CN101019825A - 3,5-取代噁唑烷酮类化合物的溶解方法 - Google Patents
3,5-取代噁唑烷酮类化合物的溶解方法 Download PDFInfo
- Publication number
- CN101019825A CN101019825A CNA2007100883940A CN200710088394A CN101019825A CN 101019825 A CN101019825 A CN 101019825A CN A2007100883940 A CNA2007100883940 A CN A2007100883940A CN 200710088394 A CN200710088394 A CN 200710088394A CN 101019825 A CN101019825 A CN 101019825A
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- China
- Prior art keywords
- oxazolidinyl
- oxo
- phenyl
- fluoro
- acid
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 3
- -1 5-substituted oxazolidone Chemical class 0.000 claims abstract description 87
- 239000002253 acid Substances 0.000 claims abstract description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 108
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 31
- 230000004907 flux Effects 0.000 claims description 30
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 claims description 26
- ABCGRFHYOYXEJV-UHFFFAOYSA-N 4-methylisoindole-1,3-dione Chemical compound CC1=CC=CC2=C1C(=O)NC2=O ABCGRFHYOYXEJV-UHFFFAOYSA-N 0.000 claims description 26
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 26
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 25
- MBABOKRGFJTBAE-UHFFFAOYSA-N methyl methanesulfonate Chemical class COS(C)(=O)=O MBABOKRGFJTBAE-UHFFFAOYSA-N 0.000 claims description 23
- RKXFFOKVCXWANY-UHFFFAOYSA-N 1-ethyl-8,8-dimethyl-3-azabicyclo[3.2.1]octane-2,4-dione Chemical compound CCC12C(=O)NC(C(C1(C)C)CC2)=O RKXFFOKVCXWANY-UHFFFAOYSA-N 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- 235000011167 hydrochloric acid Nutrition 0.000 claims description 19
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 15
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 13
- 235000015165 citric acid Nutrition 0.000 claims description 12
- 238000010438 heat treatment Methods 0.000 claims description 9
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 235000011007 phosphoric acid Nutrition 0.000 claims description 7
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 claims description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 6
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 6
- 238000009835 boiling Methods 0.000 claims description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 claims description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- 235000011054 acetic acid Nutrition 0.000 claims description 5
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 5
- 239000001630 malic acid Substances 0.000 claims description 5
- 235000011090 malic acid Nutrition 0.000 claims description 5
- 235000006408 oxalic acid Nutrition 0.000 claims description 5
- 239000001117 sulphuric acid Substances 0.000 claims description 5
- 235000011149 sulphuric acid Nutrition 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 3
- ZBXNFTFKKOSPLD-UHFFFAOYSA-N 5-methylsulfanyl-2h-tetrazole Chemical compound CSC1=NN=NN1 ZBXNFTFKKOSPLD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- ZCHPKWUIAASXPV-UHFFFAOYSA-N acetic acid;methanol Chemical compound OC.CC(O)=O ZCHPKWUIAASXPV-UHFFFAOYSA-N 0.000 claims description 3
- 239000001361 adipic acid Substances 0.000 claims description 3
- 235000011037 adipic acid Nutrition 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000001530 fumaric acid Substances 0.000 claims description 3
- 229960004275 glycolic acid Drugs 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 claims description 3
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- ZHOQLKOZLOACPD-UHFFFAOYSA-N C[S].C1(=CC=CC=C1)O Chemical compound C[S].C1(=CC=CC=C1)O ZHOQLKOZLOACPD-UHFFFAOYSA-N 0.000 claims description 2
- MTJGVAJYTOXFJH-UHFFFAOYSA-N 3-aminonaphthalene-1,5-disulfonic acid Chemical compound C1=CC=C(S(O)(=O)=O)C2=CC(N)=CC(S(O)(=O)=O)=C21 MTJGVAJYTOXFJH-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 64
- 239000002904 solvent Substances 0.000 abstract description 13
- 238000001514 detection method Methods 0.000 abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 31
- 238000012360 testing method Methods 0.000 description 23
- 239000000523 sample Substances 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000004090 dissolution Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000003814 drug Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 125000000160 oxazolidinyl group Chemical group 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 241000192125 Firmicutes Species 0.000 description 4
- 108010059993 Vancomycin Proteins 0.000 description 4
- 238000005352 clarification Methods 0.000 description 4
- 229960003165 vancomycin Drugs 0.000 description 4
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 4
- MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- QQUNOUMTXXCEBH-UHFFFAOYSA-N O1[CH-]C(C=C1)=O Chemical class O1[CH-]C(C=C1)=O QQUNOUMTXXCEBH-UHFFFAOYSA-N 0.000 description 3
- 241000191940 Staphylococcus Species 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
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- 230000036457 multidrug resistance Effects 0.000 description 3
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229940127007 Compound 39 Drugs 0.000 description 2
- 241000194033 Enterococcus Species 0.000 description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 2
- 229930182555 Penicillin Natural products 0.000 description 2
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
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- 230000000694 effects Effects 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229960003194 meglumine Drugs 0.000 description 2
- 229940049954 penicillin Drugs 0.000 description 2
- 239000012488 sample solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical class NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
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- 208000008745 Healthcare-Associated Pneumonia Diseases 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 206010029803 Nosocomial infection Diseases 0.000 description 1
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- 241000191967 Staphylococcus aureus Species 0.000 description 1
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- 239000012445 acidic reagent Substances 0.000 description 1
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- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000005252 bulbus oculi Anatomy 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 239000006184 cosolvent Substances 0.000 description 1
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Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
Description
样品 | 溶解度(%) | ||||
10℃ | 20℃ | 40℃ | 70℃ | 80℃ | |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺; | 80 | 100 | 100 | 100 | 100 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲醇 | 90 | 95 | 100 | 100 | 100 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺; | 88 | 98 | 100 | 100 | 100 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 70 | 90 | 100 | 100 | 100 |
(S)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 85 | 100 | 100 | 100 | 100 |
样品 | 含量(%) | |||||
0小时 | 1小时 | 2小时 | 4小时 | 6小时 | 8小时 | |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺; | 99.1 | 99.0 | 99.3 | 98.9 | 99.2 | 99.0 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲醇 | 98.3 | 98.4 | 98.1 | 98.3 | 98.3 | 98.4 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺; | 97.2 | 97.0 | 97.3 | 97.1 | 97.2 | 97.0 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 98.5 | 98.4 | 98.5 | 98.6 | 98.5 | 98.6 |
(S)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 97.6 | 97.5 | 97.4 | 97.7 | 97.6 | 97.5 |
pH值 | 溶剂 | 温度(℃) | 时间(min) | 溶解率(%) |
1.5 | 盐酸 | 25 | 1 | 100 |
2.1 | 磷酸 | 25 | 2 | 100 |
2.8 | 丙二酸 | 25 | 2 | 100 |
3.1 | 柠檬酸 | 25 | 2 | 100 |
3.5 | 苹果酸 | 25 | 3 | 100 |
7.0 | 水 | 25 | 30 | 5 |
6.848 | 乙二胺 | 25 | 30 | 0 |
9.244 | 氨水 | 25 | 30 | 0 |
11.57 | 氢氧化钙 | 25 | 30 | 0 |
溶剂 | 温度(℃) | 时间(min) | 溶解率(%) | |
实施例3 | 盐酸 | 25 | 1 | 100 |
实施例4 | 磷酸 | 25 | 2 | 100 |
实施例5 | 丙二酸 | 25 | 2 | 100 |
实施例6 | 柠檬酸 | 25 | 2 | 100 |
实施例7 | 苹果酸 | 25 | 3 | 100 |
比较例1 | 乙醇 | 50 | 30 | 70 |
比较例2 | 丙酮 | 35 | 30 | 50 |
比较例3 | 甲醇 | 40 | 30 | 40 |
比较例4 | 异丙醇 | 50 | 30 | 60 |
样品名称 | 溶剂 | ||||
盐酸(%) | 磷酸(%) | 柠檬酸(%) | 丙酮(%) | 甲醇(%) | |
(S)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 30 | 20 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 35 | 22 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 33 | 30 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇对甲苯磺酸酯 | 100 | 100 | 100 | 25 | 19 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇乙酸酯 | 100 | 100 | 100 | 40 | 30 |
(S)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基咪唑 | 100 | 100 | 100 | 35 | 25 |
5-甲基-2-[(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基]巯基-1,3,4-噻二唑 | 100 | 100 | 100 | 31 | 20 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 34 | 25 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基-1H-四氮唑 | 100 | 100 | 100 | 15 | 30 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 45 | 22 |
1-甲基-5-[(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基巯基四氮唑 | 100 | 100 | 100 | 38 | 20 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 26 | 15 |
(S)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 33 | 20 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基硫酚 | 100 | 100 | 100 | 35 | 32 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 40 | 35 |
(R)-[N-3-(3′-氟-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基苯并三氮唑 | 100 | 100 | 100 | 38 | 28 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 35 | 30 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 40 | 28 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 30 | 40 |
(S)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 10 | 15 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 40 | 39 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 39 | 49 |
(R)-[N-3-(4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 25 | 34 |
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 39 | 43 |
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 20 | 25 |
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基-邻苯二酰亚胺 | 100 | 100 | 100 | 31 | 42 |
(S)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 28 | 35 |
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基 | 100 | 100 | 100 | 38 | 37 |
-1,2,4-1H-三氮唑 | |||||
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 25 | 28 |
(R)-[N-3-(3′-氯-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 35 | 22 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 42 | 40 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 25 | 34 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 30 | 15 |
(S)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 35 | 36 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 23 | 34 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 26 | 29 |
(R)-[N-3-(3′-三氟甲基-4′-吗啉基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 40 | 39 |
(R)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 35 | 42 |
(R)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基)苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 23 | 34 |
(R)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基)苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 38 | 32 |
(R)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基)苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 28 | 30 |
(R)-[N-3-(3′-氟-4′-(4″-苯基哌嗪基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 35 | 42 |
(R)-[N-3-(3′-氟-4′-(4″-(4-甲氧基)苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 33 | 30 |
(R)-[N-3-(3′-氟-4′-(4″-(4-甲氧基)苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 29 | 26 |
(R)-[N-3-(3′-氟-4′-(4″-(4-甲氧基)苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 28 | 24 |
(R)-[N-3-(3′-氟-4′-(4″-(4-甲氧基)苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 25 | 42 |
(R)-[N-3-(3′-氟-4′-(4″-(4-甲氧基)苯基哌嗪基))苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 23 | 40 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 35 | 28 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲醇甲磺酸酯 | 100 | 100 | 100 | 34 | 25 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基邻苯二酰亚胺 | 100 | 100 | 100 | 33 | 29 |
(S)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基乙酰胺 | 100 | 100 | 100 | 33 | 40 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 35 | 28 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 31 | 23 |
(R)-[N-3-(3′-氟-4′-(4″-苄基哌啶基))苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 35 | 26 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 36 | 38 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲醇 | 100 | 100 | 100 | 24 | 28 |
甲磺酸酯 | |||||
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基邻苯二甲酰亚胺 | 100 | 100 | 100 | 33 | 25 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基-1,2,4-1H-三氮唑 | 100 | 100 | 100 | 25 | 42 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基樟脑酰亚胺 | 100 | 100 | 100 | 23 | 30 |
(R)-[N-3-(3′-氟-4′-哌啶基)苯基-2-氧代-5-噁唑烷基]甲基丁二酰亚胺 | 100 | 100 | 100 | 33 | 22 |
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HK08100900.1A HK1111338A1 (en) | 2007-03-19 | 2008-01-24 | Process of dissolving 3,5 substituted oxazolidone |
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CN102256951A (zh) * | 2009-11-04 | 2011-11-23 | 四川贝力克生物技术有限责任公司 | 结晶水合物、药物组合物及其制备方法和用途 |
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CN102256951A (zh) * | 2009-11-04 | 2011-11-23 | 四川贝力克生物技术有限责任公司 | 结晶水合物、药物组合物及其制备方法和用途 |
JP2013510098A (ja) * | 2009-11-04 | 2013-03-21 | シセン ペイリコク バイオテクノロジー リミテッド ライアビリティ カンパニー | 特定の結晶性水和物、その医薬組成物、ならびにその調製方法および使用方法 |
CN102256951B (zh) * | 2009-11-04 | 2013-07-17 | 四川贝力克生物技术有限责任公司 | 结晶水合物、药物组合物及其用途 |
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