IE921972A1 - Amino-4-aryl-thiazoles with antiasthmatic and¹antiinflammatory activities on the respiratory tract - Google Patents
Amino-4-aryl-thiazoles with antiasthmatic and¹antiinflammatory activities on the respiratory tractInfo
- Publication number
- IE921972A1 IE921972A1 IE197292A IE921972A IE921972A1 IE 921972 A1 IE921972 A1 IE 921972A1 IE 197292 A IE197292 A IE 197292A IE 921972 A IE921972 A IE 921972A IE 921972 A1 IE921972 A1 IE 921972A1
- Authority
- IE
- Ireland
- Prior art keywords
- bis
- thiazol
- piperazine
- pyrrolidin
- aminocarbonyl
- Prior art date
Links
- 210000002345 respiratory system Anatomy 0.000 title abstract description 6
- 230000001088 anti-asthma Effects 0.000 title description 4
- 239000000924 antiasthmatic agent Substances 0.000 title description 3
- 230000000694 effects Effects 0.000 title description 2
- 208000006673 asthma Diseases 0.000 claims abstract description 10
- 206010066091 Bronchial Hyperreactivity Diseases 0.000 claims abstract description 7
- 230000036427 bronchial hyperreactivity Effects 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
- -1 bis(phenyl)methyl Chemical group 0.000 claims description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 14
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 claims description 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical compound NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical compound NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004799 bromophenyl group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 2
- JIQNWFBLYKVZFY-UHFFFAOYSA-N methoxycyclohexatriene Chemical compound COC1=C[C]=CC=C1 JIQNWFBLYKVZFY-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000000068 chlorophenyl group Chemical group 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000004885 piperazines Chemical class 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 282
- 229960005141 piperazine Drugs 0.000 description 141
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 56
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 53
- 229910052799 carbon Inorganic materials 0.000 description 48
- 125000004682 aminothiocarbonyl group Chemical group NC(=S)* 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000003557 thiazoles Chemical class 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- NYIZXMGNIUSNKL-UHFFFAOYSA-N 2,3-diacetyloxybenzoic acid Chemical compound CC(=O)OC1=CC=CC(C(O)=O)=C1OC(C)=O NYIZXMGNIUSNKL-UHFFFAOYSA-N 0.000 description 2
- GLDQAMYCGOIJDV-UHFFFAOYSA-N 2,3-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1O GLDQAMYCGOIJDV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QQPUUIMNKZFCBR-UHFFFAOYSA-N [2-acetyloxy-3-(2-amino-1,3-thiazol-4-yl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC(C=2N=C(N)SC=2)=C1OC(C)=O QQPUUIMNKZFCBR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000035874 hyperreactivity Effects 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 210000004877 mucosa Anatomy 0.000 description 2
- WEYVCQFUGFRXOM-UHFFFAOYSA-N perazine Chemical compound C1CN(C)CCN1CCCN1C2=CC=CC=C2SC2=CC=CC=C21 WEYVCQFUGFRXOM-UHFFFAOYSA-N 0.000 description 2
- 229960002195 perazine Drugs 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229940082044 2,3-dihydroxybenzoic acid Drugs 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- VINOSHDRVYFKLH-UHFFFAOYSA-N 2-n,2-n,5-n,5-n-tetraethyl-6-piperazin-1-ylpyridine-2,5-diamine Chemical compound CCN(CC)C1=CC=C(N(CC)CC)C(N2CCNCC2)=N1 VINOSHDRVYFKLH-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- HRYMMVNAXNCMRR-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)piperazine-1-carboxamide Chemical compound C1CN(C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)CCN1C(=O)NC(SC=1)=NC=1C1=CC=CN=C1 HRYMMVNAXNCMRR-UHFFFAOYSA-N 0.000 description 1
- VPWIGQSHASWZCZ-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(2-fluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound FC1=CC=CC=C1C1=CSC(NC(=S)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 VPWIGQSHASWZCZ-UHFFFAOYSA-N 0.000 description 1
- TYUDERRNGBEGAX-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(3-methoxyphenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound COC1=CC=CC(C=2N=C(NC(=S)N3CCN(CC3)C=3N=C(N=C(C=3)N3CCCC3)N3CCCC3)SC=2)=C1 TYUDERRNGBEGAX-UHFFFAOYSA-N 0.000 description 1
- YLXGLXWRJGMMCC-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(NC(=O)N3CCN(CC3)C=3N=C(N=C(C=3)N3CCCC3)N3CCCC3)SC=2)=C1 YLXGLXWRJGMMCC-UHFFFAOYSA-N 0.000 description 1
- OJPZZIPCGSVVFX-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound C1=CC(F)=CC=C1C1=CSC(NC(=S)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 OJPZZIPCGSVVFX-UHFFFAOYSA-N 0.000 description 1
- GGCVZYNTEZKKKY-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxamide Chemical compound C1=CC(F)=CC=C1C1=CSC(NC(=O)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 GGCVZYNTEZKKKY-UHFFFAOYSA-N 0.000 description 1
- XNQPUPDCTJVCSI-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=S)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 XNQPUPDCTJVCSI-UHFFFAOYSA-N 0.000 description 1
- JFVYBLOPJYLIDS-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=O)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 JFVYBLOPJYLIDS-UHFFFAOYSA-N 0.000 description 1
- VVAHIQFLSSDLNY-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(NC(=S)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 VVAHIQFLSSDLNY-UHFFFAOYSA-N 0.000 description 1
- SIFVZVGPRLASJY-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]piperazine-1-carboxamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CSC(NC(=O)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 SIFVZVGPRLASJY-UHFFFAOYSA-N 0.000 description 1
- KRBKVCZUZHQPNQ-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-(4-phenylsulfanylphenyl)-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound C1CN(C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)CCN1C(=S)NC(SC=1)=NC=1C(C=C1)=CC=C1SC1=CC=CC=C1 KRBKVCZUZHQPNQ-UHFFFAOYSA-N 0.000 description 1
- NKHRHOPMZCAMJK-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(NC(=S)N3CCN(CC3)C=3N=C(N=C(C=3)N3CCCC3)N3CCCC3)SC=2)=C1 NKHRHOPMZCAMJK-UHFFFAOYSA-N 0.000 description 1
- VCVFJHMHKAFZQI-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-[3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]piperazine-1-carboxamide Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(NC(=O)N3CCN(CC3)C=3N=C(N=C(C=3)N3CCCC3)N3CCCC3)SC=2)=C1 VCVFJHMHKAFZQI-UHFFFAOYSA-N 0.000 description 1
- DLSSZULDWSDJOE-UHFFFAOYSA-N 4-(2,6-dipyrrolidin-1-ylpyrimidin-4-yl)-n-[4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl]piperazine-1-carbothioamide Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=CSC(NC(=S)N2CCN(CC2)C=2N=C(N=C(C=2)N2CCCC2)N2CCCC2)=N1 DLSSZULDWSDJOE-UHFFFAOYSA-N 0.000 description 1
- YTHMKVBIIVWCKQ-UHFFFAOYSA-N 4-(4,6-dipyrrolidin-1-yl-1,3,5-triazin-2-yl)-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)piperazine-1-carboxamide Chemical compound C1CN(C=2N=C(N=C(N=2)N2CCCC2)N2CCCC2)CCN1C(=O)NC(SC=1)=NC=1C1=CC=CN=C1 YTHMKVBIIVWCKQ-UHFFFAOYSA-N 0.000 description 1
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- SZYLTNZMUUXCGA-UHFFFAOYSA-N n-[4-[4-(pyrrolidin-1-ylmethyl)phenyl]-1,3-thiazol-2-yl]piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)NC(SC=1)=NC=1C(C=C1)=CC=C1CN1CCCC1 SZYLTNZMUUXCGA-UHFFFAOYSA-N 0.000 description 1
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- 230000007170 pathology Effects 0.000 description 1
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- 231100000719 pollutant Toxicity 0.000 description 1
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Classifications
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/48—Acylated amino or imino radicals by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof, e.g. carbonylguanidines
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI911714A IT1248526B (it) | 1991-06-21 | 1991-06-21 | 2-ammino-4-aril-tiazoli ad attivita' antiasmatica e antiinfiammatoria delle vie aeree |
| ITMI920786A IT1255077B (it) | 1992-04-01 | 1992-04-01 | 2-ammino-4-aril-tiazoli ad attivita' antiasmatica e antiinfiammatoria delle vie aeree |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE921972A1 true IE921972A1 (en) | 1992-12-30 |
Family
ID=26330730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE197292A IE921972A1 (en) | 1991-06-21 | 1992-07-01 | Amino-4-aryl-thiazoles with antiasthmatic and¹antiinflammatory activities on the respiratory tract |
Country Status (8)
| Country | Link |
|---|---|
| EP (2) | EP0519449A1 (OSRAM) |
| JP (1) | JPH07502014A (OSRAM) |
| AU (1) | AU2000092A (OSRAM) |
| IE (1) | IE921972A1 (OSRAM) |
| MX (1) | MX9202978A (OSRAM) |
| NZ (1) | NZ243206A (OSRAM) |
| TW (1) | TW206968B (OSRAM) |
| WO (1) | WO1993000342A1 (OSRAM) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL115420A0 (en) | 1994-09-26 | 1995-12-31 | Zeneca Ltd | Aminoheterocyclic derivatives |
| AU1608397A (en) | 1996-02-02 | 1997-08-22 | Zeneca Limited | Heterocyclic compounds useful as pharmaceutical agents |
| GB9602166D0 (en) | 1996-02-02 | 1996-04-03 | Zeneca Ltd | Aminoheterocyclic derivatives |
| IL128428A0 (en) * | 1996-08-14 | 2000-01-31 | Zeneca Ltd | Substituted pyrimidine derivatives and their pharmaceutical use |
| UA56197C2 (uk) | 1996-11-08 | 2003-05-15 | Зенека Лімітед | Гетероциклічні похідні |
| WO1998035956A1 (en) | 1997-02-13 | 1998-08-20 | Zeneca Limited | Heterocyclic compounds useful as oxido-squalene cyclase inhibitors |
| US6391880B1 (en) | 1997-02-13 | 2002-05-21 | Zeneca Limited | Heterocyclic compounds useful as oxido-squalene cyclase inhibitors |
| GB9715895D0 (en) | 1997-07-29 | 1997-10-01 | Zeneca Ltd | Heterocyclic compounds |
| GB9902989D0 (en) | 1999-02-11 | 1999-03-31 | Zeneca Ltd | Heterocyclic derivatives |
| DE60234453D1 (de) * | 2001-07-02 | 2009-12-31 | High Point Pharmaceuticals Llc | Substituierte piperazin- und diazepanderivate zur verwendung als histamin h3 rezeptormodulatoren |
| WO2003057693A1 (fr) * | 2001-12-28 | 2003-07-17 | Sumitomo Pharmaceuticals Co., Ltd. | Composes cycliques a 5 chainons |
| TWI336696B (en) * | 2003-01-27 | 2011-02-01 | Astellas Pharma Inc | Thiazole derivatives |
| CN100491361C (zh) * | 2003-01-27 | 2009-05-27 | 安斯泰来制药有限公司 | 噻唑衍生物及其作为vap-1抑制剂的用途 |
| FR2854158B1 (fr) | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| GB0320197D0 (en) * | 2003-08-28 | 2003-10-01 | Novartis Ag | Organic compounds |
| FR2872813B1 (fr) * | 2004-07-09 | 2007-01-19 | Sanofi Synthelabo | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| US7820654B2 (en) | 2004-09-23 | 2010-10-26 | Dr. Reddy's Laboratories Ltd. | Pyrimidine compounds, process for their preparation and compositions containing them |
| FR2876692B1 (fr) | 2004-10-19 | 2007-02-23 | Sanofi Aventis Sa | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
| GB0428327D0 (en) * | 2004-12-24 | 2005-02-02 | Astrazeneca Ab | Method |
| BRPI0519288A2 (pt) * | 2004-12-24 | 2009-01-06 | Astrazeneca Ab | compostos heterocÍclicos como antagonistas de ccr2b |
| DK2937341T3 (en) | 2004-12-30 | 2017-09-11 | Janssen Pharmaceutica Nv | 4- (BENZYL) -PIPERAZINE-1-CARBOXYLIC ACID PHENYLAMIDE DERIVATIVES AND RELATED COMPOUNDS AS MODULATORS OF FATTY ACID HYDROLASE (FAAH) FOR TREATING ANALYSIS, PAIN AND OTHER CONDITIONS |
| AU2006227833A1 (en) | 2005-03-18 | 2006-09-28 | The Regents Of The University Of California | Compounds having activity in correcting mutant-CFTR processing and uses thereof |
| CA2618653A1 (en) * | 2005-08-12 | 2007-02-22 | Takeda Pharmaceutical Company Limited | Brain/neuronal cell-protecting agent and therapeutic agent for sleep disorder |
| FR2895989B1 (fr) | 2006-01-06 | 2010-04-30 | Sanofi Aventis | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
| CN101627038A (zh) * | 2006-12-04 | 2010-01-13 | 阿斯利康(瑞典)有限公司 | 抗菌多环脲化合物 |
| BRPI0915471A2 (pt) | 2008-06-04 | 2017-06-27 | Astrazeneca Ab | composto, composição farmacêutica, métodos de inibir dna girase bacteriana e/ou topoisomerase bacteriana iv, para produzir um efeito antibacteriano em um animal de sangue quente e para tratar uma infecção bacteriana em um animal de sangue quente, e, uso de um composto |
| TW201102065A (en) * | 2009-05-29 | 2011-01-16 | Astrazeneca Ab | Heterocyclic urea derivatives and methods of use thereof |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| CN102166214B (zh) * | 2011-03-02 | 2012-12-12 | 华中科技大学同济医学院附属同济医院 | 氨基噻唑类MyD88特异性抑制剂在医学上的用途 |
| CN102336720B (zh) * | 2011-03-02 | 2016-01-13 | 华中科技大学 | 2-氨基噻唑衍生物及制备方法和应用 |
| CN102351854B (zh) * | 2011-07-29 | 2014-06-04 | 华中科技大学 | 氨基噻唑衍生物及制备方法和医药用途 |
| DE102011083283A1 (de) * | 2011-09-23 | 2013-03-28 | Beiersdorf Ag | Heteroalkylamidothiazole, deren kosmetische oder dermatologische Verwendung sowie kosmetische oder dermatologische Zubereitungen mit einem Gehalt an solchen Heteroalkylamidothiazolen |
| WO2022232919A1 (en) * | 2021-05-03 | 2022-11-10 | UNIVERSITé LAVAL | Viral rna polymerase inhibitors and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2602792A (en) * | 1950-11-24 | 1952-07-08 | American Cyanamid Co | 1-carbocycliccarbamyl-4-heterocyclic-piperazines |
| US4217355A (en) * | 1978-04-24 | 1980-08-12 | Pfizer Inc. | Amide therapeutic agents |
| FR2429210A1 (fr) * | 1978-06-19 | 1980-01-18 | Fabre Sa Pierre | Derives de phenyl-4 thiazolyl-2 oxamates utiles dans le traitement de l'asthme |
| JPS57136579A (en) * | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| WO1982002383A1 (en) * | 1981-01-13 | 1982-07-22 | Sakano Isao | Novel thiazole compounds,process for their preparation,and medicinal composition containing same |
-
1992
- 1992-06-17 EP EP92110267A patent/EP0519449A1/en active Pending
- 1992-06-17 EP EP92912406A patent/EP0589985A1/en not_active Withdrawn
- 1992-06-17 WO PCT/EP1992/001377 patent/WO1993000342A1/en not_active Application Discontinuation
- 1992-06-17 AU AU20000/92A patent/AU2000092A/en not_active Abandoned
- 1992-06-17 JP JP5501313A patent/JPH07502014A/ja active Pending
- 1992-06-18 TW TW081104768A patent/TW206968B/zh active
- 1992-06-18 NZ NZ24320692A patent/NZ243206A/xx unknown
- 1992-06-18 MX MX9202978A patent/MX9202978A/es unknown
- 1992-07-01 IE IE197292A patent/IE921972A1/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1993000342A1 (en) | 1993-01-07 |
| TW206968B (OSRAM) | 1993-06-01 |
| EP0519449A1 (en) | 1992-12-23 |
| EP0589985A1 (en) | 1994-04-06 |
| JPH07502014A (ja) | 1995-03-02 |
| AU2000092A (en) | 1993-01-25 |
| NZ243206A (en) | 1994-07-26 |
| MX9202978A (es) | 1993-02-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FC9A | Application refused sect. 31(1) |