FI58326C - Foerfarande foer framstaellning av som beta-adrenergiskt stimulerande medel anvaendbara alfa-aminometyl-4-hydroksi-3-metylsulfonyl-metylbensylalkoholer - Google Patents
Foerfarande foer framstaellning av som beta-adrenergiskt stimulerande medel anvaendbara alfa-aminometyl-4-hydroksi-3-metylsulfonyl-metylbensylalkoholer Download PDFInfo
- Publication number
- FI58326C FI58326C FI778/73A FI77873A FI58326C FI 58326 C FI58326 C FI 58326C FI 778/73 A FI778/73 A FI 778/73A FI 77873 A FI77873 A FI 77873A FI 58326 C FI58326 C FI 58326C
- Authority
- FI
- Finland
- Prior art keywords
- hydroxy
- aminomethyl
- methylsulfonyl
- acid
- alcohol
- Prior art date
Links
- 229940126601 medicinal product Drugs 0.000 title 1
- 230000000638 stimulation Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 16
- -1 methylsulfonylmethylbenzyl alcohols Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 239000000021 stimulant Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
- 241000700199 Cavia porcellus Species 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 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
- 238000002474 experimental method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LAMHAMBOLINJML-UHFFFAOYSA-N 1-[3-(chloromethyl)-4-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=CC=C(O)C(CCl)=C1 LAMHAMBOLINJML-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 230000001746 atrial effect Effects 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000000875 corresponding effect Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- BSMGLVDZZMBWQB-UHFFFAOYSA-N 2-methyl-1-phenylpropan-1-one Chemical compound CC(C)C(=O)C1=CC=CC=C1 BSMGLVDZZMBWQB-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- XFWAPSSEBBURNO-UHFFFAOYSA-N CC(C)(C1=CC(=CC=C1)OCC2=CC=CC=C2)NCC3=CC=CC=C3 Chemical compound CC(C)(C1=CC(=CC=C1)OCC2=CC=CC=C2)NCC3=CC=CC=C3 XFWAPSSEBBURNO-UHFFFAOYSA-N 0.000 description 1
- RFRZNXUIYCHLIY-UHFFFAOYSA-N CC(C)(CC1=CC(=CC=C1)OC)NCC2=CC=CC=C2 Chemical compound CC(C)(CC1=CC(=CC=C1)OC)NCC2=CC=CC=C2 RFRZNXUIYCHLIY-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 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
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- JWZZKOKVBUJMES-NSHDSACASA-N L-isoprenaline Chemical compound CC(C)NC[C@H](O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-NSHDSACASA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 229910000831 Steel Inorganic materials 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
- 241001122767 Theaceae Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 210000005091 airway smooth muscle Anatomy 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229950006191 gluconic acid Drugs 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 229950008384 levisoprenaline Drugs 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- NSFUOQCLHUVYCH-UHFFFAOYSA-L magnesium;methanesulfinate Chemical compound [Mg+2].CS([O-])=O.CS([O-])=O NSFUOQCLHUVYCH-UHFFFAOYSA-L 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- MMNNFMKNCOKXLZ-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine;hydrobromide Chemical compound Br.CC(C)(C)NCC1=CC=CC=C1 MMNNFMKNCOKXLZ-UHFFFAOYSA-N 0.000 description 1
- KCAPTTPXCZRLTD-UHFFFAOYSA-N n-benzylcyclobutanamine Chemical compound C=1C=CC=CC=1CNC1CCC1 KCAPTTPXCZRLTD-UHFFFAOYSA-N 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 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
- 230000000241 respiratory effect Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000005062 tracheal ring Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Pulmonology (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23617772A | 1972-03-20 | 1972-03-20 | |
| US23617772 | 1972-03-20 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI58326B FI58326B (fi) | 1980-09-30 |
| FI58326C true FI58326C (fi) | 1981-01-12 |
Family
ID=22888442
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI778/73A FI58326C (fi) | 1972-03-20 | 1973-03-14 | Foerfarande foer framstaellning av som beta-adrenergiskt stimulerande medel anvaendbara alfa-aminometyl-4-hydroksi-3-metylsulfonyl-metylbensylalkoholer |
Country Status (22)
| Country | Link |
|---|---|
| JP (1) | JPS5636188B2 (xx) |
| AR (1) | AR196924A1 (xx) |
| AU (1) | AU469666B2 (xx) |
| BE (1) | BE796894A (xx) |
| BR (1) | BR7301986D0 (xx) |
| CA (1) | CA1007662A (xx) |
| CH (1) | CH576435A5 (xx) |
| DE (1) | DE2313625C2 (xx) |
| DK (1) | DK145082C (xx) |
| ES (1) | ES412799A1 (xx) |
| FI (1) | FI58326C (xx) |
| FR (1) | FR2183681B1 (xx) |
| GB (2) | GB1386029A (xx) |
| HU (1) | HU166931B (xx) |
| IE (1) | IE38206B1 (xx) |
| IL (1) | IL41758A (xx) |
| IT (1) | IT1061426B (xx) |
| LU (1) | LU67220A1 (xx) |
| NL (1) | NL7303715A (xx) |
| PH (1) | PH9436A (xx) |
| SE (1) | SE403773B (xx) |
| ZA (1) | ZA731903B (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966770A (en) * | 1975-03-25 | 1976-06-29 | Smithkline Corporation | 4-Hydroxy-α-[(3,4-methylenedioxyphenyl)isopropylaminoethyl]-3-(methylsulfonylmethyl)benzyl alcohol |
| EP0284561B1 (de) * | 1987-03-26 | 1993-05-12 | Ciba-Geigy Ag | Neue alpha-Aminoacetophenone als Photoinitiatoren |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE34545B1 (en) * | 1969-10-01 | 1975-06-11 | Continental Pharma | Amino-alcohols,their salts and process for preparing the same |
| ZA723611B (en) * | 1971-06-01 | 1973-03-28 | Smith Kline French Lab | N,n'-bis(2-(3-substituted-4-hydroxyphenyl)-ethyl or-2-hydroxyethyl)-polymethylene-diamines |
-
1973
- 1973-03-06 GB GB2471474A patent/GB1386029A/en not_active Expired
- 1973-03-06 GB GB1076873A patent/GB1386028A/en not_active Expired
- 1973-03-13 IL IL41758A patent/IL41758A/en unknown
- 1973-03-13 IE IE409/73A patent/IE38206B1/xx unknown
- 1973-03-14 FR FR7309051A patent/FR2183681B1/fr not_active Expired
- 1973-03-14 SE SE7303544A patent/SE403773B/xx unknown
- 1973-03-14 FI FI778/73A patent/FI58326C/fi active
- 1973-03-15 AR AR247078A patent/AR196924A1/es active
- 1973-03-15 LU LU67220A patent/LU67220A1/xx unknown
- 1973-03-15 IT IT21683/73A patent/IT1061426B/it active
- 1973-03-15 CA CA166,212A patent/CA1007662A/en not_active Expired
- 1973-03-15 JP JP3048873A patent/JPS5636188B2/ja not_active Expired
- 1973-03-15 DK DK139673A patent/DK145082C/da active
- 1973-03-15 HU HUSI1298A patent/HU166931B/hu unknown
- 1973-03-16 PH PH14433*UA patent/PH9436A/en unknown
- 1973-03-16 AU AU53410/73A patent/AU469666B2/en not_active Expired
- 1973-03-16 BE BE128895A patent/BE796894A/xx not_active IP Right Cessation
- 1973-03-16 NL NL7303715A patent/NL7303715A/xx unknown
- 1973-03-17 ES ES412799A patent/ES412799A1/es not_active Expired
- 1973-03-19 ZA ZA731903A patent/ZA731903B/xx unknown
- 1973-03-19 CH CH396473A patent/CH576435A5/xx not_active IP Right Cessation
- 1973-03-19 DE DE2313625A patent/DE2313625C2/de not_active Expired
- 1973-03-20 BR BR731986A patent/BR7301986D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5636188B2 (xx) | 1981-08-22 |
| PH9436A (en) | 1975-11-26 |
| GB1386029A (en) | 1975-03-05 |
| DE2313625A1 (de) | 1973-10-25 |
| NL7303715A (xx) | 1973-09-24 |
| LU67220A1 (xx) | 1973-05-22 |
| DE2313625C2 (de) | 1986-03-13 |
| DK145082B (da) | 1982-08-23 |
| GB1386028A (en) | 1975-03-05 |
| SE403773B (sv) | 1978-09-04 |
| IT1061426B (it) | 1983-02-28 |
| IL41758A0 (en) | 1973-05-31 |
| AU5341073A (en) | 1974-09-19 |
| FR2183681A1 (xx) | 1973-12-21 |
| AU469666B2 (en) | 1976-02-19 |
| BE796894A (fr) | 1973-09-17 |
| ES412799A1 (es) | 1976-06-01 |
| JPS4911846A (xx) | 1974-02-01 |
| CH576435A5 (xx) | 1976-06-15 |
| AR196924A1 (es) | 1974-02-28 |
| CA1007662A (en) | 1977-03-29 |
| IL41758A (en) | 1976-03-31 |
| BR7301986D0 (pt) | 1974-07-25 |
| FI58326B (fi) | 1980-09-30 |
| FR2183681B1 (xx) | 1976-10-22 |
| DK145082C (da) | 1983-03-21 |
| IE38206L (en) | 1973-09-20 |
| IE38206B1 (en) | 1978-01-18 |
| ZA731903B (en) | 1974-01-30 |
| HU166931B (xx) | 1975-06-28 |
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