JPS601300B2 - 第三アミンの製造方法 - Google Patents
第三アミンの製造方法Info
- Publication number
- JPS601300B2 JPS601300B2 JP50040839A JP4083975A JPS601300B2 JP S601300 B2 JPS601300 B2 JP S601300B2 JP 50040839 A JP50040839 A JP 50040839A JP 4083975 A JP4083975 A JP 4083975A JP S601300 B2 JPS601300 B2 JP S601300B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- group
- carbon atoms
- mathematical
- following formula
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003512 tertiary amines Chemical class 0.000 title claims description 15
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 239000000126 substance Substances 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000007513 acids Chemical class 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- -1 ethylenedioxy group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000002560 nitrile group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 230000000911 decarboxylating effect Effects 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 210000001015 abdomen Anatomy 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 125000000468 ketone group Chemical group 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 210000002460 smooth muscle Anatomy 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-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
- 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000269851 Sarda sarda Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 2
- 229960004484 carbachol Drugs 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- OBNCKNCVKJNDBV-UHFFFAOYSA-N ethyl butyrate Chemical compound CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 210000002229 urogenital system Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AFFCAKKBRLTNFX-UHFFFAOYSA-N 2-(4-chlorobutyl)-2-methyl-1,3-dioxolane Chemical compound ClCCCCC1(C)OCCO1 AFFCAKKBRLTNFX-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 208000004998 Abdominal Pain Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000700198 Cavia Species 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 206010020651 Hyperkinesia Diseases 0.000 description 1
- 208000000269 Hyperkinesis Diseases 0.000 description 1
- 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 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 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
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 229940090012 bentyl Drugs 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 206010009887 colitis Diseases 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000002183 duodenal effect Effects 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 238000005259 measurement Methods 0.000 description 1
- 230000000956 myotropic effect Effects 0.000 description 1
- 230000002276 neurotropic effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012260 resinous material Substances 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 210000000626 ureter Anatomy 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NLAANVRAGE7404733,A NL178686C (nl) | 1974-04-08 | 1974-04-08 | Werkwijze ter bereiding of vervaardiging van spasmolytisch werkzame preparaten en werkwijze ter bereiding van n-alkyl-n-gesubstitueerd alkylbeta-fenylethylaminen met spasmolytische werking. |
| NL7404733 | 1974-04-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50135038A JPS50135038A (en, 2012) | 1975-10-25 |
| JPS601300B2 true JPS601300B2 (ja) | 1985-01-14 |
Family
ID=19821134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50040839A Expired JPS601300B2 (ja) | 1974-04-08 | 1975-04-05 | 第三アミンの製造方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (2) | US3996245A (en, 2012) |
| JP (1) | JPS601300B2 (en, 2012) |
| AR (3) | AR214280A1 (en, 2012) |
| AT (1) | AT344694B (en, 2012) |
| BE (1) | BE827703A (en, 2012) |
| CA (1) | CA1060457A (en, 2012) |
| CH (3) | CH615151A5 (en, 2012) |
| DE (1) | DE2514914C2 (en, 2012) |
| DK (1) | DK144975A (en, 2012) |
| ES (1) | ES436340A1 (en, 2012) |
| FR (1) | FR2266496B1 (en, 2012) |
| GB (1) | GB1500434A (en, 2012) |
| IL (1) | IL47015A (en, 2012) |
| NL (1) | NL178686C (en, 2012) |
| PH (1) | PH13033A (en, 2012) |
| SE (1) | SE439008B (en, 2012) |
| ZA (1) | ZA752003B (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4125623A (en) * | 1974-04-08 | 1978-11-14 | U.S. Philips Corporation | Spasmolytics |
| FI70205C (fi) * | 1978-05-17 | 1986-09-15 | Degussa | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara l-/3-hydroxi-3-fenylpropyl-(2)/-/3-oxo-propyl/aminer |
| US4908027A (en) * | 1986-09-12 | 1990-03-13 | Alza Corporation | Subsaturated transdermal therapeutic system having improved release characteristics |
| US5344656A (en) * | 1986-09-12 | 1994-09-06 | Alza Corporation | Subsaturated transdermal therapeutic system having improved release characteristics |
| NL8700842A (en, 2012) * | 1987-04-10 | 1988-11-01 | Duphar Int Res | |
| US4781924A (en) | 1987-11-09 | 1988-11-01 | Alza Corporation | Transdermal drug delivery device |
| US5004610A (en) * | 1988-06-14 | 1991-04-02 | Alza Corporation | Subsaturated nicotine transdermal therapeutic system |
| US5508038A (en) * | 1990-04-16 | 1996-04-16 | Alza Corporation | Polyisobutylene adhesives for transdermal devices |
| GB9727470D0 (en) * | 1997-12-30 | 1998-02-25 | Genencor Int Bv | Proteases from gram positive organisms |
| US20050008607A1 (en) * | 2003-06-05 | 2005-01-13 | L'oreal | Composition containing a carbonyl amine |
| SE543957C2 (en) | 2019-12-23 | 2021-10-05 | Elfa Int Ab | Storage system for assembly without tools, comprising a connector element comprising an insert and a dowel extending from the insert into the shelf |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1768500A1 (de) * | 1968-05-18 | 1972-01-05 | Degussa | Verfahren zur Herstellung von Alkoxygruppen enthaltenden Aminoketonen II |
| US3950335A (en) * | 1970-05-02 | 1976-04-13 | Boehringer Ingelheim Gmbh | 1-(3'-trifluoromethyl-4'-chloro-phenyl)-2-amino-propanes and salts thereof |
-
1974
- 1974-04-08 NL NLAANVRAGE7404733,A patent/NL178686C/xx not_active IP Right Cessation
-
1975
- 1975-04-01 ZA ZA752003A patent/ZA752003B/xx unknown
- 1975-04-03 US US05/564,777 patent/US3996245A/en not_active Expired - Lifetime
- 1975-04-04 PH PH17019A patent/PH13033A/en unknown
- 1975-04-04 IL IL47015A patent/IL47015A/xx unknown
- 1975-04-04 GB GB13911/75A patent/GB1500434A/en not_active Expired
- 1975-04-04 CH CH430675A patent/CH615151A5/de not_active IP Right Cessation
- 1975-04-04 DK DK144975A patent/DK144975A/da not_active IP Right Cessation
- 1975-04-05 JP JP50040839A patent/JPS601300B2/ja not_active Expired
- 1975-04-05 DE DE2514914A patent/DE2514914C2/de not_active Expired
- 1975-04-05 ES ES436340A patent/ES436340A1/es not_active Expired
- 1975-04-07 AT AT262775A patent/AT344694B/de not_active IP Right Cessation
- 1975-04-07 SE SE7503952A patent/SE439008B/xx not_active IP Right Cessation
- 1975-04-08 AR AR258243A patent/AR214280A1/es active
- 1975-04-08 CA CA224,082A patent/CA1060457A/en not_active Expired
- 1975-04-08 BE BE155207A patent/BE827703A/xx not_active IP Right Cessation
- 1975-04-08 FR FR7510952A patent/FR2266496B1/fr not_active Expired
-
1977
- 1977-04-28 AR AR267392A patent/AR214315A1/es active
- 1977-04-28 AR AR267393A patent/AR214316A1/es active
-
1979
- 1979-07-13 US US06/057,223 patent/US4308282A/en not_active Expired - Lifetime
- 1979-07-25 CH CH689079A patent/CH620899A5/de not_active IP Right Cessation
- 1979-07-25 CH CH688979A patent/CH620898A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| SE439008B (sv) | 1985-05-28 |
| AT344694B (de) | 1978-08-10 |
| NL178686C (nl) | 1986-05-01 |
| DK144975A (en, 2012) | 1975-10-09 |
| CH620898A5 (en, 2012) | 1980-12-31 |
| AU7985975A (en) | 1976-10-14 |
| AR214280A1 (es) | 1979-05-31 |
| US3996245A (en) | 1976-12-07 |
| CA1060457A (en) | 1979-08-14 |
| ZA752003B (en) | 1976-11-24 |
| AR214315A1 (es) | 1979-05-31 |
| FR2266496B1 (en, 2012) | 1980-01-25 |
| DE2514914A1 (de) | 1975-10-09 |
| AR214316A1 (es) | 1979-05-31 |
| ES436340A1 (es) | 1977-05-01 |
| BE827703A (fr) | 1975-10-08 |
| NL178686B (nl) | 1985-12-02 |
| IL47015A (en) | 1978-06-15 |
| ATA262775A (de) | 1977-12-15 |
| JPS50135038A (en, 2012) | 1975-10-25 |
| FR2266496A1 (en, 2012) | 1975-10-31 |
| CH615151A5 (en, 2012) | 1980-01-15 |
| SE7503952L (sv) | 1975-10-09 |
| GB1500434A (en) | 1978-02-08 |
| CH620899A5 (en, 2012) | 1980-12-31 |
| IL47015A0 (en) | 1976-10-31 |
| US4308282A (en) | 1981-12-29 |
| NL7404733A (nl) | 1975-10-10 |
| PH13033A (en) | 1979-11-15 |
| DE2514914C2 (de) | 1985-03-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0099148B1 (en) | Piperazine derivatives, processes for their preparation and pharmaceutical preparations containing them | |
| JPS6026776B2 (ja) | 新規オキシムエーテル化合物 | |
| IE46278B1 (en) | Piperazine derivatives | |
| CH644348A5 (fr) | Amino-ethers oxydes, leur procede de preparation et medicament les contenant. | |
| JPS601300B2 (ja) | 第三アミンの製造方法 | |
| GB2042525A (en) | Benzylalcohol derivative and process for preparing the same | |
| CN1056691A (zh) | 新的磺酰化合物及其制备方法 | |
| JPH0245629B2 (en, 2012) | ||
| CA2087855A1 (en) | 1,4-disubstituted piperazines | |
| EP0061149A1 (en) | Alkylenedioxybenzene derivatives and acid addition salts thereof and a process for their preparation | |
| EP0015615B1 (en) | Phenyl piperazine derivatives, their preparation and antiagressive medicines containing them | |
| JPS6047255B2 (ja) | ２−アミノ−５−スルフアモイル−安息香酸アミドの製法 | |
| US4125623A (en) | Spasmolytics | |
| JP2002527515A (ja) | 精神障害の処置のための３−テトラヒドロピリジン−４−イルインドール類 | |
| FR2523965A1 (fr) | (benzimidazolyl-1)-1, n-((hydroxy-4 methoxy-3 phenyl)-2 hydroxy-2 ethyl) amino-3 butane et ses sels a activite b-adrenergique, leurs applications therapeutiques, et procede pour les preparer | |
| JPS5948831B2 (ja) | ベンゾチアゾ−ル誘導体、およびそれらの製造法 | |
| GB2195634A (en) | Thiophene derivatives | |
| PL101949B1 (pl) | A method of producing new ether derivatives of oxime | |
| KR20100046256A (ko) | 치료 조성물 | |
| EP0520882B1 (fr) | Dérivés de 2-aminopyrimidine-4-carboxamide, leur préparation et leur application en thérapeutique | |
| US4065501A (en) | Basic enol ether and acid addition salts thereof | |
| JPH0920758A (ja) | 新規環状ジアミン誘導体及びその製造法 | |
| JPH03294277A (ja) | ピペリジン誘導体 | |
| CH620913A5 (en, 2012) | ||
| JP2825643B2 (ja) | 新規アリールオキシーアルキルアミン、その製法及びこれを含有する心臓循環系疾患治療用の医薬品 |