ZA200601264B - Purification process - Google Patents
Purification process Download PDFInfo
- Publication number
- ZA200601264B ZA200601264B ZA200601264A ZA200601264A ZA200601264B ZA 200601264 B ZA200601264 B ZA 200601264B ZA 200601264 A ZA200601264 A ZA 200601264A ZA 200601264 A ZA200601264 A ZA 200601264A ZA 200601264 B ZA200601264 B ZA 200601264B
- Authority
- ZA
- South Africa
- Prior art keywords
- terbinafine
- ppm
- distillation
- free base
- palladium
- Prior art date
Links
- 238000000746 purification Methods 0.000 title claims description 8
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 claims description 50
- 229960002722 terbinafine Drugs 0.000 claims description 49
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 43
- 238000004821 distillation Methods 0.000 claims description 29
- 239000010949 copper Substances 0.000 claims description 24
- 229910052802 copper Inorganic materials 0.000 claims description 23
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 22
- 239000012458 free base Substances 0.000 claims description 22
- 229910052763 palladium Inorganic materials 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 19
- 239000000047 product Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 150000003839 salts Chemical group 0.000 claims description 12
- 238000000526 short-path distillation Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000012264 purified product Substances 0.000 claims description 8
- 239000012043 crude product Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 5
- PPWNCLVNXGCGAF-UHFFFAOYSA-N 3,3-dimethylbut-1-yne Chemical compound CC(C)(C)C#C PPWNCLVNXGCGAF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 description 19
- 239000006227 byproduct Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 239000000356 contaminant Substances 0.000 description 6
- 238000004817 gas chromatography Methods 0.000 description 6
- 235000019483 Peanut oil Nutrition 0.000 description 5
- -1 allylamine compound Chemical class 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000000312 peanut oil Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000009835 boiling Methods 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
- 239000010408 film Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- YYGNTYWPHWGJRM-UHFFFAOYSA-N (6E,10E,14E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene Chemical compound CC(C)=CCCC(C)=CCCC(C)=CCCC=C(C)CCC=C(C)CCC=C(C)C YYGNTYWPHWGJRM-UHFFFAOYSA-N 0.000 description 2
- VCVMWFDNPLLHKP-UHFFFAOYSA-N 2,2,7,7-tetramethylocta-3,5-diyne Chemical compound CC(C)(C)C#CC#CC(C)(C)C VCVMWFDNPLLHKP-UHFFFAOYSA-N 0.000 description 2
- 241001480043 Arthrodermataceae Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- BHEOSNUKNHRBNM-UHFFFAOYSA-N Tetramethylsqualene Natural products CC(=C)C(C)CCC(=C)C(C)CCC(C)=CCCC=C(C)CCC(C)C(=C)CCC(C)C(C)=C BHEOSNUKNHRBNM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000000998 batch distillation Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000000498 cooling water Substances 0.000 description 2
- 230000001351 cycling effect Effects 0.000 description 2
- 230000037304 dermatophytes Effects 0.000 description 2
- PRAKJMSDJKAYCZ-UHFFFAOYSA-N dodecahydrosqualene Natural products CC(C)CCCC(C)CCCC(C)CCCCC(C)CCCC(C)CCCC(C)C PRAKJMSDJKAYCZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000008686 ergosterol biosynthesis Effects 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229940031439 squalene Drugs 0.000 description 2
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- QYIMSPSDBYKPPY-BANQPHDMSA-N 2,3-epoxysqualene Chemical compound CC(C)=CCC\C(C)=C\CC\C(C)=C\CC\C=C(/C)CC\C=C(/C)CCC1OC1(C)C QYIMSPSDBYKPPY-BANQPHDMSA-N 0.000 description 1
- NQFDBNASDXPZGS-UHFFFAOYSA-N 6,7-dimethyldodeca-1,11-dien-4,8-diyne-6,7-diol Chemical compound C=CCC#CC(O)(C)C(C)(O)C#CCC=C NQFDBNASDXPZGS-UHFFFAOYSA-N 0.000 description 1
- 241000478345 Afer Species 0.000 description 1
- OMUOKNFTKFFOMI-SFECMWDFSA-N C#C\C=C/C#C\C=C/C#C Chemical compound C#C\C=C/C#C\C=C/C#C OMUOKNFTKFFOMI-SFECMWDFSA-N 0.000 description 1
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 208000007163 Dermatomycoses Diseases 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 208000031888 Mycoses Diseases 0.000 description 1
- 241000223252 Rhodotorula Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 206010039509 Scab Diseases 0.000 description 1
- 102000005782 Squalene Monooxygenase Human genes 0.000 description 1
- 108020003891 Squalene monooxygenase Proteins 0.000 description 1
- 229920006362 Teflon® Polymers 0.000 description 1
- 241000223238 Trichophyton Species 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000001857 anti-mycotic effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000002543 antimycotic Substances 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940089474 lamisil Drugs 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-L malate(2-) Chemical compound [O-]C(=O)C(O)CC([O-])=O BJEPYKJPYRNKOW-UHFFFAOYSA-L 0.000 description 1
- 150000004701 malic acid derivatives Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- FPCAUUABCRPODB-UHFFFAOYSA-N penta-1,2-dien-4-yne Chemical compound C=C=CC#C FPCAUUABCRPODB-UHFFFAOYSA-N 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 210000000434 stratum corneum Anatomy 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/82—Purification; Separation; Stabilisation; Use of additives
- C07C209/84—Purification
-
- 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
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/27—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring having amino groups linked to the six-membered aromatic ring by saturated carbon chains
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/30—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the six-membered aromatic ring being part of a condensed ring system formed by two rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0320312.2A GB0320312D0 (en) | 2003-08-29 | 2003-08-29 | Purification process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200601264B true ZA200601264B (en) | 2007-06-27 |
Family
ID=28686596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200601264A ZA200601264B (en) | 2003-08-29 | 2006-02-13 | Purification process |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US20060076227A1 (fr) |
| EP (1) | EP1694631A2 (fr) |
| JP (1) | JP5208416B2 (fr) |
| KR (2) | KR20120054109A (fr) |
| CN (1) | CN100491334C (fr) |
| AR (1) | AR045506A1 (fr) |
| AU (1) | AU2004268051B2 (fr) |
| BR (1) | BRPI0413896A (fr) |
| CA (1) | CA2536498C (fr) |
| EC (1) | ECSP066382A (fr) |
| GB (1) | GB0320312D0 (fr) |
| IL (1) | IL173709A (fr) |
| IS (1) | IS8369A (fr) |
| MA (1) | MA28030A1 (fr) |
| MX (1) | MXPA06002348A (fr) |
| MY (1) | MY149357A (fr) |
| NO (1) | NO20061404L (fr) |
| NZ (1) | NZ545445A (fr) |
| PE (1) | PE20050873A1 (fr) |
| RU (1) | RU2367649C2 (fr) |
| SG (1) | SG145782A1 (fr) |
| TN (1) | TNSN06066A1 (fr) |
| TW (1) | TWI350829B (fr) |
| WO (1) | WO2005021483A2 (fr) |
| ZA (1) | ZA200601264B (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0503942D0 (en) * | 2005-02-25 | 2005-04-06 | Novartis Ag | Purification process |
| EP1900378A1 (fr) * | 2006-08-31 | 2008-03-19 | Novartis AG | Compositions pharmaceutiques pour le traitment d'infections fongiques |
| NZ604902A (en) | 2008-09-05 | 2014-06-27 | Teikoku Pharma Usa Inc | Iontophoretic drug delivery packaging |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2862103D1 (en) * | 1977-08-19 | 1982-11-18 | Sandoz Ag | Propenyl amines, processes for their production and pharmaceutical compositions containing them |
| DE3069633D1 (en) | 1979-08-22 | 1984-12-20 | Sandoz Ag | Propenylamines, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals |
| US5132459A (en) * | 1979-08-22 | 1992-07-21 | Sandoz Ltd. | Propenylamines, processes for their production, pharmaceutical compositions containing them and their use as pharmaceuticals |
| CH678527A5 (en) | 1989-06-22 | 1991-09-30 | Sandoz Ag | Trans(E)-N-(1-naphthyl:methyl)-heptenyl-amine prepn. - by simultaneously converting crude mixt. contg. cis and trans isomers to salt and precipitating trans isomer |
| JP3116364B2 (ja) * | 1989-10-02 | 2000-12-11 | 萬有製薬株式会社 | エンイン誘導体の製造法 |
| NZ280065A (en) * | 1995-09-20 | 1998-04-27 | Apotex Inc | Preparation of n-alkyl-n-(1-naphthylmethyl)alk-2-en-4-ynylamine derivatives |
| US6248363B1 (en) | 1999-11-23 | 2001-06-19 | Lipocine, Inc. | Solid carriers for improved delivery of active ingredients in pharmaceutical compositions |
| ES2203190T3 (es) | 1999-10-22 | 2004-04-01 | Richter Gedeon Vegyeszeti Gyar R.T. | Procedimiento para la preparacion de (e)-n-metil-n-(1-naftil-metil)-6,6-dimetil-hept-2-en-4-inil-1-amina. |
| GB2357762B (en) | 2000-03-13 | 2002-01-30 | Lundbeck & Co As H | Crystalline base of citalopram |
| ITMI20010421A1 (it) | 2001-03-01 | 2002-09-02 | Ausimont Spa | Membrane porose semipermeabili di fluoropolimeri semicristallini |
| ITMI20010430A1 (it) * | 2001-03-02 | 2002-09-02 | Dinamite Dipharma S P A In For | Metodo per la sintesi di terbinafina |
| KR100459275B1 (ko) | 2001-12-28 | 2004-12-03 | 주식회사유한양행 | 터비나핀 또는 그의 염산염의 제조방법 |
| ITMI20022534A1 (it) * | 2002-11-29 | 2004-05-30 | Dinamite Dipharma S P A | Procedimento per la preparazione di terbinafina mediante l'uso di platino come catalizzatore. |
| US20060004230A1 (en) * | 2004-06-30 | 2006-01-05 | Joseph Kaspi | Process for the preparation of terbinafine and salts thereof |
-
2003
- 2003-08-29 GB GBGB0320312.2A patent/GB0320312D0/en not_active Ceased
-
2004
- 2004-08-26 AR ARP040103068A patent/AR045506A1/es not_active Application Discontinuation
- 2004-08-27 BR BRPI0413896-1A patent/BRPI0413896A/pt not_active IP Right Cessation
- 2004-08-27 RU RU2006109640/04A patent/RU2367649C2/ru not_active IP Right Cessation
- 2004-08-27 MY MYPI20043511A patent/MY149357A/en unknown
- 2004-08-27 US US10/522,828 patent/US20060076227A1/en not_active Abandoned
- 2004-08-27 EP EP04764561A patent/EP1694631A2/fr not_active Withdrawn
- 2004-08-27 CN CNB2004800249663A patent/CN100491334C/zh not_active Expired - Fee Related
- 2004-08-27 JP JP2006524338A patent/JP5208416B2/ja not_active Expired - Fee Related
- 2004-08-27 KR KR1020127012618A patent/KR20120054109A/ko not_active Application Discontinuation
- 2004-08-27 PE PE2004000823A patent/PE20050873A1/es not_active Application Discontinuation
- 2004-08-27 NZ NZ545445A patent/NZ545445A/en not_active IP Right Cessation
- 2004-08-27 MX MXPA06002348A patent/MXPA06002348A/es active IP Right Grant
- 2004-08-27 KR KR1020067003979A patent/KR101233024B1/ko not_active IP Right Cessation
- 2004-08-27 AU AU2004268051A patent/AU2004268051B2/en not_active Ceased
- 2004-08-27 CA CA2536498A patent/CA2536498C/fr not_active Expired - Fee Related
- 2004-08-27 TW TW093125943A patent/TWI350829B/zh not_active IP Right Cessation
- 2004-08-27 SG SG200806418-0A patent/SG145782A1/en unknown
- 2004-08-27 WO PCT/EP2004/009587 patent/WO2005021483A2/fr active Search and Examination
-
2006
- 2006-02-13 ZA ZA200601264A patent/ZA200601264B/en unknown
- 2006-02-13 IL IL173709A patent/IL173709A/en not_active IP Right Cessation
- 2006-02-17 EC EC2006006382A patent/ECSP066382A/es unknown
- 2006-02-27 TN TNP2006000066A patent/TNSN06066A1/en unknown
- 2006-03-08 MA MA28862A patent/MA28030A1/fr unknown
- 2006-03-23 IS IS8369A patent/IS8369A/is unknown
- 2006-03-28 NO NO20061404A patent/NO20061404L/no not_active Application Discontinuation
-
2008
- 2008-11-14 US US12/291,863 patent/US7985323B2/en not_active Expired - Fee Related
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