CZ2011767A3 - Zpusob prípravy a izolace solí vardenafilu s kyselinami - Google Patents
Zpusob prípravy a izolace solí vardenafilu s kyselinami Download PDFInfo
- Publication number
- CZ2011767A3 CZ2011767A3 CZ20110767A CZ2011767A CZ2011767A3 CZ 2011767 A3 CZ2011767 A3 CZ 2011767A3 CZ 20110767 A CZ20110767 A CZ 20110767A CZ 2011767 A CZ2011767 A CZ 2011767A CZ 2011767 A3 CZ2011767 A3 CZ 2011767A3
- Authority
- CZ
- Czechia
- Prior art keywords
- vardenafil
- acid
- solution
- aqueous
- formula
- Prior art date
Links
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical class CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 title claims abstract description 137
- 239000002253 acid Substances 0.000 title claims abstract description 38
- 238000002955 isolation Methods 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229960002381 vardenafil Drugs 0.000 claims abstract description 123
- 239000000243 solution Substances 0.000 claims abstract description 80
- 238000000034 method Methods 0.000 claims abstract description 67
- 230000008569 process Effects 0.000 claims abstract description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 54
- 150000003839 salts Chemical class 0.000 claims abstract description 44
- 239000007864 aqueous solution Substances 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 239000002904 solvent Substances 0.000 claims abstract description 26
- 229910052751 metal Inorganic materials 0.000 claims abstract description 8
- 239000002184 metal Substances 0.000 claims abstract description 8
- 150000004677 hydrates Chemical class 0.000 claims abstract description 7
- 239000011260 aqueous acid Substances 0.000 claims abstract description 5
- 239000006286 aqueous extract Substances 0.000 claims abstract description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 72
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 48
- FBCDRHDULQYRTB-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-4-one;trihydrate;hydrochloride Chemical compound O.O.O.Cl.CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 FBCDRHDULQYRTB-UHFFFAOYSA-N 0.000 claims description 26
- 239000002585 base Substances 0.000 claims description 23
- 239000003960 organic solvent Substances 0.000 claims description 23
- 229960004573 vardenafil hydrochloride trihydrate Drugs 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 18
- 150000007513 acids Chemical class 0.000 claims description 13
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 12
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 12
- WGCYRFWNGRMRJA-UHFFFAOYSA-N 1-ethylpiperazine Chemical compound CCN1CCNCC1 WGCYRFWNGRMRJA-UHFFFAOYSA-N 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
- -1 2-ethoxyphenyl Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- YRRWQMBIMZMVDB-UHFFFAOYSA-N 2-(2-ethoxyphenyl)-5-methyl-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-4-one Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C1=CC=CC=C1OCC YRRWQMBIMZMVDB-UHFFFAOYSA-N 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 claims description 3
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 claims description 2
- XTMCEBZOWCIYQF-UHFFFAOYSA-N 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-2-yl)benzenesulfonic acid Chemical class CCCC1=NC(C)=C(C(N2)=O)N1N=C2C1=CC(S(O)(=O)=O)=CC=C1OCC XTMCEBZOWCIYQF-UHFFFAOYSA-N 0.000 claims description 2
- ITOAVBRRRCBWLU-UHFFFAOYSA-N 4-ethoxy-3-(5-methyl-4-oxo-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-2-yl)benzenesulfonyl chloride Chemical compound CCCC1=NC(C)=C(C(N2)=O)N1N=C2C1=CC(S(Cl)(=O)=O)=CC=C1OCC ITOAVBRRRCBWLU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-M chlorosulfate Chemical compound [O-]S(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-M 0.000 claims description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- ZCVDYMMNVAZSTH-UHFFFAOYSA-N nitric acid hydrobromide Chemical compound Br.O[N+]([O-])=O ZCVDYMMNVAZSTH-UHFFFAOYSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 abstract 1
- 229910021653 sulphate ion Inorganic materials 0.000 abstract 1
- 239000012458 free base Substances 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 239000000203 mixture Substances 0.000 description 22
- 239000000047 product Substances 0.000 description 21
- 238000002425 crystallisation Methods 0.000 description 15
- 230000008025 crystallization Effects 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- NOIHTGOGFDFCBN-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-4-one;dihydrochloride Chemical compound Cl.Cl.CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 NOIHTGOGFDFCBN-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000012736 aqueous medium Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 238000010979 pH adjustment Methods 0.000 description 4
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 208000010228 Erectile Dysfunction Diseases 0.000 description 2
- 102000011016 Type 5 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 description 2
- 108010037581 Type 5 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 2
- 238000002479 acid--base titration Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 201000001881 impotence Diseases 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 125000001174 sulfone group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 238000000954 titration curve Methods 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- 229960001540 vardenafil hydrochloride Drugs 0.000 description 2
- 238000004131 Bayer process Methods 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000010669 acid-base reaction Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000001838 alkalimetric titration Methods 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- UETQVDZZPKAQIC-UHFFFAOYSA-N chlorane Chemical compound Cl.Cl.Cl.Cl UETQVDZZPKAQIC-UHFFFAOYSA-N 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- CKQQMPJQZXIYMJ-UHFFFAOYSA-N dihydrate;dihydrochloride Chemical compound O.O.Cl.Cl CKQQMPJQZXIYMJ-UHFFFAOYSA-N 0.000 description 1
- 239000013583 drug formulation Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229940097443 levitra Drugs 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Gynecology & Obstetrics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20110767A CZ2011767A3 (cs) | 2011-11-24 | 2011-11-24 | Zpusob prípravy a izolace solí vardenafilu s kyselinami |
| PCT/CZ2012/000120 WO2013075680A1 (en) | 2011-11-24 | 2012-11-26 | A method for the preparation and isolation of salts of vardenafil with acids |
| IN1308KON2014 IN2014KN01308A (enExample) | 2011-11-24 | 2012-11-26 | |
| BR112014012430A BR112014012430A2 (pt) | 2011-11-24 | 2012-11-26 | métodos para a preparação e isolamento de sais de vardenafila e para a preparação de vardenafila, e, uso de sais de vardenafila com ácidos |
| HU1400334A HUP1400334A3 (en) | 2011-11-24 | 2012-11-26 | A method for the preparation and isolation of salts of vardenafil with acids |
| CN201280057517.3A CN103946225B (zh) | 2011-11-24 | 2012-11-26 | 用于制备和分离伐地那非与酸的盐的方法 |
| IL232652A IL232652A (en) | 2011-11-24 | 2014-05-15 | A method for the preparation and isolation of Vardenafil salts with acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20110767A CZ2011767A3 (cs) | 2011-11-24 | 2011-11-24 | Zpusob prípravy a izolace solí vardenafilu s kyselinami |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CZ303877B6 CZ303877B6 (cs) | 2013-06-05 |
| CZ2011767A3 true CZ2011767A3 (cs) | 2013-06-05 |
Family
ID=47435673
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ20110767A CZ2011767A3 (cs) | 2011-11-24 | 2011-11-24 | Zpusob prípravy a izolace solí vardenafilu s kyselinami |
Country Status (7)
| Country | Link |
|---|---|
| CN (1) | CN103946225B (enExample) |
| BR (1) | BR112014012430A2 (enExample) |
| CZ (1) | CZ2011767A3 (enExample) |
| HU (1) | HUP1400334A3 (enExample) |
| IL (1) | IL232652A (enExample) |
| IN (1) | IN2014KN01308A (enExample) |
| WO (1) | WO2013075680A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20160317542A1 (en) | 2013-12-09 | 2016-11-03 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
| PL223869B1 (pl) | 2013-12-16 | 2016-11-30 | Starogardzkie Zakłady Farm Polpharma Spółka Akcyjna | Sposób otrzymywania wardenafilu i jego soli |
| CN107445964A (zh) * | 2017-07-29 | 2017-12-08 | 合肥创新医药技术有限公司 | 一种盐酸伐地那非杂质的合成方法 |
| MX2020005890A (es) | 2017-12-20 | 2020-10-19 | Klaria Pharma Holding Ab | Formulacion de pelicula que comprende vardenafil, metodo para su preparacion y uso de la misma. |
| BR112021009958A2 (pt) * | 2018-11-28 | 2021-08-17 | Topadur Pharma Ag | modo duplo de ação de ativadores de guanilato ciclase solúveis e inibidores de fosfodiesterase e seus usos |
| CN114085225A (zh) * | 2021-06-04 | 2022-02-25 | 广东西捷药业有限公司 | 一种伐地那非类似物及其合成方法和应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2395558C (en) * | 1997-11-12 | 2007-07-17 | Bayer Aktiengesellschaft | Intermediates for 2-phenyl substituted imidazotriazinones as phosphodiesterase inhibitors |
| DE10063108A1 (de) * | 2000-12-18 | 2002-06-20 | Bayer Ag | Verfahren zur Herstellung von Sulfonamid-substituierten Imidazotriazinonen |
| DE10232113A1 (de) | 2002-07-16 | 2004-01-29 | Bayer Ag | Vardenafil Hydrochlorid Trihydrat enthaltende Arzneimittel |
| DE102004023069A1 (de) | 2004-05-11 | 2005-12-08 | Bayer Healthcare Ag | Neue Darreichungsformen des PDE 5-Inhibitors Vardenafil |
| US7977478B2 (en) | 2006-03-13 | 2011-07-12 | Dr. Reddy's Laboratories Limited | Polymorphic forms of vardenafil |
| DE102007027067A1 (de) | 2007-06-12 | 2008-12-18 | Ratiopharm Gmbh | Verfahren zur Herstellung eines Arzneimittels enthaltend Vardenafil Hydrochlorid Trihydrat |
| CN101965348B (zh) | 2007-09-06 | 2013-11-13 | 上海特化医药科技有限公司 | 伐地那非的制备方法及其中间体 |
| PL2228370T3 (pl) | 2007-12-28 | 2012-10-31 | Topharman Shanghai Co Ltd | N-{1-[3-(2-etoksy-5-(4-etylopiperazynylo)benzenosulfonylo)-4,5-dihydro-5-okso-1,2,4-triazyn-6-yl]etylo}butyroamid, sposób jego wytwarzania i zastosowanie |
| DE102009020888A1 (de) | 2009-05-12 | 2010-11-18 | Ratiopharm Gmbh | Schmelztablette, enthaltend ein Vardenafil-Salz |
| PL390079A1 (pl) * | 2009-12-30 | 2011-07-04 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Sposób otrzymywania wardenafilu i jego izolacji jako soli z kwasem cytrynowym oraz krystaliczna postać tej soli |
| CN101870698B (zh) * | 2010-04-02 | 2012-10-17 | 漆又毛 | 磺酰苯基咪唑并三嗪衍生物及制备方法 |
-
2011
- 2011-11-24 CZ CZ20110767A patent/CZ2011767A3/cs not_active IP Right Cessation
-
2012
- 2012-11-26 HU HU1400334A patent/HUP1400334A3/hu unknown
- 2012-11-26 BR BR112014012430A patent/BR112014012430A2/pt not_active Application Discontinuation
- 2012-11-26 IN IN1308KON2014 patent/IN2014KN01308A/en unknown
- 2012-11-26 WO PCT/CZ2012/000120 patent/WO2013075680A1/en not_active Ceased
- 2012-11-26 CN CN201280057517.3A patent/CN103946225B/zh active Active
-
2014
- 2014-05-15 IL IL232652A patent/IL232652A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BR112014012430A2 (pt) | 2017-06-06 |
| CZ303877B6 (cs) | 2013-06-05 |
| CN103946225B (zh) | 2016-06-15 |
| IN2014KN01308A (enExample) | 2015-10-16 |
| CN103946225A (zh) | 2014-07-23 |
| WO2013075680A1 (en) | 2013-05-30 |
| IL232652A (en) | 2017-05-29 |
| HUP1400334A2 (hu) | 2014-10-28 |
| HUP1400334A3 (en) | 2014-12-29 |
| IL232652A0 (en) | 2014-06-30 |
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| MM4A | Patent lapsed due to non-payment of fee |
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