DE2366625C2 - - Google Patents

Info

Publication number: DE2366625C2
Authority: DE; Germany
Prior art keywords: benzyl; benzyloxy; mixture; methyl; reduced pressure
Prior art date: 1972-02-05
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

Application number

DE19732366625

Other languages

German (de)

English (en)

Inventor

Masuo Murakami

Kozo Takahashi

Toshiyasu Tokio/Tokyo Jp Mase

Kiyoshi Urawa Saitama Jp Murase

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Yamanouchi Pharmaceutical Co Ltd

Original Assignee

Yamanouchi Pharmaceutical Co Ltd

Priority date (The priority date 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 date listed.)

1972-02-05

Filing date

1973-02-02

Publication date

1988-06-09

1972-02-05 Priority claimed from JP1312172A external-priority patent/JPS5653537B2/ja

1972-04-19 Priority claimed from JP3941672A external-priority patent/JPS49237A/ja

1972-05-23 Priority claimed from JP5101372A external-priority patent/JPS495934A/ja

1973-02-02 Application filed by Yamanouchi Pharmaceutical Co Ltd filed Critical Yamanouchi Pharmaceutical Co Ltd

1988-06-09 Application granted granted Critical

1988-06-09 Publication of DE2366625C2 publication Critical patent/DE2366625C2/de

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 13
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 141
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 105
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 87
239000000203 mixture Substances 0.000 description 82
239000000243 solution Substances 0.000 description 67
-1 α- aminomethylbenzyl alcohol derivatives Chemical class 0.000 description 67
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
235000019445 benzyl alcohol Nutrition 0.000 description 66
229960004217 benzyl alcohol Drugs 0.000 description 66
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
239000000047 product Substances 0.000 description 44
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 34
239000000284 extract Substances 0.000 description 34
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
239000007795 chemical reaction product Substances 0.000 description 24
238000002844 melting Methods 0.000 description 19
230000008018 melting Effects 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
239000002904 solvent Substances 0.000 description 18
238000002360 preparation method Methods 0.000 description 17
229910000029 sodium carbonate Inorganic materials 0.000 description 17
239000000706 filtrate Substances 0.000 description 16
239000013078 crystal Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
PBAAKBQGBSUCTG-UHFFFAOYSA-N 2-bromo-1-(3-nitro-4-phenylmethoxyphenyl)ethanone Chemical compound [O-][N+](=O)C1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 PBAAKBQGBSUCTG-UHFFFAOYSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 10
238000001914 filtration Methods 0.000 description 10
238000010898 silica gel chromatography Methods 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
239000007858 starting material Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
229910052794 bromium Inorganic materials 0.000 description 6
239000000463 material Substances 0.000 description 6
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
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 6
238000003756 stirring Methods 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 5
150000001412 amines Chemical class 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000003480 eluent Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 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
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000000725 suspension 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
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 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
239000003054 catalyst Substances 0.000 description 3
238000010531 catalytic reduction reaction Methods 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 3
238000000034 method Methods 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 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
CBLXRVBEZHRFJW-UHFFFAOYSA-N 2-[1-(4-methoxyphenyl)propan-2-yl-[(3-nitro-4-phenylmethoxyphenyl)methyl]amino]-1-phenylethanone Chemical compound C1=CC(OC)=CC=C1CC(C)N(CC=1C=C(C(OCC=2C=CC=CC=2)=CC=1)[N+]([O-])=O)CC(=O)C1=CC=CC=C1 CBLXRVBEZHRFJW-UHFFFAOYSA-N 0.000 description 2
STIBLONETZHESW-UHFFFAOYSA-N 2-[benzyl-[1-(4-methoxyphenyl)propan-2-yl]amino]-1-(3-nitro-4-phenylmethoxyphenyl)ethanol Chemical compound C1=CC(OC)=CC=C1CC(C)N(CC=1C=CC=CC=1)CC(O)C(C=C1[N+]([O-])=O)=CC=C1OCC1=CC=CC=C1 STIBLONETZHESW-UHFFFAOYSA-N 0.000 description 2
PERIVIQDKWIEHE-UHFFFAOYSA-N 2-[tert-butyl-[(3-nitro-4-phenylmethoxyphenyl)methyl]amino]-1-phenylethanone Chemical compound C=1C=C(OCC=2C=CC=CC=2)C([N+]([O-])=O)=CC=1CN(C(C)(C)C)CC(=O)C1=CC=CC=C1 PERIVIQDKWIEHE-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
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 2
YUTDGOVQYYDZKB-UHFFFAOYSA-N CC(C)N(CC1=CC(=C(C=C1)OCC2=CC=CC=C2)NC(=O)C)CC(=O)C3=CC=CC=C3 Chemical compound CC(C)N(CC1=CC(=C(C=C1)OCC2=CC=CC=C2)NC(=O)C)CC(=O)C3=CC=CC=C3 YUTDGOVQYYDZKB-UHFFFAOYSA-N 0.000 description 2
XJNHTIROSFZROW-UHFFFAOYSA-N CC(CC1=CC=C(C=C1)O)N(CC2=CC(=C(C=C2)OCC3=CC=CC=C3)NC(=O)C)CC(=O)C4=CC=CC=C4 Chemical compound CC(CC1=CC=C(C=C1)O)N(CC2=CC(=C(C=C2)OCC3=CC=CC=C3)NC(=O)C)CC(=O)C4=CC=CC=C4 XJNHTIROSFZROW-UHFFFAOYSA-N 0.000 description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 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
229940124630 bronchodilator Drugs 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
QFGMPZQFEMHAQE-UHFFFAOYSA-N ethyl acetate;phenylmethanol Chemical compound CCOC(C)=O.OCC1=CC=CC=C1 QFGMPZQFEMHAQE-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000001257 hydrogen Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
TVLLMHMSGGBZNO-UHFFFAOYSA-N 1-(3-amino-4-phenylmethoxyphenyl)-2-[benzyl-[1-(4-methoxyphenyl)propan-2-yl]amino]ethanol Chemical compound C1=CC(OC)=CC=C1CC(C)N(CC=1C=CC=CC=1)CC(O)C(C=C1N)=CC=C1OCC1=CC=CC=C1 TVLLMHMSGGBZNO-UHFFFAOYSA-N 0.000 description 1
MKYMYZJJFMPDOA-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 MKYMYZJJFMPDOA-UHFFFAOYSA-N 0.000 description 1
OPOKHFVSCLJARP-UHFFFAOYSA-N 2-[(3-nitro-4-phenylmethoxyphenyl)methyl-propan-2-ylamino]-1-phenylethanone Chemical compound C=1C=C(OCC=2C=CC=CC=2)C([N+]([O-])=O)=CC=1CN(C(C)C)CC(=O)C1=CC=CC=C1 OPOKHFVSCLJARP-UHFFFAOYSA-N 0.000 description 1
IICIGOLKJHKNPI-UHFFFAOYSA-N 2-[1-(4-hydroxyphenyl)propan-2-yl-[(3-nitro-4-phenylmethoxyphenyl)methyl]amino]-1-phenylethanone Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(CN(C(CC2=CC=C(C=C2)O)C)CC(=O)C2=CC=CC=C2)C=C1)[N+](=O)[O-] IICIGOLKJHKNPI-UHFFFAOYSA-N 0.000 description 1
ADFUHIYILOQDHG-UHFFFAOYSA-N 2-bromo-1-(4-hydroxy-3-nitrophenyl)ethanone Chemical compound OC1=CC=C(C(=O)CBr)C=C1[N+]([O-])=O ADFUHIYILOQDHG-UHFFFAOYSA-N 0.000 description 1
MMNKVWGVSHRIJL-UHFFFAOYSA-N 4'-hydroxy-3'-nitroacetophenone Chemical compound CC(=O)C1=CC=C(O)C([N+]([O-])=O)=C1 MMNKVWGVSHRIJL-UHFFFAOYSA-N 0.000 description 1
FZDQMPNZNWBSFV-UHFFFAOYSA-N CC(CC1=CC(C(C=C1)(O)O)NC(=O)C)NCC(=O)C2=CC=CC=C2 Chemical compound CC(CC1=CC(C(C=C1)(O)O)NC(=O)C)NCC(=O)C2=CC=CC=C2 FZDQMPNZNWBSFV-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-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
VHSQLIUMHWMWBL-UHFFFAOYSA-N N-[2-hydroxy-5-[[phenacyl-[1-(4-propoxyphenyl)propan-2-yl]amino]methyl]phenyl]-2-phenylmethoxyacetamide Chemical compound C1=CC(OCCC)=CC=C1CC(C)N(CC=1C=C(NC(=O)COCC=2C=CC=CC=2)C(O)=CC=1)CC(=O)C1=CC=CC=C1 VHSQLIUMHWMWBL-UHFFFAOYSA-N 0.000 description 1
LJLLAWRMBZNPMO-UHFFFAOYSA-N N-acetyl-beta-alanine Chemical compound CC(=O)NCCC(O)=O LJLLAWRMBZNPMO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
125000004442 acylamino group Chemical group 0.000 description 1
230000001800 adrenalinergic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000006673 asthma Diseases 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
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
239000000470 constituent Substances 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-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
PEIJPMBOGRPKQJ-UHFFFAOYSA-N n-benzylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCC1=CC=CC=C1 PEIJPMBOGRPKQJ-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
238000010992 reflux Methods 0.000 description 1
210000003019 respiratory muscle Anatomy 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000011282 treatment Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000005406 washing Methods 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

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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)

DE19732366625 1972-02-05 1973-02-02 Expired DE2366625C2 (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
JP1312172A JPS5653537B2 (fr)	1972-02-05	1972-02-05
JP3941672A JPS49237A (fr)	1972-04-19	1972-04-19
JP5101372A JPS495934A (fr)	1972-05-23	1972-05-23
JP5291572		1972-05-27

Publications (1)

Publication Number	Publication Date
DE2366625C2 true DE2366625C2 (fr)	1988-06-09

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 (fr)	1972-02-05	1973-02-02

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
DE19732305092 Granted DE2305092A1 (de)	1972-02-05	1973-02-02	Alpha-aminomethylbenzylalkoholderivate

Country Status (1)

Country	Link
DE (2)	DE2305092A1 (fr)

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WO1992005147A1 (fr) *	1990-09-26	1992-04-02	Aktiebolaget Astra	Nouveau procede de preparation du formoterole et de composes associes

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GB1531718A (en) *	1974-11-20	1978-11-08	Pharmacia As	Phenylethanolamines
EP0068669A1 (fr) *	1981-06-20	1983-01-05	Beecham Group Plc	Phényléthanolamines secondaires, procédés de leur préparation et leur application pharmaceutique
ES8606847A1 (es) *	1984-11-08	1986-05-16	Syntex Inc	Procedimiento para la preparacion de derivados de dialquila-mino-etilanilina antihipertensos
PH25150A (en) *	1986-06-05	1991-03-13	Ciba Geigy Ag	Novel pharmaceutical preparation for topical application
US5369117A (en) *	1992-09-02	1994-11-29	Ciba-Geigy Corporation	5-(3-formylamino-4-hydroxyphenyl)-3-(1-(4-methoxyphenyl)prop-2-yl)-oxazolidines
US6713651B1 (en)	1999-06-07	2004-03-30	Theravance, Inc.	β2-adrenergic receptor agonists
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
UA73965C2 (en)	1999-12-08	2005-10-17	Theravance Inc	b2 ADRENERGIC RECEPTOR ANTAGONISTS
US20030055026A1 (en)	2001-04-17	2003-03-20	Dey L.P.	Formoterol/steroid bronchodilating compositions and methods of use thereof
US6667344B2 (en)	2001-04-17	2003-12-23	Dey, L.P.	Bronchodilating compositions and methods
TWI359675B (en)	2003-07-10	2012-03-11	Dey L P	Bronchodilating β-agonist compositions
MY155277A (en)	2006-08-22	2015-09-30	Ranbaxy Lab Ltd	Matrix metalloproteinase inhibitors
US8501994B2 (en)	2007-08-28	2013-08-06	Sunovion Pharmaceuticals Inc.	Acetamide stereoisomer
US7718822B2 (en)	2007-08-28	2010-05-18	Sepracor Inc.	Carbamate Stereoisomer

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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

Non-Patent Citations (1)

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Title
NICHTS ERMITTELT *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO1992005147A1 (fr) *	1990-09-26	1992-04-02	Aktiebolaget Astra	Nouveau procede de preparation du formoterole et de composes associes
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

Also Published As

Publication number	Publication date
DE2305092A1 (de)	1973-08-16
DE2305092C2 (fr)	1987-10-01

Legal Events

Date	Code	Title	Description
1987-05-14	Q172	Divided out of (supplement):	Ref country code: DE Ref document number: 2305092
1987-08-13	8181	Inventor (new situation)	Free format text: MURAKAMI, MASUO TAKAHASHI, KOZO MASE, TOSHIYASU, TOKIO/TOKYO, JP MURASE, KIYOSHI, URAWA, SAITAMA, JP
1987-10-01	AC	Divided out of	Ref country code: DE Ref document number: 2305092 Format of ref document f/p: P
1988-06-09	AC	Divided out of	Ref country code: DE Ref document number: 2305092 Format of ref document f/p: P
1988-06-09	D2	Grant after examination
1988-12-08	8364	No opposition during term of opposition

Publication	Publication Date	Title
DE2366625C2 (fr)	1988-06-09
EP0026848B1 (fr)	1983-05-04	Dérivés de tétraline, leur préparation et médicaments contenant ces composés
DE3642105A1 (de)	1988-06-16	Substituierte aminomethyl-5,6,7,8-tetrahydronaphtyl-oxyessigsaeuren, neue zwischenprodukte, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln
CH636856A5 (en)	1983-06-30	4-(3-Aminopropoxy)indole derivatives, their preparation and medicines containing them
CH636858A5 (de)	1983-06-30	Verfahren zur herstellung neuer phenylazacycloalkane.
DE2354931C2 (de)	1983-12-08	trans-2-Phenylbicyclooctan-Verbindungen, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zubereitungen
CH417630A (de)	1966-07-31	Verfahren zur Herstellung von neuen cyclischen 2,3-O-Acetalen und 2,3-O-Ketalen von Butantetrolestern
CH441291A (de)	1967-08-15	Verfahren zur Herstellung von organischen Aminen
CH535767A (de)	1973-04-15	Verfahren zur Herstellung neuer N-Phenäthylpiperidinderivate
AT360992B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
DE2623257A1 (de)	1977-06-30	Verfahren zur herstellung von n-alkenyl-2-aminomethyl-pyrrolidinen
EP0102929B1 (fr)	1987-07-01	Dérivés de propylamine, procédé de leur préparation, compositions pharmaceutiques contenant ces composés, ainsi que leur usage thérapeutique
AT266075B (de)	1968-11-11	Verfahren zur Herstellung von neuen Sulfonaniliden und deren Säureadditions- und Metallsalzen
AT384018B (de)	1987-09-25	Verfahren zur herstellung von neuen aminen und deren salzen
AT360007B (de)	1980-12-10	Verfahren zur herstellung von 2-(phenylamino)- imidazolin-(2)derivaten und deren salzen
AT363094B (de)	1981-07-10	Verfahren zur herstellung von neuen piperazinderivaten und deren salzen
AT336018B (de)	1977-04-12	Verfahren zur herstellung von neuen heterocyclischen verbindungen
AT347448B (de)	1978-12-27	Verfahren zur herstellung von n-alkenyl-2- aminomethyl-pyrrolidinen
EP0239533B1 (fr)	1992-09-16	Dérivés de la pyridine
AT381088B (de)	1986-08-25	Verfahren zur herstellung von neuen aminen und deren salzen
AT258280B (de)	1967-11-10	Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen
CH532037A (de)	1972-12-31	Verfahren zur Herstellung von Pyrrolverbindungen
AT360993B (de)	1981-02-10	Verfahren zur herstellung neuer phenylazacyclo- alkane und von deren salzen und optisch aktiven verbindungen
AT337682B (de)	1977-07-11	Verfahren zur herstellung von neuen benzocycloalkencarbonsauren sowie ihren estern und salzen
AT267516B (de)	1969-01-10	Verfahren zur Herstellung von neuen Benzofuranderivaten und ihren Salzen