DE2525512A1 - Aminotetralolverbindungen, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittel - Google Patents
Aminotetralolverbindungen, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittelInfo
- Publication number
- DE2525512A1 DE2525512A1 DE19752525512 DE2525512A DE2525512A1 DE 2525512 A1 DE2525512 A1 DE 2525512A1 DE 19752525512 DE19752525512 DE 19752525512 DE 2525512 A DE2525512 A DE 2525512A DE 2525512 A1 DE2525512 A1 DE 2525512A1
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydronaphthalene
- benzyloxy
- compounds according
- trans
- amino
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 title claims description 137
- 238000000034 method Methods 0.000 title claims description 54
- 230000008569 process Effects 0.000 title claims description 24
- 238000004519 manufacturing process Methods 0.000 title description 3
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 acyl radical Chemical class 0.000 claims description 242
- 239000000203 mixture Substances 0.000 claims description 142
- 229910052739 hydrogen Inorganic materials 0.000 claims description 67
- 239000001257 hydrogen Substances 0.000 claims description 65
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 39
- 230000009467 reduction Effects 0.000 claims description 38
- 125000006239 protecting group Chemical group 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000002252 acyl group Chemical group 0.000 claims description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 22
- 150000002430 hydrocarbons Chemical group 0.000 claims description 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 125000001424 substituent group Chemical group 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000002015 acyclic group Chemical group 0.000 claims description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- BRGJIYTULBITAY-TZMCWYRMSA-N (1r,2r)-5-(hydroxymethyl)-2-(propan-2-ylamino)-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound OC1=CC=C2[C@@H](O)[C@H](NC(C)C)CCC2=C1CO BRGJIYTULBITAY-TZMCWYRMSA-N 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims 2
- FXPNGEPPURGWNP-IUODEOHRSA-N (1r,2r)-2-(cyclobutylamino)-5-(methylamino)-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound N([C@H]1[C@H](O)C=2C=CC(O)=C(C=2CC1)NC)C1CCC1 FXPNGEPPURGWNP-IUODEOHRSA-N 0.000 claims 1
- YRUWGIXIPBLADI-GDBMZVCRSA-N (1r,2r)-2-(cyclopentylamino)-5-(hydroxymethyl)-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound N([C@H]1[C@H](O)C=2C=CC(O)=C(C=2CC1)CO)C1CCCC1 YRUWGIXIPBLADI-GDBMZVCRSA-N 0.000 claims 1
- KAURIVRDBQNCPC-ZWNOBZJWSA-N (1r,2r)-5-amino-2-(propan-2-ylamino)-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound OC1=CC=C2[C@@H](O)[C@H](NC(C)C)CCC2=C1N KAURIVRDBQNCPC-ZWNOBZJWSA-N 0.000 claims 1
- APBBTKKLSNPFDP-UHFFFAOYSA-N 1-methyl-1,2,3,4-tetrahydronaphthalene Chemical compound C1=CC=C2C(C)CCCC2=C1 APBBTKKLSNPFDP-UHFFFAOYSA-N 0.000 claims 1
- VVYHZMSGIRDAEH-UHFFFAOYSA-N 5-amino-2-(tert-butylamino)-1,2,3,4-tetrahydronaphthalene-1,6-diol Chemical compound OC1=CC=C2C(O)C(NC(C)(C)C)CCC2=C1N VVYHZMSGIRDAEH-UHFFFAOYSA-N 0.000 claims 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 217
- 238000002844 melting Methods 0.000 description 209
- 230000008018 melting Effects 0.000 description 209
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 171
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 160
- 238000000921 elemental analysis Methods 0.000 description 159
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 152
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 133
- 239000000243 solution Substances 0.000 description 112
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 96
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 86
- ZIGMNVVOTWRPER-UHFFFAOYSA-N methyl 5-hydroxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound OC1CCCC2=C1C=CC=C2C(=O)OC ZIGMNVVOTWRPER-UHFFFAOYSA-N 0.000 description 85
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 77
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 66
- 239000013078 crystal Substances 0.000 description 56
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 55
- 239000000047 product Substances 0.000 description 46
- 239000002904 solvent Substances 0.000 description 45
- 239000000706 filtrate Substances 0.000 description 43
- 238000006722 reduction reaction Methods 0.000 description 38
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 37
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 36
- 239000003054 catalyst Substances 0.000 description 34
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 31
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 31
- 238000003756 stirring Methods 0.000 description 30
- 229960000583 acetic acid Drugs 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 25
- 238000010531 catalytic reduction reaction Methods 0.000 description 23
- 239000010410 layer Substances 0.000 description 22
- 239000002244 precipitate Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 230000001476 alcoholic effect Effects 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
- 238000001816 cooling Methods 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 18
- 235000017557 sodium bicarbonate Nutrition 0.000 description 18
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 18
- 125000003277 amino group Chemical group 0.000 description 17
- 239000007858 starting material Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- 239000012279 sodium borohydride Substances 0.000 description 15
- 229910000033 sodium borohydride Inorganic materials 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 230000000875 corresponding effect Effects 0.000 description 14
- 229920006395 saturated elastomer Polymers 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 13
- 239000011780 sodium chloride Substances 0.000 description 13
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000005457 ice water Substances 0.000 description 11
- 230000003647 oxidation Effects 0.000 description 11
- 238000007254 oxidation reaction Methods 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 10
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 239000012280 lithium aluminium hydride Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- IPHFEAMSIOVYCA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalene;hydrochloride Chemical compound Cl.C1=CC=C2CCCCC2=C1 IPHFEAMSIOVYCA-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 238000011282 treatment Methods 0.000 description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 239000001530 fumaric acid Substances 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- 239000007800 oxidant agent Substances 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- RZPFVRFSYMUDJO-UHFFFAOYSA-N 2h-naphthalen-1-one Chemical compound C1=CC=C2C(=O)CC=CC2=C1 RZPFVRFSYMUDJO-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 229940124630 bronchodilator Drugs 0.000 description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
- 208000006673 asthma Diseases 0.000 description 6
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- 238000011946 reduction process Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- QTNZYLCXEAGSRT-UHFFFAOYSA-N 2-amino-5-nitro-6-phenylmethoxy-1,2,3,4-tetrahydronaphthalen-1-ol;hydrochloride Chemical compound Cl.OC1C(N)CCC(C=2[N+]([O-])=O)=C1C=CC=2OCC1=CC=CC=C1 QTNZYLCXEAGSRT-UHFFFAOYSA-N 0.000 description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 5
- 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 5
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 4
- IWLBJIULEDJUBH-UHFFFAOYSA-N 5-chloro-2-(propan-2-ylamino)-1,2,3,4-tetrahydronaphthalene-1,6-diol;hydrochloride Chemical compound Cl.OC1=CC=C2C(O)C(NC(C)C)CCC2=C1Cl IWLBJIULEDJUBH-UHFFFAOYSA-N 0.000 description 4
- PQJCBJVNMUQEIE-UHFFFAOYSA-N 5-nitro-6-phenylmethoxy-2-(propan-2-ylamino)-1,2,3,4-tetrahydronaphthalen-1-ol;hydrochloride Chemical compound Cl.OC1C(NC(C)C)CCC(C=2[N+]([O-])=O)=C1C=CC=2OCC1=CC=CC=C1 PQJCBJVNMUQEIE-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000001118 alkylidene group Chemical group 0.000 description 4
- 125000000304 alkynyl group Chemical group 0.000 description 4
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- LBSANEJBGMCTBH-UHFFFAOYSA-N manganate Chemical compound [O-][Mn]([O-])(=O)=O LBSANEJBGMCTBH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- UWKNSERDYSXFIX-WIYYLYMNSA-N methyl (5r,6r)-5-hydroxy-2-phenylmethoxy-6-(propan-2-ylamino)-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound C([C@H]([C@H](O)C=1C=C2)NC(C)C)CC=1C(C(=O)OC)=C2OCC1=CC=CC=C1 UWKNSERDYSXFIX-WIYYLYMNSA-N 0.000 description 1
- LRQJFFSQDMUVPO-DENIHFKCSA-N methyl (5r,6r)-6-acetamido-5-acetyloxy-2-phenylmethoxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound C([C@H]([C@H](OC(C)=O)C=1C=C2)NC(C)=O)CC=1C(C(=O)OC)=C2OCC1=CC=CC=C1 LRQJFFSQDMUVPO-DENIHFKCSA-N 0.000 description 1
- WYSCFKFGGBXOPQ-CRAIPNDOSA-N methyl (5r,6r)-6-bromo-5-hydroxy-2-phenylmethoxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound C([C@@H](Br)[C@H](O)C=1C=C2)CC=1C(C(=O)OC)=C2OCC1=CC=CC=C1 WYSCFKFGGBXOPQ-CRAIPNDOSA-N 0.000 description 1
- XQIFVCKBPSZMDF-UHFFFAOYSA-N methyl 2-acetyloxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound C1CCCC2=C1C=CC(OC(C)=O)=C2C(=O)OC XQIFVCKBPSZMDF-UHFFFAOYSA-N 0.000 description 1
- LEENMPKUUNPLHM-UHFFFAOYSA-N methyl 2-hydroxynaphthalene-1-carboxylate Chemical compound C1=CC=C2C(C(=O)OC)=C(O)C=CC2=C1 LEENMPKUUNPLHM-UHFFFAOYSA-N 0.000 description 1
- OVXLVWVHNOGVFM-UHFFFAOYSA-N methyl 5-(tert-butylamino)-6-hydroxy-2-phenylmethoxy-5,6,7,8-tetrahydronaphthalene-1-carboxylate Chemical compound C1=CC=2C(NC(C)(C)C)C(O)CCC=2C(C(=O)OC)=C1OCC1=CC=CC=C1 OVXLVWVHNOGVFM-UHFFFAOYSA-N 0.000 description 1
- AVNDYZYKECWLSA-UHFFFAOYSA-N methyl 6-amino-5-oxo-2-phenylmethoxy-7,8-dihydro-6h-naphthalene-1-carboxylate;hydrochloride Chemical compound Cl.C1=CC=2C(=O)C(N)CCC=2C(C(=O)OC)=C1OCC1=CC=CC=C1 AVNDYZYKECWLSA-UHFFFAOYSA-N 0.000 description 1
- DDIZAANNODHTRB-UHFFFAOYSA-N methyl p-anisate Chemical compound COC(=O)C1=CC=C(OC)C=C1 DDIZAANNODHTRB-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- MBKYYHWDNVFUTN-UHFFFAOYSA-N n-(5-oxo-2-phenylmethoxy-7,8-dihydro-6h-naphthalen-1-yl)methanesulfonamide Chemical compound CS(=O)(=O)NC1=C2CCCC(=O)C2=CC=C1OCC1=CC=CC=C1 MBKYYHWDNVFUTN-UHFFFAOYSA-N 0.000 description 1
- PGXJQKOCADKOBF-UHFFFAOYSA-N n-(6-amino-5-hydroxy-2-phenylmethoxy-5,6,7,8-tetrahydronaphthalen-1-yl)-n-benzylmethanesulfonamide;hydrochloride Chemical compound Cl.C=1C=CC=CC=1COC=1C=CC=2C(O)C(N)CCC=2C=1N(S(=O)(=O)C)CC1=CC=CC=C1 PGXJQKOCADKOBF-UHFFFAOYSA-N 0.000 description 1
- SFXKVSBCXXPKON-SHQCIBLASA-N n-[(1r,2r)-5-[benzyl(methyl)amino]-1-hydroxy-6-phenylmethoxy-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C([C@H]([C@H](O)C=1C=CC=2OCC=3C=CC=CC=3)NC(C)=O)CC=1C=2N(C)CC1=CC=CC=C1 SFXKVSBCXXPKON-SHQCIBLASA-N 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
- RNLFQICIOHQSJI-UHFFFAOYSA-N n-benzyl-n-methyl-2-phenylmethoxy-7,8-dihydronaphthalen-1-amine Chemical compound C=1C=CC=CC=1COC=1C=CC=2C=CCCC=2C=1N(C)CC1=CC=CC=C1 RNLFQICIOHQSJI-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PZVFQOBASICMME-UHFFFAOYSA-N n-ethylmethanesulfonamide Chemical compound CCNS(C)(=O)=O PZVFQOBASICMME-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- NVVRCZVFMOXSDF-UHFFFAOYSA-N n-propan-2-yl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(NC(C)C)CCC2=C1 NVVRCZVFMOXSDF-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 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
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000012419 sodium bis(2-methoxyethoxy)aluminum hydride Substances 0.000 description 1
- PXLIDIMHPNPGMH-UHFFFAOYSA-N sodium chromate Chemical compound [Na+].[Na+].[O-][Cr]([O-])(=O)=O PXLIDIMHPNPGMH-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
- LYPGDCWPTHTUDO-UHFFFAOYSA-M sodium;methanesulfinate Chemical compound [Na+].CS([O-])=O LYPGDCWPTHTUDO-UHFFFAOYSA-M 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003450 sulfenic acids Chemical class 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/335—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/42—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/44—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having amino groups or hydroxy groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton bound to carbon atoms of the same ring or condensed ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/84—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems
- C07C215/86—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems being formed by two rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/38—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D303/40—Compounds containing oxirane rings with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals by ester radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/20—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hydrogen atoms and substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- 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
- C07D317/72—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 spiro-condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP49067539A JPS5833219B2 (ja) | 1974-06-12 | 1974-06-12 | テトラロ−ルカゴウブツノ セイゾウホウ |
JP12353974 | 1974-10-25 | ||
JP49137883A JPS51125265A (en) | 1974-11-29 | 1974-11-29 | Process for preparing tetralone compounds |
JP814875A JPS5186456A (ja) | 1975-01-17 | 1975-01-17 | Tetoraroorukagobutsuno seizoho |
Publications (2)
Publication Number | Publication Date |
---|---|
DE2525512A1 true DE2525512A1 (de) | 1975-12-18 |
DE2525512C2 DE2525512C2 (en, 2012) | 1987-11-26 |
Family
ID=27454881
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19752525512 Granted DE2525512A1 (de) | 1974-06-12 | 1975-06-07 | Aminotetralolverbindungen, verfahren zu ihrer herstellung sowie sie enthaltende arzneimittel |
Country Status (11)
Country | Link |
---|---|
US (1) | US4035512A (en, 2012) |
CA (1) | CA1039297A (en, 2012) |
CH (1) | CH625780A5 (en, 2012) |
DE (1) | DE2525512A1 (en, 2012) |
DK (1) | DK254975A (en, 2012) |
ES (2) | ES438451A1 (en, 2012) |
FI (1) | FI751755A7 (en, 2012) |
GB (1) | GB1516331A (en, 2012) |
NL (1) | NL7506975A (en, 2012) |
NO (1) | NO752053L (en, 2012) |
SE (1) | SE7506687L (en, 2012) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0026848B1 (de) * | 1979-09-14 | 1983-05-04 | Sandoz Ag | Tetralinderivate, ihre Herstellung und Heilmittel, welche diese Verbindungen enthalten |
US4530919A (en) * | 1980-10-21 | 1985-07-23 | Pfizer Inc. | Carboxylic acid therapeutic agents |
FR2512814A1 (fr) * | 1981-09-16 | 1983-03-18 | Synthelabo | Derives d'amino-2 tetrahydro-1,2,3,4 naphtalene, leur preparation et leur application en therapeutique |
JPS5970653A (ja) * | 1982-10-15 | 1984-04-21 | Takeda Chem Ind Ltd | 眼圧低下剤 |
US4737519A (en) * | 1983-12-14 | 1988-04-12 | The Upjohn Company | Substituted naphthalenes, indoles, benzofurans, and benzothiophenes as lipoxygenase inhibitors |
IL79323A (en) * | 1985-07-10 | 1990-03-19 | Sanofi Sa | Phenylethanolaminotetralines,their preparation and pharmaceutical compositions containing them |
JPH0696521B2 (ja) * | 1986-01-31 | 1994-11-30 | 千寿製薬株式会社 | 眼局所投与用眼圧降下剤 |
US4975461A (en) * | 1986-06-19 | 1990-12-04 | E. R. Squibb & Sons, Inc. | P-aminophenols, derivatives thereof and method of use |
DE3623941A1 (de) * | 1986-07-16 | 1988-01-28 | Bayer Ag | Substituierte amino-5,6,7,8-tetrahydronaphthyl-oxyessigsaeuren, verfahren zu deren herstellung sowie die verwendung als arzneimittel |
IT1224405B (it) * | 1987-12-23 | 1990-10-04 | Simes | Composti attivi sul sistema cardiovascolare |
US5071875A (en) * | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
US5151446A (en) * | 1989-09-25 | 1992-09-29 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
US5382596A (en) * | 1993-08-05 | 1995-01-17 | Whitby Research, Inc. | Substituted 2-aminotetralins |
US5776983A (en) * | 1993-12-21 | 1998-07-07 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
US5770615A (en) * | 1996-04-04 | 1998-06-23 | Bristol-Myers Squibb Company | Catecholamine surrogates useful as β3 agonists |
US11590089B2 (en) | 2017-12-04 | 2023-02-28 | The Board Of Trustees Of The Leland Stanford Junior University | Beta-2 selective adrenergic receptor agonists |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2549685A (en) * | 1948-09-30 | 1951-04-17 | Upjohn Co | Dioxy substituted 2-aminoindanols |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2549684A (en) * | 1948-09-29 | 1951-04-17 | Upjohn Co | Methoxy substituted 2-aminoindanols |
US3458577A (en) * | 1966-06-23 | 1969-07-29 | Sandoz Ag | 6-amino-6,7,8,9-tetrahydro-5h-benzocyclohepten-5-ols |
US3930022A (en) * | 1972-07-03 | 1975-12-30 | Squibb & Sons Inc | Certain tetrahydronaphthalenes used in the treatment of cardiac arrhythmia |
-
1975
- 1975-06-06 DK DK254975A patent/DK254975A/da unknown
- 1975-06-07 DE DE19752525512 patent/DE2525512A1/de active Granted
- 1975-06-09 CA CA228,816A patent/CA1039297A/en not_active Expired
- 1975-06-09 GB GB24612/75A patent/GB1516331A/en not_active Expired
- 1975-06-10 NO NO752053A patent/NO752053L/no unknown
- 1975-06-11 ES ES438451A patent/ES438451A1/es not_active Expired
- 1975-06-11 CH CH758075A patent/CH625780A5/de not_active IP Right Cessation
- 1975-06-11 NL NL7506975A patent/NL7506975A/xx not_active Application Discontinuation
- 1975-06-11 SE SE7506687A patent/SE7506687L/xx unknown
- 1975-06-12 FI FI751755A patent/FI751755A7/fi not_active Application Discontinuation
- 1975-06-12 US US05/586,282 patent/US4035512A/en not_active Expired - Lifetime
-
1976
- 1976-12-31 ES ES454747A patent/ES454747A1/es not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2549685A (en) * | 1948-09-30 | 1951-04-17 | Upjohn Co | Dioxy substituted 2-aminoindanols |
Non-Patent Citations (2)
Title |
---|
J. Chem. Soc. 1967, 288 ff * |
Liebigs Am. Chem. 685 (1965), 141 * |
Also Published As
Publication number | Publication date |
---|---|
DK254975A (da) | 1975-12-13 |
NO752053L (en, 2012) | 1975-12-15 |
US4035512A (en) | 1977-07-12 |
SE7506687L (sv) | 1975-12-15 |
CA1039297A (en) | 1978-09-26 |
ES438451A1 (es) | 1977-06-01 |
CH625780A5 (en, 2012) | 1981-10-15 |
AU8194375A (en) | 1976-12-16 |
ES454747A1 (es) | 1978-01-01 |
NL7506975A (nl) | 1975-12-16 |
GB1516331A (en) | 1978-07-05 |
DE2525512C2 (en, 2012) | 1987-11-26 |
FI751755A7 (en, 2012) | 1975-12-13 |
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