DE2305092A1 - Alpha-aminomethylbenzylalkoholderivate - Google Patents
Alpha-aminomethylbenzylalkoholderivateInfo
- Publication number
- DE2305092A1 DE2305092A1 DE19732305092 DE2305092A DE2305092A1 DE 2305092 A1 DE2305092 A1 DE 2305092A1 DE 19732305092 DE19732305092 DE 19732305092 DE 2305092 A DE2305092 A DE 2305092A DE 2305092 A1 DE2305092 A1 DE 2305092A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- benzyl
- alcohol
- added
- methyl
- 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
- -1 Alpha-aminomethylbenzyl alcohol Chemical compound 0.000 title claims description 94
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 242
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 228
- 239000000203 mixture Substances 0.000 claims description 104
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 32
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 229940124630 bronchodilator Drugs 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 3
- 241001465754 Metazoa Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 7
- 210000003019 respiratory muscle Anatomy 0.000 abstract description 2
- 239000000021 stimulant Substances 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 126
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 120
- 229960004217 benzyl alcohol Drugs 0.000 description 100
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
- 239000000047 product Substances 0.000 description 65
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 64
- 239000013078 crystal Substances 0.000 description 53
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 50
- 238000001914 filtration Methods 0.000 description 43
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 36
- 239000000284 extract Substances 0.000 description 36
- 239000007795 chemical reaction product Substances 0.000 description 35
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 34
- 239000003054 catalyst Substances 0.000 description 32
- 238000010531 catalytic reduction reaction Methods 0.000 description 31
- 239000002904 solvent Substances 0.000 description 31
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- 239000000706 filtrate Substances 0.000 description 27
- 238000000921 elemental analysis Methods 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 19
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- 229910000029 sodium carbonate Inorganic materials 0.000 description 18
- 239000001530 fumaric acid Substances 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 15
- 239000000463 material Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 7
- 238000000862 absorption spectrum Methods 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 238000010438 heat treatment Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- RDCOMWQFSWWPJG-UHFFFAOYSA-N acetyl acetate;formic acid Chemical compound OC=O.CC(=O)OC(C)=O RDCOMWQFSWWPJG-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- OWKGFSOHSDMRJL-UHFFFAOYSA-N 1-(3-nitro-4-phenylmethoxyphenyl)ethanone Chemical compound [O-][N+](=O)C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 OWKGFSOHSDMRJL-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 241000700199 Cavia porcellus Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 3
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 3
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 3
- 235000019253 formic acid Nutrition 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
- JHPHVAVFUYTVCL-UHFFFAOYSA-M methacholine chloride Chemical compound [Cl-].C[N+](C)(C)CC(C)OC(C)=O JHPHVAVFUYTVCL-UHFFFAOYSA-M 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- OTKGBARXKHAVQS-UHFFFAOYSA-N 2-[(4-hydroxy-3-nitrophenyl)methyl-propan-2-ylamino]-1-phenylethanone Chemical compound C=1C=C(O)C([N+]([O-])=O)=CC=1CN(C(C)C)CC(=O)C1=CC=CC=C1 OTKGBARXKHAVQS-UHFFFAOYSA-N 0.000 description 2
- QISAUDWTBBNJIR-UHFFFAOYSA-N 2-phenylmethoxyacetyl chloride Chemical compound ClC(=O)COCC1=CC=CC=C1 QISAUDWTBBNJIR-UHFFFAOYSA-N 0.000 description 2
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 206010013975 Dyspnoeas Diseases 0.000 description 2
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- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
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- 150000007513 acids Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- QFGMPZQFEMHAQE-UHFFFAOYSA-N ethyl acetate;phenylmethanol Chemical compound CCOC(C)=O.OCC1=CC=CC=C1 QFGMPZQFEMHAQE-UHFFFAOYSA-N 0.000 description 2
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- 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
- OFNCPXJFDNCYLF-UHFFFAOYSA-N N-[1-(4-hydroxy-4-phenylmethoxycyclohexa-1,5-dien-1-yl)-3-(phenacylamino)butyl]formamide Chemical compound C(=O)NC(CC(C)NCC(=O)C1=CC=CC=C1)C1=CCC(C=C1)(O)OCC1=CC=CC=C1 OFNCPXJFDNCYLF-UHFFFAOYSA-N 0.000 description 1
- JSULJKCZDJIOMZ-UHFFFAOYSA-N N-[3-[[tert-butyl-(3-oxo-3-phenylpropyl)amino]methyl]phenyl]formamide Chemical compound C(=O)NC=1C=C(CN(C(C)(C)C)CCC(=O)C2=CC=CC=C2)C=CC1 JSULJKCZDJIOMZ-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010042618 Surgical procedure repeated Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000001088 anti-asthma Effects 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- FIDLYNBSMRFNLL-UHFFFAOYSA-N benzyl(propan-2-yl)azanium;bromide Chemical compound Br.CC(C)NCC1=CC=CC=C1 FIDLYNBSMRFNLL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004044 bronchoconstricting agent Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- DUJUMYHBHNIXHQ-UHFFFAOYSA-N ethanol;1-phenylethanone Chemical compound CCO.CC(=O)C1=CC=CC=C1 DUJUMYHBHNIXHQ-UHFFFAOYSA-N 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- GGQOPZKTDHXXON-UHFFFAOYSA-N hexane;methanol Chemical compound OC.CCCCCC GGQOPZKTDHXXON-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- UHSXRTHJCJGEKG-UHFFFAOYSA-N hydron;1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;chloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 UHSXRTHJCJGEKG-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- RVGUTXYKHMDBPX-UHFFFAOYSA-N n-[5-[2-[benzyl-[1-(4-methoxyphenyl)propan-2-yl]amino]-1-hydroxyethyl]-2-phenylmethoxyphenyl]formamide Chemical compound C1=CC(OC)=CC=C1CC(C)N(CC=1C=CC=CC=1)CC(O)C(C=C1NC=O)=CC=C1OCC1=CC=CC=C1 RVGUTXYKHMDBPX-UHFFFAOYSA-N 0.000 description 1
- KTHDTJVBEPMMGL-GSVOUGTGSA-N n-acetylalanine Chemical compound OC(=O)[C@@H](C)NC(C)=O KTHDTJVBEPMMGL-GSVOUGTGSA-N 0.000 description 1
- CVGPWMGXKOKNFD-UHFFFAOYSA-N n-benzyl-1-(4-methoxyphenyl)propan-2-amine Chemical compound C1=CC(OC)=CC=C1CC(C)NCC1=CC=CC=C1 CVGPWMGXKOKNFD-UHFFFAOYSA-N 0.000 description 1
- DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 1
- MMNNFMKNCOKXLZ-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine;hydrobromide Chemical compound Br.CC(C)(C)NCC1=CC=CC=C1 MMNNFMKNCOKXLZ-UHFFFAOYSA-N 0.000 description 1
- BCYXATWYHNOEHW-UHFFFAOYSA-N n-benzyl-4-methyl-n-propan-2-ylaniline Chemical compound C=1C=C(C)C=CC=1N(C(C)C)CC1=CC=CC=C1 BCYXATWYHNOEHW-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
- 239000006199 nebulizer Substances 0.000 description 1
- 125000005484 neopentoxy group Chemical group 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/205—Amine addition salts of organic acids; Inner quaternary ammonium salts, e.g. betaine, carnitine
-
- 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
- C07C215/76—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 of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1312172A JPS5653537B2 (enrdf_load_html_response) | 1972-02-05 | 1972-02-05 | |
| JP3941672A JPS49237A (enrdf_load_html_response) | 1972-04-19 | 1972-04-19 | |
| JP5101372A JPS495934A (enrdf_load_html_response) | 1972-05-23 | 1972-05-23 | |
| JP5291572 | 1972-05-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2305092A1 true DE2305092A1 (de) | 1973-08-16 |
| DE2305092C2 DE2305092C2 (enrdf_load_html_response) | 1987-10-01 |
Family
ID=27455936
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732305092 Granted DE2305092A1 (de) | 1972-02-05 | 1973-02-02 | Alpha-aminomethylbenzylalkoholderivate |
| DE19732366625 Expired DE2366625C2 (enrdf_load_html_response) | 1972-02-05 | 1973-02-02 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19732366625 Expired DE2366625C2 (enrdf_load_html_response) | 1972-02-05 | 1973-02-02 |
Country Status (1)
| Country | Link |
|---|---|
| DE (2) | DE2305092A1 (enrdf_load_html_response) |
Cited By (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072760A (en) * | 1974-11-20 | 1978-02-07 | Pharmacia As | Bronchospasmolytic phenylethanolamines |
| EP0068669A1 (en) * | 1981-06-20 | 1983-01-05 | Beecham Group Plc | Secondary phenylethanol amines, processes for their preparation and their pharmaceutical application |
| EP0180994A3 (en) * | 1984-11-08 | 1987-09-23 | Syntex (U.S.A.) Inc. | Antihypertensive dialkyl aminoethylaniline derivatives |
| US4975466A (en) * | 1986-06-05 | 1990-12-04 | Ciba-Geigy Corporation | Pharmaceutical preparations for topical application and their use in the treatment of inflammatory skin diseases |
| EP0586344A1 (de) * | 1992-09-02 | 1994-03-09 | Ciba-Geigy Ag | Oxazolidin Verbindungen und ihre Verwendung als Arzneimittel |
| LT3813B (en) | 1990-09-26 | 1996-03-25 | Astra Ab | Process for preparing 3-formamido-4-hydroxy-alpha£n£1-methyl-2(p-methoxyphenyl)ethylaminomethyl|benzyl alkohol fumarate (formoterol) and related compounds and derivatives thereof |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6576793B1 (en) | 1999-12-08 | 2003-06-10 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6667344B2 (en) | 2001-04-17 | 2003-12-23 | Dey, L.P. | Bronchodilating compositions and methods |
| US6683115B2 (en) | 1999-06-02 | 2004-01-27 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6713651B1 (en) | 1999-06-07 | 2004-03-30 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US7348362B2 (en) | 2003-07-10 | 2008-03-25 | Dey, L.P. | Bronchodilating β-agonist compositions and methods |
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| US8173829B2 (en) | 2007-08-28 | 2012-05-08 | Sunovion Pharmaceuticals Inc. | Carbamate stereoisomer |
| US8507670B2 (en) | 2006-08-22 | 2013-08-13 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| US8623851B2 (en) | 2001-04-17 | 2014-01-07 | Mylan Specialty L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE739678A (fr) * | 1969-10-01 | 1970-04-01 | Amino-alcools et leur preparation |
-
1973
- 1973-02-02 DE DE19732305092 patent/DE2305092A1/de active Granted
- 1973-02-02 DE DE19732366625 patent/DE2366625C2/de not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE739678A (fr) * | 1969-10-01 | 1970-04-01 | Amino-alcools et leur preparation |
Cited By (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4072760A (en) * | 1974-11-20 | 1978-02-07 | Pharmacia As | Bronchospasmolytic phenylethanolamines |
| EP0068669A1 (en) * | 1981-06-20 | 1983-01-05 | Beecham Group Plc | Secondary phenylethanol amines, processes for their preparation and their pharmaceutical application |
| EP0180994A3 (en) * | 1984-11-08 | 1987-09-23 | Syntex (U.S.A.) Inc. | Antihypertensive dialkyl aminoethylaniline derivatives |
| US4975466A (en) * | 1986-06-05 | 1990-12-04 | Ciba-Geigy Corporation | Pharmaceutical preparations for topical application and their use in the treatment of inflammatory skin diseases |
| LT3813B (en) | 1990-09-26 | 1996-03-25 | Astra Ab | Process for preparing 3-formamido-4-hydroxy-alpha£n£1-methyl-2(p-methoxyphenyl)ethylaminomethyl|benzyl alkohol fumarate (formoterol) and related compounds and derivatives thereof |
| EP0586344A1 (de) * | 1992-09-02 | 1994-03-09 | Ciba-Geigy Ag | Oxazolidin Verbindungen und ihre Verwendung als Arzneimittel |
| US6541669B1 (en) | 1998-06-08 | 2003-04-01 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6683115B2 (en) | 1999-06-02 | 2004-01-27 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6713651B1 (en) | 1999-06-07 | 2004-03-30 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6576793B1 (en) | 1999-12-08 | 2003-06-10 | Theravance, Inc. | β2-adrenergic receptor agonists |
| US6667344B2 (en) | 2001-04-17 | 2003-12-23 | Dey, L.P. | Bronchodilating compositions and methods |
| US9597396B2 (en) | 2001-04-17 | 2017-03-21 | Mylan Specialty Lp | Formoterol/steroid bronchodilating compositions and methods of use thereof |
| US8716348B2 (en) | 2001-04-17 | 2014-05-06 | Dey Pharma, L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
| US8623851B2 (en) | 2001-04-17 | 2014-01-07 | Mylan Specialty L.P. | Formoterol/steroid bronchodilating compositions and methods of use thereof |
| US7541385B2 (en) | 2003-07-10 | 2009-06-02 | Chaudry Imtiaz A | Bronchodilating β-agonist compositions and methods |
| US7465756B2 (en) | 2003-07-10 | 2008-12-16 | Jpmorgan Chase Bank, N.A. | Bronchodilating beta-agonist compositions and methods |
| US7473710B2 (en) | 2003-07-10 | 2009-01-06 | Jpmorgan Chase Bank, N.A. | Bronchodilating beta-agonist compositions and methods |
| US9730890B2 (en) | 2003-07-10 | 2017-08-15 | Mylan Pharmaceuticals, Inc. | Bronchodilating beta-agonist compositions and methods |
| US7348362B2 (en) | 2003-07-10 | 2008-03-25 | Dey, L.P. | Bronchodilating β-agonist compositions and methods |
| US7462645B2 (en) | 2003-07-10 | 2008-12-09 | Jpmorgan Chase Bank, N.A. | Bronchodilating beta-agonist compositions and methods |
| US8507670B2 (en) | 2006-08-22 | 2013-08-13 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| US8816073B2 (en) | 2006-08-22 | 2014-08-26 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| US8846910B2 (en) | 2006-08-22 | 2014-09-30 | Ranbaxy Laboratories Limited | Matrix metalloproteinase inhibitors |
| AU2008296458B2 (en) * | 2007-08-28 | 2014-01-16 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| US8664441B2 (en) | 2007-08-28 | 2014-03-04 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| KR101398775B1 (ko) * | 2007-08-28 | 2014-05-27 | 선오비온 파마슈티컬스 인코포레이티드 | 아세트아미드 입체이성체 |
| US9040588B2 (en) | 2007-08-28 | 2015-05-26 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| TWI505826B (zh) * | 2007-08-28 | 2015-11-01 | Sepracor Inc | 乙醯胺立體異構物 |
| US9499476B2 (en) | 2007-08-28 | 2016-11-22 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| US8501994B2 (en) | 2007-08-28 | 2013-08-06 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| US8173829B2 (en) | 2007-08-28 | 2012-05-08 | Sunovion Pharmaceuticals Inc. | Carbamate stereoisomer |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2366625C2 (enrdf_load_html_response) | 1988-06-09 |
| DE2305092C2 (enrdf_load_html_response) | 1987-10-01 |
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