NO324352B1 - Aminotiazolderivater, fremgangsmate for deres fremstilling, deres anvendelse samt farmasoytisk preparat - Google Patents

Info

Publication number

NO324352B1

NO324352B1 NO20020155A NO20020155A NO324352B1 NO 324352 B1 NO324352 B1 NO 324352B1 NO 20020155 A NO20020155 A NO 20020155A NO 20020155 A NO20020155 A NO 20020155A NO 324352 B1 NO324352 B1 NO 324352B1

Authority

NO

Norway

Prior art keywords

methylphenyl

methoxy

prop

chloro

group

Prior art date

1999-07-15

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• 238000000034 method Methods 0.000 title claims description 38
• 238000002360 preparation method Methods 0.000 title claims description 23
• 230000008569 process Effects 0.000 title claims description 5
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title description 12
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims description 126
• IKXNIQJDNKPPCH-UHFFFAOYSA-N hydron;prop-2-yn-1-amine;chloride Chemical compound [Cl-].[NH3+]CC#C IKXNIQJDNKPPCH-UHFFFAOYSA-N 0.000 claims description 47
• -1 2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl Chemical group 0.000 claims description 32
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 208000035475 disorder Diseases 0.000 claims description 20
• 150000003839 salts Chemical class 0.000 claims description 15
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 230000007170 pathology Effects 0.000 claims description 8
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 7
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• 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 6
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• 150000004677 hydrates Chemical class 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 5
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• 229940127554 medical product Drugs 0.000 claims description 5
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• IXWGQFWPELLZJB-BQAIUKQQSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1r)-2-methoxy-1-[4-(methoxymethyl)phenyl]ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](COC)C=1C=CC(COC)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl IXWGQFWPELLZJB-BQAIUKQQSA-N 0.000 claims description 4
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• MVDKSBBYWLMXJQ-UQIIZPHYSA-N n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-4-(4-methoxy-2,5-dimethylphenyl)-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(C)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=C(F)C(C)=CC=2)=N1 MVDKSBBYWLMXJQ-UQIIZPHYSA-N 0.000 claims description 4
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• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
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• OGDZLWPYOXRRQG-BQAIUKQQSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-n-[(1s)-1-phenylpentyl]-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCCC)C=1C=CC=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl OGDZLWPYOXRRQG-BQAIUKQQSA-N 0.000 claims 2
• APSCIIYYEZZAFL-FTBISJDPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1r)-1-(3-fluoro-4-methylphenyl)-2-methoxyethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](COC)C=1C=C(F)C(C)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl APSCIIYYEZZAFL-FTBISJDPSA-N 0.000 claims 2
• LWWDYICCOYDRAV-JIDHJSLPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-(3-fluoro-4-methylphenyl)pentyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCCC)C=1C=C(F)C(C)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl LWWDYICCOYDRAV-JIDHJSLPSA-N 0.000 claims 2
• JRFDJIVNQOIVMA-BQAIUKQQSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-(4-chlorophenyl)-2-cyclopropylethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=CC(Cl)=CC=2)=N1 JRFDJIVNQOIVMA-BQAIUKQQSA-N 0.000 claims 2
• CSNMMZFZVWGSBL-FTBISJDPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-(4-fluorophenyl)butyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCC)C=1C=CC(F)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl CSNMMZFZVWGSBL-FTBISJDPSA-N 0.000 claims 2
• XNLZVDGMPUXCEL-BQAIUKQQSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-(4-fluorophenyl)pentyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCCC)C=1C=CC(F)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl XNLZVDGMPUXCEL-BQAIUKQQSA-N 0.000 claims 2
• GXLIBRLAEKOOLG-JIDHJSLPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-[3-fluoro-4-(methoxymethyl)phenyl]butyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCC)C=1C=C(F)C(COC)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl GXLIBRLAEKOOLG-JIDHJSLPSA-N 0.000 claims 2
• GTWWNSQCSNGXQO-UQIIZPHYSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-1-[4-(methoxymethyl)phenyl]pentyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C#CCN([C@@H](CCCC)C=1C=CC(COC)=CC=1)C(SC=1C)=NC=1C1=CC(C)=C(OC)C=C1Cl GTWWNSQCSNGXQO-UQIIZPHYSA-N 0.000 claims 2
• NHYMDRBLBZKOIA-JIDHJSLPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclobutyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CCC2)C=2C=CC(F)=CC=2)=N1 NHYMDRBLBZKOIA-JIDHJSLPSA-N 0.000 claims 2
• BMXALUHUEGRRCH-JIDHJSLPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(3-fluoro-4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=C(F)C(C)=CC=2)=N1 BMXALUHUEGRRCH-JIDHJSLPSA-N 0.000 claims 2
• JZQNRGUPKOUARB-BQAIUKQQSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(4-fluorophenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=CC(F)=CC=2)=N1 JZQNRGUPKOUARB-BQAIUKQQSA-N 0.000 claims 2
• KLXZVXJPVWCXGB-JIDHJSLPSA-N 4-(2-chloro-4-methoxy-5-methylphenyl)-n-[(1s)-2-cyclopropyl-1-(4-methylphenyl)ethyl]-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=CC(C)=CC=2)=N1 KLXZVXJPVWCXGB-JIDHJSLPSA-N 0.000 claims 2
• MGKRHGBJYMGBOI-BQAIUKQQSA-N n-[(1s)-1-(4-bromophenyl)-2-cyclopropylethyl]-4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-n-prop-2-ynyl-1,3-thiazol-2-amine;hydrochloride Chemical compound Cl.C1=C(C)C(OC)=CC(Cl)=C1C1=C(C)SC(N(CC#C)[C@@H](CC2CC2)C=2C=CC(Br)=CC=2)=N1 MGKRHGBJYMGBOI-BQAIUKQQSA-N 0.000 claims 2
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