GB1596383A - Isoxazole derivatives process for their manufacture and preparations containing these compounds - Google Patents
Isoxazole derivatives process for their manufacture and preparations containing these compounds Download PDFInfo
- Publication number
- GB1596383A GB1596383A GB5034777A GB5034777A GB1596383A GB 1596383 A GB1596383 A GB 1596383A GB 5034777 A GB5034777 A GB 5034777A GB 5034777 A GB5034777 A GB 5034777A GB 1596383 A GB1596383 A GB 1596383A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- formula
- radical
- unsubstituted
- methylisoxazole
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000002545 isoxazoles Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 nitro, hydroxyl Chemical group 0.000 claims abstract description 44
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000005864 Sulphur Substances 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 3
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 238000000354 decomposition reaction Methods 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 7
- 230000008018 melting Effects 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 9
- 150000002148 esters Chemical class 0.000 abstract description 4
- RRGRQQFUASVDPO-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxamide Chemical class CC=1ON=CC=1C(N)=O RRGRQQFUASVDPO-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001412 amines Chemical class 0.000 abstract description 2
- 230000000202 analgesic effect Effects 0.000 abstract description 2
- 230000001754 anti-pyretic effect Effects 0.000 abstract description 2
- 239000002221 antipyretic Substances 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 230000002496 gastric effect Effects 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- DIFJDTRJMXNHQY-UHFFFAOYSA-N (2,4-dichlorophenyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical compound O1N=CC(C(=O)OC=2C(=CC(Cl)=CC=2)Cl)=C1C DIFJDTRJMXNHQY-UHFFFAOYSA-N 0.000 description 9
- ZKAQPVQEYCFRTK-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carbonyl chloride Chemical compound CC=1ON=CC=1C(Cl)=O ZKAQPVQEYCFRTK-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VQBXUKGMJCPBMF-UHFFFAOYSA-N 5-methyl-1,2-oxazole-4-carboxylic acid Chemical compound CC=1ON=CC=1C(O)=O VQBXUKGMJCPBMF-UHFFFAOYSA-N 0.000 description 6
- HYUZHACAFWKOCL-UHFFFAOYSA-N phenylmethoxycarbonyl 5-methyl-1,2-oxazole-4-carboxylate Chemical compound CC1=C(C=NO1)C(=O)OC(=O)OCC1=CC=CC=C1 HYUZHACAFWKOCL-UHFFFAOYSA-N 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- WGOLHUGPTDEKCF-UHFFFAOYSA-N 5-bromopyridin-2-amine Chemical compound NC1=CC=C(Br)C=N1 WGOLHUGPTDEKCF-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- ZINWLWNICFZQQO-UHFFFAOYSA-N n-(5-bromopyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=CC(Br)=CC=2)=C1C ZINWLWNICFZQQO-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZSOSULCXAHAKEN-UHFFFAOYSA-N (5-methyl-1,2-oxazole-4-carbonyl) 5-methyl-1,2-oxazole-4-carboxylate Chemical class O1N=CC(C(=O)OC(=O)C2=C(ON=C2)C)=C1C ZSOSULCXAHAKEN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SLMHHOVQRSSRCV-UHFFFAOYSA-N 2,3-dibromopyridine Chemical compound BrC1=CC=CN=C1Br SLMHHOVQRSSRCV-UHFFFAOYSA-N 0.000 description 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
- 229940018167 2-amino-5-nitrothiazole Drugs 0.000 description 1
- JWYUFVNJZUSCSM-UHFFFAOYSA-N 2-aminobenzimidazole Chemical compound C1=CC=C2NC(N)=NC2=C1 JWYUFVNJZUSCSM-UHFFFAOYSA-N 0.000 description 1
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 description 1
- MEQBJJUWDCYIAB-UHFFFAOYSA-N 2-chloropyridin-3-amine Chemical compound NC1=CC=CN=C1Cl MEQBJJUWDCYIAB-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- REGFWZVTTFGQOJ-UHFFFAOYSA-N 4,5-dihydro-1,3-thiazol-2-amine Chemical compound NC1=NCCS1 REGFWZVTTFGQOJ-UHFFFAOYSA-N 0.000 description 1
- OEQQFQXMCPMEIH-UHFFFAOYSA-N 4-chloro-1,3-benzothiazol-2-amine Chemical compound C1=CC=C2SC(N)=NC2=C1Cl OEQQFQXMCPMEIH-UHFFFAOYSA-N 0.000 description 1
- OUQMXTJYCAJLGO-UHFFFAOYSA-N 4-methyl-1,3-thiazol-2-amine Chemical compound CC1=CSC(N)=N1 OUQMXTJYCAJLGO-UHFFFAOYSA-N 0.000 description 1
- HFOFPDGUBCVRIQ-UHFFFAOYSA-N 4-methylthiophen-3-amine Chemical compound CC1=CSC=C1N HFOFPDGUBCVRIQ-UHFFFAOYSA-N 0.000 description 1
- XFDCNXIWKCIBAE-UHFFFAOYSA-N 5-bromo-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.NC1=NC=C(Br)S1 XFDCNXIWKCIBAE-UHFFFAOYSA-N 0.000 description 1
- SWQWTDAWUSBMGA-UHFFFAOYSA-N 5-chloro-1,3-thiazol-2-amine Chemical compound NC1=NC=C(Cl)S1 SWQWTDAWUSBMGA-UHFFFAOYSA-N 0.000 description 1
- MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 1
- HIKGTJQVRNMKRY-UHFFFAOYSA-N 5-methyl-N-(4-methylthiophen-3-yl)-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC1=CSC=C1C HIKGTJQVRNMKRY-UHFFFAOYSA-N 0.000 description 1
- QDGQPHTUGDESHL-UHFFFAOYSA-N 5-methyl-n-(5-nitro-1,3-thiazol-2-yl)-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.O1N=CC(C(=O)NC=2SC(=CN=2)[N+]([O-])=O)=C1C QDGQPHTUGDESHL-UHFFFAOYSA-N 0.000 description 1
- ZJZOIMSLULDHKI-UHFFFAOYSA-N 5-methyl-n-(5-nitropyridin-2-yl)-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=CC(=CC=2)[N+]([O-])=O)=C1C ZJZOIMSLULDHKI-UHFFFAOYSA-N 0.000 description 1
- ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 5-methyl-n-phenyl-1,2-oxazole-4-carboxamide Chemical class O1N=CC(C(=O)NC=2C=CC=CC=2)=C1C ZYEWRBNSDKQNSJ-UHFFFAOYSA-N 0.000 description 1
- IVMLITIRBUUIEX-UHFFFAOYSA-N 5-methyl-n-pyridin-2-yl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.O1N=CC(C(=O)NC=2N=CC=CC=2)=C1C IVMLITIRBUUIEX-UHFFFAOYSA-N 0.000 description 1
- KHKCNKQUCRMCEW-UHFFFAOYSA-N 5-methyl-n-pyridin-3-yl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.O1N=CC(C(=O)NC=2C=NC=CC=2)=C1C KHKCNKQUCRMCEW-UHFFFAOYSA-N 0.000 description 1
- WQMODDXDPPDGIM-UHFFFAOYSA-N 5-methyl-n-pyridin-4-yl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.O1N=CC(C(=O)NC=2C=CN=CC=2)=C1C WQMODDXDPPDGIM-UHFFFAOYSA-N 0.000 description 1
- UGSBCCAHDVCHGI-UHFFFAOYSA-N 5-nitropyridin-2-amine Chemical compound NC1=CC=C([N+]([O-])=O)C=N1 UGSBCCAHDVCHGI-UHFFFAOYSA-N 0.000 description 1
- VFGRNTYELNYSKJ-UHFFFAOYSA-N 6-amino-1,3-dimethylpyrimidine-2,4-dione Chemical compound CN1C(N)=CC(=O)N(C)C1=O VFGRNTYELNYSKJ-UHFFFAOYSA-N 0.000 description 1
- KOYJWFGMEBETBU-UHFFFAOYSA-N 6-ethoxy-1,3-benzothiazol-2-amine Chemical compound CCOC1=CC=C2N=C(N)SC2=C1 KOYJWFGMEBETBU-UHFFFAOYSA-N 0.000 description 1
- KZHGPDSVHSDCMX-UHFFFAOYSA-N 6-methoxy-1,3-benzothiazol-2-amine Chemical compound COC1=CC=C2N=C(N)SC2=C1 KZHGPDSVHSDCMX-UHFFFAOYSA-N 0.000 description 1
- UUVDJIWRSIJEBS-UHFFFAOYSA-N 6-methoxypyridin-3-amine Chemical compound COC1=CC=C(N)C=N1 UUVDJIWRSIJEBS-UHFFFAOYSA-N 0.000 description 1
- HHJDZLCAIVTTRY-UHFFFAOYSA-N Cl.CC1=C(C=NO1)C(=O)NC=1SCCN1 Chemical compound Cl.CC1=C(C=NO1)C(=O)NC=1SCCN1 HHJDZLCAIVTTRY-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- DDFNLSDLPRZWRP-UHFFFAOYSA-N N-(1,3-dimethyl-2,6-dioxopyrimidin-4-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC1=CC(N(C(N1C)=O)C)=O DDFNLSDLPRZWRP-UHFFFAOYSA-N 0.000 description 1
- HSJXMLWGJMWMMO-UHFFFAOYSA-N N-(1H-benzimidazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide hydrochloride Chemical compound Cl.CC1=C(C=NO1)C(=O)NC=1NC2=C(N1)C=CC=C2 HSJXMLWGJMWMMO-UHFFFAOYSA-N 0.000 description 1
- XGIWVQRGZMQHOL-UHFFFAOYSA-N N-(5-chloro-1,3-thiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC=1SC(=CN1)Cl XGIWVQRGZMQHOL-UHFFFAOYSA-N 0.000 description 1
- FUJJDUPFBHNJHA-UHFFFAOYSA-N N-(6-ethoxy-1,3-benzothiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC=1SC2=C(N1)C=CC(=C2)OCC FUJJDUPFBHNJHA-UHFFFAOYSA-N 0.000 description 1
- YTEZDKGRPNRFNG-UHFFFAOYSA-N N-(6-methoxy-1,3-benzothiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC=1SC2=C(N1)C=CC(=C2)OC YTEZDKGRPNRFNG-UHFFFAOYSA-N 0.000 description 1
- HKLILPGXUIHYHH-UHFFFAOYSA-N N-(6-methoxypyridin-3-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound CC1=C(C=NO1)C(=O)NC=1C=CC(=NC1)OC HKLILPGXUIHYHH-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- YGCODSQDUUUKIV-UHFFFAOYSA-N Zoxazolamine Chemical compound ClC1=CC=C2OC(N)=NC2=C1 YGCODSQDUUUKIV-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 230000001741 anti-phlogistic effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical class C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- GBXWAENVCUHDMN-UHFFFAOYSA-N n-(1,3-benzothiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide;hydrochloride Chemical compound Cl.O1N=CC(C(=O)NC=2SC3=CC=CC=C3N=2)=C1C GBXWAENVCUHDMN-UHFFFAOYSA-N 0.000 description 1
- CWHKJJSMEOYBOQ-UHFFFAOYSA-N n-(2-chloropyridin-3-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C(=NC=CC=2)Cl)=C1C CWHKJJSMEOYBOQ-UHFFFAOYSA-N 0.000 description 1
- DLHLVDVLFFKGNH-UHFFFAOYSA-N n-(3,5-dibromopyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2C(=CC(Br)=CN=2)Br)=C1C DLHLVDVLFFKGNH-UHFFFAOYSA-N 0.000 description 1
- YFDJWJKEOAAFML-UHFFFAOYSA-N n-(4-chloro-1,3-benzothiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=C1C YFDJWJKEOAAFML-UHFFFAOYSA-N 0.000 description 1
- XMAJBHKZXZYOJB-UHFFFAOYSA-N n-(5-bromo-1,3-thiazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2SC(Br)=CN=2)=C1C XMAJBHKZXZYOJB-UHFFFAOYSA-N 0.000 description 1
- BTWFRBYPZKLTMS-UHFFFAOYSA-N n-(5-chloro-1,3-benzoxazol-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2OC3=CC=C(Cl)C=C3N=2)=C1C BTWFRBYPZKLTMS-UHFFFAOYSA-N 0.000 description 1
- QHDXHVAUPGUMRX-UHFFFAOYSA-N n-(5-chloropyridin-2-yl)-5-methyl-1,2-oxazole-4-carboxamide Chemical compound O1N=CC(C(=O)NC=2N=CC(Cl)=CC=2)=C1C QHDXHVAUPGUMRX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- LGVXPSMGABFXST-UHFFFAOYSA-N phenyl 5-methyl-1,2-oxazole-4-carboxylate Chemical class C1(=CC=CC=C1)OC(=O)C=1C=NOC=1C LGVXPSMGABFXST-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655009 DE2655009A1 (de) | 1976-12-04 | 1976-12-04 | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1596383A true GB1596383A (en) | 1981-08-26 |
Family
ID=5994666
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5034777A Expired GB1596383A (en) | 1976-12-04 | 1977-12-02 | Isoxazole derivatives process for their manufacture and preparations containing these compounds |
Country Status (13)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892963A (en) * | 1986-08-08 | 1990-01-09 | Lilly Industries Limited | N-phenyl amide compounds |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| US4983619A (en) * | 1986-08-08 | 1991-01-08 | Lilly Industries Limited | Pharmaceutical compounds |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| CN103772376A (zh) * | 2012-10-24 | 2014-05-07 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| US10195181B2 (en) | 2014-05-14 | 2019-02-05 | Novartis Ag | Carboxamide derivatives |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035285A3 (en) * | 1979-08-17 | 1981-10-14 | American Cyanamid Company | Novel isoxazole carboxylic acid phenyl esters, pharmaceutical compositions containing certain of said esters, and process for preparing said esters |
| JPS55500866A (enrdf_load_stackoverflow) * | 1978-11-03 | 1980-10-30 | ||
| DE2854438A1 (de) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | Isoxazolderivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende mittel und ihre verwendung |
| DE3247454A1 (de) * | 1982-12-22 | 1984-06-28 | Laboratorios Bago S.A., Buenos Aires | Substituierte 3-phenyl-5-methyl-isoxazol-4-carboxy-anilide, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| IT1228288B (it) * | 1989-01-09 | 1991-06-07 | Zambon Spa | Composti ad attivita' antiserotoninica |
| US5001124A (en) * | 1990-02-02 | 1991-03-19 | Syntex (U.S.A.) Inc. | 4-isoxazolecarboxamide derivatives |
| ZA913762B (en) | 1990-05-18 | 1992-01-29 | Hoechst Ag | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides,pharmaceuticals containing these compounds and their use |
| CA2083179C (en) * | 1990-05-18 | 2001-10-23 | Robert Ryder Bartlett | Isoxazole-4-carboxamides and hydroxyalkylidenecyanoacetamides, pharmaceuticals containing these compounds and their use |
| US20170088545A1 (en) * | 2014-05-14 | 2017-03-30 | Novartis Ag | Carboxamide inhibitors |
-
1976
- 1976-12-04 DE DE19762655009 patent/DE2655009A1/de active Granted
-
1977
- 1977-11-15 CH CH1393477A patent/CH608498A5/xx not_active IP Right Cessation
- 1977-11-29 NL NL7713151A patent/NL7713151A/xx not_active Application Discontinuation
- 1977-12-02 LU LU78628A patent/LU78628A1/xx unknown
- 1977-12-02 GB GB5034777A patent/GB1596383A/en not_active Expired
- 1977-12-02 IE IE245277A patent/IE46269B1/en unknown
- 1977-12-02 AT AT866377A patent/AT362366B/de not_active IP Right Cessation
- 1977-12-02 CA CA292,302A patent/CA1102341A/en not_active Expired
- 1977-12-02 IT IT3035277A patent/IT1126219B/it active
- 1977-12-02 DK DK538677A patent/DK538677A/da unknown
- 1977-12-03 JP JP14562277A patent/JPS5371070A/ja active Pending
- 1977-12-05 BE BE183170A patent/BE861503R/xx not_active IP Right Cessation
- 1977-12-05 FR FR7736547A patent/FR2372830A2/fr active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4892963A (en) * | 1986-08-08 | 1990-01-09 | Lilly Industries Limited | N-phenyl amide compounds |
| US4983619A (en) * | 1986-08-08 | 1991-01-08 | Lilly Industries Limited | Pharmaceutical compounds |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| US7338956B2 (en) * | 2002-08-07 | 2008-03-04 | Sanofi-Aventis Deutschland Gmbh | Acylamino-substituted heteroaromatic compounds and their use as pharmaceuticals |
| CN103772376A (zh) * | 2012-10-24 | 2014-05-07 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| CN103772376B (zh) * | 2012-10-24 | 2017-01-11 | 中国医学科学院医药生物技术研究所 | 取代的苯并-1,3-杂唑类化合物、其制备方法及用途 |
| US10195181B2 (en) | 2014-05-14 | 2019-02-05 | Novartis Ag | Carboxamide derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372830A2 (fr) | 1978-06-30 |
| DK538677A (da) | 1978-06-05 |
| IE46269B1 (en) | 1983-04-20 |
| AT362366B (de) | 1981-05-11 |
| CA1102341A (en) | 1981-06-02 |
| IT1126219B (it) | 1986-05-14 |
| FR2372830B2 (enrdf_load_stackoverflow) | 1980-06-20 |
| NL7713151A (nl) | 1978-06-06 |
| CH608498A5 (en) | 1979-01-15 |
| ATA866377A (de) | 1980-10-15 |
| LU78628A1 (enrdf_load_stackoverflow) | 1978-07-11 |
| JPS5371070A (en) | 1978-06-24 |
| DE2655009C2 (enrdf_load_stackoverflow) | 1990-03-29 |
| IE46269L (en) | 1978-06-04 |
| BE861503R (fr) | 1978-06-05 |
| DE2655009A1 (de) | 1978-06-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19960603 |