FI68613C - Foerfarande foer framstaellning av terapeutiskt aktiva svavelhaltiga n-bensylaminsyror - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiva svavelhaltiga n-bensylaminsyror Download PDFInfo
- Publication number
- FI68613C FI68613C FI771834A FI771834A FI68613C FI 68613 C FI68613 C FI 68613C FI 771834 A FI771834 A FI 771834A FI 771834 A FI771834 A FI 771834A FI 68613 C FI68613 C FI 68613C
- Authority
- FI
- Finland
- Prior art keywords
- compound
- formula
- eller
- cooh
- benzyl
- Prior art date
Links
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 title 2
- 230000004913 activation Effects 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 36
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- -1 N-benzyl amino Chemical class 0.000 claims description 7
- 150000001413 amino acids Chemical class 0.000 claims description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 235000005985 organic acids Nutrition 0.000 claims description 4
- 239000012429 reaction media Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 238000005984 hydrogenation reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- 229940126062 Compound A Drugs 0.000 description 15
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 15
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 210000003097 mucus Anatomy 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 9
- GBFLZEXEOZUWRN-VKHMYHEASA-N S-carboxymethyl-L-cysteine Chemical compound OC(=O)[C@@H](N)CSCC(O)=O GBFLZEXEOZUWRN-VKHMYHEASA-N 0.000 description 8
- GFVBKHKXRAULAJ-JTQLQIEISA-N (2s)-2-[(2-amino-3,5-dibromophenyl)methylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NCC1=CC(Br)=CC(Br)=C1N GFVBKHKXRAULAJ-JTQLQIEISA-N 0.000 description 7
- 241000700198 Cavia Species 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LUJWNXWCZWQXCO-NSHDSACASA-N (2s)-2-[(2-aminophenyl)methylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NCC1=CC=CC=C1N LUJWNXWCZWQXCO-NSHDSACASA-N 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 238000005119 centrifugation Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 210000000621 bronchi Anatomy 0.000 description 4
- 230000028327 secretion Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical class NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229930182817 methionine Natural products 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 238000010186 staining Methods 0.000 description 3
- IAGPZEOZZJOSGZ-JTQLQIEISA-N (2r)-2-[(2-aminophenyl)methylamino]-3-methylsulfanylpropanoic acid Chemical compound CSC[C@@H](C(O)=O)NCC1=CC=CC=C1N IAGPZEOZZJOSGZ-JTQLQIEISA-N 0.000 description 2
- VHDHVFRJTSLCJT-VIFPVBQESA-N (2r)-3-(carboxymethylsulfanyl)-2-[(2-nitrophenyl)methylamino]propanoic acid Chemical compound OC(=O)CSC[C@@H](C(O)=O)NCC1=CC=CC=C1[N+]([O-])=O VHDHVFRJTSLCJT-VIFPVBQESA-N 0.000 description 2
- WRJSCDDNDFJHJJ-VIFPVBQESA-N (2r)-3-methylsulfanyl-2-[(2-nitrophenyl)methylamino]propanoic acid Chemical compound CSC[C@@H](C(O)=O)NCC1=CC=CC=C1[N+]([O-])=O WRJSCDDNDFJHJJ-VIFPVBQESA-N 0.000 description 2
- YIOCEYOHSWFMBX-JTQLQIEISA-N (2s)-4-methylsulfanyl-2-[(2-nitrophenyl)methylamino]butanoic acid Chemical compound CSCC[C@@H](C(O)=O)NCC1=CC=CC=C1[N+]([O-])=O YIOCEYOHSWFMBX-JTQLQIEISA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- OJGDCBLYJGHCIH-UHFFFAOYSA-N bromhexine Chemical compound C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N OJGDCBLYJGHCIH-UHFFFAOYSA-N 0.000 description 2
- 229960003870 bromhexine Drugs 0.000 description 2
- 210000003123 bronchiole Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 229960003646 lysine Drugs 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- DPTCLRBQMTZFJL-JTQLQIEISA-N (2r)-2-[(2-aminophenyl)methylamino]-3-(carboxymethylsulfanyl)propanoic acid Chemical compound NC1=CC=CC=C1CN[C@@H](CSCC(O)=O)C(O)=O DPTCLRBQMTZFJL-JTQLQIEISA-N 0.000 description 1
- UDLOZWHLGVKBBG-NWASOUNVSA-N (2s)-2-[(2-amino-3,5-dibromophenyl)methylamino]-4-methylsulfanylbutanoic acid;(z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.CSCC[C@@H](C(O)=O)NCC1=CC(Br)=CC(Br)=C1N UDLOZWHLGVKBBG-NWASOUNVSA-N 0.000 description 1
- CSLYTJVKUOGOGG-PPHPATTJSA-N (2s)-2-[(2-amino-3,5-dibromophenyl)methylamino]-4-methylsulfanylbutanoic acid;hydrochloride Chemical compound Cl.CSCC[C@@H](C(O)=O)NCC1=CC(Br)=CC(Br)=C1N CSLYTJVKUOGOGG-PPHPATTJSA-N 0.000 description 1
- 240000000073 Achillea millefolium Species 0.000 description 1
- 235000007754 Achillea millefolium Nutrition 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 206010062530 Increased bronchial secretion Diseases 0.000 description 1
- 241000880493 Leptailurus serval Species 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IDIDJDIHTAOVLG-UHFFFAOYSA-N S-methyl-L-cysteine Natural products CSCC(N)C(O)=O IDIDJDIHTAOVLG-UHFFFAOYSA-N 0.000 description 1
- ILVGMCVCQBJPSH-WDSKDSINSA-N Ser-Val Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)[C@@H](N)CO ILVGMCVCQBJPSH-WDSKDSINSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 230000003542 behavioural effect Effects 0.000 description 1
- UCDKONUHZNTQPY-UHFFFAOYSA-N bromhexine hydrochloride Chemical compound Cl.C1CCCCC1N(C)CC1=CC(Br)=CC(Br)=C1N UCDKONUHZNTQPY-UHFFFAOYSA-N 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- 210000000424 bronchial epithelial cell Anatomy 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 235000014413 iron hydroxide Nutrition 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960001913 mecysteine Drugs 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- XOSXWYQMOYSSKB-LDKJGXKFSA-L water blue Chemical compound CC1=CC(/C(\C(C=C2)=CC=C2NC(C=C2)=CC=C2S([O-])(=O)=O)=C(\C=C2)/C=C/C\2=N\C(C=C2)=CC=C2S([O-])(=O)=O)=CC(S(O)(=O)=O)=C1N.[Na+].[Na+] XOSXWYQMOYSSKB-LDKJGXKFSA-L 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
- C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762628911 DE2628911A1 (de) | 1976-06-28 | 1976-06-28 | Neue schwefelhaltige n-benzylaminosaeuren und verfahren zu ihrer herstellung |
| DE2628911 | 1976-06-28 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771834A FI771834A (pt) | 1977-12-29 |
| FI68613B FI68613B (fi) | 1985-06-28 |
| FI68613C true FI68613C (fi) | 1985-10-10 |
Family
ID=5981605
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771834A FI68613C (fi) | 1976-06-28 | 1977-06-10 | Foerfarande foer framstaellning av terapeutiskt aktiva svavelhaltiga n-bensylaminsyror |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4185114A (pt) |
| JP (1) | JPS5331630A (pt) |
| AT (4) | AT348983B (pt) |
| AU (1) | AU506886B2 (pt) |
| BE (1) | BE856157A (pt) |
| CH (1) | CH629483A5 (pt) |
| DE (1) | DE2628911A1 (pt) |
| DK (1) | DK146445C (pt) |
| ES (3) | ES460117A1 (pt) |
| FI (1) | FI68613C (pt) |
| FR (1) | FR2357539A1 (pt) |
| GB (3) | GB1565411A (pt) |
| GR (1) | GR64597B (pt) |
| IE (1) | IE45519B1 (pt) |
| LU (1) | LU77633A1 (pt) |
| NL (1) | NL7707085A (pt) |
| NO (1) | NO144421C (pt) |
| PT (1) | PT66725B (pt) |
| SE (1) | SE441093B (pt) |
| ZA (1) | ZA773835B (pt) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6112230B2 (pt) * | 1974-02-13 | 1986-04-07 | Sharp Kk | |
| FR2423483A2 (fr) * | 1978-04-20 | 1979-11-16 | Boehringer Sohn Ingelheim | Procede de preparation de n-benzyl-aminoacides soufres |
| GB2102792B (en) | 1981-07-07 | 1984-09-26 | Recordati Chem Pharm | Cystine derivatives |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3177222A (en) * | 1963-02-12 | 1965-04-06 | Sterling Drug Inc | 3-aralkyl-4-thiazolidone-2-carboxylic and-2-alkanoic acids, and derivatives thereof |
| US3950542A (en) * | 1967-02-21 | 1976-04-13 | L'oreal | Cysteamine derivatives for oral treatment of seborrhea |
-
1976
- 1976-06-28 DE DE19762628911 patent/DE2628911A1/de not_active Withdrawn
-
1977
- 1977-06-10 FI FI771834A patent/FI68613C/fi not_active IP Right Cessation
- 1977-06-15 AT AT421577A patent/AT348983B/de not_active IP Right Cessation
- 1977-06-24 NO NO772237A patent/NO144421C/no unknown
- 1977-06-25 GR GR53803A patent/GR64597B/el unknown
- 1977-06-27 US US05/810,087 patent/US4185114A/en not_active Expired - Lifetime
- 1977-06-27 CH CH787377A patent/CH629483A5/de not_active IP Right Cessation
- 1977-06-27 JP JP7643877A patent/JPS5331630A/ja active Pending
- 1977-06-27 PT PT66725A patent/PT66725B/pt unknown
- 1977-06-27 DK DK285477A patent/DK146445C/da not_active IP Right Cessation
- 1977-06-27 LU LU77633A patent/LU77633A1/xx unknown
- 1977-06-27 NL NL7707085A patent/NL7707085A/xx not_active Application Discontinuation
- 1977-06-27 ES ES460117A patent/ES460117A1/es not_active Expired
- 1977-06-27 SE SE7707418A patent/SE441093B/xx not_active IP Right Cessation
- 1977-06-27 BE BE178820A patent/BE856157A/xx not_active IP Right Cessation
- 1977-06-27 ZA ZA00773835A patent/ZA773835B/xx unknown
- 1977-06-28 IE IE1329/77A patent/IE45519B1/en unknown
- 1977-06-28 GB GB27068/77A patent/GB1565411A/en not_active Expired
- 1977-06-28 AU AU26520/77A patent/AU506886B2/en not_active Expired
- 1977-06-28 GB GB198/79A patent/GB1565413A/en not_active Expired
- 1977-06-28 GB GB197/79A patent/GB1565412A/en not_active Expired
- 1977-06-28 FR FR7719825A patent/FR2357539A1/fr active Granted
-
1978
- 1978-05-02 AT AT314578A patent/AT351507B/de not_active IP Right Cessation
- 1978-05-02 AT AT314478A patent/AT351506B/de not_active IP Right Cessation
- 1978-05-02 AT AT314378A patent/AT350523B/de not_active IP Right Cessation
- 1978-06-16 ES ES470892A patent/ES470892A1/es not_active Expired
- 1978-06-16 ES ES470890A patent/ES470890A1/es not_active Expired
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: C.H. BOEHRINGER SOHN |