JP2009534425A5 - - Google Patents
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- Publication number
- JP2009534425A5 JP2009534425A5 JP2009506810A JP2009506810A JP2009534425A5 JP 2009534425 A5 JP2009534425 A5 JP 2009534425A5 JP 2009506810 A JP2009506810 A JP 2009506810A JP 2009506810 A JP2009506810 A JP 2009506810A JP 2009534425 A5 JP2009534425 A5 JP 2009534425A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- haloalkyl
- substituted
- compound
- independently
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 91
- 239000000203 mixture Substances 0.000 claims description 73
- 238000009472 formulation Methods 0.000 claims description 69
- 150000001875 compounds Chemical class 0.000 claims description 51
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 40
- 125000000623 heterocyclic group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- -1 nitro , Amino Chemical group 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 230000002092 calcimimetic effect Effects 0.000 claims description 27
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 26
- 150000002367 halogens Chemical class 0.000 claims description 26
- 229910052760 oxygen Inorganic materials 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000001188 haloalkyl group Chemical group 0.000 claims description 22
- 125000004429 atom Chemical group 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- 239000003381 stabilizer Substances 0.000 claims description 18
- 125000001624 naphthyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 14
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 13
- 239000011575 calcium Substances 0.000 claims description 13
- 229910052791 calcium Inorganic materials 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 13
- 239000012071 phase Substances 0.000 claims description 13
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 239000003921 oil Substances 0.000 claims description 12
- 239000000872 buffer Substances 0.000 claims description 11
- 239000003995 emulsifying agent Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 150000003904 phospholipids Chemical class 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000002950 monocyclic group Chemical group 0.000 claims description 9
- 210000000557 podocyte Anatomy 0.000 claims description 9
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 8
- 239000008346 aqueous phase Substances 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 239000008344 egg yolk phospholipid Substances 0.000 claims description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 7
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 claims description 6
- 201000002980 Hyperparathyroidism Diseases 0.000 claims description 6
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 6
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000000839 emulsion Substances 0.000 claims description 6
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 6
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 6
- 230000002209 hydrophobic effect Effects 0.000 claims description 6
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 claims description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 6
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 5
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 5
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005642 Oleic acid Substances 0.000 claims description 5
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 5
- 235000021313 oleic acid Nutrition 0.000 claims description 5
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 5
- 208000005475 Vascular calcification Diseases 0.000 claims description 4
- 229930003316 Vitamin D Natural products 0.000 claims description 4
- 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 description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 4
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims description 4
- 229940068998 egg yolk phospholipid Drugs 0.000 claims description 4
- 230000007794 irritation Effects 0.000 claims description 4
- 229960004488 linolenic acid Drugs 0.000 claims description 4
- 239000003589 local anesthetic agent Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229940083466 soybean lecithin Drugs 0.000 claims description 4
- 239000008347 soybean phospholipid Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 4
- 235000019166 vitamin D Nutrition 0.000 claims description 4
- 239000011710 vitamin D Substances 0.000 claims description 4
- 150000003710 vitamin D derivatives Chemical class 0.000 claims description 4
- 229940046008 vitamin d Drugs 0.000 claims description 4
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 3
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 claims description 3
- 235000021357 Behenic acid Nutrition 0.000 claims description 3
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- 235000021314 Palmitic acid Nutrition 0.000 claims description 3
- 235000021319 Palmitoleic acid Nutrition 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 3
- 235000021342 arachidonic acid Nutrition 0.000 claims description 3
- 229940114079 arachidonic acid Drugs 0.000 claims description 3
- 229940116226 behenic acid Drugs 0.000 claims description 3
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000001681 protective effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- JRFWKLXVTAAZAB-MRXNPFEDSA-N (1r)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-1-phenylethanamine Chemical compound C1([C@@H](C)NCC2=CC=C(C(=C2)C=2C=CC(=CC=2)C(F)(F)F)OC)=CC=CC=C1 JRFWKLXVTAAZAB-MRXNPFEDSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 2
- GSOMMFLMCBOYKC-UHFFFAOYSA-N 1-(3-chlorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC(Cl)=C1 GSOMMFLMCBOYKC-UHFFFAOYSA-N 0.000 claims description 2
- VWINXACDKLTYJX-UHFFFAOYSA-N 1-(3-fluorophenyl)-n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]ethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC(F)=C1 VWINXACDKLTYJX-UHFFFAOYSA-N 0.000 claims description 2
- CTDLKHPKIDQPAH-UHFFFAOYSA-N 2-[[1-[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]-1-phenylethyl]amino]ethanol Chemical compound COC1=CC=C(C(C)(NCCO)C=2C=CC=CC=2)C=C1C1=CC=C(C(F)(F)F)C=C1 CTDLKHPKIDQPAH-UHFFFAOYSA-N 0.000 claims description 2
- ZVQUCWXZCKWZBP-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-[1-(3-methoxyphenyl)ethyl]propan-1-amine Chemical compound COC1=CC=CC(C(C)NCCCC=2C(=CC=CC=2)Cl)=C1 ZVQUCWXZCKWZBP-UHFFFAOYSA-N 0.000 claims description 2
- 108010001237 Cytochrome P-450 CYP2D6 Proteins 0.000 claims description 2
- 102100021704 Cytochrome P450 2D6 Human genes 0.000 claims description 2
- 208000037147 Hypercalcaemia Diseases 0.000 claims description 2
- 206010020707 Hyperparathyroidism primary Diseases 0.000 claims description 2
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims description 2
- 201000000981 Primary Hyperparathyroidism Diseases 0.000 claims description 2
- 208000005770 Secondary Hyperparathyroidism Diseases 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 239000002535 acidifier Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 239000003429 antifungal agent Substances 0.000 claims description 2
- 229940121375 antifungal agent Drugs 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 230000003078 antioxidant effect Effects 0.000 claims description 2
- 210000000709 aorta Anatomy 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 229960005274 benzocaine Drugs 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 208000020832 chronic kidney disease Diseases 0.000 claims description 2
- VDHAWDNDOKGFTD-MRXNPFEDSA-N cinacalcet Chemical compound N([C@H](C)C=1C2=CC=CC=C2C=CC=1)CCCC1=CC=CC(C(F)(F)F)=C1 VDHAWDNDOKGFTD-MRXNPFEDSA-N 0.000 claims description 2
- 229960003315 cinacalcet Drugs 0.000 claims description 2
- 230000009918 complex formation Effects 0.000 claims description 2
- 210000004351 coronary vessel Anatomy 0.000 claims description 2
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003792 electrolyte Substances 0.000 claims description 2
- 239000003623 enhancer Substances 0.000 claims description 2
- 210000003709 heart valve Anatomy 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 230000000148 hypercalcaemia Effects 0.000 claims description 2
- 208000030915 hypercalcemia disease Diseases 0.000 claims description 2
- 238000001802 infusion Methods 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 238000002347 injection Methods 0.000 claims description 2
- 239000007924 injection Substances 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229960005015 local anesthetics Drugs 0.000 claims description 2
- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims description 2
- ZQLAZWPQJIPJAJ-UHFFFAOYSA-N n-[1-[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]ethyl]-1-phenylethanamine Chemical compound COC1=CC=C(C(C)NC(C)C=2C=CC=CC=2)C=C1C1=CC=C(C(F)(F)F)C=C1 ZQLAZWPQJIPJAJ-UHFFFAOYSA-N 0.000 claims description 2
- SLBPHKGSJJETHF-UHFFFAOYSA-N n-[2-chloro-5-[(1-phenylethylamino)methyl]phenyl]pyridine-2-carboxamide Chemical compound C=1C=CC=CC=1C(C)NCC(C=1)=CC=C(Cl)C=1NC(=O)C1=CC=CC=N1 SLBPHKGSJJETHF-UHFFFAOYSA-N 0.000 claims description 2
- KPKPTMKHISVLPY-UHFFFAOYSA-N n-[[1-ethyl-3-[3-(trifluoromethyl)phenyl]indol-5-yl]methyl]-1-phenylethanamine Chemical compound C12=CC(CNC(C)C=3C=CC=CC=3)=CC=C2N(CC)C=C1C1=CC=CC(C(F)(F)F)=C1 KPKPTMKHISVLPY-UHFFFAOYSA-N 0.000 claims description 2
- NKOAOWVEYKHEIX-UHFFFAOYSA-N n-[[4-chloro-3-(3-fluorophenyl)phenyl]methyl]-1-(3-chlorophenyl)ethanamine Chemical compound C=1C=CC(Cl)=CC=1C(C)NCC(C=1)=CC=C(Cl)C=1C1=CC=CC(F)=C1 NKOAOWVEYKHEIX-UHFFFAOYSA-N 0.000 claims description 2
- XZOGOAODTAIQCG-UHFFFAOYSA-N n-[[4-methoxy-3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]-1-naphthalen-1-ylethanamine Chemical compound COC1=CC=C(CNC(C)C=2C3=CC=CC=C3C=CC=2)C=C1C1=CC=C(OC(F)(F)F)C=C1 XZOGOAODTAIQCG-UHFFFAOYSA-N 0.000 claims description 2
- GGCMGVRNCAZBRK-UHFFFAOYSA-N n-[[4-methoxy-3-[4-(trifluoromethoxy)phenyl]phenyl]methyl]-1-phenylethanamine Chemical compound C1=C(C=2C=CC(OC(F)(F)F)=CC=2)C(OC)=CC=C1CNC(C)C1=CC=CC=C1 GGCMGVRNCAZBRK-UHFFFAOYSA-N 0.000 claims description 2
- JRFWKLXVTAAZAB-UHFFFAOYSA-N n-[[4-methoxy-3-[4-(trifluoromethyl)phenyl]phenyl]methyl]-1-phenylethanamine Chemical compound C1=C(C=2C=CC(=CC=2)C(F)(F)F)C(OC)=CC=C1CNC(C)C1=CC=CC=C1 JRFWKLXVTAAZAB-UHFFFAOYSA-N 0.000 claims description 2
- 239000007764 o/w emulsion Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 230000002335 preservative effect Effects 0.000 claims description 2
- 229960004919 procaine Drugs 0.000 claims description 2
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
- 239000008137 solubility enhancer Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000008181 tonicity modifier Substances 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 15
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 10
- 238000002360 preparation method Methods 0.000 claims 7
- 229910003827 NRaRb Inorganic materials 0.000 claims 6
- 101150100019 NRDC gene Proteins 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 2
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 1
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
- KBOSIRPMGVGOEP-UHFFFAOYSA-N 5-methyl-1,2-oxazole-3-carboxamide Chemical compound CC1=CC(C(N)=O)=NO1 KBOSIRPMGVGOEP-UHFFFAOYSA-N 0.000 claims 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 1
- 206010020850 Hyperthyroidism Diseases 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- 208000030761 polycystic kidney disease Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2928387A1 (en) | 2004-05-03 | 2005-11-17 | Merrimack Pharmaceuticals, Inc. | Drug delivery liposomes containing anionic polyols or anionic sugars |
| WO2008008650A1 (en) * | 2006-07-10 | 2008-01-17 | Indiana University Research And Technology Corporation | Methods for treating cystic kidney diseases |
| WO2008075173A2 (en) * | 2006-12-15 | 2008-06-26 | Ruprecht-Karls-Universität Heidelberg | Methods for treating podocyte-related disorders |
| CA2681582C (en) | 2007-03-30 | 2015-07-14 | Amgen Inc. | Methods of treating bowel disorders |
| US8609655B2 (en) * | 2008-03-28 | 2013-12-17 | Amgen Inc. | Calcimimetic compound for use in the treatment of epithelial injury |
| JP5468221B2 (ja) * | 2008-08-04 | 2014-04-09 | 株式会社 メドレックス | 難溶性薬物の静注用分散製剤 |
| WO2010042642A1 (en) * | 2008-10-08 | 2010-04-15 | Amgen Inc. | Calcium receptor modulating agents |
| US9012511B2 (en) * | 2010-05-19 | 2015-04-21 | Alkermes Pharma Ireland Limited | Nanoparticulate cinacalcet compositions |
| US9468638B2 (en) * | 2010-09-24 | 2016-10-18 | Texas Southern University | Itraconazole formulations |
| US8658676B2 (en) * | 2010-10-12 | 2014-02-25 | The Medicines Company | Clevidipine emulsion formulations containing antimicrobial agents |
| US20120213855A1 (en) * | 2011-02-17 | 2012-08-23 | Cima Labs Inc. | Dosage forms for weakly ionizable compounds |
| EP2785406A4 (en) | 2011-11-30 | 2015-10-21 | 3M Innovative Properties Co | MICRONADEL DEVICE WITH A PEPTIDE THERAPEUTIC AND AN AMINO ACID AND METHOD FOR THE PRODUCTION AND USE THEREOF |
| ES2611787T3 (es) * | 2012-06-07 | 2017-05-10 | Cargill, Incorporated | Composiciones de grasa bombeables, utilización en alimento para animales y método para reducir su viscosidad |
| US9212209B2 (en) * | 2012-07-13 | 2015-12-15 | Indiana University Research And Technology Corporation | Screening methods for spinal muscular atrophy |
| CN102895187B (zh) * | 2012-09-13 | 2015-05-06 | 西安力邦制药有限公司 | 注射用本芴醇脂肪乳的制备及其在疟疾治疗中的应用 |
| CA2888843C (en) * | 2012-10-24 | 2021-02-23 | Cargill, Incorporated | Phospholipid-containing emulsifier composition |
| KR101951933B1 (ko) | 2013-03-12 | 2019-02-25 | 주식회사 아리바이오 | 라이소포스파티딜콜린 또는 이의 유도체를 포함하는 지질나노물질 및 이의 제조방법 |
| CN103142477B (zh) * | 2013-04-08 | 2015-09-30 | 薛巍 | 一种缓释秋水仙碱的含纳米载体微乳制剂的制备方法 |
| FI3834824T3 (fi) | 2014-03-28 | 2025-12-05 | Univ Duke | Estrogeenireseptoripositiivisen rintasyövän hoito selektiivisellä estrogeenireseptorin modulaattorilla |
| EP3199150A4 (en) * | 2014-09-25 | 2017-08-09 | Fujifilm Corporation | Propofol-containing oil-in-water emulsion composition and method for producing same |
| JP7019422B2 (ja) | 2015-04-29 | 2022-02-15 | ラジウス ファーマシューティカルズ，インコーポレイテッド | 癌を治療するための方法 |
| MX382522B (es) | 2015-10-16 | 2025-03-13 | Ipsen Biopharm Ltd | Composiciones farmaceuticas estabilizantes de camptotecina. |
| KR101744203B1 (ko) * | 2016-01-12 | 2017-06-20 | (주)노터스생명과학 | 포스파티딜콜린을 유효성분으로 포함하는 신장질환 예방 또는 치료용 약학 조성물 |
| CN105769765A (zh) * | 2016-03-22 | 2016-07-20 | 辅必成（上海）医药科技有限公司 | 己酸羟孕酮脂肪乳注射液 |
| KR101898282B1 (ko) * | 2016-05-24 | 2018-09-13 | 주식회사 고려비엔피 | 항생제의 서방형 수의학적 조성물 및 이의 제조방법 |
| KR102707399B1 (ko) | 2017-01-05 | 2024-09-13 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
| CN109200024A (zh) * | 2017-07-07 | 2019-01-15 | 江苏恒瑞医药股份有限公司 | 西那卡塞药物组合物及其医药用途 |
| CN109953979A (zh) * | 2017-12-25 | 2019-07-02 | 江苏恒瑞医药股份有限公司 | 西那卡塞药物组合物及其医药用途 |
| IL279853B2 (en) | 2018-07-04 | 2025-01-01 | Radius Pharmaceuticals Inc | Polymorphic forms of RAD 1901-2HCL |
| KR102158824B1 (ko) * | 2018-09-27 | 2020-09-23 | 한국화학연구원 | 자가미세유화 약물전달시스템을 이용한 난용성 약물의 약학적 제제 |
| JP2022536222A (ja) * | 2018-11-02 | 2022-08-15 | アンパサンド バイオファーマシューティカルズ インコーポレイテッド | 局所的に施用される緩衝液によるカチオン過負荷および電解質平衡異常のリスクの管理 |
| CN113348163B (zh) | 2019-02-12 | 2024-10-08 | 雷迪厄斯制药公司 | 方法和化合物 |
| US11992483B2 (en) | 2021-03-31 | 2024-05-28 | Cali Biosciences Us, Llc | Emulsions for local anesthetics |
| CN115554261A (zh) * | 2021-07-02 | 2023-01-03 | 杭州中美华东制药有限公司 | 一种包含西那卡塞的组合物 |
Family Cites Families (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR511940A (fr) | 1916-12-08 | 1921-01-07 | Rene Emile Trottier | Dispositif pour la commande des appareils destinés au classement ou à la séparation des matières solides de tous genres |
| JPS60258110A (ja) * | 1984-06-05 | 1985-12-20 | Daigo Eiyou Kagaku Kk | 静脈注射可能なプロゲステロン乳化注射液 |
| US6001884A (en) | 1991-08-23 | 1999-12-14 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5763569A (en) | 1991-08-23 | 1998-06-09 | The Brigham And Women's Hospital, Inc | Calcium receptor-active molecules |
| US5688938A (en) | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6011068A (en) | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5858684A (en) | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| RU2147574C1 (ru) | 1991-08-23 | 2000-04-20 | Эн-Пи-Эс Фармасьютикалз, Инк. | Арилалкиламины, композиции, способы лечения и диагностики, способы идентификации соединения |
| CN1192011C (zh) | 1991-08-23 | 2005-03-09 | Nps药物有限公司 | 对钙受体具活性的芳烷基胺化合物 |
| US6031003A (en) | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5962314A (en) | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| EP0637237B1 (en) | 1993-02-23 | 2004-05-19 | Brigham And Women's Hospital, Inc. | Calcium receptor-active molecules |
| US6211244B1 (en) | 1994-10-21 | 2001-04-03 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| EP1258471B1 (en) | 1996-05-01 | 2007-01-24 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| EP0907631B1 (en) | 1996-05-01 | 2003-06-18 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| US6362231B1 (en) | 1996-07-08 | 2002-03-26 | Nps Pharmaceuticals, Inc. | Calcium receptor active compounds |
| TW483881B (en) | 1996-12-03 | 2002-04-21 | Nps Pharma Inc | Calcilytic compounds |
| EP2198854B1 (en) | 1997-09-18 | 2011-11-30 | Pacira Pharmaceuticals, Inc. | Sustained-release liposomal anesthetic compositions |
| US6146659A (en) * | 1998-07-01 | 2000-11-14 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
| ES2211151T3 (es) | 1998-08-19 | 2004-07-01 | Skyepharma Canada Inc. | Dispersiones acuosas inyectables de propofol. |
| AU760889B2 (en) | 1998-10-14 | 2003-05-22 | Ortho-Mcneil Pharmaceutical, Inc. | 1,2-disubstituted cyclopropanes |
| FR2800735B1 (fr) | 1999-11-09 | 2002-02-01 | Centre Nat Rech Scient | Nouvelles aralkyle-1,2-diamines possedant une activite calcimimetique et leur mode de preparation |
| FR2809396B1 (fr) | 2000-05-24 | 2005-10-14 | Centre Nat Rech Scient | Nouvelles molecules possedant une activite calcimimetique et leur mode de preparation |
| EP2036540A3 (en) | 2000-06-16 | 2009-12-16 | Jagotec AG | Improved injectable dispersions of propofol |
| FR2812875B1 (fr) | 2000-08-08 | 2003-12-12 | Centre Nat Rech Scient | Nouvelles diamines possedant une activite modulatrice des casr et leur mode de preparation |
| DE60136187D1 (de) | 2000-08-11 | 2008-11-27 | Japan Tobacco Inc | Calciumrezeptor-antagonisten |
| FR2820136A1 (fr) | 2001-01-26 | 2002-08-02 | Aventis Pharma Sa | Nouveaux derives de l'uree, leur procede de preparation, leur application a titre de medicaments, compositions pharmaceutiques et nouvelle utilisation |
| US6908935B2 (en) | 2002-05-23 | 2005-06-21 | Amgen Inc. | Calcium receptor modulating agents |
| US7176322B2 (en) * | 2002-05-23 | 2007-02-13 | Amgen Inc. | Calcium receptor modulating agents |
| KR101050700B1 (ko) | 2002-08-26 | 2011-07-20 | 다케다 야쿠힌 고교 가부시키가이샤 | 칼슘 수용체 조절 화합물 및 이의 용도 |
| US20050101576A1 (en) | 2003-11-06 | 2005-05-12 | Novacea, Inc. | Methods of using vitamin D compounds in the treatment of myelodysplastic syndromes |
| AU2003289163A1 (en) * | 2002-12-06 | 2004-06-30 | Otsuka Pharmaceutical Factory, Inc. | Propofol-containing fat emulsions |
| DK1619180T3 (da) | 2003-04-23 | 2010-03-29 | Japan Tobacco Inc | CaSR-antagonist |
| CN1225242C (zh) | 2003-05-21 | 2005-11-02 | 浙江天皇药业有限公司 | 一种抗肿瘤药物毛兰素脂肪乳剂及其制备方法 |
| WO2004106280A1 (ja) | 2003-05-28 | 2004-12-09 | Japan Tobacco Inc. | ＣａＳＲアンタゴニスト |
| DK1648413T3 (da) * | 2003-07-23 | 2010-01-11 | Theravance Inc | Farmaceutiske præparater af kortvirkende sedativt sövndyssende middel |
| US20060276534A1 (en) | 2005-03-17 | 2006-12-07 | Amgen Inc. | Methods of decreasing calcification |
| FR2885129B1 (fr) | 2005-04-29 | 2007-06-15 | Proskelia Sas | Nouveaux derives de l'ureee substituee parun thiazole ou benzothiazole, leur procede de preparation, leur application a titre de medicaments, les compositions pharmaceutiques les renfermant et utilisation. |
| WO2006123725A1 (ja) | 2005-05-19 | 2006-11-23 | Astellas Pharma Inc. | ピロリジン誘導体またはその塩 |
| ES2400693T3 (es) | 2005-09-02 | 2013-04-11 | Amgen Inc. | Regulación del equilibrio de fluido intestinal usando calcimiméticos |
| WO2008075173A2 (en) | 2006-12-15 | 2008-06-26 | Ruprecht-Karls-Universität Heidelberg | Methods for treating podocyte-related disorders |
-
2007
- 2007-04-20 CN CNA2007800140077A patent/CN101437490A/zh active Pending
- 2007-04-20 AU AU2007240317A patent/AU2007240317B2/en active Active
- 2007-04-20 BR BRPI0710814-1A patent/BRPI0710814A2/pt not_active IP Right Cessation
- 2007-04-20 EA EA200802166A patent/EA200802166A1/ru unknown
- 2007-04-20 MX MX2008013339A patent/MX2008013339A/es active IP Right Grant
- 2007-04-20 KR KR1020087027937A patent/KR20080110681A/ko not_active Withdrawn
- 2007-04-20 EP EP07761072A patent/EP2010150A2/en not_active Withdrawn
- 2007-04-20 CA CA2648939A patent/CA2648939C/en active Active
- 2007-04-20 WO PCT/US2007/067155 patent/WO2007124465A2/en not_active Ceased
- 2007-04-20 JP JP2009506810A patent/JP5199239B2/ja active Active
- 2007-04-20 US US11/738,444 patent/US8779004B2/en active Active
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2008
- 2008-10-14 ZA ZA200808773A patent/ZA200808773B/xx unknown
- 2008-10-17 NO NO20084368A patent/NO20084368L/no not_active Application Discontinuation
- 2008-10-21 CR CR10384A patent/CR10384A/es not_active Application Discontinuation
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