DD263050A5 - Verfahren zur herstellung von n,n-dimethyl-1-[1-(4-chlorphenyl)-cyclobutyl]-3-methylbutylamin-hydrochlorid-monohydrat - Google Patents
Verfahren zur herstellung von n,n-dimethyl-1-[1-(4-chlorphenyl)-cyclobutyl]-3-methylbutylamin-hydrochlorid-monohydrat Download PDFInfo
- Publication number
- DD263050A5 DD263050A5 DD86297631A DD29763186A DD263050A5 DD 263050 A5 DD263050 A5 DD 263050A5 DD 86297631 A DD86297631 A DD 86297631A DD 29763186 A DD29763186 A DD 29763186A DD 263050 A5 DD263050 A5 DD 263050A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- dimethyl
- chlorophenyl
- cyclobutyl
- water
- methylbutylamine hydrochloride
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- KFNNPQDSPLWLCX-UHFFFAOYSA-N 1-[1-(4-chlorophenyl)cyclobutyl]-n,n,3-trimethylbutan-1-amine;hydron;chloride;hydrate Chemical compound O.Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 KFNNPQDSPLWLCX-UHFFFAOYSA-N 0.000 title description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 38
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 8
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 claims abstract description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims abstract description 4
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229940093475 2-ethoxyethanol Drugs 0.000 claims abstract description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims abstract description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000008096 xylene Substances 0.000 claims abstract description 4
- 239000011928 denatured alcohol Substances 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 7
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- UWAOJIWUVCMBAZ-UHFFFAOYSA-N [1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl]-dimethylazanium;chloride Chemical compound Cl.C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UWAOJIWUVCMBAZ-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000009835 boiling Methods 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 208000020401 Depressive disease Diseases 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
- C07C211/29—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by halogen atoms or by nitro or nitroso groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858531071A GB8531071D0 (en) | 1985-12-17 | 1985-12-17 | Therapeutic compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD263050A5 true DD263050A5 (de) | 1988-12-21 |
Family
ID=10589895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86297631A DD263050A5 (de) | 1985-12-17 | 1986-12-15 | Verfahren zur herstellung von n,n-dimethyl-1-[1-(4-chlorphenyl)-cyclobutyl]-3-methylbutylamin-hydrochlorid-monohydrat |
Country Status (34)
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8704777D0 (en) * | 1987-02-28 | 1987-04-01 | Boots Co Plc | Medical treatment |
| CA2139000A1 (en) * | 1992-06-23 | 1994-01-06 | James W. Young | Methods and compositions for treating depression and other disorders using optically pure(+) sibutramine |
| AU4542893A (en) * | 1992-06-23 | 1994-01-24 | Sepracor, Inc. | Methods and compositions for treating depression and other disorders using optically pure (-) sibutramine |
| US5459164A (en) * | 1994-02-03 | 1995-10-17 | Boots Pharmaceuticals, Inc. | Medical treatment |
| DE4443891A1 (de) | 1994-12-09 | 1996-06-13 | Bayer Ag | Heterocyclisch substituierte Oxy-phenyl-(phenyl)glycinolamide |
| GB9619757D0 (en) * | 1996-09-21 | 1996-11-06 | Knoll Ag | Chemical process |
| GB9619961D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
| GB9619962D0 (en) * | 1996-09-25 | 1996-11-13 | Knoll Ag | Medical treatment |
| GB9727131D0 (en) | 1997-12-24 | 1998-02-25 | Knoll Ag | Therapeutic agents |
| US6476078B2 (en) | 1999-08-11 | 2002-11-05 | Sepracor, Inc. | Methods of using sibutramine metabolites in combination with a phosphodiesterase inhibitor to treat sexual dysfunction |
| US6974838B2 (en) * | 1998-08-24 | 2005-12-13 | Sepracor Inc. | Methods of treating or preventing pain using sibutramine metabolites |
| US6339106B1 (en) | 1999-08-11 | 2002-01-15 | Sepracor, Inc. | Methods and compositions for the treatment and prevention of sexual dysfunction |
| US6331571B1 (en) * | 1998-08-24 | 2001-12-18 | Sepracor, Inc. | Methods of treating and preventing attention deficit disorders |
| US6696495B2 (en) * | 1998-12-02 | 2004-02-24 | Snowden Pharmaceuticals, Llc | Treatment of disorders secondary to organic impairments |
| US6323242B1 (en) | 1998-12-02 | 2001-11-27 | Peter Sterling Mueller | Treatment of disorders secondary to organic impairments |
| WO2000043002A1 (en) * | 1999-01-20 | 2000-07-27 | Knoll Pharmaceutical Company | Method to aid smoking cessation |
| BG65170B1 (bg) * | 1999-03-17 | 2007-05-31 | Knoll Gmbh | Използване на n-заместени производни на 1-[1-(4-хлорофенил)циклобутил]-3-метилбутиламин за производство на лекарство за лечение на разстройства при храненето |
| US6803387B1 (en) | 1999-03-19 | 2004-10-12 | Abbott Gmbh & Co. Kg | Treatment of neuropathic pain or fibromyalgia |
| PL351958A1 (en) * | 1999-03-19 | 2003-07-14 | Knoll Gmbh | Treatment of some tumours associated with gain in weight |
| US6372798B1 (en) | 1999-03-19 | 2002-04-16 | Knoll Pharmaceutical Company | Treatment of hyperactivity disorders |
| AU3896900A (en) | 1999-03-19 | 2000-10-09 | Knoll Pharmaceutical Company | Treatment of pain |
| CA2366660A1 (en) * | 1999-03-19 | 2000-09-28 | Carl M. Mendel | Treatment of osteoarthritis |
| WO2000056312A1 (en) | 1999-03-19 | 2000-09-28 | Knoll Gmbh | Treatment of pulmonary hypertension |
| US6433020B1 (en) | 1999-03-19 | 2002-08-13 | Knoll Pharmaceutical Company | Treatment of cardiovascular disease |
| US6376554B1 (en) | 1999-03-19 | 2002-04-23 | Knoll Pharmaceutical Company | Method of treating sexual dysfunction |
| US6552087B1 (en) | 1999-03-19 | 2003-04-22 | Abbott Gmbh & Co. Kg | Therapeutic agent comprising (+)-sibutramine |
| US6441046B1 (en) | 1999-03-19 | 2002-08-27 | Abbott Gmbh & Co. Kg | Control of metabolism |
| WO2000056319A1 (en) | 1999-03-19 | 2000-09-28 | Knoll Pharmaceutical Company | Treatment of orthostatic hypotension |
| AU3895300A (en) | 1999-03-19 | 2000-10-09 | Knoll Pharmaceutical Company | Treatment of chronic fatigue syndrome |
| HUP0200501A3 (en) * | 1999-03-19 | 2004-03-29 | Abbott Gmbh & Co Kg | Use of n,n-dimethyl-1-[1-(4chlorophenyl)cyclobutyl]-3-methylbutylamine for treating sleep apnoea |
| US6399826B1 (en) | 1999-08-11 | 2002-06-04 | Sepracor Inc. | Salts of sibutramine metabolites, methods of making sibutramine metabolites and intermediates useful in the same, and methods of treating pain |
| US6380200B1 (en) | 1999-12-07 | 2002-04-30 | Pfizer, Inc. | Combination of aldose reductase inhibitors and selective serotonin reuptake inhibitors for the treatment of diabetic complications |
| US6562974B2 (en) | 2000-02-01 | 2003-05-13 | The Procter & Gamble Company | Process for making geminal bisphosphonates |
| PE20011061A1 (es) | 2000-02-01 | 2001-11-20 | Procter & Gamble | Cristalizacion selectiva del acido 3-piridil-1-hidroxi-etiliden-1,1-bisfosfonico sodio como el hemipentahidrato o el monohidrato |
| US6232347B1 (en) | 2000-03-17 | 2001-05-15 | Knoll Pharmaceutical Company | Treatment of osteoarthritis |
| WO2002083631A1 (en) * | 2001-04-13 | 2002-10-24 | Sepracor Inc. | Methods of preparing didesmethylsibutramine and other sibutramine derivatives |
| ATE486842T1 (de) * | 2002-03-12 | 2010-11-15 | Merck Sharp & Dohme | Substituierte amide |
| MXPA05003355A (es) * | 2002-10-05 | 2005-10-18 | Hanmi Pharm Ind Co Ltd | Composicion farmaceutica que comprende semihidrato de metansulfonato de sibutramina cristalino. |
| KR100536750B1 (ko) * | 2002-10-05 | 2005-12-16 | 한미약품 주식회사 | 시부트라민 메탄술폰산염의 결정성 반수화물을 포함하는약학 조성물 |
| US20040122033A1 (en) * | 2002-12-10 | 2004-06-24 | Nargund Ravi P. | Combination therapy for the treatment of obesity |
| GB0310361D0 (en) * | 2003-05-06 | 2003-06-11 | Cipla Ltd | Pharmaceutical compound |
| US7649002B2 (en) | 2004-02-04 | 2010-01-19 | Pfizer Inc | (3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists |
| US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| ES2328384T3 (es) * | 2004-11-23 | 2009-11-12 | Warner-Lambert Company Llc | Derivados del acido 7-(2h-pirazol-3-il)-3,5-dihidroxi-heptanoico como inhibidores de hmg co-a reductasa para el tratamiento de la lipidemia. |
| WO2006073292A1 (en) | 2005-01-06 | 2006-07-13 | Cj Corporation | Inorganic acid salts of sibutramine |
| US8283312B2 (en) * | 2005-02-04 | 2012-10-09 | The Research Foundation Of State University Of New York | Compositions and methods for modulating body weight and treating obesity-related disorders |
| KR100781882B1 (ko) * | 2005-07-12 | 2007-12-05 | 주식회사유한양행 | 시부트라민을 함유하는 약제학적 조성물 |
| CA2617654A1 (en) * | 2005-08-04 | 2007-02-08 | Pfizer Limited | Piperidinoyl-pyrrolidine and piperidinoyl-piperidine compounds |
| US20090203738A1 (en) * | 2005-09-22 | 2009-08-13 | Eisai R&D Management Co., Ltd. | Pharmaceutical Composition for Treating Bulimia and Depression Arising from Bulimia |
| US8911751B2 (en) * | 2005-10-11 | 2014-12-16 | Yissum Research Development Company Of The Hebrew University Of Jerusalem | Compositions for nasal delivery |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| AU2007219236B2 (en) * | 2006-02-23 | 2012-06-21 | Pfizer Limited | Melanocortin type 4 receptor agonist piperidinoylpyrrolidines |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| MX2009002781A (es) | 2006-09-15 | 2009-03-30 | Reviva Pharmaceuticals Inc | Sintesis, metodos de uso y composiciones de cicloalquilmetilaminas . |
| CN101583593A (zh) | 2006-11-13 | 2009-11-18 | 辉瑞产品公司 | 二芳基、二吡啶基和芳基-吡啶基衍生物及其用途 |
| JP2010510201A (ja) * | 2006-11-20 | 2010-04-02 | グレンマーク・ファーマシューティカルズ・エスエー | ステアリン酸ＣｏＡ脱飽和酵素阻害剤としてのアセチレン誘導体 |
| ATE547394T1 (de) | 2006-12-01 | 2012-03-15 | Bristol Myers Squibb Co | N-((3-benzyl)-2,2-(bis-phenyl)-propan-1- aminderivate als cetp-hemmer für die behandlung von atherosklerose und herz-kreislauf- erkrankungen |
| US20080221057A1 (en) * | 2007-02-16 | 2008-09-11 | Wyeth | Secreted protein ccdc80 regulates adipocyte differentiation |
| US20080249156A1 (en) * | 2007-04-09 | 2008-10-09 | Palepu Nageswara R | Combinations of statins and anti-obesity agent and glitazones |
| WO2008124120A1 (en) * | 2007-04-09 | 2008-10-16 | Scidose, Llc | Combinations of statins and anti-obesity agent |
| WO2009037542A2 (en) | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
| JP5530438B2 (ja) * | 2008-08-06 | 2014-06-25 | ファイザー・リミテッド | Ｍｃ４作動薬としてのジアゼピンおよびジアゾカン化合物 |
| TWI478712B (zh) | 2008-09-30 | 2015-04-01 | Astellas Pharma Inc | 釋控性醫藥組成物 |
| US20120053172A1 (en) | 2009-02-12 | 2012-03-01 | Cooperatieve Mirzorg U.A. | Use of a combination of diazoxide and metformin for treating obesity or obesity related disorders |
| US8669380B2 (en) | 2009-11-02 | 2014-03-11 | Pfizer Inc. | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
| ES2665467T3 (es) | 2010-03-29 | 2018-04-25 | Astellas Pharma Inc. | Composición farmacéutica de liberación modificada |
| WO2012003501A2 (en) | 2010-07-02 | 2012-01-05 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives |
| EA201291384A1 (ru) | 2010-07-06 | 2013-07-30 | Астразенека Аб | Терапевтические агенты 976 |
| MX366925B (es) | 2010-11-04 | 2019-07-31 | Albireo Ab | Inhibidores de ibat para el tratamiento de enfermedades hepaticas. |
| US20130236541A1 (en) | 2010-11-08 | 2013-09-12 | Albireo Ab | Pharmaceutical combination comprising an ibat inhibitor and a bile acid binder |
| UY34194A (es) | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
| EP2890370B1 (en) | 2012-08-31 | 2019-10-09 | The Regents of the University of California | Agents useful for treating obesity, diabetes and related disorders |
| CN110372522B (zh) * | 2019-07-30 | 2020-10-02 | 南京工业大学 | 一种从含有戊二胺的固相中汽提回收戊二胺的方法 |
| US12097189B1 (en) | 2024-02-09 | 2024-09-24 | Astellas Pharma Inc. | Pharmaceutical composition for modified release |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1124485B (de) * | 1960-02-12 | 1962-03-01 | Hoechst Ag | Verfahren zur Herstellung von analeptisch wirksamen Phenylcycloalkylmethylaminen |
| SE7600674L (sv) * | 1975-02-05 | 1976-08-06 | Rohm & Haas | Fungicider |
| ZA821577B (en) * | 1981-04-06 | 1983-03-30 | Boots Co Plc | Therapeutic agents |
| US4443449A (en) * | 1981-04-06 | 1984-04-17 | The Boots Company Limited | Arylcyclobutylalkylamines and anti-depression composition and methods using same |
| IE52768B1 (en) * | 1981-04-06 | 1988-02-17 | Boots Co Ltd | 1-arylcyclobutylalkylamine compounds useful as therapeutic agents |
| GB2115409B (en) * | 1982-02-24 | 1985-08-07 | Zyma Sa | Novel crystal modifications of (+)-catechin |
| DK101683A (da) * | 1982-03-12 | 1983-09-13 | Duphar Int Res | Phenylpiperazinderivater og fremgangsmaade til fremstilling heraf |
| IE56001B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylmethylamine compounds |
| ZA836848B (en) * | 1982-09-30 | 1984-05-30 | Boots Co Plc | Therapeutic agents |
| IE56000B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylalkylamine compounds |
| GB8501192D0 (en) * | 1985-01-17 | 1985-02-20 | Boots Co Plc | Therapeutic agents |
| GB8704777D0 (en) * | 1987-02-28 | 1987-04-01 | Boots Co Plc | Medical treatment |
| JP2675573B2 (ja) * | 1988-03-31 | 1997-11-12 | 科研製薬株式会社 | 脳機能改善剤 |
| IE61928B1 (en) * | 1988-11-29 | 1994-11-30 | Boots Co Plc | Treatment of obesity |
-
1985
- 1985-12-17 GB GB858531071A patent/GB8531071D0/en active Pending
-
1986
- 1986-11-25 IE IE310286A patent/IE59429B1/en not_active IP Right Cessation
- 1986-11-28 IN IN921/MAS/86A patent/IN163129B/en unknown
- 1986-12-02 ZA ZA869078A patent/ZA869078B/xx unknown
- 1986-12-02 YU YU205086A patent/YU46033B/sh unknown
- 1986-12-04 PH PH34552A patent/PH22481A/en unknown
- 1986-12-05 DK DK585786A patent/DK170770B1/da not_active IP Right Cessation
- 1986-12-10 NZ NZ218578A patent/NZ218578A/xx unknown
- 1986-12-10 EP EP86309631A patent/EP0230742B1/en not_active Expired - Lifetime
- 1986-12-10 IL IL80934A patent/IL80934A/xx not_active IP Right Cessation
- 1986-12-10 ES ES86309631T patent/ES2018163T4/es not_active Expired - Lifetime
- 1986-12-10 FI FI865030A patent/FI90413C/fi not_active IP Right Cessation
- 1986-12-10 AT AT86309631T patent/ATE56942T1/de not_active IP Right Cessation
- 1986-12-10 DE DE8686309631T patent/DE3674570D1/de not_active Expired - Lifetime
- 1986-12-11 AU AU66442/86A patent/AU601167B2/en not_active Expired
- 1986-12-15 CS CS869305A patent/CS259545B2/cs not_active IP Right Cessation
- 1986-12-15 UA UA4028642A patent/UA7206A1/uk unknown
- 1986-12-15 DD DD86297631A patent/DD263050A5/de not_active IP Right Cessation
- 1986-12-15 SU SU4028642A patent/SU1443796A3/ru active
- 1986-12-16 JP JP61299806A patent/JPS62155240A/ja active Granted
- 1986-12-16 PL PL1986263020A patent/PL149519B1/pl unknown
- 1986-12-16 MX MX468486A patent/MX4684A/es unknown
- 1986-12-16 KR KR1019860010764A patent/KR940008913B1/ko not_active Expired - Lifetime
- 1986-12-16 NO NO865093A patent/NO165540C/no not_active IP Right Cessation
- 1986-12-16 HU HU865232A patent/HU201901B/hu unknown
- 1986-12-17 CN CN86108547A patent/CN1016245B/zh not_active Expired
- 1986-12-17 EG EG774/86A patent/EG17770A/xx active
- 1986-12-17 PT PT83958A patent/PT83958B/pt unknown
- 1986-12-17 CA CA000525648A patent/CA1266278A/en not_active Expired - Lifetime
-
1989
- 1989-04-19 US US07/342,638 patent/US4929629A/en not_active Expired - Lifetime
-
1990
- 1990-01-19 US US07/467,471 patent/US5068440A/en not_active Expired - Lifetime
- 1990-11-08 GR GR90400895T patent/GR3001069T3/el unknown
-
1994
- 1994-01-20 GE GEAP19941745A patent/GEP19970812B/en unknown
-
2001
- 2001-10-04 NL NL300065C patent/NL300065I1/nl unknown
- 2001-12-18 LU LU90865C patent/LU90865I2/fr unknown
-
2005
- 2005-09-14 NO NO2005022C patent/NO2005022I1/no unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69830503T2 (de) | Tablette mit verlängerter wirkstoffabgabe zur behandlung der parkinsonkrankheit | |
| EP0956281B1 (de) | Neue modifikationen des 2-amino-4-(4-fluorbenzylamino)-1-ethoxycarbonyl-aminobenzen sowie verfahren zu ihrer herstellung | |
| DE3152519C2 (de) | Neues Fenofibrat-Fertigpr{parat mit verz¦gerter Wirkstofffreisetzung | |
| EP1523303B1 (de) | Vardenafil hydrochlorid trihydrat enthaltende arzneimittel und deren herstellungsverfahren | |
| DE69605800T2 (de) | Maleinsäuresalz des (r)-(z)-azabycyclo(2.2.1)heptan-3-one,0-(3-(3-methoxyphenyl)-2-propynyl)oxims | |
| DE19546249A1 (de) | Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE69229339T2 (de) | Kristallines tiagabinehydrochlorid-monohydrat, seine herstellung und verwendung | |
| WO2007140917A2 (de) | KRISTALLINE FORMEN VON 11 ß-(4-ACETYLPHENYL)-20, 20, 21,21, 21-PENTAFLUOR-17- HYDROXY-19-NOR-17α-PREGNA-4,9-DIEN-3-ON | |
| CH631700A5 (de) | Verfahren zur herstellung von neuen substituierten diphenylsulfiden. | |
| DE1949813A1 (de) | Substituierte Pyrazole | |
| DE1940566C3 (de) | 1- (2-Nitrilophenoxy)-2-hydroxy-3äthylaminopropan, Verfahren zu dessen Herstellung und dieses enthaltende Arzneimittel | |
| EP0496274B1 (de) | Tricyclisches Pyridonderivat | |
| DE1620541C3 (de) | Neue in 3-Stellung substituierte 6,8-Dibrom-tetrahydro-chinazoline | |
| DE69715196T2 (de) | Modifizierte form des hydrochlorids der r(-)-n-(4,4-di(-3-methylthien-2-yl)but-3-enyl)-nipecotinsäure | |
| DE1695298C3 (de) | S-Acetamido-e-methyl-e-n-propyl-striazolo eckige Klammer auf 4,3-a eckige Klammer zu pyrazin und Verfahren zu seiner Herstellung und Arzneimittel | |
| DE4235133A1 (de) | Kristallines (R)-(-)-2-Cycloheptyl-N-methylsulfonyl-[4-(2-chinolinyl-methoxy)-phenyl]-acetamid | |
| DE2127812C2 (de) | 3-Methyl-7-phenyl-5H-pyrimido [1,2-a] [1,4] benzodiazepin-1-one und Verfahren zu deren Herstellung | |
| DE1959402A1 (de) | Neue 2-(5-Nitro-2-furyl)-4-oxi-thieno[3,2-d]pyrimidine und Verfahren zu ihrer Herstellung | |
| DE69908771T2 (de) | Tilidin-mesylat, verfahren zu dessen herstellung und pharmazeutische zusammensetzungen | |
| EP0253293B1 (de) | Neue Guanidiniumasparaginate | |
| DE69929315T2 (de) | Kristalline formen von 1s-ä1alpha(2s*,3r*),9alphaü-6,10-dioxo-n- (2-ethoxy-5-oxo-tetrahydro-3-furanyl)-9-ää(1-isochinolyl)carbonylü- aminoüoctahydro-6h-piridazinoä1,2-aüä1,2üdiazepin-1-carboxyamid | |
| DE2748794A1 (de) | Malonylharnstoffderivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen | |
| DE2817112C2 (enExample) | ||
| DE2629133C2 (de) | 5"-Amino-3',5"-didesoxyribostamycin, Verfahren zu dessen Herstellung sowie antimikrobielle Zubereitungen | |
| DE2316802A1 (de) | Neue derivate des phenylbutazons |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |