CA2643503A1

CA2643503A1 - Purine compounds and methods of use thereof

Purine compounds and methods of use thereof Download PDF

Info

Publication number: CA2643503A1
Authority: CA; Canada
Prior art keywords: compound; formula; alkyl; monocyclic; subject
Prior art date: 2006-03-23
Legal status : Abandoned

Application number

CA002643503A

Other languages

English (en)

French (fr)

Inventor

Andrew L. Salzman

Prakash Jagtap

Current Assignee

Rocket Pharmaceuticals Inc

Original Assignee

Individual

Priority date

2006-03-23

Filing date

2007-03-22

Publication date

2007-10-04

2007-03-22 Application filed by Individual filed Critical Individual

2007-10-04 Publication of CA2643503A1 publication Critical patent/CA2643503A1/en

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 297
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title description 249
-1 Purine Compound Chemical class 0.000 claims abstract description 459
239000000203 mixture Substances 0.000 claims abstract description 103
210000002216 heart Anatomy 0.000 claims abstract description 67
230000004060 metabolic process Effects 0.000 claims abstract description 50
230000003680 myocardial damage Effects 0.000 claims abstract description 39
208000008589 Obesity Diseases 0.000 claims abstract description 22
235000020824 obesity Nutrition 0.000 claims abstract description 21
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 18
208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 17
230000000302 ischemic effect Effects 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
208000010399 Wasting Syndrome Diseases 0.000 claims abstract description 14
150000001875 compounds Chemical class 0.000 claims description 286
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 212
125000000217 alkyl group Chemical group 0.000 claims description 187
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 176
150000003839 salts Chemical class 0.000 claims description 109
125000004432 carbon atom Chemical group C* 0.000 claims description 61
125000001475 halogen functional group Chemical group 0.000 claims description 59
150000001413 amino acids Chemical class 0.000 claims description 52
229910052799 carbon Inorganic materials 0.000 claims description 47
101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 39
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
101100294106 Caenorhabditis elegans nhr-3 gene Proteins 0.000 claims description 33
239000003795 chemical substances by application Substances 0.000 claims description 27
125000002950 monocyclic group Chemical group 0.000 claims description 27
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 24
230000036757 core body temperature Effects 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 22
230000001939 inductive effect Effects 0.000 claims description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
230000036284 oxygen consumption Effects 0.000 claims description 18
125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
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 8
125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 4
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 3
125000006370 trihalo methyl group Chemical group 0.000 claims description 2
KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract description 378
208000027418 Wounds and injury Diseases 0.000 abstract description 41
230000006378 damage Effects 0.000 abstract description 27
208000014674 injury Diseases 0.000 abstract description 27
208000027866 inflammatory disease Diseases 0.000 abstract description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 20
206010052428 Wound Diseases 0.000 abstract description 19
230000005855 radiation Effects 0.000 abstract description 19
230000001413 cellular effect Effects 0.000 abstract description 7
230000002062 proliferating effect Effects 0.000 abstract description 7
150000003212 purines Chemical class 0.000 abstract description 7
208000017520 skin disease Diseases 0.000 abstract description 7
125000004093 cyano group Chemical group *C#N 0.000 description 99
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 76
235000002639 sodium chloride Nutrition 0.000 description 69
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 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
125000002947 alkylene group Chemical group 0.000 description 50
229940024606 amino acid Drugs 0.000 description 49
235000001014 amino acid Nutrition 0.000 description 49
206010028980 Neoplasm Diseases 0.000 description 48
239000003814 drug Substances 0.000 description 48
125000001309 chloro group Chemical group Cl* 0.000 description 47
239000000543 intermediate Substances 0.000 description 44
229940124597 therapeutic agent Drugs 0.000 description 40
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 39
201000011510 cancer Diseases 0.000 description 39
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 39
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 34
239000002126 C01EB10 - Adenosine Substances 0.000 description 33
229960005305 adenosine Drugs 0.000 description 33
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 33
238000011282 treatment Methods 0.000 description 33
238000001356 surgical procedure Methods 0.000 description 32
239000003981 vehicle Substances 0.000 description 32
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
229910019142 PO4 Inorganic materials 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 26
210000004027 cell Anatomy 0.000 description 26
229910001868 water Inorganic materials 0.000 description 26
125000003118 aryl group Chemical group 0.000 description 24
125000004122 cyclic group Chemical group 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
125000000304 alkynyl group Chemical group 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
150000001412 amines Chemical class 0.000 description 20
210000000056 organ Anatomy 0.000 description 20
101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 description 19
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 19
101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 description 19
230000002829 reductive effect Effects 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 17
241000282414 Homo sapiens Species 0.000 description 17
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
238000011394 anticancer treatment Methods 0.000 description 16
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
229910052760 oxygen Inorganic materials 0.000 description 15
230000001225 therapeutic effect Effects 0.000 description 15
210000001519 tissue Anatomy 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
238000013270 controlled release Methods 0.000 description 14
230000002265 prevention Effects 0.000 description 14
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 13
208000035475 disorder Diseases 0.000 description 13
239000000243 solution Substances 0.000 description 13
238000013268 sustained release Methods 0.000 description 13
239000012730 sustained-release form Substances 0.000 description 13
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000002246 antineoplastic agent Substances 0.000 description 12
230000000694 effects Effects 0.000 description 12
239000000546 pharmaceutical excipient Substances 0.000 description 12
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 11
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 11
230000000069 prophylactic effect Effects 0.000 description 11
238000001959 radiotherapy Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
210000004379 membrane Anatomy 0.000 description 10
239000012528 membrane Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
208000006011 Stroke Diseases 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000002552 dosage form Substances 0.000 description 9
239000007924 injection Substances 0.000 description 9
238000002347 injection Methods 0.000 description 9
208000028867 ischemia Diseases 0.000 description 9
239000001301 oxygen Substances 0.000 description 9
230000010412 perfusion Effects 0.000 description 9
210000003491 skin Anatomy 0.000 description 9
238000002054 transplantation Methods 0.000 description 9
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 8
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 8
238000002512 chemotherapy Methods 0.000 description 8
239000012634 fragment Substances 0.000 description 8
239000002777 nucleoside Substances 0.000 description 8
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
208000002193 Pain Diseases 0.000 description 7
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HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 7
230000027455 binding Effects 0.000 description 7
210000004556 brain Anatomy 0.000 description 7
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DCFKHNIGBAHNSS-UHFFFAOYSA-N chloro(triethyl)silane Chemical compound CC[Si](Cl)(CC)CC DCFKHNIGBAHNSS-UHFFFAOYSA-N 0.000 description 7
125000000392 cycloalkenyl group Chemical group 0.000 description 7
125000000753 cycloalkyl group Chemical group 0.000 description 7
238000011161 development Methods 0.000 description 7
230000018109 developmental process Effects 0.000 description 7
229940079593 drug Drugs 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 7
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
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VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 6
QCHPKSFMDHPSNR-UHFFFAOYSA-N 3-aminoisobutyric acid Chemical compound NCC(C)C(O)=O QCHPKSFMDHPSNR-UHFFFAOYSA-N 0.000 description 6
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 6
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DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
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239000007983 Tris buffer Substances 0.000 description 6
239000000556 agonist Substances 0.000 description 6
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125000000654 isopropylidene group Chemical class C(C)(C)=* 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
229940083251 peripheral vasodilators purine derivative Drugs 0.000 description 6
230000029058 respiratory gaseous exchange Effects 0.000 description 6
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229910052708 sodium Inorganic materials 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
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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 6
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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
206010058467 Lung neoplasm malignant Diseases 0.000 description 4
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 4
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NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 4
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208000029028 brain injury Diseases 0.000 description 4
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