SK2592002A3 - Tricyclic inhibitors of poly(adp-ribose) polymerases - Google Patents

Tricyclic inhibitors of poly(adp-ribose) polymerases Download PDF

Info

Publication number: SK2592002A3
Authority: SK; Slovakia
Prior art keywords: aryl; heterocycloalkyl; cycloalkyl; alkynyl; alkenyl
Prior art date: 1999-08-31

Application number

SK259-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Stephen Evan Webber

Donald James Skalitzky

Jayashree Girish Tikhe

Robert Arnold Kumpf

Joseph Timothy Marakovits

Brian Walter Eastman

Original Assignee

Agouron Pharma

Cancer Res Campaign Tech

Priority date (The priority date 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 date listed.)

1999-08-31

Filing date

2000-08-31

Publication date

2002-10-08

2000-08-31 Application filed by Agouron Pharma, Cancer Res Campaign Tech filed Critical Agouron Pharma

2002-10-08 Publication of SK2592002A3 publication Critical patent/SK2592002A3/sk

Links

229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 title claims description 68
108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 title claims description 60
102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 title claims description 59
239000003112 inhibitor Substances 0.000 title description 8
150000001875 compounds Chemical class 0.000 claims abstract description 273
230000000694 effects Effects 0.000 claims abstract description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 253
229910052757 nitrogen Inorganic materials 0.000 claims description 237
238000000034 method Methods 0.000 claims description 198
125000003118 aryl group Chemical group 0.000 claims description 184
125000001072 heteroaryl group Chemical group 0.000 claims description 153
125000000753 cycloalkyl group Chemical group 0.000 claims description 144
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 143
125000000304 alkynyl group Chemical group 0.000 claims description 140
125000003342 alkenyl group Chemical group 0.000 claims description 139
125000000547 substituted alkyl group Chemical group 0.000 claims description 120
125000000217 alkyl group Chemical group 0.000 claims description 92
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 70
229910052736 halogen Inorganic materials 0.000 claims description 68
150000002367 halogens Chemical class 0.000 claims description 68
125000001424 substituent group Chemical group 0.000 claims description 60
150000003839 salts Chemical class 0.000 claims description 50
239000012453 solvate Substances 0.000 claims description 40
239000002207 metabolite Substances 0.000 claims description 38
125000004093 cyano group Chemical group *C#N 0.000 claims description 37
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
229940002612 prodrug Drugs 0.000 claims description 37
239000000651 prodrug Substances 0.000 claims description 37
230000002401 inhibitory effect Effects 0.000 claims description 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 35
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 31
239000003795 chemical substances by application Substances 0.000 claims description 29
229910052760 oxygen Inorganic materials 0.000 claims description 28
102000004190 Enzymes Human genes 0.000 claims description 23
108090000790 Enzymes Proteins 0.000 claims description 23
229910052717 sulfur Inorganic materials 0.000 claims description 23
241000124008 Mammalia Species 0.000 claims description 19
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
230000005764 inhibitory process Effects 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 10
230000003389 potentiating effect Effects 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
238000003556 assay Methods 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 8
125000004104 aryloxy group Chemical group 0.000 claims description 7
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
125000005553 heteroaryloxy group Chemical group 0.000 claims description 7
108010017601 Tankyrases Proteins 0.000 claims description 4
125000005418 aryl aryl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
101710179684 Poly [ADP-ribose] polymerase Proteins 0.000 claims 14
102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 claims 14
230000003013 cytotoxicity Effects 0.000 claims 4
231100000135 cytotoxicity Toxicity 0.000 claims 4
102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 claims 2
125000005017 substituted alkenyl group Chemical group 0.000 claims 1
208000006011 Stroke Diseases 0.000 abstract description 10
230000004770 neurodegeneration Effects 0.000 abstract description 8
206010019196 Head injury Diseases 0.000 abstract description 7
208000015122 neurodegenerative disease Diseases 0.000 abstract description 7
239000003814 drug Substances 0.000 abstract description 6
206010028980 Neoplasm Diseases 0.000 abstract description 2
239000003558 transferase inhibitor Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 476
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 286
239000007787 solid Substances 0.000 description 253
229910052799 carbon Inorganic materials 0.000 description 233
239000000047 product Substances 0.000 description 146
235000019439 ethyl acetate Nutrition 0.000 description 142
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 118
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 113
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 102
-1 oxygen radicals Chemical class 0.000 description 101
239000011541 reaction mixture Substances 0.000 description 98
239000002904 solvent Substances 0.000 description 89
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 76
238000004128 high performance liquid chromatography Methods 0.000 description 76
239000000243 solution Substances 0.000 description 69
150000001412 amines Chemical class 0.000 description 58
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 48
ARDQOKBQXMKAJW-UHFFFAOYSA-N 5h-azulen-6-one Chemical compound C1=CC(=O)CC=C2C=CC=C21 ARDQOKBQXMKAJW-UHFFFAOYSA-N 0.000 description 41
239000000203 mixture Substances 0.000 description 40
238000006243 chemical reaction Methods 0.000 description 38
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 37
238000003818 flash chromatography Methods 0.000 description 36
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
239000000741 silica gel Substances 0.000 description 31
229910002027 silica gel Inorganic materials 0.000 description 31
150000004985 diamines Chemical class 0.000 description 29
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
238000002360 preparation method Methods 0.000 description 23
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 22
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 22
239000012044 organic layer Substances 0.000 description 22
235000002639 sodium chloride Nutrition 0.000 description 22
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
238000000746 purification Methods 0.000 description 21
238000010992 reflux Methods 0.000 description 20
150000001299 aldehydes Chemical class 0.000 description 19
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 17
239000002253 acid Substances 0.000 description 17
230000035484 reaction time Effects 0.000 description 17
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 17
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 16
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 16
239000012267 brine Substances 0.000 description 16
239000012661 PARP inhibitor Substances 0.000 description 15
229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 15
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000004809 thin layer chromatography Methods 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 14
229910052763 palladium Inorganic materials 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 12
239000012043 crude product Substances 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
125000004432 carbon atom Chemical group C* 0.000 description 11
238000004440 column chromatography Methods 0.000 description 11
201000010099 disease Diseases 0.000 description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 11
150000002576 ketones Chemical class 0.000 description 11
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 11
239000000725 suspension Substances 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
238000011282 treatment Methods 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 10
238000000354 decomposition reaction Methods 0.000 description 10
238000006268 reductive amination reaction Methods 0.000 description 10
230000002829 reductive effect Effects 0.000 description 10
239000011734 sodium Substances 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
108091026813 Poly(ADPribose) Proteins 0.000 description 9
239000000284 extract Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000005534 decanoate group Chemical class 0.000 description 8
238000011161 development Methods 0.000 description 8
230000018109 developmental process Effects 0.000 description 8
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 8
150000003951 lactams Chemical class 0.000 description 8
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125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 8
MFUIXAMVRWIMMR-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenyl]-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound C1=CC(OCCO)=CC=C1C1=NC2=CC=CC3=C2N1CCNC3=O MFUIXAMVRWIMMR-UHFFFAOYSA-N 0.000 description 7
QRHVTJIEPZZTNF-UHFFFAOYSA-N 3,4-dihydropyrrolo(3,2,1-jk)(1,4)benzodiazepin-1(2h)-one Chemical compound O=C1NCCN2C=CC3=CC=CC1=C23 QRHVTJIEPZZTNF-UHFFFAOYSA-N 0.000 description 7
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PEVSPCKJWXKQHX-UHFFFAOYSA-N chembl189670 Chemical compound C=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C1=CC=CC=C1 PEVSPCKJWXKQHX-UHFFFAOYSA-N 0.000 description 7
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125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 7
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NXVQPQIEEULMJF-UHFFFAOYSA-N 1-[4-(2-hydroxy-ethyl)-phenyl]-8,9-dihydro-7h-2,7,9a-triaza-benzo[cd]azulen-6-one Chemical compound C1=CC(CCO)=CC=C1C(N1CC2)=NC=C3C1=C2NC(=O)C=C3 NXVQPQIEEULMJF-UHFFFAOYSA-N 0.000 description 6
DBYXBLQLOHDHBJ-UHFFFAOYSA-N 4-(4-fluoro-6-oxo-6,7,8,9-tetrahydro-2,7,9a-triaza-benzo[cd]azulen-1-yl)-benzaldehyde Chemical compound N=1C=C2C(F)=CC(=O)NC(CC3)=C2N3C=1C1=CC=C(C=O)C=C1 DBYXBLQLOHDHBJ-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
XQVZDADGTFJAFM-UHFFFAOYSA-N Indole-7-carboxaldehyde Chemical compound O=CC1=CC=CC2=C1NC=C2 XQVZDADGTFJAFM-UHFFFAOYSA-N 0.000 description 6
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YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
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230000004913 activation Effects 0.000 description 6
239000012298 atmosphere Substances 0.000 description 6
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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230000006378 damage Effects 0.000 description 6
206010012601 diabetes mellitus Diseases 0.000 description 6
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238000010438 heat treatment Methods 0.000 description 6
125000005842 heteroatom Chemical group 0.000 description 6
239000010410 layer Substances 0.000 description 6
229940098779 methanesulfonic acid Drugs 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
239000012071 phase Substances 0.000 description 6
125000003367 polycyclic group Chemical group 0.000 description 6
GVEMORXNDBIEEV-UHFFFAOYSA-N 2-methylsulfinyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound O=C1NCCN2C(S(=O)C)=NC3=CC=CC1=C32 GVEMORXNDBIEEV-UHFFFAOYSA-N 0.000 description 5
108020004414 DNA Proteins 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
XKAKJEGRGQDPNT-UHFFFAOYSA-N N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1C1CCCN1 Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1C1CCCN1 XKAKJEGRGQDPNT-UHFFFAOYSA-N 0.000 description 5
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 5
125000001588 azulen-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C([H])C([H])=C([H])C2=C1* 0.000 description 5
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239000006227 byproduct Substances 0.000 description 5
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
210000004027 cell Anatomy 0.000 description 5
230000030833 cell death Effects 0.000 description 5
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 5
125000002950 monocyclic group Chemical group 0.000 description 5
238000002953 preparative HPLC Methods 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
WCNVOWWRJIZZKA-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-one Chemical compound O=C1NCCNC2=CC=CC=C12 WCNVOWWRJIZZKA-UHFFFAOYSA-N 0.000 description 4
QPASZTZXNVXHCZ-UHFFFAOYSA-N 2-(4-pyridin-4-ylphenyl)-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1C(C=C1)=CC=C1C1=CC=NC=C1 QPASZTZXNVXHCZ-UHFFFAOYSA-N 0.000 description 4
JIXQFXKGXBGVDC-UHFFFAOYSA-N 2-benzylsulfanyl-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-9-one Chemical compound N=1C(C2=3)=CC=CC=3C(=O)NCCN2C=1SCC1=CC=CC=C1 JIXQFXKGXBGVDC-UHFFFAOYSA-N 0.000 description 4
HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 4
HMLHYKQHJLCOEE-UHFFFAOYSA-N 3-(9-oxo-1,3,10-triazatricyclo[6.4.1.04,13]trideca-2,4,6,8(13)-tetraen-2-yl)benzaldehyde Chemical compound O=CC1=CC=CC(C=2N3CCNC(=O)C=4C=CC=C(C3=4)N=2)=C1 HMLHYKQHJLCOEE-UHFFFAOYSA-N 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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SK259-2002A 1999-08-31 2000-08-31 Tricyclic inhibitors of poly(adp-ribose) polymerases SK2592002A3 (en)

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Application Number	Priority Date	Filing Date	Title
US15214299P	1999-08-31	1999-08-31
PCT/US2000/023882 WO2001016136A2 (fr)	1999-08-31	2000-08-31	Inhibiteurs tricycliques de poly(adp-ribose) polymerases

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JP2002515488A (ja)	1998-05-15	2002-05-28	ギルフォードファーマシューティカルズインコーポレイテッド	カルボキサミド化合物、組成物、及びｐａｒｐ活性の抑制方法
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2000
- 2000-08-29 EC EC2000003637A patent/ECSP003637A/es unknown
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- 2000-08-30 CO CO00065062A patent/CO5200769A1/es not_active Application Discontinuation
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- 2000-08-31 DE DE60017575T patent/DE60017575T2/de not_active Expired - Lifetime
- 2000-08-31 KR KR1020027002629A patent/KR20020038742A/ko not_active Abandoned
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- 2000-08-31 SK SK259-2002A patent/SK2592002A3/sk unknown
- 2000-08-31 ES ES00961437T patent/ES2234657T3/es not_active Expired - Lifetime
- 2000-08-31 CN CN00815066A patent/CN1384835A/zh active Pending
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- 2000-08-31 AU AU73389/00A patent/AU781826B2/en not_active Ceased
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- 2000-08-31 WO PCT/US2000/023882 patent/WO2001016136A2/fr not_active Ceased
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- 2000-08-31 JP JP2001519702A patent/JP4272375B2/ja not_active Expired - Lifetime
- 2000-08-31 CA CA002382404A patent/CA2382404C/fr not_active Expired - Fee Related
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2002
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- 2002-02-27 IS IS6289A patent/IS6289A/is unknown
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Also Published As

Publication number	Publication date
ES2234657T3 (es)	2005-07-01
IL147863A0 (en)	2002-08-14
MA25876A1 (fr)	2003-10-01
NZ516793A (en)	2004-03-26
DOP2000000069A (es)	2002-08-30
YU15102A (sh)	2004-12-31
PT1208104E (pt)	2005-04-29
JP2003513015A (ja)	2003-04-08
EP1208104B1 (fr)	2005-01-19
PE20010538A1 (es)	2001-05-22
CA2382404C (fr)	2009-03-24
BR0015051A (pt)	2002-06-25
NO20020421L (no)	2002-04-25
HUP0202703A2 (hu)	2002-12-28
CO5200769A1 (es)	2002-09-27
KR20020038742A (ko)	2002-05-23
UY26323A1 (es)	2001-04-30
WO2001016136B1 (fr)	2001-11-15
AU7338900A (en)	2001-03-26
ATE287406T1 (de)	2005-02-15
GT200000145A (es)	2002-02-21
NO20020421D0 (no)	2002-01-28
PA8501801A1 (es)	2002-08-26
AR035162A1 (es)	2004-05-05
OA12016A (en)	2006-04-19
SV2003000162A (es)	2003-07-29
HK1045509A1 (en)	2002-11-29
EP1208104A2 (fr)	2002-05-29
UA73144C2 (en)	2005-06-15
DE60017575T2 (de)	2005-06-09
ECSP003637A (es)	2002-03-25
EE200200100A (et)	2003-06-16
AU781826B2 (en)	2005-06-16
PL354242A1 (en)	2003-12-29
JP4272375B2 (ja)	2009-06-03
HK1045509B (en)	2005-04-29
AP1553A (en)	2006-01-18
MXPA02002138A (es)	2003-08-20
HRP20020271A2 (en)	2005-12-31
US6548494B1 (en)	2003-04-15
WO2001016136A2 (fr)	2001-03-08
CN1384835A (zh)	2002-12-11
DK1208104T3 (da)	2005-05-02
IS6289A (is)	2002-02-27
HUP0202703A3 (en)	2004-12-28
CR6577A (es)	2003-12-05
NO322475B1 (no)	2006-10-09
DE60017575D1 (de)	2005-02-24
CA2382404A1 (fr)	2001-03-08
ZA200200830B (en)	2003-03-26
SI1208104T1 (en)	2005-06-30
GEP20043268B (en)	2004-06-25
BG106562A (bg)	2003-03-31
MY135910A (en)	2008-07-31
DZ3216A1 (fr)	2001-03-08
EA200200306A1 (ru)	2002-08-29
WO2001016136A3 (fr)	2001-06-21
CZ2002613A3 (cs)	2002-08-14

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