CH617180A5 - Process for the preparation of novel aminotetralol compounds - Google Patents
Process for the preparation of novel aminotetralol compounds Download PDFInfo
- Publication number
- CH617180A5 CH617180A5 CH432175A CH432175A CH617180A5 CH 617180 A5 CH617180 A5 CH 617180A5 CH 432175 A CH432175 A CH 432175A CH 432175 A CH432175 A CH 432175A CH 617180 A5 CH617180 A5 CH 617180A5
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- CH
- Switzerland
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- formula
- compound
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- reaction
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- 150000001875 compounds Chemical class 0.000 title claims description 76
- 238000000034 method Methods 0.000 title claims description 38
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000002015 acyclic group Chemical group 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 13
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 5
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- -1 i-pentyl Chemical group 0.000 description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 63
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- 239000000203 mixture Substances 0.000 description 29
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 23
- 238000000354 decomposition reaction Methods 0.000 description 21
- 238000006722 reduction reaction Methods 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 239000013078 crystal Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 230000000875 corresponding effect Effects 0.000 description 14
- 238000000921 elemental analysis Methods 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 238000010531 catalytic reduction reaction Methods 0.000 description 13
- 125000000623 heterocyclic group Chemical group 0.000 description 13
- 150000002430 hydrocarbons Chemical group 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000004432 carbon atom Chemical group C* 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- 238000001953 recrystallisation Methods 0.000 description 12
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000005917 acylation reaction Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 208000006673 asthma Diseases 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 238000004108 freeze drying Methods 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 125000006239 protecting group Chemical group 0.000 description 6
- KHYYLUWDNOPFOQ-UHFFFAOYSA-N 2-amino-5,6-dimethoxy-3,4-dihydro-2h-naphthalen-1-one;hydrochloride Chemical compound Cl.O=C1C(N)CCC2=C(OC)C(OC)=CC=C21 KHYYLUWDNOPFOQ-UHFFFAOYSA-N 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HBZZEMVKWVIVTO-UHFFFAOYSA-N 2-amino-5,6-dihydroxy-3,4-dihydro-2h-naphthalen-1-one;hydrobromide Chemical compound Br.OC1=CC=C2C(=O)C(N)CCC2=C1O HBZZEMVKWVIVTO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 206010003119 arrhythmia Diseases 0.000 description 4
- 230000006793 arrhythmia Effects 0.000 description 4
- 230000003182 bronchodilatating effect Effects 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229940039009 isoproterenol Drugs 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000011946 reduction process Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- XSAYODARBWKMMM-UHFFFAOYSA-N 2-(cyclohexylamino)-5,6-dihydroxy-3,4-dihydro-2h-naphthalen-1-one;hydrobromide Chemical compound Br.C1CC2=C(O)C(O)=CC=C2C(=O)C1NC1CCCCC1 XSAYODARBWKMMM-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000000903 blocking effect Effects 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
- 244000309466 calf Species 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 235000011087 fumaric acid Nutrition 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
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- 238000000926 separation method Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
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- 238000011282 treatment Methods 0.000 description 3
- NRIVMXXOUOBRAG-UHFFFAOYSA-N 2-(4-methoxyphenyl)acetaldehyde Chemical compound COC1=CC=C(CC=O)C=C1 NRIVMXXOUOBRAG-UHFFFAOYSA-N 0.000 description 2
- KDZNBHSLWMXDGH-UHFFFAOYSA-N 2-(cyclobutylamino)-5,6-dihydroxy-3,4-dihydro-2h-naphthalen-1-one;hydrobromide Chemical compound Br.C1CC2=C(O)C(O)=CC=C2C(=O)C1NC1CCC1 KDZNBHSLWMXDGH-UHFFFAOYSA-N 0.000 description 2
- FFGFJAKGXHZCOT-UHFFFAOYSA-N 2-(cyclobutylamino)-5,6-dimethoxy-3,4-dihydro-2h-naphthalen-1-one;hydrochloride Chemical compound Cl.C1CC2=C(OC)C(OC)=CC=C2C(=O)C1NC1CCC1 FFGFJAKGXHZCOT-UHFFFAOYSA-N 0.000 description 2
- URYODHGMNCAEPV-UHFFFAOYSA-N 2-(cyclohexylamino)-5,6-dimethoxy-3,4-dihydro-2h-naphthalen-1-one;hydrochloride Chemical compound Cl.C1CC2=C(OC)C(OC)=CC=C2C(=O)C1NC1CCCCC1 URYODHGMNCAEPV-UHFFFAOYSA-N 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
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- PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
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- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4463174A JPS50148341A (en, 2012) | 1974-04-19 | 1974-04-19 | |
| JP4609774A JPS50140432A (en, 2012) | 1974-04-23 | 1974-04-23 | |
| JP49047211A JPS5826332B2 (ja) | 1974-04-25 | 1974-04-25 | テトラロ−ルカゴウブツ ノ セイゾウホウ |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617180A5 true CH617180A5 (en) | 1980-05-14 |
Family
ID=27291968
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH432175A CH617180A5 (en) | 1974-04-19 | 1975-04-04 | Process for the preparation of novel aminotetralol compounds |
Country Status (10)
| Country | Link |
|---|---|
| CH (1) | CH617180A5 (en, 2012) |
| DE (1) | DE2514455A1 (en, 2012) |
| DK (1) | DK87275A (en, 2012) |
| ES (1) | ES435624A1 (en, 2012) |
| FI (1) | FI751146A7 (en, 2012) |
| FR (1) | FR2267763B1 (en, 2012) |
| GB (1) | GB1502155A (en, 2012) |
| NL (1) | NL7504551A (en, 2012) |
| NO (1) | NO750835L (en, 2012) |
| SE (1) | SE7504450L (en, 2012) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5314916A (en) * | 1993-04-19 | 1994-05-24 | Alcon Laboratories, Inc. | B2 adrenegic agonists and use thereof in the treatment of glaucoma |
-
1975
- 1975-03-04 DK DK87275*#A patent/DK87275A/da unknown
- 1975-03-12 NO NO750835A patent/NO750835L/no unknown
- 1975-03-14 ES ES435624A patent/ES435624A1/es not_active Expired
- 1975-03-24 FR FR7509116A patent/FR2267763B1/fr not_active Expired
- 1975-04-03 DE DE19752514455 patent/DE2514455A1/de not_active Withdrawn
- 1975-04-04 CH CH432175A patent/CH617180A5/de not_active IP Right Cessation
- 1975-04-16 NL NL7504551A patent/NL7504551A/xx not_active Application Discontinuation
- 1975-04-17 FI FI751146A patent/FI751146A7/fi not_active Application Discontinuation
- 1975-04-17 SE SE7504450A patent/SE7504450L/xx unknown
- 1975-04-21 GB GB16345/75A patent/GB1502155A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI751146A7 (en, 2012) | 1975-10-20 |
| FR2267763A1 (en, 2012) | 1975-11-14 |
| DK87275A (da) | 1975-10-20 |
| NL7504551A (nl) | 1975-10-21 |
| SE7504450L (sv) | 1975-10-20 |
| ES435624A1 (es) | 1977-03-16 |
| GB1502155A (en) | 1978-02-22 |
| FR2267763B1 (en, 2012) | 1978-06-30 |
| DE2514455A1 (de) | 1975-10-30 |
| NO750835L (en, 2012) | 1975-10-21 |
| AU7904575A (en) | 1976-09-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |