KR20070085395A - 2-아미도-4-페닐티아졸 유도체, 그의 제조 방법 및 치료적용도 - Google Patents
2-아미도-4-페닐티아졸 유도체, 그의 제조 방법 및 치료적용도 Download PDFInfo
- Publication number
- KR20070085395A KR20070085395A KR1020077011308A KR20077011308A KR20070085395A KR 20070085395 A KR20070085395 A KR 20070085395A KR 1020077011308 A KR1020077011308 A KR 1020077011308A KR 20077011308 A KR20077011308 A KR 20077011308A KR 20070085395 A KR20070085395 A KR 20070085395A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- groups
- alkoxy
- formula
- thiazol
- 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.)
- Withdrawn
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- 238000002360 preparation method Methods 0.000 title claims description 22
- 230000001225 therapeutic effect Effects 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 239000002253 acid Substances 0.000 claims abstract description 19
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 150000007513 acids Chemical class 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 71
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 34
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 20
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 14
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 14
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 14
- 150000001204 N-oxides Chemical group 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- BOQOXLAQTDFJKU-UHFFFAOYSA-N morpholine-4-carbonitrile Chemical compound N#CN1CCOCC1 BOQOXLAQTDFJKU-UHFFFAOYSA-N 0.000 claims description 12
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 8
- 125000000355 1,3-benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 7
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 7
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 claims description 7
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- SRUSSDUBONXALX-UHFFFAOYSA-N N-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound C1(CCCCC1)C=1C=CC(=C(C=1)C=1N=C(SC=1)NC(=O)C1CNCCC1)OC SRUSSDUBONXALX-UHFFFAOYSA-N 0.000 claims description 6
- 125000005336 allyloxy group Chemical group 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- MVHAQXYRERDMGX-UHFFFAOYSA-N N-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]pyrrolidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C1CCNC1 MVHAQXYRERDMGX-UHFFFAOYSA-N 0.000 claims description 5
- 239000007822 coupling agent Substances 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000001684 chronic effect Effects 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- LKIZXBUWQPNTQF-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-4-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(CC1)CCN1C(=O)C1=CN=CC=N1 LKIZXBUWQPNTQF-UHFFFAOYSA-N 0.000 claims description 3
- UZGCRIGUQOVVFR-HXUWFJFHSA-N (3r)-n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound C([C@H](C1)C(=O)NC=2SC=C(N=2)C2=CC(=CC=C2OC)C2CCCCC2)CCN1C(=O)C1=CN=CC=N1 UZGCRIGUQOVVFR-HXUWFJFHSA-N 0.000 claims description 2
- UZGCRIGUQOVVFR-FQEVSTJZSA-N (3s)-n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound C([C@@H](C1)C(=O)NC=2SC=C(N=2)C2=CC(=CC=C2OC)C2CCCCC2)CCN1C(=O)C1=CN=CC=N1 UZGCRIGUQOVVFR-FQEVSTJZSA-N 0.000 claims description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- GJYGAFGYZQSTMH-UHFFFAOYSA-N 1-(5-chloro-1-methylpyrazole-4-carbonyl)-n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C=1C=NN(C)C=1Cl GJYGAFGYZQSTMH-UHFFFAOYSA-N 0.000 claims description 2
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000035143 Bacterial infection Diseases 0.000 claims description 2
- KPUVQTHFXBMWQV-UHFFFAOYSA-N N-[4-(5-butyl-2-methoxyphenyl)-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound C(CCC)C=1C=CC(=C(C=1)C=1N=C(SC=1)NC(=O)C1CNCCC1)OC KPUVQTHFXBMWQV-UHFFFAOYSA-N 0.000 claims description 2
- UTQIURRSMLULQB-UHFFFAOYSA-N N-[4-(5-cyclopentyl-2-methoxyphenyl)-1,3-thiazol-2-yl]piperidine-3-carboxamide Chemical compound C1(CCCC1)C=1C=CC(=C(C=1)C=1N=C(SC=1)NC(=O)C1CNCCC1)OC UTQIURRSMLULQB-UHFFFAOYSA-N 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 230000001154 acute effect Effects 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 230000002491 angiogenic effect Effects 0.000 claims description 2
- POAIOYTYGFGBOY-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-ethoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound CCOC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 POAIOYTYGFGBOY-UHFFFAOYSA-N 0.000 claims description 2
- KZJNCUDYCCMESU-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(1,5-dimethylpyrazole-3-carbonyl)piperidine-3-carboxamide Chemical class COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C=1C=C(C)N(C)N=1 KZJNCUDYCCMESU-UHFFFAOYSA-N 0.000 claims description 2
- UGAMCDRWOXXFRA-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(1-methylimidazole-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=NC=CN1C UGAMCDRWOXXFRA-UHFFFAOYSA-N 0.000 claims description 2
- AEXQESOTSPPIIR-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(2-oxo-1h-pyridine-3-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=CN=C1O AEXQESOTSPPIIR-UHFFFAOYSA-N 0.000 claims description 2
- DISBKTYXVGZBQY-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(2-pyridin-2-ylacetyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)CC1=CC=CC=N1 DISBKTYXVGZBQY-UHFFFAOYSA-N 0.000 claims description 2
- KEFVPSJTLZONNL-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(furan-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=CO1 KEFVPSJTLZONNL-UHFFFAOYSA-N 0.000 claims description 2
- AEEPZDSCOILTDI-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-2-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C1CCCCN1C(=O)C1=CN=CC=N1 AEEPZDSCOILTDI-UHFFFAOYSA-N 0.000 claims description 2
- UZGCRIGUQOVVFR-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 UZGCRIGUQOVVFR-UHFFFAOYSA-N 0.000 claims description 2
- DEEOSPIQFYSNIA-UHFFFAOYSA-N n-[4-(5-cyclohexyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrimidine-4-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CC=NC=N1 DEEOSPIQFYSNIA-UHFFFAOYSA-N 0.000 claims description 2
- GCNRKXBJZHYOQD-UHFFFAOYSA-N n-[4-(5-cyclopentyl-2-methoxyphenyl)-1,3-thiazol-2-yl]-1-(pyrazine-2-carbonyl)piperidine-3-carboxamide Chemical compound COC1=CC=C(C2CCCC2)C=C1C(N=1)=CSC=1NC(=O)C(C1)CCCN1C(=O)C1=CN=CC=N1 GCNRKXBJZHYOQD-UHFFFAOYSA-N 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 230000003612 virological effect Effects 0.000 claims description 2
- 230000000495 immunoinflammatory effect Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 105
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 42
- 239000007787 solid Substances 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000012074 organic phase Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- RROBIDXNTUAHFW-UHFFFAOYSA-N benzotriazol-1-yloxy-tris(dimethylamino)phosphanium Chemical compound C1=CC=C2N(O[P+](N(C)C)(N(C)C)N(C)C)N=NC2=C1 RROBIDXNTUAHFW-UHFFFAOYSA-N 0.000 description 15
- -1 oxazozolyl Chemical group 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 238000001816 cooling Methods 0.000 description 9
- 235000019439 ethyl acetate Nutrition 0.000 description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- 239000012317 TBTU Substances 0.000 description 8
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 8
- 229910052794 bromium Inorganic materials 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 6
- 102000019034 Chemokines Human genes 0.000 description 6
- 108010012236 Chemokines Proteins 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
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- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000003818 flash chromatography Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 239000012346 acetyl chloride Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 229910000024 caesium carbonate Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 229960004592 isopropanol Drugs 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
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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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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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
- C07D417/14—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 three or more hetero rings
Landscapes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
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- General Health & Medical Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
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- Oncology (AREA)
- Communicable Diseases (AREA)
- Child & Adolescent Psychology (AREA)
- Virology (AREA)
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- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0411083 | 2004-10-19 | ||
| FR0411083A FR2876692B1 (fr) | 2004-10-19 | 2004-10-19 | Derives de 2-amido-4-phenylthiazole, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20070085395A true KR20070085395A (ko) | 2007-08-27 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020077011308A Withdrawn KR20070085395A (ko) | 2004-10-19 | 2005-10-17 | 2-아미도-4-페닐티아졸 유도체, 그의 제조 방법 및 치료적용도 |
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|---|---|
| US (1) | US7598392B2 (https=) |
| EP (1) | EP1807421B1 (https=) |
| JP (1) | JP2008517042A (https=) |
| KR (1) | KR20070085395A (https=) |
| CN (1) | CN101065376A (https=) |
| AR (1) | AR051334A1 (https=) |
| AT (1) | ATE502035T1 (https=) |
| AU (1) | AU2005296958A1 (https=) |
| BR (1) | BRPI0518231A2 (https=) |
| CA (1) | CA2584774A1 (https=) |
| DE (1) | DE602005026964D1 (https=) |
| EA (1) | EA200700901A1 (https=) |
| EC (1) | ECSP077402A (https=) |
| FR (1) | FR2876692B1 (https=) |
| GT (1) | GT200500292A (https=) |
| IL (1) | IL182624A0 (https=) |
| MA (1) | MA29017B1 (https=) |
| MX (1) | MX2007004740A (https=) |
| NO (1) | NO20072515L (https=) |
| PA (1) | PA8649901A1 (https=) |
| PE (1) | PE20060585A1 (https=) |
| SV (1) | SV2006002274A (https=) |
| TN (1) | TNSN07145A1 (https=) |
| TW (1) | TW200630364A (https=) |
| UY (1) | UY29169A1 (https=) |
| WO (1) | WO2006042954A1 (https=) |
| ZA (1) | ZA200703876B (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024191268A1 (ko) * | 2023-03-15 | 2024-09-19 | 현대약품 주식회사 | 신규한 화합물, 및 이를 포함하는 약학적 조성물 |
| WO2026054614A1 (ko) * | 2024-09-09 | 2026-03-12 | 현대약품 주식회사 | 신규한 화합물, 및 이를 포함하는 약학적 조성물 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2854158B1 (fr) | 2003-04-25 | 2006-11-17 | Sanofi Synthelabo | Derives de 2-acylamino-4-phenylethiazole, leur preparation et leur application en therapeutique |
| FR2872813B1 (fr) | 2004-07-09 | 2007-01-19 | Sanofi Synthelabo | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
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| FR2895989B1 (fr) | 2006-01-06 | 2010-04-30 | Sanofi Aventis | Derives de 2-carbamide-4-phenylthiazole, leur preparation et leur application en therapeutique |
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| PT2661433T (pt) | 2011-01-04 | 2017-10-24 | Novartis Ag | Compostos de indole ou seus análogos úteis para o tratamento da degeneração macular relacionada com a idade (amd) |
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| US2146898A (en) * | 1937-12-06 | 1939-02-14 | Int Harvester Co | Potato digger |
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| WO1993000342A1 (en) | 1991-06-21 | 1993-01-07 | Boehringer Mannheim Italia S.P.A. | 2-amino-4-aryl-thiazoles with antiasthmatic and anti-inflammatory activities on the respiratory tract |
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| TW200423931A (en) | 2003-04-30 | 2004-11-16 | Hoffmann La Roche | Novel aniline derivatives, their manufacture and use as pharmaceutical agents |
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-
2004
- 2004-10-19 FR FR0411083A patent/FR2876692B1/fr not_active Expired - Fee Related
-
2005
- 2005-10-17 AU AU2005296958A patent/AU2005296958A1/en not_active Withdrawn
- 2005-10-17 ZA ZA200703876A patent/ZA200703876B/xx unknown
- 2005-10-17 EA EA200700901A patent/EA200700901A1/ru unknown
- 2005-10-17 JP JP2007537324A patent/JP2008517042A/ja active Pending
- 2005-10-17 MX MX2007004740A patent/MX2007004740A/es not_active Application Discontinuation
- 2005-10-17 CN CNA2005800396968A patent/CN101065376A/zh active Pending
- 2005-10-17 BR BRPI0518231-0A patent/BRPI0518231A2/pt not_active IP Right Cessation
- 2005-10-17 AT AT05809089T patent/ATE502035T1/de not_active IP Right Cessation
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- 2005-10-17 EP EP05809089A patent/EP1807421B1/fr not_active Expired - Lifetime
- 2005-10-17 UY UY29169A patent/UY29169A1/es not_active Application Discontinuation
- 2005-10-17 WO PCT/FR2005/002565 patent/WO2006042954A1/fr not_active Ceased
- 2005-10-17 GT GT200500292A patent/GT200500292A/es unknown
- 2005-10-17 KR KR1020077011308A patent/KR20070085395A/ko not_active Withdrawn
- 2005-10-17 CA CA002584774A patent/CA2584774A1/fr not_active Abandoned
- 2005-10-18 PA PA20058649901A patent/PA8649901A1/es unknown
- 2005-10-18 TW TW094136365A patent/TW200630364A/zh unknown
- 2005-10-18 AR ARP050104349A patent/AR051334A1/es unknown
- 2005-10-19 PE PE2005001227A patent/PE20060585A1/es not_active Application Discontinuation
- 2005-10-19 SV SV2005002274A patent/SV2006002274A/es unknown
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- 2007-04-18 EC EC2007007402A patent/ECSP077402A/es unknown
- 2007-04-18 US US11/736,770 patent/US7598392B2/en not_active Expired - Fee Related
- 2007-04-19 TN TNP2007000145A patent/TNSN07145A1/fr unknown
- 2007-05-11 MA MA29894A patent/MA29017B1/fr unknown
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2024191268A1 (ko) * | 2023-03-15 | 2024-09-19 | 현대약품 주식회사 | 신규한 화합물, 및 이를 포함하는 약학적 조성물 |
| WO2026054614A1 (ko) * | 2024-09-09 | 2026-03-12 | 현대약품 주식회사 | 신규한 화합물, 및 이를 포함하는 약학적 조성물 |
Also Published As
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|---|---|
| UY29169A1 (es) | 2006-05-31 |
| EA200700901A1 (ru) | 2007-10-26 |
| PA8649901A1 (es) | 2006-06-02 |
| CA2584774A1 (fr) | 2006-04-27 |
| AR051334A1 (es) | 2007-01-03 |
| EP1807421B1 (fr) | 2011-03-16 |
| ATE502035T1 (de) | 2011-04-15 |
| US20070259847A1 (en) | 2007-11-08 |
| WO2006042954A8 (fr) | 2008-03-13 |
| NO20072515L (no) | 2007-06-28 |
| WO2006042954A1 (fr) | 2006-04-27 |
| DE602005026964D1 (de) | 2011-04-28 |
| IL182624A0 (en) | 2007-07-24 |
| FR2876692A1 (fr) | 2006-04-21 |
| EP1807421A1 (fr) | 2007-07-18 |
| FR2876692B1 (fr) | 2007-02-23 |
| PE20060585A1 (es) | 2006-08-18 |
| AU2005296958A1 (en) | 2006-04-27 |
| BRPI0518231A2 (pt) | 2008-11-11 |
| GT200500292A (es) | 2006-05-11 |
| ECSP077402A (es) | 2007-05-30 |
| CN101065376A (zh) | 2007-10-31 |
| MA29017B1 (fr) | 2007-11-01 |
| SV2006002274A (es) | 2006-06-28 |
| MX2007004740A (es) | 2007-06-18 |
| ZA200703876B (en) | 2008-12-31 |
| JP2008517042A (ja) | 2008-05-22 |
| TNSN07145A1 (fr) | 2008-11-21 |
| TW200630364A (en) | 2006-09-01 |
| US7598392B2 (en) | 2009-10-06 |
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