LU80596A1 - Amides subsittues de l- et dl-phenylglycine,leur procede de production et compostition pharmaceutique les contenant - Google Patents

Amides subsittues de l- et dl-phenylglycine,leur procede de production et compostition pharmaceutique les contenant Download PDF

Info

Publication number: LU80596A1
Authority: LU; Luxembourg
Prior art keywords: group; formula; compound; amino; solution
Prior art date: 1977-11-30

Application number

LU80596A

Other languages

English (en)

French (fr)

Inventor

P Cross

J Danilewicz

I Barnish

Original Assignee

Pfizer

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.)

1977-11-30

Filing date

1978-11-29

Publication date

1980-06-05

1978-11-29 Application filed by Pfizer filed Critical Pfizer

1980-06-05 Publication of LU80596A1 publication Critical patent/LU80596A1/fr

Links

150000001408 amides Chemical class 0.000 title claims description 11
ZGUNAGUHMKGQNY-UHFFFAOYSA-N alpha-phenylglycine Chemical compound OC(=O)C(N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-UHFFFAOYSA-N 0.000 title claims description 5
238000004519 manufacturing process Methods 0.000 title claims description 3
239000008194 pharmaceutical composition Substances 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims description 37
238000000034 method Methods 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 9
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
150000001412 amines Chemical class 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 7
230000008569 process Effects 0.000 claims description 6
-1 carboxy, amino Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical group OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
GXUAKXUIILGDKW-UHFFFAOYSA-N 2-azaniumyl-2-(4-methoxyphenyl)acetate Chemical compound COC1=CC=C(C(N)C(O)=O)C=C1 GXUAKXUIILGDKW-UHFFFAOYSA-N 0.000 claims description 3
125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
150000008064 anhydrides Chemical class 0.000 claims description 3
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000000304 alkynyl group Chemical group 0.000 claims description 2
125000004663 dialkyl amino group Chemical group 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000002844 melting Methods 0.000 description 9
230000008018 melting Effects 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
241000700159 Rattus Species 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
230000006870 function Effects 0.000 description 6
239000007787 solid Substances 0.000 description 6
238000001914 filtration Methods 0.000 description 5
239000007789 gas Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
150000004728 pyruvic acid derivatives Chemical class 0.000 description 5
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
239000002904 solvent Substances 0.000 description 4
230000000638 stimulation Effects 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000126 substance Substances 0.000 description 4
210000001519 tissue Anatomy 0.000 description 4
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
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 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 3
229940024606 amino acid Drugs 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
150000001413 amino acids Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
150000001720 carbohydrates Chemical class 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
239000000902 placebo Substances 0.000 description 3
229940068196 placebo Drugs 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 2
RQJDUEKERVZLLU-UHFFFAOYSA-N 4-Hydroxybenzylamine Chemical compound NCC1=CC=C(O)C=C1 RQJDUEKERVZLLU-UHFFFAOYSA-N 0.000 description 2
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-NJFSPNSNSA-N Carbon-14 Chemical compound [14C] OKTJSMMVPCPJKN-NJFSPNSNSA-N 0.000 description 2
101710088194 Dehydrogenase Proteins 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
239000004471 Glycine Substances 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000017531 blood circulation Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
230000023852 carbohydrate metabolic process Effects 0.000 description 2
235000021256 carbohydrate metabolism Nutrition 0.000 description 2
210000000748 cardiovascular system Anatomy 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000008103 glucose Substances 0.000 description 2
229960002449 glycine Drugs 0.000 description 2
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 2
235000009200 high fat diet Nutrition 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
238000010253 intravenous injection 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
230000004060 metabolic process Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
235000021317 phosphate Nutrition 0.000 description 2
150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000001665 trituration Methods 0.000 description 2
JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
LJCWONGJFPCTTL-UHFFFAOYSA-N 4-hydroxyphenylglycine Chemical compound OC(=O)C(N)C1=CC=C(O)C=C1 LJCWONGJFPCTTL-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
206010002383 Angina Pectoris Diseases 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
108010016626 Dipeptides Proteins 0.000 description 1
206010019280 Heart failures Diseases 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
208000008589 Obesity Diseases 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
GZCGUPFRVQAUEE-SLPGGIOYSA-N aldehydo-D-glucose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-SLPGGIOYSA-N 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 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
150000001371 alpha-amino acids Chemical class 0.000 description 1
235000008206 alpha-amino acids Nutrition 0.000 description 1
238000010640 amide synthesis reaction Methods 0.000 description 1
229940089206 anhydrous dextrose Drugs 0.000 description 1
210000001557 animal structure Anatomy 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000006630 butoxycarbonylamino group Chemical group 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
150000001733 carboxylic acid esters Chemical group 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
230000000295 complement effect Effects 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000008878 coupling Effects 0.000 description 1
239000007822 coupling agent Substances 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
231100000673 dose–response relationship Toxicity 0.000 description 1
230000000694 effects Effects 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
230000005284 excitation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229960001269 glycine hydrochloride Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000004464 hydroxyphenyl group Chemical group 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
229960001317 isoprenaline Drugs 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
150000002632 lipids Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
MWZPENIJLUWBSY-VIFPVBQESA-N methyl L-tyrosinate Chemical compound COC(=O)[C@@H](N)CC1=CC=C(O)C=C1 MWZPENIJLUWBSY-VIFPVBQESA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
PBMIETCUUSQZCG-UHFFFAOYSA-N n'-cyclohexylmethanediimine Chemical compound N=C=NC1CCCCC1 PBMIETCUUSQZCG-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000021590 normal diet Nutrition 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
230000008557 oxygen metabolism Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
150000005331 phenylglycines Chemical class 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000001020 rhythmical effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
NGSFWBMYFKHRBD-UHFFFAOYSA-M sodium lactate Chemical compound [Na+].CC(O)C([O-])=O NGSFWBMYFKHRBD-UHFFFAOYSA-M 0.000 description 1
229940074404 sodium succinate Drugs 0.000 description 1
ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003899 tartaric acid esters Chemical class 0.000 description 1
230000029305 taxis Effects 0.000 description 1
ISHLCKAQWKBMAU-UHFFFAOYSA-N tert-butyl n-diazocarbamate Chemical compound CC(C)(C)OC(=O)N=[N+]=[N-] ISHLCKAQWKBMAU-UHFFFAOYSA-N 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
229960004441 tyrosine Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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LU80596A 1977-11-30 1978-11-29 Amides subsittues de l- et dl-phenylglycine,leur procede de production et compostition pharmaceutique les contenant LU80596A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB4997577		1977-11-30
GB4997577		1977-11-30

Publications (1)

Publication Number	Publication Date
LU80596A1 true LU80596A1 (fr)	1980-06-05

Family

ID=10454182

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU80596A LU80596A1 (fr)	1977-11-30	1978-11-29	Amides subsittues de l- et dl-phenylglycine,leur procede de production et compostition pharmaceutique les contenant

Country Status (20)

Country	Link
US (1)	US4218474A (de)
JP (1)	JPS5484546A (de)
AR (1)	AR219957A1 (de)
AT (1)	AT362770B (de)
AU (1)	AU507028B2 (de)
BE (1)	BE872347A (de)
CA (1)	CA1101846A (de)
DE (1)	DE2851435C2 (de)
DK (1)	DK531178A (de)
ES (1)	ES475514A1 (de)
FI (1)	FI783638A7 (de)
FR (1)	FR2410644A2 (de)
IE (1)	IE47635B1 (de)
IL (1)	IL56064A (de)
IT (1)	IT1192590B (de)
LU (1)	LU80596A1 (de)
NL (1)	NL7811692A (de)
PH (1)	PH14681A (de)
PT (1)	PT68834A (de)
SE (1)	SE7812268L (de)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5921656A (ja) *	1982-07-28	1984-02-03	Takeda Chem Ind Ltd	ポリペプチド誘導体
US4563352A (en) *	1982-10-04	1986-01-07	The Salk Institute For Biological Studies	Human pancreatic GRF
US4595677A (en) *	1982-12-03	1986-06-17	Ciba-Geigy Corporation	Substituted tetrapeptides
JPS59141547A (ja) *	1983-02-01	1984-08-14	Eisai Co Ltd	鎮痛作用を有する新規ペプタイドおよび製法
GB8322414D0 (en) *	1983-08-19	1983-09-21	Szelke M	Renin inhibitors
WO1985003873A1 (en) *	1984-03-01	1985-09-12	Vernon Erk	Method of treating hypertension in vertebrates
JPS61501564A (ja) *	1984-03-01	1986-07-31	ア−ク，バ−ノン	老人の記憶疾患の治療方法
EP0174978B1 (de) *	1984-03-01	1990-11-07	ERK, Vernon	Prophylaxeverfahren oder behandlung von atherosklerose
EP0175714A4 (de) *	1984-03-01	1987-11-09	Vernon Erk	Behandlungsverfahren von hypoglycemia bei wirbeltieren.
DE3587988D1 (de) *	1984-03-01	1995-03-23	Vernon Erk	Behandlungsverfahren für depressionen bei wirbeltieren.
US4661473A (en) *	1984-03-27	1987-04-28	Merck & Co., Inc.	Renin inhibitors containing peptide isosteres
US4668663A (en) *	1984-03-27	1987-05-26	Merck & Co., Inc.	Renin inhibitors containing homophe8
US4659693A (en) *	1984-04-30	1987-04-21	Syntex (U.S.A.) Inc.	N,N'-dialkyl substituted guanidino amino acyl residue substituted GRF-analog peptides
DE3527356A1 (de) *	1985-07-31	1987-02-05	Degussa	Verfahren zur verbesserung der fruchtbarkeit von haustieren
US5252718A (en) *	1986-04-22	1993-10-12	The Salk Institute For Biological Studies	Fibroblast growth factor antagonists
DE68922602T2 (de) *	1988-01-28	1995-12-07	Polygen Holding Corp	Polypeptide mit hormonwachstumsbefreiender wirkung.
NL1010506C2 (nl) *	1998-11-06	2000-05-09	Dsm Nv	Werkwijze voor de bereiding van bêta-lactam antibiotica.
KR100389644B1 (ko) *	2001-02-26	2003-06-27	한미약품 주식회사	4-히드록시페닐글리신 무수물 및 이의 제조방법
US7230097B2 (en) *	2003-03-10	2007-06-12	Lupin Ltd.	Process for preparation of 7-[α-Amino (4-hydroxyphenyl) acetamido]-3-substituted-3-cephem-4-carboxylic acid
JP1610197S (de)	2017-09-25	2018-07-30

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2868818A (en) *	1953-12-15	1959-01-13	Merck & Co Inc	Alpha methyl phenylalanines
US2833764A (en) *	1954-11-18	1958-05-06	American Cyanamid Co	O-methyl-l-tyrosyl amides and their preparation
US3725470A (en) *	1969-05-14	1973-04-03	Hoffmann La Roche	Amino acid derivatives
ES400897A1 (es) *	1972-03-18	1975-02-01	Beecham Group Ltd	Un procedimiento para la preparacion de alfa-amino-p-hidro-xibencilpenicilina o de un ester de grafito.
DE2510634A1 (de) *	1975-03-12	1976-09-23	Boehringer Mannheim Gmbh	L-3-(3,4-dihydroxy-phenyl)-2- methyl-alanin-peptide und verfahren zu deren herstellung
NL7514300A (nl) *	1975-12-09	1977-06-13	Stamicarbon	Werkwijze voor de bereiding van optisch actief fenylglycineamide.
US4107440A (en) *	1975-12-15	1978-08-15	Smithkline Corporation	Intermediates for preparing substituted phenylglycylcephalosporins
GB1547206A (en) *	1976-09-28	1979-06-06	Pfizer Ltd	Pharmaceutical compositions
PH14064A (en) *	1977-05-06	1981-01-26	Pfizer	Phenylgycine derivatives,pharmaceutical compositions and method of use

1978
- 1978-10-13 PH PH21703A patent/PH14681A/en unknown
- 1978-10-30 US US05/955,644 patent/US4218474A/en not_active Expired - Lifetime
- 1978-11-28 FI FI783638A patent/FI783638A7/fi unknown
- 1978-11-28 ES ES475514A patent/ES475514A1/es not_active Expired
- 1978-11-28 CA CA316,991A patent/CA1101846A/en not_active Expired
- 1978-11-28 IL IL56064A patent/IL56064A/xx unknown
- 1978-11-28 AU AU42008/78A patent/AU507028B2/en not_active Expired
- 1978-11-28 SE SE7812268A patent/SE7812268L/xx unknown
- 1978-11-28 DK DK531178A patent/DK531178A/da not_active Application Discontinuation
- 1978-11-28 PT PT68834A patent/PT68834A/pt unknown
- 1978-11-28 AR AR274600A patent/AR219957A1/es active
- 1978-11-28 AT AT0850678A patent/AT362770B/de not_active IP Right Cessation
- 1978-11-28 BE BE191995A patent/BE872347A/xx not_active IP Right Cessation
- 1978-11-28 IT IT30290/78A patent/IT1192590B/it active
- 1978-11-28 DE DE2851435A patent/DE2851435C2/de not_active Expired
- 1978-11-29 FR FR7833687A patent/FR2410644A2/fr active Granted
- 1978-11-29 JP JP14773078A patent/JPS5484546A/ja active Granted
- 1978-11-29 IE IE2359/78A patent/IE47635B1/en unknown
- 1978-11-29 LU LU80596A patent/LU80596A1/fr unknown
- 1978-11-29 NL NL7811692A patent/NL7811692A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL56064A0 (en)	1979-01-31
CA1101846A (en)	1981-05-26
US4218474A (en)	1980-08-19
IT1192590B (it)	1988-04-20
AT362770B (de)	1981-06-10
ATA850678A (de)	1980-11-15
IE782359L (en)	1979-05-30
JPS5484546A (en)	1979-07-05
IT7830290A0 (it)	1978-11-28
AU507028B2 (en)	1980-01-31
AR219957A1 (es)	1980-09-30
DE2851435A1 (de)	1979-06-13
NL7811692A (nl)	1979-06-01
IE47635B1 (en)	1984-05-16
DK531178A (da)	1979-05-31
FI783638A7 (fi)	1979-05-31
ES475514A1 (es)	1979-04-01
PH14681A (en)	1981-11-10
SE7812268L (sv)	1979-05-31
BE872347A (fr)	1979-05-28
IL56064A (en)	1982-01-31
DE2851435C2 (de)	1982-11-25
JPS5740139B2 (de)	1982-08-25
PT68834A (en)	1978-12-01
FR2410644B2 (de)	1982-10-08
AU4200878A (en)	1979-06-07
FR2410644A2 (fr)	1979-06-29

Publication	Publication Date	Title
LU80596A1 (fr)	1980-06-05	Amides subsittues de l- et dl-phenylglycine,leur procede de production et compostition pharmaceutique les contenant
EP0679161B1 (de)	1998-06-24	Thiazolidinederivate ihre herstellung und sie enthaltende medikamente
LU79761A1 (fr)	1980-01-22	Procede de preparation de nouveaux composes de phtalazine et de composition pharmaceutique les contenant
CH642618A5 (fr)	1984-04-30	Phenethanolamines et compositions pharmaceutiques en contenant.
CH639653A5 (fr)	1983-11-30	Aminothiazoles et composition pharmaceutique les contenant.
CA1213280A (fr)	1986-10-28	PROCEDE DE PREPARATION DE NOUVEAUX DERIVES DE 4-(1H- INDOL-3-YL) .alpha.-METHYL PIPERIDINE-1-ETHANOL ET DE LEURS SELS
EP0005689B1 (de)	1981-03-18	Lactam-N-Essigsäuren und ihre Amide, Verfahren zu ihrer Herstellung und Heilmittel, die sie enthalten
CH641759A5 (fr)	1984-03-15	Phenethanolamines et composition pharmaceutique antineoplastique les contenant.
EP0888289A1 (de)	1999-01-07	Krampflösende, enantiomere aminosäure-derivate
CA2101058A1 (fr)	1993-05-23	Composes a structure guanidique et composition pharmaceutique les contenant
FR2493311A1 (fr)	1982-05-07	Derives 2,6-c-dimethyltyrosine1-(d-amino-acide)2-(acide e-amino-caproique et acide g-aminobutyrique)5 de la methionine-encephaline, utiles notamment comme analgesiques
EP0005658A1 (de)	1979-11-28	Peptidderivate, Analoga von Enkephalinen, Verfahren zu deren Herstellung und deren therapeutische Verwendung
EP0004494B1 (de)	1982-02-17	1,3-Dihydro-3-(1-(2-(2,3-dihydro-1,4-benzodioxin-2-yl)2-hydroxy-äthyl)piperidin-4-yl)2H-indol-2-on Derivate, Verfahren zu ihrer Herstellung, ihre Verwendung als Arzneimittel und diese enthaltende pharmazeutische Zubereitungen
EP0024960A2 (de)	1981-03-11	Substituierte heterocyclische Phenoxyamine, Verfahren zu ihrer Herstellung und ihre Verwendung als Mittel für lokale Anästhesie
EP0262053A2 (de)	1988-03-30	Aminosäure-Derivate, Herstellungsverfahren und pharmazeutisches Mittel
FR2503149A1 (fr)	1982-10-08	Esters de mercaptoacyl-carnitines, procede pour leur preparation et leurs utilisations therapeutiques, notamment dans le traitement des intoxications et des brulures et en tant qu'agents mucolytiques
EP0385848A1 (de)	1990-09-05	Benzoxazolinon-Derivate, Verfahren zu deren Herstellung und pharmazeutische Zusammensetzungen, die sie enthalten
CH625214A5 (de)	1981-09-15
FR2548187A1 (fr)	1985-01-04	Composes d'organo-germanium et leurs utilisations therapeutiques en tant qu'inhibiteurs des enzymes qui degradent les peptides opioides
CA1053679A (fr)	1979-05-01	N-(trifluoromethyl-3-phenyl)-1-propyl-2 glycinate de aminoalkyle
EP0150139A2 (de)	1985-07-31	Indol-Ethylphenyl-Derivate, ihre Salze, Vefahren zur Herstellung, Anwendung als Heilmittel und Zusammensetzungen die sie enthalten
FR2597865A1 (fr)	1987-10-30	Nouveaux derives d'un acide benzyl alkyl carboxylique substitue par un radical 4-pyridinyl aminocarbonyle, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant
CH675998A5 (de)	1990-11-30
EP0635495A2 (de)	1995-01-25	Benzospiroalken-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
EP0022017B1 (de)	1982-05-05	Derivate von 2-Benzoyl-4-nitro-aniliden, deren Herstellung und deren Verwendung als Heilmittel