TW200843739A - Novel pyrrolinone derivative and composition containing the same - Google Patents
Novel pyrrolinone derivative and composition containing the same Download PDFInfo
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- TW200843739A TW200843739A TW097111332A TW97111332A TW200843739A TW 200843739 A TW200843739 A TW 200843739A TW 097111332 A TW097111332 A TW 097111332A TW 97111332 A TW97111332 A TW 97111332A TW 200843739 A TW200843739 A TW 200843739A
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- 239000000203 mixture Substances 0.000 title claims description 45
- HMXQIFUGFZEJEO-UHFFFAOYSA-N 1,2-dihydropyrrol-3-one Chemical class O=C1CNC=C1 HMXQIFUGFZEJEO-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 326
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 239000012453 solvate Substances 0.000 claims abstract description 39
- 102100040460 P2X purinoceptor 3 Human genes 0.000 claims abstract description 32
- 101710189970 P2X purinoceptor 3 Proteins 0.000 claims abstract description 29
- TZHOVNUCGUXMCS-UHFFFAOYSA-N 5-(2-ethynyl-5-propan-2-ylpyridin-4-yl)oxypyrimidine-2,4-diamine Chemical compound C(#C)C1=NC=C(C(=C1)OC=1C(=NC(=NC=1)N)N)C(C)C TZHOVNUCGUXMCS-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000001424 substituent group Chemical group 0.000 claims description 240
- -1 substituent Amine thiol Chemical class 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 125000000623 heterocyclic group Chemical group 0.000 claims description 48
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000003545 alkoxy group Chemical group 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
- 125000003277 amino group Chemical group 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 29
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 25
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 22
- 102000005962 receptors Human genes 0.000 claims description 19
- 108020003175 receptors Proteins 0.000 claims description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 239000002464 receptor antagonist Substances 0.000 claims description 14
- 229940044551 receptor antagonist Drugs 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 150000003973 alkyl amines Chemical class 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 5
- 125000000747 amidyl group Chemical group [H][N-]* 0.000 claims description 4
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 238000001354 calcination Methods 0.000 claims description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000002844 melting Methods 0.000 description 143
- 230000008018 melting Effects 0.000 description 143
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 78
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 43
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 208000002193 Pain Diseases 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 239000013078 crystal Substances 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
- 238000004519 manufacturing process Methods 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- 235000019439 ethyl acetate Nutrition 0.000 description 28
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- 239000000047 product Substances 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
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- 238000000034 method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- 238000001914 filtration Methods 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 230000035484 reaction time Effects 0.000 description 13
- 238000001953 recrystallisation Methods 0.000 description 13
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- 239000002253 acid Substances 0.000 description 12
- 238000004440 column chromatography Methods 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 150000002170 ethers Chemical class 0.000 description 11
- 150000002367 halogens Chemical group 0.000 description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 11
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 229910052736 halogen Inorganic materials 0.000 description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
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- 239000012046 mixed solvent Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000008194 pharmaceutical composition Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- 239000008096 xylene Substances 0.000 description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- 102100040479 P2X purinoceptor 2 Human genes 0.000 description 7
- 101710189968 P2X purinoceptor 2 Proteins 0.000 description 7
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- 230000000202 analgesic effect Effects 0.000 description 6
- 230000003042 antagnostic effect Effects 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 150000002430 hydrocarbons Chemical group 0.000 description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 229910052707 ruthenium Inorganic materials 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
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- 150000001335 aliphatic alkanes Chemical class 0.000 description 5
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 5
- 238000007796 conventional method Methods 0.000 description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
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- 125000002883 imidazolyl group Chemical group 0.000 description 5
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- 238000010992 reflux Methods 0.000 description 5
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- 208000011580 syndromic disease Diseases 0.000 description 5
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
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- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
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- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
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- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 description 3
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- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- POOSGDOYLQNASK-UHFFFAOYSA-N tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 1
- ZYXWYDDFNXBTFO-UHFFFAOYSA-N tetrazolidine Chemical compound C1NNNN1 ZYXWYDDFNXBTFO-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 206010048627 thoracic outlet syndrome Diseases 0.000 description 1
- 208000004371 toothache Diseases 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- YOWGRWHKDCHINP-UHFFFAOYSA-N tributyl(1,3-oxazol-2-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=NC=CO1 YOWGRWHKDCHINP-UHFFFAOYSA-N 0.000 description 1
- 229940066528 trichloroacetate Drugs 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 206010044652 trigeminal neuralgia Diseases 0.000 description 1
- DLQYXUGCCKQSRJ-UHFFFAOYSA-N tris(furan-2-yl)phosphane Chemical compound C1=COC(P(C=2OC=CC=2)C=2OC=CC=2)=C1 DLQYXUGCCKQSRJ-UHFFFAOYSA-N 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 208000014001 urinary system disease Diseases 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 210000000707 wrist Anatomy 0.000 description 1
Classifications
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- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- A61K31/4025—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil not condensed and containing further heterocyclic rings, e.g. cromakalim
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- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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- A61K31/445—Non condensed piperidines, e.g. piperocaine
- A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
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- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
- A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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Description
200843739 九、發明說明: 【發明所屬之技彳軒領域】 技術領域 本發明關於一種在治療Ρ2χ受體、特別是ρ2χ3&^ 5 P2X2/3受體相關疾病或狀態上有用之化合物以及含有該化 合物之藥學組成物。 【先前技術3 背景技術 已知ATP(二填酸腺苷)係細胞内之能量源及填酸化基 10質,另一方面,亦作為細胞外之資訊傳達物質來發揮作用。 ATP除了因細胞損傷、炎症、侵害刺激、血中氧濃度降低等 各種刺激而被放出至細胞外之外,亦會與其他神經傳導物 貝起攸初級感覺神經(Primary sensory nerve cell)末端放 出到細胞外。已放出至細胞外之ATp將會經由ATp受體而進 15行各種細胞外之資訊傳達(非專利文獻6、非專利文獻7)。 ATP受體可大致區分為離子通道型之ρ2χ家族與G蛋白 質共軛型之P2Y家族。P2X受體家族已有7種亞型(subtype) 被報告,與同貝二聚體或其他Ρ2χ亞型形成雜三聚體,而作 為非選擇性陽離子通道發揮其功能(非專利文獻8)。 20 已知ATP會引起疼痛,使用剔除(knockout)或弱化 (knockdown) P2X3技術之研究更顯示出ρ2χ3受體與慢性疼 痛之傳達相關。P2X3受體專一性地表現在末梢感覺神經, 與同質複合物或P2X2形成雜複合物非專利文獻υ。 其後,亦有一種用作Ρ2Χ3及Ρ2Χ2,3受體之專一性拮抗劑 5 200843739 且稱為Α-3Π491之化合物被報導。A_317491係以下述通式 表不之三取代-N-[(1SH,2,3,4四氫小萘基]苯甲醯胺衍生 物(專利文獻1) ’已有報導指出其對ρ2χ3及ρ2χ2/3受體顯示 出括抗活性’在大鼠之神經障礙性疼痛樣本及炎症性疼痛 5樣本中顯示出鎮痛作用(非專利文獻9)。 【化1】
此一事實顯示出,痛覺係透過Ρ2Χ3或Ρ2Χ2/3受體來傳 達’且Ρ2Χ3或Ρ2Χ2/3受體拮抗劑可用作為鎮痛藥。此外,專 1〇利文獻2〜7亦記載顯示有Ρ2Χ3或Ρ2Χ2/3受體拮抗作用之化 合物。 此外’近年有報告指出,Ρ2Χ3基因剔除小鼠顯示出顯 著之膀胱反射降低(非專利文獻2),暗示了 ρ2χ3拮抗藥在因 膀胱過度活動而引起之疾病治療上亦有用。 非專利文獻3及4記載到,與本發明化合物類似之化合 物頒不出鎮痛活性’但該等均與本發明化合物結構不同。 【專利文獻1】國際申請案WO02/094767號公開公報 【專利文獻2】國際申請案w〇2005/095359號公開公報 【專利文獻3】美國申請案US20070037974公開公報 6 200843739 【專利文獻4】美國申請案US20070049758號公開公報 【專利文獻5】美國申請案US20070049610號公開公報 【專利文獻6】美國申請案US20070049609號公開公報 【專利文獻7】美國申請案US20070049534號公開公報 5 【非專利文獻 1】Neuroscientist 11 (2005) ρρ·345-356 【非專利文獻2】J· Physiol. 567.2 (2005) ρρ·621-639 【非專利文獻 3 】Pharmaceutical Chemistry Journal Vol.39, Νο·9,(2005),pp484-487 【非專利文獻 4 】Pharmaceutical Chemistry Journal 10 Vol.31, No.5, (1997), pp251-254 【非專利文獻5】Expert Opin· Ther· Patens (2006) 16(8) 113-1127. 【非專利文獻6】J· Physiology (2003),554(2),301-308 【非專利文獻7】J· Physiology (2003),553(3), 683-694 15 【非專利文獻8】Pflungers Arch Eur J physiol (2006), 452, 513-537 【非專利文獻9】PNAS (2002),99(26),17179-17184 I:發明内容]J 發明之揭示 20 發明欲解決之課題 本發明提供一種新穎之P2X3及/或P2X2/3受體拮抗劑。 解決課題之手段 本案發明人為了達成上述目的而反覆精心研討,結果 發現與P2X3及/或P2X2/3受體專一性結合而顯示出拮抗作用 7 200843739 之新穎化合物,而完成了下述記載之發明。 (1)一種P2X3及/或P2X2/3受體拮抗劑,含有如下通式(I) 所示之化合物、其製藥上可接受之鹽或是該等之溶劑合物; 通式(I): 【化2】
式中,Z1為可任擇受到保護之羥基、可任擇受到保護 之羥胺基或可任擇具有取代基之胺基,Z2為=0或=N-E(E為 氫、羥基、可任擇具有取代基之低級烷基、可任擇具有取 10 代基之低級烷氧基或是可任擇具有取代基之胺基);或是 【化3】
R4及R5各自獨立為氫或低級烷基,R6為氫、可任擇具 有取代基之低級烷基或醯基,r為0〜2之整數;
Ra&Rb各自獨立為氫或低級烷基; q為0~4之整數; A為環烷基、環烯基、芳基或雜環基; 8 200843739 r1各自獨立為i素、羥基、可任擇具有取代基之低級 烷基、可任擇具有取代基之低級烯基、可任擇具有取代基 之低級炔基、可任擇具有取代基之低級烷氧基、可任擇具 有取代基之低級烷硫基、可任擇具有取代基之醯基、羧基、 5 可任擇具有取代基之低級烷氧羰基、可任擇具有取代基之 胺甲醯基、可任擇具有取代基之低級烷基胺甲醯基、可任 擇具有取代基之胺基、可任擇具有取代基之胺磺醯基、氰 基、硝基、可任擇具有取代基之環烷基、可任擇具有取代 基之環烯基、可任擇具有取代基之芳基或可任擇具有取代 10 基之雜環基; N為0〜3之整數(但, 【化4】
時,Α-(ί^)η亦可為氫); R2為可任擇具有取代基之烧基、可任擇具有取代基之 15低級烧氧基、可任擇具有取代基之低級烧基胺甲醯基、可 任擇具有取代基之環烷基、可任擇具有取代基之環烯基、 可任擇具有取代基之芳基或可任擇具有取代基之雜環基; R3為氫、可任擇具有取代基之烷基、可任擇具有取代 基之環烧基、可任擇具有取代基之環烯基、可任擇具有取 20代基之芳基或可任擇具有取代基之雜環基。 (2)如前述⑴之P2X3及/或P2X2,3受體拮抗劑,其中/為 羥基,Z2為=〇。 9 0 ° 200843739 ⑶如前述⑴之p2X3及/或P2X2/3受體拮抗劑,其中r為 (4)如前述⑴〜(3)中任一項之P2X3及/或P2X2/3受體拮抗 劑,其中環A為笨基、吼啶基或噻唑基。 5 (5)如前述(1)〜(4)中任一項之P2X3及/或P2X2/3受體拮抗 劑’其中R1為可任擇具有取代基之低級烷氧羰基或可任擇 具有取代基之雜環基。 (6) 如前述(1)〜(5)中任一項之P2X3及/或P2X2/3受體拮抗 劑’其中R2為可任擇具有取代基之低級烷基、可任擇具有 10取代基之笨基或可任擇具有取代基之吼啶基。 (7) 如前述(1)〜(6)中任一項之P2X3及/或P2X2/3受體拮抗 劑’其中R3為碳原子數3〜1〇之烷基、環烷基或可任擇具有 取代基之笨基。 (8) 如前述⑴〜(7)中任一項之P2X3及/或P2X2/3受體拮抗 15 劑,其中q為〇。 (9) 如前述⑴〜(7)中任一項之P2X3及/或P2X2/3受體拮抗 劑,其中q為1。 (10) —種如下通式(1,)所示之化合物、其製藥上可接受 之鹽或是該等之溶劑合物,其中通式·· 2〇【化5】 200843739
(R1D)p 式中,z1為可任擇受到保護之羥基、可受任擇保護之 爹工月女基或可任擇具有取代基之胺基,為=〇或=]\^士(e為 氫、羥基、可任擇具有取代基之低級烷基、可任擇具有取 5代基之低級烷氧基或是可任擇具有取代基之胺基;或 【化6】
1 , A ⑶ 5 R及R各自獨立為氫或低級烧基,r6為氫、可任擇具 有取代基之低級烷基或醯基,r為0〜2之整數; 10 環A及環B各自獨立為環烷基、環烯基、芳基或雜環基;
Rla&Rlb各自獨立為_素、羥基、可任擇具有取代基之 低級烷基、可任擇具有取代基之低級烯基、可任擇具有取 代基之低級炔基、可任擇具有取代基之低級烷氧基、可任 擇具有取代基之低級烷硫基、可任擇具有取代基之醯基、 15羧基、可任擇具有取代基之低級烷氧羰基、可任擇具有取 代基之胺甲醯基、可任擇具有取代基之低級烷基胺甲醯 11 200843739 基、可任擇具有取代基之胺基、可任擇具有取代基之胺磺 醯基、氰基或硝基; m及p各自獨立為〇〜2之整數; R2為可任擇具有取代基之烷基、可任擇具有取代基之 5低級烧氧基、可任擇具有取代基之低級烧基胺甲醯基、可 任擇具有取代基之環烷基、可任擇具有取代基之環烯基、 可任擇具有取代基之芳基或可任擇具有取代基之雜環基; R為氫、可任擇具有取代基之低級烧基、可任擇具有 取代基之環烷基、可任擇具有取代基之環烯基、可任擇具 10有取代基之芳基或可任擇具有取代基之雜環基; 但是,環A為吡唑酮且環b為苯基之化合物除外。 (11) 如前述(10)之化合物、其製藥上可接受之鹽或是該 等之溶劑合物,其中Z1為可任擇受到保護之羥基,22為=〇, R2為可任擇具有取代基之烷基、可任擇具有取代基之低級 15烷氧基、可任擇具有取代基之環烷基、可任擇具有取代基 之環烯基、可任擇具有取代基之芳基或可任擇具有取代基 之雜壤基。 (12) 如前述(10)之化合物、其製藥上可接受之鹽或是該 等之溶劑合物,其中r為〇, R2為可任擇具有取代基之烧基, 2〇可任擇具有取代基之低級烧氧基、可任擇具有取代基之環 烷基、可任擇具有取代基之環烯基、可任擇具有取代基之 芳基或可任擇具有取代基之雜環基。 (13) 如前述(1〇)〜(12)中任一項之化合物、其製藥上可接 X之鹽或是該等之溶劑合物,其中環A為苯基、呢啶基或噻 12 200843739 σ坐基。 (14)一種如下述通式(ι,,)所示之化合物、其製藥上可接 受之鹽或是該等之溶劑合物; 【化7】 % Ζ1 R3 乂 Ν〆 、〇 (Γ) y(R1a)m /r1c _1 J R1d 式中,Z1為可任擇受到保護之羥基、可任擇受到保護 之羥胺基或可任擇具有取代基之胺基,Z2為=0或=N-E(E為 氫、羥基、可任擇具有取代基之低級烷基、可任擇具有取 代基之低級烷氧基或可任擇具有取代基之胺基;或者 10 【化8】 ^ ^ 必 i^HCR^r \=/形成 R4及R5各自獨立形成氫或低級院基,r6為氫、可任擇 具有取代基之低級烷基或醯基,r為〇〜2之整數; 環A為環烷基、環烯基、芳基或雜環基; 15 rU各自獨立為A素、羥基、可任擇具有取代基之低級 烧基、可任擇具有取代基之低級烧氧基、可任擇具有取代 基之低級烷硫基、可任擇具有取代基之醯基、羧基、可任 13 200843739 擇具有取代基之低級烧氧幾基、可任擇具有取代基之胺甲 醯基、可任擇具有取代基之低級烷基胺甲醯基、可任擇具 有取代基之胺基、可任擇具有取代基之胺磺醯基、氰基或 硝基; 5 m為0〜2之整數;
Rle及Rld各自獨立為氫或可任擇具有取代基之低級烷 基; R2為可任擇具有取代基之烷基、可任擇具有取代基之 低級烷氧基、可任擇具有取代基之低級烷基胺甲醯基、可 ίο任擇具有取代基之環烷基、可任擇具有取代基之環烯基、 可任擇具有取代基之芳基或可任擇具有取代基之雜環基; R3為氫、可任擇具有取代基之低級烷基、可任擇具有 取代基之環烷基、可任擇具有取代基之環烯基、可任擇具 有取代基之芳基、可任擇具有取代基之雜環基。 15 (15)如前述(14)之化合物、其製藥上可接受之鹽或是該 等之溶劑合物,其中Z1為可任擇受到保護之經基,22為=〇, R2為可任擇具有取代基之烷基、可任擇具有取代基之低級 烷氧基、可任擇具有取代基之環烷基、可任擇具有取代基 之環烯基、可任擇具有取代基之芳基或可任擇具有取代基 20 之雜環基。 (16)如前述(14)之化合物、其製藥上可接受之鹽或是該 等之溶劑合物,其中r為〇, R2為可任擇具有取代基之烷基、 可任擇具有取代基之低級烧氧基、可任擇具有取代基之環 烷基、可任擇具有取代基之環烯基、可任擇具有取代基之 200843739 芳基或可任擇具有取代基之雜環基。 (17)如前述(14)〜(16)中任一項之化合物、其製藥上可接 受之鹽或是該等之溶劑合物,其中環A為苯基、定基或唉 U坐基。 5 (18)—種藥學組成物,含有如前述(1〇)〜(17)中任一項之 化合物、其製藥上可接受之鹽或是該等之溶劑合物。 (19) 一種P2X3及/或P2XW受體拮抗劑,含有如前述 (10)〜(17)中任一項之化合物、其製藥上可接受之鹽或是該 等之溶劑合物。 10 (2〇)—種如前述(10)〜(17)中任一項之化合物、其製藥上 可接受之鹽或是該等之溶劑合物的用途,係將如前述 (10)〜(17)中任一項之化合物、其製藥上可接受之鹽或是該 等之溶劑合物用於治療及/或預防P2X3及/或P2X2/3受體相 關疾病者。 15 (2D 一種P2X3及/或P2XW受體相關疾病之治療及/或預 防方法,係將如前述(10)〜(17)中任一項之化合物、其製藥 上可接受之鹽或是該等之溶劑合物進行投藥者。 此外,更以其他態樣來達成以下記載之發明。 (Γ)一種P2X3或P2X2,3受體拮抗劑,包含如下通式⑴所 2〇 示化合物、其製藥上可接受之鹽或該等之溶劑合物; 通式(I): 【化9】 15 200843739
(CRaRb)q ,,丄' '、A^~(R1)n 式中’ z1為可任擇受到保護之羥基、可任擇受到保護 之爹里胺基或可任擇具有取代基之胺基,z2為〇或NQH;或是 【化10】
R及R各自獨立為氫或低級烧基,R5為氫、低級烧基 或醯基,r為0〜2之整數; A為環烷基、環烯基、芳基或雜環基; R及R各自獨立為氫或低級烧基; q為0或1 ; R1各自獨立為_素、羥基、可任擇具有取代基之低級 烧基、可任擇具有取代基之低級烷氧基、可任擇具有取代 基之低級烧硫基、可任擇具有取代基之醯基、可任擇具有 取代基之羧基、可任擇具有取代基之低級烧氧羰基、可任 15擇具有取代基之胺曱醯基、可任擇具有取代基之低級烷基 胺甲醯基、可任擇具有取代基之胺基、可任擇具有取代基 之胺磺醯基、氰基、硝基、可任擇具有取代基之環烷基、 16 200843739 可任擇具有取代基之環烯基、可任擇具有取代基之芳基或 可任擇具有取代基之雜環基; N為〇〜3之整數;但 【化11】
R2為可任擇具有取代基之低級烷基、可任擇具有取代 基之環烷基、可任擇具有取代基之環烯基、可任擇具有取 代基之芳基或可任擇具有取代基之雜環基; R3為氫、可任擇具有取代基之烷基、可任擇具有取代 10 基之環烷基、可任擇具有取代基之環烯基、可任擇具有取 代基之芳基或可任擇具有取代基之雜環基; (2’)如前述(1,)之Ρ2χ3或ρ2χ2/3受體拮抗劑,其中/為 羥基,Z2為〇。 (3’)如前述(1,)或(2,)之Ρ2χ3或ρ2χ2/3受體拮抗劑,其中 15 A為苯基。 (4’)如前述(Γ)〜(3,)中任一項之P2X3或P2X2/3受體拮抗 劑’其中R為可任擇具有取代基之低級烷氧羰基或可任擇 具有取代基之雜環基。 (5 )如前述(1 ’)〜(4,)中任一項之P2X3或P2X2/3受體拮抗 20劑’其中r2為可任擇具有取代基之苯基或可任擇具有取代 基之σ定基。 (6 )如$述(1,)〜(5,)中任一項之Ρ2Χ3或Ρ2Χ2/3受體拮抗 17 200843739 劑’其中R3為可任擇具有取代基之碳原子數3〜10的烷基、 環烧基或可任擇具有取代基之苯基。 (7’)如前述(1,)〜(6,)中任一項之P2X3或P2X2/3受體拮抗 劑,其中q為0。 (8’)一種如下述通式(1,)所示之化合物、其製藥上可接 受之鹽或該等之溶劑合物;通式(I,)·· 【化12】
式中’ Z1為可任擇受到保護之經基、可任擇受到保護 10之羥胺基或可任擇受到保護之胺基,Z2為0或NOH ;或是 【化13】
R4及R5各自獨立為氫或低級烷基,R6為氫、低級燒基 或醯基,r為0〜2之整數; 15 環A及環B各自獨立為環烷基、環烯基、芳基或雜環基;
Rla及Rlb各自獨立為鹵素、輕基、可任擇具有取代基之 18 200843739 低級烧基、可任擇具有取代基之低級烧氧基、可任擇具有 取代基之低級烷硫基、可任擇具有取代基之醯基、羧基、 可任擇具有取代基之低級烷氧羰基、可任擇具有取代基之 胺甲酸基、可任擇具有取代基之低級烷基胺甲醯基、可任 5擇具有取代基之胺基、可任擇具有取代基之胺磺醯基、氰 基或硝基; m及p各自獨立為〇〜2之整數; R為可任擇具有取代基之低級烧基、可任擇具有取代 基之環烷基、可任擇具有取代基之環烯基、可任擇具有取 1〇代基之芳基可任擇具有取代基之雜環基; R為可任擇具有取代基之低級烧基、可任擇具有取代 基之環烷基、可任擇具有取代基之環烯基、可任擇具有取 代基之芳基或可任擇具有取代基之雜環基; 但,環A為吡唑酮且環B為苯基之化合物除外。 15 (9 )如前述(8’)之化合物、其製藥上可接受之鹽或是該 專之溶劑合物,其中Z1為可任擇受到保護之經基,z2為〇, R為可任擇具有取代基之環烷基、可任擇具有取代基之環 烯基、可任擇具有取代基之芳基或可任擇具有取代基之雜 環基。 20 (10’)一種如下述通式(I,,)所示之化合物、其製藥上可 接受之鹽或是該等之溶劑合物; 式(I”): 【化14】 19 200843739
式中,z1為可任擇受到保護之羥基、可任擇受到保護 之羥胺基或可任擇具有取代基之胺基; Z2為Ο或NOH ;或是 5 【化15】
形成 N-(CR4F^)r NR6 R及R5各自獨立為氫或低級烧基,r6為氫、低級统基 或醯基,r為0〜2之整數; 王衣A為ί衣烧基、ί哀細基、芳基或雜環基; ίο Rla各自獨立為鹵素、羥基、可任擇具有取代基之低級 院基、可任擇具有取代基之低級烧氧基、可任擇具有取代 基之低級烧硫基、可任擇具有取代基之醯基、叛基、可任 擇具有取代基之低級烧氧羰基、可任擇具有取代基之胺甲 醯基、可任擇具有取代基之低級烷基胺甲醯基、可任擇具 15有取代基之胺基、可任擇具有取代基之胺磺醯基、氰基或 硝基; m為〇〜2之整數;Rle及Rld各自獨立為氫或可任擇具有 20 200843739 取代基之低級烷基; R2為可任擇具有取代基之低級烷基、可任擇具有取代 基之環燒基、可任擇具有取代基之環稀基、可任擇具有取 代基之芳基或可任擇具有取代基之雜環基; R3為可任擇具有取代基之低級烷基、可任擇具有取代 基之環烷基、可任擇具有取代基之環婦基、可任擇具有取 代基之芳基、可任擇具有取代基之雜環基。 (1Γ) 一種藥學組成物,含有如前述(8,)〜(1〇,)中任/頊 之化B物其製藥上可接受之鹽或是該等之溶劑合物。 (12’)一種P2&或P2X2,3受體拮抗劑,含有如前述 ⑹〜⑽中任—項之化合物〜其製藥上可接受之鹽或是該 專之溶劑合物。 ⑴,)如前述(1,H7,)中任一項之ρ2χ3或ρ2χ2/3 抗劑,其係一種鎮痛劑 15 20 (14 )種鎮痛劑,含有如前述(8,)〜(1〇,)中任一項之化 合物、其製藥上可接受 , 丧又之鹽或疋该等之溶劑合物。 ()種鎮痛方法,係將如前述(1,)〜(10,)中任-項之 化合物、其製藥上可桩&)甲仕 藥者。 了接又之鹽或是該等之溶劑合物進行投 上可接為一之種骑如前述(1,)〜(1〇,)中任-項之化合物、其製藥 夕-卞,入⑶ 合物、其製藥上可接受之鹽或其等 之洛劑合物以製造鎮痛劑者。 【實施冷式】 21 200843739 本發明之最佳實施形態 本發明之化合物具有下述結構上之特徵: 1)具有吼咯啉-2-酮環作為基本骨架; 2-1)吡咯啉環之3位為烯醇型(enol form)羥基;或 2-2)吡咯啉環3位及4位之取代基共同形成下式所示之 含氮雜環(R4、R5、R6及r與前述者意義相同); 【化16】
N~(CR4R5)r NR6 ίο 3)比各啉嶮丨位之氮被下式所示之基取代(a、r1、Ra Rb、η及q與前述者意義相同); 【化17】 (CRaRb)qV A)-(R1)n 但,前述(2、2)的情況下、灿位之氮亦可不被取 代; 3-1)吼咯啉環丨位之氮被下
Rib 飞所示之基取代(A、B、Rla、 R 、m及p與别述者意義相同); 【化18】
(R1b)p 22 200843739 3-2)鱗琳環!位之氮被下式所示之基取代(a、Ria、 “。、尺^及^與前述者意義相同)。 【化19】
(R1a)m 5 此外’式(1)、(1,)及(I,,)中,n、m及/或p為2以上之整數 時’多數之R1、多數之Rla及/或多數之Rlb各自可相同或不 同。 兹將本說明書中所用之用語說明如下。各用語在未特 別§己載的箣提下具有下述意義。 10 「烷基」係指碳原子數1〜1〇(較佳為碳原子數1〜8,且 更宜為碳原子數1〜6)之直鏈或分枝狀之1價烴基,例如甲 基、乙基、正丙基、異丙基、正丁基、異丁基、第二丁基、 第三丁基、正戊基、異戊基、新戊基、正己基、異己基、 正庚基、異庚基、正辛基、異辛基、正壬基及正癸基等。 15 「低級烷基」係指碳原子數1〜6(較佳為碳原子數丨〜^ 之直鏈或分枝鏈狀1價烴基,可列舉如甲基、乙基、正丙基、 異丙基、正丁基、異丁基、第二丁基、第三丁基、正戊基、 異戊基、新戊基、正己基及異己基等。 「醯基」係指R-CO-所示之基(例如,R為前述「低級燒 20基」或後述之「低級烯基」、「芳基」、「雜環基」、「環烷基」 或「環浠基」)。 23 200843739 碳鏈。原子數3,之單環或多環狀飽和環 奴鏈。早城魏基可崎如環丙基、環丁基、 衣 環己基、職基、環辛基、環壬基 ^ 土、 烧基可列舉如降妓基等。 、“。夕城環 「環烯基」係指含有至少1個碳,雙鍵之碳原子數 3〜10的非芳㈣單環❹環狀基團。單環狀_基可列舉 «戊縣及環己稀基等。多環狀環烯可列舉如降 芳基」係指單環或縮合環之芳麵烴,可列舉如苯 10基、1-萘基、2-萘基、蒽基、菲基及茚基等。 「雜壤基」係指環内具有至少Η@氮原子、氧原子及/ 或硫原子之5〜7員環、縮合有2個以上該等原子之環,或者 是裱内具有至少1個氮原子、氧原子及/或硫原子之5〜7員環 與已縮合有至少1個前述「芳基」、「環烷基」或「環烯基」 15之環衍生出的芳香族或非芳香族單環或縮合環基。可列舉 如:吡咯啉基、吡咯啶并基(pyrr〇lidin〇)、吡咯啶基 (pyrrolidinyl)、咪唑啉基、咪唑啶基、吡唑啉基、吡唾咬基、 N-六氫吡啶基、六氫咄啶基、六氫吡畊并、 六氫°比°井基(piperazinyl)、嗎福琳基(morpholinyl)、嗎福琳 20 并基(morPholin〇)、硫代嗎福啉基、硫代嗎福啉并基、四氫 °底σ南基、二氫吼σ定基、二氫σ荅嘴基、二氫吼。井基、二。夸垸 基、氧硫雜環戊烧基(oxathiolanyl)、硫雜環己烧基 (thianyl)、四氫咬喃基、四氫旅喃基、四氫嗜β坐琳基 (tetrahydrothiazolinyl)及四氫異噻唑啉基等之非芳香族雜 24 200843739 環基;以及 °比略基、°比喷基、咕峻基、四η坐基、吱喃基、嘴吩夷、 吡啶基、咪唑基、三唑基、四唑基、三畊基、嗒啡基、旅 σ定基、吼°井基、異噚峻基、嗟。坐基、異嗟唾基、疏二唾美 5 (thiadiazolyl)、噚唑基及噚二唑基(oxadiaz〇lyl)等之單環芳 香族雜環基;及 吲垛基、異吲哚基、吲唑基、吲啡基、吲哚啉基、異 吲哚啉基、喳啉基、異喳啉基、啐喏啉基、呔畊基、喳唑 啉基、嘹啶、喳噚啉基、嘌呤基、喋啶基、苯并哌喃基、 10苯并咪唑基、苯并異噚唑基、苯并嘮唑基、苯并噚二唑基、 苯并異噻唑基、苯并噻唑基、苯并硫二唑基、苯并呋喃基、 異本弁σ夫喃基、本弁σ塞吩基、苯弁三唾基、味ϋ坐并呢σ定美 三唑并吼啶基、咪唑并噻唑基、吼畊并嗒畊基、苯并咪唑 琳基、苯并二nf烧基、四氫唆琳及四氫苯并。塞吩基等,與 15 其他環縮合而成之雜環基。 「1¾素」係指氣、氣、>臭及峨。 「低級烧氧基」係指R〇-所示之基,可列舉如R與前述 低級烷基意義相同之甲氧基、乙氧基、丙氧基、異丙氧基、 丁氧基、異丁氧基、第二丁氧基、第三丁氧基、戊氧基、 2〇異戊氧基、新戊氧基、己氧基等低級烷氧基。 「低級烧硫基」係指RS-所示之基,可列舉如r與前述 低級烷基意義相同之甲硫基、乙硫基、丙硫基、異丙硫美、 丁硫基、異丁硫基、第二丁硫基、第三丁硫基、戊硫基、 異戊硫基、新戊硫基及己硫基等低級烷硫基。 25 200843739 「低級烧氧魏基」係指ROCO-所示之基,可列舉如R 與前述低級烷基意義相同之甲氧羰基、乙氧羰基、正丙氧 羰基、異丙氧羰基、正丁氧羰基、第三丁氧羰基、正戊氧 羰基等之低級烷氧羰基。 5 「低級烷基胺甲醯基」可列舉如甲基胺曱醯基、乙基 胺甲醯基、正丙基胺甲醯基、異丙基胺曱醯基、正丁基胺 甲醯基、二甲基胺甲醯基、二乙基胺甲醯基、二丙基胺甲 基專之烧基部分碳原子數為1〜6的單或二低級烧基胺甲 醯基。 10 「亦可任擇具有取代基之低級烧基」、「亦可任擇具有 取代基之低級烯基」、「亦可任擇具有取代基之低級炔基」、 「亦可任擇具有取代基之低級烷氧基」、「亦可任擇具有取 代基之低級烷硫基」、「亦可任擇具有取代基之低級烷氧羰 基」、「亦可任擇具有取代基之低級烷基胺甲醯基」之取代 15 基可列舉如選自以下群組中1個或以上之相同或不同的取 代基,但並未僅侷限於此: 羥基、羧基、鹵素(F、a、Bp I)、卤化低級烷氧基(如 CFsO)、環烷基(如環丙基)、環烯基(如環丙烯基)、低級烷 氧基(如甲氧基、乙氧基、丙氧基、丁氧基等”低級烯氧基 20 (如乙烯氧基、烯丙氧基等)、低級烷氧羰基(如甲氧羰基、 乙氧羰基、第三丁氧羰基等)、硝基、亞硝基、胺基、低級 烷基胺基(如甲基胺基、乙基胺基、二甲基胺基等)、醯基胺 基(如乙醯基胺基、苯甲醯胺基等)、芳烷基胺基(如苄基胺 基、三苯甲基胺基)、羥基胺基、亞胺基、羥亞胺基、低級 26 200843739 烷基亞胺基(如甲基亞胺基、乙基亞胺基、二曱基亞胺基 等)、低級烷氧基亞胺基(如曱氧基亞胺基、乙氧基亞胺基 等)、醯基亞胺基(如乙醯基亞胺基、苯甲醯基亞胺基等)、 疊氮基、芳基(如苯基等)、芳烷基(如节基等)、芳烷氧基(如 5苄氧基)、氰基、異氰基、異氰酸基、氰硫基、異氰硫基、 巯基、低級烷硫基(如甲硫基等)、低級烷基磺醯基(如甲磺 醯基、乙磺醯基)、胺甲醯基、低級烷基胺甲醯基(如甲基胺 甲醯基、乙基胺曱醯基、二甲基胺甲醯基等)、胺磺醯基、 低級烷基胺磺醯基、醯基(如甲醯基、乙醯基等)、甲醯氧基、 10硫代甲醯基、硫代羧基、二硫代羧基、硫代胺曱醯基、亞 石黃酸基、磺酸基、肼基、疊氮基、脲基、甲脒基、脈基、 鄰苯二甲醯亞胺基、三低級烷基矽基(三甲矽基等)、酮基及 以下實施例所示取代基。 「可任擇具有取代基之醯基」之取代基係與前述「可 15任擇具有取代基之低級烷基」之取代基相同。醯基(R-C〇_) 之R為「方基」、「雜j哀基」、「環烧基」或「環烯基」時,亦 可令低級烷基(如甲基、乙基、異丙基、第三丁基等)、鹵化 低級烷基(如CF3、CHzCF3、C^CCl3等)、低級烯基、低級 炔基(如乙炔基)等作為取代基。 20 「可任擇具有取代基之胺甲醯基」、「可任擇具有取代 基之胺績醯基」的取代基可列舉如選自下述者所構成群組 中之1個或以上各自相同或不同的取代基’但並不限於此· 羥基、羧基、鹵素(F、Cl、Br、I)、低級烯基(如乙稀基)、 低級炔基(如乙快基)、環烧基(如環丙基)、環稀基(如環丙烯 27 200843739 基)、低級烷氧羰基(如甲氧羰基、乙氧羰基、第三丁氧羰基 荨)、月女基、低級烧胺基(如甲胺基、乙胺基、二甲基胺基等)、 醯基胺基(如乙醯基胺基、苯甲醯胺基等)、芳烷基胺基(如 苄胺基、三苯甲基胺基)、羥胺基、芳基(如苯基等)、氰基、 5異氰基、異氰酸基、氰硫基、異氰硫基、醯基(如甲醯基、 乙酿基等)及以下實施例所示之取代基。 「可任擇具有取代基之胺基」的取代基可列舉如下述 者所構成群組中之1個或以上各自相同或不同的取代基,但 並不限於此:羥基、_素〇?、0:卜;81·、;!)、函化低級烷基(如 cf3、CH2CF3、CH2CC13等)、羥基低級烷基(如羥乙基、 •C(CH3)2CH2〇H等)、鹵化低級烷氧基(如Cf3〇)、低級烷基 (如曱基、乙基、異丙基、第三丁基等)、低級烯基(如乙烯 基)、低級炔基(如乙炔基)、環烷基(如環丙基)、環烯基(如 環丙烯基)、低級烷氧基(如甲氧基、乙氧基、丙氧基、丁氧 15基等)、低級烷氧羰基(第三丁氧羰基等)、低級烯氧基(如乙 烯氧基、烯丙氧基等)、胺基、低級烷胺基(如曱胺基、乙胺 基、一甲基胺基等)、st基胺基(如乙醢基胺基、苯曱酿胺基 等)、芳院基胺基(如苄胺基、三笨甲基胺基羥胺基、亞 胺基、羥亞胺基、低級烷基亞胺基(如甲基亞胺基、乙基亞 20胺基、二曱基亞胺基等)、低級烷氧基亞胺基(如曱氧基亞胺 基、乙氧基亞胺基等)、醯基亞胺基(如乙醯基胺基、苯曱醯 基亞胺基等)、芳基(如苯基等)、芳烷基(如苄基等)、氰基、 醯基(如曱醯基、乙醯基等)及以下實施例所示取代基。 「可任擇具有取代基之環烷基」、「可任擇具有取代基 28 200843739 之環烯基」、「可任擇具有取代基之芳基」、「可任擇具有取 代基之雜環基」、「可任擇具有取代基之苯基」、「可任擇具 有取代基之吼啶基」的取代基可列舉如下述者所構成群組 中之1個或以上各自相同或不同的取代基,但並不限於此: 5羥基、羧基、鹵素(?'〇、61«、1)、_化低級烷基(如〇?3、 CH2CF3、CHfCl3等)、鹵化低級烷氧基(如CF3〇)、低級垸 基(如甲基、乙基、異丙基、第三丁基等)、低級烯基(如乙 烯基)、低級炔基(如乙炔基)、環烷基(如環丙基)、環烯基(如 環丙烯基)、低級烷氧基(如甲氧基、乙氧基、丙氧基、丁氧 10基等)、低級烯氧基(如乙烯氧基、烯丙氧基等)、低級烷氧 羰基(如甲氧羰基、乙氧羰基、第三丁氧羰基等)、硝基、亞 硝基、胺基、低級烷胺基(如甲胺基、乙胺基、二甲基胺基 等)、醯基胺基(如乙醯基胺基、苯甲醯胺基等)、芳烷基胺 基(如苄胺基、三苯甲基胺基)、羥胺基、亞胺基、羥亞胺基、 15低級烷基亞胺基(如甲基亞胺基、乙基亞胺基、二甲基亞胺 基等)、低級烷氧基亞胺基(如甲氧基亞胺基、乙氧基亞胺基 等)、醯基亞胺基(如乙醯基亞胺基、苯甲醯基亞胺基等)、 豐氮基、芳基(如苯基等)、芳烷基(如苄基等)、芳烷氧基(如 节氧基等)、氰基、異氰基、異氰酸基、氰硫基、異氛硫基、 20巯基、低級烷硫基(如甲硫基等)、低級烷基磺醯基(如甲磺 醯基、乙磺醯基)、可任擇具有取代基之胺甲醯基(如胺甲醯 基、N-甲基-N-甲氧基胺甲酸基等)、可任擇具有取代基之 低級烷基胺甲醯基(如甲基胺甲醯基、乙基胺甲醯基、二甲 基胺甲醯基、經乙基胺甲酿基、三氟甲基胺甲酸基、三氟 29 200843739 乙基胺甲醯基等)、胺磺醯基、低級烷基胺磺醯基、醯基(如 甲醯基、乙醯基等)、甲醯氧基、硫代甲醯基、硫代羧基、 二硫代魏基、硫代胺甲酸基、亞橫酸基、續酸基、肼基、 疊氮基、脲基、曱脒基、胍基、鄰苯二甲醯亞胺基、酮基 5 及以下實施例所示之取代基。 於此,鹵化低級烷基、_化低級烷氧基之_素部分與 前述「鹵素」相同。 鹵化低級烧基、低級烧胺基、低級燒基亞胺基、低級 烷基磺醯基、低級烷基胺磺醯基、低級烷基胺甲醯基、芳 10 烷基及芳烷基胺基之烷基或低級烷基部分與前述「低級烷 基」相同。 鹵化低級烷氧基及低級烷氧基亞胺基之低級烷氧基部 分與前述「低級烷氧基」相同。 「低級烯基」包含任意位置上具有1個以上雙鍵之碳原 15子數2〜6(較佳為碳原子數2〜3)之直鏈或分枝狀烯基。具體 來說,包含乙細基、丙細基、異丙烯基、丁浠基、異丁烯 基、異戊二烯基(prenyl)、丁二烯基、戊烯基、異戊烯基、 戍一炸基、己細基、異己細基及己二稀基等。 低級烯氧基之低級烯基部分與前述「低級烯基」相同。 20 「低級炔基」係指碳原子數2〜6(較佳為碳原子數2〜3) 之直鏈狀或分枝狀炔基,具體而言可列舉如乙快基、丙快 基、丁炔基、戊快基及己快基等。該等可於任意位置上具 有1個以上之三鍵,且可更具有雙鍵。 芳烧基胺基及芳烧基之芳基部分與前述「芳基」相同。 30 200843739 隨基、醯基胺基及醯基亞胺基之醯基部分與 「贫 基」相同。 「可任擇受保護之經基」及「可任擇受保護之輕胺基」 中之保護基於所屬技術領域中為習用公知者,舉例來說,」 5 醚及取代醚形成基(如甲基、甲氧基甲基、第三丁氧美甲 基、L乙氧基乙基及苄基等);矽基醚形成基(如三甲矽基、 三乙矽基、第三丁基二甲矽基及甲基-二異丙基矽基等);酯 形成基(如甲酸酯、乙酸酯及三氯乙酸酯等);碳酸酯基(如 甲基奴酸酯、2,2,2-三氯乙基碳酸酯及對硝基苯基碳酸 1〇酯等);磺醯基形成基(甲磺醯基、對甲苯磺醯基)等。 本發明化合物(1)、(1,)或(1,,)中,較佳態様係如下所示: Ζ1為羥基或羥胺基之化合物; 21為羥基之化合物; Ζ2為Ο或ΝΟΗ之化合物; Ζ為Ο之化合物;
之化合物; Α為芳基或雜環基之化合物; Α為苯基之化合物; 2〇 ^ R為可任擇具有取代基之芳基或可任擇具有取代基之 #曰麵雜環基(如嘍吩基、吡啶基、咪唑基、嘧啶基、異噚 X基塞唑基、異噻唑基、硫二唑基、噚唑基、吡唑基及 咢一 σ坐基等)的化合物,· 31 200843739 R2為可任擇具有取代基之苯基的化合物; R3為可任擇具有取代基之烷基、可任擇具有取代基之 環烷基、可任擇具有取代基之芳基或可任擇具有取代基之 雜環基的化合物; 5 r3為烷基、環烷基、可任擇具有取代基之苯基或可任 擇具有取代基之芳香族雜環基(如噻吩基、吡啶基、咪唑 基、嘧啶基、異噚唑基、噻唑基、異噻唑基、硫二唑基、 噚唑基、吡唑基及噚二唑基、喳啉基等)的化合物;及 R3為烷基、環烷基、可任擇具有取代基之苯基的化合 10 物0 本發明化合物(I)中,較佳態樣係如下所示: q為0之化合物; η為1或2,R1為鹵素、可任擇具有取代基之低級烷基、 羧基、可任擇具有取代基之低級烧氧魏基、可任擇具有取 15代基之芳基或可任擇具有取代基之雜環基的化合物; η為1或2 ’ R1為可任擇具有取代基之低級烧氧羰基、可 任擇具有取代基之芳基或可任擇具有取代基之雜環基的化 合物; η為1或2 ’ R1為可任擇具有取代基之低級烧氧羰基、可 20任擇具有取代基之苯基、可任擇具有取代基之非芳香族雜 環基(如間二氧雜環戊烧基(dioxolanyl)、味唾琳基、味峻淀 基、咐唑啉基、異噚唑琳基、噚唑琳基、噻唑啉基、異噻 唑琳基等)、可任擇具有取代基之芳香族雜環基(如嘍吩 基、吼啶基、咪唑基、嘧啶基、異噚唑基、噻唑基、異噻 32 200843739 唑基、硫二唑基、嘮唑基、吡唑基及嘮二唑基等)之化合物。 本發明化合物(I,)中,較佳態樣係如下所示: 襄B為可任擇具有取代基之非芳香族雜環基(如間二氧 /晨戊燒基、味。坐琳基、味嗤σ定基、吼唾琳基、異$唾琳 5基、圬唑啉基、噻唑啉基、異噻唑啉基等)、可任擇具有取 代基之芳香族雜環基(如噻吩基、吡啶基、咪唑基、嘧啶基、 異噚唑基、噻唑基、異噻唑基、硫二唑基、噚唑基、吡唑 基及,二啥基等)的化合物;及 m及p各自獨立為〇或丨之整數,且Rla及Rlb各自獨立為 1〇齒素、羥基、低級烷基或低級烷氧基之化合物。 本發明化合物(I,,)中,較佳態樣係如下所示·· m為0或1之整數,尺^為齒素、羥基、低級烷基或低級 烷氧基之化合物; R C為氫、可任擇具有取代基之低級烷基的化合物; 15 Rld為氫、可任擇具有取代基之低級烷基的化合物;及 R及Rld各自獨立為可任擇具有氫或取代基之低級烷 基的化合物。 紙將本發明化合物之一般合成方法顯示如下。該等合 成所用之起始物質及反應試劑均是可在商業上取得,或是 使用商業上可取得之化合物並依照所屬技術領域中周知之 方法即可製得者。 本發明之化合物(I)(即,通式⑴所示化合物。以下,其 他通式所示之化合物亦有以同樣方式略記者。)舉例來說可 經由以下所示合成路徑而製得。 33 200843739 [路徑1] 【化21】
〇 〇 R2^X^Y〇R7 +(Rl)nT〇\ 〇
Τ AV(CRaRb)q-NH2+ R3~CHO (Π) (in) (IV) (la) (^-(R1)n 式中’ R7為低級烷基,其他記號與前述者意義相同。 5 即,可使化合物(II)、化合物(III)及化合物(IV)在酸存 在下或不存在下、於無溶劑或適當溶劑中進行反應而製得 通式(la)所示之本發明化合物。 本反應中’化合物(111)及化合物(IV)相對於化合物(π) 可使用1當量或以上,且較佳可使用^當量。 10 可使用之酸可列舉如乙酸、對甲苯磺酸及鹽酸等。 可使用之溶劑可列舉如芳香族烴類(例如甲苯、笨、二 甲苯等)、飽和烴類(如環己燒、己烧等)、鍵類(如四氯咬喃、 一乙醚、二噚烷等)及該等之混合溶劑等。 反應溫度為-l〇〜15(rc,較佳為2〇〜⑽。C。反應時間雖 15依化合物而異,但使其反應10分鐘〜80小時即可。 獲知之所而化合物(Ia)可依需要而依照常法(如管柱層 析法、再結晶法等)進行純化。 [路徑2] 【化22】 34 200843739 :A^A^〇R7 + (R )n^^_(CRaRb)q、/TT, O 心 〇R7 (R1)n (II) w (V)
式中之記號與前述者意義相同。 即,使化合物(II)及化合物(V)在酸存在下或不存在 下,於無溶劑或適當溶劑中反應,可製得通式(la)所示本發 5 明化合物。 本反應中,化合物(V)相對於化合物(II)可使用1當量或 以上,且較佳為1〜3當量。 可使用之酸<!:可列舉如乙酸、對甲苯磺酸及鹽酸等。 可使用之溶劑可列舉如芳香族烴類(如甲苯、苯、二甲 10 苯等)、飽和烴類(如環己烧、己烧等)、醚類(如四氫吱喃、 二乙醚、二哼烷等)及該等之混合溶劑等。 反應溫度為-10〜150°C,較佳為20〜100°c。反應時間係 依化合物而異,但使其反應10分鐘〜80小時即可。 獲得之所需化合物(la)可依需要而以常法(如管柱層析 15 法、再結晶法等)加以純化。 [路徑3] 【化23】
Z2 71 Z2 71
0 + R1-Q 丨、 (VII) 35 200843739 式中,L及Q中之一者為二羥基硼、二低級烷基硼或二 低級烷氧基硼,另一者為鹵素或-〇S02(CsF2s+1)(s為1〜4之整 數),其他記號則與前述者意義相同。 即,可使用铃木耦合反應,使化合物(VI)及化合物(VII) 5 於鈀催化劑及鹼存在下,於適當溶劑中反應而製得通式(lb) 所示之本發明化合物。 本反應中,化合物(VII)相對於化合物(VI),可使用1當 量或以上,較佳為1〜3當量。 可使用之鹼可列舉如金屬氫氧化物(如氫氧化鈉、氫氧 10化鉀等)、金屬氫化物(如氫化鈉、氫化鋰等)、金屬碳酸鹽(如 碳酸鈉、碳酸鉀、碳酸铯等)等,相對於化合物(VI)可使用i 當ϊ或以上’且較佳為1〜5當量。 可使用之鈀催化劑可列舉如三(二亞苄基丙酮)二鈀 (〇)、乙酸鈀(II)、一氣雙二苯基膦鈀(π)或四(三苯基膦)鈀(η) 15等,相對於化合物(VI)可使用0·001當量或以上,且較佳為 0.01〜1當量。 可使用之溶劑可列舉如芳香族烴類(如甲苯、苯、二曱 苯等)、飽和烴類(如環己烧、己燒等)、_類(如四氯^南、 二乙醚、H二甲氧基乙燒等)、N,Nc甲基甲酿胺、 20 水及該等之混合溶劑等。 反應溫度為-10〜18(TC,依情況而異可微波照射化,且 宜為20~120°c。反應時間依化合物而異,但使其反應1〇分 鐘〜80小時即可。 獲得之所需化合物(Ib)可依需要而以常法(如管柱層析 36 200843739 法、再結晶法等)來進行純化。 [路徑4] 【化24】 Z2 Z1
Z2 Z1
(CRaRb)q
〇 + R1-M . (νιπ) (lb) 5 式中,L及M中之一者為三烷基錫(如_SnBu3等),另_ 者為鹵素或-〇S〇2(CsF2s+1)(s為1〜4之整數),其他記號與前 述者意義相同。 即,可使用史蒂爾氏耦合(Stillee〇upling)反應,使化合 物(VI)及化合物(VIII)於催化劑存在下於適當溶劑中反應, 10而製得通式(lb)所示之本發明化合物。 本反應中,化合物(VIII)相對於化合物(VI)可使用工當量 或以上,且較佳為1〜3當量。
等)、醚類(如四氫呋喃、 37 200843739 二乙醚、二噚烷、二甲氧基乙烷等)、N,N-二甲基甲醯胺 及該等之混合溶劑等。 反應溫度為-10〜180°C,依情況而異可照射微波,且宜 為20〜120°C。反應時間可依化合物而異,但使其反應10分 5 鐘〜80小時即可。 獲得之所需化合物(I b)可依需要而以常法(如管柱層析 法、再結晶法等)來加以純化。 [路徑5] 【化25】
式中,記號與前述者意義相同。 即,使化合物(IX)於氧化劑存在下,於適當溶劑中反 應即可製得通式(X)所示之本發明化合物。 可使用之氧化劑可列舉如二氧化錳、2-碘氧基苯甲酸 15 等,相對於化合物(IX)可使用1當量或以上,且較佳為1〜1.5 當量。 可使用之溶劑可列舉如芳香族烴類(如甲苯、苯、二曱 苯等)、飽和烴類(如環己烷、己烷等)、i化烴類(如二氯甲 烷、1,2-二氯乙烷等)、醚類(如四氫呋喃、二噚烷等)、酮 20 類(如丙酮、甲基乙基酮等)、腈類(如乙腈等)及該等之混合 溶劑等。 38 200843739 反應溫度為-10〜15(TC,較佳為2〇〜麵。c。反應時間雖 依化合物而異,但使其反應1〇分鐘〜8〇小時即可。 化合物(IX)可以粗製物型態或以常法(如管柱層析法、 再結晶法等)加以純化後用於下一步驟中。 5 [路徑5(續)] 【化26】
(c/2^b)q X1 (Ic) \^)~{ 2 JCH2)t (R1a)m 式中’ t為0〜3之整數,X1及X2各自獨立為NR8、〇或s, R8為氫或低級烷基,其他記號與前述者意義相同。 10 即,可使化合物(x)及化合物(XI)於酸存在下或不存在 下,於無溶劑或適當溶劑中反應,即可製得通式(Ic)所示本 發明化合物。 本反應中,化合物(XI)相對於化合物(X)可使用i當量或 以上,且較佳為1〜3當量。 15 可使用之酸可列舉如對甲苯磺酸、硫酸、對甲苯磺酸 0比ϋ定鐵鹽等。 可使用之溶劑可列舉如芳香族烴類(如曱苯、苯、二曱 苯等)、飽和烴類(如環己烷、己烷等)以及該等之混合溶劑 等。 20 反應溫度為-10〜17〇°C,較佳為20~150°C。反應時間係 39 200843739 依化合物而異’但使其反應10分鐘〜80小時即可。 獲得之所需化合物(1C)可依需要而以常法(如管柱層析 法、再結晶法等)來加以純化。 [路徑6] 5 【化27】
式中,記號與前述者意義相同。 即’可使化合物(X)與化合物(ΧΙΙ)或其鹽於適當溶劑中 反應,來製得通式(Id)所示本發明化合物。化合物(ΧΙΙ)及其 10鹽相對於化合物(X)係使用1〜4當量,且較佳為i〜2.5當量。 化合物(XII)之鹽可列舉如鹽酸鹽、硫酸鹽等礦酸鹽 等。使用該鹽時,係以鹼中和後進行反應。 可使用之鹼可列舉如乙酸鈉、胺類(吡啶等)等,其使用量相 對於化合物(XI)之鹽為U當量,較佳為i〜2當量。 15 可使用之〉谷劑可列舉如烴類(如苯、甲苯、二甲苯等)、 鹵化烴類(如氣仿、1,2-二氣乙烷等)、醚類(如四氫呋喃、 二哼烷等)、醇類(如甲醇、乙醇、正丙醇、異丙醇等)、水 及該等之混合溶劑等。 反應溫度為0~150°C,較佳為2〇〜120°C。 反應日ττ間通S為10分鐘〜24小時程度。 40 20 200843739 獲得之所需化合物(I d)可依需要而以常法(如管柱層析 法、再結晶法等)來加以純化。 [路徑7] 【化28】
式中,Hal為鹵素,R9為羥基之保護基,其他記號與前 述者同義。 即,可使化合物(la)與化合物(XIII)於鹼存在下,於適 當溶劑中進行反應而製得通式(Ie)所示之本發明化合物。化 10 合物(XII)相對於化合物(la)可使用1〜4當量,較佳為1〜2.5當 量。 可使用之鹼可列舉如胺類(三乙胺、吡啶等)等,其使用 量相對於化合物(la)為1〜3當量,較佳為1〜2當量。 可使用之溶劑可列舉如烴類(如苯、曱苯、二甲苯等)、 15 _化烴類(如氯仿、1,2-二氯乙烧等)、醚類(如四氫吱喃、 二噚烷等)、Ν,Ν-二曱基甲醯胺、二曱基亞砜及該等之混 合溶劑等。 反應溫度為-20〜150°C,較佳為0〜120°C。 反應時間通常為10分鐘〜24小時程度。 20 獲得之所需化合物(Ie)可依需要而以常法(如管柱層析 41 200843739 法、再結晶法等)來加以純化。 [路徑8] 【化29】
5 式中,記號與前述者同義。 即,使化合物(la)與胺類或其鹽於適當溶劑中反應,可 製得通式(If)或通式(Ig)所示本發明化合物。胺類及其鹽相 對於化合物(la)係使用1〜4當量,且較佳為1〜2.5當量。 羥基胺之鹽可列舉如鹽酸鹽、硫酸鹽等之礦酸鹽等。 10 使用該鹽時,係以鹼進行中和而使其反應。 可使用之鹼可列舉如乙酸鈉、胺類(吡啶等)等,其使用 量相對於胺類之鹽為1〜3當量,且較佳為1〜2當量。 可使用之溶劑可列舉如烴類(如苯、甲苯、二甲苯等)、 鹵化烴類(如氯仿、1,2-二氯乙烷等)、醚類(如四氫呋喃、 15 二噚烷等)、醇類(如甲醇、乙醇、正丙醇、異丙醇等)、水 及該等之混合溶劑等。 反應溫度為0〜150°C,且較宜為20〜120°C。 反應時間通常為15分鐘〜24小時程度。 獲得之所需化合物(If)或化合物(Ig)可依需要而以常法 20 (如管柱層析法、再結晶法等)來加以純化。 [路徑9] 42 200843739 【化30】
式中,記號與前述者同義。 5 10 15 即,可使化合物(la)與化合物(χιν)於適當溶劑中反 應,而製得通式(ih)所示本發明化合物。化合物(χιν)相對 於化合物(la)係使用1〜4當量,且較佳為^2 5當量。 可使用之溶劑可列舉如乙酸、煙類(如苯、甲苯、二甲 苯等)、醚類(如四氫吱喃、二桃等)、醇類(如甲醇、乙醇、 正丙醇、異丙醇等)及該等之混合溶劑等。 反應溫度為〇〜i5(rc,較佳為5〇〜i3(rc。 反應時間通常為10分鐘〜24小時程度。 獲得之所需化合物⑽可依需要而;常法(如管柱層析 法、再結晶法等)來加以純化。 _ % 可形成製藥學上可接受之其與酸或驗之 鹽酸、硫酸、碩酸、磷酸、氟化氫酸、 酒石酸、乳酸、棒樣;Λ 、號· 三乙基銨;:機 以及,簡㈣、鉀祕金屬之鹽; 本么月化合物或前述製藥上可接受之鹽亦可製 43 20 200843739 成其溶劑合物(較佳為水合物)之溶劑合物。溶劑合物可列舉 如與有機溶劑及/或水之溶劑合物。形成溶劑合物時,可與 任意數量之溶劑分子任擇地配位。 本發明化合物(I)並不限於特定之異構物,而包含所有 5 可能之異構物及消旋體。例如,含有下述之互變異構物。 【化31】
本發明之化合物可為具有特定立體配置且業經離析之 鏡向異構物、或是該等鏡向異構物之混合物。舉例來說, 10 本發明之化合物可以是在吡咯啶并環之5位上具有特定立 44 200843739 體配置且經離析之鏡向異構物或該鏡向異構物之混合物。 舉例來說,當業者可採用結晶化、酶反應、層析法等所屬 技術項域中j貝用之技術而容易地離析出具有特定立體配置 之鏡向異構物。 5 10 15 20 月ίΐ述通式(1)所示本發明化合物具有對於ρ2Χ3及/或 P2X2/3文體之拮抗作用,作為P2X3及/或ρ2χ奶相關疾病之治 療劑甚為有用。P^3及/或似的受體被認為與疼痛及泌尿 系統疾病相 _咖e 撕,26, um_1()15 (2_),Nature,
Vo副,No.26, 1015韻(2_)、非專利文獻卜非專利文 _ ) 頜風濕性關節炎所伴隨之疼痛、變形性關節 炎所伴隨之疼痛、頭痛、偏頭痛、口腔顏面痛、牙痛、舌 痛症、顳f員關節炎所倖左 、/人所机之疼痛、三叉神經痛、肩痛、椎 曰:大扣所伴隨之疼痛、變形性頸椎症所伴隨之疼痛、脊 狹乍所伴隨之疼痛、胸廓出口綜合症⑽ rrzrm腕神《損傷症候群所伴隨之疼 =膽結石所伴隨之疼痛、胰扁 迢結石症、過敏性腸症 、眉尿 骨神經痛、骨折所伴腰肺部痛、坐 S气Μ虑、s 涌、月質疏鬆症所伴隨之疼痛、 二生二風所伴隨m馬尾症候群所伴隨之疼痛 僵直性錄炎所伴隨 得&之疼痛、 症候群、纖維肌痛症候群 手肌㈣ 痛、柏格氏症所伴隨之疼/^"動脈硬化症所伴隨之疼 帶狀癌療所伴隨之料U諾氏現象所伴隨之疼痛、 3熱痛、神經壓迫症候群所伴隨 45 200843739 痛、道症候群所伴隨之疼痛、糖尿病所伴隨之疼 藥物療法:隨ΓΓΓ之疼痛、韓森氏病所伴隨之疼痛、 4- ^ 您、痛、放射線療法所伴隨之瘃痛、ϋ 5 10 15
Xir; r 交感神經維持.二::;=(Dr— 病所伴、、 w候群、夕發性硬化症、皮膚 揀癌性疼痛、術後痛、外傷所伴隨之疼痛、 =、冑之疼痛、心身症所伴隨之疼痛、體化症所伴隨 、痛、«症所伴隨之疼痛、帕金森氏症 =節痛、關節炎所伴隨之疼痛、生理痛、中二 痛專神經障礙性_、t錄賴、錢接受性疼痛、心 因性疼細及駿_胱、尿失禁、縣、尿意緊迫⑽ urgency)、膀胱萎縮、前列腺肥大、前列腺炎、射_、 逼尿肌過度反射(detrusor hyperreflesxia)、排尿障礙、神經 性頻尿、慢性前列腺炎、慢性膀胱炎等,而在治療、緩和 症狀或預防上有效。 本發明之化合物對於ATP受體、特別是现受體具有 高親和性,亞型選擇性及對於其他受體之選擇性亦高了而 可成為副作用(如對運動機能之影響等)降低之藥物。此外, 2〇本發明之化合物亦具有安定性高、經口吸收性佳、顯示出 良好之生體利用率、清除率(ciearance)低、半衰期長、藥效 持續性高及/或肝酶阻礙活性低等優點。 於其他態樣中,本發明提供一種藥學組成物,其含有 有效量之本發明化合物與製藥學上可接受之载體的組合。 46 200843739 將本發明化合物用作藥品時,舉例來說,可使用賦形 刮、結合劑、崩解劑、滑澤劑、著色劑、續味劑、端臭劑、 界面活性劑等所屬技術領域中周知之製藥上可接受之載 體而依常法來製造藥學組成物。 5、=本發明之藥學組成物投料包含人類之哺乳動物以 ^者療日^ ’投藥單位劑形可依治療目的及投藥路徑來加 以適當選擇。具體來說,可列舉如旋劑、膜衣錠、粉劑、 、、/州膠暴劑、液劑、丸劑、懸濁劑、乳劑等經口製劑, ^及及注射劑、栓劑、軟膏、貼劑、噴霧劑等非經口製劑。 10该等投藥單位劑形可以所屬領域巾周知之方法進行製劑 化。 鈾述敁劑中應含之本發明化合物量可依照劑型、投藥 路徑、投藥計畫等來適當變更。 本發明之藥學組成物之投藥方法可依製劑之劑形、患 15者年齡、性別、體重、症狀程度及其他條件等來適當地決 疋,可選擇經口、皮下、經皮、直腸、鼻内、口腔等各種 路梭。 本舍明之樂學組成物所含有之本發明化合物的用量可 依所選擇之投藥路徑、患者年齡、性別、體重、疾病狀態、 20所投藥之本發明化合物種類以及其他條件等加以適當選 擇’但對成人實施經口投藥時,通常為〇.〇5〜i〇〇〇mg/kg/曰, 較佳為0.1〜l〇mg/kg/曰之範圍内。非經口投藥時,將依投藥 路控而大為不同,但通常為0.005〜l〇〇mg/kg/日,且較佳為 〇·〇1〜lmg/kg/曰之範圍内。該等本發明之藥學組成物可1曰i 47 200843739 次或分成數次進行投藥。 本發明化合物之較佳態樣係於下式(a)〜(f)中具有下述 基團者。 【化32】
(4 ⑻ m Pf0*1* 48 200843739 表1
Z1 ZA OH ZB OAc ZC NHOH 表2 R1 R1A COOEt RIB cf3 R1C ocf3 RID scf3 R1E Ac RIF Br RIG 2-或5-呤唑基 R1H 異哼唑-3-基 R1I 3-Me-異噚唑-5-基 R1J 5-Me-異噚唑-3-基 R1K 1,2,4-噚二唑-3-基 R1L 1,3,4-哼二唑-2-基 RIM 5-Me-l,2,4-哼二唑-3-基 R1N 3-Me-l,2,4-哼二唑-5-基 RIO C(Me)=NOMe RIP CH=NOMe R1Q 2-哼唑啉基 R1R 2-嘆唾琳基 R1S 1,3-二噚烷-2-基 表3 R2 R2A iPr R2B nBu R2C tBu R2D cBu R2E cHex R2F Ph R2G 4-C1 或 F-Ph R2H 4-N02-Ph R2I 4-CF3-Ph R2J 4-Me2N-Ph R2K 2-或3-噻吩基 R2L 3-°比°定基 R2M 6-ΜθΟ-3-σΛσ定基 R2N 2 或 3 或 4-MeO-Ph 49 200843739 表4 R3 R3A iPr R3B Et2CH R3C Pr2CH R3D nBu2CH R3E Pr(Me)CH R3F Ph(Me)CH R3G cPent R3H cHex R3I Ph R3J 2-Cl-Ph R3K 2-或 3-或 4-Me-Ph R3L 2-或 3-或 4-MeO-Ph R3M 2-或 3-或 4-F-Ph R3N 3-或 4-Cl-Ph R30 2-σΛσ定基 R3P 4-六氮吼σ定基 R3Q l_Ac-4-六鼠ϋΐί»σ定基 R3R 四氫哌喃-4-基 前述表中,Ac為乙醯基、Me為甲基、Et為乙基、Pr為 丙基、iPr為異丙基、nBu為正丁基、tBu為第三丁基、cBu 為環丁基、cPent為環戊基、cHex為環己基、Ph為苯基。 5 Z1、R1、R2及R3之組合01,111,112,尺3)為下述各化合物。
(Z1,R1,R2,R3)=(ZA,R1A,R2A,R3A),(ZA,R1A,R2A,R3 B),(ZA,R1A,R2A,R3C),(ZA,R1A,R2A,R3D),(ZA,R1A,R2A, R3E),(ZA,R1A,R2A,R3F),(ZA,R1A,R2A,R3G),(ZA,R1A,R2 A,R3H),(ZA,R1A,R2A,R3I),(ZA,R1A,R2A,R3J),(ZA,R1A,R 10 2A,R3K),(ZA,R1A,R2A,R3L),(ZA,R1A,R2A,R3M),(ZA,R1A ,R2A,R3N),(ZA,R1A,R2A,R30),(ZA,R1A,R2A,R3P),(ZA,R1 A,R2A,R3Q),(ZA,R1A,R2A,R3R),(ZA,R1A,R2B,R3A),(ZA, R1A,R2B,R3B),(ZA,R1A,R2B,R3C),(ZA,R1A,R2B,R3D),(Z A,R1A,R2B,R3E),(ZA,R1A,R2B,R3F),(ZA,R1A,R2B,R3G),( 50 200843739 ZA,R1A,R2B,R3H),(ZA,R1A,R2B,R3I),(ZA,R1A,R2B,R3J),( ZA,R1A,R2B,R3K),(ZA,R1A,R2B,R3L),(ZA,R1A,R2B,R3M) ,(ZA,R1A,R2B,R3N),(ZA,R1A,R2B,R30),(ZA,R1A,R2B,R3 P),(ZA,R1A,R2B,R3Q),(ZA,R1A,R2B,R3R),(ZA,R1A,R2C,R 5 3A),(ZA,R1A,R2C,R3B),(ZA,R1A,R2C,R3C),(ZA,R1A,R2C,
R3D),(ZA,R1A,R2C,R3E),(ZA,R1A,R2C,R3F),(ZA,R1A,R2 C,R3G),(ZA,R1A,R2C,R3H),(ZA,R1A,R2C,R3I),(ZA,R1A,R 2C,R3J),(ZA,R1A,R2C,R3K),(ZA,R1A,R2C,R3L),(ZA,R1A, R2C,R3M),(ZA,R1A,R2C,R3N),(ZA,R1A,R2C,R30),(ZA,R1 10 A,R2C,R3P),(ZA,R1A,R2C,R3Q),(ZA,R1A,R2C,R3R),(ZA,R 1A,R2D,R3A),(ZA,R1A,R2D,R3B),(ZA,R1A,R2D,R3C),(ZA, R1A,R2D,R3D),(ZA,R1A,R2D,R3E),(ZA,R1A,R2D,R3F),(Z A,R1A,R2D,R3G),(ZA,R1A,R2D,R3H),(ZA,R1A,R2D,R3I),( ZA,R1A,R2D,R3J),(ZA,R1A,R2D,R3K),(ZA,R1A,R2D,R3L), 15 (ZA,R1A,R2D,R3M),(ZA,R1A,R2D,R3N),(ZA,R1A,R2D,R3 0),(ZA,R1A,R2D,R3P),(ZA,R1A,R2D,R3Q),(ZA,R1A,R2D, R3R),(ZA,R1A,R2E,R3A),(ZA,R1A,R2E,R3B),(ZA,R1A,R2 E,R3C),(ZA,R1A,R2E,R3D),(ZA,R1A,R2E,R3E),(ZA,R1A,R 2E,R3F),(ZA,R1A,R2E,R3G),(ZA,R1A,R2E,R3H),(ZA,R1A, 20 R2E,R3I),(ZA,R1A,R2E,R3J),(ZA,R1A,R2E,R3K),(ZA,R1A, R2E,R3L),(ZA,R1A,R2E,R3M),(ZA,R1A,R2E,R3N),(ZA,R1 A,R2E,R30),(ZA,R1A,R2E,R3P),(ZA,R1A,R2E,R3Q),(ZA,R 1A,R2E,R3R),(ZA,R1A,R2F,R3A),(ZA,R1A,R2F,R3B),(ZA, R1A,R2F,R3C),(ZA,R1A,R2F,R3D),(ZA,R1A,R2F,R3E),(ZA, 51 200843739
R1A,R2F,R3F),(ZA,R1A,R2F,R3G),(ZA,R1A,R2F,R3H),(ZA, R1A,R2F,R3I),(ZA,R1A,R2F,R3J),(ZA,R1A,R2F,R3K),(ZA, R1A,R2F,R3L),(ZA,R1A,R2F,R3M),(ZA,R1A,R2F,R3N),(ZA ,R1A,R2F,R30),(ZA,R1A,R2F,R3P),(ZA,R1A,R2F,R3Q),(ZA 5 ,R1A,R2F,R3R),(ZA,R1A,R2G,R3A),(ZA,R1A,R2G,R3B),(Z A,R1A,R2G,R3C),(ZA,R1A,R2G,R3D),(ZA,R1A,R2G,R3E),( ZA,R1A,R2G,R3F),(ZA,R1A,R2G,R3G),(ZA,R1A,R2G,R3H), (ZA,R1A,R2G,R3I),(ZA,R1A,R2G,R3J),(ZA,R1A,R2G,R3K), (ZA,R1A,R2G,R3L),(ZA,R1A,R2G,R3M),(ZA,R1A,R2G,R3N 10 ),(ZA,R1A,R2G,R30),(ZA,R1A,R2G,R3P),(ZA,R1A,R2G,R3 Q),(ZA,R1A,R2G,R3R),(ZA,R1A,R2H,R3A),(ZA,R1A,R2H, R3B),(ZA,R1A,R2H,R3C),(ZA,R1A,R2H,R3D),(ZA,R1A,R2 H,R3E),(ZA,R1A,R2H,R3F),(ZA,R1A,R2H,R3G),(ZA,R1A,R 2H,R3H),(ZA,R1A,R2H,R3I),(ZA,R1A,R2H,R3J),(ZA,R1A, 15 R2H,R3K),(ZA,R1A,R2H,R3L),(ZA,R1A,R2H,R3M),(ZA,R1 A,R2H,R3N),(ZA,R1A,R2H,R30),(ZA,R1A,R2H,R3P),(ZA, R1A,R2H,R3Q),(ZA,R1A,R2H,R3R),(ZA,R1A,R2I,R3A),(Z A,R1A,R2I,R3B),(ZA,R1A,R2I,R3C),(ZA,R1A,R2I,R3D),(Z A,R1A,R2I,R3E),(ZA,R1A,R2I,R3F),(ZA,R1A,R2I,R3G),(Z 20 A,R1A,R2I,R3H),(ZA,R1A,R2I,R3I),(ZA,R1A,R2I,R3J),(ZA, R1A,R2I,R3K),(ZA,R1A,R2I,R3L),(ZA,R1A,R2I,R3M),(ZA, R1A,R2I,R3N),(ZA,R1A,R2I,R30),(ZA,R1A,R2I,R3P),(ZA, R1A,R2I,R3Q),(ZA,R1A,R2I,R3R),(ZA,R1A,R2J,R3A),(ZA, R1A,R2J,R3B),(ZA,R1A,R2J,R3C),(ZA,R1A,R2J,R3D),(ZA, 52 200843739 R1A,R2J,R3E),(ZA,R1A,R2J,R3F),(ZA,R1A,R2J,R3G),(ZA, R1A,R2J,R3H),(ZA,R1A,R2J,R3I),(ZA,R1A,R2J,R3J),(ZA,R 1A,R2J,R3K),(ZA,R1A,R2J,R3L),(ZA,R1A,R2J,R3M),(ZA,R 1A,R2J,R3N),(ZA,R1A,R2J,R30),(ZA,R1A,R2J,R3P),(ZA,R 5 1A,R2J,R3Q),(ZA,R1A,R2J,R3R),(ZA,R1A,R2K,R3A),(ZA, R1A,R2K,R3B),(ZA,R1A,R2K,R3C),(ZA,R1A,R2K,R3D),(Z A,R1A,R2K,R3E),(ZA,R1A,R2K,R3F),(ZA,R1A,R2K,R3G),( ZA,R1A,R2K,R3H),(ZA,R1A,R2K,R3I),(ZA,R1A,R2K,R3J), (ZA,R1A,R2K,R3K),(ZA,R1A,R2K,R3L),(ZA,R1A,R2K,R3 10 M),(ZA,R1A,R2K,R3N),(ZA,R1A,R2K,R30),(ZA,R1A,R2K,
R3P),(ZA,R1A,R2K,R3Q),(ZA,R1A,R2K,R3R),(ZA,R1A,R2 L,R3A),(ZA,R1A,R2L,R3B),(ZA,R1A,R2L,R3C),(ZA,R1A,R 2L,R3D),(ZA,R1A,R2L,R3E),(ZA,R1A,R2L,R3F),(ZA,R1A, R2L,R3G),(ZA,R1A,R2L,R3H),(ZA,R1A,R2L,R3I),(ZA,R1A 15 ,R2L,R3J),(ZA,R1A,R2L,R3K),(ZA,R1A,R2L,R3L),(ZA,R1A ,R2L,R3M),(ZA,R1A,R2L,R3N),(ZA,R1A,R2L,R30),(ZA,R1 A,R2L,R3P),(ZA,R1A,R2L,R3Q),(ZA,R1A,R2L,R3R),(ZA,R 1A,R2M,R3A),(ZA,R1A,R2M,R3B),(ZA,R1A,R2M,R3C),(Z A,R1A,R2M,R3D),(ZA,R1A,R2M,R3E),(ZA,R1A,R2M,R3F), 20 (ZA,R1A,R2M,R3G),(ZA,R1A,R2M,R3H),(ZA,R1A,R2M,R3 I),(ZA,R1A,R2M,R3J),(ZA,R1A,R2M,R3K),(ZA,R1A,R2M,R 3L),(ZA,R1A,R2M,R3M),(ZA,R1A,R2M,R3N),(ZA,R1A,R2 M,R30),(ZA,R1A,R2M,R3P),(ZA,R1A,R2M,R3Q),(ZA,R1A, R2M,R3R),(ZA,R1A,R2N,R3A),(ZA,R1A,R2N,R3B),(ZA,R1 53 200843739 A,R2N,R3C),(ZA,R1A,R2N,R3D),(ZA,R1A,R2N,R3E),(ZA, R1A,R2N,R3F),(ZA,R1A,R2N,R3G),(ZA,R1A,R2N,R3H),(Z A,R1A,R2N,R3I),(ZA,R1A,R2N,R3J),(ZA,R1A,R2N,R3K),( ZA,R1A,R2N,R3L),(ZA,R1A,R2N,R3M),(ZA,R1A,R2N,R3N 5 ),(ZA,R1A,R2N,R30),(ZA,R1A,R2N,R3P),(ZA,R1A,R2N,R3 Q),(ZA,R1A,R2N,R3R),(ZA,R1B,R2A,R3A),(ZA,R1B,R2A, R3B),(ZA,R1B,R2A,R3C),(ZA,R1B,R2A,R3D),(ZA,R1B,R2 A,R3E),(ZA,R1B,R2A,R3F),(ZA,R1B,R2A,R3G),(ZA,R1B,R 2A,R3H),(ZA,R1B,R2A,R3I),(ZA,R1B,R2A,R3J),(ZA,R1B,R 10 2A,R3K),(ZA,R1B,R2A,R3L),(ZA,R1B,R2A,R3M),(ZA,R1B,
R2A,R3N),(ZA,R1B,R2A,R30),(ZA,R1B,R2A,R3P),(ZA,R1 B,R2A,R3Q),(ZA,R1B,R2A,R3R),(ZA,R1B,R2B,R3A),(ZA,R 1B,R2B,R3B),(ZA,R1B,R2B,R3C),(ZA,R1B,R2B,R3D),(ZA, R1B,R2B,R3E),(ZA,R1B,R2B,R3F),(ZA,R1B,R2B,R3G),(ZA 15 ,R1B,R2B,R3H),(ZA,R1B,R2B,R3I),(ZA,R1B,R2B,R3J),(ZA ,R1B,R2B,R3K),(ZA,R1B,R2B,R3L),(ZA,R1B,R2B,R3M),(Z A,R1B,R2B,R3N),(ZA,R1B,R2B,R30),(ZA,R1B,R2B,R3P),( ZA,R1B,R2B,R3Q),(ZA,R1B,R2B,R3R),(ZA,R1B,R2C,R3A), (ZA,R1B,R2C,R3B),(ZA,R1B,R2C,R3C),(ZA,R1B,R2C,R3D 20 ),(ZA,R1B,R2C,R3E),(ZA,R1B,R2C,R3F),(ZA,R1B,R2C,R3
G),(ZA,R1B,R2C,R3H),(ZA,R1B,R2C,R3I),(ZA,R1B,R2C,R 3J),(ZA,R1B,R2C,R3K),(ZA,R1B,R2C,R3L),(ZA,R1B,R2C,R 3M),(ZA,R1B,R2C,R3N),(ZA,R1B,R2C,R30),(ZA,R1B,R2C, R3P),(ZA,R1B,R2C,R3Q),(ZA,R1B,R2C,R3R),(ZA,R1B,R2D 54 200843739
,R3A),(ZA,R1B,R2D,R3B),(ZA,R1B,R2D,R3C),(ZA,R1B,R2 D,R3D),(ZA,R1B,R2D,R3E),(ZA,R1B,R2D,R3F),(ZA,R1B,R 2D,R3G),(ZA,R1B,R2D,R3H),(ZA,R1B,R2D,R3I),(ZA,R1B, R2D,R3J),(ZA,R1B,R2D,R3K),(ZA,R1B,R2D,R3L),(ZA,R1B 5 ,R2D,R3M),(ZA,R1B,R2D,R3N),(ZA,R1B,R2D,R30),(ZA,R
1B,R2D,R3P),(ZA,R1B,R2D,R3Q),(ZA,R1B,R2D,R3R),(ZA, R1B,R2E,R3A),(ZA,R1B,R2E,R3B),(ZA,R1B,R2E,R3C),(ZA ,R1B,R2E,R3D),(ZA,R1B,R2E,R3E),(ZA,R1B,R2E,R3F),(ZA ,R1B,R2E,R3G),(ZA,R1B,R2E,R3H),(ZA,R1B,R2E,R3I),(ZA 10 ,R1B,R2E,R3J),(ZA,R1B,R2E,R3K),(ZA,R1B,R2E,R3L),(ZA ,R1B,R2E,R3M),(ZA,R1B,R2E,R3N),(ZA,R1B,R2E,R30),(Z A,R1B,R2E,R3P),(ZA,R1B,R2E,R3Q),(ZA,R1B,R2E,R3R),( ZA,R1B,R2F,R3A),(ZA,R1B,R2F,R3B),(ZA,R1B,R2F,R3C),( ZA,R1B,R2F,R3D),(ZA,R1B,R2F,R3E),(ZA,R1B,R2F,R3F),( 15 ZA,R1B,R2F,R3G),(ZA,R1B,R2F,R3H),(ZA,R1B,R2F,R3I),( ZA,R1B,R2F,R3J),(ZA,R1B,R2F,R3K),(ZA,R1B,R2F,R3L),( ZA,R1B,R2F,R3M),(ZA,R1B,R2F,R3N),(ZA,R1B,R2F,R30), (ZA,R1B,R2F,R3P),(ZA,R1B,R2F,R3Q),(ZA,R1B,R2F,R3R), (ZA,R1B,R2G,R3A),(ZA,R1B,R2G,R3B),(ZA,R1B,R2G,R3C) 20 ,(ZA,R1B,R2G,R3D),(ZA,R1B,R2G,R3E),(ZA,R1B,R2G,R3F)
,(ZA,R1B,R2G,R3G),(ZA,R1B,R2G,R3H),(ZA,R1B,R2G,R3I) ,(ZA,R1B,R2G,R3J),(ZA,R1B,R2G,R3K),(ZA,R1B,R2G,R3L) ,(ZA,R1B,R2G,R3M),(ZA,R1B,R2G,R3N),(ZA,R1B,R2G,R3 0),(ZA,R1B,R2G,R3P),(ZA,R1B,R2G,R3Q),(ZA,R1B,R2G,R 55 200843739 3R),(ZA,R1B,R2H,R3A),(ZA,R1B,R2H,R3B),(ZA,R1B,R2H9 R3C),(ZA,R1B,R2H,R3D),(ZA,R1B,R2H,R3E),(ZA,R1B,R2 H,R3F),(ZA,R1B,R2H,R3G),(ZA,R1B,R2H,R3H),(ZA,R1B,R 2H,R3I),(ZA,R1B,R2H,R3J),(ZA,R1B,R2H,R3K),(ZA,R1B,R 5 2H,R3L),(ZA,R1B,R2H,R3M),(ZA,R1B,R2H,R3N),(ZA,R1B, R2H,R30),(ZA,R1B,R2H,R3P),(ZA,R1B,R2H,R3Q),(ZA,R1 B,R2H,R3R),(ZA,R1B,R2I,R3A),(ZA,R1B,R2I,R3B),(ZA,R1 B,R2I,R3C),(ZA,R1B,R2I,R3D),(ZA,R1B,R2I,R3E),(ZA,R1B ,R2I,R3F),(ZA,R1B,R2I,R3G),(ZA,R1B,R2I,R3H),(ZA,R1B, 10 R2I,R3I),(ZA,R1B,R2I,R3J),(ZA,R1B,R2I,R3K),(ZA,R1B,R2 I,R3L),(ZA,R1B,R2I,R3M),(ZA,R1B,R2I,R3N),(ZA,R1B,R2I ,R30),(ZA,R1B,R2I,R3P),(ZA,R1B,R2I,R3Q),(ZA,R1B,R2I, R3R),(ZA,R1B,R2J,R3A),(ZA,R1B,R2J,R3B),(ZA,R1B,R2J, R3C),(ZA,R1B,R2J,R3D),(ZA,R1B,R2J,R3E),(ZA,R1B,R2J, 15 R3F),(ZA,R1B,R2J,R3G),(ZA,R1B,R2J,R3H),(ZA,R1B,R2J, R3I),(ZA,R1B,R2J,R3J),(ZA,R1B,R2J,R3K),(ZA,R1B,R2J,R 3L),(ZA,R1B,R2J,R3M),(ZA,R1B,R2J,R3N),(ZA,R1B,R2J,R 30),(ZA,R1B,R2J,R3P),(ZA,R1B,R2J,R3Q),(ZA,R1B,R2J,R3 R),(ZA,R1B,R2K,R3A),(ZA,R1B,R2K,R3B),(ZA,R1B,R2K,R 20 3C),(ZA,R1B,R2K,R3D),(ZA,R1B,R2K,R3E),(ZA,R1B,R2K, R3F),(ZA,R1B,R2K,R3G),(ZA,R1B,R2K,R3H),(ZA,R1B,R2 K,R3I),(ZA,R1B,R2K,R3J),(ZA,R1B,R2K,R3K),(ZA,R1B,R2 K,R3L),(ZA,R1B,R2K,R3M),(ZA,R1B,R2K,R3N),(ZA,R1B, R2K,R30),(ZA,R1B,R2K,R3P),(ZA,R1B,R2K,R3Q),(ZA,R1 56 200843739
B,R2K,R3R),(ZA,R1B,R2L,R3A),(ZA,R1B,R2L,R3B),(ZA,R 1B,R2L,R3C),(ZA,R1B,R2L,R3D),(ZA,R1B,R2L,R3E),(ZA, R1B,R2L,R3F),(ZA,R1B,R2L,R3G),(ZA,R1B,R2L,R3H),(ZA ,R1B,R2L,R3I),(ZA,R1B,R2L,R3J),(ZA,R1B,R2L,R3K),(ZA, 5 R1B,R2L,R3L),(ZA,R1B,R2L,R3M),(ZA,R1B,R2L,R3N),(Z A,R1B,R2L,R30),(ZA,R1B,R2L,R3P),(ZA,R1B,R2L,R3Q),( ZA,R1B,R2L,R3R),(ZA,R1B,R2M,R3A),(ZA,R1B,R2M,R3B ),(ZA,R1B,R2M,R3C),(ZA,R1B,R2M,R3D),(ZA,R1B,R2M,R 3E),(ZA,R1B,R2M,R3F),(ZA,R1B,R2M,R3G),(ZA,R1B,R2M 10 ,R3H),(ZA,R1B,R2M,R3I),(ZA,R1B,R2M,R3J),(ZA,R1B,R2 M,R3K),(ZA,R1B,R2M,R3L),(ZA,R1B,R2M,R3M),(ZA,R1B, R2M,R3N),(ZA,R1B,R2M,R30),(ZA,R1B,R2M,R3P),(ZA,R1 B,R2M,R3Q),(ZA,R1B,R2M,R3R),(ZA,R1B,R2N,R3A),(ZA, R1B,R2N,R3B),(ZA,R1B,R2N,R3C),(ZA,R1B,R2N,R3D),(Z 15 A,R1B,R2N,R3E),(ZA,R1B,R2N,R3F),(ZA,R1B,R2N,R3G),( ZA,R1B,R2N,R3H),(ZA,R1B,R2N,R3I),(ZA,R1B,R2N,R3J),( ZA,R1B,R2N,R3K),(ZA,R1B,R2N,R3L),(ZA,R1B,R2N,R3M) ,(ZA,R1B,R2N,R3N),(ZA,R1B,R2N,R30),(ZA,R1B,R2N,R3 P),(ZA,R1B,R2N,R3Q),(ZA,R1B,R2N,R3R),(ZA,R1C,R2A,R 20 3A),(ZA,R1C,R2A,R3B),(ZA,R1C,R2A,R3C),(ZA,R1C,R2A, R3D),(ZA,R1C,R2A,R3E),(ZA,R1C,R2A,R3F),(ZA,R1C,R2 A,R3G),(ZA,R1C,R2A,R3H),(ZA,R1C,R2A,R3I),(ZA,R1C,R 2A,R3J),(ZA,R1C,R2A,R3K),(ZA,R1C,R2A,R3L),(ZA,R1C, R2A,R3M),(ZA,R1C,R2A,R3N),(ZA,R1C,R2A,R30),(ZA,R1 57 200843739
C,R2A,R3P),(ZA,R1C,R2A,R3Q),(ZA,R1C,R2A,R3R),(ZA,R 1C,R2B,R3A),(ZA,R1C,R2B,R3B),(ZA,R1C,R2B,R3C),(ZA, R1C,R2B,R3D),(ZA,R1C,R2B,R3E),(ZA,R1C,R2B,R3F),(ZA ,R1C,R2B,R3G),(ZA,R1C,R2B,R3H),(ZA,R1C,R2B,R3I),(Z 5 A,R1C,R2B,R3J),(ZA,R1C,R2B,R3K),(ZA,R1C,R2B,R3L),(Z
A,R1C,R2B,R3M),(ZA,R1C,R2B,R3N),(ZA,R1C,R2B,R30),( ZA,R1C,R2B,R3P),(ZA,R1C,R2B,R3Q),(ZA,R1C,R2B,R3R), (ZA,R1C,R2C,R3A),(ZA,R1C,R2C,R3B),(ZA,R1C,R2C,R3C ),(ZA,R1C,R2C,R3D),(ZA,R1C,R2C,R3E),(ZA,R1C,R2C,R3 10 F),(ZA,R1C,R2C,R3G),(ZA,R1C,R2C,R3H),(ZA,R1C,R2C,R
3I),(ZA,R1C,R2C,R3J),(ZA,R1C,R2C,R3K),(ZA,R1C,R2C,R 3L),(ZA,R1C,R2C,R3M),(ZA,R1C,R2C,R3N),(ZA,R1C,R2C, R30),(ZA,R1C,R2C,R3P),(ZA,R1C,R2C,R3Q),(ZA,R1C,R2C ,R3R),(ZA,R1C,R2D,R3A),(ZA,R1C,R2D,R3B),(ZA,R1C,R2 15 D,R3C),(ZA,R1C,R2D,R3D),(ZA,R1C,R2D,R3E),(ZA,R1C,R 2D,R3F),(ZA,R1C,R2D,R3G),(ZA,R1C,R2D,R3H),(ZA,R1C, R2D,R3I),(ZA,R1C,R2D,R3J),(ZA,R1C,R2D,R3K),(ZA,R1C, R2D,R3L),(ZA,R1C,R2D,R3M),(ZA,R1C,R2D,R3N),(ZA,R1 C,R2D,R30),(ZA,R1C,R2D,R3P),(ZA,R1C,R2D,R3Q),(ZA,R 20 1C,R2D,R3R),(ZA,R1C,R2E,R3A),(ZA,R1C,R2E,R3B),(ZA, R1C,R2E,R3C),(ZA,R1C,R2E,R3D),(ZA,R1C,R2E,R3E),(ZA ,R1C,R2E,R3F),(ZA,R1C,R2E,R3G),(ZA,R1C,R2E,R3H),(Z A,R1C,R2E,R3I),(ZA,R1C,R2E,R3J),(ZA,R1C,R2E,R3K),(Z A,R1C,R2E,R3L),(ZA,R1C,R2E,R3M),(ZA,R1C,R2E,R3N),( 58 200843739 ZA,R1C,R2E,R30),(ZA,R1C,R2E,R3P),(ZA,R1C,R2E,R3Q), (ZA,R1C,R2E,R3R),(ZA,R1C,R2F,R3A),(ZA,R1C,R2F,R3B), (ZA,R1C,R2F,R3C),(ZA,R1C,R2F,R3D),(ZA,R1C,R2F,R3E), (ZA,R1C,R2F,R3F),(ZA,R1C,R2F,R3G),(ZA,R1C,R2F,R3H), 5 (ZA,R1C,R2F,R3I),(ZA,R1C,R2F,R3J),(ZA,R1C,R2F,R3K),(
ZA,R1C,R2F,R3L),(ZA,R1C,R2F,R3M),(ZA,R1C,R2F,R3N),( ZA,R1C,R2F,R30),(ZA,R1C,R2F,R3P),(ZA,R1C,R2F,R3Q),( ZA,R1C,R2F,R3R),(ZA,R1C,R2G,R3A),(ZA,R1C,R2G,R3B), (ZA,R1C,R2G,R3C),(ZA,R1C,R2G,R3D),(ZA,R1C,R2G,R3E) 10 ,(ZA,R1C,R2G,R3F),(ZA,R1C,R2G,R3G),(ZA,R1C,R2G,R3H ),(ZA,R1C,R2G,R3I),(ZA,R1C,R2G,R3J),(ZA,R1C,R2G,R3K) ,(ZA,R1C,R2G,R3L),(ZA,R1C,R2G,R3M),(ZA,R1C,R2G,R3N ),(ZA,R1C,R2G,R30),(ZA,R1C,R2G,R3P),(ZA,R1C,R2G,R3 Q),(ZA,R1C,R2G,R3R),(ZA,R1C,R2H,R3A),(ZA,R1C,R2H,R 15 3B),(ZA,R1C,R2H,R3C),(ZA,R1C,R2H,R3D),(ZA,R1C,R2H,
R3E),(ZA,R1C,R2H,R3F),(ZA,R1C,R2H,R3G),(ZA,R1C,R2 H,R3H),(ZA,R1C,R2H,R3I),(ZA,R1C,R2H,R3J),(ZA,R1C,R2 H,R3K),(ZA,R1C,R2H,R3L),(ZA,R1C,R2H,R3M),(ZA,R1C, R2H,R3N),(ZA,R1C,R2H,R30),(ZA,R1C,R2H,R3P),(ZA,R1 20 C,R2H,R3Q),(ZA,R1C,R2H,R3R),(ZA,R1C,R2I,R3A),(ZA,R
1C,R2I,R3B),(ZA,R1C,R2I,R3C),(ZA,R1C,R2I,R3D),(ZA,R1 C,R2I,R3E),(ZA,R1C,R2I,R3F),(ZA,R1C,R2I,R3G),(ZA,R1C ,R2I,R3H),(ZA,R1C,R2I,R3I),(ZA,R1C,R2I,R3J),(ZA,R1C,R 2I,R3K),(ZA,R1C,R2I,R3L),(ZA,R1C,R2I,R3M),(ZA,R1C,R 59 200843739 2I,R3N),(ZA,R1C,R2I,R30),(ZA,R1C,R2I,R3P),(ZA,R1C,R2
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3Q),(ZA,R1D,R2B,R3R),(ZA,R1D,R2C,R3A),(ZA,R1D,R2C, R3B),(ZA,R1D,R2C,R3C),(ZA,R1D,R2C,R3D),(ZA,R1D,R2 C,R3E),(ZA,R1D,R2C,R3F),(ZA,R1D,R2C,R3G),(ZA,R1D,R 2C,R3H),(ZA,R1D,R2C,R3I),(ZA,R1D,R2C,R3J),(ZA,R1D,R 61 200843739 2C,R3K),(ZA,R1D,R2C,R3L),(ZA,R1D,R2C,R3M),(ZA,R1D, R2C,R3N),(ZA,R1D,R2C,R30),(ZA,R1D,R2C,R3P),(ZA,R1 D,R2C,R3Q),(ZA,R1D,R2C,R3R),(ZA,R1D,R2D,R3A),(ZA, R1D,R2D,R3B),(ZA,R1D,R2D,R3C),(ZA,R1D,R2D,R3D),(Z 5 A,R1D,R2D,R3E),(ZA,R1D,R2D,R3F),(ZA,R1D,R2D,R3G),(
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R2I,R3R),(ZA,R1D,R2J,R3A),(ZA,R1D,R2J,R3B),(ZA,R1D, R2J,R3C),(ZA,R1D,R2J,R3D),(ZA,R1D,R2J,R3E),(ZA,R1D, R2J,R3F),(ZA,R1D,R2J,R3G),(ZA,R1D,R2J,R3H),(ZA,R1D, R2J,R3I),(ZA,R1D,R2J,R3J),(ZA,R1D,R2J,R3K),(ZA,R1D,R 20 2J,R3L),(ZA,R1D,R2J,R3M),(ZA,R1D,R2J,R3N),(ZA,R1D,R 2J,R30),(ZA,R1D,R2J,R3P),(ZA,R1D,R2J,R3Q),(ZA,R1D,R 2J,R3R),(ZA,R1D,R2K,R3A),(ZA,R1D,R2K,R3B),(ZA,R1D, R2K,R3C),(ZA,R1D,R2K,R3D),(ZA,R1D,R2K,R3E),(ZA,R1 D,R2K,R3F),(ZA,R1D,R2K,R3G),(ZA,R1D,R2K,R3H),(ZA, 63 200843739
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R2M,R3B),(ZA,R1D,R2M,R3C),(ZA,R1D,R2M,R3D),(ZA,R 1D,R2M,R3E),(ZA,R1D,R2M,R3F),(ZA,R1D,R2M,R3G),(ZA ,R1D,R2M,R3H),(ZA,R1D,R2M,R3I),(ZA,R1D,R2M,R3J),(Z A,R1D,R2M,R3K),(ZA,R1D,R2M,R3L),(ZA,R1D,R2M,R3M) 15 ,(ZA,R1D,R2M,R3N),(ZA,R1D,R2M,R30),(ZA,R1D,R2M,R 3P),(ZA,R1D,R2M,R3Q),(ZA,R1D,R2M,R3R),(ZA,R1D,R2N ,R3A),(ZA,R1D,R2N,R3B),(ZA,R1D,R2N,R3C),(ZA,R1D,R2 N,R3D),(ZA,R1D,R2N,R3E),(ZA,R1D,R2N,R3F),(ZA,R1D,R 2N,R3G),(ZA,R1D,R2N,R3H),(ZA,R1D,R2N,R3I),(ZA,R1D, 20 R2N,R3J),(ZA,R1D,R2N,R3K),(ZA,R1D,R2N,R3L),(ZA,R1 D,R2N,R3M),(ZA,R1D,R2N,R3N),(ZA,R1D,R2N,R30),(ZA, R1D,R2N,R3P),(ZA,R1D,R2N,R3Q),(ZA,R1D,R2N,R3R),(Z A,R1E,R2A,R3A),(ZA,R1E,R2A,R3B),(ZA,R1E,R2A,R3C),( ZA,R1E,R2A,R3D),(ZA,R1E,R2A,R3E),(ZA,R1E,R2A,R3F), 64 200843739 (ZA,R1E,R2A,R3G),(ZA,R1E,R2A,R3H),(ZA,R1E,R2A,R3I) ,(ZA,R1E,R2A,R3J),(ZA,R1E,R2A,R3K),(ZA,R1E,R2A,R3L) ,(ZA,R1E,R2A,R3M),(ZA,R1E,R2A,R3N),(ZA,R1E,R2A,R3 0),(ZA,R1E,R2A,R3P),(ZA,R1E,R2A,R3Q),(ZA,R1E,R2A,R 5 3R),(ZA,R1E,R2B,R3A),(ZA,R1E,R2B,R3B),(ZA,R1E,R2B, R3C),(ZA,R1E,R2B,R3D),(ZA,R1E,R2B,R3E),(ZA,R1E,R2B ,R3F),(ZA,R1E,R2B,R3G),(ZA,R1E,R2B,R3H),(ZA,R1E,R2 B,R3I),(ZA,R1E,R2B,R3J),(ZA,R1E,R2B,R3K),(ZA,R1E,R2 B,R3L),(ZA,R1E,R2B,R3M),(ZA,R1E,R2B,R3N),(ZA,R1E,R 10 2B,R30),(ZA,R1E,R2B,R3P),(ZA,R1E,R2B,R3Q),(ZA,R1E, R2B,R3R),(ZA,R1E,R2C,R3A),(ZA,R1E,R2C,R3B),(ZA,R1E ,R2C,R3C),(ZA,R1E,R2C,R3D),(ZA,R1E,R2C,R3E),(ZA,R1 E,R2C,R3F),(ZA,R1E,R2C,R3G),(ZA,R1E,R2C,R3H),(ZA,R 1E,R2C,R3I),(ZA,R1E,R2C,R3J),(ZA,R1E,R2C,R3K),(ZA,R 15 1E,R2C,R3L),(ZA,R1E,R2C,R3M),(ZA,R1E,R2C,R3N),(ZA, R1E,R2C,R30),(ZA,R1E,R2C,R3P),(ZA,R1E,R2C,R3Q),(ZA ,R1E,R2C,R3R),(ZA,R1E,R2D,R3A),(ZA,R1E,R2D,R3B),(Z A,R1E,R2D,R3C),(ZA,R1E,R2D,R3D),(ZA,R1E,R2D,R3E),( ZA,R1E,R2D,R3F),(ZA,R1E,R2D,R3G),(ZA,R1E,R2D,R3H), 20 (ZA,R1E,R2D,R3I),(ZA,R1E,R2D,R3J),(ZA,R1E,R2D,R3K),
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1E,R2J,R3R),(ZA,R1E,R2K,R3A),(ZA,R1E,R2K,R3B),(ZA,R 1E,R2K,R3C),(ZA,R1E,R2K,R3D),(ZA,R1E,R2K,R3E),(ZA, R1E,R2K,R3F),(ZA,R1E,R2K,R3G),(ZA,R1E,R2K,R3H),(ZA ,R1E,R2K,R3I),(ZA,R1E,R2K,R3J),(ZA,R1E,R2K,R3K),(ZA 15 ,R1E,R2K,R3L),(ZA,R1E,R2K,R3M),(ZA,R1E,R2K,R3N),(Z A,R1E,R2K,R30),(ZA,R1E,R2K,R3P),(ZA,R1E,R2K,R3Q),( ZA,R1E,R2K,R3R),(ZA,R1E,R2L,R3A),(ZA,R1E,R2L,R3B), (ZA,R1E,R2L,R3C),(ZA,R1E,R2L,R3D),(ZA,R1E,R2L,R3E), (ZA,R1E,R2L,R3F),(ZA,R1E,R2L,R3G),(ZA,R1E,R2L,R3H), 20 (ZA,R1E,R2L,R3I),(ZA,R1E,R2L,R3J),(ZA,R1E,R2L,R3K),(
ZA,R1E,R2L,R3L),(ZA,R1E,R2L,R3M),(ZA,R1E,R2L,R3N), (ZA,R1E,R2L,R30),(ZA,R1E,R2L,R3P),(ZA,R1E,R2L,R3Q), (ZA,R1E,R2L,R3R),(ZA,R1E,R2M,R3A),(ZA,R1E,R2M,R3B ),(ZA,R1E,R2M,R3C),(ZA,R1E,R2M,R3D),(ZA,R1E,R2M,R 67 200843739
3E),(ZA,R1E,R2M,R3F),(ZA,R1E,R2M,R3G),(ZA,R1E,R2M, R3H),(ZA,R1E,R2M,R3I),(ZA,R1E,R2M,R3J),(ZA,R1E,R2M ,R3K),(ZA,R1E,R2M,R3L),(ZA,R1E,R2M,R3M),(ZA,R1E,R 2M,R3N),(ZA,R1E,R2M,R30),(ZA,R1E,R2M,R3P),(ZA,R1E 5 ,R2M,R3Q),(ZA,R1E,R2M,R3R),(ZA,R1E,R2N,R3A),(ZA,R 1E,R2N,R3B),(ZA,R1E,R2N,R3C),(ZA,R1E,R2N,R3D),(ZA, R1E,R2N,R3E),(ZA,R1E,R2N,R3F),(ZA,R1E,R2N,R3G),(ZA ,R1E,R2N,R3H),(ZA,R1E,R2N,R3I),(ZA,R1E,R2N,R3J),(ZA ,R1E,R2N,R3K),(ZA,R1E,R2N,R3L),(ZA,R1E,R2N,R3M),(Z 10 A,R1E,R2N,R3N),(ZA,R1E,R2N,R30),(ZA,R1E,R2N,R3P),( ZA,R1E,R2N,R3Q),(ZA,R1E,R2N,R3R),(ZA,R1F,R2A,R3A), (ZA,R1F,R2A,R3B),(ZA,R1F,R2A,R3C),(ZA,R1F,R2A,R3D), (ZA,R1F,R2A,R3E),(ZA,R1F,R2A,R3F),(ZA,R1F,R2A,R3G), (ZA,R1F,R2A,R3H),(ZA,R1F,R2A,R3I),(ZA,R1F,R2A,R3J),( 15 ZA,R1F,R2A,R3K),(ZA,R1F,R2A,R3L),(ZA,R1F,R2A,R3M),
(ZA,R1F,R2A,R3N),(ZA,R1F,R2A,R30),(ZA,R1F,R2A,R3P), (ZA,R1F,R2A,R3Q),(ZA,R1F,R2A,R3R),(ZA,R1F,R2B,R3A), (ZA,R1F,R2B,R3B),(ZA,R1F,R2B,R3C),(ZA,R1F,R2B,R3D), (ZA,R1F,R2B,R3E),(ZA,R1F,R2B,R3F),(ZA,R1F,R2B,R3G),( 20 ZA,R1F,R2B,R3H),(ZA,R1F,R2B,R3I),(ZA,R1F,R2B,R3J),(Z
A,R1F,R2B,R3K),(ZA,R1F,R2B,R3L),(ZA,R1F,R2B,R3M),(Z A,R1F,R2B,R3N),(ZA,R1F,R2B,R30),(ZA,R1F,R2B,R3P),(Z A,R1F,R2B,R3Q),(ZA,R1F,R2B,R3R),(ZA,R1F,R2C,R3A),(Z A,R1F,R2C,R3B),(ZA,R1F,R2C,R3C),(ZA,R1F,R2C,R3D),(Z 68 200843739
A,R1F,R2C,R3E),(ZA,R1F,R2C,R3F),(ZA,R1F,R2C,R3G),(Z A,R1F,R2C,R3H),(ZA,R1F,R2C,R3I),(ZA,R1F,R2C,R3J),(ZA ,R1F,R2C,R3K),(ZA,R1F,R2C,R3L),(ZA,R1F,R2C,R3M),(ZA ,R1F,R2C,R3N),(ZA,R1F,R2C,R30),(ZA,R1F,R2C,R3P),(ZA 5 ,R1F,R2C,R3Q),(ZA,R1F,R2C,R3R),(ZA,R1F,R2D,R3A),(ZA
,R1F,R2D,R3B),(ZA,R1F,R2D,R3C),(ZA,R1F,R2D,R3D),(ZA ,R1F,R2D,R3E),(ZA,R1F,R2D,R3F),(ZA,R1F,R2D,R3G),(ZA ,R1F,R2D,R3H),(ZA,R1F,R2D,R3I),(ZA,R1F,R2D,R3J),(ZA, R1F,R2D,R3K),(ZA,R1F,R2D,R3L),(ZA,R1F,R2D,R3M),(ZA 10 ,R1F,R2D,R3N),(ZA,R1F,R2D,R30),(ZA,R1F,R2D,R3P),(ZA
,R1F,R2D,R3Q),(ZA,R1F,R2D,R3R),(ZA,R1F,R2E,R3A),(ZA ,R1F,R2E,R3B),(ZA,R1F,R2E,R3C),(ZA,R1F,R2E,R3D),(ZA, R1F,R2E,R3E),(ZA,R1F,R2E,R3F),(ZA,R1F,R2E,R3G),(ZA, R1F,R2E,R3H),(ZA,R1F,R2E,R3I),(ZA,R1F,R2E,R3J),(ZA,R 15 1F,R2E,R3K),(ZA,R1F,R2E,R3L),(ZA,R1F,R2E,R3M),(ZA,R 1F,R2E,R3N),(ZA,R1F,R2E,R30),(ZA,R1F,R2E,R3P),(ZA,R 1F,R2E,R3Q),(ZA,R1F,R2E,R3R),(ZA,R1F,R2F,R3A),(ZA,R 1F,R2F,R3B),(ZA,R1F,R2F,R3C),(ZA,R1F,R2F,R3D),(ZA,R1 F,R2F,R3E),(ZA,R1F,R2F,R3F),(ZA,R1F,R2F,R3G),(ZA,R1F, 20 R2F,R3H),(ZA,R1F,R2F,R3I),(ZA,R1F,R2F,R3J),(ZA,R1F,R2 F,R3K),(ZA,R1F,R2F,R3L),(ZA,R1F,R2F,R3M),(ZA,R1F,R2F ,R3N),(ZA,R1F,R2F,R30),(ZA,R1F,R2F,R3P),(ZA,R1F,R2F, R3Q),(ZA,R1F,R2F,R3R),(ZA,R1F,R2G,R3A),(ZA,R1F,R2G, R3B),(ZA,R1F,R2G,R3C),(ZA,R1F,R2G,R3D),(ZA,R1F,R2G, 69 200843739
R3E),(ZA,R1F,R2G,R3F),(ZA,R1F,R2G,R3G),(ZA,R1F,R2G, R3H),(ZA,R1F,R2G,R3I),(ZA,R1F,R2G,R3J),(ZA,R1F,R2G,R 3K),(ZA,R1F,R2G,R3L),(ZA,R1F,R2G,R3M),(ZA,R1F,R2G,R 3N),(ZA,R1F,R2G,R30),(ZA,R1F,R2G,R3P),(ZA,R1F,R2G,R 5 3Q),(ZA,R1F,R2G,R3R),(ZA,R1F,R2H,R3A),(ZA,R1F,R2H,R
3B),(ZA,R1F,R2H,R3C),(ZA,R1F,R2H,R3D),(ZA,R1F,R2H,R 3E),(ZA,R1F,R2H,R3F),(ZA,R1F,R2H,R3G),(ZA,R1F,R2H,R 3H),(ZA,R1F,R2H,R3I),(ZA,R1F,R2H,R3J),(ZA,R1F,R2H,R3 K),(ZA,R1F,R2H,R3L),(ZA,R1F,R2H,R3M),(ZA,R1F,R2H,R 10 3N),(ZA,R1F,R2H,R30),(ZA,R1F,R2H,R3P),(ZA,R1F,R2H,R
3Q),(ZA,R1F,R2H,R3R),(ZA,R1F,R2I,R3A),(ZA,R1F,R2I,R3 B),(ZA,R1F,R2I,R3C),(ZA,R1F,R2I,R3D),(ZA,R1F,R2I,R3E) ,(ZA,R1F,R2I,R3F),(ZA,R1F,R2I,R3G),(ZA,R1F,R2I,R3H),( ZA,R1F,R2I,R3I),(ZA,R1F,R2I,R3J),(ZA,R1F,R2I,R3K),(ZA, 15 R1F,R2I,R3L),(ZA,R1F,R2I,R3M),(ZA,R1F,R2I,R3N),(ZA,R 1F,R2I,R30),(ZA,R1F,R2I,R3P),(ZA,R1F,R2I,R3Q),(ZA,R1F ,R2I,R3R),(ZA,R1F,R2J,R3A),(ZA,R1F,R2J,R3B),(ZA,R1F,R 2J,R3C),(ZA,R1F,R2J,R3D),(ZA,R1F,R2J,R3E),(ZA,R1F,R2J ,R3F),(ZA,R1F,R2J,R3G),(ZA,R1F,R2J,R3H),(ZA,R1F,R2J,R 20 3I),(ZA,R1F,R2J,R3J),(ZA,R1F,R2J,R3K),(ZA,R1F,R2J,R3L)
,(ZA,R1F,R2J,R3M),(ZA,R1F,R2J,R3N),(ZA,R1F,R2J,R30),( ZA,R1F,R2J,R3P),(ZA,R1F,R2J,R3Q),(ZA,R1F,R2J,R3R),(Z A,R1F,R2K,R3A),(ZA,R1F,R2K,R3B),(ZA,R1F,R2K,R3C),(Z A,R1F,R2K,R3D),(ZA,R1F,R2K,R3E),(ZA,R1F,R2K,R3F),(Z 70 200843739 A,R1F,R2K,R3G),(ZA,R1F,R2K,R3H),(ZA,R1F,R2K,R3I),(Z A,R1F,R2K,R3J),(ZA,R1F,R2K,R3K),(ZA,R1F,R2K,R3L),(Z A,R1F,R2K,R3M),(ZA,R1F,R2K,R3N),(ZA,R1F,R2K,R30),( ZA,R1F,R2K,R3P),(ZA,R1F,R2K,R3Q),(ZA,R1F,R2K,R3R),( 5 ZA,R1F,R2L,R3A),(ZA,R1F,R2L,R3B),(ZA,R1F,R2L,R3C),(
ZA,R1F,R2L,R3D),(ZA,R1F,R2L,R3E),(ZA,R1F,R2L,R3F),( ZA,R1F,R2L,R3G),(ZA,R1F,R2L,R3H),(ZA,R1F,R2L,R3I),(Z A,R1F,R2L,R3J),(ZA,R1F,R2L,R3K),(ZA,R1F,R2L,R3L),(Z A,R1F,R2L,R3M),(ZA,R1F,R2L,R3N),(ZA,R1F,R2L,R30),(Z 10 A,R1F,R2L,R3P),(ZA,R1F,R2L,R3Q),(ZA,R1F,R2L,R3R),(Z A,R1F,R2M,R3A),(ZA,R1F,R2M,R3B),(ZA,R1F,R2M,R3C),( ZA,R1F,R2M,R3D),(ZA,R1F,R2M,R3E),(ZA,R1F,R2M,R3F), (ZA,R1F,R2M,R3G),(ZA,R1F,R2M,R3H),(ZA,R1F,R2M,R3I) ,(ZA,R1F,R2M,R3J),(ZA,R1F,R2M,R3K),(ZA,R1F,R2M,R3L 15 ),(ZA,R1F,R2M,R3M),(ZA,R1F,R2M,R3N),(ZA,R1F,R2M,R3 0),(ZA,R1F,R2M,R3P),(ZA,R1F,R2M,R3Q),(ZA,R1F,R2M,R 3R),(ZA,R1F,R2N,R3A),(ZA,R1F,R2N,R3B),(ZA,R1F,R2N,R 3C),(ZA,R1F,R2N,R3D),(ZA,R1F,R2N,R3E),(ZA,R1F,R2N,R 3F),(ZA,R1F,R2N,R3G),(ZA,R1F,R2N,R3H),(ZA,R1F,R2N,R 20 3I),(ZA,R1F,R2N,R3J),(ZA,R1F,R2N,R3K),(ZA,R1F,R2N,R3
L),(ZA,R1F,R2N,R3M),(ZA,R1F,R2N,R3N),(ZA,R1F,R2N,R 30),(ZA,R1F,R2N,R3P),(ZA,R1F,R2N,R3Q),(ZA,R1F,R2N,R 3R),(ZA,R1G,R2A,R3A),(ZA,R1G,R2A,R3B),(ZA,R1G,R2A, R3C),(ZA,R1G,R2A,R3D),(ZA,R1G,R2A,R3E),(ZA,R1G,R2A 71 200843739 ,R3F),(ZA,R1G,R2A,R3G),(ZA,R1G,R2A,R3H),(ZA,R1G,R2 A,R3I),(ZA,R1G,R2A,R3J),(ZA,R1G,R2A,R3K),(ZA,R1G,R2
A,R3L),(ZA,R1G,R2A,R3M),(ZA,R1G,R2A,R3N),(ZA,R1G,R 2A,R30),(ZA,R1G,R2A,R3P),(ZA,R1G,R2A,R3Q),(ZA,R1G,
5 R2A,R3R),(ZA,R1G,R2B,R3A),(ZA,R1G,R2B,R3B),(ZA,R1G
,R2B,R3C),(ZA,R1G,R2B,R3D),(ZA,R1G,R2B,R3E),(ZA,R1 G,R2B,R3F),(ZA,R1G,R2B,R3G),(ZA,R1G,R2B,R3H),(ZA,R 1G,R2B,R3I),(ZA,R1G,R2B,R3J),(ZA,R1G,R2B,R3K),(ZA,R 1G,R2B,R3L),(ZA,R1G,R2B,R3M),(ZA,R1G,R2B,R3N),(ZA, 10 R1G,R2B,R30),(ZA,R1G,R2B,R3P),(ZA,R1G,R2B,R3Q),(ZA ,R1G,R2B,R3R),(ZA,R1G,R2C,R3A),(ZA,R1G,R2C,R3B),(Z A,R1G,R2C,R3C),(ZA,R1G,R2C,R3D),(ZA,R1G,R2C,R3E),( ZA,R1G,R2C,R3F),(ZA,R1G,R2C,R3G),(ZA,R1G,R2C,R3H), (ZA,R1G,R2C,R3I),(ZA,R1G,R2C,R3J),(ZA,R1G,R2C,R3K),( 15 ZA,R1G,R2C,R3L),(ZA,R1G,R2C,R3M),(ZA,R1G,R2C,R3N),
(ZA,R1G,R2C,R30),(ZA,R1G,R2C,R3P),(ZA,R1G,R2C,R3Q) ,(ZA,R1G,R2C,R3R),(ZA,R1G,R2D,R3A),(ZA,R1G,R2D,R3B ),(ZA,R1G,R2D,R3C),(ZA,R1G,R2D,R3D),(ZA,R1G,R2D,R3 E),(ZA,R1G,R2D,R3F),(ZA,R1G,R2D,R3G),(ZA,R1G,R2D,R 20 3H),(ZA,R1G,R2D,R3I),(ZA,R1G,R2D,R3J),(ZA,R1G,R2D,R 3K),(ZA,R1G,R2D,R3L),(ZA,R1G,R2D,R3M),(ZA,R1G,R2D, R3N),(ZA,R1G,R2D,R30),(ZA,R1G,R2D,R3P),(ZA,R1G,R2D ,R3Q),(ZA,R1G,R2D,R3R),(ZA,R1G,R2E,R3A),(ZA,R1G,R2 E,R3B),(ZA,R1G,R2E,R3C),(ZA,R1G,R2E,R3D),(ZA,R1G,R2 72 200843739
E,R3E),(ZA,R1G,R2E,R3F),(ZA,R1G,R2E,R3G),(ZA,R1G,R2 E,R3H),(ZA,R1G,R2E,R3I),(ZA,R1G,R2E,R3J),(ZA,R1G,R2 E,R3K),(ZA,R1G,R2E,R3L),(ZA,R1G,R2E,R3M),(ZA,R1G,R 2E,R3N),(ZA,R1G,R2E,R30),(ZA,R1G,R2E,R3P),(ZA,R1G,R 5 2E,R3Q),(ZA,R1G,R2E,R3R),(ZA,R1G,R2F,R3A),(ZA,R1G,R 2F,R3B),(ZA,R1G,R2F,R3C),(ZA,R1G,R2F,R3D),(ZA,R1G,R 2F,R3E),(ZA,R1G,R2F,R3F),(ZA,R1G,R2F,R3G),(ZA,R1G,R2 F,R3H),(ZA,R1G,R2F,R3I),(ZA,R1G,R2F,R3J),(ZA,R1G,R2F, R3K),(ZA,R1G,R2F,R3L),(ZA,R1G,R2F,R3M),(ZA,R1G,R2F, 10 R3N),(ZA,R1G,R2F,R30),(ZA,R1G,R2F,R3P),(ZA,R1G,R2F,
R3Q),(ZA,R1G,R2F,R3R),(ZA,R1G,R2G,R3A),(ZA,R1G,R2G, R3B),(ZA,R1G,R2G,R3C),(ZA,R1G,R2G,R3D),(ZA,R1G,R2G, R3E),(ZA,R1G,R2G,R3F),(ZA,R1G,R2G,R3G),(ZA,R1G,R2G, R3H),(ZA,R1G,R2G,R3I),(ZA,R1G,R2G,R3J),(ZA,R1G,R2G, 15 R3K),(ZA,R1G,R2G,R3L),(ZA,R1G,R2G,R3M),(ZA,R1G,R2G ,R3N),(ZA,R1G,R2G,R30),(ZA,R1G,R2G,R3P),(ZA,R1G,R2G ,R3Q),(ZA,R1G,R2G,R3R),(ZA,R1G,R2H,R3A),(ZA,R1G,R2 H,R3B),(ZA,R1G,R2H,R3C),(ZA,R1G,R2H,R3D),(ZA,R1G,R 2H,R3E),(ZA,R1G,R2H,R3F),(ZA,R1G,R2H,R3G),(ZA,R1G, 20 R2H,R3H),(ZA,R1G,R2H,R3I),(ZA,R1G,R2H,R3J),(ZA,R1G, R2H,R3K),(ZA,R1G,R2H,R3L),(ZA,R1G,R2H,R3M),(ZA,R1 G,R2H,R3N),(ZA,R1G,R2H,R30),(ZA,R1G,R2H,R3P),(ZA,R 1G,R2H,R3Q),(ZA,R1G,R2H,R3R),(ZA,R1G,R2I,R3A),(ZA,R 1G,R2I,R3B),(ZA,R1G,R2I,R3C),(ZA,R1G,R2I,R3D),(ZA,R1 73 200843739 G,R2I,R3E),(ZA,R1G,R2I,R3F),(ZA,R1G,R2I,R3G),(ZA,R1G, R2I,R3H),(ZA,R1G,R2I,R3I),(ZA,R1G,R2I,R3J),(ZA,R1G,R2 I,R3K),(ZA,R1G,R2I,R3L),(ZA,R1G,R2I,R3M),(ZA,R1G,R2I, R3N),(ZA,R1G,R2I,R30),(ZA,R1G,R2I,R3P),(ZA,R1G,R2I,R 5 3Q),(ZA,R1G,R2I,R3R),(ZA,R1G,R2J,R3A),(ZA,R1G,R2J,R3
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N),(ZA,R1P,R2A,R30),(ZA,R1P,R2A,R3P),(ZA,R1P,R2A,R3 Q),(ZA,R1P,R2A,R3R),(ZA,R1P,R2B,R3A),(ZA,R1P,R2B,R3 B),(ZA,R1P,R2B,R3C),(ZA,R1P,R2B,R3D),(ZA,R1P,R2B,R3 E),(ZA,R1P,R2B,R3F),(ZA,R1P,R2B,R3G),(ZA,R1P,R2B,R3 5 H),(ZA,R1P,R2B,R3I),(ZA,R1P,R2B,R3J),(ZA,R1P,R2B,R3K ),(ZA,R1P,R2B,R3L),(ZA,R1P,R2B,R3M),(ZA,R1P,R2B,R3N ),(ZA,R1P,R2B,R30),(ZA,R1P,R2B,R3P),(ZA,R1P,R2B,R3Q) ,(ZA,R1P,R2B,R3R),(ZA,R1P,R2C,R3A),(ZA,R1P,R2C,R3B), (ZA,R1P,R2C,R3C),(ZA,R1P,R2C,R3D),(ZA,R1P,R2C,R3E),( 10 ZA,R1P,R2C,R3F),(ZA,R1P,R2C,R3G),(ZA,R1P,R2C,R3H),(
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R1P,R2E,R3C),(ZA,R1P,R2E,R3D),(ZA,R1P,R2E,R3E),(ZA, R1P,R2E,R3F),(ZA,R1P,R2E,R3G),(ZA,R1P,R2E,R3H),(ZA, R1P,R2E,R3I),(ZA,R1P,R2E,R3J),(ZA,R1P,R2E,R3K),(ZA,R 1P,R2E,R3L),(ZA,R1P,R2E,R3M),(ZA,R1P,R2E,R3N),(ZA,R 104 200843739 1P,R2E,R30),(ZA,R1P,R2E,R3P),(ZA,R1P,R2E,R3Q),(ZA,R1 P,R2E,R3R),(ZA,R1P,R2F,R3A),(ZA,R1P,R2F,R3B),(ZA,R1P ,R2F,R3C),(ZA,R1P,R2F,R3D),(ZA,R1P,R2F,R3E),(ZA,R1P, R2F,R3F),(ZA,R1P,R2F,R3G),(ZA,R1P,R2F,R3H),(ZA,R1P,R 5 2F,R3I),(ZA,R1P,R2F,R3J),(ZA,R1P,R2F,R3K),(ZA,R1P,R2F,
R3L),(ZA,R1P,R2F,R3M),(ZA,R1P,R2F,R3N),(ZA,R1P,R2F,R 30),(ZA,R1P,R2F,R3P),(ZA,R1P,R2F,R3Q),(ZA,R1P,R2F,R3 R),(ZA,R1P,R2G,R3A),(ZA,R1P,R2G,R3B),(ZA,R1P,R2G,R3 C),(ZA,R1P,R2G,R3D),(ZA,R1P,R2G,R3E),(ZA,R1P,R2G,R3 10 F),(ZA,R1P,R2G,R3G),(ZA,R1P,R2G,R3H),(ZA,R1P,R2G,R3I ),(ZA,R1P,R2G,R3J),(ZA,R1P,R2G,R3K),(ZA,R1P,R2G,R3L), (ZA,R1P,R2G,R3M),(ZA,R1P,R2G,R3N),(ZA,R1P,R2G,R30), (ZA,R1P,R2G,R3P),(ZA,R1P,R2G,R3Q),(ZA,R1P,R2G,R3R),( ZA,R1P,R2H,R3A),(ZA,R1P,R2H,R3B),(ZA,R1P,R2H,R3C),( 15 ZA,R1P,R2H,R3D),(ZA,R1P,R2H,R3E),(ZA,R1P,R2H,R3F),(
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A,R1P,R2I,R3D),(ZA,R1P,R2I,R3E),(ZA,R1P,R2I,R3F),(ZA, R1P,R2I,R3G),(ZA,R1P,R2I,R3H),(ZA,R1P,R2I,R3I),(ZA,R1 P,R2I,R3J),(ZA,R1P,R2I,R3K),(ZA,R1P,R2I,R3L),(ZA,R1P,R 2I,R3M),(ZA,R1P,R2I,R3N),(ZA,R1P,R2I,R30),(ZA,R1P,R2I 105 200843739
,R3P),(ZA,R1P,R2I,R3Q),(ZA,R1P,R2I,R3R),(ZA,R1P,R2J,R 3A),(ZA,R1P,R2J,R3B),(ZA,R1P,R2J,R3C),(ZA,R1P,R2J,R3 D),(ZA,R1P,R2J,R3E),(ZA,R1P,R2J,R3F),(ZA,R1P,R2J,R3G) ,(ZA,R1P,R2J,R3H),(ZA,R1P,R2J,R3I),(ZA,R1P,R2J,R3J),(Z 5 A,R1P,R2J,R3K),(ZA,R1P,R2J,R3L),(ZA,R1P,R2J,R3M),(ZA
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R2L,R3H),(ZA,R1P,R2L,R3I),(ZA,R1P,R2L,R3J),(ZA,R1P,R 2L,R3K),(ZA,R1P,R2L,R3L),(ZA,R1P,R2L,R3M),(ZA,R1P,R 2L,R3N),(ZA,R1P,R2L,R30),(ZA,R1P,R2L,R3P),(ZA,R1P,R2 L,R3Q),(ZA,R1P,R2L,R3R),(ZA,R1P,R2M,R3A),(ZA,R1P,R2 20 M,R3B),(ZA,R1P,R2M,R3C),(ZA,R1P,R2M,R3D),(ZA,R1P,R
2M,R3E),(ZA,R1P,R2M,R3F),(ZA,R1P,R2M,R3G),(ZA,R1P, R2M,R3H),(ZA,R1P,R2M,R3I),(ZA,R1P,R2M,R3J),(ZA,R1P, R2M,R3K),(ZA,R1P,R2M,R3L),(ZA,R1P,R2M,R3M),(ZA,R1 P,R2M,R3N),(ZA,R1P,R2M,R30),(ZA,R1P,R2M,R3P),(ZA,R 106 200843739
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0),(ZA,R1Q,R2C,R3P),(ZA,R1Q,R2C,R3Q),(ZA,R1Q,R2C,R 3R),(ZA,R1Q,R2D,R3A),(ZA,R1Q,R2D,R3B),(ZA,R1Q,R2D, R3C),(ZA,R1Q,R2D,R3D),(ZA,R1Q,R2D,R3E),(ZA,R1Q,R2 D,R3F),(ZA,R1Q,R2D,R3G),(ZA,R1Q,R2D,R3H),(ZA,R1Q,
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S,R2A,R3P),(ZA,R1S,R2A,R3Q),(ZA,R1S,R2A,R3R),(ZA,R 1S,R2B,R3A),(ZA,R1S,R2B,R3B),(ZA,R1S,R2B,R3C),(ZA,R 1S,R2B,R3D),(ZA,R1S,R2B,R3E),(ZA,R1S,R2B,R3F),(ZA,R 1S,R2B,R3G),(ZA,R1S,R2B,R3H),(ZA,R1S,R2B,IGI),(ZA,R 20 1S,R2B,R3J),(ZA,R1S,R2B,R3K),(ZA,R1S,R2B,R3L),(ZA,R 1S,R2B,R3M),(ZA,R1S,R2B,R3N),(ZA,R1S,R2B,R30),(ZA, R1S,R2B,R3P),(ZA,R1S,R2B,R3Q),(ZA,R1S,R2B,R3R),(ZA, R1S,R2C,R3A),(ZA,R1S,R2C,R3B),(ZA,R1S,R2C,R3C),(ZA, R1S,R2C,R3D),(ZA,R1S,R2C,R3E),(ZA,R1S,R2C,R3F),(ZA, 114 200843739
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R3C),(ZB,R1D,R2B,R3D),(ZB,R1D,R2B,R3E),(ZB,R1D,R2B ,R3F),(ZB,R1D,R2B,R3G),(ZB,R1D,R2B,R3H),(ZB,R1D,R2 B,R3I),(ZB,R1D,R2B,R3J),(ZB,R1D,R2B,R3K),(ZB,R1D,R2 B,R3L),(ZB,R1D,R2B,R3M),(ZB,R1D,R2B,R3N),(ZB,R1D,R 128 200843739 2B,R30),(ZB,R1D,R2B,R3P),(ZB,R1D,R2B,R3Q),(ZB,R1D, R2B,R3R),(ZB,R1D,R2C,R3A),(ZB,R1D,R2C,R3B),(ZB,R1 D,R2C,R3C),(ZB,R1D,R2C,R3D),(ZB,R1D,R2C,R3E),(ZB,R 1D,R2C,R3F),(ZB,R1D,R2C,R3G),(ZB,R1D,R2C,R3H),(ZB, 5 R1D,R2C,R3I),(ZB,R1D,R2C,R3J),(ZB,R1D,R2C,R3K),(ZB,
R1D,R2C,R3L),(ZB,R1D,R2C,R3M),(ZB,R1D,R2C,R3N),(Z B,R1D,R2C,R30),(ZB,R1D,R2C,R3P),(ZB,R1D,R2C,R3Q),( ZB,R1D,R2C,R3R),(ZB,R1D,R2D,R3A),(ZB,R1D,R2D,R3B) ,(ZB,R1D,R2D,R3C),(ZB,R1D,R2D,R3D),(ZB,R1D,R2D,R3 10 E),(ZB,R1D,R2D,R3F),(ZB,R1D,R2D,R3G),(ZB,R1D,R2D,R 3H),(ZB,R1D,R2D,RM),(ZB,R1D,R2D,R3J),(ZB,R1D,R2D,R 3K),(ZB,R1D,R2D,R3L),(ZB,R1D,R2D,R3M),(ZB,R1D,R2D, R3N),(ZB,R1D,R2D,R30),(ZB,R1D,R2D,R3P),(ZB,R1D,R2 D,R3Q),(ZB,R1D,R2D,R3R),(ZB,R1D,R2E,R3A),(ZB,R1D,R 15 2E,R3B),(ZB,R1D,R2E,R3C),(ZB,R1D,R2E,R3D),(ZB,R1D, R2E,R3E),(ZB,R1D,R2E,R3F),(ZB,R1D,R2E,R3G),(ZB,R1D, R2E,R3H),(ZB,R1D,R2E,R3I),(ZB,R1D,R2E,R3J),(ZB,R1D, R2E,R3K),(ZB,R1D,R2E,R3L),(ZB,R1D,R2E,R3M),(ZB,R1 D,R2E,R3N),(ZB,R1D,R2E,R30),(ZB,R1D,R2E,R3P),(ZB,R 20 1D,R2E,R3Q),(ZB,R1D,R2E,R3R),(ZB,R1D,R2F,R3A),(ZB,
R1D,R2F,R3B),(ZB,R1D,R2F,R3C),(ZB,R1D,R2F,R3D),(ZB, R1D,R2F,R3E),(ZB,R1D,R2F,R3F),(ZB,R1D,R2F,R3G),(ZB, R1D,R2F,R3H),(ZB,R1D,R2F,R3I),(ZB,R1D,R2F,R3J),(ZB,R 1D,R2F,R3K),(ZB,R1D,R2F,R3L),(ZB,R1D,R2F,R3M),(ZB,R 129 200843739 1D,R2F,R3N),(ZB,R1D,R2F,R30),(ZB,R1D,R2F,R3P),(ZB,R 1D,R2F,R3Q),(ZB,R1D,R2F,R3R),(ZB,R1D,R2G,R3A),(ZB,R 1D,R2G,R3B),(ZB,R1D,R2G,R3C),(ZB,R1D,R2G,R3D),(ZB, R1D,R2G,R3E),(ZB,R1D,R2G,R3F),(ZB,R1D,R2G,R3G),(ZB, 5 R1D,R2G,R3H),(ZB,R1D,R2G,R3I),(ZB,R1D,R2G,R3J),(ZB,
R1D,R2G,R3K),(ZB,R1D,R2G,R3L),(ZB,R1D,R2G,R3M),(ZB ,R1D,R2G,R3N),(ZB,R1D,R2G,R30),(ZB,R1D,R2G,R3P),(Z B,R1D,R2G,R3Q),(ZB,R1D,R2G,R3R),(ZB,R1D,R2H,R3A),( ZB,R1D,R2H,R3B),(ZB,R1D,R2H,R3C),(ZB,R1D,R2H,R3D) 10 ,(ZB,R1D,R2H,R3E),(ZB,R1D,R2H,R3F),(ZB,R1D,R2H,R3G ),(ZB,R1D,R2H,R3H),(ZB,R1D,R2H,R3I),(ZB,R1D,R2H,R3J ),(ZB,R1D,R2H,R3K),(ZB,R1D,R2H,R3L),(ZB,R1D,R2H,R3 M),(ZB,R1D,R2H,R3N),(ZB,R1D,R2H,R30),(ZB,R1D,R2H, R3P),(ZB,R1D,R2H,R3Q),(ZB,R1D,R2H,R3R),(ZB,R1D,R2I, 15 R3A),(ZB,R1D,R2I,R3B),(ZB,R1D,R2I,R3C),(ZB,R1D,R2I, R3D),(ZB,R1D,R2I,R3E),(ZB,R1D,R2I,R3F),(ZB,R1D,R2I,R 3G),(ZB,R1D,R2I,R3H),(ZB,R1D,R2I,R3I),(ZB,R1D,R2I,R3 J),(ZB,R1D,R2I,R3K),(ZB,R1D,R2I,R3L),(ZB,R1D,R2I,R3M ),(ZB,R1D,R2I,R3N),(ZB,R1D,R2I,R30),(ZB,R1D,R2I,R3P), 20 (ZB,R1D,R2I,R3Q),(ZB,R1D,R2I,R3R),(ZB,R1D,R2J,R3A),( ZB,R1D,R2J,R3B),(ZB,R1D,R2J,R3C),(ZB,R1D,R2J,R3D),( ZB,R1D,R2J,R3E),(ZB,R1D,R2J,R3F),(ZB,R1D,R2J,R3G),(Z B,R1D,R2J,R3H),(ZB,R1D,R2J,R3I),(ZB,R1D,R2J,R3J),(ZB, R1D,R2J,R3K),(ZB,R1D,R2J,R3L),(ZB,R1D,R2J,R3M),(ZB, 130 200843739 R1D,R2J,R3N),(ZB,R1D,R2J,R30),(ZB,R1D,R2J,R3P),(ZB, R1D,R2J,R3Q),(ZB,R1D,R2J,R3R),(ZB,R1D,R2K,R3A),(ZB, R1D,R2K,R3B),(ZB,R1D,R2K,R3C),(ZB,R1D,R2K,R3D),(Z B,R1D,R2K,R3E),(ZB,R1D,R2K,R3F),(ZB,R1D,R2K,R3G),( 5 ZB,R1D,R2K,R3H),(ZB,R1D,R2K,R3I),(ZB,R1D,R2K,R3J),( ZB,R1D,R2K,R3K),(ZB,R1D,R2K,R3L),(ZB,R1D,R2K,R3M) ,(ZB,R1D,R2K,R3N),(ZB,R1D,R2K,R30),(ZB,R1D,R2K,R3 P),(ZB,R1D,R2K,R3Q),(ZB,R1D,R2K,R3R),(ZB,R1D,R2L,R 3A),(ZB,R1D,R2L,R3B),(ZB,R1D,R2L,R3C),(ZB,R1D,R2L, 10 R3D),(ZB,R1D,R2L,R3E),(ZB,R1D,R2L,R3F),(ZB,R1D,R2L,
R3G),(ZB,R1D,R2L,R3H),(ZB,R1D,R2L,R3I),(ZB,R1D,R2L, R3J),(ZB,R1D,R2L,R3K),(ZB,R1D,R2L,R3L),(ZB,R1D,R2L, R3M),(ZB,R1D,R2L,R3N),(ZB,R1D,R2L,R30),(ZB,R1D,R2 L,R3P),(ZB,R1D,R2L,R3Q),(ZB,R1D,R2L,R3R),(ZB,R1D,R 15 2M,R3A),(ZB,R1D,R2M,R3B),(ZB,R1D,R2M,R3C),(ZB,R1D ,R2M,R3D),(ZB,R1D,R2M,R3E),(ZB,R1D,R2M,R3F),(ZB,R 1D,R2M,R3G),(ZB,R1D,R2M,R3H),(ZB,R1D,R2M,R3I),(ZB, R1D,R2M,R3J),(ZB,R1D,R2M,R3K),(ZB,R1D,R2M,R3L),(Z B,R1D,R2M,R3M),(ZB,R1D,R2M,R3N),(ZB,R1D,R2M,R30) 20 ,(ZB,R1D,R2M,R3P),(ZB,R1D,R2M,R3Q),(ZB,R1D,R2M,R3 R),(ZB,R1D,R2N,R3A),(ZB,R1D,R2N,R3B),(ZB,R1D,R2N,R 3C),(ZB,R1D,R2N,R3D),(ZB,R1D,R2N,R3E),(ZB,R1D,R2N, R3F),(ZB,R1D,R2N,R3G),(ZB,R1D,R2N,R3H),(ZB,R1D,R2 N,R3I),(ZB,R1D,R2N,R3J),(ZB,R1D,R2N,R3K),(ZB,R1D,R2 131 200843739 N,R3L),(ZB,R1D,R2N,R3M),(ZB,R1D,R2N,R3N),(ZB,R1D, R2N,R30),(ZB,R1D,R2N,R3P),(ZB,R1D,R2N,R3Q),(ZB,R1
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5 R1E,R2A,R3F),(ZB,R1E,R2A,R3G),(ZB,R1E,R2A,R3H),(ZB ,R1E,R2A,R3I),(ZB,R1E,R2A,R3J),(ZB,R1E,R2A,R3K),(ZB, R1E,R2A,R3L),(ZB,R1E,R2A,R3M),(ZB,R1E,R2A,R3N),(Z B,R1E,R2A,R30),(ZB,R1E,R2A,R3P),(ZB,R1E,R2A,R3Q),( ZB,R1E,R2A,R3R),(ZB,R1E,R2B,R3A),(ZB,R1E,R2B,R3B), 10 (ZB,R1E,R2B,R3C),(ZB,R1E,R2B,R3D),(ZB,R1E,R2B,R3E), (ZB,R1E,R2B,R3F),(ZB,R1E,R2B,R3G),(ZB,R1E,R2B,R3H), (ZB,R1E,R2B,R3I),(ZB,R1E,R2B,R3J),(ZB,R1E,R2B,R3K),( ZB,R1E,R2B,R3L),(ZB,R1E,R2B,R3M),(ZB,R1E,R2B,R3N), (ZB,R1E,R2B,R30),(ZB,R1E,R2B,R3P),(ZB,R1E,R2B,R3Q), 15 (ZB,R1E,R2B,R3R),(ZB,R1E,R2C,R3A),(ZB,R1E,R2C,R3B), (ZB,R1E,R2C,R3C),(ZB,R1E,R2C,R3D),(ZB,R1E,R2C,R3E), (ZB,R1E,R2C,R3F),(ZB,R1E,R2C,R3G),(ZB,R1E,R2C,R3H), (ZB,R1E,R2C,RM),(ZB,R1E,R2C,R3J),(ZB,R1E,R2C,R3K),( ZB,R1E,R2C,R3L),(ZB,R1E,R2C,R3M),(ZB,R1E,R2C,R3N), 20 (ZB,R1E,R2C,R30),(ZB,R1E,R2C,R3P),(ZB,R1E,R2C,R3Q), (ZB,R1E,R2C,R3R),(ZB,R1E,R2D,R3A),(ZB,R1E,R2D,R3B) ,(ZB,R1E,R2D,R3C),(ZB,R1E,R2D,R3D),(ZB,R1E,R2D,R3E ),(ZB,R1E,R2D,R3F),(ZB,R1E,R2D,R3G),(ZB,R1E,R2D,R3 H),(ZB,R1E,R2D,R3I),(ZB,R1E,R2D,R3J),(ZB,R1E,R2D,R3 132 200843739 K),(ZB,R1E,R2D,R3L),(ZB,R1E,R2D,R3M),(ZB,R1E,R2D,R 3N),(ZB,R1E,R2D,R30),(ZB,R1E,R2D,R3P),(ZB,R1E,R2D, R3Q),(ZB,R1E,R2D,R3R),(ZB,R1E,R2E,R3A),(ZB,R1E,R2E, R3B),(ZB,R1E,R2E,R3C),(ZB,R1E,R2E,R3D),(ZB,R1E,R2E, 5 R3E),(ZB,R1E,R2E,R3F),(ZB,R1E,R2E,R3G),(ZB,R1E,R2E, R3H),(ZB,R1E,R2E,R3I),(ZB,R1E,R2E,R3J),(ZB,R1E,R2E,R 3K),(ZB,R1E,R2E,R3L),(ZB,R1E,R2E,R3M),(ZB,R1E,R2E,R 3N),(ZB,R1E,R2E,R30),(ZB,R1E,R2E,R3P),(ZB,R1E,R2E,R 3Q),(ZB,R1E,R2E,R3R),(ZB,R1E,R2F,R3A),(ZB,R1E,R2F,R 10 3B),(ZB,R1E,R2F,R3C),(ZB,R1E,R2F,R3D),(ZB,R1E,R2F,R3 E),(ZB,R1E,R2F,R3F),(ZB,R1E,R2F,R3G),(ZB,R1E,R2F,R3 H),(ZB,R1E,R2F,R3I),(ZB,R1E,R2F,R3J),(ZB,R1E,R2F,R3K) ,(ZB,R1E,R2F,R3L),(ZB,R1E,R2F,R3M),(ZB,R1E,R2F,R3N), (ZB,R1E,R2F,R30),(ZB,R1E,R2F,R3P),(ZB,R1E,R2F,R3Q),( 15 ZB,R1E,R2F,R3R),(ZB,R1E,R2G,R3A),(ZB,R1E,R2G,R3B),(
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R3H),(ZB,R1F,R2C,R3I),(ZB,R1F,R2C,R3J),(ZB,R1F,R2C,R 3K),(ZB,R1F,R2C,R3L),(ZB,R1F,R2C,R3M),(ZB,R1F,R2C,R 3N),(ZB,R1F,R2C,R30),(ZB,R1F,R2C,R3P),(ZB,R1F,R2C,R 3Q),(ZB,R1F,R2C,R3R),(ZB,R1F,R2D,R3A),(ZB,R1F,R2D,R 10 3B),(ZB,R1F,R2D,R3C),(ZB,R1F,R2D,R3D),(ZB,R1F,R2D,R 3E),(ZB,R1F,R2D,R3F),(ZB,R1F,R2D,R3G),(ZB,R1F,R2D,R 3H),(ZB,R1F,R2D,R;3I),(ZB,R1F,R2D,R3J),(ZB,R1F,R2D,R3 K),(ZB,R1F,R2D,R3L),(ZB,R1F,R2D,R3M),(ZB,R1F,R2D,R3 N),(ZB,R1F,R2D,R30),(ZB,R1F,R2D,R3P),(ZB,R1F,R2D,R3 15 Q),(ZB,R1F,R2D,R3R),(ZB,R1F,R2E,R3A),(ZB,R1F,R2E,R3 B),(ZB,R1F,R2E,R3C),(ZB,R1F,R2E,R3D),(ZB,R1F,R2E,R3 E),(ZB,R1F,R2E,R3F),(ZB,R1F,R2E,R3G),(ZB,R1F,R2E,R3 H),(ZB,R1F,R2E,R3I),(ZB,R1F,R2E,R3J),(ZB,R1F,R2E,R3K) ,(ZB,R1F,R2E,R3L),(ZB,R1F,R2E,R3M),(ZB,R1F,R2E,R3N), 20 (ZB,R1F,R2E,R30),(ZB,R1F,R2E,R3P),(ZB,R1F,R2E,R3Q),( ZB,R1F,R2E,R3R),(ZB,R1F,R2F,R3A),(ZB,R1F,R2F,R3B),(Z B,R1F,R2F,R3C),(ZB,R1F,R2F,R3D),(ZB,R1F,R2F,R3E),(ZB, R1F,R2F,R3F),(ZB,R1F,R2F,R3G),(ZB,R1F,R2F,R3H),(ZB,R 1F,R2F,R3I),(ZB,R1F,R2F,R3J),(ZB,R1F,R2F,R3K),(ZB,R1F, 136 200843739
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R3G),(ZB,R1K,R2L,R3H),(ZB,R1K,R2L,R3I),(ZB,R1K,R2L, R3J),(ZB,R1K,R2L,R3K),(ZB,R1K,R2L,R3L),(ZB,R1K,R2L, R3M),(ZB,R1K,R2L,R3N),(ZB,R1K,R2L,R30),(ZB,R1K,R2 L,R3P),(ZB,R1K,R2L,R3Q),(ZB,R1K,R2L,R3R),(ZB,R1K,R 155 200843739 2M,R3A),(ZB,R1K,R2M,R3B),(ZB,R1K,R2M,R3C),(ZB,R1K ,R2M,R3D),(ZB,R1K,R2M,R3E),(ZB,R1K,R2M,R3F),(ZB,R 1K,R2M,R3G),(ZB,R1K,R2M,R3H),(ZB,R1K,R2M,R3I),(ZB, R1K,R2M,R3J),(ZB,R1K,R2M,R3K),(ZB,R1K,R2M,R3L),(Z 5 B,R1K,R2M,R3M),(ZB,R1K,R2M,R3N),(ZB,R1K,R2M,R30) ,(ZB,R1K,R2M,R3P),(ZB,R1K,R2M,R3Q),(ZB,R1K,R2M,R3 R),(ZB,R1K,R2N,R3A),(ZB,R1K,R2N,R3B),(ZB,R1K,R2N,R 3C),(ZB,R1K,R2N,R3D),(ZB,R1K,R2N,R3E),(ZB,R1K,R2N, R3F),(ZB,R1K,R2N,R3G),(ZB,R1K,R2N,R3H),(ZB,R1K,R2 10 N,R3I),(ZB,R1K,R2N,R3J),(ZB,R1K,R2N,R3K),(ZB,R1K,R2 N,R3L),(ZB,R1K,R2N,R3M),(ZB,R1K,R2N,R3N),(ZB,R1K, R2N,R30),(ZB,R1K,R2N,R3P),(ZB,R1K,R2N,R3Q),(ZB,R1 K,R2N,R3R),(ZB,R1L,R2A,R3A),(ZB,R1L,R2A,R3B),(ZB,R 1L,R2A,R3C),(ZB,R1L,R2A,R3D),(ZB,R1L,R2A,R3E),(ZB,
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ZB,R1L,R2F,R3R),(ZB,R1L,R2G,R3A),(ZB,R1L,R2G,R3B),( ZB,R1L,R2G,R3C),(ZB,R1L,R2G,R3D),(ZB,R1L,R2G,R3E),( ZB,R1L,R2G,R3F),(ZB,R1L,R2G,R3G),(ZB,R1L,R2G,R3H),( ZB,R1L,R2G,R3I),(ZB,R1L,R2G,R3J),(ZB,R1L,R2G,R3K),(Z 5 B,R1L,R2G,R3L),(ZB,R1L,R2G,R3M),(ZB,R1L,R2G,R3N),(Z B,R1L,R2G,R30),(ZB,R1L,R2G,R3P),(ZB,R1L,R2G,R3Q),(Z B,R1L,R2G,R3R),(ZB,R1L,R2H,R3A),(ZB,R1L,R2H,R3B),( ZB,R1L,R2H,R3C),(ZB,R1L,R2H,R3D),(ZB,R1L,R2H,R3E), (ZB,R1L,R2H,R3F),(ZB,R1L,R2H,R3G),(ZB,R1L,R2H,R3H) 10 ,(ZB,R1L,R2H,R3I),(ZB,R1L,R2H,R3J),(ZB,R1L,R2H,R3K), (ZB,R1L,R2H,R3L),(ZB,R1L,R2H,R3M),(ZB,R1L,R2H,R3N ),(ZB,R1L,R2H,R30),(ZB,R1L,R2H,R3P),(ZB,R1L,R2H,R3 Q),(ZB,R1L,R2H,R3R),(ZB,R1L,R2I,R3A),(ZB,R1L,R2I,R3 B),(ZB,R1L,R2I,R3C),(ZB,R1L,R2I,R3D),(ZB,R1L,R2I,R3E 15 ),(ZB,R1L,R2I,R3F),(ZB,R1L,R2I,R3G),(ZB,R1L,R2I,R3H),
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R2N,R3K),(ZC,R1D,R2N,R3L),(ZC,R1D,R2N,R3M),(ZC,R1 D,R2N,R3N),(ZC,R1D,R2N,R30),(ZC,R1D,R2N,R3P),(ZC,R 1D,R2N,R3Q),(ZC,R1D,R2N,R3R),(ZC,R1E,R2A,R3A),(ZC, R1E,R2A,R3B),(ZC,R1E,R2A,R3C),(ZC,R1E,R2A,R3D),(ZC 198 200843739
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R1E,R2A,R3K),(ZC,R1E,R2A,R3L),(ZC,R1E,R2A,R3M),(Z C,R1E,R2A,R3N),(ZC,R1E,R2A,R30),(ZC,R1E,R2A,R3P),( 5 ZC,R1E,R2A,R3Q),(ZC,R1E,R2A,R3R),(ZC,R1E,R2B,R3A), (ZC,R1E,R2B,R3B),(ZC,R1E,R2B,R3C),(ZC,R1E,R2B,R3D), (ZC,R1E,R2B,R3E),(ZC,R1E,R2B,R3F),(ZC,R1E,R2B,R3G), (ZC,R1E,R2B,R3H),(ZC,R1E,R2B,R3I),(ZC,R1E,R2B,R3J),( ZC,R1E,R2B,R3K),(ZC,R1E,R2B,R3L),(ZC,R1E,R2B,R3M), 10 (ZC,R1E,R2B,R3N),(ZC,R1E,R2B,R30),(ZC,R1E,R2B,R3P), (ZC,R1E,R2B,R3Q),(ZC,R1E,R2B,R3R),(ZC,R1E,R2C,R3A) ,(ZC,R1E,R2C,R3B),(ZC,R1E,R2C,R3C),(ZC,R1E,R2C,R3D) ,(ZC,R1E,R2C,R3E),(ZC,R1E,R2C,R3F),(ZC,R1E,R2C,R3G) ,(ZC,R1E,R2C,R3H),(ZC,R1E,R2C,R3I),(ZC,R1E,R2C,R3J), 15 (ZC,R1E,R2C,R3K),(ZC,R1E,R2C,R3L),(ZC,R1E,R2C,R3M) ,(ZC,R1E,R2C,R3N),(ZC,R1E,R2C,R30),(ZC,R1E,R2C,R3P) ,(ZC,R1E,R2C,R3Q),(ZC,R1E,R2C,R3R),(ZC,R1E,R2D,R3A ),(ZC,R1E,R2D,R3B),(ZC,R1E,R2D,R3C),(ZC,R1E,R2D,R3 D),(ZC,R1E,R2D,R3E),(ZC,R1E,R2D,R3F),(ZC,R1E,R2D,R3 20 G),(ZC,R1E,R2D,R3H),(ZC,R1E,R2D,R3I),(ZC,R1E,R2D,R3
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3J),(ZC,R1E,R2E,R3K),(ZC,R1E,R2E,R3L),(ZC,R1E,R2E,R 3M),(ZC,R1E,R2E,R3N),(ZC,R1E,R2E,R30),(ZC,R1E,R2E, 5 R3P),(ZC,R1E,R2E,R3Q),(ZC,R1E,R2E,R3R),(ZC,R1E,R2F, R3A),(ZC,R1E,R2F,R3B),(ZC,R1E,R2F,R3C),(ZC,R1E,R2F, R3D),(ZC,R1E,R2F,R3E),(ZC,R1E,R2F,R3F),(ZC,R1E,R2F,R 3G),(ZC,R1E,R2F,R3H),(ZC,R1E,R2F,R3I),(ZC,R1E,R2F,R3 J),(ZC,R1E,R2F,R3K),(ZC,R1E,R2F,R3L),(ZC,R1E,R2F,R3 10 M),(ZC,R1E,R2F,R3N),(ZC,R1E,R2F,R30),(ZC,R1E,R2F,R3
P),(ZC,R1E,R2F,R3Q),(ZC,R1E,R2F,R3R),(ZC,R1E,R2G,R3 A),(ZC,R1E,R2G,R3B),(ZC,R1E,R2G,R3C),(ZC,R1E,R2G,R3 D),(ZC,R1E,R2G,R3E),(ZC,R1E,R2G,R3F),(ZC,R1E,R2G,R3 G),(ZC,R1E,R2G,R3H),(ZC,R1E,R2G,R3I),(ZC,R1E,R2G,R3J 15 ),(ZC,R1E,R2G,R3K),(ZC,R1E,R2G,R3L),(ZC,R1E,R2G,R3M ),(ZC,R1E,R2G,R3N),(ZC,R1E,R2G,R30),(ZC,R1E,R2G,R3P ),(ZC,R1E,R2G,R3Q),(ZC,R1E,R2G,R3R),(ZC,R1E,R2H,R3A ),(ZC,R1E,R2H,R3B),(ZC,R1E,R2H,R3C),(ZC,R1E,R2H,R3 D),(ZC,R1E,R2H,R3E),(ZC,R1E,R2H,R3F),(ZC,R1E,R2H,R3 20 G),(ZC,R1E,R2H,R3H),(ZC,R1E,R2H,R3I),(ZC,R1E,R2H,R3 J),(ZC,R1E,R2H,R3K),(ZC,R1E,R2H,R3L),(ZC,R1E,R2H,R3 M),(ZC,R1E,R2H,R3N),(ZC,R1E,R2H,R30),(ZC,R1E,R2H,R 3P),(ZC,R1E,R2H,R3Q),(ZC,R1E,R2H,R3R),(ZC,R1E,R2I,R 3A),(ZC,R1E,R2I,R3B),(ZC,R1E,R2I,R3C),(ZC,R1E,R2I,R3 200 200843739 D),(ZC,R1E,R2I,R3E),(ZC,R1E,R2I,R3F),(ZC,R1E,R2I,R3G) ,(ZC,R1E,R2I,R3H),(ZC,R1E,R2I,R3I),(ZC,R1E,R2I,R3J),(Z C,R1E,R2I,R3K),(ZC,R1E,R2I,R3L),(ZC,R1E,R2I,R3M),(ZC ,R1E,R2I,R3N),(ZC,R1E,R2I,R30),(ZC,R1E,R2I,R3P),(ZC,R 5 1E,R2I,R3Q),(ZC,R1E,R2I,R3R),(ZC,R1E,R2J,R3A),(ZC,R1 E,R2J,R3B),(ZC,R1E,R2J,R3C),(ZC,R1E,R2J,R3D),(ZC,R1E ,R2J,R3E),(ZC,R1E,R2J,R3F),(ZC,R1E,R2J,R3G),(ZC,R1E, R2J,R3H),(ZC,R1E,R2J,R3I),(ZC,R1E,R2J,R3J),(ZC,R1E,R2 J,R3K),(ZC,R1E,R2J,R3L),(ZC,R1E,R2J,R3M),(ZC,R1E,R2J 10 ,R3N),(ZC,R1E,R2J,R30),(ZC,R1E,R2J,R3P),(ZC,R1E,R2J, R3Q),(ZC,R1E,R2J,R3R),(ZC,R1E,R2K,R3A),(ZC,R1E,R2K, R3B),(ZC,R1E,R2K,R3C),(ZC,R1E,R2K,R3D),(ZC,R1E,R2K ,R3E),(ZC,R1E,R2K,R3F),(ZC,R1E,R2K,R3G),(ZC,R1E,R2K ,R3H),(ZC,R1E,R2K,R3I),(ZC,R1E,R2K,R3J),(ZC,R1E,R2K, 15 R3K),(ZC,R1E,R2K,R3L),(ZC,R1E,R2K,R3M),(ZC,R1E,R2
K,R3N),(ZC,R1E,R2K,R30),(ZC,R1E,R2K,R3P),(ZC,R1E,R 2K,R3Q),(ZC,R1E,R2K,R3R),(ZC,R1E,R2L,R3A),(ZC,R1E, R2L,R3B),(ZC,R1E,R2L,R3C),(ZC,R1E,R2L,R3D),(ZC,R1E, R2L,R3E),(ZC,R1E,R2L,R3F),(ZC,R1E,R2L,R3G),(ZC,R1E, 20 R2L,R3H),(ZC,R1E,R2L,R3I),(ZC,R1E,R2L,R3J),(ZC,R1E,R 2L,R3K),(ZC,R1E,R2L,R3L),(ZC,R1E,R2L,R3M),(ZC,R1E,R 2L,R3N),(ZC,R1E,R2L,R30),(ZC,R1E,R2L,R3P),(ZC,R1E,R 2L,R3Q),(ZC,R1E,R2L,R3R),(ZC,R1E,R2M,R3A),(ZC,R1E, R2M,R3B),(ZC,R1E,R2M,R3C),(ZC,R1E,R2M,R3D),(ZC,R1 201 200843739 E,R2M,R3E),(ZC,R1E,R2M,R3F),(ZC,R1E,R2M,R3G),(ZC,R 1E,R2M,R3H),(ZC,R1E,R2M,R3I),(ZC,R1E,R2M,R3J),(ZC, R1E,R2M,R3K),(ZC,R1E,R2M,R3L),(ZC,R1E,R2M,R3M),(Z C,R1E,R2M,R3N),(ZC,R1E,R2M,R30),(ZC,R1E,R2M,R3P),( 5 ZC,R1E,R2M,R3Q),(ZC,R1E,R2M,R3R),(ZC,R1E,R2N,R3A) ,(ZC,R1E,R2N,R3B),(ZC,R1E,R2N,R3C),(ZC,R1E,R2N,R3D ),(ZC,R1E,R2N,R3E),(ZC,R1E,R2N,R3F),(ZC,R1E,R2N,R3G ),(ZC,R1E,R2N,R3H),(ZC,R1E,R2N,R3I),(ZC,R1E,R2N,R3J) ,(ZC,R1E,R2N,R3K),(ZC,R1E,R2N,R3L),(ZC,R1E,R2N,R3M 10 ),(ZC,R1E,R2N,R3N),(ZC,R1E,R2N,R30),(ZC,R1E,R2N,R3
P),(ZC,R1E,R2N,R3Q),(ZC,R1E,R2N,R3R),(ZC,R1F,R2A,R3 A),(ZC,R1F,R2A,R3B),(ZC,R1F,R2A,R3C),(ZC,R1F,R2A,R3 D),(ZC,R1F,R2A,R3E),(ZC,R1F,R2A,R3F),(ZC,R1F,R2A,R3 G),(ZC,R1F,R2A,R3H),(ZC,R1F,R2A,R3I),(ZC,R1F,R2A,R3J 15 ),(ZC,R1F,R2A,R3K),(ZC,R1F,R2A,R3L),(ZC,R1F,R2A,R3M ),(ZC,R1F,R2A,R3N),(ZC,R1F,R2A,R30),(ZC,R1F,R2A,R3P ),(ZC,R1F,R2A,R3Q),(ZC,R1F,R2A,R3R),(ZC,R1F,R2B,R3A ),(ZC,R1F,R2B,R3B),(ZC,R1F,R2B,R3C),(ZC,R1F,R2B,R3D) ,(ZC,R1F,R2B,R3E),(ZC,R1F,R2B,R3F),(ZC,R1F,R2B,R3G), 20 (ZC,R1F,R2B,R3H),(ZC,R1F,R2B,R3I),(ZC,R1F,R2B,R3J),( ZC,R1F,R2B,R3K),(ZC,R1F,R2B,R3L),(ZC,R1F,R2B,R3M),( ZC,R1F,R2B,R3N),(ZC,R1F,R2B,R30),(ZC,R1F,R2B,R3P),( ZC,R1F,R2B,R3Q),(ZC,R1F,R2B,R3R),(ZC,R1F,R2C,R3A),( ZC,R1F,R2C,R3B),(ZC,R1F,R2C,R3C),(ZC,R1F,R2C,R3D),( 202 200843739
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R2L,R3D),(ZC,R1K,R2L,R3E),(ZC,R1K,R2L,R3F),(ZC,R1K, R2L,R3G),(ZC,R1K,R2L,R3H),(ZC,R1K,R2L,R3I),(ZC,R1K, R2L,R3J),(ZC,R1K,R2L,R3K),(ZC,R1K,R2L,R3L),(ZC,R1K, R2L,R3M),(ZC,R1K,R2L,R3N),(ZC,R1K,R2L,R30),(ZC,R1 20 K,R2L,R3P),(ZC,R1K,R2L,R3Q),(ZC,R1K,R2L,R3R),(ZC,R 1K,R2M,R3A),(ZC,R1K,R2M,R3B),(ZC,R1K,R2M,R3C),(ZC ,R1K,R2M,R3D),(ZC,R1K,R2M,R3E),(ZC,R1K,R2M,R3F),( ZC,R1K,R2M,R3G),(ZC,R1K,R2M,R3H),(ZC,R1K,R2M,R3I ),(ZC,R1K,R2M,R3J),(ZC,R1K,R2M,R3K),(ZC,R1K,R2M,R3 222 200843739
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(ZC,R1L,R2A,R3F),(ZC,R1L,R2A,R3G),(ZC,R1L,R2A,R3H) ,(ZC,R1L,R2A,R3I),(ZC,R1L,R2A,R3J),(ZC,R1L,R2A,R3K), (ZC,R1L,R2A,R3L),(ZC,R1L,R2A,R3M),(ZC,R1L,R2A,R3N ),(ZC,R1L,R2A,R30),(ZC,R1L,R2A,R3P),(ZC,R1L,R2A,R3 15 Q),(ZC,R1L,R2A,R3R),(ZC,R1L,R2B,R3A),(ZC,R1L,R2B,R
3B),(ZC,R1L,R2B,R3C),(ZC,R1L,R2B,R3D),(ZC,R1L,R2B,R 3E),(ZC,R1L,R2B,R3F),(ZC,R1L,R2B,R3G),(ZC,R1L,R2B,R 3H),(ZC,R1L,R2B,R3I),(ZC,R1L,R2B,R3J),(ZC,R1L,R2B,R3 K),(ZC,R1L,R2B,R3L),(ZC,R1L,R2B,R3M),(ZC,R1L,R2B,R 20 3N),(ZC,R1L,R2B,R30),(ZC,R1L,R2B,R3P),(ZC,R1L,R2B,R 3Q),(ZC,R1L,R2B,R3R),(ZC,R1L,R2C,R3A),(ZC,R1L,R2C, R3B),(ZC,R1L,R2C,R3C),(ZC,R1L,R2C,R3D),(ZC,R1L,R2C, R3E),(ZC,R1L,R2C,R3F),(ZC,R1L,R2C,R3G),(ZC,R1L,R2C, R3H),(ZC,R1L,R2C,R3I),(ZC,R1L,R2C,R3J),(ZC,R1L,R2C, 223 200843739
R3K),(ZC,R1L,R2C,R3L),(ZC,R1L,R2C,R3M),(ZC,R1L,R2C ,R3N),(ZC,R1L,R2C,R30),(ZC,R1L,R2C,R3P),(ZC,R1L,R2C ,R3Q),(ZC,R1L,R2C,R3R),(ZC,R1L,R2D,R3A),(ZC,R1L,R2 D,R3B),(ZC,R1L,R2D,R3C),(ZC,R1L,R2D,R3D),(ZC,R1L,R 5 2D,R3E),(ZC,R1L,R2D,R3F),(ZC,R1L,R2D,R3G),(ZC,R1L,R 2D,R3H),(ZC,R1L,R2D,R3I),(ZC,R1L,R2D,R3J),(ZC,R1L,R 2D,R3K),(ZC,R1L,R2D,R3L),(ZC,R1L,R2D,R3M),(ZC,R1L, R2D,R3N),(ZC,R1L,R2D,R30),(ZC,R1L,R2D,R3P),(ZC,R1L ,R2D,R3Q),(ZC,R1L,R2D,R3R),(ZC,R1L,R2E,R3A),(ZC,R1 10 L,R2E,R3B),(ZC,R1L,R2E,R3C),(ZC,R1L,R2E,R3D),(ZC,R1
L,R2E,R3E),(ZC,R1L,R2E,R3F),(ZC,R1L,R2E,R3G),(ZC,R1 L,R2E,R3H),(ZC,R1L,R2E,R3I),(ZC,R1L,R2E,R3J),(ZC,R1L ,R2E,R3K),(ZC,R1L,R2E,R3L),(ZC,R1L,R2E,R3M),(ZC,R1L ,R2E,R3N),(ZC,R1L,R2E,R30),(ZC,R1L,R2E,R3P),(ZC,R1L 15 ,R2E,R3Q),(ZC,R1L,R2E,R3R),(ZC,R1L,R2F,R3A),(ZC,R1L ,R2F,R3B),(ZC,R1L,R2F,R3C),(ZC,R1L,R2F,R3D),(ZC,R1L, R2F,R3E),(ZC,R1L,R2F,R3F),(ZC,R1L,R2F,R3G),(ZC,R1L,R 2F,R3H),(ZC,R1L,R2F,R3I),(ZC,R1L,R2F,R3J),(ZC,R1L,R2F ,R3K),(ZC,R1L,R2F,R3L),(ZC,R1L,R2F,R3M),(ZC,R1L,R2F, 20 R3N),(ZC,R1L,R2F,R30),(ZC,R1L,R2F,R3P),(ZC,R1L,R2F,
R3Q),(ZC,R1L,R2F,R3R),(ZC,R1L,R2G,R3A),(ZC,R1L,R2G, R3B),(ZC,R1L,R2G,R3C),(ZC,R1L,R2G,R3D),(ZC,R1L,R2G, R3E),(ZC,R1L,R2G,R3F),(ZC,R1L,R2G,R3G),(ZC,R1L,R2G, R3H),(ZC,R1L,R2G,R3I),(ZC,R1L,R2G,R3J),(ZC,R1L,R2G,R 224 200843739
3K),(ZC,R1L,R2G,R3L),(ZC,R1L,R2G,R3M),(ZC,R1L,R2G,R 3N),(ZC,R1L,R2G,R30),(ZC,R1L,R2G,R3P),(ZC,R1L,R2G,R 3Q),(ZC,R1L,R2G,R3R),(ZC,R1L,R2H,R3A),(ZC,R1L,R2H, R3B),(ZC,R1L,R2H,R3C),(ZC,R1L,R2H,R3D),(ZC,R1L,R2H 5 ,R3E),(ZC,R1L,R2H,R3F),(ZC,R1L,R2H,R3G),(ZC,R1L,R2H
,R3H),(ZC,R1L,R2H,R3I),(ZC,R1L,R2H,R3J),(ZC,R1L,R2H, R3K),(ZC,R1L,R2H,R3L),(ZC,R1L,R2H,R3M),(ZC,R1L,R2 H,R3N),(ZC,R1L,R2H,R30),(ZC,R1L,R2H,R3P),(ZC,R1L,R 2H,R3Q),(ZC,R1L,R2H,R3R),(ZC,R1L,R2I,R3A),(ZC,R1L,R 10 2I,R3B),(ZC,R1L,R2I,R3C),(ZC,R1L,R2I,R3D),(ZC,R1L,R2I
,R3E),(ZC,R1L,R2I,R3F),(ZC,R1L,R2I,R3G),(ZC,R1L,R2I,R 3H),(ZC,R1L,R2I,R3I),(ZC,R1L,R2I,R3J),(ZC,R1L,R2I,R3K ),(ZC,R1L,R2I,R3L),(ZC,R1L,R2I,R3M),(ZC,R1L,R2I,R3N), (ZC,R1L,R2I,R30),(ZC,R1L,R2I,R3P),(ZC,R1L,R2I,R3Q),(Z 15 C,R1L,R2I,R3R),(ZC,R1L,R2J,R3A),(ZC,R1L,R2J,R3B),(ZC
,R1L,R2J,R3C),(ZC,R1L,R2J,R3D),(ZC,R1L,R2J,R3E),(ZC, R1L,R2J,R3F),(ZC,R1L,R2J,R3G),(ZC,R1L,R2J,R3H),(ZC,R 1L,R2J,R3I),(ZC,R1L,R2J,R3J),(ZC,R1L,R2J,R3K),(ZC,R1L ,R2J,R3L),(ZC,R1L,R2J,R3M),(ZC,R1L,R2J,R3N),(ZC,R1L, 20 R2J,R30),(ZC,R1L,R2J,R3P),(ZC,R1L,R2J,R3Q),(ZC,R1L,R 2J,R3R),(ZC,R1L,R2K,R3A),(ZC,R1L,R2K,R3B),(ZC,R1L,R 2K,R3C),(ZC,R1L,R2K,R3D),(ZC,R1L,R2K,R3E),(ZC,R1L, R2K,R3F),(ZC,R1L,R2K,R3G),(ZC,R1L,R2K,R3H),(ZC,R1L ,R2K,R3I),(ZC,R1L,R2K,R3J),(ZC,R1L,R2K,R3K),(ZC,R1L, 225 200843739
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R1L,R2M,R3F),(ZC,R1L,R2M,R3G),(ZC,R1L,R2M,R3H),(Z C,R1L,R2M,R3I),(ZC,R1L,R2M,R3J),(ZC,R1L,R2M,R3K),( ZC,R1L,R2M,R3L),(ZC,R1L,R2M,R3M),(ZC,R1L,R2M,R3N ),(ZC,R1L,R2M,R30),(ZC,R1L,R2M,R3P),(ZC,R1L,R2M,R3 15 Q),(ZC,R1L,R2M,R3R),(ZC,R1L,R2N,R3A),(ZC,R1L,R2N,R
3B),(ZC,R1L,R2N,R3C),(ZC,R1L,R2N,R3D),(ZC,R1L,R2N, R3E),(ZC,R1L,R2N,R3F),(ZC,R1L,R2N,R3G),(ZC,R1L,R2N, R3H),(ZC,R1L,R2N,R3I),(ZC,R1L,R2N,R3J),(ZC,R1L,R2N, R3K),(ZC,R1L,R2N,R3L),(ZC,R1L,R2N,R3M),(ZC,R1L,R2 20 N,R3N),(ZC,R1L,R2N,R30),(ZC,R1L,R2N,R3P),(ZC,R1L,R
2N,R3Q),(ZC,R1L,R2N,R3R),(ZC,R1M,R2A,R3A),(ZC,R1M ,R2A,R3B),(ZC,R1M,R2A,R3C),(ZC,R1M,R2A,R3D),(ZC,R 1M,R2A,R3E),(ZC,R1M,R2A,R3F),(ZC,R1M,R2A,R3G),(ZC ,R1M,R2A,R3H),(ZC,R1M,R2A,R3I),(ZC,R1M,R2A,R3J),(Z 226 200843739 C,R1M,R2A,R3K),(ZC,R1M,R2A,R3L),(ZC,R1M,R2A,R3M) ,(ZC,R1M,R2A,R3N),(ZC,R1M,R2A,R30),(ZC,R1M,R2A,R3 P),(ZC,R1M,R2A,R3Q),(ZC,R1M,R2A,R3R),(ZC,R1M,R2B, R3A),(ZC,R1M,R2B,R3B),(ZC,R1M,R2B,R3C),(ZC,R1M,R2 5 B,R3D),(ZC,R1M,R2B,R3E),(ZC,R1M,R2B,R3F),(ZC,R1M, R2B,R3G),(ZC,R1M,R2B,R3H),(ZC,R1M,R2B,R3I),(ZC,R1 M,R2B,R3J),(ZC,R1M,R2B,R3K),(ZC,R1M,R2B,R3L),(ZC,R 1M,R2B,R3M),(ZC,R1M,R2B,R3N),(ZC,R1M,R2B,R30),(Z C,R1M,R2B,R3P),(ZC,R1M,R2B,R3Q),(ZC,R1M,R2B,R3R), 10 (ZC,R1M,R2C,R3A),(ZC,R1M,R2C,R3B),(ZC,R1M,R2C,R3 C),(ZC,R1M,R2C,R3D),(ZC,R1M,R2C,R3E),(ZC,R1M,R2C, R3F),(ZC,R1M,R2C,R3G),(ZC,R1M,R2C,R3H),(ZC,R1M,R2 C,R3I),(ZC,R1M,R2C,R3J),(ZC,R1M,R2C,R3K),(ZC,R1M,R 2C,R3L),(ZC,R1M,R2C,R3M),(ZC,R1M,R2C,R3N),(ZC,R1M 15 ,R2C,R30),(ZC,R1M,R2C,R3P),(ZC,R1M,R2C,R3Q),(ZC,R1
M,R2C,R3R),(ZC,R1M,R2D,R3A),(ZC,R1M,R2D,R3B),(ZC, R1M,R2D,R3C),(ZC,R1M,R2D,R3D),(ZC,R1M,R2D,R3E),(Z C,R1M,R2D,R3F),(ZC,R1M,R2D,R3G),(ZC,R1M,R2D,R3H), (ZC,R1M,R2D,R3I),(ZC,R1M,R2D,R3J),(ZC,R1M,R2D,R3K 20 ),(ZC,R1M,R2D,R3L),(ZC,R1M,R2D,R3M),(ZC,R1M,R2D,R 3N),(ZC,R1M,R2D,R30),(ZC,R1M,R2D,R3P),(ZC,R1M,R2D ,R3Q),(ZC,R1M,R2D,R3R),(ZC,R1M,R2E,R3A),(ZC,R1M,R 2E,R3B),(ZC,R1M,R2E,R3C),(ZC,R1M,R2E,R3D),(ZC,R1M, R2E,R3E),(ZC,R1M,R2E,R3F),(ZC,R1M,R2E,R3G),(ZC,R1 227 200843739 M,R2E,R3H),(ZC,R1M,R2E,R3I),(ZC,R1M,R2E,R3J),(ZC,R 1M,R2E,R3K),(ZC,R1M,R2E,R3L),(ZC,R1M,R2E,R3M),(ZC ,R1M,R2E,R3N),(ZC,R1M,R2E,R30),(ZC,R1M,R2E,R3P),(Z C,R1M,R2E,R3Q),(ZC,R1M,R2E,R3R),(ZC,R1M,R2F,R3A),( 5 ZC,R1M,R2F,R3B),(ZC,R1M,R2F,R3C),(ZC,R1M,R2F,R3D),
(ZC,R1M,R2F,R3E),(ZC,R1M,R2F,R3F),(ZC,R1M,R2F,R3G) ,(ZC,R1M,R2F,R3H),(ZC,R1M,R2F,R3I),(ZC,R1M,R2F,R3J), (ZC,R1M,R2F,R3K),(ZC,R1M,R2F,R3L),(ZC,R1M,R2F,R3M ),(ZC,R1M,R2F,R3N),(ZC,R1M,R2F,R30),(ZC,R1M,R2F,R3 10 P),(ZC,R1M,R2F,R3Q),(ZC,R1M,R2F,R3R),(ZC,R1M,R2G,R 3A),(ZC,R1M,R2G,R3B),(ZC,R1M,R2G,R3C),(ZC,R1M,R2G, R3D),(ZC,R1M,R2G,R3E),(ZC,R1M,R2G,R3F),(ZC,R1M,R2 G,R3G),(ZC,R1M,R2G,R3H),(ZC,R1M,R2G,R3I),(ZC,R1M,R 2G,R3J),(ZC,R1M,R2G,R3K),(ZC,R1M,R2G,R3L),(ZC,R1M, 15 R2G,R3M),(ZC,R1M,R2G,R3N),(ZC,R1M,R2G,R30),(ZC,R1 M,R2G,R3P),(ZC,R1M,R2G,R3Q),(ZC,R1M,R2G,R3R),(ZC,R 1M,R2H,R3A),(ZC,R1M,R2H,R3B),(ZC,R1M,R2H,R3C),(ZC ,R1M,R2H,R3D),(ZC,R1M,R2H,R3E),(ZC,R1M,R2H,R3F),( ZC,R1M,R2H,R3G),(ZC,R1M,R2H,R3H),(ZC,R1M,R2H,R3I 20 ),(ZC,R1M,R2H,R3J),(ZC,R1M,R2H,R3K),(ZC,R1M,R2H,R3
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R2L,R3K),(ZC,R1M,R2L,R3L),(ZC,R1M,R2L,R3M),(ZC,R1 M,R2L,R3N),(ZC,R1M,R2L,R30),(ZC,R1M,R2L,R3P),(ZC, R1M,R2L,R3Q),(ZC,R1M,R2L,R3R),(ZC,R1M,R2M,R3A),(Z C,R1M,R2M,R3B),(ZC,R1M,R2M,R3C),(ZC,R1M,R2M,R3D 229 200843739
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K),(ZC,R1R,R2J,R3L),(ZC,R1R,R2J,R3M),(ZC,R1R,R2J,R3 N),(ZC,R1R,R2J,R30),(ZC,R1R,R2J,R3P),(ZC,R1R,R2J,R3 Q),(ZC,R1R,R2J,R3R),(ZC,R1R,R2K,R3A),(ZC,R1R,R2K,R 3B),(ZC,R1R,R2K,R3C),(ZC,R1R,R2K,R3D),(ZC,R1R,R2K, 5 R3E),(ZC,R1R,R2K,R3F),(ZC,R1R,R2K,R3G),(ZC,R1R,R2K ,R3H),(ZC,R1R,R2K,R3I),(ZC,R1R,R2K,R3J),(ZC,R1R,R2K ,R3K),(ZC,R1R,R2K,R3L),(ZC,R1R,R2K,R3M),(ZC,R1R,R2 K,R3N),(ZC,R1R,R2K,R30),(ZC,R1R,R2K,R3P),(ZC,R1R,R 2K,R3Q),(ZC,R1R,R2K,R3R),(ZC,R1R,R2L,R3A),(ZC,R1R, 10 R2L,R3B),(ZC,R1R,R2L,R3C),(ZC,R1R,R2L,R3D),(ZC,R1R, R2L,R3E),(ZC,R1R,R2L,R3F),(ZC,R1R,R2L,R3G),(ZC,R1R, R2L,R3H),(ZC,R1R,R2L,R3I),(ZC,R1R,R2L,R3J),(ZC,R1R, R2L,R3K),(ZC,R1R,R2L,R3L),(ZC,R1R,R2L,R3M),(ZC,R1R ,R2L,R3N),(ZC,R1R,R2L,R30),(ZC,R1R,R2L,R3P),(ZC,R1R 15 ,R2L,R3Q),(ZC,R1R,R2L,R3R),(ZC,R1R,R2M,R3A),(ZC,R1
R,R2M,R3B),(ZC,R1R,R2M,R3C),(ZC,R1R,R2M,R3D),(ZC, R1R,R2M,R3E),(ZC,R1R,R2M,R3F),(ZC,R1R,R2M,R3G),(Z C,R1R,R2M,R3H),(ZC,R1R,R2M,R3I),(ZC,R1R,R2M,R3J),( ZC,R1R,R2M,R3K),(ZC,R1R,R2M,R3L),(ZC,R1R,R2M,R3M 20 ),(ZC,R1R,R2M,R3N),(ZC,R1R,R2M,R30),(ZC,R1R,R2M,R 3P),(ZC,R1R,R2M,R3Q),(ZC,R1R,R2M,R3R),(ZC,R1R,R2N, R3A),(ZC,R1R,R2N,R3B),(ZC,R1R,R2N,R3C),(ZC,R1R,R2 N,R3D),(ZC,R1R,R2N,R3E),(ZC,R1R,R2N,R3F),(ZC,R1R,R 2N,R3G),(ZC,R1R,R2N,R3H),(ZC,R1R,R2N,R3I),(ZC,R1R, 247 200843739
R2N,R3J),(ZC,R1R,R2N,R3K),(ZC,R1R,R2N,R3L),(ZC,R1R, R2N,R3M),(ZC,R1R,R2N,R3N),(ZC,R1R,R2N,R30),(ZC,R1 R,R2N,R3P),(ZC,R1R,R2N,R3Q),(ZC,R1R,R2N,R3R),(ZC,R 1S,R2A,R3A),(ZC,R1S,R2A,R3B),(ZC,R1S,R2A,R3C),(ZC,R 5 1S,R2A,R3D),(ZC,R1S,R2A,R3E),(ZC,R1S,R2A,R3F),(ZC,R 1S,R2A,R3G),(ZC,R1S,R2A,R3H),(ZC,R1S,R2A,R3I),(ZC,R 1S,R2A,R3J),(ZC,R1S,R2A,R3K),(ZC,R1S,R2A,R3L),(ZC,R 1S,R2A,R3M),(ZC,R1S,R2A,R3N),(ZC,R1S,R2A,R30),(ZC, R1S,R2A,R3P),(ZC,R1S,R2A,R3Q),(ZC,R1S,R2A,R3R),(ZC, 10 R1S,R2B,R3A),(ZC,R1S,R2B,R3B),(ZC,R1S,R2B,R3C),(ZC,
R1S,R2B,R3D),(ZC,R1S,R2B,R3E),(ZC,R1S,R2B,R3F),(ZC, R1S,R2B,R3G),(ZC,R1S,R2B,R3H),(ZC,R1S,R2B,R3I),(ZC, R1S,R2B,R3J),(ZC,R1S,R2B,R3K),(ZC,R1S,R2B,R3L),(ZC, R1S,R2B,R3M),(ZC,R1S,R2B,R3N),(ZC,R1S,R2B,R30),(ZC 15 ,R1S,R2B,R3P),(ZC,R1S,R2B,R3Q),(ZC,R1S,R2B,R3R),(ZC
,R1S,R2C,R3A),(ZC,R1S,R2C,R3B),(ZC,R1S,R2C,R3C),(ZC ,R1S,R2C,R3D),(ZC,R1S,R2C,R3E),(ZC,R1S,R2C,R3F),(ZC, R1S,R2C,R3G),(ZC,R1S,R2C,R3H),(ZC,R1S,R2C,R3I),(ZC, R1S,R2C,R3J),(ZC,R1S,R2C,R3K),(ZC,R1S,R2C,R3L),(ZC, 20 R1S,R2C,R3M),(ZC,R1S,R2C,R3N),(ZC,R1S,R2C,R30),(ZC
,R1S,R2C,R3P),(ZC,R1S,R2C,R3Q),(ZC,R1S,R2C,R3R),(ZC ,R1S,R2D,R3A),(ZC,R1S,R2D,R3B),(ZC,R1S,R2D,R3C),(ZC ,R1S,R2D,R3D),(ZC,R1S,R2D,R3E),(ZC,R1S,R2D,R3F),(ZC ,R1S,R2D,R3G),(ZC,R1S,R2D,R3H),(ZC,R1S,R2D,R3I),(ZC 248 200843739 ,R1S,R2D,R3J),(ZC,R1S,R2D,R3K),(ZC,R1S,R2D,R3L),(ZC, R1S,R2D,R3M),(ZC,R1S,R2D,R3N),(ZC,R1S,R2D,R30),(ZC ,R1S,R2D,R3P),(ZC,R1S,R2D,R3Q),(ZC,R1S,R2D,R3R),(ZC ,R1S,R2E,R3A),(ZC,R1S,R2E,R3B),(ZC,R1S,R2E,R3C),(ZC, 5 R1S,R2E,R3D),(ZC,R1S,R2E,R3E),(ZC,R1S,R2E,R3F),(ZC,
R1S,R2E,R3G),(ZC,R1S,R2E,R3H),(ZC,R1S,R2E,R3I),(ZC, R1S,R2E,R3J),(ZC,R1S,R2E,R3K),(ZC,R1S,R2E,R3L),(ZC, R1S,R2E,R3M),(ZC,R1S,R2E,R3N),(ZC,R1S,R2E,R30),(ZC, R1S,R2E,R3P),(ZC,R1S,R2E,R3Q),(ZC,R1S,R2E,R3R),(ZC, 10 R1S,R2F,R3A),(ZC,R1S,R2F,R3B),(ZC,R1S,R2F,R3C),(ZC,R 1S,R2F,R3D),(ZC,R1S,R2F,R3E),(ZC,R1S,R2F,R3F),(ZC,R1 S,R2F,R3G),(ZC,R1S,R2F,R3H),(ZC,R1S,R2F,R3I),(ZC,R1S, R2F,R3J),(ZC,R1S,R2F,R3K),(ZC,R1S,R2F,R3L),(ZC,R1S,R 2F,R3M),(ZC,R1S,R2F,R3N),(ZC,R1S,R2F,R30),(ZC,R1S,R 15 2F,R3P),(ZC,R1S,R2F,R3Q),(ZC,R1S,R2F,R3R),(ZC,R1S,R2
G,R3A),(ZC,R1S,R2G,R3B),(ZC,R1S,R2G,R3C),(ZC,R1S,R2 G,R3D),(ZC,R1S,R2G,R3E),(ZC,R1S,R2G,R3F),(ZC,R1S,R2 G,R3G),(ZC,R1S,R2G,R3H),(ZC,R1S,R2G,R3I),(ZC,R1S,R2 G,R3J),(ZC,R1S,R2G,R3K),(ZC,R1S,R2G,R3L),(ZC,R1S,R2G 20 ,R3M),(ZC,R1S,R2G,R3N),(ZC,R1S,R2G,R30),(ZC,R1S,R2G ,R3P),(ZC,R1S,R2G,R3Q),(ZC,R1S,R2G,R3R),(ZC,R1S,R2H, R3A),(ZC,R1S,R2H,R3B),(ZC,R1S,R2H,R3C),(ZC,R1S,R2H, R3D),(ZC,R1S,R2H,R3E),(ZC,R1S,R2H,R3F),(ZC,R1S,R2H, R3G),(ZC,R1S,R2H,R3H),(ZC,R1S,R2H,R3I),(ZC,R1S,R2H, 249 200843739
R3J),(ZC,R1S,R2H,R3K),(ZC,R1S,R2H,R3L),(ZC,R1S,R2H, R3M),(ZC,R1S,R2H,R3N),(ZC,R1S,R2H,R30),(ZC,R1S,R2H ,R3P),(ZC,R1S,R2H,R3Q),(ZC,R1S,R2H,R3R),(ZC,R1S,R2I, R3A),(ZC,R1S,R2I,R3B),(ZC,R1S,R2I,R3C),(ZC,R1S,R2I,R 5 3D),(ZC,R1S,R2I,R3E),(ZC,R1S,R2I,R3F),(ZC,R1S,R2I,R3G ),(ZC,R1S,R2I,R3H),(ZC,R1S,R2I,R3I),(ZC,R1S,R2I,R3J),(Z C,R1S,R2I,R3K),(ZC,R1S,R2I,R3L),(ZC,R1S,R2I,R3M),(ZC ,R1S,R2I,R3N),(ZC,R1S,R2I,R30),(ZC,R1S,R2I,R3P),(ZC,R 1S,R2I,R3Q),(ZC,R1S,R2I,R3R),(ZC,R1S,R2J,R3A),(ZC,R1 10 S,R2J,R3B),(ZC,R1S,R2J,R3C),(ZC,R1S,R2J,R3D),(ZC,R1S, R2J,R3E),(ZC,R1S,R2J,R3F),(ZC,R1S,R2J,R3G),(ZC,R1S,R 2J,R3H),(ZC,R1S,R2J,R3I),(ZC,R1S,R2J,R3J),(ZC,R1S,R2J, R3K),(ZC,R1S,R2J,R3L),(ZC,R1S,R2J,R3M),(ZC,R1S,R2J,R 3N),(ZC,R1S,R2J,R30),(ZC,R1S,R2J,R3P),(ZC,R1S,R2J,R3 15 Q),(ZC,R1S,R2J,R3R),(ZC,R1S,R2K,R3A),(ZC,R1S,R2K,R3
B),(ZC,R1S,R2K,R3C),(ZC,R1S,R2K,R3D),(ZC,R1S,R2K,R3 E),(ZC,R1S,R2K,R3F),(ZC,R1S,R2K,R3G),(ZC,R1S,R2K,R3 H),(ZC,R1S,R2K,R3I),(ZC,R1S,R2K,R3J),(ZC,R1S,R2K,R3 K),(ZC,R1S,R2K,R3L),(ZC,R1S,R2K,R3M),(ZC,R1S,R2K,R 20 3N),(ZC,R1S,R2K,R30),(ZC,R1S,R2K,R3P),(ZC,R1S,R2K,R 3Q),(ZC,R1S,R2K,R3R),(ZC,R1S,R2L,R3A),(ZC,R1S,R2L,R 3B),(ZC,R1S,R2L,R3C),(ZC,R1S,R2L,R3D),(ZC,R1S,R2L,R 3E),(ZC:,R1S,R2L,R3F),(ZC,R1S,R2L,R3G),(ZC,R1S,R2L,R 3H),(ZC,R1S,R2L,R3I),(ZC,R1S,R2L,R3J),(ZC,R1S,R2L,R3 250 200843739 K),(ZC,R1S,R2L,R3L),(ZC,R1S,R2L,R3M),(ZC,R1S,R2L,R3 N),(ZC,R1S,R2L,R30),(ZC,R1S,R2L,R3P),(ZC,R1S,R2L,R3 Q),(ZC,R1S,R2L,R3R),(ZC,R1S,R2M,R3A),(ZC,R1S,R2M,R 3B),(ZC,R1S,R2M,R3C),(ZC,R1S,R2M,R3D),(ZC,R1S,R2M, 5 R3E),(ZC,R1S,R2M,R3F),(ZC,R1S,R2M,R3G),(ZC,R1S,R2
M,R3H),(ZC,R1S,R2M,R3I),(ZC,R1S,R2M,R3J),(ZC,R1S,R2 M,R3K),(ZC,R1S,R2M,R3L),(ZC,R1S,R2M,R3M),(ZC,R1S, R2M,R3N),(ZC,R1S,R2M,R30),(ZC,R1S,R2M,R3P),(ZC,R1 S,R2M,R3Q),(ZC,R1S,R2M,R3R),(ZC,R1S,R2N,R3A),(ZC,R 10 1S,R2N,R3B),(ZC,R1S,R2N,R3C),(ZC,R1S,R2N,R3D),(ZC,R 1S,R2N,R3E),(ZC,R1S,R2N,R3F),(ZC,R1S,R2N,R3G),(ZC,R 1S,R2N,R3H),(ZC,R1S,R2N,R3I),(ZC,R1S,R2N,R3J),(ZC,R1 S,R2N,R3K),(ZC,R1S,R2N,R3L),(ZC,R1S,R2N,R3M),(ZC,R 1S,R2N,R3N),(ZC,R1S,R2N,R30),(ZC,R1S,R2N,R3P),(ZC,R 15 1S,R2N,R3Q),(ZC,R1S,R2N,R3R)。 其他較佳態樣係於下式(g)〜(n)中具有以下基團者。 251 200843739 【化33】
表5 R2 R20 iPr R2P tBu R2Q cHex R2R Ph R2S 4-OMe-Ph R2T 3-0比°定基 R2U 噻吩基 表6 R3S iPr R3T tBu R3U cHex R3V Ph R3W 2-Cl-Ph R3X 2-吡啶基 252 200843739 表7 A, (僅(h),(i),(j),(k),(m^(n)) A1 2-或 3-或 4-COOEt A2 2-或 3-或 4-CF3 A3 2-或 3-或 4-OCF3 A4 2-或 3-或 4-SCF3 A5 2-或3-或4-異噚唑-3-基 A6 2-或 3-或 4-CH=NOH A7 2-或 3-或 4-CH=NOMe 前述表中,Me為甲基,Et為乙基,iPi:為異丙基,tBu 為第三丁基,cHex為環己基,Ph為苯基。 5 R2、R3及A’之組合(R2, R3, A’)為以下之化合物。
(R2,R3,A,)=(R20,R3S,A1),(R20,R3S,A2),(R20,R3S,A3 ),(R20,R3S,A4),(R20,R3S,A5),(R20,R3S,A6),(R20,R3S,A7 ),(R20,R3T,A1),(R20,R3T,A2),(R20,R3T,A3),(R20,R3T,A4 ),(R20,R3T,A5),(R20,R3T,A6),(R20,R3T,A7),(R20,R3U,A1 10 ),(R20,R3U,A2),(R20,R3U,A3),(R20,R3U,A4),(R20,R3U,A 5),(R20,R3U,A6),(R20,R3U,A7),(R20,R3V,A1),(R20,R3V, A2),(R20,R3V,A3),(R20,R3V,A4),(R20,R3V,A5),(R20,R3V, A6),(R20,R3V,A7),(R20,R3W,A1),(R20,R3W,A2),(R20,R3 W,A3),(R20,R3W,A4),(R20,R3W,A5),(R20,R3W,A6),(R20, 15 R3W,A7),(R20,R3X,A1),(R20,R3X,A2),(R20,R3X,A3),(R2
0,R3X,A4),(R20,R3X,A5),(R20,R3X,A6),(R20,R3X,A7),(R 2P,R3S,A1),(R2P,R3S,A2),(R2P,R3S,A3),(R2P,R3S,A4),(R2P ,R3S,A5),(R2P,R3S,A6),(R2P,R3S,A7),(R2P,R3T,A1),(R2P,R 3T,A2),(R2P,R3T,A3),(R2P,R3T,A4),(R2P,R3T,A5),(R2P,R3T 253 200843739 ,A6),(R2P,R3T,A7),(R2P,R3U,A1),(R2P,R3U,A2),(R2P,R3U, A3),(R2P,R3U,A4),(R2P,R3U,A5),(R2P,R3U,A6),(R2P,R3U,
A7),(R2P,R3V,A1),(R2P,R3V,A2),(R2P,R3V,A3),(R2P,R3V,A 4) ,(R2P,R3V,A5),(R2P,R3V,A6),(R2P,R3V,A7),(R2P,R3W,A1 5 ),(R2P,R3W,A2),(R2P,R3W,A3),(R2P,R3W,A4),(R2P,R3W,A5 ),(R2P,R3W,A6),(R2P,R3W,A7),(R2P,R3X,A1),(R2P,R3X,A2 ),(R2P,R3X,A3),(R2P,R3X,A4),(R2P,R3X,A5),(R2P,R3X,A6) ,(R2P,R3X,A7),(R2Q,R3S,A1),(R2Q,R3S,A2),(R2Q,R3S,A3) ,(R2Q,R3S,A4),(R2Q,R3S,A5),(R2Q,R3S,A6),(R2Q,R3S,A7) 10 ,(R2Q,R3T,A1),(R2Q,R3T,A2),(R2Q,R3T,A3),(R2Q,R3T,A4)
,(R2Q,R3T,A5),(R2Q,R3T,A6),(R2Q,R3T,A7),(R2Q,R3U,A1) ,(R2Q,R3U,A2),(R2Q,R3U,A3),(R2Q,R3U,A4),(R2Q,R3U,A 5) ,(R2Q,R3U,A6),(R2Q,R3U,A7),(R2Q,R3V,A1),(R2Q,R3V, A2),(R2Q,R3V,A3),(R2Q,R3V,A4),(R2Q,R3V,A5),(R2Q,R3V, 15 A6),(R2Q,R3V,A7),(R2Q,R3W,A1),(R2Q,R3W,A2),(R2Q,R3
W,A3),(R2Q,R3W,A4),(R2Q,R3W,A5),(R2Q,R3W,A6),(R2Q, R3W,A7),(R2Q,R3X,A1),(R2Q,R3X,A2),(R2Q,R3X,A3),(R2 Q,R3X,A4),(R2Q,R3X,A5),(R2Q,R3X,A6),(R2Q,R3X,A7),(R 2R,R3S,A1),(R2R,R3S,A2),(R2R,R3S,A3),(R2R,R3S,A4),(R 20 2R,R3S,A5),(R2R,R3S,A6),(R2R,R3S,A7),(R2R,R3T,A1),(R 2R,R3T,A2),(R2R,R3T,A3),(R2R,R3T,A4),(R2R,R3T,A5),(R 2R,R3T,A6),(R2R,R3T,A7),(R2R,R3U,A1),(R2R,R3U,A2),(R 2R,R3U,A3),(R2R,R3U,A4),(R2R,R3U,A5),(R2R,R3U,A6),( R2R,R3U,A7),(R2R,R3V,A1),(R2R,R3V,A2),(R2R,R3V,A3),( 254 200843739
R2R,R3V,A4),(R2R,R3V,A5),(R2R,R3V,A6),(R2R,R3V,A7),( R2R,R3W,A1),(R2R,R3W,A2),(R2R,R3W,A3),(R2R,R3W,A4 ),(R2R,R3W,A5),(R2R,R3W,A6),(R2R,R3W,A7),(R2R,R3X, A1),(R2R,R3X,A2),(R2R,R3X,A3),(R2R,R3X,A4),(R2R,R3X 5 ,A5),(R2R,R3X,A6),(R2R,R3X,A7),(R2S,R3S,A1),(R2S,R3S ,A2),(R2S,R3S,A3),(R2S,R3S,A4),(R2S,R3S,A5),(R2S,R3S, A6),(R2S,R3S,A7),(R2S,R3T,A1),(R2S,R3T,A2),(R2S,R3T,A 3),(R2S,R3T,A4),(R2S,R3T,A5),(R2S,R3T,A6),(R2S,R3T,A7 ),(R2S,R3U,A1),(R2S,R3U,A2),(R2S,R3U,A3),(R2S,R3U,A4 10 ),(R2S,R3U,A5),(R2S,R3U,A6),(R2S,R3U,A7),(R2S,R3V,A1 ),(R2S,R3V,A2),(R2S,R3V,A3),(R2S,R3V,A4),(R2S,R3V,A5), (R2S,R3V,A6),(R2S,R3V,A7),(R2S,R3W,A1),(R2S,R3W,A2), (R2S,R3W,A3),(R2S,R3W,A4),(R2S,R3W,A5),(R2S,R3W,A6 ),(R2S,R3W,A7),(R2S,R3X,A1),(R2S,R3X,A2),(R2S,R3X,A3 15 ),(R2S,R3X,A4),(R2S,R3X,A5),(R2S,R3X,A6),(R2S,R3X,A7 ),(R2T,R3S,A1),(R2T,R3S,A2),(R2T,R3S,A3),(R2T,R3S,A4), (R2T,R3S,A5),(R2T,R3S,A6),(R2T,R3S,A7),(R2T,R3T,A1),( R2T,R3T,A2),(R2T,R3T,A3),(R2T,R3T,A4),(R2T,R3T,A5),(R 2T,R3T,A6),(R2T,R3T,A7),(R2T,R3U,A1),(R2T,R3U,A2),(R2 20 T,R3U,A3),(R2T,R3U,A4),(R2T,R3U,A5),(R2T,R3U,A6),(R2 T,R3U,A7),(R2T,R3V,A1),(R2T,R3V,A2),(R2T,R3V,A3),(R2T ,R3V,A4),(R2T,R3V,A5),(R2T,R3V,A6),(R2T,R3V,A7),(R2T, R3W,A1),(R2T,R3W,A2),(R2T,R3W,A3),(R2T,R3W,A4),(R2T ,R3W,A5),(R2T,R3W,A6),(R2T,R3W,A7),(R2T,R3X,A1),(R2 255 200843739 T,R3X,A2),(R2T,R3X,A3),(R2T,R3X,A4),(R2T,R3X,A5),(R2 T,R3X,A6),(R2T,R3X,A7),(R2U,R3S,A1),(R2U,R3S,A2),(R2 U,R3S,A3),(R2U,R3S,A4),(R2U,R3S,A5),(R2U,R3S,A6),(R2 U,R3S,A7),(R2U,R3T,A1),(R2U,R3T,A2),(R2U,R3T,A3),(R2 5 U,R3T,A4),(R2U,R3T,A5),(R2U,R3T,A6),(R2U,R3T,A7),(R2 U,R3U,A1),(R2U,R3U,A2),(R2U,R3U,A3),(R2U,R3U,A4),(R 2U,R3U,A5),(R2U,R3U,A6),(R2U,R3U,A7),(R2U,R3V,A1),( R2U,R3V,A2),(R2U,R3V,A3),(R2U,R3V,A4),(R2U,R3V,A5),( R2U,R3V,A6),(R2U,R3V,A7),(R2U,R3W,A1),(R2U,R3W,A2) 10 ,(R2U,R3W,A3),(R2U,R3W,A4),(R2U,R3W,A5),(R2U,R3W, A6),(R2U,R3W,A7),(R2U,R3X,A1),(R2U,R3X,A2),(R2U,R3 X,A3),(R2U,R3X,A4),(R2U,R3X,A5),(R2U,R3X,A6),(R2U,R 3X,A7)。 實施例 15 以下顯示實施例俾更具體地說明本發明,但本發明並 不侷限於此等實施例。此外,各略號具有以下所示之意義。 Me :曱基 Et :乙基 Bu : 丁基 20 Ac :乙醯基 TMS :四曱基矽烷 TMS-C1 :三甲矽基氯 DMSO :二甲基亞颯 rt :室溫 256 200843739 實施例1 製造5-環己基_4-(2,2-二曱基丙醯基)-3-羥基-1-(4-異噚唑-3 基本基)-1,5-二氫吼略·2_酮(1-32) 【化34】
於三甲基丙酮酸乙醋(1.00 g,5 mmol)、4-異σ号唾冬基 笨胺(0.80 g,5 mmol)與乙酸(4 mL)之混合液中加入環己院 甲醛(0·61 mL,5 mmol),以95°C攪拌5小時。反應後,冷卻 至室溫,以乙酸乙g旨一邊洗淨一邊滤取已析出之結晶,而 10 獲得呈淡黃色結晶之5-環己基-4-(2,2-二甲基丙醯基)-3_羥 基-1-(4-異嘮唑-3-基苯基)-1,5-二氫吡咯-2-酮(0.60 g,收率: 30%) 〇 熔點:259〜260°C、1H-NMR (δ ppm TMS / DMSO-d6) 〇·62-1·78 (11H,m),1·27 (9H,s),5·28 (1H,d,J=2.4 Hz), 15 7.20 (1H,d,J=1.8 Hz),7.75 (2H,d,J=8.7 Hz),7·98 (2H,d, J=8.7 Hz), 9·03 (1H,d,J=1.8 Hz),11.84 (1H,s) 實施例2 製造5-(3-氟苯基)-3-羥基-H4-異噚唑-3-基苯基)-4-(4-甲氧 基苯曱醯基)-1,5-二氫吼咯-2-酮(1-26) 20【化35】 257 200843739
於(4-甲氧基苯甲醯基)丙酮酸甲酯(0.24 g,1 mmol)、4-異噚唑-3-基苯胺(0.16 g,1 mmol)與二噚烷(1 mL)之混合液 中加入3-氟苯甲酸(0.11 mL, 1 mmol)並於室溫下攪拌2天。 5 反應後,加入二乙醚(3 mL),濾取已析出之結晶,而製得 呈微黃色結晶之5-(3-氟苯基)-3-羥基-1-(4-異噚唑-3-基苯 基)_4-(4-甲氧基苯甲醯基)-1,5-二氫吡咯-2-酮(0.16 g,收率: 34%) 〇 熔點:273 〜274°C (分解)、1H-NMR (δ ppm TMS / 10 DMSO-d6) 3·83 (3H, s),6.43 (1H,s),6.90-7.02 (3H,m), 7.11 (1H,d,J=1.7 Hz),7·23-7·35 (3H,m),7.75-7.87 (6H,m), 8.97 (1H,d,J=1.7 Hz), 11.75 (1H,brs). 實施例3 製造3 -弟二丁基-4-i哀己基-5-(4-異崎σ坐-3-基苯基)-4,5-二氮 15 -1Η-σ 比口各[3,4-c]a 比唾-6-酮(1-96) 【化36】
於5-環己基-4-(2,2-二甲基丙醯基)-3-羥基-1-(4-異噚唑 258 200843739 -3-基苯基)-1,5-二氫吡咯-2-酮(〇.1〇8,〇.25 111111〇1)與乙酸(1 mL)之混合液中加入肼之單水合物(〇·〇36 mL,0.75 mmol), 以85°C攪拌3小時。於反應液中加入水(8〇 mL),再以乙酸 乙酯(100 mL)抽提之。以飽和碳酸氫鈉水(8〇 mLx2)水洗抽 5 取液,再以無水硫酸鎂乾燥後’將減壓濃縮所得殘渣以二 氧化矽凝膠管柱層析法(乙酸乙酯/正己烷)純化,並使所得 結晶進行再結晶(乙酸乙酯),而製得呈無色結晶之3-第三丁 基-4-環己基-5-(4-異°号σ坐-3-基苯基)-4,5-二鼠-1H- 0比洛 [3,4-〇]°比唾-6-酮(0.072 g,收率:71%)。 10 熔點:251 〜252°C、1H-NMR (δ ppm TMS / DMSO-d6) 0.50-2.03 (11H,m), 1·39 (9H,s),5·60 (1H,s),7·20 (1H,d, J=1.8 Hz),7·72 (2H,d,J=8.7 Hz),7·96 (2H,d,J=8.7 Hz), 9.02 (1H, d, J=1.8 Hz), 13.28 (1H, s). 實施例4 15 製造4-(1-乙基丙基)-5-(4-異呤唑-3-基苯基)-3-(6-酮基-1,6- 二氫吡啶-3-基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮(1-198) 【化37】
於4-(1-乙基丙基)-5-(4-異噚唑-3-基苯基)-3-(6-甲氧基 20 吡啶-3-基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮(0.067 g,0.15 mmol)、碘化鈉(〇·〇67 g,0.45 mmol)與乙腈(3 mL)之混合液 259 200843739 中添加氯三甲基石夕烧(〇·〇58 mL,〇·45 mmol),回流下攢;拌1 小時。於反應液中加入水(50 mL)與乙酸乙酯(5〇 mL),渡取 析出之結晶,而製得呈微黃色結晶之4-(1-乙基丙基)-5-(4-異噚唑-3-基苯基)-3-(6-酮基-1,6-二氫吼唆-3-基)-4,5-二氫 5 -1Η-σ比洛[3,4-c]°比。坐-6-酮(0.041 g,收率:64%)。 熔點·· >290°C (分解)、1H-NMR (δ ppm TMS / DMSO-d6) 0·50-1·55 (11H,m),6·00 (1H,d,J=2.5 Ηζ),6·49 (1H,d, J=9.4 Hz),7.18 (1H,d,J=1.8 Hz),7.70-7.90 (4H,m),8.01 (2H,d,J=8.4 Hz),9.02 (1H,d,J=1.8 Hz), 12.04 (1H,brs), 10 13.78 (1H, brs). 實施例5 製造3-羥基-4-(4-甲氧基苯甲醯基)-i-(4_甲氧基亞胺基甲基 苯基)-5-苯基-1,5-二氯ϋ比洛-2-嗣(1-199) 【化38】
於3-羥基-1-(4-羥曱基苯基)-4-(4-甲氧基苯曱醯基)-5-本基-1,5-二鐵^比洛-2-酮(0.125 g,0.3 mmol)與丙酮(20 mL) 之混合液中加入氧化錳(IV)(0.625 g,7.18 mmol)並以室溫 攪拌2.5小時後,更加入氧化鐘(1¥)(0.625 §,7.18111111〇1), 20以室溫攪拌4·5小時。反應後,以矽藻土除去不溶之氧化錳 (IV)’濃縮濾液而製得ι·(4_甲酿基苯基)_3__經基_4_(4_甲氧基 260 200843739 苯甲醯基)-5-苯基-1,5-二氫吡咯-2-_之粗製物。於所得粗製 物中加入甲醇,調製成〇·1Μ之曱醇溶液。 於1-(4-曱&&基苯基)-3-經基-4-(4,甲氧基苯甲贐基)-5~ 苯基-1,5-二氫吼咯-2-酮之〇·1Μ甲醇溶液(1 mL,相當於0.1 5 mmo1)加入〇-甲基羥基銨氯化物(0.025 g,0.3 mmol)與乙 酸鈉(0.025 g,0·3 mmol),於回流下授拌3小時。於反應液中 添加水(50 mL)後,以乙酸乙酯(5〇 mL)抽提。以飽和食鹽水 (50 mL)水洗該抽提液,並以無水硫酸鈉乾燥後,於減壓濃 务百所得之殘渣中加入乙酸乙酯,濾取已析出之結晶,而製 10 得呈微黃色結晶之’3-羥基-4-(4-甲氧基苯甲醯基)-1-(4-甲氧 基亞胺基甲基苯基)-5-苯基-1,5-二氫°比嘻-2-酮(1.3 mg,收 率:3%)。 熔點·· 226〜229°C、1H-NMR (δ ppm TMS / DMS0-d6) 3·82 (3H,s),3·85 (3H,s),6·31 (1H,s),6.95-7.75 (13H,m), 15 8.12(1H,s),11.63 (lH,brs). 實施例6 製造1-(1,3-二σ号戍烧-2-基)-3-經基-4-(4_曱氧基苯曱酸 基>5-苯基-1,5-二氫吡咯-2-酮(1-200) 【化39】
將1-(4-甲醯基苯基)-3-羥基-4-(4-甲氧基苯甲醯基)_孓 261 200843739 苯基-1,5-二氫吡咯-2-酮之0.1M甲醇溶液(1 mL,相當於〇」 mmol)濃縮後,力口入甲苯(1 mL)、乙二醇(0.033 mL,〇·6 mm〇i) 與對甲苯磺酸之單水合物(3.8 mg,0·02 mmol),進行共沸脫 水3小時。於反應液中加入水(100 mL),並以乙酸乙醋(wo 5 mL)進行抽提。以飽和食鹽水(1〇〇 mL)水洗抽提液,並以無 水硫酸鈉乾燥後,於減壓濃縮所得殘渣中加入乙酸乙醋, 濾、取析出之結晶,而製得呈淡黃色結晶之二噚戊烧 -2-基)-3-羥基-4-(4-甲氧基苯曱醯基)-5-苯基-1,5-二氫吡咯 -2-酮(3.8mg,收率:8%)。 10 溶點:216〜219°C、1H-NMR (δ ppm TMS / DMSO-d6) 3.81 (3H,s),3.89-4.00 (4H,m),5·63 (1H,s),6.26 (1H,s), 6.94-7.75 (13H,m),11.65 (1H,brs)· 實施例7 製造3-羥基-1-(4-異嘮唑-3-基苯基)-4-(4-甲氧基苯甲醯 15 基)-5-(4-哌啶)-1,5-二氳吡咯-2-酮之鹽酸鹽(1-201) 【化40】
於5-(1-第三丁氧羰基-4-哌啶)-3-羥基-1-(4-異噚唾·3_ 基苯基)-4-(4-甲氧基苯甲酿基)-1,5-二氫°比洛-2-酮(〇.1120 20 0.2 mmol)與甲醇(1 mL)之混合液中加入4 mol/L鹽酸之二 崂烷溶液(0.2 mL,0.8 mmol),以室溫攪拌2·5小時後,更力口 262 200843739 入4 mol/L鹽酸之二噚烧溶液(〇·2 mL,0.8 mmol),於回流下 攪拌0.5小時。反應後,減壓濃縮而製得呈微褐色結晶之3_ 羥基-1-(4-異噚唑-3-基苯基)-4-(4-甲氧基苯甲醯基)-5-(4-哌 啶)-1,5-二氫吡咯-2-酮之鹽酸鹽(0.098 g,收率·· 100%)。 5 1H-NMR (δρριη TMS / DMSO-d6) 1.25-2.09 (5H, m), 2·50-2·74 (2H,m),3.09-3.17 (2H,m),3.90 (3H,s),5.58 (1H, s),7.09 (2H,d,J=8.6 Hz),7·21 (1H,d,J=1.5 Hz),7·82-7·89 (4H,m),8.02 (2H,d,J=8.6 Hz),8·11 (1H,brs),8.58 (1H, brs),9.04 (1H,d,J=1.5 Hz),11.55 (1H,brs)· !〇 實施例8 製造3-(4-甲氧基苯基)-5-(4_噚唑基苯基)_4_苯基-4,5-二 氫-1H』比洛[3,4-c]吼唾-6-酮(1-247) 【化41】
將5-(4-溴苯基甲氧基苯基苯基-4,5-二氫_1Η· 〇比咯[3,4-小比唑4_(〇 138 g,〇 3 mm〇1)與噚唑基三丁基 錫(〇·134 g,0.37 mmol)、三-(2_ 呋喃基)膦(〇〇14 匕 〇 恥 mm〇1)、三(二亞苄基丙酮)二鈀(0)(0.027 g,0.03 mm〇1)、二 可烷(1·5 mL)之混合液於微波照射下以130°C攪拌75分鐘。 使反應液採二氧化石夕凝膠管柱層析法(乙酸乙酉旨/正己燒), I辰縮所得目的物之分液一邊濾取已析出之結晶,而势 263 200843739 得呈無色結晶之3-(4-甲氧基苯基)-5-(4-噚唑-2-基苯基)-4-苯基-4,5-二氫-1H-σ比洛[3,4-c]吼吐-6-酮(12 mg,收率: 10%)。 1H-NMR (δρρπι TMS / DMSO-d6) 3.75 (3H, s), 6.86 5 (1H,s),6.91-7.92 (13H,m),8·17 (1H, s),14.00 (1H,brs)· 實施例9 製造5-環己基-3 -經基-1-(4-異4嗤-3 -基苯基)-4-(4-魏基苯 曱醮基)-1,5-二氫σ比口各-2-酮 【化42】
於5-環己基-3-羥基-1-(4-異噚唑-3-基苯基)-4-(4-甲氧 魏基苯曱醯基)-1,5-二氫吼洛-2-酮(1.98g,4.07mmol)、 THF(20mL)與甲醇(13mL)之混合液中加入2N氫氧化鈉水溶 液(5.09mL),以80°C油浴攪拌2小時。反應後,於冰冷下加 15 入2N鹽酸(5.09mL)後,更加入乙酸乙酯與水,以室溫放置 一夜後濾取析出之結晶,製得呈黃色結晶之5-環己基-3-經 基-1-(4-異噚唑-3-基苯基)-4-(4-羧基苯曱醯基H,5_二氯吼 洛-2-酮(1.70g,收率:88%)。 lH-NMR(6ppmTMS/DMSO-d6)0.73-1.80(HH , m) 20 5.49(1H,d,J=2.4H z ),7·21(1Η,d,j=1.7H z ), 7·80-8·11(8Η,m),9.04(1H,d,J=1.7H z )。 264 200843739 實施例ίο 製造5-環己基-3-羥基-1-(4-異噚唑-3-基苯基)-4-(4-甲基胺 甲醯基苯甲醯基)-1,5-二氫吡咯-2-酮 【化43】
於5-環己基-3-羥基-1-(4-異哼唑-3-基苯基)-4-(4-羧基 苯甲酿基)-1,5-二氫°比口各-2-酉同(0.095g,0.2mmol)與 DMF(2mL)之混合液中加入甲基胺之鹽酸鹽(0.020g, 0.3mmol)、1-經基苯并三。坐(0.041g,0.3mmol)、4-二曱基胺 10 基%b^(0.005g,0.04mmol)、鹽酸 1-乙基-3-(3-二甲基胺基 丙基)羱二亞胺(〇.〇58g ,0.3mmol)及三乙胺 (0.042mL,0.3mmol),並以室溫授拌1小時。反應後,加入乙 酸乙酯與水,濾取已析出之結晶,製得呈淡黃色結晶之5-壞己基-3-經基-1-(4-異σ号峻-3-基苯基)-4-(4-甲基胺甲酿基 15 苯曱醯基)-1,5-二氫吡咯-2-酮(0.062g,收率:64%)。 lH-NMR(5ppmTMS/DMSO-d6)0.72-1.80(1 lH9m) , 2.81(3H,d,J=4.5H z ) , 5.48(lH,d,J=2.5H z ), 7.21(lH,d,J=1.7Hz),7.80-8.03(8H,m),8.64(lH,d,J=4.5H z ),9.04(lH,d,J=1.7H z ),11.73(lH,brs)。 20 實施例11 製造3-第三丁基-5-(4-異噚唑-4-基苯基)-4-(2-甲氧基苯 265 200843739 基)-4,5-二氫-111-°比略[3,4-(:]11比。坐-6-酮 【化44】
將5-(4- >臭苯基)-3-第二丁基-4-(2-甲氧基苯基)-4,5-二 5 氫-1Η-σ比口各[3,4-0]〇比°坐-6-酮(0.10g,0.23mmol)、4-(4,4,5,5- 四甲基-l,3-2-二崎硼烧-2-基)異 _ 吐(0.066g,0.34mmol)、 磷酸三鉀(0· 145g,0.68mmol)、乙二醇二甲醚(3mL)與水 (0.6mL)之混合液作氮取代後,加入[1,1、雙(二苯基膦基)二 茂鐵]二氯鈀(Π)二氯甲烷附加物(0.018g,0.023mmol),回 10 流下攪拌4小時。將反應液以二氧化矽凝膠管柱層析法(乙 酸乙酯/正己烷)純化,製得呈無色結晶之3-第三丁基-5-(4-異噚唑-4-基苯基)-4-(2-甲氧基苯基)-4,5-二氫-1H j比咯 [3,4-c]吡唑-6-酮(0.012g,收率·· 12%)。 lH-NMR0ppmTMS/DMSO-d6)l.O5(9H,s),3·91(3Η, 15 s),6·22-7·61(9Η,m),9·09(1Η,s),9·36(1Η,s),13·34(1Η, s) ° 實施例12 製造3-第三丁基-5-(4-呋喃-3-基苯基)-4-(2-曱氧基苯 基)-4,5-二氫-111-°比洛[3,4-(:]吼哇-6-酮 20 【化45】 266 200843739
將5-(4-溴苯基)-3-第三丁基-4-(2-曱氧基苯基)-4,5-二 氫-111-11比洛[3,4-(:]11比°坐-6-嗣(0.1〇8,0.23111111〇1)、吱喃-3-基 硼酸(0.038g,0.34mmol)、磷酸三鉀(0.096g,0.45mmol)與 5 丁醇(lmL)之混合液作氮取代後,加入(2’,4’,6’-三異丙基聯 苯-2-基)膦(0.009g,0.02mmol)與三(二亞苄基丙酮)二|巴 (0)(0.004g,0.004mmol),於回流下攪拌3小時。使反應液以 二氧化矽凝膠管柱層析法(乙酸乙酯/正己烷)將所得目的物 之分液一邊濃縮一邊析出,濾取結晶而獲得呈無色結晶之 10 3 -弟二丁基-5-(4-咬喃-3 -基苯基)-4-(2-甲氧基苯基)-4,5 -二 氫-1Η-σ比洛[3,4-c]a比唾-6-酮(0.061g,收率:63%)。 lH-NMR(5ppmTMS/DMSO-d6)1.05(9H,s) , 3.90(3H,s),6.37-7.56(10H,m),7.70(lH,s),8.11(lH,s), 13.32(lH,s)。 15 實施例13 製造5-環己基-3-羥基-4-(4-羥基苯曱醯基)-1-(4-異噚唑-3-基本基)-1,5 - ->氮π比1^ - 2 -酉同 【化46】 267 200843739
在冰冷下,於5-環己基-3-羥基-1-(4-異哼唑-3-基苯 基)-4-(4-甲氧基苯甲醯基)-1,5-二氫吡咯-2-酮(0.229g, 0.5mmol)與二氯甲烷(10mL)之混合液中加入1M三溴化硼 5 二氣甲烧溶液(5.0mL,5mmol),並以室溫攪拌溫3天。反應 後,於冰冷下加入少量碳酸鉀分解過剩之三溴化硼,加入 1N氫氧化鈉水溶液後,以乙酸乙酯洗淨。使水層以1N鹽酸 中和,濾取析出之結晶,熱時以乙酸乙酯洗淨,製得呈無 色結晶之5-壤己基-3-控基-4-(4-經基苯甲酸基)-1-(4-異。号13坐 10 -3-基本基)-1,5-*—氮^比咯-2-嗣(0.068g ’ 收率· 31 %)。 lH-NMR(3ppmTMS/DMSO-d6)0.73-1.80(llH,m), 5·41(1Η,d,J=2.5H z ),6·88-6·91(2Η,m),7·20(1Η,d, J=1.7H z ),7·78-8·01(6Η,m),9·03(1Η,d,J=1.7H z ), 10·42(1Η,brs),11.14(lH.brs)。 15 實施例14 製造5-環己基-3-羥基-4-(4-羥甲基苯甲醯基)-1-(4-異噚唑 -3-基苯基)-1,5_二鼠ϋ比略-2-酉同 【化47】 268 200843739
於曱基4-(2-四氫比喃氧基甲基)苯曱醯基丙酮酸 酯(0.178,0.53111111〇1)、4-異噚唑-3-基苯胺(0.0858,0.53111111〇1) 與乙酸(lmL)之混合液中加入環己烷甲醛 5 (0.064mL,0.53mmol),並以95°C攪拌0.5小時。反應後,冷 卻至室溫,一邊以乙酸乙酯洗淨一邊濾取已析出之結晶, 於所得粗製物中加入甲醇(5mL)、THF(5mL)及對甲苯磺酸 吼啶鏽(0.027g,O.llmmol),以60°C攪拌〇·5小時。於反應 液中加入水,以氯仿抽提並以無水硫酸鎂乾燥後,將減壓 10 濃縮所得之殘渣實施再結晶(乙酸乙酯),而製得無色結晶之 5-環己基-3-羥基-4-(4-羥甲基苯甲醯基)-1-(4-異噚唑-3-基 苯基)-1,5-二氫吡咯-2-酮(0.022g,收率:9%)。 lH-NMR(3ppmTMS/DMSO-d6)0.62-1.78(llH,m), 4·61(2Η,d,J=5.6H z ),5·38(1Η,t,J=5.6H z ),5·47(1Η, 15 d,J=2.0H z ),7·21(1Η,d,J=1.7H z ),7·49-8·02(8Η,m), 9.03(1H,d,J=1.7H z ),11·40(1Η,brs) 一般製造法1 製造經離析之鏡向異構物 【化48】 269 200843739
(Γ-1) 式中記號與前述者同義。 使化合物(Γ-l)及光學分割劑(如(S)-曱基2-羥基-2-苯基 乙酸酯)於適當溶劑中與縮合劑(如偶氮二甲酸異丙酯)反 5 應,使所得混合物以常法(如管柱層析法、再結晶法等)純 化,而離析出具有所需立體配置之非鏡向異構物。將所得 非鏡向異構物進行脫保護反應(如加氫反應)即可製造出目 的之鏡向異構物。光學分割劑相對於化合物(Γ-1)係使用 1〜4等量,且較佳為1〜2.5等量。 10 可使用之溶劑可列舉如:芳香族烴類(如甲苯、苯、二 甲苯等)、飽和烴類(如環己烷、己烷等)、醚類(如四氫呋喃、 二乙醚、二哼烷等)醯胺類(如二甲基甲醯胺、二甲基乙醯 胺、Ν-甲基吡咯啶酮)及其等之混合溶劑等。 反應溫度為-10〜150°C,較佳為0〜50°C。反應時間雖依 15 化合物而異,但使其反應10分鐘〜48小時即可。 依照一般製造法1來製造以下化合物。 實施例15 製造( + )-4-(2,2-二甲基丙醯基)-3-羥基-1-(4-異噚唑-3-基苯 基)-5-(2-甲氧基苯基)-1,5-二氫吡咯-2-酮 20 【化49】 270 200843739
於冰冷下,於4-(2,2-二甲基丙醯基)-3-經基-:1-(4-異十坐 -3-基苯基)一5-(2-甲氧基苯基)-1,5-二氫°比嘻-2-酮(〇.43g, lmmol)、(S)-甲基 2-羥基-2-苯基乙酸酯(〇.23g,l.4mmol)、 5三苯基膦(〇.34g,1.3mmol)與THF(lOmL)之混合液中加入偶 氮二甲酸異丙g旨(〇.26mL,1.3mmol),並以室溫授摔〇 5小 時。將反應液減壓濃縮,並使已藉二氧化矽凝膠管柱層析 法(乙酸乙酯/正己烷)純化而獲得之非鏡向異構物混合物再 結晶(乙酸乙酯/正己烷),製得呈無色結晶之非鏡向異構物 10 (0.14g,收率:25%)。 使所得非鏡向異構物(0.058g,O.lmmol)溶解於二。号垸 (3mL)中,加入1〇%鈀碳(〇.〇26g),以室溫進行2小時加氫。 以矽藻土過濾反應液後,將濃縮所得殘渣以二氧化石夕凝膠 管柱層析法(乙酸乙酯/正己烷)純化,製得呈無色結晶之 15 ( + )冰(2,2-二甲基丙酿基)-3-經基-1-(4-異噚tr坐-3-基苯 基)-5-(2-甲氧基苯基)-1,5-二氫吼咯-2-酮(〇.〇43g,收率: 100%,光學純度:100%ee)。 [a]D ·· + 62.5±2.0°.(inCHC13) , lH-NMR0ppmTMS/DMSO-d6)l.lO(9H,s),3·89(3Η,brs), 20 6·39(1Η,brs),6·70-7·82(9Η,m),8·95(1Η,d,J=1.8H z ), 271 200843739 12·08(1Η,brs) 〇 一般製造法2 製造噚唑體 【化50】
式中,X為鹵素,其他記號與前述者同義。 可使化合物(I -2)、輕亞胺基函化物及驗於適當溶劑中 反應而製彳于。獲得之所需化合物可視需要而以常法(如管柱 層析法、再結晶法等)進行純化。羥亞胺基_化物相對於化 10合物(F-2)係使用1〜5等量,較佳為1〜2.5等量。 可使用之溶劑可列舉如:芳香族烴類(如甲苯、苯、二 甲苯等)、飽和烴類(如環己烧、己烧等)、醚類(如四氫呋喃、 二乙醚、二噚烧等)、醯胺類(如二甲基甲醯胺、二甲基乙醯 胺、Ν-甲基吼洛啶酮)及該等之混合溶劑等。 15 可使用之驗可列列舉如金屬氫氧化物(如氫氧化鈉、氫 氧化鉀等)、金屬氫化物(如氫化鈉、氫化鋰等)、金屬碳酸 鹽(如碳酸鈉、碳酸鉀、碳酸鉋等)等,相對於化合物(Γ-2) 可使用2當量或以上,且較佳為2〜10當量。 反應溫度為-40〜150°C,較佳為0〜50°C。反應時間雖依 272 200843739 化合物而異,但使其反應10分鐘〜48小時即可。 依照前述之一般製造法2來製造下述化合物。 實施例16 製造3-第三丁基-5-[4-(3-乙氧羰基異噚唑基)苯基]冬(2_ 5甲氧基本基)-4,5- —鼠比嘻[3,4-c]a比哇-6-酮 【化51】
於冰冷下,於3-第三丁基-5-(4-乙炔基苯基)冰(2-曱氧 基笨基)-4,5- 一氫-1H- σ比洛[3,4-c]吼唾-6-自同(1.51g, 10 3.9mmol)、乙基2-氣-2-羥亞胺基乙酸酯(1.19g,7 8mm〇1) 與THF(4mL)之混合液中緩緩加人三乙胺(! 〇9mL7 8mm〇1) 之THF(3mL)溶液’以〇°c攪拌4小時。於反應液中加入乙基 2-氯-2-經亞胺基乙酸酯(i.i9g,7.8mmol)後,更徐徐加入三 乙胺(0.81mL,5.9mmol)之THF(3mL)溶液,以〇。〇攪拌2小時 15後放置一夜。除去已析出之結晶,將減壓濃縮所得殘渣純 化,而製得呈無色固體之3-第三丁基-5-[4-(3-乙氧魏基-5-異D.坐基)苯基M-(2-曱氧基苯基)-4,5-二氫-lH-t各[3,4-C] °比哇-6-明(1.26g,收率:64%)。 lH-NMR(8ppmTMS/DMSO-d6)1.13(9H,s),1·43(3Η, 20 t,J=7.l),3·50(0·5Η,S),4·01(2·5Η,s),4·45(2Η,q,J=7.3), 6·01(0·3Η,s),6·74-6·88(2·7Η,m),6·91(1Η,d,J=8.6), 273 200843739 7·19(1Η,t,J=7.4),7·70(2Η,d,J=8.6),7·81(2Η,d,J=8.6)。 實施例17 製造3-第三丁基-5-[4-(3-羧基-5-異噚唑基)苯基]_4_(2_甲氧 基苯基)-4,5-二氫-1^1-°比嘻[3,4-〇]°比唾-6-酮 5 【化52】
於3·第三丁基-5-[4-(3-乙氧羰基各異噚唑基)苯 基]冰(2-甲氧基苯基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮 (1.26g,2.5mmol)、甲醇(4mL)、THF(4mL)及水(3mL)之混 10 合液中加入2N氫乳化納水溶液(1.5mL,3mmol),以50°C撲摔 1小時。反應後,加入水(40mL)與1N鹽酸(2mL),以乙酸乙 酯抽提後再以飽和食鹽水洗淨,並以無水硫酸鈉乾燥之。 乾燥後,使減壓濃縮所得之粗製物懸濁於醚,濾取已析出 之結晶後,製得呈淡黃色結晶之3-第三丁基-5-[4-(3-羧基-5-15 異噚唑基)苯基]-4-(2-甲氧基苯基)-4,5-二氫-1H·-比咯[3,4-c] 吡唑-6-酮(0.84g,收率:71%)。 lH-NMR0ppmTMS/DMSO_d6)l.O5(9H,s),3·96(3Η, s),6·50(0.3Η,s),6·68-6·94(2·7Η,m),7.00-7·25(2Η,m) ’ 7·29(1Η,s),7·77(2Η,d,J=8.6),7.87(2Η,d,J=8.6), 20 13·43(1Η,brs),13·97(1Η,brs)。 實施例18 274 200843739 製造3-第三丁基-5-[4-(3-二甲基胺曱醯基_5-異4 σ坐基)苯 基]-4-(2-曱氧基苯基)-4,5-二氣-1Η-σ比略[3,4-c]0比σ坐-6-嗣 【化53】
於3-第三丁基-5-[4-(3-羧基-5-異噚唑基)苯基]-4-(2-甲 氧基本基)-4,5-二氮-1Η-吼略[3,4-c]吼 坐-6-嗣(0.080g, 0.17mmol)與DMF(2mL·)之混合液中力口人二甲胺鹽酸鹽 (0.021g,〇.25mmol)、1-羥基苯并三唑(〇.〇34g,0.25mmol)、 4- 二甲基胺基吼咬(0.004g,0.03mmol)、鹽酸1-乙基-3-(3-10 二甲基胺基丙基)碳二亞胺(0.048g,0.25mmol)及三乙胺 (0.035mL,0.25mmol),以室溫攪拌2小時。反應後,加入乙 酸乙酯與水,濾取已析出之結晶,而製得呈淡黃色結晶之 5- 環己基-3-每基-1-(4-異$ σ坐-3-基苯基)-4-(4-曱基胺甲酿 基苯甲醯基)-1,5-二氫吡咯-2-酮(0.055g,收率:65%)。 15 lH-NMR(5ppmTMS/DMSO-d6)1.05(9H,s),3·02(3Η, s),3·39(1Η,s),6·50(0·3Η,m),6·65-6·96(2·7Η,m),7·06(1Η, d,J=8.1),7·14(1Η,s),7·19(1Η,t,J=7.6),7·76(2Η,d, J=8.6),7·84(2Η,d,J=8.6),13·32(1Η,brs)。 實施例19 20 製造3-第三丁基-5-[4-(3-羥甲基-5-異噚唑基)苯基]-4-(2-甲 氧基苯基)-4,5-二氫-1士°比嘻[3,4-〇]吼嗤-6-酮 275 200843739 【化54】
於冰冷下,在3-第三丁基-5-[4-(3-羧基-5-異°号峻基)苯 基]-4-(2-曱氧基苯基)-4,5-二氫比 π各[3,4-(:]〇比嗤-6-_ 5 (〇.〇80g,0.17mmol)、三乙胺(〇.〇3imL,0.22mmol)與 THF(2mL)之混合液中加入氯碳酸乙酯 (0.019mL,0.20mmol),並以室溫攪拌2小時。接著,於反應 液中加入氫化硼鈉(0.026g,0.68mmol)與水(〇.3mL)之溶液 後,更加入甲醇(lmL)並以室溫攪拌1〇分鐘。反應後加入 10 水,以乙酸乙酯抽提後,再以1N鹽酸、飽和碳酸鈉水及飽 和食鹽水洗淨,以無水硫酸鈉乾燥之。乾燥後,使減壓濃 縮所獲得之殘渣以二氣甲烷、二乙醚及乙酸乙酯結晶,濾 取已析出之結晶,而製得呈無色結晶之3-第三丁基-5-[4-(3-羥甲基-5-異噚唑基)苯基]-4-(2-甲氧基苯基)-4,5-二氫-1H-15 π比洛[3,4-。]°比唾-6-酮(0.068g,收率:88%)。 1H-NMR(8ppmTMS/DMSO-d6)1.03(9H,s),3·39(1Η, s),3·94(2Η,s),4·51(2Η,d,J=26.9),5·52(5·52(1Η,t, J=5.8),6·47(0·3Η,s),6·65-6·84(2·7Η,m),6·88(1Η,s), 7·05(1Η,d,J=8.1),7·19(1Η,t,J=7.6),7·73(2Η,d,J=8.6), 20 7.78(2H,d,J=8.6),13·13(0·3Η,brs),13·39(0·6Η,brs), 13·58(0·1Η,brs)。 276 200843739 一般製造法3 製造Boc-保護胺體 【化55】
5式中§己號與前述者同義。 將化合物(1’-3)、驗及疊氮化觸(如二苯_酸基疊氮) 於適當溶劑中反應,接著,於反應液中加入第三丁醇與乾 峨如硫酸納、粉末分子篩)即可製得。獲得之所需化合物 可依需要而以常法(如管;^主厚杯_、、表 $ 中g狂層析法、再結晶、抽提等)進行純 10化。疊氮化試劑相對於化合物(1,_3)係使用W等量,且較 佳為1〜2.5等量。 可使用之溶劑可列舉如芳香族烴類(如甲苯、苯、二甲 苯等)、飽和烴類(如環己烷、己烷等)、醚類(如四氫呋喃、 二乙醚、二噚烷等)以及該等之混合溶劑等。 15 可使用之鹼可列舉如金屬氫氧化物(如氫氧化鈉、氫氧 化鉀等)、金屬氫化物(如氫化鈉、氫化鋰等)、金屬碳酸鹽(如 碳酸鈉、碳酸鉀、碳酸鉋等)等,相對於化合物(1,-2)可使用 1當夏或以上’且較佳為1〜5當量。 反應溫度為0~15(TC,較佳為40〜120°C。反應時間係依 20 化合物而異,但使其反應1〇分〜48小時即可。 依照一般製造法3製造以下化合物。 277 200843739 實施例20 製造3-第三丁基-5-[4-(3-第三丁氧羰基胺基-5-異噚唑基)苯 基]-4-(2-甲氧基苯基)-4,5-二氮-111-11比略[3,4-〇]0比嗤-6-酉同 【化56】
於3-第三丁基-5-[4-(3-羧基-5-異噚唑基)苯基]-4-(2-甲 乳基本基)-4,5-二鼠-1H- °比略[3,4-c] °比哇-6- S同(0.948g ’ 2.0mmol)、三乙胺(0.33mL,2.4mmol)與 DMF(15mL)之混合液 中加入二苯基磷酸基疊氮(0.52mL,2.4mmol)並以60°C攪拌2 10 小時。接著,於反應液中加入第三丁醇(15mL)與粉末分子 篩4A(2g)後,更以90°C攪拌3小時。反應後,過濾除去不溶 物,加入水並以乙酸乙S旨抽提後,以氣化銨水溶液及飽和 食鹽水洗淨,並以無水硫酸鈉乾燥之。乾燥後,使減壓濃 縮所得之殘渣以二氯甲烷來結晶化,濾取已析出之結晶, 15 而獲得呈無色結晶之3-第三丁基-5-[4-(3-第三丁氧羰基胺 基-5-異噚唑基)苯基]-4-(2-甲氧基苯基)-4,5-二氫-1H-吼咯 [3,4-c]°比吐-6-酮(0.566g,收率:52%)。 lH-NMR(5ppmTMS/DMSO-d6)1.05(9H,s),1·47(9Η, s),3·95(3Η,s),6·77-6·80(3Η,m),7·00-7·11(2Η,m), 20 7·19(1Η,m),7·72(2Η,d,J=8.6),7·77(2Η,d,J=8.6), 10·34(1Η,s),13.24(1H,brs)。 278 200843739 實施例21 製造3-第三丁基-5-[4-(3-胺基-5-異噚唑基)苯基]-4-(2-甲氧 基苯基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮 【化57】
於3-第三丁基-5-[4-(3-第三丁氧羰基胺基-5-異哼唑基) 苯基]-4-(2-甲氧基苯基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮 (0.036g,0.7mmol)與甲醇(2mL)之混合液中加入濃鹽酸 (0.07mL)並以60°C攪拌2小時。反應後濾取析出之結晶,使 10 所得結晶進行再結晶(甲醇/二氯甲烷),而製得呈淡黃色結 晶之3-第三丁基-5-[4-(3-胺基-5-異噚唑基)苯基]-4-(2-甲氧 基苯基)-4,5-二氫-1H-吡咯[3,4-c]吡唑-6-酮(0.02g,收率: 68%) 〇 lH-NMR(SppmTMS/DMSO-d6)1.05(9H,s),3·38(1Η, 15 s),3·94(2Η,s),5·60(2Η,s),6·21(1Η,s),6·44(0·3Η, s),6·65-6·94(2·7Η,m),7·04(1Η,d,J=8.1),7·19(1Η,t, J=7.6),7·67(4Η,s),13·11(0·2Η,brs),13·37(0·7Η,brs), 13·56(0·1Η,brs) 實施例22 20 製造4-(l,2-二酮基丙基)-3-羥基-1-(4-異哼唑-3-基苯 基)-5-(2-甲氧基苯基)-1,5-二氫吼咯-2-酮 279 200843739 【化58】
MeC MeO
;ν°· 於甲基二甲氧基(甲基)乙醯丙酮酸鈉鹽(〇.24g, lmmol)、4-異噚唑-3-基苯胺(〇.16g,lmmol)與乙酸(2mL) 5 之混合液中加入2-曱氧基苯曱駿(〇.14g,lmmol),以室溫攪 拌一夜。反應後加入水濾取已析出之結晶,使所得結晶再 結晶(二氣甲烧/鍵)’而製得呈淡黃色結晶之二_(2,2_二甲氧 基丙醯基)-3-羥基-1 -(4-異呤唑-3-基苯基)-5-(2-甲氧基苯 基)-1,5-二氫°比11 各-2-_(〇.22g,收率:47%)。 10 於4-(2,2-^一甲氧基丙酿基)-3-經基-1-(4-異。号〇坐-3-基苯 基)-5-(2-甲氧基苯基)-1,5-二氫吡咯-2-酮(〇.〇8g,0.17mmol) 中加入乙酸(O.lmL)及水(〇.9mL),以95°C室溫攪拌15分鐘。 反應後加水,以乙酸乙酯抽提後再以無水硫酸鈉乾燥之。 乾燥後,使減壓濃縮所得殘渣以二氣甲烷與醚進行結晶 15化,濾取析出之結晶,而製得呈黃色結晶之4-(1,2-二酮基 丙基)-3-羥基-1-(4-異噚唑基苯基)-5-(2-甲氧基苯基 二氫^比17各-2-酮(0.05g,收率·· 7〇%)。 lH-NMR(3ppmTMS/DMSO-d6)2.24(3H,s),3·80(3Η, s),6·38(1Η,s),6·82(1Η,t,J=7.3),6·93(1Η,d,J=7.3), 20 7·〇8(1Η,d,J=1.6),7·13-7·18(2Η,m),7.70-7·84(4Η,m), 8·96(1Η,d,J=1.6)。 280 200843739 以前述合成路徑、一般製造法及實施例所記載之方法 為準,獲得以下各化合物。茲將構造及物性顯示如下。
281 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-3 Η。。 1 〇 〇 492 1-4 〇^s 〇 ) PHARMEKS 社 PHAR123923 458 1-5 〇 / PHARMEKS 社 PHAR136129 476 282 200843739 化合 物編 號 結構 熔點(°c)或 講入來源及品項 MS m/z [M+] 1-6 1。 ϋ 271-273 459 1-7 Iqn〇2 、 PHARMEKS 社 PHAR135367 503 1-8 Cr1。' 。攀f 0 / PHARMEKS 社 PHAR137229 476 283 200843739
284 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+]
PHARMEKS 社 PHAR139255
285 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-15 SPECS AG-690/12867290 476 1-16 〇^ζ)^0^ ψ /° PHARMEKS 社 PHAR146510 492 1-17 ><H f ο人^ 471 286 200843739
熔點(°C)或 購入來源及品項 269-274)d) 221-223 MS m/z [M+] 471 483 424 287 200843739
288 200843739
289 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-27 /°^〇K_/〇h P^o 心 238-240 487 1-28 °ό ο人^ 408 I - 29 \。 〇^( 〇 PHARMEKS 社 PHAR057684 473 290 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 〇
291 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-33
0^\ PHARMEKS 社 PHAR019403
292 200843739 化合 物編 結構 號 熔點(°C)或 講入來源及品項 MS m/z [M+]
434 卜37
500 〇
PHARMEKS 社 PHAR040562 293 200843739 化合 物編 號 結構 熔點(°c)或 講入來源及品項 MS m/z [M+] 卜39 y。' 。讲 〇 / PHARMEKS 社 PHAR135263 537 1-40 〇 / 254-258(d) 487 1-41 °ψ α PHARMEKS 社 PHAR131877 480 294 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-42 0 ) PHARMEKS 社 PHAR127015 488 1-43 458 1-44 ^yCr1。' ψ 0 / 473 295 200843739
296 200843739
297 200843739 化合 物編 號 結構 熔點(°c)或 iV1; 購入來源及品項 1-51 Ο
〇 〇 483
298 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+]
PHARMEKS 社 PHAR027786 〇
299 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] I 一 57 Μ Π
〇 431
〇
300 200843739 %, 化合 物編 號 1-60 卜61 結構
C
C
〇 〇
熔點(°c)或 購入來源及品項 PHARMEKS 社 PHAR142165 PHARMEKS 社 PHAR105869 MS m/z [M+] 488 468 301 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-63
〇 PHARMEKS 社 PHAR026958 1-64 Ο
〇 245-246 471
PHARMEKS 社 PHAR128015 302 200843739
303 200843739
304 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-72 Ο
366 1-73
245-247 434 457 305 200843739
306 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-78 Ο
〇 253-254 453
472
506 307 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-81 分。 〇 / 458 1-83 。十〆 。承 〇 / PHARMEKS 社 PHAR032514 495 1-84 PHARMEKS 社 PHAR137490 416 308 200843739 化合 物編 號 結構 熔點(°c)或 講入來源及品項 MS m/z [M+] 1-85 丫0 6 〇 )SrQr 〇 PHARMEKS 社 PHAR140664 477 1-86 °ψ 〇 / 473 1-87 '畔 0 268-271 430 309 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-88 条, (° PHARMEKS 社 PHAR124071 464 1-89 〇 PHARMEKS 社 PHAR127988 448 1-90 。彳 XT! 。杂 〇 / PHARMEKS 社 PHAR138301 434 310 200843739
熔點rc)或 講入來源及品項 MS m/z [M+] INTERBIOSCREEN 社 STOCK2S-84529 PHARMEKS 社 PHAR068896 PHARMEKS 社 PHAR012733 398 509 416 311 200843739 化合 物編 號 結構 熔點(°c)或 講入來源及品項 MS m/z [M+] 卜94 σ1 °i)Q W/ V二0 〇— PHARMEKS 社 PHAR106162 443 1-95 F-<\ ^y>N IFLAB 社 F0851-0720 414 1-96 u0 h 251-252 405 312 200843739 化合 物編 號 結構 熔點(°c)或 講入來源及品項 MS m/z [M+] 1-97 o~c, 〇 CSC社 D34650002 418 1-98 CHEMDIV 社 C390-0063 491 1-99 Q-(\ /)-N N 0 CHEMDIV 社 C390-0059 416 313 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-100
Br CHEMDIV 社 C390-0113 535 1-101
CHEMDIV 社 C390-0021 525 1-102
Br
CHEMDIV 社 C390-0023 525 314 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 〇 Br
Br Br
315 200843739 化合 物編 結構 號 熔點(°C)或 講入來源及品項 MS m/z [M+] 1-106 〇
Br CHEMDIV 社 C390-0083 〇
316 200843739 化合 物編 結構 號 熔點(°C)或 講入來源及品項 MS m/z [M+] —〇 Br
CHEMDIV 社 5340-2243 〇
317 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+]
〇
318 200843739 化合 物編 結構 號 熔點(°C)或 講入來源及品項 MS m/z [M+] 〇
CSC社 D50050967 438
319 200843739
320 200843739 化合 物編 結構 號 熔點rc)或 講入來源及品項 MS m/z [M+]
321 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+]
322 200843739 化合 物編 號 1-127 卜128 1-129
熔點(°C)或 購入來源及品項 MS m/z [M+] CHEMDIV 社 C390-0571 CHEMDIV 社 C390-0605 CHEMDIV 社 C390-0540 324 324 310 323 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 卜130
CHEMDIV 社 C390-0594 1-131
CHEMDIV 社 C390-0569
CHEMDIV 社 C390-0545 324 200843739 化合 物編 結構 號 熔點rc)或 購入來源及品項 MS m/z [M+]
N 〇 325 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-136 〇 9 〇 CHEMDIV 社 C390-0562 277 1-137 °γνΟ^°\ INTERBIOSCREEN 社 STOCK3S-19371 卜138 r INTERBIOSCREEN 社 STOCK3S-27961 326 200843739 化合 物編 號 構 結 熔點rc)或 購入來源及品項 MS m/z [M+] I 一 139
CHEMICALBLOCK 社 A2826/0119344 1-140
CHEMICALBLOCK 社 A2846/0120094 1-141
CHEMICALBLOCK 社 A2864/0120776 327 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 卜142 C^Br CHEMICALBLOCK 社 A2921/0123016 1-143 r/ 夂Vv CHEMICALBLOCK 社 A2956/0124459 卜144 0^N-O^° PHARMEKS 社 PHAR020271 328 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+]
PHARMEKS 社 PHAR033094 1-146
PHARMEKS 社 PHAR036801 1-147
PHARMEKS 社 PHAR050263 329 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+]
1-148
PHARMEKS 社 PHAR062175
PHARMEKS 社 PHAR067480
1-150
PHARMEKS 社 PHAR070697 330 200843739 化合 物編 結構 號 熔點rc)或 講入來源及品項 MS m/z [M+]
PHARMEKS 社 PHAR071219 1-152
PHARMEKS 社 PHAR079682 1-153 〇
PHARMEKS 社 PHAR087561 331 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 卜154 〇
〇 PHARMEKS 社 PHAR094621 1-155
PHARMEKS 社 PHAR104096
PHARMEKS 社 PHAR107350 332 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 卜157
PHARMEKS 社 PHAR111534 M58
PHARMEKS 社 PHAR115440
PHARMEKS 社 PHAR117573 333 200843739 化合 物編 號 1-160 1-161 1-162
熔點(°C)或 講入來源及品項 MS m/z [M+] PHARMEKS 社 PHAR118326 PHARMEKS 社 PHAR119097 PHARMEKS 社 PHAR120941 334 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-163
Ο PHARMEKS 社 PHAR127775
PHARMEKS 社 PHAR128943 1-165
PHARMEKS 社 PHAR130612 335 200843739 化合 物編 號 構 結 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-166
PHARMEKS 社 PHAR134114 1-167 ο
0 PHARMEKS 社 PHAR135268 1-168
ό PHARMEKS 社 PHAR137109 336 200843739 化合 物編 號 結構 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-169
〇 PHARMEKS 社 PHAR138274 M70
PHARMEKS 社 PHAR138772 1-171
〇 F PHARMEKS 社 PHAR140674 337 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-172
F PHARMEKS 社 PHAR144655
338 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 〇
339 200843739 化合 物編 結構 號 熔點(°C)S iV1; 購入來源及品項 1-178
382
340 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-182
〇 498
〇
341 200843739 化合 物編 結構 號 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-185 Ο
193-196 471
377 1-191
416 342 200843739 化合 物編 結構
熔點(°C)或 購入來源及品項 MS m/z [M+] 533 255-256 424 245-246 406 343 200843739 化合 物編 號 結構 熔點(°C)或 講入來源及品項 MS m/z [M+] 1-195 Cnr° s' 〇 479 1-196 o' 449 1-197 〇rr° S^N 〇 479 344 200843739 化合 物編 號 結構 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-198 >290 430 1-199 9 OH OMe 226-229 443 1-200 9 OH 216-219 458 345 200843739
346 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-202
〇 177-178
347 200843739 化合物 編號 結構式 熔點CC)或 購入來源及品項 MS m/z [M+]
348 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-208
〇 >290 434
232-235 461
349 200843739
350 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-215 Ο
〇 〇 207-210 503 1-216 Ο
Ο 229-232 489
351 200843739 化合物 編號 結構式 熔點rc)或 購入來源及品項 MS m/z [M+] 1-218
1-219 Ο
249-252 485
352 200843739 化合物 編號 結構式 熔點(°C)或 講入來源及品項 MS m/z [M+]
〇 241-244 481 247-249 560
353 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-224 Ο
〇 〇 268-272 461
354 200843739 化合物 編號 結構式 熔點rc)或 構入來源及品項 MS m/z [M+] 1-227
221-224 475 1-228
217-218 468 1-229
213-215 355 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-230
229-230 433 1-231
〇 245-248 474 1-232
〇 223-225 462 356 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-233 〇
〇 247-250 477 1-234 Ο
Ο 230-233 465 1-235 Ο
〇 502 357 200843739 化合物 編號 結構式 熔點rc)或 講入來源及品項 MS m/z [M+]
〇 232-234 454
358 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-239 Ο
〇 227-228 433
〇 430 1-241
455 359 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-242
〇 〇- 429 1-243
498 1-244
〇 461 360 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-245 〇
〇 /〇 462 1-246 Ο
〇 435 1-247
449 361 200843739 化合物 編號 結構式 熔點(°C)或 講入來源及品項 MS m/z [M+] 1-248
〇 390 1-249
〇 401 1-250
197-204 362 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-251 Ο Ν
cr 、〇 468 1-252 Ο
〇 434 1-253 Ο
〇 384 363 200843739 化合物 編號 結構式 熔點(°C)或 構入來源及品項 MS m/z [M+] 1-254
〇 430 1-255
〇 380 1-256
482 364 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-257
448 1-258
F 444 1-259
ο 380 365 200843739 化合物 編號 結構式 熔點(°C)或 講入來源及品項 MS m/z [M+] 1-260
378 1-261
382 1-262 η
〇 384 366 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-263
394 1-264
405 1-265 〇
〇 404 367 200843739 化合物 編號 結構式 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-266 Μ 哼。 〇丨 400 1-267 傳 473 1-268 461 368 200843739 化合物 編號 結構式 熔點(°c)或 購入來源及品項 MS m/z [M+] 1-269 373 1-270 448 1-271 7 X) 448 369 200843739 化合物 編號 結構式 熔點rc)或 講入來源及品項 MS m/z [M+] 1-272
434 1-273
462 1-274
468 370 200843739 化合物 編號 結構式 熔點rc)或 購入來源及品項 MS m/z [M+] 1-275
444
371 200843739 化合物 編號 結構式 熔點rc)或 講入來源及品項 MS m/z [M+] 1-278
458 1-279
0 469 1-281 Ο
F F 484 372 200843739 化合物 編號 結構式 熔點(°C)或 購入來源及品項 MS m/z [M+] 1-282
434 1-283
〇 〇 450 1-284
430 373 200843739 化合物 編號 結構式 熔點fC)或 購入來源及品項 MS m/z [M+] 1-285
F F 480 374 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] II-1
422 II-2
〇 404 ΙΙ-3
〇 418 375 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] ΙΙ-4
〇 433 ΙΙ-5
〇 418 ΙΙ-6
〇 400 376 200843739 化合物 編號 II-7
377 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-10
396 11-11 〇
〇 446
411 378 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-13
〇 469 11-14
〇 479 11-15
429 379 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-16
487
380 200843739
381 200843739
382 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-25
〇
420
383 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-28
433 11-29 η
451 11-30
429 384 200843739
385 200843739
386 200843739
387 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-40
〇
Chiral 433 11-41
〇
Chiral 429 11-42
Chiral 429 388 200843739 化合物 編號 構 結 溶點rc) MS m/z [M+] II-43
448 11-44
444 ΙΙ-45 ^ ν/ο ρ 〇
ο
417 389 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-46
413 11-47 Ο
432 11-48
428 390 200843739 化合物 編號 結構 MS m/z [M+] 11-49
454 11-50
454 11-51
419 391 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] II-52
450 II-53
487 ΙΙ-54
460 392 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-55
456 11-56
415 11-57
〇 428 393 200843739
394 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+]
11-61
〇 486 11-62
472 11-63
378 395 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-64
〇 374
396 200843739
397 200843739
398 200843739
399 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-76
〇 444 11-77
444 11-78
463 400 200843739
401 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] II-82
433 ΙΙ-83
〇 459 ΙΙ-84
434 402 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+]
II-85 ο
Ο 511 11-86
Ο 430 11-87
ο 507 403 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-88 °0 ό 459 11-89 J V ry^N^o τ Br 477 11-90 /TV^N 九 V Br 417 404 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-91
413 II-92 ΙΙ-93
469 439 405 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-94
429 11-95
476 11-96
461 406 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-97
〇 434
407 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] II-100
〇 404 II-101
〇 454 II-102
554 408 200843739 化合物 編號 II-103 II-104 II-105
溶點(〇C) MS m/z [M+] 516 516 439 409 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-106
453 11-107
426 11-108
390 410 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-109 〇
450
411 200843739 化合物 編號 結構 熔點fC) MS m/z [M+] 11-112
428 11-113
430 11-114
400 412 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-115
400 11-116
446 11-117
386 413 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-118 ο 445 11-119 % 472 11-120 Ό^ΝΧΝ 〇^。 472 414 200843739
415 200843739
416 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] II -127
〇 447 11-128
468 11-129 π
449 417 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-130
〇 444 11-131
471 11-132
445 418 200843739
419 200843739
420 200843739
421 200843739
422 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-145
〇 441 11-146
410 11-147
410 423 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-148
473 11-149
476 11-150
457 424 200843739
425 200843739
426 200843739
427 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-160 rV^° 人 Ο 472 11-161 V ο 6 ά 403 11-162 Cr ό ό 413 428 200843739
429 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-166
399 II-167
〇 N 401 II-168
490 430 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-169 476 11-170 成。 α 506 11-171 号 〇 459 431 200843739 化合物 編號 II-172 II-173 II-174
溶點rc) MS m/z [M+] 500 467 409 432 200843739
433 200843739
434 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-181
483 11-182
449 11-183
519 435 200843739
436 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-187
〇* 516 11-188
〇
404 II-189
451 437 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-190 今。 ό 465 11-191 471 11-192 〇i? 〇 / 479 438 200843739
439 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-196
394 11-197
447 11-198
443 440 200843739
441 200843739 化合物 編號 II-202 II-203 II-204
熔點(〇C) MS m/z [M+] 482 434 458 442 200843739
443 200843739
444 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+]
445 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+]
446 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-217
〇 413 11-218 〇
459
11-219
455 447 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-220 〇
〇 489 11-221
437 11-222
433 448 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-223
413 11-224 〇
423
449 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-226 祜。 443 11-227 \。供 ό 434 11-228 故。 % 〇/ 457 450 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] II - 229
437 II - 230
419 11-231
437 451 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-232
433 11-233
454 II-234 〇
485 452 200843739 化合物 編號 結構 熔點(°c) MS m/z [M+] 11-235 Ο
〇 473
453 444 453 200843739
454 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+]
455 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-244
455 11-245
453
456 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] II-247
〇- 540 ΙΙ-248
Ο- 542
C ΙΙ-249 Γ\
530 457 200843739
458 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-253
Ο 475
461 447 459 200843739 化合物 編號 結構 熔點(°C) MS m/z [M+] 11-256 Ο
〇 487 11-257
459 11-258
Ο
Ο 455 460 200843739
461 200843739 化合物 編號 結構 熔點rc) MS m/z [M+] 11-262 441 462 200843739 表中: 【化59】
試驗例 5 將導入有人類P2X3受體基因(GenBank註冊序列 Y07683)之C6BU-1細胞的安定表現細胞株播種於塗佈pDL 之96井微滴定盤,使每1井為8〇〇〇個,並於培養基(含有8·3% 牛胎兒血清、8.3%馬血清、1%抗生物質抗真菌劑混合溶液 之DMEM)中以37°C、5%二氧化碳下培養1天。將培養基換 10 為含有 Fluo-3-ΑΜ 4μΜ之添加液(2〇mM HEPES、137mM NaCn、2.7mM KQ、0.9mM MgCl2、5.0mMCaCl2、5.6mM D-葡萄糖、2.5mM 丙磺舒(probenecid)、10%BSA、 0.08%PLURONIC® F-127、ρΗ7·5),以37°C、5%二氧化碳 下培養1小時。以洗淨用缓衝液(20mM HEPES、137mM 15 NaQ、2.7mMKCn、0.9mM MgCl2、5.0mM CaCl2、5.6mM D-葡萄糖、2.5mM丙磺舒、ρΗ7·5)洗淨,以每井4〇μι之洗淨 用緩衝液充滿之。將微滴定盤設於大量快速篩檢系統(High 463 200843739 throughput screening system)FDSS 3000(濱松光子學株式 會社)。開始以FDSS 3000測定螢光強度,並以FDSS 3000 内藏之自動分注裝置,將已藉稀釋用緩衝液(2〇mM HEPES、137mM Nad、2.7mM Κα、0.9mM MgCl2、5.0mM 5 CaCl2、5.6mM D-葡萄糖、2.5mM 丙磺舒、0.1% PLURONIC® F-127、ρΗ7·5)稀釋成不同濃度之被測化合物 DMSO溶液分注為每1井40μ1。5分鐘後,以内藏在FDSS 3000之自動分注裝置分注業已藉稀釋用緩衝液稀釋之 40nM ATP溶液50μ1,持續測定之後3分鐘之螢光強度。從所 10測定之螢光強度值算出微滴定盤每1井之比最大螢光強 度,該比最大螢光強度係將ΑΤΡ溶液添加後之螢光強度最大 值以相對於測定開始時之螢光強度的比表示者。令不含被 測化合物時之比最大螢光強度值為拮抗〇%,且添加稀釋用 緩衝液取代ΑΤΡ時之比最大螢光強度值為拮抗1〇〇%,算出 15拮抗50%之濃度(IC5〇)來評估被測化合物之拮抗活性。比最 大螢光強度之計算係使用FDSS軟體(濱松光子學株式會社) 進行者。ICso之計算係使用微軟ExcEL(Microsoft社)及 XLfit(idbs社)之軟體進行者。 兹將本發明化合物之試驗結果示於下表。 20 464 200843739 化合物編號 P2X3 IC50_) 1-1 0.01 1-2 0.01 1-4 0.02 1-6 0.03 1-20 0.14 1-21 0.16 1-24 0.18 1-25 0.18 1-28 0.26 1-36 0.38 1-44 0.56 1-45 0.58 1-48 0.97 1-49 1.02 1-52 1.27 1-53 1.28 1-57 1.53 1-62 1.96 1-66 3.46 1-69 3.78 1-72 4.79 1-74 5.92 1-76 6.48 1-77 8.01 1-79 8.95 1-88 15.43 1-95 0.56 1-96 0.92 1-118 17.80 1-122 19.30 Μ 24 22.00 1-251 1.40 1-260 5.63 1-273 2.20 1-278 1.40 465 200843739 化合物編號 Ρ2Χ3 IC50_ 1.37 〜 ϊτΤ· 0.86 ' II-13 057 〜 ΪΓΪ4 0.38 ΪΜ6 1.51 〜 ΪΓΠ 0.31 〜 11¾ 2.31 ^ ΪΜ9 0.59 〜 ΙΙ-30 069 〜 ΙΙ-40 0.37 ^^ ΪΜΓ 0.17 ^ ΙΙ-45 1.07 ^ ΙΙ-57 1.68 〜 ΙΙ-64 Γ31 ^ ΙΙ-72 0.66 〜 ΰ^75 0.37 〜 1^85 2.52 〜 1^87 1.32 〜 11-95 0.71 〜 1^98" 1 0.07 ^' II-106 2.08 ΙΙ-123 2.09 〜' II-129 0.74 〜 11-130 0.13 〜 11-171 095 〜 1^72 2.00 ΙΜ81 0.33 〜 II-183 0.03 〜 ΙΙ_193 ττ rCTT---- 一~127 ^ 11-201 0.01 〜' 11-202 1.62 〜 11-217 1.87 〜 本發明之化合物顯示出對P2XS受體之拮抗活性 外,本發明之化合物係對P2X3亞型作用,因此可知,此 對於 έ有P2X2亞型而構成之P2XW受體同樣地亦會顯示出拮抗 5 活性。 〇几 產業上之可利用性 本發明之化合物對於Ρ2Χ3及/或Ρ2Χ2/3受體具有拮抗作 用,而對於Ρ2Χ3及/或Ρ2Χ2/3受體相關疾病或狀態,例如慢 466 200843739 性疼痛、過活動膀胱甚為有用。 L圖式簡單說明3 (無) 【主要元件符號說明】 (無) 467
Claims (1)
- 200843739 十、申請專利範圍: 1· 一種P2X3及/或P2X2,3受體拮抗劑,含有如下通式(I)所示 之化合物、其製藥上可接受之鹽或是該等之溶劑合物; 通式(I): 5 【化1】式中’ Z1為可任擇受到保護之羥基、可任擇受到保 護之羥胺基或可任擇具有取代基之胺基,z2為=〇或 =N-E(E為氫、羥基、可任擇具有取代基之低級烷基、可 10 任擇具有取代基之低級烷氧基或是可任擇具有取代基 之胺基);或是 【化2】形成 R4及R5各自獨立為氫或低級烷基,R6為氫、可任擇 具有取代基之低級烷基或醯基,r為0〜2之整數; Ra及Rb各自獨立為氫或低級烷基; q為0〜4之整數; A為環烷基、環烯基、芳基或雜環基; 468 15 200843739 R1各自獨立為_素、羥基、可任擇具有取代基之低 級烷基、可任擇具有取代基之低級烯基、可任擇具有取 代基之低級炔基、可任擇具有取代基之低級烷氧基、可 任擇具有取代基之低級烷硫基、可任擇具有取代基之醯 基、羧基、可任擇具有取代基之低級烷氧羰基、可任擇 具有取代基之胺甲醯基、可任擇具有取代基之低級烷基 胺曱醯基、可任擇具有取代基之胺基、可任擇具有取代 基之胺磺醯基、氰基、硝基、可任擇具有取代基之環烷 基、可任擇具有取代基之環烯基、可任擇具有取代基之 芳基或可任擇具有取代基之雜環基; N為0〜3之整數(但, 【化3】AJR1)!!亦可為氫); 15 r2為可任擇具有取代基之烷基、可任擇具有取代基 之低級烧氧基、可任擇具有取代基之低級烧基胺甲醯 基、可任擇具有取代基之環烷基、可任擇具有取代基之 環烯基、可任擇具有取代基之芳基或可任擇具有取代基 之雜環基; 20 r3為氫、可任擇具有取代基之烷基、可任擇具有取 代基之環烷基、可任擇具有取代基之環烯基、可任擇具 有取代基之芳基或可任擇具有取代基之雜環基。 469 200843739 2·如申請專利範圍第1項之P2X3及/或P2X2/3受體拮抗劑, 其中Z1為羥基,22為=〇。 3·如申請專利範圍第1項之P2X3及/或P2X2/3受體拮抗劑, 其中r為〇。 5 4·如申請專利範圍第1〜3項中任一項之P2X3及/或P2X2/3受 體拮抗劑,其中環A為苯基、吡啶基或噻唑基。 5.如申請專利範圍第1項之P2X3及/或P2X2/3受體拮抗劑, 其中R1為可任擇具有取代基之低級烷氧羰基或可任擇 具有取代基之雜環基。 10 6·如申請專利範圍第丨項之或ρ2χ2/3受體拮抗劑, 其中R2為可任擇具有取代基之低級烷基、可任擇具有取 代基之笨基或可任擇具有取代基之吼啶基。 7·如申請專利範圍第i項之Ρ2χ3及/或Ρ2χ2/3受體拮抗劑, 其中R3為碳原子數3〜10之烷基、環烷基或可任擇具有取 15 代基之苯基。 8·如申請專利範圍第丨項之ρ2Χ3及^ρ2χ2/3受體拮抗劑, 其中q為0。 9·如申請專利範圍第!項之p2Xs及域!^2,3受體拮抗劑, 其中q為1。 20 ι〇· 一種如下通式(I,)所示之化合物、其製藥上可接受之鹽 或是該等之溶劑合物,其中通式(Γ): 【化4】 470 200843739(R1D)P 式中,z1為可任擇受到保護之羥基、可受任擇保護 之羥胺基或可任擇具有取代基之胺基,22為:=:〇或 =N-E(E為氫、羥基、可任擇具有取代基之低級烷基、可 任擇具有取代基之低級烷氧基或是可任擇具有取代基 之胺基;或 【化5】R及R各自獨立為氫或低級烧基,r6為氫、可任擇 具有取代基之低級烧基或酿基,r為〇〜2之整數; 環A及環B各自獨立為環烷基、環烯基、芳基或雜 環基; Rla&Rlb各自獨立為_素、羥基、可任擇具有取代 基之低級烷基、可任擇具有取代基之低級烯基、可任擇 具有取代基之低級炔基、可任擇具有取代基之低級烷氧 基、可任擇具有取代基之低級烷硫基、可任擇具有取代 基之醯基、羧基、可任擇具有取代基之低級烷氧羰基、 可任擇具有取代基之胺甲醯基、可任擇具有取代基之低 471 200843739 級烷基胺甲醯基、可任擇具有取代基之胺基、可任擇具 有取代基之胺續醯基、氰基或硝基; m及ρ各自獨立為〇〜2之整數; R2為可任擇具有取代基之烷基、可任擇具有取代基 5 之低級烷氧基、可任擇具有取代基之低級烷基胺甲醯 基、可任擇具有取代基之環烷基、可任擇具有取代基之 環烯基、可任擇具有取代基之芳基或可任擇具有取代基 之雜環基; R3為氫、可任擇具有取代基之低級烧基、可任擇具 ίο 有取代基之環烷基、可任擇具有取代基之環烯基、可任 擇具有取代基之芳基或可任擇具有取代基之雜環基; 但是,環A為吡唑酮且環B為苯基之化合物除外。 11 ·如申清專利範圍弟1 〇項之化合物、其製藥上可接受之鹽 或是該等之溶劑合物,其中Z1為可任擇受到保護之羥 15 基’ z為=〇 ’ R2為可任擇具有取代基之烧基、可任擇具 有取代基之低級烷氧基、可任擇具有取代基之環烷基、 可任擇具有取代基之環烯基、可任擇具有取代基之芳基 或可任擇具有取代基之雜環基。 12·如申請專利範圍第10項之化合物、其製藥上可接受之鹽 20 或是該等之溶劑合物,其中r為0,R2為可任擇具有取代 基之烧基,可任擇具有取代基之低級烷氧基、可任擇具 有取代基之環烷基、可任擇具有取代基之環烯基、可任 擇具有取代基之芳基或可任擇具有取代基之雜環基。 13·如申請專利範圍第10〜12項之化合物、其製藥上可接受 472 200843739 之鹽或是該等之溶劑合物,其中環A為苯基、 噻唑基。 °比啶基或 14· -種如下述通式(1,,)所示之化合物、#製藥上可接受 鹽或是該等之溶劑合物: 【化6】 之(Γ,) 10 式中’ Z1為可任擇受到保護之羥基、可任擇受到保 護之經胺基或可任擇具有取代基之胺基,Z2為=〇或 =N-E(E為氫、羥基、可任擇具有取代基之低級烷基、可 任擇具有取代基之低級烷氧基或可任擇具有取代基之 胺基;或者 【化7】 Z2 r 21 ^ 形成 N-fCR^r R及R各自獨立形成氯或低級烧基,r6為氯、可任 擇具有取代基之低級烷基或醯基,r為〇〜2之整數; 環A為環烷基、環烯基、芳基或雜環基; R各自獨立為_素、經基、可任擇具有取代基之 473 15 200843739 低級烷基、可任擇具有取代基之低級烷氧基、可任擇具 有取代基之低級烷硫基、可任擇具有取代基之醯基、羧 基、可任擇具有取代基之低級烷氧羰基、可任擇具有取 代基之胺甲醯基、可任擇具有取代基之低級烷基胺曱醯 基、可任擇具有取代基之胺基、可任擇具有取代基之胺 續醯基、氰基或硝基; m為0〜2之整數; Rle及Rld各自獨立為氫或可任擇具有取代基之低 級烷基; R2為可任擇具有取代基之烷基、可任擇具有取代基 之低級烧氧基、可任擇具有取代基之低級烷基胺甲醯 基、可任擇具有取代基之環烷基、可任擇具有取代基之 環烯基、可任擇具有取代基之芳基或可任擇具有取代基 之雜壤基; R3為氫、可任擇具有取代基之低級烷基、可任擇具 有取代基之環烷基、可任擇具有取代基之環烯基、可任 擇具有取代基之芳基、可任擇具有取代基之雜環基。 15·如申請專利範圍第14項之化合物、其製藥上可接受之鹽 或是該等之溶劑合物,其中ζι為可任擇受到保護之羥 基,Z2為=〇,R2為可任擇具有取代基之烷基、可任擇具 有取代基之低級烷氧基、可任擇具有取代基之環烷基、 可任擇具有取代基之環烯基、可任擇具有取代基之芳基 或可任擇具有取代基之雜環基。 16·如申請專利範圍第14項之化合物、其製藥上可接受之鹽 474 200843739 或是該等之溶劑合物,其中r為〇,R2為可任擇具有取代 基之、丨元基、可任擇具有取代基之低級烧氡基、可任擇具 有取代基之環烷基、可任擇具有取代基之環烯基、可任 擇具有取代基之芳基或可任擇具有取代基之雜環基。 5 I7·如申請專利範圍第14〜16項中任一項之化合物、其製藥 上可接受之鹽或是該等之溶劑合物,其中環人為苯基、 。比°定基或嗟唾基。 18. —種藥學組成物,含有如申請專利範圍第1〇〜17項中任 一項之化合物、其製藥上可接受之鹽或是該等之溶劑合 0 物。 19. 一種P2XS及/或P2X2,3受體拮抗劑,含有如申請專利範圍 第10〜17項中任一項之化合物、其製藥上可接受之鹽或 是該等之溶劑合物。 20. 一種如申請專利範圍第10〜17項中任一項之化合物、其 5 製藥上可接受之鹽或是該等之溶劑合物的用途,係將如 申請專利範圍第10〜17項中任一項之化合物、其製藥上 可接受之鹽或是該等之溶劑合物用於治療及/或預防 P2X3及/或Ρ2χ2/3受體相關疾病者。 475 200843739 七、指定代表圖: (一) 本案指定代表圖為:第(無)圖。 (二) 本代表圖之元件符號簡單說明: (無) 八、本案若有化學式時,請揭示最能顯示發明特徵的化學式:(CRaRb)q 丄 » A^(R1)n ⑴
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MX2015016344A (es) | 2013-05-27 | 2016-03-01 | Novartis Ag | Derivados de imidazo-pirrolidinona y su uso en el tratamiento de enfermedades. |
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MX2015016425A (es) | 2013-05-28 | 2016-03-03 | Novartis Ag | Derivados de pirazolo-pirrolidin-4-ona y su uso en el tratamiento de enfermedades. |
EA028175B1 (ru) * | 2013-05-28 | 2017-10-31 | Новартис Аг | Производные пиразолопирролидин-4-она в качестве ингибиторов вет и их применение при лечении заболевания |
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KR20100016076A (ko) * | 2007-03-30 | 2010-02-12 | 시오노기 앤드 컴파니, 리미티드 | 신규 피롤리논 유도체 및 그것을 함유하는 의약 조성물 |
TW201016702A (en) * | 2008-09-25 | 2010-05-01 | Shionogi & Co | Novel pyrrolinone derivative and pharmaceutical composition comprising the same |
-
2008
- 2008-03-28 KR KR1020097022735A patent/KR20100016076A/ko not_active Application Discontinuation
- 2008-03-28 WO PCT/JP2008/056107 patent/WO2008120725A1/ja active Application Filing
- 2008-03-28 TW TW097111332A patent/TW200843739A/zh unknown
- 2008-03-28 CA CA002682473A patent/CA2682473A1/en not_active Abandoned
- 2008-03-28 EP EP08739225A patent/EP2143713A4/en not_active Withdrawn
- 2008-03-28 US US12/450,548 patent/US8101644B2/en not_active Expired - Fee Related
- 2008-03-28 JP JP2009507522A patent/JP5624762B2/ja not_active Expired - Fee Related
- 2008-03-28 CN CN200880017760A patent/CN101679246A/zh active Pending
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2011
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JPWO2008120725A1 (ja) | 2010-07-15 |
KR20100016076A (ko) | 2010-02-12 |
US20100210632A1 (en) | 2010-08-19 |
EP2143713A1 (en) | 2010-01-13 |
US8101644B2 (en) | 2012-01-24 |
US8497263B2 (en) | 2013-07-30 |
CN101679246A (zh) | 2010-03-24 |
JP5624762B2 (ja) | 2014-11-12 |
EP2143713A4 (en) | 2011-04-20 |
US20120010199A1 (en) | 2012-01-12 |
CA2682473A1 (en) | 2008-10-09 |
WO2008120725A1 (ja) | 2008-10-09 |
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