CA2351075A1 - Pyridinium derivatives for the treatment of diabetic and aging-related vascular complications - Google Patents
Pyridinium derivatives for the treatment of diabetic and aging-related vascular complications 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
- 229920002472 Starch Polymers 0.000 claims description 3
- 230000001476 alcoholic effect Effects 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 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
- 239000008101 lactose Substances 0.000 claims description 3
- 235000019359 magnesium stearate Nutrition 0.000 claims description 3
- 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 3
- 239000008107 starch Substances 0.000 claims description 3
- 235000019698 starch Nutrition 0.000 claims description 3
- 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
- 229940034610 toothpaste Drugs 0.000 claims description 2
- 239000000606 toothpaste Substances 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 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
- QCWKWVVLPBTMKH-UHFFFAOYSA-N n-(2-hydroxyethyl)-1-(2-oxopropyl)pyridin-1-ium-3-carboxamide;bromide Chemical compound [Br-].CC(=O)C[N+]1=CC=CC(C(=O)NCCO)=C1 QCWKWVVLPBTMKH-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 238000007865 diluting Methods 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000003511 endothelial effect Effects 0.000 claims 1
- 230000002255 enzymatic effect Effects 0.000 claims 1
- 239000000644 isotonic solution Substances 0.000 claims 1
- 230000021368 organ growth Effects 0.000 claims 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
- 238000005956 quaternization reaction Methods 0.000 claims 1
- 108010005094 Advanced Glycation End Products Proteins 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 16
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 8
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 7
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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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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
-
- 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
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Ophthalmology & Optometry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN827CAL99 | 1999-10-06 | ||
| IN827CA1999 | 1999-10-06 | ||
| PCT/IB1999/001687 WO2001025209A1 (en) | 1999-10-06 | 1999-10-15 | Pyridinium derivatives for the treatment of diabetic and aging-related vascular complications |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2351075A1 true CA2351075A1 (en) | 2001-04-12 |
Family
ID=11084921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002351075A Abandoned CA2351075A1 (en) | 1999-10-06 | 1999-10-15 | Pyridinium derivatives for the treatment of diabetic and aging-related vascular complications |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP1220843A1 (zh) |
| JP (1) | JP2003511370A (zh) |
| CN (1) | CN1329597A (zh) |
| AU (1) | AU5994499A (zh) |
| BR (1) | BR9915962A (zh) |
| CA (1) | CA2351075A1 (zh) |
| CZ (1) | CZ20011808A3 (zh) |
| HK (1) | HK1044336A1 (zh) |
| HU (1) | HUP0301687A2 (zh) |
| MX (1) | MXPA02003496A (zh) |
| PL (1) | PL348049A1 (zh) |
| WO (1) | WO2001025209A1 (zh) |
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 |
|---|---|---|---|---|
| JP2004525904A (ja) * | 2000-12-29 | 2004-08-26 | アルテオン インコーポレイテッド | 線維性疾患又は他の適応症ｉｉｉｃの治療方法 |
| 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 |
| PT1243581E (pt) * | 2001-03-21 | 2005-11-30 | Torrent Pharmaceuticals Ltd | Compostos de piridinio uteis no tratamento de doencas relacionadas com age |
| CN1259316C (zh) | 2001-04-05 | 2006-06-14 | 托伦脱药品有限公司 | 用于老龄相关性和糖尿病性血管系统并发症的杂环类化合物 |
| HUP0104831A2 (hu) * | 2001-10-19 | 2003-08-28 | Torrent Pharmaceuticals Ltd. | Készítmény és eljárás piridíniumszármazékok gyógyászati alkalmazására |
| GB0328314D0 (en) * | 2003-12-05 | 2004-01-07 | Univ Bath | Therapeutics |
| WO2007132179A2 (en) * | 2006-05-15 | 2007-11-22 | University Of Bath | Therapeutics comprising pyridinium derivatives |
| JP2009155315A (ja) * | 2007-12-26 | 2009-07-16 | Fujiyakuhin Co Ltd | 注射剤 |
| KR20120018185A (ko) * | 2009-05-07 | 2012-02-29 | 토렌트 파마슈티칼스 리미티드 | 당뇨병 치료에 유용한 피페리딘 유도체 |
| JP6621329B2 (ja) * | 2012-10-05 | 2019-12-18 | スファエラ ファーマ ピーティーイー リミテッド | 新規化合物、それらの合成及びそれらの使用 |
Family Cites Families (9)
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|---|---|---|---|---|
| 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 |
| JP4067562B2 (ja) * | 1995-01-18 | 2008-03-26 | アルテオン インコーポレイテッド | 進行性グリコシル化最終生成物の生成を阻止し、反転するためのチアゾリウム化合物の使用 |
| 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 CA CA002351075A patent/CA2351075A1/en not_active Abandoned
- 1999-10-15 AU AU59944/99A patent/AU5994499A/en not_active Abandoned
- 1999-10-15 PL PL99348049A patent/PL348049A1/xx not_active Application Discontinuation
- 1999-10-15 CN CN99814055A patent/CN1329597A/zh active Pending
- 1999-10-15 CZ CZ20011808A patent/CZ20011808A3/cs unknown
- 1999-10-15 JP JP2001528155A patent/JP2003511370A/ja 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 WO PCT/IB1999/001687 patent/WO2001025209A1/en not_active Application Discontinuation
- 1999-10-15 EP EP99974071A patent/EP1220843A1/en not_active Withdrawn
- 1999-10-15 HU HU0301687A patent/HUP0301687A2/hu unknown
-
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 |
|---|---|
| CZ20011808A3 (cs) | 2001-08-15 |
| BR9915962A (pt) | 2003-01-07 |
| WO2001025209A1 (en) | 2001-04-12 |
| HK1044336A1 (zh) | 2002-10-18 |
| MXPA02003496A (es) | 2005-06-20 |
| JP2003511370A (ja) | 2003-03-25 |
| AU5994499A (en) | 2001-05-10 |
| CN1329597A (zh) | 2002-01-02 |
| PL348049A1 (en) | 2002-05-06 |
| EP1220843A1 (en) | 2002-07-10 |
| HUP0301687A2 (hu) | 2003-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |