CA2819400A1 - Bicyclic compound - Google Patents
Bicyclic compound Download PDFInfo
- Publication number
- CA2819400A1 CA2819400A1 CA2819400A CA2819400A CA2819400A1 CA 2819400 A1 CA2819400 A1 CA 2819400A1 CA 2819400 A CA2819400 A CA 2819400A CA 2819400 A CA2819400 A CA 2819400A CA 2819400 A1 CA2819400 A1 CA 2819400A1
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- optionally substituted
- ring
- reaction
- Prior art date
- 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
- -1 Bicyclic compound Chemical class 0.000 title description 247
- 150000001875 compounds Chemical class 0.000 claims abstract description 610
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 31
- 238000011282 treatment Methods 0.000 claims abstract description 25
- 238000011321 prophylaxis Methods 0.000 claims abstract description 22
- 208000008589 Obesity Diseases 0.000 claims abstract description 20
- 235000020824 obesity Nutrition 0.000 claims abstract description 20
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 11
- 125000005843 halogen group Chemical group 0.000 claims description 260
- 125000001424 substituent group Chemical group 0.000 claims description 233
- 125000000217 alkyl group Chemical group 0.000 claims description 130
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 109
- 125000003118 aryl group Chemical group 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 85
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 72
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 60
- 125000003277 amino group Chemical group 0.000 claims description 55
- 238000004519 manufacturing process Methods 0.000 claims description 54
- 239000003795 chemical substances by application Substances 0.000 claims description 52
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 51
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 40
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 36
- 125000002619 bicyclic group Chemical group 0.000 claims description 35
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 30
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 28
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 25
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 24
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 21
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 18
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 18
- 108010018763 Biotin carboxylase Proteins 0.000 claims description 18
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 18
- 230000004927 fusion Effects 0.000 claims description 18
- 241000124008 Mammalia Species 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229940121373 acetyl-coa carboxylase inhibitor Drugs 0.000 claims description 2
- ADHDEZRLSWZHKE-LBPRGKRZSA-N n-[(2s)-1-[6-(6-ethoxy-1,3-benzoxazol-2-yl)pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound O1C2=CC(OCC)=CC=C2N=C1C1=CC=C(OC[C@H](C)NC(C)=O)C=N1 ADHDEZRLSWZHKE-LBPRGKRZSA-N 0.000 claims 1
- CBRJFLKXQUUGQV-LBPRGKRZSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]-5-fluoropyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound FC1=CC(OC[C@H](C)NC(C)=O)=CN=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 CBRJFLKXQUUGQV-LBPRGKRZSA-N 0.000 claims 1
- ZAAOFSTVMJFFPI-ZDUSSCGKSA-N n-[(2s)-1-[6-[6-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl]oxypropan-2-yl]acetamide Chemical compound N1=CC(OC[C@H](C)NC(C)=O)=CC=C1C(OC1=C2)=NC1=CC=C2OCC1CC1 ZAAOFSTVMJFFPI-ZDUSSCGKSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 230
- 239000002904 solvent Substances 0.000 description 211
- 229910052731 fluorine Inorganic materials 0.000 description 113
- 125000001153 fluoro group Chemical group F* 0.000 description 112
- 239000012442 inert solvent Substances 0.000 description 112
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 96
- 229910052751 metal Inorganic materials 0.000 description 93
- 239000002184 metal Substances 0.000 description 93
- 239000002585 base Substances 0.000 description 89
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 71
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 60
- 230000035484 reaction time Effects 0.000 description 58
- 125000000753 cycloalkyl group Chemical group 0.000 description 56
- 150000001408 amides Chemical class 0.000 description 52
- 239000004210 ether based solvent Substances 0.000 description 52
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 48
- 239000000203 mixture Substances 0.000 description 48
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 47
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 45
- 150000008282 halocarbons Chemical class 0.000 description 45
- 150000002430 hydrocarbons Chemical group 0.000 description 45
- 239000003849 aromatic solvent Substances 0.000 description 44
- 239000004215 Carbon black (E152) Substances 0.000 description 41
- 229930195733 hydrocarbon Natural products 0.000 description 41
- 125000003545 alkoxy group Chemical group 0.000 description 40
- 125000000623 heterocyclic group Chemical group 0.000 description 35
- 239000003054 catalyst Substances 0.000 description 34
- 238000002360 preparation method Methods 0.000 description 34
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 33
- 229910052801 chlorine Inorganic materials 0.000 description 33
- 125000001309 chloro group Chemical group Cl* 0.000 description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 32
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
- 229940079593 drug Drugs 0.000 description 25
- 150000002825 nitriles Chemical class 0.000 description 25
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000003112 inhibitor Substances 0.000 description 24
- 125000005915 C6-C14 aryl group Chemical group 0.000 description 23
- 238000010511 deprotection reaction Methods 0.000 description 23
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 22
- 239000005456 alcohol based solvent Substances 0.000 description 22
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 22
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 22
- 125000000842 isoxazolyl group Chemical group 0.000 description 22
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 21
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 125000003226 pyrazolyl group Chemical group 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- 239000008103 glucose Substances 0.000 description 19
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 18
- 238000005804 alkylation reaction Methods 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- 125000006239 protecting group Chemical group 0.000 description 18
- 125000004076 pyridyl group Chemical group 0.000 description 18
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 17
- 239000012190 activator Substances 0.000 description 17
- 150000004982 aromatic amines Chemical class 0.000 description 17
- 238000005859 coupling reaction Methods 0.000 description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 17
- 125000002971 oxazolyl group Chemical group 0.000 description 17
- 125000000335 thiazolyl group Chemical group 0.000 description 17
- 238000007254 oxidation reaction Methods 0.000 description 16
- 150000003512 tertiary amines Chemical class 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 15
- 238000007112 amidation reaction Methods 0.000 description 15
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 15
- 125000001786 isothiazolyl group Chemical group 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 14
- 125000004429 atom Chemical group 0.000 description 14
- 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 14
- 150000007524 organic acids Chemical class 0.000 description 14
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 14
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 13
- 239000002253 acid Substances 0.000 description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 13
- 150000007529 inorganic bases Chemical class 0.000 description 13
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 13
- 238000007363 ring formation reaction Methods 0.000 description 13
- 238000006467 substitution reaction Methods 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 208000001145 Metabolic Syndrome Diseases 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 206010028980 Neoplasm Diseases 0.000 description 12
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 12
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 12
- 125000005018 aryl alkenyl group Chemical group 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 12
- 230000002140 halogenating effect Effects 0.000 description 12
- 238000001990 intravenous administration Methods 0.000 description 12
- 239000003446 ligand Substances 0.000 description 12
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 description 12
- 239000007800 oxidant agent Substances 0.000 description 12
- 230000001590 oxidative effect Effects 0.000 description 12
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 12
- 125000001113 thiadiazolyl group Chemical group 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 206010020772 Hypertension Diseases 0.000 description 11
- 206010056997 Impaired fasting glucose Diseases 0.000 description 11
- 150000001447 alkali salts Chemical class 0.000 description 11
- 150000004703 alkoxides Chemical class 0.000 description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 11
- 230000037396 body weight Effects 0.000 description 11
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- 230000003197 catalytic effect Effects 0.000 description 11
- 229910052739 hydrogen Inorganic materials 0.000 description 11
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 11
- 229940002612 prodrug Drugs 0.000 description 11
- 239000000651 prodrug Substances 0.000 description 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 10
- 150000001350 alkyl halides Chemical class 0.000 description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 230000032050 esterification Effects 0.000 description 10
- 150000004820 halides Chemical class 0.000 description 10
- 150000004678 hydrides Chemical class 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000011261 inert gas Substances 0.000 description 10
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000001340 alkali metals Chemical class 0.000 description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 9
- 201000011510 cancer Diseases 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 9
- 201000010099 disease Diseases 0.000 description 9
- 235000019441 ethanol Nutrition 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 8
- 206010006895 Cachexia Diseases 0.000 description 8
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 8
- 208000031226 Hyperlipidaemia Diseases 0.000 description 8
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 8
- 150000001342 alkaline earth metals Chemical class 0.000 description 8
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 8
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 8
- 239000003759 ester based solvent Substances 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000004434 sulfur atom Chemical group 0.000 description 8
- 125000006717 (C3-C10) cycloalkenyl group Chemical group 0.000 description 7
- 208000002249 Diabetes Complications Diseases 0.000 description 7
- 206010012655 Diabetic complications Diseases 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 235000011054 acetic acid Nutrition 0.000 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 238000005917 acylation reaction Methods 0.000 description 7
- 239000000556 agonist Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 125000001485 cycloalkadienyl group Chemical group 0.000 description 7
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 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 7
- 125000002950 monocyclic group Chemical group 0.000 description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 7
- 235000019786 weight gain Nutrition 0.000 description 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 6
- 208000002705 Glucose Intolerance Diseases 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 150000001639 boron compounds Chemical class 0.000 description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 6
- 239000001768 carboxy methyl cellulose Substances 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- 239000012024 dehydrating agents Substances 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000007888 film coating Substances 0.000 description 6
- 238000009501 film coating Methods 0.000 description 6
- 239000012025 fluorinating agent Substances 0.000 description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 6
- 238000007410 oral glucose tolerance test Methods 0.000 description 6
- 125000004430 oxygen atom Chemical group O* 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 201000009104 prediabetes syndrome Diseases 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 208000001076 sarcopenia Diseases 0.000 description 6
- 229940124597 therapeutic agent Drugs 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- 241000283690 Bos taurus Species 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 206010019280 Heart failures Diseases 0.000 description 5
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/423—Oxazoles condensed with carbocyclic rings
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
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- A61P3/00—Drugs for disorders of the metabolism
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
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| JP2010266097 | 2010-11-30 | ||
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| JP2011-175330 | 2011-08-10 | ||
| JP2011175330 | 2011-08-10 | ||
| PCT/JP2011/078010 WO2012074126A1 (en) | 2010-11-30 | 2011-11-29 | Bicyclic compound |
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| US9133129B2 (en) | 2011-10-24 | 2015-09-15 | Takeda Pharmaceutical Company Limited | Bicyclic compound |
| EP2928473B1 (en) * | 2012-12-07 | 2017-06-28 | Merck Sharp & Dohme Corp. | Regioselective n-2 arylation of indazoles |
| PL403149A1 (pl) * | 2013-03-14 | 2014-09-15 | Celon Pharma Spółka Akcyjna | Nowe związki pochodne pirazolilobenzo[d]imidazolu |
| JP6417401B2 (ja) | 2013-05-10 | 2018-11-07 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| JP6417402B2 (ja) | 2013-05-10 | 2018-11-07 | ギリアド アポロ， エルエルシー | Ａｃｃ阻害剤及びその使用 |
| EP2994139B1 (en) * | 2013-05-10 | 2019-04-10 | Gilead Apollo, LLC | Acc inhibitors and uses thereof |
| AU2014262547A1 (en) | 2013-05-10 | 2015-11-26 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| US20160220557A1 (en) | 2013-09-12 | 2016-08-04 | Pfizer Inc. | Use of acetyl-coa carboxylase inhibitors for treating acne vulgaris |
| EP3068788A1 (en) | 2013-11-14 | 2016-09-21 | Cadila Healthcare Limited | Novel heterocyclic compounds |
| CR20170077A (es) | 2014-08-04 | 2017-06-26 | Nuevolution As | Derivados de heterociclilo opcionalmente condensados de pirimidina útiles para el tratamiento de enfermedades inflamatorias, metabólicas, oncológicas y autoinmunitarias |
| CN104193731B (zh) * | 2014-08-27 | 2017-03-15 | 广东东阳光药业有限公司 | 一种脲取代联苯类化合物及其组合物及用途 |
| EA035646B1 (ru) * | 2014-08-29 | 2020-07-21 | Сиэйчдиай Фаундэйшн, Инк. | Зонды для визуализации белка хантингтина |
| JP2016079168A (ja) * | 2014-10-17 | 2016-05-16 | 塩野義製薬株式会社 | ９員縮合環誘導体 |
| CN104447725B (zh) * | 2014-10-22 | 2018-02-02 | 浙江大学 | 一种手性含亚胺吡啶噁唑啉的化合物及其制备方法 |
| WO2016130501A1 (en) | 2015-02-09 | 2016-08-18 | Incyte Corporation | Aza-heteroaryl compounds as pi3k-gamma inhibitors |
| BR112018006005A2 (pt) | 2015-09-29 | 2018-10-30 | Oncotherapy Science Inc | composto bicíclico e uso do mesmo para inibição de suv39h2 |
| CN105601626A (zh) * | 2015-11-04 | 2016-05-25 | 浙江大学 | 一种含2-取代噁唑啉衍生物的制备方法 |
| PT3371190T (pt) | 2015-11-06 | 2022-07-08 | Incyte Corp | Compostos heterocíclicos como inibidores de pi3k-gamma |
| US20170190689A1 (en) | 2016-01-05 | 2017-07-06 | Incyte Corporation | Pyridine and pyridimine compounds as pi3k-gamma inhibitors |
| US10138248B2 (en) | 2016-06-24 | 2018-11-27 | Incyte Corporation | Substituted imidazo[2,1-f][1,2,4]triazines, substituted imidazo[1,2-a]pyridines, substituted imidazo[1,2-b]pyridazines and substituted imidazo[1,2-a]pyrazines as PI3K-γ inhibitors |
| MA48475A (fr) | 2017-04-24 | 2020-03-04 | Tesaro Inc | Procédés de fabrication de niraparib |
| KR102717072B1 (ko) | 2017-10-18 | 2024-10-15 | 인사이트 코포레이션 | Pi3k-감마 저해제로서의 3차 하이드록시기로 치환된 축합된 이미다졸 유도체 |
| CR20250050A (es) | 2018-09-05 | 2025-03-19 | Incyte Corp | Formas cristalinas de un inhibidor de fosfoinositida 3–quinasa (pi3k) (divisional 2021-0165) |
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| JP2026500298A (ja) | 2022-12-15 | 2026-01-06 | シンジェンタ クロップ プロテクション アクチェンゲゼルシャフト | 殺有害生物剤として有用である新規な二環式カルボキサミド化合物 |
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| CA2288224A1 (en) * | 1997-04-30 | 1998-11-05 | Mary George Johnson | Antithrombotic agents |
| AR035016A1 (es) | 1999-08-25 | 2004-04-14 | Takeda Chemical Industries Ltd | Composicion de azol promotor de produccion/secrecion de neurotrofina, compuesto prodroga del mismo, composicion farmaceutica que lo comprende y uso del mismo para preparar esta ultima. |
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| US8492405B2 (en) | 2006-10-18 | 2013-07-23 | Takeda Pharmaceutical Company Limited | Glucokinase-activating fused heterocyclic compounds and methods of treating diabetes and obesity |
| RU2454415C9 (ru) | 2006-10-19 | 2013-02-27 | Такеда Фармасьютикал Компани Лимитед | Производное индола |
| EP2128138A1 (en) | 2007-01-29 | 2009-12-02 | Takeda Pharmaceutical Company Limited | Pyrazole compound |
| JP2010517935A (ja) | 2007-02-09 | 2010-05-27 | 武田薬品工業株式会社 | Ｐｐａｒ−ガンマのパーシャルアゴニストとしての縮合環化合物 |
| JPWO2008136428A1 (ja) | 2007-04-27 | 2010-07-29 | 武田薬品工業株式会社 | 含窒素５員複素環化合物 |
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| WO2010050445A1 (ja) | 2008-10-27 | 2010-05-06 | 武田薬品工業株式会社 | 二環性化合物 |
| WO2010118009A1 (en) * | 2009-04-06 | 2010-10-14 | Ptc Therapeutics, Inc. | Hcv inhibitor and therapeutic agent combinations |
| WO2011136385A1 (en) | 2010-04-27 | 2011-11-03 | Takeda Pharmaceutical Company Limited | Bicyclic compound derivatives and their use as acc inhibitors. |
| WO2012108478A1 (ja) | 2011-02-09 | 2012-08-16 | 武田薬品工業株式会社 | 単環化合物 |
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2011
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- 2011-11-29 JP JP2013524677A patent/JP5824517B2/ja not_active Expired - Fee Related
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- 2011-11-29 US US13/306,069 patent/US8729102B2/en not_active Expired - Fee Related
- 2011-11-29 BR BR112013013417A patent/BR112013013417A2/pt not_active IP Right Cessation
- 2011-11-29 UY UY0001033756A patent/UY33756A/es not_active Application Discontinuation
- 2011-11-29 WO PCT/JP2011/078010 patent/WO2012074126A1/en not_active Ceased
- 2011-11-29 MX MX2013006113A patent/MX2013006113A/es not_active Application Discontinuation
- 2011-11-29 CA CA2819400A patent/CA2819400A1/en not_active Abandoned
- 2011-11-29 AU AU2011337565A patent/AU2011337565A1/en not_active Abandoned
- 2011-11-29 EA EA201390794A patent/EA201390794A1/ru unknown
- 2011-11-29 CN CN201180066388.XA patent/CN103347872B/zh not_active Expired - Fee Related
- 2011-11-29 KR KR1020137016850A patent/KR20140001965A/ko not_active Withdrawn
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2013
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- 2013-06-24 CO CO13149620A patent/CO6751239A2/es not_active Application Discontinuation
- 2013-06-25 EC ECSP13012719 patent/ECSP13012719A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN103347872A (zh) | 2013-10-09 |
| JP2013545718A (ja) | 2013-12-26 |
| ES2536319T3 (es) | 2015-05-22 |
| WO2012074126A9 (en) | 2013-06-06 |
| BR112013013417A2 (pt) | 2019-09-24 |
| EA201390794A1 (ru) | 2013-11-29 |
| CO6751239A2 (es) | 2013-09-16 |
| SG190925A1 (en) | 2013-07-31 |
| PH12013501099A1 (en) | 2013-07-08 |
| AU2011337565A2 (en) | 2013-07-11 |
| DOP2013000118A (es) | 2013-09-30 |
| AU2011337565A1 (en) | 2013-07-11 |
| EP2649062A1 (en) | 2013-10-16 |
| US20120142714A1 (en) | 2012-06-07 |
| EP2649062B1 (en) | 2015-04-08 |
| UY33756A (es) | 2012-06-29 |
| WO2012074126A1 (en) | 2012-06-07 |
| US8729102B2 (en) | 2014-05-20 |
| ECSP13012719A (es) | 2013-12-31 |
| PE20140161A1 (es) | 2014-02-19 |
| MA34713B1 (fr) | 2013-12-03 |
| JP5824517B2 (ja) | 2015-11-25 |
| CR20130281A (es) | 2013-10-07 |
| CL2013001520A1 (es) | 2013-10-18 |
| KR20140001965A (ko) | 2014-01-07 |
| TW201242951A (en) | 2012-11-01 |
| CN103347872B (zh) | 2014-12-24 |
| AR084032A1 (es) | 2013-04-17 |
| MX2013006113A (es) | 2013-11-01 |
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