NO120030B - - Google Patents
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- Publication number
- NO120030B NO120030B NO162689A NO16268966A NO120030B NO 120030 B NO120030 B NO 120030B NO 162689 A NO162689 A NO 162689A NO 16268966 A NO16268966 A NO 16268966A NO 120030 B NO120030 B NO 120030B
- Authority
- NO
- Norway
- Prior art keywords
- phenyl
- compounds
- acid
- formula
- dimethylaminopropyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- -1 alkali metal amide Chemical class 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 229960000482 pethidine Drugs 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 5
- 229960004193 dextropropoxyphene Drugs 0.000 description 5
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 description 5
- BCXHDORHMMZBBZ-DORFAMGDSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;sulfuric acid Chemical compound OS(O)(=O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC BCXHDORHMMZBBZ-DORFAMGDSA-N 0.000 description 4
- CVZWTVDMZYGOSX-UHFFFAOYSA-N 2-methyl-2-phenyl-3h-inden-1-one Chemical compound C1C2=CC=CC=C2C(=O)C1(C)C1=CC=CC=C1 CVZWTVDMZYGOSX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 description 4
- 229960003871 codeine sulfate Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic 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
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229960004126 codeine Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000001630 malic acid Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 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
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- ZVZHMMFRKNJLTD-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-2-methyl-2-phenyl-3H-inden-1-ol Chemical compound CN(C)CCCC1(O)C2=CC=CC=C2CC1(C)C1=CC=CC=C1 ZVZHMMFRKNJLTD-UHFFFAOYSA-N 0.000 description 1
- MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
- DZMDPHNGKBEVRE-UHFFFAOYSA-N 1-chloroheptane Chemical compound CCCCCCCCl DZMDPHNGKBEVRE-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- FHONLNCEDWDJSX-UHFFFAOYSA-N 2-methyl-2-phenyl-3,4-dihydronaphthalen-1-one Chemical compound C1CC2=CC=CC=C2C(=O)C1(C)C1=CC=CC=C1 FHONLNCEDWDJSX-UHFFFAOYSA-N 0.000 description 1
- WRFYIYOXJWKONR-UHFFFAOYSA-N 4-bromo-2-methoxyaniline Chemical compound COC1=CC(Br)=CC=C1N WRFYIYOXJWKONR-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- AQNQQHJNRPDOQV-UHFFFAOYSA-N bromocyclohexane Chemical compound BrC1CCCCC1 AQNQQHJNRPDOQV-UHFFFAOYSA-N 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KMGBZBJJOKUPIA-UHFFFAOYSA-N butyl iodide Chemical compound CCCCI KMGBZBJJOKUPIA-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 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
- 229960000278 theophylline Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/38—2,3-Dihydro derivatives, e.g. isoflavanones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G17/00—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process
- G03G17/04—Electrographic processes using patterns other than charge patterns, e.g. an electric conductivity pattern; Processes involving a migration, e.g. photoelectrophoresis, photoelectrosolography; Processes involving a selective transfer, e.g. electrophoto-adhesive processes; Apparatus essentially involving a single such process using photoelectrophoresis
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03G—ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY
- G03G5/00—Recording members for original recording by exposure, e.g. to light, to heat, to electrons; Manufacture thereof; Selection of materials therefor
- G03G5/12—Recording members for multicolour processes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Physics & Mathematics (AREA)
- Molecular Biology (AREA)
- Electrochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Electrochromic Elements, Electrophoresis, Or Variable Reflection Or Absorption Elements (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Vertical, Hearth, Or Arc Furnaces (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Optical Filters (AREA)
Applications Claiming Priority (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US41110665A | 1965-03-19 | 1965-03-19 | |
US44110665A | 1965-03-19 | 1965-03-19 | |
US45265165A | 1965-05-03 | 1965-05-03 | |
US45496265A | 1965-05-11 | 1965-05-11 | |
US504122A US3419560A (en) | 1965-03-19 | 1965-10-23 | 1-aminoalkyl 2-aryl indanes and tetrahydronaphthalenes |
US59066666A | 1966-10-31 | 1966-10-31 | |
US79882868A | 1968-11-01 | 1968-11-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
NO120030B true NO120030B (de) | 1970-08-17 |
Family
ID=27569758
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO162166A NO123368B (de) | 1965-03-19 | 1966-03-18 | |
NO162689A NO120030B (de) | 1965-03-19 | 1966-04-21 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO162166A NO123368B (de) | 1965-03-19 | 1966-03-18 |
Country Status (11)
Country | Link |
---|---|
US (5) | US3553093A (de) |
AT (3) | AT285326B (de) |
BE (1) | BE680863A (de) |
CH (3) | CH479100A (de) |
DE (1) | DE1522742A1 (de) |
FR (2) | FR1568731A (de) |
GB (4) | GB1157671A (de) |
IL (1) | IL25304A (de) |
NL (1) | NL6606339A (de) |
NO (2) | NO123368B (de) |
SE (2) | SE341330B (de) |
Families Citing this family (51)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE371190B (de) * | 1972-03-24 | 1974-11-11 | Kabi Ab | |
US3804508A (en) * | 1965-05-28 | 1974-04-16 | V Mihajlov | Photoelectrophoretic apparatus for heat fixing an image |
US3504031A (en) * | 1966-05-24 | 1970-03-31 | Mead Johnson & Co | 1-aminoalkyl-1-phenylindene process and intermediate therefor |
US3477934A (en) * | 1966-06-29 | 1969-11-11 | Xerox Corp | Imaging process |
US3680955A (en) * | 1968-07-16 | 1972-08-01 | Minolta Camera Kk | Apparatus for forming an electrostatic image in a camera |
US3620950A (en) * | 1968-10-03 | 1971-11-16 | Xerox Corp | Electrophoretic imaging employing periodic electromagnetic radiation |
US3784302A (en) * | 1968-10-03 | 1974-01-08 | Xerox Corp | Electrophoretic imaging apparatus including application of dynamic stress on the particle suspension |
US3657091A (en) * | 1968-10-03 | 1972-04-18 | Xerox Corp | Electrophoretic imaging method employing a periodic electric field |
US3811764A (en) * | 1968-10-03 | 1974-05-21 | Xerox Corp | Apparatus for photoelectrophoretic imaging using a periodic electric field |
US3743404A (en) * | 1968-10-03 | 1973-07-03 | Xerox Corp | Photoelectrophoretic imaging apparatus including means to simultaneously apply a compressive stress and shear stress to the imaging suspension |
US3853556A (en) * | 1969-05-02 | 1974-12-10 | Xerox Corp | Method for eliminating electrical arcing during photoelectrophoretic imaging |
BE756481A (fr) * | 1969-09-23 | 1971-03-22 | Xerox Corp | Procede de formation d'image photoelectrophoretique par reflexion |
USRE28360E (en) * | 1969-10-03 | 1975-03-04 | Electrophoretic color display device | |
US3761174A (en) * | 1969-10-31 | 1973-09-25 | Xerox Corp | Manifold web handling |
US3690754A (en) * | 1969-11-14 | 1972-09-12 | Xerox Corp | Control system for an optical imaging system |
JPS527348B1 (de) * | 1970-01-09 | 1977-03-01 | ||
US3909262A (en) * | 1970-12-14 | 1975-09-30 | Xerox Corp | Imaging migration member employing a gelatin overcoating |
US3719484A (en) * | 1971-01-06 | 1973-03-06 | Xerox Corp | Photoelectrophoretic imaging method |
US3751420A (en) * | 1971-04-01 | 1973-08-07 | Squibb & Sons Inc | Monoolmonoene amines |
US3859438A (en) * | 1971-07-08 | 1975-01-07 | Boehringer Sohn Ingelheim | Pharmaceutical compositions containing an n-(1-bicyclic aryl-propyl-2)-n-bicyclic aryl-piperazine and method of use |
US3984464A (en) * | 1972-10-06 | 1976-10-05 | A. Christiaens Societe Anonyme | Derivatives of 2-amino-(1,2,3,4-tetrahydronaphthalene), the preparation and use thereof |
US3859576A (en) * | 1973-02-15 | 1975-01-07 | Xerox Corp | High performance blocking electrode for electrophotophoresis |
US3905812A (en) * | 1973-04-23 | 1975-09-16 | Xerox Corp | Imaging process |
US3917880A (en) * | 1973-06-27 | 1975-11-04 | Xerox Corp | Electrophoretic imaging system |
US3945724A (en) * | 1974-06-04 | 1976-03-23 | Xerox Corporation | Velocity compensation for bead bypass |
US4078928A (en) * | 1975-03-03 | 1978-03-14 | Xerox Corporation | Photoelectrophoretic imaging method |
US4084896A (en) * | 1975-04-24 | 1978-04-18 | Xerox Corporation | Photoelectrophoretic web imaging apparatus |
CH619701A5 (de) * | 1975-08-07 | 1980-10-15 | Bayer Ag | |
US4013673A (en) * | 1976-04-13 | 1977-03-22 | Warner-Lambert Company | 2,3-dihydro-3-(2-pyridinyl)-4h-1-benzopyran-4-one n-oxides |
US4130359A (en) * | 1976-07-23 | 1978-12-19 | Eastman Kodak Company | Electrophoretic migration imaging apparatus and method utilizing enlarged migration environment |
DE2814983A1 (de) * | 1978-04-07 | 1979-10-18 | Bayer Ag | Neue chromanon-derivate |
CH641147A5 (de) * | 1979-01-17 | 1984-02-15 | Sandoz Ag | 3-amino-2-hydroxypropoxyaryl-derivat, seine herstellung und dieses enthaltende heilmittel. |
NL8003141A (nl) * | 1980-05-30 | 1982-01-04 | Akzo Nv | Biologisch aktieve tricyclische aminen. |
CH648030A5 (de) * | 1980-12-15 | 1985-02-28 | Sandoz Ag | Benzopyran-allylaminderivate, verfahren zu ihrer herstellung und ihre verwendung. |
US4321270A (en) * | 1981-01-29 | 1982-03-23 | E. R. Squibb & Sons, Inc. | Substituted chromans |
US4452801A (en) * | 1981-09-24 | 1984-06-05 | E. R. Squibb & Sons, Inc. | Chromans including heterocyclic substituent |
US4505932A (en) * | 1983-05-13 | 1985-03-19 | Abbott Laboratories | Method of producing α2 -adrenergic receptor agonist activity |
GB8704572D0 (en) * | 1987-02-26 | 1987-04-01 | Lundbeck & Co As H | Organic compounds |
JP2693843B2 (ja) * | 1988-01-15 | 1997-12-24 | アボツト・ラボラトリーズ | 1―アミノメチル―1,2,3,4―テトラヒドロナフタレン |
US5128362A (en) * | 1988-01-15 | 1992-07-07 | Abbott Laboratories | 1-aminomethyl-1,2,3,4-tetrahydronaphthalenes |
US5086074A (en) * | 1988-01-15 | 1992-02-04 | Abbott Laboratories | 1-aminomethyl-1,2,3,4-tetrahydronaphthalenes |
WO1990012010A1 (en) * | 1989-04-07 | 1990-10-18 | Pfizer Inc. | Substituted chromans in the treatment of asthma, arthritis and related diseases |
US5500444A (en) * | 1989-11-14 | 1996-03-19 | Hoechst Marion Roussel, Inc. | Cardioprotective tocopherol analogs |
US5063397A (en) * | 1990-05-25 | 1991-11-05 | Xerox Corporation | Variable-thickness imaging members |
EP0550292A1 (de) * | 1992-01-02 | 1993-07-07 | Merrell Dow Pharmaceuticals Inc. | Tocopherol-Analog zum Gewebeschutz |
US5510373A (en) * | 1992-04-06 | 1996-04-23 | Merrell Pharmaceuticals Inc. | Cardioprotective agents |
US5721233A (en) * | 1992-04-06 | 1998-02-24 | Merrell Pharmaceuticals Inc. | Derivatives of 2,3-dihydro benzofuranols |
US5545660A (en) * | 1992-04-07 | 1996-08-13 | Merrell Pharmaceuticals Inc. | Hydrazide derivatives of 3,4-dihydro-2H-1-benzopyrans |
IL143780A (en) * | 2001-06-14 | 2007-06-03 | Cerel Ceramic Technologies Ltd | Process for manufacturing electrode |
US7339715B2 (en) * | 2003-03-25 | 2008-03-04 | E Ink Corporation | Processes for the production of electrophoretic displays |
DE102005010000A1 (de) * | 2005-03-04 | 2006-09-07 | Merck Patent Gmbh | Indane |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2758939A (en) * | 1953-12-30 | 1956-08-14 | Rca Corp | Electrostatic printing |
US2987660A (en) * | 1955-06-06 | 1961-06-06 | Haloid Xerox Inc | Xerographic charging |
US2902974A (en) * | 1956-06-14 | 1959-09-08 | Ibm | Latent electrostatic image developing apparatus |
US2884434A (en) * | 1957-03-07 | 1959-04-28 | Dow Corning | Haloorgano silcarbane siloxanes |
US2940847A (en) * | 1957-07-03 | 1960-06-14 | None i red | |
US3068479A (en) * | 1958-05-09 | 1962-12-11 | Burroughs Corp | Electrographic recording apparatus |
US3251685A (en) * | 1959-10-19 | 1966-05-17 | Xerox Corp | Method of controlling contrast in a xerographic reproduction process |
US3142682A (en) * | 1961-11-21 | 1964-07-28 | Ciba Geigy Corp | Tertiary amino derivatives of chromans and homo-chromans |
US3271145A (en) * | 1963-12-23 | 1966-09-06 | Eastman Kodak Co | Process for producing an electrostatic charge image |
US3301866A (en) * | 1965-08-12 | 1967-01-31 | Rexall Drug Chemical | Substituted indenopyridines |
-
1965
- 1965-03-19 US US441106A patent/US3553093A/en not_active Expired - Lifetime
- 1965-05-03 US US452651A patent/US3474019A/en not_active Expired - Lifetime
- 1965-10-23 US US504122A patent/US3419560A/en not_active Expired - Lifetime
-
1966
- 1966-03-04 IL IL25304A patent/IL25304A/en unknown
- 1966-03-17 GB GB11857/66A patent/GB1157671A/en not_active Expired
- 1966-03-17 GB GB34793/68A patent/GB1149666A/en not_active Expired
- 1966-03-17 GB GB11856/66A patent/GB1149665A/en not_active Expired
- 1966-03-17 DE DE19661522742 patent/DE1522742A1/de active Pending
- 1966-03-18 AT AT262066A patent/AT285326B/de not_active IP Right Cessation
- 1966-03-18 NO NO162166A patent/NO123368B/no unknown
- 1966-03-18 CH CH393866A patent/CH479100A/fr not_active IP Right Cessation
- 1966-03-18 CH CH393766A patent/CH479099A/fr not_active IP Right Cessation
- 1966-03-18 SE SE03639/66A patent/SE341330B/xx unknown
- 1966-03-18 SE SE03640/66A patent/SE334540B/xx unknown
- 1966-03-18 AT AT261966A patent/AT286783B/de active
- 1966-04-19 GB GB17156/66A patent/GB1149615A/en not_active Expired
- 1966-04-21 NO NO162689A patent/NO120030B/no unknown
- 1966-05-10 NL NL6606339A patent/NL6606339A/xx unknown
- 1966-05-11 AT AT447466A patent/AT279598B/de not_active IP Right Cessation
- 1966-05-11 BE BE680863D patent/BE680863A/xx unknown
- 1966-05-11 FR FR1568731D patent/FR1568731A/fr not_active Expired
- 1966-05-11 CH CH682366A patent/CH466305A/fr unknown
- 1966-08-10 FR FR72633A patent/FR5864M/fr not_active Expired
- 1966-10-31 US US590666A patent/US3448025A/en not_active Expired - Lifetime
-
1968
- 1968-11-01 US US798828*A patent/US3551320A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
BE680863A (de) | 1966-11-14 |
CH466305A (fr) | 1968-12-15 |
IL25304A (en) | 1969-11-30 |
DE1522742A1 (de) | 1969-10-30 |
GB1149666A (en) | 1969-04-23 |
GB1157671A (en) | 1969-07-09 |
DE1522743B2 (de) | 1972-07-27 |
US3553093A (en) | 1971-01-05 |
GB1149615A (en) | 1969-04-23 |
NO123368B (de) | 1971-11-01 |
AT286783B (de) | 1970-12-28 |
SE341330B (de) | 1971-12-20 |
NL6606339A (de) | 1966-11-14 |
AT285326B (de) | 1970-10-27 |
FR1568731A (de) | 1969-05-30 |
GB1149665A (en) | 1969-04-23 |
FR5864M (de) | 1968-03-11 |
SE334540B (de) | 1971-04-26 |
US3419560A (en) | 1968-12-31 |
US3474019A (en) | 1969-10-21 |
CH479099A (fr) | 1969-09-30 |
CH479100A (fr) | 1969-09-30 |
DE1522743A1 (de) | 1969-10-30 |
AT279598B (de) | 1970-03-10 |
US3448025A (en) | 1969-06-03 |
US3551320A (en) | 1970-12-29 |
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