ZA200308777B - Adenosine analogues for the treatment of the insulin resistance syndrome and diabetes - Google Patents
Adenosine analogues for the treatment of the insulin resistance syndrome and diabetes Download PDFInfo
- Publication number
- ZA200308777B ZA200308777B ZA200308777A ZA200308777A ZA200308777B ZA 200308777 B ZA200308777 B ZA 200308777B ZA 200308777 A ZA200308777 A ZA 200308777A ZA 200308777 A ZA200308777 A ZA 200308777A ZA 200308777 B ZA200308777 B ZA 200308777B
- Authority
- ZA
- South Africa
- Prior art keywords
- purin
- ylamino
- diol
- pyrrolidin
- hydroxymethyl
- Prior art date
Links
- 238000011282 treatment Methods 0.000 title claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 title claims description 4
- 208000031773 Insulin resistance syndrome Diseases 0.000 title claims description 3
- 150000003838 adenosines Chemical class 0.000 title description 21
- GBLRQXKSCRCLBZ-YVQAASCFSA-N (1R,2S,1'R,2'S)-doxacurium Chemical compound COC1=C(OC)C(OC)=CC(C[C@H]2[N@+](CCC3=C2C(=C(OC)C(OC)=C3)OC)(C)CCCOC(=O)CCC(=O)OCCC[N@@+]2(C)[C@@H](C3=C(OC)C(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 GBLRQXKSCRCLBZ-YVQAASCFSA-N 0.000 claims description 137
- 239000000203 mixture Substances 0.000 claims description 74
- 150000001875 compounds Chemical class 0.000 claims description 67
- -1 trifluoromethylpyridin-2-yl Chemical group 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000012453 solvate Substances 0.000 claims description 18
- 150000001204 N-oxides Chemical class 0.000 claims description 11
- VCVOSERVUCJNPR-UHFFFAOYSA-N cyclopentane-1,2-diol Chemical compound OC1CCCC1O VCVOSERVUCJNPR-UHFFFAOYSA-N 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- GBLRQXKSCRCLBZ-AJSYEDJNSA-N (1S,2R,1'S,2'R)-doxacurium Chemical compound COC1=C(OC)C(OC)=CC(C[C@@H]2[N@@+](CCC3=C2C(=C(OC)C(OC)=C3)OC)(C)CCCOC(=O)CCC(=O)OCCC[N@+]2(C)[C@H](C3=C(OC)C(OC)=C(OC)C=C3CC2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 GBLRQXKSCRCLBZ-AJSYEDJNSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
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- SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
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- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
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- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 3
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- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
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- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- SLFZPSKIMUPQSR-VIFPVBQESA-N tert-butyl (3s)-3-acetamidopyrrolidine-1-carboxylate Chemical compound CC(=O)N[C@H]1CCN(C(=O)OC(C)(C)C)C1 SLFZPSKIMUPQSR-VIFPVBQESA-N 0.000 description 1
- BFRSOEPNARQSRV-UEWDXFNNSA-N tert-butyl (3s)-4-amino-1-benzyl-5-oxopyrrolidine-3-carboxylate Chemical compound O=C1C(N)[C@@H](C(=O)OC(C)(C)C)CN1CC1=CC=CC=C1 BFRSOEPNARQSRV-UEWDXFNNSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 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
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 230000001196 vasorelaxation Effects 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Epidemiology (AREA)
- Obesity (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01111651A EP1258247A1 (fr) | 2001-05-14 | 2001-05-14 | Analogues d'adénosine pour le traitement de le diabete et de la resistance à l' insuline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308777B true ZA200308777B (en) | 2006-04-26 |
Family
ID=8177414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308777A ZA200308777B (en) | 2001-05-14 | 2003-11-11 | Adenosine analogues for the treatment of the insulin resistance syndrome and diabetes |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US20030176390A1 (fr) |
| EP (2) | EP1258247A1 (fr) |
| JP (1) | JP2004533448A (fr) |
| KR (1) | KR20040002962A (fr) |
| CN (1) | CN1518450A (fr) |
| BG (1) | BG108356A (fr) |
| BR (1) | BR0209650A (fr) |
| CA (1) | CA2447408A1 (fr) |
| CO (1) | CO5540288A2 (fr) |
| CZ (1) | CZ20033079A3 (fr) |
| EA (1) | EA007253B1 (fr) |
| EE (1) | EE200300551A (fr) |
| HR (1) | HRP20030928A2 (fr) |
| HU (1) | HUP0400464A3 (fr) |
| IL (1) | IL158794A0 (fr) |
| MX (1) | MXPA03010336A (fr) |
| NO (1) | NO20035056D0 (fr) |
| NZ (1) | NZ529390A (fr) |
| PL (1) | PL364573A1 (fr) |
| SK (1) | SK14052003A3 (fr) |
| WO (1) | WO2002092093A1 (fr) |
| YU (1) | YU90203A (fr) |
| ZA (1) | ZA200308777B (fr) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| EP1889846A1 (fr) | 2006-07-13 | 2008-02-20 | Novartis AG | Dérivés de purine comme agonistes du recepteur A2a |
| EP1903044A1 (fr) * | 2006-09-14 | 2008-03-26 | Novartis AG | Derivés de l'adénosine en tant qu' agonistes du récepteur A2A |
| MX2009004991A (es) * | 2006-11-10 | 2009-05-20 | Novartis Ag | Derivados de monoacetato de ciclopenteno-diol. |
| EP2025674A1 (fr) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament |
| WO2009131196A1 (fr) * | 2008-04-24 | 2009-10-29 | 武田薬品工業株式会社 | Dérivé de pyrrolidine substituée et ses utilisations |
| WO2011157827A1 (fr) | 2010-06-18 | 2011-12-22 | Sanofi | Dérivés d'azolopyridin-3-one en tant qu'inhibiteurs de lipases et de phospholipases |
| EP2567959B1 (fr) | 2011-09-12 | 2014-04-16 | Sanofi | Dérivés d'amide d'acide 6-(4-hydroxy-phényl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylique en tant qu'inhibiteurs de kinase |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8729994D0 (en) * | 1987-12-23 | 1988-02-03 | Glaxo Group Ltd | Chemical compounds |
| US5055569A (en) * | 1989-10-19 | 1991-10-08 | G. D. Searle & Co. | N-(6)-substituted adenosine compounds |
| HUT61567A (en) * | 1990-12-07 | 1993-01-28 | Sandoz Ag | Process for producing new pharmaceutical compositions comprising 2'-o-alkyladenosine derivatives and for producing 6-cyclohexyl-2'-o-methyladenosinehydrate |
| US6376472B1 (en) * | 1996-07-08 | 2002-04-23 | Aventis Pharmaceuticals, Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| UA51716C2 (uk) * | 1996-07-08 | 2002-12-16 | Авентіс Фармасьютікалз Продактс Інк. | Сполуки, що мають гіпотензивну, кардіопротекторну, анти-ішемічну та антиліполітичну властивості, фармацевтична композиція та способи лікування |
| GB9723590D0 (en) * | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| US6258793B1 (en) * | 1999-12-03 | 2001-07-10 | Cv Therapeutics, Inc. | N6 heterocyclic 5′ modified adenosine derivatives |
-
2001
- 2001-05-14 EP EP01111651A patent/EP1258247A1/fr not_active Withdrawn
-
2002
- 2002-05-14 PL PL02364573A patent/PL364573A1/xx not_active Application Discontinuation
- 2002-05-14 MX MXPA03010336A patent/MXPA03010336A/es not_active Application Discontinuation
- 2002-05-14 YU YU90203A patent/YU90203A/sh unknown
- 2002-05-14 CA CA002447408A patent/CA2447408A1/fr not_active Abandoned
- 2002-05-14 CN CNA028112393A patent/CN1518450A/zh active Pending
- 2002-05-14 EA EA200301231A patent/EA007253B1/ru not_active IP Right Cessation
- 2002-05-14 JP JP2002589010A patent/JP2004533448A/ja not_active Abandoned
- 2002-05-14 CZ CZ20033079A patent/CZ20033079A3/cs unknown
- 2002-05-14 WO PCT/EP2002/005301 patent/WO2002092093A1/fr not_active Application Discontinuation
- 2002-05-14 NZ NZ529390A patent/NZ529390A/en unknown
- 2002-05-14 IL IL15879402A patent/IL158794A0/xx unknown
- 2002-05-14 EP EP02769485A patent/EP1404338A1/fr not_active Withdrawn
- 2002-05-14 SK SK1405-2003A patent/SK14052003A3/sk unknown
- 2002-05-14 US US10/145,207 patent/US20030176390A1/en not_active Abandoned
- 2002-05-14 KR KR10-2003-7014888A patent/KR20040002962A/ko not_active Application Discontinuation
- 2002-05-14 BR BR0209650-1A patent/BR0209650A/pt not_active IP Right Cessation
- 2002-05-14 HU HU0400464A patent/HUP0400464A3/hu unknown
- 2002-05-14 EE EEP200300551A patent/EE200300551A/xx unknown
-
2003
- 2003-11-11 ZA ZA200308777A patent/ZA200308777B/en unknown
- 2003-11-12 CO CO03100204A patent/CO5540288A2/es not_active Application Discontinuation
- 2003-11-13 BG BG108356A patent/BG108356A/bg unknown
- 2003-11-13 HR HR20030928A patent/HRP20030928A2/xx not_active Application Discontinuation
- 2003-11-13 NO NO20035056A patent/NO20035056D0/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NZ529390A (en) | 2006-06-30 |
| JP2004533448A (ja) | 2004-11-04 |
| YU90203A (sh) | 2006-08-17 |
| KR20040002962A (ko) | 2004-01-07 |
| EP1404338A1 (fr) | 2004-04-07 |
| BG108356A (bg) | 2004-12-30 |
| CA2447408A1 (fr) | 2002-11-21 |
| US20030176390A1 (en) | 2003-09-18 |
| HUP0400464A2 (hu) | 2004-07-28 |
| PL364573A1 (en) | 2004-12-13 |
| BR0209650A (pt) | 2004-07-13 |
| HRP20030928A2 (en) | 2005-10-31 |
| IL158794A0 (en) | 2004-05-12 |
| CO5540288A2 (es) | 2005-07-29 |
| MXPA03010336A (es) | 2004-03-16 |
| WO2002092093A1 (fr) | 2002-11-21 |
| EP1258247A1 (fr) | 2002-11-20 |
| EA200301231A1 (ru) | 2004-04-29 |
| CZ20033079A3 (cs) | 2004-08-18 |
| EE200300551A (et) | 2004-02-16 |
| CN1518450A (zh) | 2004-08-04 |
| EA007253B1 (ru) | 2006-08-25 |
| HUP0400464A3 (en) | 2007-03-28 |
| SK14052003A3 (sk) | 2004-07-07 |
| NO20035056D0 (no) | 2003-11-13 |
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