CA2731442A1

CA2731442A1 - Substituted aminothiazole derivatives, pharmaceutical compositions, and methods of use

Substituted aminothiazole derivatives, pharmaceutical compositions, and methods of use Download PDF

Info

Publication number: CA2731442A1
Authority: CA; Canada
Prior art keywords: group; methyl; alkyl; cyclohexyl; compound
Prior art date: 2008-08-29
Legal status : Abandoned

Application number

CA2731442A

Other languages

English (en)

French (fr)

Inventor

Adnan M. M. Mjalli

Bapu Gaddam

Robert C. Andrews

Samuel Victory

Suparna Gupta

Current Assignee

vTv Therapeutics LLC

Original Assignee

Trans Tech Pharma Inc

Priority date

2008-08-29

Filing date

2009-08-25

Publication date

2010-03-04

2009-08-25 Application filed by Trans Tech Pharma Inc filed Critical Trans Tech Pharma Inc

2010-03-04 Publication of CA2731442A1 publication Critical patent/CA2731442A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 234
239000008194 pharmaceutical composition Chemical class 0.000 title claims abstract description 28
RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 273
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 53
208000008589 Obesity Diseases 0.000 claims abstract description 26
235000020824 obesity Nutrition 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims description 88
-1 -phenyl Chemical group 0.000 claims description 81
239000001257 hydrogen Substances 0.000 claims description 76
229910052739 hydrogen Inorganic materials 0.000 claims description 76
125000000217 alkyl group Chemical group 0.000 claims description 65
239000000203 mixture Substances 0.000 claims description 47
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 43
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 33
125000001424 substituent group Chemical group 0.000 claims description 29
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 20
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 20
125000004432 carbon atom Chemical group C* 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 13
206010057671 Female sexual dysfunction Diseases 0.000 claims description 12
235000019786 weight gain Nutrition 0.000 claims description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
230000004584 weight gain Effects 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
206010057672 Male sexual dysfunction Diseases 0.000 claims description 9
239000003937 drug carrier Substances 0.000 claims description 9
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
230000004580 weight loss Effects 0.000 claims description 5
230000007423 decrease Effects 0.000 claims description 4
XOMZJWSIQIBUQR-QAQDUYKDSA-N S1C(C)=CC=C1CN(CCC(O)=O)C1=NC([C@@H]2CC[C@H](CC2)C(C)(C)C)=CS1 Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC([C@@H]2CC[C@H](CC2)C(C)(C)C)=CS1 XOMZJWSIQIBUQR-QAQDUYKDSA-N 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
FRFAQMKDIVZURC-UHFFFAOYSA-N 3-[[4-[4-(4-fluorophenyl)cyclohexyl]-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(CC2)C=2C=CC(F)=CC=2)=CS1 FRFAQMKDIVZURC-UHFFFAOYSA-N 0.000 claims description 2
ASTROQQYUQIBSQ-MXVIHJGJSA-N S1C(C)=CC=C1CN(CCC(O)=O)C1=NC([C@@H]2CC[C@H](CC2)C=2C=CC=CC=2)=CS1 Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC([C@@H]2CC[C@H](CC2)C=2C=CC=CC=2)=CS1 ASTROQQYUQIBSQ-MXVIHJGJSA-N 0.000 claims description 2
QBCAGJGPWFAZDH-UHFFFAOYSA-N 3-[[4-(4-methoxycyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound C1CC(OC)CCC1C1=CSC(N(CCC(O)=O)CC=2SC(C)=CC=2)=N1 QBCAGJGPWFAZDH-UHFFFAOYSA-N 0.000 claims 2
YOOZBJQEMOPTJW-UHFFFAOYSA-N 3-[(5-methylthiophen-2-yl)methyl-[4-(4-propan-2-ylcyclohexyl)-1,3-thiazol-2-yl]amino]propanoic acid Chemical compound C1CC(C(C)C)CCC1C1=CSC(N(CCC(O)=O)CC=2SC(C)=CC=2)=N1 YOOZBJQEMOPTJW-UHFFFAOYSA-N 0.000 claims 1
FGGSHTCNGFCULE-UHFFFAOYSA-N 3-[(5-methylthiophen-2-yl)methyl-[4-(4-propylcyclohexyl)-1,3-thiazol-2-yl]amino]propanoic acid Chemical compound C1CC(CCC)CCC1C1=CSC(N(CCC(O)=O)CC=2SC(C)=CC=2)=N1 FGGSHTCNGFCULE-UHFFFAOYSA-N 0.000 claims 1
IEOGVWBPUKXEQF-UHFFFAOYSA-N 3-[(5-methylthiophen-2-yl)methyl-[4-[4-(trifluoromethyl)cyclohexyl]-1,3-thiazol-2-yl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(CC2)C(F)(F)F)=CS1 IEOGVWBPUKXEQF-UHFFFAOYSA-N 0.000 claims 1
PPVPBVSDDKTQRT-UHFFFAOYSA-N 3-[[4-(4,4-difluorocyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(F)(F)CC2)=CS1 PPVPBVSDDKTQRT-UHFFFAOYSA-N 0.000 claims 1
ZRZZQCNAIDQHNS-UHFFFAOYSA-N 3-[[4-(4,4-dimethylcyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(C)(C)CC2)=CS1 ZRZZQCNAIDQHNS-UHFFFAOYSA-N 0.000 claims 1
VQUUBEMPSSADJM-UHFFFAOYSA-N 3-[[4-(4-cyclohexylcyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(CC2)C2CCCCC2)=CS1 VQUUBEMPSSADJM-UHFFFAOYSA-N 0.000 claims 1
UGOGHKGNOQEGPJ-UHFFFAOYSA-N 3-[[4-(4-ethylcyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound C1CC(CC)CCC1C1=CSC(N(CCC(O)=O)CC=2SC(C)=CC=2)=N1 UGOGHKGNOQEGPJ-UHFFFAOYSA-N 0.000 claims 1
XOMZJWSIQIBUQR-UHFFFAOYSA-N 3-[[4-(4-tert-butylcyclohexyl)-1,3-thiazol-2-yl]-[(5-methylthiophen-2-yl)methyl]amino]propanoic acid Chemical compound S1C(C)=CC=C1CN(CCC(O)=O)C1=NC(C2CCC(CC2)C(C)(C)C)=CS1 XOMZJWSIQIBUQR-UHFFFAOYSA-N 0.000 claims 1
102000004378 Melanocortin Receptors Human genes 0.000 abstract description 34
108090000950 Melanocortin Receptors Proteins 0.000 abstract description 34
201000010099 disease Diseases 0.000 abstract description 26
238000002360 preparation method Methods 0.000 abstract description 19
241000282414 Homo sapiens Species 0.000 abstract description 13
241001465754 Metazoa Species 0.000 abstract description 8
239000003112 inhibitor Substances 0.000 abstract description 7
230000009471 action Effects 0.000 abstract description 5
229950003476 aminothiazole Drugs 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 210
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 208
238000006243 chemical reaction Methods 0.000 description 118
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 112
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 102
239000000243 solution Substances 0.000 description 99
235000019439 ethyl acetate Nutrition 0.000 description 86
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 84
239000002904 solvent Substances 0.000 description 57
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 55
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
239000002253 acid Substances 0.000 description 47
230000002829 reductive effect Effects 0.000 description 44
239000000047 product Substances 0.000 description 42
238000010626 work up procedure Methods 0.000 description 41
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 38
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 36
239000011734 sodium Substances 0.000 description 36
229910052938 sodium sulfate Inorganic materials 0.000 description 36
235000011152 sodium sulphate Nutrition 0.000 description 36
238000001704 evaporation Methods 0.000 description 35
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 34
235000015424 sodium Nutrition 0.000 description 33
229910052708 sodium Inorganic materials 0.000 description 33
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
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150000002576 ketones Chemical class 0.000 description 28
159000000000 sodium salts Chemical class 0.000 description 28
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230000000694 effects Effects 0.000 description 26
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 26
229910000030 sodium bicarbonate Inorganic materials 0.000 description 26
235000017557 sodium bicarbonate Nutrition 0.000 description 26
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238000003756 stirring Methods 0.000 description 20
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 19
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
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GFSIWZOMVZZZOU-UHFFFAOYSA-N tert-butyl 3-[carbamothioyl-[(5-methylthiophen-2-yl)methyl]amino]propanoate Chemical compound CC1=CC=C(CN(CCC(=O)OC(C)(C)C)C(N)=S)S1 GFSIWZOMVZZZOU-UHFFFAOYSA-N 0.000 description 11
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 8
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