CH622780A5 - - Google Patents

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Publication number: CH622780A5
Authority: CH; Switzerland
Prior art keywords: hydrogen atom; formula; carbon atoms; radical; phenyl
Prior art date: 1975-08-09

Application number

CH1002076A

Other languages

German (de)

English (en)

Inventor

Derek Victor Gardner

Original Assignee

Beecham Group Ltd

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

1975-08-09

Filing date

1976-08-05

Publication date

1981-04-30

1976-08-05 Application filed by Beecham Group Ltd filed Critical Beecham Group Ltd

1981-04-30 Publication of CH622780A5 publication Critical patent/CH622780A5/de

Links

150000001875 compounds Chemical class 0.000 claims description 64
-1 alkyl radicals Chemical class 0.000 claims description 47
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 35
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
125000004432 carbon atom Chemical group C* 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 14
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
238000000034 method Methods 0.000 claims description 9
230000000694 effects Effects 0.000 claims description 8
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
150000003254 radicals Chemical class 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 5
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
230000001430 anti-depressive effect Effects 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims 2
125000003277 amino group Chemical group 0.000 claims 1
230000000055 hyoplipidemic effect Effects 0.000 claims 1
239000000543 intermediate Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 70
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
235000019441 ethanol Nutrition 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
230000002829 reductive effect Effects 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
239000003921 oil Substances 0.000 description 13
239000012458 free base Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
239000000203 mixture Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
230000036528 appetite Effects 0.000 description 6
235000019789 appetite Nutrition 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000000354 decomposition reaction Methods 0.000 description 6
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
229910000041 hydrogen chloride Inorganic materials 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
229940126601 medicinal product Drugs 0.000 description 4
239000012071 phase Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 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
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 3
QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002585 base Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 3
229960003147 reserpine Drugs 0.000 description 3
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 2
125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 2
WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 2
KFPUXPZOUPYDIW-UHFFFAOYSA-N 7-methoxy-1,2-dimethyl-4-phenyl-1,3-dihydroisoquinolin-4-ol Chemical compound C=1C(OC)=CC=C2C=1C(C)N(C)CC2(O)C1=CC=CC=C1 KFPUXPZOUPYDIW-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000004093 cyano group Chemical group *C#N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
238000006266 etherification reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000006260 foam Substances 0.000 description 2
230000037406 food intake Effects 0.000 description 2
235000012631 food intake Nutrition 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
235000009518 sodium iodide Nutrition 0.000 description 2
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
YONLFQNRGZXBBF-KBPBESRZSA-N (2s,3s)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@H](C(=O)O)[C@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-KBPBESRZSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
XLQSXGGDTHANLN-UHFFFAOYSA-N 1-bromo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Br)C=C1 XLQSXGGDTHANLN-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
PTAPBGKYBVWNJY-UHFFFAOYSA-N 2,3-dibenzoyl-2,3-dihydroxybutanedioic acid;hydrate Chemical compound O.C=1C=CC=CC=1C(=O)C(O)(C(O)=O)C(O)(C(=O)O)C(=O)C1=CC=CC=C1 PTAPBGKYBVWNJY-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
OJKONCJPCULNOW-DYVFJYSZSA-N 5-chloro-2-fluoro-4-[(1s,2r)-2-(2-methylpyrazol-3-yl)cyclohexyl]oxy-n-pyrimidin-4-ylbenzenesulfonamide Chemical compound CN1N=CC=C1[C@@H]1[C@@H](OC=2C(=CC(=C(F)C=2)S(=O)(=O)NC=2N=CN=CC=2)Cl)CCCC1 OJKONCJPCULNOW-DYVFJYSZSA-N 0.000 description 1
RXBIGSSOCNQLCS-UHFFFAOYSA-N 7-methoxy-2,3-dimethyl-1,3-dihydroisoquinolin-4-one Chemical compound O=C1C(C)N(C)CC2=CC(OC)=CC=C21 RXBIGSSOCNQLCS-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
COQVPNCPQDPYPI-UHFFFAOYSA-N [Li]C1=CC=C(C(F)(F)F)C=C1 Chemical compound [Li]C1=CC=C(C(F)(F)F)C=C1 COQVPNCPQDPYPI-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000002830 appetite depressant Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
125000005518 carboxamido group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
UADVRJABKWXUEN-UHFFFAOYSA-N chloroethane;n-methylmethanamine Chemical compound CCCl.CNC UADVRJABKWXUEN-UHFFFAOYSA-N 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000010779 crude oil Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
229960001270 d- tartaric acid Drugs 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
125000002474 dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000008098 formaldehyde solution Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
230000002631 hypothermal effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
238000005259 measurement Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Psychiatry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)

CH1002076A 1975-08-09 1976-08-05 CH622780A5 (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB33283/75A GB1504424A (en)	1975-08-09	1975-08-09	Isoquinoline-derived aminoethers

Publications (1)

Publication Number	Publication Date
CH622780A5 true CH622780A5 (cs)	1981-04-30

Family

ID=10350917

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH1002076A CH622780A5 (cs)	1975-08-09	1976-08-05
CH52281A CH626611A5 (cs)	1975-08-09	1981-01-27

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH52281A CH626611A5 (cs)	1975-08-09	1981-01-27

Country Status (19)

Country	Link
US (1)	US4113869A (cs)
JP (1)	JPS5223083A (cs)
AT (2)	AT354448B (cs)
AU (1)	AU498422B2 (cs)
BE (1)	BE844783A (cs)
CA (1)	CA1076119A (cs)
CH (2)	CH622780A5 (cs)
DE (1)	DE2635276A1 (cs)
DK (1)	DK357976A (cs)
ES (6)	ES450550A1 (cs)
FR (1)	FR2320755A1 (cs)
GB (1)	GB1504424A (cs)
HU (1)	HU173560B (cs)
IE (1)	IE43506B1 (cs)
IL (1)	IL50176A (cs)
NL (1)	NL7608856A (cs)
NZ (1)	NZ181619A (cs)
SE (1)	SE7608641L (cs)
ZA (1)	ZA764555B (cs)

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US4340600A (en)	1980-05-22	1982-07-20	Smithkline Corporation	Renal dilating methods and compositions using 4-(3,4-dihydroxyphenyl)-1,2,3,4-tetrahydroisoquinolines
US4766131A (en) *	1980-10-17	1988-08-23	Pennwalt Corporation	2-amino (or hydroxy) phenethyl-1,2,3,4-tetrahydroisoquinolines as analgesics
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US4551474A (en) *	1981-02-19	1985-11-05	Hoechst-Roussel Pharmaceuticals Incorporated	Methods of alleviating convulsions and pain employing 4-aryloxy-1,2,3,4 tetrahydroisoquinolines
US6562837B1 (en) *	1998-10-21	2003-05-13	Korea Institute Of Science & Technology	Use of tetrahydroisoquinoline compounds for the treatment of septicemia
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US20060111394A1 (en) *	2004-11-22	2006-05-25	Molino Bruce F	Aryl-and heteroaryl-substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin
US20060111393A1 (en) *	2004-11-22	2006-05-25	Molino Bruce F	4-Phenyl substituted tetrahydroisoquinolines and use thereof to block reuptake of norepinephrine, dopamine and serotonin
CN101128432A (zh) *	2004-12-17	2008-02-20	詹森药业有限公司	用于治疗中枢神经系统疾病的四氢异喹啉化合物
AU2006261162A1 (en)	2005-06-17	2006-12-28	Janssen Pharmaceutica N.V.	Naphthyridine compounds
AU2006259257A1 (en) *	2005-06-17	2006-12-28	Janssen Pharmaceutica N.V.	Hexahydro-pyrrolo-isoquinoline compounds for the treatment of CNS disorders
US7956050B2 (en)	2005-07-15	2011-06-07	Albany Molecular Research, Inc.	Aryl- and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin
WO2008144305A1 (en) *	2007-05-18	2008-11-27	Janssen Pharmaceutica N.V.	Diaryl-substituted tetrahydroisoquinolines as histamine h3 receptor and serotonin transporter modulators
US9156812B2 (en)	2008-06-04	2015-10-13	Bristol-Myers Squibb Company	Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
AR071997A1 (es) *	2008-06-04	2010-07-28	Bristol Myers Squibb Co	Forma cristalina de 6-((4s)-2-metil-4-(2-naftil)-1,2,3,4-tetrahidroisoquinolin-7-il)piridazin-3-amina
BRPI0923225A2 (pt)	2008-12-02	2016-10-04	Chiralgen Ltd	metodo para sintese de acidos nucleicos modificados no atomo de fosforo
JP5739415B2 (ja)	2009-05-12	2015-06-24	ブリストル−マイヤーズスクウィブカンパニー	（Ｓ）−７−（［１，２，４］トリアゾロ［１，５−ａ］ピリジン−６−イル）−４−（３，４−ジクロロフェニル）−１，２，３，４−テトラヒドロイソキノリンの結晶形態およびその使用
CN102595902B (zh)	2009-05-12	2015-04-29	阿尔巴尼分子研究公司	7-([1,2,4]三唑并[1,5-a]吡啶-6-基)-4-(3,4-二氯苯基)-1,2,3,4-四氢异喹啉及其用途
ES2446971T3 (es)	2009-05-12	2014-03-11	Albany Molecular Research, Inc.	Tetrahidroisoquinolinas sustituidas con arilo, heteroarilo, y heterociclo y su uso
EP2451461A4 (en)	2009-07-06	2013-05-29	Ontorii Inc	NOVEL NUCLEIC ACID PRODRUGS AND METHOD OF USE THEREOF
DK2620428T3 (da) *	2010-09-24	2019-07-01	Wave Life Sciences Ltd	Asymmetrisk hjælpegruppe
CN107365339A (zh)	2011-07-19	2017-11-21	波涛生命科学有限公司	合成官能化核酸的方法
SG11201500243WA (en)	2012-07-13	2015-04-29	Shin Nippon Biomedical Lab Ltd	Chiral nucleic acid adjuvant
DK2872147T3 (da)	2012-07-13	2023-02-20	Wave Life Sciences Ltd	Fremgangsmåde til fremstilling af kirale oligonukleotider
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GB1058822A (en) *	1963-07-30	1967-02-15	Ici Ltd	3-amino-2-hydroxypropoxy heterocyclic derivatives
US3479358A (en) *	1966-09-19	1969-11-18	Warner Lambert Pharmaceutical	Hexahydro-9,4a - iminoethano-4a-h-xanthenes and process for their production
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US3666763A (en) *	1970-01-06	1972-05-30	Hoffmann La Roche	4-phenyl isoquinolines and process for preparing same
US3878215A (en) *	1971-12-01	1975-04-15	Sandoz Ag	2-Alkyl-3-substituted-4-aryl isoquinolines
US3910924A (en) *	1972-04-13	1975-10-07	Otsuka Pharma Co Ltd	3,4-Dihydrocarbostyril derivatives and a process for preparing the same
US3855227A (en) *	1972-05-08	1974-12-17	C Hollander	({31 )-di-o-isopropylidene-2-keto-l-gulonates
JPS5239035B2 (cs) *	1972-12-14	1977-10-03
US3872125A (en) *	1973-03-03	1975-03-18	Sandoz Ag	3-substituted-4-aryl isoquinolines
US3870722A (en) *	1973-11-02	1975-03-11	Sandoz Ag	2-Methyl-3-substituted-4-aryl isoquinolines
AR206061A1 (es) *	1974-11-15	1976-06-23	Knoll Ag	Procedimiento para la produccion de nuevas 2-alcanoil (c1-c4)-1, 2, 3, 4-tetrahidro-8-respectivamente 7-, 6- o 5-(2-hidroxi-3-alquil (c3-c4)-aminopropoxi)-isoquinolinas de 2-alcanoil (c1-c4)-1, 2, 3, 4-tetrahidro-8-respectivamente 7- o 5-(2-hidroxi-3-alquil (c3-c4)-aminopropoxi)-6-metoxi-isoquinolinas y de 2-alcanoil (c1-c4)-1, 2, 3, 4-tetrahidro-8-respectivamente 6- o 5-(2-hidroxi-3-alquil (c3-c4)-aminopropoxi)-7-metoxi-isoquinolinas eventualmente metiladas en la posicion 1

1975
- 1975-08-09 GB GB33283/75A patent/GB1504424A/en not_active Expired
1976
- 1976-07-28 IE IE1668/76A patent/IE43506B1/en unknown
- 1976-07-29 ZA ZA764555A patent/ZA764555B/xx unknown
- 1976-07-29 NZ NZ181619A patent/NZ181619A/xx unknown
- 1976-07-30 IL IL50176A patent/IL50176A/xx unknown
- 1976-07-30 BE BE169475A patent/BE844783A/xx unknown
- 1976-07-30 SE SE7608641A patent/SE7608641L/xx not_active Application Discontinuation
- 1976-08-02 US US05/710,446 patent/US4113869A/en not_active Expired - Lifetime
- 1976-08-05 CH CH1002076A patent/CH622780A5/de not_active IP Right Cessation
- 1976-08-05 DE DE19762635276 patent/DE2635276A1/de not_active Withdrawn
- 1976-08-06 DK DK357976A patent/DK357976A/da not_active Application Discontinuation
- 1976-08-06 AT AT586876A patent/AT354448B/de not_active IP Right Cessation
- 1976-08-06 ES ES450550A patent/ES450550A1/es not_active Expired
- 1976-08-06 CA CA258,633A patent/CA1076119A/en not_active Expired
- 1976-08-09 FR FR7624258A patent/FR2320755A1/fr active Granted
- 1976-08-09 HU HU76BE1265A patent/HU173560B/hu unknown
- 1976-08-09 JP JP51094721A patent/JPS5223083A/ja active Pending
- 1976-08-09 AU AU16702/76A patent/AU498422B2/en not_active Expired
- 1976-08-09 NL NL7608856A patent/NL7608856A/xx not_active Application Discontinuation
1977
- 1977-09-01 ES ES462059A patent/ES462059A1/es not_active Expired
- 1977-09-01 ES ES77462062A patent/ES462062A1/es not_active Expired
- 1977-09-01 ES ES462058A patent/ES462058A1/es not_active Expired
- 1977-09-01 ES ES462061A patent/ES462061A1/es not_active Expired
- 1977-09-01 ES ES462060A patent/ES462060A1/es not_active Expired
1978
- 1978-10-05 AT AT717378A patent/AT353793B/de not_active IP Right Cessation
1981
- 1981-01-27 CH CH52281A patent/CH626611A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES462061A1 (es)	1978-06-16
ES462059A1 (es)	1978-06-16
ES462058A1 (es)	1978-06-16
ES450550A1 (es)	1977-12-16
NZ181619A (en)	1979-08-31
IL50176A0 (en)	1976-09-30
AU498422B2 (en)	1979-03-15
DK357976A (da)	1977-02-10
FR2320755A1 (fr)	1977-03-11
DE2635276A1 (de)	1977-02-17
ATA586876A (de)	1979-06-15
AT354448B (de)	1979-01-10
ZA764555B (en)	1977-07-27
NL7608856A (nl)	1977-02-11
FR2320755B1 (cs)	1979-09-14
ES462060A1 (es)	1978-06-16
IL50176A (en)	1979-10-31
SE7608641L (sv)	1977-02-10
CH626611A5 (cs)	1981-11-30
US4113869A (en)	1978-09-12
HU173560B (hu)	1979-06-28
BE844783A (fr)	1977-01-31
AT353793B (de)	1979-12-10
GB1504424A (en)	1978-03-22
IE43506L (en)	1977-02-09
ATA717378A (de)	1979-05-15
AU1670276A (en)	1978-02-16
ES462062A1 (es)	1978-06-16
IE43506B1 (en)	1981-03-11
JPS5223083A (en)	1977-02-21
CA1076119A (en)	1980-04-22

Legal Events

Date	Code	Title	Description
1984-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2635276A1 (de)	1977-02-17	Tetrahydroisochinolin-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
EP0253327B1 (de)	1992-05-06	Neue Diphenylpropylamin-Derivate, ihre Herstellung sowie ihre pharmazeutische Verwendung
CH621115A5 (cs)	1981-01-15
DE2047658C3 (de)	1980-11-13	2-Styryl- und 2-Phenyläthinylbenzylaminderivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE3402601A1 (de)	1984-08-02	Neue pharmazeutisch aktive 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)chinolinderivate, deren herstellung und verwendung
US2993899A (en)	1961-07-25	Acetylenically unsaturated piperazine derivatives
CH623584A5 (cs)	1981-06-15
US4109088A (en)	1978-08-22	2-(indenyloxymethyl) morpholine derivatives
EP0064685A1 (de)	1982-11-17	Dibenzo(de,g)chinolin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
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