CA2602772A1 - Composes heterocycliques d'acide boronique - Google Patents

Info

Publication number

CA2602772A1

CA2602772A1 CA002602772A CA2602772A CA2602772A1 CA 2602772 A1 CA2602772 A1 CA 2602772A1 CA 002602772 A CA002602772 A CA 002602772A CA 2602772 A CA2602772 A CA 2602772A CA 2602772 A1 CA2602772 A1 CA 2602772A1

Authority

CA

Canada

Prior art keywords

alkyl

independently

phenyl

optionally mono

cycloalkyl

Prior art date

2003-11-12

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• -1 Heterocyclic boronic acid compounds Chemical class 0.000 title claims description 275
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 326
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 162
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 157
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 104
• 150000002367 halogens Chemical class 0.000 claims abstract description 104
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 17
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 10
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 8
• 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 8
• IPZJQDSFZGZEOY-UHFFFAOYSA-N dimethylmethylene Chemical compound C[C]C IPZJQDSFZGZEOY-UHFFFAOYSA-N 0.000 claims abstract description 5
• 125000000217 alkyl group Chemical group 0.000 claims description 393
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 283
• 229910052739 hydrogen Inorganic materials 0.000 claims description 216
• 239000001257 hydrogen Substances 0.000 claims description 214
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 206
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 184
• 125000003118 aryl group Chemical group 0.000 claims description 154
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 144
• 125000003545 alkoxy group Chemical group 0.000 claims description 143
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 136
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 125
• 125000003342 alkenyl group Chemical group 0.000 claims description 123
• 125000000304 alkynyl group Chemical group 0.000 claims description 121
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 109
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 104
• 229920006395 saturated elastomer Polymers 0.000 claims description 76
• 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 66
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 63
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 55
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 55
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 54
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 52
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 52
• OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 claims description 52
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 50
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 46
• 125000001624 naphthyl group Chemical group 0.000 claims description 46
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 46
• 125000004076 pyridyl group Chemical group 0.000 claims description 46
• 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 45
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 43
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 40
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 40
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 40
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 40
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 39
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 37
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 37
• 125000004122 cyclic group Chemical group 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 31
• 125000003282 alkyl amino group Chemical group 0.000 claims description 24
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 24
• 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 23
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 22
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 22
• 125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 22
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 22
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 20
• 125000004429 atom Chemical group 0.000 claims description 19
• 125000002252 acyl group Chemical group 0.000 claims description 18
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 17
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 16
• 125000005089 alkenylaminocarbonyl group Chemical group 0.000 claims description 15
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 15
• 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 15
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 15
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 15
• 125000004414 alkyl thio group Chemical group 0.000 claims description 15
• 125000005095 alkynylaminocarbonyl group Chemical group 0.000 claims description 15
• 125000001091 aminosulfinyl group Chemical group [H]N([H])S(*)=O 0.000 claims description 15
• 125000001769 aryl amino group Chemical group 0.000 claims description 15
• 150000001602 bicycloalkyls Chemical group 0.000 claims description 15
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
• 125000005350 hydroxycycloalkyl group Chemical group 0.000 claims description 15
• 125000005592 polycycloalkyl group Polymers 0.000 claims description 15
• 125000006684 polyhaloalkyl group Polymers 0.000 claims description 15
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 14
• 125000005241 heteroarylamino group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 11
• 125000003277 amino group Chemical group 0.000 claims description 11
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 10
• 125000004423 acyloxy group Chemical group 0.000 claims description 10
• 125000002947 alkylene group Chemical group 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• WWODQSMOSOXYQQ-UHFFFAOYSA-N 1-pentylbicyclo[2.2.2]octan-4-amine Chemical compound C1CC2(N)CCC1(CCCCC)CC2 WWODQSMOSOXYQQ-UHFFFAOYSA-N 0.000 claims description 9
• 239000007864 aqueous solution Substances 0.000 claims description 9
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 9
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 9
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 8
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 7
• 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 7
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
• 125000005620 boronic acid group Chemical group 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 6
• 239000013060 biological fluid Substances 0.000 claims description 6
• 150000004677 hydrates Chemical class 0.000 claims description 6
• 239000012453 solvate Substances 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 3
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 2
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
• 125000003396 thiol group Chemical class [H]S* 0.000 claims 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims 1
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims 1
• 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
• 150000001875 compounds Chemical class 0.000 abstract description 264
• 238000000034 method Methods 0.000 abstract description 62
• 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 abstract description 59
• 239000003472 antidiabetic agent Substances 0.000 abstract description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 32
• 229940125708 antidiabetic agent Drugs 0.000 abstract description 28
• 201000010099 disease Diseases 0.000 abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 abstract description 21
• 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract description 20
• 206010012601 diabetes mellitus Diseases 0.000 abstract description 15
• 230000002401 inhibitory effect Effects 0.000 abstract description 7
• 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 abstract 2
• 239000003112 inhibitor Substances 0.000 description 78
• 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 description 57
• 238000011282 treatment Methods 0.000 description 52
• 239000003795 chemical substances by application Substances 0.000 description 48
• 239000000460 chlorine Substances 0.000 description 31
• 239000003814 drug Substances 0.000 description 30
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 30
• 239000000203 mixture Substances 0.000 description 26
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
• 239000000556 agonist Substances 0.000 description 20
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
• 230000000694 effects Effects 0.000 description 19
• 208000008589 Obesity Diseases 0.000 description 18
• 125000006254 cycloalkyl carbonyl group Chemical group 0.000 description 18
• 238000004519 manufacturing process Methods 0.000 description 18
• 235000020824 obesity Nutrition 0.000 description 18
• 125000000714 pyrimidinyl group Chemical group 0.000 description 18
• 102000004877 Insulin Human genes 0.000 description 15
• 108090001061 Insulin Proteins 0.000 description 15
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 15
• 125000005842 heteroatom Chemical group 0.000 description 15
• 229940125396 insulin Drugs 0.000 description 15
• 201000001320 Atherosclerosis Diseases 0.000 description 14
• 239000003524 antilipemic agent Substances 0.000 description 14
• 230000001276 controlling effect Effects 0.000 description 14
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 13
• 230000005764 inhibitory process Effects 0.000 description 13
• 238000002360 preparation method Methods 0.000 description 13
• 230000002265 prevention Effects 0.000 description 13
• 150000003573 thiols Chemical class 0.000 description 13
• 239000002253 acid Substances 0.000 description 12
• 239000003085 diluting agent Substances 0.000 description 12
• OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 12
• 239000000018 receptor agonist Substances 0.000 description 12
• 229940044601 receptor agonist Drugs 0.000 description 12
• 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 11
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• 239000000883 anti-obesity agent Substances 0.000 description 11
• 229940125710 antiobesity agent Drugs 0.000 description 11
• 239000002775 capsule Substances 0.000 description 11
• HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 11
• 239000003937 drug carrier Substances 0.000 description 11
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• 208000035475 disorder Diseases 0.000 description 10
• 208000011580 syndromic disease Diseases 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• 102100031939 Erythropoietin Human genes 0.000 description 9
• 102100031545 Microsomal triglyceride transfer protein large subunit Human genes 0.000 description 9
• 229940100389 Sulfonylurea Drugs 0.000 description 9
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 9
• 125000003367 polycyclic group Chemical group 0.000 description 9
• 102000004190 Enzymes Human genes 0.000 description 8
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• 102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 8
• 229940122355 Insulin sensitizer Drugs 0.000 description 8
• WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 8
• 235000014113 dietary fatty acids Nutrition 0.000 description 8
• VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 229930195729 fatty acid Natural products 0.000 description 8
• 239000000194 fatty acid Substances 0.000 description 8
• 201000001421 hyperglycemia Diseases 0.000 description 8
• IVDFJHOHABJVEH-UHFFFAOYSA-N pinacol Chemical compound CC(C)(O)C(C)(C)O IVDFJHOHABJVEH-UHFFFAOYSA-N 0.000 description 8
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 8
• 229940123208 Biguanide Drugs 0.000 description 7
• DTHNMHAUYICORS-KTKZVXAJSA-N Glucagon-like peptide 1 Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCNC(N)=N)C(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@H](CC=1C=CC=CC=1)NC(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@@H](N)CC=1N=CNC=1)[C@@H](C)O)[C@@H](C)O)C(C)C)C1=CC=CC=C1 DTHNMHAUYICORS-KTKZVXAJSA-N 0.000 description 7
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• 108010007622 LDL Lipoproteins Proteins 0.000 description 6
• PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
• TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 6
• YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 6
• RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 6
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• 125000002619 bicyclic group Chemical group 0.000 description 6
• OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 6
• YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 6
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