CA2561987A1 - Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type - Google Patents

Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type Download PDF

Info

Publication number: CA2561987A1
Authority: CA; Canada
Prior art keywords: formula; process according; compound; compounds; group
Prior art date: 2006-10-02
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.): Abandoned

Application number

CA 2561987

Other languages

English (en)

Inventor

Daqing Che

Bhaskar Reddy Guntoori

Sammy Chris Duncan

Laura Kaye Montemayor

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Apotex Pharmachem Inc

Original Assignee

Apotex Pharmachem Inc

Priority date (The priority date 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 date listed.)

2006-10-02

Filing date

2006-10-02

Publication date

2008-04-02

2006-10-02 Application filed by Apotex Pharmachem Inc filed Critical Apotex Pharmachem Inc

2006-10-02 Priority to CA 2561987 priority Critical patent/CA2561987A1/fr

2008-04-02 Publication of CA2561987A1 publication Critical patent/CA2561987A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 84
150000003839 salts Chemical class 0.000 title claims abstract description 39
238000002360 preparation method Methods 0.000 title claims description 8
XXSMGPRMXLTPCZ-UHFFFAOYSA-N hydroxychloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-UHFFFAOYSA-N 0.000 title description 31
229960004171 hydroxychloroquine Drugs 0.000 title description 28
150000001875 compounds Chemical class 0.000 claims abstract description 146
239000000203 mixture Substances 0.000 claims abstract description 29
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 26
239000002904 solvent Substances 0.000 claims abstract description 25
239000000376 reactant Substances 0.000 claims abstract description 23
229910000000 metal hydroxide Inorganic materials 0.000 claims abstract description 20
150000004692 metal hydroxides Chemical class 0.000 claims abstract description 20
229910052751 metal Inorganic materials 0.000 claims abstract description 18
239000002184 metal Substances 0.000 claims abstract description 18
239000002253 acid Substances 0.000 claims abstract description 16
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims abstract description 14
229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
230000007062 hydrolysis Effects 0.000 claims abstract description 12
238000006460 hydrolysis reaction Methods 0.000 claims abstract description 12
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 8
125000005843 halogen group Chemical group 0.000 claims abstract description 8
150000002367 halogens Chemical class 0.000 claims abstract description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 claims description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 14
239000003960 organic solvent Substances 0.000 claims description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 12
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 8
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
238000001914 filtration Methods 0.000 claims description 7
238000002955 isolation Methods 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
125000002015 acyclic group Chemical group 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 5
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
238000010626 work up procedure Methods 0.000 claims description 5
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
239000012346 acetyl chloride Substances 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
150000001263 acyl chlorides Chemical class 0.000 claims description 3
150000001266 acyl halides Chemical class 0.000 claims description 3
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims 4
150000001408 amides Chemical class 0.000 description 17
239000012535 impurity Substances 0.000 description 16
239000003795 chemical substances by application Substances 0.000 description 13
238000006243 chemical reaction Methods 0.000 description 11
XFICNUNWUREFDP-UHFFFAOYSA-N 2-[4-[(7-chloroquinolin-4-yl)amino]pentylamino]ethanol Chemical compound ClC1=CC=C2C(NC(CCCNCCO)C)=CC=NC2=C1 XFICNUNWUREFDP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
ZAVJTSLIGAGALR-UHFFFAOYSA-N 2-(2,2,2-trifluoroacetyl)cyclooctan-1-one Chemical compound FC(F)(F)C(=O)C1CCCCCCC1=O ZAVJTSLIGAGALR-UHFFFAOYSA-N 0.000 description 6
229940043265 methyl isobutyl ketone Drugs 0.000 description 6
239000002585 base Substances 0.000 description 5
239000012458 free base Substances 0.000 description 5
229960002927 hydroxychloroquine sulfate Drugs 0.000 description 5
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000000047 product Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
125000005910 alkyl carbonate group Chemical group 0.000 description 2
239000003430 antimalarial agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
150000004649 carbonic acid derivatives Chemical class 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000013341 scale-up Methods 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
JCBIVZZPXRZKTI-UHFFFAOYSA-N 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol;sulfuric acid Chemical compound OS(O)(=O)=O.ClC1=CC=C2C(NC(C)CCCN(CCO)CC)=CC=NC2=C1 JCBIVZZPXRZKTI-UHFFFAOYSA-N 0.000 description 1
XUVXSSOPXQRCGL-UHFFFAOYSA-N 2-[4-aminopentyl(ethyl)amino]ethanol Chemical compound OCCN(CC)CCCC(C)N XUVXSSOPXQRCGL-UHFFFAOYSA-N 0.000 description 1
XXSMGPRMXLTPCZ-AWEZNQCLSA-N 2-[[(4s)-4-[(7-chloroquinolin-4-yl)amino]pentyl]-ethylamino]ethanol Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CCO)CC)=CC=NC2=C1 XXSMGPRMXLTPCZ-AWEZNQCLSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 1
208000006926 Discoid Lupus Erythematosus Diseases 0.000 description 1
FXXACINHVKSMDR-UHFFFAOYSA-N acetyl bromide Chemical compound CC(Br)=O FXXACINHVKSMDR-UHFFFAOYSA-N 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
230000000078 anti-malarial effect Effects 0.000 description 1
230000003356 anti-rheumatic effect Effects 0.000 description 1
239000012296 anti-solvent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
LMEKQMALGUDUQG-UHFFFAOYSA-N azathioprine Chemical compound CN1C=NC([N+]([O-])=O)=C1SC1=NC=NC2=C1NC=N2 LMEKQMALGUDUQG-UHFFFAOYSA-N 0.000 description 1
229960002170 azathioprine Drugs 0.000 description 1
SVXPPSFKJQWISH-UHFFFAOYSA-N benzyl carbamoperoxoate Chemical compound NC(=O)OOCC1=CC=CC=C1 SVXPPSFKJQWISH-UHFFFAOYSA-N 0.000 description 1
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
208000004921 cutaneous lupus erythematosus Diseases 0.000 description 1
229960004397 cyclophosphamide Drugs 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-N diphosphoric acid Chemical class OP(O)(=O)OP(O)(O)=O XPPKVPWEQAFLFU-UHFFFAOYSA-N 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-M ethanimidate Chemical compound CC([O-])=N DLFVBJFMPXGRIB-UHFFFAOYSA-M 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000004537 pulping Methods 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
201000000596 systemic lupus erythematosus Diseases 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
- C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 2561987 2006-10-02 2006-10-02 Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type Abandoned CA2561987A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2561987 CA2561987A1 (fr)	2006-10-02	2006-10-02	Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2561987 CA2561987A1 (fr)	2006-10-02	2006-10-02	Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type

Publications (1)

Publication Number	Publication Date
CA2561987A1 true CA2561987A1 (fr)	2008-04-02

Family

ID=39264261

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2561987 Abandoned CA2561987A1 (fr)	2006-10-02	2006-10-02	Methode de preparation d'hydroxychloroquine de tres haute purete ou d'un sel du meme type

Country Status (1)

Country	Link
CA (1)	CA2561987A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN102050781A (zh) *	2010-12-21	2011-05-11	重庆康乐制药有限公司	一种硫酸羟氯喹的工业化制备方法
KR101115412B1 (ko) *	2008-09-08	2012-06-12	주식회사 대희화학	하이드록시클로로퀸의 신규 제조방법
CN102718707A (zh) *	2012-06-27	2012-10-10	武汉武药科技有限公司	羟基氯喹衍生物及其制备方法
CN103724261A (zh) *	2013-12-13	2014-04-16	武汉武药制药有限公司	一种硫酸羟基氯喹啉的工业化新方法
CN104230803A (zh) *	2014-08-28	2014-12-24	重庆康乐制药有限公司	一种硫酸羟氯喹的制备方法
CN108658858A (zh) *	2017-06-27	2018-10-16	上海中西三维药业有限公司	一种羟氯喹的制备和精制方法及其硫酸盐的制备方法
CN108727263A (zh) *	2018-07-05	2018-11-02	上海中西三维药业有限公司	硫酸羟氯喹晶型a及其制备方法
CN109456266A (zh) *	2018-11-12	2019-03-12	南京天际联盟医药科技有限公司	硫酸羟氯喹的制备新方法
CN110790705A (zh) *	2018-08-01	2020-02-14	华东理工大学	羟基氯喹衍生物及其制备方法、应用
CN111635358A (zh) *	2020-06-29	2020-09-08	北京成宇化工有限公司	一种羟氯喹的制备方法
CN111793026A (zh) *	2020-07-23	2020-10-20	珠海润都制药股份有限公司	一种硫酸羟氯喹及其对映体的晶型和制备方法
CN113149904A (zh) *	2021-03-02	2021-07-23	南京海纳医药科技股份有限公司	一种羟氯喹粗品的精制方法
CN114920694A (zh) *	2022-07-18	2022-08-19	康瑞鑫(天津)药物研究院有限公司	羟氯喹粗品的精制方法及制备的羟氯喹产品
WO2024261606A1 (fr)	2023-06-22	2024-12-26	Tübi̇tak	Procédé de production d'hydroxychloroquine dans des conditions concentrées

2006
- 2006-10-02 CA CA 2561987 patent/CA2561987A1/fr not_active Abandoned

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR101115412B1 (ko) *	2008-09-08	2012-06-12	주식회사 대희화학	하이드록시클로로퀸의 신규 제조방법
CN102050781A (zh) *	2010-12-21	2011-05-11	重庆康乐制药有限公司	一种硫酸羟氯喹的工业化制备方法
CN102718707A (zh) *	2012-06-27	2012-10-10	武汉武药科技有限公司	羟基氯喹衍生物及其制备方法
CN103724261A (zh) *	2013-12-13	2014-04-16	武汉武药制药有限公司	一种硫酸羟基氯喹啉的工业化新方法
CN103724261B (zh) *	2013-12-13	2016-05-25	武汉武药制药有限公司	一种硫酸羟基氯喹啉的工业化制备方法
CN104230803A (zh) *	2014-08-28	2014-12-24	重庆康乐制药有限公司	一种硫酸羟氯喹的制备方法
CN108658858B (zh) *	2017-06-27	2022-02-25	上海中西三维药业有限公司	一种羟氯喹的制备和精制方法及其硫酸盐的制备方法
CN108658858A (zh) *	2017-06-27	2018-10-16	上海中西三维药业有限公司	一种羟氯喹的制备和精制方法及其硫酸盐的制备方法
CN108727263A (zh) *	2018-07-05	2018-11-02	上海中西三维药业有限公司	硫酸羟氯喹晶型a及其制备方法
CN110790705A (zh) *	2018-08-01	2020-02-14	华东理工大学	羟基氯喹衍生物及其制备方法、应用
CN109456266A (zh) *	2018-11-12	2019-03-12	南京天际联盟医药科技有限公司	硫酸羟氯喹的制备新方法
CN111635358A (zh) *	2020-06-29	2020-09-08	北京成宇化工有限公司	一种羟氯喹的制备方法
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