CA2482669A1 - Crystal forms of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine - Google Patents
Crystal forms of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine Download PDFInfo
- Publication number
- CA2482669A1 CA2482669A1 CA002482669A CA2482669A CA2482669A1 CA 2482669 A1 CA2482669 A1 CA 2482669A1 CA 002482669 A CA002482669 A CA 002482669A CA 2482669 A CA2482669 A CA 2482669A CA 2482669 A1 CA2482669 A1 CA 2482669A1
- Authority
- CA
- Canada
- Prior art keywords
- nateglinide
- solvent
- crystal form
- crystals
- solution
- 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
- 239000013078 crystal Substances 0.000 title claims abstract description 64
- OELFLUMRDSZNSF-OFLPRAFFSA-N (2R)-2-[[oxo-(4-propan-2-ylcyclohexyl)methyl]amino]-3-phenylpropanoic acid Chemical compound C1CC(C(C)C)CCC1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-OFLPRAFFSA-N 0.000 title abstract description 4
- OELFLUMRDSZNSF-BRWVUGGUSA-N nateglinide Chemical compound C1C[C@@H](C(C)C)CC[C@@H]1C(=O)N[C@@H](C(O)=O)CC1=CC=CC=C1 OELFLUMRDSZNSF-BRWVUGGUSA-N 0.000 claims abstract description 69
- 229960000698 nateglinide Drugs 0.000 claims abstract description 69
- 239000002904 solvent Substances 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims abstract description 28
- 238000001556 precipitation Methods 0.000 claims abstract description 10
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 238000001035 drying Methods 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 5
- 238000002844 melting Methods 0.000 claims abstract description 4
- 230000008018 melting Effects 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 claims description 4
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 claims description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 claims description 4
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 239000003973 paint Substances 0.000 claims 1
- 238000002441 X-ray diffraction Methods 0.000 abstract 1
- 238000002329 infrared spectrum Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 150000004677 hydrates Chemical class 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 230000009102 absorption Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000000881 depressing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002955 isolation Methods 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/57—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C233/63—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of rings other than six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37262502P | 2002-04-15 | 2002-04-15 | |
| US60/372,625 | 2002-04-15 | ||
| PCT/EP2003/003864 WO2003087038A1 (en) | 2002-04-15 | 2003-04-14 | Crystal forms of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2482669A1 true CA2482669A1 (en) | 2003-10-23 |
Family
ID=29250881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002482669A Abandoned CA2482669A1 (en) | 2002-04-15 | 2003-04-14 | Crystal forms of n-(trans-4-isopropylcyclohexylcarbonyl)-d-phenylalanine |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US7247746B2 (enExample) |
| EP (1) | EP1497258A1 (enExample) |
| JP (2) | JP4615866B2 (enExample) |
| CN (1) | CN1304366C (enExample) |
| AU (1) | AU2003242520A1 (enExample) |
| BR (1) | BR0309210A (enExample) |
| CA (1) | CA2482669A1 (enExample) |
| WO (1) | WO2003087038A1 (enExample) |
Families Citing this family (58)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6861553B2 (en) | 2002-07-03 | 2005-03-01 | Teva Pharmaceuticals Industries Ltd. | Process for preparing nateglinide and intermediates thereof |
| US7358390B2 (en) | 2002-07-18 | 2008-04-15 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7534913B2 (en) | 2002-07-18 | 2009-05-19 | Teva Pharmaceutica Industries Ltd. | Crystalline form of nateglinide |
| US7148376B2 (en) | 2002-07-18 | 2006-12-12 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US7420084B2 (en) * | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| WO2004020396A1 (en) * | 2002-08-28 | 2004-03-11 | Dr. Reddy's Laboratories Limited | Crystalline form of nateglinide and process for preparation thereof |
| US7449519B2 (en) * | 2003-02-18 | 2008-11-11 | Konishi Co., Ltd. | Curing resin, method for producing same and curing resin composition |
| HU227073B1 (hu) * | 2003-07-10 | 2010-06-28 | Richter Gedeon Nyrt | Eljárás királisan tiszta N-(transz-4-izopropil-ciklohexilkarbonil)-D-fenil-alanin (nateglinid) és kristálymódosulatainak elõállítására, valamint a G-kristálymódosulata |
| US9303038B2 (en) | 2011-09-06 | 2016-04-05 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy and neurological diseases |
| WO2013167990A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of depression |
| JP2015522531A (ja) | 2012-05-07 | 2015-08-06 | セリックスビオ プライヴェート リミテッド | 神経筋疾患及び神経変性疾患の治療のための組成物及び方法 |
| US9738631B2 (en) | 2012-05-07 | 2017-08-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| WO2013167987A1 (en) * | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of diabetes |
| US9309233B2 (en) | 2012-05-08 | 2016-04-12 | Cellix Bio Private Limited | Compositions and methods for the treatment of blood clotting disorders |
| US9266823B2 (en) | 2012-05-08 | 2016-02-23 | Cellix Bio Private Limited | Compositions and methods for the treatment of parkinson's disease |
| US9403826B2 (en) | 2012-05-08 | 2016-08-02 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory disorders |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| US9499526B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| SG11201407318UA (en) | 2012-05-10 | 2014-12-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of metabolic syndrome |
| US9499527B2 (en) | 2012-05-10 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of familial amyloid polyneuropathy |
| US9315461B2 (en) | 2012-05-10 | 2016-04-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurologic diseases |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
| WO2013167997A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of metabolic syndrome |
| WO2013168011A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of chronic pain |
| WO2013168015A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of asthma and allergy |
| US9339484B2 (en) | 2012-05-10 | 2016-05-17 | Cellix Bio Private Limited | Compositions and methods for the treatment of restless leg syndrome and fibromyalgia |
| WO2013168004A2 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of fibromyalgia pain |
| WO2013168000A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of severe pain |
| US9242939B2 (en) | 2012-05-10 | 2016-01-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of respiratory disorders |
| AU2013264820A1 (en) | 2012-05-23 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for treatment of mucositis |
| WO2013175376A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of local pain |
| WO2013175344A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of periodontitis and rheumatoid arthritis |
| AU2013264896A1 (en) | 2012-05-23 | 2014-11-27 | Cellixbio Private Limited | Compositions and methods for the treatment of multiple sclerosis |
| US9498461B2 (en) | 2012-05-23 | 2016-11-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| WO2013175347A2 (en) | 2012-05-23 | 2013-11-28 | Mahesh Kandula | Compositions and methods for the treatment of respiratory disorders |
| US9108942B1 (en) | 2014-11-05 | 2015-08-18 | Mahesh Kandula | Compositions and methods for the treatment of moderate to severe pain |
| WO2014020480A2 (en) | 2012-08-03 | 2014-02-06 | Mahesh Kandula | Compositions and methods for the treatment migraine and neurologic diseases |
| US9624168B2 (en) | 2012-09-06 | 2017-04-18 | Cellix Bio Private Limited | Compositions and methods for the treatment inflammation and lipid disorders |
| CA2873029A1 (en) | 2012-09-08 | 2014-03-13 | Cellixbio Private Limited | Compositions and methods for the treatment of inflammation and lipid disorders |
| US9333187B1 (en) | 2013-05-15 | 2016-05-10 | Cellix Bio Private Limited | Compositions and methods for the treatment of inflammatory bowel disease |
| SG11201509782TA (en) | 2013-06-04 | 2015-12-30 | Cellix Bio Private Ltd | Compositions and methods for the treatment of diabetes and pre-diabetes |
| US9096537B1 (en) | 2014-12-31 | 2015-08-04 | Mahesh Kandula | Compositions and methods for the treatment of mucositis |
| EP3240779B1 (en) | 2014-09-26 | 2020-10-28 | Cellixbio Private Limited | Compositions and methods for the treatment of epilepsy and neurological disorders |
| ES2799309T3 (es) | 2014-09-29 | 2020-12-16 | Cellix Bio Private Ltd | Compuestos y composiciones para el tratamiento de esclerosis múltiple |
| CA2965449C (en) | 2014-10-27 | 2020-11-10 | Cellix Bio Private Limited | Three component salts of fumaric acid monomethyl ester with piperazine or ethylene diamine for the treatment of multiple sclerosis |
| US9321716B1 (en) | 2014-11-05 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic syndrome |
| US10208014B2 (en) | 2014-11-05 | 2019-02-19 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological disorders |
| US9175008B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Prodrugs of anti-platelet agents |
| US9284287B1 (en) | 2014-11-05 | 2016-03-15 | Cellix Bio Private Limited | Compositions and methods for the suppression of carbonic anhydrase activity |
| US9290486B1 (en) | 2014-11-05 | 2016-03-22 | Cellix Bio Private Limited | Compositions and methods for the treatment of epilepsy |
| US9173877B1 (en) | 2014-11-05 | 2015-11-03 | Cellix Bio Private Limited | Compositions and methods for the treatment of local pain |
| US9150557B1 (en) | 2014-11-05 | 2015-10-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of hyperglycemia |
| CN107207411A (zh) | 2014-12-01 | 2017-09-26 | 塞尔利克斯生物私人有限公司 | 用于治疗多发性硬化的组合物和方法 |
| US9206111B1 (en) | 2014-12-17 | 2015-12-08 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological diseases |
| ES2905771T3 (es) | 2015-01-06 | 2022-04-12 | Cellix Bio Private Ltd | Composiciones y procedimientos para el tratamiento de la inflamación y del dolor |
| CN109100430A (zh) * | 2017-06-20 | 2018-12-28 | 珠海同益制药有限公司 | 一种那格列奈手性异构体色谱分析方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6354321A (ja) * | 1985-03-27 | 1988-03-08 | Ajinomoto Co Inc | 血糖降下剤 |
| US5463116A (en) * | 1991-07-30 | 1995-10-31 | Ajinomoto Co., Inc. | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them |
| DE69217762T2 (de) * | 1991-07-30 | 1997-10-09 | Ajinomoto Kk | Kristalle von N-(Trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanin und Verfahren zu ihrer Herstellung |
| EP1435912A4 (en) | 2001-09-12 | 2005-03-30 | Alembic Ltd | NOVEL STABLE CRYSTAL FORM OF N- (TRANS-4-ISOPROPYLCYCLOHEXYL CARBONYL) -D-PHENYLALANINE AND PREPARATION METHOD THEREOF |
| WO2003087039A1 (en) * | 2002-04-15 | 2003-10-23 | Ajinomoto Co., Inc. | Novel nateglinide crystal |
-
2003
- 2003-04-14 US US10/510,927 patent/US7247746B2/en not_active Expired - Fee Related
- 2003-04-14 EP EP03746296A patent/EP1497258A1/en not_active Withdrawn
- 2003-04-14 WO PCT/EP2003/003864 patent/WO2003087038A1/en not_active Ceased
- 2003-04-14 AU AU2003242520A patent/AU2003242520A1/en not_active Abandoned
- 2003-04-14 CN CNB038084368A patent/CN1304366C/zh not_active Expired - Lifetime
- 2003-04-14 JP JP2003583994A patent/JP4615866B2/ja not_active Expired - Fee Related
- 2003-04-14 BR BR0309210-0A patent/BR0309210A/pt not_active IP Right Cessation
- 2003-04-14 CA CA002482669A patent/CA2482669A1/en not_active Abandoned
-
2007
- 2007-06-20 US US11/765,818 patent/US20080081927A1/en not_active Abandoned
-
2008
- 2008-07-21 US US12/220,061 patent/US20080319222A1/en not_active Abandoned
-
2010
- 2010-07-09 JP JP2010156749A patent/JP2010265295A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP1497258A1 (en) | 2005-01-19 |
| AU2003242520A1 (en) | 2003-10-27 |
| CN1646481A (zh) | 2005-07-27 |
| JP2005522503A (ja) | 2005-07-28 |
| CN1304366C (zh) | 2007-03-14 |
| JP4615866B2 (ja) | 2011-01-19 |
| US20080319222A1 (en) | 2008-12-25 |
| US7247746B2 (en) | 2007-07-24 |
| US20050256336A1 (en) | 2005-11-17 |
| WO2003087038A1 (en) | 2003-10-23 |
| US20080081927A1 (en) | 2008-04-03 |
| BR0309210A (pt) | 2005-02-09 |
| JP2010265295A (ja) | 2010-11-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US7247746B2 (en) | Crystal forms of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine | |
| US5463116A (en) | Crystals of N- (trans-4-isopropylcyclohexlycarbonyl)-D-phenylalanine and methods for preparing them | |
| EP0526171B1 (en) | Crystals of N-(trans-4-isopropylcyclohexylcarbonyl)-D-phenylalanine and methods for preparing them | |
| JP5305248B2 (ja) | 新規ナテグリニド結晶 | |
| GB2037754A (en) | Threo - 3 -protected amino - 2 - hydroxy-4oxobutanoic acids or esters, their preparation and their use in the preparation of threo - 3 - amino - 2 - hydroxy-butanoylaminoacetic acids | |
| JP2005522503A5 (enExample) | ||
| AU2018371771A1 (en) | Solid state form of Valbenazine | |
| CN109575023A (zh) | 一种苦参碱长链脂肪酸离子液体及其制备方法与应用 | |
| RU2134690C1 (ru) | 5-ацетамидо-2,3,4,5-тетрадеокси-4-гуанидино-d-глицеро-d-галакто-нон-2- енопиранозоновая кислота в кристаллической форме, способы получения, фармацевтическая композиция и способ ее получения | |
| US7977507B2 (en) | Nateglinide crystals | |
| CN101759708B (zh) | 头孢地嗪钠晶型及其制备方法和含有该晶型的药物组合物 | |
| CN110372635A (zh) | 氢溴酸沃替西汀α晶型的制备方法 | |
| CN109293548A (zh) | 一种高品质HMG-CoA还原酶抑制剂阿托伐他汀钙的制备方法 | |
| JPH11315088A (ja) | 脂溶性白金（ｉｉ）錯体水和物 | |
| JPH078853B2 (ja) | ドーパミン誘導体の製法 | |
| JP2007510715A (ja) | アトバコンの新規な多形およびその調製のプロセス | |
| CN109535060B (zh) | 一种刺猬通路抑制剂及其制备方法和应用 | |
| WO2001068587A1 (en) | Novel crystal of stilbene derivative and process for producing the same | |
| JP3001975B2 (ja) | 結晶性チアガビン塩酸塩−水和物、その製造方法および用途 | |
| US20200002282A1 (en) | Forms of (R)-N-(4-chlorophenyl)-2-(cis-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanamide | |
| CN104945392A (zh) | 结晶型卡格列净一水合物、制备方法及其应用 | |
| FR2521555A1 (fr) | Nouveaux n-((alkylamino) carbonyl) n-(((alkylamino)carbonyl)oxy)-acylamides utiles notamment comme medicaments antineoplasiques | |
| WO2018149327A1 (zh) | 一种卡格列净无定型的制备方法 | |
| Ghosh | Synthesis and Characterization of Polymers Having Steroid Sex Hormones as Pendent Moieties | |
| JPH01228989A (ja) | アスコルビン酸誘導体及びその製造方法並びにアスコルビン酸誘導体からなる抗酸化剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |