NZ561414A - Method and composition for treating peripheral vascular diseases - Google Patents

Info

Publication number

NZ561414A

NZ561414A NZ561414A NZ56141406A NZ561414A NZ 561414 A NZ561414 A NZ 561414A NZ 561414 A NZ561414 A NZ 561414A NZ 56141406 A NZ56141406 A NZ 56141406A NZ 561414 A NZ561414 A NZ 561414A

Authority

NZ

New Zealand

Prior art keywords

preparation

alkyl

group

alkoxy

product

Prior art date

2005-03-04

Links

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• Global Dossier
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• 208000018262 Peripheral vascular disease Diseases 0.000 title abstract 2
• 238000000034 method Methods 0.000 title description 58
• 238000002360 preparation method Methods 0.000 claims description 438
• 150000001875 compounds Chemical class 0.000 claims description 147
• 125000000217 alkyl group Chemical group 0.000 claims description 57
• -1 -NR7R8 Chemical group 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 42
• 150000003839 salts Chemical class 0.000 claims description 27
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
• 125000001246 bromo group Chemical group Br* 0.000 claims description 23
• 125000001424 substituent group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 208000018737 Parkinson disease Diseases 0.000 claims description 18
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000004432 carbon atom Chemical group C* 0.000 claims description 15
• 125000004429 atom Chemical group 0.000 claims description 14
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 13
• 229910052760 oxygen Inorganic materials 0.000 claims description 13
• 239000003795 chemical substances by application Substances 0.000 claims description 12
• 208000005793 Restless legs syndrome Diseases 0.000 claims description 10
• 208000014094 Dystonic disease Diseases 0.000 claims description 9
• WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims description 9
• WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims description 9
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• 125000005843 halogen group Chemical group 0.000 claims description 9
• 229910052717 sulfur Inorganic materials 0.000 claims description 9
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• 239000008194 pharmaceutical composition Substances 0.000 claims description 8
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
• 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 7
• 125000004966 cyanoalkyl group Chemical group 0.000 claims description 7
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 206010039966 Senile dementia Diseases 0.000 claims description 6
• 125000004414 alkyl thio group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
• 230000000694 effects Effects 0.000 claims description 6
• 239000003112 inhibitor Substances 0.000 claims description 6
• 229910052757 nitrogen Inorganic materials 0.000 claims description 6
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
• 125000004434 sulfur atom Chemical group 0.000 claims description 6
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• 125000004122 cyclic group Chemical group 0.000 claims description 5
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• 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 4
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• 125000002619 bicyclic group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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• 125000001153 fluoro group Chemical group F* 0.000 claims description 4
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• 150000002367 halogens Chemical class 0.000 claims description 4
• 125000005842 heteroatom Chemical group 0.000 claims description 4
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 4
• 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 4
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• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims description 3
• 208000015114 central nervous system disease Diseases 0.000 claims description 3
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
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• 208000035475 disorder Diseases 0.000 claims description 3
• 239000001257 hydrogen Substances 0.000 claims description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
• 125000002346 iodo group Chemical group I* 0.000 claims description 3
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• 125000003342 alkenyl group Chemical group 0.000 claims description 2
• 125000005081 alkoxyalkoxyalkyl group Chemical group 0.000 claims description 2
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
• 125000005159 cyanoalkoxy group Chemical group 0.000 claims description 2
• 230000006735 deficit Effects 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
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• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
• 238000005192 partition Methods 0.000 description 69
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• 235000019439 ethyl acetate Nutrition 0.000 description 33
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 32
• 239000000243 solution Substances 0.000 description 32
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• 239000012267 brine Substances 0.000 description 27
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 27
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 24
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
• 229910000104 sodium hydride Inorganic materials 0.000 description 22
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
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• 238000010992 reflux Methods 0.000 description 17
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• 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 17
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• ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
• 230000028838 turning behavior Effects 0.000 description 1
• ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
• 230000025033 vasoconstriction Effects 0.000 description 1
• 230000024883 vasodilation Effects 0.000 description 1
• 229940124549 vasodilator Drugs 0.000 description 1
• 239000003071 vasodilator agent Substances 0.000 description 1
• 239000003039 volatile agent Substances 0.000 description 1