CN116178275A - 氯比普兰氢溴酸盐晶型及其制备方法 - Google Patents
氯比普兰氢溴酸盐晶型及其制备方法 Download PDFInfo
- Publication number
- CN116178275A CN116178275A CN202111425148.6A CN202111425148A CN116178275A CN 116178275 A CN116178275 A CN 116178275A CN 202111425148 A CN202111425148 A CN 202111425148A CN 116178275 A CN116178275 A CN 116178275A
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- Prior art keywords
- chlorpyrifos
- hydrobromide
- crystalline form
- crystal form
- preparation
- 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.)
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- 239000005944 Chlorpyrifos Substances 0.000 title claims abstract description 62
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 title claims abstract description 57
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000013078 crystal Substances 0.000 title claims abstract description 32
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 238000000354 decomposition reaction Methods 0.000 claims description 5
- 239000002244 precipitate Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 20
- 150000003839 salts Chemical class 0.000 abstract description 17
- -1 solubility Chemical class 0.000 abstract description 10
- 229940079593 drug Drugs 0.000 abstract description 9
- 238000002474 experimental method Methods 0.000 abstract description 8
- 238000002844 melting Methods 0.000 abstract description 8
- 230000008018 melting Effects 0.000 abstract description 8
- 239000007787 solid Substances 0.000 abstract description 5
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 3
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 abstract description 3
- 230000008859 change Effects 0.000 abstract description 2
- 238000009509 drug development Methods 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 12
- 230000006872 improvement Effects 0.000 description 9
- 238000002050 diffraction method Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 238000012512 characterization method Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005352 clarification Methods 0.000 description 2
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 2
- 229960003608 clomifene Drugs 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- GDLIGKIOYRNHDA-UHFFFAOYSA-N Clomipramine Chemical compound C1CC2=CC=C(Cl)C=C2N(CCCN(C)C)C2=CC=CC=C21 GDLIGKIOYRNHDA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229960004606 clomipramine Drugs 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- OLZQTUCTGLHFTQ-UHFFFAOYSA-N octan-2-yl 2-(4-amino-3,5-dichloro-6-fluoropyridin-2-yl)oxyacetate Chemical group CCCCCCC(C)OC(=O)COC1=NC(F)=C(Cl)C(N)=C1Cl OLZQTUCTGLHFTQ-UHFFFAOYSA-N 0.000 description 1
- YGSFNCRAZOCNDJ-UHFFFAOYSA-N propan-2-one Chemical compound CC(C)=O.CC(C)=O YGSFNCRAZOCNDJ-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Description
对离子名称 | 分子量 |
氢溴酸 | 80.91 |
溶剂 | 溶解度(mg/mL) |
异丙醇 | 5~12.5 |
水 | <1 |
丙酮 | 25~50 |
2-Theta | d | Height | I% | Area | I% |
6.842 | 12.9089 | 192 | 11.9 | 1598 | 10 |
11.293 | 7.8288 | 58 | 3.6 | 119 | 0.7 |
13.562 | 6.5235 | 1607 | 100 | 15992 | 100 |
13.963 | 6.3371 | 211 | 13.1 | 2414 | 15.1 |
14.478 | 6.1127 | 177 | 11 | 1771 | 11.1 |
15.306 | 5.7841 | 464 | 28.9 | 9886 | 61.8 |
15.561 | 5.6898 | 757 | 47.1 | 12055 | 75.4 |
16.42 | 5.3941 | 177 | 11 | 2370 | 14.8 |
16.947 | 5.2274 | 93 | 5.8 | 2078 | 13 |
19.503 | 4.5479 | 130 | 8.1 | 1247 | 7.8 |
20.42 | 4.3455 | 594 | 37 | 8719 | 54.5 |
21.084 | 4.2103 | 63 | 3.9 | 269 | 1.7 |
22.021 | 4.0331 | 276 | 17.2 | 3472 | 21.7 |
24.101 | 3.6895 | 65 | 4 | 1048 | 6.6 |
24.944 | 3.5667 | 84 | 5.2 | 2132 | 13.3 |
25.285 | 3.5193 | 126 | 7.8 | 2783 | 17.4 |
27.261 | 3.2686 | 250 | 15.6 | 3988 | 24.9 |
27.764 | 3.2106 | 84 | 5.2 | 1836 | 11.5 |
29.006 | 3.0759 | 80 | 5 | 962 | 6 |
29.511 | 3.0244 | 70 | 4.4 | 972 | 6.1 |
Claims (10)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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CN202111425148.6A CN116178275A (zh) | 2021-11-27 | 2021-11-27 | 氯比普兰氢溴酸盐晶型及其制备方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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CN202111425148.6A CN116178275A (zh) | 2021-11-27 | 2021-11-27 | 氯比普兰氢溴酸盐晶型及其制备方法 |
Publications (1)
Publication Number | Publication Date |
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CN116178275A true CN116178275A (zh) | 2023-05-30 |
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Application Number | Title | Priority Date | Filing Date |
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CN202111425148.6A Pending CN116178275A (zh) | 2021-11-27 | 2021-11-27 | 氯比普兰氢溴酸盐晶型及其制备方法 |
Country Status (1)
Country | Link |
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CN (1) | CN116178275A (zh) |
-
2021
- 2021-11-27 CN CN202111425148.6A patent/CN116178275A/zh active Pending
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PB01 | Publication | ||
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Effective date of registration: 20240715 Address after: Room 1303-D, 3rd Floor, Self built Building 1, No. 96 Banhe Road, Huangpu District, Guangzhou City, Guangdong Province 510700 Applicant after: Lanshi Ming Pharmaceutical Technology (Guangzhou) Co.,Ltd. Country or region after: China Address before: 215127 unit B, plant 6, modern industrial building, No. 28, Xiasheng Road, Suzhou Industrial Park, Suzhou area, China (Jiangsu) pilot Free Trade Zone, Suzhou City, Jiangsu Province Applicant before: Lansheng Biomedicine (Suzhou) Co.,Ltd. Country or region before: China |
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