CA2730493A1 - Modulators of acetyl-coenzyme a carboxylase and methods of use thereof - Google Patents

Info

Publication number

CA2730493A1

CA2730493A1 CA2730493A CA2730493A CA2730493A1 CA 2730493 A1 CA2730493 A1 CA 2730493A1 CA 2730493 A CA2730493 A CA 2730493A CA 2730493 A CA2730493 A CA 2730493A CA 2730493 A1 CA2730493 A1 CA 2730493A1

Authority

CA

Canada

Prior art keywords

compound

carbonyl

piperidin

benzoxazin

spiro

Prior art date

2008-07-14

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

• 238000000034 method Methods 0.000 title claims abstract description 136
• 108010016219 Acetyl-CoA carboxylase Proteins 0.000 title description 40
• 102000000452 Acetyl-CoA carboxylase Human genes 0.000 title description 40
• 150000001875 compounds Chemical class 0.000 claims abstract description 413
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 30
• 201000011510 cancer Diseases 0.000 claims abstract description 28
• 238000011282 treatment Methods 0.000 claims abstract description 28
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 24
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 18
• 230000002829 reductive effect Effects 0.000 claims abstract description 15
• 230000004060 metabolic process Effects 0.000 claims abstract description 13
• 208000008589 Obesity Diseases 0.000 claims abstract description 12
• 235000020824 obesity Nutrition 0.000 claims abstract description 12
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 11
• 230000001537 neural effect Effects 0.000 claims abstract description 11
• 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 9
• 208000001145 Metabolic Syndrome Diseases 0.000 claims abstract description 9
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 9
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 473
• -1 cyano, amino Chemical group 0.000 claims description 300
• 125000003003 spiro group Chemical group 0.000 claims description 223
• XJHSSTMIDVOYQO-UHFFFAOYSA-N spiro[3h-1,3-benzoxazine-2,4'-piperidine]-4-one Chemical compound O1C2=CC=CC=C2C(=O)NC21CCNCC2 XJHSSTMIDVOYQO-UHFFFAOYSA-N 0.000 claims description 142
• 125000001072 heteroaryl group Chemical group 0.000 claims description 102
• 125000003118 aryl group Chemical group 0.000 claims description 100
• 125000000217 alkyl group Chemical group 0.000 claims description 88
• 239000000203 mixture Substances 0.000 claims description 79
• 229910052736 halogen Inorganic materials 0.000 claims description 61
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 125000002252 acyl group Chemical group 0.000 claims description 59
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 59
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 57
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 57
• 125000004414 alkyl thio group Chemical group 0.000 claims description 54
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 53
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 52
• 125000001188 haloalkyl group Chemical group 0.000 claims description 49
• 125000003282 alkyl amino group Chemical group 0.000 claims description 38
• 125000003302 alkenyloxy group Chemical group 0.000 claims description 36
• 125000005133 alkynyloxy group Chemical group 0.000 claims description 36
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 35
• 150000003839 salts Chemical class 0.000 claims description 35
• 150000002367 halogens Chemical group 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 30
• 125000004432 carbon atom Chemical group C* 0.000 claims description 27
• 239000001257 hydrogen Substances 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 208000026310 Breast neoplasm Diseases 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 239000000651 prodrug Substances 0.000 claims description 13
• 229940002612 prodrug Drugs 0.000 claims description 13
• 206010006187 Breast cancer Diseases 0.000 claims description 12
• 206010061217 Infestation Diseases 0.000 claims description 12
• 125000004442 acylamino group Chemical group 0.000 claims description 12
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 12
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 12
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
• 206010017533 Fungal infection Diseases 0.000 claims description 11
• 208000031888 Mycoses Diseases 0.000 claims description 11
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 11
• 208000024827 Alzheimer disease Diseases 0.000 claims description 10
• 206010033128 Ovarian cancer Diseases 0.000 claims description 10
• 206010061535 Ovarian neoplasm Diseases 0.000 claims description 10
• 206010060862 Prostate cancer Diseases 0.000 claims description 10
• 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 10
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 10
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 10
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 10
• 239000003795 chemical substances by application Substances 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 10
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
• 206010009944 Colon cancer Diseases 0.000 claims description 9
• 208000029742 colonic neoplasm Diseases 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 claims description 8
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 206010014733 Endometrial cancer Diseases 0.000 claims description 8
• 206010014759 Endometrial neoplasm Diseases 0.000 claims description 8
• 208000002495 Uterine Neoplasms Diseases 0.000 claims description 8
• 229910052757 nitrogen Inorganic materials 0.000 claims description 8
• 206010046766 uterine cancer Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
• 206010060378 Hyperinsulinaemia Diseases 0.000 claims description 7
• 208000010877 cognitive disease Diseases 0.000 claims description 7
• 244000000004 fungal plant pathogen Species 0.000 claims description 7
• 201000008980 hyperinsulinism Diseases 0.000 claims description 7
• 201000007270 liver cancer Diseases 0.000 claims description 7
• 208000014018 liver neoplasm Diseases 0.000 claims description 7
• 208000027061 mild cognitive impairment Diseases 0.000 claims description 7
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 7
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 125000005291 haloalkenyloxy group Chemical group 0.000 claims description 6
• 125000000232 haloalkynyl group Chemical group 0.000 claims description 6
• 125000005292 haloalkynyloxy group Chemical group 0.000 claims description 6
• 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 5
• LIMFPAAAIVQRRD-BCGVJQADSA-N N-[2-[(3S,4R)-3-fluoro-4-methoxypiperidin-1-yl]pyrimidin-4-yl]-8-[(2R,3S)-2-methyl-3-(methylsulfonylmethyl)azetidin-1-yl]-5-propan-2-ylisoquinolin-3-amine Chemical compound F[C@H]1CN(CC[C@H]1OC)C1=NC=CC(=N1)NC=1N=CC2=C(C=CC(=C2C=1)C(C)C)N1[C@@H]([C@H](C1)CS(=O)(=O)C)C LIMFPAAAIVQRRD-BCGVJQADSA-N 0.000 claims description 5
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
• 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 5
• 239000003472 antidiabetic agent Substances 0.000 claims description 5
• 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 5
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 5
• 239000003085 diluting agent Substances 0.000 claims description 5
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
• 125000004434 sulfur atom Chemical group 0.000 claims description 5
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
• 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 3
• KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims description 3
• 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 3
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
• 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 3
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 3
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
• 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
• HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical group C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 claims description 3
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
• 208000002249 Diabetes Complications Diseases 0.000 claims description 3
• 206010012655 Diabetic complications Diseases 0.000 claims description 3
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 3
• 206010019280 Heart failures Diseases 0.000 claims description 3
• 208000035150 Hypercholesterolemia Diseases 0.000 claims description 3
• 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
• 206010020772 Hypertension Diseases 0.000 claims description 3
• 206010021024 Hypolipidaemia Diseases 0.000 claims description 3
• 206010033307 Overweight Diseases 0.000 claims description 3
• 206010036049 Polycystic ovaries Diseases 0.000 claims description 3
• 208000006011 Stroke Diseases 0.000 claims description 3
• 230000000879 anti-atherosclerotic effect Effects 0.000 claims description 3
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
• 208000029078 coronary artery disease Diseases 0.000 claims description 3
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
• 230000003451 hyperinsulinaemic effect Effects 0.000 claims description 3
• 208000006575 hypertriglyceridemia Diseases 0.000 claims description 3
• 208000029498 hypoalphalipoproteinemia Diseases 0.000 claims description 3
• 125000002883 imidazolyl group Chemical group 0.000 claims description 3
• 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 201000010065 polycystic ovary syndrome Diseases 0.000 claims description 3
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
• 239000000883 anti-obesity agent Substances 0.000 claims description 2
• 229940125708 antidiabetic agent Drugs 0.000 claims description 2
• 229940125710 antiobesity agent Drugs 0.000 claims description 2
• 239000002327 cardiovascular agent Substances 0.000 claims description 2
• 229940125692 cardiovascular agent Drugs 0.000 claims description 2
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims 5
• 230000003920 cognitive function Effects 0.000 claims 2
• 241000196324 Embryophyta Species 0.000 abstract description 33
• 241001465754 Metazoa Species 0.000 abstract description 29
• 241000233866 Fungi Species 0.000 abstract description 11
• 241000607479 Yersinia pestis Species 0.000 abstract description 9
• 239000003814 drug Substances 0.000 abstract description 8
• 208000024172 Cardiovascular disease Diseases 0.000 abstract description 7
• 241000238631 Hexapoda Species 0.000 abstract description 5
• 244000052769 pathogen Species 0.000 abstract description 3
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
• 239000011734 sodium Substances 0.000 description 91
• 238000005481 NMR spectroscopy Methods 0.000 description 86
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 82
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
• 239000000243 solution Substances 0.000 description 39
• 108010018763 Biotin carboxylase Proteins 0.000 description 38
• 210000004027 cell Anatomy 0.000 description 34
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 31
• 239000002904 solvent Substances 0.000 description 31
• 125000005843 halogen group Chemical group 0.000 description 29
• 238000012360 testing method Methods 0.000 description 28
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 24
• 239000011541 reaction mixture Substances 0.000 description 23
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
• 230000000694 effects Effects 0.000 description 22
• 230000005764 inhibitory process Effects 0.000 description 22
• 239000000463 material Substances 0.000 description 21
• 239000012267 brine Substances 0.000 description 20
• 238000006243 chemical reaction Methods 0.000 description 20
• 235000014113 dietary fatty acids Nutrition 0.000 description 20
• 239000000194 fatty acid Substances 0.000 description 20
• 229930195729 fatty acid Natural products 0.000 description 20
• 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 20
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 20
• 239000007832 Na2SO4 Substances 0.000 description 19
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 19
• 238000009472 formulation Methods 0.000 description 19
• 229910052938 sodium sulfate Inorganic materials 0.000 description 19
• 235000011152 sodium sulphate Nutrition 0.000 description 19
• 150000004665 fatty acids Chemical class 0.000 description 18
• 210000002966 serum Anatomy 0.000 description 18
• 241000282414 Homo sapiens Species 0.000 description 17
• LTYOQGRJFJAKNA-KKIMTKSISA-N Malonyl CoA Natural products S(C(=O)CC(=O)O)CCNC(=O)CCNC(=O)[C@@H](O)C(CO[P@](=O)(O[P@](=O)(OC[C@H]1[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](n2c3ncnc(N)c3nc2)O1)O)O)(C)C LTYOQGRJFJAKNA-KKIMTKSISA-N 0.000 description 17
• LTYOQGRJFJAKNA-DVVLENMVSA-N malonyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC(O)=O)O[C@H]1N1C2=NC=NC(N)=C2N=C1 LTYOQGRJFJAKNA-DVVLENMVSA-N 0.000 description 17
• 239000003981 vehicle Substances 0.000 description 17
• ZSLZBFCDCINBPY-ZSJPKINUSA-N acetyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 ZSLZBFCDCINBPY-ZSJPKINUSA-N 0.000 description 16
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 16
• 238000012746 preparative thin layer chromatography Methods 0.000 description 16
• 239000007787 solid Substances 0.000 description 16
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
• 239000012043 crude product Substances 0.000 description 15
• 239000007788 liquid Substances 0.000 description 14
• 241000700159 Rattus Species 0.000 description 13
• 238000001727 in vivo Methods 0.000 description 13
• 210000001519 tissue Anatomy 0.000 description 13
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
• 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 description 12
• 239000000411 inducer Substances 0.000 description 12
• 239000007821 HATU Substances 0.000 description 11
• 239000004480 active ingredient Substances 0.000 description 11
• ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 11
• VRJHQPZVIGNGMX-UHFFFAOYSA-N 4-piperidinone Chemical compound O=C1CCNCC1 VRJHQPZVIGNGMX-UHFFFAOYSA-N 0.000 description 10
• 102000004877 Insulin Human genes 0.000 description 10
• 108090001061 Insulin Proteins 0.000 description 10
• 239000002253 acid Substances 0.000 description 10
• 230000037396 body weight Effects 0.000 description 10
• 229940125396 insulin Drugs 0.000 description 10
• 230000003647 oxidation Effects 0.000 description 10
• 238000007254 oxidation reaction Methods 0.000 description 10
• 238000010561 standard procedure Methods 0.000 description 10
• 241000124008 Mammalia Species 0.000 description 9
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
• 210000000577 adipose tissue Anatomy 0.000 description 9
• 150000002431 hydrogen Chemical group 0.000 description 9
• WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 8
• YPFZNQWLNDDXEJ-UHFFFAOYSA-N 4,8-dimethoxyquinoline-2-carboxylic acid Chemical compound C1=C(C(O)=O)N=C2C(OC)=CC=CC2=C1OC YPFZNQWLNDDXEJ-UHFFFAOYSA-N 0.000 description 8
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