TW201113269A

TW201113269A - New compounds, pharmaceutical composition and methods relating thereto

New compounds, pharmaceutical composition and methods relating thereto Download PDF

Info

Publication number: TW201113269A
Authority: TW; Taiwan
Prior art keywords: alkyl; group; aryl; compound; independently
Prior art date: 2009-06-24

Application number

TW099120497A

Other languages

English (en)

Chinese (zh)

Inventor

Joe A Tran

Chen Chen

Original Assignee

Boehringer Ingelheim Int

Neurocrine Biosciences Inc

Priority date

2009-06-24

Filing date

2010-06-23

Publication date

2011-04-16

2010-06-23 Application filed by Boehringer Ingelheim Int, Neurocrine Biosciences Inc filed Critical Boehringer Ingelheim Int

2011-04-16 Publication of TW201113269A publication Critical patent/TW201113269A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 87
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
238000000034 method Methods 0.000 title abstract description 81
239000000203 mixture Substances 0.000 claims abstract description 103
150000003839 salts Chemical class 0.000 claims abstract description 37
238000011282 treatment Methods 0.000 claims abstract description 22
239000012453 solvate Substances 0.000 claims abstract description 13
-1 cyano, hydroxyl Chemical group 0.000 claims description 86
125000000217 alkyl group Chemical group 0.000 claims description 64
125000001424 substituent group Chemical group 0.000 claims description 39
125000003118 aryl group Chemical group 0.000 claims description 38
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 33
125000000623 heterocyclic group Chemical group 0.000 claims description 32
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
201000010099 disease Diseases 0.000 claims description 26
101000996752 Homo sapiens Glucose-dependent insulinotropic receptor Proteins 0.000 claims description 21
102100033839 Glucose-dependent insulinotropic receptor Human genes 0.000 claims description 19
239000003814 drug Substances 0.000 claims description 19
208000024891 symptom Diseases 0.000 claims description 18
229910052736 halogen Inorganic materials 0.000 claims description 15
150000002367 halogens Chemical class 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
239000000126 substance Substances 0.000 claims description 11
230000000694 effects Effects 0.000 claims description 10
229940079593 drug Drugs 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 8
229940124597 therapeutic agent Drugs 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000000468 ketone group Chemical group 0.000 claims description 5
229930194542 Keto Natural products 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
150000002923 oximes Chemical class 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 2
239000008024 pharmaceutical diluent Substances 0.000 claims description 2
150000002576 ketones Chemical class 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
241000233866 Fungi Species 0.000 claims 1
235000009499 Vanilla fragrans Nutrition 0.000 claims 1
244000263375 Vanilla tahitensis Species 0.000 claims 1
235000012036 Vanilla tahitensis Nutrition 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
239000008177 pharmaceutical agent Substances 0.000 claims 1
239000003937 drug carrier Substances 0.000 abstract description 2
150000002148 esters Chemical class 0.000 abstract description 2
230000002503 metabolic effect Effects 0.000 abstract 1
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 53
239000000243 solution Substances 0.000 description 52
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235000019439 ethyl acetate Nutrition 0.000 description 46
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 28
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 27
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 27
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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 25
239000008103 glucose Substances 0.000 description 25
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
239000012267 brine Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 17
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
238000002953 preparative HPLC Methods 0.000 description 16
229910000104 sodium hydride Inorganic materials 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
208000001072 type 2 diabetes mellitus Diseases 0.000 description 14
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239000012044 organic layer Substances 0.000 description 13
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AJJISMLYIMQAKP-OAHLLOKOSA-N 5-[4-[(2r)-4-(3-fluoro-4-methylsulfonylphenoxy)butan-2-yl]piperidin-1-yl]-3-propan-2-yl-1,2,4-oxadiazole Chemical compound CC(C)C1=NOC(N2CCC(CC2)[C@H](C)CCOC=2C=C(F)C(=CC=2)S(C)(=O)=O)=N1 AJJISMLYIMQAKP-OAHLLOKOSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229940100607 GPR119 agonist Drugs 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
206010012601 diabetes mellitus Diseases 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
229910052731 fluorine Inorganic materials 0.000 description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
239000010410 layer Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
239000000725 suspension Substances 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000004429 atom Chemical group 0.000 description 9
239000008280 blood Substances 0.000 description 9
210000004369 blood Anatomy 0.000 description 9
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239000007789 gas Substances 0.000 description 9
229920006395 saturated elastomer Polymers 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
150000001412 amines Chemical class 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
239000000651 prodrug Substances 0.000 description 7
229940002612 prodrug Drugs 0.000 description 7
229940044601 receptor agonist Drugs 0.000 description 7
239000000018 receptor agonist Substances 0.000 description 7
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 6
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208000008589 Obesity Diseases 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000003818 flash chromatography Methods 0.000 description 6
229910052739 hydrogen Inorganic materials 0.000 description 6
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
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235000020824 obesity Nutrition 0.000 description 6
239000000047 product Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
HNSDLXPSAYFUHK-UHFFFAOYSA-N 1,4-bis(2-ethylhexyl) sulfosuccinate Chemical compound CCCCC(CC)COC(=O)CC(S(O)(=O)=O)C(=O)OCC(CC)CCCC HNSDLXPSAYFUHK-UHFFFAOYSA-N 0.000 description 5
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
239000007995 HEPES buffer Substances 0.000 description 5
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230000037396 body weight Effects 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000003085 diluting agent Substances 0.000 description 5
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000001072 heteroaryl group Chemical group 0.000 description 5
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
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DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 5
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 4
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CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
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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 3
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