HU201901B - Process for producing n,n-dimethyl-1-(1-)4-chloro-phenyl(-cyclobutyl)-3-methyl-butyl-amine-hydrochloride-monohydrate - Google Patents
Process for producing n,n-dimethyl-1-(1-)4-chloro-phenyl(-cyclobutyl)-3-methyl-butyl-amine-hydrochloride-monohydrate Download PDFInfo
- Publication number
- HU201901B HU201901B HU865232A HU523286A HU201901B HU 201901 B HU201901 B HU 201901B HU 865232 A HU865232 A HU 865232A HU 523286 A HU523286 A HU 523286A HU 201901 B HU201901 B HU 201901B
- Authority
- HU
- Hungary
- Prior art keywords
- cyclobutyl
- dimethyl
- water
- chlorophenyl
- hydrochloride
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 title description 2
- 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 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 4
- 239000002609 medium Substances 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims description 3
- 229940093475 2-ethoxyethanol Drugs 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- -1 N, N-dimethyl-1- [1- (4-chlorophenyl) cyclobutyl] -3-methylbutylamine hydride Chemical compound 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 5
- 208000020401 Depressive disease Diseases 0.000 abstract description 2
- 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 12
- 239000000203 mixture Substances 0.000 description 10
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001914 filtration Methods 0.000 description 7
- 239000008194 pharmaceutical composition Substances 0.000 description 7
- 150000004682 monohydrates Chemical class 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 239000011928 denatured alcohol Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000004677 hydrates Chemical class 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 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 2
- 230000002745 absorbent Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AOZISORLJJDLBQ-UHFFFAOYSA-N butyl(methyl)azanium;chloride Chemical compound Cl.CCCCNC AOZISORLJJDLBQ-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000007911 parenteral administration Methods 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
- 239000007858 starting material Substances 0.000 description 1
- 238000011200 topical administration 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
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB858531071A GB8531071D0 (en) | 1985-12-17 | 1985-12-17 | Therapeutic compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT45964A HUT45964A (en) | 1988-09-28 |
| HU201901B true HU201901B (en) | 1991-01-28 |
Family
ID=10589895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU865232A HU201901B (en) | 1985-12-17 | 1986-12-16 | Process for producing n,n-dimethyl-1-(1-)4-chloro-phenyl(-cyclobutyl)-3-methyl-butyl-amine-hydrochloride-monohydrate |
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 |
| CA2138998A1 (en) * | 1992-06-23 | 1994-01-06 | James W. Young | Methods and compositions for treating depression and other disorders using optically pure(-) sibutramine |
| CA2139000A1 (en) * | 1992-06-23 | 1994-01-06 | James W. Young | 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 |
| US6331571B1 (en) | 1998-08-24 | 2001-12-18 | Sepracor, Inc. | Methods of treating and preventing attention deficit disorders |
| 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 |
| 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 |
| ID30432A (id) * | 1999-01-20 | 2001-12-06 | Knoll Pharmaceutical Co | Metode untuk membantu menghentikan merokok |
| 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 |
| WO2000056306A1 (en) * | 1999-03-19 | 2000-09-28 | Knoll Gmbh | Treatment of osteoarthritis |
| US6376554B1 (en) | 1999-03-19 | 2002-04-23 | Knoll Pharmaceutical Company | Method of treating sexual dysfunction |
| AU3895300A (en) | 1999-03-19 | 2000-10-09 | Knoll Pharmaceutical Company | Treatment of chronic fatigue syndrome |
| US6803387B1 (en) | 1999-03-19 | 2004-10-12 | Abbott Gmbh & Co. Kg | Treatment of neuropathic pain or fibromyalgia |
| US6552087B1 (en) | 1999-03-19 | 2003-04-22 | Abbott Gmbh & Co. Kg | Therapeutic agent comprising (+)-sibutramine |
| HK1044462B (en) * | 1999-03-19 | 2006-03-03 | Abbott Gmbh & Co. Kg | Use of sibutramine or its derivative for the treatment of sleep disorders |
| AU3760600A (en) | 1999-03-19 | 2000-10-09 | Knoll Pharmaceutical Company | Treatment of orthostatic hypotension |
| US6433020B1 (en) | 1999-03-19 | 2002-08-13 | Knoll Pharmaceutical Company | Treatment of cardiovascular disease |
| US6441046B1 (en) | 1999-03-19 | 2002-08-27 | Abbott Gmbh & Co. Kg | Control of metabolism |
| EP1171106A1 (en) * | 1999-03-19 | 2002-01-16 | Knoll GmbH | Treatment of certain cancers associated with weight gain |
| WO2000056321A1 (en) | 1999-03-19 | 2000-09-28 | Knoll Pharmaceutical Company | Treatment of hyperactivity disorders |
| AU3896900A (en) | 1999-03-19 | 2000-10-09 | Knoll Pharmaceutical Company | Treatment of pain |
| MXPA01009468A (es) | 1999-03-19 | 2004-03-19 | Knoll Gmbh | Tratamiento de hipertension pulmonar. |
| 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 |
| 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 |
| US6562974B2 (en) | 2000-02-01 | 2003-05-13 | The Procter & Gamble Company | Process for making geminal bisphosphonates |
| US6232347B1 (en) | 2000-03-17 | 2001-05-15 | Knoll Pharmaceutical Company | Treatment of osteoarthritis |
| US6610887B2 (en) | 2001-04-13 | 2003-08-26 | Sepracor Inc. | Methods of preparing didesmethylsibutramine and other sibutramine derivatives |
| DE60334787D1 (de) * | 2002-03-12 | 2010-12-16 | Merck Sharp & Dohme | Substituierte amide |
| WO2004030663A1 (en) * | 2002-10-05 | 2004-04-15 | Hanmi Pharm. Co., Ltd. | Pharmaceutical composition comprising crystalline sibutramine methanesulfonate hemihydrate |
| 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 |
| WO2006056845A1 (en) * | 2004-11-23 | 2006-06-01 | Warner-Lambert Company Llc | 7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as hmg co-a reductase inhibitors for the treatment of lipidemia |
| EP1846359A4 (en) | 2005-01-06 | 2010-03-31 | Cj Cheiljedang Corp | 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 |
| EP1912968A1 (en) * | 2005-08-04 | 2008-04-23 | Pfizer Limited | Piperidinoyl-pyrrolidine and piperidinoyl-piperidine compounds |
| WO2007034910A1 (ja) * | 2005-09-22 | 2007-03-29 | Eisai R & D Management Co., Ltd. | 過食症及び過食症に伴ううつ病の治療用医薬組成物 |
| 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 |
| RS20080371A (en) * | 2006-02-23 | 2009-07-15 | Pfizer Limited, | Melanocortin type 4 receptor agonist piperidinoylpyrrolidines |
| US8383660B2 (en) | 2006-03-10 | 2013-02-26 | Pfizer Inc. | Dibenzyl amine compounds and derivatives |
| US8604244B2 (en) | 2010-07-02 | 2013-12-10 | Reviva Pharmaceuticals, Inc. | Compositions, synthesis, and methods of using cycloalkylmethylamine derivatives |
| MX2009002781A (es) * | 2006-09-15 | 2009-03-30 | Reviva Pharmaceuticals Inc | Sintesis, metodos de uso y composiciones de cicloalquilmetilaminas . |
| AU2007320906A1 (en) | 2006-11-13 | 2008-05-22 | Pfizer Products Inc. | Diaryl, dipyridinyl and aryl-pyridinyl derivatives and uses thereof |
| AU2007323193A1 (en) * | 2006-11-20 | 2008-05-29 | Glenmark Pharmaceuticals S.A. | Acetylene derivatives as Stearoyl CoA Desaturase inhibitors |
| ES2382009T3 (es) | 2006-12-01 | 2012-06-04 | Bristol-Myers Squibb Company | Derivados de N-((3-bencil)-2,2-(bis-fenil-)-propan-1-amina como inhibidores de CETP para el tratamiento de aterosclerosis y enfermedades cardiovasculares |
| US20080221057A1 (en) * | 2007-02-16 | 2008-09-11 | Wyeth | Secreted protein ccdc80 regulates adipocyte differentiation |
| US20080248115A1 (en) * | 2007-04-09 | 2008-10-09 | Palepu Nageswara R | Combinations of statins and anti-obesity agent |
| WO2008124122A1 (en) * | 2007-04-09 | 2008-10-16 | Scidose, Llc | Combinations of statins and anti-obesity agent and glitazones |
| WO2009037542A2 (en) | 2007-09-20 | 2009-03-26 | Glenmark Pharmaceuticals, S.A. | Spirocyclic compounds as stearoyl coa desaturase inhibitors |
| CN102171206B (zh) * | 2008-08-06 | 2014-06-25 | 辉瑞股份有限公司 | 作为mc4激动剂的二氮杂环庚烷和二氮杂环辛烷 |
| TWI478712B (zh) | 2008-09-30 | 2015-04-01 | Astellas Pharma Inc | 釋控性醫藥組成物 |
| WO2010093243A1 (en) | 2009-02-12 | 2010-08-19 | Coöperatieve Mirzorg U.A., Arnhem | Use of a combination of diazoxide and metformin for treating obesity or obesity related disorders |
| DK2496583T3 (en) | 2009-11-02 | 2015-02-02 | Pfizer | Dioxa-bicyclo [3.2.1] octane-2,3,4-triol DERIVATIVES |
| TR201802207T4 (tr) | 2010-03-29 | 2018-03-21 | Astellas Pharma Inc | Kontrollü Salımlı Farmasötik Bileşim. |
| SG186275A1 (en) | 2010-07-06 | 2013-01-30 | Astrazeneca Ab | Therapeutic agents 976 |
| AU2011326871B2 (en) | 2010-11-04 | 2015-02-12 | Albireo Ab | IBAT inhibitors for the treatment of liver diseases |
| DK2637646T3 (en) | 2010-11-08 | 2016-08-29 | Albireo Ab | PHARMACEUTICAL COMBINATION CONTAINING 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 |
| IE52768B1 (en) * | 1981-04-06 | 1988-02-17 | Boots Co Ltd | 1-arylcyclobutylalkylamine compounds useful as therapeutic agents |
| US4443449A (en) * | 1981-04-06 | 1984-04-17 | The Boots Company Limited | Arylcyclobutylalkylamines and anti-depression composition and methods using same |
| ZA821577B (en) * | 1981-04-06 | 1983-03-30 | Boots Co Plc | 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 |
| IE56000B1 (en) * | 1982-09-30 | 1991-03-13 | Boots Co Plc | 1-arylcyclobutylalkylamine compounds |
| ZA836848B (en) * | 1982-09-30 | 1984-05-30 | Boots Co Plc | Therapeutic agents |
| 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 YU YU205086A patent/YU46033B/sh unknown
- 1986-12-02 ZA ZA869078A patent/ZA869078B/xx 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 FI FI865030A patent/FI90413C/fi not_active IP Right Cessation
- 1986-12-10 NZ NZ218578A patent/NZ218578A/xx unknown
- 1986-12-10 IL IL80934A patent/IL80934A/xx not_active IP Right Cessation
- 1986-12-10 EP EP86309631A patent/EP0230742B1/en not_active Expired - Lifetime
- 1986-12-10 ES ES86309631T patent/ES2018163T4/es not_active Expired - Lifetime
- 1986-12-10 DE DE8686309631T patent/DE3674570D1/de not_active Expired - Lifetime
- 1986-12-10 AT AT86309631T patent/ATE56942T1/de not_active IP Right Cessation
- 1986-12-11 AU AU66442/86A patent/AU601167B2/en not_active Expired
- 1986-12-15 SU SU4028642A patent/SU1443796A3/ru active
- 1986-12-15 UA UA4028642A patent/UA7206A1/uk unknown
- 1986-12-15 CS CS869305A patent/CS259545B2/cs not_active IP Right Cessation
- 1986-12-15 DD DD86297631A patent/DD263050A5/de not_active IP Right Cessation
- 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 PL PL1986263020A patent/PL149519B1/pl unknown
- 1986-12-16 HU HU865232A patent/HU201901B/hu unknown
- 1986-12-16 JP JP61299806A patent/JPS62155240A/ja active Granted
- 1986-12-16 MX MX468486A patent/MX4684A/es unknown
- 1986-12-17 PT PT83958A patent/PT83958B/pt unknown
- 1986-12-17 EG EG774/86A patent/EG17770A/xx active
- 1986-12-17 CN CN86108547A patent/CN1016245B/zh not_active Expired
- 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 |
|---|---|---|
| HU201901B (en) | Process for producing n,n-dimethyl-1-(1-)4-chloro-phenyl(-cyclobutyl)-3-methyl-butyl-amine-hydrochloride-monohydrate | |
| Ettlinger | Synthesis of the Natural Antithyroid Factor l-5-Vinyl-2-thioöxazolidone1 | |
| US4942166A (en) | Crystalline purine compounds | |
| HU211862A9 (en) | Azithromycin dihydrate | |
| SK285303B6 (sk) | Modifikácie 2-amino-4-(4-fluórbenzylamino)-1- etoxykarbonylaminobenzénu, spôsob ich prípravy, ich použitie a liečivá s ich obsahom | |
| JP2003530321A (ja) | Ｎ−［４−［２−（２−アミノ−４，７−ジヒドロ−４−オキソ−３Ｈ−ピロロ［２，３−ｄ］ピリミジン−５−イル）エチル］ベンゾイル］−Ｌ−グルタミン酸の新規結晶形およびその製造方法 | |
| EP3433233B1 (en) | Novel crystalline form of 1-(5-(2,4-difluorophenyl)-1-((3- fluorophenyl)sulfonyl)-4-methoxy-1h-pyrrol-3-yl)-n- methylmethanamine salt | |
| EP0579681B1 (en) | Crystalline tiagabine hydrochloride monohydrate, its preparation and use | |
| JP3726291B2 (ja) | 安定な結晶構造を有するベンゾオキサジン化合物およびその製造法 | |
| CN102321019B (zh) | 喹啉化合物的晶形及其生产方法 | |
| US7132541B2 (en) | Crystalline fluoroquinolone arginine salt form | |
| US4279914A (en) | Thrombocyte aggregation inhibiting composition and methods | |
| GB2184122A (en) | N,n-dimethyl-1-1-(4-chlorophenyl)cyclobutyl-3-methylbutylamine saltt | |
| HU187644B (en) | Process for preparing 2-amino-3-/halogen-benzoyl/-methyl-phenylacetic acid, esters and salts thereof | |
| JPS6256478A (ja) | ジアゼピン−１１−オン、その単離法および医薬組成物 | |
| HU192799B (en) | Process for producing rolling cristalline cristalline oxytetracycline-hydrochloride | |
| JP2676113B2 (ja) | 安定な結晶性の塩およびそれを含有するトロンボキサン受容体拮抗剤 | |
| KR20020005055A (ko) | 엔케이-1 수용체 길항물질로서 사용하기 위한 결정성(2-벤즈하이드릴-1-아자비사이클로[2.2.2]옥트-3-일)-(5-이소프로필-2-메톡시벤질)-아민 시트레이트의 다형태 | |
| HU210876A9 (en) | Arginine derivatives | |
| SK143697A3 (en) | A process for preparing form 1 ranitidine hydrochloride | |
| JP4693236B2 (ja) | １−メチル−５−ｐ−トルオイルピロール−２−アセトアミド酢酸グアイアシルエステル（ＭＥＤ１５）の新規多形結晶 | |
| JP2860385B2 (ja) | ビスべンジルイソキノリン誘導体 | |
| KR880001235B1 (ko) | 결정성 무수 소듐 19-데옥시아글리콘 디아네마이신의 제조 방법 | |
| US3944563A (en) | 1-Amino-pyrazolic derivatives | |
| FI94248B (fi) | Menetelmä terapeuttisesti käyttökelpoisen 2-(1-(pentyyli-3-guanidino)-2-metyyli-4-imidatsolyyli)tiatsolihemifosfaattihemihydraattisuolan valmistamiseksi |