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 |
|---|---|---|---|---|
| KR101462825B1 (ko) | 2004-05-03 | 2014-11-21 | 헤르메스 바이오사이언스, 인코포레이티드 | 약물 전달에 유용한 리포좀 |
| US20080027052A1 (en) * | 2006-07-10 | 2008-01-31 | Sharon Moe | Methods for treating cystic kidney disease |
| 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 |
| CA2719256A1 (en) * | 2008-03-28 | 2009-10-01 | Amgen Inc. | Methods of treating 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 |
| WO2012039768A2 (en) * | 2010-09-24 | 2012-03-29 | 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 |
| AU2012345777B2 (en) | 2011-11-30 | 2016-05-12 | Kindeva Drug Delivery L.P. | Microneedle device including a peptide therapeutic agent and an amino acid and methods of making and using the same |
| EP2858513B1 (en) * | 2012-06-07 | 2016-11-23 | Cargill, Incorporated | Pumpable fat compositions, use in feed and method for reducing their viscosity. |
| 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 |
| EA028569B1 (ru) * | 2012-10-24 | 2017-12-29 | Карджилл, Инкорпорейтед | Композиция эмульгатора, содержащего фосфолипиды |
| 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 |
| ES2939940T3 (es) | 2014-03-28 | 2023-04-28 | Univ Duke | Tratamiento del cáncer de mama utilizando moduladores selectivos de los receptores de estrógenos |
| CN106714787A (zh) * | 2014-09-25 | 2017-05-24 | 富士胶片株式会社 | 含丙泊酚的水包油型乳液组合物及其制造方法 |
| MX384605B (es) | 2015-04-29 | 2025-03-14 | Radius Pharmaceuticals Inc | Combinación de palbociclib y rad1901 para usarse en el tratamiento de cáncer de mama en un sujeto con cáncer positivo a receptor de estrógeno. |
| ES3036518T3 (en) | 2015-10-16 | 2025-09-19 | Ipsen Biopharm Ltd | Stabilizing camptothecin pharmaceutical compositions |
| 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 |
| EP3565542B1 (en) | 2017-01-05 | 2024-04-10 | Radius Pharmaceuticals, Inc. | Polymorphic forms of rad1901-2hcl |
| 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 |
| SG11202013177WA (en) | 2018-07-04 | 2021-01-28 | 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 |
| AU2019370565A1 (en) * | 2018-11-02 | 2021-06-24 | Ampersand Biopharmaceuticals, Inc. | Management of risk of cation overload and electrolyte imbalance with topically applied buffers |
| US12441745B2 (en) | 2019-02-12 | 2025-10-14 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| 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 |
| AU702629B2 (en) | 1991-08-23 | 1999-02-25 | Nps Pharmaceuticals, Inc. | Calcium receptor-active arylalkyl amines |
| US6011068A (en) * | 1991-08-23 | 2000-01-04 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US6313146B1 (en) * | 1991-08-23 | 2001-11-06 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| DE69233586T2 (de) | 1991-08-23 | 2006-09-28 | NPS Pharmaceuticals, Inc., Salt Lake City | Kalzium-Rezeptor aktive Verbindungen |
| 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 |
| US5858684A (en) * | 1991-08-23 | 1999-01-12 | The Brigham And Women's Hospital, Inc. | Method of screening calcium receptor-active molecules |
| US6031003A (en) * | 1991-08-23 | 2000-02-29 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| US5688938A (en) * | 1991-08-23 | 1997-11-18 | The Brigham & Women's Hospital, Inc. | Calcium receptor-active molecules |
| US5962314A (en) * | 1993-02-23 | 1999-10-05 | Nps Pharmaceuticals, Inc. | Calcium receptor-active molecules |
| AU3777093A (en) | 1993-02-23 | 1994-09-14 | Brigham And Women's Hospital | Calcium receptor-active molecules |
| EP1275635A1 (en) * | 1994-10-21 | 2003-01-15 | Nps Pharmaceuticals, Inc. | Calcium receptor-active compounds |
| JP4117506B2 (ja) * | 1996-05-01 | 2008-07-16 | エヌピーエス ファーマシューティカルズ インコーポレイテッド | 無機イオン活性化合物 |
| EP1258471B1 (en) | 1996-05-01 | 2007-01-24 | Nps Pharmaceuticals, Inc. | Inorganic ion receptor-active compounds |
| WO1998001417A1 (en) * | 1996-07-08 | 1998-01-15 | Kirin Beer Kabushiki Kaisha | Calcium receptor-active compounds |
| TW483881B (en) * | 1996-12-03 | 2002-04-21 | Nps Pharma Inc | Calcilytic compounds |
| US6045824A (en) | 1997-09-18 | 2000-04-04 | Skyepharma Inc. | Sustained-release liposomal anesthetic compositions |
| US6146659A (en) * | 1998-07-01 | 2000-11-14 | Neopharm, Inc. | Method of administering liposomal encapsulated taxane |
| CN1221249C (zh) * | 1998-08-19 | 2005-10-05 | 斯凯伊药品加拿大公司 | 普鲁泊福的可注射水分散体 |
| 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 |
| WO2001097779A2 (en) * | 2000-06-16 | 2001-12-27 | Rtp Pharma Inc. | 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 |
| US6916956B2 (en) * | 2000-08-11 | 2005-07-12 | Japan Tobacco, Inc. | Calcium receptor antagonist |
| 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 |
| US7176322B2 (en) | 2002-05-23 | 2007-02-13 | Amgen Inc. | Calcium receptor modulating agents |
| US6908935B2 (en) * | 2002-05-23 | 2005-06-21 | Amgen Inc. | Calcium receptor modulating agents |
| PL382706A1 (pl) | 2002-08-26 | 2007-11-26 | Takeda Pharmaceutical Company Limited | Związek modulujący receptor wapnia i jego zastosowanie |
| US20050101576A1 (en) * | 2003-11-06 | 2005-05-12 | Novacea, Inc. | Methods of using vitamin D compounds in the treatment of myelodysplastic syndromes |
| JPWO2004052354A1 (ja) * | 2002-12-06 | 2006-04-06 | 株式会社大塚製薬工場 | プロポフォール含有脂肪乳剤 |
| PE20050460A1 (es) | 2003-04-23 | 2005-07-08 | Japan Tobacco Inc | COMPUESTOS HETEROCICLICOS COMO ANTAGONISTAS CaSR (RECEPTOR SENSIBLE AL CALCIO) |
| 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 |
| CA2527203C (en) * | 2003-05-28 | 2010-08-17 | Japan Tobacco Inc. | Casr antagonist |
| PL1648413T3 (pl) * | 2003-07-23 | 2010-03-31 | Theravance Inc | Kompozycje farmaceutyczne zawierające jako składnik czynny krótko działający środek uspokajający i usypiający |
| CA2601669A1 (en) * | 2005-03-17 | 2006-09-28 | 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. |
| EP1882684B1 (en) | 2005-05-19 | 2014-12-10 | Astellas Pharma Inc. | Pyrrolidine derivative or salt thereof |
| CA2620469C (en) | 2005-09-02 | 2014-04-01 | Amgen Inc. | Methods of modulating intestinal fluid balance |
| WO2008075173A2 (en) | 2006-12-15 | 2008-06-26 | Ruprecht-Karls-Universität Heidelberg | Methods for treating podocyte-related disorders |
-
2007
- 2007-04-20 WO PCT/US2007/067155 patent/WO2007124465A2/en not_active Ceased
- 2007-04-20 MX MX2008013339A patent/MX2008013339A/es active IP Right Grant
- 2007-04-20 BR BRPI0710814-1A patent/BRPI0710814A2/pt not_active IP Right Cessation
- 2007-04-20 JP JP2009506810A patent/JP5199239B2/ja active Active
- 2007-04-20 EA EA200802166A patent/EA200802166A1/ru unknown
- 2007-04-20 AU AU2007240317A patent/AU2007240317B2/en active Active
- 2007-04-20 CN CNA2007800140077A patent/CN101437490A/zh active Pending
- 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 US US11/738,444 patent/US8779004B2/en active Active
- 2007-04-20 CA CA2648939A patent/CA2648939C/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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