JP2004527503A5 - - Google Patents
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- Publication number
- JP2004527503A5 JP2004527503A5 JP2002569829A JP2002569829A JP2004527503A5 JP 2004527503 A5 JP2004527503 A5 JP 2004527503A5 JP 2002569829 A JP2002569829 A JP 2002569829A JP 2002569829 A JP2002569829 A JP 2002569829A JP 2004527503 A5 JP2004527503 A5 JP 2004527503A5
- Authority
- JP
- Japan
- Prior art keywords
- carbonyl
- amino
- lower alkyl
- optionally substituted
- carboxamide
- 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.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 161
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- 125000003107 substituted aryl group Chemical group 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 40
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 125000003118 aryl group Chemical group 0.000 claims 31
- 125000000753 cycloalkyl group Chemical group 0.000 claims 29
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 29
- 150000002431 hydrogen Chemical class 0.000 claims 28
- -1 —CF 3 Chemical group 0.000 claims 25
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 23
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 21
- 229910052736 halogen Inorganic materials 0.000 claims 17
- 150000002367 halogens Chemical class 0.000 claims 17
- 125000003342 alkenyl group Chemical group 0.000 claims 16
- 229910052760 oxygen Inorganic materials 0.000 claims 15
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000000304 alkynyl group Chemical group 0.000 claims 11
- 208000023275 Autoimmune disease Diseases 0.000 claims 10
- 125000001475 halogen functional group Chemical group 0.000 claims 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 8
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 206010020751 Hypersensitivity Diseases 0.000 claims 5
- 206010061218 Inflammation Diseases 0.000 claims 5
- 230000007815 allergy Effects 0.000 claims 5
- 230000004054 inflammatory process Effects 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 229940095102 methyl benzoate Drugs 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 3
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims 3
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- JHQSXEMJFFLDQR-UHFFFAOYSA-N 2-[2-chloro-4-(quinoxaline-6-carbonylcarbamoylamino)phenoxy]acetic acid Chemical compound C1=C(Cl)C(OCC(=O)O)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 JHQSXEMJFFLDQR-UHFFFAOYSA-N 0.000 claims 2
- WKUPRCDZNFWXOH-UHFFFAOYSA-N 2-chloro-4-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 WKUPRCDZNFWXOH-UHFFFAOYSA-N 0.000 claims 2
- GVJLCTNSSRYHNA-UHFFFAOYSA-N 2-hydroxy-4-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 GVJLCTNSSRYHNA-UHFFFAOYSA-N 0.000 claims 2
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 2
- 201000001320 Atherosclerosis Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000007342 Diabetic Nephropathies Diseases 0.000 claims 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 2
- 206010018364 Glomerulonephritis Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- KFJPXYHXHOOENW-UHFFFAOYSA-N N-[(3-methylphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C KFJPXYHXHOOENW-UHFFFAOYSA-N 0.000 claims 2
- 206010033645 Pancreatitis Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 208000033679 diabetic kidney disease Diseases 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- WFYHWQNNGKPZJL-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)carbamoyl]-4-methyl-2,3-dihydro-1,4-benzoxazine-7-carboxamide Chemical compound C=1C=C2N(C)CCOC2=CC=1C(=O)NC(=O)NC1=CC=C(Cl)C(Cl)=C1 WFYHWQNNGKPZJL-UHFFFAOYSA-N 0.000 claims 2
- POQOCDNKLLQVEH-UHFFFAOYSA-N n-[(3-propan-2-yloxyphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound CC(C)OC1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 POQOCDNKLLQVEH-UHFFFAOYSA-N 0.000 claims 2
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 2
- 208000037803 restenosis Diseases 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 238000002054 transplantation Methods 0.000 claims 2
- JCTRSHYQUOJCGB-UHFFFAOYSA-N 2-chloro-5-(2,3-dihydro-1,4-benzodioxine-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 JCTRSHYQUOJCGB-UHFFFAOYSA-N 0.000 claims 1
- CTYRPBKUPNOXMR-UHFFFAOYSA-N 2-chloro-5-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 CTYRPBKUPNOXMR-UHFFFAOYSA-N 0.000 claims 1
- YZIBETAXVFMICO-UHFFFAOYSA-N 2-chloro-6-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=C(Cl)C=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 YZIBETAXVFMICO-UHFFFAOYSA-N 0.000 claims 1
- DZEIUSMCLZIEIB-UHFFFAOYSA-N 2-phenoxy-4-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC=C(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)C=C1OC1=CC=CC=C1 DZEIUSMCLZIEIB-UHFFFAOYSA-N 0.000 claims 1
- ATWZWWAIOSHOTC-UHFFFAOYSA-N 2-propan-2-yloxy-4-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=C(C(O)=O)C(OC(C)C)=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 ATWZWWAIOSHOTC-UHFFFAOYSA-N 0.000 claims 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 1
- RKLNGQBXZBWJOC-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxine-6-carbonylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 RKLNGQBXZBWJOC-UHFFFAOYSA-N 0.000 claims 1
- OBELLAKXAHXDNH-UHFFFAOYSA-N 3-(quinoxaline-6-carbonylcarbamoylamino)-5-(trifluoromethyl)benzoic acid Chemical compound FC(F)(F)C1=CC(C(=O)O)=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 OBELLAKXAHXDNH-UHFFFAOYSA-N 0.000 claims 1
- DLDRGTKDMKRQHP-UHFFFAOYSA-N 3-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 DLDRGTKDMKRQHP-UHFFFAOYSA-N 0.000 claims 1
- ZFUCQBFVCLXMOR-UHFFFAOYSA-N 4-(2,3-dihydro-1,4-benzodioxine-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 ZFUCQBFVCLXMOR-UHFFFAOYSA-N 0.000 claims 1
- OFSZIDOVOFBWAK-UHFFFAOYSA-N 4-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 OFSZIDOVOFBWAK-UHFFFAOYSA-N 0.000 claims 1
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims 1
- KBKCJCHPFABMCT-UHFFFAOYSA-N 5-chloro-2-(quinoxaline-6-carbonylcarbamoylamino)benzoic acid Chemical compound OC(=O)C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 KBKCJCHPFABMCT-UHFFFAOYSA-N 0.000 claims 1
- OPJQLYHXJLAUGI-UHFFFAOYSA-N C1=C(C(F)(F)F)C(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 Chemical compound C1=C(C(F)(F)F)C(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 OPJQLYHXJLAUGI-UHFFFAOYSA-N 0.000 claims 1
- DDOGEROJPSRHSE-UHFFFAOYSA-N C1=C(C(F)(F)F)C(C)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 Chemical compound C1=C(C(F)(F)F)C(C)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 DDOGEROJPSRHSE-UHFFFAOYSA-N 0.000 claims 1
- KJYDAIDIVRCAJH-UHFFFAOYSA-N C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 KJYDAIDIVRCAJH-UHFFFAOYSA-N 0.000 claims 1
- ZZWVUDNYURUZGO-UHFFFAOYSA-N C1=C(I)C(C)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 Chemical compound C1=C(I)C(C)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 ZZWVUDNYURUZGO-UHFFFAOYSA-N 0.000 claims 1
- KJYNYZFHIFJYLH-UHFFFAOYSA-N C1=C2N(CCO)CCNC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C1=C2N(CCO)CCNC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 KJYNYZFHIFJYLH-UHFFFAOYSA-N 0.000 claims 1
- ZHDQQXYCBXKALR-UHFFFAOYSA-N C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(Br)=C1 Chemical compound C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(Br)=C1 ZHDQQXYCBXKALR-UHFFFAOYSA-N 0.000 claims 1
- DCAXTIBAFMXSSP-UHFFFAOYSA-N C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C#N)=C1 Chemical compound C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C#N)=C1 DCAXTIBAFMXSSP-UHFFFAOYSA-N 0.000 claims 1
- BHDYKZNYKLVBJR-UHFFFAOYSA-N C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 BHDYKZNYKLVBJR-UHFFFAOYSA-N 0.000 claims 1
- CJHPGOAESUKDKU-UHFFFAOYSA-N C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=C(NCCN2)C2=C1 Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=C(NCCN2)C2=C1 CJHPGOAESUKDKU-UHFFFAOYSA-N 0.000 claims 1
- LVRBXWHTSGGMGQ-UHFFFAOYSA-N C=1C=C2N(C)CCN(C)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C=1C=C2N(C)CCN(C)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 LVRBXWHTSGGMGQ-UHFFFAOYSA-N 0.000 claims 1
- NSXIBYCAKHUNJF-UHFFFAOYSA-N C=1C=C2N(C)CCOC2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C=1C=C2N(C)CCOC2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 NSXIBYCAKHUNJF-UHFFFAOYSA-N 0.000 claims 1
- RPCKZNIZLZRVMU-UHFFFAOYSA-N C=1C=C2N(CC)CCN(CC)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C=1C=C2N(CC)CCN(CC)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 RPCKZNIZLZRVMU-UHFFFAOYSA-N 0.000 claims 1
- RYFUSYDRFQRZFF-UHFFFAOYSA-N C=1C=C2N(CCO)CCN(CCO)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 Chemical compound C=1C=C2N(CCO)CCN(CCO)C2=CC=1C(=O)NC(=O)NC1=CC=CC(C(F)(F)F)=C1 RYFUSYDRFQRZFF-UHFFFAOYSA-N 0.000 claims 1
- LFYQTGJRYOMNQK-UHFFFAOYSA-N C=1C=C2OCCOC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 Chemical compound C=1C=C2OCCOC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 LFYQTGJRYOMNQK-UHFFFAOYSA-N 0.000 claims 1
- MCELGMQCCILXPA-UHFFFAOYSA-N C=1C=C2OCCOC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=NC=CS1 Chemical compound C=1C=C2OCCOC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=NC=CS1 MCELGMQCCILXPA-UHFFFAOYSA-N 0.000 claims 1
- IMFPNUOXDVGYLQ-UHFFFAOYSA-N CC(C)(C)C1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound CC(C)(C)C1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 IMFPNUOXDVGYLQ-UHFFFAOYSA-N 0.000 claims 1
- IENMIVXDOPOYTE-UHFFFAOYSA-N CCC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound CCC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 IENMIVXDOPOYTE-UHFFFAOYSA-N 0.000 claims 1
- CQWUFNJRPFVUTG-UHFFFAOYSA-N CCOC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound CCOC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 CQWUFNJRPFVUTG-UHFFFAOYSA-N 0.000 claims 1
- 229940126062 Compound A Drugs 0.000 claims 1
- 102000004127 Cytokines Human genes 0.000 claims 1
- 108090000695 Cytokines Proteins 0.000 claims 1
- JUNSFILCRFSAQC-UHFFFAOYSA-N FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 JUNSFILCRFSAQC-UHFFFAOYSA-N 0.000 claims 1
- GDFPEDHEWNVYKY-UHFFFAOYSA-N FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3C=CC=NC3=CC=2)=C1 Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3C=CC=NC3=CC=2)=C1 GDFPEDHEWNVYKY-UHFFFAOYSA-N 0.000 claims 1
- JQSFVMSWJVHBTN-UHFFFAOYSA-N FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 JQSFVMSWJVHBTN-UHFFFAOYSA-N 0.000 claims 1
- KXJBIEGYMKPDSZ-UHFFFAOYSA-N FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 KXJBIEGYMKPDSZ-UHFFFAOYSA-N 0.000 claims 1
- NBKMROOYNKMVHQ-UHFFFAOYSA-N FC(F)(F)OC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 NBKMROOYNKMVHQ-UHFFFAOYSA-N 0.000 claims 1
- CDMJMVSAUGGVKK-UHFFFAOYSA-N FC(F)(F)SC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 Chemical compound FC(F)(F)SC1=CC=CC(NC(=O)NC(=O)C=2C=C3OCCOC3=CC=2)=C1 CDMJMVSAUGGVKK-UHFFFAOYSA-N 0.000 claims 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 1
- IIQRZXPPFHLKSN-UHFFFAOYSA-N N-[(2,4-dichlorophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=C(C=C(C=C1)Cl)Cl IIQRZXPPFHLKSN-UHFFFAOYSA-N 0.000 claims 1
- WUQUCPZRCAVKFV-UHFFFAOYSA-N N-[(2-iodophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=C(C=CC=C1)I WUQUCPZRCAVKFV-UHFFFAOYSA-N 0.000 claims 1
- LQUQAUROGRZBCG-UHFFFAOYSA-N N-[(3,4-dichlorophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound Clc1ccc(NC(=O)NC(=O)C2COCCO2)cc1Cl LQUQAUROGRZBCG-UHFFFAOYSA-N 0.000 claims 1
- OWEFTAFPFOVATR-UHFFFAOYSA-N N-[(3,5-dichlorophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC(=C1)Cl)Cl OWEFTAFPFOVATR-UHFFFAOYSA-N 0.000 claims 1
- HPWNARXJWPNSKV-UHFFFAOYSA-N N-[(3-acetylphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C(C)=O HPWNARXJWPNSKV-UHFFFAOYSA-N 0.000 claims 1
- UBQIDRBGQSDSRT-UHFFFAOYSA-N N-[(3-bromophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)Br UBQIDRBGQSDSRT-UHFFFAOYSA-N 0.000 claims 1
- XSKVJRKZFHEKFA-UHFFFAOYSA-N N-[(3-chloro-4-hydroxyphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=C(C=C1)O)Cl XSKVJRKZFHEKFA-UHFFFAOYSA-N 0.000 claims 1
- SMZSKLWUWSGCOJ-UHFFFAOYSA-N N-[(3-chloro-4-hydroxyphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C1=C(Cl)C(O)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 SMZSKLWUWSGCOJ-UHFFFAOYSA-N 0.000 claims 1
- AVWPFQANRDXZHV-UHFFFAOYSA-N N-[(3-chlorophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)Cl AVWPFQANRDXZHV-UHFFFAOYSA-N 0.000 claims 1
- FAVUDGAZOIRUER-UHFFFAOYSA-N N-[(3-cyanophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C#N FAVUDGAZOIRUER-UHFFFAOYSA-N 0.000 claims 1
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| AU2002217999A1 (en) | 2000-11-01 | 2002-05-15 | Cor Therapeutics, Inc. | Process for the production of 4-quinazolinylpiperazin-1-carboxylic acid phenylamides |
| US7732162B2 (en) | 2003-05-05 | 2010-06-08 | Probiodrug Ag | Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases |
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-
2002
- 2002-02-25 TW TW091103254A patent/TWI245761B/zh not_active IP Right Cessation
- 2002-02-27 US US10/087,208 patent/US6809113B2/en not_active Expired - Fee Related
- 2002-02-28 KR KR10-2003-7011481A patent/KR20040018336A/ko not_active Abandoned
- 2002-02-28 ES ES02709746T patent/ES2254653T3/es not_active Expired - Lifetime
- 2002-02-28 DE DE60208159T patent/DE60208159T2/de not_active Expired - Fee Related
- 2002-02-28 BR BR0207750-7A patent/BR0207750A/pt not_active IP Right Cessation
- 2002-02-28 MX MXPA03007861A patent/MXPA03007861A/es active IP Right Grant
- 2002-02-28 AT AT02709746T patent/ATE313537T1/de not_active IP Right Cessation
- 2002-02-28 AR ARP020100728A patent/AR035759A1/es unknown
- 2002-02-28 CA CA002439849A patent/CA2439849A1/en not_active Abandoned
- 2002-02-28 WO PCT/US2002/006256 patent/WO2002070509A2/en not_active Ceased
- 2002-02-28 EP EP02709746A patent/EP1363897B1/en not_active Expired - Lifetime
- 2002-02-28 CN CNB028057929A patent/CN1259315C/zh not_active Expired - Fee Related
- 2002-02-28 JP JP2002569829A patent/JP4291576B2/ja not_active Expired - Fee Related
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2004
- 2004-10-19 US US10/969,440 patent/US7297696B2/en not_active Expired - Fee Related
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