ES2468546T3

ES2468546T3 - Nuevos inhibidores de glutaminil ciclasa

Nuevos inhibidores de glutaminil ciclasa Download PDF

Info

Publication number: ES2468546T3
Authority: ES; Spain
Prior art keywords: imidazolidin; phenyl; benzoimidazol; propyl; imidazol
Prior art date: 2006-11-09
Legal status : Active

Application number

ES07822338.5T

Other languages

English (en)

Spanish (es)

Inventor

Michael Thormann

Michael Almstetter

Andreas Treml

Ulrich Heiser

Mirko Buchholz

Current Assignee

Vivoryon Therapeutics AG

Original Assignee

Probiodrug AG

Priority date

2006-11-09

Filing date

2007-11-08

Publication date

2014-06-16

2007-11-08 Application filed by Probiodrug AG filed Critical Probiodrug AG

2014-06-16 Application granted granted Critical

2014-06-16 Publication of ES2468546T3 publication Critical patent/ES2468546T3/es

Status Active legal-status Critical Current

2027-11-08 Anticipated expiration legal-status Critical

Links

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239000003377 acid catalyst Substances 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
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ZZTVPHBKVVIGHH-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(3,5-dibromophenyl)-5-(3-phenylpropylamino)-4h-imidazole-2-thione Chemical compound BrC1=CC(Br)=CC(C2C(NC(=S)N2C=2C=C3N=CNC3=CC=2)=NCCCC=2C=CC=CC=2)=C1 ZZTVPHBKVVIGHH-UHFFFAOYSA-N 0.000 claims 1
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WJMJUTUDZQWFRF-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(3-bromophenyl)-5-(2-morpholin-4-ylethylamino)-4h-imidazol-2-one Chemical compound BrC1=CC=CC(C2C(NC(=O)N2C=2C=C3NC=NC3=CC=2)=NCCN2CCOCC2)=C1 WJMJUTUDZQWFRF-UHFFFAOYSA-N 0.000 claims 1
FSTBCHQHVOOGBK-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(4-bromophenyl)-5-(cyclopropylamino)-4h-imidazol-2-one Chemical compound C1=CC(Br)=CC=C1C(N(C(=O)N1)C=2C=C3NC=NC3=CC=2)C1=NC1CC1 FSTBCHQHVOOGBK-UHFFFAOYSA-N 0.000 claims 1
XLYWTRVQFRWIFS-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(4-bromothiophen-2-yl)-5-(cyclohexylamino)-4h-imidazol-2-one Chemical compound BrC1=CSC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=NC2CCCCC2)=C1 XLYWTRVQFRWIFS-UHFFFAOYSA-N 0.000 claims 1
ISMZHGDSIFUQQB-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(4-chloro-3-fluorophenyl)-5-(cyclopropylamino)-4h-imidazol-2-one Chemical compound C1=C(Cl)C(F)=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=NC2CC2)=C1 ISMZHGDSIFUQQB-UHFFFAOYSA-N 0.000 claims 1
KYOZZNDKLFCJRA-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(4-chloro-3-fluorophenyl)-5-(methylamino)-4h-imidazol-2-one Chemical compound CN=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=C(Cl)C(F)=C1 KYOZZNDKLFCJRA-UHFFFAOYSA-N 0.000 claims 1
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YKXOQVNJMNGFKT-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-bromo-1,3-benzodioxol-5-yl)-5-(2-thiophen-2-ylethylamino)-4h-imidazol-2-one Chemical compound BrC1=CC=2OCOC=2C=C1C1N(C=2C=C3NC=NC3=CC=2)C(=O)NC1=NCCC1=CC=CS1 YKXOQVNJMNGFKT-UHFFFAOYSA-N 0.000 claims 1
KLNSVNIZSJEAJX-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-bromo-1,3-benzodioxol-5-yl)-5-(2-thiophen-2-ylethylamino)-4h-imidazole-2-thione Chemical compound BrC1=CC=2OCOC=2C=C1C1N(C=2C=C3NC=NC3=CC=2)C(=S)NC1=NCCC1=CC=CS1 KLNSVNIZSJEAJX-UHFFFAOYSA-N 0.000 claims 1
QMSPTAIVKQJJGD-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-bromo-1,3-benzodioxol-5-yl)-5-(cyclohexylamino)-4h-imidazole-2-thione Chemical compound BrC1=CC=2OCOC=2C=C1C1N(C=2C=C3NC=NC3=CC=2)C(=S)NC1=NC1CCCCC1 QMSPTAIVKQJJGD-UHFFFAOYSA-N 0.000 claims 1
YAAFDPBKNHBPDO-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-bromo-1,3-benzodioxol-5-yl)-5-[(2-oxo-2-piperidin-1-ylethyl)amino]-4h-imidazol-2-one Chemical compound BrC1=CC=2OCOC=2C=C1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCC(=O)N1CCCCC1 YAAFDPBKNHBPDO-UHFFFAOYSA-N 0.000 claims 1
JWSFUPNQFAQFOT-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-fluoro-1h-indol-3-yl)-5-(2-pyridin-2-ylethylamino)-4h-imidazol-2-one Chemical compound C=1NC2=CC(F)=CC=C2C=1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCCC1=CC=CC=N1 JWSFUPNQFAQFOT-UHFFFAOYSA-N 0.000 claims 1
RLEUPVJVTRTXOJ-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-methyl-1h-indol-3-yl)-5-(3-phenylpropylamino)-4h-imidazol-2-one Chemical compound C=1NC2=CC(C)=CC=C2C=1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCCCC1=CC=CC=C1 RLEUPVJVTRTXOJ-UHFFFAOYSA-N 0.000 claims 1
PAUXINXKZRSWLV-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-(6-methyl-4-oxochromen-3-yl)-5-(3-phenylpropylamino)-4h-imidazol-2-one Chemical compound O=C1C2=CC(C)=CC=C2OC=C1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCCCC1=CC=CC=C1 PAUXINXKZRSWLV-UHFFFAOYSA-N 0.000 claims 1
LZAQOBVBXNKZNA-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-4-naphthalen-2-yl-5-(pyridin-3-ylmethylamino)-4h-imidazol-2-one Chemical compound C=1C=C2C=CC=CC2=CC=1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCC1=CC=CN=C1 LZAQOBVBXNKZNA-UHFFFAOYSA-N 0.000 claims 1
MYGLNZCYGMEPFB-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(1h-indol-5-ylmethylamino)-4-(4-methylphenyl)-4h-imidazole-2-thione Chemical compound C1=CC(C)=CC=C1C(N(C(=S)N1)C=2C=C3N=CNC3=CC=2)C1=NCC1=CC=C(NC=C2)C2=C1 MYGLNZCYGMEPFB-UHFFFAOYSA-N 0.000 claims 1
LUMNQYKHVOEBRY-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(2-bromoanilino)-4-(2,4-dimethylcyclohex-3-en-1-yl)-4h-imidazole-2-thione Chemical compound CC1C=C(C)CCC1C(N(C(=S)N1)C=2C=C3N=CNC3=CC=2)C1=NC1=CC=CC=C1Br LUMNQYKHVOEBRY-UHFFFAOYSA-N 0.000 claims 1
LVYCBVWSHOFYOO-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(2-methoxyethylamino)-4-(4-methylphenyl)-4h-imidazol-2-one Chemical compound COCCN=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=C(C)C=C1 LVYCBVWSHOFYOO-UHFFFAOYSA-N 0.000 claims 1
QKEBMMSATYMIFA-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(2-morpholin-4-ylethylamino)-4-naphthalen-2-yl-4h-imidazol-2-one Chemical compound C=1C=C2C=CC=CC2=CC=1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NCCN1CCOCC1 QKEBMMSATYMIFA-UHFFFAOYSA-N 0.000 claims 1
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QNAQHAJEKANCOV-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(4-fluoroanilino)-4-quinolin-4-yl-4h-imidazole-2-thione Chemical compound C1=CC(F)=CC=C1N=C1C(C=2C3=CC=CC=C3N=CC=2)N(C=2C=C3N=CNC3=CC=2)C(=S)N1 QNAQHAJEKANCOV-UHFFFAOYSA-N 0.000 claims 1
LXIXQHFZFJFZSJ-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-4h-imidazole-2-thione Chemical compound O1CCOC2=CC(C3C(=NCN4C5=CC=CC=C5N=N4)NC(N3C=3C=C4N=CNC4=CC=3)=S)=CC=C21 LXIXQHFZFJFZSJ-UHFFFAOYSA-N 0.000 claims 1
GPPQGFOWARWCLH-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(3,5-difluorophenyl)-4h-imidazol-2-one Chemical compound FC1=CC(F)=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=NCN2C3=CC=CC=C3N=N2)=C1 GPPQGFOWARWCLH-UHFFFAOYSA-N 0.000 claims 1
YYWCHZBGYSIJRD-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(3-methylphenyl)-4h-imidazol-2-one Chemical compound CC1=CC=CC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=NCN2C3=CC=CC=C3N=N2)=C1 YYWCHZBGYSIJRD-UHFFFAOYSA-N 0.000 claims 1
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XWTMQZINIMMKGI-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(4-methylsulfanylphenyl)-4h-imidazol-2-one Chemical compound C1=CC(SC)=CC=C1C(N(C(=O)N1)C=2C=C3N=CNC3=CC=2)C1=NCN1C2=CC=CC=C2N=N1 XWTMQZINIMMKGI-UHFFFAOYSA-N 0.000 claims 1
SXDQGMYYHLYDPF-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(6-bromo-1,3-benzodioxol-5-yl)-4h-imidazol-2-one Chemical compound C1=C2N=CNC2=CC(N2C(C(NC2=O)=NCN2C3=CC=CC=C3N=N2)C2=CC=3OCOC=3C=C2Br)=C1 SXDQGMYYHLYDPF-UHFFFAOYSA-N 0.000 claims 1
JJQSNZYJSDJFIN-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-(6-methylpyridin-2-yl)-4h-imidazole-2-thione Chemical compound CC1=CC=CC(C2C(NC(=S)N2C=2C=C3NC=NC3=CC=2)=NCN2C3=CC=CC=C3N=N2)=N1 JJQSNZYJSDJFIN-UHFFFAOYSA-N 0.000 claims 1
VODGDBVZJFCOIR-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-[4-(dimethylamino)phenyl]-4h-imidazol-2-one Chemical compound C1=CC(N(C)C)=CC=C1C(N(C(=O)N1)C=2C=C3N=CNC3=CC=2)C1=NCN1C2=CC=CC=C2N=N1 VODGDBVZJFCOIR-UHFFFAOYSA-N 0.000 claims 1
JTTXPJUFJJVUMF-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-[4-(dimethylamino)phenyl]-4h-imidazole-2-thione Chemical compound C1=CC(N(C)C)=CC=C1C(N(C(=S)N1)C=2C=C3N=CNC3=CC=2)C1=NCN1C2=CC=CC=C2N=N1 JTTXPJUFJJVUMF-UHFFFAOYSA-N 0.000 claims 1
PAMJAHXKFHNFEF-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-naphthalen-2-yl-4h-imidazole-2-thione Chemical compound C1=CC=CC2=CC(C3C(=NCN4C5=CC=CC=C5N=N4)NC(N3C=3C=C4N=CNC4=CC=3)=S)=CC=C21 PAMJAHXKFHNFEF-UHFFFAOYSA-N 0.000 claims 1
ZEOJXUROSSATEY-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4-quinolin-4-yl-4h-imidazole-2-thione Chemical compound C1=CC=C2C(C3C(=NCN4C5=CC=CC=C5N=N4)NC(N3C=3C=C4NC=NC4=CC=3)=S)=CC=NC2=C1 ZEOJXUROSSATEY-UHFFFAOYSA-N 0.000 claims 1
MRENILCPHDDBAK-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzotriazol-1-ylmethylamino)-4h-imidazol-2-one Chemical compound N1=NC2=CC=CC=C2N1CN=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1 MRENILCPHDDBAK-UHFFFAOYSA-N 0.000 claims 1
AMAOHHMKMGXZNU-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(benzylamino)-4-(4-chlorophenyl)-4h-imidazole-2-thione Chemical compound C1=CC(Cl)=CC=C1C(N(C(=S)N1)C=2C=C3N=CNC3=CC=2)C1=NCC1=CC=CC=C1 AMAOHHMKMGXZNU-UHFFFAOYSA-N 0.000 claims 1
ZLUJQEPYOXEWFP-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(cycloheptylamino)-4-(2,4,4-trimethylpentyl)-4h-imidazole-2-thione Chemical compound CC(C)(C)CC(C)CC1N(C=2C=C3NC=NC3=CC=2)C(=S)NC1=NC1CCCCCC1 ZLUJQEPYOXEWFP-UHFFFAOYSA-N 0.000 claims 1
WAFXZWPYVKCTQX-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(cycloheptylamino)-4-(2,4-dimethylphenyl)-4h-imidazol-2-one Chemical compound CC1=CC(C)=CC=C1C(N(C(=O)N1)C=2C=C3NC=NC3=CC=2)C1=NC1CCCCCC1 WAFXZWPYVKCTQX-UHFFFAOYSA-N 0.000 claims 1
MUFNLLRIKMXOLP-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(cycloheptylamino)-4-(2,4-dimethylphenyl)-4h-imidazole-2-thione Chemical compound CC1=CC(C)=CC=C1C(N(C(=S)N1)C=2C=C3NC=NC3=CC=2)C1=NC1CCCCCC1 MUFNLLRIKMXOLP-UHFFFAOYSA-N 0.000 claims 1
AWBMZOINVAPHRZ-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(cyclopentylamino)-4-(4-oxochromen-3-yl)-4h-imidazol-2-one Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NC1CCCC1 AWBMZOINVAPHRZ-UHFFFAOYSA-N 0.000 claims 1
YJAJEGWBQZIVMQ-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(cyclopentylamino)-4-(4-pyrrolidin-1-ylphenyl)-4h-imidazole-2-thione Chemical compound C=1C=C(N2CCCC2)C=CC=1C1N(C=2C=C3N=CNC3=CC=2)C(=S)NC1=NC1CCCC1 YJAJEGWBQZIVMQ-UHFFFAOYSA-N 0.000 claims 1
QNOIVZWYTWCASX-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-(methylamino)-4-(4-methylphenyl)-4h-imidazole-2-thione Chemical compound CN=C1NC(=S)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=C(C)C=C1 QNOIVZWYTWCASX-UHFFFAOYSA-N 0.000 claims 1
OCNMREFQTCMWON-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-[(2-hydroxycyclohexyl)amino]-4-(1h-indol-5-yl)-4h-imidazol-2-one Chemical compound OC1CCCCC1N=C1C(C=2C=C3C=CNC3=CC=2)N(C=2C=C3N=CNC3=CC=2)C(=O)N1 OCNMREFQTCMWON-UHFFFAOYSA-N 0.000 claims 1
UEZWVXZOMIIVKH-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-[(2-hydroxycyclohexyl)amino]-4-(4-oxochromen-3-yl)-4h-imidazol-2-one Chemical compound OC1CCCCC1N=C1C(C=2C(C3=CC=CC=C3OC=2)=O)N(C=2C=C3N=CNC3=CC=2)C(=O)N1 UEZWVXZOMIIVKH-UHFFFAOYSA-N 0.000 claims 1
GFFJTMNNXMHKCP-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-[(2-hydroxycyclohexyl)amino]-4-(5-methyl-1h-imidazol-4-yl)-4h-imidazol-2-one Chemical compound N1=CNC(C2C(NC(=O)N2C=2C=C3N=CNC3=CC=2)=NC2C(CCCC2)O)=C1C GFFJTMNNXMHKCP-UHFFFAOYSA-N 0.000 claims 1
RZHJKHODLHXNND-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-[(2-hydroxycyclohexyl)amino]-4-(6-methyl-4-oxochromen-3-yl)-4h-imidazol-2-one Chemical compound O=C1C2=CC(C)=CC=C2OC=C1C1N(C=2C=C3N=CNC3=CC=2)C(=O)NC1=NC1CCCCC1O RZHJKHODLHXNND-UHFFFAOYSA-N 0.000 claims 1
ANXYEINYVVJTBW-UHFFFAOYSA-N 3-(3h-benzimidazol-5-yl)-5-[3-(dimethylamino)propylamino]-4-(3-methylphenyl)-4h-imidazol-2-one Chemical compound CN(C)CCCN=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=CC(C)=C1 ANXYEINYVVJTBW-UHFFFAOYSA-N 0.000 claims 1
ZGCRCRQRJWRGRY-UHFFFAOYSA-N 3-[3-(3h-benzimidazol-5-yl)-2-oxo-5-(propan-2-ylamino)-4h-imidazol-4-yl]benzonitrile Chemical compound CC(C)N=C1NC(=O)N(C=2C=C3N=CNC3=CC=2)C1C1=CC=CC(C#N)=C1 ZGCRCRQRJWRGRY-UHFFFAOYSA-N 0.000 claims 1
XXLQGSMMBSUAGQ-UHFFFAOYSA-N 3-[3-(3h-benzimidazol-5-yl)-5-(3-phenylpropylamino)-2-sulfanylidene-4h-imidazol-4-yl]-6-methylchromen-4-one Chemical compound O=C1C2=CC(C)=CC=C2OC=C1C1N(C=2C=C3N=CNC3=CC=2)C(=S)NC1=NCCCC1=CC=CC=C1 XXLQGSMMBSUAGQ-UHFFFAOYSA-N 0.000 claims 1
NAEDKPUUEJPXTB-UHFFFAOYSA-N 3-[3-(3h-benzimidazol-5-yl)-5-(benzylamino)-2-sulfanylidene-4h-imidazol-4-yl]chromen-4-one Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1N(C=2C=C3N=CNC3=CC=2)C(=S)NC1=NCC1=CC=CC=C1 NAEDKPUUEJPXTB-UHFFFAOYSA-N 0.000 claims 1
CUUCNRZIWPNVQV-UHFFFAOYSA-N 3-[3-(3h-benzimidazol-5-yl)-5-[(2-hydroxycyclohexyl)amino]-2-sulfanylidene-4h-imidazol-4-yl]-6-methylchromen-4-one Chemical compound O=C1C2=CC(C)=CC=C2OC=C1C1N(C=2C=C3N=CNC3=CC=2)C(=S)NC1=NC1CCCCC1O CUUCNRZIWPNVQV-UHFFFAOYSA-N 0.000 claims 1
LHFWVYIZRKAMSD-UHFFFAOYSA-N 3-[[3-(3h-benzimidazol-5-yl)-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-2-sulfanylidene-4h-imidazol-5-yl]amino]benzonitrile Chemical compound C=1C=C2OCCOC2=CC=1C1N(C=2C=C3N=CNC3=CC=2)C(=S)NC1=NC1=CC=CC(C#N)=C1 LHFWVYIZRKAMSD-UHFFFAOYSA-N 0.000 claims 1
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