DE1768655B2 - - Google Patents

Info

Publication number: DE1768655B2
Authority: DE; Germany
Prior art keywords: acid; water; zinc; salts; manganese
Prior art date: 1967-06-13
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.): Granted

Application number

DE19681768655

Other languages

German (de)

English (en)

Other versions

DE1768655C3 (xx

DE1768655A1 (de

Inventor

Ernani Dell'acqua

Rodolfo Ferrari

Guiseppe Ghielmetti

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.)

SPA-SOCIETA PRODOTTI ANTIBIOTICI SpA MAILAND (ITALIEN)

Original Assignee

SPA-SOCIETA PRODOTTI ANTIBIOTICI SpA MAILAND (ITALIEN)

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.)

1967-06-13

Filing date

1968-06-12

Publication date

1974-03-07

1968-06-12 Application filed by SPA-SOCIETA PRODOTTI ANTIBIOTICI SpA MAILAND (ITALIEN) filed Critical SPA-SOCIETA PRODOTTI ANTIBIOTICI SpA MAILAND (ITALIEN)

1971-11-18 Publication of DE1768655A1 publication Critical patent/DE1768655A1/de

1974-03-07 Publication of DE1768655B2 publication Critical patent/DE1768655B2/de

1974-10-24 Application granted granted Critical

1974-10-24 Publication of DE1768655C3 publication Critical patent/DE1768655C3/de

Status Granted legal-status Critical Current

Links

OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
239000000203 mixture Substances 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
229910052751 metal Inorganic materials 0.000 claims description 10
239000002184 metal Substances 0.000 claims description 10
239000011701 zinc Substances 0.000 claims description 9
239000000047 product Substances 0.000 claims description 8
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 7
239000004202 carbamide Substances 0.000 claims description 7
239000000243 solution Substances 0.000 claims description 6
239000004475 Arginine Substances 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 5
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 5
239000000843 powder Substances 0.000 claims description 5
229910052725 zinc Inorganic materials 0.000 claims description 5
LCQLHJZYVOQKHU-UHFFFAOYSA-N N-carbamoylglutamic acid Chemical compound NC(=O)NC(C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-UHFFFAOYSA-N 0.000 claims description 4
239000000706 filtrate Substances 0.000 claims description 4
239000003960 organic solvent Substances 0.000 claims description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
150000003751 zinc Chemical class 0.000 claims description 4
238000001784 detoxification Methods 0.000 claims description 3
230000000694 effects Effects 0.000 claims description 3
239000007788 liquid Substances 0.000 claims description 3
239000002244 precipitate Substances 0.000 claims description 3
239000007787 solid Substances 0.000 claims description 3
239000000725 suspension Substances 0.000 claims description 3
206010067125 Liver injury Diseases 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims description 2
150000001868 cobalt Chemical class 0.000 claims description 2
150000002148 esters Chemical class 0.000 claims description 2
238000001914 filtration Methods 0.000 claims description 2
231100000234 hepatic damage Toxicity 0.000 claims description 2
230000008818 liver damage Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
229960005137 succinic acid Drugs 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 8
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 7
239000002253 acid Substances 0.000 claims 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 5
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims 3
235000013495 cobalt Nutrition 0.000 claims 3
239000011572 manganese Substances 0.000 claims 3
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims 3
150000002739 metals Chemical class 0.000 claims 3
238000000034 method Methods 0.000 claims 3
238000003756 stirring Methods 0.000 claims 3
HLKXYZVTANABHZ-REOHCLBHSA-N N-carbamoyl-L-aspartic acid Chemical compound NC(=O)N[C@H](C(O)=O)CC(O)=O HLKXYZVTANABHZ-REOHCLBHSA-N 0.000 claims 2
150000007513 acids Chemical class 0.000 claims 2
239000007864 aqueous solution Substances 0.000 claims 2
LCQLHJZYVOQKHU-VKHMYHEASA-N carglumic acid Chemical compound NC(=O)N[C@H](C(O)=O)CCC(O)=O LCQLHJZYVOQKHU-VKHMYHEASA-N 0.000 claims 2
239000010941 cobalt Substances 0.000 claims 2
229910017052 cobalt Inorganic materials 0.000 claims 2
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 2
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
239000002207 metabolite Substances 0.000 claims 2
210000002569 neuron Anatomy 0.000 claims 2
230000000241 respiratory effect Effects 0.000 claims 2
239000002904 solvent Substances 0.000 claims 2
PMPZMFJQCCSPGS-REOHCLBHSA-N (2s)-4-amino-2-(carbamoylamino)-4-oxobutanoic acid Chemical compound NC(=O)C[C@@H](C(O)=O)NC(N)=O PMPZMFJQCCSPGS-REOHCLBHSA-N 0.000 claims 1
208000014644 Brain disease Diseases 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims 1
208000032274 Encephalopathy Diseases 0.000 claims 1
102000004190 Enzymes Human genes 0.000 claims 1
108090000790 Enzymes Proteins 0.000 claims 1
-1 Isopro- found N 11.8 Substances 0.000 claims 1
AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 1
RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 1
RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 1
AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 1
UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 1
FMRLDPWIRHBCCC-UHFFFAOYSA-L Zinc carbonate Chemical compound [Zn+2].[O-]C([O-])=O FMRLDPWIRHBCCC-UHFFFAOYSA-L 0.000 claims 1
150000001298 alcohols Chemical class 0.000 claims 1
229940024606 amino acid Drugs 0.000 claims 1
235000001014 amino acid Nutrition 0.000 claims 1
150000001413 amino acids Chemical class 0.000 claims 1
229960003121 arginine Drugs 0.000 claims 1
235000003704 aspartic acid Nutrition 0.000 claims 1
150000007514 bases Chemical class 0.000 claims 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 1
230000004071 biological effect Effects 0.000 claims 1
239000008280 blood Substances 0.000 claims 1
210000004369 blood Anatomy 0.000 claims 1
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
229960002173 citrulline Drugs 0.000 claims 1
235000013477 citrulline Nutrition 0.000 claims 1
ZOTKGJBKKKVBJZ-UHFFFAOYSA-L cobalt(2+);carbonate Chemical compound [Co+2].[O-]C([O-])=O ZOTKGJBKKKVBJZ-UHFFFAOYSA-L 0.000 claims 1
229910000001 cobalt(II) carbonate Inorganic materials 0.000 claims 1
201000010099 disease Diseases 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
230000035987 intoxication Effects 0.000 claims 1
231100000566 intoxication Toxicity 0.000 claims 1
150000002576 ketones Chemical class 0.000 claims 1
210000003734 kidney Anatomy 0.000 claims 1
235000006748 manganese carbonate Nutrition 0.000 claims 1
239000011656 manganese carbonate Substances 0.000 claims 1
229940093474 manganese carbonate Drugs 0.000 claims 1
WJZHMLNIAZSFDO-UHFFFAOYSA-N manganese zinc Chemical compound [Mn].[Zn] WJZHMLNIAZSFDO-UHFFFAOYSA-N 0.000 claims 1
229910000016 manganese(II) carbonate Inorganic materials 0.000 claims 1
XMWCXZJXESXBBY-UHFFFAOYSA-L manganese(ii) carbonate Chemical compound [Mn+2].[O-]C([O-])=O XMWCXZJXESXBBY-UHFFFAOYSA-L 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
230000002503 metabolic effect Effects 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
229960003104 ornithine Drugs 0.000 claims 1
239000008024 pharmaceutical diluent Substances 0.000 claims 1
238000001556 precipitation Methods 0.000 claims 1
238000000926 separation method Methods 0.000 claims 1
159000000000 sodium salts Chemical class 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
UMFCIIBZHQXRCJ-NSCUHMNNSA-N trans-anol Chemical compound C\C=C\C1=CC=C(O)C=C1 UMFCIIBZHQXRCJ-NSCUHMNNSA-N 0.000 claims 1
235000004416 zinc carbonate Nutrition 0.000 claims 1
239000011667 zinc carbonate Substances 0.000 claims 1
229910000010 zinc carbonate Inorganic materials 0.000 claims 1
241000700159 Rattus Species 0.000 description 12
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 10
150000001875 compounds Chemical class 0.000 description 8
210000004185 liver Anatomy 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
239000000126 substance Substances 0.000 description 4
241001465754 Metazoa Species 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
239000000654 additive Substances 0.000 description 3
239000003701 inert diluent Substances 0.000 description 3
230000017074 necrotic cell death Effects 0.000 description 3
231100000167 toxic agent Toxicity 0.000 description 3
239000003440 toxic substance Substances 0.000 description 3
108010082126 Alanine transaminase Proteins 0.000 description 2
206010001605 Alcohol poisoning Diseases 0.000 description 2
102000002260 Alkaline Phosphatase Human genes 0.000 description 2
108020004774 Alkaline Phosphatase Proteins 0.000 description 2
108010003415 Aspartate Aminotransferases Proteins 0.000 description 2
102000004625 Aspartate Aminotransferases Human genes 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
206010020575 Hyperammonaemia Diseases 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000002440 hepatic effect Effects 0.000 description 2
238000007912 intraperitoneal administration Methods 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
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
230000001172 regenerating effect Effects 0.000 description 2
230000008929 regeneration Effects 0.000 description 2
238000011069 regeneration method Methods 0.000 description 2
210000002966 serum Anatomy 0.000 description 2
239000008247 solid mixture Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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
LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
241000196324 Embryophyta Species 0.000 description 1
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 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
241001072332 Monia Species 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
108090000340 Transaminases Proteins 0.000 description 1
102000003929 Transaminases Human genes 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000011888 autopsy Methods 0.000 description 1
GHAFORRTMVIXHS-UHFFFAOYSA-L bromosulfophthalein sodium Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C(O)=CC=C1C1(C=2C=C(C(O)=CC=2)S([O-])(=O)=O)C(C(Br)=C(Br)C(Br)=C2Br)=C2C(=O)O1 GHAFORRTMVIXHS-UHFFFAOYSA-L 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000007891 compressed tablet Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004945 emulsification Methods 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
230000000763 evoking effect Effects 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012634 fragment Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
210000005229 liver cell Anatomy 0.000 description 1
230000003908 liver function Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002696 manganese Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
238000012753 partial hepatectomy Methods 0.000 description 1
230000037361 pathway Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
229960001734 sulfobromophthalein Drugs 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

DE19681768655 1967-06-13 1968-06-12 Neue Salze der N-Carbamylglutaminsaeure und der N-Carbamylasparaginsaeure Granted DE1768655A1 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB27168/67A GB1182815A (en)	1967-06-13	1967-06-13	New Salts of N-Carbamyl-Glutamic Acid and of N-Carbamyl-Aspartic Acid.

Publications (3)

Publication Number	Publication Date
DE1768655A1 DE1768655A1 (de)	1971-11-18
DE1768655B2 true DE1768655B2 (xx)	1974-03-07
DE1768655C3 DE1768655C3 (xx)	1974-10-24

Family

ID=10255306

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DE19681768655 Granted DE1768655A1 (de)	1967-06-13	1968-06-12	Neue Salze der N-Carbamylglutaminsaeure und der N-Carbamylasparaginsaeure

Country Status (3)

Country	Link
DE (1)	DE1768655A1 (xx)
FR (1)	FR7642M (xx)
GB (1)	GB1182815A (xx)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1297080A (xx) *	1970-04-17	1972-11-22
FR2230094A1 (en) *	1973-05-14	1974-12-13	Mascart Francis	Safety plug has circular insulating housing with contact pins - and is held to wall socket front by strip of adhesive tape
EP0029000A1 (fr) *	1979-08-03	1981-05-20	Interco S.A.	Sels mixtes d'un métal alcalino-terreux et de diméthylamino-éthanol d'acides N-acyl-glutamiques et N-acyl-aspartiques
CN102599347A (zh) *	2010-03-12	2012-07-25	广州英赛特生物技术有限公司	谷氨酸铜或其衍生物作为动物促生长饲料添加剂的应用
CN102718685A (zh) *	2012-06-01	2012-10-10	广州九益生物技术有限公司	N-氨基甲酰-l-谷氨酸锰络合物的制备方法及应用
CN108017561B (zh) *	2016-11-04	2021-03-30	武汉武药科技有限公司	一种精制卡谷氨酸的方法
CN107445868A (zh) *	2017-08-04	2017-12-08	仲恺农业工程学院	N‑氨甲酰谷氨酸螯合锰及其制备方法
CN111100039A (zh) *	2019-12-24	2020-05-05	长沙兴嘉生物工程股份有限公司	精氨酸生素锌的制备方法及应用

1967
- 1967-06-13 GB GB27168/67A patent/GB1182815A/en not_active Expired
1968
- 1968-06-12 DE DE19681768655 patent/DE1768655A1/de active Granted
- 1968-06-13 FR FR154834A patent/FR7642M/fr not_active Expired

Also Published As

Publication number	Publication date
DE1768655C3 (xx)	1974-10-24
FR7642M (xx)	1970-02-02
DE1768655A1 (de)	1971-11-18
GB1182815A (en)	1970-03-04

Publication	Publication Date	Title
DE2902297A1 (de)	1979-08-02	Inklusionskomplex des cyclodextrins mit indomethacin und verfahren zur herstellung des komplexes
DE69633178T2 (de)	2005-08-11	Eisenverbindungen, zusammensetzungen, herstellungsverfahren und verwendungen davon
DE1768655B2 (xx)	1974-03-07
DE69217819T2 (de)	1997-09-04	Hematoporphyrinderivate Komplexsalze und deren Verwendung bei der Entdeckung und Behandlung von Neoplasmen
DE69807745T2 (de)	2003-05-15	Monoargininylsalz der (e)-3-[1-n-butyl-5-[(2-(2-carboxyphenyl)methoxy-4-chlorphenyl]-1h-pyrazol-4-yl]-2-[(5-methoxy-2,3-dihydrobenzofuran-6-yl)methyl]-prop-2-en carbonsäure
CH624383A5 (xx)	1981-07-31
CH647677A5 (de)	1985-02-15	4'-(acridinylamino)-methansulfon-anisidid enthaltende pharmazeutische zusammensetzung.
EP0091114B1 (de)	1986-06-04	Pharmazeutisch wirksame organische Germaniumverbindungen
DE2705002A1 (de)	1977-08-18	Therapeutische zubereitung
DE2428639A1 (de)	1975-01-09	Therapeutische mittel
DE2820794B1 (de)	1979-05-23	Salze der(-)-(cis)-1,2-Epoxypropylphosphonsaeure,Verfahren zu ihrer Herstellung und diese enthaltendes pharmazeutisches Praeparat
DE1936723C2 (de)	1983-12-22	Salze von Chinarindenalkoloiden und Verfahren zu ihrer Herstellung
DE3025656C2 (xx)	1989-06-22
DE1620177C3 (de)	1975-10-02	N-(2-Hydroxyäthyl)-piperazinocarboxymethyl-tetracyclin, dessen pharmakologisch verwendbaren Salze, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel
DE1493618A1 (de)	1969-07-10	Cumarinderivate und ein Verfahren zu ihrer Herstellung
EP0308665B1 (de)	1993-04-14	Salze der 5-Aminosalicylsäure und sie enthaltende Arzneimittelzubereitungen
DE2364704A1 (de)	1974-09-05	Lysinocalciumchlorid, verfahren zu seiner herstellung und seine verwendung in arzneimitteln
DE2759032C2 (xx)	1988-09-22
EP0061654B1 (de)	1985-07-10	Vincamin-cyclamat, Verfahren zu seiner Herstellung und dieses enthaltende Arzneimittel
EP0253293B1 (de)	1990-02-28	Neue Guanidiniumasparaginate
DE2164988C3 (de)	1982-01-14	2,2-Diphenylcyclopropancarbonsäureesterderivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE2415064A1 (de)	1974-10-10	N-arylsulfonylharnstoffderivate, sie enthaltende arzneimittel und ihre herstellung
EP0054215A1 (de)	1982-06-23	(8-(Dialkylaminoalkoxy)-coffein)-Platinkomplexe, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel
DE1770889A1 (de)	1972-01-13	Wasserloesliche Mischungen von Sulfonamid- und Tetracyclin-Saeuresalzen
DE3415666A1 (de)	1984-11-08	Neue acylaminophenolderivate

Legal Events

Date	Code	Title
1974-10-24	C3	Grant after two publication steps (3rd publication)
1977-12-31	E77	Valid patent as to the heymanns-index 1977
1983-09-08	8339	Ceased/non-payment of the annual fee