NO131985B - - Google Patents
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- Publication number
- NO131985B NO131985B NO2029/71A NO202971A NO131985B NO 131985 B NO131985 B NO 131985B NO 2029/71 A NO2029/71 A NO 2029/71A NO 202971 A NO202971 A NO 202971A NO 131985 B NO131985 B NO 131985B
- Authority
- NO
- Norway
- Prior art keywords
- aluminum
- acetyl
- glutamine
- rats
- salt
- Prior art date
Links
- KSMRODHGGIIXDV-YFKPBYRVSA-N N-acetyl-L-glutamine Chemical class CC(=O)N[C@H](C(O)=O)CCC(N)=O KSMRODHGGIIXDV-YFKPBYRVSA-N 0.000 claims description 29
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 18
- -1 aluminum alkoxide Chemical class 0.000 claims description 16
- 229910052782 aluminium Inorganic materials 0.000 claims description 14
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 241000700159 Rattus Species 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 16
- 150000003839 salts Chemical class 0.000 description 14
- 208000007107 Stomach Ulcer Diseases 0.000 description 13
- 239000000243 solution Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 208000025865 Ulcer Diseases 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 150000007524 organic acids Chemical class 0.000 description 9
- 231100000397 ulcer Toxicity 0.000 description 9
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 8
- 208000008469 Peptic Ulcer Diseases 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 230000037396 body weight Effects 0.000 description 7
- 208000011906 peptic ulcer disease Diseases 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 4
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960001340 histamine Drugs 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 4
- 229960003147 reserpine Drugs 0.000 description 4
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 231100000419 toxicity Toxicity 0.000 description 4
- 230000001988 toxicity Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 150000004703 alkoxides Chemical class 0.000 description 3
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 3
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000035876 healing Effects 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 2
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 2
- MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- VAYMRGDBPHCZCI-NUBCRITNSA-N aluminum;(2r)-2-acetamido-5-amino-5-oxopentanoic acid Chemical compound [Al+3].CC(=O)N[C@@H](C(O)=O)CCC(N)=O VAYMRGDBPHCZCI-NUBCRITNSA-N 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000000767 anti-ulcer Effects 0.000 description 2
- 229960004544 cortisone Drugs 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 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
- PYUSRTGWUATZCI-UHFFFAOYSA-K C(C)(=O)NCC(=O)[O-].[Al+3].C(C)(=O)NCC(=O)[O-].C(C)(=O)NCC(=O)[O-] Chemical compound C(C)(=O)NCC(=O)[O-].[Al+3].C(C)(=O)NCC(=O)[O-].C(C)(=O)NCC(=O)[O-] PYUSRTGWUATZCI-UHFFFAOYSA-K 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 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 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000004411 aluminium Substances 0.000 description 1
- 229910000329 aluminium sulfate Inorganic materials 0.000 description 1
- JPUHCPXFQIXLMW-UHFFFAOYSA-N aluminium triethoxide Chemical compound CCO[Al](OCC)OCC JPUHCPXFQIXLMW-UHFFFAOYSA-N 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011076 safety test Methods 0.000 description 1
- 210000002151 serous membrane Anatomy 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- UAEJRRZPRZCUBE-UHFFFAOYSA-N trimethoxyalumane Chemical compound [Al+3].[O-]C.[O-]C.[O-]C UAEJRRZPRZCUBE-UHFFFAOYSA-N 0.000 description 1
- MDDPTCUZZASZIQ-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]alumane Chemical compound [Al+3].CC(C)(C)[O-].CC(C)(C)[O-].CC(C)(C)[O-] MDDPTCUZZASZIQ-UHFFFAOYSA-N 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/06—Aluminium, calcium or magnesium; Compounds thereof, e.g. clay
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4803170 | 1970-06-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO131985B true NO131985B (de) | 1975-05-26 |
| NO131985C NO131985C (de) | 1975-09-03 |
Family
ID=12791928
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2029/71A NO131985C (de) | 1970-06-05 | 1971-05-28 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3787466A (de) |
| BE (1) | BE768003A (de) |
| CH (1) | CH562779A5 (de) |
| DK (1) | DK151798C (de) |
| ES (1) | ES391855A1 (de) |
| FR (1) | FR2100722B1 (de) |
| NL (1) | NL154724B (de) |
| NO (1) | NO131985C (de) |
| SE (1) | SE384366B (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1433314A (en) * | 1973-08-09 | 1976-04-28 | Rhone Poulenc Sa | Aluminium and/or magnesium salts |
| US4229446A (en) * | 1979-03-13 | 1980-10-21 | Kyowa Hakko Kogyo Co., Ltd. | Aluminum acetylsalicylate glutaminate |
| US5286480A (en) * | 1992-06-29 | 1994-02-15 | The Procter & Gamble Company | Use of N-acetylated amino acid complexes in oral care compositions |
| CN1047162C (zh) * | 1993-04-17 | 1999-12-08 | 夏小琳 | 乙酰谷氨酰胺锌化合物及其制备和应用 |
| US20030099722A1 (en) * | 2001-10-09 | 2003-05-29 | Baxter Jeffrey H. | Methods and compositions for providing glutamine |
| US20030134851A1 (en) * | 2001-10-09 | 2003-07-17 | Baxter Jeffrey H. | Methods and compositions for providing glutamine |
| WO2004032653A1 (en) * | 2002-10-08 | 2004-04-22 | Abbott Laboratories | Methods and compositions for providing glutamine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2480743A (en) * | 1946-05-03 | 1949-08-30 | Krantz | Basic aluminum salt of an aliphatic amino acid and method of preparing the same |
| GB1108819A (en) * | 1964-07-31 | 1968-04-03 | Rotta Research Lab | Derivatives of 2-acylaminobicarboxylic acids and method for preparing same |
| GB1168302A (en) * | 1967-05-12 | 1969-10-22 | Roland-Yves Mauvernay | Aluminium N-Acetylglycinate and Pharmaceutical Compositions containing the same |
-
1971
- 1971-05-28 NO NO2029/71A patent/NO131985C/no unknown
- 1971-06-01 NL NL717107518A patent/NL154724B/xx not_active IP Right Cessation
- 1971-06-02 CH CH799471A patent/CH562779A5/xx not_active IP Right Cessation
- 1971-06-02 FR FR7119906A patent/FR2100722B1/fr not_active Expired
- 1971-06-02 US US00149336A patent/US3787466A/en not_active Expired - Lifetime
- 1971-06-02 DK DK268171A patent/DK151798C/da active
- 1971-06-02 ES ES391855A patent/ES391855A1/es not_active Expired
- 1971-06-02 BE BE768003A patent/BE768003A/xx not_active IP Right Cessation
- 1971-06-03 SE SE7107177A patent/SE384366B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2127176B2 (de) | 1976-04-08 |
| CH562779A5 (de) | 1975-06-13 |
| DK151798C (da) | 1988-06-06 |
| US3787466A (en) | 1974-01-22 |
| NO131985C (de) | 1975-09-03 |
| BE768003A (fr) | 1971-11-03 |
| FR2100722B1 (de) | 1974-08-23 |
| NL7107518A (de) | 1971-12-07 |
| FR2100722A1 (de) | 1972-03-24 |
| SE384366B (sv) | 1976-05-03 |
| NL154724B (nl) | 1977-10-17 |
| DK151798B (da) | 1988-01-04 |
| DE2127176A1 (de) | 1971-12-09 |
| ES391855A1 (es) | 1974-06-01 |
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