CA2351075A1 - Derives de pyridinium destines au traitement de complications vasculaires liees au diabete et au vieillissement - Google Patents
Derives de pyridinium destines au traitement de complications vasculaires liees au diabete et au vieillissement Download PDFInfo
- Publication number
- CA2351075A1 CA2351075A1 CA002351075A CA2351075A CA2351075A1 CA 2351075 A1 CA2351075 A1 CA 2351075A1 CA 002351075 A CA002351075 A CA 002351075A CA 2351075 A CA2351075 A CA 2351075A CA 2351075 A1 CA2351075 A1 CA 2351075A1
- Authority
- CA
- Canada
- Prior art keywords
- pharmaceutically acceptable
- oxoethyl
- acceptable salt
- pyridinium bromide
- aminocarbonyl
- 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.)
- Abandoned
Links
- 206010012601 diabetes mellitus Diseases 0.000 title claims abstract description 15
- 230000032683 aging Effects 0.000 title claims abstract description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 230000002792 vascular Effects 0.000 title claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 63
- 150000003839 salts Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 8
- 208000002249 Diabetes Complications Diseases 0.000 claims abstract description 8
- 208000017442 Retinal disease Diseases 0.000 claims abstract description 8
- 239000003814 drug Substances 0.000 claims abstract description 8
- 208000017169 kidney disease Diseases 0.000 claims abstract description 8
- 208000028389 Nerve injury Diseases 0.000 claims abstract description 7
- 206010038923 Retinopathy Diseases 0.000 claims abstract description 7
- 238000002845 discoloration Methods 0.000 claims abstract description 7
- 230000008764 nerve damage Effects 0.000 claims abstract description 7
- 230000003178 anti-diabetic effect Effects 0.000 claims abstract description 5
- 239000003472 antidiabetic agent Substances 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 5
- 239000004480 active ingredient Substances 0.000 claims abstract description 4
- -1 -Oalkyl Chemical group 0.000 claims description 28
- BBFCIBZLAVOLCF-UHFFFAOYSA-N pyridin-1-ium;bromide Chemical compound Br.C1=CC=NC=C1 BBFCIBZLAVOLCF-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 238000009472 formulation Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 206010012655 Diabetic complications Diseases 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 206010062198 microangiopathy Diseases 0.000 claims description 5
- 230000004768 organ dysfunction Effects 0.000 claims description 5
- 150000003222 pyridines Chemical class 0.000 claims description 5
- 206010048554 Endothelial dysfunction Diseases 0.000 claims description 4
- ZPMGJNQUSYNXAV-UHFFFAOYSA-N butyl 1-(2-anilino-2-oxoethyl)pyridin-1-ium-3-carboxylate;chloride Chemical compound [Cl-].CCCCOC(=O)C1=CC=C[N+](CC(=O)NC=2C=CC=CC=2)=C1 ZPMGJNQUSYNXAV-UHFFFAOYSA-N 0.000 claims description 4
- 230000008694 endothelial dysfunction Effects 0.000 claims description 4
- JJPCPHMZUOFGRD-UHFFFAOYSA-N n-butyl-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]pyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].CCCCNC(=O)C1=CC=C[N+](CC(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 JJPCPHMZUOFGRD-UHFFFAOYSA-N 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- DADJMTZDNBKVQT-UHFFFAOYSA-M 2-(3-benzoylpyridin-1-ium-1-yl)-1-phenylethanone;bromide Chemical compound [Br-].C=1C=CC=CC=1C(=O)C[N+](C=1)=CC=CC=1C(=O)C1=CC=CC=C1 DADJMTZDNBKVQT-UHFFFAOYSA-M 0.000 claims description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 3
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- HEBZOWPEXHXCJQ-UHFFFAOYSA-M butyl 1-[2-(2,4-dichlorophenyl)-2-oxoethyl]pyridin-1-ium-3-carboxylate;bromide Chemical compound [Br-].CCCCOC(=O)C1=CC=C[N+](CC(=O)C=2C(=CC(Cl)=CC=2)Cl)=C1 HEBZOWPEXHXCJQ-UHFFFAOYSA-M 0.000 claims description 3
- 239000003153 chemical reaction reagent Substances 0.000 claims description 3
- CBQHPQSLJHFWSK-UHFFFAOYSA-N ethyl 2-[3-(2-hydroxyethylcarbamoyl)pyridin-1-ium-1-yl]acetate;bromide Chemical compound [Br-].CCOC(=O)C[N+]1=CC=CC(C(=O)NCCO)=C1 CBQHPQSLJHFWSK-UHFFFAOYSA-N 0.000 claims description 3
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- CKXHCIGYEMYBFL-UHFFFAOYSA-M methyl 1-phenacylpyridin-1-ium-3-carboxylate;bromide Chemical compound [Br-].COC(=O)C1=CC=C[N+](CC(=O)C=2C=CC=CC=2)=C1 CKXHCIGYEMYBFL-UHFFFAOYSA-M 0.000 claims description 3
- 210000000214 mouth Anatomy 0.000 claims description 3
- VIOBNLFICFEKRB-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-phenacylpyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].OCCNC(=O)C1=CC=C[N+](CC(=O)C=2C=CC=CC=2)=C1 VIOBNLFICFEKRB-UHFFFAOYSA-N 0.000 claims description 3
- CIXPPOWOBNYQAD-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)-1-phenacylpyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].CC1=CSC(NC(=O)C=2C=[N+](CC(=O)C=3C=CC=CC=3)C=CC=2)=N1 CIXPPOWOBNYQAD-UHFFFAOYSA-N 0.000 claims description 3
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- 239000000454 talc Substances 0.000 claims description 3
- 229910052623 talc Inorganic materials 0.000 claims description 3
- QCVLYYNXACQGJF-UHFFFAOYSA-N 1-(2-anilino-2-oxoethyl)-n-(2-hydroxyethyl)pyridin-1-ium-3-carboxamide;chloride Chemical compound [Cl-].OCCNC(=O)C1=CC=C[N+](CC(=O)NC=2C=CC=CC=2)=C1 QCVLYYNXACQGJF-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-L Oxalate Chemical compound [O-]C(=O)C([O-])=O MUBZPKHOEPUJKR-UHFFFAOYSA-L 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 claims description 2
- 239000006210 lotion Substances 0.000 claims description 2
- 229940051866 mouthwash Drugs 0.000 claims description 2
- QARTURCDVYEVIZ-UHFFFAOYSA-N n-(2,3,3a,4-tetrahydro-1,3-benzothiazol-2-yl)-1-[2-(2,4-dichlorophenyl)-2-oxoethyl]pyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].ClC1=CC(Cl)=CC=C1C(=O)C[N+]1=CC=CC(C(=O)NC2SC3=CC=CCC3N2)=C1 QARTURCDVYEVIZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Chemical compound [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- 229940085991 phosphate ion Drugs 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 2
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- GHCXALOJXYUCCD-UHFFFAOYSA-N 1-(2-anilino-2-oxoethyl)-n-butylpyridin-1-ium-3-carboxamide;chloride Chemical compound [Cl-].CCCCNC(=O)C1=CC=C[N+](CC(=O)NC=2C=CC=CC=2)=C1 GHCXALOJXYUCCD-UHFFFAOYSA-N 0.000 claims 2
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
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- QQFYLZXBFWWJHR-UHFFFAOYSA-M benzyl(triethyl)phosphanium;bromide Chemical compound [Br-].CC[P+](CC)(CC)CC1=CC=CC=C1 QQFYLZXBFWWJHR-UHFFFAOYSA-M 0.000 description 1
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- BTNXXHGEWCIWTR-UHFFFAOYSA-M propan-2-yl 1-phenacylpyridin-1-ium-3-carboxylate;bromide Chemical compound [Br-].CC(C)OC(=O)C1=CC=C[N+](CC(=O)C=2C=CC=CC=2)=C1 BTNXXHGEWCIWTR-UHFFFAOYSA-M 0.000 description 1
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- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
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- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- 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
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- 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
- A61P37/00—Drugs for immunological or allergic disorders
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- 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
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Immunology (AREA)
- Ophthalmology & Optometry (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
Abstract
L'invention concerne des composés de la série du pyridinium utiles dans la gestion de complications vasculaires liées au diabète et au vieillissement, et en particulier dans le traitement de complications d'états liés au diabète sucré et autres états liés au vieillissement, notamment les hépathopathies, des lésions nerveuses, l'athérosclérose, la rétinopathie, des états dermatologiques et la décoloration des dents par rupture de produits finaux de glycation avancée (AGE) préformés, de la formule générale (I), ou ses sels acceptables sur le plan pharmaceutique, dans laquelle R?1¿, R?2¿ et X ont la définition figurant dans la description. L'invention concerne également une méthode de préparation des composés de la série ainsi qu'une composition pharmaceutique contenant un ou plusieurs composés tels que ci-dessus définis en tant que principes actifs. L'invention concerne également une méthode de traitement d'un patient diabétique par administration des composés précités, soit individuellement soit en combinaison avec d'autres médicaments destinés à une thérapie antidiabétique.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN827CA1999 | 1999-10-06 | ||
| IN827CAL99 | 1999-10-06 | ||
| PCT/IB1999/001687 WO2001025209A1 (fr) | 1999-10-06 | 1999-10-15 | Derives de pyridinium destines au traitement de complications vasculaires liees au diabete et au vieillissement |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2351075A1 true CA2351075A1 (fr) | 2001-04-12 |
Family
ID=11084921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351075A Abandoned CA2351075A1 (fr) | 1999-10-06 | 1999-10-15 | Derives de pyridinium destines au traitement de complications vasculaires liees au diabete et au vieillissement |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1220843A1 (fr) |
| JP (1) | JP2003511370A (fr) |
| CN (1) | CN1329597A (fr) |
| AU (1) | AU5994499A (fr) |
| BR (1) | BR9915962A (fr) |
| CA (1) | CA2351075A1 (fr) |
| CZ (1) | CZ20011808A3 (fr) |
| HK (1) | HK1044336A1 (fr) |
| HU (1) | HUP0301687A2 (fr) |
| MX (1) | MXPA02003496A (fr) |
| PL (1) | PL348049A1 (fr) |
| WO (1) | WO2001025209A1 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107438604A (zh) * | 2015-04-08 | 2017-12-05 | 托伦特药物有限公司 | 新吡啶化合物 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2433425A1 (fr) * | 2000-12-29 | 2002-09-06 | Alteon, Inc. | Procede de traitement ou d'amelioration de maladies fibreuses ou autres etats iiic |
| CZ303214B6 (cs) * | 2001-03-21 | 2012-05-30 | Torrent Pharmaceuticals Ltd | Pyridiniová sloucenina, zpusob její výroby, její použití, farmaceutický prostredek ji obsahující, zpusob jeho výroby a jeho použití |
| DE60111919T2 (de) * | 2001-03-21 | 2006-04-20 | Torrent Pharmaceuticals Ltd., Ahmedabad | Pyridiniumverbindungen zur Behandlung von AGE-relatierten Krankheiten |
| DK1373263T3 (da) | 2001-04-05 | 2005-03-07 | Torrent Pharmaceuticals Ltd | Heterocycliske forbindelser til aldringsrelaterede og diabetesbetingede vaskulære sygdomme |
| JP2003137783A (ja) * | 2001-10-19 | 2003-05-14 | Torrent Pharmaceuticals Ltd | 美容及び治療用途におけるピリジニウム誘導体の使用のための組成物及び方法 |
| GB0328314D0 (en) * | 2003-12-05 | 2004-01-07 | Univ Bath | Therapeutics |
| WO2007132179A2 (fr) * | 2006-05-15 | 2007-11-22 | University Of Bath | Agents thérapeutiques |
| JP2009155315A (ja) * | 2007-12-26 | 2009-07-16 | Fujiyakuhin Co Ltd | 注射剤 |
| AU2010245596A1 (en) * | 2009-05-07 | 2011-12-22 | Torrent Pharmaceuticals Limited | Piperidine derivatives useful for treatment of diebetes |
| CN104812388A (zh) * | 2012-10-05 | 2015-07-29 | 斯菲拉制药私人有限公司 | 新型化合物、其合成及其用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH335521A (de) * | 1955-06-02 | 1959-01-15 | Cilag Ag | Verfahren zur Herstellung neuer quaternärer Salze |
| US3318787A (en) * | 1964-02-07 | 1967-05-09 | Udylite Corp | Electrodeposition of zinc |
| US3823076A (en) * | 1972-05-23 | 1974-07-09 | Du Pont | Zinc electroplating additive |
| JPS5936247B2 (ja) * | 1977-04-20 | 1984-09-03 | ティーディーケイ株式会社 | 電気的表示装置 |
| JPS55138742A (en) * | 1979-04-17 | 1980-10-29 | Fuji Photo Film Co Ltd | Silver halide emulsion developing method |
| JPH0253759A (ja) * | 1988-08-18 | 1990-02-22 | Hamari Yakuhin Kogyo Kk | 新規な４級アンモニウム化合物 |
| DD275872A1 (de) * | 1988-09-27 | 1990-02-07 | Univ Dresden Tech | Verfahren zur herstellung von 5h-pyrido[1',2':1,2]imidazo[5,4-c]chinolin-6-onen |
| DE69629176T2 (de) * | 1995-01-18 | 2004-06-03 | Alteon Inc. | Verwendung von thiazoliumverbindungen zum verhindern und umkehren der bildung von endprodukten der fortgeschrittenen glykosylierung |
| JP2001519813A (ja) * | 1997-04-04 | 2001-10-23 | スミスクライン・ビーチャム・コーポレイション | カルシウム溶解性化合物 |
-
1999
- 1999-10-15 WO PCT/IB1999/001687 patent/WO2001025209A1/fr not_active Application Discontinuation
- 1999-10-15 CZ CZ20011808A patent/CZ20011808A3/cs unknown
- 1999-10-15 EP EP99974071A patent/EP1220843A1/fr not_active Withdrawn
- 1999-10-15 CN CN99814055A patent/CN1329597A/zh active Pending
- 1999-10-15 BR BR9915962-7A patent/BR9915962A/pt not_active IP Right Cessation
- 1999-10-15 MX MXPA02003496A patent/MXPA02003496A/es unknown
- 1999-10-15 AU AU59944/99A patent/AU5994499A/en not_active Abandoned
- 1999-10-15 CA CA002351075A patent/CA2351075A1/fr not_active Abandoned
- 1999-10-15 PL PL99348049A patent/PL348049A1/xx not_active Application Discontinuation
- 1999-10-15 HU HU0301687A patent/HUP0301687A2/hu unknown
- 1999-10-15 JP JP2001528155A patent/JP2003511370A/ja active Pending
-
2002
- 2002-08-12 HK HK02105890.8A patent/HK1044336A1/zh unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107438604A (zh) * | 2015-04-08 | 2017-12-05 | 托伦特药物有限公司 | 新吡啶化合物 |
| CN107438604B (zh) * | 2015-04-08 | 2021-12-03 | 托伦特药物有限公司 | 新吡啶化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| PL348049A1 (en) | 2002-05-06 |
| AU5994499A (en) | 2001-05-10 |
| HK1044336A1 (zh) | 2002-10-18 |
| MXPA02003496A (es) | 2005-06-20 |
| HUP0301687A2 (hu) | 2003-08-28 |
| WO2001025209A1 (fr) | 2001-04-12 |
| JP2003511370A (ja) | 2003-03-25 |
| CN1329597A (zh) | 2002-01-02 |
| EP1220843A1 (fr) | 2002-07-10 |
| CZ20011808A3 (cs) | 2001-08-15 |
| BR9915962A (pt) | 2003-01-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |