BRPI0809509A2

BRPI0809509A2 - Composto, composição farmacêutica, métodos para inibir a adesão intracelular mediada pela selectina, e para tratar ou prevenir uma doença ou distúrbio em um mamífero, e, uso de um composto.

Composto, composição farmacêutica, métodos para inibir a adesão intracelular mediada pela selectina, e para tratar ou prevenir uma doença ou distúrbio em um mamífero, e, uso de um composto. Download PDF

Info

Publication number: BRPI0809509A2
Authority: BR; Brazil
Prior art keywords: carboxylic acid; group; hydroxy; compound; quinoline
Prior art date: 2007-03-30

Application number

BRPI0809509-4A

Other languages

English (en)

Portuguese (pt)

Inventor

Kristin Marie Janz

Adrian Huang

Alessandro Fabio Moretto

Patricia Ward Bedard

Neelu Kaila

Original Assignee

Wyeth Corp

Priority date

2007-03-30

Filing date

2008-03-28

Publication date

2014-09-16

2008-03-28 Application filed by Wyeth Corp filed Critical Wyeth Corp

2014-09-16 Publication of BRPI0809509A2 publication Critical patent/BRPI0809509A2/pt

Links

150000001875 compounds Chemical class 0.000 title claims description 297
238000000034 method Methods 0.000 title claims description 265
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 54
201000010099 disease Diseases 0.000 title claims description 30
102000003800 Selectins Human genes 0.000 title claims description 25
108090000184 Selectins Proteins 0.000 title claims description 25
230000001404 mediated effect Effects 0.000 title claims description 19
AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 title claims description 17
239000008194 pharmaceutical composition Substances 0.000 title claims description 10
230000003834 intracellular effect Effects 0.000 title claims description 8
-1 1- (4-chlorophenyl) cyclopropyl Chemical group 0.000 claims description 220
VQMSRUREDGBWKT-UHFFFAOYSA-N quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=NC2=C1 VQMSRUREDGBWKT-UHFFFAOYSA-N 0.000 claims description 102
125000000753 cycloalkyl group Chemical group 0.000 claims description 84
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 84
125000000217 alkyl group Chemical group 0.000 claims description 69
125000003118 aryl group Chemical group 0.000 claims description 69
150000003839 salts Chemical class 0.000 claims description 64
239000002253 acid Substances 0.000 claims description 62
150000002148 esters Chemical class 0.000 claims description 59
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 42
125000000304 alkynyl group Chemical group 0.000 claims description 40
125000001072 heteroaryl group Chemical group 0.000 claims description 40
125000006708 (C5-C14) heteroaryl group Chemical group 0.000 claims description 35
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 32
150000001721 carbon Chemical group 0.000 claims description 22
208000035475 disorder Diseases 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 21
241000124008 Mammalia Species 0.000 claims description 19
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000005915 C6-C14 aryl group Chemical group 0.000 claims description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
208000011580 syndromic disease Diseases 0.000 claims description 18
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 11
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125000001188 haloalkyl group Chemical group 0.000 claims description 10
125000003342 alkenyl group Chemical group 0.000 claims description 8
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
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125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 4
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208000036971 interstitial lung disease 2 Diseases 0.000 claims description 4
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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230000001988 toxicity Effects 0.000 claims description 4
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VZFQHPLEOOFYOH-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 VZFQHPLEOOFYOH-UHFFFAOYSA-N 0.000 claims description 3
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OFXKYYRRMSAALR-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-methyl-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C(F)(F)F)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 OFXKYYRRMSAALR-UHFFFAOYSA-N 0.000 claims description 2
DPVQYMWEZYNTPN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-propan-2-ylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C(C)C)=CC=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 DPVQYMWEZYNTPN-UHFFFAOYSA-N 0.000 claims description 2
FUHSQIQHVOBKIJ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 FUHSQIQHVOBKIJ-UHFFFAOYSA-N 0.000 claims description 2
RACDNEQBIMTJPQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 RACDNEQBIMTJPQ-UHFFFAOYSA-N 0.000 claims description 2
IXWBEGRJSCDREE-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-fluoro-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 IXWBEGRJSCDREE-UHFFFAOYSA-N 0.000 claims description 2
MFNPLSQDVZJJAG-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-6-methoxyquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(OC)=CC=C2N=C1C1(C=2C=CC(F)=CC=2)CC1 MFNPLSQDVZJJAG-UHFFFAOYSA-N 0.000 claims description 2
YVRANBPIBKYHJI-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-phenylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(F)=CC=3)=NC2=C1C1=CC=CC=C1 YVRANBPIBKYHJI-UHFFFAOYSA-N 0.000 claims description 2
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KTPGQSXLTNRPNH-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 KTPGQSXLTNRPNH-UHFFFAOYSA-N 0.000 claims description 2
MPGXRRXKAUTZJI-UHFFFAOYSA-N 3-hydroxy-2-(2-methyl-1-phenylpropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C(C)C)C1=CC=CC=C1 MPGXRRXKAUTZJI-UHFFFAOYSA-N 0.000 claims description 2
RDOYLDVSTACHBF-UHFFFAOYSA-N 3-hydroxy-2-(2-phenylpropan-2-yl)-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C(C)(C)C1=CC=CC=C1 RDOYLDVSTACHBF-UHFFFAOYSA-N 0.000 claims description 2
CNLBINRGSCCRJQ-UHFFFAOYSA-N 3-hydroxy-6-phenyl-2-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC=CC=3)=NC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 CNLBINRGSCCRJQ-UHFFFAOYSA-N 0.000 claims description 2
VGKABSFOSBEDFO-UHFFFAOYSA-N 3-hydroxy-7,8-dimethyl-2-(2-phenylpropan-2-yl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=CC=C1 VGKABSFOSBEDFO-UHFFFAOYSA-N 0.000 claims description 2
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125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
GBMKBFZHOBTDHH-UHFFFAOYSA-N 6-chloro-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 GBMKBFZHOBTDHH-UHFFFAOYSA-N 0.000 claims description 2
DPASIEUQVVRKBJ-UHFFFAOYSA-N 7-bromo-2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC(Br)=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 DPASIEUQVVRKBJ-UHFFFAOYSA-N 0.000 claims description 2
JFZVQHMNQGBFAG-UHFFFAOYSA-N 7-chloro-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC(Cl)=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 JFZVQHMNQGBFAG-UHFFFAOYSA-N 0.000 claims description 2
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BMYTWYXDPHHYRU-UHFFFAOYSA-N 8-cyclopropyl-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC=CC=3)=NC2=C1C1CC1 BMYTWYXDPHHYRU-UHFFFAOYSA-N 0.000 claims description 2
NOSNVLUHKFZQME-UHFFFAOYSA-N 8-tert-butyl-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 NOSNVLUHKFZQME-UHFFFAOYSA-N 0.000 claims description 2
239000003814 drug Substances 0.000 claims description 2
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PPHSJAKBSFBRHC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3,6-dihydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(O)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 PPHSJAKBSFBRHC-UHFFFAOYSA-N 0.000 claims 2
UJSGGWGSBUIARQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6,8-dimethylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 UJSGGWGSBUIARQ-UHFFFAOYSA-N 0.000 claims 2
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JGSWEULRSNETKL-UHFFFAOYSA-N 2-[1-(2-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C(=CC=CC=2)Cl)CC1 JGSWEULRSNETKL-UHFFFAOYSA-N 0.000 claims 1
RZKOUEJUNBPRAT-UHFFFAOYSA-N 2-[1-(3-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=C(Cl)C=CC=2)CC1 RZKOUEJUNBPRAT-UHFFFAOYSA-N 0.000 claims 1
GCNAFZVEBJYFGK-UHFFFAOYSA-N 2-[1-(4-bromophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Br)=CC=2)CC1 GCNAFZVEBJYFGK-UHFFFAOYSA-N 0.000 claims 1
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ZDMKJBNVEQUZJB-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 ZDMKJBNVEQUZJB-UHFFFAOYSA-N 0.000 claims 1
IRGQKCRMKVVJIZ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-methylquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 IRGQKCRMKVVJIZ-UHFFFAOYSA-N 0.000 claims 1
LVACEZHKXJVGAN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-6-phenyl-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C(C(F)(F)F)C=C1C1=CC=CC=C1 LVACEZHKXJVGAN-UHFFFAOYSA-N 0.000 claims 1
PFIBJPOPGOFTTQ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 PFIBJPOPGOFTTQ-UHFFFAOYSA-N 0.000 claims 1
CVBBIOBLWGAMGU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-7-methylquinoline-4-carboxylic acid Chemical compound N=1C2=CC(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 CVBBIOBLWGAMGU-UHFFFAOYSA-N 0.000 claims 1
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IFQLLHTYMVUKBN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-phenyl-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C1=CC=CC=C1 IFQLLHTYMVUKBN-UHFFFAOYSA-N 0.000 claims 1
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XAFZGDJJCFQQPF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-thiophen-3-ylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C=1C=CSC=1 XAFZGDJJCFQQPF-UHFFFAOYSA-N 0.000 claims 1
IWVVLMAAJRPMKY-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-6-ethyl-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(CC)=CC(C(F)(F)F)=C2N=C1C1(C=2C=CC(Cl)=CC=2)CC1 IWVVLMAAJRPMKY-UHFFFAOYSA-N 0.000 claims 1
URDILIYTWGPYKJ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-6-fluoro-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 URDILIYTWGPYKJ-UHFFFAOYSA-N 0.000 claims 1
RYHAEGXAXZNHAF-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-7-ethyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC(CC)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 RYHAEGXAXZNHAF-UHFFFAOYSA-N 0.000 claims 1
QODXCZMKVRXXDD-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(C(O)(C(F)(F)F)C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 QODXCZMKVRXXDD-UHFFFAOYSA-N 0.000 claims 1
XWNWOISRVSYKKL-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-cyclopropyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(Cl)=CC=3)=NC2=C1C1CC1 XWNWOISRVSYKKL-UHFFFAOYSA-N 0.000 claims 1
ULTHLRANTPUCEP-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-8-ethyl-3-hydroxyquinoline-4-carboxylic acid Chemical compound N1=C2C(CC)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(Cl)=CC=2)CC1 ULTHLRANTPUCEP-UHFFFAOYSA-N 0.000 claims 1
BKICHBVPINNNHC-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)ethyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(O)=O)=C(O)C=1C(C)C1=CC=C(Cl)C=C1 BKICHBVPINNNHC-UHFFFAOYSA-N 0.000 claims 1
CQVVFEIRAFOBNR-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 CQVVFEIRAFOBNR-UHFFFAOYSA-N 0.000 claims 1
VEWHRKWTVOQXGW-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-methylquinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(F)=CC=2)CC1 VEWHRKWTVOQXGW-UHFFFAOYSA-N 0.000 claims 1
AUBXSTRGUCAKQJ-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxy-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(F)=CC=2)CC1 AUBXSTRGUCAKQJ-UHFFFAOYSA-N 0.000 claims 1
KAMSXBGBEJDMLV-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)cyclopropyl]-8-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(C(O)(C(F)(F)F)C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 KAMSXBGBEJDMLV-UHFFFAOYSA-N 0.000 claims 1
IDYNSQYYAXZSOJ-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=C(Cl)C=C1 IDYNSQYYAXZSOJ-UHFFFAOYSA-N 0.000 claims 1
XFZAQDNDHUIIJG-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-7,8-dimethylquinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=C(Cl)C=C1 XFZAQDNDHUIIJG-UHFFFAOYSA-N 0.000 claims 1
KAUONQSAQQAYOC-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=C(Cl)C=C1 KAUONQSAQQAYOC-UHFFFAOYSA-N 0.000 claims 1
PAOZFKVRYUJFGX-UHFFFAOYSA-N 2-[2-(4-chlorophenyl)propan-2-yl]-3-hydroxy-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C(C)(C)C1=CC=C(Cl)C=C1 PAOZFKVRYUJFGX-UHFFFAOYSA-N 0.000 claims 1
UIDHNPTVQFNWOJ-UHFFFAOYSA-N 2-methylquinoline-4-carboxylic acid Chemical compound C1=CC=CC2=NC(C)=CC(C(O)=O)=C21 UIDHNPTVQFNWOJ-UHFFFAOYSA-N 0.000 claims 1
RHFOZYDMSOPOTF-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-6-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 RHFOZYDMSOPOTF-UHFFFAOYSA-N 0.000 claims 1
IOOAVNABRMYUPR-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 IOOAVNABRMYUPR-UHFFFAOYSA-N 0.000 claims 1
GYVVMTCGGLXNBU-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC=CC=2)CC1 GYVVMTCGGLXNBU-UHFFFAOYSA-N 0.000 claims 1
OXXNELGTWXKFPS-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylcyclopropyl)-8-thiophen-3-ylquinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC=CC=3)=NC2=C1C=1C=CSC=1 OXXNELGTWXKFPS-UHFFFAOYSA-N 0.000 claims 1
OWVOXVUWUMLQMP-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylethyl)-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 OWVOXVUWUMLQMP-UHFFFAOYSA-N 0.000 claims 1
XHHONXOGMOGSEV-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylethyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C)C1=CC=CC=C1 XHHONXOGMOGSEV-UHFFFAOYSA-N 0.000 claims 1
XMBMVBQURZBLNA-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylpropan-2-yl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C)CC1=CC=CC=C1 XMBMVBQURZBLNA-UHFFFAOYSA-N 0.000 claims 1
WAQWHVVAEADNNQ-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylpropan-2-yl)-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C(C)CC1=CC=CC=C1 WAQWHVVAEADNNQ-UHFFFAOYSA-N 0.000 claims 1
FXNCIPDGYFHEIX-UHFFFAOYSA-N 3-hydroxy-2-(1-phenylpropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(CC)C1=CC=CC=C1 FXNCIPDGYFHEIX-UHFFFAOYSA-N 0.000 claims 1
IECOEXWJRKITTI-UHFFFAOYSA-N 3-hydroxy-2-(1-thiophen-2-ylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2SC=CC=2)CC1 IECOEXWJRKITTI-UHFFFAOYSA-N 0.000 claims 1
KQMMUJXTLDVGQI-UHFFFAOYSA-N 3-hydroxy-2-(1-thiophen-3-ylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C2=CSC=C2)CC1 KQMMUJXTLDVGQI-UHFFFAOYSA-N 0.000 claims 1
GNLSNPOOWYTXOS-UHFFFAOYSA-N 3-hydroxy-2-(2-methyl-1-phenylpropyl)-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N=1C2=C(C(C)C)C=CC=C2C(C(O)=O)=C(O)C=1C(C(C)C)C1=CC=CC=C1 GNLSNPOOWYTXOS-UHFFFAOYSA-N 0.000 claims 1
FAIUMLORHPQXLI-UHFFFAOYSA-N 3-hydroxy-2-(2-phenylpropan-2-yl)-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical group N=1C2=C3CCCCC3=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=CC=C1 FAIUMLORHPQXLI-UHFFFAOYSA-N 0.000 claims 1
WRGMUHMNOMIGEO-UHFFFAOYSA-N 3-hydroxy-2-(2-phenylpropan-2-yl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1C(C)(C)C1=CC=CC=C1 WRGMUHMNOMIGEO-UHFFFAOYSA-N 0.000 claims 1
SSHNMLMCVGDTMX-UHFFFAOYSA-N 3-hydroxy-2-(2-phenylpropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(O)=O)=C(O)C=1CC(C)C1=CC=CC=C1 SSHNMLMCVGDTMX-UHFFFAOYSA-N 0.000 claims 1
VPTBFAYGJQGYKT-UHFFFAOYSA-N 3-hydroxy-2-(2-phenylpropyl)-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1CC(C)C1=CC=CC=C1 VPTBFAYGJQGYKT-UHFFFAOYSA-N 0.000 claims 1
LCVIFSMRTRHAJQ-UHFFFAOYSA-N 3-hydroxy-2-[1-(4-methoxyphenyl)cyclopropyl]-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1(C=2C(=C(C(O)=O)C3=CC=CC(=C3N=2)C(F)(F)F)O)CC1 LCVIFSMRTRHAJQ-UHFFFAOYSA-N 0.000 claims 1
SHWKDMILSVNFPL-UHFFFAOYSA-N 3-hydroxy-2-[1-(4-methylphenyl)cyclopropyl]-8-propan-2-ylquinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(C)=CC=2)CC1 SHWKDMILSVNFPL-UHFFFAOYSA-N 0.000 claims 1
RMINXZUDJBOGEW-UHFFFAOYSA-N 3-hydroxy-2-[1-[4-(trifluoromethoxy)phenyl]cyclopropyl]-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(OC(F)(F)F)=CC=2)CC1 RMINXZUDJBOGEW-UHFFFAOYSA-N 0.000 claims 1
NTZBRWNPHGIZPW-UHFFFAOYSA-N 3-hydroxy-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid Chemical compound N=1C2=C3CCCCC3=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(=CC=2)C(F)(F)F)CC1 NTZBRWNPHGIZPW-UHFFFAOYSA-N 0.000 claims 1
XMKCHVVGHGMMSX-UHFFFAOYSA-N 3-hydroxy-6,8-dimethyl-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC(C)=C2N=C1C1(C=2C=CC=CC=2)CC1 XMKCHVVGHGMMSX-UHFFFAOYSA-N 0.000 claims 1
YXVNWMVNSHIGTN-UHFFFAOYSA-N 3-hydroxy-6-(trifluoromethoxy)-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(OC(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(=CC=2)C(F)(F)F)CC1 YXVNWMVNSHIGTN-UHFFFAOYSA-N 0.000 claims 1
GQFPMLZVRWFOBB-UHFFFAOYSA-N 3-hydroxy-6-methyl-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(C)=CC=C2N=C1C1(C=2C=CC=CC=2)CC1 GQFPMLZVRWFOBB-UHFFFAOYSA-N 0.000 claims 1
JKCUIWQHHAXRQN-UHFFFAOYSA-N 3-hydroxy-7,8-dimethyl-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 JKCUIWQHHAXRQN-UHFFFAOYSA-N 0.000 claims 1
OSBMWCYVEUGOJP-UHFFFAOYSA-N 3-hydroxy-7,8-dimethyl-2-(1-phenylpropan-2-yl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(C)CC1=CC=CC=C1 OSBMWCYVEUGOJP-UHFFFAOYSA-N 0.000 claims 1
HXRFVWCNNTWJHA-UHFFFAOYSA-N 3-hydroxy-7,8-dimethyl-2-(1-phenylpropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(CC)C1=CC=CC=C1 HXRFVWCNNTWJHA-UHFFFAOYSA-N 0.000 claims 1
GMSPHVIDWCNYRJ-UHFFFAOYSA-N 3-hydroxy-7,8-dimethyl-2-(2-methyl-1-phenylpropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C)C(C)=CC=C2C(C(O)=O)=C(O)C=1C(C(C)C)C1=CC=CC=C1 GMSPHVIDWCNYRJ-UHFFFAOYSA-N 0.000 claims 1
VXTGHMRCLPFDRG-UHFFFAOYSA-N 3-hydroxy-8-(trifluoromethyl)-2-[1-[2-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C(=CC=CC=2)C(F)(F)F)CC1 VXTGHMRCLPFDRG-UHFFFAOYSA-N 0.000 claims 1
RSAORFITHZBNFF-UHFFFAOYSA-N 3-hydroxy-8-(trifluoromethyl)-2-[1-[3-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=C(C=CC=2)C(F)(F)F)CC1 RSAORFITHZBNFF-UHFFFAOYSA-N 0.000 claims 1
SNTFIFNSACXSIX-UHFFFAOYSA-N 3-hydroxy-8-(trifluoromethyl)-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(=CC=2)C(F)(F)F)CC1 SNTFIFNSACXSIX-UHFFFAOYSA-N 0.000 claims 1
VYPALNRECWAXBO-UHFFFAOYSA-N 3-hydroxy-8-methyl-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound N1=C2C(C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC=CC=2)CC1 VYPALNRECWAXBO-UHFFFAOYSA-N 0.000 claims 1
BVCJVEJXDCOMTM-UHFFFAOYSA-N 3-hydroxy-8-phenyl-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC=CC=3)=NC2=C1C1=CC=CC=C1 BVCJVEJXDCOMTM-UHFFFAOYSA-N 0.000 claims 1
MNMZJXDVZGIWBW-UHFFFAOYSA-N 3-hydroxy-8-phenyl-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=C(O)C(C3(CC3)C=3C=CC(=CC=3)C(F)(F)F)=NC2=C1C1=CC=CC=C1 MNMZJXDVZGIWBW-UHFFFAOYSA-N 0.000 claims 1
GJVUBPPEIGKMII-UHFFFAOYSA-N 3-hydroxy-8-propan-2-yl-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N1=C2C(C(C)C)=CC=CC2=C(C(O)=O)C(O)=C1C1(C=2C=CC(=CC=2)C(F)(F)F)CC1 GJVUBPPEIGKMII-UHFFFAOYSA-N 0.000 claims 1
BKGZWFPRXSWJNO-UHFFFAOYSA-N 6-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(C(O)(C(F)(F)F)C(F)(F)F)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 BKGZWFPRXSWJNO-UHFFFAOYSA-N 0.000 claims 1
HSAWPUIDOQVIKW-UHFFFAOYSA-N 6-bromo-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound N=1C2=C(C(F)(F)F)C=C(Br)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 HSAWPUIDOQVIKW-UHFFFAOYSA-N 0.000 claims 1
JLPKYTBNIQXGEI-UHFFFAOYSA-N 6-bromo-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(Br)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 JLPKYTBNIQXGEI-UHFFFAOYSA-N 0.000 claims 1
DFYULGCQUNMAIR-UHFFFAOYSA-N 6-bromo-2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(Br)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 DFYULGCQUNMAIR-UHFFFAOYSA-N 0.000 claims 1
JIYRLQXZMAPYPK-UHFFFAOYSA-N 6-chloro-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 JIYRLQXZMAPYPK-UHFFFAOYSA-N 0.000 claims 1
XEPTYCBHPBGDCT-UHFFFAOYSA-N 6-chloro-2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 XEPTYCBHPBGDCT-UHFFFAOYSA-N 0.000 claims 1
OEIICKOCQUGAGD-UHFFFAOYSA-N 6-chloro-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC=C(Cl)C=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 OEIICKOCQUGAGD-UHFFFAOYSA-N 0.000 claims 1
YVWKXAZYJJSRGH-UHFFFAOYSA-N 6-ethyl-2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(CC)=CC=C2N=C1C1(C=2C=CC(F)=CC=2)CC1 YVWKXAZYJJSRGH-UHFFFAOYSA-N 0.000 claims 1
OKGIRFQYPOUVPO-UHFFFAOYSA-N 6-ethyl-3-hydroxy-2-(1-phenylcyclopropyl)-8-(trifluoromethyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(CC)=CC(C(F)(F)F)=C2N=C1C1(C=2C=CC=CC=2)CC1 OKGIRFQYPOUVPO-UHFFFAOYSA-N 0.000 claims 1
FEKDCPIKJRWZSZ-UHFFFAOYSA-N 6-ethyl-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound OC1=C(C(O)=O)C2=CC(CC)=CC=C2N=C1C1(C=2C=CC=CC=2)CC1 FEKDCPIKJRWZSZ-UHFFFAOYSA-N 0.000 claims 1
SZKJVSFIWRDFOZ-UHFFFAOYSA-N 7-chloro-3-hydroxy-2-(1-phenylcyclopropyl)quinoline-4-carboxylic acid Chemical compound N=1C2=CC(Cl)=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC=CC=2)CC1 SZKJVSFIWRDFOZ-UHFFFAOYSA-N 0.000 claims 1
RIMNMRAJJGZDQE-UHFFFAOYSA-N 7-ethyl-2-[1-(4-fluorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=CC(CC)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(F)=CC=2)CC1 RIMNMRAJJGZDQE-UHFFFAOYSA-N 0.000 claims 1
LXRHXFGPAJSZER-UHFFFAOYSA-N 7-ethyl-3-hydroxy-2-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]quinoline-4-carboxylic acid Chemical compound N=1C2=CC(CC)=CC=C2C(C(O)=O)=C(O)C=1C1(C=2C=CC(=CC=2)C(F)(F)F)CC1 LXRHXFGPAJSZER-UHFFFAOYSA-N 0.000 claims 1
MOYDXBYWUNSHJY-UHFFFAOYSA-N 8-bromo-2-[1-(4-chlorophenyl)cyclopropyl]-3-hydroxyquinoline-4-carboxylic acid Chemical compound N=1C2=C(Br)C=CC=C2C(C(=O)O)=C(O)C=1C1(C=2C=CC(Cl)=CC=2)CC1 MOYDXBYWUNSHJY-UHFFFAOYSA-N 0.000 claims 1
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