CA1117949A - Aminothiazoles - Google Patents
AminothiazolesInfo
- Publication number
- CA1117949A CA1117949A CA000328805A CA328805A CA1117949A CA 1117949 A CA1117949 A CA 1117949A CA 000328805 A CA000328805 A CA 000328805A CA 328805 A CA328805 A CA 328805A CA 1117949 A CA1117949 A CA 1117949A
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- grams
- carbon atoms
- group
- hydrogen
- 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
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title description 16
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 12
- -1 monosubstituted phenyl Chemical group 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000001246 bromo group Chemical group Br* 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 230000000694 effects Effects 0.000 abstract description 15
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
- UXZPFPLPTODLCU-UHFFFAOYSA-N 4,5-diphenyl-n-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N=1C(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)SC=1NCCC1=CC=CC=C1 UXZPFPLPTODLCU-UHFFFAOYSA-N 0.000 abstract description 2
- JUGUBOQRAJASOS-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-(thiophen-2-ylmethyl)-1,3-thiazol-2-amine Chemical compound C1=CC(F)=CC=C1C1=CSC(NCC=2SC=CC=2)=N1 JUGUBOQRAJASOS-UHFFFAOYSA-N 0.000 abstract description 2
- WUJMSYVUUQROPB-UHFFFAOYSA-N 4-phenyl-5-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound S1C(N)=NC(C=2C=CC=CC=2)=C1CCC1=CC=CC=C1 WUJMSYVUUQROPB-UHFFFAOYSA-N 0.000 abstract 1
- MFBJXMMGIRSWAP-UHFFFAOYSA-N 4-phenyl-n-(thiophen-2-ylmethyl)-1,3-thiazol-2-amine Chemical compound C=1C=CSC=1CNC(SC=1)=NC=1C1=CC=CC=C1 MFBJXMMGIRSWAP-UHFFFAOYSA-N 0.000 abstract 1
- NTUXEUGLSZFNPX-UHFFFAOYSA-N 5-methyl-4-phenyl-n-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N=1C(C=2C=CC=CC=2)=C(C)SC=1NCCC1=CC=CC=C1 NTUXEUGLSZFNPX-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 51
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 30
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 22
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 238000010992 reflux Methods 0.000 description 17
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 14
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000004458 analytical method Methods 0.000 description 13
- 108010062580 Concanavalin A Proteins 0.000 description 11
- 238000001816 cooling Methods 0.000 description 9
- 239000003814 drug Substances 0.000 description 9
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- HLFSDGLLUJUHTE-SNVBAGLBSA-N Levamisole Chemical compound C1([C@H]2CN3CCSC3=N2)=CC=CC=C1 HLFSDGLLUJUHTE-SNVBAGLBSA-N 0.000 description 7
- 229960001614 levamisole Drugs 0.000 description 7
- 235000010418 carrageenan Nutrition 0.000 description 6
- 229920001525 carrageenan Polymers 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 229950003476 aminothiazole Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000028993 immune response Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- OFVGPHQYOCKLLM-UHFFFAOYSA-N 2-phenylethylthiourea Chemical compound NC(=S)NCCC1=CC=CC=C1 OFVGPHQYOCKLLM-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 description 4
- 239000002260 anti-inflammatory agent Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- UCGFRIAOVLXVKL-UHFFFAOYSA-N benzylthiourea Chemical compound NC(=S)NCC1=CC=CC=C1 UCGFRIAOVLXVKL-UHFFFAOYSA-N 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 210000004698 lymphocyte Anatomy 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 150000002431 hydrogen Chemical group 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001556 precipitation Methods 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 210000001541 thymus gland Anatomy 0.000 description 3
- WLOXAUTXAOGCCI-UHFFFAOYSA-N 1,3-dibenzhydrylthiourea Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)NC(=S)NC(C=1C=CC=CC=1)C1=CC=CC=C1 WLOXAUTXAOGCCI-UHFFFAOYSA-N 0.000 description 2
- RXDYOLRABMJTEF-UHFFFAOYSA-N 2-chloro-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Cl)C(=O)C1=CC=CC=C1 RXDYOLRABMJTEF-UHFFFAOYSA-N 0.000 description 2
- WZBBWWWJHUVYIC-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-(4-methoxyphenyl)ethyl]-1,3-thiazol-2-amine Chemical compound C1=CC(OC)=CC=C1CCNC1=NC(C=2C=CC(F)=CC=2)=CS1 WZBBWWWJHUVYIC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 102000053602 DNA Human genes 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 2
- 241001529936 Murinae Species 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- 230000002456 anti-arthritic effect Effects 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 206010003246 arthritis Diseases 0.000 description 2
- 238000003556 assay Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000004113 cell culture Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- WEEYMMXMBFJUAI-UHFFFAOYSA-N fanetizole Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1NCCC1=CC=CC=C1 WEEYMMXMBFJUAI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- ZIPQNVVCEHWMBV-UHFFFAOYSA-N furan-2-ylmethanamine;hydrochloride Chemical compound Cl.NCC1=CC=CO1 ZIPQNVVCEHWMBV-UHFFFAOYSA-N 0.000 description 2
- XSWHIPZJAMCLRZ-UHFFFAOYSA-N furan-2-ylmethylthiourea Chemical compound NC(=S)NCC1=CC=CO1 XSWHIPZJAMCLRZ-UHFFFAOYSA-N 0.000 description 2
- 125000001475 halogen functional group Chemical group 0.000 description 2
- SKHIBNDAFWIOPB-UHFFFAOYSA-N hydron;2-phenylethanamine;chloride Chemical compound Cl.NCCC1=CC=CC=C1 SKHIBNDAFWIOPB-UHFFFAOYSA-N 0.000 description 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XHAHWNWJFYVXIU-UHFFFAOYSA-N n'-phenylethane-1,2-diamine;hydrochloride Chemical compound Cl.NCCNC1=CC=CC=C1 XHAHWNWJFYVXIU-UHFFFAOYSA-N 0.000 description 2
- DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229940048346 phenethylamine hydrochloride Drugs 0.000 description 2
- 229960002895 phenylbutazone Drugs 0.000 description 2
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- 239000011550 stock solution Substances 0.000 description 2
- XARZSESQHPGTIA-UHFFFAOYSA-N thiophen-2-ylmethylthiourea Chemical compound NC(=S)NCC1=CC=CS1 XARZSESQHPGTIA-UHFFFAOYSA-N 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- KEEKMOIRJUWKNK-CABZTGNLSA-N (2S)-2-[[2-[(4R)-4-(difluoromethyl)-2-oxo-1,3-thiazolidin-3-yl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepin-9-yl]amino]propanamide Chemical compound FC([C@H]1N(C(SC1)=O)C=1N=C2N(CCOC3=C2C=CC(=C3)N[C@H](C(=O)N)C)C=1)F KEEKMOIRJUWKNK-CABZTGNLSA-N 0.000 description 1
- ORECNKBJIMKZNX-UHFFFAOYSA-N 1,3-thiazol-3-ium;chloride Chemical compound Cl.C1=CSC=N1 ORECNKBJIMKZNX-UHFFFAOYSA-N 0.000 description 1
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 description 1
- SYGLPNDHSSTGNF-UHFFFAOYSA-N 2-anilinoethylthiourea Chemical compound N(C1=CC=CC=C1)CCNC(=S)N SYGLPNDHSSTGNF-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- WYKHSBAVLOPISI-UHFFFAOYSA-N 2-phenyl-1,3-thiazole Chemical compound C1=CSC(C=2C=CC=CC=2)=N1 WYKHSBAVLOPISI-UHFFFAOYSA-N 0.000 description 1
- XBHYCJAPPFRNJY-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-(thiophen-2-ylmethyl)-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=CSC(NCC=2SC=CC=2)=N1 XBHYCJAPPFRNJY-UHFFFAOYSA-N 0.000 description 1
- FQAIZUCKLCQVKB-UHFFFAOYSA-N 4-benzhydryl-1,3-thiazol-2-amine Chemical class S1C(N)=NC(C(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 FQAIZUCKLCQVKB-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- NZNLNNGLRKGPJB-UHFFFAOYSA-N 4-phenyl-1,3-thiazole hydrobromide Chemical compound Br.C1(=CC=CC=C1)C=1N=CSC1 NZNLNNGLRKGPJB-UHFFFAOYSA-N 0.000 description 1
- QEWKOYRPGOBKIS-UHFFFAOYSA-N 4-phenyl-n-(2-phenylethyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.N=1C(C=2C=CC=CC=2)=CSC=1NCCC1=CC=CC=C1 QEWKOYRPGOBKIS-UHFFFAOYSA-N 0.000 description 1
- ZJFKIIKXYWYFEK-UHFFFAOYSA-N 4-phenyl-n-(thiophen-2-ylmethyl)-1,3-thiazol-2-amine;hydrobromide Chemical compound Br.C=1C=CSC=1CNC(SC=1)=NC=1C1=CC=CC=C1 ZJFKIIKXYWYFEK-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
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- 230000002917 arthritic effect Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- CIHWJRSPVJBHGT-UHFFFAOYSA-N benzhydrylazanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(N)C1=CC=CC=C1 CIHWJRSPVJBHGT-UHFFFAOYSA-N 0.000 description 1
- XKXHCNPAFAXVRZ-UHFFFAOYSA-N benzylazanium;chloride Chemical compound [Cl-].[NH3+]CC1=CC=CC=C1 XKXHCNPAFAXVRZ-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
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- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 229960001334 corticosteroids Drugs 0.000 description 1
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- 230000007812 deficiency Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical class C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
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- 235000019634 flavors Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- DDRPCXLAQZKBJP-UHFFFAOYSA-N furfurylamine Chemical compound NCC1=CC=CO1 DDRPCXLAQZKBJP-UHFFFAOYSA-N 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 208000026278 immune system disease Diseases 0.000 description 1
- 230000004957 immunoregulator effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229960000905 indomethacin Drugs 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- OCIDXARMXNJACB-UHFFFAOYSA-N n'-phenylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=C1 OCIDXARMXNJACB-UHFFFAOYSA-N 0.000 description 1
- JRFFAPQYMPSJBZ-UHFFFAOYSA-N n-(2-phenylethyl)-1,3-thiazol-2-amine Chemical compound N=1C=CSC=1NCCC1=CC=CC=C1 JRFFAPQYMPSJBZ-UHFFFAOYSA-N 0.000 description 1
- QSLBXMRJPQRVER-UHFFFAOYSA-N n-benzyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC1=NC=CS1 QSLBXMRJPQRVER-UHFFFAOYSA-N 0.000 description 1
- GJRJECJQBNZINV-UHFFFAOYSA-N n-benzyl-4-phenyl-1,3-thiazol-2-amine Chemical compound C=1C=CC=CC=1CNC(SC=1)=NC=1C1=CC=CC=C1 GJRJECJQBNZINV-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- NZYMHENLAOOTLV-UHFFFAOYSA-N thiophen-2-ylmethylazanium;chloride Chemical compound Cl.NCC1=CC=CS1 NZYMHENLAOOTLV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- 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
- A61P37/02—Immunomodulators
-
- 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
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F16—ENGINEERING ELEMENTS AND UNITS; GENERAL MEASURES FOR PRODUCING AND MAINTAINING EFFECTIVE FUNCTIONING OF MACHINES OR INSTALLATIONS; THERMAL INSULATION IN GENERAL
- F16B—DEVICES FOR FASTENING OR SECURING CONSTRUCTIONAL ELEMENTS OR MACHINE PARTS TOGETHER, e.g. NAILS, BOLTS, CIRCLIPS, CLAMPS, CLIPS OR WEDGES; JOINTS OR JOINTING
- F16B15/00—Nails; Staples
- F16B15/0023—Nail plates
- F16B2015/0076—Nail plates with provisions for additional fastening means, e.g. hooks, holes for separate screws or nails, adhesive
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91183078A | 1978-06-02 | 1978-06-02 | |
| US911,830 | 1978-06-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1117949A true CA1117949A (en) | 1982-02-09 |
Family
ID=25430923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000328805A Expired CA1117949A (en) | 1978-06-02 | 1979-05-31 | Aminothiazoles |
Country Status (36)
| Country | Link |
|---|---|
| JP (1) | JPS5936988B2 (es) |
| AR (1) | AR226285A1 (es) |
| AT (1) | AT373248B (es) |
| AU (1) | AU511242B2 (es) |
| BE (1) | BE876732A (es) |
| CA (1) | CA1117949A (es) |
| CH (1) | CH639653A5 (es) |
| CS (1) | CS216927B2 (es) |
| DD (1) | DD144055A5 (es) |
| DE (1) | DE2922523C2 (es) |
| DK (1) | DK150068C (es) |
| EG (1) | EG14354A (es) |
| ES (1) | ES481220A1 (es) |
| FI (1) | FI68820C (es) |
| FR (1) | FR2427333A1 (es) |
| GB (1) | GB2022085B (es) |
| GR (1) | GR73142B (es) |
| HK (1) | HK66487A (es) |
| HU (1) | HU180045B (es) |
| IE (1) | IE48426B1 (es) |
| IL (1) | IL57450A (es) |
| IT (1) | IT1121238B (es) |
| KE (1) | KE3459A (es) |
| LU (1) | LU81349A1 (es) |
| MY (1) | MY8500318A (es) |
| NL (1) | NL178421C (es) |
| NO (1) | NO150760C (es) |
| NZ (1) | NZ190623A (es) |
| PH (1) | PH17020A (es) |
| PL (1) | PL117515B1 (es) |
| PT (1) | PT69718A (es) |
| SE (1) | SE438333B (es) |
| SG (1) | SG56184G (es) |
| SU (1) | SU843746A3 (es) |
| YU (1) | YU40997B (es) |
| ZA (1) | ZA792729B (es) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57501565A (es) * | 1980-10-24 | 1982-09-02 | ||
| JPS57136579A (en) * | 1981-01-21 | 1982-08-23 | Mitsui Toatsu Chem Inc | Thiazolylurea derivative, its preparation, and pharmaceutical composition containing the same |
| EP0068033B1 (en) * | 1981-01-08 | 1985-07-10 | Mitsui Toatsu Kagaku Kabushiki Kaisha | N-(4-phenyl-2-thiazolyl)carbamate derivatives, process for their preparation, and medicinal composition containing same |
| JPS57116067A (en) * | 1981-01-12 | 1982-07-19 | Sankyo Kagaku Kk | Novel 8-quinolinesulfonyl derivative, its synthesis and use |
| US4501750A (en) * | 1981-01-13 | 1985-02-26 | Mitsui Toatsu Kaguku Kabushiki Kaisha | Thiazole compounds, a process for preparing same and a pharmaceutical composition containing the thiazole compounds |
| WO1982002386A1 (en) * | 1981-01-13 | 1982-07-22 | Sakano Isao | Aminothiazole derivatives,process for their preparation,and medicinal composition containing same |
| JPS57154175A (en) * | 1981-03-16 | 1982-09-22 | Mitsui Toatsu Chem Inc | 2-thiazoleamine derivative, its preparation, and drug composition comprising it |
| DE3227329A1 (de) * | 1982-07-22 | 1984-01-26 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 2-n,n-disubstituierten aminothiazolen |
| WO1986003203A1 (en) * | 1984-11-22 | 1986-06-05 | Yoshitomi Pharmaceutical Industries, Ltd. | Thienylthiazole derivatives |
| FR2581063B1 (fr) * | 1985-04-30 | 1987-07-17 | Chauvin Blache Lab | Amino-2 thiazoles n-substitues, leur procede de preparation et leur application en therapeutique |
| JPS63152368A (ja) * | 1986-06-03 | 1988-06-24 | Sumitomo Pharmaceut Co Ltd | 新規なアミノアゾ−ル誘導体およびその酸付加塩 |
| JPH075579B2 (ja) * | 1986-09-01 | 1995-01-25 | 吉富製薬株式会社 | アミノチアゾ−ル化合物 |
| JPH0753666B2 (ja) * | 1987-09-14 | 1995-06-07 | 久光製薬株式会社 | 置換ジフェニルチアゾール誘導体からなる抗炎症剤 |
| ATE159622T1 (de) * | 1989-08-10 | 1997-11-15 | Commw Scient Ind Res Org | Verfahren zur herstellung von einer elektrosuspension von mikropartikeln |
| DE69132293D1 (de) * | 1991-03-07 | 2000-08-10 | Hisamitsu Pharmaceutical Co | Diphenylthiazolderivate mit antiinflammatorischer aktivität |
| FR2692893B1 (fr) * | 1992-06-24 | 1994-09-02 | Sanofi Elf | Dérivés alkylamino ramifiés du thiazole, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent. |
| CA2195847A1 (en) * | 1994-07-27 | 1996-02-08 | John J. Talley | Substituted thiazoles for the treatment of inflammation |
| FR2754258B1 (fr) | 1996-10-08 | 1998-12-31 | Sanofi Sa | Derives d'aminothiazole, leur procede de preparation et les compositions pharmaceutiques les contenant |
| US7105550B2 (en) * | 2000-03-01 | 2006-09-12 | Christopher Love | 2,4-disubstituted thiazolyl derivatives |
| EP1423113A4 (en) * | 2001-08-13 | 2007-04-18 | Phenex Pharmaceuticals Ag | NR1H4 NUCLEAR RECEPTOR BINDING COMPOUNDS |
| WO2003027096A1 (en) * | 2001-09-26 | 2003-04-03 | Bayer Pharmaceuticals Corporation | Substituted 3-pyridyl imidazoles as c17,20 lyase inhibitors |
| PT1471054E (pt) | 2002-01-11 | 2009-09-23 | Daiichi Sankyo Co Ltd | Derivado de aminoálcool ou derivado de ácido fosfónico e composição medicinal que os contém |
| EP1555264A1 (en) * | 2004-01-15 | 2005-07-20 | Sireen AG | Five-membered heterocyclic compounds as inhibitors of SRC family protein kinase. |
| KR20110136901A (ko) | 2004-02-24 | 2011-12-21 | 상꾜 가부시키가이샤 | 아미노 알코올 화합물 |
| KR20080019213A (ko) | 2005-05-09 | 2008-03-03 | 아칠리온 파르마세우티칼스 인코포레이티드 | 티아졸 화합물 및 그 사용방법 |
| ES2389062T3 (es) | 2006-01-18 | 2012-10-22 | Amgen, Inc | Compuestos de tiazol como inhibidores de proteína cinasa B (PKB) |
| AU2008276521B2 (en) | 2007-07-17 | 2011-11-03 | Amgen Inc. | Heterocyclic modulators of PKB |
| AU2008276512A1 (en) | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
| WO2012170951A2 (en) * | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US20120316182A1 (en) | 2011-06-10 | 2012-12-13 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| US9856240B2 (en) | 2011-10-19 | 2018-01-02 | Calcimedica, Inc. | Compounds that modulate intracellular calcium |
| CN110590785B (zh) * | 2019-09-23 | 2021-02-02 | 武汉大学 | 一种氨基噻唑类化合物及其制备方法与抗肠道病毒71型的应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3458526A (en) * | 1966-09-26 | 1969-07-29 | Upjohn Co | Certain 2-amino-4,5-bis(p-methoxyphenyl)thiazoles |
-
1979
- 1979-04-30 DK DK177679A patent/DK150068C/da not_active IP Right Cessation
- 1979-05-23 GB GB7917872A patent/GB2022085B/en not_active Expired
- 1979-05-29 CH CH501679A patent/CH639653A5/fr not_active IP Right Cessation
- 1979-05-30 CS CS793728A patent/CS216927B2/cs unknown
- 1979-05-30 EG EG333/79A patent/EG14354A/xx active
- 1979-05-31 SE SE7904798A patent/SE438333B/sv not_active IP Right Cessation
- 1979-05-31 YU YU1288/79A patent/YU40997B/xx unknown
- 1979-05-31 LU LU81349A patent/LU81349A1/xx unknown
- 1979-05-31 IL IL57450A patent/IL57450A/xx unknown
- 1979-05-31 SU SU792773929A patent/SU843746A3/ru active
- 1979-05-31 AU AU47634/79A patent/AU511242B2/en not_active Ceased
- 1979-05-31 CA CA000328805A patent/CA1117949A/en not_active Expired
- 1979-05-31 HU HU79PI679A patent/HU180045B/hu not_active IP Right Cessation
- 1979-05-31 PH PH22588A patent/PH17020A/en unknown
- 1979-06-01 AR AR276782A patent/AR226285A1/es active
- 1979-06-01 PL PL1979216030A patent/PL117515B1/pl unknown
- 1979-06-01 NZ NZ190623A patent/NZ190623A/en unknown
- 1979-06-01 NO NO791831A patent/NO150760C/no unknown
- 1979-06-01 NL NLAANVRAGE7904337,A patent/NL178421C/xx not_active IP Right Cessation
- 1979-06-01 DD DD79213371A patent/DD144055A5/de not_active IP Right Cessation
- 1979-06-01 GR GR59240A patent/GR73142B/el unknown
- 1979-06-01 AT AT0401679A patent/AT373248B/de not_active IP Right Cessation
- 1979-06-01 BE BE0/195534A patent/BE876732A/xx not_active IP Right Cessation
- 1979-06-01 ZA ZA792729A patent/ZA792729B/xx unknown
- 1979-06-01 FR FR7914164A patent/FR2427333A1/fr active Granted
- 1979-06-01 PT PT69718A patent/PT69718A/pt unknown
- 1979-06-01 JP JP54068781A patent/JPS5936988B2/ja not_active Expired
- 1979-06-01 IT IT23228/79A patent/IT1121238B/it active
- 1979-06-01 FI FI791754A patent/FI68820C/fi not_active IP Right Cessation
- 1979-06-01 ES ES481220A patent/ES481220A1/es not_active Expired
- 1979-06-01 DE DE2922523A patent/DE2922523C2/de not_active Expired
- 1979-08-08 IE IE1069/79A patent/IE48426B1/en unknown
-
1984
- 1984-08-13 SG SG561/84A patent/SG56184G/en unknown
- 1984-09-24 KE KE3459A patent/KE3459A/xx unknown
-
1985
- 1985-12-30 MY MY318/85A patent/MY8500318A/xx unknown
-
1987
- 1987-09-17 HK HK664/87A patent/HK66487A/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |