EA031201B1 - Соединения имидазопиридазина - Google Patents

Info

Publication number

EA031201B1

EA031201B1 EA201700042A EA201700042A EA031201B1 EA 031201 B1 EA031201 B1 EA 031201B1 EA 201700042 A EA201700042 A EA 201700042A EA 201700042 A EA201700042 A EA 201700042A EA 031201 B1 EA031201 B1 EA 031201B1

Authority

EA

Eurasian Patent Office

Prior art keywords

imidazo

carboxamide

pyridazin

pyridazine

chloro

Prior art date

2014-08-06

Links

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• 150000005233 imidazopyridazines Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 157
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 67
• 238000000034 method Methods 0.000 claims abstract description 39
• 150000003839 salts Chemical class 0.000 claims abstract description 28
• 201000010099 disease Diseases 0.000 claims abstract description 24
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
• -1 4-chloro-3-fluorophenyl Chemical group 0.000 claims description 329
• XPYGVSPRBCZOBS-UHFFFAOYSA-N 1h-pyridazine-2-carboxamide Chemical compound NC(=O)N1NC=CC=C1 XPYGVSPRBCZOBS-UHFFFAOYSA-N 0.000 claims description 161
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 66
• 102000001708 Protein Isoforms Human genes 0.000 claims description 43
• 108010029485 Protein Isoforms Proteins 0.000 claims description 43
• 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims description 43
• WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 34
• 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 32
• DJUSZKBLNSVQLI-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound N1=CC=CC2=NC(C(=O)N)=CN21 DJUSZKBLNSVQLI-UHFFFAOYSA-N 0.000 claims description 31
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 25
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
• 201000000980 schizophrenia Diseases 0.000 claims description 13
• 208000024827 Alzheimer disease Diseases 0.000 claims description 12
• 208000019901 Anxiety disease Diseases 0.000 claims description 12
• 208000018737 Parkinson disease Diseases 0.000 claims description 12
• 206010061218 Inflammation Diseases 0.000 claims description 11
• 230000004054 inflammatory process Effects 0.000 claims description 11
• 201000006417 multiple sclerosis Diseases 0.000 claims description 11
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 11
• 208000006673 asthma Diseases 0.000 claims description 10
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 9
• 206010010744 Conjunctivitis allergic Diseases 0.000 claims description 8
• 208000006011 Stroke Diseases 0.000 claims description 8
• 208000002205 allergic conjunctivitis Diseases 0.000 claims description 8
• 230000036506 anxiety Effects 0.000 claims description 8
• 208000024998 atopic conjunctivitis Diseases 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
• 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 6
• SCHCQOLPISHKOS-UHFFFAOYSA-N N1(CCC1)C(=O)C=1N=C2N(N=CC=C2)C=1C1=CC(=C(C(=C1)F)OC)F Chemical compound N1(CCC1)C(=O)C=1N=C2N(N=CC=C2)C=1C1=CC(=C(C(=C1)F)OC)F SCHCQOLPISHKOS-UHFFFAOYSA-N 0.000 claims description 6
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 claims description 6
• 150000004675 formic acid derivatives Chemical class 0.000 claims description 6
• YOCIPGYKDZCTFU-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C(N=C2N1N=CC=C2)C(=O)NC1CC1 Chemical compound ClC1=CC=C(C=C1)C1=C(N=C2N1N=CC=C2)C(=O)NC1CC1 YOCIPGYKDZCTFU-UHFFFAOYSA-N 0.000 claims description 5
• 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 5
• GLYPDLWNQYDRTQ-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)imidazo[1,2-b]pyridazin-3-yl]-2,5-difluorobenzonitrile Chemical compound FC1=CC(C#N)=C(F)C=C1C1=C(N=C2C=CC=NN12)C(=O)N1CCC1 GLYPDLWNQYDRTQ-UHFFFAOYSA-N 0.000 claims description 4
• COQGBMKNVJUVAB-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)imidazo[1,2-b]pyridazin-3-yl]-2-fluorobenzonitrile Chemical compound FC1=C(C=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCC1)C#N COQGBMKNVJUVAB-UHFFFAOYSA-N 0.000 claims description 4
• GGBPMJVCUHMAJB-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)imidazo[1,2-b]pyridazin-3-yl]-5-fluoro-2-methylbenzonitrile Chemical compound CC1=C(C=C(F)C(=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCC1)C#N GGBPMJVCUHMAJB-UHFFFAOYSA-N 0.000 claims description 4
• VGOMARAKBZMHJT-UHFFFAOYSA-N ClC1=CC=C(C=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCCC1 Chemical compound ClC1=CC=C(C=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCCC1 VGOMARAKBZMHJT-UHFFFAOYSA-N 0.000 claims description 4
• WFFUVTXNYNORQT-UHFFFAOYSA-N O=C(N1CCC1)C1=C(N2N=CC=CC2=N1)C1=CN2N=CN=C2C=C1 Chemical compound O=C(N1CCC1)C1=C(N2N=CC=CC2=N1)C1=CN2N=CN=C2C=C1 WFFUVTXNYNORQT-UHFFFAOYSA-N 0.000 claims description 4
• PKGAXGNVVMHTJZ-UHFFFAOYSA-N [3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-2-yl]-(3,3-difluoroazetidin-1-yl)methanone Chemical compound FC1(F)CN(C1)C(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 PKGAXGNVVMHTJZ-UHFFFAOYSA-N 0.000 claims description 4
• WJDDXTCEGQNYBD-UHFFFAOYSA-N [3-(4-chlorophenyl)imidazo[1,2-b]pyridazin-2-yl]-(3-methoxyazetidin-1-yl)methanone Chemical compound COC1CN(C1)C(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 WJDDXTCEGQNYBD-UHFFFAOYSA-N 0.000 claims description 4
• RINAWWCARFNGLM-UHFFFAOYSA-N azetidin-1-yl-(3-pyrazolo[1,5-a]pyrimidin-6-ylimidazo[1,2-b]pyridazin-2-yl)methanone Chemical compound O=C(N1CCC1)C1=C(N2N=CC=CC2=N1)C1=CN2N=CC=C2N=C1 RINAWWCARFNGLM-UHFFFAOYSA-N 0.000 claims description 4
• UGUNGNPFDJUJNI-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-3,5-difluorophenyl)imidazo[1,2-b]pyridazin-2-yl]methanone Chemical compound FC1=CC(=CC(F)=C1Cl)C1=C(N=C2C=CC=NN12)C(=O)N1CCC1 UGUNGNPFDJUJNI-UHFFFAOYSA-N 0.000 claims description 4
• IVSBLXFZMFGIAK-UHFFFAOYSA-N azetidin-1-yl-[3-(4-chloro-3-fluorophenyl)imidazo[1,2-b]pyridazin-2-yl]methanone Chemical compound FC1=C(Cl)C=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCC1 IVSBLXFZMFGIAK-UHFFFAOYSA-N 0.000 claims description 4
• QELHEVBSVCAUHV-UHFFFAOYSA-N azetidin-1-yl-[3-(5-chloropyridin-3-yl)imidazo[1,2-b]pyridazin-2-yl]methanone Chemical compound ClC1=CC(=CN=C1)C1=C(N=C2C=CC=NN12)C(=O)N1CCC1 QELHEVBSVCAUHV-UHFFFAOYSA-N 0.000 claims description 4
• 230000001404 mediated effect Effects 0.000 claims description 4
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
• KNOPWXCBOLJCAA-UHFFFAOYSA-N 3-cyclopropylimidazo[1,2-b]pyridazine-2-carboxamide Chemical compound C1(CC1)C1=C(N=C2N1N=CC=C2)C(=O)N KNOPWXCBOLJCAA-UHFFFAOYSA-N 0.000 claims description 3
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims description 2
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 2
• MKZIIZYJPRYKMM-UHFFFAOYSA-N 3-fluoroazetidine-1-carbaldehyde Chemical compound FC1CN(C=O)C1 MKZIIZYJPRYKMM-UHFFFAOYSA-N 0.000 claims description 2
• NJCCFDZQRIVPQK-UHFFFAOYSA-N 4-[2-(azetidine-1-carbonyl)imidazo[1,2-b]pyridazin-3-yl]-2-fluoro-5-methylbenzonitrile Chemical compound CC1=CC(C#N)=C(F)C=C1C1=C(N=C2C=CC=NN12)C(=O)N1CCC1 NJCCFDZQRIVPQK-UHFFFAOYSA-N 0.000 claims description 2
• SDZFOFNADNADKA-UHFFFAOYSA-N C1(CC1)NC(=O)C=1N=C2N(N=CC=C2)C=1C=1C=NC(=NC=1)OC Chemical compound C1(CC1)NC(=O)C=1N=C2N(N=CC=C2)C=1C=1C=NC(=NC=1)OC SDZFOFNADNADKA-UHFFFAOYSA-N 0.000 claims description 2
• 101000988424 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4B Proteins 0.000 claims description 2
• KQJWGLFCGGXBHN-UHFFFAOYSA-N N1(CCC1)C(=O)C=1N=C2N(N=CC=C2)C=1C1=CC2=C(OCCO2)C=C1 Chemical compound N1(CCC1)C(=O)C=1N=C2N(N=CC=C2)C=1C1=CC2=C(OCCO2)C=C1 KQJWGLFCGGXBHN-UHFFFAOYSA-N 0.000 claims description 2
• FQEXMVRMBJXJHA-UHFFFAOYSA-N azetidin-1-yl-[3-(3-chloro-2,4-dimethylphenyl)imidazo[1,2-b]pyridazin-2-yl]methanone Chemical compound N1(CCC1)C(=O)C=1N=C2N(N=CC=C2)C=1C1=C(C(=C(C=C1)C)Cl)C FQEXMVRMBJXJHA-UHFFFAOYSA-N 0.000 claims description 2
• IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 16
• GAGSQLMTGCAMOG-QWHCGFSZSA-N 3-(3-chloro-4-methylphenyl)-N-[(1R,2S)-2-fluorocyclopropyl]imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CC1=CC=C(C=C1Cl)C1=C(N=C2C=CC=NN12)C(=O)N[C@@H]1C[C@@H]1F GAGSQLMTGCAMOG-QWHCGFSZSA-N 0.000 claims 1
• JMTGAAJHYHUEQI-UHFFFAOYSA-N 3-(4-chloro-2,5-difluorophenyl)-N-propan-2-ylimidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CC(C)NC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1F JMTGAAJHYHUEQI-UHFFFAOYSA-N 0.000 claims 1
• OPBIZTGCIJZSGG-NWDGAFQWSA-N 3-(4-chloro-2-fluorophenyl)-N-[(1R,2S)-2-fluorocyclopropyl]imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound F[C@H]1C[C@H]1NC(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1F OPBIZTGCIJZSGG-NWDGAFQWSA-N 0.000 claims 1
• XIVVDTJZCTVMFP-QWHCGFSZSA-N 3-(4-chloro-2-methylphenyl)-N-[(1R,2S)-2-fluorocyclopropyl]imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CC1=CC(Cl)=CC=C1C1=C(N=C2C=CC=NN12)C(=O)N[C@@H]1C[C@@H]1F XIVVDTJZCTVMFP-QWHCGFSZSA-N 0.000 claims 1
• VTRNMYGATDHWOK-UHFFFAOYSA-N 3-(4-chloro-3-fluorophenyl)-N-cyclopropyl-N-methylimidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CN(C1CC1)C(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1 VTRNMYGATDHWOK-UHFFFAOYSA-N 0.000 claims 1
• VJEYWPJLEFUOTH-UHFFFAOYSA-N 3-(4-chloro-5-fluoro-2-methylphenyl)-N-propan-2-ylimidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CC(C)NC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1C VJEYWPJLEFUOTH-UHFFFAOYSA-N 0.000 claims 1
• VSOPHYORBVNBMU-UHFFFAOYSA-N 3-(4-chlorophenyl)-N-(2-methylcyclopropyl)imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound CC1CC1NC(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 VSOPHYORBVNBMU-UHFFFAOYSA-N 0.000 claims 1
• LROCAZWHWFXPFN-NWDGAFQWSA-N 3-(4-chlorophenyl)-N-[(1R,2S)-2-fluorocyclopropyl]imidazo[1,2-b]pyridazine-2-carboxamide Chemical compound F[C@H]1C[C@H]1NC(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 LROCAZWHWFXPFN-NWDGAFQWSA-N 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• SAWDLJNAAJBRMX-UHFFFAOYSA-N CC1=C(C=C(F)C(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1)C#N Chemical compound CC1=C(C=C(F)C(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1)C#N SAWDLJNAAJBRMX-UHFFFAOYSA-N 0.000 claims 1
• PMXQBXHVHKGVCD-UHFFFAOYSA-N CC1=CC(C#N)=C(F)C=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 Chemical compound CC1=CC(C#N)=C(F)C=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 PMXQBXHVHKGVCD-UHFFFAOYSA-N 0.000 claims 1
• SRRULVNTICTTGE-UHFFFAOYSA-N CC1=CC(Cl)=CC=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 Chemical compound CC1=CC(Cl)=CC=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 SRRULVNTICTTGE-UHFFFAOYSA-N 0.000 claims 1
• AYAPJFYFCDHLKN-UHFFFAOYSA-N CC1=CC=C(C=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1)C#N Chemical compound CC1=CC=C(C=C1C1=C(N=C2C=CC=NN12)C(=O)NC1CC1)C#N AYAPJFYFCDHLKN-UHFFFAOYSA-N 0.000 claims 1
• ZOPYTZDTLDQKKZ-UHFFFAOYSA-N CCCNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1 Chemical compound CCCNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1 ZOPYTZDTLDQKKZ-UHFFFAOYSA-N 0.000 claims 1
• VDPHNQHKTFMQPH-UHFFFAOYSA-N CCCNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 Chemical compound CCCNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 VDPHNQHKTFMQPH-UHFFFAOYSA-N 0.000 claims 1
• YRYSHRMLXGRWSA-UHFFFAOYSA-N CN(C1CC1)C(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 Chemical compound CN(C1CC1)C(=O)C1=C(N2N=CC=CC2=N1)C1=CC=C(Cl)C=C1 YRYSHRMLXGRWSA-UHFFFAOYSA-N 0.000 claims 1
• APQCTKWSIMEXKR-UHFFFAOYSA-N CNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1C Chemical compound CNC(=O)C1=C(N2N=CC=CC2=N1)C1=CC(F)=C(Cl)C=C1C APQCTKWSIMEXKR-UHFFFAOYSA-N 0.000 claims 1
• QJYXPHGWTACNMO-UHFFFAOYSA-N FC(F)(F)C1=NC=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 Chemical compound FC(F)(F)C1=NC=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 QJYXPHGWTACNMO-UHFFFAOYSA-N 0.000 claims 1
• DSCLXJMGAQHPPO-UHFFFAOYSA-N FC(F)OC1=NC=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 Chemical compound FC(F)OC1=NC=CC(=C1)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 DSCLXJMGAQHPPO-UHFFFAOYSA-N 0.000 claims 1
• VPDYRGHPOFWFHI-UHFFFAOYSA-N FC1=CC(=CC=C1Cl)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 Chemical compound FC1=CC(=CC=C1Cl)C1=C(N=C2C=CC=NN12)C(=O)NC1CC1 VPDYRGHPOFWFHI-UHFFFAOYSA-N 0.000 claims 1
• JPCMESYDFZRYOL-UHFFFAOYSA-N N-propan-2-ylimidazo[1,2-b]pyridazine-2-carboxamide Chemical compound C(C)(C)NC(=O)C=1N=C2N(N=CC=C2)C1 JPCMESYDFZRYOL-UHFFFAOYSA-N 0.000 claims 1
• HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 1
• 102100029168 cAMP-specific 3',5'-cyclic phosphodiesterase 4B Human genes 0.000 claims 1
• 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims 1
• 208000035475 disorder Diseases 0.000 abstract description 41
• 210000003169 central nervous system Anatomy 0.000 abstract description 9
• 208000027866 inflammatory disease Diseases 0.000 abstract description 6
• 208000023275 Autoimmune disease Diseases 0.000 abstract description 4
• 230000001363 autoimmune Effects 0.000 abstract description 4
• 230000002503 metabolic effect Effects 0.000 abstract description 2
• 208000030159 metabolic disease Diseases 0.000 abstract 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
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• 239000000460 chlorine Substances 0.000 description 46
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• 239000000203 mixture Substances 0.000 description 38
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• 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 31
• 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 31
• 238000005481 NMR spectroscopy Methods 0.000 description 30
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• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 16
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
• 239000011780 sodium chloride Substances 0.000 description 16
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• 229910052736 halogen Inorganic materials 0.000 description 15
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• 241000238631 Hexapoda Species 0.000 description 12
• ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 description 12
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