IL133387A - Multi-shaped crystals of -8 chloro-6, -11 dihydro-11 (-4-piperidylidene) - H5 - benzo [5, 6] cyclohepta [1, 2 - [b pyridine - Google Patents
Multi-shaped crystals of -8 chloro-6, -11 dihydro-11 (-4-piperidylidene) - H5 - benzo [5, 6] cyclohepta [1, 2 - [b pyridineInfo
- Publication number
- IL133387A IL133387A IL13338798A IL13338798A IL133387A IL 133387 A IL133387 A IL 133387A IL 13338798 A IL13338798 A IL 13338798A IL 13338798 A IL13338798 A IL 13338798A IL 133387 A IL133387 A IL 133387A
- Authority
- IL
- Israel
- Prior art keywords
- polymorph form
- descarbonylethoxyloratadine
- crystalline polymorph
- approximately
- characteristic peaks
- Prior art date
Links
- JAUOIFJMECXRGI-UHFFFAOYSA-N Neoclaritin Chemical compound C=1C(Cl)=CC=C2C=1CCC1=CC=CN=C1C2=C1CCNCC1 JAUOIFJMECXRGI-UHFFFAOYSA-N 0.000 title 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 15
- 239000007787 solid Substances 0.000 claims description 19
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 17
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 17
- 239000002480 mineral oil Substances 0.000 claims description 16
- 235000010446 mineral oil Nutrition 0.000 claims description 16
- 238000002329 infrared spectrum Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 206010020751 Hypersensitivity Diseases 0.000 claims description 6
- 230000003266 anti-allergic effect Effects 0.000 claims description 5
- 229960003088 loratadine Drugs 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- JCCNYMKQOSZNPW-UHFFFAOYSA-N loratadine Chemical compound C1CN(C(=O)OCC)CCC1=C1C2=NC=CC=C2CCC2=CC(Cl)=CC=C21 JCCNYMKQOSZNPW-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 4
- 238000001816 cooling Methods 0.000 claims 2
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 238000002798 spectrophotometry method Methods 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 230000001387 anti-histamine Effects 0.000 description 4
- 238000011194 good manufacturing practice Methods 0.000 description 4
- 230000000704 physical effect Effects 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- -1 alkane ethers Chemical class 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000012430 stability testing Methods 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 239000012049 topical pharmaceutical composition Substances 0.000 description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 239000004264 Petrolatum Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229940066842 petrolatum Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88676697A | 1997-07-02 | 1997-07-02 | |
| PCT/US1998/013433 WO1999001450A1 (en) | 1997-07-02 | 1998-07-01 | POLYMORPHS OF 8-CHLORO-6, 11-DIHYDRO-11- (4-PIPERIDYLIDENE) -5H-BENZO[5,6] CYCLOHEPTA[1,2-b]PYRIDINE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL133387A0 IL133387A0 (en) | 2001-04-30 |
| IL133387A true IL133387A (en) | 2004-02-08 |
Family
ID=25389724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL13338798A IL133387A (en) | 1997-07-02 | 1998-07-01 | Multi-shaped crystals of -8 chloro-6, -11 dihydro-11 (-4-piperidylidene) - H5 - benzo [5, 6] cyclohepta [1, 2 - [b pyridine |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP0993455B1 (https=) |
| JP (2) | JP2002507991A (https=) |
| KR (1) | KR20010014316A (https=) |
| CN (1) | CN1261886A (https=) |
| AR (1) | AR013161A1 (https=) |
| AT (1) | ATE239010T1 (https=) |
| AU (1) | AU734487B2 (https=) |
| BR (1) | BR9811658A (https=) |
| CA (1) | CA2294352C (https=) |
| CO (1) | CO4940423A1 (https=) |
| DE (1) | DE69814076T2 (https=) |
| ES (1) | ES2197480T3 (https=) |
| HU (1) | HUP0004308A3 (https=) |
| IL (1) | IL133387A (https=) |
| MY (1) | MY132943A (https=) |
| NO (1) | NO996547L (https=) |
| NZ (1) | NZ501417A (https=) |
| PE (1) | PE86399A1 (https=) |
| PL (1) | PL337712A1 (https=) |
| RU (1) | RU2197485C2 (https=) |
| SK (1) | SK185299A3 (https=) |
| TR (1) | TR199903308T2 (https=) |
| UA (1) | UA62976C2 (https=) |
| WO (1) | WO1999001450A1 (https=) |
| ZA (1) | ZA985783B (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7405223B2 (en) | 2000-02-03 | 2008-07-29 | Schering Corporation | Treating allergic and inflammatory conditions |
| US7678908B2 (en) * | 2002-04-15 | 2010-03-16 | Sun Pharmaceutical Industries Limited | Process of preparing desaloratadine |
| WO2004012738A1 (en) * | 2002-08-05 | 2004-02-12 | Sandoz Ag | Novel salt and polymorphs of desloratadine hemifumarate |
| US20060135547A1 (en) * | 2003-03-12 | 2006-06-22 | Toth Zoltan G | Stable pharmaceutical compositions of desloratadine and processes for preparation of polymorphic forms of desloratadine |
| WO2004080461A2 (en) * | 2003-03-12 | 2004-09-23 | TEVA Gyógyszergyár Részvénytársaság | Stable pharmaceutical compositions of desloratadine |
| SK50112007A3 (sk) * | 2004-07-07 | 2007-07-06 | Egis Gy�gyszergy�r Nyrt. | Nový pseudopolymorf desloratadínu vytvorený s oxidom uhličitým |
| TW200735871A (en) * | 2005-11-17 | 2007-10-01 | Teva Pharma | Desloratadine crystalline forms mixtures having a low level of residual solvents |
| HU230417B1 (hu) * | 2006-10-26 | 2016-05-30 | Egis Gyógyszergyár Zrt | Eljárás desloratadine szén-dioxiddal képezett adduktjának előállítására |
| EP2164470A1 (en) * | 2007-05-11 | 2010-03-24 | ratiopharm GmbH | Pharmaceutical composition comprising desloratadine |
| EP2269586B1 (en) | 2009-07-01 | 2011-09-21 | Alfred E. Tiefenbacher (GmbH & Co. KG) | Pharmaceutical composition comprising desloratadine |
| PT2568970T (pt) | 2010-05-10 | 2019-02-11 | Lesvi Laboratorios Sl | Formulações farmacêuticas estáveis contendo um anti-histamínico |
| EP2727592A1 (en) | 2012-11-05 | 2014-05-07 | Kücükgüzel, Sükriye Güniz | A combination of desloratadine and paracetamol |
| CN103755682A (zh) * | 2013-12-30 | 2014-04-30 | 山东达因海洋生物制药股份有限公司 | 一种地氯雷他定新晶型及制备方法 |
| CN108358892A (zh) * | 2018-04-11 | 2018-08-03 | 常州方圆制药有限公司 | 一种地氯雷他定粗品的提纯方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1985003707A1 (en) * | 1984-02-15 | 1985-08-29 | Schering Corporation | 8-CHLORO-6,11-DIHYDRO-11-(4-PIPERIDYLIDENE)-5H-BENZO AD5,6 BDCYCLOHEPTA AD1,2-b BDPYRIDINE AND ITS SALTS, PROCESSES FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL COMPOSITIONS CONTAINING THESE COMPOUNDS |
| EP0208855B1 (en) * | 1985-05-13 | 1991-03-06 | Schering Corporation | process for preparing piperidylidene dihydrodibenzo(a,d)cycloheptenes and aza derivatives thereof, compounds obtained by such process and the use of such compounds for preparing useful pharmaceutical compositions |
| IE68935B1 (en) * | 1990-06-22 | 1996-07-24 | Schering Corp | Bis-benzo or benzopyrido cyclohepta piperidene piperidylidene and piperazine compounds compositions and methods of use |
-
1998
- 1998-01-07 UA UA2000010519A patent/UA62976C2/uk unknown
- 1998-07-01 PL PL98337712A patent/PL337712A1/xx unknown
- 1998-07-01 AT AT98932930T patent/ATE239010T1/de not_active IP Right Cessation
- 1998-07-01 EP EP98932930A patent/EP0993455B1/en not_active Expired - Lifetime
- 1998-07-01 IL IL13338798A patent/IL133387A/en not_active IP Right Cessation
- 1998-07-01 ES ES98932930T patent/ES2197480T3/es not_active Expired - Lifetime
- 1998-07-01 BR BR9811658-4A patent/BR9811658A/pt not_active IP Right Cessation
- 1998-07-01 CO CO98037139A patent/CO4940423A1/es unknown
- 1998-07-01 AR ARP980103203A patent/AR013161A1/es unknown
- 1998-07-01 KR KR1019997012456A patent/KR20010014316A/ko not_active Ceased
- 1998-07-01 HU HU0004308A patent/HUP0004308A3/hu unknown
- 1998-07-01 CN CN98806712A patent/CN1261886A/zh active Pending
- 1998-07-01 TR TR1999/03308T patent/TR199903308T2/xx unknown
- 1998-07-01 RU RU2000102669/04A patent/RU2197485C2/ru not_active IP Right Cessation
- 1998-07-01 NZ NZ501417A patent/NZ501417A/xx unknown
- 1998-07-01 DE DE69814076T patent/DE69814076T2/de not_active Expired - Lifetime
- 1998-07-01 JP JP50726599A patent/JP2002507991A/ja active Pending
- 1998-07-01 AU AU82710/98A patent/AU734487B2/en not_active Ceased
- 1998-07-01 CA CA002294352A patent/CA2294352C/en not_active Expired - Fee Related
- 1998-07-01 WO PCT/US1998/013433 patent/WO1999001450A1/en not_active Ceased
- 1998-07-01 ZA ZA985783A patent/ZA985783B/xx unknown
- 1998-07-01 SK SK1852-99A patent/SK185299A3/sk unknown
- 1998-07-02 MY MYPI98003024A patent/MY132943A/en unknown
- 1998-07-02 PE PE1998000594A patent/PE86399A1/es not_active Application Discontinuation
-
1999
- 1999-12-29 NO NO996547A patent/NO996547L/no not_active Application Discontinuation
-
2009
- 2009-07-27 JP JP2009174701A patent/JP2009242436A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0004308A3 (en) | 2004-07-28 |
| EP0993455A1 (en) | 2000-04-19 |
| DE69814076T2 (de) | 2004-02-26 |
| SK185299A3 (en) | 2000-07-11 |
| AR013161A1 (es) | 2000-12-13 |
| PL337712A1 (en) | 2000-08-28 |
| PE86399A1 (es) | 1999-10-23 |
| ES2197480T3 (es) | 2004-01-01 |
| ATE239010T1 (de) | 2003-05-15 |
| BR9811658A (pt) | 2000-09-05 |
| UA62976C2 (en) | 2004-01-15 |
| HUP0004308A2 (hu) | 2001-10-28 |
| CN1261886A (zh) | 2000-08-02 |
| MY132943A (en) | 2007-10-31 |
| JP2002507991A (ja) | 2002-03-12 |
| CO4940423A1 (es) | 2000-07-24 |
| NO996547L (no) | 2000-03-01 |
| ZA985783B (en) | 1999-01-19 |
| AU8271098A (en) | 1999-01-25 |
| NZ501417A (en) | 2000-10-27 |
| NO996547D0 (no) | 1999-12-29 |
| TR199903308T2 (xx) | 2000-11-21 |
| KR20010014316A (ko) | 2001-02-26 |
| WO1999001450A1 (en) | 1999-01-14 |
| DE69814076D1 (de) | 2003-06-05 |
| HK1024687A1 (en) | 2000-10-20 |
| AU734487B2 (en) | 2001-06-14 |
| JP2009242436A (ja) | 2009-10-22 |
| IL133387A0 (en) | 2001-04-30 |
| CA2294352A1 (en) | 1999-01-14 |
| CA2294352C (en) | 2008-05-06 |
| RU2197485C2 (ru) | 2003-01-27 |
| EP0993455B1 (en) | 2003-05-02 |
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