CA1294274C - Methode de traitement de la tension musculaire, de la spasticite musculaire et de l'anxiete a l'aide de 3-aryloxy-azetidinecarboxamides - Google Patents
Methode de traitement de la tension musculaire, de la spasticite musculaire et de l'anxiete a l'aide de 3-aryloxy-azetidinecarboxamidesInfo
- Publication number
- CA1294274C CA1294274C CA000502877A CA502877A CA1294274C CA 1294274 C CA1294274 C CA 1294274C CA 000502877 A CA000502877 A CA 000502877A CA 502877 A CA502877 A CA 502877A CA 1294274 C CA1294274 C CA 1294274C
- Authority
- CA
- Canada
- Prior art keywords
- phenoxy
- trifluoromethyl
- methyl
- compound
- azetidinecarboxamide
- 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
- 238000000034 method Methods 0.000 title claims abstract description 110
- 208000019901 Anxiety disease Diseases 0.000 title claims abstract description 15
- 230000036506 anxiety Effects 0.000 title claims abstract description 15
- 206010049816 Muscle tightness Diseases 0.000 title claims abstract description 12
- 208000008238 Muscle Spasticity Diseases 0.000 title claims description 11
- -1 lower-alkyl Chemical group 0.000 claims abstract description 64
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 45
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 23
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 16
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 15
- 241001465754 Metazoa Species 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 11
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims abstract description 10
- 125000005843 halogen group Chemical group 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000011593 sulfur Substances 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract 18
- 150000001875 compounds Chemical class 0.000 claims description 116
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 59
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 46
- 239000002253 acid Substances 0.000 claims description 39
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 37
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 8
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 claims description 8
- 230000037396 body weight Effects 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000003254 radicals Chemical class 0.000 claims description 7
- CCDAHKDEKOTDGR-UHFFFAOYSA-N 3-phenoxyazetidine Chemical compound C1NCC1OC1=CC=CC=C1 CCDAHKDEKOTDGR-UHFFFAOYSA-N 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- PFCBHFDNVFQUJI-UHFFFAOYSA-N 3-methylbut-2-en-1-amine Chemical compound CC(C)=CCN PFCBHFDNVFQUJI-UHFFFAOYSA-N 0.000 claims description 4
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- CMUOJBJRZUHRMU-UHFFFAOYSA-N nitrourea Chemical compound NC(=O)N[N+]([O-])=O CMUOJBJRZUHRMU-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- QFUSOYKIDBRREL-NSCUHMNNSA-N (e)-but-2-en-1-amine Chemical compound C\C=C\CN QFUSOYKIDBRREL-NSCUHMNNSA-N 0.000 claims description 3
- VXDHQYLFEYUMFY-UHFFFAOYSA-N 2-methylprop-2-en-1-amine Chemical compound CC(=C)CN VXDHQYLFEYUMFY-UHFFFAOYSA-N 0.000 claims description 3
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 3
- 125000002393 azetidinyl group Chemical group 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- QPBVKSLJBRCKIF-UHFFFAOYSA-N n,n-diethyl-3-isothiocyanatopropan-1-amine Chemical compound CCN(CC)CCCN=C=S QPBVKSLJBRCKIF-UHFFFAOYSA-N 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- UULUECCNPPJFBU-UHFFFAOYSA-N 2-isothiocyanato-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1N=C=S UULUECCNPPJFBU-UHFFFAOYSA-N 0.000 claims description 2
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 claims description 2
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 claims description 2
- ADXWWNMHZFPXKW-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenoxy]azetidine Chemical compound FC(F)(F)C1=CC=CC(OC2CNC2)=C1 ADXWWNMHZFPXKW-UHFFFAOYSA-N 0.000 claims 15
- RKANEZKQFZAZHZ-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenoxy]azetidine Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CNC1 RKANEZKQFZAZHZ-UHFFFAOYSA-N 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims 4
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 claims 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 4
- 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims 4
- FCFCOZCXFMJOIC-OIBJUYFYSA-N (2s,3r)-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine Chemical compound C[C@@H]1NC[C@H]1OC1=CC=CC(C(F)(F)F)=C1 FCFCOZCXFMJOIC-OIBJUYFYSA-N 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 3
- HBJYHGBMEHJJOL-UHFFFAOYSA-N 2-[1-(1-phenylethyl)azetidin-3-yl]oxypyridine Chemical compound C=1C=CC=CC=1C(C)N(C1)CC1OC1=CC=CC=N1 HBJYHGBMEHJJOL-UHFFFAOYSA-N 0.000 claims 3
- GIGBKRYORFPUJJ-UHFFFAOYSA-N 3-(3-chlorophenoxy)azetidine-1-carbonyl chloride Chemical compound C1N(C(=O)Cl)CC1OC1=CC=CC(Cl)=C1 GIGBKRYORFPUJJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000068 chlorophenyl group Chemical group 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- XSUIKYPOQZDEOG-OIBJUYFYSA-N (2s,3r)-2-methyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(N)=O)[C@@H](C)[C@@H]1OC1=CC=CC(C(F)(F)F)=C1 XSUIKYPOQZDEOG-OIBJUYFYSA-N 0.000 claims 2
- SYPFZJKKALJQSR-GXFFZTMASA-N (2s,3r)-2-methyl-n-prop-2-enyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NCC=C)[C@@H](C)[C@@H]1OC1=CC=CC(C(F)(F)F)=C1 SYPFZJKKALJQSR-GXFFZTMASA-N 0.000 claims 2
- RZEDFQAVBLOJCZ-GZMMTYOYSA-N (2s,3r)-n,2-dimethyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C[C@@H]1N(C(=O)NC)C[C@H]1OC1=CC=CC(C(F)(F)F)=C1 RZEDFQAVBLOJCZ-GZMMTYOYSA-N 0.000 claims 2
- QPRDRWVXFKBVNC-UHFFFAOYSA-N 3-(3-chlorophenoxy)-n-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1OC1=CC=CC(Cl)=C1 QPRDRWVXFKBVNC-UHFFFAOYSA-N 0.000 claims 2
- MFEIFYBOANETOF-UHFFFAOYSA-N 3-(3-chlorophenoxy)-n-prop-2-enylazetidine-1-carboxamide Chemical compound ClC1=CC=CC(OC2CN(C2)C(=O)NCC=C)=C1 MFEIFYBOANETOF-UHFFFAOYSA-N 0.000 claims 2
- CBVMWQNDRJMCEB-UHFFFAOYSA-N 3-(3-fluorophenoxy)-n-methylazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1OC1=CC=CC(F)=C1 CBVMWQNDRJMCEB-UHFFFAOYSA-N 0.000 claims 2
- SJTBRFHBXDZMPS-UHFFFAOYSA-N 3-fluorophenol Chemical compound OC1=CC=CC(F)=C1 SJTBRFHBXDZMPS-UHFFFAOYSA-N 0.000 claims 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- UEPPOGPDSWZLLR-UHFFFAOYSA-N imidazol-1-yl-[3-[4-(trifluoromethyl)phenoxy]azetidin-1-yl]methanone Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)N2C=NC=C2)C1 UEPPOGPDSWZLLR-UHFFFAOYSA-N 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- HMIPZRSSZUEYBQ-UHFFFAOYSA-N n,n-diethyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)N(CC)CC)CC1OC1=CC=CC(C(F)(F)F)=C1 HMIPZRSSZUEYBQ-UHFFFAOYSA-N 0.000 claims 2
- XBATZUYJQTUPLP-UHFFFAOYSA-N n,n-dimethyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)N(C)C)CC1OC1=CC=CC(C(F)(F)F)=C1 XBATZUYJQTUPLP-UHFFFAOYSA-N 0.000 claims 2
- GLHHXODPLUSSIJ-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carbothioamide Chemical compound CC1=CC=CC(C)=C1NC(=S)N1CC(OC=2C=C(C=CC=2)C(F)(F)F)C1 GLHHXODPLUSSIJ-UHFFFAOYSA-N 0.000 claims 2
- FWTJJBXHVPRPSF-UHFFFAOYSA-N n-(2-methylprop-2-enyl)-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NCC(=C)C)CC1OC1=CC=CC(C(F)(F)F)=C1 FWTJJBXHVPRPSF-UHFFFAOYSA-N 0.000 claims 2
- MQARANLCIMLXGF-UHFFFAOYSA-N n-(2-methylprop-2-enyl)-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NCC(=C)C)CC1OC1=CC=C(C(F)(F)F)C=C1 MQARANLCIMLXGF-UHFFFAOYSA-N 0.000 claims 2
- XQILPDVSZBCNKN-UHFFFAOYSA-N n-(3-methylbut-2-enyl)-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NCC=C(C)C)CC1OC1=CC=CC(C(F)(F)F)=C1 XQILPDVSZBCNKN-UHFFFAOYSA-N 0.000 claims 2
- SEALWFDYCNCLNY-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NCC2CC2)=C1 SEALWFDYCNCLNY-UHFFFAOYSA-N 0.000 claims 2
- KYMQEKDBADKHBY-UHFFFAOYSA-N n-(cyclopropylmethyl)-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)NCC2CC2)C1 KYMQEKDBADKHBY-UHFFFAOYSA-N 0.000 claims 2
- GDPMPUCKDZXLRK-NSCUHMNNSA-N n-[(e)-but-2-enyl]-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1N(C(=O)NC/C=C/C)CC1OC1=CC=CC(C(F)(F)F)=C1 GDPMPUCKDZXLRK-NSCUHMNNSA-N 0.000 claims 2
- XYTDLEDSAYYSHI-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carbothioamide Chemical compound C1N(C(=S)NCCCN(CC)CC)CC1OC1=CC=CC(C(F)(F)F)=C1 XYTDLEDSAYYSHI-UHFFFAOYSA-N 0.000 claims 2
- XJZPWSFVNVZQIC-UHFFFAOYSA-N n-[3-(diethylamino)propyl]-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carbothioamide Chemical compound C1N(C(=S)NCCCN(CC)CC)CC1OC1=CC=C(C(F)(F)F)C=C1 XJZPWSFVNVZQIC-UHFFFAOYSA-N 0.000 claims 2
- WQDZXCYGRNEPDO-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carbothioamide Chemical compound C1N(C(=S)NCCCN(C)C)CC1OC1=CC=CC(C(F)(F)F)=C1 WQDZXCYGRNEPDO-UHFFFAOYSA-N 0.000 claims 2
- ZLCBZXPTJIWYLB-UHFFFAOYSA-N n-benzyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NCC=2C=CC=CC=2)=C1 ZLCBZXPTJIWYLB-UHFFFAOYSA-N 0.000 claims 2
- KUYNTRFCAQCQJH-UHFFFAOYSA-N n-cyclohexyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NC2CCCCC2)=C1 KUYNTRFCAQCQJH-UHFFFAOYSA-N 0.000 claims 2
- RUIRVJJAJMNBAP-UHFFFAOYSA-N n-cyclopropyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NC2CC2)=C1 RUIRVJJAJMNBAP-UHFFFAOYSA-N 0.000 claims 2
- LWSGVXPNSPXCRK-UHFFFAOYSA-N n-cyclopropyl-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)NC2CC2)C1 LWSGVXPNSPXCRK-UHFFFAOYSA-N 0.000 claims 2
- JWBUJRUMOWMXCS-UHFFFAOYSA-N n-methyl-3-pyridin-2-yloxyazetidine-1-carboxamide Chemical compound C1N(C(=O)NC)CC1OC1=CC=CC=N1 JWBUJRUMOWMXCS-UHFFFAOYSA-N 0.000 claims 2
- JTFRITVGJZKYBU-UHFFFAOYSA-N n-phenyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NC=2C=CC=CC=2)=C1 JTFRITVGJZKYBU-UHFFFAOYSA-N 0.000 claims 2
- GACNVLGLEIQNGN-UHFFFAOYSA-N n-phenyl-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)NC=2C=CC=CC=2)C1 GACNVLGLEIQNGN-UHFFFAOYSA-N 0.000 claims 2
- IMBLCCKKMAIZEU-UHFFFAOYSA-N n-prop-2-enyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NCC=C)=C1 IMBLCCKKMAIZEU-UHFFFAOYSA-N 0.000 claims 2
- ZUTYSNQEFFGMKG-UHFFFAOYSA-N n-prop-2-enyl-3-pyridin-2-yloxyazetidine-1-carboxamide Chemical compound C1N(C(=O)NCC=C)CC1OC1=CC=CC=N1 ZUTYSNQEFFGMKG-UHFFFAOYSA-N 0.000 claims 2
- UYKNKYCPRSVIIG-UHFFFAOYSA-N n-prop-2-ynyl-3-[3-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CN(C2)C(=O)NCC#C)=C1 UYKNKYCPRSVIIG-UHFFFAOYSA-N 0.000 claims 2
- LARJYCSCHUFOPG-UHFFFAOYSA-N n-prop-2-ynyl-3-[4-(trifluoromethyl)phenoxy]azetidine-1-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1OC1CN(C(=O)NCC#C)C1 LARJYCSCHUFOPG-UHFFFAOYSA-N 0.000 claims 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims 2
- 150000003141 primary amines Chemical class 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- SUCGVQHNGIQXGD-UHFFFAOYSA-N 1,3-dichloro-2-isothiocyanatobenzene Chemical compound ClC1=CC=CC(Cl)=C1N=C=S SUCGVQHNGIQXGD-UHFFFAOYSA-N 0.000 claims 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims 1
- ZOGZOXRETBBBJI-UHFFFAOYSA-N 2-cyclopropylethanamine Chemical compound NCCC1CC1 ZOGZOXRETBBBJI-UHFFFAOYSA-N 0.000 claims 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical compound OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 claims 1
- YTRPOSQFCMQDPK-UHFFFAOYSA-N 3-(3-chlorophenoxy)azetidine-1-carboxamide Chemical compound C1N(C(=O)N)CC1OC1=CC=CC(Cl)=C1 YTRPOSQFCMQDPK-UHFFFAOYSA-N 0.000 claims 1
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- LDXHWJITNCSIJC-UHFFFAOYSA-N 3-isothiocyanato-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCN=C=S LDXHWJITNCSIJC-UHFFFAOYSA-N 0.000 claims 1
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- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70663285A | 1985-02-28 | 1985-02-28 | |
| US706,632 | 1985-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1294274C true CA1294274C (fr) | 1992-01-14 |
Family
ID=24838427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000502877A Expired - Lifetime CA1294274C (fr) | 1985-02-28 | 1986-02-27 | Methode de traitement de la tension musculaire, de la spasticite musculaire et de l'anxiete a l'aide de 3-aryloxy-azetidinecarboxamides |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPH0699386B2 (fr) |
| AU (1) | AU599312B2 (fr) |
| CA (1) | CA1294274C (fr) |
| DK (2) | DK168422B1 (fr) |
| ES (1) | ES8802300A1 (fr) |
| GR (1) | GR860531B (fr) |
| IL (1) | IL77995A (fr) |
| IN (1) | IN162808B (fr) |
| NZ (1) | NZ215312A (fr) |
| PH (1) | PH25525A (fr) |
| PT (1) | PT82118B (fr) |
| ZA (1) | ZA861215B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3641343A1 (de) * | 1986-12-03 | 1988-06-16 | Hoechst Ag | Carbamoylimidazol-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide |
| HUE025411T2 (en) * | 2008-03-04 | 2016-02-29 | Vernalis R&D Ltd | azetidine |
| CN113754541A (zh) * | 2020-06-02 | 2021-12-07 | 深圳湾实验室 | 靶向eb病毒核抗原蛋白的小分子抑制剂、制备方法及其应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4226861A (en) * | 1978-04-18 | 1980-10-07 | A. H. Robins Company, Inc. | N-Lower-alkyl 3-phenoxy-1-azetidinecarboxamides |
| IL68699A (en) * | 1982-08-19 | 1986-08-31 | Robins Co Inc A H | 3-phenoxy-1-azetidine-carboxamides,their preparation and pharmaceutical compositions containing them |
| US4505907A (en) * | 1982-09-02 | 1985-03-19 | A. H. Robins Company, Inc. | N-Formyl and N-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides |
| US4594189A (en) * | 1983-07-06 | 1986-06-10 | A. H. Robins Company, Inc. | Process for preparing 3-phenoxy-1-azetidines and carboxamide derivatives |
-
1986
- 1986-02-10 IN IN90/MAS/86A patent/IN162808B/en unknown
- 1986-02-18 ZA ZA861215A patent/ZA861215B/xx unknown
- 1986-02-21 AU AU53888/86A patent/AU599312B2/en not_active Ceased
- 1986-02-25 GR GR860531A patent/GR860531B/el unknown
- 1986-02-26 IL IL7799586A patent/IL77995A/xx not_active IP Right Cessation
- 1986-02-26 PH PH33452A patent/PH25525A/en unknown
- 1986-02-27 NZ NZ21531286A patent/NZ215312A/xx unknown
- 1986-02-27 DK DK90186A patent/DK168422B1/da not_active IP Right Cessation
- 1986-02-27 CA CA000502877A patent/CA1294274C/fr not_active Expired - Lifetime
- 1986-02-27 ES ES552472A patent/ES8802300A1/es not_active Expired
- 1986-02-28 JP JP61043906A patent/JPH0699386B2/ja not_active Expired - Lifetime
- 1986-02-28 PT PT8211886A patent/PT82118B/pt not_active IP Right Cessation
-
1993
- 1993-03-29 DK DK36893A patent/DK170270B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK90186A (da) | 1986-08-29 |
| AU5388886A (en) | 1986-09-04 |
| IL77995A (en) | 1989-06-30 |
| AU599312B2 (en) | 1990-07-19 |
| JPH0699386B2 (ja) | 1994-12-07 |
| PH25525A (en) | 1991-07-24 |
| NZ215312A (en) | 1990-02-26 |
| DK36893A (da) | 1993-03-29 |
| PT82118A (en) | 1986-03-01 |
| DK36893D0 (da) | 1993-03-29 |
| DK170270B1 (da) | 1995-07-24 |
| DK168422B1 (da) | 1994-03-28 |
| DK90186D0 (da) | 1986-02-27 |
| IN162808B (fr) | 1988-07-09 |
| ES552472A0 (es) | 1987-05-01 |
| JPS61205254A (ja) | 1986-09-11 |
| PT82118B (pt) | 1988-07-01 |
| ES8802300A1 (es) | 1987-05-01 |
| ZA861215B (en) | 1986-10-29 |
| GR860531B (en) | 1986-06-24 |
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| Date | Code | Title | Description |
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| MKLA | Lapsed |