JP2003514808A5 - - Google Patents
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- JP2003514808A5 JP2003514808A5 JP2001538892A JP2001538892A JP2003514808A5 JP 2003514808 A5 JP2003514808 A5 JP 2003514808A5 JP 2001538892 A JP2001538892 A JP 2001538892A JP 2001538892 A JP2001538892 A JP 2001538892A JP 2003514808 A5 JP2003514808 A5 JP 2003514808A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- branched
- partially
- twenty
- phenyl
- 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 description 99
- -1 prinyl Chemical group 0.000 description 98
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 32
- 125000003545 alkoxy group Chemical group 0.000 description 26
- 229910052717 sulfur Inorganic materials 0.000 description 23
- 125000004076 pyridyl group Chemical group 0.000 description 21
- 125000001624 naphthyl group Chemical group 0.000 description 17
- 229910052760 oxygen Inorganic materials 0.000 description 17
- 150000001875 compounds Chemical class 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 229910052736 halogen Inorganic materials 0.000 description 14
- 150000002367 halogens Chemical class 0.000 description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 12
- 125000002883 imidazolyl group Chemical group 0.000 description 12
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 description 11
- 125000004093 cyano group Chemical group *C#N 0.000 description 10
- 125000001072 heteroaryl group Chemical group 0.000 description 10
- 125000004043 oxo group Chemical group O=* 0.000 description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 10
- 125000000168 pyrrolyl group Chemical group 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 9
- 239000001257 hydrogen Substances 0.000 description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
- 125000003373 pyrazinyl group Chemical group 0.000 description 9
- 125000003282 alkyl amino group Chemical group 0.000 description 8
- 125000003226 pyrazolyl group Chemical group 0.000 description 8
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000304 alkynyl group Chemical group 0.000 description 6
- 125000002541 furyl group Chemical group 0.000 description 6
- 150000002431 hydrogen Chemical class 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 125000002098 pyridazinyl group Chemical group 0.000 description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 6
- 125000001544 thienyl group Chemical group 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 description 5
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 5
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 5
- 125000001041 indolyl group Chemical group 0.000 description 5
- 125000001786 isothiazolyl group Chemical group 0.000 description 5
- 125000000842 isoxazolyl group Chemical group 0.000 description 5
- 125000003386 piperidinyl group Chemical group 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000001154 acute effect Effects 0.000 description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 125000004193 piperazinyl group Chemical group 0.000 description 4
- 125000005494 pyridonyl group Chemical group 0.000 description 4
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 4
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 4
- 125000003831 tetrazolyl group Chemical group 0.000 description 4
- 125000006698 (C1-C3) dialkylamino group Chemical group 0.000 description 3
- ZGXFVYOWURGVSM-UHFFFAOYSA-N 4-[4-(2-morpholin-4-yl-2-thiomorpholin-4-ylthiomorpholin-4-yl)sulfinyl-2-thiomorpholin-4-ylthiomorpholin-2-yl]morpholine Chemical compound C1CSC(N2CCSCC2)(N2CCOCC2)CN1S(=O)N(C1)CCSC1(N1CCSCC1)N1CCOCC1 ZGXFVYOWURGVSM-UHFFFAOYSA-N 0.000 description 3
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 3
- 125000002933 cyclohexyloxy group Chemical class C1(CCCCC1)O* 0.000 description 3
- 125000005436 dihydrobenzothiophenyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 125000005241 heteroarylamino group Chemical group 0.000 description 3
- 125000005553 heteroaryloxy group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 description 3
- ZQKVJTVUSZBVQO-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-(4-pyridin-3-yloxynaphthalen-1-yl)urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=CN=C1 ZQKVJTVUSZBVQO-UHFFFAOYSA-N 0.000 description 2
- WQCKNOHLEAQFAP-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-(4-pyridin-4-yloxynaphthalen-1-yl)urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC=C1 WQCKNOHLEAQFAP-UHFFFAOYSA-N 0.000 description 2
- ZFKFZYAWPJMVGZ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methylphenyl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OCCN1CCOCC1 ZFKFZYAWPJMVGZ-UHFFFAOYSA-N 0.000 description 2
- XXHQUBQLTYBRTG-UHFFFAOYSA-N 1-(5-tert-butyl-2-morpholin-4-ylphenyl)-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=C(OCCN2CCOCC2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1N1CCOCC1 XXHQUBQLTYBRTG-UHFFFAOYSA-N 0.000 description 2
- QYCGBAJADAGLLK-UHFFFAOYSA-N 1-(cyclohepten-1-yl)cycloheptene Chemical group C1CCCCC=C1C1=CCCCCC1 QYCGBAJADAGLLK-UHFFFAOYSA-N 0.000 description 2
- VSIYJQNFMOOGCU-UHFFFAOYSA-N 1-(cyclohexen-1-yl)cyclohexene Chemical group C1CCCC(C=2CCCCC=2)=C1 VSIYJQNFMOOGCU-UHFFFAOYSA-N 0.000 description 2
- XVLWJROIONAKQB-UHFFFAOYSA-N 1-[3-bromo-5-tert-butyl-2-(2-morpholin-4-ylethylamino)phenyl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea Chemical compound C=1C=C(OCCN2CCOCC2)C2=CC=CC=C2C=1NC(=O)NC1=CC(C(C)(C)C)=CC(Br)=C1NCCN1CCOCC1 XVLWJROIONAKQB-UHFFFAOYSA-N 0.000 description 2
- MGKPCLNUSDGXGT-UHFFFAOYSA-N 1-benzofuran-3-one Chemical compound C1=CC=C2C(=O)COC2=C1 MGKPCLNUSDGXGT-UHFFFAOYSA-N 0.000 description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 2
- QRCGFTXRXYMJOS-UHFFFAOYSA-N 4h-1,4-benzoxazin-3-one Chemical compound C1=CC=C2NC(=O)COC2=C1 QRCGFTXRXYMJOS-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 102000004127 Cytokines Human genes 0.000 description 2
- 108090000695 Cytokines Proteins 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 2
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 description 2
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 2
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 2
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 150000004982 aromatic amines Chemical class 0.000 description 2
- 125000003435 aroyl group Chemical group 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 2
- 125000003678 cyclohexadienyl group Chemical group C1(=CC=CCC1)* 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000005046 dihydronaphthyl group Chemical group 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 2
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 2
- BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 1
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 1
- 125000005940 1,4-dioxanyl group Chemical group 0.000 description 1
- DKROPLKBDHUKRT-UHFFFAOYSA-N 1-[4-(2-aminopyridin-4-yl)oxynaphthalen-1-yl]-3-(5-tert-butyl-2-methylphenyl)urea Chemical compound CC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C1=CC=CC=C11)=CC=C1OC1=CC=NC(N)=C1 DKROPLKBDHUKRT-UHFFFAOYSA-N 0.000 description 1
- NZUUXQSBKZPFKK-UHFFFAOYSA-N 4-piperazin-1-ylmorpholine Chemical compound C1CNCCN1N1CCOCC1 NZUUXQSBKZPFKK-UHFFFAOYSA-N 0.000 description 1
- KQTGCJMBUBYSLL-UHFFFAOYSA-N 4-piperidin-1-ylmorpholine Chemical compound C1CCCCN1N1CCOCC1 KQTGCJMBUBYSLL-UHFFFAOYSA-N 0.000 description 1
- SSXTZEGNWOYWNY-UHFFFAOYSA-N 6,7,8,9-tetrahydro-5h-cyclohepta[b]pyrazine Chemical compound C1CCCCC2=NC=CN=C21 SSXTZEGNWOYWNY-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- JPZCTPYNLCZLQB-UHFFFAOYSA-N CC(=O)NC1=C(C(=CC(=C1)C(C)(C)C)NC(=O)NC2C(=CC3=CC=NC=C3)C=CC4=CC=CC=C24)OC Chemical compound CC(=O)NC1=C(C(=CC(=C1)C(C)(C)C)NC(=O)NC2C(=CC3=CC=NC=C3)C=CC4=CC=CC=C24)OC JPZCTPYNLCZLQB-UHFFFAOYSA-N 0.000 description 1
- DQXOHEONGSWKRM-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C(=C1)NC(=O)N(C)C)OC)NC(=O)NC2C(=CC3=CC=NC=C3)C=CC4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(C(=C1)NC(=O)N(C)C)OC)NC(=O)NC2C(=CC3=CC=NC=C3)C=CC4=CC=CC=C24 DQXOHEONGSWKRM-UHFFFAOYSA-N 0.000 description 1
- VGXRGIMBBBUPCJ-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C(=C1)NC(=O)N2CCOCC2)OC)NC(=O)NC3C(=CC4=CC=NC=C4)C=CC5=CC=CC=C35 Chemical compound CC(C)(C)C1=CC(=C(C(=C1)NC(=O)N2CCOCC2)OC)NC(=O)NC3C(=CC4=CC=NC=C4)C=CC5=CC=CC=C35 VGXRGIMBBBUPCJ-UHFFFAOYSA-N 0.000 description 1
- RVYCZCKPTXJYGZ-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 RVYCZCKPTXJYGZ-UHFFFAOYSA-N 0.000 description 1
- HJGYWSBTOJFHEK-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)NC)C4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)NC)C4=CC=CC=C24 HJGYWSBTOJFHEK-UHFFFAOYSA-N 0.000 description 1
- IOUUKLOBUSZXNL-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)OC)C4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(C(=C1)OC)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)OC)C4=CC=CC=C24 IOUUKLOBUSZXNL-UHFFFAOYSA-N 0.000 description 1
- HMOJKZVAYIDXRR-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(C=C1)OC)NC(=O)NC2=CCC(=CC3=CC(=C)NC=C3)C4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(C=C1)OC)NC(=O)NC2=CCC(=CC3=CC(=C)NC=C3)C4=CC=CC=C24 HMOJKZVAYIDXRR-UHFFFAOYSA-N 0.000 description 1
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- KZBTYTJSQCUCCE-UHFFFAOYSA-N CC(C)(C)C1=CC(=C(N=C1)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 Chemical compound CC(C)(C)C1=CC(=C(N=C1)OC)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 KZBTYTJSQCUCCE-UHFFFAOYSA-N 0.000 description 1
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- UWVJQHGDCLERCS-UHFFFAOYSA-N CC(C1=CC=CC=C1)NC2=NC=CC(=C2)C=C3CC=C(C4=CC=CC=C34)NC(=O)NC5=C(N=CC(=C5)C(C)(C)C)OC Chemical compound CC(C1=CC=CC=C1)NC2=NC=CC(=C2)C=C3CC=C(C4=CC=CC=C34)NC(=O)NC5=C(N=CC(=C5)C(C)(C)C)OC UWVJQHGDCLERCS-UHFFFAOYSA-N 0.000 description 1
- KJIXACNTXVJWGL-UHFFFAOYSA-N CC1=C(C=C(C=C1)C(C)(C)C)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 Chemical compound CC1=C(C=C(C=C1)C(C)(C)C)NC(=O)NC2=CCC(=CC3=CC(=NC=C3)N)C4=CC=CC=C24 KJIXACNTXVJWGL-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- 206010051920 Glomerulonephropathy Diseases 0.000 description 1
- 208000009329 Graft vs Host Disease Diseases 0.000 description 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 description 1
- 208000034486 Multi-organ failure Diseases 0.000 description 1
- 208000010718 Multiple Organ Failure Diseases 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 125000003113 cycloheptyloxy group Chemical class C1(CCCCCC1)O* 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- XOVJAYNMQDTIJD-UHFFFAOYSA-N cyclopentobarbital Chemical compound C1CC=CC1C1(CC=C)C(=O)NC(=O)NC1=O XOVJAYNMQDTIJD-UHFFFAOYSA-N 0.000 description 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000004652 decahydroisoquinolinyl group Chemical group C1(NCCC2CCCCC12)* 0.000 description 1
- 125000004856 decahydroquinolinyl group Chemical group N1(CCCC2CCCCC12)* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005044 dihydroquinolinyl group Chemical group N1(CC=CC2=CC=CC=C12)* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
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| DE19631303C2 (de) | 1996-08-02 | 1998-07-02 | Kettner Karl Ulrich Prof Dr | Vorrichtung zum Schutz von Gefäßen bei chirurgischen Eingriffen |
| WO1998050346A2 (en) * | 1997-04-18 | 1998-11-12 | Smithkline Beecham Plc | Acetamide and urea derivatives, process for their preparation and their use in the treatment of cns disorders |
| EP1019040B1 (en) | 1997-05-23 | 2004-09-29 | Bayer Corporation | Aryl ureas for the treatment of inflammatory or immunomodulatory diseases |
| DE69819903T2 (de) * | 1997-08-09 | 2004-11-11 | Smithkline Beecham P.L.C., Brentford | Bicyclische verbindungen als liganden der 5-ht1 rezeptoren |
| AUPP003197A0 (en) * | 1997-09-03 | 1997-11-20 | Fujisawa Pharmaceutical Co., Ltd. | New heterocyclic compounds |
| AU1367599A (en) * | 1997-11-03 | 1999-05-24 | Boehringer Ingelheim Pharmaceuticals, Inc. | Aromatic heterocyclic compounds as anti-inflammatory agents |
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-
2000
- 2000-11-16 ES ES00978751T patent/ES2292488T3/es not_active Expired - Lifetime
- 2000-11-16 MX MXPA02004594A patent/MXPA02004594A/es active IP Right Grant
- 2000-11-16 US US09/714,539 patent/US6492393B1/en not_active Expired - Lifetime
- 2000-11-16 JP JP2001538892A patent/JP4955171B2/ja not_active Expired - Lifetime
- 2000-11-16 MX MXPA02004879A patent/MXPA02004879A/es unknown
- 2000-11-16 AU AU16179/01A patent/AU1617901A/en not_active Abandoned
- 2000-11-16 WO PCT/US2000/031582 patent/WO2001036403A1/en not_active Ceased
- 2000-11-16 AT AT00978751T patent/ATE375334T1/de active
- 2000-11-16 CA CA002389360A patent/CA2389360C/en not_active Expired - Lifetime
- 2000-11-16 DE DE60036726T patent/DE60036726T2/de not_active Expired - Lifetime
- 2000-11-16 EP EP00978751A patent/EP1232150B1/en not_active Expired - Lifetime
-
2002
- 2002-10-15 US US10/271,301 patent/US7241758B2/en not_active Expired - Lifetime
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