NO803653L - Fremgangsmaate til fremstilling av nye derivater til 2-amino-etanol. - Google Patents

Fremgangsmaate til fremstilling av nye derivater til 2-amino-etanol.

Info

Publication number: NO803653L
Authority: NO; Norway
Prior art keywords: hydroxy; formula; residue; group; hydrogen
Prior art date: 1979-12-04

Application number

NO803653A

Other languages

English (en)

Norwegian (no)

Inventor

Franz Ostermayer

Markus Zimmermann

Walter Fuhrer

Original Assignee

Ciba Geigy Ag

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.)

1979-12-04

Filing date

1980-12-03

Publication date

1981-06-05

1980-12-03 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1981-06-05 Publication of NO803653L publication Critical patent/NO803653L/no

Links

238000000034 method Methods 0.000 title claims description 45
238000002360 preparation method Methods 0.000 title claims description 12
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 title 2
-1 methylene- Chemical class 0.000 claims description 214
150000001875 compounds Chemical class 0.000 claims description 188
125000000217 alkyl group Chemical group 0.000 claims description 119
239000000203 mixture Substances 0.000 claims description 79
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 77
229910052739 hydrogen Inorganic materials 0.000 claims description 76
239000001257 hydrogen Substances 0.000 claims description 76
150000003839 salts Chemical class 0.000 claims description 74
125000001424 substituent group Chemical group 0.000 claims description 59
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 51
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
125000004432 carbon atom Chemical group C* 0.000 claims description 37
150000002431 hydrogen Chemical class 0.000 claims description 33
125000002947 alkylene group Chemical group 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 27
230000009467 reduction Effects 0.000 claims description 27
125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
125000003277 amino group Chemical group 0.000 claims description 22
230000003287 optical effect Effects 0.000 claims description 19
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 18
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
125000004430 oxygen atom Chemical group O* 0.000 claims description 16
238000007098 aminolysis reaction Methods 0.000 claims description 10
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
238000012546 transfer Methods 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
230000007062 hydrolysis Effects 0.000 claims description 6
238000006460 hydrolysis reaction Methods 0.000 claims description 6
125000003700 epoxy group Chemical group 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
229920006395 saturated elastomer Polymers 0.000 claims description 4
150000002169 ethanolamines Chemical class 0.000 claims description 3
125000000464 thioxo group Chemical group S=* 0.000 claims description 3
UWBHMRBRLOJJAA-UHFFFAOYSA-N oxaluric acid Chemical compound NC(=O)NC(=O)C(O)=O UWBHMRBRLOJJAA-UHFFFAOYSA-N 0.000 claims description 2
230000001747 exhibiting effect Effects 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 155
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 108
238000002844 melting Methods 0.000 description 76
230000008018 melting Effects 0.000 description 75
239000000243 solution Substances 0.000 description 75
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 68
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 65
239000002253 acid Substances 0.000 description 59
125000003545 alkoxy group Chemical group 0.000 description 54
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 53
239000007858 starting material Substances 0.000 description 47
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 40
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
238000006243 chemical reaction Methods 0.000 description 39
239000003054 catalyst Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
229910052736 halogen Inorganic materials 0.000 description 32
150000002367 halogens Chemical class 0.000 description 29
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
238000001704 evaporation Methods 0.000 description 26
125000002252 acyl group Chemical group 0.000 description 25
235000011167 hydrochloric acid Nutrition 0.000 description 25
125000003342 alkenyl group Chemical group 0.000 description 24
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
238000006722 reduction reaction Methods 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 23
239000002904 solvent Substances 0.000 description 23
239000000126 substance Substances 0.000 description 23
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
230000008020 evaporation Effects 0.000 description 22
239000003921 oil Substances 0.000 description 22
238000010992 reflux Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 21
229910021529 ammonia Inorganic materials 0.000 description 20
125000003282 alkyl amino group Chemical group 0.000 description 19
239000000706 filtrate Substances 0.000 description 19
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 18
229910052801 chlorine Inorganic materials 0.000 description 18
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 17
239000003795 chemical substances by application Substances 0.000 description 17
239000000460 chlorine Substances 0.000 description 17
238000001953 recrystallisation Methods 0.000 description 17
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 16
229910052740 iodine Inorganic materials 0.000 description 16
231100000252 nontoxic Toxicity 0.000 description 16
230000003000 nontoxic effect Effects 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
125000006239 protecting group Chemical group 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
125000004656 alkyl sulfonylamino group Chemical group 0.000 description 15
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 15
230000002829 reductive effect Effects 0.000 description 15
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
239000013543 active substance Substances 0.000 description 14
239000013078 crystal Substances 0.000 description 14
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 14
239000012279 sodium borohydride Substances 0.000 description 14
229910000033 sodium borohydride Inorganic materials 0.000 description 14
125000003302 alkenyloxy group Chemical group 0.000 description 13
125000005133 alkynyloxy group Chemical group 0.000 description 13
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 13
239000012074 organic phase Substances 0.000 description 13
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 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
125000004423 acyloxy group Chemical group 0.000 description 12
125000005236 alkanoylamino group Chemical group 0.000 description 12
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 11
125000005115 alkyl carbamoyl group Chemical group 0.000 description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
125000004453 alkoxycarbonyl group Chemical group 0.000 description 10
150000001412 amines Chemical class 0.000 description 10
239000002585 base Substances 0.000 description 10
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 10
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000000155 melt Substances 0.000 description 10
239000000725 suspension Substances 0.000 description 10
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
229920002472 Starch Polymers 0.000 description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
125000004414 alkyl thio group Chemical group 0.000 description 9
125000001118 alkylidene group Chemical group 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
239000003638 chemical reducing agent Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
229910052794 bromium Inorganic materials 0.000 description 8
238000003776 cleavage reaction Methods 0.000 description 8
125000000753 cycloalkyl group Chemical group 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000004312 hexamethylene tetramine Substances 0.000 description 8
235000010299 hexamethylene tetramine Nutrition 0.000 description 8
238000005984 hydrogenation reaction Methods 0.000 description 8
229910052500 inorganic mineral Inorganic materials 0.000 description 8
229910052943 magnesium sulfate Inorganic materials 0.000 description 8
235000019341 magnesium sulphate Nutrition 0.000 description 8
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
235000010755 mineral Nutrition 0.000 description 8
239000011707 mineral Substances 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 8
239000000047 product Substances 0.000 description 8
102000005962 receptors Human genes 0.000 description 8
108020003175 receptors Proteins 0.000 description 8
230000007017 scission Effects 0.000 description 8
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 7
GPWXTFYFEXNIBL-UHFFFAOYSA-N 5-(2-aminoethoxy)-2-hydroxybenzamide Chemical compound NCCOC1=CC=C(O)C(C(N)=O)=C1 GPWXTFYFEXNIBL-UHFFFAOYSA-N 0.000 description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 7
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 7
238000001914 filtration Methods 0.000 description 7
239000006260 foam Substances 0.000 description 7
230000009249 intrinsic sympathomimetic activity Effects 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
241000282326 Felis catus Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
125000005153 alkyl sulfamoyl group Chemical group 0.000 description 6
125000000304 alkynyl group Chemical group 0.000 description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
230000003197 catalytic effect Effects 0.000 description 6
239000012043 crude product Substances 0.000 description 6
238000001035 drying Methods 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 6
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 6
235000015497 potassium bicarbonate Nutrition 0.000 description 6
229910000028 potassium bicarbonate Inorganic materials 0.000 description 6
239000011736 potassium bicarbonate Substances 0.000 description 6
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
229940100445 wheat starch Drugs 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
ZLZFPUSDGLSOSA-UHFFFAOYSA-N 2-hydroxy-4-(2-oxopropoxy)benzamide Chemical compound CC(=O)COC1=CC=C(C(N)=O)C(O)=C1 ZLZFPUSDGLSOSA-UHFFFAOYSA-N 0.000 description 5
QTKGGSMALHCAKN-UHFFFAOYSA-N 2-hydroxy-5-(2-oxopropoxy)benzamide Chemical compound CC(=O)COC1=CC=C(O)C(C(N)=O)=C1 QTKGGSMALHCAKN-UHFFFAOYSA-N 0.000 description 5
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 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
125000004442 acylamino group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
238000009835 boiling Methods 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
150000001728 carbonyl compounds Chemical class 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
239000012280 lithium aluminium hydride Substances 0.000 description 5
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
229960000581 salicylamide Drugs 0.000 description 5
230000004936 stimulating effect Effects 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
238000010626 work up procedure Methods 0.000 description 5
KBTBVMCLXUBQLM-UHFFFAOYSA-N 2,2-dimethyl-6-(2-oxopropoxy)-3h-1,3-benzoxazin-4-one Chemical compound O1C(C)(C)NC(=O)C2=CC(OCC(=O)C)=CC=C21 KBTBVMCLXUBQLM-UHFFFAOYSA-N 0.000 description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
KWBNVKBWZBMYMA-UHFFFAOYSA-N 5-(2-bromoethoxy)-2-hydroxybenzamide Chemical compound NC(=O)C1=CC(OCCBr)=CC=C1O KWBNVKBWZBMYMA-UHFFFAOYSA-N 0.000 description 4
FOQTVXMTYFCHSL-UHFFFAOYSA-N 5-[2-(benzylamino)ethoxy]-2-hydroxybenzamide Chemical compound C1=C(O)C(C(=O)N)=CC(OCCNCC=2C=CC=CC=2)=C1 FOQTVXMTYFCHSL-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
239000004593 Epoxy Substances 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
239000002841 Lewis acid Substances 0.000 description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
239000007868 Raney catalyst Substances 0.000 description 4
229910000564 Raney nickel Inorganic materials 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
230000009471 action Effects 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
150000001340 alkali metals Chemical class 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
230000000747 cardiac effect Effects 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
229960004698 dichlorobenzyl alcohol Drugs 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000005457 ice water Substances 0.000 description 4
239000011261 inert gas Substances 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
150000007517 lewis acids Chemical class 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
238000002156 mixing Methods 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
150000007524 organic acids Chemical class 0.000 description 4
239000004033 plastic Substances 0.000 description 4
229920003023 plastic Polymers 0.000 description 4
229910052697 platinum Inorganic materials 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000000454 talc Substances 0.000 description 4
229910052623 talc Inorganic materials 0.000 description 4
235000012222 talc Nutrition 0.000 description 4
230000007306 turnover Effects 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 3
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
GJRPNOHCETUYBP-UHFFFAOYSA-N 2,2-dimethyl-7-(2-oxopropoxy)-3h-1,3-benzoxazin-4-one Chemical compound O=C1NC(C)(C)OC2=CC(OCC(=O)C)=CC=C21 GJRPNOHCETUYBP-UHFFFAOYSA-N 0.000 description 3
XKBSNEQPMAWXEL-UHFFFAOYSA-N 2-[(2,2-dimethyl-4-oxo-3h-1,3-benzoxazin-6-yl)oxy]acetaldehyde Chemical compound O=CCOC1=CC=C2OC(C)(C)NC(=O)C2=C1 XKBSNEQPMAWXEL-UHFFFAOYSA-N 0.000 description 3
QIVRPVCGOHFXBZ-UHFFFAOYSA-N 2-chloro-5-(oxiran-2-yl)benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C2OC2)=C1 QIVRPVCGOHFXBZ-UHFFFAOYSA-N 0.000 description 3
IYKSOIDBIWOCQA-UHFFFAOYSA-N 4-(2-aminoethoxy)-2-hydroxybenzamide Chemical compound NCCOC1=CC=C(C(N)=O)C(O)=C1 IYKSOIDBIWOCQA-UHFFFAOYSA-N 0.000 description 3
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150000002366 halogen compounds Chemical class 0.000 description 1
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125000004970 halomethyl group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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JSVBYPAVUWZQHA-UHFFFAOYSA-M magnesium;1-methanidyl-2-methylbenzene;bromide Chemical compound [Mg+2].[Br-].CC1=CC=CC=C1[CH2-] JSVBYPAVUWZQHA-UHFFFAOYSA-M 0.000 description 1
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HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
DGEYTDCFMQMLTH-UHFFFAOYSA-N methanol;propan-2-ol Chemical compound OC.CC(C)O DGEYTDCFMQMLTH-UHFFFAOYSA-N 0.000 description 1
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RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 description 1
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MICGBQSMTKKKJM-UHFFFAOYSA-N methyl 4-(2-methoxyethoxy)benzoate Chemical compound COCCOC1=CC=C(C(=O)OC)C=C1 MICGBQSMTKKKJM-UHFFFAOYSA-N 0.000 description 1
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239000012285 osmium tetroxide Substances 0.000 description 1
229910000489 osmium tetroxide Inorganic materials 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
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238000007911 parenteral administration Methods 0.000 description 1
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150000002989 phenols Chemical class 0.000 description 1
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DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
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239000001267 polyvinylpyrrolidone Substances 0.000 description 1
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235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
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229910052952 pyrrhotite Inorganic materials 0.000 description 1
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
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BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
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MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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238000007086 side reaction Methods 0.000 description 1
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235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
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239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
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230000006794 tachycardia Effects 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
OFBPGACXRPVDQW-UHFFFAOYSA-N thiirane 1,1-dioxide Chemical compound O=S1(=O)CC1 OFBPGACXRPVDQW-UHFFFAOYSA-N 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
125000005505 thiomorpholino group Chemical group 0.000 description 1
238000003971 tillage Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
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LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 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
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
- 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
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
- 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
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
- 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
- C07D303/34—Compounds containing oxirane rings with hydrocarbon radicals, substituted by sulphur, selenium or tellurium 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
- C07D317/44—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 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—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 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
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Public Health (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

NO803653A 1979-12-04 1980-12-03 Fremgangsmaate til fremstilling av nye derivater til 2-amino-etanol. NO803653L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1074479		1979-12-04

Publications (1)

Publication Number	Publication Date
NO803653L true NO803653L (no)	1981-06-05

Family

ID=4366378

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO803653A NO803653L (no)	1979-12-04	1980-12-03	Fremgangsmaate til fremstilling av nye derivater til 2-amino-etanol.

Country Status (15)

Country	Link
EP (1)	EP0030030A1 (es)
JP (1)	JPS5692844A (es)
KR (1)	KR830004203A (es)
AU (1)	AU6503380A (es)
CA (1)	CA1146575A (es)
DD (2)	DD157796A5 (es)
DK (1)	DK516480A (es)
ES (5)	ES497444A0 (es)
FI (1)	FI803732L (es)
GB (1)	GB2065645B (es)
GR (1)	GR73998B (es)
IL (1)	IL61625A0 (es)
NO (1)	NO803653L (es)
PT (1)	PT72140B (es)
ZA (1)	ZA807545B (es)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57185243A (en) *	1981-05-08	1982-11-15	Ciba Geigy Ag	Substituted 2-aminoethanol
EG18188A (en) *	1986-05-01	1992-09-30	Pfizer Ltd	Process for preparation anti-arhythmia agents
US6436914B1 (en)	1998-06-30	2002-08-20	Bristol-Myers Squibb Company	2-hydroxy-3—(4-hydroxy-3-sulfonamidophenyl)—propylamines useful as beta 3 adrenergic agonists
US6696573B1 (en)	1999-09-03	2004-02-24	Asahi Kasei Kabushiki Kaisha	Processes for the preparation of tricyclic amino alcohol derivatives
NZ548098A (en)	2003-12-31	2010-05-28	Schering Plough Ltd	Control of parasites in animals by the use of imidazo[1,2-b]pyridazine derivatives

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
LU74760A1 (es) *	1975-04-17	1977-02-04
CA1147342A (en) *	1977-10-12	1983-05-31	Kazuo Imai	Process of producing novel phenylethanolamine derivatives
FI791727A (fi) *	1978-06-05	1979-12-06	Ciba Geigy Ag	Foerfarande foer framstaellning av n-alkylerade aminoalkoholer

1980
- 1980-11-28 DD DD80225571A patent/DD157796A5/de unknown
- 1980-11-28 DD DD80239910A patent/DD202692A5/de unknown
- 1980-12-01 FI FI803732A patent/FI803732L/fi not_active Application Discontinuation
- 1980-12-01 EP EP80107499A patent/EP0030030A1/de not_active Withdrawn
- 1980-12-01 GB GB8038525A patent/GB2065645B/en not_active Expired
- 1980-12-02 CA CA000365897A patent/CA1146575A/en not_active Expired
- 1980-12-02 GR GR63532A patent/GR73998B/el unknown
- 1980-12-03 ZA ZA00807545A patent/ZA807545B/xx unknown
- 1980-12-03 DK DK516480A patent/DK516480A/da unknown
- 1980-12-03 AU AU65033/80A patent/AU6503380A/en not_active Abandoned
- 1980-12-03 PT PT72140A patent/PT72140B/pt unknown
- 1980-12-03 NO NO803653A patent/NO803653L/no unknown
- 1980-12-03 IL IL61625A patent/IL61625A0/xx unknown
- 1980-12-04 ES ES497444A patent/ES497444A0/es active Granted
- 1980-12-04 JP JP17034080A patent/JPS5692844A/ja active Pending
- 1980-12-04 KR KR1019800004643A patent/KR830004203A/ko unknown
1981
- 1981-12-15 ES ES507982A patent/ES507982A0/es active Granted
- 1981-12-15 ES ES507980A patent/ES8300081A1/es not_active Expired
- 1981-12-15 ES ES507981A patent/ES8300082A1/es not_active Expired
- 1981-12-15 ES ES507983A patent/ES507983A0/es active Granted

Also Published As

Publication number	Publication date
JPS5692844A (en)	1981-07-27
ES507981A0 (es)	1982-10-01
EP0030030A1 (de)	1981-06-10
ES8300083A1 (es)	1982-10-01
ES8300084A1 (es)	1982-10-01
GB2065645A (en)	1981-07-01
GR73998B (es)	1984-06-06
KR830004203A (ko)	1983-07-06
DD202692A5 (de)	1983-09-28
IL61625A0 (en)	1981-01-30
ZA807545B (en)	1981-11-25
PT72140A (de)	1981-01-01
ES8205192A1 (es)	1982-06-01
ES8300082A1 (es)	1982-10-01
ES507980A0 (es)	1982-10-01
CA1146575A (en)	1983-05-17
ES507982A0 (es)	1982-10-01
AU6503380A (en)	1981-06-11
DK516480A (da)	1981-06-05
ES8300081A1 (es)	1982-10-01
ES497444A0 (es)	1982-06-01
GB2065645B (en)	1983-06-02
ES507983A0 (es)	1982-10-01
PT72140B (de)	1981-10-27
DD157796A5 (de)	1982-12-08
FI803732L (fi)	1981-06-05

Publication	Publication Date	Title
US4460580A (en)	1984-07-17	N-Alkylated aminoalcohols and their pharmaceutical compositions useful for the treatment of cardiac insufficiency
KR850000020B1 (ko)	1985-02-11	3-아미노프로판-1,2-디올 유도체의 제조방법
JP4212117B2 (ja)	2009-01-21	選択的β▲下３▼アドレナリン作動性アゴニスト
CS197304B2 (en)	1980-04-30	Method of producing novel 1-aryloxy- 2-hydroxy-3-alkylenamino propanes
US4328155A (en)	1982-05-04	Meta-sulfonamido-benzamides
NO812466L (no)	1982-06-17	Analogifremgangsmaate ved fremstilling av terapeutisk aktive 7-substituerte benzopyraner
WO1998031669A1 (fr)	1998-07-23	Nouvelles arylpiperazines derivees de piperidine comme medicaments antidepresseurs
NO803653L (no)	1981-06-05	Fremgangsmaate til fremstilling av nye derivater til 2-amino-etanol.
DK158460B (da)	1990-05-21	Analogifremgangsmaade til fremstilling af substituerede oxocarboxylsyrer
NZ196086A (en)	1984-08-24	1-phenyl-2-cyclohexene-1-alkylamine derivatives and pharmaceutical compositions
NO803693L (no)	1981-06-09	2,3-indoldion-derivater.
EP0127143B1 (en)	1990-03-21	Novel aryloxycycloalkanolaminoalkylene aryl ketones
IE45692B1 (en)	1982-10-20	1-amino-2-hydroxy-3-heterocyclyloxy-propanes
US4868315A (en)	1989-09-19	Novel aryloxycycloalkanolaminoalkylene aryl ketones
US4304790A (en)	1981-12-08	2-(Alkylthio, alkylsulfinyl or alkylsulfonyl)-4-[2-anilinoalkylamino)-1-hydroxyethyl]phenols and derivatives thereof
US4321398A (en)	1982-03-23	Thienyl and benzothienyl-tertiary butylaminophenoxypropanols
EP0045964A1 (de)	1982-02-17	Derivate des 3-Amino-1,2-propandiols
NO821510L (no)	1982-11-09	Fremgangsmaate til fremstilling av nye substituerte 2-aminoetanoler.
KR820001235B1 (ko)	1982-07-07	알킬티오페녹시프로파놀아민의 제조방법
IE49176B1 (en)	1985-08-21	N-alkylated aminoalcohols and their salts,processes for their preparation and pharmaceutical preparations containing these compounds