HRP990074A2 - Compound and its use - Google Patents
Compound and its use Download PDFInfo
- Publication number
- HRP990074A2 HRP990074A2 HR990074A HRP990074A HRP990074A2 HR P990074 A2 HRP990074 A2 HR P990074A2 HR 990074 A HR990074 A HR 990074A HR P990074 A HRP990074 A HR P990074A HR P990074 A2 HRP990074 A2 HR P990074A2
- Authority
- HR
- Croatia
- Prior art keywords
- sample
- solution
- lamotrigine
- compound
- dichlorophenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 57
- PYZRQGJRPPTADH-UHFFFAOYSA-N lamotrigine Chemical compound NC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl PYZRQGJRPPTADH-UHFFFAOYSA-N 0.000 claims description 81
- 229960001848 lamotrigine Drugs 0.000 claims description 80
- 239000000243 solution Substances 0.000 claims description 57
- 239000000523 sample Substances 0.000 claims description 37
- 239000012086 standard solution Substances 0.000 claims description 31
- 239000012488 sample solution Substances 0.000 claims description 28
- 238000012360 testing method Methods 0.000 claims description 24
- 239000003550 marker Substances 0.000 claims description 22
- 238000004809 thin layer chromatography Methods 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 17
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 15
- OVNGWOHWYFBGKF-UHFFFAOYSA-N 3-amino-6-(2,3-dichlorophenyl)-2h-1,2,4-triazin-5-one Chemical compound OC1=NC(N)=NN=C1C1=CC=CC(Cl)=C1Cl OVNGWOHWYFBGKF-UHFFFAOYSA-N 0.000 claims description 12
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 12
- 230000015556 catabolic process Effects 0.000 claims description 11
- 238000006731 degradation reaction Methods 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- RDUGDEWOUWFKPL-UHFFFAOYSA-N n-[5-amino-6-(2,3-dichlorophenyl)-1,2,4-triazin-3-yl]-2,3-dichlorobenzamide Chemical compound N=1N=C(C=2C(=C(Cl)C=CC=2)Cl)C(N)=NC=1NC(=O)C1=CC=CC(Cl)=C1Cl RDUGDEWOUWFKPL-UHFFFAOYSA-N 0.000 claims description 7
- FIBBFBXFASKAON-UHFFFAOYSA-N 2,3-dichlorobenzoyl cyanide Chemical compound ClC1=CC=CC(C(=O)C#N)=C1Cl FIBBFBXFASKAON-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 claims description 4
- YBONBWJSFMTXLE-UHFFFAOYSA-N 2,3-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(Cl)=C1Cl YBONBWJSFMTXLE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 229940126062 Compound A Drugs 0.000 description 21
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000004458 analytical method Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- 239000000356 contaminant Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000012490 blank solution Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000012085 test solution Substances 0.000 description 5
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- 238000011109 contamination Methods 0.000 description 4
- 239000007857 degradation product Substances 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229940126601 medicinal product Drugs 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 238000003860 storage Methods 0.000 description 4
- FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229940126534 drug product Drugs 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000012907 medicinal substance Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 229940085605 saccharin sodium Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 238000000451 chemical ionisation Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000007919 dispersible tablet Substances 0.000 description 2
- 229940088679 drug related substance Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004949 mass spectrometry Methods 0.000 description 2
- 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 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000013074 reference sample Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000010186 staining Methods 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- BXDSJOGMJUKSAE-CHHVJCJISA-N (1e)-2,3-dichloro-n-(diaminomethylideneamino)benzenecarboximidoyl cyanide Chemical compound NC(N)=N\N=C(\C#N)C1=CC=CC(Cl)=C1Cl BXDSJOGMJUKSAE-CHHVJCJISA-N 0.000 description 1
- GKNCZOMKFQSLCL-WYMPLXKRSA-N (1z)-2,3-dichloro-n-[[n'-(2,3-dichlorobenzoyl)carbamimidoyl]amino]benzenecarboximidoyl cyanide Chemical compound C=1C=CC(Cl)=C(Cl)C=1C(=O)N=C(N)N\N=C(/C#N)C1=CC=CC(Cl)=C1Cl GKNCZOMKFQSLCL-WYMPLXKRSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000012863 analytical testing Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/15—Medicinal preparations ; Physical properties thereof, e.g. dissolubility
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines 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
- C07D253/075—Two hetero atoms, in positions 3 and 5
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/02—Column chromatography
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N30/00—Investigating or analysing materials by separation into components using adsorption, absorption or similar phenomena or using ion-exchange, e.g. chromatography or field flow fractionation
- G01N30/90—Plate chromatography, e.g. thin layer or paper chromatography
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/10—Composition for standardization, calibration, simulation, stabilization, preparation or preservation; processes of use in preparation for chemical testing
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/145555—Hetero-N
- Y10T436/147777—Plural nitrogen in the same ring [e.g., barbituates, creatinine, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pharmacology & Pharmacy (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Immunology (AREA)
- Pathology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analyzing Non-Biological Materials By The Use Of Chemical Means (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9812413.4A GB9812413D0 (en) | 1998-06-10 | 1998-06-10 | Compound and its use |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP990074A2 true HRP990074A2 (en) | 2000-10-31 |
Family
ID=10833464
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR990074A HRP990074A2 (en) | 1998-06-10 | 1999-03-09 | Compound and its use |
Country Status (31)
Country | Link |
---|---|
US (1) | US6333198B1 (no) |
EP (2) | EP0963980B1 (no) |
JP (1) | JP2989189B1 (no) |
KR (1) | KR100322354B1 (no) |
CN (2) | CN1238454A (no) |
AP (3) | AP9901481A0 (no) |
AR (1) | AR014074A1 (no) |
AT (1) | ATE218552T1 (no) |
AU (1) | AU2031999A (no) |
BR (1) | BR9900984A (no) |
CA (1) | CA2265194C (no) |
DE (1) | DE69901656T2 (no) |
DK (1) | DK0963980T3 (no) |
EA (1) | EA000666B1 (no) |
ES (1) | ES2178342T3 (no) |
GB (1) | GB9812413D0 (no) |
HR (1) | HRP990074A2 (no) |
HU (1) | HUP9900592A3 (no) |
ID (1) | ID22957A (no) |
MA (1) | MA24777A1 (no) |
NO (2) | NO991151L (no) |
NZ (1) | NZ334590A (no) |
PE (1) | PE20000332A1 (no) |
PL (1) | PL331870A1 (no) |
PT (1) | PT963980E (no) |
SG (1) | SG85628A1 (no) |
SI (1) | SI0963980T1 (no) |
TR (1) | TR199900520A2 (no) |
UY (1) | UY25946A1 (no) |
YU (1) | YU12399A (no) |
ZA (1) | ZA991951B (no) |
Families Citing this family (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20020055177A1 (en) * | 1999-03-10 | 2002-05-09 | Glaxo Wellcome Inc. | Compound and its use |
AU763244B2 (en) * | 2000-01-03 | 2003-07-17 | Rpg Life Sciences Limited | A process for the preparation of 6-(2,3-dichlorophenyl)-1,2,4-triazine-3,5-diamine, commonly known as lamotrigine |
US7335380B2 (en) | 2000-12-29 | 2008-02-26 | Synthon Ip Inc. | Amlodipine free base |
MXPA03005884A (es) | 2000-12-29 | 2005-04-08 | Pfizer Ltd | Hemimaleato de amlodipina. |
SI1309555T1 (sl) | 2000-12-29 | 2005-12-31 | Pfizer Ltd | Postopek izdelave amlodipin-maleata |
AT5874U1 (de) | 2000-12-29 | 2003-01-27 | Bioorg Bv | Pharmazeutische zubereitungen enthaltend amlodipinmaleat |
MXPA03005886A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado de aspartato de amlodipina como antagonista del canal de calcio. |
MXPA03005882A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado amida de amlodipina. |
WO2002054062A2 (en) * | 2000-12-29 | 2002-07-11 | Pfizer Limited | Reference standards and processes for determining the purity or stability of amlodipine maleate |
CA2433181C (en) | 2000-12-29 | 2005-11-22 | Pfizer Limited | Amlodipine hemifumarate |
US6653481B2 (en) | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
BR0116554A (pt) | 2000-12-29 | 2004-02-03 | Pfizer Ltd | Composto, composição farmacêutica para o tratamento da angina ou hipertensão, processo, processo para o tratamento ou prevenção da angina ou hipertensão, composição do ingrediente farmaceuticamente ativo e composição farmacêutica para o tratamento ou prevenção da angina ou hipertensão |
DE10134980C2 (de) | 2001-07-17 | 2003-05-28 | Helm Ag | Verfahren zur Herstellung von Lamotrigin |
CA2366521C (en) | 2001-12-24 | 2007-03-06 | Brantford Chemicals Inc. | A new and efficient process for the preparation of lamotrigine and related 3,5-diamino-6-substituted-1,2,4-triazines |
US20030216376A1 (en) * | 2002-03-20 | 2003-11-20 | Revital Lifshitz-Liron | Crystalline forms of quetiapine hemifumarate |
HU225667B1 (en) * | 2002-09-20 | 2007-05-29 | Richter Gedeon Nyrt | Method for producing high-purity 3,5-diamino-6-(2,3-dichlorophenyl)-1,2,4-triazine |
ES2209639B1 (es) | 2002-10-31 | 2005-08-01 | Vita Cientifica, S.L. | Procedimiento para la obtencion de un compuesto farmaceuticamente activo y obtencion de su intermedio. |
GB2395483A (en) * | 2003-07-03 | 2004-05-26 | Jubilant Organosys Ltd | Crystalline lamotrigine and its monohydrate |
EP1562912A2 (en) | 2003-08-28 | 2005-08-17 | Teva Pharmaceutical Industries Limited | Process for preparation of rosuvastatin calcium |
CA2546701C (en) * | 2003-11-24 | 2010-07-27 | Teva Pharmaceutical Industries Ltd. | Crystalline ammonium salts of rosuvastatin |
KR100887264B1 (ko) | 2003-12-02 | 2009-03-06 | 테바 파마슈티컬 인더스트리즈 리미티드 | 로수바스타틴의 특성화를 위한 기준 표준물 |
US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
EP1708708A1 (en) * | 2004-01-30 | 2006-10-11 | Teva Pharmaceutical Industries Ltd. | Montelukast free acid polymorphs |
CA2554789A1 (en) * | 2004-01-30 | 2005-08-18 | Teva Pharmaceutical Industries, Ltd. | Montelukast sodium polymorphs |
MD2823G2 (ro) * | 2004-02-12 | 2006-05-31 | Институт Химии Академии Наук Молдовы | Procedeu de determinare cantitativă a sclareolului în extractele, obţinute din salvia de muscat |
JP2007532686A (ja) * | 2004-04-21 | 2007-11-15 | テバ ファーマシューティカル インダストリーズ リミティド | モンテルカストナトリウムを調製する方法 |
JP2007532585A (ja) | 2004-04-26 | 2007-11-15 | テバ ジョジセルジャール ザ−トケルエン ムケド レ−スベニュタ−ルシャシャ−グ | ミコフェノール酸及びそのエステル誘導体の調製方法 |
EP1740563A2 (en) * | 2004-04-27 | 2007-01-10 | Teva Gyógyszergyár Zártköruen Muködo Részvenytarsaság | Mycophenolate mofetil impurity |
US7439399B2 (en) * | 2004-06-28 | 2008-10-21 | Teva Pharmaceutical Fine Chemicals | Processes for the preparation of atomoxetine hydrochloride |
ATE407111T1 (de) * | 2004-06-28 | 2008-09-15 | Teva Pharm Fine Chemicals Srl | Isolierte atomoxetinverunreinigung, verfahren zur herstellung von atomoxetinverunreinigungen und deren verwendung als referenzstandards |
US7179916B2 (en) * | 2004-07-13 | 2007-02-20 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of rosuvastatin |
WO2006012379A2 (en) * | 2004-07-20 | 2006-02-02 | Teva Gyógyszergyár Zàrtköruen Muködo Rèszvènytàrsasàg | Processes for preparation of crystalline mycophenolate sodium |
WO2006020348A2 (en) * | 2004-07-22 | 2006-02-23 | Teva Pharmaceutical Fine Chemicals S.R.L. | Polymorphs of atomoxetine hydrochloride |
CA2578750A1 (en) * | 2004-09-04 | 2006-03-16 | Teva Pharmaceutical Industries, Ltd. | A valacyclovir impurity, process for the preparation of valacyclovir impurity and use as a reference standard |
US20060081361A1 (en) * | 2004-09-13 | 2006-04-20 | Gabbey Lawrence W | Oil cooler with integral filter |
ES2263407T1 (es) * | 2004-09-28 | 2006-12-16 | Teva Pharmaceutical Industries Ltd | Procedimiento para la preparacion de formas de atorvastatina calcica sustancialmente libres de impurezas. |
CA2582090A1 (en) * | 2004-10-19 | 2006-04-27 | Teva Pharmaceutical Industries Ltd. | Purification of tegaserod maleate |
US7678551B2 (en) * | 2004-10-25 | 2010-03-16 | Seradyn, Inc. | Immunoassays for lamotrigine |
WO2006071868A2 (en) * | 2004-12-23 | 2006-07-06 | Teva Pharmaceutical Industries Ltd. | Process for preparing pharmaceutically acceptable salts of duloxetine and intermediates thereof |
PT1836157E (pt) * | 2005-01-11 | 2009-11-24 | Teva Pharm Fine Chemicals Srl | Polimorfos de cloridrato de memantina |
US20070037979A1 (en) * | 2005-02-22 | 2007-02-15 | Valerie Niddam-Hildesheim | Preparation of rosuvastatin |
ES2389565T3 (es) | 2005-02-22 | 2012-10-29 | Teva Pharmaceutical Industries Ltd. | Rosuvastatina y sales de la misma carentes de alquiléter de rosuvatatina y un procedimiento para la preparación de las mismas |
US20070167625A1 (en) * | 2005-02-22 | 2007-07-19 | Anna Balanov | Preparation of rosuvastatin |
CA2602073A1 (en) * | 2005-02-24 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of linezolid intermediate |
US7534900B2 (en) * | 2005-03-14 | 2009-05-19 | Teva Pharmaceutical Industries Ltd | Process for the purification of duloxetine hydrochloride |
US7569729B2 (en) * | 2005-04-05 | 2009-08-04 | Teva Pharmaceutical Fine Chemicals S.R.L. | Stable atomoxetine hydrochloride, a process for the preparation thereof, and an analytical control of its stability |
CN101160281A (zh) * | 2005-04-06 | 2008-04-09 | 特瓦制药工业有限公司 | 结晶形态的普瑞巴林 |
US7488846B2 (en) * | 2005-04-11 | 2009-02-10 | Teva Pharmaceuical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
US20070066846A1 (en) * | 2005-04-11 | 2007-03-22 | Asher Maymon | Process for making (S)-Pregabalin |
JP2008502707A (ja) * | 2005-04-14 | 2008-01-31 | テバ ファーマシューティカル インダストリーズ リミティド | クエチアピンフマレートの調製方法 |
US20080280977A1 (en) * | 2005-04-26 | 2008-11-13 | Sandor Molnar | Process for preparation of mycophenolate mofetil and other esters of mycophenolic acid |
CA2604600A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Pregabalin free of isobutylglutaric acid and a process for preparation thereof |
KR100893312B1 (ko) * | 2005-05-10 | 2009-04-15 | 테바 파마슈티컬 인더스트리즈 리미티드 | 프레가발린 및 이의 염의 제조 방법 |
CA2604624A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Optical resolution of 3-carbamoylmethyl-5-methyl hexanoic acid |
WO2006121557A1 (en) * | 2005-05-10 | 2006-11-16 | Teva Pharmaceutical Industries Ltd. | Pregabalin free of lactam and a process for preparation thereof |
EP1975150A1 (en) | 2005-05-23 | 2008-10-01 | Teva Pharmaceutical Industries Ltd. | Cinacalcet salts |
WO2007002720A2 (en) * | 2005-06-27 | 2007-01-04 | Sicor, Inc. | An impurity of anastrozole intermediate, and uses thereof |
KR20080015438A (ko) * | 2005-06-27 | 2008-02-19 | 시코르, 인크. | 아나스트로졸 중간체의 불순물, 및 이의 용도 |
JP2008510840A (ja) * | 2005-07-05 | 2008-04-10 | テバ ファーマシューティカル インダストリーズ リミティド | モンテルカストの精製 |
WO2007022488A2 (en) * | 2005-08-16 | 2007-02-22 | Teva Pharmaceutical Industries Ltd. | Crystalline rosuvastatin intermediate |
KR20070087596A (ko) * | 2005-09-19 | 2007-08-28 | 테바 파마슈티컬 인더스트리즈 리미티드 | (s)-(+)-3-(아미노메틸)-5-메틸헥산산의 비대칭 합성 |
US20070197529A1 (en) * | 2005-12-01 | 2007-08-23 | Viviana Braude | Isolated desfluoro-linezolid, preparation thereof and its use as a reference marker and standard |
US7759500B2 (en) * | 2005-12-05 | 2010-07-20 | Teva Pharmaceutical Industries Ltd. | 2-(N-methyl-propanamine)-3-(2-naphthol)thiophene, an impurity of duloxetine hydrochloride |
WO2007069264A2 (en) * | 2005-12-15 | 2007-06-21 | Alembic Limited | Reference standards for determining the purity of telithromycin and processes therefor |
US20070203221A1 (en) * | 2005-12-27 | 2007-08-30 | Valeriano Merli | Processes for preparing darifenacin hydrobromide |
CA2644819A1 (en) * | 2006-03-27 | 2007-11-08 | Teva Pharmaceutical Fine Chemicals S.R.L. | Process for preparing memantine hydrochloride substantially free of impurities |
US20080146675A1 (en) * | 2006-04-05 | 2008-06-19 | Eugenio Castelli | Stable Atomoxetine Hydrochloride, a process for the preparation thereof, and an analytical control of its stability |
GB0609835D0 (en) * | 2006-05-18 | 2006-06-28 | Pliva Istrazivanje I Razvoj D | Impurities of a pharmaceutical product |
KR20080027880A (ko) * | 2006-05-24 | 2008-03-28 | 테바 파마슈티컬 인더스트리즈 리미티드 | R-(+)-3-(카바모일메틸)-5-메틸헥산산 및 이의 염의 제조방법 |
EP1912931A2 (en) * | 2006-05-31 | 2008-04-23 | Teva Pharmaceutical Industries Ltd. | Preparation of (s)-pregabalin-nitrile |
KR20080036060A (ko) * | 2006-05-31 | 2008-04-24 | 테바 파마슈티컬 인더스트리즈 리미티드 | 프레가발린의 중간체의 제조에 효소 분할을 이용하는 방법 |
ES2339297T3 (es) * | 2006-06-29 | 2010-05-18 | Ivax Pharmaceuticals S.R.O. | Regulacion de la produccion de metabolitos acidos. |
US20120142919A1 (en) * | 2006-08-02 | 2012-06-07 | Medichem, S.A. | Method for synthesizing lamotrigine |
CN101506178A (zh) * | 2006-08-14 | 2009-08-12 | 隆沙有限公司 | 制备拉莫三嗪的方法 |
EP2139845A1 (en) * | 2007-02-26 | 2010-01-06 | Teva Pharmaceutical Industries Ltd. | Intermediates and processes for the synthesis of ramelteon |
BRPI0803092A2 (pt) * | 2007-03-22 | 2011-08-30 | Teva Pharma | sìntese de (s)-(+)-3-(aminometil)-5-metil ácido hexanóico, (s)-pregabalina |
BRPI0803097A2 (pt) * | 2007-04-11 | 2011-11-08 | Teva Gyogyszergyar ... | método para redução do nìvel de impurezas na fermentação do ácido micofenólico |
WO2008151170A2 (en) * | 2007-05-31 | 2008-12-11 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
US20090137842A1 (en) * | 2007-10-03 | 2009-05-28 | Vollerner Yuri | Pregabalin -4-eliminate, pregabalin 5-eliminate, their use as reference marker and standard, and method to produce pregabalin containing low levels thereof |
JP2010539156A (ja) * | 2007-10-23 | 2010-12-16 | テバ ファーマシューティカル インダストリーズ リミティド | ダサチニブ多形体およびその調製プロセス |
US20090281176A1 (en) * | 2007-11-01 | 2009-11-12 | Vinod Kumar Kansal | Process for the synthesis of ramelteon and its intermediates |
WO2009061513A1 (en) * | 2007-11-09 | 2009-05-14 | Thar Pharmaceuticals | Crystalline forms of lamotrigine |
CA2717580A1 (en) * | 2008-03-06 | 2009-12-17 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation of o-desmethylvenlafaxine, free from its dimer impurities |
US20100087525A1 (en) * | 2008-06-23 | 2010-04-08 | Lilach Hedvati | Stereoselective enzymatic synthesis of (s) or (r)-iso-butyl-glutaric ester |
WO2010045565A1 (en) * | 2008-10-16 | 2010-04-22 | Teva Pharmaceutical Industries Ltd. | Process for the synthesis of ramelteon and its intermediates |
CA2795023A1 (en) * | 2010-03-29 | 2011-10-06 | Pliva Hrvatska D.O.O. | Crystal forms of o-desmethylvenlafaxine fumarate |
WO2012034065A1 (en) | 2010-09-09 | 2012-03-15 | Teva Pharmaceutical Industries Ltd. | Aliskiren intermediates and a process for analyzing the purity of aliskiren |
CN102766104A (zh) * | 2012-08-20 | 2012-11-07 | 三金集团湖南三金制药有限责任公司 | 一种治疗双向情感障碍及癫痫病药物拉莫三嗪的合成方法 |
WO2015092819A2 (en) * | 2013-12-21 | 2015-06-25 | Nektar Therapeutics (India) Pvt. Ltd. | Derivatives of 6-(2,3-dichlorophenyl)-1,2,4-triazin-5- amine |
CN110467560A (zh) | 2018-05-09 | 2019-11-19 | 深圳微芯生物科技股份有限公司 | 一种苯基氨基丙酸钠衍生物、其制备方法和应用 |
KR102270026B1 (ko) * | 2020-01-31 | 2021-06-28 | 현대약품 주식회사 | (3s)-3-(4-(3-(1,4-다이옥사스파이로[4,5]데스-7-엔-8-일)벤질옥시)페닐)헥스-4-이노익산의 품질 평가 방법 |
CN113156009B (zh) * | 2021-04-20 | 2023-12-22 | 三金集团湖南三金制药有限责任公司 | 高效液相色谱分析拉莫三嗪的方法 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK153787C (da) | 1979-06-01 | 1989-01-16 | Wellcome Found | Analogifremgangsmaade til fremstilling af substituerede 3,5-diamino-6-phenyl-1,2,4-triaziner og alfa-cyanobenzyliden-aminoguanidinforbindelser til anvendelse som mellemprodukter herved |
EP0021120B1 (en) | 1979-06-01 | 1983-04-06 | The Wellcome Foundation Limited | 3,5-diamino-1,2,4-triazine derivatives, process for preparing such compounds and pharmaceutical compositions containing them |
GB8613183D0 (en) | 1986-05-30 | 1986-07-02 | Wellcome Found | Triazine salt |
GB9426448D0 (en) * | 1994-12-30 | 1995-03-01 | Wellcome Found | Process |
WO1996020934A1 (en) * | 1994-12-30 | 1996-07-11 | The Wellcome Foundation Limited | Process for the preparation of lamotrigine |
GB9512854D0 (en) * | 1995-06-23 | 1995-08-23 | Wellcome Found | Novel formulation |
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