JP5501256B2

JP5501256B2 - 新規スピロクロマノンカルボン酸

新規スピロクロマノンカルボン酸 Download PDF

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Publication number: JP5501256B2
Authority: JP; Japan
Prior art keywords: group; ring; alkyl; methyl; chroman
Prior art date: 2008-07-04
Legal status : Expired - Fee Related

Application number

JP2010550957A

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English (en)

Japanese (ja)

Other versions

JP2011526584A5 (enExample

JP2011526584A (ja

Inventor

英毅常名

芳宏柴田

健山川

Original Assignee

Ｍｓｄ株式会社

Priority date

2008-07-04

Filing date

2009-06-29

Publication date

2014-05-21

2009-06-29 Application filed by Ｍｓｄ株式会社 filed Critical Ｍｓｄ株式会社

2009-06-29 Priority to JP2010550957A priority Critical patent/JP5501256B2/ja

2011-10-13 Publication of JP2011526584A publication Critical patent/JP2011526584A/ja

2012-08-16 Publication of JP2011526584A5 publication Critical patent/JP2011526584A5/ja

2014-05-21 Application granted granted Critical

2014-05-21 Publication of JP5501256B2 publication Critical patent/JP5501256B2/ja

Status Expired - Fee Related legal-status Critical Current

2029-06-29 Anticipated expiration legal-status Critical

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150000001732 carboxylic acid derivatives Chemical class 0.000 title claims description 8
-1 Group Chemical group 0.000 claims description 458
150000001875 compounds Chemical class 0.000 claims description 244
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 206
125000001424 substituent group Chemical group 0.000 claims description 125
125000005843 halogen group Chemical group 0.000 claims description 101
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 85
208000008589 Obesity Diseases 0.000 claims description 63
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 63
235000020824 obesity Nutrition 0.000 claims description 63
125000006828 (C2-C7) alkoxycarbonyl group Chemical group 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 58
150000002148 esters Chemical class 0.000 claims description 54
238000011282 treatment Methods 0.000 claims description 54
125000000623 heterocyclic group Chemical group 0.000 claims description 50
206010012601 diabetes mellitus Diseases 0.000 claims description 49
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 48
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 46
125000003118 aryl group Chemical group 0.000 claims description 44
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 40
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 39
125000005647 linker group Chemical group 0.000 claims description 38
239000003814 drug Substances 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
125000002252 acyl group Chemical group 0.000 claims description 34
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 32
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 31
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
125000003831 tetrazolyl group Chemical group 0.000 claims description 30
125000003545 alkoxy group Chemical group 0.000 claims description 29
125000001841 imino group Chemical group [H]N=* 0.000 claims description 27
125000004430 oxygen atom Chemical group O* 0.000 claims description 26
229910052717 sulfur Inorganic materials 0.000 claims description 26
125000004434 sulfur atom Chemical group 0.000 claims description 24
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 23
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
208000031226 Hyperlipidaemia Diseases 0.000 claims description 20
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
208000001145 Metabolic Syndrome Diseases 0.000 claims description 17
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 17
125000003226 pyrazolyl group Chemical group 0.000 claims description 17
125000004093 cyano group Chemical group *C#N 0.000 claims description 16
125000001041 indolyl group Chemical group 0.000 claims description 16
125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 15
BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims description 15
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 15
125000004043 oxo group Chemical group O=* 0.000 claims description 15
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 14
125000004414 alkyl thio group Chemical group 0.000 claims description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 12
208000004930 Fatty Liver Diseases 0.000 claims description 12
206010019708 Hepatic steatosis Diseases 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
125000005236 alkanoylamino group Chemical group 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 12
208000010706 fatty liver disease Diseases 0.000 claims description 12
231100000240 steatosis hepatitis Toxicity 0.000 claims description 12
125000000842 isoxazolyl group Chemical group 0.000 claims description 11
125000000464 thioxo group Chemical group S=* 0.000 claims description 11
208000032841 Bulimia Diseases 0.000 claims description 10
206010006550 Bulimia nervosa Diseases 0.000 claims description 10
208000035473 Communicable disease Diseases 0.000 claims description 10
125000004423 acyloxy group Chemical group 0.000 claims description 10
125000003386 piperidinyl group Chemical group 0.000 claims description 10
125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 9
125000002947 alkylene group Chemical group 0.000 claims description 9
125000004193 piperazinyl group Chemical group 0.000 claims description 9
125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 claims description 8
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 8
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 8
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 7
201000011510 cancer Diseases 0.000 claims description 7
125000002971 oxazolyl group Chemical group 0.000 claims description 7
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 6
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 6
125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 5
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
239000011593 sulfur Substances 0.000 claims description 5
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical group C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims description 4
FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical group C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 claims description 4
239000000654 additive Substances 0.000 claims description 4
150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
150000001345 alkine derivatives Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
YYWVRTPENAIUKN-UHFFFAOYSA-N 1-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]piperidine-4-carboxylic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(N3CCC(CC3)C(O)=O)C=2)CC2=O)C2=C1 YYWVRTPENAIUKN-UHFFFAOYSA-N 0.000 claims description 3
RPGUOTFDTHAZGZ-UHFFFAOYSA-N 2-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C(=CC=CC=3)C(O)=O)C=2)CC2=O)C2=C1 RPGUOTFDTHAZGZ-UHFFFAOYSA-N 0.000 claims description 3
QBNMFGKAJVVWLF-UHFFFAOYSA-N 3-[3-methyl-5-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)C=C2C(C)=NN1C1=CC=CC(C(O)=O)=C1 QBNMFGKAJVVWLF-UHFFFAOYSA-N 0.000 claims description 3
ZHUGFFNVTFZWFT-UHFFFAOYSA-N 3-[3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC=C2C(C)=NN1C1=CC=CC(C(O)=O)=C1 ZHUGFFNVTFZWFT-UHFFFAOYSA-N 0.000 claims description 3
GEVPVZRXWSVVMY-UHFFFAOYSA-N 4-[1-cyclopropyl-3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC(C=3C=CC(=CC=3)C(O)=O)=C2C(C)=CN1C1CC1 GEVPVZRXWSVVMY-UHFFFAOYSA-N 0.000 claims description 3
KUAQKYFWNGPOOJ-UHFFFAOYSA-N 4-[3-methyl-5-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC=C(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)C=C2C(C)=NN1C1=CC=C(C(O)=O)C=C1 KUAQKYFWNGPOOJ-UHFFFAOYSA-N 0.000 claims description 3
RFFNQUCMTARUDN-UHFFFAOYSA-N 4-[3-methyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indazol-1-yl]benzoic acid Chemical compound C12=CC(C(=O)N3CCC4(CC3)OC3=CC=C(C=C3C(=O)C4)C3=CN(C)N=C3)=CC=C2C(C)=NN1C1=CC=C(C(O)=O)C=C1 RFFNQUCMTARUDN-UHFFFAOYSA-N 0.000 claims description 3
BWOWFRSWPGTPRJ-UHFFFAOYSA-N 4-[4-[6-(5-carbamoylpyridin-3-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(N)=O)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 BWOWFRSWPGTPRJ-UHFFFAOYSA-N 0.000 claims description 3
VTVVHLRLIQMBJM-UHFFFAOYSA-N 4-[8-cyclopropyl-2-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]quinolin-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2N=C3C(C4CC4)=CC=CC3=C(C=3C=CC(=CC=3)C(O)=O)C=2)CC2=O)C2=C1 VTVVHLRLIQMBJM-UHFFFAOYSA-N 0.000 claims description 3
FCTRNZBHYXMXRM-UHFFFAOYSA-N 5-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CN=CC(C(O)=O)=C1 FCTRNZBHYXMXRM-UHFFFAOYSA-N 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical group N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 claims description 2
DINMYSLVSVQBBA-UHFFFAOYSA-N 2-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]oxyacetic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(OCC(O)=O)C=2)CC2=O)C2=C1 DINMYSLVSVQBBA-UHFFFAOYSA-N 0.000 claims description 2
RIYBBKHBXOJHCO-UHFFFAOYSA-N 3-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C=C(C=CC=3)C(O)=O)C=2)CC2=O)C2=C1 RIYBBKHBXOJHCO-UHFFFAOYSA-N 0.000 claims description 2
AYEBUJMKYQXOSE-UHFFFAOYSA-N 3-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 AYEBUJMKYQXOSE-UHFFFAOYSA-N 0.000 claims description 2
QAVDIZMXLQQANA-UHFFFAOYSA-N 3-[4-[6-(5-carbamoylpyridin-2-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2N=CC(=CC=2)C(N)=O)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 QAVDIZMXLQQANA-UHFFFAOYSA-N 0.000 claims description 2
XKDIWNWAQOIGJT-UHFFFAOYSA-N 3-[4-[6-(5-carbamoylpyridin-3-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=NC=2)C(N)=O)=CC(OCC)=C1C1=CC=CC(C(O)=O)=C1 XKDIWNWAQOIGJT-UHFFFAOYSA-N 0.000 claims description 2
ATPHQKDTAWCVJB-UHFFFAOYSA-N 4-[1-cyclopropyl-6-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]indol-4-yl]benzoic acid Chemical compound C1=NN(C)C=C1C1=CC=C(OC2(CCN(CC2)C(=O)C=2C=C3N(C4CC4)C=CC3=C(C=3C=CC(=CC=3)C(O)=O)C=2)CC2=O)C2=C1 ATPHQKDTAWCVJB-UHFFFAOYSA-N 0.000 claims description 2
BXSZEGCHOFMLTE-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[4-oxo-6-(1h-pyrazol-5-yl)spiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2NN=CC=2)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 BXSZEGCHOFMLTE-UHFFFAOYSA-N 0.000 claims description 2
YYLXNNDOTVAVPQ-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]-2-fluorobenzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=C(C(O)=O)C(F)=C1 YYLXNNDOTVAVPQ-UHFFFAOYSA-N 0.000 claims description 2
UFEOVVIQNNPRKL-UHFFFAOYSA-N 4-[2,6-diethoxy-4-[6-(1-methylpyrazol-4-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]phenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C2=CN(C)N=C2)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 UFEOVVIQNNPRKL-UHFFFAOYSA-N 0.000 claims description 2
KOFXRJJZZLORNM-UHFFFAOYSA-N 4-[4-[6-(5-carbamoylpyridin-2-yl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]benzoic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2N=CC(=CC=2)C(N)=O)=CC(OCC)=C1C1=CC=C(C(O)=O)C=C1 KOFXRJJZZLORNM-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000001183 hydrocarbyl group Chemical group 0.000 claims 2
WZBZVGAYGYZBQT-UHFFFAOYSA-N 5-[4-[6-(3-carbamoylphenyl)-4-oxospiro[3h-chromene-2,4'-piperidine]-1'-carbonyl]-2,6-diethoxyphenyl]pyridine-3-carboxylic acid Chemical compound CCOC1=CC(C(=O)N2CCC3(CC2)OC2=CC=C(C=C2C(=O)C3)C=2C=C(C=CC=2)C(N)=O)=CC(OCC)=C1C1=CN=CC(C(O)=O)=C1 WZBZVGAYGYZBQT-UHFFFAOYSA-N 0.000 claims 1
ZVTRWPJJQREMAS-UHFFFAOYSA-N C(N)(=O)C=1C=CC(=NC1)C=1C=C2C(CC3(CCN(CC3)C(=O)C3=CC(=C(C(=C3)OCC)C3=CC=CC=C3)OCC)OC2=CC1)=O.[Na] Chemical group C(N)(=O)C=1C=CC(=NC1)C=1C=C2C(CC3(CCN(CC3)C(=O)C3=CC(=C(C(=C3)OCC)C3=CC=CC=C3)OCC)OC2=CC1)=O.[Na] ZVTRWPJJQREMAS-UHFFFAOYSA-N 0.000 claims 1
PFHMRFPCXMUWEJ-UHFFFAOYSA-N CC1=C(C=CC=C1)C1=C(C=C(C=C1OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2=NC=C(C=C2)C(N)=O)OCC Chemical group CC1=C(C=CC=C1)C1=C(C=C(C=C1OCC)C(=O)N1CCC2(CC1)OC1=CC=C(C=C1C(C2)=O)C2=NC=C(C=C2)C(N)=O)OCC PFHMRFPCXMUWEJ-UHFFFAOYSA-N 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
125000002009 alkene group Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 description 151
239000000203 mixture Substances 0.000 description 89
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
239000003112 inhibitor Substances 0.000 description 56
239000007787 solid Substances 0.000 description 56
238000000034 method Methods 0.000 description 54
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 47
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 45
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 41
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