HUE026662T2 - C-28 amides of modified C-3 betulinic acid derivatives as anti-HIV agents - Google Patents

Info

Publication number

HUE026662T2

HUE026662T2 HUE11726564A HUE11726564A HUE026662T2 HU E026662 T2 HUE026662 T2 HU E026662T2 HU E11726564 A HUE11726564 A HU E11726564A HU E11726564 A HUE11726564 A HU E11726564A HU E026662 T2 HUE026662 T2 HU E026662T2

Authority

HU

Hungary

Prior art keywords

cyclopenta

pentamethyl

prop

chrysen

octadecahydro

Prior art date

2010-06-04

Links

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• 239000003112 inhibitor Substances 0.000 title description 33
• 150000001408 amides Chemical class 0.000 title description 17
• QGJZLNKBHJESQX-FZFNOLFKSA-N betulinic acid Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C QGJZLNKBHJESQX-FZFNOLFKSA-N 0.000 title description 17
• 230000035800 maturation Effects 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 274
• 208000030507 AIDS Diseases 0.000 claims description 88
• 125000000217 alkyl group Chemical group 0.000 claims description 60
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 238000011282 treatment Methods 0.000 claims description 22
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 19
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 11
• 208000015181 infectious disease Diseases 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 4
• 210000004556 brain Anatomy 0.000 claims 2
• 229910052742 iron Inorganic materials 0.000 claims 2
• 239000004575 stone Substances 0.000 claims 2
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
• 108700028369 Alleles Proteins 0.000 claims 1
• 241001449342 Chlorocrambe hastata Species 0.000 claims 1
• 241000237858 Gastropoda Species 0.000 claims 1
• HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
• MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
• 238000004299 exfoliation Methods 0.000 claims 1
• 239000013461 intermediate chemical Substances 0.000 claims 1
• 239000004816 latex Substances 0.000 claims 1
• 229920000126 latex Polymers 0.000 claims 1
• 238000011144 upstream manufacturing Methods 0.000 claims 1
• 238000000034 method Methods 0.000 description 333
• 238000002360 preparation method Methods 0.000 description 223
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 189
• 239000000047 product Substances 0.000 description 172
• 238000005160 1H NMR spectroscopy Methods 0.000 description 167
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 167
• 239000007787 solid Substances 0.000 description 164
• 150000001412 amines Chemical class 0.000 description 119
• 239000000376 reactant Substances 0.000 description 107
• 230000007062 hydrolysis Effects 0.000 description 103
• 238000006460 hydrolysis reaction Methods 0.000 description 103
• 239000000543 intermediate Substances 0.000 description 103
• 238000010640 amide synthesis reaction Methods 0.000 description 102
• -1 substituted Chemical class 0.000 description 92
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 86
• 239000000203 mixture Substances 0.000 description 84
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 72
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
• 239000011541 reaction mixture Substances 0.000 description 67
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
• 208000031886 HIV Infections Diseases 0.000 description 62
• 208000037357 HIV infectious disease Diseases 0.000 description 61
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 61
• 230000002829 reductive effect Effects 0.000 description 54
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 51
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 47
• 239000000243 solution Substances 0.000 description 46
• 241000725303 Human immunodeficiency virus Species 0.000 description 41
• 239000005711 Benzoic acid Substances 0.000 description 40
• 235000010233 benzoic acid Nutrition 0.000 description 40
• 229960004365 benzoic acid Drugs 0.000 description 40
• 229940050390 benzoate Drugs 0.000 description 39
• 125000001072 heteroaryl group Chemical group 0.000 description 39
• QTBSBXVTEAMEQO-GUEYOVJQSA-N acetic acid-d4 Chemical compound [2H]OC(=O)C([2H])([2H])[2H] QTBSBXVTEAMEQO-GUEYOVJQSA-N 0.000 description 37
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 36
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 35
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 31
• 230000015572 biosynthetic process Effects 0.000 description 29
• 239000007858 starting material Substances 0.000 description 29
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 29
• 235000019439 ethyl acetate Nutrition 0.000 description 25
• 229960002555 zidovudine Drugs 0.000 description 23
• 239000002904 solvent Substances 0.000 description 22
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 21
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 239000000284 extract Substances 0.000 description 19
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 238000006069 Suzuki reaction reaction Methods 0.000 description 18
• 239000003814 drug Substances 0.000 description 18
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
• 229910052938 sodium sulfate Inorganic materials 0.000 description 18
• 235000011152 sodium sulphate Nutrition 0.000 description 18
• 238000002953 preparative HPLC Methods 0.000 description 17
• 239000012153 distilled water Substances 0.000 description 16
• 229910052796 boron Inorganic materials 0.000 description 15
• 229940079593 drug Drugs 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 150000003839 salts Chemical class 0.000 description 15
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 14
• WREGKURFCTUGRC-POYBYMJQSA-N Zalcitabine Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](CO)CC1 WREGKURFCTUGRC-POYBYMJQSA-N 0.000 description 14
• ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 14
• 238000006243 chemical reaction Methods 0.000 description 14
• 239000003153 chemical reaction reagent Substances 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
• 210000004027 cell Anatomy 0.000 description 13
• 239000012044 organic layer Substances 0.000 description 13
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 13
• 239000008194 pharmaceutical composition Substances 0.000 description 13
• 239000000741 silica gel Substances 0.000 description 13
• 229910002027 silica gel Inorganic materials 0.000 description 13
• XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 12
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 125000003118 aryl group Chemical group 0.000 description 12
• 238000010511 deprotection reaction Methods 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 11
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 11
• 241000700605 Viruses Species 0.000 description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
• 238000003818 flash chromatography Methods 0.000 description 11
• 125000001475 halogen functional group Chemical group 0.000 description 11
• 239000000546 pharmaceutical excipient Substances 0.000 description 11
• 208000007766 Kaposi sarcoma Diseases 0.000 description 10
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
• 230000000840 anti-viral effect Effects 0.000 description 10
• 125000004432 carbon atom Chemical group C* 0.000 description 10
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
• 239000003085 diluting agent Substances 0.000 description 10
• XPOQHMRABVBWPR-ZDUSSCGKSA-N efavirenz Chemical compound C([C@]1(C2=CC(Cl)=CC=C2NC(=O)O1)C(F)(F)F)#CC1CC1 XPOQHMRABVBWPR-ZDUSSCGKSA-N 0.000 description 10
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 10
• VCMJCVGFSROFHV-WZGZYPNHSA-N tenofovir disoproxil fumarate Chemical class OC(=O)\C=C\C(O)=O.N1=CN=C2N(C[C@@H](C)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C)C=NC2=C1N VCMJCVGFSROFHV-WZGZYPNHSA-N 0.000 description 10
• 238000004809 thin layer chromatography Methods 0.000 description 10
• QGJZLNKBHJESQX-UHFFFAOYSA-N 3-Epi-Betulin-Saeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(=C)C)C5C4CCC3C21C QGJZLNKBHJESQX-UHFFFAOYSA-N 0.000 description 9
• KAALSBMCRVYZDM-JENLPSNGSA-N 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[2-[bis(carboxymethyl)amino]ethylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid Chemical compound C([C@]1(C)[C@H]2CC[C@H]3[C@@]([C@@]2(CC[C@H]1C1(C)C)C)(C)CC[C@]2(CC[C@H]([C@H]32)C(=C)C)C(=O)NCCN(CC(O)=O)CC(O)=O)C=C1C1=CC=C(C(O)=O)C=C1 KAALSBMCRVYZDM-JENLPSNGSA-N 0.000 description 9
• 125000003545 alkoxy group Chemical group 0.000 description 9
• 230000000694 effects Effects 0.000 description 9
• 239000006260 foam Substances 0.000 description 9
• 229910000027 potassium carbonate Inorganic materials 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
• CLOUCVRNYSHRCF-UHFFFAOYSA-N 3beta-Hydroxy-20(29)-Lupen-3,27-oic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C CLOUCVRNYSHRCF-UHFFFAOYSA-N 0.000 description 8
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 8
• USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 8
• 239000005695 Ammonium acetate Substances 0.000 description 8
• DIZWSDNSTNAYHK-XGWVBXMLSA-N Betulinic acid Natural products CC(=C)[C@@H]1C[C@H]([C@H]2CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]12)C(=O)O DIZWSDNSTNAYHK-XGWVBXMLSA-N 0.000 description 8
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
• 239000002253 acid Substances 0.000 description 8
• 235000019257 ammonium acetate Nutrition 0.000 description 8
• 229940043376 ammonium acetate Drugs 0.000 description 8
• 239000003443 antiviral agent Substances 0.000 description 8
• 150000001732 carboxylic acid derivatives Chemical group 0.000 description 8
• 239000002274 desiccant Substances 0.000 description 8
• 238000011161 development Methods 0.000 description 8
• PZXJOHSZQAEJFE-UHFFFAOYSA-N dihydrobetulinic acid Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C(C)C)C5C4CCC3C21C PZXJOHSZQAEJFE-UHFFFAOYSA-N 0.000 description 8
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
• MQYXUWHLBZFQQO-UHFFFAOYSA-N nepehinol Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C)CCC(C(=C)C)C5C4CCC3C21C MQYXUWHLBZFQQO-UHFFFAOYSA-N 0.000 description 8
• FSRMWCVZAUEPEQ-UHFFFAOYSA-N 3-(1,1-dioxo-1,4-thiazinan-4-yl)propan-1-amine Chemical compound NCCCN1CCS(=O)(=O)CC1 FSRMWCVZAUEPEQ-UHFFFAOYSA-N 0.000 description 7
• GSOLBTUGHFVALR-IVTMKUIASA-N 4-[(1r,3as,5ar,5br,7ar,11as,11br,13ar,13br)-3a-[2-[2-carboxyethyl(ethyl)amino]ethylcarbamoyl]-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid Chemical compound C([C@]1(C)[C@H]2CC[C@@H]3[C@H]4[C@@H](CC[C@@]4(CC[C@@]3(C)[C@]2(C)CC[C@H]1C1(C)C)C(=O)NCCN(CC)CCC(O)=O)C(C)=C)C=C1C1=CC=C(C(O)=O)C=C1 GSOLBTUGHFVALR-IVTMKUIASA-N 0.000 description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
• 150000001733 carboxylic acid esters Chemical class 0.000 description 7
• 125000004093 cyano group Chemical group *C#N 0.000 description 7
• 239000003937 drug carrier Substances 0.000 description 7
• 239000002835 hiv fusion inhibitor Substances 0.000 description 7
• 239000002955 immunomodulating agent Substances 0.000 description 7
• 229940121354 immunomodulator Drugs 0.000 description 7
• 229960001936 indinavir Drugs 0.000 description 7
• CBVCZFGXHXORBI-PXQQMZJSSA-N indinavir Chemical compound C([C@H](N(CC1)C[C@@H](O)C[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H]2C3=CC=CC=C3C[C@H]2O)C(=O)NC(C)(C)C)N1CC1=CC=CN=C1 CBVCZFGXHXORBI-PXQQMZJSSA-N 0.000 description 7
• DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 7
• 229910052757 nitrogen Inorganic materials 0.000 description 7
• 239000002777 nucleoside Substances 0.000 description 7
• 238000000746 purification Methods 0.000 description 7
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 7
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 7
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• 108010019625 Atazanavir Sulfate Proteins 0.000 description 6
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
• 108010010369 HIV Protease Proteins 0.000 description 6
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• XNKLLVCARDGLGL-JGVFFNPUSA-N Stavudine Chemical compound O=C1NC(=O)C(C)=CN1[C@H]1C=C[C@@H](CO)O1 XNKLLVCARDGLGL-JGVFFNPUSA-N 0.000 description 6
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• 125000004104 aryloxy group Chemical group 0.000 description 6
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• FVWJYYTZTCVBKE-ROUWMTJPSA-N betulin Chemical class C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(CO)CC[C@@H](C(=C)C)[C@@H]5[C@H]4CC[C@@H]3[C@]21C FVWJYYTZTCVBKE-ROUWMTJPSA-N 0.000 description 6
• 239000012043 crude product Substances 0.000 description 6
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• 125000005553 heteroaryloxy group Chemical group 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• 150000003833 nucleoside derivatives Chemical class 0.000 description 6
• 239000003921 oil Substances 0.000 description 6
• 230000003647 oxidation Effects 0.000 description 6
• 238000007254 oxidation reaction Methods 0.000 description 6
• 229910052763 palladium Inorganic materials 0.000 description 6
• NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
• XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
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