JP2016519665A5 - - Google Patents
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- Publication number
- JP2016519665A5 JP2016519665A5 JP2016502587A JP2016502587A JP2016519665A5 JP 2016519665 A5 JP2016519665 A5 JP 2016519665A5 JP 2016502587 A JP2016502587 A JP 2016502587A JP 2016502587 A JP2016502587 A JP 2016502587A JP 2016519665 A5 JP2016519665 A5 JP 2016519665A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- propyl
- pharmaceutical composition
- butyl
- piperazinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- -1 and R 1 Chemical compound 0.000 claims 353
- 239000008194 pharmaceutical composition Substances 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 33
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 27
- 239000001506 calcium phosphate Substances 0.000 claims 23
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims 23
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 22
- 239000011159 matrix material Substances 0.000 claims 18
- 229910000389 calcium phosphate Inorganic materials 0.000 claims 16
- 235000011010 calcium phosphates Nutrition 0.000 claims 16
- 210000004027 cell Anatomy 0.000 claims 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 12
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- 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 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 10
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 10
- 210000002901 mesenchymal stem cell Anatomy 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 8
- 239000000919 ceramic Substances 0.000 claims 7
- 125000001153 fluoro group Chemical group F* 0.000 claims 7
- 230000002138 osteoinductive effect Effects 0.000 claims 7
- 229910000391 tricalcium phosphate Inorganic materials 0.000 claims 7
- 235000019731 tricalcium phosphate Nutrition 0.000 claims 7
- 229940078499 tricalcium phosphate Drugs 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000004404 heteroalkyl group Chemical group 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- SKYXZSVBBFFJQQ-UHFFFAOYSA-N 1-methyl-2h-pyrazine Chemical group CN1CC=NC=C1 SKYXZSVBBFFJQQ-UHFFFAOYSA-N 0.000 claims 5
- OIZYJWFQAQGBRX-UHFFFAOYSA-N 1-propyl-2h-pyrazine Chemical group CCCN1CC=NC=C1 OIZYJWFQAQGBRX-UHFFFAOYSA-N 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 210000000988 bone and bone Anatomy 0.000 claims 5
- 210000002449 bone cell Anatomy 0.000 claims 5
- 210000001185 bone marrow Anatomy 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 5
- MBTRIEAIKAONJJ-UHFFFAOYSA-N 1-ethyl-2h-pyrazine Chemical group CCN1CC=NC=C1 MBTRIEAIKAONJJ-UHFFFAOYSA-N 0.000 claims 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 4
- 239000011575 calcium Substances 0.000 claims 4
- 229910052791 calcium Inorganic materials 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 239000000463 material Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- 239000011593 sulfur Chemical group 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 210000001519 tissue Anatomy 0.000 claims 3
- 125000004867 1,1-dimethylpropylcarbonyl group Chemical group CC(CC)(C(=O)*)C 0.000 claims 2
- 125000001766 1,2,4-oxadiazol-3-yl group Chemical group [H]C1=NC(*)=NO1 0.000 claims 2
- 125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 0.000 claims 2
- 125000004868 1,2-dimethylpropylcarbonyl group Chemical group CC(C(C)C)C(=O)* 0.000 claims 2
- 125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 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
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- 125000000782 4-ethoxyphenylcarbonyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])C([H])([H])[H])C(*)=O 0.000 claims 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 125000005018 aryl alkenyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000000254 aspartoyl group Chemical group 0.000 claims 2
- 125000006251 butylcarbonyl group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 claims 2
- 125000006637 cyclobutyl carbonyl group Chemical group 0.000 claims 2
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 claims 2
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 2
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000003978 glutamoyl group Chemical group [H]N([H])[C@]([H])(C(=O)[*])C([H])([H])C([H])([H])C(N([H])[H])=O 0.000 claims 2
- 125000006328 iso-butylcarbonyl group Chemical group [H]C([H])([H])C([H])(C(*)=O)C([H])([H])[H] 0.000 claims 2
- 239000007788 liquid Substances 0.000 claims 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000004675 pentylcarbonyl group Chemical group C(CCCC)C(=O)* 0.000 claims 2
- 125000005062 perfluorophenyl group Chemical group FC1=C(C(=C(C(=C1F)F)F)F)* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004673 propylcarbonyl group Chemical group 0.000 claims 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 210000000130 stem cell Anatomy 0.000 claims 2
- 125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- XXGPNEDZNRZWPK-QMMMGPOBSA-N (2s)-2-(carboxyamino)-3-phenylpropanoic acid Chemical compound OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 XXGPNEDZNRZWPK-QMMMGPOBSA-N 0.000 claims 1
- UUBCYMOEZWLGBD-WHFBIAKZSA-N (2s,3s)-2-(carboxyamino)-3-methylpentanoic acid Chemical compound CC[C@H](C)[C@@H](C(O)=O)NC(O)=O UUBCYMOEZWLGBD-WHFBIAKZSA-N 0.000 claims 1
- 125000001399 1,2,3-triazolyl group Chemical group N1N=NC(=C1)* 0.000 claims 1
- GMRQFYUYWCNGIN-ZVUFCXRFSA-N 1,25-dihydroxy vitamin D3 Chemical compound C1([C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@@H](CCCC(C)(C)O)C)=CC=C1C[C@@H](O)C[C@H](O)C1=C GMRQFYUYWCNGIN-ZVUFCXRFSA-N 0.000 claims 1
- FVTVMQPGKVHSEY-UHFFFAOYSA-N 1-AMINOCYCLOBUTANE CARBOXYLIC ACID Chemical compound OC(=O)C1(N)CCC1 FVTVMQPGKVHSEY-UHFFFAOYSA-N 0.000 claims 1
- PAJPWUMXBYXFCZ-UHFFFAOYSA-N 1-aminocyclopropanecarboxylic acid Chemical compound OC(=O)C1(N)CC1 PAJPWUMXBYXFCZ-UHFFFAOYSA-N 0.000 claims 1
- 125000005808 2,4,6-trimethoxyphenyl group Chemical group [H][#6]-1=[#6](-[#8]C([H])([H])[H])-[#6](-*)=[#6](-[#8]C([H])([H])[H])-[#6]([H])=[#6]-1-[#8]C([H])([H])[H] 0.000 claims 1
- FUOOLUPWFVMBKG-UHFFFAOYSA-N 2-Aminoisobutyric acid Chemical compound CC(C)(N)C(O)=O FUOOLUPWFVMBKG-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 102000002260 Alkaline Phosphatase Human genes 0.000 claims 1
- 108020004774 Alkaline Phosphatase Proteins 0.000 claims 1
- 108010007726 Bone Morphogenetic Proteins Proteins 0.000 claims 1
- 102000007350 Bone Morphogenetic Proteins Human genes 0.000 claims 1
- 102100024506 Bone morphogenetic protein 2 Human genes 0.000 claims 1
- 102000015775 Core Binding Factor Alpha 1 Subunit Human genes 0.000 claims 1
- 108010024682 Core Binding Factor Alpha 1 Subunit Proteins 0.000 claims 1
- 108050007372 Fibroblast Growth Factor Proteins 0.000 claims 1
- 102000018233 Fibroblast Growth Factor Human genes 0.000 claims 1
- 102000018997 Growth Hormone Human genes 0.000 claims 1
- 108010051696 Growth Hormone Proteins 0.000 claims 1
- 101000762366 Homo sapiens Bone morphogenetic protein 2 Proteins 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- MIJPAVRNWPDMOR-ZAFYKAAXSA-N L-ascorbic acid 2-phosphate Chemical compound OC[C@H](O)[C@H]1OC(=O)C(OP(O)(O)=O)=C1O MIJPAVRNWPDMOR-ZAFYKAAXSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- 102000010780 Platelet-Derived Growth Factor Human genes 0.000 claims 1
- 108010038512 Platelet-Derived Growth Factor Proteins 0.000 claims 1
- 108010049264 Teriparatide Proteins 0.000 claims 1
- 102000002689 Toll-like receptor Human genes 0.000 claims 1
- 108020000411 Toll-like receptor Proteins 0.000 claims 1
- 102000009618 Transforming Growth Factors Human genes 0.000 claims 1
- 108010009583 Transforming Growth Factors Proteins 0.000 claims 1
- 229930003316 Vitamin D Natural products 0.000 claims 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 claims 1
- 102000013814 Wnt Human genes 0.000 claims 1
- 108050003627 Wnt Proteins 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 1
- 210000004381 amniotic fluid Anatomy 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- DHCLVCXQIBBOPH-UHFFFAOYSA-N beta-glycerol phosphate Natural products OCC(CO)OP(O)(O)=O DHCLVCXQIBBOPH-UHFFFAOYSA-N 0.000 claims 1
- GHRQXJHBXKYCLZ-UHFFFAOYSA-L beta-glycerolphosphate Chemical compound [Na+].[Na+].CC(CO)OOP([O-])([O-])=O GHRQXJHBXKYCLZ-UHFFFAOYSA-L 0.000 claims 1
- 239000000227 bioadhesive Substances 0.000 claims 1
- 210000004369 blood Anatomy 0.000 claims 1
- 239000008280 blood Substances 0.000 claims 1
- 229940112869 bone morphogenetic protein Drugs 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 210000003321 cartilage cell Anatomy 0.000 claims 1
- 230000021164 cell adhesion Effects 0.000 claims 1
- 230000002338 cryopreservative effect Effects 0.000 claims 1
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 1
- 125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims 1
- 210000003074 dental pulp Anatomy 0.000 claims 1
- UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 claims 1
- 229960003957 dexamethasone Drugs 0.000 claims 1
- 210000001671 embryonic stem cell Anatomy 0.000 claims 1
- 210000004700 fetal blood Anatomy 0.000 claims 1
- 229940126864 fibroblast growth factor Drugs 0.000 claims 1
- 230000008014 freezing Effects 0.000 claims 1
- 238000007710 freezing Methods 0.000 claims 1
- 230000005714 functional activity Effects 0.000 claims 1
- 239000000122 growth hormone Substances 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000011534 incubation Methods 0.000 claims 1
- 125000001998 leucyl group Chemical group 0.000 claims 1
- 108020004999 messenger RNA Proteins 0.000 claims 1
- 210000003098 myoblast Anatomy 0.000 claims 1
- 230000011164 ossification Effects 0.000 claims 1
- 210000000963 osteoblast Anatomy 0.000 claims 1
- 230000000849 parathyroid Effects 0.000 claims 1
- 210000003668 pericyte Anatomy 0.000 claims 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 210000001778 pluripotent stem cell Anatomy 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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| WO2017003461A1 (en) * | 2015-06-30 | 2017-01-05 | University Of South Florida | Osteoconductive and osteoinductive implant for augmentation, stabilization, or defect reconstruction |
| JP6742575B2 (ja) * | 2015-07-02 | 2020-08-19 | 株式会社東洋新薬 | 関節機能改善組成物 |
| MX374683B (es) | 2015-11-03 | 2025-03-04 | Zoetis Services Llc | Compuestos polimericos sol-gel y sus usos. |
| KR102127852B1 (ko) * | 2016-06-13 | 2020-06-30 | 차이나 메디컬 유니버시티 | 커큐미노이드의 신규한 유도체 및 항암제로서 이의 용도 |
| CN108060121B (zh) * | 2016-11-07 | 2021-05-28 | 惠州市正多实业有限公司 | 小分子化合物组合及利用该小分子化合物组合诱导分化的细胞制备成骨细胞的方法 |
| EP3607046A4 (en) | 2017-04-07 | 2020-05-27 | Epibone, Inc. | SOWING AND CROP SYSTEM AND METHOD |
| EP3714909A1 (en) * | 2019-03-28 | 2020-09-30 | Industrie Biomediche Insubri S.A. | Improved bone implant matrix comprising proline-rich peptide and method of preparing the same |
| KR102482319B1 (ko) * | 2020-09-29 | 2022-12-29 | 주식회사 시지바이오 | 고탄성의 인산 칼슘계 주입형 골 이식재 조성물 및 이의 제조방법 |
| CN113599396B (zh) * | 2021-09-26 | 2024-02-02 | 遵义医科大学附属医院 | 天然化合物联合人间充质干细胞在制备治疗骨质疏松症药物中的应用 |
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| CN116425649B (zh) * | 2023-03-30 | 2024-09-17 | 八叶草生物科技(三明)有限公司 | 一种氨基酸-姜黄素衍生物及其制备方法和应用 |
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| US6462019B1 (en) * | 1998-07-10 | 2002-10-08 | Osteoscreen, Inc. | Inhibitors of proteasomal activity and production for stimulating bone growth |
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| US9387094B2 (en) * | 2000-07-19 | 2016-07-12 | Warsaw Orthopedic, Inc. | Osteoimplant and method of making same |
| EP1325914A4 (en) * | 2000-09-14 | 2004-11-17 | Kaken Pharma Co Ltd | TETRAHYDROQUINOLINE COMPOUNDS |
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| EP1758651A2 (en) | 2004-06-24 | 2007-03-07 | Galapagos N.V. | Lxr agonists to promote bone homeostasis |
| EP2199283A1 (en) * | 2007-09-27 | 2010-06-23 | Kowa Company, Ltd. | Prophylactic and/or therapeutic agent for anemia, comprising tetrahydroquinoline compound as active ingredient |
| CN104357381A (zh) * | 2008-10-31 | 2015-02-18 | 辛西斯有限责任公司 | 用于活化干细胞的方法和装置 |
| US20120040976A1 (en) * | 2008-12-11 | 2012-02-16 | Human Biomolecular Research Institute | Small molecule immunomodulators for alzheimer's disease |
| WO2010086040A1 (en) | 2009-01-29 | 2010-08-05 | Biomarin Iga, Ltd. | Pyrazolo-pyrimidines for treatment of duchenne muscular dystrophy |
| JP5572154B2 (ja) * | 2009-03-31 | 2014-08-13 | 興和株式会社 | テトラヒドロキノリン化合物を有効成分とする貧血の予防及び／又は治療剤 |
| DK3284818T3 (da) * | 2010-01-26 | 2022-06-20 | Celularity Inc | Behandling af knoglerelateret kræft ved hjælp af placenta stamceller |
| EP2678052B1 (en) * | 2011-02-24 | 2018-09-26 | Emory University | Jab1 blocking compositions for ossification and methods related thereto |
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2015
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2019
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