BRPI0719650A2 - Derivados de azabiciclo-octano, método de fabricação deles e usos dos mesmos como inibidores de dipeptidil peptidade iv - Google Patents
Derivados de azabiciclo-octano, método de fabricação deles e usos dos mesmos como inibidores de dipeptidil peptidade iv Download PDFInfo
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- BRPI0719650A2 BRPI0719650A2 BRPI0719650-4A BRPI0719650A BRPI0719650A2 BR PI0719650 A2 BRPI0719650 A2 BR PI0719650A2 BR PI0719650 A BRPI0719650 A BR PI0719650A BR PI0719650 A2 BRPI0719650 A2 BR PI0719650A2
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- Brazil
- Prior art keywords
- alkyl
- group
- aryl
- heterocycloalkyl
- heteroaryl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 6
- 239000003112 inhibitor Substances 0.000 title abstract description 13
- QUIJMHDIAFOPRK-UHFFFAOYSA-N 1-cyclooctylazocane Chemical class C1CCCCCCC1N1CCCCCCC1 QUIJMHDIAFOPRK-UHFFFAOYSA-N 0.000 title abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 187
- 125000003118 aryl group Chemical group 0.000 claims description 167
- 125000001072 heteroaryl group Chemical group 0.000 claims description 149
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 147
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 119
- 150000001875 compounds Chemical class 0.000 claims description 116
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
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- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 24
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- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 22
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 10
- 239000012321 sodium triacetoxyborohydride Substances 0.000 claims description 9
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
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- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
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- 150000007513 acids Chemical class 0.000 claims description 4
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- 239000007858 starting material Substances 0.000 claims description 4
- 238000011287 therapeutic dose Methods 0.000 claims description 4
- SFWORHKMPZNOTF-UHFFFAOYSA-N 5-oxo-1,3,3a,4,6,6a-hexahydrocyclopenta[c]pyrrole-2-carboxylic acid Chemical compound C1C(=O)CC2CN(C(=O)O)CC21 SFWORHKMPZNOTF-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 3
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- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 150000001263 acyl chlorides Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
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- 239000011975 tartaric acid Substances 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 150000001735 carboxylic acids Chemical group 0.000 claims 22
- 150000001408 amides Chemical group 0.000 claims 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical group C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 abstract description 25
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- 239000000243 solution Substances 0.000 description 59
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- 230000001988 toxicity Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000004385 trihaloalkyl group Chemical group 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Diabetes (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2007100043308A CN101230058A (zh) | 2007-01-23 | 2007-01-23 | 双环氮杂烷类衍生物、其制备方法及其在医药上的用途 |
| CN200710004330.8 | 2007-01-23 | ||
| PCT/CN2007/070990 WO2008089636A1 (en) | 2007-01-23 | 2007-10-30 | Derivatives of azabicyclo octane, the method of making them and the uses thereof as inhibitors of dipeptidyl peptidase iv |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0719650A2 true BRPI0719650A2 (pt) | 2013-12-10 |
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Family Applications (1)
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| BRPI0719650-4A BRPI0719650A2 (pt) | 2007-01-23 | 2007-10-30 | Derivados de azabiciclo-octano, método de fabricação deles e usos dos mesmos como inibidores de dipeptidil peptidade iv |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8178575B2 (enExample) |
| EP (1) | EP2133077B1 (enExample) |
| JP (1) | JP5424256B2 (enExample) |
| KR (1) | KR101482159B1 (enExample) |
| CN (2) | CN101230058A (enExample) |
| AU (1) | AU2007345133B8 (enExample) |
| BR (1) | BRPI0719650A2 (enExample) |
| CA (1) | CA2673164C (enExample) |
| MX (1) | MX2009007765A (enExample) |
| RU (1) | RU2447063C2 (enExample) |
| WO (1) | WO2008089636A1 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2712352C (en) * | 2008-01-23 | 2016-05-10 | Jiangsu Hansoh Pharmaceutical Co., Ltd. | Dicycloazaalkane derivates, preparation processes and medical uses thereof |
| CN101919851B (zh) * | 2009-06-09 | 2012-02-08 | 江苏恒瑞医药股份有限公司 | 治疗哺乳动物包括人2型糖尿病的药物组合物 |
| WO2011107494A1 (de) | 2010-03-03 | 2011-09-09 | Sanofi | Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2582709B1 (de) | 2010-06-18 | 2018-01-24 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013091539A1 (zh) * | 2011-12-21 | 2013-06-27 | 江苏恒瑞医药股份有限公司 | 吡咯并六元杂芳环类衍生物、其制备方法及其在医药上的应用 |
| CN102827064B (zh) * | 2012-08-14 | 2014-01-29 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| CN102827063B (zh) * | 2012-08-14 | 2014-06-25 | 华东师范大学 | 一种氮杂双环[3.3.0]辛烷衍生物的合成方法 |
| CN103709150B (zh) * | 2012-10-09 | 2017-06-30 | 江苏豪森药业集团有限公司 | 托西酸贝格列汀晶型及其制备方法和用途 |
| IN2015DN03795A (enExample) | 2012-10-24 | 2015-10-02 | Inserm Inst Nat De La Santé Et De La Rech Médicale | |
| US9540324B2 (en) | 2013-09-26 | 2017-01-10 | Luc Therapeutics, Inc. | Selective octahydro-cyclopenta[C] pyrrole negative modulators of NR2B |
| US10426818B2 (en) | 2015-03-24 | 2019-10-01 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Method and pharmaceutical composition for use in the treatment of diabetes |
| JP6937828B2 (ja) | 2016-11-23 | 2021-09-22 | 江蘇恒瑞医薬股▲ふん▼有限公司 | ピロロ６員複素芳香環誘導体の製造方法、および中間体 |
| CN111491920B (zh) * | 2017-10-20 | 2024-01-30 | 范德比尔特大学 | 毒蕈碱性乙酰胆碱受体m4的拮抗剂 |
| US11352344B2 (en) | 2017-10-31 | 2022-06-07 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor M4 |
| SG11202005563YA (en) | 2017-12-15 | 2020-07-29 | Praxis Biotech LLC | Inhibitors of fibroblast activation protein |
| CA3090130A1 (en) | 2018-02-02 | 2019-08-08 | Vanderbilt University | Antagonists of the muscarinic acetylcholine receptor m4 |
| JP2022514352A (ja) | 2018-12-21 | 2022-02-10 | プラクシス バイオテック エルエルシー | 線維芽細胞活性化タンパク質の阻害剤 |
| CN111620816B (zh) * | 2020-05-27 | 2023-06-02 | 上海赛默罗生物科技有限公司 | 螺桨烷类衍生物、其制备方法、药物组合物和用途 |
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| US5280028A (en) * | 1992-06-24 | 1994-01-18 | G. D. Searle & Co. | Benzimidazole compounds |
| US5736550A (en) * | 1994-05-18 | 1998-04-07 | Nisshin Flour Milling Co., Ltd. | Pyrimidine derivatives |
| TW492957B (en) | 1996-11-07 | 2002-07-01 | Novartis Ag | N-substituted 2-cyanopyrrolidnes |
| US6110949A (en) | 1999-06-24 | 2000-08-29 | Novartis Ag | N-(substituted glycyl)-4-cyanothiazolidines, pharmaceutical compositions containing them and their use in inhibiting dipeptidyl peptidase-IV |
| US6395767B2 (en) * | 2000-03-10 | 2002-05-28 | Bristol-Myers Squibb Company | Cyclopropyl-fused pyrrolidine-based inhibitors of dipeptidyl peptidase IV and method |
| HUP0200849A2 (hu) * | 2002-03-06 | 2004-08-30 | Sanofi-Synthelabo | N-aminoacetil-2-ciano-pirrolidin-származékok, e vegyületeket tartalmazó gyógyszerkészítmények és eljárás előállításukra |
| TW200401635A (en) * | 2002-07-23 | 2004-02-01 | Yamanouchi Pharma Co Ltd | 2-Cyano-4-fluoropyrrolidine derivative or salt thereof |
| CA2517888C (en) * | 2003-03-14 | 2012-05-01 | Ono Pharmaceutical Co., Ltd. | Nitrogen-containing heterocyclic derivatives and drugs containing the same as the active ingredient |
| GB0307856D0 (en) | 2003-04-04 | 2003-05-14 | Novartis Ag | Organic compounds |
| CA2521271C (en) * | 2003-04-04 | 2011-01-04 | Novartis Ag | Quinoline-2-one-derivatives for the treatment of airways diseases |
| US7288563B2 (en) * | 2004-02-19 | 2007-10-30 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US7381738B2 (en) * | 2004-02-19 | 2008-06-03 | Bristol-Myers Squibb Company | Substituted bicycloalkylamine derivatives as modulators of chemokine receptor activity |
| US20070270417A1 (en) * | 2004-07-22 | 2007-11-22 | Glaxo Group Limited | Antibacterial Agents |
| WO2006028961A2 (en) * | 2004-09-03 | 2006-03-16 | Athersys, Inc. | Tricyclic heteroaryl piperazines, pyrrolidines and azetidines as serotonin receptor modulators |
| CN101050194B (zh) | 2006-04-05 | 2013-08-21 | 上海恒瑞医药有限公司 | 双环辛烷类衍生物、其制备方法及其在医药上的用途 |
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2007
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- 2007-10-30 RU RU2009124304/04A patent/RU2447063C2/ru not_active IP Right Cessation
- 2007-10-30 WO PCT/CN2007/070990 patent/WO2008089636A1/zh not_active Ceased
- 2007-10-30 AU AU2007345133A patent/AU2007345133B8/en not_active Ceased
- 2007-10-30 KR KR1020097017567A patent/KR101482159B1/ko not_active Expired - Fee Related
- 2007-10-30 MX MX2009007765A patent/MX2009007765A/es active IP Right Grant
- 2007-10-30 BR BRPI0719650-4A patent/BRPI0719650A2/pt not_active IP Right Cessation
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- 2007-10-30 EP EP07817181.6A patent/EP2133077B1/en active Active
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2008
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Also Published As
| Publication number | Publication date |
|---|---|
| CN101914092B (zh) | 2012-12-26 |
| JP2010516635A (ja) | 2010-05-20 |
| WO2008089636A1 (en) | 2008-07-31 |
| CN101230058A (zh) | 2008-07-30 |
| AU2007345133A1 (en) | 2008-07-31 |
| KR20090108093A (ko) | 2009-10-14 |
| AU2007345133B8 (en) | 2013-05-02 |
| EP2133077B1 (en) | 2014-08-13 |
| MX2009007765A (es) | 2009-07-30 |
| RU2447063C2 (ru) | 2012-04-10 |
| CA2673164A1 (en) | 2008-07-31 |
| RU2009124304A (ru) | 2011-02-27 |
| US8178575B2 (en) | 2012-05-15 |
| AU2007345133B2 (en) | 2013-02-21 |
| US20100016314A1 (en) | 2010-01-21 |
| HK1117164A1 (en) | 2009-01-09 |
| CN101914092A (zh) | 2010-12-15 |
| EP2133077A4 (en) | 2010-12-22 |
| JP5424256B2 (ja) | 2014-02-26 |
| CA2673164C (en) | 2016-05-10 |
| EP2133077A1 (en) | 2009-12-16 |
| KR101482159B1 (ko) | 2015-01-13 |
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