FI63741C - Analogifoerfarande foer framstaellning av nya substituerade feoxipropanolaminer med hjaertselektiv beta-receptor blocke rade verkan - Google Patents

Analogifoerfarande foer framstaellning av nya substituerade feoxipropanolaminer med hjaertselektiv beta-receptor blocke rade verkan Download PDF

Info

Publication number: FI63741C
Authority: FI; Finland
Prior art keywords: phenoxy; isopropylamino; formula; propanol; residue
Prior art date: 1972-04-04

Application number

FI1026/73A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI63741B (fi

Inventor

Peder Bernhard Berntsson

Arne Elof Braendstroem

Enar Ingemar Carlsson

Stig Aoke Ingemar Carlsson

Lars Ek

Benny Roger Samuelsson

Sven Erik Sjoestrand

Gert Christer Strandlund

Bengt Arne Hjalmar Aoblad

Original Assignee

Haessle Ab

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.)

1972-04-04

Filing date

1973-04-03

Publication date

1983-08-10

1973-04-03 Application filed by Haessle Ab filed Critical Haessle Ab

1983-04-29 Application granted granted Critical

1983-04-29 Publication of FI63741B publication Critical patent/FI63741B/fi

1983-08-10 Publication of FI63741C publication Critical patent/FI63741C/fi

Links

102000012740 beta Adrenergic Receptors Human genes 0.000 title description 9
108010079452 beta Adrenergic Receptors Proteins 0.000 title description 9
-1 2-ethoxyethyl Chemical group 0.000 description 181
150000001875 compounds Chemical class 0.000 description 103
125000004432 carbon atom Chemical group C* 0.000 description 87
125000000217 alkyl group Chemical group 0.000 description 74
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 66
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 66
239000000203 mixture Substances 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
238000000034 method Methods 0.000 description 51
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
238000006243 chemical reaction Methods 0.000 description 35
125000003545 alkoxy group Chemical group 0.000 description 34
239000000243 solution Substances 0.000 description 34
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
238000002844 melting Methods 0.000 description 30
230000008018 melting Effects 0.000 description 30
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 27
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 description 23
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 23
238000002360 preparation method Methods 0.000 description 23
239000001257 hydrogen Substances 0.000 description 22
229910052739 hydrogen Inorganic materials 0.000 description 22
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 22
230000009467 reduction Effects 0.000 description 22
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 21
150000001412 amines Chemical class 0.000 description 20
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 19
239000000460 chlorine Substances 0.000 description 19
229910052801 chlorine Inorganic materials 0.000 description 19
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
229910052794 bromium Inorganic materials 0.000 description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 18
150000003839 salts Chemical class 0.000 description 18
239000002253 acid Substances 0.000 description 17
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 16
229910000027 potassium carbonate Inorganic materials 0.000 description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
239000004480 active ingredient Substances 0.000 description 14
125000003118 aryl group Chemical group 0.000 description 14
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 13
238000009472 formulation Methods 0.000 description 13
239000008187 granular material Substances 0.000 description 13
229910052736 halogen Inorganic materials 0.000 description 13
150000002367 halogens Chemical class 0.000 description 13
230000007062 hydrolysis Effects 0.000 description 13
238000006460 hydrolysis reaction Methods 0.000 description 13
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 13
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
230000000747 cardiac effect Effects 0.000 description 12
239000012071 phase Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
125000001424 substituent group Chemical group 0.000 description 12
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
239000002585 base Substances 0.000 description 11
238000005984 hydrogenation reaction Methods 0.000 description 11
238000001990 intravenous administration Methods 0.000 description 11
239000011734 sodium Substances 0.000 description 11
239000002904 solvent Substances 0.000 description 11
241000282326 Felis catus Species 0.000 description 10
229910021529 ammonia Inorganic materials 0.000 description 10
229910052763 palladium Inorganic materials 0.000 description 10
239000000126 substance Substances 0.000 description 10
230000009471 action Effects 0.000 description 9
125000003342 alkenyl group Chemical group 0.000 description 9
239000003054 catalyst Substances 0.000 description 9
239000007789 gas Substances 0.000 description 9
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 8
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
108010010803 Gelatin Proteins 0.000 description 8
208000001871 Tachycardia Diseases 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000013543 active substance Substances 0.000 description 8
239000003513 alkali Substances 0.000 description 8
125000004849 alkoxymethyl group Chemical group 0.000 description 8
239000002775 capsule Substances 0.000 description 8
239000008273 gelatin Substances 0.000 description 8
229920000159 gelatin Polymers 0.000 description 8
235000019322 gelatine Nutrition 0.000 description 8
235000011852 gelatine desserts Nutrition 0.000 description 8
238000010253 intravenous injection Methods 0.000 description 8
229960001317 isoprenaline Drugs 0.000 description 8
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239000011541 reaction mixture Substances 0.000 description 8
230000006794 tachycardia Effects 0.000 description 8
229920002261 Corn starch Polymers 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
239000007868 Raney catalyst Substances 0.000 description 7
229910000564 Raney nickel Inorganic materials 0.000 description 7
125000004466 alkoxycarbonylamino group Chemical group 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000008120 corn starch Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
238000002347 injection Methods 0.000 description 7
239000007924 injection Substances 0.000 description 7
125000004433 nitrogen atom Chemical group N* 0.000 description 7
239000000843 powder Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000012279 sodium borohydride Substances 0.000 description 7
229910000033 sodium borohydride Inorganic materials 0.000 description 7
239000007787 solid Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
229920002472 Starch Polymers 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
238000009835 boiling Methods 0.000 description 6
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
238000007906 compression Methods 0.000 description 6
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229940079593 drug Drugs 0.000 description 6
239000003814 drug Substances 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
238000000855 fermentation Methods 0.000 description 6
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125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
239000008107 starch Substances 0.000 description 6
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 6
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 5
229910052783 alkali metal Inorganic materials 0.000 description 5
150000001340 alkali metals Chemical class 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
238000005915 ammonolysis reaction Methods 0.000 description 5
230000008485 antagonism Effects 0.000 description 5
239000005557 antagonist Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000002876 beta blocker Substances 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
238000001914 filtration Methods 0.000 description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
230000002401 inhibitory effect Effects 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
238000004806 packaging method and process Methods 0.000 description 5
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235000020357 syrup Nutrition 0.000 description 5
238000012360 testing method Methods 0.000 description 5
238000011282 treatment Methods 0.000 description 5
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GRXITKOCHGVOMH-UHFFFAOYSA-N 2-chloro-4-(2-methoxyethyl)phenol Chemical compound COCCC1=CC=C(O)C(Cl)=C1 GRXITKOCHGVOMH-UHFFFAOYSA-N 0.000 description 4
JWZZKOKVBUJMES-LLVKDONJSA-N 4-[(1S)-1-hydroxy-2-(propan-2-ylamino)ethyl]benzene-1,2-diol Chemical compound CC(C)NC[C@@H](O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-LLVKDONJSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 4
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ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
JWZZKOKVBUJMES-NSHDSACASA-N L-isoprenaline Chemical compound CC(C)NC[C@H](O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-NSHDSACASA-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
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241000277284 Salvelinus fontinalis Species 0.000 description 4
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230000002378 acidificating effect Effects 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000004414 alkyl thio group Chemical group 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
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TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
239000003086 colorant Substances 0.000 description 4
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VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 4
230000036571 hydration Effects 0.000 description 4
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238000000338 in vitro Methods 0.000 description 4
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GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 4
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BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
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UZHDGDDPOPDJGM-UHFFFAOYSA-N Stigmatellin A Natural products COC1=CC(OC)=C2C(=O)C(C)=C(CCC(C)C(OC)C(C)C(C=CC=CC(C)=CC)OC)OC2=C1O UZHDGDDPOPDJGM-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
244000126014 Valeriana officinalis Species 0.000 description 1
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150000003973 alkyl amines Chemical class 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
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PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
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238000011068 loading method Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229960002510 mandelic acid Drugs 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
229910001092 metal group alloy Inorganic materials 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
125000004492 methyl ester group Chemical group 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
239000011707 mineral Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
101150009274 nhr-1 gene Proteins 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical group N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
239000010690 paraffinic oil Substances 0.000 description 1
239000013618 particulate matter Substances 0.000 description 1
239000002304 perfume Substances 0.000 description 1
230000036513 peripheral conductance Effects 0.000 description 1
230000036581 peripheral resistance Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
PYOZTOXFQNWBIS-UHFFFAOYSA-N phenol;sodium Chemical compound [Na].OC1=CC=CC=C1 PYOZTOXFQNWBIS-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000003825 pressing Methods 0.000 description 1
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XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
239000001294 propane Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
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239000010453 quartz Substances 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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238000011160 research Methods 0.000 description 1
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
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
229960000953 salsalate Drugs 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
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HSFQBFMEWSTNOW-UHFFFAOYSA-N sodium;carbanide Chemical group [CH3-].[Na+] HSFQBFMEWSTNOW-UHFFFAOYSA-N 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
238000004544 sputter deposition Methods 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229950000244 sulfanilic acid Drugs 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
230000026683 transduction Effects 0.000 description 1
238000010361 transduction Methods 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical group C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
230000003827 upregulation Effects 0.000 description 1
238000011144 upstream manufacturing Methods 0.000 description 1
235000016788 valerian Nutrition 0.000 description 1
239000002966 varnish Substances 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Epoxy Compounds (AREA)

FI1026/73A 1972-04-04 1973-04-03 Analogifoerfarande foer framstaellning av nya substituerade feoxipropanolaminer med hjaertselektiv beta-receptor blocke rade verkan FI63741C (fi)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE7204321A SE384853B (sv)	1972-04-04	1972-04-04	Forfarande for framstellning av nya aminer
SE432172		1972-04-04

Publications (2)

Publication Number	Publication Date
FI63741B FI63741B (fi)	1983-04-29
FI63741C true FI63741C (fi)	1983-08-10

Family

ID=20263926

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI1026/73A FI63741C (fi)	1972-04-04	1973-04-03	Analogifoerfarande foer framstaellning av nya substituerade feoxipropanolaminer med hjaertselektiv beta-receptor blocke rade verkan

Country Status (19)

Country	Link
US (1)	US3996382A (de)
JP (1)	JPS5924971B2 (de)
AR (1)	AR204982A1 (de)
AT (1)	AT321276B (de)
BE (1)	BE797414A (de)
BR (1)	BR7302430D0 (de)
CA (1)	CA1017755A (de)
CH (3)	CH587224A5 (de)
DE (1)	DE2316727C3 (de)
ES (3)	ES413316A1 (de)
FI (1)	FI63741C (de)
FR (1)	FR2179069B1 (de)
GB (1)	GB1421824A (de)
IE (1)	IE38302B1 (de)
NL (1)	NL7304606A (de)
NO (1)	NO139167C (de)
SE (1)	SE384853B (de)
SU (1)	SU533336A3 (de)
ZA (1)	ZA732119B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU169464B (de) *	1974-02-20	1976-11-28
IL48309A (en) *	1974-10-25	1980-01-31	Robins Co Inc A H	1-aryloxy-4-amino-2-butanols and pharmaceutical compositions containing them
JPS5337126A (en) *	1976-09-17	1978-04-06	Nishida Marine Boiler	Obtaining method of nickel from low grade nickel ore
JPS55161036A (en) *	1979-06-05	1980-12-15	Ooeyama Nickel Kk	Nickel oxide ore smelting method
ZW9881A1 (en) *	1980-06-02	1981-12-23	Hoffmann La Roche	Substituted phenoxyaminopropanol derivatives
FR2497194B1 (fr) *	1980-08-07	1985-06-14	Sandoz Sa	Nouveaux composes phenoliques
CH643527A5 (en) *	1980-10-24	1984-06-15	Ciba Geigy Ag	Process for the preparation of 1-alkylamino-3-(4-(2-lower alkoxy-ethyl)phenoxy)-2-propanols
DE3125636A1 (de) *	1981-06-30	1983-01-13	Merck Patent Gmbh, 6100 Darmstadt	1-(p-2-isopropoxyethoxymethyl-phenoxy)-3-isopropylamino-propan-2-ol zur senkung des augeninnendrucks und ophtalmikum, enthalten diese verbindung
SE457505B (sv) *	1984-01-10	1989-01-09	Lejus Medical Ab	Laminatbelagd oral farmaceutisk komposition och foerfarande foer dess framstaellning
US5064827A (en) *	1988-12-15	1991-11-12	Du Pont Merck Pharmaceutical Company	Polyhydroxybenzyloxpropanolamines
US4959390A (en) *	1988-12-15	1990-09-25	E. I. Du Pont De Nemours And Company	Polyhydroxybenzyloxypropanolamines
KR100489649B1 (ko) *	1998-04-14	2005-09-02	삼성정밀화학 주식회사	(s)-3-치환-2-히드록시프로필아민의제조방법
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1972
- 1972-04-04 SE SE7204321A patent/SE384853B/xx unknown
1973
- 1973-01-01 AR AR250907A patent/AR204982A1/es active
- 1973-03-27 ZA ZA732119A patent/ZA732119B/xx unknown
- 1973-03-28 BE BE129334A patent/BE797414A/xx not_active IP Right Cessation
- 1973-04-03 CA CA167,812A patent/CA1017755A/en not_active Expired
- 1973-04-03 FR FR7312015A patent/FR2179069B1/fr not_active Expired
- 1973-04-03 SU SU1907907A patent/SU533336A3/ru active
- 1973-04-03 FI FI1026/73A patent/FI63741C/fi active
- 1973-04-03 ES ES413316A patent/ES413316A1/es not_active Expired
- 1973-04-03 NL NL7304606A patent/NL7304606A/xx not_active Application Discontinuation
- 1973-04-03 IE IE520/73A patent/IE38302B1/xx unknown
- 1973-04-03 GB GB1584673A patent/GB1421824A/en not_active Expired
- 1973-04-04 JP JP48037950A patent/JPS5924971B2/ja not_active Expired
- 1973-04-04 DE DE2316727A patent/DE2316727C3/de not_active Expired
- 1973-04-04 US US05/347,625 patent/US3996382A/en not_active Expired - Lifetime
- 1973-04-04 CH CH237976A patent/CH587224A5/xx not_active IP Right Cessation
- 1973-04-04 BR BR732430A patent/BR7302430D0/pt unknown
- 1973-04-04 NO NO1377/73A patent/NO139167C/no unknown
- 1973-04-04 AT AT293873A patent/AT321276B/de active
- 1973-04-04 CH CH481673A patent/CH587222A5/xx not_active IP Right Cessation
- 1973-04-04 CH CH238076A patent/CH587225A5/xx not_active IP Right Cessation
1975
- 1975-07-29 ES ES439803A patent/ES439803A1/es not_active Expired
- 1975-07-29 ES ES439804A patent/ES439804A1/es not_active Expired

Also Published As

Publication number	Publication date
CH587222A5 (de)	1977-04-29
GB1421824A (en)	1976-01-21
DE2316727B2 (de)	1978-06-22
DE2316727A1 (de)	1974-01-10
AR204982A1 (es)	1976-03-31
ES439804A1 (es)	1977-04-16
IE38302L (en)	1973-10-04
FR2179069A1 (de)	1973-11-16
BE797414A (fr)	1973-07-16
AT321276B (de)	1975-03-25
NO139167C (no)	1979-01-17
CH587225A5 (de)	1977-04-29
DE2316727C3 (de)	1979-02-22
CA1017755A (en)	1977-09-20
ZA732119B (en)	1974-01-30
ES413316A1 (es)	1976-06-01
BR7302430D0 (pt)	1974-02-07
IE38302B1 (en)	1978-02-15
ES439803A1 (es)	1977-04-16
SU533336A3 (ru)	1976-10-25
SE384853B (sv)	1976-05-24
NL7304606A (de)	1973-10-08
US3996382A (en)	1976-12-07
NO139167B (no)	1978-10-09
JPS5924971B2 (ja)	1984-06-13
CH587224A5 (de)	1977-04-29
FI63741B (fi)	1983-04-29
JPS4913129A (de)	1974-02-05
FR2179069B1 (de)	1976-04-09

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