CH535739A - Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen - Google Patents

Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen

Info

Publication number: CH535739A
Authority: CH; Switzerland
Prior art keywords: dihydroxyphenyl; propanol; amino; compounds; formula
Prior art date: 1970-09-30

Application number

CH1445970A

Other languages

German (de)

English (en)

Inventor

Ebnoether Anton

Hasspacher Klaus

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.)

1970-09-30

Filing date

1970-09-30

Publication date

1973-04-15

1970-09-30 Application filed by Sandoz Ag filed Critical Sandoz Ag

1970-09-30 Priority to CH1445970A priority Critical patent/CH535739A/de

1971-06-29 Priority to CH951371A priority patent/CH540881A/de

1971-09-21 Priority to NL7112938A priority patent/NL7112938A/xx

1971-09-24 Priority to US00183633A priority patent/US3804899A/en

1971-09-27 Priority to GB4481071A priority patent/GB1359871A/en

1971-09-28 Priority to HUSA2250A priority patent/HU162651B/hu

1971-09-28 Priority to BE773204A priority patent/BE773204A/xx

1971-09-28 Priority to ES395494A priority patent/ES395494A1/es

1971-09-28 Priority to CS388071A priority patent/CS158713B2/cs

1971-09-29 Priority to FR7134986A priority patent/FR2108100B1/fr

1971-09-29 Priority to DE19712148551 priority patent/DE2148551A1/de

1971-09-29 Priority to AU34036/71A priority patent/AU3403671A/en

1971-09-29 Priority to DD158025A priority patent/DD99159A5/xx

1973-04-15 Publication of CH535739A publication Critical patent/CH535739A/de

Links

PRMGRTGQYYZJCJ-UHFFFAOYSA-N 4-(1-amino-3-hydroxypropan-2-yl)benzene-1,2-diol Chemical class NCC(CO)C1=CC=C(O)C(O)=C1 PRMGRTGQYYZJCJ-UHFFFAOYSA-N 0.000 title description 2
229940124630 bronchodilator Drugs 0.000 title description 2
239000000168 bronchodilator agent Substances 0.000 title 1
-1 3,4-methylene Chemical group 0.000 claims abstract description 34
238000000034 method Methods 0.000 claims abstract description 33
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 39
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
239000012280 lithium aluminium hydride Substances 0.000 abstract description 4
241000790917 Dioxys <bee> Species 0.000 abstract 1
229910010084 LiAlH4 Inorganic materials 0.000 abstract 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
150000002148 esters Chemical class 0.000 abstract 1
150000002170 ethers Chemical class 0.000 abstract 1
YBATZPPHUXODLM-UHFFFAOYSA-N ethyl 2-(3,4-dimethoxyphenyl)prop-2-enoate Chemical compound CCOC(=O)C(=C)C1=CC=C(OC)C(OC)=C1 YBATZPPHUXODLM-UHFFFAOYSA-N 0.000 abstract 1
230000007062 hydrolysis Effects 0.000 abstract 1
238000006460 hydrolysis reaction Methods 0.000 abstract 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000003054 catalyst Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
239000000203 mixture Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
208000009079 Bronchial Spasm Diseases 0.000 description 3
208000014181 Bronchial disease Diseases 0.000 description 3
206010006482 Bronchospasm Diseases 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 2
IADQVXRMSNIUEL-UHFFFAOYSA-N 3,4-dihydroxyphenylacetaldehyde Chemical compound OC1=CC=C(CC=O)C=C1O IADQVXRMSNIUEL-UHFFFAOYSA-N 0.000 description 2
LLTMJMRLIPCICJ-UHFFFAOYSA-N 3-amino-2-(3,4-dimethoxyphenyl)propan-1-ol Chemical compound COC1=CC=C(C(CN)CO)C=C1OC LLTMJMRLIPCICJ-UHFFFAOYSA-N 0.000 description 2
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 2
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
230000001813 broncholytic effect Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
FXHGMKSSBGDXIY-UHFFFAOYSA-N heptanal Chemical compound CCCCCCC=O FXHGMKSSBGDXIY-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229910052763 palladium Inorganic materials 0.000 description 2
DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000003756 stirring Methods 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
IPRPPFIAVHPVJH-UHFFFAOYSA-N (4-hydroxyphenyl)acetaldehyde Chemical compound OC1=CC=C(CC=O)C=C1 IPRPPFIAVHPVJH-UHFFFAOYSA-N 0.000 description 1
OIIOPWHTJZYKIL-PMACEKPBSA-N (5S)-5-[[[5-[2-chloro-3-[2-chloro-3-[6-methoxy-5-[[[(2S)-5-oxopyrrolidin-2-yl]methylamino]methyl]pyrazin-2-yl]phenyl]phenyl]-3-methoxypyrazin-2-yl]methylamino]methyl]pyrrolidin-2-one Chemical compound C1(=C(N=C(C2=C(C(C3=CC=CC(=C3Cl)C3=NC(OC)=C(N=C3)CNC[C@H]3NC(=O)CC3)=CC=C2)Cl)C=N1)OC)CNC[C@H]1NC(=O)CC1 OIIOPWHTJZYKIL-PMACEKPBSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HLLGFGBLKOIZOM-UHFFFAOYSA-N 2,2-diphenylacetaldehyde Chemical compound C=1C=CC=CC=1C(C=O)C1=CC=CC=C1 HLLGFGBLKOIZOM-UHFFFAOYSA-N 0.000 description 1
VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
NRIVMXXOUOBRAG-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1 NRIVMXXOUOBRAG-UHFFFAOYSA-N 0.000 description 1
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 1
BYNJCCMGUBTMJZ-UHFFFAOYSA-N 3,3-diphenylpropanal Chemical compound C=1C=CC=CC=1C(CC=O)C1=CC=CC=C1 BYNJCCMGUBTMJZ-UHFFFAOYSA-N 0.000 description 1
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-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
REEQXZCFSBLNDH-UHFFFAOYSA-N 4-Hydroxydihydrocinnamaldehyde Chemical compound OC1=CC=C(CCC=O)C=C1 REEQXZCFSBLNDH-UHFFFAOYSA-N 0.000 description 1
JXIFWXDHQGBCPD-UHFFFAOYSA-N 4-[1-hydroxy-3-(propan-2-ylamino)propan-2-yl]benzene-1,2-diol Chemical compound CC(C)NCC(CO)C1=CC=C(O)C(O)=C1 JXIFWXDHQGBCPD-UHFFFAOYSA-N 0.000 description 1
NHFRGTVSKOPUBK-UHFFFAOYSA-N 4-phenylbutanal Chemical compound O=CCCCC1=CC=CC=C1 NHFRGTVSKOPUBK-UHFFFAOYSA-N 0.000 description 1
241000700198 Cavia Species 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
229960004373 acetylcholine Drugs 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
239000002585 base Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000005661 deetherification reaction Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
125000001033 ether group Chemical group 0.000 description 1
YHESBDUINPOZFB-UHFFFAOYSA-N ethyl 2-cyano-2-(3,4-dimethoxyphenyl)acetate Chemical compound CCOC(=O)C(C#N)C1=CC=C(OC)C(OC)=C1 YHESBDUINPOZFB-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
229960001340 histamine Drugs 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
229940071870 hydroiodic acid Drugs 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
150000004694 iodide salts Chemical class 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
229940100595 phenylacetaldehyde Drugs 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
230000007017 scission Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH1445970A 1970-09-30 1970-09-30 Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen CH535739A (de)

Priority Applications (13)

Application Number	Priority Date	Filing Date	Title
CH1445970A CH535739A (de)	1970-09-30	1970-09-30	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen
CH951371A CH540881A (de)	1970-09-30	1971-06-29	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen
NL7112938A NL7112938A (cs)	1970-09-30	1971-09-21
US00183633A US3804899A (en)	1970-09-30	1971-09-24	3-alkylamino-2-(3,4-dihydroxyphenyl)propanols and the salts thereof
GB4481071A GB1359871A (en)	1970-09-30	1971-09-27	Amino propanol
HUSA2250A HU162651B (cs)	1970-09-30	1971-09-28
BE773204A BE773204A (fr)	1970-09-30	1971-09-28	Nouveaux derives du 3-amino-2 (3,4-dihydroxyphenyl) propanol, leur preparation et medicaments contenants ces derives
ES395494A ES395494A1 (es)	1970-09-30	1971-09-28	Procedimiento para la obtencion de derivados de aminopropa-nol.
CS388071A CS158713B2 (cs)	1970-09-30	1971-09-28
FR7134986A FR2108100B1 (cs)	1970-09-30	1971-09-29
DE19712148551 DE2148551A1 (de)	1970-09-30	1971-09-29	Verfahren zur Herstellung neuer carbocyclischer Verbindungen
AU34036/71A AU3403671A (en)	1970-09-30	1971-09-29	Organic compounds
DD158025A DD99159A5 (cs)	1970-09-30	1971-09-29

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1445970A CH535739A (de)	1970-09-30	1970-09-30	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen

Publications (1)

Publication Number	Publication Date
CH535739A true CH535739A (de)	1973-04-15

Family

ID=4400992

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1445970A CH535739A (de)	1970-09-30	1970-09-30	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen

Country Status (2)

Country	Link
CH (1)	CH535739A (cs)
CS (1)	CS158713B2 (cs)

1970
- 1970-09-30 CH CH1445970A patent/CH535739A/de not_active IP Right Cessation
1971
- 1971-09-28 CS CS388071A patent/CS158713B2/cs unknown

Also Published As

Publication number	Publication date
CS158713B2 (cs)	1974-11-25

Legal Events

Date	Code	Title	Description
1976-04-30	PL	Patent ceased

Publication	Publication Date	Title
CH635841A5 (de)	1983-04-29	Spiroaminderivate, verfahren zu ihrer herstellung und diese enthaltende arzneimittel.
DE2148551A1 (de)	1972-05-10	Verfahren zur Herstellung neuer carbocyclischer Verbindungen
CH550768A (de)	1974-06-28	Verfahren zur herstellung neuer bis((4-hydroxy-3-hydroxymethylphenyl)aethanol)diamin-derivate.
DE2401374A1 (de)	1974-07-18	Tetrahydronaphthyloxyaminderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate
EP0000395B1 (de)	1981-01-07	2-Piperazinotetraline, ihre Herstellung und Verwendung als Arzneimittel
CH535739A (de)	1973-04-15	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen
EP0082461A2 (de)	1983-06-29	Substituierte Phenoxyalkanolamine und Phenoxyalkanol-cycloalkylamine, Verfahren zu ihrer Herstellung, diese Verbindungen enthaltende pharmazeutische Zubereitungen und Zwischenprodukte
DE2359773C2 (cs)	1990-06-28
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CH534658A (de)	1973-03-15	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen
DE2351281A1 (de)	1975-04-24	Neue amino-phenyl-aethanolamine und deren oxazolidine
DE2241027A1 (de)	1973-03-01	Verfahren zur herstellung neuer heterocyclischer verbindungen
CH540881A (de)	1973-08-31	Verfahren zur Herstellung neuer Dihydroxyphenylverbindungen
CH553154A (de)	1974-08-30	Verfahren zur herstellung neuer dihydroxyphenylverbindungen.
DE2061864B2 (de)	1979-06-28	Acylderivate von substituierten Bis-Arylalkylaminen
DE2230539A1 (de)	1973-01-11	Verfahren zur herstellung neuer carbocyclischer verbindungen
US4218472A (en)	1980-08-19	Geminally disubstituted indene derivatives
CH546737A (de)	1974-03-15	Verfahren zur herstellung neuer bis ((3,4-dihydroxyphenyl)-propanol)diamin-derivate.
AT257605B (de)	1967-10-10	Verfahren zur Herstellung von neuen 4-substituierten Pyridinverbindungen
CH545763A (en)	1974-02-15	N,n'-bis-(3-hydroxy 2-(3,4-dihydroxyphenyl) 1-propyl) - diamines - useful as bronchospasmolytics
AT252233B (de)	1967-02-10	Verfahren zur Herstellung von neuen basisch substituierten Pseudoindolen
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CH511840A (de)	1971-08-31	Verfahren zur Herstellung von neuen Indolderivaten
DE1618386C3 (de)	1976-04-29	Basisch substituierte Cyclopentenylphenoläther und Verfahren zu ihrer Herstellung
DE1141995B (de)	1963-01-03	Verfahren zur Herstellung von Derivaten des 4-Oxycumarins