TWI660952B - 抗增生化合物及其使用方法 - Google Patents

Info

Publication number

TWI660952B

TWI660952B TW104122680A TW104122680A TWI660952B TW I660952 B TWI660952 B TW I660952B TW 104122680 A TW104122680 A TW 104122680A TW 104122680 A TW104122680 A TW 104122680A TW I660952 B TWI660952 B TW I660952B

Authority

TW

Taiwan

Prior art keywords

methyl

dioxopiperidin

alkyl

difluoro

compound

Prior art date

2014-07-11

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 442
• 238000000034 method Methods 0.000 title claims abstract description 154
• 230000001028 anti-proliverative effect Effects 0.000 title 1
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 168
• 201000011510 cancer Diseases 0.000 claims abstract description 92
• 208000032839 leukemia Diseases 0.000 claims abstract description 60
• 238000011282 treatment Methods 0.000 claims abstract description 57
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
• 125000000217 alkyl group Chemical group 0.000 claims description 321
• -1 3-chloro-4-methylphenyl Chemical group 0.000 claims description 254
• 239000000203 mixture Substances 0.000 claims description 195
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 186
• 150000003839 salts Chemical class 0.000 claims description 169
• 229910052739 hydrogen Inorganic materials 0.000 claims description 157
• 239000001257 hydrogen Substances 0.000 claims description 157
• 125000005843 halogen group Chemical group 0.000 claims description 152
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 152
• 125000001424 substituent group Chemical group 0.000 claims description 121
• 125000000623 heterocyclic group Chemical group 0.000 claims description 115
• 150000002431 hydrogen Chemical class 0.000 claims description 92
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 57
• 125000002947 alkylene group Chemical group 0.000 claims description 57
• 229910052757 nitrogen Inorganic materials 0.000 claims description 52
• 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 47
• 229910052717 sulfur Chemical group 0.000 claims description 47
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 46
• 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 45
• 229910052760 oxygen Inorganic materials 0.000 claims description 45
• 239000003814 drug Substances 0.000 claims description 44
• 239000013543 active substance Substances 0.000 claims description 32
• 238000002560 therapeutic procedure Methods 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 25
• 239000002246 antineoplastic agent Substances 0.000 claims description 24
• 210000001185 bone marrow Anatomy 0.000 claims description 18
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 16
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
• 239000011593 sulfur Chemical group 0.000 claims description 16
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• 239000001301 oxygen Chemical group 0.000 claims description 15
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 102000004127 Cytokines Human genes 0.000 claims description 12
• 108090000695 Cytokines Proteins 0.000 claims description 12
• 238000011443 conventional therapy Methods 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 239000002904 solvent Substances 0.000 claims description 10
• 230000001225 therapeutic effect Effects 0.000 claims description 9
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
• 239000002253 acid Substances 0.000 claims description 6
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 230000001154 acute effect Effects 0.000 claims description 5
• 239000003242 anti bacterial agent Substances 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
• 239000000427 antigen Substances 0.000 claims description 4
• 108091007433 antigens Proteins 0.000 claims description 4
• 102000036639 antigens Human genes 0.000 claims description 4
• 229940111134 coxibs Drugs 0.000 claims description 4
• 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 4
• 230000003319 supportive effect Effects 0.000 claims description 4
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
• 239000002955 immunomodulating agent Substances 0.000 claims description 3
• 229940121354 immunomodulator Drugs 0.000 claims description 3
• 230000002584 immunomodulator Effects 0.000 claims description 3
• 239000003018 immunosuppressive agent Substances 0.000 claims description 3
• 230000003647 oxidation Effects 0.000 claims description 3
• 238000007254 oxidation reaction Methods 0.000 claims description 3
• 230000009467 reduction Effects 0.000 claims description 2
• WENKGSGGXGQHSH-UHFFFAOYSA-N 3-(3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O WENKGSGGXGQHSH-UHFFFAOYSA-N 0.000 claims 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 6
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 5
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 5
• CYJAWBVQRMVFEO-UHFFFAOYSA-N piperazine-2,6-dione Chemical compound O=C1CNCC(=O)N1 CYJAWBVQRMVFEO-UHFFFAOYSA-N 0.000 claims 5
• KNCYXPMJDCCGSJ-UHFFFAOYSA-N piperidine-2,6-dione Chemical compound O=C1CCCC(=O)N1 KNCYXPMJDCCGSJ-UHFFFAOYSA-N 0.000 claims 5
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 4
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
• 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 2
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims 2
• 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 2
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
• 108010002386 Interleukin-3 Proteins 0.000 claims 2
• 102100039064 Interleukin-3 Human genes 0.000 claims 2
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 2
• 230000003115 biocidal effect Effects 0.000 claims 2
• 239000003246 corticosteroid Substances 0.000 claims 2
• 230000032050 esterification Effects 0.000 claims 2
• 238000005886 esterification reaction Methods 0.000 claims 2
• 229940125721 immunosuppressive agent Drugs 0.000 claims 2
• GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 claims 2
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 1
• GOYDNIKZWGIXJT-UHFFFAOYSA-N 1,2-difluorobenzene Chemical compound FC1=CC=CC=C1F GOYDNIKZWGIXJT-UHFFFAOYSA-N 0.000 claims 1
• WMKGGPCROCCUDY-UHFFFAOYSA-N 1,5-diphenylpenta-1,4-dien-3-one Chemical compound C=1C=CC=CC=1C=CC(=O)C=CC1=CC=CC=C1 WMKGGPCROCCUDY-UHFFFAOYSA-N 0.000 claims 1
• DZXMMDCITYLSRC-UHFFFAOYSA-N 2-(4-chlorophenyl)-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)C1=CC=C(Cl)C=C1 DZXMMDCITYLSRC-UHFFFAOYSA-N 0.000 claims 1
• XXOZRQAXDWOASO-UHFFFAOYSA-N 2-(4-cyclopropylphenyl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound C1(CC1)C1=CC=C(C=C1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F XXOZRQAXDWOASO-UHFFFAOYSA-N 0.000 claims 1
• KHOFGXWGIVOQDL-UHFFFAOYSA-N 2-(5-bromopyridin-2-yl)-N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoroacetamide Chemical compound BrC=1C=CC(=NC=1)C(C(=O)NCC=1C=C2CN(C(C2=CC=1)=O)C1C(NC(CC1)=O)=O)(F)F KHOFGXWGIVOQDL-UHFFFAOYSA-N 0.000 claims 1
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
• CMRQAKJTXKOGSF-UHFFFAOYSA-N 3-(6-bromo-3-oxo-1h-isoindol-2-yl)piperidine-2,6-dione Chemical compound C1C2=CC(Br)=CC=C2C(=O)N1C1CCC(=O)NC1=O CMRQAKJTXKOGSF-UHFFFAOYSA-N 0.000 claims 1
• YCPULGHBTPQLRH-UHFFFAOYSA-N 3-aminopiperidine-2,6-dione;hydron;chloride Chemical compound Cl.NC1CCC(=O)NC1=O YCPULGHBTPQLRH-UHFFFAOYSA-N 0.000 claims 1
• RVCJOGNLYVNRDN-UHFFFAOYSA-N 4-bromo-2-methylbenzoic acid Chemical compound CC1=CC(Br)=CC=C1C(O)=O RVCJOGNLYVNRDN-UHFFFAOYSA-N 0.000 claims 1
• HCVSOVGAGSUPOO-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(1-hydroxycyclopentyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1(CCCC1)O)(F)F)=O)=O)=O HCVSOVGAGSUPOO-UHFFFAOYSA-N 0.000 claims 1
• NUFAWRNBHUWJFG-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-fluoro-4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=C(C=C1)OC(C)C)F)(F)F)=O)=O)=O NUFAWRNBHUWJFG-UHFFFAOYSA-N 0.000 claims 1
• SBVXMVCDPWXTDN-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-fluorophenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=CC=C1)F)(F)F)=O)=O)=O SBVXMVCDPWXTDN-UHFFFAOYSA-N 0.000 claims 1
• BFORLTWCVIRSQY-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(3-methyl-4-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC(=C(C=C1)OC(C)C)C)(F)F)=O)=O)=O BFORLTWCVIRSQY-UHFFFAOYSA-N 0.000 claims 1
• PSIXNTKRSHRNNV-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-fluoro-2-propan-2-yloxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)F)OC(C)C)(F)F)=O)=O)=O PSIXNTKRSHRNNV-UHFFFAOYSA-N 0.000 claims 1
• AMQUQDRMUDITED-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(4-methoxyphenyl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=CC=C(C=C1)OC)(F)F)=O)=O)=O AMQUQDRMUDITED-UHFFFAOYSA-N 0.000 claims 1
• QAXYIRJMJNSMJY-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-(5-fluoropyridin-2-yl)acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=NC=C(C=C1)F)(F)F)=O)=O)=O QAXYIRJMJNSMJY-UHFFFAOYSA-N 0.000 claims 1
• DUJSYJNRJSCIBC-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[2-(trifluoromethoxy)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=CC=C1)OC(F)(F)F)(F)F)=O)=O)=O DUJSYJNRJSCIBC-UHFFFAOYSA-N 0.000 claims 1
• SORWFPATQRTPID-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-methoxy-2-(trifluoromethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)OC)C(F)(F)F)(F)F)=O)=O)=O SORWFPATQRTPID-UHFFFAOYSA-N 0.000 claims 1
• GVBWAGDULNKFNC-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2,2-difluoro-2-[4-methyl-2-(trifluoromethyl)phenyl]acetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(C1=C(C=C(C=C1)C)C(F)(F)F)(F)F)=O)=O)=O GVBWAGDULNKFNC-UHFFFAOYSA-N 0.000 claims 1
• PSZTVISAVWNYGJ-UHFFFAOYSA-N N-[[2-(2,6-dioxopiperidin-3-yl)-1-oxo-3H-isoindol-5-yl]methyl]-2-(3-ethoxypyridin-2-yl)-2,2-difluoroacetamide Chemical compound O=C1NC(CCC1N1C(C2=CC=C(C=C2C1)CNC(C(F)(F)C1=NC=CC=C1OCC)=O)=O)=O PSZTVISAVWNYGJ-UHFFFAOYSA-N 0.000 claims 1
• ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims 1
• WFKAJVHLWXSISD-UHFFFAOYSA-N anhydrous dimethyl-acetamide Natural products CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 claims 1
• 230000031709 bromination Effects 0.000 claims 1
• 238000005893 bromination reaction Methods 0.000 claims 1
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
• 229940098779 methanesulfonic acid Drugs 0.000 claims 1
• RPVGZMHRZNHDLO-UHFFFAOYSA-N methanesulfonic acid;piperidine-2,6-dione Chemical compound CS(O)(=O)=O.O=C1CCCC(=O)N1 RPVGZMHRZNHDLO-UHFFFAOYSA-N 0.000 claims 1
• SGFACFBLUAWICV-UHFFFAOYSA-N methyl 4-bromo-2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1CBr SGFACFBLUAWICV-UHFFFAOYSA-N 0.000 claims 1
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
• 229910052763 palladium Inorganic materials 0.000 claims 1
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
• QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 1
• 230000002194 synthesizing effect Effects 0.000 claims 1
• 239000004246 zinc acetate Substances 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 abstract description 14
• 230000002265 prevention Effects 0.000 abstract description 11
• 239000002552 dosage form Substances 0.000 abstract description 9
• UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 217
• 125000001188 haloalkyl group Chemical group 0.000 description 147
• 239000012453 solvate Substances 0.000 description 132
• 239000013078 crystal Substances 0.000 description 131
• 125000001072 heteroaryl group Chemical group 0.000 description 107
• 125000004183 alkoxy alkyl group Chemical group 0.000 description 66
• 125000005346 substituted cycloalkyl group Chemical group 0.000 description 58
• 125000002768 hydroxyalkyl group Chemical group 0.000 description 57
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• 125000003118 aryl group Chemical group 0.000 description 53
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• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 46
• 125000004415 heterocyclylalkyl group Chemical group 0.000 description 45
• 150000004677 hydrates Chemical class 0.000 description 45
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• 239000004480 active ingredient Substances 0.000 description 15
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