NO131887B - - Google Patents
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- Publication number
- NO131887B NO131887B NO3034/71A NO303471A NO131887B NO 131887 B NO131887 B NO 131887B NO 3034/71 A NO3034/71 A NO 3034/71A NO 303471 A NO303471 A NO 303471A NO 131887 B NO131887 B NO 131887B
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- azepine
- tetrahydro
- azepinone
- hexahydro
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 59
- -1 alkyl radical Chemical class 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000004202 carbamide Substances 0.000 claims description 24
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000004434 sulfur atom Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 5
- 150000007524 organic acids Chemical class 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 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000001538 azepines Chemical class 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229960003424 phenylacetic acid Drugs 0.000 claims description 3
- 239000003279 phenylacetic acid Substances 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 46
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 23
- 239000012362 glacial acetic acid Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 21
- 238000009835 boiling Methods 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 9
- 239000002026 chloroform extract Substances 0.000 description 9
- 235000011121 sodium hydroxide Nutrition 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 8
- ZZDGQQSLBXLAHI-UHFFFAOYSA-N 6-benzyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=CC=C1 ZZDGQQSLBXLAHI-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 230000000954 anitussive effect Effects 0.000 description 5
- 230000001741 anti-phlogistic effect Effects 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- POXAIQSXNOEQGM-UHFFFAOYSA-N propan-2-ylthiourea Chemical compound CC(C)NC(N)=S POXAIQSXNOEQGM-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000001624 sedative effect Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- GMEHFXXZSWDEDB-UHFFFAOYSA-N N-ethylthiourea Chemical compound CCNC(N)=S GMEHFXXZSWDEDB-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000003444 anaesthetic effect Effects 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
- 238000003776 cleavage reaction Methods 0.000 description 3
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- ONPQCAFYBLFOMG-UHFFFAOYSA-N 4-ethoxy-1-propyl-2,3,6,7-tetrahydroazepine Chemical compound CCCN1CCC=C(OCC)CC1 ONPQCAFYBLFOMG-UHFFFAOYSA-N 0.000 description 2
- BDEHEFQLNAXGKD-UHFFFAOYSA-N 6-[(4-methylphenyl)methyl]-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1OC=2CCN(CCC2N1)CC1=CC=C(C=C1)C BDEHEFQLNAXGKD-UHFFFAOYSA-N 0.000 description 2
- QZNXRXDPYHWXAF-UHFFFAOYSA-N 6-benzyl-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1OC=2CCN(CCC2N1)CC1=CC=CC=C1 QZNXRXDPYHWXAF-UHFFFAOYSA-N 0.000 description 2
- HBLPYIOKPJVFQW-UHFFFAOYSA-N 6-ethyl-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine;hydron;dichloride Chemical compound Cl.Cl.C1CN(CC)CCC2=C1OC(N)=N2 HBLPYIOKPJVFQW-UHFFFAOYSA-N 0.000 description 2
- FRFBYBDFQYKFKP-UHFFFAOYSA-N 6-ethyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1CN(CC)CCC2=C1SC(N)=N2 FRFBYBDFQYKFKP-UHFFFAOYSA-N 0.000 description 2
- SBORZAVOKSPZHY-UHFFFAOYSA-N 6-propan-2-yl-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine Chemical compound NC=1OC=2CCN(CCC2N1)C(C)C SBORZAVOKSPZHY-UHFFFAOYSA-N 0.000 description 2
- YMVIOJYYCBEICH-UHFFFAOYSA-N C(C)NC=1SC=2CCN(CCC2N1)CC1=CC=CC=C1 Chemical compound C(C)NC=1SC=2CCN(CCC2N1)CC1=CC=CC=C1 YMVIOJYYCBEICH-UHFFFAOYSA-N 0.000 description 2
- DLLLWCJNDAJMBI-UHFFFAOYSA-N Cl.Cl.NC=1OC=2CCN(CCC2N1)CC(C)C Chemical compound Cl.Cl.NC=1OC=2CCN(CCC2N1)CC(C)C DLLLWCJNDAJMBI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 description 2
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 description 2
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 2
- 206010030113 Oedema Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UHGKYJXJYJWDAM-UHFFFAOYSA-N Propylthiourea Chemical compound CCCNC(N)=S UHGKYJXJYJWDAM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000004531 blood pressure lowering effect Effects 0.000 description 2
- 230000031709 bromination Effects 0.000 description 2
- 238000005893 bromination reaction Methods 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 description 1
- PJHKXESPJOFGOA-UHFFFAOYSA-N 1h-azepine;dihydrochloride Chemical compound Cl.Cl.N1C=CC=CC=C1 PJHKXESPJOFGOA-UHFFFAOYSA-N 0.000 description 1
- GNHGSSSQCHAIEL-UHFFFAOYSA-N 1h-azepine;hydrobromide Chemical compound Br.N1C=CC=CC=C1 GNHGSSSQCHAIEL-UHFFFAOYSA-N 0.000 description 1
- AJUMGSLQADLWKL-UHFFFAOYSA-N 1h-azepine;hydrochloride Chemical compound Cl.N1C=CC=CC=C1 AJUMGSLQADLWKL-UHFFFAOYSA-N 0.000 description 1
- ONOBXDPYDHTSBQ-UHFFFAOYSA-N 2,3,4,7-tetrahydro-1h-diazepine Chemical compound C1CC=CCNN1 ONOBXDPYDHTSBQ-UHFFFAOYSA-N 0.000 description 1
- NMDVYJBWTSMCMH-UHFFFAOYSA-N 2-(2-amino-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-6-yl)ethanol;dihydrochloride Chemical compound Cl.Cl.C1CN(CCO)CCC2=C1N=C(N)S2 NMDVYJBWTSMCMH-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
- IEMQYHVGZVYHNP-UHFFFAOYSA-N 5,6,7,8-tetrahydro-4h-[1,3]thiazolo[4,5-d]azepin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1CNCCC2=C1N=C(N)S2 IEMQYHVGZVYHNP-UHFFFAOYSA-N 0.000 description 1
- CEUCVLQJAZKIJP-UHFFFAOYSA-N 6-(2-methylpropyl)-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC(C)C CEUCVLQJAZKIJP-UHFFFAOYSA-N 0.000 description 1
- VWXJHCIEEKARTG-UHFFFAOYSA-N 6-[(3-bromophenyl)methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=CC=C1)Br VWXJHCIEEKARTG-UHFFFAOYSA-N 0.000 description 1
- WTTJIGYGBGMDKD-UHFFFAOYSA-N 6-[(4-bromophenyl)methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)Br WTTJIGYGBGMDKD-UHFFFAOYSA-N 0.000 description 1
- GJPGAKKPKZEVGZ-UHFFFAOYSA-N 6-[(4-chlorophenyl)methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine;dihydrochloride Chemical compound Cl.Cl.C1CC=2SC(N)=NC=2CCN1CC1=CC=C(Cl)C=C1 GJPGAKKPKZEVGZ-UHFFFAOYSA-N 0.000 description 1
- KXMZOYAZPOOVQC-UHFFFAOYSA-N 6-[(4-methylphenyl)methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)C KXMZOYAZPOOVQC-UHFFFAOYSA-N 0.000 description 1
- MUXSAUXLYSCZLI-UHFFFAOYSA-N 6-[[4-(trifluoromethyl)phenyl]methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)C(F)(F)F MUXSAUXLYSCZLI-UHFFFAOYSA-N 0.000 description 1
- AMLGULYIHSPYOW-UHFFFAOYSA-N 6-[[4-(trifluoromethyl)phenyl]methyl]-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)C(F)(F)F AMLGULYIHSPYOW-UHFFFAOYSA-N 0.000 description 1
- ZXYTWCOGVQEDAT-UHFFFAOYSA-N 6-benzyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound C1CC=2SC(N)=NC=2CCN1CC1=CC=CC=C1 ZXYTWCOGVQEDAT-UHFFFAOYSA-N 0.000 description 1
- DYAVCPODANMGPD-UHFFFAOYSA-N 6-benzyl-N-methyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound CNC=1SC=2CCN(CCC2N1)CC1=CC=CC=C1 DYAVCPODANMGPD-UHFFFAOYSA-N 0.000 description 1
- VLYDCWRAWTYSPH-UHFFFAOYSA-N 6-benzyl-N-propyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound C(CC)NC=1SC=2CCN(CCC2N1)CC1=CC=CC=C1 VLYDCWRAWTYSPH-UHFFFAOYSA-N 0.000 description 1
- UXNVRLIUJATYAB-UHFFFAOYSA-N 6-butyl-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1OC=2CCN(CCC2N1)CCCC UXNVRLIUJATYAB-UHFFFAOYSA-N 0.000 description 1
- AGQSUEFQXOKJMY-UHFFFAOYSA-N 6-butyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound NC=1SC=2CCN(CCC2N1)CCCC AGQSUEFQXOKJMY-UHFFFAOYSA-N 0.000 description 1
- ZNXAJGZPUQOEDZ-UHFFFAOYSA-N 6-ethyl-4,5,7,8-tetrahydro-[1,3]oxazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CC)CCC2=C1OC(N)=N2 ZNXAJGZPUQOEDZ-UHFFFAOYSA-N 0.000 description 1
- DAARCUOIXKLMOK-UHFFFAOYSA-N 6-ethyl-N-methyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.CNC=1SC=2CCN(CCC2N1)CC DAARCUOIXKLMOK-UHFFFAOYSA-N 0.000 description 1
- WDLILJPUTYYQMM-UHFFFAOYSA-N 6-methyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)C WDLILJPUTYYQMM-UHFFFAOYSA-N 0.000 description 1
- KIFFPFKVDOQZPY-UHFFFAOYSA-N 6-phenyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine dihydrochloride Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)C1=CC=CC=C1 KIFFPFKVDOQZPY-UHFFFAOYSA-N 0.000 description 1
- JECKWLWVOQPAKJ-UHFFFAOYSA-N 6-propyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound C1CN(CCC)CCC2=C1SC(N)=N2 JECKWLWVOQPAKJ-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- CSDJVKBNDXZYLL-UHFFFAOYSA-N Cl.Cl.C(C)NC=1SC=2CCN(CCC2N1)CC Chemical compound Cl.Cl.C(C)NC=1SC=2CCN(CCC2N1)CC CSDJVKBNDXZYLL-UHFFFAOYSA-N 0.000 description 1
- AQNWQMLTIBKRPH-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=C(C=C(C=C1)Cl)Cl Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=C(C=C(C=C1)Cl)Cl AQNWQMLTIBKRPH-UHFFFAOYSA-N 0.000 description 1
- OOQNNAZYPLZESC-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=C(C=CC=C1)Br Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=C(C=CC=C1)Br OOQNNAZYPLZESC-UHFFFAOYSA-N 0.000 description 1
- YEXKDDQNEUCBBB-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=C(C(=C1)OC)OC)OC Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=C(C(=C1)OC)OC)OC YEXKDDQNEUCBBB-UHFFFAOYSA-N 0.000 description 1
- OAQXZHRUPKWERC-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=CC=C1)C Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=CC=C1)C OAQXZHRUPKWERC-UHFFFAOYSA-N 0.000 description 1
- UACDEVWISPJYPZ-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=CC=C1)C(F)(F)F Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC(=CC=C1)C(F)(F)F UACDEVWISPJYPZ-UHFFFAOYSA-N 0.000 description 1
- RMPFIUASXPPUCY-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)F Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)F RMPFIUASXPPUCY-UHFFFAOYSA-N 0.000 description 1
- MXBKKDQFRDZSSV-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)OC Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)OC MXBKKDQFRDZSSV-UHFFFAOYSA-N 0.000 description 1
- YHRGHEMLCOERLH-UHFFFAOYSA-N Cl.Cl.NC=1SC=2CCN(CCC2N1)CCCC Chemical compound Cl.Cl.NC=1SC=2CCN(CCC2N1)CCCC YHRGHEMLCOERLH-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 238000006228 Dieckmann condensation reaction Methods 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 101100042676 Mus musculus Skap2 gene Proteins 0.000 description 1
- FQBRNHBOSXFTIU-UHFFFAOYSA-N N-(5,6,7,8-tetrahydro-4H-[1,3]thiazolo[4,5-d]azepin-2-yl)benzamide hydrobromide Chemical compound Br.C(C1=CC=CC=C1)(=O)NC=1SC=2CCNCCC2N1 FQBRNHBOSXFTIU-UHFFFAOYSA-N 0.000 description 1
- 150000007945 N-acyl ureas Chemical class 0.000 description 1
- DEFQULRUMNNRKT-UHFFFAOYSA-N N-ethyl-6-propyl-4,5,7,8-tetrahydro-[1,3]thiazolo[4,5-d]azepin-2-amine Chemical compound C(C)NC=1SC=2CCN(CCC2N1)CCC DEFQULRUMNNRKT-UHFFFAOYSA-N 0.000 description 1
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical compound NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 description 1
- SNLDSSYNIVAHDX-UHFFFAOYSA-N NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)F Chemical compound NC=1SC=2CCN(CCC2N1)CC1=CC=C(C=C1)F SNLDSSYNIVAHDX-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- GXDVEXJTVGRLNW-UHFFFAOYSA-N [Cr].[Cu] Chemical compound [Cr].[Cu] GXDVEXJTVGRLNW-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- HTKFORQRBXIQHD-UHFFFAOYSA-N allylthiourea Chemical compound NC(=S)NCC=C HTKFORQRBXIQHD-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000002322 anti-exudative effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- LEEHHPPLIOFGSC-UHFFFAOYSA-N cyclohexylthiourea Chemical compound NC(=S)NC1CCCCC1 LEEHHPPLIOFGSC-UHFFFAOYSA-N 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DQMWMUMCNOJLSI-UHFFFAOYSA-N n-carbamothioylbenzamide Chemical compound NC(=S)NC(=O)C1=CC=CC=C1 DQMWMUMCNOJLSI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001151 other effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- KIYXXKTUEPCNLC-UHFFFAOYSA-N pentylthiourea Chemical compound CCCCCNC(N)=S KIYXXKTUEPCNLC-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2040510A DE2040510C3 (de) | 1970-08-14 | 1970-08-14 | Oxazole- und Thiazole eckige Klammer auf 5,4-d] azepin- Derivate |
| DE19712127267 DE2127267A1 (en) | 1971-06-02 | 1971-06-02 | 2-amino-4,5,7,8-tetrahydro-6h-thiazolo-or oxazolo(5,4-d) - azepines - as hypotensive, antiphlogistic, sedative and bechic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131887B true NO131887B (xx) | 1975-05-12 |
| NO131887C NO131887C (xx) | 1975-08-20 |
Family
ID=25759588
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3034/71A NO131887C (xx) | 1970-08-14 | 1971-08-13 |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3804849A (xx) |
| JP (1) | JPS5246236B1 (xx) |
| AT (1) | AT310174B (xx) |
| AU (1) | AU462319B2 (xx) |
| BE (1) | BE771330A (xx) |
| BG (3) | BG17786A3 (xx) |
| CA (1) | CA965423A (xx) |
| CH (1) | CH571003A5 (xx) |
| CS (1) | CS178084B2 (xx) |
| DK (1) | DK136654C (xx) |
| ES (3) | ES393881A1 (xx) |
| FI (1) | FI54925C (xx) |
| FR (1) | FR2102192B1 (xx) |
| GB (1) | GB1321509A (xx) |
| HU (1) | HU162343B (xx) |
| IE (1) | IE35517B1 (xx) |
| IL (1) | IL37492A (xx) |
| NL (1) | NL168516C (xx) |
| NO (1) | NO131887C (xx) |
| PL (1) | PL85080B1 (xx) |
| RO (4) | RO60635A (xx) |
| SE (1) | SE380529B (xx) |
| YU (5) | YU35027B (xx) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3907996A (en) * | 1970-08-14 | 1975-09-23 | Boehringer Sohn Ingelheim | Pharmaceutical composition containing a 2-amino-4,5,7,8-tetrahydro-6H-thiazolo or -oxazolo 5,4-D azepine and method of use |
| BE795257A (fr) * | 1972-02-10 | 1973-08-09 | Thomae Gmbh Dr K | Nouveaux oxazols |
| DE2820808A1 (de) * | 1978-05-12 | 1979-11-22 | Thomae Gmbh Dr K | Arzneimittel mit einer antanginoesen wirksamkeit |
| US4400378A (en) * | 1981-11-02 | 1983-08-23 | Karl Thomae Gesellschaft Mit Beschrankter Haftung | Pharmaceutical composition for the treatment of glaucoma |
| EP0192098B1 (de) | 1985-02-06 | 1991-08-21 | Boehringer Ingelheim Kg | Verwendung des 2-Amino-6-allyl-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepins zur Herstellung eines zur Behandlung der Parkinsonschen Erkrankung bzw. des Parkinsonismus geeigneten Arzneimittels |
| US4826686A (en) * | 1985-12-14 | 1989-05-02 | Boehringer Ingelheim Kg | Therapeutic system |
| DE3820775A1 (de) * | 1988-06-20 | 1989-12-21 | Thomae Gmbh Dr K | Neue 4,5,7,8-tetrahydro-6h-thiazolo(5,4,-d)azepine, ihre herstellung und ihre verwendung als arzneimittel |
| JP3054738B2 (ja) * | 1988-07-22 | 2000-06-19 | 武田薬品工業株式会社 | チアゾロ［５，４―ｂ］アゼピン誘導体 |
| US5424431A (en) * | 1990-10-24 | 1995-06-13 | Yamanouchi Pharmaceutical Co., Ltd. | Thiazole derivatives |
| US6369222B1 (en) * | 2000-07-18 | 2002-04-09 | Hoffmann-La Roche Inc. | mGluR antagonists and a method for their synthesis |
| BRPI0619159B1 (pt) * | 2005-12-08 | 2016-04-12 | Huntsman Int Llc | processo para a preparação de diamino difenil metano e poli-(diamino difenil metano), e, processo para a preparação de metileno difenileno diisocianato e poli-(metileno difenileno diisocianato) |
| EP2236511A4 (en) | 2007-12-21 | 2011-04-13 | Alla Chem Llc | LIGANDS OF ALPHA ADRENOCEPTORS AND OF DOPAMINE, HISTAMIN, IMIDAZOLIN AND SEROTONIN RECEPTORS AND THEIR APPLICATION THEREOF |
| RU2374245C1 (ru) | 2008-08-22 | 2009-11-27 | Андрей Александрович Иващенко | Лиганд с широким спектром одновременной рецепторной активности, фармацевтическая композиция, способ ее получения и лекарственное средство |
| EP2327704A4 (en) * | 2008-08-29 | 2012-05-09 | Shionogi & Co | RING-CONDENSED AZOL DERIVATIVE WITH PI3K-INHIBITING EFFECT |
| TWI537274B (zh) | 2011-03-14 | 2016-06-11 | 橘生藥品工業股份有限公司 | 新穎之八氫噻吩并喹啉衍生物、含有其之醫藥組成物及該等之用途 |
| WO2014092006A1 (ja) | 2012-12-10 | 2014-06-19 | キッセイ薬品工業株式会社 | 新規なオクタヒドロピリドキナゾリン誘導体、それを含有する医薬組成物およびそれらの用途 |
| CN104031072A (zh) * | 2014-06-24 | 2014-09-10 | 重庆植恩药业有限公司 | 一种盐酸他利克索的制备方法 |
-
1971
- 1971-07-30 BG BG19142A patent/BG17786A3/xx unknown
- 1971-07-30 BG BG19141A patent/BG17785A3/xx unknown
- 1971-07-30 BG BG18197A patent/BG17968A3/xx unknown
- 1971-08-04 RO RO67900A patent/RO60635A/ro unknown
- 1971-08-04 US US00169065A patent/US3804849A/en not_active Expired - Lifetime
- 1971-08-04 RO RO70469A patent/RO59925A/ro unknown
- 1971-08-04 ES ES393881A patent/ES393881A1/es not_active Expired
- 1971-08-04 RO RO70457A patent/RO59127A/ro unknown
- 1971-08-04 RO RO70468A patent/RO59129A/ro unknown
- 1971-08-11 CH CH1180571A patent/CH571003A5/xx not_active IP Right Cessation
- 1971-08-12 HU HUTO858A patent/HU162343B/hu unknown
- 1971-08-12 IL IL37492A patent/IL37492A/xx unknown
- 1971-08-12 CS CS5856A patent/CS178084B2/cs unknown
- 1971-08-12 DK DK394071A patent/DK136654C/da not_active IP Right Cessation
- 1971-08-13 NL NLAANVRAGE7111176,A patent/NL168516C/xx not_active IP Right Cessation
- 1971-08-13 BE BE771330A patent/BE771330A/xx unknown
- 1971-08-13 PL PL1971150004D patent/PL85080B1/pl unknown
- 1971-08-13 YU YU2084/71A patent/YU35027B/xx unknown
- 1971-08-13 SE SE7110347A patent/SE380529B/xx unknown
- 1971-08-13 FI FI2265/71A patent/FI54925C/fi active
- 1971-08-13 CA CA120,522A patent/CA965423A/en not_active Expired
- 1971-08-13 AT AT711071A patent/AT310174B/de active
- 1971-08-13 JP JP46061588A patent/JPS5246236B1/ja active Pending
- 1971-08-13 GB GB3816071A patent/GB1321509A/en not_active Expired
- 1971-08-13 FR FR7129692A patent/FR2102192B1/fr not_active Expired
- 1971-08-13 NO NO3034/71A patent/NO131887C/no unknown
- 1971-08-13 IE IE1027/71A patent/IE35517B1/xx unknown
- 1971-08-16 AU AU32411/71A patent/AU462319B2/en not_active Expired
- 1971-10-28 ES ES396453A patent/ES396453A1/es not_active Expired
- 1971-10-28 ES ES396454A patent/ES396454A1/es not_active Expired
-
1978
- 1978-12-06 YU YU2884/78A patent/YU42168B/xx unknown
- 1978-12-08 YU YU2882/78A patent/YU40542B/xx unknown
- 1978-12-08 YU YU2883/78A patent/YU35029B/xx unknown
- 1978-12-08 YU YU2881/78A patent/YU35028B/xx unknown
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