CA1068282A - 1,2-benzisoxazole derivatives and the production thereof - Google Patents
1,2-benzisoxazole derivatives and the production thereofInfo
- Publication number
- CA1068282A CA1068282A CA259,405A CA259405A CA1068282A CA 1068282 A CA1068282 A CA 1068282A CA 259405 A CA259405 A CA 259405A CA 1068282 A CA1068282 A CA 1068282A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxy
- methyl
- benzisoxazole
- tert
- formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 150000008316 benzisoxazoles Chemical class 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 31
- -1 3,4-dimethoxyphenethyl Chemical group 0.000 claims abstract description 24
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 22
- 230000008569 process Effects 0.000 claims abstract description 21
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims abstract description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 5
- 150000001412 amines Chemical class 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 3
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- ZKVFSZLNHACPAF-UHFFFAOYSA-N 1-[(3-methyl-1,2-benzoxazol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1C(C)=NO2 ZKVFSZLNHACPAF-UHFFFAOYSA-N 0.000 claims description 3
- WBPSCTOWKUOPDB-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-methyl-1,2-benzoxazol-7-yl)oxy]propan-2-ol Chemical compound C1=CC=C2C(C)=NOC2=C1OCC(O)CNC(C)(C)C WBPSCTOWKUOPDB-UHFFFAOYSA-N 0.000 claims description 2
- SEWSVIDLVGPPCI-UHFFFAOYSA-N 1-[(3-methyl-1,2-benzoxazol-7-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC2=C1ON=C2C SEWSVIDLVGPPCI-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 150000002431 hydrogen Chemical class 0.000 claims 4
- 230000000694 effects Effects 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 15
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229940039009 isoproterenol Drugs 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 210000002837 heart atrium Anatomy 0.000 description 7
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 7
- 229960003712 propranolol Drugs 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- NYLPSNFIVDBFDH-UHFFFAOYSA-N 3-methyl-4-(oxiran-2-ylmethoxy)-1,2-benzoxazole Chemical compound C=12C(C)=NOC2=CC=CC=1OCC1CO1 NYLPSNFIVDBFDH-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 150000002118 epoxides Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- NHUHCSRWZMLRLA-UHFFFAOYSA-N Sulfisoxazole Chemical compound CC1=NOC(NS(=O)(=O)C=2C=CC(N)=CC=2)=C1C NHUHCSRWZMLRLA-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- QJKWESZXKFJXGT-UHFFFAOYSA-N chembl1984042 Chemical compound C1=CC(O)=C2C(C)=NOC2=C1 QJKWESZXKFJXGT-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FTAMKSAHBKIDEQ-UHFFFAOYSA-N 1-(propan-2-ylamino)-3-[(3-propyl-1,2-benzoxazol-4-yl)oxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=C2C(CCC)=NOC2=C1 FTAMKSAHBKIDEQ-UHFFFAOYSA-N 0.000 description 1
- IBXHEIGAGGCXAB-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-butyl-1,2-benzoxazol-6-yl)oxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C2C(CCCC)=NOC2=C1 IBXHEIGAGGCXAB-UHFFFAOYSA-N 0.000 description 1
- SJSYXLXESXTZOJ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-butyl-1,2-benzoxazol-7-yl)oxy]propan-2-ol Chemical compound C1=CC=C2C(CCCC)=NOC2=C1OCC(O)CNC(C)(C)C SJSYXLXESXTZOJ-UHFFFAOYSA-N 0.000 description 1
- BTWLSNYHPQATEZ-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-ethyl-1,2-benzoxazol-4-yl)oxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=C2C(CC)=NOC2=C1 BTWLSNYHPQATEZ-UHFFFAOYSA-N 0.000 description 1
- LMSDMNOANBPZML-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-ethyl-1,2-benzoxazol-5-yl)oxy]propan-2-ol Chemical compound C1=C(OCC(O)CNC(C)(C)C)C=C2C(CC)=NOC2=C1 LMSDMNOANBPZML-UHFFFAOYSA-N 0.000 description 1
- AEBBLOLBJVSKSA-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-ethyl-1,2-benzoxazol-6-yl)oxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C2C(CC)=NOC2=C1 AEBBLOLBJVSKSA-UHFFFAOYSA-N 0.000 description 1
- NVWNNIWVMQEWIX-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-methyl-1,2-benzoxazol-4-yl)oxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=C2C(C)=NOC2=C1 NVWNNIWVMQEWIX-UHFFFAOYSA-N 0.000 description 1
- KDXOWQJSTXIBCR-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-methyl-1,2-benzoxazol-5-yl)oxy]propan-2-ol Chemical compound C1=C(OCC(O)CNC(C)(C)C)C=C2C(C)=NOC2=C1 KDXOWQJSTXIBCR-UHFFFAOYSA-N 0.000 description 1
- IDUXUIJWTOMXBB-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-methyl-1,2-benzoxazol-6-yl)oxy]propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C2C(C)=NOC2=C1 IDUXUIJWTOMXBB-UHFFFAOYSA-N 0.000 description 1
- JOIZGXULQCCBEN-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-phenyl-1,2-benzoxazol-5-yl)oxy]propan-2-ol Chemical compound C12=CC(OCC(O)CNC(C)(C)C)=CC=C2ON=C1C1=CC=CC=C1 JOIZGXULQCCBEN-UHFFFAOYSA-N 0.000 description 1
- FWBFGRXYFNNDQE-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-phenyl-1,2-benzoxazol-6-yl)oxy]propan-2-ol Chemical compound N=1OC2=CC(OCC(O)CNC(C)(C)C)=CC=C2C=1C1=CC=CC=C1 FWBFGRXYFNNDQE-UHFFFAOYSA-N 0.000 description 1
- FGIVIUQWHXMPFC-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-phenyl-1,2-benzoxazol-7-yl)oxy]propan-2-ol Chemical compound N=1OC=2C(OCC(O)CNC(C)(C)C)=CC=CC=2C=1C1=CC=CC=C1 FGIVIUQWHXMPFC-UHFFFAOYSA-N 0.000 description 1
- YVGAQXDKGVJLJX-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-propyl-1,2-benzoxazol-4-yl)oxy]propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=C2C(CCC)=NOC2=C1 YVGAQXDKGVJLJX-UHFFFAOYSA-N 0.000 description 1
- QBZYEPKZBZGPRN-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-propyl-1,2-benzoxazol-5-yl)oxy]propan-2-ol Chemical compound C1=C(OCC(O)CNC(C)(C)C)C=C2C(CCC)=NOC2=C1 QBZYEPKZBZGPRN-UHFFFAOYSA-N 0.000 description 1
- FSYKCANGACBXCR-UHFFFAOYSA-N 1-(tert-butylamino)-3-[(3-propyl-1,2-benzoxazol-7-yl)oxy]propan-2-ol Chemical compound C1=CC=C2C(CCC)=NOC2=C1OCC(O)CNC(C)(C)C FSYKCANGACBXCR-UHFFFAOYSA-N 0.000 description 1
- SOCISMITGHAWSB-UHFFFAOYSA-N 1-[(3-butyl-1,2-benzoxazol-4-yl)oxy]-3-(2-phenoxyethylamino)propan-2-ol Chemical compound C=12C(CCCC)=NOC2=CC=CC=1OCC(O)CNCCOC1=CC=CC=C1 SOCISMITGHAWSB-UHFFFAOYSA-N 0.000 description 1
- JWCHXLYRDPFWLE-UHFFFAOYSA-N 1-[(3-butyl-1,2-benzoxazol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=C2C(CCCC)=NOC2=C1 JWCHXLYRDPFWLE-UHFFFAOYSA-N 0.000 description 1
- XTHKEBARFQVEKB-UHFFFAOYSA-N 1-[(3-butyl-1,2-benzoxazol-4-yl)oxy]-3-[2-(3,4-dimethoxyphenyl)ethylamino]propan-2-ol Chemical compound C=12C(CCCC)=NOC2=CC=CC=1OCC(O)CNCCC1=CC=C(OC)C(OC)=C1 XTHKEBARFQVEKB-UHFFFAOYSA-N 0.000 description 1
- XCQQTBABIQGWCG-UHFFFAOYSA-N 1-[(3-butyl-1,2-benzoxazol-5-yl)oxy]-3-[2-(3,4-dimethoxyphenyl)ethylamino]propan-2-ol Chemical compound C1=C2C(CCCC)=NOC2=CC=C1OCC(O)CNCCC1=CC=C(OC)C(OC)=C1 XCQQTBABIQGWCG-UHFFFAOYSA-N 0.000 description 1
- MAZVQXVFXCDUNJ-UHFFFAOYSA-N 1-[(3-ethyl-1,2-benzoxazol-5-yl)oxy]-2-(propan-2-ylamino)propan-2-ol Chemical compound C1=C(OCC(C)(O)NC(C)C)C=C2C(CC)=NOC2=C1 MAZVQXVFXCDUNJ-UHFFFAOYSA-N 0.000 description 1
- QUDKRFWYOURDIQ-UHFFFAOYSA-N 1-[(3-ethyl-1,2-benzoxazol-7-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC=C2C(CC)=NOC2=C1OCC(O)CNC(C)C QUDKRFWYOURDIQ-UHFFFAOYSA-N 0.000 description 1
- CMTCMHNTDWYZKE-UHFFFAOYSA-N 1-[(3-methyl-1,2-benzoxazol-5-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C2ON=C(C)C2=C1 CMTCMHNTDWYZKE-UHFFFAOYSA-N 0.000 description 1
- ZEPKLQWDXYMNTJ-UHFFFAOYSA-N 1-[(3-phenyl-1,2-benzoxazol-4-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=2C(OCC(O)CNC(C)C)=CC=CC=2ON=C1C1=CC=CC=C1 ZEPKLQWDXYMNTJ-UHFFFAOYSA-N 0.000 description 1
- YBOWPULGGNCGGZ-UHFFFAOYSA-N 1-[(3-phenyl-1,2-benzoxazol-5-yl)oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C12=CC(OCC(O)CNC(C)C)=CC=C2ON=C1C1=CC=CC=C1 YBOWPULGGNCGGZ-UHFFFAOYSA-N 0.000 description 1
- MOAAWCFZIBCYIM-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[(3-methyl-1,2-benzoxazol-5-yl)oxy]propan-2-ol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=C(ON=C2C)C2=C1 MOAAWCFZIBCYIM-UHFFFAOYSA-N 0.000 description 1
- LQZXHUYURJPWSR-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethylamino]-3-[(3-methyl-1,2-benzoxazol-7-yl)oxy]propan-2-ol Chemical compound C1=C(OC)C(OC)=CC=C1CCNCC(O)COC1=CC=CC2=C1ON=C2C LQZXHUYURJPWSR-UHFFFAOYSA-N 0.000 description 1
- ZFOAELFEFIUWNX-UHFFFAOYSA-N 1-[3-butyl-4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-1,2-benzoxazol-7-yl]-3-cyclohexylurea Chemical compound C1=CC(OCC(O)CNC(C)C)=C2C(CCCC)=NOC2=C1NC(=O)NC1CCCCC1 ZFOAELFEFIUWNX-UHFFFAOYSA-N 0.000 description 1
- CXAMKQFJGNAUIV-UHFFFAOYSA-N 1-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methyl-1,2-benzoxazol-5-yl]ethanone Chemical compound CC(=O)C1=CC=C2ON=C(C)C2=C1OCC(O)CNC(C)(C)C CXAMKQFJGNAUIV-UHFFFAOYSA-N 0.000 description 1
- AKQDDTBCNYMLPW-UHFFFAOYSA-N 1-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-methyl-1,2-benzoxazol-7-yl]-3-phenylurea Chemical compound CC1=NOC2=C1C(=CC=C2NC(=O)NC2=CC=CC=C2)OCC(CNC(C)(C)C)O AKQDDTBCNYMLPW-UHFFFAOYSA-N 0.000 description 1
- SRXIZNYQNYNXQE-UHFFFAOYSA-N 1-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-propan-2-yl-1,2-benzoxazol-5-yl]ethanone Chemical compound C1=C(C(C)=O)C(OCC(O)CNC(C)(C)C)=C2C(C(C)C)=NOC2=C1 SRXIZNYQNYNXQE-UHFFFAOYSA-N 0.000 description 1
- IJSUXCYQDCBRSJ-UHFFFAOYSA-N 1-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-7-cyclohexyl-1,2-benzoxazol-3-yl]-3-methylurea Chemical compound CNC(NC1=NOC2=C1C(=CC=C2C1CCCCC1)OCC(CNC(C)(C)C)O)=O IJSUXCYQDCBRSJ-UHFFFAOYSA-N 0.000 description 1
- GHCJBYNAGSZMLJ-UHFFFAOYSA-N 1-[5-acetyl-4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-phenyl-1,2-benzoxazol-7-yl]ethanone Chemical compound C12=C(OCC(O)CNC(C)(C)C)C(C(=O)C)=CC(C(C)=O)=C2ON=C1C1=CC=CC=C1 GHCJBYNAGSZMLJ-UHFFFAOYSA-N 0.000 description 1
- CQCPUHDAWBUIIJ-UHFFFAOYSA-N 1-[6-[3-(tert-butylamino)-2-hydroxypropoxy]-3-propyl-1,2-benzoxazol-5-yl]-3-phenylurea Chemical compound C(CC)C1=NOC2=C1C=C(C(=C2)OCC(CNC(C)(C)C)O)NC(=O)NC2=CC=CC=C2 CQCPUHDAWBUIIJ-UHFFFAOYSA-N 0.000 description 1
- BFWMXCAKAVAAML-UHFFFAOYSA-N 1-[[3-(2-methylpropyl)-1,2-benzoxazol-4-yl]oxy]-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=CC(OCC(O)CNC(C)C)=C2C(CC(C)C)=NOC2=C1 BFWMXCAKAVAAML-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- HEJLFBLJYFSKCE-UHFFFAOYSA-N 2',3'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1O HEJLFBLJYFSKCE-UHFFFAOYSA-N 0.000 description 1
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical compound NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 description 1
- KVDVGWLYHGQSSC-UHFFFAOYSA-N 3,4-dimethyl-1,2-benzoxazole Chemical compound C1=CC(C)=C2C(C)=NOC2=C1 KVDVGWLYHGQSSC-UHFFFAOYSA-N 0.000 description 1
- DJYDENKPEXOWFH-UHFFFAOYSA-N 3-[(3-methyl-1,2-benzoxazol-4-yl)oxy]-n-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCCOC1=CC=CC2=C1C(C)=NO2 DJYDENKPEXOWFH-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 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
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000002425 cardiocirculatory effect Effects 0.000 description 1
- 210000000845 cartilage Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000007689 inspection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 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
- 239000008101 lactose Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 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
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OEVUKEPVTTWFAA-UHFFFAOYSA-N n-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]-3-methyl-1,2-benzoxazol-7-yl]acetamide Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C2=C1C(C)=NO2 OEVUKEPVTTWFAA-UHFFFAOYSA-N 0.000 description 1
- LPSYQQOKGHUEOS-UHFFFAOYSA-N n-[4-[3-(tert-butylamino)-2-hydroxypropoxy]-3-(2-methylpropyl)-1,2-benzoxazol-7-yl]acetamide Chemical compound C1=CC(OCC(O)CNC(C)(C)C)=C2C(CC(C)C)=NOC2=C1NC(C)=O LPSYQQOKGHUEOS-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
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical class OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229940093932 potassium hydroxide Drugs 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 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
- 230000001960 triggered effect Effects 0.000 description 1
- 231100000691 up-and-down procedure Toxicity 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB37132/75A GB1513446A (en) | 1975-09-09 | 1975-09-09 | 1,2-benzisoxazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068282A true CA1068282A (en) | 1979-12-18 |
Family
ID=10393994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA259,405A Expired CA1068282A (en) | 1975-09-09 | 1976-08-19 | 1,2-benzisoxazole derivatives and the production thereof |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4085114A (en]) |
| JP (1) | JPS5233669A (en]) |
| AU (1) | AU501382B2 (en]) |
| BE (1) | BE846010A (en]) |
| CA (1) | CA1068282A (en]) |
| CH (1) | CH605856A5 (en]) |
| DE (1) | DE2640652A1 (en]) |
| DK (1) | DK402776A (en]) |
| ES (1) | ES451329A1 (en]) |
| FR (1) | FR2323691A1 (en]) |
| GB (1) | GB1513446A (en]) |
| NL (1) | NL7609746A (en]) |
| SE (1) | SE7609769L (en]) |
| ZA (1) | ZA764847B (en]) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4314943A (en) * | 1977-07-13 | 1982-02-09 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| US4728662A (en) * | 1977-11-21 | 1988-03-01 | Hoechst-Roussel Pharmaceuticals Inc. | 1,2-benzisoxazoloxyacetic acids and related compounds |
| US4673746A (en) * | 1978-10-06 | 1987-06-16 | Hoechst-Roussel Pharmaceuticals, Inc. | 1,2-benzisoxazoloxyacetic acids and related compounds |
| US4495352A (en) * | 1979-02-13 | 1985-01-22 | Mead Johnson & Company | Heterocyclic substituted aryloxy 3-indolyl-tertiary butylaminopropanols |
| DE2946524A1 (de) * | 1979-11-17 | 1981-06-11 | Bayer Ag, 5090 Leverkusen | Azolyloxy-carbonsaeure-n-oxy-amide, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
| US4427691A (en) | 1981-02-25 | 1984-01-24 | Hoechst-Roussel Pharmaceuticals Inc. | 1,2-Benzisoxazoloxyethylamines and intermediates for the preparation thereof |
| US7253165B2 (en) * | 1999-09-14 | 2007-08-07 | Aventis Pharmaceuticals Inc. | Benzisoxazolyl-, pyridoisoxazolyl-and benzthienyl-phenoxy derivatives useful as D4 antagonists |
| US7091199B1 (en) | 1999-09-14 | 2006-08-15 | Aventis Pharmaceuticals Inc. | Thienoisoxazole phenoxy unsubstituted ethyl and propyl derivatives useful as d4 antagonists |
| US7125903B1 (en) | 1999-09-14 | 2006-10-24 | Aventis Pharmaceuticals Inc. | Thienoisoxazolyl-and thienylpyrrazolyl-phenoxy substituted propyl derivatives useful as D4 antagonists |
-
1975
- 1975-09-09 GB GB37132/75A patent/GB1513446A/en not_active Expired
-
1976
- 1976-08-09 US US05/713,044 patent/US4085114A/en not_active Expired - Lifetime
- 1976-08-19 CA CA259,405A patent/CA1068282A/en not_active Expired
- 1976-08-23 CH CH1068576A patent/CH605856A5/xx not_active IP Right Cessation
- 1976-09-01 NL NL7609746A patent/NL7609746A/xx not_active Application Discontinuation
- 1976-09-03 JP JP51106178A patent/JPS5233669A/ja active Pending
- 1976-09-03 SE SE7609769A patent/SE7609769L/xx unknown
- 1976-09-07 DK DK402776A patent/DK402776A/da unknown
- 1976-09-08 FR FR7627042A patent/FR2323691A1/fr active Granted
- 1976-09-08 ES ES451329A patent/ES451329A1/es not_active Expired
- 1976-09-09 AU AU17596/76A patent/AU501382B2/en not_active Expired
- 1976-09-09 BE BE170484A patent/BE846010A/xx unknown
- 1976-09-09 DE DE19762640652 patent/DE2640652A1/de not_active Withdrawn
- 1976-10-11 ZA ZA764847A patent/ZA764847B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH605856A5 (en]) | 1978-10-13 |
| NL7609746A (nl) | 1977-03-11 |
| ZA764847B (en) | 1977-07-27 |
| SE7609769L (sv) | 1977-03-10 |
| AU1759676A (en) | 1978-03-16 |
| US4085114A (en) | 1978-04-18 |
| FR2323691B1 (en]) | 1979-03-09 |
| AU501382B2 (en) | 1979-06-21 |
| GB1513446A (en) | 1978-06-07 |
| BE846010A (fr) | 1976-12-31 |
| FR2323691A1 (fr) | 1977-04-08 |
| ES451329A1 (es) | 1977-11-01 |
| DE2640652A1 (de) | 1977-03-17 |
| DK402776A (da) | 1977-03-10 |
| JPS5233669A (en) | 1977-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IE58608B1 (en) | Piperazine derivatives | |
| US4659710A (en) | 1,7-Naphthyridine derivatives and pharmaceutical compositions | |
| CA1068282A (en) | 1,2-benzisoxazole derivatives and the production thereof | |
| US3705907A (en) | 4-(2-hydroxy)-3-aminopropoxy)-indole derivatives | |
| US3280122A (en) | Diphenylalkyloxadiazoles | |
| US4478750A (en) | 1-Phenyl-azepinoindoles | |
| US2820817A (en) | Oxygenated indan compounds and method of making the same | |
| US4540691A (en) | Dopamine agonists and use thereof | |
| IE46376B1 (en) | Isoquinoline and naphthyridine substituted aminoalkoxyphenyl derivatives | |
| US4109088A (en) | 2-(indenyloxymethyl) morpholine derivatives | |
| US3254120A (en) | N-(tertiaryaminoalkoxy-benzoyl) anilides | |
| NO145841B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive 2,3-substituerte, 5,6-kondenserte 4(2h)-aminoalkoksy-pyranoner med hypotensiv, anti-ischaemia- og anti-hostevirkning | |
| US3734915A (en) | N-(-(4-phenyl-1-piperazinyl)alkyl)benzo(b)thiophene or benzofuran-2-carboxamides | |
| US3665074A (en) | Certain benzofuran derivatives useful for relief of pain,inflammation,pyresis and tussive irritation | |
| US4268513A (en) | Pyrrolo [3,4-c]quinoline compounds and pharmaceutical compositions, methods for their use and preparation | |
| US3944581A (en) | 5-Substituted-2,4-diphenylpyrimidines | |
| CA1207774A (en) | 1-phenylindazol-3-one compounds, a method of preparing them and pharmaceutical compositions containing these compounds | |
| US4714702A (en) | Quinazolinone derivative | |
| JPS5948831B2 (ja) | ベンゾチアゾ−ル誘導体、およびそれらの製造法 | |
| US3872130A (en) | 1-hydroxyisoquinolones | |
| GB1599181A (en) | Oxyalkanoic acid derivatives | |
| KR790001381B1 (ko) | 1, 2-벤즈이속사졸 유도체의 제조법 | |
| US3485835A (en) | 2-benzoyl-3-tertiaryamino alkoxy benzofuran derivatives | |
| GB2030133A (en) | Tetrahydrothiopyrano (2,3-b) indole derivatives | |
| US3935236A (en) | Aminopropanol substituted isochromanones and phthalides |