AR066191A1 - Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona - Google Patents
Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 onaInfo
- Publication number
- AR066191A1 AR066191A1 ARP080101154A AR066191A1 AR 066191 A1 AR066191 A1 AR 066191A1 AR P080101154 A ARP080101154 A AR P080101154A AR 066191 A1 AR066191 A1 AR 066191A1
- Authority
- AR
- Argentina
- Prior art keywords
- phenyl
- compounds
- espiro
- trifluorometil
- etoxi
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 230000008569 process Effects 0.000 title abstract 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 title 1
- 239000002184 metal Substances 0.000 title 1
- 229910052751 metal Inorganic materials 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- -1 lactam compound Chemical class 0.000 abstract 3
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 abstract 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- 102100021260 Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1 Human genes 0.000 abstract 1
- 101000894906 Homo sapiens Galactosylgalactosylxylosylprotein 3-beta-glucuronosyltransferase 1 Proteins 0.000 abstract 1
- 206010028813 Nausea Diseases 0.000 abstract 1
- 206010047700 Vomiting Diseases 0.000 abstract 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000003951 lactams Chemical class 0.000 abstract 1
- 230000008693 nausea Effects 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000011701 zinc Substances 0.000 abstract 1
- 229910052725 zinc Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- A61P25/06—Antimigraine agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/38—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/10—Spiro-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Los compuestos de la presente se pueden utilizar, por ejemplo, como compuestos inhibidores de NK-1 en preparaciones farmacéuticas y son utiles en el tratamiento de náuseas y emesis. Reivindicacion 1: Un proceso para producir un compuesto de lactama de formula 1 el proceso que comprende hacer reaccionar un compuesto de la formula 27a-sulfonato con zinc en presencia de ácido acético, formando de este modo la lactama de formula 1, donde R1 se selecciona de alquilo lineal, ramificado o cíclico que tiene hasta 6 átomos de carbono, fenilo, 2-metoxi-etilo, 2-(dimetilamino)etilo, (L)-mentilo, (D)-mentilo, dimetilamida, (R)-bencil-oxazolidinonamida, (S)-bencil-oxazolidinonamida, isobornilo, cis-pinan-2-ilo, isopinocamfeílo, adamantilmetilo, 2-adamantilo, 1-adamantilo, y (-)-8-fenilmentilo.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US91966607P | 2007-03-22 | 2007-03-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR066191A1 true AR066191A1 (es) | 2009-08-05 |
Family
ID=39789180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP080101154 AR066191A1 (es) | 2007-03-22 | 2008-03-19 | Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8552191B2 (es) |
| EP (2) | EP2137151B1 (es) |
| JP (2) | JP5451404B2 (es) |
| CN (2) | CN101679257B (es) |
| AR (1) | AR066191A1 (es) |
| CA (1) | CA2682221C (es) |
| ES (1) | ES2579771T3 (es) |
| MX (1) | MX2009010211A (es) |
| SG (1) | SG182226A1 (es) |
| WO (1) | WO2008118328A2 (es) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUE028908T2 (en) | 2006-04-05 | 2017-01-30 | Opko Health Inc | The hydrochloride salt of 8 - [{1- (3,5-bis (trifluoromethyl) phenyl) ethoxy} methyl] -8-phenyl-1,7-diazaspiro [4.5] decan-2-one, and process |
| CN103751186B (zh) | 2006-04-05 | 2016-08-24 | 欧科生医股份有限公司 | 药物制剂:8-[{1-(3,5-双-(三氟甲基)苯基)-乙氧基}-甲基]-8-苯基-1,7-二氮杂-螺[4.5]癸-2-酮的盐及用其治疗的方法 |
| AR066191A1 (es) | 2007-03-22 | 2009-08-05 | Schering Corp | Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona |
| EP3034493A1 (en) * | 2008-09-05 | 2016-06-22 | OPKO Health, Inc. | Process for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
| CN102573475B (zh) * | 2009-08-14 | 2016-01-20 | 欧科生医股份有限公司 | 神经激肽-1拮抗剂的静脉内制剂 |
| GB2504076A (en) | 2012-07-16 | 2014-01-22 | Nicoventures Holdings Ltd | Electronic smoking device |
| GB2504075A (en) | 2012-07-16 | 2014-01-22 | Nicoventures Holdings Ltd | Electronic smoking device |
| GB201505595D0 (en) | 2015-03-31 | 2015-05-13 | British American Tobacco Co | Cartridge for use with apparatus for heating smokeable material |
| GB201505597D0 (en) | 2015-03-31 | 2015-05-13 | British American Tobacco Co | Article for use with apparatus for heating smokable material |
| CN105017251B (zh) * | 2015-06-30 | 2018-06-29 | 齐鲁制药有限公司 | 一种nk-1受体拮抗剂的制备方法及其中间体 |
| JP6384536B2 (ja) * | 2015-10-23 | 2018-09-05 | 信越化学工業株式会社 | フッ化イットリウム溶射材料及びオキシフッ化イットリウム成膜部品の製造方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3094522A (en) * | 1961-07-25 | 1963-06-18 | Merck & Co Inc | Alkanoylthio and pyrazolo androstane derivatives |
| AU678409B2 (en) * | 1992-10-28 | 1997-05-29 | Merck Sharp & Dohme Limited | 4-arylmethyloxymethyl piperidines as tachykinin antagonists |
| US5661162A (en) | 1992-12-14 | 1997-08-26 | Merck Sharp & Dohme Limited | 4-aminomethyl/thiomethyl/sulfonylmethyl-4-phenylpiperdines as tachykinin receptor antagonists |
| ES2120170T3 (es) | 1994-01-13 | 1998-10-16 | Merck Sharp & Dohme | Antagonistas azaciclicos gem-disustituidos de taquiquininas. |
| GB9601680D0 (en) | 1996-01-27 | 1996-03-27 | Pfizer Ltd | Therapeutic agents |
| GB9626746D0 (en) | 1996-12-23 | 1997-02-12 | Knoll Ag | Process |
| EP0977573A1 (en) * | 1997-04-24 | 2000-02-09 | MERCK SHARP & DOHME LTD. | Use of an nk-1 receptor antagonist and an ssri for treating obesity |
| DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| US6215019B1 (en) * | 1998-09-01 | 2001-04-10 | Tilliechem, Inc. | Synthesis of 5-decenyl acetate and other pheromone components |
| WO2000038677A1 (en) * | 1998-12-23 | 2000-07-06 | Allelix Biopharmaceuticals Inc. | Indole and indolizidine derivatives for the treatment of migraine |
| CN1213032C (zh) | 1999-05-24 | 2005-08-03 | 加州理工学院 | 咪唑烷基金属卡宾易位催化剂 |
| US6858414B2 (en) * | 1999-12-01 | 2005-02-22 | BIOGAL Gyógyszergyár Rt. | Multistage process for the preparation of highly pure deferoxamine mesylate salt |
| ES2258485T3 (es) | 1999-12-17 | 2006-09-01 | Schering Corporation | Antagonistas selectivos de neuroquinina. |
| US6436928B1 (en) * | 1999-12-17 | 2002-08-20 | Schering Corporation | Selective neurokinin antagonists |
| GB0004699D0 (en) * | 2000-02-28 | 2000-04-19 | Merck Sharp & Dohme | Chemical synthesis |
| EP1313559B2 (en) | 2000-08-10 | 2012-10-24 | Trustees of Boston College | Recyclable metathesis catalysts |
| DE60222693T2 (de) * | 2001-11-13 | 2008-07-17 | Schering Corp. | Nk1-antagonisten |
| PE20030762A1 (es) * | 2001-12-18 | 2003-09-05 | Schering Corp | Compuestos heterociclicos como antagonistas nk1 |
| CN1678317B (zh) * | 2002-07-03 | 2010-10-27 | 先灵公司 | 用作治疗呕吐、抑郁症、焦虑症和咳嗽的神经激肽-1(nk-1)拮抗剂的1-酰氨基-4-苯基-4-苄氧基甲基-哌啶衍生物和相关化合物 |
| PL199412B1 (pl) | 2002-10-15 | 2008-09-30 | Boehringer Ingelheim Int | Nowe kompleksy rutenu jako (pre)katalizatory reakcji metatezy, pochodne 2-alkoksy-5-nitrostyrenu jako związki pośrednie i sposób ich wytwarzania |
| ATE447575T1 (de) * | 2003-04-23 | 2009-11-15 | Merck & Co Inc | Selektive spirocyclische glucocorticoid-rezeptor- modulatoren |
| AR046769A1 (es) * | 2003-12-22 | 2005-12-21 | Schering Corp | Composiciones farmaceuticas |
| CA2562138A1 (en) | 2004-04-07 | 2005-10-27 | Schering Corporation | Fused ring nk1 antagonists |
| EP3269713A1 (en) * | 2004-07-01 | 2018-01-17 | OPKO Health, Inc. | Piperidine derivatives as nk1 antagonists |
| JP4444745B2 (ja) * | 2004-07-08 | 2010-03-31 | キヤノン株式会社 | 偏光分離素子および画像投射装置 |
| US7354922B2 (en) * | 2004-12-14 | 2008-04-08 | Schering Corporation | Bridged ring NK1 antagonists |
| TW200630380A (en) * | 2005-02-18 | 2006-09-01 | Nat Univ Chung Hsing | N-acylamino acid racemase of Deinococcus radiodurans and producing method thereof, and L-amino acid production method therefrom |
| RU2435778C2 (ru) | 2005-07-04 | 2011-12-10 | Заннан Сайтех Ко., Лтд. | Лиганд комплекса рутения, комплекс рутения, катализатор комплекса рутения и способы его получения и применения |
| HUE028908T2 (en) | 2006-04-05 | 2017-01-30 | Opko Health Inc | The hydrochloride salt of 8 - [{1- (3,5-bis (trifluoromethyl) phenyl) ethoxy} methyl] -8-phenyl-1,7-diazaspiro [4.5] decan-2-one, and process |
| CN103751186B (zh) * | 2006-04-05 | 2016-08-24 | 欧科生医股份有限公司 | 药物制剂:8-[{1-(3,5-双-(三氟甲基)苯基)-乙氧基}-甲基]-8-苯基-1,7-二氮杂-螺[4.5]癸-2-酮的盐及用其治疗的方法 |
| WO2007114922A2 (en) | 2006-04-05 | 2007-10-11 | Schering Corporation | Salts of 8-[{1-(3,5-bis-(trifluoromethyl) phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one and preparation process therefor |
| AR066191A1 (es) | 2007-03-22 | 2009-08-05 | Schering Corp | Proceso e intermediarios para la sintesis de compuestos 8- [ ( 1- (3,5- bis- ( trifluorometil) fenil) - etoxi ) - metil]- 8 fenil - 1,7- diaza - espiro (4, 5) decan -2 ona |
| AR065802A1 (es) * | 2007-03-22 | 2009-07-01 | Schering Corp | Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas |
| EP3034493A1 (en) | 2008-09-05 | 2016-06-22 | OPKO Health, Inc. | Process for the synthesis of 8-[{1-(3,5-bis-(trifluoromethyl)phenyl)-ethoxy}-methyl]-8-phenyl-1,7-diaza-spiro[4.5]decan-2-one compounds |
| CN102573475B (zh) | 2009-08-14 | 2016-01-20 | 欧科生医股份有限公司 | 神经激肽-1拮抗剂的静脉内制剂 |
-
2008
- 2008-03-19 AR ARP080101154 patent/AR066191A1/es unknown
- 2008-03-20 CN CN200880017063.0A patent/CN101679257B/zh not_active Expired - Fee Related
- 2008-03-20 CN CN201410738810.7A patent/CN104447510B/zh not_active Expired - Fee Related
- 2008-03-20 ES ES08742144.2T patent/ES2579771T3/es active Active
- 2008-03-20 US US12/531,859 patent/US8552191B2/en active Active
- 2008-03-20 CA CA2682221A patent/CA2682221C/en active Active
- 2008-03-20 SG SG2012046439A patent/SG182226A1/en unknown
- 2008-03-20 WO PCT/US2008/003640 patent/WO2008118328A2/en not_active Ceased
- 2008-03-20 MX MX2009010211A patent/MX2009010211A/es active IP Right Grant
- 2008-03-20 JP JP2009554566A patent/JP5451404B2/ja not_active Expired - Fee Related
- 2008-03-20 EP EP08742144.2A patent/EP2137151B1/en active Active
- 2008-03-20 EP EP16168286.9A patent/EP3138836A1/en not_active Withdrawn
-
2013
- 2013-09-27 US US14/039,367 patent/US9260428B2/en active Active
- 2013-12-26 JP JP2013268922A patent/JP2014144951A/ja not_active Withdrawn
-
2016
- 2016-02-12 US US15/043,129 patent/US10000493B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US10000493B2 (en) | 2018-06-19 |
| US8552191B2 (en) | 2013-10-08 |
| ES2579771T3 (es) | 2016-08-16 |
| MX2009010211A (es) | 2009-10-19 |
| SG182226A1 (en) | 2012-07-30 |
| WO2008118328A2 (en) | 2008-10-02 |
| CN104447510B (zh) | 2018-03-30 |
| JP5451404B2 (ja) | 2014-03-26 |
| JP2010522171A (ja) | 2010-07-01 |
| EP2137151B1 (en) | 2016-05-11 |
| US20170008893A1 (en) | 2017-01-12 |
| US20100087426A1 (en) | 2010-04-08 |
| JP2014144951A (ja) | 2014-08-14 |
| US20140024834A1 (en) | 2014-01-23 |
| CA2682221C (en) | 2017-04-25 |
| CN101679257B (zh) | 2015-01-07 |
| CN101679257A (zh) | 2010-03-24 |
| WO2008118328A3 (en) | 2009-03-05 |
| HK1136297A1 (zh) | 2010-06-25 |
| CN104447510A (zh) | 2015-03-25 |
| CA2682221A1 (en) | 2008-10-02 |
| US9260428B2 (en) | 2016-02-16 |
| EP3138836A1 (en) | 2017-03-08 |
| EP2137151A2 (en) | 2009-12-30 |
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