JP2004527503A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- LWFYNHPVYRUBPC-UHFFFAOYSA-N N-[(3-iodophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)I LWFYNHPVYRUBPC-UHFFFAOYSA-N 0.000 claims 1
- PDVFLPUXMWLPSE-UHFFFAOYSA-N N-[(3-nitrophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound [O-][N+](=O)c1cccc(NC(=O)NC(=O)C2COCCO2)c1 PDVFLPUXMWLPSE-UHFFFAOYSA-N 0.000 claims 1
- DEVDOLVUDYZWFH-UHFFFAOYSA-N N-[(3-phenoxyphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)OC1=CC=CC=C1 DEVDOLVUDYZWFH-UHFFFAOYSA-N 0.000 claims 1
- XSNASYYIVYVJLY-UHFFFAOYSA-N N-[(3-pyridin-2-ylphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C1=NC=CC=C1 XSNASYYIVYVJLY-UHFFFAOYSA-N 0.000 claims 1
- ZDDFAMLDCVZAIR-UHFFFAOYSA-N N-[(3-thiophen-2-ylphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C=1SC=CC=1 ZDDFAMLDCVZAIR-UHFFFAOYSA-N 0.000 claims 1
- CAHLYYTWTGBBAS-UHFFFAOYSA-N N-[(3-thiophen-3-ylphenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C1=CSC=C1 CAHLYYTWTGBBAS-UHFFFAOYSA-N 0.000 claims 1
- DOLSVXRHAVSCFE-UHFFFAOYSA-N N-[(4-chlorophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC=C(C=C1)Cl DOLSVXRHAVSCFE-UHFFFAOYSA-N 0.000 claims 1
- QREJGFZWWLKXIU-UHFFFAOYSA-N N-[(4-iodophenyl)carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC=C(C=C1)I QREJGFZWWLKXIU-UHFFFAOYSA-N 0.000 claims 1
- HGLPWPPZQKEGIM-UHFFFAOYSA-N N-[[3-(2H-tetrazol-5-yl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C1=NN=NN1 HGLPWPPZQKEGIM-UHFFFAOYSA-N 0.000 claims 1
- MTLOOSGPAYZVTJ-UHFFFAOYSA-N N-[[3-(furan-2-yl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)C=1OC=CC=1 MTLOOSGPAYZVTJ-UHFFFAOYSA-N 0.000 claims 1
- HFAYSWLELYRFGX-UHFFFAOYSA-N N-[[3-(trifluoromethoxy)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC=C1)OC(F)(F)F HFAYSWLELYRFGX-UHFFFAOYSA-N 0.000 claims 1
- YQXPVKUUECMONY-UHFFFAOYSA-N N-[[3-hydroxy-5-(trifluoromethyl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=CC(=C1)C(F)(F)F)O YQXPVKUUECMONY-UHFFFAOYSA-N 0.000 claims 1
- LAGHQFVCZJJHQQ-UHFFFAOYSA-N N-[[4-(2H-tetrazol-5-yl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC=C(C=C1)C1=NN=NN1 LAGHQFVCZJJHQQ-UHFFFAOYSA-N 0.000 claims 1
- QSGFHTBYRQXBGP-UHFFFAOYSA-N N-[[4-(trifluoromethyl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC=C(C=C1)C(F)(F)F QSGFHTBYRQXBGP-UHFFFAOYSA-N 0.000 claims 1
- YFCVHBJUZXRYQM-UHFFFAOYSA-N N-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]-1,4-dioxane-2-carboxamide Chemical compound O1CCOCC1C(=O)NC(=O)NC1=CC(=C(C=C1)Cl)C(F)(F)F YFCVHBJUZXRYQM-UHFFFAOYSA-N 0.000 claims 1
- MWHVKNLKNIXWIC-UHFFFAOYSA-N O1CCOC2=C1C=CC(=C2)C(=O)NC(=O)NC2=CC(=CC=C2)OC(C)C Chemical compound O1CCOC2=C1C=CC(=C2)C(=O)NC(=O)NC2=CC(=CC=C2)OC(C)C MWHVKNLKNIXWIC-UHFFFAOYSA-N 0.000 claims 1
- 238000009825 accumulation Methods 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 229960004050 aminobenzoic acid Drugs 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000002955 immunomodulating agent Substances 0.000 claims 1
- 230000002584 immunomodulator Effects 0.000 claims 1
- 229940121354 immunomodulator Drugs 0.000 claims 1
- 210000004698 lymphocyte Anatomy 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000001616 monocyte Anatomy 0.000 claims 1
- CIIWRLCXEMMCAL-UHFFFAOYSA-N n-[(2,4-dichlorophenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 CIIWRLCXEMMCAL-UHFFFAOYSA-N 0.000 claims 1
- ZFSVUPSUMZSQBX-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)carbamoyl]-2,3-dimethylquinoxaline-6-carboxamide Chemical compound C1=C2N=C(C)C(C)=NC2=CC=C1C(=O)NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ZFSVUPSUMZSQBX-UHFFFAOYSA-N 0.000 claims 1
- SABBIASKTUVLDU-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)carbamoyl]quinoline-6-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=C2)C2=C1 SABBIASKTUVLDU-UHFFFAOYSA-N 0.000 claims 1
- UIUZGEYXVCZEHX-UHFFFAOYSA-N n-[(3,4-dichlorophenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 UIUZGEYXVCZEHX-UHFFFAOYSA-N 0.000 claims 1
- AGMGIMKEAPUIFP-UHFFFAOYSA-N n-[(3-benzoylphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C(=O)C1=CC=CC=C1 AGMGIMKEAPUIFP-UHFFFAOYSA-N 0.000 claims 1
- UAWNBIDDBPBKHZ-UHFFFAOYSA-N n-[(3-bromophenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound BrC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 UAWNBIDDBPBKHZ-UHFFFAOYSA-N 0.000 claims 1
- QCIOXVXREYECSX-UHFFFAOYSA-N n-[(3-bromophenyl)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=CC(Br)=C1 QCIOXVXREYECSX-UHFFFAOYSA-N 0.000 claims 1
- VMWRPXNXFGZLOJ-UHFFFAOYSA-N n-[(3-bromophenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound BrC1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 VMWRPXNXFGZLOJ-UHFFFAOYSA-N 0.000 claims 1
- USSURGJNWHXJIV-UHFFFAOYSA-N n-[(3-chloro-2,6-diethylphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound CCC1=CC=C(Cl)C(CC)=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 USSURGJNWHXJIV-UHFFFAOYSA-N 0.000 claims 1
- YUDXSUBMEPRTKG-UHFFFAOYSA-N n-[(3-chloro-4-hydroxyphenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C1=C(Cl)C(O)=CC=C1NC(=O)NC(=O)C1=CC=C(NCCN2)C2=C1 YUDXSUBMEPRTKG-UHFFFAOYSA-N 0.000 claims 1
- VKDBQHLSIPFKHL-UHFFFAOYSA-N n-[(3-chloro-4-methylphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound C1=C(Cl)C(C)=CC=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 VKDBQHLSIPFKHL-UHFFFAOYSA-N 0.000 claims 1
- XZXWJRGRWYCPEI-UHFFFAOYSA-N n-[(3-chlorophenyl)-(methoxymethyl)carbamoyl]-n-(methoxymethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound C=1C=C2OCCOC2=CC=1C(=O)N(COC)C(=O)N(COC)C1=CC=CC(Cl)=C1 XZXWJRGRWYCPEI-UHFFFAOYSA-N 0.000 claims 1
- VSNTXPPXIFRFKX-UHFFFAOYSA-N n-[(3-chlorophenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound ClC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 VSNTXPPXIFRFKX-UHFFFAOYSA-N 0.000 claims 1
- QAPKCNVMZBOTNO-UHFFFAOYSA-N n-[(3-chlorophenyl)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=CC(Cl)=C1 QAPKCNVMZBOTNO-UHFFFAOYSA-N 0.000 claims 1
- MZKPODNJRQOBIT-UHFFFAOYSA-N n-[(3-chlorophenyl)carbamoyl]-n-(2-methoxyethoxymethyl)-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound C=1C=C2OCCOC2=CC=1C(=O)N(COCCOC)C(=O)NC1=CC=CC(Cl)=C1 MZKPODNJRQOBIT-UHFFFAOYSA-N 0.000 claims 1
- NGGFEKHYBQZMDY-UHFFFAOYSA-N n-[(3-chlorophenyl)carbamoyl]quinoline-6-carboxamide Chemical compound ClC1=CC=CC(NC(=O)NC(=O)C=2C=C3C=CC=NC3=CC=2)=C1 NGGFEKHYBQZMDY-UHFFFAOYSA-N 0.000 claims 1
- XPZYTTWFQSVEPA-UHFFFAOYSA-N n-[(3-chlorophenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound ClC1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 XPZYTTWFQSVEPA-UHFFFAOYSA-N 0.000 claims 1
- HGPCKKQYNXNVHL-UHFFFAOYSA-N n-[(3-cyanophenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C=1C=C2NCCNC2=CC=1C(=O)NC(=O)NC1=CC=CC(C#N)=C1 HGPCKKQYNXNVHL-UHFFFAOYSA-N 0.000 claims 1
- LHGNDIBJNJEQEQ-UHFFFAOYSA-N n-[(3-cyanophenyl)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=CC(C#N)=C1 LHGNDIBJNJEQEQ-UHFFFAOYSA-N 0.000 claims 1
- XDMKEQZRRSZDKD-UHFFFAOYSA-N n-[(3-cyanophenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC1=CC=CC(C#N)=C1 XDMKEQZRRSZDKD-UHFFFAOYSA-N 0.000 claims 1
- ZUGGJVLYVSMTSV-UHFFFAOYSA-N n-[(3-ethynylphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound C=1C=C2OCCOC2=CC=1C(=O)NC(=O)NC1=CC=CC(C#C)=C1 ZUGGJVLYVSMTSV-UHFFFAOYSA-N 0.000 claims 1
- PGLXFIPIAABWRJ-UHFFFAOYSA-N n-[(3-iodophenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound IC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 PGLXFIPIAABWRJ-UHFFFAOYSA-N 0.000 claims 1
- WRBBQALERFQKBE-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C=1C=C2NCCNC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 WRBBQALERFQKBE-UHFFFAOYSA-N 0.000 claims 1
- BZYXGADGPVGIKQ-UHFFFAOYSA-N n-[(3-phenoxyphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1OC1=CC=CC=C1 BZYXGADGPVGIKQ-UHFFFAOYSA-N 0.000 claims 1
- ZVXDYWQPHGTRMX-UHFFFAOYSA-N n-[(3-phenylphenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C=1C=C2NCCNC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 ZVXDYWQPHGTRMX-UHFFFAOYSA-N 0.000 claims 1
- CEHDPNIVRONKKX-UHFFFAOYSA-N n-[(3-phenylphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CC=C1 CEHDPNIVRONKKX-UHFFFAOYSA-N 0.000 claims 1
- GFTAZVGNUNMYGJ-UHFFFAOYSA-N n-[(3-propan-2-yloxyphenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound CC(C)OC1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 GFTAZVGNUNMYGJ-UHFFFAOYSA-N 0.000 claims 1
- UCSKVPFEIKAMCE-UHFFFAOYSA-N n-[(3-propan-2-ylphenyl)carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound CC(C)C1=CC=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 UCSKVPFEIKAMCE-UHFFFAOYSA-N 0.000 claims 1
- BUPOMLLHLSKRKI-UHFFFAOYSA-N n-[(3-propan-2-ylphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound CC(C)C1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 BUPOMLLHLSKRKI-UHFFFAOYSA-N 0.000 claims 1
- FAWWZRZKRBALGV-UHFFFAOYSA-N n-[(3-pyridin-2-ylphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CC=N1 FAWWZRZKRBALGV-UHFFFAOYSA-N 0.000 claims 1
- OUHPJKZOUVQVOQ-UHFFFAOYSA-N n-[(3-thiophen-2-ylphenyl)carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CS1 OUHPJKZOUVQVOQ-UHFFFAOYSA-N 0.000 claims 1
- HUHMNUBMKANCAD-UHFFFAOYSA-N n-[(5-chloro-2-methoxyphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 HUHMNUBMKANCAD-UHFFFAOYSA-N 0.000 claims 1
- KPAJDZCRJADJPU-UHFFFAOYSA-N n-[(5-chloro-2-methylphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound CC1=CC=C(Cl)C=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 KPAJDZCRJADJPU-UHFFFAOYSA-N 0.000 claims 1
- YEBTXYKCOIBIPO-UHFFFAOYSA-N n-[(5-iodo-2-methylphenyl)carbamoyl]-2,3-dihydro-1,4-benzodioxine-6-carboxamide Chemical compound CC1=CC=C(I)C=C1NC(=O)NC(=O)C1=CC=C(OCCO2)C2=C1 YEBTXYKCOIBIPO-UHFFFAOYSA-N 0.000 claims 1
- FYDSHNUQIOMSNC-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 FYDSHNUQIOMSNC-UHFFFAOYSA-N 0.000 claims 1
- NGFZLQBDWGGKTK-UHFFFAOYSA-N n-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 NGFZLQBDWGGKTK-UHFFFAOYSA-N 0.000 claims 1
- UXFSYMISVNCSNO-UHFFFAOYSA-N n-[[3-(1,3-thiazol-2-yl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=NC=CS1 UXFSYMISVNCSNO-UHFFFAOYSA-N 0.000 claims 1
- SEZFKCBTJLIAIL-UHFFFAOYSA-N n-[[3-(furan-2-yl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound C=1C=C2N=CC=NC2=CC=1C(=O)NC(=O)NC(C=1)=CC=CC=1C1=CC=CO1 SEZFKCBTJLIAIL-UHFFFAOYSA-N 0.000 claims 1
- DXQSGAJNQMHTRU-UHFFFAOYSA-N n-[[3-(trifluoromethoxy)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound FC(F)(F)OC1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 DXQSGAJNQMHTRU-UHFFFAOYSA-N 0.000 claims 1
- DVQDOLKEIYCZFT-UHFFFAOYSA-N n-[[3-(trifluoromethyl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 DVQDOLKEIYCZFT-UHFFFAOYSA-N 0.000 claims 1
- KDXZOEPYDFHYAL-UHFFFAOYSA-N n-[[4-(trifluoromethyl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 KDXZOEPYDFHYAL-UHFFFAOYSA-N 0.000 claims 1
- JICZSYIXBRGOPY-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3NCCNC3=CC=2)=C1 JICZSYIXBRGOPY-UHFFFAOYSA-N 0.000 claims 1
- CGKCHNCCHBHMBU-UHFFFAOYSA-N n-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(NC(=O)NC(=O)C=2C=C3N=CC=NC3=CC=2)=C1 CGKCHNCCHBHMBU-UHFFFAOYSA-N 0.000 claims 1
- UBJCAYGEQKJEPP-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]carbamoyl]-1,2,3,4-tetrahydroquinoxaline-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC(=O)C1=CC=C(NCCN2)C2=C1 UBJCAYGEQKJEPP-UHFFFAOYSA-N 0.000 claims 1
- NAYUELBXBSUANY-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]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(F)C(C(F)(F)F)=C1 NAYUELBXBSUANY-UHFFFAOYSA-N 0.000 claims 1
- CYFFGEQJLLXYDJ-UHFFFAOYSA-N n-[[4-fluoro-3-(trifluoromethyl)phenyl]carbamoyl]quinoxaline-6-carboxamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1NC(=O)NC(=O)C1=CC=C(N=CC=N2)C2=C1 CYFFGEQJLLXYDJ-UHFFFAOYSA-N 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27279201P | 2001-03-01 | 2001-03-01 | |
| PCT/US2002/006256 WO2002070509A2 (en) | 2001-03-01 | 2002-02-28 | Antagonists of mcp-1 function and methods of use thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004527503A JP2004527503A (ja) | 2004-09-09 |
| JP2004527503A5 true JP2004527503A5 (enExample) | 2006-01-19 |
| JP4291576B2 JP4291576B2 (ja) | 2009-07-08 |
Family
ID=23041292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002569829A Expired - Fee Related JP4291576B2 (ja) | 2001-03-01 | 2002-02-28 | Ｍｃｐ−１機能のアンタゴニストおよびその使用方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US6809113B2 (enExample) |
| EP (1) | EP1363897B1 (enExample) |
| JP (1) | JP4291576B2 (enExample) |
| KR (1) | KR20040018336A (enExample) |
| CN (1) | CN1259315C (enExample) |
| AR (1) | AR035759A1 (enExample) |
| AT (1) | ATE313537T1 (enExample) |
| BR (1) | BR0207750A (enExample) |
| CA (1) | CA2439849A1 (enExample) |
| DE (1) | DE60208159T2 (enExample) |
| ES (1) | ES2254653T3 (enExample) |
| MX (1) | MXPA03007861A (enExample) |
| TW (1) | TWI245761B (enExample) |
| WO (1) | WO2002070509A2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US20080187508A1 (en) * | 2004-09-08 | 2008-08-07 | Boys Town National Research Hospital | Treatment of Golmerular Basement Membrane Disease Involving Matrix Metalloproteinase-12 |
| NZ560917A (en) | 2005-03-31 | 2011-01-28 | Pfizer Prod Inc | Cyclopentapyridine and tetrahydroquinoline derivatives |
| WO2007066496A1 (en) * | 2005-12-07 | 2007-06-14 | Sumitomo Chemical Company, Limited | Benzoylurea compound and use thereof |
| US7601716B2 (en) * | 2006-05-01 | 2009-10-13 | Cephalon, Inc. | Pyridopyrazines and derivatives thereof as ALK and c-Met inhibitors |
| JP2009544690A (ja) * | 2006-07-24 | 2009-12-17 | イェダ リサーチ アンド デベロップメント カンパニー リミテッド | Ｃｃｌ２を含む医薬組成物および炎症の処置のためのその使用 |
| US20080076120A1 (en) * | 2006-09-14 | 2008-03-27 | Millennium Pharmaceuticals, Inc. | Methods for the identification, evaluation and treatment of patients having CC-Chemokine receptor 2 (CCR-2) mediated disorders |
| US8278345B2 (en) | 2006-11-09 | 2012-10-02 | Probiodrug Ag | Inhibitors of glutaminyl cyclase |
| DK2091948T3 (da) | 2006-11-30 | 2012-07-23 | Probiodrug Ag | Nye inhibitorer af glutaminylcyclase |
| US20100303777A1 (en) * | 2006-12-14 | 2010-12-02 | Actogenix N.V. | Delivery of binding molecules to induce immunomodulation |
| EA200901140A1 (ru) | 2007-03-01 | 2010-04-30 | Пробиодруг Аг | Новое применение ингибиторов глутаминилциклазы |
| DK2142514T3 (da) | 2007-04-18 | 2015-03-23 | Probiodrug Ag | Thioureaderivater som glutaminylcyclase-inhibitorer |
| US8356920B2 (en) * | 2007-12-12 | 2013-01-22 | Levine Jonathan E | Lighting device |
| US20100152160A1 (en) * | 2008-12-12 | 2010-06-17 | Khamrai Uttam | Novel benzodioxane and benzoxazine derivatives useful as cc chemokine receptor ligands |
| KR101755737B1 (ko) | 2009-09-11 | 2017-07-07 | 프로비오드룩 아게 | 글루타미닐 사이클라제의 억제제로서 헤테로사이클릭 유도체 |
| ES2586231T3 (es) | 2010-03-03 | 2016-10-13 | Probiodrug Ag | Inhibidores de glutaminil ciclasa |
| WO2011110613A1 (en) | 2010-03-10 | 2011-09-15 | Probiodrug Ag | Heterocyclic inhibitors of glutaminyl cyclase (qc, ec 2.3.2.5) |
| WO2011131748A2 (en) | 2010-04-21 | 2011-10-27 | Probiodrug Ag | Novel inhibitors |
| WO2012123563A1 (en) | 2011-03-16 | 2012-09-20 | Probiodrug Ag | Benz imidazole derivatives as inhibitors of glutaminyl cyclase |
| EP2522341A1 (en) * | 2011-05-13 | 2012-11-14 | Tragex Pharma | Pharmaceutical compositions comprising Neuropilin inhibitors, and their use for the prevention and/or treatment of angiogenic disorders and cancers |
| HUE053645T2 (hu) | 2013-11-18 | 2021-07-28 | Forma Therapeutics Inc | Tetrahidrokinolin kompozíciók mint BET bromodomén inhibitorok |
| RU2720237C2 (ru) | 2013-11-18 | 2020-04-28 | Форма Терапеутикс, Инк. | Композиции, содержащие бензопиперазин, в качестве ингибиторов бромодоменов вет |
| WO2018106959A1 (en) | 2016-12-07 | 2018-06-14 | Progenity Inc. | Gastrointestinal tract detection methods, devices and systems |
| US10980739B2 (en) | 2016-12-14 | 2021-04-20 | Progenity, Inc. | Treatment of a disease of the gastrointestinal tract with a chemokine/chemokine receptor inhibitor |
| WO2018201091A1 (en) * | 2017-04-27 | 2018-11-01 | Washington University | Chemokine decoy receptors of rodent gammaherpesviruses and uses thereof |
| PL3461819T3 (pl) | 2017-09-29 | 2020-11-30 | Probiodrug Ag | Inhibitory cyklazy glutaminylowej |
| EP3643711A1 (en) | 2018-10-24 | 2020-04-29 | Bayer Animal Health GmbH | New anthelmintic compounds |
| WO2020106750A1 (en) | 2018-11-19 | 2020-05-28 | Progenity, Inc. | Methods and devices for treating a disease with biotherapeutics |
| EP3870261B1 (en) | 2019-12-13 | 2024-01-31 | Biora Therapeutics, Inc. | Ingestible device for delivery of therapeutic agent to the gastrointestinal tract |
Family Cites Families (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1250611A (enExample) | 1968-02-03 | 1971-10-20 | ||
| IE32700B1 (en) | 1968-02-03 | 1973-10-31 | Beecham Group Ltd | Penicillins |
| DE2131034A1 (de) * | 1971-06-23 | 1973-01-11 | Hoechst Ag | Acylharnstoffe und verfahren zu ihrer herstellung |
| DE2652004C3 (de) * | 1976-11-15 | 1979-09-13 | Basf Ag, 6700 Ludwigshafen | l-Acyl-2-arylamino-2-imidazoline, Verfahren zu ihrer Herstellung und ihre Verwendung |
| US4163784A (en) | 1978-03-09 | 1979-08-07 | Pfizer Inc. | Heterocyclylcarbonyl derivatives of urea, agents for dissolution of gallstones |
| GB8528234D0 (en) | 1985-11-15 | 1985-12-18 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| JP2650055B2 (ja) | 1988-11-28 | 1997-09-03 | キヤノン株式会社 | 電子写真感光体 |
| FR2672888B1 (fr) | 1991-02-14 | 1994-02-04 | Fabre Medicament Pierre | Nouvelles urees et thiourees, leur preparation et leur application en therapeutique. |
| JP3964478B2 (ja) * | 1995-06-30 | 2007-08-22 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | ヘテロ環含有カルボン酸誘導体及びそれを含有する医薬 |
| AU1208397A (en) | 1995-12-28 | 1997-07-28 | Takeda Chemical Industries Ltd. | Diphenylmethane derivatives as mip-1alpha/rantes receptor antagonists |
| JPH09255572A (ja) | 1996-03-26 | 1997-09-30 | Takeda Chem Ind Ltd | ケモカイン受容体拮抗剤 |
| WO1997044329A1 (en) | 1996-05-20 | 1997-11-27 | Teijin Limited | Diarylalkyl cyclic diamine derivatives as chemokine receptor antagonists |
| EP0920306A2 (en) | 1996-07-12 | 1999-06-09 | Leukosite, Inc. | Chemokine receptor antagonists and methods of use therefor |
| CA2261633A1 (en) * | 1996-07-29 | 1998-02-05 | Banyu Pharmaceutical Co., Ltd. | Chemokine receptor antagonists |
| EP0927167A1 (en) | 1996-08-14 | 1999-07-07 | Warner-Lambert Company | 2-phenyl benzimidazole derivatives as mcp-1 antagonists |
| WO1998027815A1 (en) | 1996-12-20 | 1998-07-02 | Merck & Co., Inc. | Substituted aminoquinolines as modulators of chemokine receptor activity |
| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| JP2002502844A (ja) | 1998-02-03 | 2002-01-29 | ベーリンガー インゲルハイム ファルマ コマンディトゲゼルシャフト | ５員複素環縮合ベンゾ誘導体、その調製及び医薬品としてのそれらの使用 |
| WO2000006550A1 (en) * | 1998-07-31 | 2000-02-10 | Nippon Soda Co., Ltd. | Phenylazole compounds, process for producing the same and drugs for hyperlipemia |
| US6316449B1 (en) * | 1999-07-08 | 2001-11-13 | Millennium Pharmaceuticals, Inc. | Chemokine receptor antagonists |
| WO2001057021A2 (en) | 2000-02-01 | 2001-08-09 | Cor Therapeutics, Inc. | 2-[1H]-QUINOLONE AND 2-[1H]-QUINOXALONE INHIBITORS OF FACTOR Xa |
| US20020013314A1 (en) | 2000-02-01 | 2002-01-31 | Bing-Yan Zhu | 3,4-dihydro-2H-benzo[1,4]oxazine inhibitors of factor Xa |
| WO2001057044A1 (en) | 2000-02-01 | 2001-08-09 | Daiichi Pharmaceutical Co., Ltd. | Pyridoxazine derivatives |
-
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 EP EP02709746A patent/EP1363897B1/en not_active Expired - Lifetime
- 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 ES ES02709746T patent/ES2254653T3/es not_active Expired - Lifetime
- 2002-02-28 JP JP2002569829A patent/JP4291576B2/ja not_active Expired - Fee Related
- 2002-02-28 CN CNB028057929A patent/CN1259315C/zh not_active Expired - Fee Related
- 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 KR KR10-2003-7011481A patent/KR20040018336A/ko not_active Abandoned
- 2002-02-28 WO PCT/US2002/006256 patent/WO2002070509A2/en not_active Ceased
- 2002-02-28 CA CA002439849A patent/CA2439849A1/en not_active Abandoned
-
2004
- 2004-10-19 US US10/969,440 patent/US7297696B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2004527503A5 (enExample) | ||
| JP2004525951A5 (enExample) | ||
| KR101245062B1 (ko) | 칼슘이온-방출-활성화-칼슘이온 채널을 조절하는 방법 | |
| JP4291576B2 (ja) | Ｍｃｐ−１機能のアンタゴニストおよびその使用方法 | |
| EP1846372B1 (en) | Compounds for inflammation and immune-related uses | |
| US6552022B1 (en) | Benzamide derivatives and their use as ApoB-100 secretion inhibitors | |
| JP2008500284A5 (enExample) | ||
| US20100234377A1 (en) | Piperazine compounds for the inhibition of haematopoietic prostaglandin d synthase | |
| JP2010501587A5 (enExample) | ||
| CA2580852A1 (en) | Compounds for inflammation and immune-related uses | |
| KR100802332B1 (ko) | 신규한 3-치환된 요소 유도체 및 그의 의학적 용도 | |
| JP2005524668A5 (enExample) | ||
| JP2005522438A5 (enExample) | ||
| RU2009148304A (ru) | Модуляторы гидролазы амидов жирных кислот на основе гетероарилзамещенной мочевины | |
| JP2004504301A5 (enExample) | ||
| RU2006123418A (ru) | Новые антагонисты м3 мускаринового ацетилхолинового рецептора | |
| JP2004517080A5 (enExample) | ||
| JP2013517273A5 (enExample) | ||
| RU2425029C2 (ru) | Соединение сульфонамида или его соль | |
| US20060223868A1 (en) | Heterocyclic amides exhibiting and inhibitory activity at the vanilloid receptor 1(vr1) | |
| HRP20140105T1 (hr) | Novi inhibitori seh i njihova upotreba | |
| US20070276011A1 (en) | Plasminogen Activator Inhibitor-1 Inhibitor | |
| JP2005514432A5 (enExample) | ||
| JP2010526051A5 (enExample) | ||
| CA2416220A1 (en) | Preparation of phosphatase inhibitors |