DE1543372A1 - Verfahren zur Herstellung von o-substituierten 3,4-Dioxyphenylalkanolaminen - Google Patents
Verfahren zur Herstellung von o-substituierten 3,4-DioxyphenylalkanolaminenInfo
- Publication number
- DE1543372A1 DE1543372A1 DE19661543372 DE1543372A DE1543372A1 DE 1543372 A1 DE1543372 A1 DE 1543372A1 DE 19661543372 DE19661543372 DE 19661543372 DE 1543372 A DE1543372 A DE 1543372A DE 1543372 A1 DE1543372 A1 DE 1543372A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- general formula
- group
- acid
- compounds
- Prior art date
- Legal status (The legal status 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 status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 239000002253 acid Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 150000004678 hydrides Chemical class 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 150000002576 ketones Chemical class 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 230000002829 reductive effect Effects 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- NVIFVTYDZMXWGX-UHFFFAOYSA-N sodium metaborate Chemical compound [Na+].[O-]B=O NVIFVTYDZMXWGX-UHFFFAOYSA-N 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 239000011630 iodine Chemical group 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- XMGMFRIEKMMMSU-UHFFFAOYSA-N phenylmethylbenzene Chemical group C=1C=CC=CC=1[C]C1=CC=CC=C1 XMGMFRIEKMMMSU-UHFFFAOYSA-N 0.000 claims description 2
- 238000007792 addition Methods 0.000 claims 3
- 230000004048 modification Effects 0.000 claims 2
- 238000012986 modification Methods 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- ZINJLDJMHCUBIP-UHFFFAOYSA-N ethametsulfuron-methyl Chemical compound CCOC1=NC(NC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC)=N1 ZINJLDJMHCUBIP-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 238000011287 therapeutic dose Methods 0.000 claims 1
- 238000009423 ventilation Methods 0.000 claims 1
- 239000001993 wax Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- -1 propio- Chemical class 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[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
- 125000006239 protecting group Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- KRQUFUKTQHISJB-YYADALCUSA-N 2-[(E)-N-[2-(4-chlorophenoxy)propoxy]-C-propylcarbonimidoyl]-3-hydroxy-5-(thian-3-yl)cyclohex-2-en-1-one Chemical compound CCC\C(=N/OCC(C)OC1=CC=C(Cl)C=C1)C1=C(O)CC(CC1=O)C1CCCSC1 KRQUFUKTQHISJB-YYADALCUSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 101100027969 Caenorhabditis elegans old-1 gene Proteins 0.000 description 1
- 201000008009 Early infantile epileptic encephalopathy Diseases 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
- 241001465754 Metazoa Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000248770 Salea Species 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
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 125000005362 aryl sulfone group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 208000013257 developmental and epileptic encephalopathy Diseases 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Chemical compound CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000006320 pegylation Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0089417 | 1966-10-18 | ||
| DEB0089476 | 1966-10-20 | ||
| DEB0090062 | 1966-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1543372A1 true DE1543372A1 (de) | 1971-04-01 |
Family
ID=27209389
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19661543372 Pending DE1543372A1 (de) | 1966-10-18 | 1966-10-18 | Verfahren zur Herstellung von o-substituierten 3,4-Dioxyphenylalkanolaminen |
| DE1543374A Expired DE1543374C3 (de) | 1966-10-18 | 1966-10-20 | 3,4 Dihydroxyphenylalkanolamine und ihre Saureadditionssalze, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1543374A Expired DE1543374C3 (de) | 1966-10-18 | 1966-10-20 | 3,4 Dihydroxyphenylalkanolamine und ihre Saureadditionssalze, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitungen |
Country Status (11)
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969410A (en) * | 1972-01-12 | 1976-07-13 | Boehringer Ingelheim Gmbh | 1-(2'-Alkyl-3',4'-dihydroxy-phenyl)-2-(phenylalkyl-amino)-alkanols-(1) and salts thereof |
| US4042713A (en) * | 1966-10-18 | 1977-08-16 | Boehringer Ingelheim Gmbh | Pharmaceutical compositions containing a 1-(2-alkyl-3,4-dihydroxy-phenyl)-2-(phenylalkyl-amino)-alkanol-(1) and method of use |
| US4138581A (en) * | 1969-04-01 | 1979-02-06 | Sterling Drugs Inc. | 3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols |
| US4336400A (en) * | 1969-04-01 | 1982-06-22 | Sterling Drug Inc. | 3-(Hydroxy or hydroxymethyl)-4-hydroxy-alpha(aminomethyl)benzyl alcohols and methods of use |
| DE1962497C3 (de) * | 1969-12-12 | 1979-09-20 | C.H. Boehringer Sohn, 6507 Ingelheim | Naphthylalkyl- a -hydroxyphenäthyl-amine, ihre Herstellung und diese enthaltende Arzneimittel |
| US4147799A (en) * | 1971-06-24 | 1979-04-03 | Kyowa Hakko Kogyo Co., Ltd. | Process for reducing blood pressure and blocking β-adrenergic receptor |
| US3868461A (en) * | 1972-11-22 | 1975-02-25 | Interx Research Corp | Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof |
| US3908017A (en) * | 1973-04-26 | 1975-09-23 | Interx Research Corp | Sympathomimetic compositions containing an ester of -3-hydroxy-{60 -{8 (methylamino)methyl{8 benzyl alcohol and methods of use |
| US4046913A (en) * | 1973-08-18 | 1977-09-06 | Boehringer Ingelheim Gmbh | 1-(M-alkanoyloxy-phenyl)-1-hydroxy-2-(N-lower alkyl-amino)-ethanes and salts thereof |
| US4192805A (en) * | 1975-11-27 | 1980-03-11 | Nicholas International Limited | Process of preparing amino ethanols |
| US4287212A (en) * | 1976-04-30 | 1981-09-01 | American Hoechst Corporation | 2-Aryl-1,2-dialkylcycloalkylamines |
| US4115585A (en) * | 1976-05-17 | 1978-09-19 | Instituto Luso Farmaco D'italia S.R.L. | Esters of 1-(p-hydroxyphenyl)-2-(1'-methyl-2'-phenoxyethylamino)-1-propanol |
| US4094983A (en) * | 1977-01-17 | 1978-06-13 | Interx Research Corporation | Method for reducing intraocular pressure in warm-blooded animals |
| US4275074A (en) * | 1979-03-09 | 1981-06-23 | Graham J. Dobbie | Catecholamine treatment of ocular hypertension |
| US4590210A (en) * | 1979-03-09 | 1986-05-20 | Langham Maurice E | Compositions for treatment of ocular hypertension |
| JPS55124742A (en) * | 1979-03-20 | 1980-09-26 | Kyowa Hakko Kogyo Co Ltd | Novel aminoalcohol derivative |
| JPS6241829Y2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-03-28 | 1987-10-26 | ||
| ATE7689T1 (de) | 1980-07-09 | 1984-06-15 | Aktiebolaget Draco | 1-(dihydroxyphenyl)-2-amino-aethanol-derivate, verfahren und mittel zu ihrer herstellung sowie diese derivate enthaltende mittel. |
| DE3128117A1 (de) * | 1980-07-29 | 1982-03-11 | Yamanouchi Pharmaceutical Co., Ltd., Tokyo | Neue phenyl-aethylaminderivate, verfahren zu ihrer herstellung |
| US4472427A (en) * | 1980-12-23 | 1984-09-18 | Merck & Co., Inc. | (Aralkylamino-2-OR-propoxy)heterocyclic compounds |
| ES502470A0 (es) * | 1981-05-13 | 1982-04-01 | Ferrer Int | Procedimiento de obtencion de nuevos aminoderivados en posi-cion 1, del 1-(3',4'-metilendioxifenil)propan-2-ol |
| US4461914A (en) * | 1983-02-01 | 1984-07-24 | American Cyanamid Company | Method for the preparation of 1-(4'-amino-3',5'-dichlorophenyl)-2-alkyl(or dialkyl)aminoethanols |
| SE8501895L (sv) * | 1984-04-17 | 1985-10-18 | Glaxo Group Ltd | Fenetanolaminforeningar |
| US4699928A (en) * | 1984-07-13 | 1987-10-13 | Merrell Dow Pharmaceuticals Inc. | Fluoroallylamine derivatives |
| US4843160A (en) * | 1984-10-01 | 1989-06-27 | The Dow Chemical Company | Preparation of alpha-aminoalkylphenols |
| US5068432A (en) * | 1988-03-30 | 1991-11-26 | Aldrich Chemical Company, Inc. | Process for producing optically pure 2-phenoxyphenylalkylamines |
| JPH02124884A (ja) * | 1988-07-08 | 1990-05-14 | Zhongguo Yixuekexueyuan Yaowo Yanjiusuo | Ｎ―置換アミド誘導体 |
| DE10246374A1 (de) * | 2002-10-04 | 2004-04-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Betamimetika mit verlängerter Wirkungsdauer, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| US6951888B2 (en) | 2002-10-04 | 2005-10-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Betamimetics with a prolonged duration of activity, processes for preparing them, and their use as pharmaceutical compositions |
| DE10253220A1 (de) * | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Dihydroxy-Methyl-Phenyl-Derivate, Verfahren zu deren Herstellung und deren Verwendung als Arzneimittel |
| CN110743544B (zh) * | 2019-11-07 | 2023-02-24 | 西安凯立新材料股份有限公司 | 一种苯乙酮选择加氢制备α-苯乙醇用钯炭催化剂及其制备方法与应用 |
-
1966
- 1966-10-18 DE DE19661543372 patent/DE1543372A1/de active Pending
- 1966-10-20 DE DE1543374A patent/DE1543374C3/de not_active Expired
-
1967
- 1967-10-14 ES ES346057A patent/ES346057A1/es not_active Expired
- 1967-10-16 US US713265A patent/US3657244A/en not_active Expired - Lifetime
- 1967-10-16 AT AT934967A patent/AT285582B/de not_active IP Right Cessation
- 1967-10-16 CH CH513370A patent/CH507200A/de not_active IP Right Cessation
- 1967-10-16 CH CH452872A patent/CH548365A/xx not_active IP Right Cessation
- 1967-10-16 AT AT1165269A patent/AT288357B/de not_active IP Right Cessation
- 1967-10-16 AT AT1165369A patent/AT288358B/de not_active IP Right Cessation
- 1967-10-16 CH CH513470A patent/CH523219A/de not_active IP Right Cessation
- 1967-10-16 CH CH1442267A patent/CH490323A/de not_active IP Right Cessation
- 1967-10-17 DK DK516167AA patent/DK130070B/da not_active IP Right Cessation
- 1967-10-18 NL NL6714161.A patent/NL158480B/xx not_active IP Right Cessation
- 1967-10-18 SE SE14280/67A patent/SE368196B/xx unknown
- 1967-10-18 GB GB47491/67A patent/GB1204195A/en not_active Expired
- 1967-10-18 BE BE705312D patent/BE705312A/xx not_active IP Right Cessation
- 1967-10-18 SE SE7106612A patent/SE380792B/xx unknown
-
1968
- 1968-01-18 FR FR136547A patent/FR7338M/fr not_active Expired
- 1968-11-30 ES ES360962A patent/ES360962A1/es not_active Expired
- 1968-11-30 ES ES360965A patent/ES360965A1/es not_active Expired
- 1968-11-30 ES ES360963A patent/ES360963A1/es not_active Expired
- 1968-11-30 ES ES360961A patent/ES360961A1/es not_active Expired
- 1968-11-30 ES ES360964A patent/ES360964A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES360964A1 (es) | 1970-10-16 |
| NL158480B (nl) | 1978-11-15 |
| ES360962A1 (es) | 1970-11-16 |
| SE380792B (sv) | 1975-11-17 |
| AT288357B (de) | 1971-03-10 |
| DE1543374B2 (de) | 1973-02-22 |
| CH523219A (de) | 1972-05-31 |
| US3657244A (en) | 1972-04-18 |
| DK130070B (da) | 1974-12-16 |
| DE1543374A1 (de) | 1972-04-20 |
| NL6714161A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-04-19 |
| ES360965A1 (es) | 1970-11-16 |
| CH490323A (de) | 1970-05-15 |
| DK130070C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1975-05-26 |
| DE1543374C3 (de) | 1973-10-04 |
| ES346057A1 (es) | 1969-03-16 |
| ES360963A1 (es) | 1970-11-16 |
| SE368196B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-06-24 |
| CH548365A (de) | 1974-04-30 |
| ES360961A1 (es) | 1970-11-16 |
| GB1204195A (en) | 1970-09-03 |
| FR7338M (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-10-13 |
| BE705312A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1968-04-18 |
| CH507200A (de) | 1971-05-15 |
| AT285582B (de) | 1970-11-10 |
| AT288358B (de) | 1971-03-10 |
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