HU176927B - Sposob poluchenija n-geteroaril-metil-benzomorfanov i - - Google Patents
Sposob poluchenija n-geteroaril-metil-benzomorfanov i - Download PDFInfo
- Publication number
- HU176927B HU176927B HU73BO1460A HUBO001607A HU176927B HU 176927 B HU176927 B HU 176927B HU 73BO1460 A HU73BO1460 A HU 73BO1460A HU BO001607 A HUBO001607 A HU BO001607A HU 176927 B HU176927 B HU 176927B
- Authority
- HU
- Hungary
- Prior art keywords
- dimethyl
- methyl
- hydroxy
- formula
- residue
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 239000012280 lithium aluminium hydride Substances 0.000 claims abstract description 6
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 239000012279 sodium borohydride Substances 0.000 claims description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 8
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- -1 1,4-butylene Chemical group 0.000 abstract description 42
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- 150000001875 compounds Chemical class 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
- 229910052938 sodium sulfate Inorganic materials 0.000 description 13
- 235000011152 sodium sulphate Nutrition 0.000 description 13
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 230000009467 reduction Effects 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229910000564 Raney nickel Inorganic materials 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000002026 chloroform extract Substances 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000005804 alkylation reaction Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 150000003556 thioamides Chemical class 0.000 description 4
- AFFZVBHMMXZNKE-UHFFFAOYSA-N 2-methylfuran-3-carbonyl chloride Chemical compound CC=1OC=CC=1C(Cl)=O AFFZVBHMMXZNKE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- NGPGDYLVALNKEG-OLXYHTOASA-N diammonium L-tartrate Chemical class [NH4+].[NH4+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O NGPGDYLVALNKEG-OLXYHTOASA-N 0.000 description 2
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007717 exclusion Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- NMTFBSFVDGFCIT-NZPFSMCRSA-N (1S,9R,10R)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-14-ol Chemical compound OC1CCC[C@H]2[C@]3([H])NCC[C@@]21C1=CC=CC=C1C3 NMTFBSFVDGFCIT-NZPFSMCRSA-N 0.000 description 1
- SLROTKFSBGWEDD-PDTFXZCISA-N (4r,4ar,7s,7ar,12bs)-3-methyl-1,2,4,4a,7,7a,10,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9,9-triol Chemical compound O[C@H]([C@@H]1O2)C=C[C@H]3[C@]4([H])N(C)CC[C@@]31C1=C2C(O)(O)CC=C1C4 SLROTKFSBGWEDD-PDTFXZCISA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FNPVYRJTBXHIPB-UHFFFAOYSA-N 1-chloro-3-fluoro-2-methylbenzene Chemical compound CC1=C(F)C=CC=C1Cl FNPVYRJTBXHIPB-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- IYNWSQDZXMGGGI-NUEKZKHPSA-N 3-hydroxymorphinan Chemical compound C1CCC[C@H]2[C@H]3CC4=CC=C(O)C=C4[C@]21CCN3 IYNWSQDZXMGGGI-NUEKZKHPSA-N 0.000 description 1
- 229910000497 Amalgam Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001079660 Phanes Species 0.000 description 1
- 101710084578 Short neurotoxin 1 Proteins 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VUXGMZFHWHYQFK-QRRVGDGBSA-N [(1R,9R,10R)-5-(furan-2-carbonyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2,4,6-trien-4-yl] furan-2-carboxylate Chemical compound O1C(=CC=C1)C(=O)C1=CC=2C[C@@H]3[C@@H]4CCCC[C@@]4(C=2C=C1OC(=O)C=1OC=CC=1)CCN3 VUXGMZFHWHYQFK-QRRVGDGBSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000002152 alkylating effect Effects 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
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000005521 carbonamide group Chemical group 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 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
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 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 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000004149 thio group Chemical group *S* 0.000 description 1
- 238000007280 thionation reaction Methods 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722243703 DE2243703A1 (de) | 1972-09-06 | 1972-09-06 | Verfahren zur herstellung von n(heteroaryl-methyl)-benzomorphanen und -morphinanen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176927B true HU176927B (hu) | 1981-06-28 |
Family
ID=5855589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU73BO1460A HU176927B (hu) | 1972-09-06 | 1973-09-04 | Sposob poluchenija n-geteroaril-metil-benzomorfanov i - |
Country Status (17)
| Country | Link |
|---|---|
| JP (1) | JPS578109B2 (en]) |
| AT (1) | AT327408B (en]) |
| BG (1) | BG22392A3 (en]) |
| CH (2) | CH590270A5 (en]) |
| CS (2) | CS168043B2 (en]) |
| DD (1) | DD107035A5 (en]) |
| DE (1) | DE2243703A1 (en]) |
| DK (1) | DK140171C (en]) |
| ES (2) | ES418488A1 (en]) |
| FI (1) | FI63027C (en]) |
| HU (1) | HU176927B (en]) |
| NL (1) | NL7312177A (en]) |
| PL (1) | PL86931B1 (en]) |
| RO (1) | RO62924A (en]) |
| SE (1) | SE417821B (en]) |
| SU (1) | SU543347A3 (en]) |
| YU (2) | YU36022B (en]) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5769970B2 (ja) * | 2007-11-16 | 2015-08-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベンゾモルファン及び関連骨格のアリール−及びヘテロアリールカルボニル誘導体、かかる化合物を含有する医薬及びこれらの使用 |
-
1972
- 1972-09-06 DE DE19722243703 patent/DE2243703A1/de active Pending
-
1973
- 1973-08-14 AT AT710973A patent/AT327408B/de not_active IP Right Cessation
- 1973-09-03 CH CH1260873A patent/CH590270A5/xx not_active IP Right Cessation
- 1973-09-03 CH CH24277A patent/CH599953A5/xx not_active IP Right Cessation
- 1973-09-04 CS CS615673A patent/CS168043B2/cs unknown
- 1973-09-04 FI FI274873A patent/FI63027C/fi active
- 1973-09-04 HU HU73BO1460A patent/HU176927B/hu unknown
- 1973-09-04 CS CS812174A patent/CS185228B2/cs unknown
- 1973-09-04 BG BG025597A patent/BG22392A3/xx unknown
- 1973-09-04 DD DD17326773A patent/DD107035A5/xx unknown
- 1973-09-04 NL NL7312177A patent/NL7312177A/xx not_active Application Discontinuation
- 1973-09-05 JP JP10010173A patent/JPS578109B2/ja not_active Expired
- 1973-09-05 YU YU236573A patent/YU36022B/xx unknown
- 1973-09-05 ES ES418488A patent/ES418488A1/es not_active Expired
- 1973-09-05 DK DK489973A patent/DK140171C/da not_active IP Right Cessation
- 1973-09-05 PL PL16504273A patent/PL86931B1/pl unknown
- 1973-09-05 SE SE7312111A patent/SE417821B/sv unknown
- 1973-09-05 RO RO7599273A patent/RO62924A/ro unknown
-
1974
- 1974-01-04 ES ES422006A patent/ES422006A1/es not_active Expired
- 1974-10-10 SU SU2065404A patent/SU543347A3/ru active
-
1979
- 1979-11-27 YU YU291379A patent/YU36023B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BG22392A3 (bg) | 1977-02-20 |
| FI63027B (fi) | 1982-12-31 |
| CS185228B2 (en) | 1978-09-15 |
| ATA710973A (de) | 1975-04-15 |
| YU236573A (en) | 1981-04-30 |
| YU36023B (en) | 1981-11-13 |
| YU36022B (en) | 1981-11-13 |
| ES418488A1 (es) | 1976-04-01 |
| DK140171C (da) | 1979-11-26 |
| ES422006A1 (es) | 1976-06-16 |
| YU291379A (en) | 1981-04-30 |
| PL86931B1 (en]) | 1976-06-30 |
| JPS578109B2 (en]) | 1982-02-15 |
| CS168043B2 (en]) | 1976-05-28 |
| DK140171B (da) | 1979-07-02 |
| SU543347A3 (ru) | 1977-01-15 |
| DE2243703A1 (de) | 1974-03-14 |
| CH599953A5 (en]) | 1978-06-15 |
| AT327408B (de) | 1976-01-26 |
| CH590270A5 (en]) | 1977-07-29 |
| DD107035A5 (en]) | 1974-07-12 |
| JPS49100085A (en]) | 1974-09-20 |
| SE417821B (sv) | 1981-04-13 |
| NL7312177A (en]) | 1974-03-08 |
| RO62924A (fr) | 1978-05-15 |
| FI63027C (fi) | 1983-04-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0179383B1 (en) | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds, a process for their preparation and their use as medicaments | |
| Ohno et al. | Nad (P)+-nad (p) h models. 57: Stereochemistry in (net) hydride transfer from and to nad (p)+-nad (p) h models: chirality sink | |
| CN105198888B (zh) | 2,3a‑二取代‑3H–吡唑并[1,5‑a]吲哚‑4(3aH)‑酮衍生物及其合成方法 | |
| HU190703B (en) | Process for preparing new 1,2,3,4,4a,5,10,10a-octahydro-benzo/g/-quinoline derivatives | |
| US3830823A (en) | Process for the preparation of deethyleburnamonines | |
| US4087532A (en) | Analgesically useful 2-tetrahydrofurfuryl-5-lower alkyl-2-oxy-6,7-benzomorphans and salts thereof | |
| US4316029A (en) | Synthesis of vincaminic acid derivatives | |
| HU176927B (hu) | Sposob poluchenija n-geteroaril-metil-benzomorfanov i - | |
| SU545260A3 (ru) | Способ получени производных октагидроиндолохинолизина или их солей,или рацемата,или оптических антиподов | |
| HU199806B (en) | Process for producing (d-cis)-1,3,4,5-tetrahydro-4-phenyl-2h-benzazepin-2-one derivatives | |
| DK153149B (da) | Analogifremgangsmaade til fremstilling af hydroxyaminoeburnanderivater eller farmaceutisk acceptable syreadditionssalte eller optisk aktiv isomerer deraf, samt octahydroindolokinolizin-monoesterderivater til anvendelse som udgangsmateriale ved fremgangsmaaden | |
| US2977365A (en) | 3-dehydroyohimbanes and their preparation | |
| US3055888A (en) | 2-alkylmercapto-9-[2'-(n-alkylpiperidyl-2" and pyrrolidyl-2")-ethylidene-1']-thiaxanthenes | |
| US4399069A (en) | Process for an enantioselective synthesis of optically active 14-oxo-E-homo-eburnane derivatives | |
| US3960926A (en) | Process for preparing azasulfonium halide salts | |
| CA1094561A (en) | 1,2,3,4,10,10a-hexahydrobenz¬g|isoquinoline compounds | |
| US3954797A (en) | Process for preparing azasulfonium halide salts | |
| US4376860A (en) | Pyridyl ketone | |
| EP0251547A2 (en) | Chiral synthesis of (+)-trans-la-2,3,4A, 5,6-hexahydro-9-hydroxy-4-propyl-4H-naphth-(1,2-B)-1,4-oxazine | |
| US4048176A (en) | 2-(3-Methyl-4-phenyl-1,2,3,4-tetrahydro-2-isoquinolyl)-acetamidoxime dihydrochloride | |
| Meese et al. | Synthesis of deuterated 1, 2, 3, 4‐tetrahydroisoquinolines | |
| KR820000182B1 (ko) | 5-페닐-2-하이드록시 테트라하이드로푸란의 제조방법 | |
| Kalyanam et al. | A General Route to 3-(Hydroxyaryl) Tetrahydro Pyridazines and 1, 2-Diazepines and Derivatives δ | |
| US3314962A (en) | Ethynylated quinolizinium | |
| HU191693B (en) | Process for production of derivatives of 9-or-11 substituated apovincamin acid |