DE3026534A1 - 3,1-benzoxazin-2-one, ihre herstellung und verwendung - Google Patents
3,1-benzoxazin-2-one, ihre herstellung und verwendungInfo
- Publication number
- DE3026534A1 DE3026534A1 DE19803026534 DE3026534A DE3026534A1 DE 3026534 A1 DE3026534 A1 DE 3026534A1 DE 19803026534 DE19803026534 DE 19803026534 DE 3026534 A DE3026534 A DE 3026534A DE 3026534 A1 DE3026534 A1 DE 3026534A1
- Authority
- DE
- Germany
- Prior art keywords
- deep
- alkyl
- hydrogen
- general formula
- group
- 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.)
- Withdrawn
Links
- GZOJTRITAZODJV-UHFFFAOYSA-N 3,1-benzoxazin-2-one Chemical compound C1=CC=CC2=COC(=O)N=C21 GZOJTRITAZODJV-UHFFFAOYSA-N 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- -1 hydroxy, methyl Chemical group 0.000 claims abstract description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 20
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 17
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 239000011737 fluorine Substances 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 238000002360 preparation method Methods 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 230000003195 tocolytic effect Effects 0.000 claims abstract description 4
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 3
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims 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 claims description 3
- 230000003276 anti-hypertensive effect Effects 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 229940124630 bronchodilator Drugs 0.000 claims description 2
- 230000001813 broncholytic effect Effects 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 229940124549 vasodilator Drugs 0.000 claims description 2
- 239000003071 vasodilator agent Substances 0.000 claims description 2
- 230000000747 cardiac effect Effects 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 4
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 208000001953 Hypotension Diseases 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 208000021822 hypotensive Diseases 0.000 abstract 1
- 230000001077 hypotensive effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 9
- 239000002585 base Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 7
- 230000036772 blood pressure Effects 0.000 description 7
- 125000006308 propyl amino group Chemical group 0.000 description 7
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000543 intermediate 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
- 229910052759 nickel Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- 239000002262 Schiff base Substances 0.000 description 2
- 150000004753 Schiff bases Chemical class 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 208000036029 Uterine contractions during pregnancy Diseases 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 2
- 239000002220 antihypertensive agent Substances 0.000 description 2
- 229940030600 antihypertensive agent Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
- 229910003446 platinum oxide Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MHJPNBAEWSRKBK-UHFFFAOYSA-N 1-aminopropane-2-thiol Chemical compound CC(S)CN MHJPNBAEWSRKBK-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 239000000043 antiallergic agent Substances 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 1
- 229960003870 bromhexine Drugs 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 239000002371 cardiac agent Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 150000002373 hemiacetals Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229960001361 ipratropium bromide Drugs 0.000 description 1
- KEWHKYJURDBRMN-ZEODDXGYSA-M ipratropium bromide hydrate Chemical compound O.[Br-].O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 KEWHKYJURDBRMN-ZEODDXGYSA-M 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- MPLHCFBMCCBBKT-UHFFFAOYSA-N methyl 2-hydroxy-5-oxaldehydoylbenzoate Chemical compound COC(=O)C1=CC(C(=O)C=O)=CC=C1O MPLHCFBMCCBBKT-UHFFFAOYSA-N 0.000 description 1
- YLGXILFCIXHCMC-JHGZEJCSSA-N methyl cellulose Chemical compound COC1C(OC)C(OC)C(COC)O[C@H]1O[C@H]1C(OC)C(OC)C(OC)OC1COC YLGXILFCIXHCMC-JHGZEJCSSA-N 0.000 description 1
- 230000003170 musculotropic effect Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- GTDQGKWDWVUKTI-UHFFFAOYSA-N o-aminoacetophenone Chemical class CC(=O)C1=CC=CC=C1N GTDQGKWDWVUKTI-UHFFFAOYSA-N 0.000 description 1
- 230000002445 parasympatholytic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000894 saliuretic effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 230000002048 spasmolytic effect Effects 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940125712 tocolytic agent Drugs 0.000 description 1
- 239000003675 tocolytic agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/18—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 2
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Priority Applications (31)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803026534 DE3026534A1 (de) | 1980-07-12 | 1980-07-12 | 3,1-benzoxazin-2-one, ihre herstellung und verwendung |
| DE8181104787T DE3166003D1 (en) | 1980-07-12 | 1981-06-22 | 3,1-benzoxazin-2-ones, their preparation and their use |
| AT81104787T ATE9336T1 (de) | 1980-07-12 | 1981-06-22 | 3,1-benzoxazin-2-one, ihre herstellung und verwendung. |
| EP81104787A EP0043940B1 (de) | 1980-07-12 | 1981-06-22 | 3,1-Benzoxazin-2-one, ihre Herstellung und Verwendung |
| US06/280,349 US4341778A (en) | 1980-07-12 | 1981-07-06 | 3,1 Benzoxazin-2-ones and use thereof |
| PH25873A PH17425A (en) | 1980-07-12 | 1981-07-07 | 3,1-benzoxazin-2-ones and pharmaceutical compositions containing the same |
| PT73338A PT73338B (en) | 1980-07-12 | 1981-07-09 | 3,1-benzoxazin-2-one ihre herstellung und verwendung |
| YU01701/81A YU170181A (en) | 1980-07-12 | 1981-07-09 | Process for preparing 3,1-benzoxazine-2-ones |
| IE1567/81A IE52508B1 (en) | 1980-07-12 | 1981-07-10 | 3,1-benzoxazin-2-ones,the preparation and use thereof |
| AU72731/81A AU540916B2 (en) | 1980-07-12 | 1981-07-10 | 3,1 benzoxazin-2-ones |
| ES503837A ES8205402A1 (es) | 1980-07-12 | 1981-07-10 | Procedimiento para la preparacion de 3,1-benzoxazin-2-onas |
| CA000381559A CA1165317A (en) | 1980-07-12 | 1981-07-10 | 3,1-benzoxazin-2-ones, the preparation and use thereof |
| NO812355A NO158578C (no) | 1980-07-12 | 1981-07-10 | Analogifremgangsmaate for fremstilling av terapeutisk aktive 3,1-benzoksazin-2-on-derivater. |
| IL63285A IL63285A (en) | 1980-07-12 | 1981-07-10 | Phenylhydroxyalkyl-aminoalkyl-3,1-benzoxazin-2-one derivatives,their preparation and pharmaceutical compositions containing them |
| ZA814687A ZA814687B (en) | 1980-07-12 | 1981-07-10 | 3,1-benzoxazin-2-ones,processes for their preparation,and pharmaceutical compositions thereof |
| DD81231670A DD202018A5 (de) | 1980-07-12 | 1981-07-10 | Verfahren zur herstellung von 3,1-benzoxazin-2-onen |
| NZ197678A NZ197678A (en) | 1980-07-12 | 1981-07-10 | 1-phenyl-2-(3-(2-oxo-1,2-dihydro-4h-3,1-benzoxazin-1-yl)propyl)aminoethanols |
| HU812036A HU183515B (en) | 1980-07-12 | 1981-07-10 | Process for preparing 3,1-benzoxazin-2-one derivatives |
| FI812183A FI74703C (fi) | 1980-07-12 | 1981-07-10 | Foerfarande foer framstaellning av terapeutiskt verksamma 3,1-bensoxazin-2-oner. |
| DK306781A DK149851C (da) | 1980-07-12 | 1981-07-10 | Analogifremgangsmaade til fremstilling af 3,1-benzoxazin-2-oner eller farmaceutisk acceptable syreadditionssalte heraf |
| GR65470A GR74333B (https=) | 1980-07-12 | 1981-07-10 | |
| GB8121321A GB2080296B (en) | 1980-07-12 | 1981-07-10 | 3,1-benzoxazin-2-ones the preparation and use thereof |
| KR8102523A KR850000755B1 (en) | 1980-07-12 | 1981-07-11 | Process for preparing 3,1-benzoxazin-2-ones and acid addition salts thereof |
| JP56109186A JPS5748975A (en) | 1980-07-12 | 1981-07-13 | Novel 3,1-benzoxazine-2-one |
| ES508653A ES508653A0 (es) | 1980-07-12 | 1982-01-12 | "procedimiento para la preparacion de 3,1-benzoxazin-2-onas". |
| ES508655A ES8300727A1 (es) | 1980-07-12 | 1982-01-12 | "procedimiento para la preparacion de 3,1-benzoxazin-2-onas". |
| ES508654A ES508654A0 (es) | 1980-07-12 | 1982-01-12 | "procedimiento para la preparacion de 3,1-benzoxazin-2-onas". |
| KR1019850001963A KR850000754B1 (ko) | 1980-07-12 | 1985-03-25 | 3, 1-벤즈옥사진-2-온 및 이의 산부가염의 제조방법 |
| KR1019850001965A KR850000741B1 (ko) | 1980-07-12 | 1985-03-25 | 3,1-벤즈옥사진-2-온 및 이의 산 부가염의 제조방법 |
| SG776/86A SG77686G (en) | 1980-07-12 | 1986-09-26 | 3,1-benzoxazin-2-ones, the preparation and use thereof |
| HK982/86A HK98286A (en) | 1980-07-12 | 1986-12-18 | 3,1-benzoxazin-2-ones,the preparation and use thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803026534 DE3026534A1 (de) | 1980-07-12 | 1980-07-12 | 3,1-benzoxazin-2-one, ihre herstellung und verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3026534A1 true DE3026534A1 (de) | 1982-03-18 |
Family
ID=6107085
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803026534 Withdrawn DE3026534A1 (de) | 1980-07-12 | 1980-07-12 | 3,1-benzoxazin-2-one, ihre herstellung und verwendung |
| DE8181104787T Expired DE3166003D1 (en) | 1980-07-12 | 1981-06-22 | 3,1-benzoxazin-2-ones, their preparation and their use |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8181104787T Expired DE3166003D1 (en) | 1980-07-12 | 1981-06-22 | 3,1-benzoxazin-2-ones, their preparation and their use |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4341778A (https=) |
| EP (1) | EP0043940B1 (https=) |
| JP (1) | JPS5748975A (https=) |
| KR (1) | KR850000755B1 (https=) |
| AT (1) | ATE9336T1 (https=) |
| AU (1) | AU540916B2 (https=) |
| CA (1) | CA1165317A (https=) |
| DD (1) | DD202018A5 (https=) |
| DE (2) | DE3026534A1 (https=) |
| DK (1) | DK149851C (https=) |
| ES (4) | ES8205402A1 (https=) |
| FI (1) | FI74703C (https=) |
| GB (1) | GB2080296B (https=) |
| GR (1) | GR74333B (https=) |
| HK (1) | HK98286A (https=) |
| HU (1) | HU183515B (https=) |
| IE (1) | IE52508B1 (https=) |
| IL (1) | IL63285A (https=) |
| NO (1) | NO158578C (https=) |
| NZ (1) | NZ197678A (https=) |
| PH (1) | PH17425A (https=) |
| PT (1) | PT73338B (https=) |
| SG (1) | SG77686G (https=) |
| YU (1) | YU170181A (https=) |
| ZA (1) | ZA814687B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4446319A (en) * | 1981-04-28 | 1984-05-01 | Takeda Chemical Industries, Ltd. | Aminocyclitols and their production |
| JPS62238288A (ja) * | 1986-04-04 | 1987-10-19 | Nippon Tokushu Noyaku Seizo Kk | 環状カルバメ−ト及び農園芸用殺菌剤 |
| FR2636065B1 (fr) * | 1988-09-08 | 1993-05-07 | Fabre Sa Pierre | Nouveaux derives de dihydro-2,3 arylacoylaminoalcoyl-3 4h-benzoxazine-1,3 ones-4, leur preparation et leur application en tant que medicaments utiles en therapeutique |
| JP2807577B2 (ja) * | 1990-06-15 | 1998-10-08 | エーザイ株式会社 | 環状アミド誘導体 |
| FR2680172B1 (fr) * | 1991-08-05 | 1993-11-19 | Fabre Medicament Pierre | Nouvelles piperazinylalcoyl-3 dihydro-2,3 4h-benzoxazine-1,3 ones-4 substituees, leur preparation et leur application en therapeutique. |
| CA2210138A1 (en) * | 1995-01-24 | 1996-08-01 | Peter D. Williams | Tocolytic oxytocin receptor antagonists |
| US5874430A (en) * | 1996-10-02 | 1999-02-23 | Dupont Pharmaceuticals Company | 4,4-disubstitued-1,4-dihydro-2H-3,1-benzoxazin-2-ones useful as HIV reverse transcriptase inhibitors and intermediates and processes for making the same |
| DE102004003428A1 (de) * | 2004-01-23 | 2005-08-11 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue langwirksame Beta-2-Agonisten, und deren Verwendung als Arzneimittel |
| EP1844768A1 (en) * | 2005-01-19 | 2007-10-17 | Dainippon Sumitomo Pharma Co., Ltd. | Aromatic sulfone compound as aldosterone receptor modulator |
| DE102005008921A1 (de) * | 2005-02-24 | 2006-08-31 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue Arzneimittel zur Behandlung von Atemwegserkrankungen |
| US7423146B2 (en) | 2005-11-09 | 2008-09-09 | Boehringer Ingelheim International Gmbh | Process for the manufacturing of pharmaceutically active 3,1-benzoxazine-2-ones |
| PE20080425A1 (es) * | 2006-08-22 | 2008-06-16 | Boehringer Ingelheim Int | Formulacion aerosol para la inhalacion de beta-agonistas |
| UY30550A1 (es) * | 2006-08-22 | 2008-03-31 | Boehringer Ingelheim Int | Nuevos beta-agonistas enantioméricamente puros, procedimientos para su preparacion y su uso como medicamentos |
| EP2056836A1 (en) * | 2006-08-22 | 2009-05-13 | Boehringer Ingelheim International GmbH | Powder formulations for inhalation containing enantiomerically pure beta-agonists |
| PE20081358A1 (es) * | 2006-08-22 | 2008-10-31 | Boehringer Ingelheim Int | Combinaciones farmacologicas para el tratamiento de enfermedades de la vias aereas |
| EP2093219A1 (de) | 2008-02-22 | 2009-08-26 | Boehringer Ingelheim International Gmbh | Kristalline, enantiomerenreine Salzform eines Betamimetikums und dessen Verwendung als Arzneimittel |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3526621A (en) * | 1966-08-03 | 1970-09-01 | Farmaceutical Italia Soc | Substituted 3,1-benzoxazin-2-one |
| DE2609645A1 (de) * | 1976-03-09 | 1977-09-15 | Boehringer Sohn Ingelheim | Aminoalkylheterocyclen |
| US4163053A (en) * | 1977-12-27 | 1979-07-31 | Schering Corporation | Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides |
| DD144050A5 (de) * | 1978-06-05 | 1980-09-24 | Ciba Geigy Ag | Verfahren zur herstellung von n-alkylierten aminoalkoholen |
| DE2833140A1 (de) * | 1978-07-28 | 1980-02-07 | Boehringer Sohn Ingelheim | Neue n-substituierte heterocyclen |
-
1980
- 1980-07-12 DE DE19803026534 patent/DE3026534A1/de not_active Withdrawn
-
1981
- 1981-06-22 DE DE8181104787T patent/DE3166003D1/de not_active Expired
- 1981-06-22 AT AT81104787T patent/ATE9336T1/de not_active IP Right Cessation
- 1981-06-22 EP EP81104787A patent/EP0043940B1/de not_active Expired
- 1981-07-06 US US06/280,349 patent/US4341778A/en not_active Expired - Fee Related
- 1981-07-07 PH PH25873A patent/PH17425A/en unknown
- 1981-07-09 PT PT73338A patent/PT73338B/pt unknown
- 1981-07-09 YU YU01701/81A patent/YU170181A/xx unknown
- 1981-07-10 NO NO812355A patent/NO158578C/no unknown
- 1981-07-10 ES ES503837A patent/ES8205402A1/es not_active Expired
- 1981-07-10 NZ NZ197678A patent/NZ197678A/en unknown
- 1981-07-10 FI FI812183A patent/FI74703C/fi not_active IP Right Cessation
- 1981-07-10 GB GB8121321A patent/GB2080296B/en not_active Expired
- 1981-07-10 CA CA000381559A patent/CA1165317A/en not_active Expired
- 1981-07-10 DK DK306781A patent/DK149851C/da not_active IP Right Cessation
- 1981-07-10 ZA ZA814687A patent/ZA814687B/xx unknown
- 1981-07-10 IE IE1567/81A patent/IE52508B1/en unknown
- 1981-07-10 IL IL63285A patent/IL63285A/xx unknown
- 1981-07-10 DD DD81231670A patent/DD202018A5/de unknown
- 1981-07-10 GR GR65470A patent/GR74333B/el unknown
- 1981-07-10 HU HU812036A patent/HU183515B/hu unknown
- 1981-07-10 AU AU72731/81A patent/AU540916B2/en not_active Ceased
- 1981-07-11 KR KR8102523A patent/KR850000755B1/ko not_active Expired
- 1981-07-13 JP JP56109186A patent/JPS5748975A/ja active Pending
-
1982
- 1982-01-12 ES ES508653A patent/ES508653A0/es active Granted
- 1982-01-12 ES ES508654A patent/ES508654A0/es active Granted
- 1982-01-12 ES ES508655A patent/ES8300727A1/es not_active Expired
-
1986
- 1986-09-26 SG SG776/86A patent/SG77686G/en unknown
- 1986-12-18 HK HK982/86A patent/HK98286A/xx unknown
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| 8139 | Disposal/non-payment of the annual fee |