JP2010514795A5

JP2010514795A5 -

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Publication number: JP2010514795A5
Authority: JP; Japan
Prior art keywords: substituted; group; alkyl; aryl; heteroaryl
Prior art date: 2007-12-27
Legal status : Granted

Application number

JP2009544271A

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English (en)

Japanese (ja)

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JP2010514795A (ja

JP5455645B2 (ja

Filing date

2007-12-27

Publication date

2012-01-26

2007-12-26 Priority claimed from US11/964,461 external-priority patent/US7638541B2/en

2007-12-27 Application filed filed Critical

2010-05-06 Publication of JP2010514795A publication Critical patent/JP2010514795A/ja

2012-01-26 Publication of JP2010514795A5 publication Critical patent/JP2010514795A5/ja

2014-03-26 Application granted granted Critical

2014-03-26 Publication of JP5455645B2 publication Critical patent/JP5455645B2/ja

Status Expired - Fee Related legal-status Critical Current

2027-12-27 Anticipated expiration legal-status Critical

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150000001875 compounds Chemical class 0.000 claims description 279
125000001072 heteroaryl group Chemical group 0.000 claims description 201
125000000217 alkyl group Chemical group 0.000 claims description 188
125000003118 aryl group Chemical group 0.000 claims description 172
125000000623 heterocyclic group Chemical group 0.000 claims description 130
-1 pin Lori Le Chemical group 0.000 claims description 123
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 claims description 100
239000000203 mixture Substances 0.000 claims description 93
125000005843 halogen group Chemical group 0.000 claims description 82
125000001424 substituent group Chemical group 0.000 claims description 74
125000003107 substituted aryl group Chemical group 0.000 claims description 70
125000000304 alkynyl group Chemical group 0.000 claims description 69
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 claims description 68
239000008103 glucose Substances 0.000 claims description 68
125000001188 haloalkyl group Chemical group 0.000 claims description 68
238000000034 method Methods 0.000 claims description 64
229910052739 hydrogen Inorganic materials 0.000 claims description 61
125000000547 substituted alkyl group Chemical group 0.000 claims description 59
125000000753 cycloalkyl group Chemical group 0.000 claims description 58
239000001257 hydrogen Substances 0.000 claims description 56
125000000714 pyrimidinyl group Chemical group 0.000 claims description 56
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 54
229910052757 nitrogen Inorganic materials 0.000 claims description 54
206010012601 diabetes mellitus Diseases 0.000 claims description 51
102000004877 Insulin Human genes 0.000 claims description 50
108090001061 Insulin Proteins 0.000 claims description 50
229940125396 insulin Drugs 0.000 claims description 50
125000004076 pyridyl group Chemical group 0.000 claims description 50
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
125000002883 imidazolyl group Chemical group 0.000 claims description 48
125000001715 oxadiazolyl group Chemical group 0.000 claims description 48
125000003831 tetrazolyl group Chemical group 0.000 claims description 47
125000001425 triazolyl group Chemical group 0.000 claims description 47
210000000227 basophil cell of anterior lobe of hypophysis Anatomy 0.000 claims description 46
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
125000000335 thiazolyl group Chemical group 0.000 claims description 46
208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 45
239000008280 blood Substances 0.000 claims description 43
210000004369 blood Anatomy 0.000 claims description 43
125000003373 pyrazinyl group Chemical group 0.000 claims description 43
125000002971 oxazolyl group Chemical group 0.000 claims description 42
125000002098 pyridazinyl group Chemical group 0.000 claims description 41
230000003914 insulin secretion Effects 0.000 claims description 38
201000010099 disease Diseases 0.000 claims description 37
241000124008 Mammalia Species 0.000 claims description 35
150000002431 hydrogen Chemical class 0.000 claims description 33
229910052760 oxygen Inorganic materials 0.000 claims description 30
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 29
229910052717 sulfur Inorganic materials 0.000 claims description 29
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical class 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 25
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 20
230000001419 dependent effect Effects 0.000 claims description 18
150000002148 esters Chemical class 0.000 claims description 16
125000005842 heteroatom Chemical group 0.000 claims description 15
239000008194 pharmaceutical composition Substances 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 14
239000000546 pharmaceutical excipient Substances 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 12
208000001145 Metabolic Syndrome Diseases 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 10
125000001153 fluoro group Chemical group F* 0.000 claims description 9
238000004519 manufacturing process Methods 0.000 claims description 9
230000004936 stimulating effect Effects 0.000 claims description 9
UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 9
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 6
125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 6
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000006648 (C1-C8) haloalkyl group Chemical group 0.000 claims description 3
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
150000001336 alkenes Chemical class 0.000 claims description 3
150000001345 alkine derivatives Chemical class 0.000 claims description 3
125000001786 isothiazolyl group Chemical group 0.000 claims description 3
125000000842 isoxazolyl group Chemical group 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
229910052727 yttrium Inorganic materials 0.000 claims description 3
125000004043 oxo group Chemical group O=* 0.000 claims description 2
125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
125000006164 6-membered heteroaryl group Chemical group 0.000 claims 1
230000001548 androgenic effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 117
239000000243 solution Substances 0.000 description 84
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 83
239000000543 intermediate Substances 0.000 description 81
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 62
239000000047 product Substances 0.000 description 60
235000019439 ethyl acetate Nutrition 0.000 description 57
239000002904 solvent Substances 0.000 description 55
230000002829 reductive effect Effects 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 45
125000005346 substituted cycloalkyl group Chemical group 0.000 description 45
125000003342 alkenyl group Chemical group 0.000 description 40
239000011734 sodium Substances 0.000 description 39
125000004426 substituted alkynyl group Chemical group 0.000 description 37
125000005017 substituted alkenyl group Chemical group 0.000 description 36
238000011282 treatment Methods 0.000 description 35
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 33
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 32
229940095074 cyclic amp Drugs 0.000 description 32
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000000556 agonist Substances 0.000 description 30
239000000741 silica gel Substances 0.000 description 30
229910002027 silica gel Inorganic materials 0.000 description 30
210000004027 cell Anatomy 0.000 description 29
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 28
239000004031 partial agonist Substances 0.000 description 28
238000002360 preparation method Methods 0.000 description 28
239000007787 solid Substances 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
230000001965 increasing effect Effects 0.000 description 27
239000012267 brine Substances 0.000 description 25
230000000694 effects Effects 0.000 description 25
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 25
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
239000003814 drug Substances 0.000 description 22
239000003112 inhibitor Substances 0.000 description 22
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
125000004432 carbon atom Chemical group C* 0.000 description 20
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 19
125000004093 cyano group Chemical group *C#N 0.000 description 19
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
238000001816 cooling Methods 0.000 description 18
MGXWVYUBJRZYPE-YUGYIWNOSA-N incretin Chemical class C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](C)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCC(N)=O)C(O)=O)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=1C=CC(O)=CC=1)[C@@H](C)O)[C@@H](C)CC)C1=CC=C(O)C=C1 MGXWVYUBJRZYPE-YUGYIWNOSA-N 0.000 description 18
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
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206010022489 Insulin Resistance Diseases 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
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 14
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125000004414 alkyl thio group Chemical group 0.000 description 14
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JP2009544271A 2006-12-28 2007-12-27 糖尿病および代謝障害を処置するためのヘテロ環式受容体アゴニスト Expired - Fee Related JP5455645B2 (ja)