CA2472954C - Aza-arylpiperazines - Google Patents
Aza-arylpiperazines Download PDFInfo
- Publication number
- CA2472954C CA2472954C CA002472954A CA2472954A CA2472954C CA 2472954 C CA2472954 C CA 2472954C CA 002472954 A CA002472954 A CA 002472954A CA 2472954 A CA2472954 A CA 2472954A CA 2472954 C CA2472954 C CA 2472954C
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- triaza
- diabetes
- fluorene
- compound
- 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.)
- Expired - Fee Related
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 26
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- 208000035475 disorder Diseases 0.000 claims abstract description 22
- 150000002148 esters Chemical class 0.000 claims abstract description 19
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- 125000000217 alkyl group Chemical group 0.000 claims description 66
- -1 hydroxyalkoxyalkyl Chemical group 0.000 claims description 64
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- 239000001257 hydrogen Substances 0.000 claims description 51
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- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical group CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 31
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 125000006239 protecting group Chemical group 0.000 claims description 25
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- VFLUBEQSNNICTK-WCABBAIRSA-N (1s)-1-[(5ar,9r)-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazin-2-yl]ethanol Chemical compound C1NC[C@@H](C)N2C3=NC([C@@H](O)C)=CC=C3C[C@@H]21 VFLUBEQSNNICTK-WCABBAIRSA-N 0.000 claims description 6
- RWHZKUHKJJABFU-VXNVDRBHSA-N (5ar,9r)-2-bromo-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1=C(Br)N=C2N3[C@H](C)CNC[C@H]3CC2=C1 RWHZKUHKJJABFU-VXNVDRBHSA-N 0.000 claims description 6
- 125000005127 aryl alkoxy alkyl group Chemical group 0.000 claims description 6
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- PYJAIOOKUMKWAJ-LDYMZIIASA-N (5ar,9r)-2-(fluoromethyl)-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1=C(CF)N=C2N3[C@H](C)CNC[C@H]3CC2=C1 PYJAIOOKUMKWAJ-LDYMZIIASA-N 0.000 claims description 4
- AUVNCNYPOJVIRZ-BXKDBHETSA-N (5ar,9r)-2-(methoxymethyl)-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1NC[C@@H](C)N2C3=NC(COC)=CC=C3C[C@@H]21 AUVNCNYPOJVIRZ-BXKDBHETSA-N 0.000 claims description 4
- OZKJKXGCRKEWKL-NTZNESFSSA-N (5ar,9r)-2-[(1s)-1-ethoxyethyl]-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1NC[C@@H](C)N2C3=NC([C@H](C)OCC)=CC=C3C[C@@H]21 OZKJKXGCRKEWKL-NTZNESFSSA-N 0.000 claims description 4
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- PKOPGQYFQBKBPB-VXNVDRBHSA-N (5ar,9r)-2-chloro-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1=C(Cl)N=C2N3[C@H](C)CNC[C@H]3CC2=C1 PKOPGQYFQBKBPB-VXNVDRBHSA-N 0.000 claims description 4
- ZRNVRGJQVCODRO-BXKDBHETSA-N (5ar,9r)-2-cyclopropyl-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C([C@@H]1CNC[C@H](N1C1=N2)C)C1=CC=C2C1CC1 ZRNVRGJQVCODRO-BXKDBHETSA-N 0.000 claims description 4
- GVCOTWGEKWXLPZ-SECBINFHSA-N (9r)-2,9-dimethyl-6,7,8,9-tetrahydropyrido[3,4]pyrrolo[3,5-a]pyrazine Chemical compound C1=C(C)N=C2N3[C@H](C)CNCC3=CC2=C1 GVCOTWGEKWXLPZ-SECBINFHSA-N 0.000 claims description 4
- MMOQJRSPKZSHHF-SSDOTTSWSA-N (9r)-2-chloro-5,9-dimethyl-6,7,8,9-tetrahydropyrido[3,4]pyrrolo[3,5-a]pyrazine Chemical compound C1=C(Cl)N=C2N3[C@H](C)CNCC3=C(C)C2=C1 MMOQJRSPKZSHHF-SSDOTTSWSA-N 0.000 claims description 4
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- LJRLAJVWAFFRLV-IAQYHMDHSA-N (5ar,9r)-2-(cyclopropylmethoxymethyl)-9-methyl-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C([C@@H]1CNC[C@H](N1C1=N2)C)C1=CC=C2COCC1CC1 LJRLAJVWAFFRLV-IAQYHMDHSA-N 0.000 claims description 3
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- CTPWPURTEYFXDP-VXNVDRBHSA-N (5ar,9r)-9-methyl-2-(trifluoromethyl)-5,5a,6,7,8,9-hexahydropyrido[1,2]pyrrolo[4,5-a]pyrazine Chemical compound C1=C(C(F)(F)F)N=C2N3[C@H](C)CNC[C@H]3CC2=C1 CTPWPURTEYFXDP-VXNVDRBHSA-N 0.000 claims description 3
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- RMECMGFJLQHTHA-WUQHVDQBSA-N tert-butyl (5ar,9r)-9-methyl-2-[2-(oxan-2-yloxy)ethoxymethyl]-5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C([C@@H]1CN(C[C@H](N1C1=N2)C)C(=O)OC(C)(C)C)C1=CC=C2COCCOC1CCCCO1 RMECMGFJLQHTHA-WUQHVDQBSA-N 0.000 description 1
- KMAXWRVCQCXZOQ-OALZAMAHSA-N tert-butyl (9R,13R)-4-(ethylcarbamoyloxymethyl)-13-methyl-1,3,11-triazatricyclo[7.4.0.02,7]trideca-2(7),3,5-triene-11-carboxylate isocyanatoethane Chemical compound C(C)N=C=O.C(C)(C)(C)OC(=O)N1C[C@H]2CC3=CC=C(N=C3N2[C@@H](C1)C)COC(NCC)=O KMAXWRVCQCXZOQ-OALZAMAHSA-N 0.000 description 1
- MKKFKQPBJLRZKF-GFCCVEGCSA-N tert-butyl (9r)-2,9-dimethyl-8,9-dihydro-6h-pyrido[3,4]pyrrolo[3,5-a]pyrazine-7-carboxylate Chemical compound C1=C(C)N=C2N3[C@H](C)CN(C(=O)OC(C)(C)C)CC3=CC2=C1 MKKFKQPBJLRZKF-GFCCVEGCSA-N 0.000 description 1
- MBJOECOHUUJLRU-SNVBAGLBSA-N tert-butyl (9r)-2-chloro-5-formyl-9-methyl-8,9-dihydro-6h-pyrido[2,3]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1=C(Cl)N=C2N3[C@H](C)CN(C(=O)OC(C)(C)C)CC3=C(C=O)C2=C1 MBJOECOHUUJLRU-SNVBAGLBSA-N 0.000 description 1
- RLCLUTODDLMAJZ-JTDNENJMSA-N tert-butyl (9r)-9-methyl-5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1=CN=C2N3[C@H](C)CN(C(=O)OC(C)(C)C)CC3CC2=C1 RLCLUTODDLMAJZ-JTDNENJMSA-N 0.000 description 1
- SETKKDROFJDPBD-LLVKDONJSA-N tert-butyl (9r)-9-methyl-8,9-dihydro-6h-pyrido[3,4]pyrrolo[3,5-a]pyrazine-7-carboxylate Chemical compound C1=CN=C2N3[C@H](C)CN(C(=O)OC(C)(C)C)CC3=CC2=C1 SETKKDROFJDPBD-LLVKDONJSA-N 0.000 description 1
- PYCGYUNBSBQZQR-UHFFFAOYSA-N tert-butyl 1,3,11-triazatricyclo[7.4.0.02,7]trideca-2(7),3,5,8,12-pentaene-11-carboxylate Chemical compound CC(C)(C)OC(=O)N1Cc2cc3cccnc3n2C=C1 PYCGYUNBSBQZQR-UHFFFAOYSA-N 0.000 description 1
- JWBPJPYJYTYIFS-UHFFFAOYSA-N tert-butyl 10-methyl-1,3,11-triazatricyclo[7.4.0.02,7]trideca-2(7),3,5,8-tetraene-11-carboxylate Chemical compound C(C)(C)(C)OC(=O)N1C(C2=CC3=CC=CN=C3N2CC1)C JWBPJPYJYTYIFS-UHFFFAOYSA-N 0.000 description 1
- UXEWNRDAJVUSOV-UHFFFAOYSA-N tert-butyl 2-(1-hydroxypropyl)-9-methyl-5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC(C)N2C3=NC(C(O)CC)=CC=C3CC21 UXEWNRDAJVUSOV-UHFFFAOYSA-N 0.000 description 1
- AFNGBOMWQSSHGJ-UHFFFAOYSA-N tert-butyl 2-(hydroxymethyl)-9-methyl-5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1=C(CO)N=C2N3C(C)CN(C(=O)OC(C)(C)C)CC3CC2=C1 AFNGBOMWQSSHGJ-UHFFFAOYSA-N 0.000 description 1
- LUMYVEBMEXTQAQ-UHFFFAOYSA-N tert-butyl 2-acetyl-9-methyl-5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1=C(C(C)=O)N=C2N3C(C)CN(C(=O)OC(C)(C)C)CC3CC2=C1 LUMYVEBMEXTQAQ-UHFFFAOYSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- UUOKXMHUKNDTOE-UHFFFAOYSA-N tert-butyl 5a,6,8,9-tetrahydro-5h-pyrido[1,2]pyrrolo[4,5-a]pyrazine-7-carboxylate Chemical compound C1=CN=C2N3CCN(C(=O)OC(C)(C)C)CC3CC2=C1 UUOKXMHUKNDTOE-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
- PCZOZSATUTWXIC-UHFFFAOYSA-N tetraethylazanium;cyanide Chemical compound N#[C-].CC[N+](CC)(CC)CC PCZOZSATUTWXIC-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 229940002552 xenical Drugs 0.000 description 1
Classifications
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- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
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- Neurology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Psychology (AREA)
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- Emergency Medicine (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Epoxy Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Photoreceptors In Electrophotography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0202015.4 | 2002-01-29 | ||
| GBGB0202015.4A GB0202015D0 (en) | 2002-01-29 | 2002-01-29 | Piperazine Derivatives |
| PCT/EP2003/000459 WO2003064423A1 (en) | 2002-01-29 | 2003-01-17 | Aza-arylpiperazines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2472954A1 CA2472954A1 (en) | 2003-08-07 |
| CA2472954C true CA2472954C (en) | 2009-04-28 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002472954A Expired - Fee Related CA2472954C (en) | 2002-01-29 | 2003-01-17 | Aza-arylpiperazines |
Country Status (33)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7405210B2 (en) | 2003-05-21 | 2008-07-29 | Osi Pharmaceuticals, Inc. | Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase |
| DE602004028122D1 (de) * | 2003-05-21 | 2010-08-26 | Prosidion Ltd | Pyrrolopyridin-2-carbonsäuren als hemmer der glycogenphosphorylase |
| GB0314967D0 (en) | 2003-06-26 | 2003-07-30 | Hoffmann La Roche | Piperazine derivatives |
| TW200528102A (en) * | 2003-10-24 | 2005-09-01 | Solvay Pharm Gmbh | Novel medical combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| RU2006117637A (ru) * | 2003-10-24 | 2007-12-10 | Зольвай Фармасьютиклз Гмбх (De) | Комбинированное лечение ожирения с применением избирательных антагонистов cb1-рецептора и ингибиторов липаз |
| EP2400300A1 (en) | 2004-08-25 | 2011-12-28 | Takeda Pharmaceutical Company Limited | Method of screening preventives/remedies for stress urinary incontinence |
| RU2007119315A (ru) | 2004-10-25 | 2008-11-27 | Зольвай Фармасьютиклз Гмбх (De) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний |
| CN101171252B (zh) * | 2005-05-03 | 2011-06-01 | 霍夫曼-拉罗奇有限公司 | 作为5-ht2配体的四环氮杂吡嗪并二氢吲哚类化合物 |
| WO2006125179A1 (en) * | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
| ATE485294T1 (de) * | 2005-11-18 | 2010-11-15 | Hoffmann La Roche | Azaindol-2-carboxamid-derivate |
| DE602006010433D1 (de) * | 2005-12-09 | 2009-12-24 | Hoffmann La Roche | Für die behandlung von obesitas geeignete tricyclische amidderivate |
| US7351708B2 (en) | 2005-12-16 | 2008-04-01 | Hoffmann-La Roche Inc. | Pyrrolo [2,3-b] pyridine derivatives |
| WO2007132841A1 (ja) | 2006-05-16 | 2007-11-22 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物およびその用途 |
| AU2007283113A1 (en) | 2006-08-08 | 2008-02-14 | Sanofi-Aventis | Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, processes for preparing them, medicaments comprising these compounds, and their use |
| JP5520051B2 (ja) | 2007-11-15 | 2014-06-11 | 武田薬品工業株式会社 | 縮合ピリジン誘導体およびその用途 |
| US8470841B2 (en) | 2008-07-09 | 2013-06-25 | Sanofi | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| JP2013503135A (ja) | 2009-08-26 | 2013-01-31 | サノフイ | 新規な結晶性複素芳香族フルオログリコシド水和物、その化合物を含んでなる医薬及びその使用 |
| JPWO2011071136A1 (ja) | 2009-12-11 | 2013-04-22 | アステラス製薬株式会社 | 線維筋痛症治療剤 |
| FR2960876B1 (fr) | 2010-06-03 | 2012-07-27 | Sanofi Aventis | Derives de 3,4-dihydropyrrolo[1,2-a]pyrazine-2,8(1h)-dicarboxamide leur preparation et leur application en therapeutique. |
| WO2012120054A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683703B1 (de) | 2011-03-08 | 2015-05-27 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2766349B1 (de) | 2011-03-08 | 2016-06-01 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683704B1 (de) | 2011-03-08 | 2014-12-17 | Sanofi | Verzweigte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120056A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Tetrasubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US8809324B2 (en) | 2011-03-08 | 2014-08-19 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| WO2012120058A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| CA2870019C (en) * | 2012-04-26 | 2020-08-18 | Francis Xavier Tavares | Synthesis of lactams |
| AR092041A1 (es) * | 2012-08-06 | 2015-03-18 | Hoffmann La Roche | Piperazino[1,2-a]indol-1-onas y [1,4]diazepino[1,2-a]indol-1-ona |
| WO2015066344A1 (en) | 2013-11-01 | 2015-05-07 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| EP3500570B1 (en) * | 2016-08-19 | 2022-10-05 | Arena Pharmaceuticals, Inc. | 5-ht2c receptor agonists and compositions and methods of use |
| US20210052600A1 (en) | 2017-12-27 | 2021-02-25 | Takeda Pharmaceutical Company Limited | Therapeutic agents for stress urinary incontinence and incotinence of feces |
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| CA1247547A (en) | 1983-06-22 | 1988-12-28 | Paul Hadvary | Leucine derivatives |
| CA1270837A (en) | 1984-12-21 | 1990-06-26 | Hoffmann-La Roche Limited | Oxetanones |
| CA1328881C (en) | 1984-12-21 | 1994-04-26 | Pierre Barbier | Process for the manufacture of oxetanones |
| CA2035972C (en) | 1990-02-23 | 2006-07-11 | Martin Karpf | Process for the preparation of oxetanones |
| US5274143A (en) | 1991-07-23 | 1993-12-28 | Hoffmann-La Roche Inc. | Process for the preparation of (R)-3-hexyl-5,6-dihydro-4-hydroxy-6-undecyl-2H-pyran-2-one and (R)-5,6-dihydro-6-undecyl-2H-pyran-2,4(3H)-dione |
| US6004996A (en) | 1997-02-05 | 1999-12-21 | Hoffman-La Roche Inc. | Tetrahydrolipstatin containing compositions |
| US6267952B1 (en) | 1998-01-09 | 2001-07-31 | Geltex Pharmaceuticals, Inc. | Lipase inhibiting polymers |
| EP1105123B1 (en) | 1998-08-14 | 2004-04-07 | F.Hoffmann-La Roche Ag | Pharmaceutical compositions containing lipase inhibitors and chitosan |
| PT1105122E (pt) | 1998-08-14 | 2005-08-31 | Hoffmann La Roche | Composicoes farmaceuticas que contem inibidores de lipase |
| GB9902047D0 (en) * | 1999-01-29 | 1999-03-17 | Cerebrus Ltd | Chemical compounds XI |
| FR2799757B1 (fr) * | 1999-10-15 | 2001-12-14 | Adir | Nouveaux derives polycycliques azaindoliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
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