CA2464145A1 - Polymorphous form of rimonabant, preparation method and pharmaceutical compositions containing same - Google Patents
Polymorphous form of rimonabant, preparation method and pharmaceutical compositions containing same Download PDFInfo
- Publication number
- CA2464145A1 CA2464145A1 CA002464145A CA2464145A CA2464145A1 CA 2464145 A1 CA2464145 A1 CA 2464145A1 CA 002464145 A CA002464145 A CA 002464145A CA 2464145 A CA2464145 A CA 2464145A CA 2464145 A1 CA2464145 A1 CA 2464145A1
- Authority
- CA
- Canada
- Prior art keywords
- une
- température
- rimonabant
- par
- caractérisé
- 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.)
- Abandoned
Links
- JZCPYUJPEARBJL-UHFFFAOYSA-N rimonabant Chemical compound CC=1C(C(=O)NN2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JZCPYUJPEARBJL-UHFFFAOYSA-N 0.000 title claims abstract description 81
- 229960003015 rimonabant Drugs 0.000 title claims abstract description 75
- 239000008194 pharmaceutical composition Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims description 24
- 238000010992 reflux Methods 0.000 claims description 12
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 10
- 239000000725 suspension Substances 0.000 claims description 8
- 230000004927 fusion Effects 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 239000002964 rayon Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 4
- 241000251184 Rajiformes Species 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 claims description 3
- 101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 claims description 2
- 238000010521 absorption reaction Methods 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 101100536354 Drosophila melanogaster tant gene Proteins 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- 239000003795 chemical substances by application Substances 0.000 description 9
- 101100322245 Caenorhabditis elegans des-2 gene Proteins 0.000 description 4
- 229920000858 Cyclodextrin Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 241001080024 Telles Species 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- CTKXFMQHOOWWEB-UHFFFAOYSA-N Ethylene oxide/propylene oxide copolymer Chemical compound CCCOC(C)COCCO CTKXFMQHOOWWEB-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229920001993 poloxamer 188 Polymers 0.000 description 2
- 229940044519 poloxamer 188 Drugs 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- BAMUEXIPKSRTBS-UHFFFAOYSA-N 1,1-dichloro-1,2,2,2-tetrafluoroethane Chemical compound FC(F)(F)C(F)(Cl)Cl BAMUEXIPKSRTBS-UHFFFAOYSA-N 0.000 description 1
- 101100119767 Caenorhabditis elegans fat-4 gene Proteins 0.000 description 1
- 101100468762 Caenorhabditis elegans ric-3 gene Proteins 0.000 description 1
- 229920002785 Croscarmellose sodium Polymers 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000005764 Theobroma cacao ssp. cacao Nutrition 0.000 description 1
- 235000005767 Theobroma cacao ssp. sphaerocarpum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- VJHCJDRQFCCTHL-UHFFFAOYSA-N acetic acid 2,3,4,5,6-pentahydroxyhexanal Chemical compound CC(O)=O.OCC(O)C(O)C(O)C(O)C=O VJHCJDRQFCCTHL-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 235000001046 cacaotero Nutrition 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 229960005168 croscarmellose Drugs 0.000 description 1
- 239000001767 crosslinked sodium carboxy methyl cellulose Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 235000013681 dietary sucrose Nutrition 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000012943 hotmelt Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 238000001565 modulated differential scanning calorimetry Methods 0.000 description 1
- 210000004985 myeloid-derived suppressor cell Anatomy 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 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
- C07D401/10—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 linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic 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)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Child & Adolescent Psychology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Steroid Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
La présente invention concerne un nouveau polymorphe cristalin du rimonabant , son mode de préparation et les compositions pharmaceutiques contenant ce nouveau polymorphe.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR01/14579 | 2001-11-08 | ||
| FR0114579A FR2831883B1 (fr) | 2001-11-08 | 2001-11-08 | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| PCT/FR2002/003765 WO2003040105A1 (fr) | 2001-11-08 | 2002-11-04 | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2464145A1 true CA2464145A1 (fr) | 2003-05-15 |
Family
ID=8869285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002464145A Abandoned CA2464145A1 (fr) | 2001-11-08 | 2002-11-04 | Polymorphous form of rimonabant, preparation method and pharmaceutical compositions containing same |
Country Status (33)
| Country | Link |
|---|---|
| US (2) | US20050043356A1 (fr) |
| EP (1) | EP1446384A1 (fr) |
| JP (2) | JP4181994B2 (fr) |
| KR (2) | KR20050043774A (fr) |
| CN (1) | CN100412063C (fr) |
| AP (1) | AP1830A (fr) |
| AR (1) | AR037253A1 (fr) |
| AU (1) | AU2002350869B2 (fr) |
| BR (1) | BR0213931A (fr) |
| CA (1) | CA2464145A1 (fr) |
| CO (1) | CO5580827A2 (fr) |
| CR (1) | CR7333A (fr) |
| EA (1) | EA006771B1 (fr) |
| EC (1) | ECSP045088A (fr) |
| FR (1) | FR2831883B1 (fr) |
| GE (1) | GEP20063894B (fr) |
| HR (1) | HRP20040403A2 (fr) |
| HU (1) | HUP0402043A3 (fr) |
| IL (2) | IL161533A0 (fr) |
| IS (1) | IS7226A (fr) |
| MA (1) | MA27080A1 (fr) |
| ME (1) | MEP21908A (fr) |
| MX (1) | MXPA04004394A (fr) |
| NO (1) | NO326648B1 (fr) |
| NZ (1) | NZ532369A (fr) |
| OA (1) | OA12721A (fr) |
| PL (1) | PL369372A1 (fr) |
| RS (1) | RS36904A (fr) |
| TN (1) | TNSN04079A1 (fr) |
| TW (1) | TW200302824A (fr) |
| UA (1) | UA76776C2 (fr) |
| WO (1) | WO2003040105A1 (fr) |
| ZA (1) | ZA200402999B (fr) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2831883B1 (fr) * | 2001-11-08 | 2004-07-23 | Sanofi Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| NZ537003A (en) | 2002-07-18 | 2008-03-28 | Cytos Biotechnology Ag | Hapten-carrier conjugates comprising virus like particles and uses thereof |
| FR2861992B1 (fr) * | 2003-11-10 | 2007-07-20 | Sanofi Synthelabo | Composition pharmaceutique destinee a l'administration orale d'un derive de pyrazole-3-carboxamide. |
| EP1910290A2 (fr) | 2005-06-30 | 2008-04-16 | Prosidion Limited | Agonistes de gpcr |
| EP1816125A1 (fr) * | 2006-02-02 | 2007-08-08 | Ranbaxy Laboratories, Ltd. | Formes cristallines d'un antagoniste du récepteur cannabinoïde CB1 et son procédé de préparation |
| FR2897060B1 (fr) * | 2006-02-08 | 2008-07-25 | Sanofi Aventis Sa | Le monohydrate de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| WO2008038143A2 (fr) * | 2006-06-22 | 2008-04-03 | Medichem, S.A. | Nouvelles formes solides du rimonabant et procédés de synthèse pour la préparation de celles-ci |
| AR062593A1 (es) * | 2006-08-29 | 2008-11-19 | Medichem Sa | 1-{[5-(4-clorofenil)-1-(2,4-diclorofenil)-4-metil-1h-pirazol-3-il]carbonil}-piperidina y proceso para preparar dicho compuesto; proceso para analizar la pureza de rimonabant,proceso para preparar rimonabant,rimonabant que se obtiene mediante dicho proceso y formulaciones. |
| WO2008026219A2 (fr) * | 2006-09-01 | 2008-03-06 | Hetero Drugs Limited | Nouveaux polymorphes de rimonabant |
| EP2061783A2 (fr) * | 2006-09-11 | 2009-05-27 | Hetero Drugs Limited | Procédé amélioré pour l'obtention de rimonabant |
| WO2008035023A1 (fr) * | 2006-09-19 | 2008-03-27 | Cipla Limited | Formes polymorphes de rimonabant |
| WO2008056377A2 (fr) * | 2006-11-06 | 2008-05-15 | Cadila Healthcare Limited | Nouvelles formes du rimonabant |
| WO2008064615A2 (fr) * | 2006-12-01 | 2008-06-05 | Zentiva, A.S. | Formes cristallines et amorphes du rimonabant et procédés permettant d'obtenir ces formes |
| EP2121659B1 (fr) * | 2006-12-18 | 2013-05-15 | 7TM Pharma A/S | Modulateurs de récepteurs cb1 |
| PE20081849A1 (es) | 2007-01-04 | 2009-01-26 | Prosidion Ltd | Derivados de piperidin-4-il-propoxi-benzamida como agonistas de gpcr |
| EA016507B1 (ru) | 2007-01-04 | 2012-05-30 | Прозидион Лимитед | Пиперидиновые агонисты gpcr |
| CL2008000018A1 (es) | 2007-01-04 | 2008-08-01 | Prosidion Ltd | Compuestos derivados de heterociclos de nitrogeno y oxigeno, agonistas de gpcr; composicion farmaceutica que comprende a dicho compuesto; y uso del compuesto para el tratamiento de la obesidad, diabetes, sindrome metabolico, hiperlipidemia, toleranci |
| GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
| US20100048632A1 (en) | 2007-01-04 | 2010-02-25 | Matthew Colin Thor Fyfe | Piperidine GPCR Agonists |
| EP1944297A1 (fr) * | 2007-01-09 | 2008-07-16 | Miklós Vértessy | Rimonabant solide et cristallin et procédés de préparation, ainsi que composition pharmaceutique correspondante |
| WO2008088900A2 (fr) * | 2007-01-18 | 2008-07-24 | Teva Pharmaceutical Industries Ltd. | Formes polymorphes d'une base de rimonabant et procédés pour leur préparation |
| EP1953144A1 (fr) | 2007-01-30 | 2008-08-06 | Sandoz AG | Nouvelles formes polymorphes de N-pipéridino-5-(4-chlorophényl)-1-(2, 4-dichlorphényl)-4-méthyl-3-pyrazolecarboxamide |
| FR2919863A1 (fr) * | 2007-08-06 | 2009-02-13 | Sanofi Aventis Sa | Le solvate de n-methylpyrrolidone de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| FR2919864A1 (fr) * | 2007-08-06 | 2009-02-13 | Sanofi Aventis Sa | Le solvate de 1,4-dioxane de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| FR2919862A1 (fr) * | 2007-08-06 | 2009-02-13 | Sanofi Aventis Sa | Le solvate de 3-methylbutan-1-ol de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| FR2919865A1 (fr) * | 2007-08-06 | 2009-02-13 | Sanofi Aventis Sa | Le solvate de dmso de rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
| FR2919867A1 (fr) * | 2007-08-06 | 2009-02-13 | Sanofi Aventis Sa | Le solvate de 2-methoxyethanol de rimonabant et son procede de preparation |
| GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
| GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
| WO2009153804A1 (fr) * | 2008-06-16 | 2009-12-23 | Cadila Healthcare Limited | Procédé de préparation de la forme 1 du rimonabant |
| WO2010079241A1 (fr) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Utilisation d'antagonistes et/ou d'agonistes inverses des récepteurs cb1 pour la préparation de médicaments qui augmentent l'excitabilité des motoneurones |
| FR3008620A1 (fr) * | 2013-07-22 | 2015-01-23 | Sanofi Sa | Formulation de comprime d'un inhibiteur de phosphatidylinositol 3-kinase |
| JP7704681B2 (ja) * | 2019-10-16 | 2025-07-08 | 大塚製薬株式会社 | センタナファジンの製造方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2692575B1 (fr) * | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
| FR2713225B1 (fr) * | 1993-12-02 | 1996-03-01 | Sanofi Sa | N-pipéridino-3-pyrazolecarboxamide substitué. |
| US7109245B2 (en) * | 2001-08-15 | 2006-09-19 | The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services | Vasoconstrictor cannabinoid analogs |
| FR2831883B1 (fr) * | 2001-11-08 | 2004-07-23 | Sanofi Synthelabo | Forme polymorphe du rimonabant, son procede de preparation et les compositions pharmaceutiques en contenant |
-
2001
- 2001-11-08 FR FR0114579A patent/FR2831883B1/fr not_active Expired - Fee Related
-
2002
- 2002-04-11 UA UA20040402974A patent/UA76776C2/uk unknown
- 2002-11-04 US US10/494,211 patent/US20050043356A1/en not_active Abandoned
- 2002-11-04 EP EP02785580A patent/EP1446384A1/fr not_active Withdrawn
- 2002-11-04 GE GE5606A patent/GEP20063894B/en unknown
- 2002-11-04 BR BR0213931-6A patent/BR0213931A/pt not_active IP Right Cessation
- 2002-11-04 AU AU2002350869A patent/AU2002350869B2/en not_active Ceased
- 2002-11-04 CN CNB028219686A patent/CN100412063C/zh not_active Expired - Fee Related
- 2002-11-04 IL IL16153302A patent/IL161533A0/xx unknown
- 2002-11-04 KR KR1020047006969A patent/KR20050043774A/ko not_active Abandoned
- 2002-11-04 MX MXPA04004394A patent/MXPA04004394A/es unknown
- 2002-11-04 HR HR20040403A patent/HRP20040403A2/hr not_active Application Discontinuation
- 2002-11-04 NZ NZ532369A patent/NZ532369A/en not_active IP Right Cessation
- 2002-11-04 JP JP2003542151A patent/JP4181994B2/ja not_active Expired - Fee Related
- 2002-11-04 PL PL02369372A patent/PL369372A1/xx not_active Application Discontinuation
- 2002-11-04 RS YU36904A patent/RS36904A/sr unknown
- 2002-11-04 HU HU0402043A patent/HUP0402043A3/hu unknown
- 2002-11-04 AP APAP/P/2004/003024A patent/AP1830A/en active
- 2002-11-04 KR KR1020097016373A patent/KR20090089485A/ko not_active Ceased
- 2002-11-04 WO PCT/FR2002/003765 patent/WO2003040105A1/fr not_active Ceased
- 2002-11-04 OA OA1200400131A patent/OA12721A/fr unknown
- 2002-11-04 EA EA200400491A patent/EA006771B1/ru not_active IP Right Cessation
- 2002-11-04 ME MEP-219/08A patent/MEP21908A/xx unknown
- 2002-11-04 CA CA002464145A patent/CA2464145A1/fr not_active Abandoned
- 2002-11-06 AR ARP020104228A patent/AR037253A1/es unknown
- 2002-11-07 TW TW091132763A patent/TW200302824A/zh unknown
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2004
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- 2004-04-20 IL IL161533A patent/IL161533A/en not_active IP Right Cessation
- 2004-04-20 ZA ZA200402999A patent/ZA200402999B/en unknown
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- 2004-04-28 MA MA27659A patent/MA27080A1/fr unknown
- 2004-05-04 CR CR7333A patent/CR7333A/es unknown
- 2004-05-04 CO CO04040840A patent/CO5580827A2/es not_active Application Discontinuation
- 2004-05-07 NO NO20041879A patent/NO326648B1/no not_active IP Right Cessation
- 2004-05-07 TN TNP2004000079A patent/TNSN04079A1/fr unknown
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2008
- 2008-07-11 JP JP2008181474A patent/JP4931874B2/ja not_active Expired - Fee Related
- 2008-10-28 US US12/259,701 patent/US20100190827A1/en not_active Abandoned
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Discontinued |