JP2002534419A5 - - Google Patents
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- Publication number
- JP2002534419A5 JP2002534419A5 JP2000592277A JP2000592277A JP2002534419A5 JP 2002534419 A5 JP2002534419 A5 JP 2002534419A5 JP 2000592277 A JP2000592277 A JP 2000592277A JP 2000592277 A JP2000592277 A JP 2000592277A JP 2002534419 A5 JP2002534419 A5 JP 2002534419A5
- Authority
- JP
- Japan
- Prior art keywords
- benzoxazin
- alkyl
- heteroaryl
- phenylamino
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 125000001072 heteroaryl group Chemical group 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 19
- 125000000217 alkyl group Chemical group 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 18
- 229910052739 hydrogen Inorganic materials 0.000 description 15
- 239000001257 hydrogen Substances 0.000 description 15
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 11
- 150000002431 hydrogen Chemical class 0.000 description 11
- -1 hydroxy, amino Chemical group 0.000 description 11
- 150000002148 esters Chemical group 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 9
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 208000008589 Obesity Diseases 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 235000020824 obesity Nutrition 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 5
- 125000004093 cyano group Chemical group *C#N 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 208000018522 Gastrointestinal disease Diseases 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 208000010643 digestive system disease Diseases 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 208000018685 gastrointestinal system disease Diseases 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- VICOSHKERFIQPS-UHFFFAOYSA-N 2-anilino-4-oxo-3,1-benzoxazine-6-carbonitrile Chemical compound N=1C2=CC=C(C#N)C=C2C(=O)OC=1NC1=CC=CC=C1 VICOSHKERFIQPS-UHFFFAOYSA-N 0.000 description 2
- IHVXUPNINOXABX-UHFFFAOYSA-N 2-anilino-7-ethyl-3,1-benzoxazin-4-one Chemical compound C=1C(CC)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 IHVXUPNINOXABX-UHFFFAOYSA-N 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 125000005418 aryl aryl group Chemical group 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 201000001421 hyperglycemia Diseases 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 2
- 0 *c(c(*)c1*I)c(*)c(C(O2)=O)c1NC2=O Chemical compound *c(c(*)c1*I)c(*)c(C(O2)=O)c1NC2=O 0.000 description 1
- ILUIOUOLLQEVNH-UHFFFAOYSA-N 2-(1h-pyrrol-3-ylamino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC=1C=CNC=1 ILUIOUOLLQEVNH-UHFFFAOYSA-N 0.000 description 1
- PRFHHLQOTVIPMG-UHFFFAOYSA-N 2-(2-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC1=CC=CC=C1OC1=CC=CC=C1 PRFHHLQOTVIPMG-UHFFFAOYSA-N 0.000 description 1
- CKYXUGFIOMLLTI-UHFFFAOYSA-N 2-(3-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC(C=1)=CC=CC=1OC1=CC=CC=C1 CKYXUGFIOMLLTI-UHFFFAOYSA-N 0.000 description 1
- HFXFOJRTNOZZRG-UHFFFAOYSA-N 2-(4-aminoanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(N)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 HFXFOJRTNOZZRG-UHFFFAOYSA-N 0.000 description 1
- SRPVIUOVOOFGQQ-UHFFFAOYSA-N 2-(4-benzoylanilino)-7-methyl-3,1-benzoxazin-4-one Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC(C=C1)=CC=C1C(=O)C1=CC=CC=C1 SRPVIUOVOOFGQQ-UHFFFAOYSA-N 0.000 description 1
- SSIOHCZFLKTZMU-UHFFFAOYSA-N 2-(4-butylanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(CCCC)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 SSIOHCZFLKTZMU-UHFFFAOYSA-N 0.000 description 1
- QBHHRJRBHXDCMO-UHFFFAOYSA-N 2-(4-chloroanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(Cl)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 QBHHRJRBHXDCMO-UHFFFAOYSA-N 0.000 description 1
- LDRACLGWMZWSGF-UHFFFAOYSA-N 2-(4-heptoxyanilino)-6-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC(OCCCCCCC)=CC=C1NC1=NC2=CC=C(C)C=C2C(=O)O1 LDRACLGWMZWSGF-UHFFFAOYSA-N 0.000 description 1
- KPJKYZYRHCKOAQ-UHFFFAOYSA-N 2-(4-hexylanilino)-6-methyl-3,1-benzoxazin-4-one Chemical compound C1=CC(CCCCCC)=CC=C1NC1=NC2=CC=C(C)C=C2C(=O)O1 KPJKYZYRHCKOAQ-UHFFFAOYSA-N 0.000 description 1
- QEHNWSOKTOFQMT-UHFFFAOYSA-N 2-(4-hydroxyanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(O)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 QEHNWSOKTOFQMT-UHFFFAOYSA-N 0.000 description 1
- UHVKKDSXQJGPDB-UHFFFAOYSA-N 2-(4-methoxyanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(OC)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 UHVKKDSXQJGPDB-UHFFFAOYSA-N 0.000 description 1
- ISKKMQHVYDPWPV-UHFFFAOYSA-N 2-(4-methylanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(C)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 ISKKMQHVYDPWPV-UHFFFAOYSA-N 0.000 description 1
- HKFRGWMWWWWFHQ-UHFFFAOYSA-N 2-(4-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC(C=C1)=CC=C1OC1=CC=CC=C1 HKFRGWMWWWWFHQ-UHFFFAOYSA-N 0.000 description 1
- VAKQOMDNWGTHHR-UHFFFAOYSA-N 2-(4-phenoxyanilino)-7-(trifluoromethyl)-3,1-benzoxazin-4-one Chemical compound C=1C(C(F)(F)F)=CC=C(C(O2)=O)C=1N=C2NC(C=C1)=CC=C1OC1=CC=CC=C1 VAKQOMDNWGTHHR-UHFFFAOYSA-N 0.000 description 1
- ZULSAVVHRIQZTI-UHFFFAOYSA-N 2-(4-propan-2-ylanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(C(C)C)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 ZULSAVVHRIQZTI-UHFFFAOYSA-N 0.000 description 1
- QRGKQGPQDLRKDU-UHFFFAOYSA-N 2-(6-phenylhexylamino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NCCCCCCC1=CC=CC=C1 QRGKQGPQDLRKDU-UHFFFAOYSA-N 0.000 description 1
- KRZHQYKKBPTALV-UHFFFAOYSA-N 2-(cyclopropylamino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC1CC1 KRZHQYKKBPTALV-UHFFFAOYSA-N 0.000 description 1
- UZCBPGZCSFBLLA-UHFFFAOYSA-N 2-(dodec-7-ynylamino)-6-methyl-3,1-benzoxazin-4-one Chemical compound C1=C(C)C=C2C(=O)OC(NCCCCCCC#CCCCC)=NC2=C1 UZCBPGZCSFBLLA-UHFFFAOYSA-N 0.000 description 1
- LVKYVTCQSYNTBW-UHFFFAOYSA-N 2-(hexadecylamino)-6-methyl-3,1-benzoxazin-4-one Chemical compound C1=C(C)C=C2C(=O)OC(NCCCCCCCCCCCCCCCC)=NC2=C1 LVKYVTCQSYNTBW-UHFFFAOYSA-N 0.000 description 1
- DURPUFUTUNPYHX-UHFFFAOYSA-N 2-(naphthalen-2-ylamino)-3,1-benzoxazin-4-one Chemical compound C1=CC=C2C(=O)OC(NC=3C=C4C=CC=CC4=CC=3)=NC2=C1 DURPUFUTUNPYHX-UHFFFAOYSA-N 0.000 description 1
- MYBXTXQHOCBQCU-UHFFFAOYSA-N 2-(piperidin-4-ylamino)-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC1CCNCC1 MYBXTXQHOCBQCU-UHFFFAOYSA-N 0.000 description 1
- AXYNLDHGDPTNLK-UHFFFAOYSA-N 2-[(7-methyl-4-oxo-3,1-benzoxazin-2-yl)amino]benzonitrile Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1C#N AXYNLDHGDPTNLK-UHFFFAOYSA-N 0.000 description 1
- NCFWNAGDFTUTSR-UHFFFAOYSA-N 2-[3-(trifluoromethyl)anilino]-3,1-benzoxazin-4-one Chemical compound FC(F)(F)C1=CC=CC(NC=2OC(=O)C3=CC=CC=C3N=2)=C1 NCFWNAGDFTUTSR-UHFFFAOYSA-N 0.000 description 1
- PALJIWYZTFQCRC-UHFFFAOYSA-N 2-[4-(trifluoromethyl)anilino]-3,1-benzoxazin-4-one Chemical compound C1=CC(C(F)(F)F)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 PALJIWYZTFQCRC-UHFFFAOYSA-N 0.000 description 1
- YWXZWFMDIOEGTG-UHFFFAOYSA-N 2-[6-(1h-pyrrol-2-yl)hexylamino]-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NCCCCCCC1=CC=CN1 YWXZWFMDIOEGTG-UHFFFAOYSA-N 0.000 description 1
- UUMLXNZZKFQMMR-UHFFFAOYSA-N 2-anilino-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC1=CC=CC=C1 UUMLXNZZKFQMMR-UHFFFAOYSA-N 0.000 description 1
- HOKWWRBMVSPSLT-UHFFFAOYSA-N 2-anilino-4-oxo-3,1-benzoxazine-6-carbaldehyde Chemical compound O1C(=O)C2=CC(C=O)=CC=C2N=C1NC1=CC=CC=C1 HOKWWRBMVSPSLT-UHFFFAOYSA-N 0.000 description 1
- USVUSBRRPAMJGT-UHFFFAOYSA-N 2-anilino-4-oxo-3,1-benzoxazine-6-sulfinic acid Chemical compound O1C(=O)C2=CC(S(=O)O)=CC=C2N=C1NC1=CC=CC=C1 USVUSBRRPAMJGT-UHFFFAOYSA-N 0.000 description 1
- IITVJIVEURYYRL-UHFFFAOYSA-N 2-anilino-5-fluoro-3,1-benzoxazin-4-one Chemical compound O1C(=O)C=2C(F)=CC=CC=2N=C1NC1=CC=CC=C1 IITVJIVEURYYRL-UHFFFAOYSA-N 0.000 description 1
- YBFOWPXXISBBCK-UHFFFAOYSA-N 2-anilino-6,7-dimethyl-3,1-benzoxazin-4-one Chemical compound O1C(=O)C=2C=C(C)C(C)=CC=2N=C1NC1=CC=CC=C1 YBFOWPXXISBBCK-UHFFFAOYSA-N 0.000 description 1
- QXUNQIOOTBDRQD-UHFFFAOYSA-N 2-anilino-6-(trifluoromethyl)-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(C(F)(F)F)=CC=C2N=C1NC1=CC=CC=C1 QXUNQIOOTBDRQD-UHFFFAOYSA-N 0.000 description 1
- ZDOKDIMOAKOXNC-UHFFFAOYSA-N 2-anilino-6-chloro-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(Cl)=CC=C2N=C1NC1=CC=CC=C1 ZDOKDIMOAKOXNC-UHFFFAOYSA-N 0.000 description 1
- CFHSAEUDMPOUPY-UHFFFAOYSA-N 2-anilino-6-cyclopropyl-3,1-benzoxazin-4-one Chemical compound N=1C2=CC=C(C3CC3)C=C2C(=O)OC=1NC1=CC=CC=C1 CFHSAEUDMPOUPY-UHFFFAOYSA-N 0.000 description 1
- WAHWHYZPYHLYTG-UHFFFAOYSA-N 2-anilino-6-methyl-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(C)=CC=C2N=C1NC1=CC=CC=C1 WAHWHYZPYHLYTG-UHFFFAOYSA-N 0.000 description 1
- RTEHSNJXVDNBKZ-UHFFFAOYSA-N 2-anilino-6-nitro-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC([N+](=O)[O-])=CC=C2N=C1NC1=CC=CC=C1 RTEHSNJXVDNBKZ-UHFFFAOYSA-N 0.000 description 1
- SHHCAUQRFUKFOP-UHFFFAOYSA-N 2-anilino-6-sulfanyl-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(S)=CC=C2N=C1NC1=CC=CC=C1 SHHCAUQRFUKFOP-UHFFFAOYSA-N 0.000 description 1
- KCTKJSZBMOZLGZ-UHFFFAOYSA-N 2-anilino-7-(trifluoromethyl)-3,1-benzoxazin-4-one Chemical compound C=1C(C(F)(F)F)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 KCTKJSZBMOZLGZ-UHFFFAOYSA-N 0.000 description 1
- WQVVOBIFVHKGNN-UHFFFAOYSA-N 2-anilino-7-butyl-3,1-benzoxazin-4-one Chemical compound C=1C(CCCC)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 WQVVOBIFVHKGNN-UHFFFAOYSA-N 0.000 description 1
- CQDBIBPUERIOBM-UHFFFAOYSA-N 2-anilino-7-cyclopropyl-3,1-benzoxazin-4-one Chemical compound N=1C2=CC(C3CC3)=CC=C2C(=O)OC=1NC1=CC=CC=C1 CQDBIBPUERIOBM-UHFFFAOYSA-N 0.000 description 1
- XKVAALZMJMWQNN-UHFFFAOYSA-N 2-anilino-7-fluoro-3,1-benzoxazin-4-one Chemical compound C=1C(F)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 XKVAALZMJMWQNN-UHFFFAOYSA-N 0.000 description 1
- FXHDRTZNZVJHBR-UHFFFAOYSA-N 2-anilino-7-hydroxy-3,1-benzoxazin-4-one Chemical compound C=1C(O)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 FXHDRTZNZVJHBR-UHFFFAOYSA-N 0.000 description 1
- ZXZWPIVFCQULBR-UHFFFAOYSA-N 2-anilino-7-methyl-3,1-benzoxazin-4-one Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 ZXZWPIVFCQULBR-UHFFFAOYSA-N 0.000 description 1
- LFNRYAMNRIQETP-UHFFFAOYSA-N 2-anilino-7-octyl-3,1-benzoxazin-4-one Chemical compound C=1C(CCCCCCCC)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 LFNRYAMNRIQETP-UHFFFAOYSA-N 0.000 description 1
- SAJWWOJXDQKTLF-UHFFFAOYSA-N 2-anilino-8-fluoro-3,1-benzoxazin-4-one Chemical compound FC1=CC=CC(C(O2)=O)=C1N=C2NC1=CC=CC=C1 SAJWWOJXDQKTLF-UHFFFAOYSA-N 0.000 description 1
- IBDJYZFNKDWXDM-UHFFFAOYSA-N 2-anilinopyrido[2,3-d][1,3]oxazin-4-one Chemical compound N=1C2=NC=CC=C2C(=O)OC=1NC1=CC=CC=C1 IBDJYZFNKDWXDM-UHFFFAOYSA-N 0.000 description 1
- MRZMCPJITHGRLA-UHFFFAOYSA-N 2-anilinopyrido[3,4-d][1,3]oxazin-4-one Chemical compound N=1C2=CN=CC=C2C(=O)OC=1NC1=CC=CC=C1 MRZMCPJITHGRLA-UHFFFAOYSA-N 0.000 description 1
- WPWUMZKCYISKMC-UHFFFAOYSA-N 3-[(7-methyl-4-oxo-3,1-benzoxazin-2-yl)amino]benzonitrile Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC(C#N)=C1 WPWUMZKCYISKMC-UHFFFAOYSA-N 0.000 description 1
- LQBGBFWFTWJVMR-UHFFFAOYSA-N 4-[(4-oxo-3,1-benzoxazin-2-yl)amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 LQBGBFWFTWJVMR-UHFFFAOYSA-N 0.000 description 1
- XBZOEFOBAZHKHZ-UHFFFAOYSA-N 4-[(4-oxo-3,1-benzoxazin-2-yl)amino]benzonitrile Chemical compound N=1C2=CC=CC=C2C(=O)OC=1NC1=CC=C(C#N)C=C1 XBZOEFOBAZHKHZ-UHFFFAOYSA-N 0.000 description 1
- ZNVZMQOFFJWFIW-UHFFFAOYSA-N 4-[(7-methyl-4-oxo-3,1-benzoxazin-2-yl)amino]benzonitrile Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC1=CC=C(C#N)C=C1 ZNVZMQOFFJWFIW-UHFFFAOYSA-N 0.000 description 1
- IZOLPXHXHCWDKH-UHFFFAOYSA-N 6-iodo-2-(octylamino)-3,1-benzoxazin-4-one Chemical compound C1=C(I)C=C2C(=O)OC(NCCCCCCCC)=NC2=C1 IZOLPXHXHCWDKH-UHFFFAOYSA-N 0.000 description 1
- WHEKXHXYMRSBOW-UHFFFAOYSA-N 6-methyl-2-(4-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(C)=CC=C2N=C1NC(C=C1)=CC=C1OC1=CC=CC=C1 WHEKXHXYMRSBOW-UHFFFAOYSA-N 0.000 description 1
- ZSZQPTPLWHGWKY-UHFFFAOYSA-N 6-methyl-2-(6-thiophen-2-ylhexylamino)-3,1-benzoxazin-4-one Chemical compound O1C(=O)C2=CC(C)=CC=C2N=C1NCCCCCCC1=CC=CS1 ZSZQPTPLWHGWKY-UHFFFAOYSA-N 0.000 description 1
- MUDRAEKRQDHCDK-UHFFFAOYSA-N 6-methyl-2-(naphthalen-2-ylamino)-3,1-benzoxazin-4-one Chemical compound C1=CC=CC2=CC(NC3=NC4=CC=C(C=C4C(=O)O3)C)=CC=C21 MUDRAEKRQDHCDK-UHFFFAOYSA-N 0.000 description 1
- JZQCLPGGDXXIOM-UHFFFAOYSA-N 7-amino-2-anilino-3,1-benzoxazin-4-one Chemical compound C=1C(N)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1 JZQCLPGGDXXIOM-UHFFFAOYSA-N 0.000 description 1
- BIIHQRAKMPLRGH-UHFFFAOYSA-N 7-butyl-2-(octylamino)-3,1-benzoxazin-4-one Chemical compound CCCCC1=CC=C2C(=O)OC(NCCCCCCCC)=NC2=C1 BIIHQRAKMPLRGH-UHFFFAOYSA-N 0.000 description 1
- GLFFSBXVUSFGBP-UHFFFAOYSA-N 7-methyl-2-(2-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC1=CC=CC=C1OC1=CC=CC=C1 GLFFSBXVUSFGBP-UHFFFAOYSA-N 0.000 description 1
- BDEDNRAOKYDITQ-UHFFFAOYSA-N 7-methyl-2-(3-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC(C=1)=CC=CC=1OC1=CC=CC=C1 BDEDNRAOKYDITQ-UHFFFAOYSA-N 0.000 description 1
- PKSPNUSISUVHGC-UHFFFAOYSA-N 7-methyl-2-(4-octylanilino)-3,1-benzoxazin-4-one Chemical compound C1=CC(CCCCCCCC)=CC=C1NC1=NC2=CC(C)=CC=C2C(=O)O1 PKSPNUSISUVHGC-UHFFFAOYSA-N 0.000 description 1
- VHJKLJMPBCXLKB-UHFFFAOYSA-N 7-methyl-2-(4-phenoxyanilino)-3,1-benzoxazin-4-one Chemical compound C=1C(C)=CC=C(C(O2)=O)C=1N=C2NC(C=C1)=CC=C1OC1=CC=CC=C1 VHJKLJMPBCXLKB-UHFFFAOYSA-N 0.000 description 1
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 102000004882 Lipase Human genes 0.000 description 1
- 108090001060 Lipase Proteins 0.000 description 1
- 239000004367 Lipase Substances 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000005018 aryl alkenyl group Chemical group 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- OGKPWJCQRPMWFU-UHFFFAOYSA-N butyl 4-[(6-methyl-4-oxo-3,1-benzoxazin-2-yl)amino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC1=NC2=CC=C(C)C=C2C(=O)O1 OGKPWJCQRPMWFU-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- RVVZOERBGTUAIP-UHFFFAOYSA-N ethyl 4-[(4-oxo-3,1-benzoxazin-2-yl)amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NC1=NC2=CC=CC=C2C(=O)O1 RVVZOERBGTUAIP-UHFFFAOYSA-N 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000004447 heteroarylalkenyl group Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 235000019421 lipase Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- FNDSACBEELZRQG-UHFFFAOYSA-N n-(2-anilino-4-oxo-3,1-benzoxazin-6-yl)acetamide Chemical compound O1C(=O)C2=CC(NC(=O)C)=CC=C2N=C1NC1=CC=CC=C1 FNDSACBEELZRQG-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000001984 thiazolidinyl group Chemical group 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9900416.0A GB9900416D0 (en) | 1999-01-08 | 1999-01-08 | Inhibitors |
| GB9900416.0 | 1999-01-08 | ||
| PCT/GB2000/000031 WO2000040569A1 (en) | 1999-01-08 | 2000-01-06 | 2-amino-benzoxazinone derivatives for the treatment of obesity |
Publications (2)
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| JP2002534419A JP2002534419A (ja) | 2002-10-15 |
| JP2002534419A5 true JP2002534419A5 (https=) | 2007-02-22 |
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Country Status (21)
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| US (2) | US6656934B2 (https=) |
| EP (1) | EP1144395B1 (https=) |
| JP (1) | JP2002534419A (https=) |
| KR (1) | KR100615914B1 (https=) |
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| AR (1) | AR022203A1 (https=) |
| AT (1) | ATE293610T1 (https=) |
| AU (1) | AU770342B2 (https=) |
| CA (1) | CA2359987C (https=) |
| DE (1) | DE60019556T2 (https=) |
| DK (1) | DK1144395T3 (https=) |
| ES (1) | ES2240051T3 (https=) |
| GB (1) | GB9900416D0 (https=) |
| HU (1) | HUP0104909A3 (https=) |
| MY (1) | MY129247A (https=) |
| NO (1) | NO321058B1 (https=) |
| NZ (1) | NZ512739A (https=) |
| PL (1) | PL350412A1 (https=) |
| PT (1) | PT1144395E (https=) |
| RU (1) | RU2244711C2 (https=) |
| WO (1) | WO2000040569A1 (https=) |
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| GB0001572D0 (en) | 2000-01-24 | 2000-03-15 | Alizyme Therapeutics Ltd | Inhibitors |
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| NZ523684A (en) | 2000-07-28 | 2005-04-29 | F | New pharmaceutical composition |
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| CA2456229A1 (en) | 2001-08-03 | 2003-02-13 | Diversa Corporation | Epoxide hydrolases, nucleic acids encoding them and methods for making and using them |
| US6943001B2 (en) | 2001-08-03 | 2005-09-13 | Diversa Corporation | Epoxide hydrolases, nucleic acids encoding them and methods for making and using them |
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| CN104374836A (zh) * | 2014-09-19 | 2015-02-25 | 安徽安科生物工程（集团）股份有限公司 | 西替利司他及有关杂质的hplc测定方法 |
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| US3450700A (en) * | 1966-12-20 | 1969-06-17 | Upjohn Co | 2-tertiary amino-4h-3,1-benzoxazin-4-ones |
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| US5985872A (en) * | 1995-05-24 | 1999-11-16 | G.D. Searle & Co. | 2-amino-benzoxazinones for the treatment of viral infections |
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| GB9900416D0 (en) * | 1999-01-08 | 1999-02-24 | Alizyme Therapeutics Ltd | Inhibitors |
-
1999
- 1999-01-08 GB GBGB9900416.0A patent/GB9900416D0/en not_active Ceased
-
2000
- 2000-01-05 AR ARP000100028A patent/AR022203A1/es active IP Right Grant
- 2000-01-06 DE DE60019556T patent/DE60019556T2/de not_active Expired - Lifetime
- 2000-01-06 CN CNB008036217A patent/CN100480245C/zh not_active Expired - Fee Related
- 2000-01-06 ES ES00900081T patent/ES2240051T3/es not_active Expired - Lifetime
- 2000-01-06 JP JP2000592277A patent/JP2002534419A/ja not_active Withdrawn
- 2000-01-06 KR KR1020017008596A patent/KR100615914B1/ko not_active Expired - Fee Related
- 2000-01-06 HU HU0104909A patent/HUP0104909A3/hu unknown
- 2000-01-06 AT AT00900081T patent/ATE293610T1/de not_active IP Right Cessation
- 2000-01-06 PL PL00350412A patent/PL350412A1/xx not_active Application Discontinuation
- 2000-01-06 RU RU2001121983/04A patent/RU2244711C2/ru not_active IP Right Cessation
- 2000-01-06 WO PCT/GB2000/000031 patent/WO2000040569A1/en not_active Ceased
- 2000-01-06 CA CA002359987A patent/CA2359987C/en not_active Expired - Fee Related
- 2000-01-06 DK DK00900081T patent/DK1144395T3/da active
- 2000-01-06 AU AU18845/00A patent/AU770342B2/en not_active Ceased
- 2000-01-06 PT PT00900081T patent/PT1144395E/pt unknown
- 2000-01-06 MY MYPI20000045A patent/MY129247A/en unknown
- 2000-01-06 EP EP00900081A patent/EP1144395B1/en not_active Expired - Lifetime
- 2000-01-06 NZ NZ512739A patent/NZ512739A/en not_active IP Right Cessation
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2001
- 2001-07-06 US US09/901,868 patent/US6656934B2/en not_active Expired - Fee Related
- 2001-07-06 NO NO20013380A patent/NO321058B1/no not_active IP Right Cessation
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2002
- 2002-11-27 US US10/306,375 patent/US7776853B2/en not_active Expired - Fee Related
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