DK2570414T3 - HETEROCYCLIC AROMATIC COMPOUNDS USED AS GROWTH HORMONE CERTAOGRAPHY - Google Patents

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Publication number

DK2570414T3

DK2570414T3 DK12191757.9T DK12191757T DK2570414T3 DK 2570414 T3 DK2570414 T3 DK 2570414T3 DK 12191757 T DK12191757 T DK 12191757T DK 2570414 T3 DK2570414 T3 DK 2570414T3

Authority

DK

Denmark

Prior art keywords

group

compound

alkyl

cycloalkyl

agents

Prior art date

2002-09-04

Links

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• 108010051696 Growth Hormone Proteins 0.000 title claims description 37
• 239000000122 growth hormone Substances 0.000 title claims description 37
• 102000018997 Growth Hormone Human genes 0.000 title claims 4
• 150000001491 aromatic compounds Chemical class 0.000 title claims 2
• 150000001875 compounds Chemical class 0.000 claims description 205
• 238000011282 treatment Methods 0.000 claims description 84
• -1 arylalkyloxyalkyl Chemical group 0.000 claims description 67
• 125000000217 alkyl group Chemical group 0.000 claims description 56
• 125000003118 aryl group Chemical group 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 38
• 125000001072 heteroaryl group Chemical group 0.000 claims description 35
• 125000000623 heterocyclic group Chemical group 0.000 claims description 35
• 239000003795 chemical substances by application Substances 0.000 claims description 33
• 239000001257 hydrogen Substances 0.000 claims description 25
• 229910052739 hydrogen Inorganic materials 0.000 claims description 25
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 210000003205 muscle Anatomy 0.000 claims description 18
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 15
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 claims description 14
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
• 125000000524 functional group Chemical group 0.000 claims description 14
• 150000002431 hydrogen Chemical class 0.000 claims description 14
• 125000003342 alkenyl group Chemical group 0.000 claims description 13
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 13
• 125000000304 alkynyl group Chemical group 0.000 claims description 13
• 229910052757 nitrogen Inorganic materials 0.000 claims description 13
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
• 229910052736 halogen Inorganic materials 0.000 claims description 11
• 150000002367 halogens Chemical class 0.000 claims description 11
• 229910052705 radium Inorganic materials 0.000 claims description 11
• 229910052701 rubidium Inorganic materials 0.000 claims description 11
• 239000005557 antagonist Substances 0.000 claims description 10
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• 235000020824 obesity Nutrition 0.000 claims description 8
• 229940095743 selective estrogen receptor modulator Drugs 0.000 claims description 8
• 239000000333 selective estrogen receptor modulator Substances 0.000 claims description 8
• 239000003529 anticholesteremic agent Substances 0.000 claims description 7
• 239000003472 antidiabetic agent Substances 0.000 claims description 7
• 229940011871 estrogen Drugs 0.000 claims description 7
• 239000000262 estrogen Substances 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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• 108090000468 progesterone receptors Proteins 0.000 claims description 7
• 239000000849 selective androgen receptor modulator Substances 0.000 claims description 7
• 230000004936 stimulating effect Effects 0.000 claims description 7
• 229960003604 testosterone Drugs 0.000 claims description 7
• 210000001685 thyroid gland Anatomy 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 229940122361 Bisphosphonate Drugs 0.000 claims description 6
• 206010007559 Cardiac failure congestive Diseases 0.000 claims description 6
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• 102000003982 Parathyroid hormone Human genes 0.000 claims description 6
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• 229940121363 anti-inflammatory agent Drugs 0.000 claims description 6
• 239000002260 anti-inflammatory agent Substances 0.000 claims description 6
• 239000000883 anti-obesity agent Substances 0.000 claims description 6
• 229940125708 antidiabetic agent Drugs 0.000 claims description 6
• 125000004104 aryloxy group Chemical group 0.000 claims description 6
• 150000004663 bisphosphonates Chemical class 0.000 claims description 6
• 229940097217 cardiac glycoside Drugs 0.000 claims description 6
• 239000002368 cardiac glycoside Substances 0.000 claims description 6
• 230000006870 function Effects 0.000 claims description 6
• 229960001319 parathyroid hormone Drugs 0.000 claims description 6
• 239000000199 parathyroid hormone Substances 0.000 claims description 6
• 238000002360 preparation method Methods 0.000 claims description 6
• 239000000018 receptor agonist Substances 0.000 claims description 6
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• 150000008143 steroidal glycosides Chemical class 0.000 claims description 6
• 208000011580 syndromic disease Diseases 0.000 claims description 6
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• 125000004450 alkenylene group Chemical group 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000004419 alkynylene group Chemical group 0.000 claims description 5
• 230000003262 anti-osteoporosis Effects 0.000 claims description 5
• 229940127226 anticholesterol agent Drugs 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
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• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 208000022531 anorexia Diseases 0.000 claims description 4
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• 239000003937 drug carrier Substances 0.000 claims description 4
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• 208000001076 sarcopenia Diseases 0.000 claims description 4
• 208000019116 sleep disease Diseases 0.000 claims description 4
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
• 238000002255 vaccination Methods 0.000 claims description 4
• 208000003577 HIV wasting syndrome Diseases 0.000 claims description 3
• 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
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• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 3
• 230000036772 blood pressure Effects 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 206010012601 diabetes mellitus Diseases 0.000 claims description 3
• 235000015872 dietary supplement Nutrition 0.000 claims description 3
• 125000005549 heteroarylene group Chemical group 0.000 claims description 3
• 208000017169 kidney disease Diseases 0.000 claims description 3
• 230000007774 longterm Effects 0.000 claims description 3
• 125000002950 monocyclic group Chemical group 0.000 claims description 3
• 125000001174 sulfone group Chemical group 0.000 claims description 3
• 229910052804 chromium Inorganic materials 0.000 claims description 2
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 230000000153 supplemental effect Effects 0.000 claims 3
• 208000018578 heart valve disease Diseases 0.000 claims 2
• 230000003178 anti-diabetic effect Effects 0.000 claims 1
• 125000002619 bicyclic group Chemical group 0.000 claims 1
• 229930182470 glycoside Natural products 0.000 claims 1
• 150000002338 glycosides Chemical class 0.000 claims 1
• 239000000243 solution Substances 0.000 description 127
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 113
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 108
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 87
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
• 238000000034 method Methods 0.000 description 72
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
• 229910001868 water Inorganic materials 0.000 description 65
• 239000007787 solid Substances 0.000 description 60
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 59
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 53
• 235000019439 ethyl acetate Nutrition 0.000 description 53
• 238000004128 high performance liquid chromatography Methods 0.000 description 52
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 48
• 239000000203 mixture Substances 0.000 description 47
• 230000014759 maintenance of location Effects 0.000 description 43
• 239000007858 starting material Substances 0.000 description 37
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
• 238000006243 chemical reaction Methods 0.000 description 36
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 35
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 35
• 102100038803 Somatotropin Human genes 0.000 description 33
• 238000000746 purification Methods 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
• 238000010511 deprotection reaction Methods 0.000 description 26
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• 239000002904 solvent Substances 0.000 description 26
• 238000003756 stirring Methods 0.000 description 26
• 238000003818 flash chromatography Methods 0.000 description 25
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 24
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• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 22
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• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
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• 238000002953 preparative HPLC Methods 0.000 description 19
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• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
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• YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 16
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• 239000006260 foam Substances 0.000 description 16
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• 125000006239 protecting group Chemical group 0.000 description 14
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• 150000001499 aryl bromides Chemical class 0.000 description 4
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