DD144050A5 - Verfahren zur herstellung von n-alkylierten aminoalkoholen - Google Patents

Verfahren zur herstellung von n-alkylierten aminoalkoholen Download PDF

Info

Publication number: DD144050A5
Authority: DD; German Democratic Republic
Prior art keywords: hydroxy; phenoxy; aminomethyl; carbamoyl; item
Prior art date: 1978-06-05

Application number

DD79213267A

Other languages

German (de)

English (en)

Inventor

Franz Ostermayer

Markus Zimmermann

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.)

1978-06-05

Filing date

1979-05-30

Publication date

1980-09-24

1979-05-30 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1980-09-24 Publication of DD144050A5 publication Critical patent/DD144050A5/de

Links

238000000034 method Methods 0.000 title claims description 53
238000002360 preparation method Methods 0.000 title description 7
150000001414 amino alcohols Chemical class 0.000 title description 3
-1 hydroxy-substituted phenyl Chemical group 0.000 claims description 118
150000001875 compounds Chemical class 0.000 claims description 81
WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 67
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
235000019445 benzyl alcohol Nutrition 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 12
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 10
230000002829 reductive effect Effects 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
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 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
XLHUBROMZOAQMV-UHFFFAOYSA-N 1,4-benzosemiquinone Chemical group [O]C1=CC=C(O)C=C1 XLHUBROMZOAQMV-UHFFFAOYSA-N 0.000 claims description 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 3
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 claims description 3
239000000376 reactant Substances 0.000 claims description 3
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000003700 epoxy group Chemical group 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000004942 pyridazin-6-yl group Chemical group N1=NC=CC=C1* 0.000 claims description 2
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 2
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
125000000464 thioxo group Chemical group S=* 0.000 claims description 2
BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 claims 4
125000003342 alkenyl group Chemical group 0.000 claims 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 125
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 57
239000000243 solution Substances 0.000 description 49
239000000203 mixture Substances 0.000 description 40
229960004217 benzyl alcohol Drugs 0.000 description 39
239000007858 starting material Substances 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
235000002639 sodium chloride Nutrition 0.000 description 36
150000003254 radicals Chemical class 0.000 description 34
239000003054 catalyst Substances 0.000 description 33
239000011541 reaction mixture Substances 0.000 description 26
238000007792 addition Methods 0.000 description 23
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
238000001704 evaporation Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
230000008020 evaporation Effects 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
238000010992 reflux Methods 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 14
238000006722 reduction reaction Methods 0.000 description 14
239000002904 solvent Substances 0.000 description 14
238000006243 chemical reaction Methods 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000000155 melt Substances 0.000 description 12
238000001953 recrystallisation Methods 0.000 description 12
229910052799 carbon Inorganic materials 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
239000013543 active substance Substances 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 10
239000002585 base Substances 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 9
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
150000002431 hydrogen Chemical class 0.000 description 8
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
235000011181 potassium carbonates Nutrition 0.000 description 8
239000012279 sodium borohydride Substances 0.000 description 8
229910000033 sodium borohydride Inorganic materials 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
229920002472 Starch Polymers 0.000 description 7
235000011114 ammonium hydroxide Nutrition 0.000 description 7
238000001914 filtration Methods 0.000 description 7
229910052736 halogen Inorganic materials 0.000 description 7
239000000543 intermediate Substances 0.000 description 7
238000002844 melting Methods 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
235000011054 acetic acid Nutrition 0.000 description 6
125000003545 alkoxy 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
229910021529 ammonia Inorganic materials 0.000 description 6
150000001735 carboxylic acids Chemical class 0.000 description 6
239000003638 chemical reducing agent Substances 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 6
239000012043 crude product Substances 0.000 description 6
239000006260 foam Substances 0.000 description 6
238000001640 fractional crystallisation Methods 0.000 description 6
150000002367 halogens Chemical class 0.000 description 6
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 6
150000004678 hydrides Chemical class 0.000 description 6
230000008018 melting Effects 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
239000000047 product Substances 0.000 description 6
125000001424 substituent group Chemical class 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
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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
150000001721 carbon Chemical group 0.000 description 5
239000013078 crystal Substances 0.000 description 5
238000005984 hydrogenation reaction Methods 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
229910052943 magnesium sulfate Inorganic materials 0.000 description 5
235000019341 magnesium sulphate Nutrition 0.000 description 5
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 5
238000000746 purification Methods 0.000 description 5
239000000454 talc Substances 0.000 description 5
235000012222 talc Nutrition 0.000 description 5
229910052623 talc Inorganic materials 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
125000001118 alkylidene group Chemical group 0.000 description 4
150000001728 carbonyl compounds Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
229910052801 chlorine Inorganic materials 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
125000006239 protecting group Chemical group 0.000 description 4
125000000714 pyrimidinyl group Chemical group 0.000 description 4
229960000581 salicylamide Drugs 0.000 description 4
229940100445 wheat starch Drugs 0.000 description 4
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
125000006016 2-bromoethoxy group Chemical group 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
FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 3
238000005727 Friedel-Crafts reaction Methods 0.000 description 3
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 3
239000002841 Lewis acid Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical group NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical compound [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001340 alkali metals Chemical class 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
235000019253 formic acid Nutrition 0.000 description 3
239000001530 fumaric acid Substances 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
239000004312 hexamethylene tetramine Substances 0.000 description 3
235000010299 hexamethylene tetramine Nutrition 0.000 description 3
239000011261 inert gas Substances 0.000 description 3
229910052500 inorganic mineral Inorganic materials 0.000 description 3
150000007517 lewis acids Chemical class 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
235000010755 mineral Nutrition 0.000 description 3
239000011707 mineral Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
125000002971 oxazolyl group Chemical group 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000825 pharmaceutical preparation Substances 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
125000003373 pyrazinyl group Chemical group 0.000 description 3
125000002098 pyridazinyl group Chemical group 0.000 description 3
125000004076 pyridyl group Chemical group 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000011975 tartaric acid Substances 0.000 description 3
235000002906 tartaric acid Nutrition 0.000 description 3
125000001544 thienyl group Chemical group 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
SEPPVOUBHWNCAW-FNORWQNLSA-N (E)-4-oxonon-2-enal Chemical compound CCCCCC(=O)\C=C\C=O SEPPVOUBHWNCAW-FNORWQNLSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 2
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 2
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
BOEUPAAUIMINEC-UHFFFAOYSA-N 4-(2-aminopropoxy)-2-hydroxybenzamide Chemical compound CC(N)COC1=CC=C(C(N)=O)C(O)=C1 BOEUPAAUIMINEC-UHFFFAOYSA-N 0.000 description 2
HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical compound NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 2
LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 description 2
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 2
YKLJEBPGBGIZGN-UHFFFAOYSA-N 5-[3-(benzylamino)-3-oxopropyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(CCC(=O)NCC=2C=CC=CC=2)=C1 YKLJEBPGBGIZGN-UHFFFAOYSA-N 0.000 description 2
GTDNMZMRNMURSX-UHFFFAOYSA-N 6-(2-bromoethoxy)-2,2-dimethyl-3h-1,3-benzoxazin-4-one Chemical compound BrCCOC1=CC=C2OC(C)(C)NC(=O)C2=C1 GTDNMZMRNMURSX-UHFFFAOYSA-N 0.000 description 2
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms

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

DD79213267A 1978-06-05 1979-05-30 Verfahren zur herstellung von n-alkylierten aminoalkoholen DD144050A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH613678		1978-06-05

Publications (1)

Publication Number	Publication Date
DD144050A5 true DD144050A5 (de)	1980-09-24

Family

ID=4304840

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD79213267A DD144050A5 (de)	1978-06-05	1979-05-30	Verfahren zur herstellung von n-alkylierten aminoalkoholen

Country Status (26)

Country	Link
US (1)	US4460580A (pl)
EP (1)	EP0005848B1 (pl)
JP (1)	JPS54163543A (pl)
KR (4)	KR840000926B1 (pl)
AR (3)	AR229022A1 (pl)
AT (1)	ATE511T1 (pl)
AU (1)	AU522483B2 (pl)
CA (1)	CA1124241A (pl)
CY (1)	CY1256A (pl)
DD (1)	DD144050A5 (pl)
DE (1)	DE2961669D1 (pl)
DK (1)	DK229879A (pl)
ES (1)	ES481238A1 (pl)
FI (1)	FI791727A7 (pl)
GB (1)	GB2026474B (pl)
GR (1)	GR74057B (pl)
HK (1)	HK15585A (pl)
HU (1)	HU182019B (pl)
IL (1)	IL57471A (pl)
MY (1)	MY8500690A (pl)
NO (1)	NO149034C (pl)
NZ (1)	NZ190632A (pl)
PL (5)	PL117155B1 (pl)
PT (1)	PT69723A (pl)
SG (1)	SG45884G (pl)
ZA (1)	ZA792748B (pl)

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EP0006735B1 (en) *	1978-06-28	1983-06-15	Beecham Group Plc	Secondary amines, their preparation, pharmaceutical compositions containing them and their use
US4316907A (en)	1979-06-29	1982-02-23	Glaxo Group Limited	Heterocyclic compounds, processes for their preparation and their use
DD157796A5 (de) *	1979-12-04	1982-12-08	Ciba Geigy Ag	Verfahren zur herstellung neuer derivate des 2-amino-aethanols
JPS5726653A (en) *	1980-05-09	1982-02-12	Ciba Geigy Ag	Substituted phenyl ether
DE3026534A1 (de) *	1980-07-12	1982-03-18	C.H. Boehringer Sohn, 6507 Ingelheim	3,1-benzoxazin-2-one, ihre herstellung und verwendung
GR74992B (pl) *	1980-08-13	1984-07-12	Ciba Geigy Ag
JPS57185243A (en) *	1981-05-08	1982-11-15	Ciba Geigy Ag	Substituted 2-aminoethanol
US4466965A (en) *	1982-07-26	1984-08-21	American Hospital Supply Corporation	Phthalazine compounds, compositions and use
FR2543139B1 (fr) *	1983-03-22	1985-08-16	Cerm Cent Europ Rech Mauvernay	Derives de (1-alcoxy 2-amino) ethyl pyridine ou pyrazine, leur preparation et leur application en therapeutique
DE3608290A1 (de) *	1986-03-13	1987-09-24	Thomae Gmbh Dr K	Neue substituierte thiazole und oxazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3621775A1 (de) *	1986-03-13	1988-01-07	Thomae Gmbh Dr K	Neue substituierte thiazole und oxazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
CA1287061C (en) *	1986-06-27	1991-07-30	F. Hoffmann-La Roche Ag	Pyridine ethanolamine derivatives
GB8714901D0 (en) *	1986-07-23	1987-07-29	Ici Plc	Amide derivatives
DE3627663A1 (de) *	1986-08-14	1988-03-03	Bayer Ag	Heteroarylethylamine, verfahren zu ihrer herstellung und ihre verwendung als leistungsfoerderer bei tieren
US5108363A (en) *	1988-02-19	1992-04-28	Gensia Pharmaceuticals, Inc.	Diagnosis, evaluation and treatment of coronary artery disease by exercise simulation using closed loop drug delivery of an exercise simulating agent beta agonist
GB8925032D0 (en) *	1989-11-06	1989-12-28	Ici Plc	Chemical compounds
JPH0466934A (ja) *	1990-07-04	1992-03-03	Fuji Photo Film Co Ltd	ハロゲン化銀写真感光材料
US5232948A (en) *	1990-09-10	1993-08-03	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Substituted monocyclic aryl compounds exhibiting selective leukotriene b4 antagonist activity
US6001884A (en) *	1991-08-23	1999-12-14	Nps Pharmaceuticals, Inc.	Calcium receptor-active molecules
US5763569A (en) *	1991-08-23	1998-06-09	The Brigham And Women's Hospital, Inc	Calcium receptor-active molecules
US6031003A (en) *	1991-08-23	2000-02-29	Nps Pharmaceuticals, Inc.	Calcium receptor-active molecules
US5688938A (en) *	1991-08-23	1997-11-18	The Brigham & Women's Hospital, Inc.	Calcium receptor-active molecules
US6313146B1 (en)	1991-08-23	2001-11-06	Nps Pharmaceuticals, Inc.	Calcium receptor-active molecules
US6011068A (en) *	1991-08-23	2000-01-04	Nps Pharmaceuticals, Inc.	Calcium receptor-active molecules
RU2147574C1 (ru) *	1991-08-23	2000-04-20	Эн-Пи-Эс Фармасьютикалз, Инк.	Арилалкиламины, композиции, способы лечения и диагностики, способы идентификации соединения
US5858684A (en) *	1991-08-23	1999-01-12	The Brigham And Women's Hospital, Inc.	Method of screening calcium receptor-active molecules
US5208252A (en) *	1992-07-24	1993-05-04	Ortho Pharmaceutical Corporation	Aminoethylthiophene derivatives
US5962314A (en) *	1993-02-23	1999-10-05	Nps Pharmaceuticals, Inc.	Calcium receptor-active molecules
AU1533495A (en) *	1994-01-12	1995-08-01	Byk Nederland Bv	Phenyl ethanol amine ethers and uses thereof as beta-adreno-receptor agonists
US6211244B1 (en)	1994-10-21	2001-04-03	Nps Pharmaceuticals, Inc.	Calcium receptor-active compounds
EP0907631B1 (en)	1996-05-01	2003-06-18	Nps Pharmaceuticals, Inc.	Inorganic ion receptor-active compounds
KR100380520B1 (ko) *	2000-09-08	2003-04-23	한국화학연구원	피리딘을 포함한 β-아미노알코올 유도체
JP2005523565A (ja) *	2002-04-22	2005-08-04	コーニンクレッカ　フィリップス　エレクトロニクス　エヌ　ヴィ	発光スクリーン
US7538141B2 (en) *	2004-03-23	2009-05-26	Alan Daniel Brown	Compounds for the treatment of diseases
CA2792407A1 (en) *	2010-03-08	2011-09-15	The University Of Tennessee Research Foundation	Beta-adrenergic receptor agonists and uses thereof
ITMI20122221A1 (it) *	2012-12-21	2014-06-22	C4T S C A R L	Nuovi composti del 2,3-diidro-4h-1,3-benzossazin-4-one, metodo per prepararli e forma farmaceutica che li comprende
CN104008939B (zh) *	2014-06-19	2016-05-11	苏州普京真空技术有限公司	一种耐用电子枪灯丝
USD954933S1 (en)	2018-06-01	2022-06-14	Chiaro Technology Limited	Breast pump accessory

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GB1178400A (en) *	1966-12-13	1970-01-21	Delalande Sa	Nitrogen Substituted Amines and their process of Preparation.
DE1543538A1 (de) *	1966-12-30	1976-02-05	Degussa	Verfahren zur herstellung neuer heterocyclischer aminoalkohole
US4012444A (en) *	1969-07-08	1977-03-15	Allen & Hanburys Limited	5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof
GB1301134A (en) *	1970-07-18	1972-12-29	Pfizer Ltd	SUBSTITUTED 1-PHENYL-2-ALLYLAMINO-ALKANOLS, 1-PHENYL-2-ALLYLAMINO-ALKANES AND alpha-AMINOALKYLPHENYL KETONES
GB1398738A (en) *	1972-12-05	1975-06-25	Pfizer Ltd	Propanolamine derivatives
US4082772A (en) *	1975-04-18	1978-04-04	American Home Products Corporation	Thiophene ethanolamines
US4146638A (en) *	1976-02-17	1979-03-27	Boehringer Ingelheim Gmbh	N-(3-phenoxy-2-hydroxy-propyl)-n-(2-phenyl-2-hydroxy-ethyl)-amines

1979
- 1979-05-30 DD DD79213267A patent/DD144050A5/de unknown
- 1979-05-30 FI FI791727A patent/FI791727A7/fi not_active Application Discontinuation
- 1979-06-01 CA CA328,929A patent/CA1124241A/en not_active Expired
- 1979-06-01 NO NO791841A patent/NO149034C/no unknown
- 1979-06-01 NZ NZ190632A patent/NZ190632A/en unknown
- 1979-06-01 AT AT79101724T patent/ATE511T1/de active
- 1979-06-01 CY CY1256A patent/CY1256A/xx unknown
- 1979-06-01 DE DE7979101724T patent/DE2961669D1/de not_active Expired
- 1979-06-01 DK DK229879A patent/DK229879A/da not_active Application Discontinuation
- 1979-06-01 EP EP79101724A patent/EP0005848B1/de not_active Expired
- 1979-06-04 KR KR7901814A patent/KR840000926B1/ko not_active Expired
- 1979-06-04 PL PL1979222397A patent/PL117155B1/pl unknown
- 1979-06-04 PT PT69723A patent/PT69723A/pt unknown
- 1979-06-04 AU AU47736/79A patent/AU522483B2/en not_active Ceased
- 1979-06-04 PL PL1979216090A patent/PL116529B1/pl unknown
- 1979-06-04 ES ES481238A patent/ES481238A1/es not_active Expired
- 1979-06-04 HU HU79CI1940A patent/HU182019B/hu unknown
- 1979-06-04 PL PL1979222400A patent/PL116597B1/pl unknown
- 1979-06-04 IL IL57471A patent/IL57471A/xx unknown
- 1979-06-04 PL PL1979222398A patent/PL117158B1/pl unknown
- 1979-06-04 GB GB7919470A patent/GB2026474B/en not_active Expired
- 1979-06-04 PL PL1979222399A patent/PL116612B1/pl unknown
- 1979-06-04 ZA ZA792748A patent/ZA792748B/xx unknown
- 1979-06-05 GR GR59274A patent/GR74057B/el unknown
- 1979-06-05 JP JP6952479A patent/JPS54163543A/ja active Pending
1980
- 1980-12-17 AR AR283668A patent/AR229022A1/es active
- 1980-12-17 AR AR283669A patent/AR229951A1/es active
- 1980-12-17 AR AR283670A patent/AR229581A1/es active
1982
- 1982-03-12 KR KR1019820001067A patent/KR830000680A/ko not_active Ceased
- 1982-03-12 KR KR1019820001066A patent/KR830000679A/ko not_active Ceased
- 1982-03-12 KR KR1019820001068A patent/KR830000681A/ko not_active Ceased
- 1982-06-24 US US06/391,814 patent/US4460580A/en not_active Expired - Fee Related
1984
- 1984-06-23 SG SG458/84A patent/SG45884G/en unknown
1985
- 1985-03-07 HK HK155/85A patent/HK15585A/xx unknown
- 1985-12-30 MY MY690/85A patent/MY8500690A/xx unknown

Also Published As

Publication number	Publication date
ATE511T1 (de)	1982-01-15
CA1124241A (en)	1982-05-25
KR830000681A (ko)	1983-04-18
KR840000926B1 (ko)	1984-06-29
ES481238A1 (es)	1980-02-16
PL116612B1 (en)	1981-06-30
AR229022A1 (es)	1983-05-31
EP0005848B1 (de)	1981-12-30
US4460580A (en)	1984-07-17
GR74057B (pl)	1984-06-06
PT69723A (de)	1979-07-01
PL117155B1 (en)	1981-07-31
NO791841L (no)	1979-12-06
SG45884G (en)	1985-03-08
DE2961669D1 (en)	1982-02-18
PL216090A1 (pl)	1980-03-24
HK15585A (en)	1985-03-15
NZ190632A (en)	1984-07-06
IL57471A (en)	1982-11-30
MY8500690A (en)	1985-12-31
NO149034B (no)	1983-10-24
KR830000679A (ko)	1983-04-18
GB2026474B (en)	1982-07-14
AR229951A1 (es)	1984-01-31
AU4773679A (en)	1979-12-13
PL116597B1 (en)	1981-06-30
CY1256A (en)	1984-11-23
PL116529B1 (en)	1981-06-30
KR830000680A (ko)	1983-04-18
JPS54163543A (en)	1979-12-26
FI791727A7 (fi)	1981-01-01
ZA792748B (en)	1980-06-25
HU182019B (en)	1983-12-28
NO149034C (no)	1984-02-01
AR229581A1 (es)	1983-09-30
PL117158B1 (en)	1981-07-31
DK229879A (da)	1979-12-06
AU522483B2 (en)	1982-06-10
EP0005848A1 (de)	1979-12-12
GB2026474A (en)	1980-02-06

Publication	Publication Date	Title
DD144050A5 (de)	1980-09-24	Verfahren zur herstellung von n-alkylierten aminoalkoholen
EP0004920B1 (de)	1981-08-05	Carbazolyl-(4)-oxy-propanolamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DD150456A5 (de)	1981-09-02	Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols
US4034009A (en)	1977-07-05	4-Ureido-2-acyl phenoxypropanolamine
EP0375791A1 (de)	1990-07-04	Neue Phenylethanolamine, deren Verwendung als Arzneimittel und als Leistungsförderer bei Tieren sowie Verfahren zu ihrer Herstellung
DE69132167T2 (de)	2000-12-14	Kondensierte benzoxa-ringverbindung, deren herstellung sowie diese enthaltendes arzneimittel
DE1922003C3 (de)	1979-10-11	N-(3-Aryloxy-2-hydroxypropyl)-aminocarbonsäuren, deren Ester, Amide und Salze, Verfahren zur Herstellung dieser Verbindungen und deren Verwendung bei der Bekämpfung von Herzinsuffizienz
DE3443998A1 (de)	1986-06-05	Amino-propanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel sowie zwischenprodukte
EP0124476A1 (de)	1984-11-07	Carboxamide, Verfahren zur Herstellung und pharmazeutische Präparate, die diese enthalten
US4914202A (en)	1990-04-03	Morpholine compounds
DE3114239A1 (de)	1982-02-18	"piperazinderivate"
FR2460294A1 (fr)	1981-01-23	Nouveaux oxime-ethers, leur procede de preparation et compositions pharmaceutiques les contenant
DE69600231T2 (de)	1998-12-17	N-Arylalkylphenylacetamidderivate
DE3014813A1 (de)	1980-11-13	2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate
US4041074A (en)	1977-08-09	1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives
FR2651227A1 (fr)	1991-03-01	Nouveaux derives de l'aminopropanol, procede pour leur preparation et compositions pharmaceutiques contenant de tels derives.
DE69315841T2 (de)	1998-04-09	Indolinyl n-hydroxyharnstoffe und n-hydroxamsäure derivate als lipoxygenese inhibitoren
US4450172A (en)	1984-05-22	Antihypertensive polyhalohydroxyisopropyl phenylalka(e)noic acid esters of alkylaminohydroxypropyloxyphenylalkyl alcohols
DD157796A5 (de)	1982-12-08	Verfahren zur herstellung neuer derivate des 2-amino-aethanols
CH655721A5 (fr)	1986-05-15	Derives du furanne et sels d'addition de ces derives leurs procedes de preparation et composition pharmaceutique les contenant.
CA1210392A (fr)	1986-08-26	Procede pour la preparation d'amides n-substitues, et les amides ainsi obtenus
EP0491243A1 (de)	1992-06-24	Alkylaminoalkylamin- und -äther- Verbindungen sowie Verfahren und Zwischenprodukte zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2324584A1 (de)	1974-01-10	Neue amine und verfahren zu ihrer herstellung
DD202286A5 (de)	1983-09-07	Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols
EP0069838A1 (de)	1983-01-19	Aralkylaminoethoxysalicylamide und deren pharmazeutische Verwendung