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(12) Patent Application Publication (10) Pub. No.: US 2008/0261947 A1 Seko Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2008/0261947 A1 Seko Et Al US 20080261947A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2008/0261947 A1 Seko et al. (43) Pub. Date: Oct. 23, 2008 (54) FUSED PYRIDAZINE DERIVATIVE Publication Classification COMPOUNDS AND DRUGS CONTAINING (51) Int. Cl. THESE COMPOUNDS AS THE ACTIVE A63L/50 I (2006.01) INGREDIENT C07D 237/32 (2006.01) C07D 40/12 (2006.01) C07D 403/2 (2006.01) (75) Inventors: Takuya Seko, Osaka-shi (JP); Jun A6II 3/55 (2006.01) Takeuchi, Mishima-gun (JP); A6IP 29/00 (2006.01) Shinya Takahashi, Mishima-gun A6IP3/10 (2006.01) A6IP27/06 (2006.01) (JP); Yoshihisa Kamanaka, A6IP 25/00 (2006.01) Mishima-gun (JP); Wataru A6IP 9/00 (2006.01) Kamoshima, Mishima-gun (JP) C07D 47L/04 (2006.01) C07D 413/14 (2006.01) A 6LX 3/5.377 (2006.01) Correspondence Address: (52) U.S. Cl. .................... 514/210.21; 544/237; 544/119: SUGHRUE MION, PLLC 514/233.8: 514/248: 514/234.2:544/117; 2100 PENNSYLVANIA AVENUE, N.W., SUITE 544/236; 540/599; 514/217.05 8OO (57) ABSTRACT WASHINGTON, DC 20037 (US) Fused pyridazine derivatives represented by formula (I) or pharmaceutically acceptable salts thereof (wherein each sym (73) Assignee: ONO PHARMACEUTICAL CO., bol has the meaning as defined in the specification.). LTD. (I) (21) Appl. No.: 12/137,267 (22) Filed: Jun. 11, 2008 Related U.S. Application Data (62) Division of application No. 10/505,012, filed on Aug. Because of inhibiting poly(ADP-ribose)polymerase, the 18, 2004, now Pat. No. 7,402,580, filed as application compounds represented by formula (I) are useful as preven No. PCT/JP2003/001694 on Feb. 18, 2003. tives and/or remedies for various ischemic diseases (in brain, cord, heart, digestive tract, skeletal muscle, retina, etc.), inflammatory diseases (inflammatory bowel disease, mul tiple cerebrosclerosis, arthritis, etc.), neurodegenerative dis eases (extrapyramidal disorder, Alzheimer's disease, muscu lar dystrophy, lumbar spinal canal Stenosis, etc.), diabetes, (30) Foreign Application Priority Data shock, head trauma, renal failure, hyperalgesia, etc. More over, these compounds are useful as agents against retrovi Feb. 19, 2002 (JP) ................................ P2002-42259 ruses (HIV etc.), sensitizers in treating cancer and immuno Jul. 9, 2002 (JP) .............................. P2002-199673 Suppressants. US 2008/026 1947 A1 Oct. 23, 2008 FUSED PYRIDAZINEDERVATIVE ease (TIPS., 19, 287 (1998); Eur J. Pharmacol., 350, 1 COMPOUNDS AND DRUGS CONTAINING (1998)) and hyperalgesia (Pain, 72, 355 (1997)) in vitro, in THESE COMPOUNDS AS THE ACTIVE vivo and in PARP knockout mouse. And it is reported that INGREDIENT PARP inhibitor is useful as an antiretroviral drug such as an anti HIV drug (Biochem. Biophys. Res. Commun., 180, 504 CROSS-REFERENCE TO RELATED (1991)), a sensitizer of anticancer therapy (Radiat. Res., 126, APPLICATIONS 367 (1991); Br. J. Cancer, 72,849 (1995)) or an immunosup 0001. This is a Divisional of U.S. application Ser. No. pressant (Int. J. Immunopharmac., 17, 265 (1995)). 10/505,012 filed Aug. 18, 2004, which is a 371 of PCT Appli 0008 PARP inhibitor is useful for prevention and/or treat cation No. PCT/JP03/01694, Feb. 18, 2003, which claims ment of various diseases, for example, ischemic diseases priority from Japanese Application No. 2002-42259 filed on (cerebral infarction, myocardial infarction, reperfusion injury or postoperative injury etc.), inflammatory diseases (inflam Feb. 19, 2002 and 2002-199673 filed on Jul. 9, 2002. The matory bowel disease, multiple Sclerosis, arthritis or lung above-noted applications are incorporated herein by refer injury etc.), neurodegenerative disorders (extrapyramidal dis ence in their entirety. ease, Parkinson's disease, Alzheimer's disease, muscular TECHNICAL FIELD dystrophy or lumbar spinal canal Stenosis etc.), glaucoma, 0002 The present invention relates to fused pyridazine diabetes, diabetic complication, shock, head trauma, spinal derivative compounds. cord injury, renal failure, hyperalgesia or blood flow obstruc tion etc. And it is useful as an antiretroviral drug Such as an 0003 More particularly, the present invention relates to anti HIV drug, a sensitizer of anticancer therapy or an immu (1) pyridazine derivative compounds represented by formula nosuppressant. (I) 0009. As PARP inhibitor, for example, in the specification of WO00/44726, it is described that 2H-phthalazin-1-one derivatives represented by formula (A) (I) (A) (wherein all symbols have the same meanings as described below), or pharmaceutically acceptable salts thereof, (2) a process for preparing thereof, and (3) an agent comprising the same as an active ingredient. BACKGROUND ART 0004 Poly(ADP-ribose)polymerase (abbreviated as (wherein R'' is PARP hereinafter), which is a nuclear enzyme activated by (i) C1-4 alkyl substituted by hydroxy or amino, or DNA strand breaks, plays a role in the transfer reaction of (ii) -A14-A24-A34, ADP-ribose moiety from nicotinamide adenine dinucleotide (0010 in which A' is NRC(O)– etc. wherein R is (abbreviated as NAD" hereinafter) to various proteins such as hydrogen or C1-4 alkyl etc., A is C1-8 alkylene etc., A' is histones, DNA-polymerases and DNA-topoisomerases, etc. (i), hydrogen, (ii) - NR'R'' or (iii) Cyc etc. wherein R is (i) hydrogen, (ii) C1-8 alkyl etc., and R'' is (i) hydro 0005) DNA strand breaks caused by Peroxynitrite gen or (ii) C1-8 alkyl etc., Cycf" is 3-10 membered mono- or (ONOO) and oxygen radicals lead to overactivation of PARP bi-heterocyclic ring containing 1-4 of nitrogen atoms, 1-2 of (PARP is activated up to 100 times when Zn finger domain of oxygen atoms and/or one sulfur atom, R’ is hydrogen or PARP binds to DNA with nicks.). It is thought that overacti halogen etc. Necessary parts were extracted from the descrip vation of PARP causes depletion of NAD", which is essential tion of groups.) have PARP inhibitory activity. for electron transport system, and consequently depletion of (0011. In the specification of DE3302021, it is described ATP leading to energy failure, ultimately resulting in cell that compounds represented by formula (B) death. (The suicide hypothesis of PARP activation: Free Radic. Biol Med., 21, 855 (1996); TIPS., 19, 287 (1998)). (B) Therefore, it is considered that PARP inhibitor is useful as O inhibitor of cell death. 0006 Since caspase-3, which is one of interleukin-1B RB converting enzyme family, specifically cleaves PARP as the t substrate (Cell., 81, 801 (1995)), it is suggested PARP is 2N associated with apoptosis. R2B 0007. It is reported that 3-aminobenzamide and nicotina H H R3B mide generally known as inhibitors of PARP are useful for 21 H 4B inhibition of cell death and improvement of diseases on vari N (CH2)R R ous models of ischemic diseases (cerebral, myocardial, intes N tinal, skeletal muscular or retinal ischemia etc.), inflamma tory diseases (arthritis, inflammatory bowel disease or O multiple Sclerosis etc.), diabetes, shock, extrapyramidal dis US 2008/026 1947 A1 Oct. 23, 2008 (wherein R' is hydrogen or C1-3 alkyl, R' is hydrogen, R' 6,7,8-tetrahydrophthalazin-1 (2H)-one (CAS Registry No. and R', taken together, are C1-4 alkylene, R. is hydrogen or 134973-24-3) are described as synthetic intermediate. methyl, nB is 0-3, R is 1-pyrrolyl. Necessary parts were DISCLOSURE OF THE INVENTION extracted from the description of groups.) have inhibitory 0019. In order to find a compound having poly(ADP-ri activity of platelet aggregation. bose)polymerase activity, the present inventors have con 0012. In the specification of WO98/31674, it is described ducted intensive studies and found, as a result, that the objects that compounds represented by formula (C) can be accomplished by the pyridazine derivative represented by formula (I), and thus the present invention has been accomplished. 0020. The present invention relates to (C) (1) a fused pyridazine derivative compound represented by formula (I) (I) O (R') - Z E se A (0021 wherein R is (wherein R' is C1-4 alkoxyetc., R is C1-8 alkoxyetc., R. (1) a hydrogen atom, (2) C1-8 alkyl, (3) C1-8 alkoxy, (4) and R' is hydrogen or RandR', taken together, are bond, hydroxy, (5) halogen atom, (6) nitro, (7) NR'R'', (8) C2-8 R is hydrogen etc. Necessary parts were extracted from the acyl, (9) C1-8 alkoxy substituted by phenyl or (10) C2-8 acyl description of groups.) have phosphodiesterase inhibitory substituted by NRR, activity. (0022 R and Rare each independently 0013. In Journal of Medicinal Chemistry., 44(16), 251 1 (1) a hydrogen atom or (2) C1-8 alkyl, 2522 and 2523-2535 (2001), it is described that 4-(3-chloro 0023 X and Y are each independently 4-methoxyphenyl)-4a,5,8,8a-tetrahydrophthalazin-1 (2H)- (1) C, (2) CH or (3) N, one (CAS Registry No. 244077-36-9) and 4-(3,4- 0024 is dimethoxyphenyl)-5,6,7,8-tetrahydrophthalazin-1 (2H)-one (1) a single bond or (2) a double bond, (CAS Registry No. 358368-98-6) have phosphodiesterase inhibitory activity. 0014. In Tetrahedron., 39(20), 3419-27 (1983), 4-phenyl x1 6,7,8,8a-tetrahydropyrrolo 1,2-d1.2.4 triazin-1 (2H)-one (CAS Registry No. 893 11-30-8) is described as synthetic YS intermediate. 0015. In Synthesis., 240-242 (1995), 4-phenyl-5,6,7,8-tet (1) partially or fully saturated C3-10 mono-carbocyclic aryl rahydrophthalazin-1 (2H)-one (CAS Registry No. 154810 or (2) partially or fully saturated 3-10 membered mono-het 22-7), 4-(4-methylphenyl)-5,6,7,8-tetrahydrophthalazin-1 ero aryl containing 1 to 4 hetero atom(s) selected from oxy (2H)-one (CAS Registry No. 154810-23-8), 4-(4- gen, nitrogen and Sulfur atoms, fluorophenyl)-5,6,7,8-tetrahydrophthalazin-1 (2H)-one 0025 A is (1) A', (2) A, (3) A, (4) A or (5) A, (CAS Registry No.
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