JP2002504539A - ホスホリパーゼ酵素の阻害剤 - Google Patents
ホスホリパーゼ酵素の阻害剤Info
- Publication number
- JP2002504539A JP2002504539A JP2000533409A JP2000533409A JP2002504539A JP 2002504539 A JP2002504539 A JP 2002504539A JP 2000533409 A JP2000533409 A JP 2000533409A JP 2000533409 A JP2000533409 A JP 2000533409A JP 2002504539 A JP2002504539 A JP 2002504539A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- methyl
- phenyl
- pharmaceutically acceptable
- acceptable salt
- 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- Withdrawn
Links
- 108010064785 Phospholipases Proteins 0.000 title claims abstract description 19
- 102000015439 Phospholipases Human genes 0.000 title claims abstract description 19
- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 239000002532 enzyme inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 191
- 238000000034 method Methods 0.000 claims abstract description 60
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 32
- 230000000694 effects Effects 0.000 claims abstract description 20
- -1 -O-phenyl Chemical group 0.000 claims description 166
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 155
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 114
- 150000003839 salts Chemical class 0.000 claims description 106
- 229910052736 halogen Inorganic materials 0.000 claims description 105
- 150000002367 halogens Chemical class 0.000 claims description 101
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 73
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 63
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 59
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 57
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 55
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 50
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 50
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 33
- 229910052717 sulfur Inorganic materials 0.000 claims description 31
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 30
- 239000005711 Benzoic acid Substances 0.000 claims description 29
- 235000010233 benzoic acid Nutrition 0.000 claims description 29
- 125000004076 pyridyl group Chemical group 0.000 claims description 29
- 125000005979 2-naphthyloxy group Chemical group 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 125000002541 furyl group Chemical group 0.000 claims description 26
- 125000001544 thienyl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 102000004190 Enzymes Human genes 0.000 claims description 22
- 108090000790 Enzymes Proteins 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 21
- 150000003536 tetrazoles Chemical class 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 19
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims description 18
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 18
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000001624 naphthyl group Chemical group 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 230000002378 acidificating effect Effects 0.000 claims description 8
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 8
- XRLDSWLMHUQECH-UHFFFAOYSA-N cyclopentanecarboxamide Chemical compound NC(=O)C1CCCC1 XRLDSWLMHUQECH-UHFFFAOYSA-N 0.000 claims description 8
- 230000028709 inflammatory response Effects 0.000 claims description 8
- 230000002401 inhibitory effect Effects 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- 125000006309 butyl amino group Chemical group 0.000 claims description 6
- 125000006518 morpholino carbonyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])N(C(*)=O)C1([H])[H] 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 claims description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims description 3
- VHRWSJSYNRPCDJ-UHFFFAOYSA-N 3-[[1-[(4-carboxyphenyl)methyl]-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-5-yl]carbamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C=3C=C(C=CC=3)C(O)=O)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 VHRWSJSYNRPCDJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- PLJCHEFJWIQVNJ-UHFFFAOYSA-N 2-[3-acetyl-2-(naphthalen-2-ylsulfanylmethyl)-5-phenylmethoxyindol-1-yl]acetic acid Chemical compound C1=C2C(C(=O)C)=C(CSC=3C=C4C=CC=CC4=CC=3)N(CC(O)=O)C2=CC=C1OCC1=CC=CC=C1 PLJCHEFJWIQVNJ-UHFFFAOYSA-N 0.000 claims description 2
- OEXARBJNOQARFV-UHFFFAOYSA-N 2-[4-[[3-(naphthalene-1-carbonyl)-5-phenylmethoxyindol-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C3=CC=CC=C3C=CC=2)=C1 OEXARBJNOQARFV-UHFFFAOYSA-N 0.000 claims description 2
- AEMVESKVBNFDCE-UHFFFAOYSA-N 2-[4-[[3-(naphthalene-2-carbonyl)-5-phenylmethoxyindol-1-yl]methyl]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1CN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C=C3C=CC=CC3=CC=2)=C1 AEMVESKVBNFDCE-UHFFFAOYSA-N 0.000 claims description 2
- HQSWGRQOMWFXMF-UHFFFAOYSA-N 3-[[5-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]-2-oxopentanoyl]amino]benzoic acid Chemical compound OC(=O)C1=CC=CC(NC(=O)C(=O)CCCN2C3=CC=C(OCC=4C=CC=CC=4)C=C3C(C(=O)C=3C=CC=CC=3)=C2COC=2C=C3C=CC=CC3=CC=2)=C1 HQSWGRQOMWFXMF-UHFFFAOYSA-N 0.000 claims description 2
- HCHSFVKTMDUFAW-UHFFFAOYSA-N 4-[5-(cyclopentanecarbonylamino)-2-(naphthalen-2-yloxymethyl)-3-(pyrrolidine-1-carbonyl)indol-1-yl]butanoic acid Chemical compound C12=CC(NC(=O)C3CCCC3)=CC=C2N(CCCC(=O)O)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)N1CCCC1 HCHSFVKTMDUFAW-UHFFFAOYSA-N 0.000 claims description 2
- UFCCKBCEUADLMV-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 UFCCKBCEUADLMV-UHFFFAOYSA-N 0.000 claims description 2
- YPIFVHRLONGTRD-UHFFFAOYSA-N 4-[[5-[3-benzoyl-2-(naphthalen-2-yloxymethyl)-5-phenylmethoxyindol-1-yl]-2-oxopentanoyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(=O)CCCN1C2=CC=C(OCC=3C=CC=CC=3)C=C2C(C(=O)C=2C=CC=CC=2)=C1COC1=CC=C(C=CC=C2)C2=C1 YPIFVHRLONGTRD-UHFFFAOYSA-N 0.000 claims description 2
- SVYRNGXSUBDSQZ-UHFFFAOYSA-N 4-[[5-[acetyl(benzyl)amino]-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C=1C=C2N(CC=3C=CC(=CC=3)C(O)=O)C(CSC=3C=C4C=CC=CC4=CC=3)=C(Cl)C2=CC=1N(C(=O)C)CC1=CC=CC=C1 SVYRNGXSUBDSQZ-UHFFFAOYSA-N 0.000 claims description 2
- GMMSBVMFOMBAGX-UHFFFAOYSA-N 4-[[5-amino-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1SCC1=C(Cl)C2=CC(N)=CC=C2N1CC1=CC=C(C(O)=O)C=C1 GMMSBVMFOMBAGX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- CZGCDUZPZBKIQB-UHFFFAOYSA-N 5-(cyclopentanecarbonylamino)-2-(naphthalen-2-yloxymethyl)-1-[4-oxo-4-(trifluoromethylsulfonylamino)butyl]indole-3-carboxylic acid Chemical compound C1=C2C(C(=O)O)=C(COC=3C=C4C=CC=CC4=CC=3)N(CCCC(=O)NS(=O)(=O)C(F)(F)F)C2=CC=C1NC(=O)C1CCCC1 CZGCDUZPZBKIQB-UHFFFAOYSA-N 0.000 claims description 2
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- WARLBQLHVRYWHC-UHFFFAOYSA-N n-[3-(morpholine-4-carbonyl)-2-(naphthalen-2-yloxymethyl)-1-[4-oxo-4-(trifluoromethylsulfonylamino)butyl]indol-5-yl]cyclopentanecarboxamide Chemical compound C12=CC(NC(=O)C3CCCC3)=CC=C2N(CCCC(=O)NS(=O)(=O)C(F)(F)F)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)N1CCOCC1 WARLBQLHVRYWHC-UHFFFAOYSA-N 0.000 claims description 2
- IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims 5
- ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 claims 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims 2
- 235000019260 propionic acid Nutrition 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- JKQJELDRSIXSBZ-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(3-phenylpropanoylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)CCC=3C=CC=CC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 JKQJELDRSIXSBZ-UHFFFAOYSA-N 0.000 claims 1
- LDVNFAGFIFYWNO-UHFFFAOYSA-N 4-[[3-chloro-2-(naphthalen-2-ylsulfanylmethyl)-5-(phenylmethoxycarbonylamino)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)OCC=3C=CC=CC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 LDVNFAGFIFYWNO-UHFFFAOYSA-N 0.000 claims 1
- WUYCLXNQVMRRNF-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-(cyclopentylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSC1CCCC1 WUYCLXNQVMRRNF-UHFFFAOYSA-N 0.000 claims 1
- QWBURGQFHRUUQV-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-(cyclopropylmethylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSCC1CC1 QWBURGQFHRUUQV-UHFFFAOYSA-N 0.000 claims 1
- GAEVLRZBLLQWCW-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]-n-(4-nitrophenyl)sulfonylbenzamide Chemical compound C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC(=O)C(C=C1)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 GAEVLRZBLLQWCW-UHFFFAOYSA-N 0.000 claims 1
- LOCRVSASNMFJSC-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-(quinolin-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=N1 LOCRVSASNMFJSC-UHFFFAOYSA-N 0.000 claims 1
- ASPUGHDOCSLMEH-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-[(2,4-dibromophenoxy)methyl]indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1COC1=CC=C(Br)C=C1Br ASPUGHDOCSLMEH-UHFFFAOYSA-N 0.000 claims 1
- CWLLTHSVUASHHO-UHFFFAOYSA-N 4-[[3-chloro-5-(cyclopentanecarbonylamino)-2-[(4-thiophen-2-ylpyrimidin-2-yl)sulfanylmethyl]indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C3CCCC3)C=C2C(Cl)=C1CSC1=NC=CC(C=2SC=CC=2)=N1 CWLLTHSVUASHHO-UHFFFAOYSA-N 0.000 claims 1
- XPPMAOGSJNBPQB-UHFFFAOYSA-N 4-[[5-(3-carboxypropanoylamino)-3-chloro-2-[(3-methylphenyl)methylsulfanylmethyl]indol-1-yl]methyl]benzoic acid Chemical compound CC1=CC=CC(CSCC=2N(C3=CC=C(NC(=O)CCC(O)=O)C=C3C=2Cl)CC=2C=CC(=CC=2)C(O)=O)=C1 XPPMAOGSJNBPQB-UHFFFAOYSA-N 0.000 claims 1
- WPCXCEXSMLDLPM-UHFFFAOYSA-N 4-[[5-(adamantane-1-carbonylamino)-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)C34CC5CC(CC(C5)C3)C4)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 WPCXCEXSMLDLPM-UHFFFAOYSA-N 0.000 claims 1
- YZMKSOWTKNRKDO-UHFFFAOYSA-N 4-[[5-(benzylcarbamoylamino)-3-chloro-2-(naphthalen-2-ylsulfanylmethyl)indol-1-yl]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CN1C2=CC=C(NC(=O)NCC=3C=CC=CC=3)C=C2C(Cl)=C1CSC1=CC=C(C=CC=C2)C2=C1 YZMKSOWTKNRKDO-UHFFFAOYSA-N 0.000 claims 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N Valeric acid Natural products CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- RSLHAOHUFVWAJP-UHFFFAOYSA-N n-[2-(naphthalen-2-yloxymethyl)-1-[4-oxo-4-(trifluoromethylsulfonylamino)butyl]-3-(pyrrolidine-1-carbonyl)indol-5-yl]cyclopentanecarboxamide Chemical compound C12=CC(NC(=O)C3CCCC3)=CC=C2N(CCCC(=O)NS(=O)(=O)C(F)(F)F)C(COC=2C=C3C=CC=CC3=CC=2)=C1C(=O)N1CCCC1 RSLHAOHUFVWAJP-UHFFFAOYSA-N 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000006187 phenyl benzyl group Chemical group 0.000 claims 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 339
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- 238000002390 rotary evaporation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 238000002821 scintillation proximity assay Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 210000001179 synovial fluid Anatomy 0.000 description 1
- QEOUGFSILBVRCP-UHFFFAOYSA-N tert-butyl-dimethyl-[(5-phenylmethoxy-1h-indol-2-yl)methoxy]silane Chemical compound C=1C=C2NC(CO[Si](C)(C)C(C)(C)C)=CC2=CC=1OCC1=CC=CC=C1 QEOUGFSILBVRCP-UHFFFAOYSA-N 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002435 venom Substances 0.000 description 1
- 210000001048 venom Anatomy 0.000 description 1
- 231100000611 venom Toxicity 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
- 229960005332 zileuton Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3006298A | 1998-02-25 | 1998-02-25 | |
US09/030,062 | 1998-02-25 | ||
PCT/US1999/003899 WO1999043651A2 (en) | 1998-02-25 | 1999-02-24 | Inhibitors of phospholipase enzymes |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2002504539A true JP2002504539A (ja) | 2002-02-12 |
Family
ID=21852314
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000533409A Withdrawn JP2002504539A (ja) | 1998-02-25 | 1999-02-24 | ホスホリパーゼ酵素の阻害剤 |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP1056719A2 (de) |
JP (1) | JP2002504539A (de) |
KR (1) | KR20010041343A (de) |
CN (1) | CN1299347A (de) |
AU (1) | AU2782699A (de) |
BG (1) | BG104780A (de) |
BR (1) | BR9908280A (de) |
CA (1) | CA2322161A1 (de) |
EA (1) | EA200000868A1 (de) |
EE (1) | EE200000486A (de) |
HR (1) | HRP20000552A2 (de) |
HU (1) | HUP0100757A3 (de) |
ID (1) | ID27280A (de) |
IL (1) | IL137718A0 (de) |
NO (1) | NO20004220L (de) |
PL (1) | PL342995A1 (de) |
SK (1) | SK12742000A3 (de) |
TR (1) | TR200002446T2 (de) |
WO (1) | WO1999043651A2 (de) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007500190A (ja) * | 2003-07-25 | 2007-01-11 | ワイス | Cpla2阻害剤の製法 |
JP2008517959A (ja) * | 2004-10-27 | 2008-05-29 | エフ.ホフマン−ラ ロシュ アーゲー | 新規なインドール又はベンゾイミダゾール誘導体 |
JP2008527029A (ja) * | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
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DE60009480T2 (de) * | 1999-05-05 | 2005-09-01 | Aventis Pharma Ltd., West Malling | Harnstoffe als modulatoren der zelladhäsion |
DE60128475T2 (de) | 2000-07-25 | 2008-02-07 | Merck & Co., Inc. | N-substituierte indole mit anwendung in der behandlung von diabetes |
CA2436130A1 (en) | 2001-01-29 | 2002-08-08 | 3-Dimensional Pharmaceuticals, Inc. | Substituted indoles and their use as integrin antagonists |
US6608196B2 (en) | 2001-05-03 | 2003-08-19 | Galileo Pharmaceuticals, Inc. | Process for solid supported synthesis of pyruvate-derived compounds |
ATE408593T1 (de) | 2001-05-03 | 2008-10-15 | Galileo Lab Inc | Pyruvatderivate |
DK1397130T3 (da) | 2001-06-20 | 2007-11-12 | Wyeth Corp | Substituerede indolsyrederivater som inhibitorer af plasminogenaktivatorinhibitor-1 (PAI-1) |
US7291639B2 (en) | 2001-06-20 | 2007-11-06 | Wyeth | Aryloxy-acetic acid compounds useful as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
TWI224101B (en) | 2001-06-20 | 2004-11-21 | Wyeth Corp | Substituted naphthyl indole derivatives as inhibitors of plasminogen activator inhibitor type-1 (PAI-1) |
US7189751B2 (en) * | 2001-06-25 | 2007-03-13 | Nippon Soda Co., Ltd. | Oxa(thia)zolidine compounds, process for preparation thereof and anti-inflammatory agents |
US7101875B2 (en) | 2001-12-03 | 2006-09-05 | Wyeth | Methods for treating arthritic disorders |
US6635771B2 (en) | 2001-12-03 | 2003-10-21 | Wyeth | N-benzhydryl indole compounds |
US7605156B2 (en) | 2001-12-03 | 2009-10-20 | Wyeth | Methods for the use of inhibitors of cytosolic phospholipase A2 |
SI1451154T1 (sl) * | 2001-12-03 | 2008-06-30 | Wyeth Corp | Zaviralci citosolne fosfolipaze a2 |
US6984735B2 (en) | 2001-12-03 | 2006-01-10 | Wyeth | Process for making an aldehyde |
US6797708B2 (en) * | 2001-12-03 | 2004-09-28 | Wyeth | Inhibitors of cytosolic phospholipase A2 |
PL370445A1 (en) * | 2001-12-03 | 2005-05-30 | Wyeth | Inhibitors of cytosolic phospholipase a2 |
US7713964B2 (en) | 2001-12-03 | 2010-05-11 | Wyeth Llc | Methods for treating asthmatic conditions |
AUPS282602A0 (en) | 2002-06-07 | 2002-06-27 | Garvan Institute Of Medical Research | Method of inhibiting cell proliferation |
JP4340232B2 (ja) | 2002-08-29 | 2009-10-07 | メルク エンド カムパニー インコーポレーテッド | 抗糖尿病活性を有するインドール類 |
PT1537078E (pt) | 2002-08-29 | 2010-06-18 | Merck Sharp & Dohme | Indoles que possuem actividade antidiabética |
KR20050072812A (ko) | 2002-11-07 | 2005-07-12 | 악조 노벨 엔.브이. | 안드로겐-수용체와 관련된 질병의 치료에 효과적인 인돌 |
US7348351B2 (en) | 2002-12-10 | 2008-03-25 | Wyeth | Substituted 3-alkyl and 3-arylalkyl 1H-indol-1yl acetic acid derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1) |
DE60306548T2 (de) | 2002-12-10 | 2007-06-21 | Wyeth | Substituierte 3-carbonyl-1-yl-essigsäure-derivate als plasminogen aktivator inhibitor(pai-1) inhibitoren |
JP2006510673A (ja) | 2002-12-10 | 2006-03-30 | ワイス | プラスミノゲンアクティベータインヒビター1(pai−1)のインヒビターとしての、アリール、アリールオキシ、および、アルキルオキシ置換1h−インドール−3−イルグリオキシル酸誘導体 |
BR0316584A (pt) | 2002-12-10 | 2005-10-04 | Wyeth Corp | Derivados de ácido acético indol oxo-acetil amino substituìdo como inibidores do inibidor-1 do ativador do plasminogênio (pai-1) |
UA80453C2 (en) | 2002-12-10 | 2007-09-25 | Derivatives of substituted dyhydropyranoindol-3,4-dion as inhibitors of plasminogen activator inhibitor-1 (pai-1) | |
US7342039B2 (en) | 2003-09-25 | 2008-03-11 | Wyeth | Substituted indole oximes |
US7332521B2 (en) | 2003-09-25 | 2008-02-19 | Wyeth | Substituted indoles |
US7163954B2 (en) | 2003-09-25 | 2007-01-16 | Wyeth | Substituted naphthyl benzothiophene acids |
US7265148B2 (en) | 2003-09-25 | 2007-09-04 | Wyeth | Substituted pyrrole-indoles |
US7351726B2 (en) | 2003-09-25 | 2008-04-01 | Wyeth | Substituted oxadiazolidinediones |
US7411083B2 (en) | 2003-09-25 | 2008-08-12 | Wyeth | Substituted acetic acid derivatives |
US7268159B2 (en) | 2003-09-25 | 2007-09-11 | Wyeth | Substituted indoles |
US7141592B2 (en) | 2003-09-25 | 2006-11-28 | Wyeth | Substituted oxadiazolidinediones |
US7446201B2 (en) | 2003-09-25 | 2008-11-04 | Wyeth | Substituted heteroaryl benzofuran acids |
US7582773B2 (en) | 2003-09-25 | 2009-09-01 | Wyeth | Substituted phenyl indoles |
US7442805B2 (en) | 2003-09-25 | 2008-10-28 | Wyeth | Substituted sulfonamide-indoles |
US7420083B2 (en) | 2003-09-25 | 2008-09-02 | Wyeth | Substituted aryloximes |
GB0324763D0 (en) | 2003-10-23 | 2003-11-26 | Oxagen Ltd | Use of compounds in therapy |
TW200602317A (en) | 2004-04-23 | 2006-01-16 | Akzo Nobel Nv | Novel androgens |
ES2315877T3 (es) | 2004-06-18 | 2009-04-01 | Biolipox Ab | Indoles utiles en el tratamiento de inflamaciones. |
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US7777040B2 (en) | 2005-05-03 | 2010-08-17 | Cgi Pharmaceuticals, Inc. | Certain substituted ureas, as modulators of kinase activity |
GT200600228A (es) * | 2005-05-27 | 2006-12-26 | Inhibidores de la fosfolipasa a2 citosolica | |
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US9062055B2 (en) | 2010-06-21 | 2015-06-23 | Incyte Corporation | Fused pyrrole derivatives as PI3K inhibitors |
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US9108984B2 (en) | 2011-03-14 | 2015-08-18 | Incyte Corporation | Substituted diamino-pyrimidine and diamino-pyridine derivatives as PI3K inhibitors |
WO2012135009A1 (en) | 2011-03-25 | 2012-10-04 | Incyte Corporation | Pyrimidine-4,6-diamine derivatives as pi3k inhibitors |
HUE030869T2 (en) | 2011-09-02 | 2017-06-28 | Incyte Holdings Corp | Heterocyclic amines as inhibitors of PI3K |
AR090548A1 (es) | 2012-04-02 | 2014-11-19 | Incyte Corp | Azaheterociclobencilaminas biciclicas como inhibidores de pi3k |
IN2014KN02993A (de) | 2012-07-17 | 2015-05-08 | Glaxosmithkline Ip No 2 Ltd | |
GB201322273D0 (en) | 2013-12-17 | 2014-01-29 | Atopix Therapeutics Ltd | Process |
WO2015191677A1 (en) | 2014-06-11 | 2015-12-17 | Incyte Corporation | Bicyclic heteroarylaminoalkyl phenyl derivatives as pi3k inhibitors |
TWI748941B (zh) | 2015-02-27 | 2021-12-11 | 美商英塞特公司 | Pi3k抑制劑之鹽及製備方法 |
WO2016183060A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Process for the synthesis of a phosphoinositide 3-kinase inhibitor |
WO2016183063A1 (en) | 2015-05-11 | 2016-11-17 | Incyte Corporation | Crystalline forms of a pi3k inhibitor |
KR20210125471A (ko) | 2018-10-05 | 2021-10-18 | 안나푸르나 바이오, 인코포레이티드 | Apj 수용체 활성과 관련된 병태를 치료하기 위한 화합물 및 조성물 |
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FR1492929A (fr) * | 1966-05-11 | 1967-08-25 | Roussel Uclaf | Nouveaux 1-(omega-carboxyalcoyl) indoles substitués et procédé de préparation |
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DE1816335A1 (de) * | 1968-12-21 | 1970-07-09 | Thiemann Gmbh Chem Pharm Fabri | Verfahren zur Herstellung von [2-Methyl-5-alkoxy-3-acyl-indol-1]-essigsaeuren und deren Estern |
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IL109311A0 (en) * | 1993-04-16 | 1994-07-31 | Lilly Co Eli | 1H-indole-3-acetamide sPla2 inhibitors |
DE4338770A1 (de) * | 1993-11-12 | 1995-05-18 | Matthias Dr Lehr | Indol-2-alkansäuren und ihre Derivate als Hemmstoffe der Phospholipase A¶2¶ |
ES2208935T3 (es) * | 1996-08-01 | 2004-06-16 | Merckle Gmbh | Acidos acil-pirrol-dicarboxilicos y acidos acil-indol-dicarboxilicos, asi como sus derivados como inhibidores de la fosfolipasa a2 citosolica. |
CA2264020A1 (en) * | 1996-08-26 | 1998-03-05 | Jean Bemis | Inhibitors of phospholipase enzymes |
-
1999
- 1999-02-24 JP JP2000533409A patent/JP2002504539A/ja not_active Withdrawn
- 1999-02-24 BR BR9908280-2A patent/BR9908280A/pt not_active IP Right Cessation
- 1999-02-24 PL PL99342995A patent/PL342995A1/xx unknown
- 1999-02-24 SK SK1274-2000A patent/SK12742000A3/sk unknown
- 1999-02-24 CA CA002322161A patent/CA2322161A1/en not_active Abandoned
- 1999-02-24 EP EP99908379A patent/EP1056719A2/de not_active Withdrawn
- 1999-02-24 TR TR2000/02446T patent/TR200002446T2/xx unknown
- 1999-02-24 IL IL13771899A patent/IL137718A0/xx unknown
- 1999-02-24 ID IDW20001594A patent/ID27280A/id unknown
- 1999-02-24 CN CN99805385A patent/CN1299347A/zh active Pending
- 1999-02-24 WO PCT/US1999/003899 patent/WO1999043651A2/en not_active Application Discontinuation
- 1999-02-24 HU HU0100757A patent/HUP0100757A3/hu unknown
- 1999-02-24 EA EA200000868A patent/EA200000868A1/ru unknown
- 1999-02-24 KR KR1020007009456A patent/KR20010041343A/ko not_active Application Discontinuation
- 1999-02-24 AU AU27826/99A patent/AU2782699A/en not_active Abandoned
- 1999-02-24 EE EEP200000486A patent/EE200000486A/xx unknown
-
2000
- 2000-08-23 NO NO20004220A patent/NO20004220L/no unknown
- 2000-08-24 HR HR20000552A patent/HRP20000552A2/hr not_active Application Discontinuation
- 2000-09-19 BG BG104780A patent/BG104780A/xx unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007500190A (ja) * | 2003-07-25 | 2007-01-11 | ワイス | Cpla2阻害剤の製法 |
JP2008517959A (ja) * | 2004-10-27 | 2008-05-29 | エフ.ホフマン−ラ ロシュ アーゲー | 新規なインドール又はベンゾイミダゾール誘導体 |
JP2008527029A (ja) * | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
Also Published As
Publication number | Publication date |
---|---|
KR20010041343A (ko) | 2001-05-15 |
WO1999043651A3 (en) | 1999-12-16 |
HUP0100757A3 (en) | 2001-11-28 |
AU2782699A (en) | 1999-09-15 |
EE200000486A (et) | 2002-02-15 |
HRP20000552A2 (en) | 2001-04-30 |
BG104780A (en) | 2001-10-31 |
EA200000868A1 (ru) | 2001-04-23 |
PL342995A1 (en) | 2001-07-16 |
ID27280A (id) | 2001-03-22 |
NO20004220D0 (no) | 2000-08-23 |
NO20004220L (no) | 2000-10-05 |
BR9908280A (pt) | 2000-10-31 |
SK12742000A3 (sk) | 2001-05-10 |
HUP0100757A1 (hu) | 2001-08-28 |
WO1999043651A2 (en) | 1999-09-02 |
EP1056719A2 (de) | 2000-12-06 |
IL137718A0 (en) | 2001-10-31 |
CA2322161A1 (en) | 1999-09-02 |
CN1299347A (zh) | 2001-06-13 |
TR200002446T2 (tr) | 2000-12-21 |
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