CA2481753A1 - Method for treating ileus with an alpha -ketoalkanoic acid or - ester or - amide - Google Patents
Method for treating ileus with an alpha -ketoalkanoic acid or - ester or - amide Download PDFInfo
- Publication number
- CA2481753A1 CA2481753A1 CA002481753A CA2481753A CA2481753A1 CA 2481753 A1 CA2481753 A1 CA 2481753A1 CA 002481753 A CA002481753 A CA 002481753A CA 2481753 A CA2481753 A CA 2481753A CA 2481753 A1 CA2481753 A1 CA 2481753A1
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- ester
- ketoalkanoic acid
- acid
- ketoalkanoic
- 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
- 239000002253 acid Substances 0.000 title claims abstract description 67
- 238000000034 method Methods 0.000 title claims abstract description 66
- 208000008384 ileus Diseases 0.000 title claims abstract description 50
- 150000002148 esters Chemical class 0.000 claims abstract description 43
- 150000001408 amides Chemical class 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 229940117360 ethyl pyruvate Drugs 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000005837 enolization reaction Methods 0.000 claims description 18
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 claims description 17
- 238000012084 abdominal surgery Methods 0.000 claims description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 11
- -1 ethyl alpha-keto-butyrate Chemical compound 0.000 claims description 10
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims description 8
- 229940076788 pyruvate Drugs 0.000 claims description 8
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 7
- 150000001768 cations Chemical class 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- 239000011575 calcium Substances 0.000 claims description 6
- 229910052791 calcium Inorganic materials 0.000 claims description 6
- 239000011777 magnesium Substances 0.000 claims description 6
- 229910052749 magnesium Inorganic materials 0.000 claims description 6
- 239000004081 narcotic agent Substances 0.000 claims description 6
- 239000002246 antineoplastic agent Substances 0.000 claims description 5
- 206010061218 Inflammation Diseases 0.000 claims description 4
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims description 4
- 230000004054 inflammatory process Effects 0.000 claims description 4
- 229940107700 pyruvic acid Drugs 0.000 claims description 4
- NPYPAHLBTDXSSS-UHFFFAOYSA-N Potassium ion Chemical compound [K+] NPYPAHLBTDXSSS-UHFFFAOYSA-N 0.000 claims description 3
- FKNQFGJONOIPTF-UHFFFAOYSA-N Sodium cation Chemical compound [Na+] FKNQFGJONOIPTF-UHFFFAOYSA-N 0.000 claims description 3
- 210000001015 abdomen Anatomy 0.000 claims description 3
- 235000001014 amino acid Nutrition 0.000 claims description 3
- 229910001414 potassium ion Inorganic materials 0.000 claims description 3
- 229910001415 sodium ion Inorganic materials 0.000 claims description 3
- 150000007970 thio esters Chemical group 0.000 claims description 3
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 229940120503 dihydroxyacetone Drugs 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- ILPVOWZUBFRIAX-UHFFFAOYSA-N propyl 2-oxopropanoate Chemical compound CCCOC(=O)C(C)=O ILPVOWZUBFRIAX-UHFFFAOYSA-N 0.000 claims description 2
- FPOLWERNILTNDK-UHFFFAOYSA-N pyruvamide Chemical compound CC(=O)C(N)=O FPOLWERNILTNDK-UHFFFAOYSA-N 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 3
- ASMDYJKWIYISFR-UHFFFAOYSA-N acetyloxymethyl 2-oxopropanoate Chemical compound CC(=O)OCOC(=O)C(C)=O ASMDYJKWIYISFR-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims 1
- MLKXVDJWUISGCA-UHFFFAOYSA-N ethoxymethyl 2-oxopropanoate Chemical compound CCOCOC(=O)C(C)=O MLKXVDJWUISGCA-UHFFFAOYSA-N 0.000 claims 1
- 230000003533 narcotic effect Effects 0.000 claims 1
- 241000700159 Rattus Species 0.000 description 31
- 239000000243 solution Substances 0.000 description 19
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- 238000002350 laparotomy Methods 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
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- 230000037396 body weight Effects 0.000 description 7
- 210000000936 intestine Anatomy 0.000 description 7
- ZTVIKZXZYLEVOL-DGKWVBSXSA-N 2-hydroxy-2-phenylacetic acid [(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] ester Chemical group C([C@H]1CC[C@@H](C2)N1C)C2OC(=O)C(O)C1=CC=CC=C1 ZTVIKZXZYLEVOL-DGKWVBSXSA-N 0.000 description 6
- 229920002307 Dextran Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
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- 206010002091 Anaesthesia Diseases 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 230000037005 anaesthesia Effects 0.000 description 5
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- 239000001110 calcium chloride Substances 0.000 description 5
- 229910001628 calcium chloride Inorganic materials 0.000 description 5
- 235000011148 calcium chloride Nutrition 0.000 description 5
- 150000002085 enols Chemical class 0.000 description 5
- FZWBNHMXJMCXLU-UHFFFAOYSA-N 2,3,4,5-tetrahydroxy-6-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyhexanal Chemical compound OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OCC(O)C(O)C(O)C(O)C=O)O1 FZWBNHMXJMCXLU-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
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- 238000003306 harvesting Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 4
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- 208000024891 symptom Diseases 0.000 description 4
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- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 3
- 239000013011 aqueous formulation Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007979 citrate buffer Substances 0.000 description 3
- 210000001072 colon Anatomy 0.000 description 3
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- 238000011161 development Methods 0.000 description 3
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- 238000011282 treatment Methods 0.000 description 3
- DLGOEMSEDOSKAD-UHFFFAOYSA-N Carmustine Chemical compound ClCCNC(=O)N(N=O)CCCl DLGOEMSEDOSKAD-UHFFFAOYSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
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- 239000000499 gel Substances 0.000 description 2
- 230000000968 intestinal effect Effects 0.000 description 2
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- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 125000005429 oxyalkyl group Chemical group 0.000 description 2
- 230000008855 peristalsis Effects 0.000 description 2
- 210000004303 peritoneum Anatomy 0.000 description 2
- 239000003186 pharmaceutical solution Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
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- DKSZLDSPXIWGFO-BLOJGBSASA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O.OP(O)(O)=O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC DKSZLDSPXIWGFO-BLOJGBSASA-N 0.000 description 1
- BQNSLJQRJAJITR-UHFFFAOYSA-N 1,1,2-trichloro-1,2-difluoroethane Chemical compound FC(Cl)C(F)(Cl)Cl BQNSLJQRJAJITR-UHFFFAOYSA-N 0.000 description 1
- NBUHTTJGQKIBMR-UHFFFAOYSA-N 4,6-dimethylpyrimidin-5-amine Chemical compound CC1=NC=NC(C)=C1N NBUHTTJGQKIBMR-UHFFFAOYSA-N 0.000 description 1
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
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- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 1
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- 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
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
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- 241000699666 Mus <mouse, genus> Species 0.000 description 1
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- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000002837 carbocyclic group Chemical group 0.000 description 1
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- 229940051129 meperidine hydrochloride Drugs 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 229960004715 morphine sulfate Drugs 0.000 description 1
- GRVOTVYEFDAHCL-RTSZDRIGSA-N morphine sulfate pentahydrate Chemical compound O.O.O.O.O.OS(O)(=O)=O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O GRVOTVYEFDAHCL-RTSZDRIGSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
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- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
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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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/223—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin of alpha-aminoacids
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
-
- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/22—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids of acyclic acids, e.g. pravastatin
- A61K31/225—Polycarboxylic acids
-
- 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
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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
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37368002P | 2002-04-17 | 2002-04-17 | |
| US60/373,680 | 2002-04-17 | ||
| PCT/US2003/012135 WO2003088956A1 (en) | 2002-04-17 | 2003-04-17 | Method for treating ileus with an alpha -ketoalkanoic acid or - ester or - amide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2481753A1 true CA2481753A1 (en) | 2003-10-30 |
Family
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Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002481753A Abandoned CA2481753A1 (en) | 2002-04-17 | 2003-04-17 | Method for treating ileus with an alpha -ketoalkanoic acid or - ester or - amide |
| CA002481749A Abandoned CA2481749A1 (en) | 2002-04-17 | 2003-04-17 | Pharmaceutical composition comprising an alpha-ketoalkanoic acid ester or -amide and lactic acid or a lactic acid salt |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002481749A Abandoned CA2481749A1 (en) | 2002-04-17 | 2003-04-17 | Pharmaceutical composition comprising an alpha-ketoalkanoic acid ester or -amide and lactic acid or a lactic acid salt |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US20030216470A1 (enExample) |
| EP (2) | EP1494659B1 (enExample) |
| JP (2) | JP2005527592A (enExample) |
| AT (1) | ATE306257T1 (enExample) |
| AU (2) | AU2003230996A1 (enExample) |
| CA (2) | CA2481753A1 (enExample) |
| DE (1) | DE60301878T2 (enExample) |
| WO (2) | WO2003088955A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602004014140D1 (de) * | 2003-06-13 | 2008-07-10 | Univ Pittsburgh | Verfahren zur behandlung von alkoholischer hepatitis |
| US7464564B2 (en) * | 2003-09-22 | 2008-12-16 | Dippin' Dots, Inc. | Method and apparatus for combining cookie dough and ice cream |
| US20050106301A1 (en) * | 2003-09-24 | 2005-05-19 | Curt Jones | Method and apparatus for cryogenically manufacturing ice cream |
| EP1689431A4 (en) * | 2003-10-27 | 2010-11-17 | Univ Pennsylvania | CYTOPROTECTIVE EFFECTS OF ETHYL PYRUVATE |
| US7316122B1 (en) | 2004-01-06 | 2008-01-08 | Dippin' Dots, Inc. | Tray for producing particulate food products |
| US20060062877A1 (en) * | 2004-09-21 | 2006-03-23 | Curt Jones | Method and apparatus for storing food products |
| US20060093714A1 (en) * | 2004-11-01 | 2006-05-04 | Dippin' Dots, Inc. | Particulate ice cream dot cake |
| US20060093719A1 (en) * | 2004-11-01 | 2006-05-04 | Dippin' Dots, Inc. | Particulate ice cream dot sandwich |
| WO2006108681A2 (en) | 2005-04-15 | 2006-10-19 | Biomac Privatinstitut Für Medizinische Und Zahnmedizinische Forschung, Entwicklung Und Diagnostik Gmbh | Substances and pharmaceutical compositions for the inhibition of glyoxalases and their use against bacteria |
| US7332315B2 (en) * | 2005-08-17 | 2008-02-19 | Colgate-Palmolive Company | Method to remove bisulfite by-products from enzyme compositions |
| US20070134394A1 (en) * | 2005-12-12 | 2007-06-14 | Dippin' Dots, Inc. | Method of manufacturing particulate ice cream for storage in conventional freezers |
| US20070140044A1 (en) * | 2005-12-15 | 2007-06-21 | Dippin' Dots, Inc. | Combined particulate and traditional ice cream |
| US20070140043A1 (en) * | 2005-12-16 | 2007-06-21 | Stan Jones | Method and apparatus of combining food particles and ice cream |
| WO2007120544A2 (en) | 2006-04-12 | 2007-10-25 | Alexander Rayna L | Compositions comprising pyruvate alkyl esters and uses thereof |
| US8603513B2 (en) * | 2007-06-28 | 2013-12-10 | The Procter & Gamble Company | Article comprising calcium for reducing the production of TSST-1 |
| EP2326317A1 (en) * | 2008-09-19 | 2011-06-01 | Cytokine Pharmasciences, Inc | Guanylhydrazones for treatment of postoperative intestinal inflammation |
| CN106727320A (zh) * | 2017-01-13 | 2017-05-31 | 江苏长泰药业有限公司 | 一种用于修复鼻粘膜、降低过敏反应、抗炎作用的组合物 |
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| US3984556A (en) * | 1973-01-19 | 1976-10-05 | Sandoz, Inc. | Alkyl-substituted-tricyclic quinazolinones for lowering blood pressure |
| US3879537A (en) * | 1973-09-04 | 1975-04-22 | Scott Eugene J Van | Treatment of ichthyosiform dermatoses |
| US3988470A (en) * | 1974-02-25 | 1976-10-26 | Scott Eugene J Van | Treatment of palmar and plant disturbed keratosis |
| US4021572A (en) * | 1975-07-23 | 1977-05-03 | Scott Eugene J Van | Prophylactic and therapeutic treatment of acne vulgaris utilizing lactamides and quaternary ammonium lactates |
| US4645764A (en) * | 1981-04-01 | 1987-02-24 | Montefiore Hospital | Method for preventing body fat deposition in animals |
| US4812479A (en) * | 1981-04-01 | 1989-03-14 | The Montefiore Hospital Society Of Western Pennsylvania, Inc. | Method for preventing body fat deposition in mammals |
| US4351835A (en) * | 1981-04-01 | 1982-09-28 | Montefiore Hospital | Method for preventing body fat deposition in mammals |
| US4548937A (en) * | 1981-04-01 | 1985-10-22 | Montefiore Hospital | Method for preventing body fat deposition in mammals |
| US4415576A (en) * | 1981-04-01 | 1983-11-15 | Montefiore Hospital | Method for preventing body fat deposition in mammals |
| DE3581407D1 (de) * | 1985-09-06 | 1991-02-21 | Nestle Sa | Bewahrung lebender gewebe. |
| WO1987003808A1 (en) * | 1985-12-18 | 1987-07-02 | Veech Richard L | Fluid therapy with l-lactate and/or pyruvate anions |
| US5389677B1 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Method of treating wrinkles using glycalic acid |
| AU618517B2 (en) * | 1986-12-23 | 1992-01-02 | Eugene J. Van Scott | Additives enhancing topical actions of therapeutic agents |
| US5091171B2 (en) * | 1986-12-23 | 1997-07-15 | Tristrata Inc | Amphoteric compositions and polymeric forms of alpha hydroxyacids and their therapeutic use |
| US6051609A (en) * | 1997-09-09 | 2000-04-18 | Tristrata Technology, Inc. | Additives enhancing the effect of therapeutic agents |
| US4988515A (en) * | 1988-01-28 | 1991-01-29 | The Regents Of The Univ. Of Calif. | Cardioplegic solution |
| EP0345082A3 (en) * | 1988-06-02 | 1990-04-04 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Enzyme formation suppressing agent |
| US5147650A (en) * | 1988-07-29 | 1992-09-15 | University Of Florida | Compositions and methods for achieving improved physiological response to exercise |
| US4981687A (en) * | 1988-07-29 | 1991-01-01 | University Of Florida | Compositions and methods for achieving improved physiological response to exercise |
| US4874790A (en) * | 1988-08-15 | 1989-10-17 | Montefiore Hospital Association Of Western Pennsylvania | Method for improving the glucose metabolism of an animal having diabetic tendencies |
| US5066578A (en) * | 1989-12-21 | 1991-11-19 | The Regents Of The University Of California | Long-term preservation of organs for transplantation |
| US5075210A (en) * | 1989-12-21 | 1991-12-24 | The Regents Of The University Of California | Preservation of the heart for transplantation |
| US5210098A (en) * | 1990-09-21 | 1993-05-11 | Regents Of The University Of Minnesota | Use of pyruvate to treat acute renal failure |
| US5134162A (en) * | 1990-12-24 | 1992-07-28 | The Montefiore Hospital Association Of Western Pennsylvania | Method for lowering high blood cholesterol levels in hyperlipidemic animals and confections as the ingestion medium |
| US5981606A (en) * | 1991-03-01 | 1999-11-09 | Warner-Lambert Company | Therapeutic TGF-beta-wound healing compositions and methods for preparing and using same |
| US5874479A (en) * | 1991-03-01 | 1999-02-23 | Warner-Lambert Company | Therapeutic permeation enhanced-wound healing compositions and methods for preparing and using same |
| US5658956A (en) * | 1991-03-01 | 1997-08-19 | Warner-Lambert Company | Bioadhesive-wound healing compositions and methods for preparing and using same |
| US5648380A (en) * | 1991-03-01 | 1997-07-15 | Warner-Lambert Company | Anti-inflammatory wound healing compositions and methods for preparing and using same |
| US5658957A (en) * | 1991-03-01 | 1997-08-19 | Warner Lambert Company | Immunostimulating wound healing compositions and method for preparing and using same |
| US5674912A (en) * | 1991-03-01 | 1997-10-07 | Warner-Lambert Company | Sunscreen-wound healing compositions and methods for preparing and using same |
| US5652274A (en) * | 1991-03-01 | 1997-07-29 | Martin; Alain | Therapeutic-wound healing compositions and methods for preparing and using same |
| US5633285A (en) * | 1991-03-01 | 1997-05-27 | Warner-Lambert Company | Cytoprotective wound healing compositions and methods for preparing and using same |
| US5863938A (en) * | 1991-03-01 | 1999-01-26 | Warner Lambert Company | Antibacterial-wound healing compositions and methods for preparing and using same |
| US5294641A (en) * | 1991-11-27 | 1994-03-15 | Montefiore - University Hospital | Method for treating a medical patient for cardiac trauma |
| US5256697A (en) * | 1992-04-16 | 1993-10-26 | Abbott Laboratories | Method of administering pyruvate and methods of synthesizing pyruvate precursors |
| US5508308A (en) * | 1992-04-16 | 1996-04-16 | Abbott Laboratories | Use of pyruvylglycine to treat ischemia/reperfusion injury following myocardial infarction |
| PT701455E (pt) * | 1993-06-04 | 2001-09-27 | Biotime Inc | Solucao semelhante a plasma |
| US5395822A (en) * | 1993-09-20 | 1995-03-07 | Izumi; Yukitoshi | Use of pyruvate to prevent neuronal degeneration associated with ischemia |
| US5612374A (en) * | 1994-02-14 | 1997-03-18 | Ronald T. Stanko | Inhibiting growth of mammary adenocarcinoma |
| US5536751A (en) * | 1994-05-09 | 1996-07-16 | The United States Of America As Represented By The Secretary Of The Army | Pharmaceutical alpha-keto carboxylic acid compositions method of making and use thereof |
| US5480909A (en) * | 1994-08-08 | 1996-01-02 | University Of Pittsburgh Medical Center | Method for inhibiting generation of free-radicals |
| US5801198A (en) * | 1995-07-13 | 1998-09-01 | University Of Pittsburgh Medical Center | Retarding neutrophil infiltration ad morphologic reduction in ischemic bowel tissues |
| US5798388A (en) * | 1996-09-06 | 1998-08-25 | Cellular Sciences, Inc. | Method and composition for treating mammalian diseases caused by inflammatory response |
| US5876916A (en) * | 1996-03-18 | 1999-03-02 | Case Western Reserve University | Pyruvate compounds and methods for use thereof |
| US6086789A (en) * | 1996-03-18 | 2000-07-11 | Case Western Reserve University | Medical uses of pyruvates |
| US5667962A (en) * | 1996-03-18 | 1997-09-16 | Case Western Reserve University | Pyruvate thiolester for the prevention of reperfusion injury |
| US5843024A (en) * | 1996-05-17 | 1998-12-01 | Breonics, Inc. | Solution and process for resuscitation and preparation of ischemically damaged tissue |
| US5756469A (en) * | 1996-07-26 | 1998-05-26 | Beale; Paxton K. | Composition of pyruvate and anti-cortisol compounds and method for increasing protein concentration in a mammal |
| US6417231B1 (en) * | 1996-12-23 | 2002-07-09 | Frank L. Greenway | Method and composition for delivering therapeutically effective amounts of pyruvate to a mammal |
| GB9724813D0 (en) * | 1997-11-25 | 1998-01-21 | Univ Nottingham | Reducing muscle fatigue |
| CN1377266A (zh) * | 1999-10-07 | 2002-10-30 | 安瑟斯生命科学公司 | 丙酮酸酯组合物和其在缺血和灌流后复苏中的应用方法 |
-
2003
- 2003-04-17 CA CA002481753A patent/CA2481753A1/en not_active Abandoned
- 2003-04-17 DE DE60301878T patent/DE60301878T2/de not_active Expired - Fee Related
- 2003-04-17 EP EP03726353A patent/EP1494659B1/en not_active Expired - Lifetime
- 2003-04-17 WO PCT/US2003/012134 patent/WO2003088955A1/en not_active Ceased
- 2003-04-17 WO PCT/US2003/012135 patent/WO2003088956A1/en not_active Ceased
- 2003-04-17 JP JP2003585708A patent/JP2005527592A/ja active Pending
- 2003-04-17 AU AU2003230996A patent/AU2003230996A1/en not_active Abandoned
- 2003-04-17 EP EP03724116A patent/EP1496883A1/en not_active Withdrawn
- 2003-04-17 US US10/419,234 patent/US20030216470A1/en not_active Abandoned
- 2003-04-17 JP JP2003585707A patent/JP2005526832A/ja active Pending
- 2003-04-17 AT AT03726353T patent/ATE306257T1/de not_active IP Right Cessation
- 2003-04-17 US US10/419,278 patent/US20030232884A1/en not_active Abandoned
- 2003-04-17 AU AU2003228593A patent/AU2003228593B2/en not_active Expired - Fee Related
- 2003-04-17 CA CA002481749A patent/CA2481749A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE60301878T2 (de) | 2006-08-10 |
| EP1494659B1 (en) | 2005-10-12 |
| CA2481749A1 (en) | 2003-10-30 |
| US20030232884A1 (en) | 2003-12-18 |
| ATE306257T1 (de) | 2005-10-15 |
| JP2005527592A (ja) | 2005-09-15 |
| AU2003230996A1 (en) | 2003-11-03 |
| WO2003088956A1 (en) | 2003-10-30 |
| AU2003228593B2 (en) | 2006-07-27 |
| AU2003228593A1 (en) | 2003-11-03 |
| WO2003088955A1 (en) | 2003-10-30 |
| EP1494659A1 (en) | 2005-01-12 |
| EP1496883A1 (en) | 2005-01-19 |
| DE60301878D1 (de) | 2006-02-23 |
| WO2003088956A8 (en) | 2004-04-15 |
| JP2005526832A (ja) | 2005-09-08 |
| US20030216470A1 (en) | 2003-11-20 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |