TW200819446A - Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor - Google Patents
Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor Download PDFInfo
- Publication number
- TW200819446A TW200819446A TW096130026A TW96130026A TW200819446A TW 200819446 A TW200819446 A TW 200819446A TW 096130026 A TW096130026 A TW 096130026A TW 96130026 A TW96130026 A TW 96130026A TW 200819446 A TW200819446 A TW 200819446A
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- formula
- salt
- crystalline
- salt form
- Prior art date
Links
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims description 15
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 title claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title abstract description 12
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 title abstract description 9
- 150000003891 oxalate salts Chemical class 0.000 title abstract description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 238000000034 method Methods 0.000 claims abstract description 57
- 150000003839 salts Chemical group 0.000 claims description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 33
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 27
- HAFWELDDNUXLCK-ODZAUARKSA-N (z)-but-2-enedioic acid;hydrate Chemical group O.OC(=O)\C=C/C(O)=O HAFWELDDNUXLCK-ODZAUARKSA-N 0.000 claims description 21
- 239000000725 suspension Substances 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- -1 dibutyl methyl Chemical group 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 17
- 239000013078 crystal Substances 0.000 claims description 16
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical group OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- 239000002002 slurry Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 9
- 206010036790 Productive cough Diseases 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 8
- 239000012458 free base Substances 0.000 claims description 8
- 210000003802 sputum Anatomy 0.000 claims description 8
- 208000024794 sputum Diseases 0.000 claims description 8
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 claims description 7
- 239000002689 soil Substances 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 6
- 238000012360 testing method Methods 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 5
- 238000001556 precipitation Methods 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- 241000283690 Bos taurus Species 0.000 claims description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000000706 filtrate Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 2
- FDYKGJFSAUBIOO-UHFFFAOYSA-N 1h-indene-1-sulfonic acid Chemical group C1=CC=C2C(S(=O)(=O)O)C=CC2=C1 FDYKGJFSAUBIOO-UHFFFAOYSA-N 0.000 claims 1
- 241001237745 Salamis Species 0.000 claims 1
- 235000019764 Soybean Meal Nutrition 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 1
- 230000000887 hydrating effect Effects 0.000 claims 1
- 238000004898 kneading Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 235000015175 salami Nutrition 0.000 claims 1
- 239000007790 solid phase Substances 0.000 claims 1
- 239000004455 soybean meal Substances 0.000 claims 1
- 241000894007 species Species 0.000 claims 1
- PVEFEIWVJKUCLJ-UHFFFAOYSA-N sulfuric acid;toluene Chemical group OS(O)(=O)=O.CC1=CC=CC=C1 PVEFEIWVJKUCLJ-UHFFFAOYSA-N 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 239000000523 sample Substances 0.000 description 44
- 238000001228 spectrum Methods 0.000 description 32
- 238000000113 differential scanning calorimetry Methods 0.000 description 22
- 238000002411 thermogravimetry Methods 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 17
- 230000004580 weight loss Effects 0.000 description 17
- 239000003814 drug Substances 0.000 description 10
- 150000004682 monohydrates Chemical class 0.000 description 10
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 238000004611 spectroscopical analysis Methods 0.000 description 9
- 238000009792 diffusion process Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 7
- 238000002076 thermal analysis method Methods 0.000 description 7
- 238000001757 thermogravimetry curve Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229940079593 drug Drugs 0.000 description 6
- 239000012453 solvate Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000012512 characterization method Methods 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000000197 pyrolysis Methods 0.000 description 4
- 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 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 238000005102 attenuated total reflection Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000003828 vacuum filtration Methods 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- 241000283899 Gazella Species 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- MVIOINXPSFUJEN-UHFFFAOYSA-N benzenesulfonic acid;hydrate Chemical group O.OS(=O)(=O)C1=CC=CC=C1 MVIOINXPSFUJEN-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000007405 data analysis Methods 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000001530 fumaric acid Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- LPNBBFKOUUSUDB-UHFFFAOYSA-N p-toluic acid Chemical compound CC1=CC=C(C(O)=O)C=C1 LPNBBFKOUUSUDB-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 238000007670 refining Methods 0.000 description 2
- 238000002834 transmittance Methods 0.000 description 2
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical compound C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 description 1
- OJMIBMNMMDPSGJ-UHFFFAOYSA-N 2-propan-2-ylbenzene-1,3-dicarboxylic acid Chemical compound CC(C)C1=C(C(O)=O)C=CC=C1C(O)=O OJMIBMNMMDPSGJ-UHFFFAOYSA-N 0.000 description 1
- 235000017166 Bambusa arundinacea Nutrition 0.000 description 1
- 235000017491 Bambusa tulda Nutrition 0.000 description 1
- 241001330002 Bambuseae Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 1
- 101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 description 1
- 206010008531 Chills Diseases 0.000 description 1
- 229920002101 Chitin Polymers 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 235000015334 Phyllostachys viridis Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- NQHAZTDQFIYTQD-UHFFFAOYSA-N SOS Chemical compound SOS NQHAZTDQFIYTQD-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- ONJMCYREMREKSA-UHFFFAOYSA-N [Cu].[Ge] Chemical compound [Cu].[Ge] ONJMCYREMREKSA-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 238000004164 analytical calibration Methods 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000011425 bamboo Substances 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- ZTHQBROSBNNGPU-UHFFFAOYSA-M butyl sulfate(1-) Chemical compound CCCCOS([O-])(=O)=O ZTHQBROSBNNGPU-UHFFFAOYSA-M 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 238000007707 calorimetry Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011094 fiberboard Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010977 jade Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical group O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 239000013074 reference sample Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000000646 scanning calorimetry Methods 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000002730 succinyl group Chemical group C(CCC(=O)*)(=O)* 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000008054 sulfonate salts Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- IYCATMXBHYXYSN-UHFFFAOYSA-N sulfuric acid;toluene;hydrate Chemical group O.OS(O)(=O)=O.CC1=CC=CC=C1 IYCATMXBHYXYSN-UHFFFAOYSA-N 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical group O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/16—Central respiratory analeptics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83766106P | 2006-08-14 | 2006-08-14 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200819446A true TW200819446A (en) | 2008-05-01 |
Family
ID=38895795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096130026A TW200819446A (en) | 2006-08-14 | 2007-08-14 | Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US7956189B2 (enExample) |
| EP (1) | EP2069337A1 (enExample) |
| JP (3) | JP2010500406A (enExample) |
| CN (1) | CN101522671A (enExample) |
| AR (1) | AR062373A1 (enExample) |
| CA (1) | CA2660703A1 (enExample) |
| CL (1) | CL2007002366A1 (enExample) |
| MX (1) | MX2009001770A (enExample) |
| PE (1) | PE20080424A1 (enExample) |
| TW (1) | TW200819446A (enExample) |
| WO (1) | WO2008021271A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2419610C2 (ru) | 2005-05-26 | 2011-05-27 | Ньюрон Системз, Инк. | Композиции и способы лечения заболевания сетчатки |
| WO2011072141A1 (en) | 2009-12-11 | 2011-06-16 | Neuron Systems, Inc. | Compositions and methods for the treatment of macular degeneration |
| WO2014012859A1 (en) * | 2012-07-19 | 2014-01-23 | Boehringer Ingelheim International Gmbh | Fumaric acid salt of 9-[4-(3-chloro-2-fluoro-phenylamino)-7-methoxy- chinazolin-6-yloxy]-1,4-diaza-spiro[5.5]undecan-5-one, its use as medicament and the preparation thereof |
| US9687481B2 (en) | 2013-01-23 | 2017-06-27 | Aldeyra Therapeutics, Inc. | Toxic aldehyde related diseases and treatment |
| EP4400106A1 (en) | 2015-08-21 | 2024-07-17 | Aldeyra Therapeutics, Inc. | Deuterated compounds and uses thereof |
| US11040039B2 (en) | 2017-10-10 | 2021-06-22 | Aldeyra Therapeutics, Inc. | Treatment of inflammatory disorders |
| US12006298B2 (en) | 2018-08-06 | 2024-06-11 | Aldeyra Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| US12098132B2 (en) | 2019-05-02 | 2024-09-24 | Aldeyra Therapeutics, Inc. | Process for preparation of aldehyde scavenger and intermediates |
| CN113784954A (zh) | 2019-05-02 | 2021-12-10 | 奥尔德拉医疗公司 | 多晶型化合物和其用途 |
| WO2021231792A1 (en) | 2020-05-13 | 2021-11-18 | Aldeyra Therapeutics, Inc. | Pharmaceutical formulations and uses thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100907354B1 (ko) | 2004-05-18 | 2009-07-10 | 쉐링 코포레이션 | Ｐｄｅ4 억제제로서 유용한 치환된 2-퀴놀릴-옥사졸 |
-
2007
- 2007-08-10 EP EP07811264A patent/EP2069337A1/en not_active Withdrawn
- 2007-08-10 MX MX2009001770A patent/MX2009001770A/es active IP Right Grant
- 2007-08-10 WO PCT/US2007/017848 patent/WO2008021271A1/en not_active Ceased
- 2007-08-10 JP JP2009524638A patent/JP2010500406A/ja not_active Withdrawn
- 2007-08-10 CN CNA2007800382818A patent/CN101522671A/zh active Pending
- 2007-08-10 US US11/891,351 patent/US7956189B2/en not_active Expired - Fee Related
- 2007-08-10 CA CA002660703A patent/CA2660703A1/en not_active Abandoned
- 2007-08-14 TW TW096130026A patent/TW200819446A/zh unknown
- 2007-08-14 PE PE2007001088A patent/PE20080424A1/es not_active Application Discontinuation
- 2007-08-14 CL CL200702366A patent/CL2007002366A1/es unknown
- 2007-08-14 AR ARP070103601A patent/AR062373A1/es not_active Application Discontinuation
-
2012
- 2012-06-19 JP JP2012137788A patent/JP2012176989A/ja not_active Withdrawn
- 2012-11-09 JP JP2012247215A patent/JP2013032394A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010500406A (ja) | 2010-01-07 |
| EP2069337A1 (en) | 2009-06-17 |
| JP2013032394A (ja) | 2013-02-14 |
| PE20080424A1 (es) | 2008-04-28 |
| US7956189B2 (en) | 2011-06-07 |
| MX2009001770A (es) | 2009-02-25 |
| CN101522671A (zh) | 2009-09-02 |
| AR062373A1 (es) | 2008-11-05 |
| CA2660703A1 (en) | 2008-02-21 |
| CL2007002366A1 (es) | 2008-03-14 |
| WO2008021271A1 (en) | 2008-02-21 |
| JP2012176989A (ja) | 2012-09-13 |
| US20080108818A1 (en) | 2008-05-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TW200819446A (en) | Maleate, tosylate, fumarate, and oxalate salts of 5-(1(s)-amino-2-hydroxyethyl)-n-[(2,4-difluorophenyl)-methyl]-2-[8-methoxy-2-(trifluoromethyl)-5-quinoline]-4-oxazolecarboxamide and preparation process therefor | |
| AU2023202085B2 (en) | Polymorphic forms of RAD1901-2HCL | |
| CN105143194B (zh) | 依洛昔巴特的结晶修饰物 | |
| TWI379681B (en) | Polymorphs of eltrombopag and eltrombopag salts and processes for preparation thereof | |
| US9610278B2 (en) | Glycopyrrolate salts | |
| CN107873029B (zh) | 依鲁替尼与羧酸的共晶体 | |
| TW202019914A (zh) | ２-（３，５-二氯-４-（（５-異丙基-６-側氧基-１，６-二氫噠嗪-３-基）氧）苯基）-３，５-二側氧基-２，３，４，５-四氫-１，２，４-三嗪-６-腈之固體型式 | |
| US11291651B2 (en) | Glycopyrrolate salts | |
| BR122018014454B1 (pt) | forma cristalina sólida a do cloridrato de (-)-(1r,2r)-3-(3-dimetilamino-1-etil-2-metilpropil)-fenol | |
| JP6691218B2 (ja) | 選択的なｓ１ｐ１受容体アゴニストの新規な結晶形及びその製造方法 | |
| WO2014082354A1 (zh) | 西达本胺的晶型及其制备方法与应用 | |
| JP2013533298A (ja) | ４−［−２−［［５−メチル−１−（２−ナフタレニル）−１ｈ−ピラゾール−３−イル］オキシ］エチル］モルホリン塩酸塩の固体形態 | |
| JP6816036B2 (ja) | ヒストン脱アセチル化阻害剤の結晶形態 | |
| TW202434233A (zh) | 化合物a的鹽和晶型、其製備方法和用途 | |
| JP2019518058A (ja) | スピロ−オキシインドール化合物の固体状態形 | |
| EA036295B1 (ru) | Твердые формы замещенных 5,6-дигидро-6-фенилбензо[f]изохинолин-2-аминовых соединений | |
| JP7152122B2 (ja) | エダラボン塩 | |
| TW201143761A (en) | Tablet formulation of ezatiostat | |
| TW202033508A (zh) | 貝前列素-314d晶體及其製備方法 | |
| TW201018660A (en) | Chemical process | |
| CN113149998B (zh) | 2-吲哚啉螺环酮类化合物或其盐、溶剂合物的无定形形式或结晶形式 | |
| JP2025510061A (ja) | 縮合三環式誘導体又はその薬学的に許容される塩の結晶 | |
| CN115246830A (zh) | 一种酸的固体形式及其制备方法 | |
| TW202502340A (zh) | 菸酸酯類化合物的無定型物、多晶型物及其製備方法和用途 | |
| WO2025180349A1 (zh) | 化合物的固体及其制备方法和用途 |