DD151165A5 - Verfahren zur herstellung von neuen aminopropanol-derivaten - Google Patents

Verfahren zur herstellung von neuen aminopropanol-derivaten Download PDF

Info

Publication number: DD151165A5
Authority: DD; German Democratic Republic
Prior art keywords: general formula; hydrogen; compound; hydroxy; propoxy
Prior art date: 1979-05-31

Application number

DD80221448A

Other languages

German (de)

English (en)

Inventor

Carl H Ross

Wolfgang Kampe

Wolfgang Bartsch

Gisbert Sponer

Egon Roesch

Original Assignee

Boehringer Mannheim Gmbh

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.)

1979-05-31

Filing date

1980-05-29

Publication date

1981-10-08

1980-05-29 Application filed by Boehringer Mannheim Gmbh filed Critical Boehringer Mannheim Gmbh

1981-10-08 Publication of DD151165A5 publication Critical patent/DD151165A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 20
MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract description 10
238000002360 preparation method Methods 0.000 title claims abstract description 10
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 24
239000001257 hydrogen Substances 0.000 claims abstract description 23
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
150000003839 salts Chemical class 0.000 claims abstract description 13
125000000217 alkyl group Chemical group 0.000 claims abstract description 12
150000002431 hydrogen Chemical class 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
-1 alkylene radical Chemical class 0.000 claims description 54
150000001875 compounds Chemical class 0.000 claims description 45
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000003254 radicals Chemical class 0.000 claims description 9
150000002367 halogens Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000002252 acyl group Chemical group 0.000 claims description 7
125000003545 alkoxy group Chemical group 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 4
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000004442 acylamino group Chemical group 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000001188 haloalkyl group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
229910052727 yttrium Inorganic materials 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
239000000126 substance Substances 0.000 abstract description 7
239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
101100072620 Streptomyces griseus ind2 gene Proteins 0.000 abstract 1
125000003282 alkyl amino group Chemical group 0.000 abstract 1
230000000903 blocking effect Effects 0.000 abstract 1
230000001077 hypotensive effect Effects 0.000 abstract 1
125000003107 substituted aryl group Chemical group 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 93
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 14
239000002253 acid Substances 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-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
239000002904 solvent Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
MQTYQCAVOMQEFJ-UHFFFAOYSA-N benzene;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC=CC=C1 MQTYQCAVOMQEFJ-UHFFFAOYSA-N 0.000 description 4
239000013078 crystal Substances 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
239000000243 solution Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
229910052801 chlorine Inorganic materials 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
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
LZLSBXOVTMIABI-UHFFFAOYSA-N 1h-quinoxalin-2-one;hydrochloride Chemical compound Cl.C1=CC=C2NC(=O)C=NC2=C1 LZLSBXOVTMIABI-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
BMIMNRPAEPIYDN-UHFFFAOYSA-N 3-methyl-2-quinoxalinol Chemical compound C1=CC=C2N=C(O)C(C)=NC2=C1 BMIMNRPAEPIYDN-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
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 2
241001465754 Metazoa Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
235000004279 alanine Nutrition 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229920006158 high molecular weight polymer Polymers 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
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 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000000746 purification Methods 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
238000011282 treatment Methods 0.000 description 2
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
XLHORNMWQFLFAF-UHFFFAOYSA-N 2-(2-aminoethoxy)phenol Chemical compound NCCOC1=CC=CC=C1O XLHORNMWQFLFAF-UHFFFAOYSA-N 0.000 description 1
125000003816 2-hydroxybenzoyl group Chemical group OC1=C(C(=O)*)C=CC=C1 0.000 description 1
DPJCXCZTLWNFOH-UHFFFAOYSA-N 2-nitroaniline Chemical class NC1=CC=CC=C1[N+]([O-])=O DPJCXCZTLWNFOH-UHFFFAOYSA-N 0.000 description 1
IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
DZBGIZOIMSCJLV-UHFFFAOYSA-N 3-ethyl-1h-quinoxalin-2-one Chemical compound C1=CC=C2N=C(O)C(CC)=NC2=C1 DZBGIZOIMSCJLV-UHFFFAOYSA-N 0.000 description 1
VPWAPWFUOOPTEO-UHFFFAOYSA-N 8-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methyl-1h-quinoxalin-2-one;hydrochloride Chemical compound Cl.C1=CC(OCC(O)CNC(C)(C)C)=C2NC(=O)C(C)=NC2=C1 VPWAPWFUOOPTEO-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
229920000945 Amylopectin Polymers 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
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 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000206672 Gelidium Species 0.000 description 1
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 1
KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
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 1
KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
235000010419 agar Nutrition 0.000 description 1
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
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
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
102000016959 beta-3 Adrenergic Receptors Human genes 0.000 description 1
108010014502 beta-3 Adrenergic Receptors Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000006309 butyl amino group Chemical group 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
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239000008139 complexing agent Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
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201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
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239000000975 dye Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
229910021485 fumed silica Inorganic materials 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
235000015243 ice cream Nutrition 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000004987 o-phenylenediamines Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 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
FFRYUAVNPBUEIC-UHFFFAOYSA-N quinoxalin-2-ol Chemical compound C1=CC=CC2=NC(O)=CN=C21 FFRYUAVNPBUEIC-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
238000004513 sizing Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000002130 sulfonic acid ester group Chemical group 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
239000004474 valine Substances 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
- C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
- C07D241/40—Benzopyrazines
- C07D241/44—Benzopyrazines with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (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)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Electroluminescent Light Sources (AREA)
Cosmetics (AREA)
Photoreceptors In Electrophotography (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

DD80221448A 1979-05-31 1980-05-29 Verfahren zur herstellung von neuen aminopropanol-derivaten DD151165A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19792922084 DE2922084A1 (de)	1979-05-31	1979-05-31	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD151165A5 true DD151165A5 (de)	1981-10-08

Family

ID=6072095

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80221448A DD151165A5 (de)	1979-05-31	1980-05-29	Verfahren zur herstellung von neuen aminopropanol-derivaten

Country Status (11)

Country	Link
US (1)	US4438116A (fr)
EP (1)	EP0019918B1 (fr)
JP (1)	JPS55162783A (fr)
AT (1)	ATE4595T1 (fr)
AU (1)	AU531232B2 (fr)
CA (1)	CA1145338A (fr)
DD (1)	DD151165A5 (fr)
DE (2)	DE2922084A1 (fr)
ES (1)	ES8101054A1 (fr)
FI (1)	FI801689A7 (fr)
ZA (1)	ZA803243B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH0276860A (ja) *	1987-10-05	1990-03-16	Toyo Jozo Co Ltd	６−置換アルコキシ−２−オキソ−１，２−ジヒドロキノキサリン誘導体
JPH09502166A (ja) *	1993-07-31	1997-03-04	スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー	アドレナリン受容体作動薬活性を有する２−ベンゾヘテロシクリルオキシまたはチオプロパノールアミン誘導体

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT242150B (de) *	1963-07-10	1965-08-25	Donau Pharmazie Gmbh	Verfahren zur Herstellung von neuen, substituierten Dihydrochinoxalonen-(2) sowie von deren Salzen und quaternären Ammoniumverbindungen
US3366628A (en) *	1966-06-23	1968-01-30	American Home Prod	1, 2-dihydro-1-polyhydroxyalkyl-2-quinoxalinones
DE1670919A1 (de) *	1967-09-09	1971-04-08	Bayer Ag	Verfahren zur Herstellung neuartiger polycyclischer,heterocyclischer Verbindungen
US3635971A (en) *	1970-06-18	1972-01-18	Abbott Lab	3 (3 4-dihydro-3-oxo-2-quinoxalinyl) propionamides
CH624395A5 (fr)	1976-01-08	1981-07-31	Ciba Geigy Ag
US4146630A (en) *	1976-11-12	1979-03-27	Boehringer Mannheim Gmbh	Blood pressure lowering and adrenergic β-receptor inhibiting 3-(4-phenoxymethylpiperidino)-propyl-phenyl ethers

1979
- 1979-05-31 DE DE19792922084 patent/DE2922084A1/de not_active Withdrawn
1980
- 1980-05-16 CA CA000352092A patent/CA1145338A/fr not_active Expired
- 1980-05-26 FI FI801689A patent/FI801689A7/fi not_active Application Discontinuation
- 1980-05-27 AU AU58786/80A patent/AU531232B2/en not_active Ceased
- 1980-05-28 ES ES491914A patent/ES8101054A1/es not_active Expired
- 1980-05-29 DD DD80221448A patent/DD151165A5/de unknown
- 1980-05-29 EP EP80103001A patent/EP0019918B1/fr not_active Expired
- 1980-05-29 AT AT80103001T patent/ATE4595T1/de not_active IP Right Cessation
- 1980-05-29 DE DE8080103001T patent/DE3064744D1/de not_active Expired
- 1980-05-30 ZA ZA00803243A patent/ZA803243B/xx unknown
- 1980-05-30 JP JP7164680A patent/JPS55162783A/ja active Pending
1981
- 1981-09-16 US US06/302,894 patent/US4438116A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
ES491914A0 (es)	1980-12-16
EP0019918A1 (fr)	1980-12-10
JPS55162783A (en)	1980-12-18
ATE4595T1 (de)	1983-09-15
CA1145338A (fr)	1983-04-26
EP0019918B1 (fr)	1983-09-07
AU531232B2 (en)	1983-08-18
ZA803243B (en)	1981-06-24
AU5878680A (en)	1980-12-04
FI801689A7 (fi)	1981-01-01
ES8101054A1 (es)	1980-12-16
DE2922084A1 (de)	1980-12-11
US4438116A (en)	1984-03-20
DE3064744D1 (en)	1983-10-13

Publication	Publication Date	Title
DE69722858T2 (de)	2004-05-13	Intimale verdickungsinhibitoren
DE69107215T2 (de)	1995-05-24	(2-imidazolin-2-ylamino)chinoxalinderivate und methoden in ihrer anwendung.
EP0047923B1 (fr)	1984-05-09	Dérivés de l'isoquinoléine, leurs procédés de préparation et compositions pharmaceutiques les contenant
DD159071A5 (de)	1983-02-16	Verfahren zur darstellung von pyridoxinderivaten und ihre verwendung in therapeutica
DE3114239C2 (de)	1986-04-03	N&uarr;4&uarr;-Carbamoylpiperazinpropanolderivate, Verfahren zu ihrer Herstellung und pharmazeutisches Mittel
DD201305A5 (de)	1983-07-13	Verfahren zur herstellung von in 7-stellung substituierten benzopyranen
DE69317399T2 (de)	1998-07-02	Aminocycloalkanobenzodioxole als beta-3 selektive adrenergische Wirkstoffe
EP1345902A1 (fr)	2003-09-24	Derives heterocyclo-norbonylamino substitues, leur procede de production, leur utilisation comme medicament ou agent de diagnostic et medicament les contenant
DE3784835T2 (de)	1993-06-24	Chinoxalinon-derivate.
EP0051077A1 (fr)	1982-05-12	Acides cétocarboxyliques substitués, procédés pour leur préparation, leur utilisation et médicaments les contenant
EP0014928A1 (fr)	1980-09-03	Dérivés de pipéridinopropyl, procédé pour leur préparation et médicaments contenant ces composés
DD271517A5 (de)	1989-09-06	Verfahren zur herstellung von neuen naphthylderivaten
EP0515940B1 (fr)	1996-07-17	2-Amino-5-cyano-1,4-dihydropyridines, procédé pour leur préparation et leur utilisation en tant que médicaments
DE102005052101A1 (de)	2007-05-03	Neue Beta-Agonisten, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel
DD151165A5 (de)	1981-10-08	Verfahren zur herstellung von neuen aminopropanol-derivaten
EP0214437B1 (fr)	1990-09-12	Préparation de dérivés de la 1,4-dihydropyridine utilisant de nouveaux intermédiares
DE3874465T2 (de)	1993-02-25	1,2,3,4-tetrahydroisochonoline als antiarrhythmische mittel.
EP0239667B1 (fr)	1991-05-02	Esters de l'acide bêta-carboline-3-carboxylique substitués en position 5 ou 6
DE3520104A1 (de)	1985-12-12	Naphthoxazine, ihre herstellung und verwendung
DE3423003A1 (de)	1986-01-02	Benzo(c)(1,8)naphthyridine, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen
DE2942065A1 (de)	1980-05-08	Neue 1,6-naphthyridinderivate, verfahren zu ihrer herstellung sowie mittel gegen schwindel und zur verbesserung der zerebralen zirkulation, die diese derivate enthalten
DE3030047A1 (de)	1982-03-11	Neue aminopropanol-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3048318A1 (de)	1982-07-22	4-alkoxyalkyl substituierte (beta)-carbolin-3-carbonsaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DE19548708A1 (de)	1997-06-26	Cyclische Sulfone
DE2551235A1 (de)	1976-05-20	Aryloxyalkylpiperidine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel