CA2608490C - Preparation of famciclovir and other purine derivatives - Google Patents
Preparation of famciclovir and other purine derivatives Download PDFInfo
- Publication number
- CA2608490C CA2608490C CA2608490A CA2608490A CA2608490C CA 2608490 C CA2608490 C CA 2608490C CA 2608490 A CA2608490 A CA 2608490A CA 2608490 A CA2608490 A CA 2608490A CA 2608490 C CA2608490 C CA 2608490C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- formula
- alkyl
- famciclovir
- amino
- 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.)
- Expired - Fee Related
Links
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 title claims description 26
- 229960004396 famciclovir Drugs 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 19
- 150000003212 purines Chemical class 0.000 title claims description 13
- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title abstract description 9
- 150000002009 diols Chemical class 0.000 claims abstract description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 41
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- -1 amino, hydroxyl Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 7
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 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 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 7
- 150000001412 amines Chemical class 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 16
- KDCGOANMDULRCW-UHFFFAOYSA-N Purine Natural products N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract description 7
- 239000007858 starting material Substances 0.000 abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract description 6
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 abstract description 5
- 238000006467 substitution reaction Methods 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical class 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229940035437 1,3-propanediol Drugs 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- RYYIULNRIVUMTQ-UHFFFAOYSA-N 6-chloroguanine Chemical compound NC1=NC(Cl)=C2N=CNC2=N1 RYYIULNRIVUMTQ-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 230000000840 anti-viral effect Effects 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 229940126214 compound 3 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000005690 diesters Chemical class 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- ZTGWXXOUUKHQLW-UHFFFAOYSA-N 1-nitropyrimidine-2,4-dione Chemical compound [O-][N+](=O)N1C=CC(=O)NC1=O ZTGWXXOUUKHQLW-UHFFFAOYSA-N 0.000 description 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- 101150041968 CDC13 gene Proteins 0.000 description 1
- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- 208000009889 Herpes Simplex Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 101100006982 Mus musculus Ppcdc gene Proteins 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 125000005910 alkyl carbonate group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000005323 carbonate salts Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0510345.2 | 2005-05-20 | ||
| GB0510345A GB2426247A (en) | 2005-05-20 | 2005-05-20 | Methods of preparing purine derivatives such as famciclovir |
| PCT/GB2006/001877 WO2006123175A1 (en) | 2005-05-20 | 2006-05-19 | Preparation of famciclovir and other purine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2608490A1 CA2608490A1 (en) | 2006-11-23 |
| CA2608490C true CA2608490C (en) | 2013-09-10 |
Family
ID=34834391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2608490A Expired - Fee Related CA2608490C (en) | 2005-05-20 | 2006-05-19 | Preparation of famciclovir and other purine derivatives |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7601835B2 (OSRAM) |
| EP (1) | EP1883639B1 (OSRAM) |
| JP (1) | JP5227166B2 (OSRAM) |
| CN (1) | CN101233134B (OSRAM) |
| AT (1) | ATE479688T1 (OSRAM) |
| AU (1) | AU2006248745B2 (OSRAM) |
| BR (1) | BRPI0609632A2 (OSRAM) |
| CA (1) | CA2608490C (OSRAM) |
| DE (1) | DE602006016593D1 (OSRAM) |
| DK (1) | DK1883639T3 (OSRAM) |
| ES (1) | ES2351925T3 (OSRAM) |
| GB (1) | GB2426247A (OSRAM) |
| NZ (1) | NZ563636A (OSRAM) |
| PL (1) | PL1883639T3 (OSRAM) |
| PT (1) | PT1883639E (OSRAM) |
| TW (1) | TW200716638A (OSRAM) |
| WO (1) | WO2006123175A1 (OSRAM) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2496684A1 (en) * | 2002-08-26 | 2004-03-04 | Teva Pharmaceutical Industries Ltd | Crystalline solid famciclovir forms i, ii, iii and preparation thereof |
| WO2004099208A1 (en) * | 2003-04-30 | 2004-11-18 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of famciclovir |
| TW200613304A (en) * | 2004-05-18 | 2006-05-01 | Teva Pharma | Drying process for preparing crystalline solid famciclovir |
| WO2008072074A1 (en) * | 2006-12-11 | 2008-06-19 | Aurobindo Pharma Limited | An improved process for the preparation of purine derivative |
| CN101555249B (zh) * | 2008-04-08 | 2011-05-11 | 浙江海正药业股份有限公司 | 泛昔洛韦的合成方法 |
| CN102924455A (zh) * | 2011-08-11 | 2013-02-13 | 重庆圣华曦药业股份有限公司 | 一种泛昔洛韦中间体的合成方法 |
| CN104496991A (zh) * | 2014-11-04 | 2015-04-08 | 常州康丽制药有限公司 | 高品质2-氨基-6-氯-9-(4-羟基-3–羟甲基丁基)嘌呤的制备方法 |
| CN104744472A (zh) * | 2015-03-12 | 2015-07-01 | 常州康丽制药有限公司 | 高品质2-氨基-6-氯-9-(4-羟基-3-羟甲基丁基)嘌呤的制备方法 |
| CN109456329B (zh) * | 2018-11-19 | 2021-03-09 | 迪嘉药业集团有限公司 | 一种泛昔洛韦的制备方法 |
| ES3037292T3 (en) | 2019-12-11 | 2025-09-30 | Taro Pharma Ind | Preparation of trifarotene and intermediates and polymorphs thereof |
| CN112979653A (zh) * | 2019-12-12 | 2021-06-18 | 上药康丽（常州）药业有限公司 | 一种利用微通道反应器合成泛昔洛韦的方法 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0141927B1 (en) * | 1983-08-18 | 1991-10-30 | Beecham Group Plc | Antiviral guanine derivatives |
| US5684153A (en) | 1984-08-16 | 1997-11-04 | Beecham Group Plc | Process for the preparation of purine derivatives |
| EP0182024B1 (en) * | 1984-09-20 | 1991-04-03 | Beecham Group Plc | Purine derivatives and their pharmaceutical use |
| SE8406538D0 (sv) | 1984-12-21 | 1984-12-21 | Astra Laekemedel Ab | Novel derivatives of purine |
| GB8817607D0 (en) * | 1988-07-23 | 1988-09-01 | Beecham Group Plc | Novel process |
| GB8822236D0 (en) | 1988-09-21 | 1988-10-26 | Beecham Group Plc | Chemical process |
| GB9402161D0 (en) | 1994-02-04 | 1994-03-30 | Wellcome Found | Chloropyrimidine intermediates |
| GB9407698D0 (en) | 1994-04-19 | 1994-06-15 | Smithkline Beecham Plc | Pharmaceuticals |
| JPH11180983A (ja) | 1997-12-24 | 1999-07-06 | Sumika Fine Chemicals Co Ltd | ９置換２−アミノ−６−ハロゲノプリンおよびその製法 |
| GB9807116D0 (en) * | 1998-04-02 | 1998-06-03 | Smithkline Beecham Plc | Novel process |
| GB9807114D0 (en) * | 1998-04-02 | 1998-06-03 | Smithkline Beecham Plc | Novel process |
| SI20022A (sl) * | 1998-07-29 | 2000-02-29 | Kemijski inštitut | Alkilno substituirani purinovi derivati in njihova priprava |
| DE60202245T2 (de) | 2001-08-30 | 2005-09-01 | Ajinomoto Co., Inc. | Herstellungsmethode von Famciclovir und Herstellungs- bzw. Kristallisationsmethode eines entsprechenden Intermediates |
| JP2003146988A (ja) * | 2001-08-30 | 2003-05-21 | Ajinomoto Co Inc | ファムシクロビルの製造方法、並びにその中間体の製造および晶析方法 |
| KR100573860B1 (ko) | 2003-06-13 | 2006-04-25 | 경동제약 주식회사 | 2-아미노-9-(2-치환에틸)푸린을 이용한 9-[4-아세톡시-3-(아세톡시메틸)부트-1-일]-2-아미노푸린의 제조방법 |
| US20050215787A1 (en) * | 2004-03-26 | 2005-09-29 | Joshi Ramesh A | An improved process for the preparation of purines |
-
2005
- 2005-05-20 GB GB0510345A patent/GB2426247A/en not_active Withdrawn
- 2005-11-10 US US11/270,777 patent/US7601835B2/en not_active Expired - Fee Related
-
2006
- 2006-05-19 EP EP06743955A patent/EP1883639B1/en not_active Not-in-force
- 2006-05-19 WO PCT/GB2006/001877 patent/WO2006123175A1/en not_active Ceased
- 2006-05-19 DE DE602006016593T patent/DE602006016593D1/de active Active
- 2006-05-19 PT PT06743955T patent/PT1883639E/pt unknown
- 2006-05-19 BR BRPI0609632-8A patent/BRPI0609632A2/pt not_active IP Right Cessation
- 2006-05-19 ES ES06743955T patent/ES2351925T3/es active Active
- 2006-05-19 AT AT06743955T patent/ATE479688T1/de active
- 2006-05-19 CA CA2608490A patent/CA2608490C/en not_active Expired - Fee Related
- 2006-05-19 CN CN200680017571XA patent/CN101233134B/zh not_active Expired - Fee Related
- 2006-05-19 PL PL06743955T patent/PL1883639T3/pl unknown
- 2006-05-19 NZ NZ563636A patent/NZ563636A/en not_active IP Right Cessation
- 2006-05-19 TW TW095117840A patent/TW200716638A/zh unknown
- 2006-05-19 DK DK06743955.4T patent/DK1883639T3/da active
- 2006-05-19 JP JP2008511798A patent/JP5227166B2/ja not_active Expired - Fee Related
- 2006-05-19 AU AU2006248745A patent/AU2006248745B2/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2008540628A (ja) | 2008-11-20 |
| DE602006016593D1 (de) | 2010-10-14 |
| US20060264629A1 (en) | 2006-11-23 |
| GB0510345D0 (en) | 2005-06-29 |
| TW200716638A (en) | 2007-05-01 |
| US7601835B2 (en) | 2009-10-13 |
| CN101233134B (zh) | 2013-01-23 |
| GB2426247A (en) | 2006-11-22 |
| AU2006248745A1 (en) | 2006-11-23 |
| PT1883639E (pt) | 2010-12-07 |
| ES2351925T3 (es) | 2011-02-14 |
| CN101233134A (zh) | 2008-07-30 |
| AU2006248745B2 (en) | 2011-06-23 |
| BRPI0609632A2 (pt) | 2011-10-18 |
| JP5227166B2 (ja) | 2013-07-03 |
| EP1883639A1 (en) | 2008-02-06 |
| DK1883639T3 (da) | 2010-11-15 |
| ATE479688T1 (de) | 2010-09-15 |
| PL1883639T3 (pl) | 2011-04-29 |
| EP1883639B1 (en) | 2010-09-01 |
| CA2608490A1 (en) | 2006-11-23 |
| NZ563636A (en) | 2010-10-29 |
| WO2006123175A1 (en) | 2006-11-23 |
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| EEER | Examination request | ||
| MKLA | Lapsed |
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