2=CC=CC=C21 DTRRHWQMEXXDFE-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- NNPNQMHEXQZXJG-UHFFFAOYSA-N Cl.O=C1CC(NCC)CCC2=CC=CC=C21 Chemical compound Cl.O=C1CC(NCC)CCC2=CC=CC=C21 NNPNQMHEXQZXJG-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
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- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- BFKVXNPJXXJUGQ-UHFFFAOYSA-N [CH2]CCCC Chemical compound [CH2]CCCC BFKVXNPJXXJUGQ-UHFFFAOYSA-N 0.000 description 1
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- YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 239000001166 ammonium sulphate Substances 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
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- 150000001555 benzenes Chemical class 0.000 description 1
- SBWVASGNXJVLND-UHFFFAOYSA-N benzo[7]annulen-5-one Chemical compound O=C1C=CC=CC2=CC=CC=C12 SBWVASGNXJVLND-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
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- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 208000016253 exhaustion Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 150000002641 lithium Chemical group 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- WUBABGHLEBDGMP-UHFFFAOYSA-N n,n-dimethyl-5-phenyl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-7-amine Chemical class C1C(N(C)C)CCC2=CC=CC=C2C1C1=CC=CC=C1 WUBABGHLEBDGMP-UHFFFAOYSA-N 0.000 description 1
- KYYGFIJWCMFGJB-UHFFFAOYSA-N n,n-dimethyl-5-phenyl-6,7,8,9-tetrahydro-5h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C1C(N(C)C)CCC2=CC=CC=C2C1C1=CC=CC=C1 KYYGFIJWCMFGJB-UHFFFAOYSA-N 0.000 description 1
- YDOHXXSVUANDDG-UHFFFAOYSA-N n,n-dimethyl-5-phenyl-8,9-dihydro-7h-benzo[7]annulen-7-amine Chemical compound C=1C(N(C)C)CCC2=CC=CC=C2C=1C1=CC=CC=C1 YDOHXXSVUANDDG-UHFFFAOYSA-N 0.000 description 1
- RTPRCMIRDVQVSX-UHFFFAOYSA-N n,n-dimethyl-8,9-dihydro-7h-benzo[7]annulen-7-amine Chemical compound C1=CC(N(C)C)CCC2=CC=CC=C21 RTPRCMIRDVQVSX-UHFFFAOYSA-N 0.000 description 1
- HPEVKMZWOAVHTR-UHFFFAOYSA-N n-ethyl-8,9-dihydro-7h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C1=CC(NCC)CCC2=CC=CC=C21 HPEVKMZWOAVHTR-UHFFFAOYSA-N 0.000 description 1
- VCGDNHIWYUGTPM-UHFFFAOYSA-N n-methyl-5-phenyl-8,9-dihydro-7h-benzo[7]annulen-7-amine Chemical compound C=1C(NC)CCC2=CC=CC=C2C=1C1=CC=CC=C1 VCGDNHIWYUGTPM-UHFFFAOYSA-N 0.000 description 1
- OHVPZDWSMXQANK-UHFFFAOYSA-N n-methyl-5-phenyl-8,9-dihydro-7h-benzo[7]annulen-7-amine;hydrochloride Chemical compound Cl.C=1C(NC)CCC2=CC=CC=C2C=1C1=CC=CC=C1 OHVPZDWSMXQANK-UHFFFAOYSA-N 0.000 description 1
- LVDLUVNNZAIWGM-UHFFFAOYSA-N n-methyl-8,9-dihydro-7h-benzo[7]annulen-7-amine Chemical compound C1=CC(NC)CCC2=CC=CC=C21 LVDLUVNNZAIWGM-UHFFFAOYSA-N 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
- C07D295/112—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
- C07D295/116—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings with the doubly bound oxygen or sulfur atoms directly attached to a carbocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/39—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton
- C07C211/41—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems
- C07C211/42—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of an unsaturated carbon skeleton containing condensed ring systems with six-membered aromatic rings being part of the condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/033—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/12—One of the condensed rings being a six-membered aromatic ring the other ring being at least seven-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7523499A FR2319332A1 (fr) | 1975-07-28 | 1975-07-28 | Nouveaux derives de l'aminobenzocycloheptene et leurs sels, procede de preparation et application a titre de medicaments desdits produits |
Publications (1)
Publication Number | Publication Date |
---|---|
CH616647A5 true CH616647A5 (d) | 1980-04-15 |
Family
ID=9158434
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH968376A CH616647A5 (d) | 1975-07-28 | 1976-07-28 |
Country Status (23)
Country | Link |
---|---|
US (1) | US4091115A (d) |
JP (1) | JPS5217455A (d) |
AT (1) | AT346303B (d) |
AU (1) | AU503674B2 (d) |
BE (1) | BE844555A (d) |
CA (1) | CA1088070A (d) |
CH (1) | CH616647A5 (d) |
DD (1) | DD126800A5 (d) |
DE (1) | DE2633889C2 (d) |
DK (1) | DK143105C (d) |
ES (2) | ES450166A1 (d) |
FI (1) | FI63014C (d) |
FR (1) | FR2319332A1 (d) |
GB (1) | GB1503119A (d) |
HU (1) | HU175289B (d) |
IE (1) | IE44014B1 (d) |
IL (1) | IL50116A (d) |
LU (1) | LU75470A1 (d) |
NL (1) | NL7608398A (d) |
PT (1) | PT65413B (d) |
SE (1) | SE7607944L (d) |
SU (1) | SU682121A3 (d) |
ZA (1) | ZA764546B (d) |
Families Citing this family (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2365339A1 (fr) * | 1976-09-23 | 1978-04-21 | Roussel Uclaf | Nouveaux derives de l'aminobenzocycloheptene, ainsi que leurs sels, procede de preparation et application a titre de medicaments de ces nouveaux produits |
DK390477A (da) * | 1977-05-23 | 1978-11-24 | Sandoz Ag | Fremgangsmaade til fremstilling af cycloheptenderivater |
FR2409256A1 (fr) * | 1977-11-18 | 1979-06-15 | Roussel Uclaf | Nouveaux derives de la 5h-benzocycloepten-7-amine et leurs sels, procede de preparation et application a titre de medicament |
FR2633617B1 (fr) * | 1988-07-04 | 1991-02-08 | Adir | Nouveaux derives du benzocycloheptene, leur procede de preparation et les compositions pharmaceutiques les renfermant |
JPH051033A (ja) * | 1991-06-18 | 1993-01-08 | Tanabe Seiyaku Co Ltd | ベンゾシクロヘプテン誘導体及びその製法 |
JP2003291819A (ja) * | 2002-03-29 | 2003-10-15 | Sanyo Electric Co Ltd | 台 車 |
CA2542077A1 (en) * | 2003-10-08 | 2005-04-21 | President And Fellows Of Harvard College | Pyrovalerone analogs and therapeutic uses thereof |
US8586634B2 (en) * | 2007-06-15 | 2013-11-19 | University Of Florida Research Foundation, Inc. | Therapeutic compounds |
US8278466B2 (en) | 2008-04-28 | 2012-10-02 | Janssen Pharmaceutica Nv | Benzocycloheptane and benzoxepine derivatives |
JP5932636B2 (ja) | 2009-05-05 | 2016-06-08 | ユニバーシティ オブ フロリダ リサーチ ファウンデーション,インコーポレイテッド | 治療化合物 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1202791B (de) * | 1960-09-19 | 1965-10-14 | Smith Kline French Lab | Verfahren zur Herstellung substituierter Cyclopropylamine |
US3253037A (en) * | 1962-06-19 | 1966-05-24 | Ciba Geigy Corp | N-2-alkynyl-amino-benzocylo-alkanes |
US3836534A (en) * | 1969-05-01 | 1974-09-17 | Colgate Palmolive Co | 5-piperazino-6-hydroxy-5h-benzo-cycloheptenes |
US3751420A (en) * | 1971-04-01 | 1973-08-07 | Squibb & Sons Inc | Monoolmonoene amines |
-
1975
- 1975-07-28 FR FR7523499A patent/FR2319332A1/fr active Granted
-
1976
- 1976-07-02 HU HU76RO889A patent/HU175289B/hu unknown
- 1976-07-12 SE SE7607944A patent/SE7607944L/xx unknown
- 1976-07-21 CA CA257,474A patent/CA1088070A/fr not_active Expired
- 1976-07-23 FI FI762107A patent/FI63014C/fi not_active IP Right Cessation
- 1976-07-23 SU SU762382454A patent/SU682121A3/ru active
- 1976-07-23 IL IL50116A patent/IL50116A/xx unknown
- 1976-07-26 ES ES450166A patent/ES450166A1/es not_active Expired
- 1976-07-26 US US05/708,749 patent/US4091115A/en not_active Expired - Lifetime
- 1976-07-27 DD DD194089A patent/DD126800A5/xx unknown
- 1976-07-27 BE BE169272A patent/BE844555A/xx not_active IP Right Cessation
- 1976-07-27 AU AU16295/76A patent/AU503674B2/en not_active Expired
- 1976-07-27 PT PT65413A patent/PT65413B/pt unknown
- 1976-07-27 LU LU75470A patent/LU75470A1/xx unknown
- 1976-07-28 DE DE2633889A patent/DE2633889C2/de not_active Expired
- 1976-07-28 GB GB31497/76A patent/GB1503119A/en not_active Expired
- 1976-07-28 JP JP51089272A patent/JPS5217455A/ja active Pending
- 1976-07-28 IE IE1671/76A patent/IE44014B1/en unknown
- 1976-07-28 ZA ZA764546A patent/ZA764546B/xx unknown
- 1976-07-28 NL NL7608398A patent/NL7608398A/xx not_active Application Discontinuation
- 1976-07-28 CH CH968376A patent/CH616647A5/fr not_active IP Right Cessation
- 1976-07-28 DK DK338376A patent/DK143105C/da active
- 1976-07-28 AT AT555776A patent/AT346303B/de not_active IP Right Cessation
-
1977
- 1977-08-01 ES ES461268A patent/ES461268A1/es not_active Expired
Also Published As
Publication number | Publication date |
---|---|
SE7607944L (sv) | 1977-01-29 |
FI762107A7 (d) | 1977-01-29 |
DE2633889A1 (de) | 1977-02-17 |
DD126800A5 (d) | 1977-08-10 |
IL50116A (en) | 1979-10-31 |
ES461268A1 (es) | 1978-08-16 |
FR2319332A1 (fr) | 1977-02-25 |
IL50116A0 (en) | 1976-09-30 |
DK338376A (da) | 1977-01-29 |
IE44014L (en) | 1977-01-28 |
BE844555A (fr) | 1977-01-27 |
CA1088070A (fr) | 1980-10-21 |
AU503674B2 (en) | 1979-09-13 |
HU175289B (hu) | 1980-06-28 |
DK143105B (da) | 1981-03-30 |
JPS5217455A (en) | 1977-02-09 |
FI63014B (fi) | 1982-12-31 |
AU1629576A (en) | 1978-02-02 |
DE2633889C2 (de) | 1982-12-23 |
PT65413A (fr) | 1976-08-01 |
GB1503119A (en) | 1978-03-08 |
ZA764546B (en) | 1977-09-28 |
IE44014B1 (en) | 1981-07-29 |
ATA555776A (de) | 1978-03-15 |
ES450166A1 (es) | 1977-11-16 |
DK143105C (da) | 1981-11-09 |
US4091115A (en) | 1978-05-23 |
FR2319332B1 (d) | 1978-11-17 |
NL7608398A (nl) | 1977-02-01 |
FI63014C (fi) | 1983-04-11 |
SU682121A3 (ru) | 1979-08-25 |
AT346303B (de) | 1978-11-10 |
PT65413B (fr) | 1978-06-09 |
LU75470A1 (d) | 1977-04-06 |
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