CA2072018A1 - Pharmacologically active amide carboxylate derivatives - Google Patents
Pharmacologically active amide carboxylate derivativesInfo
- Publication number
- CA2072018A1 CA2072018A1 CA002072018A CA2072018A CA2072018A1 CA 2072018 A1 CA2072018 A1 CA 2072018A1 CA 002072018 A CA002072018 A CA 002072018A CA 2072018 A CA2072018 A CA 2072018A CA 2072018 A1 CA2072018 A1 CA 2072018A1
- Authority
- CA
- Canada
- Prior art keywords
- amino
- enyl
- acid
- methyl
- oxodec
- 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.)
- Abandoned
Links
- -1 amide carboxylate Chemical class 0.000 title claims abstract description 70
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 75
- 125000003118 aryl group Chemical group 0.000 claims abstract description 52
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 38
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 33
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 16
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 50
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 20
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 9
- 150000001412 amines Chemical class 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 235000010290 biphenyl Nutrition 0.000 claims description 6
- 125000005469 ethylenyl group Chemical group 0.000 claims description 6
- 101100294103 Caenorhabditis elegans nhr-31 gene Proteins 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 238000006460 hydrolysis reaction Methods 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000004968 inflammatory condition Effects 0.000 claims description 3
- FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 claims 4
- LEPWUMPXISBPIB-UHFFFAOYSA-N 4-phenylbutanamide Chemical compound NC(=O)CCCC1=CC=CC=C1 LEPWUMPXISBPIB-UHFFFAOYSA-N 0.000 claims 3
- KQWCITXJXWHUGA-UHFFFAOYSA-N dec-3-enamide Chemical compound CCCCCCC=CCC(N)=O KQWCITXJXWHUGA-UHFFFAOYSA-N 0.000 claims 2
- UQRVRSJVZGTTQB-QGZVFWFLSA-N (3r)-3-(dodecanoylamino)-5-methylhexanoic acid Chemical compound CCCCCCCCCCCC(=O)N[C@H](CC(C)C)CC(O)=O UQRVRSJVZGTTQB-QGZVFWFLSA-N 0.000 claims 1
- KRXHUKOIHOKPGS-OAQYLSRUSA-N (3r)-3-(hexadecanoylamino)-5-methylhexanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@H](CC(C)C)CC(O)=O KRXHUKOIHOKPGS-OAQYLSRUSA-N 0.000 claims 1
- HDVXAQLYEYFXSJ-BOLDSZDNSA-N (3r)-3-[[(e)-dec-3-enoyl]amino]-5-methylhexanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@H](CC(C)C)CC(O)=O HDVXAQLYEYFXSJ-BOLDSZDNSA-N 0.000 claims 1
- BFJQXRAYKLYVRY-XVJNWHFHSA-N (3r)-3-[[(e)-dec-4-enoyl]amino]-5-methylhexanoic acid Chemical compound CCCCC\C=C\CCC(=O)N[C@H](CC(C)C)CC(O)=O BFJQXRAYKLYVRY-XVJNWHFHSA-N 0.000 claims 1
- BOOPSDAMHCGRTO-VFCOFNOGSA-N (3r)-3-[[(z)-hexadec-9-enoyl]amino]-5-methylhexanoic acid Chemical compound CCCCCC\C=C/CCCCCCCC(=O)N[C@H](CC(C)C)CC(O)=O BOOPSDAMHCGRTO-VFCOFNOGSA-N 0.000 claims 1
- XUSSMVCMQALSDZ-OAQYLSRUSA-N (3r)-5-methyl-3-(10-phenyldecanoylamino)hexanoic acid Chemical compound CC(C)C[C@H](CC(O)=O)NC(=O)CCCCCCCCCC1=CC=CC=C1 XUSSMVCMQALSDZ-OAQYLSRUSA-N 0.000 claims 1
- LDQZXBIWNDEKLA-GOSISDBHSA-N (3r)-5-methyl-3-(7-phenylheptanoylamino)hexanoic acid Chemical compound CC(C)C[C@H](CC(O)=O)NC(=O)CCCCCCC1=CC=CC=C1 LDQZXBIWNDEKLA-GOSISDBHSA-N 0.000 claims 1
- HEFJRFSPQJKBTR-LJQANCHMSA-N (3r)-5-methyl-3-(8-phenyloctanoylamino)hexanoic acid Chemical compound CC(C)C[C@H](CC(O)=O)NC(=O)CCCCCCCC1=CC=CC=C1 HEFJRFSPQJKBTR-LJQANCHMSA-N 0.000 claims 1
- IDQUVTYHZLKRNE-CYBMUJFWSA-N (3r)-5-methyl-3-(octanoylamino)hexanoic acid Chemical compound CCCCCCCC(=O)N[C@H](CC(C)C)CC(O)=O IDQUVTYHZLKRNE-CYBMUJFWSA-N 0.000 claims 1
- NRGLRUITDAPSND-HVMBHNBBSA-N (3r)-5-methyl-3-[[(z)-octadec-6-enoyl]amino]hexanoic acid Chemical compound CCCCCCCCCCC\C=C/CCCCC(=O)N[C@H](CC(C)C)CC(O)=O NRGLRUITDAPSND-HVMBHNBBSA-N 0.000 claims 1
- VLKMIUWPUORDKH-NRFANRHFSA-N (3s)-3-(octanoylamino)-4-(3-phenylphenyl)sulfanylbutanoic acid Chemical compound CCCCCCCC(=O)N[C@@H](CC(O)=O)CSC1=CC=CC(C=2C=CC=CC=2)=C1 VLKMIUWPUORDKH-NRFANRHFSA-N 0.000 claims 1
- MTBZQZIXZXIQJC-NRFANRHFSA-N (3s)-3-(octanoylamino)-4-(4-phenylphenyl)sulfanylbutanoic acid Chemical compound C1=CC(SC[C@@H](NC(=O)CCCCCCC)CC(O)=O)=CC=C1C1=CC=CC=C1 MTBZQZIXZXIQJC-NRFANRHFSA-N 0.000 claims 1
- FBELLXNPVQVYDX-SFHVURJKSA-N (3s)-3-(octanoylamino)-4-octylsulfanylbutanoic acid Chemical compound CCCCCCCCSC[C@H](CC(O)=O)NC(=O)CCCCCCC FBELLXNPVQVYDX-SFHVURJKSA-N 0.000 claims 1
- GVWUIRHQVZGZEW-WAVCKPEOSA-N (3s)-3-[[(e)-dec-3-enoyl]amino]-4-(4-nitrophenyl)sulfanylbutanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)CSC1=CC=C([N+]([O-])=O)C=C1 GVWUIRHQVZGZEW-WAVCKPEOSA-N 0.000 claims 1
- UCVBUYTVQOAQJO-CQQBXOTJSA-N (3s)-3-[[(e)-dec-3-enoyl]amino]-4-naphthalen-2-ylsulfanylbutanoic acid Chemical compound C1=CC=CC2=CC(SC[C@@H](NC(=O)C/C=C/CCCCCC)CC(O)=O)=CC=C21 UCVBUYTVQOAQJO-CQQBXOTJSA-N 0.000 claims 1
- CBZCAUILHUNILM-ZBZNSMLMSA-N (3s)-3-[[(e)-dec-3-enoyl]amino]-4-phenylsulfanylbutanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)CSC1=CC=CC=C1 CBZCAUILHUNILM-ZBZNSMLMSA-N 0.000 claims 1
- TYBFDQTXWGAXAO-SSVWKNEZSA-N (3s)-4-benzylsulfanyl-3-[[(e)-dec-3-enoyl]amino]butanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CC(O)=O)CSCC1=CC=CC=C1 TYBFDQTXWGAXAO-SSVWKNEZSA-N 0.000 claims 1
- UHRGMABFWRSNQA-SANMLTNESA-N (3s)-4-hexadecylsulfanyl-3-(octanoylamino)butanoic acid Chemical compound CCCCCCCCCCCCCCCCSC[C@H](CC(O)=O)NC(=O)CCCCCCC UHRGMABFWRSNQA-SANMLTNESA-N 0.000 claims 1
- JMTPEIGXLDLEOK-IBGZPJMESA-N (3s)-4-naphthalen-2-ylsulfanyl-3-(octanoylamino)butanoic acid Chemical compound C1=CC=CC2=CC(SC[C@@H](NC(=O)CCCCCCC)CC(O)=O)=CC=C21 JMTPEIGXLDLEOK-IBGZPJMESA-N 0.000 claims 1
- NOWCXTBBUOUQSA-YSSOQSIOSA-N (4r)-2,6-dimethyl-4-(octanoylamino)heptanoic acid Chemical compound CCCCCCCC(=O)N[C@H](CC(C)C)CC(C)C(O)=O NOWCXTBBUOUQSA-YSSOQSIOSA-N 0.000 claims 1
- XCWQWNGKLDMZPR-OMCHYFTCSA-N (4s)-2-benzyl-4-[[(e)-dec-3-enoyl]amino]-5-naphthalen-2-ylsulfanylpentanoic acid Chemical compound C([C@@H](CSC=1C=C2C=CC=CC2=CC=1)NC(=O)C/C=C/CCCCCC)C(C(O)=O)CC1=CC=CC=C1 XCWQWNGKLDMZPR-OMCHYFTCSA-N 0.000 claims 1
- KAFFBEMNVOAZNP-VWLOTQADSA-N (4s)-4-(7-ethylnonanoylamino)-5-(3-phenylphenyl)sulfanylpentanoic acid Chemical compound CCC(CC)CCCCCC(=O)N[C@@H](CCC(O)=O)CSC1=CC=CC(C=2C=CC=CC=2)=C1 KAFFBEMNVOAZNP-VWLOTQADSA-N 0.000 claims 1
- KRGSLWUYJHMKOG-DEOSSOPVSA-N (4s)-4-(dodecanoylamino)-5-naphthalen-2-ylsulfanylpentanoic acid Chemical compound C1=CC=CC2=CC(SC[C@H](CCC(O)=O)NC(=O)CCCCCCCCCCC)=CC=C21 KRGSLWUYJHMKOG-DEOSSOPVSA-N 0.000 claims 1
- QZZNSDIHVTVAOH-ZVQQDINOSA-N (4s)-4-[[(e)-dec-3-enoyl]amino]-5-(2,4-ditert-butylphenyl)sulfanylpentanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CCC(O)=O)CSC1=CC=C(C(C)(C)C)C=C1C(C)(C)C QZZNSDIHVTVAOH-ZVQQDINOSA-N 0.000 claims 1
- GOQHWYCIGQMZKV-KIUWMYQTSA-N (4s)-4-[[(e)-dec-3-enoyl]amino]-5-(3h-thiadiazol-2-ylsulfanyl)pentanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CCC(O)=O)CSN1NC=CS1 GOQHWYCIGQMZKV-KIUWMYQTSA-N 0.000 claims 1
- VMKBHZWOTXJKMA-IWXKUNQBSA-N (4s)-4-[[(e)-dec-3-enoyl]amino]-5-(4-phenylphenyl)sulfanylpentanoic acid Chemical compound C1=CC(SC[C@H](CCC(O)=O)NC(=O)C/C=C/CCCCCC)=CC=C1C1=CC=CC=C1 VMKBHZWOTXJKMA-IWXKUNQBSA-N 0.000 claims 1
- QHLBAAQFJXZSNQ-OEMHODTASA-N (4s)-4-[[(e)-dec-3-enoyl]amino]-5-[(3-phenyl-1,2,4-triazol-1-yl)sulfanyl]pentanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CCC(O)=O)CSN1C=NC(C=2C=CC=CC=2)=N1 QHLBAAQFJXZSNQ-OEMHODTASA-N 0.000 claims 1
- HXHHZKUQQXIUHB-OZSKJFCKSA-N (4s)-4-[[(e)-dec-3-enoyl]amino]-5-pyridin-4-ylsulfanylpentanoic acid Chemical compound CCCCCC\C=C\CC(=O)N[C@@H](CCC(O)=O)CSC1=CC=NC=C1 HXHHZKUQQXIUHB-OZSKJFCKSA-N 0.000 claims 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 1
- KRXHUKOIHOKPGS-UHFFFAOYSA-N 3-(hexadecanoylamino)-5-methylhexanoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NC(CC(C)C)CC(O)=O KRXHUKOIHOKPGS-UHFFFAOYSA-N 0.000 claims 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
- MUAMBZYBXQGZJM-ZSXSBBPPSA-N C1=C(C=CC2=CC=CC=C12)SC[C@H](CC(C(=O)OC)CC1=CC=CC=C1)NC(CC=CCCCCCC)=O Chemical compound C1=C(C=CC2=CC=CC=C12)SC[C@H](CC(C(=O)OC)CC1=CC=CC=C1)NC(CC=CCCCCCC)=O MUAMBZYBXQGZJM-ZSXSBBPPSA-N 0.000 claims 1
- BRQYFQOVSBACFS-QGZVFWFLSA-N ethyl (4r)-2,6-dimethyl-4-(octanoylamino)hept-2-enoate Chemical compound CCCCCCCC(=O)N[C@H](CC(C)C)C=C(C)C(=O)OCC BRQYFQOVSBACFS-QGZVFWFLSA-N 0.000 claims 1
- NXVPMTQHNZPYNA-ZYMOGRSISA-N ethyl (4r)-2,6-dimethyl-4-(octanoylamino)heptanoate Chemical compound CCCCCCCC(=O)N[C@H](CC(C)C)CC(C)C(=O)OCC NXVPMTQHNZPYNA-ZYMOGRSISA-N 0.000 claims 1
- CITCURYAOVSTCW-XMMPIXPASA-N ethyl (4r)-4-(hexadecanoylamino)-6-methylheptanoate Chemical compound CCCCCCCCCCCCCCCC(=O)N[C@@H](CC(C)C)CCC(=O)OCC CITCURYAOVSTCW-XMMPIXPASA-N 0.000 claims 1
- VPUIDSONZVYYCG-MRXNPFEDSA-N methyl (3R)-3-[[(E)-dec-3-enoyl]amino]-5-methylhexanoate Chemical compound CC(C[C@H](CC(=O)OC)NC(CC=CCCCCCC)=O)C VPUIDSONZVYYCG-MRXNPFEDSA-N 0.000 claims 1
- JVZQNAVNYKZDSI-SFHVURJKSA-N methyl (3S)-3-[[(E)-dec-3-enoyl]amino]-4-phenylsulfanylbutanoate Chemical compound O=C(CC=CCCCCCC)N[C@@H](CC(=O)OC)CSC1=CC=CC=C1 JVZQNAVNYKZDSI-SFHVURJKSA-N 0.000 claims 1
- IFGAIHBRILRHKP-ZMFCMNQTSA-N methyl (3r)-3-(2-hydroxyhexadecanoylamino)-5-methylhexanoate Chemical compound CCCCCCCCCCCCCCC(O)C(=O)N[C@H](CC(C)C)CC(=O)OC IFGAIHBRILRHKP-ZMFCMNQTSA-N 0.000 claims 1
- PGFCWCKYJMIGCP-GOSISDBHSA-N methyl (3r)-3-(dodecanoylamino)-5-methylhexanoate Chemical compound CCCCCCCCCCCC(=O)N[C@H](CC(C)C)CC(=O)OC PGFCWCKYJMIGCP-GOSISDBHSA-N 0.000 claims 1
- NCQAISRSOOJWCJ-INIZCTEOSA-N methyl (3s)-3-(octanoylamino)-4-phenylsulfanylbutanoate Chemical compound CCCCCCCC(=O)N[C@@H](CC(=O)OC)CSC1=CC=CC=C1 NCQAISRSOOJWCJ-INIZCTEOSA-N 0.000 claims 1
- AESHOYNIJBHMEG-VWLOTQADSA-N methyl (4S)-4-[[(E)-dec-3-enoyl]amino]-5-(3-phenylphenoxy)pentanoate Chemical compound C1(=CC(=CC=C1)OC[C@H](CCC(=O)OC)NC(CC=CCCCCCC)=O)C1=CC=CC=C1 AESHOYNIJBHMEG-VWLOTQADSA-N 0.000 claims 1
- LGKJHPPZJGNPJL-VWLOTQADSA-N methyl (4s)-4-(dec-3-enoylamino)-5-(3-phenylphenyl)sulfanylpentanoate Chemical compound CCCCCCC=CCC(=O)N[C@@H](CCC(=O)OC)CSC1=CC=CC(C=2C=CC=CC=2)=C1 LGKJHPPZJGNPJL-VWLOTQADSA-N 0.000 claims 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 40
- 230000000144 pharmacologic effect Effects 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 67
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 62
- 239000000047 product Substances 0.000 description 44
- 229910001868 water Inorganic materials 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
- 239000003921 oil Substances 0.000 description 34
- 229910052757 nitrogen Inorganic materials 0.000 description 33
- 239000007787 solid Substances 0.000 description 33
- 238000001819 mass spectrum Methods 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000377 silicon dioxide Substances 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 11
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 10
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 9
- 125000002837 carbocyclic group Chemical group 0.000 description 9
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 229920006395 saturated elastomer Polymers 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 102100026918 Phospholipase A2 Human genes 0.000 description 7
- 101710096328 Phospholipase A2 Proteins 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
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- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 1
- 208000009326 ileitis Diseases 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002555 ionophore Substances 0.000 description 1
- 230000000236 ionophoric effect Effects 0.000 description 1
- 208000002551 irritable bowel syndrome Diseases 0.000 description 1
- 210000001503 joint Anatomy 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- VOVZXURTCKPRDQ-CQSZACIVSA-N n-[4-[chloro(difluoro)methoxy]phenyl]-6-[(3r)-3-hydroxypyrrolidin-1-yl]-5-(1h-pyrazol-5-yl)pyridine-3-carboxamide Chemical compound C1[C@H](O)CCN1C1=NC=C(C(=O)NC=2C=CC(OC(F)(F)Cl)=CC=2)C=C1C1=CC=NN1 VOVZXURTCKPRDQ-CQSZACIVSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- HHXMXAQDOUCLDN-RXMQYKEDSA-N penem Chemical compound S1C=CN2C(=O)C[C@H]21 HHXMXAQDOUCLDN-RXMQYKEDSA-N 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001175 peptic effect Effects 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RQSBRFZHUKLKNO-SECBINFHSA-N tert-butyl n-[(2r)-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound CC(C)C[C@H](C=O)NC(=O)OC(C)(C)C RQSBRFZHUKLKNO-SECBINFHSA-N 0.000 description 1
- 101150050634 thiQ gene Proteins 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- HLCHESOMJVGDSJ-UHFFFAOYSA-N thiq Chemical compound C1=CC(Cl)=CC=C1CC(C(=O)N1CCC(CN2N=CN=C2)(CC1)C1CCCCC1)NC(=O)C1NCC2=CC=CC=C2C1 HLCHESOMJVGDSJ-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 1
- JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 230000036269 ulceration Effects 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
Classifications
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- 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
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/49—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/51—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/06—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to hydrogen atoms or to acyclic carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
- C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- 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
- C07D277/22—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile 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
- C07D333/26—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 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
- C07D333/30—Hetero atoms other than halogen
- C07D333/34—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Use Of Switch Circuits For Exchanges And Methods Of Control Of Multiplex Exchanges (AREA)
- Time-Division Multiplex Systems (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8928456.6 | 1989-12-16 | ||
| GB898928456A GB8928456D0 (en) | 1989-12-16 | 1989-12-16 | Compounds |
| GB909023645A GB9023645D0 (en) | 1990-10-31 | 1990-10-31 | Compounds |
| GB9023645.6 | 1990-10-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2072018A1 true CA2072018A1 (en) | 1991-06-17 |
Family
ID=26296380
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002072018A Abandoned CA2072018A1 (en) | 1989-12-16 | 1990-12-12 | Pharmacologically active amide carboxylate derivatives |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP0505467A1 (pt) |
| JP (1) | JPH05502233A (pt) |
| CA (1) | CA2072018A1 (pt) |
| FI (1) | FI922720A0 (pt) |
| IE (1) | IE904522A1 (pt) |
| PT (1) | PT96210A (pt) |
| WO (1) | WO1991008737A2 (pt) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5639746A (en) * | 1994-12-29 | 1997-06-17 | The Procter & Gamble Company | Hydroxamic acid-containing inhibitors of matrix metalloproteases |
| US5672598A (en) * | 1995-03-21 | 1997-09-30 | The Procter & Gamble Company | Lactam-containing hydroxamic acids |
| ES2247604T3 (es) * | 1995-06-12 | 2006-03-01 | G.D. SEARLE & CO. | Composiciones que comprenden un inhibidor de ciclooxigenasa-2 y un inhibidor de 5-lipoxigenasa. |
| UA59384C2 (uk) | 1996-12-20 | 2003-09-15 | Пфайзер, Інк. | Похідні сульфонамідів та амідів як агоністи простагландину, фармацевтична композиція та способи лікування на їх основі |
| CA2417127A1 (en) | 2000-07-24 | 2002-01-31 | The University Of Queensland | Compounds and inhibitors of phospholipases |
| AU2002216249A1 (en) * | 2000-12-21 | 2002-07-01 | De Novo Pharmaceuticals Ltd | Antimicrobial agents |
| GB0112324D0 (en) * | 2001-05-21 | 2001-07-11 | Croda Int Plc | Compounds |
| ES2273560B1 (es) * | 2005-02-25 | 2008-04-01 | Consejo Superior Investig. Cientificas | Compuesto inhibidor de la enzima ceramidasa, procedimiento de sintesis, composicion farmaceutica que lo contenga y sus aplicaciones. |
| FR2968952A1 (fr) * | 2010-12-17 | 2012-06-22 | Oreal | Ester d'acide amine n-acyle a titre d'agent apaisant |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790592A (pt) * | 1971-10-28 | 1973-04-26 | Oreal | |
| PH24782A (en) * | 1985-10-24 | 1990-10-30 | Sankyo Co | Composition containing a penem or carbapenem antibiotic and the use of the same |
-
1990
- 1990-12-12 WO PCT/GB1990/001941 patent/WO1991008737A2/en not_active Ceased
- 1990-12-12 FI FI922720A patent/FI922720A0/fi not_active Application Discontinuation
- 1990-12-12 CA CA002072018A patent/CA2072018A1/en not_active Abandoned
- 1990-12-12 JP JP3501855A patent/JPH05502233A/ja active Pending
- 1990-12-12 EP EP91901593A patent/EP0505467A1/en not_active Withdrawn
- 1990-12-14 IE IE452290A patent/IE904522A1/en unknown
- 1990-12-14 PT PT96210A patent/PT96210A/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO1991008737A2 (en) | 1991-06-27 |
| PT96210A (pt) | 1991-09-30 |
| IE904522A1 (en) | 1991-06-19 |
| FI922720A7 (fi) | 1992-06-12 |
| FI922720A0 (fi) | 1992-06-12 |
| EP0505467A1 (en) | 1992-09-30 |
| WO1991008737A3 (en) | 1992-04-16 |
| JPH05502233A (ja) | 1993-04-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |