MX2008012185A

MX2008012185A - Compuestos de purina y metodos de uso de los mismos.

Compuestos de purina y metodos de uso de los mismos.

Info

Publication number: MX2008012185A
Authority: MX; Mexico
Prior art keywords: carbon atoms; compound; formula; alkyl; monocyclic
Prior art date: 2006-03-23

Application number

MX2008012185A

Other languages

English (en)

Spanish (es)

Inventor

Prakash Jagtap

Andrew L Salzmar

Original Assignee

Inotek Pharmaceuticals Corp

Priority date

2006-03-23

Filing date

2007-03-22

Publication date

2008-10-02

2007-03-22 Application filed by Inotek Pharmaceuticals Corp filed Critical Inotek Pharmaceuticals Corp

2008-10-02 Publication of MX2008012185A publication Critical patent/MX2008012185A/es

Links

238000000034 method Methods 0.000 title claims abstract description 278
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 257
-1 Purine Compound Chemical class 0.000 claims abstract description 428
239000000203 mixture Substances 0.000 claims abstract description 92
210000002216 heart Anatomy 0.000 claims abstract description 53
230000003680 myocardial damage Effects 0.000 claims abstract description 42
208000008589 Obesity Diseases 0.000 claims abstract description 22
235000020824 obesity Nutrition 0.000 claims abstract description 22
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 20
230000000302 ischemic effect Effects 0.000 claims abstract description 18
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 17
206010063837 Reperfusion injury Diseases 0.000 claims abstract description 16
208000012902 Nervous system disease Diseases 0.000 claims abstract description 14
230000004060 metabolic process Effects 0.000 claims abstract description 13
208000010399 Wasting Syndrome Diseases 0.000 claims abstract description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 1238
150000001875 compounds Chemical class 0.000 claims description 285
125000000217 alkyl group Chemical group 0.000 claims description 226
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 206
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 128
150000003839 salts Chemical class 0.000 claims description 108
238000011282 treatment Methods 0.000 claims description 97
229910052799 carbon Inorganic materials 0.000 claims description 83
125000002947 alkylene group Chemical group 0.000 claims description 77
229910052736 halogen Inorganic materials 0.000 claims description 67
125000002619 bicyclic group Chemical group 0.000 claims description 65
150000001413 amino acids Chemical class 0.000 claims description 49
150000001721 carbon Chemical group 0.000 claims description 48
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 38
230000037323 metabolic rate Effects 0.000 claims description 36
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 35
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 34
229910052757 nitrogen Inorganic materials 0.000 claims description 32
125000000732 arylene group Chemical group 0.000 claims description 28
239000003795 chemical substances by application Substances 0.000 claims description 28
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 22
125000004429 atom Chemical group 0.000 claims description 20
125000000304 alkynyl group Chemical group 0.000 claims description 17
230000001939 inductive effect Effects 0.000 claims description 16
125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
230000001101 cardioplegic effect Effects 0.000 claims description 14
230000036284 oxygen consumption Effects 0.000 claims description 14
230000036757 core body temperature Effects 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
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 7
150000002367 halogens Chemical class 0.000 claims description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract description 321
208000027866 inflammatory disease Diseases 0.000 abstract description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 18
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230000002062 proliferating effect Effects 0.000 abstract description 6
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230000001413 cellular effect Effects 0.000 abstract description 4
230000005855 radiation Effects 0.000 abstract description 3
206010028980 Neoplasm Diseases 0.000 description 64
125000004093 cyano group Chemical group *C#N 0.000 description 61
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OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 56
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 48
230000002265 prevention Effects 0.000 description 47
229940024606 amino acid Drugs 0.000 description 46
235000001014 amino acid Nutrition 0.000 description 46
239000003814 drug Substances 0.000 description 44
239000000543 intermediate Substances 0.000 description 43
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238000002360 preparation method Methods 0.000 description 34
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239000002126 C01EB10 - Adenosine Substances 0.000 description 29
229910019142 PO4 Inorganic materials 0.000 description 29
229960005305 adenosine Drugs 0.000 description 29
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 29
239000010452 phosphate Substances 0.000 description 29
125000000753 cycloalkyl group Chemical group 0.000 description 27
238000001356 surgical procedure Methods 0.000 description 25
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125000003161 (C1-C6) alkylene group Chemical group 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
238000011277 treatment modality Methods 0.000 description 24
210000004027 cell Anatomy 0.000 description 23
125000004122 cyclic group Chemical group 0.000 description 23
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101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
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150000001412 amines Chemical class 0.000 description 18
125000003118 aryl group Chemical group 0.000 description 17
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239000002253 acid Substances 0.000 description 15
125000001309 chloro group Chemical group Cl* 0.000 description 15
210000000056 organ Anatomy 0.000 description 13
239000000546 pharmaceutical excipient Substances 0.000 description 13
230000002829 reductive effect Effects 0.000 description 13
238000013268 sustained release Methods 0.000 description 13
239000012730 sustained-release form Substances 0.000 description 13
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
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238000000926 separation method Methods 0.000 description 11
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical compound CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
238000002512 chemotherapy Methods 0.000 description 8
125000000392 cycloalkenyl group Chemical group 0.000 description 8
150000002148 esters Chemical class 0.000 description 8
239000003379 purinergic P1 receptor agonist Substances 0.000 description 8
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210000003491 skin Anatomy 0.000 description 8
239000000243 solution Substances 0.000 description 8
201000009030 Carcinoma Diseases 0.000 description 7
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
239000002775 capsule Substances 0.000 description 7
DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 7
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229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 7
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MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 6
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
208000005189 Embolism Diseases 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
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HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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238000009903 catalytic hydrogenation reaction Methods 0.000 description 6
125000003636 chemical group Chemical group 0.000 description 6
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125000000654 isopropylidene group Chemical class C(C)(C)=* 0.000 description 6
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 6
239000002777 nucleoside Substances 0.000 description 6
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230000002195 synergetic effect Effects 0.000 description 6
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 5
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 5
BPPJDUPAHNSENM-YQBTWGSQSA-N (2r,3r,4s,5r)-2-(6-amino-6-chloro-8h-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol Chemical class C1N=C2C(N)(Cl)N=CN=C2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O BPPJDUPAHNSENM-YQBTWGSQSA-N 0.000 description 4
XNMQEEKYCVKGBD-UHFFFAOYSA-N 2-butyne Chemical compound CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 4
NKTDTMONXHODTI-UHFFFAOYSA-N 2-pentyne Chemical group CCC#CC NKTDTMONXHODTI-UHFFFAOYSA-N 0.000 description 4
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101100516572 Caenorhabditis elegans nhr-8 gene Proteins 0.000 description 4
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
206010058314 Dysplasia Diseases 0.000 description 4
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
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NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 4
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
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206010049771 Shock haemorrhagic Diseases 0.000 description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
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239000002585 base Substances 0.000 description 4
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AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 description 4
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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 description 4
OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 description 4
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CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 description 4
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FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 4
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