CH597236A5 - 1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols - Google Patents

1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols

Info

Publication number: CH597236A5
Authority: CH; Switzerland
Prior art keywords: carbon atoms; formula; tert; compounds; butyl
Prior art date: 1974-08-27

Application number

CH1169074A

Other languages

German (de)

English (en)

Inventor

Erik Wiskott

Franz Troxler

Original Assignee

Sandoz 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.)

1974-08-27

Filing date

1974-08-27

Publication date

1978-03-31

1974-08-27 Application filed by Sandoz Ag filed Critical Sandoz Ag

1974-08-27 Priority to CH1169074A priority Critical patent/CH597236A5/de

1975-08-18 Priority to DK372475A priority patent/DK372475A/da

1975-08-18 Priority to DE19752536675 priority patent/DE2536675A1/de

1975-08-18 Priority to FI752331A priority patent/FI752331A7/fi

1975-08-19 Priority to NO752881A priority patent/NO752881L/no

1975-08-19 Priority to SE7509270A priority patent/SE7509270L/xx

1975-08-22 Priority to GB34917/75A priority patent/GB1509256A/en

1975-08-22 Priority to NL7509943A priority patent/NL7509943A/xx

1975-08-22 Priority to FR7525983A priority patent/FR2282886A1/fr

1975-08-25 Priority to ES440430A priority patent/ES440430A1/es

1975-08-25 Priority to BE159439A priority patent/BE832717A/fr

1975-08-26 Priority to DD188030A priority patent/DD121945A5/xx

1975-08-26 Priority to AU84277/75A priority patent/AU8427775A/en

1975-08-26 Priority to JP50102626A priority patent/JPS5148693A/ja

1975-08-26 Priority to IL47991A priority patent/IL47991A0/xx

1975-08-27 Priority to ZA755479A priority patent/ZA755479B/xx

1978-03-31 Publication of CH597236A5 publication Critical patent/CH597236A5/de

Links

RFECPMXPPTXUEU-UHFFFAOYSA-N 1-amino-3-thieno[3,2-c]pyridin-4-yloxypropan-2-ol Chemical class NCC(COC1=NC=CC2=C1C=CS2)O RFECPMXPPTXUEU-UHFFFAOYSA-N 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims description 36
125000004432 carbon atom Chemical group C* 0.000 claims description 25
239000002253 acid Substances 0.000 claims description 14
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
-1 1-tert-butylamino-3- (2-methyl-4-thieno [3, 2-c] pyridinyl oxy) -2-propanol Chemical compound 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 8
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical class N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims description 2
201000005577 familial hyperlipidemia Diseases 0.000 abstract 1
WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical compound N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 abstract 1
201000001421 hyperglycemia Diseases 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
239000011737 fluorine Substances 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
SQYMXIHEANTFFY-FBLFFUNLSA-N (2R)-3-tert-butyl-5-[(2-methylthieno[3,2-c]pyridin-4-yl)oxymethyl]-2-phenyl-1,3-oxazolidine Chemical compound C1([C@@H]2N(CC(O2)COC2=C3C=C(SC3=CC=N2)C)C(C)(C)C)=CC=CC=C1 SQYMXIHEANTFFY-FBLFFUNLSA-N 0.000 description 2
JWBMVCAZXJMSOX-LURJTMIESA-N (2s)-3-(tert-butylamino)propane-1,2-diol Chemical compound CC(C)(C)NC[C@H](O)CO JWBMVCAZXJMSOX-LURJTMIESA-N 0.000 description 2
JMWVYCBWLOCZAB-UHFFFAOYSA-N 4-chloro-2-methylthieno[3,2-c]pyridine Chemical compound N1=CC=C2SC(C)=CC2=C1Cl JMWVYCBWLOCZAB-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
MNQZXJOMYWMBOU-VKHMYHEASA-N D-glyceraldehyde Chemical compound OC[C@@H](O)C=O MNQZXJOMYWMBOU-VKHMYHEASA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
MNQZXJOMYWMBOU-GSVOUGTGSA-N L-(-)-glyceraldehyde Chemical compound OC[C@H](O)C=O MNQZXJOMYWMBOU-GSVOUGTGSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000011282 treatment Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
JUKXEIULFQWJAK-NSHDSACASA-N (2S)-1-(tert-butylamino)-3-(2-methylthieno[3,2-c]pyridin-4-yl)oxypropan-2-ol Chemical compound N1=CC=C2SC(C)=CC2=C1OC[C@@H](O)CNC(C)(C)C JUKXEIULFQWJAK-NSHDSACASA-N 0.000 description 1
JERBWURCWWHQBK-UHFFFAOYSA-N (3-tert-butyl-2-phenyl-1,3-oxazolidin-5-yl)methanol Chemical compound CC(C)(C)N1CC(CO)OC1C1=CC=CC=C1 JERBWURCWWHQBK-UHFFFAOYSA-N 0.000 description 1
125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
CZZYGMSEVJJFRE-UHFFFAOYSA-N 2-methyl-5h-thieno[3,2-c]pyridin-4-one Chemical compound N1=CC=C2SC(C)=CC2=C1O CZZYGMSEVJJFRE-UHFFFAOYSA-N 0.000 description 1
SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
VAUMDUIUEPIGHM-UHFFFAOYSA-N 5-Methyl-2-thiophenecarboxaldehyde Chemical compound CC1=CC=C(C=O)S1 VAUMDUIUEPIGHM-UHFFFAOYSA-N 0.000 description 1
VFTOHJFKIJLYKN-UHFFFAOYSA-N 7-nitro-9h-fluoren-2-ol Chemical group [O-][N+](=O)C1=CC=C2C3=CC=C(O)C=C3CC2=C1 VFTOHJFKIJLYKN-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241000700199 Cavia porcellus Species 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical group OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
IVPUXZWDWVRYTI-UHFFFAOYSA-N S1C(=CC=C1)C(C(=O)N=[N+]=[N-])=C Chemical class S1C(=CC=C1)C(C(=O)N=[N+]=[N-])=C IVPUXZWDWVRYTI-UHFFFAOYSA-N 0.000 description 1
208000001871 Tachycardia Diseases 0.000 description 1
JERBWURCWWHQBK-ZGTCLIOFSA-N [(2r)-3-tert-butyl-2-phenyl-1,3-oxazolidin-5-yl]methanol Chemical compound CC(C)(C)N1CC(CO)O[C@@H]1C1=CC=CC=C1 JERBWURCWWHQBK-ZGTCLIOFSA-N 0.000 description 1
JERBWURCWWHQBK-ABLWVSNPSA-N [(2s)-3-tert-butyl-2-phenyl-1,3-oxazolidin-5-yl]methanol Chemical compound CC(C)(C)N1CC(CO)O[C@H]1C1=CC=CC=C1 JERBWURCWWHQBK-ABLWVSNPSA-N 0.000 description 1
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
210000001789 adipocyte Anatomy 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
206010003119 arrhythmia Diseases 0.000 description 1
238000010009 beating Methods 0.000 description 1
102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
230000031709 bromination Effects 0.000 description 1
238000005893 bromination reaction Methods 0.000 description 1
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000005660 chlorination reaction Methods 0.000 description 1
208000029078 coronary artery disease Diseases 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
201000010063 epididymitis Diseases 0.000 description 1
230000001834 epinephrinelike Effects 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-M fumarate(1-) Chemical compound OC(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-M 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000297 inotrophic effect Effects 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
WARQUFORVQESFF-UHFFFAOYSA-N isocyanatoethene Chemical class C=CN=C=O WARQUFORVQESFF-UHFFFAOYSA-N 0.000 description 1
229940039009 isoproterenol Drugs 0.000 description 1
230000004130 lipolysis Effects 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000002503 metabolic effect Effects 0.000 description 1
230000008986 metabolic interaction Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002917 oxazolidines Chemical class 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
WLMSZVULHUTVRG-UHFFFAOYSA-N prop-2-enoyl azide Chemical compound C=CC(=O)N=[N+]=[N-] WLMSZVULHUTVRG-UHFFFAOYSA-N 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000006794 tachycardia Effects 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002560 therapeutic procedure Methods 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

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D263/06—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by oxygen atoms, attached to ring carbon atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1169074A 1974-08-27 1974-08-27 1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols CH597236A5 (en)

Priority Applications (16)

Application Number	Priority Date	Filing Date	Title
CH1169074A CH597236A5 (en)	1974-08-27	1974-08-27	1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols
DK372475A DK372475A (da)	1974-08-27	1975-08-18	Fremgangsmade til fremsilling af organiske forbindelser
DE19752536675 DE2536675A1 (de)	1974-08-27	1975-08-18	Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung
FI752331A FI752331A7 (fr)	1974-08-27	1975-08-18
NO752881A NO752881L (fr)	1974-08-27	1975-08-19
SE7509270A SE7509270L (sv)	1974-08-27	1975-08-19	Organiska foreningar, deras anvendning och framstellning
GB34917/75A GB1509256A (en)	1974-08-27	1975-08-22	1-amino-3-pyridinyloxy-2-propanol derivatives
NL7509943A NL7509943A (nl)	1974-08-27	1975-08-22	Werkwijze voor het bereiden van een geneesmiddel waarin een gesubstitueerd derivaat van pyrido- thiofeen of pyridofuran is opgenomen, het volgens deze werkwijze verkregen geneesmiddel en werkwijze voor het bereiden van deze actieve verbindingen.
FR7525983A FR2282886A1 (fr)	1974-08-27	1975-08-22	Nouveaux derives de l'aminopropane-2-ol, leur preparation et leur application comme medicaments
ES440430A ES440430A1 (es)	1974-08-27	1975-08-25	Procedimiento para la produccion de derivados de piridina fundidos.
BE159439A BE832717A (fr)	1974-08-27	1975-08-25	Nouveaux procedes de l'amino-propane-2-01, leur preparation et leur application comme medicaments
DD188030A DD121945A5 (fr)	1974-08-27	1975-08-26
AU84277/75A AU8427775A (en)	1974-08-27	1975-08-26	Thieno- and furanopyridines
JP50102626A JPS5148693A (fr)	1974-08-27	1975-08-26
IL47991A IL47991A0 (en)	1974-08-27	1975-08-26	New furopyridines and thienopyridines,their production and pharmaceutical compositions containing them
ZA755479A ZA755479B (en)	1974-08-27	1975-08-27	Improvements in or relating to organic compounds

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1169074A CH597236A5 (en)	1974-08-27	1974-08-27	1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols

Publications (1)

Publication Number	Publication Date
CH597236A5 true CH597236A5 (en)	1978-03-31

Family

ID=4375921

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1169074A CH597236A5 (en)	1974-08-27	1974-08-27	1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols

Country Status (3)

Country	Link
BE (1)	BE832717A (fr)
CH (1)	CH597236A5 (fr)
ZA (1)	ZA755479B (fr)

1974
- 1974-08-27 CH CH1169074A patent/CH597236A5/de not_active IP Right Cessation
1975
- 1975-08-25 BE BE159439A patent/BE832717A/fr unknown
- 1975-08-27 ZA ZA755479A patent/ZA755479B/xx unknown

Also Published As

Publication number	Publication date
BE832717A (fr)	1976-02-25
ZA755479B (en)	1977-04-27

Legal Events

Date	Code	Title	Description
1982-04-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2130393A1 (de)	1971-12-30	Tetrahydronaphthyloxyaminopropanole,Verfahren zu ihrer Herstellung sowie pharmazeutische Praeparate,welche diese Verbindungen als Wirkstoff enthalten
DE2447756A1 (de)	1975-04-10	Verfahren zur herstellung neuer heterocyclischer verbindungen
DD272648A5 (de)	1989-10-18	Chromon-derivate
EP0150015B1 (fr)	1987-06-16	Amides d'acides carboxyliques de norbornane et norbornène, et procédé de leur préparation
DE2128375C3 (de)	1982-05-13	Basische substituierte Alkylidenamino-oxyalkyl-carbonsäureester, deren Säureadditionssalze, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE1493912A1 (de)	1969-07-10	Naphthylessigsaeuren und Verfahren zu deren Herstellung
DE2702092A1 (de)	1977-07-28	Chroman-derivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
CH542835A (de)	1973-10-15	Verfahren zur Herstellung von neuen Aryloxy- und Arylthioalkansäuren und ihren Salzen
CH597236A5 (en)	1978-03-31	1-Amino-3-(thieno (3,2-c)pyridine-4-yl-oxy)-2-propanols
DE1518042C3 (de)	1975-04-10	1,4-Benzodioxanderivate und Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
DE2458911A1 (de)	1975-06-26	11,12-secoprostaglandine und verfahren zu ihrer herstellung
DD150060A5 (de)	1981-08-12	Verfahren zur herstellung von neuen phenthiazin-derivaten
DE2611148A1 (de)	1976-10-14	Organische verbindungen, ihre verwendung und herstellung
DE2736106A1 (de)	1978-02-23	Neuartige aryloxy-1-amino-3-propanole-2, verfahren zum herstellen und therapeutische anwendung derselben
DE2331081A1 (de)	1975-01-23	Neue cyclopentanderivate und verfahren zu ihrer herstellung
CH622796A5 (en)	1981-04-30	Process for the preparation of novel thieno[3,2-c]pyridine derivatives
CH461489A (de)	1968-08-31	Verfahren zur Herstellung von neuen Oxazolderivaten
CH619954A5 (en)	1980-10-31	Process for the preparation of novel thieno- or furo[3,2-c]pyridine derivatives
EP0575361B1 (fr)	1996-06-26	Nouveaux nitriles d'acide 1-aryl-4-piperazinyl-cyclohexanocarboxylique, leur preparation et leur utilisation
DD201678A5 (de)	1983-08-03	Verfahren zur herstellung von 1,5-bis-(1,4-benzodioxin-2-yl)-3-azapentan-1,5-diolen, verfahren zu ihrer herstellung, pharmazeutische praeparate enthaltend diese verbindungen, sowie ihre therapeutische verwendung
DE2536675A1 (de)	1976-03-11	Neue 3-(4-thieno-bzw.-furo eckige klammer auf 3,2-c eckige klammer zu pyridinyloxy) -2- propanol-derivate, ihre verwendung und herstellung
AT346844B (de)	1978-11-27	Verfahren zur herstellung von neuen oxazolderivaten
DE2528070A1 (de)	1976-01-08	9-thia-, 9-oxothia- und 9-dioxothia- 11,12-secoprostaglandine
AT336617B (de)	1977-05-10	Verfahren zur herstellung von neuen heterocyclischen verbindungen
AT336556B (de)	1977-05-10	Verfahren zur herstellung von neuen, gegebenenfalls fluorierten n-alkylsulfonyl- (oder -sulfinyl-) -hydroxyazacarbonsauren