CA1162856A - Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique - Google Patents

Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique

Info

Publication number: CA1162856A
Authority: CA; Canada
Prior art keywords: methyl; indole; chlorobenzoyl; acetic acid; methoxy
Prior art date: 1981-07-20
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

Application number

CA000382065A

Other languages

English (en)

Inventor

Dushan M. Dvornik

Nicole Simard-Duquesne

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Wyeth Canada Inc

Original Assignee

Ayerst Mckenna and Harrison Inc

Priority date (The priority date 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 date listed.)

1981-07-20

Filing date

1981-07-20

Publication date

1984-02-28

1981-07-20 Application filed by Ayerst Mckenna and Harrison Inc filed Critical Ayerst Mckenna and Harrison Inc

1981-07-20 Priority to CA000382065A priority Critical patent/CA1162856A/fr

1982-07-20 Priority to JP57127445A priority patent/JPS5824518A/ja

1984-02-28 Application granted granted Critical

1984-02-28 Publication of CA1162856A publication Critical patent/CA1162856A/fr

Status Expired legal-status Critical Current

Links

102000016912 Aldehyde Reductase Human genes 0.000 title claims abstract description 9
108010053754 Aldehyde reductase Proteins 0.000 title claims abstract description 9
CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 title claims description 49
230000005764 inhibitory process Effects 0.000 title description 3
150000003839 salts Chemical class 0.000 claims abstract description 22
150000007529 inorganic bases Chemical class 0.000 claims abstract description 12
150000007530 organic bases Chemical class 0.000 claims abstract description 11
239000000203 mixture Substances 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
239000002552 dosage form Substances 0.000 claims description 4
230000002401 inhibitory effect Effects 0.000 claims description 4
208000002249 Diabetes Complications Diseases 0.000 claims description 3
206010012655 Diabetic complications Diseases 0.000 claims description 3
238000007911 parenteral administration Methods 0.000 claims description 3
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239000003937 drug carrier Substances 0.000 claims description 2
239000002997 ophthalmic solution Substances 0.000 claims description 2
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206010012601 diabetes mellitus Diseases 0.000 abstract description 15
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238000000034 method Methods 0.000 abstract description 8
150000001875 compounds Chemical class 0.000 abstract description 5
229960000905 indomethacin Drugs 0.000 description 23
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 10
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000002253 acid Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
102000004877 Insulin Human genes 0.000 description 5
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239000003538 oral antidiabetic agent Substances 0.000 description 5
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150000001412 amines Chemical class 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 description 3
208000017442 Retinal disease Diseases 0.000 description 3
206010038923 Retinopathy Diseases 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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235000019441 ethanol Nutrition 0.000 description 3
FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 3
239000003617 indole-3-acetic acid Substances 0.000 description 3
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201000001119 neuropathy Diseases 0.000 description 3
230000007823 neuropathy Effects 0.000 description 3
208000033808 peripheral neuropathy Diseases 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
241000283690 Bos taurus Species 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000008103 glucose Substances 0.000 description 2
NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
229910017053 inorganic salt Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
239000007787 solid Substances 0.000 description 2
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239000000600 sorbitol Substances 0.000 description 2
229960000894 sulindac Drugs 0.000 description 2
MLKXDPUZXIRXEP-MFOYZWKCSA-N sulindac Chemical compound CC1=C(CC(O)=O)C2=CC(F)=CC=C2\C1=C/C1=CC=C(S(C)=O)C=C1 MLKXDPUZXIRXEP-MFOYZWKCSA-N 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
WAAPEIZFCHNLKK-UFBFGSQYSA-N (2s,4s)-6-fluoro-2',5'-dioxospiro[2,3-dihydrochromene-4,4'-imidazolidine]-2-carboxamide Chemical compound C([C@H](OC1=CC=C(F)C=C11)C(=O)N)[C@@]21NC(=O)NC2=O WAAPEIZFCHNLKK-UFBFGSQYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
HCQVOEBHAJXJSJ-UHFFFAOYSA-N 2-(4-methylmorpholin-4-ium-4-yl)ethanol Chemical compound OCC[N+]1(C)CCOCC1 HCQVOEBHAJXJSJ-UHFFFAOYSA-N 0.000 description 1
KZTWONRVIPPDKH-UHFFFAOYSA-N 2-(piperidin-1-yl)ethanol Chemical compound OCCN1CCCCC1 KZTWONRVIPPDKH-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
RKWGIWYCVPQPMF-UHFFFAOYSA-N Chloropropamide Chemical compound CCCNC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 RKWGIWYCVPQPMF-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 description 1
241000283973 Oryctolagus cuniculus Species 0.000 description 1
102000004316 Oxidoreductases Human genes 0.000 description 1
108090000854 Oxidoreductases Proteins 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000700159 Rattus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
229960001466 acetohexamide Drugs 0.000 description 1
VGZSUPCWNCWDAN-UHFFFAOYSA-N acetohexamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(=O)NC1CCCCC1 VGZSUPCWNCWDAN-UHFFFAOYSA-N 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
229960001761 chlorpropamide Drugs 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
150000004985 diamines Chemical class 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000003467 diminishing effect Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
229930182830 galactose Natural products 0.000 description 1
150000002402 hexoses Chemical class 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000009434 installation Methods 0.000 description 1
210000003734 kidney Anatomy 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
NNCAWEWCFVZOGF-UHFFFAOYSA-N mepiquat Chemical class C[N+]1(C)CCCCC1 NNCAWEWCFVZOGF-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
KVNYFPKFSJIPBJ-UHFFFAOYSA-N ortho-diethylbenzene Natural products CCC1=CC=CC=C1CC KVNYFPKFSJIPBJ-UHFFFAOYSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
229960003243 phenformin Drugs 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
238000012956 testing procedure Methods 0.000 description 1
125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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OUDSBRTVNLOZBN-UHFFFAOYSA-N tolazamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(=O)NN1CCCCCC1 OUDSBRTVNLOZBN-UHFFFAOYSA-N 0.000 description 1
229960005371 tolbutamide Drugs 0.000 description 1
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230000036642 wellbeing Effects 0.000 description 1

Classifications

- 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
- A61K31/404—Indoles, e.g. pindolol
- A61K31/405—Indole-alkanecarboxylic acids; Derivatives thereof, e.g. tryptophan, indomethacin
- 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
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- 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
- 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
- A61P27/16—Otologicals
- 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
- 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

Landscapes

Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Obesity (AREA)
Hematology (AREA)
Emergency Medicine (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Epidemiology (AREA)
Urology & Nephrology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Pyrrole Compounds (AREA)

CA000382065A 1981-07-20 1981-07-20 Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique Expired CA1162856A (fr)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CA000382065A CA1162856A (fr)	1981-07-20	1981-07-20	Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique
JP57127445A JPS5824518A (ja)	1981-07-20	1982-07-20	糖尿病併発症治療用医薬組成物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000382065A CA1162856A (fr)	1981-07-20	1981-07-20	Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique

Publications (1)

Publication Number	Publication Date
CA1162856A true CA1162856A (fr)	1984-02-28

Family

ID=4120472

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000382065A Expired CA1162856A (fr)	1981-07-20	1981-07-20	Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique

Country Status (2)

Country	Link
JP (1)	JPS5824518A (fr)
CA (1)	CA1162856A (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2001513497A (ja) *	1997-08-08	2001-09-04	メドサン、リセルカエス．アール．エル．	胃分泌過多および腎損傷の予防作用を有する抗炎症剤の製造のための化合物２−メトキシフェニル−１−メチル−５ｐ−メチルベンゾイル−ピロール−２−アセトアミドアセテートの使用

1981
- 1981-07-20 CA CA000382065A patent/CA1162856A/fr not_active Expired
1982
- 1982-07-20 JP JP57127445A patent/JPS5824518A/ja active Pending

Also Published As

Publication number	Publication date
JPS5824518A (ja)	1983-02-14

Legal Events

Date	Code	Title	Description
2001-02-28	MKEX	Expiry

Publication	Publication Date	Title
US4423075A (en)	1983-12-27	Aldose reductase inhibition by 5-fluoro-2-methyl-1-[[4-(methylsulfonyl)phenyl]methylene]-1H-indene-3-acetic acid
US5393772A (en)	1995-02-28	Use of, and method of treatment using, hydroxycarbazole compounds for inhibition of smooth muscle migration and proliferation
EP1243270B2 (fr)	2009-03-25	Neuroprotectuer pour l'oeil d'un mammifère par l'administration d'agents de blocage du canal potassium
US6117844A (en)	2000-09-12	Method and composition for antiviral therapy
IE52170B1 (en)	1987-07-22	(-)-n-methyl-3-(2-methylphenoxy)-3-phenylpropylamine,antidepressant
WO1996017608A1 (fr)	1996-06-13	Utilisation d'inhibiteurs de la guanylate cyclase pour reduire la pression intra-oculaire
JPS5940388B2 (ja)	1984-09-29	ヒダントイン誘導体治療剤
EP0610444B1 (fr)	2003-01-29	Utilisation d'un polyhydroxybenzamide ou de l'un de ses dérivés dans la fabrication d'un médicament destiné au traitement d'infections virales
US4254109A (en)	1981-03-03	1H-Benz[de]isoquinoline-2(3H)-acetic acid derivatives
US5998467A (en)	1999-12-07	Medicine for oculopathy
US5559151A (en)	1996-09-24	Method for reducing intraocular pressure in the mammalian eye by administration of chloride channel blockers
US4307114A (en)	1981-12-22	Aldose reductase inhibition by (Z)-5-fluoro-2-methyl-1-[[4-(methylsulfinyl)phenyl]methylene]-1H-indene-3-acetic acid
US4442118A (en)	1984-04-10	Aldose reductase inhibition by 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid
KR920002328B1 (ko)	1992-03-21	T-세포기능 억제를 위한 3-치환된-2-옥신돌-1-카복스 아마이드
CA1162856A (fr)	1984-02-28	Inhibition de l'aldose-reductase grace a l'acide 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1h-indole- 3-acetique
US5202355A (en)	1993-04-13	Method of inhibiting aldose reductase in diabetic hosts using phenol derivatives
US4423060A (en)	1983-12-27	Aldose reductase inhibition by 1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid
US4361582A (en)	1982-11-30	Aldose reductase inhibition by γ-oxo-8-fluoranthenebutanoic acid
EP0545805A1 (fr)	1993-06-09	Utilisation de la D-fenfluramine et de dérivés de la fenfluramine dans le traitement de l'hypertension chez des sujets insulino-résistants
US4556668A (en)	1985-12-03	Ethylenediamine derivatives of aryloxypropanolamine aryl esters having various medicinal properties
US5837709A (en)	1998-11-17	Use of castanospermine as an anti-inflammatory and immunosupressant agent
EP0444546B1 (fr)	1996-09-11	Dérivés de l'hydantoine pour l'utilisation comme agents hypoglycémiques et/ou hypolipidémiques
US4369188A (en)	1983-01-18	2-Thioxobenz[cd]indole-1(2H)-acetic acid derivatives
EP1200079B1 (fr)	2003-09-24	Derives de 2-aminotetraline destines au traitement du glaucome
NZ239215A (en)	1997-07-27	3-(benzothiazol-2-ylmethyl)-4-oxo-3h-phthalazin-1-ylacetic acid derivatives are used to make a blood uric acid level lowering medicament