JP2004509953A5 - - Google Patents
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- Publication number
- JP2004509953A5 JP2004509953A5 JP2002531107A JP2002531107A JP2004509953A5 JP 2004509953 A5 JP2004509953 A5 JP 2004509953A5 JP 2002531107 A JP2002531107 A JP 2002531107A JP 2002531107 A JP2002531107 A JP 2002531107A JP 2004509953 A5 JP2004509953 A5 JP 2004509953A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- morpholin
- dichlorobenzyl
- urea
- amino
- 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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- 150000001875 compounds Chemical class 0.000 description 42
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 24
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 22
- 125000000217 alkyl group Chemical group 0.000 description 20
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 18
- -1 aryl-C2-6Alkenyl Chemical group 0.000 description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000012453 solvate Substances 0.000 description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
- 229910052760 oxygen Inorganic materials 0.000 description 10
- 239000001301 oxygen Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000011593 sulfur Substances 0.000 description 10
- 239000004202 carbamide Substances 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- 229910052717 sulfur Inorganic materials 0.000 description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 125000001072 heteroaryl group Chemical group 0.000 description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- 125000000753 cycloalkyl group Chemical group 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 3
- HFKSPOZYFRZZBJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 HFKSPOZYFRZZBJ-UHFFFAOYSA-N 0.000 description 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- JZBGNRGEOVQVEE-LBPRGKRZSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(2-methyltetrazol-5-yl)methyl]urea Chemical compound CN1N=NC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 JZBGNRGEOVQVEE-LBPRGKRZSA-N 0.000 description 2
- RLGDJANJVUKARK-SFHVURJKSA-N 4-[[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]-n-methylbenzamide Chemical compound C1=CC(C(=O)NC)=CC=C1CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 RLGDJANJVUKARK-SFHVURJKSA-N 0.000 description 2
- GPLUUMAKBFSDIE-KRWDZBQOSA-N 4-[[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]methyl]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 GPLUUMAKBFSDIE-KRWDZBQOSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- IJYMVDXPULPUGS-OWOJBTEDSA-N (E)-4-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methylcarbamoylamino]but-2-enoic acid Chemical compound C1COC(CNC(=O)NC/C=C/C(=O)O)CN1Cc1ccc(Cl)c(Cl)c1 IJYMVDXPULPUGS-OWOJBTEDSA-N 0.000 description 1
- OFASZEVOCQKUAG-UHFFFAOYSA-N 1,3-bis[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)OCC1 OFASZEVOCQKUAG-UHFFFAOYSA-N 0.000 description 1
- WVCDSELVRXKGKD-UHFFFAOYSA-N 1-(1-benzoylpiperidin-4-yl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NC2CCN(CC2)C(=O)C=2C=CC=CC=2)OCC1 WVCDSELVRXKGKD-UHFFFAOYSA-N 0.000 description 1
- QZYUSYJXVMRQNM-UHFFFAOYSA-N 1-(3-bromophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NC=2C=C(Br)C=CC=2)OCC1 QZYUSYJXVMRQNM-UHFFFAOYSA-N 0.000 description 1
- CETNYFPESALINJ-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound ClC1=CC=CC(NC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 CETNYFPESALINJ-UHFFFAOYSA-N 0.000 description 1
- GEKMNZWPOKHNJK-UHFFFAOYSA-N 1-(3-cyanophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NC=2C=C(C=CC=2)C#N)OCC1 GEKMNZWPOKHNJK-UHFFFAOYSA-N 0.000 description 1
- QIKALZSPXCSEAT-INIZCTEOSA-N 1-(3-tert-butylsulfonylpropyl)-3-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1CO[C@@H](CNC(=O)NCCCS(=O)(=O)C(C)(C)C)CN1CC1=CC=C(Cl)C(Cl)=C1 QIKALZSPXCSEAT-INIZCTEOSA-N 0.000 description 1
- MKBLQSFKFNDVLX-UHFFFAOYSA-N 1-(4-bromophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NC=2C=CC(Br)=CC=2)OCC1 MKBLQSFKFNDVLX-UHFFFAOYSA-N 0.000 description 1
- CUEKMUYPOKHPEE-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(2-methoxyethyl)morpholin-2-yl]methyl]urea Chemical compound C1N(CCOC)CCOC1CNC(=O)NC1=CC=C(Cl)C=C1 CUEKMUYPOKHPEE-UHFFFAOYSA-N 0.000 description 1
- DNEKWVAUXSDQFQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(2-phenylsulfanylethyl)morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CCSC=2C=CC=CC=2)C1 DNEKWVAUXSDQFQ-UHFFFAOYSA-N 0.000 description 1
- MZOYOSRKYQNISE-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(3,4-dichlorobenzoyl)morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(C(=O)C=2C=C(Cl)C(Cl)=CC=2)C1 MZOYOSRKYQNISE-UHFFFAOYSA-N 0.000 description 1
- GXCPRHGMOJUQCQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(cyanomethyl)morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC#N)C1 GXCPRHGMOJUQCQ-UHFFFAOYSA-N 0.000 description 1
- RKDCDFYJHFQLBQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(naphthalen-1-ylmethyl)morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C3=CC=CC=C3C=CC=2)C1 RKDCDFYJHFQLBQ-UHFFFAOYSA-N 0.000 description 1
- VOVMLQSVJMKLEN-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-(naphthalen-2-ylmethyl)morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=C3C=CC=CC3=CC=2)C1 VOVMLQSVJMKLEN-UHFFFAOYSA-N 0.000 description 1
- UWRSYIYMRLWCPN-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(3-chlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=C(Cl)C=CC=2)C1 UWRSYIYMRLWCPN-UHFFFAOYSA-N 0.000 description 1
- ZEEVVNROOCMRQZ-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(3-iodophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=C(I)C=CC=2)C1 ZEEVVNROOCMRQZ-UHFFFAOYSA-N 0.000 description 1
- CIKUSCIEGFQUJK-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(4-ethenylphenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=CC(C=C)=CC=2)C1 CIKUSCIEGFQUJK-UHFFFAOYSA-N 0.000 description 1
- HPAOEQJGXJKTTP-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(4-phenylphenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CC=2C=CC(=CC=2)C=2C=CC=CC=2)C1 HPAOEQJGXJKTTP-UHFFFAOYSA-N 0.000 description 1
- NSVOKHWMZIYXRT-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[(5-chlorothiophen-2-yl)methyl]morpholin-2-yl]methyl]urea Chemical compound S1C(Cl)=CC=C1CN1CC(CNC(=O)NC=2C=CC(Cl)=CC=2)OCC1 NSVOKHWMZIYXRT-UHFFFAOYSA-N 0.000 description 1
- MNTQHEQUOPXTHV-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[[4-[2-(4-fluorophenoxy)ethyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(F)=CC=C1OCCN1CC(CNC(=O)NC=2C=CC(Cl)=CC=2)OCC1 MNTQHEQUOPXTHV-UHFFFAOYSA-N 0.000 description 1
- JSFRQVBURHCSRQ-UHFFFAOYSA-N 1-(4-cyanophenyl)-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NC=2C=CC(=CC=2)C#N)OCC1 JSFRQVBURHCSRQ-UHFFFAOYSA-N 0.000 description 1
- KDWWACJTGVYXJA-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C(=CC=CC=2)Cl)OCC1 KDWWACJTGVYXJA-UHFFFAOYSA-N 0.000 description 1
- LNLSTUJGFCXOQC-UHFFFAOYSA-N 1-[(3,5-dichlorophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound ClC1=CC(Cl)=CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 LNLSTUJGFCXOQC-UHFFFAOYSA-N 0.000 description 1
- ORWBPAROFHCSAZ-UHFFFAOYSA-N 1-[(3-chlorophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound ClC1=CC=CC(CNC(=O)NCC2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=C1 ORWBPAROFHCSAZ-UHFFFAOYSA-N 0.000 description 1
- NXWWILBKOCCPEA-UHFFFAOYSA-N 1-[(3-cyanophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=C(C=CC=2)C#N)OCC1 NXWWILBKOCCPEA-UHFFFAOYSA-N 0.000 description 1
- XFOKYSOGMLELDG-UHFFFAOYSA-N 1-[(4-but-3-enylmorpholin-2-yl)methyl]-3-(4-chlorophenyl)urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NCC1OCCN(CCC=C)C1 XFOKYSOGMLELDG-UHFFFAOYSA-N 0.000 description 1
- SIGUZGFURPEAFO-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=CC(Cl)=CC=C1CNC(=O)NCC1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 SIGUZGFURPEAFO-UHFFFAOYSA-N 0.000 description 1
- KKDZSEQGEKNRQW-UHFFFAOYSA-N 1-[(4-cyanophenyl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCC=2C=CC(=CC=2)C#N)OCC1 KKDZSEQGEKNRQW-UHFFFAOYSA-N 0.000 description 1
- XLUKYSBCGPFVOU-UHFFFAOYSA-N 1-[(5-amino-1-phenylpyrazol-4-yl)methyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=NN(C=2C=CC=CC=2)C(N)=C1CNC(=O)NCC(OCC1)CN1CC1=CC=C(Cl)C(Cl)=C1 XLUKYSBCGPFVOU-UHFFFAOYSA-N 0.000 description 1
- WXFNYPNDMNETIN-UHFFFAOYSA-N 1-[3-(benzenesulfonyl)propyl]-3-[[4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1CC(CNC(=O)NCCCS(=O)(=O)C=2C=CC=CC=2)OCC1 WXFNYPNDMNETIN-UHFFFAOYSA-N 0.000 description 1
- ZMLBFPWNXWIJCP-CYBMUJFWSA-N 1-[[(2r)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-prop-2-ynylurea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@@H](CNC(=O)NCC#C)OCC1 ZMLBFPWNXWIJCP-CYBMUJFWSA-N 0.000 description 1
- LAHSCJWLPCJWQW-ZDUSSCGKSA-N 1-[[(2s)-4-[(2,3-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-prop-2-ynylurea Chemical compound ClC1=CC=CC(CN2C[C@H](CNC(=O)NCC#C)OCC2)=C1Cl LAHSCJWLPCJWQW-ZDUSSCGKSA-N 0.000 description 1
- CHFLRXHBQCODJY-ZDUSSCGKSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(1,3-thiazol-2-ylmethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@H](CNC(=O)NCC=2SC=CN=2)OCC1 CHFLRXHBQCODJY-ZDUSSCGKSA-N 0.000 description 1
- IIDLTYKRGNHTEA-SFHVURJKSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(2-phenoxyethyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@H](CNC(=O)NCCOC=2C=CC=CC=2)OCC1 IIDLTYKRGNHTEA-SFHVURJKSA-N 0.000 description 1
- QZYFSWGSMHRMHM-HNNXBMFYSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(3-ethylsulfonylpropyl)urea Chemical compound C1CO[C@@H](CNC(=O)NCCCS(=O)(=O)CC)CN1CC1=CC=C(Cl)C(Cl)=C1 QZYFSWGSMHRMHM-HNNXBMFYSA-N 0.000 description 1
- VMIHJDOWTRWMEG-INIZCTEOSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(3-propan-2-ylsulfonylpropyl)urea Chemical compound C1CO[C@@H](CNC(=O)NCCCS(=O)(=O)C(C)C)CN1CC1=CC=C(Cl)C(Cl)=C1 VMIHJDOWTRWMEG-INIZCTEOSA-N 0.000 description 1
- CEIGWVODZRCVMH-INIZCTEOSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(3-propylsulfonylpropyl)urea Chemical compound C1CO[C@@H](CNC(=O)NCCCS(=O)(=O)CCC)CN1CC1=CC=C(Cl)C(Cl)=C1 CEIGWVODZRCVMH-INIZCTEOSA-N 0.000 description 1
- FXOLBPVVGGAMSU-KRWDZBQOSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-(3-pyrrolidin-1-ylsulfonylpropyl)urea Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C[C@H](CNC(=O)NCCCS(=O)(=O)N2CCCC2)OCC1 FXOLBPVVGGAMSU-KRWDZBQOSA-N 0.000 description 1
- PCMVUEJROCBCFO-KRWDZBQOSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(1-methylsulfonylpiperidin-4-yl)methyl]urea Chemical compound C1CN(S(=O)(=O)C)CCC1CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 PCMVUEJROCBCFO-KRWDZBQOSA-N 0.000 description 1
- ICBCSZQUXHMHIO-SFHVURJKSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(4-methoxyphenyl)methyl]urea Chemical compound C1=CC(OC)=CC=C1CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 ICBCSZQUXHMHIO-SFHVURJKSA-N 0.000 description 1
- SOANXCFVMUFQHE-AWEZNQCLSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[(4-methyl-1,3-thiazol-2-yl)methyl]urea Chemical compound CC1=CSC(CNC(=O)NC[C@@H]2OCCN(CC=3C=C(Cl)C(Cl)=CC=3)C2)=N1 SOANXCFVMUFQHE-AWEZNQCLSA-N 0.000 description 1
- ODWDLPNSSPJZKN-SFHVURJKSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[2-(4-methoxyphenyl)-2-oxoethyl]urea Chemical compound C1=CC(OC)=CC=C1C(=O)CNC(=O)NC[C@@H]1OCCN(CC=2C=C(Cl)C(Cl)=CC=2)C1 ODWDLPNSSPJZKN-SFHVURJKSA-N 0.000 description 1
- DKUHRBJUMSGGJZ-AWEZNQCLSA-N 1-[[(2s)-4-[(3,4-dichlorophenyl)methyl]morpholin-2-yl]methyl]-3-[3-(methylsulfamoyl)propyl]urea Chemical compound C1CO[C@@H](CNC(=O)NCCCS(=O)(=O)NC)CN1CC1=CC=C(Cl)C(Cl)=C1 DKUHRBJUMSGGJZ-AWEZNQCLSA-N 0.000 description 1
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| US6777399B2 (en) | 2000-08-05 | 2004-08-17 | Smithkline Beecham Corporation | Anti-inflammatory androstane derivative compositions |
| UA77656C2 (en) | 2001-04-07 | 2007-01-15 | Glaxo Group Ltd | S-fluoromethyl ester of 6-alpha, 9-alpha-difluoro-17-alpha-[(2-furanylcarbonyl)oxy]-11-beta-hydroxy-16- alpha-methyl-3-oxoandrosta-1,4-dien-17-beta-carbothioacid as anti-inflammatory agent |
| KR100831534B1 (ko) | 2001-04-30 | 2008-05-22 | 글락소 그룹 리미티드 | 17.알파 위치에 시클릭 에스테르기를 지닌 항염증성의안드로스탄의 17.베타.-카르보티오에이트 에스테르 유도체 |
| GB0207439D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
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| TW200400035A (en) | 2002-03-28 | 2004-01-01 | Glaxo Group Ltd | Novel compounds |
| GB0207449D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
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| GB0207447D0 (en) * | 2002-03-28 | 2002-05-08 | Glaxo Group Ltd | Novel compounds |
| GB0211759D0 (en) * | 2002-05-22 | 2002-07-03 | Glaxo Group Ltd | Novel compounds |
| GB0212357D0 (en) * | 2002-05-29 | 2002-07-10 | Glaxo Group Ltd | Novel compounds |
| GB2389530B (en) | 2002-06-14 | 2007-01-10 | Cipla Ltd | Pharmaceutical compositions |
| WO2004028530A1 (en) | 2002-09-26 | 2004-04-08 | Bristol-Myers Squibb Company | N-substituted heterocyclic amines as modulators of chemokine receptor activity |
| EP1486488B1 (en) * | 2003-06-10 | 2009-10-28 | Biondi, Ricardo, Miguel | Use of a compound of formula I for making a pharmaceutical composition |
| US7825147B2 (en) | 2003-08-29 | 2010-11-02 | Ranbaxy Laboratories Limited | Inhibitors of phosphodiesterase type-IV |
| IN2014CN03493A (enExample) | 2004-09-08 | 2015-07-03 | Mitsubishi Tanabe Pharma Corp | |
| EP1992628A1 (en) | 2007-05-18 | 2008-11-19 | Glaxo Group Limited | Derivatives and analogs of N-ethylquinolones and N-ethylazaquinolones |
| US20080207659A1 (en) | 2007-02-15 | 2008-08-28 | Asit Kumar Chakraborti | Inhibitors of phosphodiesterase type 4 |
| BRPI0721451A2 (pt) * | 2007-03-13 | 2014-03-25 | Arete Therapeutics Inc | Compostos de 4-piperidiniluréia como inibidores de epóxido hidrolase solúvel |
| EP2143714B1 (en) | 2007-04-04 | 2013-06-05 | Kowa Company, Ltd. | Tetrahydroisoquinoline compound |
| US20110059969A1 (en) | 2007-12-05 | 2011-03-10 | Astrazeneca Ab | Piperazines as anti-obesity agents |
| CA2707248A1 (en) | 2007-12-05 | 2009-06-11 | Astrazeneca Ab | New compounds ii |
| EP2785338A1 (en) | 2011-12-01 | 2014-10-08 | Glaxo Group Limited | Methods of treatment and prevention of eye diseases |
| FR3022142B1 (fr) | 2014-06-16 | 2019-07-12 | Universite Paul Sabatier - Toulouse Iii | Inhibition de la chimiokine ccl7 ou de son recepteur ccr3 pour le traitement et le diagnostic du cancer de la prostate |
| US10702521B2 (en) | 2014-08-22 | 2020-07-07 | Glaxosmithkline Intellectual Property Development Limited | Methods for treating neisseria gonorrhoeae infection with substituted 1,2-dihydro-2A,5,8A-triazaacenaphthylene-3,8-diones |
| US20190336489A1 (en) | 2017-01-17 | 2019-11-07 | Glaxosmithkline Intellectual Property Development Limited | Non peptide heterobivalent molecules for treating inflammatory diseases |
| TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法 |
| CN111269340B (zh) * | 2020-03-31 | 2020-12-29 | 台州学院 | 一种以1-甲烷磺酰哌嗪为配体的螯合树脂及其制备方法和应用 |
| CN120132049B (zh) * | 2025-03-05 | 2025-08-26 | 西南医科大学附属口腔医院 | 茶多酚涂层改性的3d打印掺锶羟基磷灰石复合支架的制备方法和应用 |
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|---|---|---|---|---|
| JP3087763B2 (ja) * | 1990-11-30 | 2000-09-11 | 三井化学株式会社 | 新規な複素環式化合物およびそれを含有する医薬組成物 |
| JPH04247074A (ja) * | 1991-02-01 | 1992-09-03 | Yoshitomi Pharmaceut Ind Ltd | ４−モルホリノ安息香酸誘導体の製造法 |
| JPH04270272A (ja) * | 1991-02-25 | 1992-09-25 | Yoshitomi Pharmaceut Ind Ltd | アミノアルキルモルホリン誘導体の製造法 |
| US5753654A (en) * | 1994-05-18 | 1998-05-19 | Nisshin Flour Milling Co., Ltd. | Diaminomethylidene derivatives |
| WO1995031431A1 (en) * | 1994-05-18 | 1995-11-23 | Nisshin Flour Milling Co., Ltd. | Novel diaminomethylidene derivative |
| CA2395558C (en) * | 1997-11-12 | 2007-07-17 | Bayer Aktiengesellschaft | Intermediates for 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors |
| IL143226A0 (en) * | 1998-11-20 | 2002-04-21 | Hoffmann La Roche | Pyrrolidine derivatives-ccr-3 receptor antagonists |
| WO2000035876A1 (en) * | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | 2-substituted-4-nitrogen heterocycles as modulators of chemokine receptor activity |
| WO2000035449A1 (en) * | 1998-12-18 | 2000-06-22 | Du Pont Pharmaceuticals Company | N-ureidoalkyl-piperidines as modulators of chemokine receptor activity |
-
2001
- 2001-09-28 BR BR0114321-2A patent/BR0114321A/pt not_active IP Right Cessation
- 2001-09-28 HU HU0303107A patent/HUP0303107A2/hu unknown
- 2001-09-28 PL PL01362984A patent/PL362984A1/xx not_active Application Discontinuation
- 2001-09-28 AT AT01970027T patent/ATE345331T1/de not_active IP Right Cessation
- 2001-09-28 JP JP2002531107A patent/JP5069392B2/ja not_active Expired - Lifetime
- 2001-09-28 NZ NZ525055A patent/NZ525055A/en unknown
- 2001-09-28 EP EP05076503A patent/EP1586567A1/en not_active Withdrawn
- 2001-09-28 EP EP01970027A patent/EP1324991B1/en not_active Expired - Lifetime
- 2001-09-28 KR KR10-2003-7004593A patent/KR20030040510A/ko not_active Withdrawn
- 2001-09-28 CZ CZ20031194A patent/CZ20031194A3/cs unknown
- 2001-09-28 AR ARP010104603A patent/AR037080A1/es not_active Application Discontinuation
- 2001-09-28 IL IL15509201A patent/IL155092A0/xx unknown
- 2001-09-28 MX MXPA03002813A patent/MXPA03002813A/es unknown
- 2001-09-28 DE DE60124576T patent/DE60124576T2/de not_active Expired - Lifetime
- 2001-09-28 ES ES01970027T patent/ES2275729T3/es not_active Expired - Lifetime
- 2001-09-28 WO PCT/GB2001/004350 patent/WO2002026723A1/en not_active Ceased
- 2001-09-28 CA CA002423305A patent/CA2423305A1/en not_active Abandoned
- 2001-09-28 AU AU2001290146A patent/AU2001290146A1/en not_active Abandoned
- 2001-09-28 CN CNA018196489A patent/CN1478084A/zh active Pending
- 2001-09-28 US US10/381,871 patent/US7157457B2/en not_active Expired - Lifetime
-
2003
- 2003-03-28 NO NO20031443A patent/NO20031443L/no unknown
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