IL41403A - 10,11-dihydro-5,10-imino-dibenzocycloheptene derivatives and their preparation - Google Patents
10,11-dihydro-5,10-imino-dibenzocycloheptene derivatives and their preparationInfo
- Publication number
- IL41403A IL41403A IL41403A IL4140373A IL41403A IL 41403 A IL41403 A IL 41403A IL 41403 A IL41403 A IL 41403A IL 4140373 A IL4140373 A IL 4140373A IL 41403 A IL41403 A IL 41403A
- Authority
- IL
- Israel
- Prior art keywords
- radical
- formula
- dibenzo
- cycloheptene
- group
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 8
- NUBPAAVFKYZAEO-UHFFFAOYSA-N 16-azatetracyclo[8.5.1.02,7.08,13]hexadeca-1,3,5,7,12,14-hexaene Chemical class N1C=2C=CC=3C(=C4C=2C=CC=C4)CC1CC=3 NUBPAAVFKYZAEO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims abstract description 9
- 150000002431 hydrogen Chemical group 0.000 claims abstract 5
- -1 alkyl radical Chemical class 0.000 claims description 36
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 15
- 239000011707 mineral Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 230000000063 preceeding effect Effects 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical class [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 claims description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 102000004157 Hydrolases Human genes 0.000 claims description 2
- 108090000604 Hydrolases Proteins 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 238000007792 addition Methods 0.000 claims 6
- 150000007522 mineralic acids Chemical class 0.000 claims 4
- 150000007524 organic acids Chemical class 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- QPJORFLSOJAUNL-UHFFFAOYSA-N dibenzo[a,d][7]annulene Chemical compound C1=CC2=CC=CC=C2CC2=CC=CC=C21 QPJORFLSOJAUNL-UHFFFAOYSA-N 0.000 claims 2
- 229910052740 iodine Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- FSVJFNAIGNNGKK-UHFFFAOYSA-N 2-[cyclohexyl(oxo)methyl]-3,6,7,11b-tetrahydro-1H-pyrazino[2,1-a]isoquinolin-4-one Chemical compound C1C(C2=CC=CC=C2CC2)N2C(=O)CN1C(=O)C1CCCCC1 FSVJFNAIGNNGKK-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 150000001350 alkyl halides Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 abstract description 3
- 210000003169 central nervous system Anatomy 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 230000004936 stimulating effect Effects 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 239000001961 anticonvulsive agent Substances 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- PJQCANLCUDUPRF-UHFFFAOYSA-N dibenzocycloheptene Chemical compound C1CC2=CC=CC=C2CC2=CC=CC=C12 PJQCANLCUDUPRF-UHFFFAOYSA-N 0.000 description 58
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 40
- 239000000284 extract Substances 0.000 description 28
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 20
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 20
- 235000019341 magnesium sulphate Nutrition 0.000 description 20
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- 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 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 235000008504 concentrate Nutrition 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- NXLKILXESHWQPQ-UHFFFAOYSA-N tricyclo[9.4.0.02,7]pentadeca-1,3,5,7,9,11-hexaene Chemical compound C1=CC=C2C=CC=CC2=C2CCCC=C21 NXLKILXESHWQPQ-UHFFFAOYSA-N 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000013019 agitation Methods 0.000 description 6
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 235000010755 mineral Nutrition 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 229940095054 ammoniac Drugs 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- MJEMIOXXNCZZFK-UHFFFAOYSA-N ethylone Chemical compound CCNC(C)C(=O)C1=CC=C2OCOC2=C1 MJEMIOXXNCZZFK-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- 229910021653 sulphate ion Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- QXECTWXEJXRAJT-UHFFFAOYSA-N tricyclo[9.4.0.02,7]pentadeca-1,4,6,8,10,12,14-heptaen-3-imine Chemical compound C1(C=CC=C2C=CC=C3C(=C21)C=CC=C3)=N QXECTWXEJXRAJT-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 235000010603 pastilles Nutrition 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- ISFGTDAAYLSOFY-QMMMGPOBSA-N (4s)-4-hydroxy-3-methyl-2-prop-2-ynylcyclopent-2-en-1-one Chemical compound CC1=C(CC#C)C(=O)C[C@@H]1O ISFGTDAAYLSOFY-QMMMGPOBSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YFVKHKCZBSGZPE-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(propylamino)propan-1-one Chemical compound CCCNC(C)C(=O)C1=CC=C2OCOC2=C1 YFVKHKCZBSGZPE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- AWFYPPSBLUWMFQ-UHFFFAOYSA-N 2-[5-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-1,3,4-oxadiazol-2-yl]-1-(1,4,6,7-tetrahydropyrazolo[4,3-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1=NN=C(O1)CC(=O)N1CC2=C(CC1)NN=C2 AWFYPPSBLUWMFQ-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- ICBZSKCTKKUQSY-YUWZRIFDSA-N 4-[(1r,2s)-1-hydroxy-2-(methylamino)propyl]phenol;hydrochloride Chemical compound Cl.CN[C@@H](C)[C@H](O)C1=CC=C(O)C=C1 ICBZSKCTKKUQSY-YUWZRIFDSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 1
- UWIULCYKVGIOPW-UHFFFAOYSA-N Glycolone Natural products CCOC1=C(CC=CC)C(=O)N(C)c2c(O)cccc12 UWIULCYKVGIOPW-UHFFFAOYSA-N 0.000 description 1
- 241000575946 Ione Species 0.000 description 1
- 241000283986 Lepus Species 0.000 description 1
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- FCVHBUFELUXTLR-UHFFFAOYSA-N [Li].[AlH3] Chemical compound [Li].[AlH3] FCVHBUFELUXTLR-UHFFFAOYSA-N 0.000 description 1
- UPLILVQBOYTEMM-UHFFFAOYSA-N [Na].C(Cl)(Cl)Cl.CO Chemical compound [Na].C(Cl)(Cl)Cl.CO UPLILVQBOYTEMM-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- AMLZDCJUSXNDOP-UHFFFAOYSA-N benzene ethyl acetate hydrochloride Chemical compound Cl.C(C)OC(C)=O.C1=CC=CC=C1 AMLZDCJUSXNDOP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Chemical compound CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000002996 emotional effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 150000004820 halides Chemical class 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
- 150000004678 hydrides Chemical class 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- KPJPHPFMCOKUMW-UHFFFAOYSA-N iodomethane Chemical compound I[CH2] KPJPHPFMCOKUMW-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- XNYQOMGRRUGAFN-UHFFFAOYSA-N n-methylmethanamine;n-propylpropan-1-amine Chemical compound CNC.CCCNCCC XNYQOMGRRUGAFN-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7203778A FR2170861B1 (de) | 1972-02-04 | 1972-02-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL41403A0 IL41403A0 (en) | 1973-03-30 |
| IL41403A true IL41403A (en) | 1977-06-30 |
Family
ID=9093003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL41403A IL41403A (en) | 1972-02-04 | 1973-01-26 | 10,11-dihydro-5,10-imino-dibenzocycloheptene derivatives and their preparation |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US3892756A (de) |
| JP (1) | JPS4886899A (de) |
| AT (1) | AT327212B (de) |
| AU (1) | AU468600B2 (de) |
| BE (1) | BE794904A (de) |
| CA (1) | CA1019732A (de) |
| CH (2) | CH567018A5 (de) |
| DD (1) | DD106837A5 (de) |
| DE (1) | DE2305496A1 (de) |
| DK (1) | DK136650B (de) |
| ES (1) | ES411262A1 (de) |
| FR (1) | FR2170861B1 (de) |
| GB (1) | GB1405711A (de) |
| HU (1) | HU166618B (de) |
| IL (1) | IL41403A (de) |
| NL (1) | NL7301610A (de) |
| SE (1) | SE405974B (de) |
| SU (2) | SU651704A3 (de) |
| ZA (1) | ZA73658B (de) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE794904A (fr) * | 1972-02-04 | 1973-08-02 | Roussel Uclaf | Nouveaux derives du dibenzocycloheptene et leur preparation |
| US4123546A (en) * | 1977-07-01 | 1978-10-31 | E. I. Du Pont De Nemours And Company | Antidepressant compounds |
| US4414154A (en) * | 1977-09-19 | 1983-11-08 | Merck & Co. Inc. | Dibenzo[a,d]cycloocten-5,12-imines |
| US4399141A (en) * | 1977-09-19 | 1983-08-16 | Merck & Co., Inc. | 5-Alkyl or hydroxyalkyl substituted-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines and anticonvulsant use thereof |
| NL7808848A (nl) * | 1977-09-19 | 1979-03-21 | Merck & Co Inc | Dibenzoa.dcyclo-octeen-5.12-(en 6.12)-iminen. |
| NL191488C (nl) * | 1977-09-19 | 1995-08-04 | Merck & Co Inc | Op de 5-plaats gesubstitueerde 10,11-dihydro-5H-dibenzo£a,d|cyclohepteen-5,10-iminen en farmaceutische preparaten die deze bevatten. |
| IL56112A0 (en) * | 1977-12-15 | 1979-03-12 | Merck & Co Inc | Imino-bridged benzocycloheptapyridines |
| US4256889A (en) * | 1978-11-09 | 1981-03-17 | Merck & Co., Inc. | Process for the preparation of imino-bridged benzocycloheptapyridines |
| US4252810A (en) * | 1978-11-15 | 1981-02-24 | Merck & Co., Inc. | 9,10-Dihydro-4H-benzo[4,5]cyclohepta [1,2-b]thiophen-4,9-imines |
| US4232158A (en) * | 1979-06-04 | 1980-11-04 | Merck & Co., Inc. | 10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imines |
| US4870079A (en) * | 1986-09-08 | 1989-09-26 | Merck & Co., Inc. | Derivatives of 5-methyl-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5,10-imine |
| GB8719199D0 (en) * | 1987-08-13 | 1987-09-23 | Merck Sharp & Dohme | Chemical compounds |
| US6017910A (en) * | 1989-04-14 | 2000-01-25 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | PCP receptor ligands and the use thereof |
| US5011834A (en) * | 1989-04-14 | 1991-04-30 | State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon | PCP receptor ligands and the use thereof |
| ES2091820T3 (es) * | 1989-05-09 | 1996-11-16 | Us Health | 5-amino-carbonil-5h-dibenzo(a,d)ciclo-hepten-5.10-iminas para tratamiento de la epilepsia y la adiccion a la cocaina. |
| US5196415A (en) * | 1989-05-09 | 1993-03-23 | The United States Of America As Represented By The Department Of Health And Human Services | 5-aminocarbonyl-5H-dibenzo[a.d]cyclohepten-5,10-imines for treatment of epilepsy and cocaine addiction |
| US5064831A (en) * | 1990-09-14 | 1991-11-12 | Bristol-Myers Squibb Co. | Naphthothiophenimines for treating neuronal disorders caused by ischemia |
| US5666677A (en) * | 1994-05-12 | 1997-09-16 | Easy Lift Care Products, Inc. | Bath tub assembly |
| US5598590A (en) * | 1994-05-12 | 1997-02-04 | Easy Lift Care Products, Inc. | Bathing apparatus |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2524856A (en) * | 1950-10-10 | Wperido-phenanthrene derivatives | ||
| US3597433A (en) * | 1968-08-19 | 1971-08-03 | Ayerst Mckenna & Harrison | 10,11 - dihydro - 5,10 - (iminomethano)-5h-dibenzo(a,d)cycloheptene and derivatives thereof |
| NL7007464A (de) * | 1969-05-30 | 1970-12-02 | ||
| BE790673A (fr) * | 1971-10-29 | 1973-04-27 | Riker Laboratories Inc | Dibenzobicyclo (3.2.1) octadienes substitues en positions 8 |
| BE794904A (fr) * | 1972-02-04 | 1973-08-02 | Roussel Uclaf | Nouveaux derives du dibenzocycloheptene et leur preparation |
-
0
- BE BE794904D patent/BE794904A/xx unknown
-
1972
- 1972-02-04 FR FR7203778A patent/FR2170861B1/fr not_active Expired
-
1973
- 1973-01-26 IL IL41403A patent/IL41403A/en unknown
- 1973-01-29 CH CH124673A patent/CH567018A5/xx not_active IP Right Cessation
- 1973-01-29 CH CH1553074A patent/CH565176A5/xx not_active IP Right Cessation
- 1973-01-30 US US328006A patent/US3892756A/en not_active Expired - Lifetime
- 1973-01-30 ZA ZA730658A patent/ZA73658B/xx unknown
- 1973-02-02 SU SU731878076A patent/SU651704A3/ru active
- 1973-02-02 JP JP48013013A patent/JPS4886899A/ja active Pending
- 1973-02-02 HU HURO702A patent/HU166618B/hu unknown
- 1973-02-02 SE SE7301485A patent/SE405974B/xx unknown
- 1973-02-02 AU AU51755/73A patent/AU468600B2/en not_active Expired
- 1973-02-03 ES ES411262A patent/ES411262A1/es not_active Expired
- 1973-02-05 DK DK58873AA patent/DK136650B/da unknown
- 1973-02-05 NL NL7301610A patent/NL7301610A/xx not_active Application Discontinuation
- 1973-02-05 DE DE2305496A patent/DE2305496A1/de active Pending
- 1973-02-05 CA CA162,927A patent/CA1019732A/en not_active Expired
- 1973-02-05 AT AT99073*#A patent/AT327212B/de not_active IP Right Cessation
- 1973-02-05 DD DD169161A patent/DD106837A5/xx unknown
- 1973-02-05 GB GB562473A patent/GB1405711A/en not_active Expired
-
1974
- 1974-12-18 SU SU7402084652A patent/SU574154A3/ru active
-
1975
- 1975-04-14 US US05/568,148 patent/US4009273A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATA99073A (de) | 1975-04-15 |
| ES411262A1 (es) | 1976-04-16 |
| DD106837A5 (de) | 1974-07-05 |
| AU5175573A (en) | 1974-08-08 |
| ZA73658B (en) | 1974-03-27 |
| AT327212B (de) | 1976-01-26 |
| DE2305496A1 (de) | 1973-08-09 |
| SE405974B (sv) | 1979-01-15 |
| US3892756A (en) | 1975-07-01 |
| CA1019732A (en) | 1977-10-25 |
| FR2170861A1 (de) | 1973-09-21 |
| CH565176A5 (de) | 1975-08-15 |
| SU651704A3 (ru) | 1979-03-05 |
| DK136650C (de) | 1978-04-10 |
| GB1405711A (en) | 1975-09-10 |
| NL7301610A (de) | 1973-08-07 |
| AU468600B2 (en) | 1976-01-15 |
| BE794904A (fr) | 1973-08-02 |
| IL41403A0 (en) | 1973-03-30 |
| CH567018A5 (de) | 1975-09-30 |
| US4009273A (en) | 1977-02-22 |
| SU574154A3 (ru) | 1977-09-25 |
| FR2170861B1 (de) | 1975-04-25 |
| HU166618B (de) | 1975-04-28 |
| DK136650B (da) | 1977-11-07 |
| JPS4886899A (de) | 1973-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL41403A (en) | 10,11-dihydro-5,10-imino-dibenzocycloheptene derivatives and their preparation | |
| HU194167B (en) | Process for production og byciclic derivatives of carbonic acid | |
| ES2201019T3 (es) | Nuevo procedimiento de preparacion de la 11-amino-3-cloro-6,11-dihidro-5,5-dioxo-6-metil-dibenzo-(c,f)-(1,2)-tiacepina y su aplicacion a la sintesis de la tianeptina. | |
| CA1244411A (en) | Aminodesoxy-1.4;3.6-dianhydrohexitol nitrates, processes for their preparation and pharmaceutical composition | |
| ES2923623T3 (es) | Procedimiento para la preparación de un análogo de prostaglandina donante de óxido nítrico | |
| CA1202626A (en) | Deazapurine derivatives | |
| CA2368815A1 (en) | Novel synthesis and crystallization of piperazine ring-containing compounds | |
| CA3146869A1 (en) | Process for the preparation of a nitric oxide donating prostaglandin analogue | |
| HU177060B (hu) | Sposob poluchenija o-metilovykh proizvodnykh gidroksi-aporfina | |
| US6576764B2 (en) | Synthesis and crystallization of piperazine ring-containing compounds | |
| FI81583C (fi) | Foerfarande foer n-demetylering av morfinanalkaloider. | |
| JPH0352465B2 (de) | ||
| EP0240986B1 (de) | D-Nor-7-ergolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Zubereitung und Verwendung | |
| US20040054230A1 (en) | Synthesis of n,n-dimethyl-3-(4-methyl) benzoyl propionamide a key intermediate of zolpidem | |
| NL7809726A (nl) | Nieuwe tetracyclische verbindingen. | |
| GB2106516A (en) | Anthranilic acid esters | |
| ES2963960T3 (es) | Procedimiento nuevo para la preparación de Tavaborol y sus intermediarios | |
| EP0033215A2 (de) | Verfahren zur Herstellung antiallergischer Naphthotriazole | |
| US4713386A (en) | Tetrahydroazeto [2,1-a]isoquinolines and methods for treating depression | |
| EP0675880B1 (de) | Chinolondisulfide als zwischenverbindungen | |
| ES2270024T3 (es) | Procedimiento para la preparacion de derivados de quinolina. | |
| Schultz et al. | Attempts to find new antimalarials. XI. Derivatives of Phenanthrene, III. Amino alcohols derived from 9-chlorophenanthrene | |
| US20040176591A1 (en) | Novel synthesis and crystallization of peperazine ring-containing compounds | |
| Takeda et al. | The stereochemistry of dihydrolycorine. | |
| US3517061A (en) | 5h-1,4-benzodiazepin-5-ones |