CH507004A - Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques - Google Patents

Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques

Info

Publication number: CH507004A
Authority: CH; Switzerland
Prior art keywords: cysteine; acid; substances; thiazolidine; derivs
Prior art date: 1966-09-12

Application number

CH1269967A

Other languages

English (en)

French (fr)

Inventor

Simion Dr Oeriu

Original Assignee

Mini Ind Chimice

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.)

1966-09-12

Filing date

1967-09-12

Publication date

1971-05-15

1967-09-12 Application filed by Mini Ind Chimice filed Critical Mini Ind Chimice

1971-05-15 Publication of CH507004A publication Critical patent/CH507004A/fr

Links

235000018417 cysteine Nutrition 0.000 title claims abstract description 17
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 title claims abstract description 17
206010063493 Premature ageing Diseases 0.000 title claims abstract description 4
239000000126 substance Substances 0.000 claims abstract description 22
125000004122 cyclic group Chemical group 0.000 claims abstract description 12
238000011282 treatment Methods 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 9
150000003573 thiols Chemical class 0.000 claims abstract description 4
230000004060 metabolic process Effects 0.000 claims abstract description 3
230000001225 therapeutic effect Effects 0.000 claims abstract description 3
XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 11
238000000034 method Methods 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 9
DZLNHFMRPBPULJ-UHFFFAOYSA-N thioproline Chemical compound OC(=O)C1CSCN1 DZLNHFMRPBPULJ-UHFFFAOYSA-N 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
208000035475 disorder Diseases 0.000 claims description 7
230000008569 process Effects 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 6
125000000468 ketone group Chemical group 0.000 claims description 4
LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 claims description 3
208000032038 Premature aging Diseases 0.000 claims description 2
150000001945 cysteines Chemical class 0.000 claims description 2
239000000463 material Substances 0.000 claims description 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
229910052757 nitrogen Inorganic materials 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
229910052791 calcium Inorganic materials 0.000 abstract description 9
MOODSJOROWROTO-UHFFFAOYSA-N salicylsulfuric acid Chemical class OC(=O)C1=CC=CC=C1OS(O)(=O)=O MOODSJOROWROTO-UHFFFAOYSA-N 0.000 abstract description 7
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 abstract description 5
229910052744 lithium Inorganic materials 0.000 abstract description 5
229940072358 xylocaine Drugs 0.000 abstract description 4
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 abstract description 3
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 abstract description 3
229960002442 glucosamine Drugs 0.000 abstract description 3
FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 abstract 1
239000004480 active ingredient Substances 0.000 abstract 1
230000003444 anaesthetic effect Effects 0.000 abstract 1
238000001727 in vivo Methods 0.000 abstract 1
239000003381 stabilizer Substances 0.000 abstract 1
OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 20
229960002433 cysteine Drugs 0.000 description 14
239000000243 solution Substances 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 description 10
235000019152 folic acid Nutrition 0.000 description 10
239000011724 folic acid Substances 0.000 description 10
229960000304 folic acid Drugs 0.000 description 10
VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
230000032683 aging Effects 0.000 description 8
239000011575 calcium Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
QIJRTFXNRTXDIP-UHFFFAOYSA-N (1-carboxy-2-sulfanylethyl)azanium;chloride;hydrate Chemical compound O.Cl.SCC(N)C(O)=O QIJRTFXNRTXDIP-UHFFFAOYSA-N 0.000 description 6
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
229960001305 cysteine hydrochloride Drugs 0.000 description 6
235000013922 glutamic acid Nutrition 0.000 description 6
239000004220 glutamic acid Substances 0.000 description 6
230000003054 hormonal effect Effects 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
230000009471 action Effects 0.000 description 5
210000004556 brain Anatomy 0.000 description 5
229940079593 drug Drugs 0.000 description 5
239000004312 hexamethylene tetramine Substances 0.000 description 5
235000010299 hexamethylene tetramine Nutrition 0.000 description 5
229960004011 methenamine Drugs 0.000 description 5
229940071103 sulfosalicylate Drugs 0.000 description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 4
239000008298 dragée Substances 0.000 description 4
230000006872 improvement Effects 0.000 description 4
JWWCMTHTYFLEPN-UHFFFAOYSA-M lithium;2-sulfooxybenzoate Chemical compound [Li+].OS(=O)(=O)OC1=CC=CC=C1C([O-])=O JWWCMTHTYFLEPN-UHFFFAOYSA-M 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 4
239000004299 sodium benzoate Substances 0.000 description 4
235000010234 sodium benzoate Nutrition 0.000 description 4
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 4
235000010262 sodium metabisulphite Nutrition 0.000 description 4
125000003396 thiol group Chemical group [H]S* 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-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
229920002134 Carboxymethyl cellulose Polymers 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
102000009127 Glutaminase Human genes 0.000 description 3
108010073324 Glutaminase Proteins 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
239000001768 carboxy methyl cellulose Substances 0.000 description 3
235000010948 carboxy methyl cellulose Nutrition 0.000 description 3
239000008112 carboxymethyl-cellulose Substances 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
235000018102 proteins Nutrition 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
229940001584 sodium metabisulfite Drugs 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
235000012222 talc Nutrition 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
-1 vitamin B1 Natural products 0.000 description 3
WXHLLJAMBQLULT-UHFFFAOYSA-N 2-[[6-[4-(2-hydroxyethyl)piperazin-1-yl]-2-methylpyrimidin-4-yl]amino]-n-(2-methyl-6-sulfanylphenyl)-1,3-thiazole-5-carboxamide;hydrate Chemical compound O.C=1C(N2CCN(CCO)CC2)=NC(C)=NC=1NC(S1)=NC=C1C(=O)NC1=C(C)C=CC=C1S WXHLLJAMBQLULT-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
206010003549 asthenia Diseases 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000005515 coenzyme Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
230000002255 enzymatic effect Effects 0.000 description 2
235000019441 ethanol Nutrition 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
230000013632 homeostatic process Effects 0.000 description 2
239000005556 hormone Substances 0.000 description 2
229940088597 hormone Drugs 0.000 description 2
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 2
229910052808 lithium carbonate Inorganic materials 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
206010027599 migraine Diseases 0.000 description 2
239000000203 mixture Substances 0.000 description 2
102000039446 nucleic acids Human genes 0.000 description 2
108020004707 nucleic acids Proteins 0.000 description 2
150000007523 nucleic acids Chemical class 0.000 description 2
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
229940076788 pyruvate Drugs 0.000 description 2
229940107700 pyruvic acid Drugs 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000011084 recovery Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
230000001568 sexual effect Effects 0.000 description 2
230000004936 stimulating effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
229950001139 timonacic Drugs 0.000 description 2
JCAKCGQZNBEITC-UHFFFAOYSA-N 2-methyl-1,3-thiazolidine-2,4-dicarboxylic acid Chemical compound OC(=O)C1(C)NC(C(O)=O)CS1 JCAKCGQZNBEITC-UHFFFAOYSA-N 0.000 description 1
WXTBYSIPOKXCPM-UHFFFAOYSA-N 3-acetyl-1,3-thiazolidine-4-carboxylic acid Chemical compound CC(=O)N1CSCC1C(O)=O WXTBYSIPOKXCPM-UHFFFAOYSA-N 0.000 description 1
208000000044 Amnesia Diseases 0.000 description 1
208000031091 Amnestic disease Diseases 0.000 description 1
LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 description 1
BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical group SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical group S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
208000005171 Dysmenorrhea Diseases 0.000 description 1
206010013935 Dysmenorrhoea Diseases 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010029333 Neurosis Diseases 0.000 description 1
108091005461 Nucleic proteins Proteins 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
229930003451 Vitamin B1 Natural products 0.000 description 1
229930003779 Vitamin B12 Natural products 0.000 description 1
125000003172 aldehyde group Chemical group 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000006986 amnesia Effects 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
230000001548 androgenic effect Effects 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
230000000721 bacterilogical effect Effects 0.000 description 1
210000001217 buttock Anatomy 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
208000013507 chronic prostatitis Diseases 0.000 description 1
AGVAZMGAQJOSFJ-WZHZPDAFSA-M cobalt(2+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(1r,2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2 Chemical compound [Co+2].N#[C-].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP(O)(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O AGVAZMGAQJOSFJ-WZHZPDAFSA-M 0.000 description 1
238000001816 cooling Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
229960003067 cystine Drugs 0.000 description 1
230000002354 daily effect Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000002074 deregulated effect Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
125000002228 disulfide group Chemical group 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
230000008482 dysregulation Effects 0.000 description 1
230000001076 estrogenic effect Effects 0.000 description 1
230000003203 everyday effect Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229940126601 medicinal product Drugs 0.000 description 1
230000009245 menopause Effects 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
208000015238 neurotic disease Diseases 0.000 description 1
239000002547 new drug Substances 0.000 description 1
231100000957 no side effect Toxicity 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
230000007170 pathology Effects 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
201000007094 prostatitis Diseases 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
230000003236 psychic effect Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000003716 rejuvenation Effects 0.000 description 1
229960003885 sodium benzoate Drugs 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
229960003495 thiamine Drugs 0.000 description 1
DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
235000010374 vitamin B1 Nutrition 0.000 description 1
239000011691 vitamin B1 Substances 0.000 description 1
235000019163 vitamin B12 Nutrition 0.000 description 1
239000011715 vitamin B12 Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

CH1269967A 1966-09-12 1967-09-12 Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques CH507004A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
RO5215866		1966-09-12

Publications (1)

Publication Number	Publication Date
CH507004A true CH507004A (fr)	1971-05-15

Family

ID=20086544

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1269967A CH507004A (fr)	1966-09-12	1967-09-12	Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques

Country Status (8)

Country	Link
AT (1)	AT290719B (de)
BE (1)	BE700255A (de)
BR (1)	BR6791411D0 (de)
CH (1)	CH507004A (de)
DE (1)	DE1617645A1 (de)
FR (1)	FR6725M (de)
GB (1)	GB1189487A (de)
NL (1)	NL6709277A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0086258A1 (de) *	1982-01-26	1983-08-24	Degussa Aktiengesellschaft	Verfahren zur Trennung des Racemats (R,S)-Cystein

1967
- 1967-06-20 GB GB2850267A patent/GB1189487A/en not_active Expired
- 1967-06-21 BE BE700255D patent/BE700255A/xx unknown
- 1967-06-29 DE DE19671617645 patent/DE1617645A1/de active Pending
- 1967-07-04 NL NL6709277A patent/NL6709277A/xx unknown
- 1967-07-21 BR BR19141167A patent/BR6791411D0/pt unknown
- 1967-07-25 FR FR115554A patent/FR6725M/fr not_active Expired
- 1967-08-10 AT AT740867A patent/AT290719B/de not_active IP Right Cessation
- 1967-09-12 CH CH1269967A patent/CH507004A/fr not_active IP Right Cessation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0086258A1 (de) *	1982-01-26	1983-08-24	Degussa Aktiengesellschaft	Verfahren zur Trennung des Racemats (R,S)-Cystein

Also Published As

Publication number	Publication date
BE700255A (de)	1967-12-01
GB1189487A (en)	1970-04-29
FR6725M (de)	1969-02-17
BR6791411D0 (pt)	1973-04-26
NL6709277A (de)	1968-03-13
AT290719B (de)	1971-06-11
DE1617645A1 (de)	1972-04-13

Legal Events

Date	Code	Title	Description
1975-04-15	PL	Patent ceased

Publication	Publication Date	Title
EP0001727B1 (de)	1981-11-11	Neue Derivate des 4-Phenyl-2-(2',2',2'-thrichlorethoxycarboxamido)-thiazols, die als Arzneimittel brauchbar sind, diese Verbindungen enthaltende pharmazeutische Zusammensetzungen und Verfahren zur Herstellung dieser Verbindungen
CH629479A5 (fr)	1982-04-30	Derives de la taurine, medicament contenant ces derives et procede de preparation de ces derives.
BE834794A (fr)	1976-02-16	Acide 3-trihydroxygermano-propionique
JPS5838421B2 (ja)	1983-08-23	分岐鎖状ケト酸のオルニチン及びアルギニン塩並びに肝臓及び腎臓障害の治療への使用
CH643529A5 (fr)	1984-06-15	Phenethanolamines.
EA004179B1 (ru)	2004-02-26	Способ лечения неопластического заболевания при введении фенилацетилглутамина, фенилацетилизоглутамина и/или фенилацетата
JPS5995894A (ja)	1984-06-02	医薬組成物
JP7352623B2 (ja)	2023-09-28	抗うつ製品の製造におけるヒドロキシチロソールおよびその誘導体の新規使用
PT1896489E (pt)	2009-04-01	Sais ou complexos de doadores de metilo com ácido fítico ou os seus derivados e método para a sua síntese
CH507004A (fr)	1971-05-15	Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques
CA2650480A1 (fr)	2007-11-08	Composes de type 1, 4-naphtoquinones, compositions les comprenant et utilisation de ces composes en tant qu'agents anti -cancereux
US4413012A (en)	1983-11-01	Method for treating depression
JPS62423A (ja)	1987-01-06	肝疾患治療剤
TWI224506B (en)	2004-12-01	Pharmaceutical composition
US4346110A (en)	1982-08-24	Method for treating depression
EP0426562A1 (de)	1991-05-08	1-(4-Aminophenyl)-2-piperidinopropanon-Derivate, Verfahren zu deren Herstellung und therapeutische Verwendung
EP0258134B1 (de)	1990-05-23	Benzhydrylthiomethan-Derivate enthaltende therapeutische Zusammensetzungen
FR2484255A1 (fr)	1981-12-18	Nouveaux medicaments veterinaires pour inhiber le developpement des protozoaires et compositions therapeutiques et formes pharmaceutiques contenant ces medicaments
CH658786A5 (fr)	1986-12-15	Medicaments qui contiennent d'alpha-(n-pyrrolyl)-acides ou de leurs sels ou esters.
CH472841A (fr)	1969-05-31	Composition stimulant la croissance et le développement des animaux, et procédé de préparation de cette composition
CA1223595A (fr)	1987-06-30	Derives de (quinolyl-4)-1 (piperidyl-4)-2 ethanamine et de (quinolyl-4)-1 (piperidyl-4)-3 propanamine, procedes pour leur preparation et medicaments les contenant
FR2512015A1 (fr)	1983-03-04	Sels de l'acide 2-oxo-1,5-pentane dioique, leur procede de fabrication et medicaments renfermant ces sels
FR2463124A1 (fr)	1981-02-20	Acides 2-amino-3-(alkylthiobenzoyl)-phenylacetiques et derives, et leur utilisation comme anti-inflammatoires, analgesiques, et inhibant l'agglomeration des plaquettes sanguines
EP0263020B1 (de)	1990-07-25	4-Phenylthiazol-Derivate
RU2293553C2 (ru)	2007-02-20	Способ снижения уровня аммиака в крови животных и человека

CH507004A - Procédé de préparation d'un médicament contenant les dérivés cycliques de la cystéine destiné au traitement des processus de vieillissement prématuré et des troubles du métabolisme des substances thioliques - Google Patents

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