JPH0534357B2 - - Google Patents
Info
- Publication number
- JPH0534357B2 JPH0534357B2 JP59034093A JP3409384A JPH0534357B2 JP H0534357 B2 JPH0534357 B2 JP H0534357B2 JP 59034093 A JP59034093 A JP 59034093A JP 3409384 A JP3409384 A JP 3409384A JP H0534357 B2 JPH0534357 B2 JP H0534357B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- normon
- oxadiazole
- mmol
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 115
- 239000000203 mixture Substances 0.000 claims description 36
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 125000006239 protecting group Chemical group 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000002541 furyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 10
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims 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 claims description 2
- 206010028470 Mycoplasma infections Diseases 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 123
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 82
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 55
- 239000000243 solution Substances 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 39
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 24
- 235000019198 oils Nutrition 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 239000003814 drug Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 19
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 239000012267 brine Substances 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 13
- IUBMRJVNZLQSHU-FDJBSCRHSA-N monate-a Chemical compound C[C@H](O)[C@H](C)[C@@H]1O[C@H]1C[C@@H]1[C@@H](O)[C@@H](O)[C@H](C\C(C)=C\C(O)=O)OC1 IUBMRJVNZLQSHU-FDJBSCRHSA-N 0.000 description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
- 239000000741 silica gel Substances 0.000 description 13
- 229910002027 silica gel Inorganic materials 0.000 description 13
- 239000000284 extract Substances 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 11
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 10
- 229940079593 drug Drugs 0.000 description 10
- 239000006260 foam Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- -1 alkali metal cation Chemical class 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 150000003512 tertiary amines Chemical class 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 8
- 229950005499 carbon tetrachloride Drugs 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000007363 ring formation reaction Methods 0.000 description 6
- 239000003981 vehicle Substances 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 235000019270 ammonium chloride Nutrition 0.000 description 5
- 230000003197 catalytic effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 206010035664 Pneumonia Diseases 0.000 description 4
- 241000282887 Suidae Species 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 230000000699 topical effect Effects 0.000 description 4
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 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
- ZMMRLWFGWQVVJD-UHFFFAOYSA-O (n,n-dimethylcarbamimidoyl)-dimethylazanium;azide Chemical compound [N-]=[N+]=[N-].CN(C)C(N)=[N+](C)C ZMMRLWFGWQVVJD-UHFFFAOYSA-O 0.000 description 3
- ODVBBZFQPGORMJ-UHFFFAOYSA-N 4-nitrobenzylamine Chemical compound NCC1=CC=C([N+]([O-])=O)C=C1 ODVBBZFQPGORMJ-UHFFFAOYSA-N 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 241000283690 Bos taurus Species 0.000 description 3
- 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 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000204031 Mycoplasma Species 0.000 description 3
- 206010057190 Respiratory tract infections Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 208000004396 mastitis Diseases 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 description 2
- NDQACJBDAQZPCW-UHFFFAOYSA-N 2-methyl-5-phenyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1C1=CC=CC=C1 NDQACJBDAQZPCW-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- ACNALMLBXHKWFO-UHFFFAOYSA-N 4-methylbenzenecarbothiohydrazide Chemical compound CC1=CC=C(C(=S)NN)C=C1 ACNALMLBXHKWFO-UHFFFAOYSA-N 0.000 description 2
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 2
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
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- 238000005886 esterification reaction Methods 0.000 description 2
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- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
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- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
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- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
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- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 1
- KYKPMNVLZRQRHZ-UHFFFAOYSA-N 3-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC(C#N)=C1 KYKPMNVLZRQRHZ-UHFFFAOYSA-N 0.000 description 1
- NQEWXLVDAVTOHM-UHFFFAOYSA-N 3-nitrobenzohydrazide Chemical compound NNC(=O)C1=CC=CC([N+]([O-])=O)=C1 NQEWXLVDAVTOHM-UHFFFAOYSA-N 0.000 description 1
- ALEVUYMOJKJJSA-UHFFFAOYSA-N 4-hydroxy-2-propylbenzoic acid Chemical class CCCC1=CC(O)=CC=C1C(O)=O ALEVUYMOJKJJSA-UHFFFAOYSA-N 0.000 description 1
- PJHWTWHVCOZCPU-UHFFFAOYSA-N 4-methylbenzenecarbothioic s-acid Chemical compound CC1=CC=C(C(O)=S)C=C1 PJHWTWHVCOZCPU-UHFFFAOYSA-N 0.000 description 1
- VRRLZUXQTZOCKJ-UHFFFAOYSA-N 5-methyl-3-phenyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(C=2C=CC=CC=2)=N1 VRRLZUXQTZOCKJ-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
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- 208000031462 Bovine Mastitis Diseases 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical compound C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
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- LXCYSACZTOKNNS-UHFFFAOYSA-N diethoxy(oxo)phosphanium Chemical compound CCO[P+](=O)OCC LXCYSACZTOKNNS-UHFFFAOYSA-N 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
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- 235000019197 fats Nutrition 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
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- SKTSVWWOAIAIKI-UHFFFAOYSA-N furan-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CO1 SKTSVWWOAIAIKI-UHFFFAOYSA-N 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
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- XOVWENKUOYOTSR-UHFFFAOYSA-N methyl 9-aminononanoate Chemical compound COC(=O)CCCCCCCCN XOVWENKUOYOTSR-UHFFFAOYSA-N 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
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- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- KFUSANSHCADHNJ-UHFFFAOYSA-N pyridine-3-carbohydrazide Chemical compound NNC(=O)C1=CC=CN=C1 KFUSANSHCADHNJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004296 sodium metabisulphite Substances 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
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- 238000003786 synthesis reaction Methods 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
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- SOGBOGBTIKMGFS-UHFFFAOYSA-N thiophene-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CS1 SOGBOGBTIKMGFS-UHFFFAOYSA-N 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
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- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
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- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- 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
- A61P15/14—Drugs for genital or sexual disorders; Contraceptives for lactation disorders, e.g. galactorrhoea
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
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Claims (1)
- ãç¹èš±è«æ±ã®ç¯å²ã ïŒ åŒïŒïŒ ïŒåŒäžããåŒãã¯ãåŒã ãåŒããåŒããŸã㯠ãåŒãããéžã°ããè€çŽ ç°åŒåºã§ããã ããã§R1ã¯ããããäœçŽã¢ã«ãã«ããªãäœçŽã¢
ã«ãã«ã¹ã«ããã«ããžïŒäœçŽïŒã¢ã«ãã«ã¢ãããŸ
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ãŸãã¯ãã³ãžã«ïŒããªãžã«ïŒããšãã«ïŒããªã«ïŒ
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ãã§ããïŒ ãæããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®ååç©ã ïŒ ååç©ãåŒïŒïŒ¢ïŒ ïŒåŒäžR1ã¯ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã§èŠå®ããé
ãã§ããïŒ ãæããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®ååç©ã ïŒ ååç©ãåŒïŒïŒ£ïŒ ïŒåŒäžR1ã¯ç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé ã§èŠå®ããé
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âãã«ã¢ã³âïŒâã€ã«ïŒâïŒïŒïŒïŒïŒâãªããµãž
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ãªãžã«ïŒâïŒïŒïŒïŒïŒâãªããµãžã¢ãŸãŒã«ïŒ¡ïŒ ïŒâïŒïŒâããªã«ïŒâïŒâïŒïŒâãã«ã¢ã³âïŒâ
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âãã«ã¢ã³âïŒâã€ã«ïŒâïŒïŒïŒïŒïŒâãªããµãž
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ãŸãã¯ãã³ãžã«ïŒããªãžã«ïŒããšãã«ïŒããªã«ïŒ
ãŸãã¯äœçŽã¢ã«ã³ãã·ã«ã«ããã«ãŸãã¯ãã®å¡©ã«
ãã眮æãããC1ã10ã¢ã«ãã«ããéžã°ããåºã§
ããïŒãæããååç©ã®æ²»çäžæå¹ãªéããã以
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ç©ã®ãã€ã³ãã©ãºãææãæ²»çããæ¹æ³ã
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5316 | 1983-02-25 | ||
| GB838305316A GB8305316D0 (en) | 1983-02-25 | 1983-02-25 | Compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196889A JPS59196889A (ja) | 1984-11-08 |
| JPH0534357B2 true JPH0534357B2 (ja) | 1993-05-21 |
Family
ID=10538629
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59034093A Granted JPS59196889A (ja) | 1983-02-25 | 1984-02-24 | æèæ§ååç©ããã®è£œæ³åã³ãã®çšé |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4861788A (ja) |
| EP (1) | EP0123378B1 (ja) |
| JP (1) | JPS59196889A (ja) |
| AU (1) | AU579311B2 (ja) |
| CA (1) | CA1240318A (ja) |
| DE (1) | DE3479657D1 (ja) |
| DK (1) | DK96184A (ja) |
| ES (4) | ES8507545A1 (ja) |
| GB (1) | GB8305316D0 (ja) |
| GR (1) | GR79823B (ja) |
| NZ (1) | NZ207261A (ja) |
| ZA (1) | ZA841366B (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8815626D0 (en) * | 1988-06-30 | 1988-08-03 | Beecham Group Plc | Novel compounds |
| IL94051A0 (en) * | 1989-04-12 | 1991-01-31 | Beecham Group Plc | 1-normon-2-yl-heterocycles,process for their preparation and pharmaceutical compositions containing them |
| GB8928839D0 (en) * | 1989-12-21 | 1990-02-28 | Beecham Group Plc | Novel compounds |
| GB9325832D0 (en) * | 1993-12-17 | 1994-02-23 | Smithkline Beecham Plc | Novel compounds |
| US6951946B2 (en) * | 2002-03-19 | 2005-10-04 | Lexicon Pharmaceuticals, Inc. | Large scale synthesis of 1,2,4- and 1,3,4-oxadiazole carboxylates |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2860726D1 (en) * | 1977-11-05 | 1981-08-27 | Beecham Group Plc | Antibacterially active amides, process for their preparation and pharmaceutical compositions containing said amides |
| EP0045150A1 (en) * | 1980-07-24 | 1982-02-03 | Beecham Group Plc | Antibacterial compounds, processes for their preparation and composititions containing them |
| PT73431B (en) * | 1980-08-02 | 1982-10-08 | Beecham Group Plc | Antibacterial compounds processes for their preparation and compositions containing them |
| US4436751A (en) * | 1980-12-31 | 1984-03-13 | Beecham Group Limited | Nitrobenzyl monates antibacterial compounds |
| EP0087953B1 (en) * | 1982-02-27 | 1988-04-27 | Beecham Group Plc | Antibacterial 1-normon-2-yl-heterocyclic compounds |
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1983
- 1983-02-25 GB GB838305316A patent/GB8305316D0/en active Pending
-
1984
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- 1984-02-16 EP EP84300991A patent/EP0123378B1/en not_active Expired
- 1984-02-23 CA CA000448133A patent/CA1240318A/en not_active Expired
- 1984-02-23 DK DK96184A patent/DK96184A/da not_active Application Discontinuation
- 1984-02-23 AU AU24860/84A patent/AU579311B2/en not_active Ceased
- 1984-02-23 NZ NZ207261A patent/NZ207261A/en unknown
- 1984-02-23 GR GR73908A patent/GR79823B/el unknown
- 1984-02-24 JP JP59034093A patent/JPS59196889A/ja active Granted
- 1984-02-24 ES ES530030A patent/ES8507545A1/es not_active Expired
- 1984-02-24 ZA ZA841366A patent/ZA841366B/xx unknown
- 1984-12-17 ES ES538698A patent/ES538698A0/es active Granted
- 1984-12-17 ES ES538699A patent/ES538699A0/es active Granted
- 1984-12-17 ES ES538697A patent/ES8601980A1/es not_active Expired
-
1987
- 1987-01-30 US US07/008,893 patent/US4861788A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| ES538697A0 (es) | 1985-11-01 |
| GB8305316D0 (en) | 1983-03-30 |
| US4861788A (en) | 1989-08-29 |
| EP0123378A2 (en) | 1984-10-31 |
| ES8601975A1 (es) | 1985-11-01 |
| DK96184A (da) | 1984-08-26 |
| ES8601981A1 (es) | 1985-11-01 |
| CA1240318A (en) | 1988-08-09 |
| ZA841366B (en) | 1985-01-30 |
| EP0123378B1 (en) | 1989-09-06 |
| EP0123378A3 (en) | 1985-09-18 |
| ES538699A0 (es) | 1985-11-01 |
| ES530030A0 (es) | 1985-09-01 |
| NZ207261A (en) | 1987-10-30 |
| ES8601980A1 (es) | 1985-11-01 |
| JPS59196889A (ja) | 1984-11-08 |
| AU579311B2 (en) | 1988-11-24 |
| DE3479657D1 (en) | 1989-10-12 |
| GR79823B (ja) | 1984-10-31 |
| ES538698A0 (es) | 1985-11-01 |
| ES8507545A1 (es) | 1985-09-01 |
| AU2486084A (en) | 1984-08-30 |
| DK96184D0 (da) | 1984-02-23 |
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