CA1051802A - Amino acid derivatives and a process for the preparation thereof - Google Patents

Amino acid derivatives and a process for the preparation thereof

Info

Publication number: CA1051802A
Authority: CA; Canada
Prior art keywords: general formula; compound; group; stands; hydrogen
Prior art date: 1974-04-29
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA225,659A

Other languages

English (en)

French (fr)

Inventor

Laszlo Feuer

Arpad Furka

Ferenc Sebestyen

Jolan Hercsel

Erzsebet Bendefy

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.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

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.)

1974-04-29

Filing date

1975-04-28

Publication date

1979-04-03

1974-04-29 Priority claimed from HU74FE00000928A external-priority patent/HU171576B/hu

1975-03-26 Priority claimed from HU74CI1558A external-priority patent/HU174114B/hu

1975-04-28 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1979-04-03 Application granted granted Critical

1979-04-03 Publication of CA1051802A publication Critical patent/CA1051802A/en

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 58
230000008569 process Effects 0.000 title claims description 44
238000002360 preparation method Methods 0.000 title claims description 26
150000003862 amino acid derivatives Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 153
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 63
239000001257 hydrogen Substances 0.000 claims abstract description 53
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 43
-1 hydroxy, amino Chemical group 0.000 claims abstract description 40
150000002431 hydrogen Chemical group 0.000 claims abstract description 35
229910052736 halogen Inorganic materials 0.000 claims abstract description 25
150000002367 halogens Chemical class 0.000 claims abstract description 24
125000000217 alkyl group Chemical group 0.000 claims abstract description 18
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 18
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 17
125000003118 aryl group Chemical group 0.000 claims abstract description 17
150000003839 salts Chemical class 0.000 claims abstract description 16
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
238000006116 polymerization reaction Methods 0.000 claims abstract description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 8
125000002252 acyl group Chemical class 0.000 claims abstract description 6
125000004104 aryloxy group Chemical group 0.000 claims abstract description 6
125000001424 substituent group Chemical group 0.000 claims abstract description 6
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000004391 aryl sulfonyl group Chemical class 0.000 claims abstract description 5
125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 4
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims abstract description 3
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000005161 aryl oxy carbonyl group Chemical class 0.000 claims abstract description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
125000004475 heteroaralkyl group Chemical class 0.000 claims abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 19
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 8
125000004663 dialkyl amino group Chemical group 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 90
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 76
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 75
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 75
239000000243 solution Substances 0.000 claims description 72
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 50
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 claims description 38
229960000583 acetic acid Drugs 0.000 claims description 37
239000012362 glacial acetic acid Substances 0.000 claims description 35
238000011282 treatment Methods 0.000 claims description 31
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 27
229960003080 taurine Drugs 0.000 claims description 27
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 25
WGXUDTHMEITUBO-YFKPBYRVSA-N glutaurine Chemical compound OC(=O)[C@@H](N)CCC(=O)NCCS(O)(=O)=O WGXUDTHMEITUBO-YFKPBYRVSA-N 0.000 claims description 24
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 18
125000006239 protecting group Chemical group 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
230000007071 enzymatic hydrolysis Effects 0.000 claims description 14
238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 14
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
230000036961 partial effect Effects 0.000 claims description 13
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
229910019142 PO4 Inorganic materials 0.000 claims description 12
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
239000010452 phosphate Substances 0.000 claims description 12
SNKZJIOFVMKAOJ-UHFFFAOYSA-N 3-Aminopropanesulfonate Chemical compound NCCCS(O)(=O)=O SNKZJIOFVMKAOJ-UHFFFAOYSA-N 0.000 claims description 11
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
239000003513 alkali Substances 0.000 claims description 11
230000007062 hydrolysis Effects 0.000 claims description 11
238000006460 hydrolysis reaction Methods 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
239000007787 solid Substances 0.000 claims description 10
239000003054 catalyst Substances 0.000 claims description 9
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 9
238000007327 hydrogenolysis reaction Methods 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 8
238000005984 hydrogenation reaction Methods 0.000 claims description 8
229960003151 mercaptamine Drugs 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
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 claims description 7
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 7
229940099500 cystamine Drugs 0.000 claims description 7
230000002829 reductive effect Effects 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 6
SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 claims description 6
UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 6
238000007127 saponification reaction Methods 0.000 claims description 6
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims description 6
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 5
229910052783 alkali metal Inorganic materials 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
239000000908 ammonium hydroxide Substances 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
229920000642 polymer Polymers 0.000 claims description 5
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
150000001340 alkali metals Chemical class 0.000 claims description 4
OOTFVKOQINZBBF-UHFFFAOYSA-N cystamine Chemical compound CCSSCCN OOTFVKOQINZBBF-UHFFFAOYSA-N 0.000 claims description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 4
RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
108090000765 processed proteins & peptides Proteins 0.000 claims description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
102000005367 Carboxypeptidases Human genes 0.000 claims description 3
108010006303 Carboxypeptidases Proteins 0.000 claims description 3
102000002704 Leucyl aminopeptidase Human genes 0.000 claims description 3
108010004098 Leucyl aminopeptidase Proteins 0.000 claims description 3
238000006114 decarboxylation reaction Methods 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 3
SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical group O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims description 2
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 2
108010024636 Glutathione Proteins 0.000 claims description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 2
239000012042 active reagent Substances 0.000 claims description 2
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 2
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
150000008064 anhydrides Chemical class 0.000 claims description 2
125000004069 aziridinyl group Chemical group 0.000 claims description 2
125000005518 carboxamido group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
229960003180 glutathione Drugs 0.000 claims description 2
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
229910000043 hydrogen iodide Inorganic materials 0.000 claims description 2
239000011159 matrix material Substances 0.000 claims description 2
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 2
150000007530 organic bases Chemical class 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 2
235000010265 sodium sulphite Nutrition 0.000 claims description 2
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
229910000272 alkali metal oxide Inorganic materials 0.000 claims 3
238000005868 electrolysis reaction Methods 0.000 claims 3
GMPYNOTVKNXELU-UHFFFAOYSA-N 1-bromoethanesulfonic acid Chemical compound CC(Br)S(O)(=O)=O GMPYNOTVKNXELU-UHFFFAOYSA-N 0.000 claims 1
PGEBOWMPCYFWAI-UHFFFAOYSA-N 1-bromopropane-1-sulfonic acid Chemical compound CCC(Br)S(O)(=O)=O PGEBOWMPCYFWAI-UHFFFAOYSA-N 0.000 claims 1
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
XPYQFIISZQCINN-QVXDJYSKSA-N 4-amino-1-[(2r,3e,4s,5r)-3-(fluoromethylidene)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrate Chemical compound O.O=C1N=C(N)C=CN1[C@H]1C(=C/F)/[C@H](O)[C@@H](CO)O1 XPYQFIISZQCINN-QVXDJYSKSA-N 0.000 claims 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
230000021736 acetylation Effects 0.000 claims 1
238000006640 acetylation reaction Methods 0.000 claims 1
229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 1
239000007864 aqueous solution Substances 0.000 claims 1
238000006480 benzoylation reaction Methods 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 9
230000001225 therapeutic effect Effects 0.000 abstract description 7
230000000144 pharmacologic effect Effects 0.000 abstract description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 42
239000000126 substance Substances 0.000 description 40
230000000694 effects Effects 0.000 description 36
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 32
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
239000000047 product Substances 0.000 description 28
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
238000001962 electrophoresis Methods 0.000 description 22
229920001467 poly(styrenesulfonates) Polymers 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
XVOYSCVBGLVSOL-REOHCLBHSA-N L-cysteic acid Chemical compound OC(=O)[C@@H](N)CS(O)(=O)=O XVOYSCVBGLVSOL-REOHCLBHSA-N 0.000 description 12
150000002500 ions Chemical class 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000000543 intermediate Substances 0.000 description 11
230000004899 motility Effects 0.000 description 11
FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 9
FPIPGXGPPPQFEQ-BOOMUCAASA-N Vitamin A Natural products OC/C=C(/C)\C=C\C=C(\C)/C=C/C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-BOOMUCAASA-N 0.000 description 9
FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 9
239000000706 filtrate Substances 0.000 description 9
235000019155 vitamin A Nutrition 0.000 description 9
239000011719 vitamin A Substances 0.000 description 9
229940045997 vitamin a Drugs 0.000 description 9
238000004458 analytical method Methods 0.000 description 8
239000012043 crude product Substances 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 7
230000001737 promoting effect Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
238000001816 cooling Methods 0.000 description 6
239000003208 petroleum Substances 0.000 description 6
239000011347 resin Substances 0.000 description 6
229920005989 resin Polymers 0.000 description 6
229910052717 sulfur Inorganic materials 0.000 description 6
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 5
239000004471 Glycine Substances 0.000 description 5
241000700159 Rattus Species 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
230000006378 damage Effects 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
208000027418 Wounds and injury Diseases 0.000 description 4
239000013543 active substance Substances 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
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239000012535 impurity Substances 0.000 description 4
210000003491 skin Anatomy 0.000 description 4
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ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 3
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical group OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
238000011109 contamination Methods 0.000 description 3
239000002537 cosmetic Substances 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
238000011161 development Methods 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
WMJRPJZQQSSDBU-UHFFFAOYSA-L disodium;sulfite;heptahydrate Chemical compound O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])=O WMJRPJZQQSSDBU-UHFFFAOYSA-L 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
208000014674 injury Diseases 0.000 description 3
210000004400 mucous membrane Anatomy 0.000 description 3
239000011573 trace mineral Substances 0.000 description 3
235000013619 trace mineral Nutrition 0.000 description 3
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239000000186 progesterone Substances 0.000 description 1
229940048914 protamine Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000000113 radiomimetic effect Effects 0.000 description 1
230000004223 radioprotective effect Effects 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002784 sclerotic effect Effects 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
NGDIAZZSCVVCEW-UHFFFAOYSA-M sodium;butyl sulfate Chemical compound [Na+].CCCCOS([O-])(=O)=O NGDIAZZSCVVCEW-UHFFFAOYSA-M 0.000 description 1
235000021055 solid food Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000011146 sterile filtration Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000000626 sulfinic acid group Chemical group 0.000 description 1
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
210000001258 synovial membrane Anatomy 0.000 description 1
229940037128 systemic glucocorticoids Drugs 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
230000001519 thymoleptic effect Effects 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
230000018889 transepithelial transport Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1
150000002266 vitamin A derivatives Chemical class 0.000 description 1
235000019154 vitamin C Nutrition 0.000 description 1
239000011718 vitamin C Substances 0.000 description 1
235000019165 vitamin E Nutrition 0.000 description 1
229940046009 vitamin E Drugs 0.000 description 1
239000011709 vitamin E Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1
150000003721 vitamin K derivatives Chemical class 0.000 description 1
229940046010 vitamin k Drugs 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/001—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof by chemical synthesis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/08—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- 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
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/12—Materials from mammals; Compositions comprising non-specified tissues or cells; Compositions comprising non-embryonic stem cells; Genetically modified cells
- A61K35/55—Glands not provided for in groups A61K35/22 - A61K35/545, e.g. thyroids, parathyroids or pineal glands
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/98—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin
- A61K8/981—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution of animal origin of mammals or bird
- 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
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- 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
- A61P3/02—Nutrients, e.g. vitamins, minerals
- 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
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/24—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a ring other than a six-membered aromatic ring of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Epidemiology (AREA)
Diabetes (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Birds (AREA)
Immunology (AREA)
Dermatology (AREA)
Zoology (AREA)
Virology (AREA)
Biophysics (AREA)
Cell Biology (AREA)
Biotechnology (AREA)
Biomedical Technology (AREA)
Nutrition Science (AREA)
Gastroenterology & Hepatology (AREA)
Developmental Biology & Embryology (AREA)
Genetics & Genomics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA225,659A 1974-04-29 1975-04-28 Amino acid derivatives and a process for the preparation thereof Expired CA1051802A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU74FE00000928A HU171576B (hu)	1974-04-29	1974-04-29	Sposob otdelenija gamma-l-glutamil-taurina
HU74CI1558A HU174114B (hu)	1975-03-26	1975-03-26	Sposob poluchenija novykh proizvodnykh aminokislot

Publications (1)

Publication Number	Publication Date
CA1051802A true CA1051802A (en)	1979-04-03

Family

ID=26318406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA225,659A Expired CA1051802A (en)	1974-04-29	1975-04-28	Amino acid derivatives and a process for the preparation thereof

Country Status (23)

Country	Link
JP (1)	JPS6012347B2 (da)
AR (3)	AR218222A1 (da)
AT (6)	AT361902B (da)
AU (1)	AU499173B2 (da)
BE (1)	BE828546A (da)
BG (4)	BG26369A4 (da)
CA (1)	CA1051802A (da)
CH (4)	CH617183A5 (da)
CS (4)	CS209855B2 (da)
DD (2)	DD122377A5 (da)
DE (2)	DE2559989C3 (da)
DK (10)	DK155433C (da)
EG (1)	EG11847A (da)
ES (4)	ES436986A1 (da)
FI (1)	FI65990C (da)
FR (1)	FR2279388A1 (da)
GB (1)	GB1504541A (da)
IL (1)	IL47149A (da)
NL (1)	NL183186C (da)
NO (2)	NO146430C (da)
PL (2)	PL111745B1 (da)
SE (2)	SE430164B (da)
SU (1)	SU747419A3 (da)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8748656B2 (en)	2006-10-12	2014-06-10	Bhi Limited Partnership	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US10471032B1 (en) *	2013-06-13	2019-11-12	Thermolife International, Llc	Substituted glutaurine compounds and substituted glutaurine derivatives

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178199B (en) *	1976-05-06	1982-03-28	Chinoin Gyogyszer Es Vegyeszet	New process for producing amides of omega-amino-carboxylic acids
HU180443B (en) *	1979-04-02	1983-03-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing a pharmaceutical preparation with synergetic action against radiation
HU185632B (en) *	1981-03-27	1985-03-28	Chinoin Gyogyszer Es Vegyeszet	New process for preparing gamma-glutamyl-taurine
CH665645A5 (fr) *	1981-07-09	1988-05-31	Michel Flork	Derives de dipeptides et leur procede de preparation.
HU208072B (en) *	1990-02-28	1993-08-30	Chinoin Gyogyszer Es Vegyeszet	Process for producing pharmaceutical composition suitable for preventing and curing autoimmune diseases and skin affections caused by heat and light radiacion
JPH0680964A (ja) *	1991-12-27	1994-03-22	Sogo Yatsukou Kk	活性酸素消去剤
JPH11180846A (ja) *	1997-12-15	1999-07-06	Sogo Pharmaceut Co Ltd	化粧料
DE10133197A1 (de) *	2001-07-07	2003-01-23	Beiersdorf Ag	Aminosäuren enthaltende kosmetische und dermatologische Zubereitungen zur Behandlung und aktiven Prävention trockener Haut und anderer negativer Veränderungen der physiologischen Homöostase der gesunden Haut

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU169462B (da) *	1971-08-04	1976-11-28

1975
- 1975-04-23 IL IL47149A patent/IL47149A/xx unknown
- 1975-04-24 AT AT314075A patent/AT361902B/de not_active IP Right Cessation
- 1975-04-24 DE DE2559989A patent/DE2559989C3/de not_active Expired
- 1975-04-24 DE DE19752518160 patent/DE2518160A1/de active Granted
- 1975-04-25 FI FI751256A patent/FI65990C/fi not_active IP Right Cessation
- 1975-04-25 ES ES436986A patent/ES436986A1/es not_active Expired
- 1975-04-25 SE SE7504828A patent/SE430164B/xx not_active IP Right Cessation
- 1975-04-28 DD DD185727A patent/DD122377A5/xx unknown
- 1975-04-28 CA CA225,659A patent/CA1051802A/en not_active Expired
- 1975-04-28 SU SU752128794A patent/SU747419A3/ru active
- 1975-04-28 CH CH539075A patent/CH617183A5/de not_active IP Right Cessation
- 1975-04-28 NO NO751504A patent/NO146430C/no unknown
- 1975-04-28 AU AU80564/75A patent/AU499173B2/en not_active Expired
- 1975-04-28 DK DK182875A patent/DK155433C/da not_active IP Right Cessation
- 1975-04-28 EG EG262/75A patent/EG11847A/xx active
- 1975-04-28 DD DD193288A patent/DD125070A5/xx unknown
- 1975-04-28 FR FR7513230A patent/FR2279388A1/fr active Granted
- 1975-04-28 GB GB17608/75A patent/GB1504541A/en not_active Expired
- 1975-04-29 PL PL1975196801A patent/PL111745B1/pl unknown
- 1975-04-29 BE BE155914A patent/BE828546A/xx not_active IP Right Cessation
- 1975-04-29 BG BG030768A patent/BG26369A4/xx unknown
- 1975-04-29 BG BG029816A patent/BG26368A3/xx unknown
- 1975-04-29 PL PL1975196798A patent/PL111746B1/pl unknown
- 1975-04-29 BG BG030770A patent/BG26370A4/xx unknown
- 1975-04-29 BG BG030769A patent/BG26517A4/xx unknown
- 1975-04-29 CS CS752987A patent/CS209855B2/cs unknown
- 1975-04-29 NL NLAANVRAGE7505075,A patent/NL183186C/xx not_active IP Right Cessation
- 1975-04-30 JP JP50051612A patent/JPS6012347B2/ja not_active Expired
1976
- 1976-04-02 AR AR262770A patent/AR218222A1/es active
- 1976-04-02 AR AR262768A patent/AR218221A1/es active
- 1976-04-02 AR AR262769A patent/AR217236A1/es active
- 1976-11-13 ES ES453304A patent/ES453304A1/es not_active Expired
- 1976-11-13 ES ES453306A patent/ES453306A1/es not_active Expired
- 1976-11-13 ES ES453305A patent/ES453305A1/es not_active Expired
1977
- 1977-08-30 AT AT624777A patent/AT359084B/de not_active Expired
- 1977-08-30 AT AT624877A patent/AT359085B/de not_active IP Right Cessation
- 1977-08-30 AT AT624977A patent/AT351007B/de not_active IP Right Cessation
- 1977-10-06 DK DK442877A patent/DK158676C/da active
- 1977-10-06 DK DK442477A patent/DK155732C/da not_active IP Right Cessation
- 1977-10-06 DK DK442677A patent/DK159654C/da not_active IP Right Cessation
- 1977-10-06 DK DK442777A patent/DK442777A/da not_active Application Discontinuation
- 1977-10-06 DK DK442377A patent/DK155520C/da not_active IP Right Cessation
- 1977-10-06 DK DK442577A patent/DK442577A/da not_active Application Discontinuation
- 1977-10-06 DK DK443077A patent/DK159267C/da not_active IP Right Cessation
- 1977-10-06 DK DK442977A patent/DK442977A/da unknown
1978
- 1978-09-22 CS CS786128A patent/CS209856B2/cs unknown
- 1978-09-22 CS CS786129A patent/CS209857B2/cs unknown
- 1978-09-22 CS CS786130A patent/CS209858B2/cs unknown
- 1978-12-14 SE SE7812884A patent/SE441356B/sv not_active IP Right Cessation
1979
- 1979-04-30 AT AT0323079A patent/AT374484B/de not_active IP Right Cessation
- 1979-04-30 AT AT0323179A patent/AT370724B/de not_active IP Right Cessation
- 1979-10-19 CH CH943379A patent/CH624098A5/de not_active IP Right Cessation
- 1979-10-19 CH CH943179A patent/CH621333A5/de not_active IP Right Cessation
- 1979-10-19 CH CH943279A patent/CH621334A5/de not_active IP Right Cessation
1981
- 1981-03-10 NO NO810816A patent/NO149036C/no unknown
1983
- 1983-05-31 DK DK245783A patent/DK155672C/da not_active IP Right Cessation

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8748656B2 (en)	2006-10-12	2014-06-10	Bhi Limited Partnership	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US9499480B2 (en)	2006-10-12	2016-11-22	Bhi Limited Partnership	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US10238611B2 (en)	2006-10-12	2019-03-26	Bellus Health Inc.	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US10857109B2 (en)	2006-10-12	2020-12-08	Bellus Health, Inc.	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US11020360B2 (en)	2006-10-12	2021-06-01	Bellus Health Inc.	Methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid
US10471032B1 (en) *	2013-06-13	2019-11-12	Thermolife International, Llc	Substituted glutaurine compounds and substituted glutaurine derivatives

Also Published As

Publication number	Publication date
DK159267C (da)	1991-02-18
DK159654C (da)	1991-04-08
AT359085B (de)	1980-10-27
GB1504541A (en)	1978-03-22
DK155520B (da)	1989-04-17
NO146430B (no)	1982-06-21
DE2559989C3 (de)	1981-11-19
JPS514121A (da)	1976-01-14
DK442477A (da)	1977-10-06
DK155732B (da)	1989-05-08
CS209856B2 (en)	1981-12-31
NL183186C (nl)	1988-08-16
DK155433B (da)	1989-04-10
NO149036B (no)	1983-10-24
AT370724B (de)	1983-04-25
DK442877A (da)	1977-10-06
DK245783A (da)	1983-05-31
DK442577A (da)	1977-10-06
IL47149A (en)	1979-05-31
DK442777A (da)	1977-10-06
AU499173B2 (en)	1979-04-05
DD122377A5 (da)	1976-10-05
DD125070A5 (da)	1977-03-30
NL7505075A (nl)	1975-10-31
DK442677A (da)	1977-10-06
ES436986A1 (es)	1977-06-16
FI751256A (da)	1975-10-30
AU8056475A (en)	1976-11-04
DK158676B (da)	1990-07-02
DK155672C (da)	1989-10-09
SE430164B (sv)	1983-10-24
FI65990B (fi)	1984-04-30
BG26368A3 (bg)	1979-03-15
DK443077A (da)	1977-10-06
DK158676C (da)	1991-01-14
ATA624877A (de)	1980-03-15
SE441356B (sv)	1985-09-30
SU747419A3 (ru)	1980-07-23
CS209857B2 (en)	1981-12-31
DE2518160A1 (de)	1975-11-20
AT374484B (de)	1984-04-25
BE828546A (fr)	1975-08-18
DK245783D0 (da)	1983-05-31
DK442377A (da)	1977-10-06
JPS6012347B2 (ja)	1985-04-01
AT351007B (de)	1979-07-10
ES453304A1 (es)	1977-11-16
AR217236A1 (es)	1980-03-14
DK155672B (da)	1989-05-01
NO810816L (no)	1975-10-30
NO146430C (no)	1982-09-29
CS209858B2 (en)	1981-12-31
FR2279388A1 (fr)	1976-02-20
ATA323179A (de)	1982-09-15
ATA624777A (de)	1980-03-15
IL47149A0 (en)	1975-06-25
AR218221A1 (es)	1980-05-30
ATA314075A (de)	1980-09-15
CS209855B2 (en)	1981-12-31
EG11847A (en)	1979-06-30
CH624098A5 (da)	1981-07-15
BG26370A4 (bg)	1979-03-15
DK159267B (da)	1990-09-24
ES453306A1 (es)	1977-11-16
SE7812884L (sv)	1978-12-14
DE2559989B1 (de)	1981-02-05
PL111746B1 (en)	1980-09-30
SE7504828L (sv)	1975-10-30
NO751504L (da)	1975-10-30
DK159654B (da)	1990-11-12
ATA624977A (de)	1978-12-15
BG26517A4 (bg)	1979-04-12
AT361902B (de)	1981-04-10
ATA323079A (de)	1983-09-15
CH617183A5 (da)	1980-05-14
DK155433C (da)	1989-10-16
NO149036C (no)	1984-02-01
DK155732C (da)	1989-10-02
ES453305A1 (es)	1977-11-16
AT359084B (de)	1980-10-27
CH621333A5 (da)	1981-01-30
BG26369A4 (bg)	1979-03-15
CH621334A5 (da)	1981-01-30
DK442977A (da)	1977-10-06
AR218222A1 (es)	1980-05-30
FR2279388B1 (da)	1978-07-28
DE2518160C2 (da)	1993-05-06
FI65990C (fi)	1984-08-10
DK182875A (da)	1975-10-30
PL111745B1 (en)	1980-09-30
DK155520C (da)	1989-10-16

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