JP2010539166A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2010539166A5 JP2010539166A5 JP2010524866A JP2010524866A JP2010539166A5 JP 2010539166 A5 JP2010539166 A5 JP 2010539166A5 JP 2010524866 A JP2010524866 A JP 2010524866A JP 2010524866 A JP2010524866 A JP 2010524866A JP 2010539166 A5 JP2010539166 A5 JP 2010539166A5
- Authority
- JP
- Japan
- Prior art keywords
- deuterated
- nhc
- coor
- nhr
- structural formula
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 22
- 229910052805 deuterium Inorganic materials 0.000 claims description 21
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 20
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 17
- 125000001188 haloalkyl group Chemical group 0.000 claims description 16
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical group C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 15
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 230000000155 isotopic effect Effects 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- AHOUBRCZNHFOSL-YOEHRIQHSA-N (+)-Casbol Chemical class C1=CC(F)=CC=C1[C@H]1[C@H](COC=2C=C3OCOC3=CC=2)CNCC1 AHOUBRCZNHFOSL-YOEHRIQHSA-N 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 150000003836 berberines Chemical class 0.000 claims description 9
- -1 deuterium Deuterated paroxetine Chemical class 0.000 claims description 8
- IEHKWSGCTWLXFU-IIBYNOLFSA-N tadalafil Chemical class C1=C2OCOC2=CC([C@@H]2C3=C([C]4C=CC=CC4=N3)C[C@H]3N2C(=O)CN(C3=O)C)=C1 IEHKWSGCTWLXFU-IIBYNOLFSA-N 0.000 claims description 7
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 5
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical group C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 230000035807 sensation Effects 0.000 claims description 2
- 230000001052 transient effect Effects 0.000 claims description 2
- 208000033830 Hot Flashes Diseases 0.000 claims 1
- 206010060800 Hot flush Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000006184 cosolvent Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- VGGNVBNNVSIGKG-UHFFFAOYSA-N n,n,2-trimethylaziridine-1-carboxamide Chemical compound CC1CN1C(=O)N(C)C VGGNVBNNVSIGKG-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 0 *C1(*)Oc2cc(OC[C@](CNCC3)[C@@]3c(cc3)ccc3F)ccc2O1 Chemical compound *C1(*)Oc2cc(OC[C@](CNCC3)[C@@]3c(cc3)ccc3F)ccc2O1 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AOBNZDKYCFWNRA-UHFFFAOYSA-N C=[O]C1(O)Oc2ccccc2O1 Chemical compound C=[O]C1(O)Oc2ccccc2O1 AOBNZDKYCFWNRA-UHFFFAOYSA-N 0.000 description 1
- BWIIFMQXXSSPDD-UHFFFAOYSA-N Cc(c(C)c1)cc2c1OC(O)(O)O2 Chemical compound Cc(c(C)c1)cc2c1OC(O)(O)O2 BWIIFMQXXSSPDD-UHFFFAOYSA-N 0.000 description 1
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99356507P | 2007-09-13 | 2007-09-13 | |
| US60/993,565 | 2007-09-13 | ||
| PCT/US2008/010643 WO2009035652A1 (en) | 2007-09-13 | 2008-09-12 | Synthesis of deuterated catechols and benzo[d][1,3] dioxoles and derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010539166A JP2010539166A (ja) | 2010-12-16 |
| JP2010539166A5 true JP2010539166A5 (OSRAM) | 2012-11-01 |
| JP5647519B2 JP5647519B2 (ja) | 2014-12-24 |
Family
ID=40116877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010524866A Expired - Fee Related JP5647519B2 (ja) | 2007-09-13 | 2008-09-12 | 重水素化カテコールおよびベンゾ［ｄ］［１，３］ジオキソールおよびその誘導体の合成 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US8822498B2 (OSRAM) |
| EP (2) | EP2727915B1 (OSRAM) |
| JP (1) | JP5647519B2 (OSRAM) |
| CN (1) | CN101855218A (OSRAM) |
| AU (1) | AU2008299921B2 (OSRAM) |
| CA (1) | CA2698808A1 (OSRAM) |
| MX (1) | MX2010002692A (OSRAM) |
| WO (1) | WO2009035652A1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101380190B1 (ko) * | 2005-07-29 | 2014-04-11 | 콘서트 파마슈티컬즈, 인크. | 벤조 〔ｄ〕〔１,３〕―디옥솔 유도체 |
| CA2629514A1 (en) * | 2005-11-14 | 2007-05-24 | Auspex Pharmaceuticals, Inc. | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| JP5647519B2 (ja) | 2007-09-13 | 2014-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | 重水素化カテコールおよびベンゾ［ｄ］［１，３］ジオキソールおよびその誘導体の合成 |
| HUE047354T2 (hu) | 2011-05-18 | 2020-04-28 | Vertex Pharmaceuticals Europe Ltd | Ivacaftor deuterizált származékai |
| ES2758028T3 (es) * | 2011-05-18 | 2020-05-04 | Vertex Pharmaceuticals Europe Ltd | Derivados deuterados de ivacaftor |
| US20120302526A1 (en) * | 2011-05-27 | 2012-11-29 | Regents Of The University Of Colorado, A Body Corporate | Methods for treating post-traumatic stress disorder |
| CN102924426B (zh) * | 2012-11-14 | 2014-07-02 | 广西师范大学 | 胡椒乙胺缩5-氯水杨醛及其合成方法和应用 |
| CN102942554B (zh) * | 2012-11-14 | 2014-05-28 | 广西师范大学 | 胡椒乙胺缩水杨醛及其合成方法和应用 |
| CN106459059B (zh) | 2014-05-13 | 2019-09-24 | 豪夫迈·罗氏有限公司 | 氘化杂环化合物和其作为成像剂的用途 |
| CN104059030B (zh) * | 2014-05-30 | 2016-05-04 | 镇江圣安医药有限公司 | [(苯硫烷基)-苯基]哌嗪的衍生物及其药物组合物和用途 |
| CN103980271B (zh) * | 2014-05-30 | 2015-12-02 | 天津长森药业有限公司 | 黄藤素及其类似物的制备方法 |
| AU2015296098B2 (en) * | 2014-07-29 | 2019-06-27 | Shenzhen Hightide Biopharmaceutical, Ltd. | Berberine salts, ursodeoxycholic salts and combinations, methods of preparation and application thereof |
| WO2016109795A1 (en) | 2014-12-31 | 2016-07-07 | Concert Pharmaceuticals, Inc. | Deuterated funapide and difluorofunapide |
| AU2016243171B2 (en) | 2015-03-31 | 2020-10-08 | Concert Pharmaceuticals, Inc. | Deuterated VX-661 |
| HK1258473A1 (zh) | 2015-09-25 | 2019-11-15 | Vertex Pharmaceuticals (Europe) Limited | 氘代cftr增效剂 |
| WO2017143874A1 (zh) * | 2016-02-25 | 2017-08-31 | 深圳市塔吉瑞生物医药有限公司 | 一种取代的恶二唑类化合物及包含该化合物的组合物及其用途 |
| KR101970326B1 (ko) * | 2016-08-05 | 2019-04-18 | 고려대학교 산학협력단 | 당 부가된 엔클로미펜, 이의 제조방법 및 이를 포함하는 약학적 조성물 |
| IL305169B2 (en) | 2017-12-01 | 2025-07-01 | Vertex Pharma | Processes for making modulators of cystic fibrosis transmembrane conductance regulator |
| CN113735847B (zh) * | 2021-09-10 | 2022-06-07 | 四川大学 | 一种盐酸小檗碱的合成制备方法 |
Family Cites Families (85)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1422263A (en) | 1973-01-30 | 1976-01-21 | Ferrosan As | 4-phenyl-piperidine compounds |
| US4585777A (en) | 1984-02-07 | 1986-04-29 | A/S Ferrosan | (-)-Trans-4-(4-fluorophenyl)-3-(4-methoxyphenoxy)methylpiperidine for potentiating 5-HT |
| EP0335918A1 (en) * | 1987-08-07 | 1989-10-11 | Mallinckrodt Diagnostica (Holland) B.V. | Diagnostic or radiotherapeutic composition comprising a hydrogen containing compound |
| US5304121A (en) | 1990-12-28 | 1994-04-19 | Boston Scientific Corporation | Drug delivery system making use of a hydrogel polymer coating |
| US5708035A (en) | 1991-02-04 | 1998-01-13 | Sepracor Inc. | Methods of use and compositions of R(-) fluoxetine |
| US5384327A (en) | 1992-12-22 | 1995-01-24 | Mcneilab, Inc. | Anticonvulsant sorbopyranose sulfamates |
| US5886026A (en) | 1993-07-19 | 1999-03-23 | Angiotech Pharmaceuticals Inc. | Anti-angiogenic compositions and methods of use |
| US6221335B1 (en) | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| CA2186371A1 (en) | 1994-03-25 | 1995-10-05 | Robert T. Foster | Enhancement of the efficacy of dihydropyridines by deuteration |
| US5597826A (en) | 1994-09-14 | 1997-01-28 | Pfizer Inc. | Compositions containing sertraline and a 5-HT1D receptor agonist or antagonist |
| US6099562A (en) | 1996-06-13 | 2000-08-08 | Schneider (Usa) Inc. | Drug coating with topcoat |
| GB9514842D0 (en) | 1995-07-20 | 1995-09-20 | Smithkline Beecham Plc | Novel formulation |
| US5958429A (en) | 1996-08-16 | 1999-09-28 | Eli Lilly And Company | Potentiation of serotonin response |
| UA56185C2 (uk) | 1996-09-30 | 2003-05-15 | Пфайзер Інк. | Аралкіл- та аралкіліденгетероциклічні лактами та іміди, фармацевтична композиція та спосіб лікування |
| US5776969A (en) | 1997-02-27 | 1998-07-07 | Eli Lilly And Company | Treatment of sleep disorders |
| CA2287397A1 (en) | 1997-04-24 | 1998-10-29 | Merck Sharp & Dohme Limited | Use of an nk-1 receptor antagonist and an ssri for treating obesity |
| IT1291320B1 (it) | 1997-05-08 | 1999-01-07 | Borregaard Italia Spa | Procedimento per la preparazione di composti aromatici contenenti un sistema eterociclico |
| SK283394B6 (sk) | 1997-06-10 | 2003-07-01 | Synthon B. V. | Zlúčeniny 4-fenylpiperidínu a jej farmaceuticky prijateľné soli, spôsob ich prípravy, liečivo s ich obsahom a ich použitie |
| JP2001518520A (ja) | 1997-10-03 | 2001-10-16 | キャリー メディカル コーポレイション | ニコチンレセプターアンタゴニストおよび抗抑うつ薬または抗不安薬を含有するニコチン嗜癖を治療する組成物 |
| US6403597B1 (en) | 1997-10-28 | 2002-06-11 | Vivus, Inc. | Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation |
| NZ506227A (en) | 1998-03-17 | 2003-06-30 | Pfizer Prod Inc | Bicyclo[2.2.1]heptanes and their use in treating neurological and psychiatric disorders |
| US20030187269A1 (en) | 1998-04-17 | 2003-10-02 | Curzons Alan David | Novel process |
| GB9817195D0 (en) | 1998-08-07 | 1998-10-07 | Smithkline Beecham Plc | Novel process |
| US6376531B1 (en) | 1998-11-13 | 2002-04-23 | Rupert Charles Bell | Method of treatment using deuterium compounds |
| US6440710B1 (en) | 1998-12-10 | 2002-08-27 | The Scripps Research Institute | Antibody-catalyzed deuteration, tritiation, dedeuteration or detritiation of carbonyl compounds |
| CA2360683A1 (en) | 1999-01-28 | 2000-08-03 | Joseph P. Yevich | Antidepressant heterocyclic compounds |
| US20030055070A1 (en) | 1999-07-01 | 2003-03-20 | Wilma Harrison | Phosphodiesterase type 5 (PDE5) inhibitors for the treatment of selective serotonin reuptake inhibitor (SSR) induced sexual dysfunction |
| GB9916187D0 (en) | 1999-07-09 | 1999-09-08 | Smithkline Beecham Plc | Novel process |
| IL137937A0 (en) | 1999-08-27 | 2001-10-31 | Pfizer Prod Inc | A pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal |
| PT1104760E (pt) | 1999-12-03 | 2003-06-30 | Pfizer Prod Inc | Compostos de sulfamoil-heteroarilpirazole como agentes analgesicos e anti-inflamatorios |
| EP1134290A3 (en) | 2000-03-14 | 2004-01-02 | Pfizer Products Inc. | Pharmacophore models for the identification of the CYP2D6 inhibitory potency of selective serotonin reuptake inhibitors |
| US20010036943A1 (en) | 2000-04-07 | 2001-11-01 | Coe Jotham W. | Pharmaceutical composition for treatment of acute, chronic pain and/or neuropathic pain and migraines |
| US20040229911A1 (en) | 2000-05-17 | 2004-11-18 | Pfizer Inc | New pharmaceutical combinations for NOS inhibitors |
| DOP2001000154A (es) | 2000-05-25 | 2002-05-15 | Pfizer Prod Inc | Combinación de secretagogos de hormona del crecimiento y antidepresivos |
| EP1181933A3 (en) | 2000-06-29 | 2002-04-10 | Pfizer Products Inc. | Use of growth hormone secretagogues for stimulating or increasing appetite |
| US6369051B1 (en) | 2000-07-06 | 2002-04-09 | American Home Products Corporation | Combinations of SSRI and estrogenic agents |
| US20020077323A1 (en) | 2000-07-12 | 2002-06-20 | Mclean Stafford | Use of delta opioid receptor ligands and serotonin reuptake inhibitors in the treatment of chemical dependencies |
| GB0025354D0 (en) | 2000-10-17 | 2000-11-29 | Glaxo Group Ltd | Chemical compounds |
| US6436938B1 (en) | 2001-01-22 | 2002-08-20 | Pfizer Inc. | Combination treatment for depression |
| US6720003B2 (en) | 2001-02-16 | 2004-04-13 | Andrx Corporation | Serotonin reuptake inhibitor formulations |
| WO2002085871A2 (en) | 2001-04-04 | 2002-10-31 | Wyeth | Serotonergic agents with long-acting in vivo effects |
| US6656951B2 (en) | 2001-04-24 | 2003-12-02 | Wyeth | 8-aza-bicyclo[3.2.1]octan-3-ol derivatives of 2,3-dihydro-1,4-benzodioxan as 5-HT1A antagonists |
| WO2002088132A1 (en) | 2001-04-26 | 2002-11-07 | Wyeth | Azaheterocyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinoline as 5-ht1aantagonists |
| US6780860B2 (en) | 2001-04-26 | 2004-08-24 | Wyeth | Azabicyclylmethyl derivatives of 7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthalene as 5-ht1a antagonists |
| US6861427B2 (en) | 2001-04-26 | 2005-03-01 | Wyeth | Azabicyclylmethyl derivatives of 2,3-dihydro-1,4-dioxino[2,3-f]quinoline as 5-HT1A antagonists |
| US6815448B2 (en) | 2001-05-07 | 2004-11-09 | Wyeth | Azaheterocyclylmethyl derivatives of 7,8-dihydro-1,6,9-trioxa-3-aza-cyclopenta[a]naphthalene as 5-HT1A antagonists |
| EP1392262A1 (en) | 2001-05-24 | 2004-03-03 | Alexza Molecular Delivery Corporation | Delivery of drug esters through an inhalation route |
| WO2003022283A1 (en) | 2001-09-13 | 2003-03-20 | Schering Corporation | Combination of an adenosine a2a receptor antagonist and an antidepressant or anxiolytic |
| US7019010B2 (en) | 2001-09-27 | 2006-03-28 | Novertis Ag | Combinations |
| JP2005519876A (ja) | 2001-11-27 | 2005-07-07 | メルク エンド カムパニー インコーポレーテッド | ２−アミノキノリン化合物 |
| WO2003045920A1 (en) | 2001-11-27 | 2003-06-05 | Merck & Co., Inc. | 4-aminoquinoline compounds |
| US20050014848A1 (en) | 2002-01-23 | 2005-01-20 | Pfizer Inc. | Combination of serotonin reuptake inhibitors and norephinephrine reuptake inhibitors |
| AU2003209388A1 (en) | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| ES2345437T3 (es) | 2002-03-13 | 2010-09-23 | Schering Corporation | Antagonistas de nk1. |
| TW200413273A (en) | 2002-11-15 | 2004-08-01 | Wako Pure Chem Ind Ltd | Heavy hydrogenation method of heterocyclic rings |
| DE10261807A1 (de) | 2002-12-19 | 2004-07-01 | Turicum Drug Development Ag | Deuterierte Catecholaminderivate sowie diese Verbindungen enthaltende Arzneimittel |
| US20040224943A1 (en) | 2003-02-19 | 2004-11-11 | Leventer Steven M. | Method of lowering body temperature with (R) - 2,3-benzodiazepines |
| BRPI0411891A (pt) | 2003-06-27 | 2006-08-29 | Pfizer Prod Inc | pirazol[3,4-b]piridin-6-onas como inibidores de gsk-3 |
| US20050070577A1 (en) | 2003-07-03 | 2005-03-31 | Pfizer Inc. | Compositions containing a serotonin selective reuptake inhibitor and a 5-HT2A receptor antagonist |
| US20050080084A1 (en) | 2003-07-11 | 2005-04-14 | Pharmacia Corporation | Compositions of a cyclooxygenase-2 selective inhibitor and a serotonin-modulating agent for the treatment of central nervous system damage |
| US20050014786A1 (en) | 2003-07-11 | 2005-01-20 | Chongqing Sun | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
| US7326706B2 (en) | 2003-08-15 | 2008-02-05 | Bristol-Myers Squibb Company | Pyrazine modulators of cannabinoid receptors |
| BRPI0413679A (pt) | 2003-08-22 | 2006-10-24 | Pharmacia Corp | formulações de um inibidor seletivo da ciclooxigenase-2 e de um agente de modulação da serotonina para o tratamento da neoplasia |
| WO2005037199A2 (en) | 2003-10-10 | 2005-04-28 | Bristol-Myers Squibb Company | Pyrazole derivatives as cannabinoid receptor modulators |
| ES2282927T3 (es) | 2003-12-19 | 2007-10-16 | Bristol-Myers Squibb Company | Heterociclos azabiciclicos como moduladores de receptores canabinoides. |
| WO2005107716A1 (en) | 2004-03-25 | 2005-11-17 | Cadila Healthcare Limited | Controlled release paroxetine-containing tablets based on a core and a coating |
| FR2869033B1 (fr) | 2004-04-20 | 2006-06-02 | Rhodia Chimie Sa | Procede de preparation de methylenedioxybenzene |
| US20050266082A1 (en) | 2004-05-26 | 2005-12-01 | Patel Satishkumar A | Preparation of stable paroxetine HC1 ER tablets using a melt granulation process |
| KR100920856B1 (ko) | 2004-11-30 | 2009-10-09 | (주)아모레퍼시픽 | 선택적 세로토닌 재흡수 억제제의 연장방출 제제 및 그제조방법 |
| US20080213381A1 (en) | 2005-03-14 | 2008-09-04 | Pharmaceutical Industries Limited | Oral Drug Delivery System |
| KR20070009934A (ko) | 2005-07-16 | 2007-01-19 | 주식회사 씨티씨바이오 | 염산 파록세틴 서방정 및 이의 제조방법 |
| US7863274B2 (en) * | 2005-07-29 | 2011-01-04 | Concert Pharmaceuticals Inc. | Deuterium enriched analogues of tadalafil as PDE5 inhibitors |
| KR101380190B1 (ko) | 2005-07-29 | 2014-04-11 | 콘서트 파마슈티컬즈, 인크. | 벤조 〔ｄ〕〔１,３〕―디옥솔 유도체 |
| BRPI0615972A2 (pt) * | 2005-07-29 | 2011-05-31 | Concert Pharmaceuticals Inc | composto isolado, mistura, composição, item de manufatura, uso de um composto, método para determinar a concentração do composto em uma amostra biológica, kit de diagnóstico e método para avaliar a estabilidade metabólica de um composto |
| US20080033011A1 (en) | 2005-07-29 | 2008-02-07 | Concert Pharmaceuticals Inc. | Novel benzo[d][1,3]-dioxol derivatives |
| WO2007015270A2 (en) | 2005-08-02 | 2007-02-08 | Lupin Limited | Novel controlled release compositions of selective serotonin reuptake inhibitors |
| CN101309917B (zh) | 2005-10-06 | 2013-09-11 | 奥斯拜客斯制药有限公司 | 具有增强治疗性质的胃h+，k+-atp酶氘代抑制剂 |
| CA2629514A1 (en) | 2005-11-14 | 2007-05-24 | Auspex Pharmaceuticals, Inc. | Substituted phenylpiperidines with serotoninergic activity and enhanced therapeutic properties |
| US7750168B2 (en) | 2006-02-10 | 2010-07-06 | Sigma-Aldrich Co. | Stabilized deuteroborane-tetrahydrofuran complex |
| JO2630B1 (en) | 2006-04-13 | 2012-06-17 | نوفارتيس ايه جي | Organic compounds |
| US20090291958A1 (en) | 2006-06-08 | 2009-11-26 | Auspex Pharmaceuticals, Inc. | Substituted PDE5 inhibitors |
| WO2008016677A2 (en) | 2006-08-02 | 2008-02-07 | Auspex Pharmaceuticals, Inc. | Preparation and utility of deuterated amphetamines |
| CA2661404A1 (en) | 2006-09-05 | 2008-03-13 | Schering Corporation | Pharmaceutical combinations for lipid management and in the treatment of atherosclerosis and hepatic steatosis |
| JP5647519B2 (ja) | 2007-09-13 | 2014-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | 重水素化カテコールおよびベンゾ［ｄ］［１，３］ジオキソールおよびその誘導体の合成 |
| WO2011011420A2 (en) * | 2009-07-21 | 2011-01-27 | Auspex Pharmaceuticals, Inc. | 3, 4-methylenedioxyphenyl inhibitors of gaba aminotransferase and/or gaba reuptake transporter inhibitor |
-
2008
- 2008-09-12 JP JP2010524866A patent/JP5647519B2/ja not_active Expired - Fee Related
- 2008-09-12 EP EP13185607.2A patent/EP2727915B1/en not_active Not-in-force
- 2008-09-12 EP EP08830527.1A patent/EP2200997B9/en not_active Not-in-force
- 2008-09-12 CN CN200880110558A patent/CN101855218A/zh active Pending
- 2008-09-12 WO PCT/US2008/010643 patent/WO2009035652A1/en not_active Ceased
- 2008-09-12 MX MX2010002692A patent/MX2010002692A/es not_active Application Discontinuation
- 2008-09-12 AU AU2008299921A patent/AU2008299921B2/en not_active Ceased
- 2008-09-12 US US12/283,621 patent/US8822498B2/en not_active Expired - Fee Related
- 2008-09-12 CA CA2698808A patent/CA2698808A1/en not_active Abandoned
-
2014
- 2014-07-24 US US14/340,143 patent/US9315483B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2010539166A5 (OSRAM) | ||
| JP7759910B2 (ja) | がんを処置するための組合せ治療 | |
| JP6046710B2 (ja) | 置換されたイミダゾピリジニル−アミノピリジン化合物 | |
| AU2020203706B2 (en) | Compositions and methods for treating proliferation disorders | |
| JP6511430B2 (ja) | がんの治療のための化合物および組成物 | |
| JP3457490B2 (ja) | 置換されたヘテロ環誘導体 | |
| JP2008530099A5 (OSRAM) | ||
| JP2013530150A5 (OSRAM) | ||
| JP2013529196A5 (OSRAM) | ||
| JP2014503574A5 (OSRAM) | ||
| US20120329793A1 (en) | Substituted Imidazopyridinyl Compounds | |
| JP2005504752A5 (OSRAM) | ||
| WO2017132518A1 (en) | Combination therapy for treating cancer | |
| JP2015501820A5 (OSRAM) | ||
| JP2008518900A5 (OSRAM) | ||
| JP2007514691A5 (OSRAM) | ||
| JP2011517443A5 (OSRAM) | ||
| JP2013540712A5 (OSRAM) | ||
| JP2023528394A (ja) | 大環状ｊａｋ阻害剤およびその適用 | |
| JP2017508733A5 (OSRAM) | ||
| JP2009533417A5 (OSRAM) | ||
| JP2004517088A5 (OSRAM) | ||
| JP2012036221A5 (OSRAM) | ||
| JPWO2019213470A5 (OSRAM) | ||
| CN116133666A (zh) | 一种硼酸酯衍生物及其用途 |