AU2007329464A1 - Thrombopoietin mimetics - Google Patents

Info

Publication number

AU2007329464A1

AU2007329464A1 AU2007329464A AU2007329464A AU2007329464A1 AU 2007329464 A1 AU2007329464 A1 AU 2007329464A1 AU 2007329464 A AU2007329464 A AU 2007329464A AU 2007329464 A AU2007329464 A AU 2007329464A AU 2007329464 A1 AU2007329464 A1 AU 2007329464A1

Authority

AU

Australia

Prior art keywords

compound

hydroxy

alkyl

substituted

methyl

Prior art date

2006-12-01

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

• Espacenet
• Global Dossier
• Discuss

• 102000036693 Thrombopoietin Human genes 0.000 title description 60
• 108010041111 Thrombopoietin Proteins 0.000 title description 60
• 150000001875 compounds Chemical class 0.000 claims description 386
• -1 alkylphosphonyloxy Chemical group 0.000 claims description 263
• 125000000217 alkyl group Chemical group 0.000 claims description 156
• 238000000034 method Methods 0.000 claims description 92
• 125000003118 aryl group Chemical group 0.000 claims description 90
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 89
• 150000003839 salts Chemical class 0.000 claims description 88
• 229910052739 hydrogen Inorganic materials 0.000 claims description 79
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 77
• 239000001257 hydrogen Substances 0.000 claims description 77
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 76
• 125000001072 heteroaryl group Chemical group 0.000 claims description 71
• 239000012453 solvate Substances 0.000 claims description 69
• 125000001188 haloalkyl group Chemical group 0.000 claims description 65
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 150000002148 esters Chemical class 0.000 claims description 60
• 206010043554 thrombocytopenia Diseases 0.000 claims description 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 52
• 238000011282 treatment Methods 0.000 claims description 50
• 125000001424 substituent group Chemical group 0.000 claims description 47
• 241001465754 Metazoa Species 0.000 claims description 43
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 43
• 201000010099 disease Diseases 0.000 claims description 43
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 42
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 40
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 38
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 38
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 36
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
• 208000035475 disorder Diseases 0.000 claims description 34
• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 33
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 33
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 33
• 239000008194 pharmaceutical composition Substances 0.000 claims description 33
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 32
• 229910052757 nitrogen Inorganic materials 0.000 claims description 32
• 125000003342 alkenyl group Chemical group 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 29
• 241000282414 Homo sapiens Species 0.000 claims description 27
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 27
• 230000009385 viral infection Effects 0.000 claims description 27
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 26
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 25
• 125000004414 alkyl thio group Chemical group 0.000 claims description 25
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 24
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 24
• 210000000130 stem cell Anatomy 0.000 claims description 24
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 23
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
• 125000003282 alkyl amino group Chemical group 0.000 claims description 22
• 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 22
• 238000002512 chemotherapy Methods 0.000 claims description 22
• 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 22
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 21
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
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• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 201000011510 cancer Diseases 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 17
• 210000004369 blood Anatomy 0.000 claims description 17
• 239000008280 blood Substances 0.000 claims description 17
• 229920006395 saturated elastomer Polymers 0.000 claims description 17
• 208000024891 symptom Diseases 0.000 claims description 17
• 208000011580 syndromic disease Diseases 0.000 claims description 16
• 208000031981 Thrombocytopenic Idiopathic Purpura Diseases 0.000 claims description 15
• 125000004949 alkyl amino carbonyl amino group Chemical group 0.000 claims description 15
• 239000003246 corticosteroid Substances 0.000 claims description 15
• 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 15
• 208000028622 Immune thrombocytopenia Diseases 0.000 claims description 14
• 125000006598 aminocarbonylamino group Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 241000725303 Human immunodeficiency virus Species 0.000 claims description 13
• 229940079593 drug Drugs 0.000 claims description 13
• 208000005176 Hepatitis C Diseases 0.000 claims description 12
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 12
• 238000010322 bone marrow transplantation Methods 0.000 claims description 12
• 229960004618 prednisone Drugs 0.000 claims description 12
• XOFYZVNMUHMLCC-ZPOLXVRWSA-N prednisone Chemical compound O=C1C=C[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 XOFYZVNMUHMLCC-ZPOLXVRWSA-N 0.000 claims description 12
• JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical group O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 12
• 239000004480 active ingredient Substances 0.000 claims description 11
• 125000000304 alkynyl group Chemical group 0.000 claims description 11
• 238000001356 surgical procedure Methods 0.000 claims description 11
• 125000002252 acyl group Chemical group 0.000 claims description 10
• 125000005195 alkyl amino carbonyloxy group Chemical group 0.000 claims description 10
• 125000002431 aminoalkoxy group Chemical group 0.000 claims description 10
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 10
• 125000004994 halo alkoxy alkyl group Chemical group 0.000 claims description 10
• 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 10
• 238000011476 stem cell transplantation Methods 0.000 claims description 10
• 108060003951 Immunoglobulin Proteins 0.000 claims description 9
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 9
• 125000005202 dialkylaminocarbonyloxy group Chemical group 0.000 claims description 9
• 125000004992 haloalkylamino group Chemical group 0.000 claims description 9
• 102000018358 immunoglobulin Human genes 0.000 claims description 9
• 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 8
• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
• 229960001334 corticosteroids Drugs 0.000 claims description 8
• 238000001990 intravenous administration Methods 0.000 claims description 8
• 210000004185 liver Anatomy 0.000 claims description 8
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 8
• 208000019155 Radiation injury Diseases 0.000 claims description 7
• 125000004442 acylamino group Chemical group 0.000 claims description 7
• 125000004423 acyloxy group Chemical group 0.000 claims description 7
• 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
• 239000002246 antineoplastic agent Substances 0.000 claims description 7
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 7
• 125000004104 aryloxy group Chemical group 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 229940127089 cytotoxic agent Drugs 0.000 claims description 7
• 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims description 7
• 125000005222 heteroarylaminocarbonyl group Chemical group 0.000 claims description 7
• 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 7
• 108090000177 Interleukin-11 Proteins 0.000 claims description 6
• 102000003815 Interleukin-11 Human genes 0.000 claims description 6
• 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 6
• 125000005154 alkyl sulfonyl amino alkyl group Chemical group 0.000 claims description 6
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims description 6
• 125000005100 aryl amino carbonyl group Chemical group 0.000 claims description 6
• 125000005164 aryl thioalkyl group Chemical group 0.000 claims description 6
• 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims description 6
• 239000003102 growth factor Substances 0.000 claims description 6
• 230000003394 haemopoietic effect Effects 0.000 claims description 6
• 125000000262 haloalkenyl group Chemical group 0.000 claims description 6
• 125000006809 haloalkylaminocarbonyl group Chemical group 0.000 claims description 6
• 125000005191 hydroxyalkylamino group Chemical group 0.000 claims description 6
• 238000002054 transplantation Methods 0.000 claims description 6
• 125000004665 trialkylsilyl group Chemical group 0.000 claims description 6
• 108010002386 Interleukin-3 Proteins 0.000 claims description 5
• 102100039064 Interleukin-3 Human genes 0.000 claims description 5
• 208000027418 Wounds and injury Diseases 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 230000006378 damage Effects 0.000 claims description 5
• 208000014674 injury Diseases 0.000 claims description 5
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 4
• 230000022131 cell cycle Effects 0.000 claims description 4
• 239000003999 initiator Substances 0.000 claims description 4
• VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 claims description 2
• 206010019280 Heart failures Diseases 0.000 claims description 2
• 208000026137 Soft tissue injury Diseases 0.000 claims description 2
• 230000003143 atherosclerotic effect Effects 0.000 claims description 2
• 210000003169 central nervous system Anatomy 0.000 claims description 2
• 208000010125 myocardial infarction Diseases 0.000 claims description 2
• 230000008439 repair process Effects 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 12
• ADOSLSYRHIHHAL-UHFFFAOYSA-N 2-[4-(2-hydroxyphenyl)piperidin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCC1C1=CC=CC=C1O ADOSLSYRHIHHAL-UHFFFAOYSA-N 0.000 claims 1
• IFHRAOOJNAECPP-UHFFFAOYSA-N 3-(2-hydroxyphenyl)cyclohexane-1-carboxylic acid Chemical compound C1C(C(=O)O)CCCC1C1=CC=CC=C1O IFHRAOOJNAECPP-UHFFFAOYSA-N 0.000 claims 1
• PBMSTBNDUFGVEP-UHFFFAOYSA-N [PH3]1CCCCC1 Chemical compound [PH3]1CCCCC1 PBMSTBNDUFGVEP-UHFFFAOYSA-N 0.000 claims 1
• 230000001580 bacterial effect Effects 0.000 claims 1
• 208000020403 chronic hepatitis C virus infection Diseases 0.000 claims 1
• 208000010710 hepatitis C virus infection Diseases 0.000 claims 1
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 83
• 150000003254 radicals Chemical class 0.000 description 70
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
• 239000000203 mixture Substances 0.000 description 55
• LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 46
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 41
• 230000002829 reductive effect Effects 0.000 description 40
• 239000002904 solvent Substances 0.000 description 39
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
• 239000000243 solution Substances 0.000 description 36
• 210000001772 blood platelet Anatomy 0.000 description 35
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
• 238000006243 chemical reaction Methods 0.000 description 32
• 150000002431 hydrogen Chemical group 0.000 description 32
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
• 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 30
• 229960000583 acetic acid Drugs 0.000 description 29
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
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