CS207785B2 - Method of making the derivatives of the n-phenylalanine or n-phenylglycine - Google Patents
Method of making the derivatives of the n-phenylalanine or n-phenylglycine Download PDFInfo
- Publication number
- CS207785B2 CS207785B2 CS791654A CS165479A CS207785B2 CS 207785 B2 CS207785 B2 CS 207785B2 CS 791654 A CS791654 A CS 791654A CS 165479 A CS165479 A CS 165479A CS 207785 B2 CS207785 B2 CS 207785B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- methyl
- hydrogen
- compounds
- general formula
- Prior art date
Links
- XWKAVQKJQBISOL-ZETCQYMHSA-N (2s)-2-anilinopropanoic acid Chemical compound OC(=O)[C@H](C)NC1=CC=CC=C1 XWKAVQKJQBISOL-ZETCQYMHSA-N 0.000 title claims description 5
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 14
- -1 chlorobenzoyl Chemical group 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000001448 anilines Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 23
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 229940035676 analgesics Drugs 0.000 abstract 1
- 239000000730 antalgic agent Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 11
- 239000000126 substance Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 241000699670 Mus sp. Species 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 235000004279 alanine Nutrition 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 230000036407 pain Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- CMGBMDFPBWVRMC-UHFFFAOYSA-N (2-methyl-3-nitrophenyl)-phenylmethanone Chemical compound C1=CC=C([N+]([O-])=O)C(C)=C1C(=O)C1=CC=CC=C1 CMGBMDFPBWVRMC-UHFFFAOYSA-N 0.000 description 3
- FUADXEJBHCKVBN-UHFFFAOYSA-N (3-aminophenyl)-phenylmethanone Chemical compound NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 FUADXEJBHCKVBN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000000202 analgesic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- BNCJTMZAEBHDBA-UHFFFAOYSA-N (3-amino-2-methylphenyl)-(4-chlorophenyl)methanone Chemical compound CC1=C(N)C=CC=C1C(=O)C1=CC=C(Cl)C=C1 BNCJTMZAEBHDBA-UHFFFAOYSA-N 0.000 description 2
- NHTALIXIQROOBT-UHFFFAOYSA-N (3-amino-2-methylphenyl)-phenylmethanone Chemical compound CC1=C(N)C=CC=C1C(=O)C1=CC=CC=C1 NHTALIXIQROOBT-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- 241000906446 Theraps Species 0.000 description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000010908 decantation Methods 0.000 description 2
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 2
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 231100000636 lethal dose Toxicity 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
- 150000004682 monohydrates Chemical class 0.000 description 2
- OBCGCWMCABAZPU-UHFFFAOYSA-N n-(3-benzoylphenyl)-4-chlorobenzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 OBCGCWMCABAZPU-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 235000011150 stannous chloride Nutrition 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- ZEAKJVAJTFSPLN-UHFFFAOYSA-N 2-(3-benzoyl-n-methylanilino)acetic acid Chemical compound OC(=O)CN(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 ZEAKJVAJTFSPLN-UHFFFAOYSA-N 0.000 description 1
- UENLNPJRTOHQIC-UHFFFAOYSA-N 2-methyl-3-nitrobenzoyl chloride Chemical compound CC1=C(C(Cl)=O)C=CC=C1[N+]([O-])=O UENLNPJRTOHQIC-UHFFFAOYSA-N 0.000 description 1
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010017076 Fracture Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010024453 Ligament sprain Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 206010034464 Periarthritis Diseases 0.000 description 1
- 206010038419 Renal colic Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000005298 acute pain Diseases 0.000 description 1
- QNAYBMKLOCPYGJ-UHFFFAOYSA-M alaninate Chemical compound CC(N)C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-M 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- YIEIHBJXRLABFK-UHFFFAOYSA-N ethyl 2-(3-benzoyl-n-methylanilino)acetate Chemical compound CCOC(=O)CN(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 YIEIHBJXRLABFK-UHFFFAOYSA-N 0.000 description 1
- AFVBQUQGYNTKPO-UHFFFAOYSA-N ethyl 2-(3-benzoylanilino)acetate Chemical compound CCOC(=O)CNC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 AFVBQUQGYNTKPO-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000000256 facial nerve Anatomy 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- CVAGXMIIJWVUAF-UHFFFAOYSA-N hypochlorous acid;hydrate Chemical compound O.ClO CVAGXMIIJWVUAF-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000013421 nuclear magnetic resonance imaging Methods 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 208000009935 visceral pain Diseases 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pain & Pain Management (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7807443A FR2419928A1 (fr) | 1978-03-15 | 1978-03-15 | Nouveaux derives de la n-phenylalanine, leur preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS207785B2 true CS207785B2 (en) | 1981-08-31 |
Family
ID=9205810
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS791654A CS207785B2 (en) | 1978-03-15 | 1979-03-13 | Method of making the derivatives of the n-phenylalanine or n-phenylglycine |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4223039A (it) |
| JP (1) | JPS54128555A (it) |
| AT (1) | ATA193279A (it) |
| AU (1) | AU4496879A (it) |
| BE (1) | BE874843A (it) |
| CS (1) | CS207785B2 (it) |
| DE (1) | DE2909742A1 (it) |
| ES (1) | ES478643A1 (it) |
| FI (1) | FI790820A7 (it) |
| FR (1) | FR2419928A1 (it) |
| GB (1) | GB2016448A (it) |
| GR (1) | GR68031B (it) |
| IL (1) | IL56816A0 (it) |
| IT (1) | IT1113449B (it) |
| LU (1) | LU81027A1 (it) |
| NL (1) | NL7902008A (it) |
| NZ (1) | NZ189896A (it) |
| PL (1) | PL214143A1 (it) |
| PT (1) | PT69344A (it) |
| SE (1) | SE7902302L (it) |
| SU (1) | SU755193A3 (it) |
| ZA (1) | ZA791043B (it) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281018A (en) * | 1978-04-12 | 1981-07-28 | American Cyanamid Company | Novel 4-[(carboxyl- and sulfamyl-substituted alkyl)-amino]benzoic acids and analogs |
| DE3042482A1 (de) * | 1980-11-11 | 1982-06-24 | A. Nattermann & Cie GmbH, 5000 Köln | N-benzoyl- (omega) -anilinoalkancarbonsaeuren, -salze und -ester, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate |
| FR2512017A1 (fr) * | 1981-08-27 | 1983-03-04 | Synthelabo | Derives de n-(benzoyl-3 phenyl) alanine, leur preparation et leur application en therapeutique |
| DE3608725A1 (de) * | 1986-03-15 | 1987-09-17 | Hoechst Ag | N-substituierte aminoalkansaeuren, verfahren zu ihrer herstellung, ihre verwendung sowie pharmazeutische praeparate auf basis dieser verbindungen |
| US5981466A (en) * | 1994-10-13 | 1999-11-09 | The Procter & Gamble Company | Detergent compositions containing amines and anionic surfactants |
| US6063815A (en) * | 1998-05-12 | 2000-05-16 | American Home Products Corporation | Benzopenones useful in the treatment of insulin resistance and hyperglycemia |
| DE60143984D1 (de) | 2000-08-18 | 2011-03-17 | Ajinomoto Kk | Neue phenylalanin-derivate |
| DE10306202A1 (de) * | 2003-02-13 | 2004-08-26 | Grünenthal GmbH | Arzneimittel enthaltend substituierte 2-Aryl-Aminoessigsäure-Verbindungen und/oder substituierte 2-Heteroaryl-Aminoessigsäure-Verbindungen |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3642887A (en) * | 1966-12-19 | 1972-02-15 | Ethyl Corp | Preparation of amino-substituted carboxylic acids |
| US3531467A (en) * | 1966-12-23 | 1970-09-29 | Hoffmann La Roche | Process for the preparation of 2,3,4,5-tetrahydro - 5 - aryl - 1h - 1,4 - benzodiazepine derivatives |
| US3520922A (en) * | 1967-09-07 | 1970-07-21 | Searle & Co | Phenoxyphenylamino acids |
| US3781095A (en) * | 1969-12-08 | 1973-12-25 | Westinghouse Electric Corp | Reflector |
| US4069344A (en) * | 1972-05-10 | 1978-01-17 | Ciba-Geigy Corporation | Insecticidal substituted phenyl derivatives |
| DE2462813C2 (de) * | 1974-04-30 | 1986-08-21 | Byk Gulden Lomberg Chemische Fabrik Gmbh, 7750 Konstanz | Verwendung von acylierten Anilinobuttersäuren bzw. deren Salzen |
| JPS5195049A (en) * | 1975-02-12 | 1976-08-20 | * **********so*****no***tsu*****************************************ni*no | |
| US4153718A (en) * | 1976-07-30 | 1979-05-08 | Beecham Group Limited | Anti-inflammatory compounds |
-
1978
- 1978-03-15 FR FR7807443A patent/FR2419928A1/fr active Granted
-
1979
- 1979-03-06 ZA ZA791043A patent/ZA791043B/xx unknown
- 1979-03-06 IT IT20786/79A patent/IT1113449B/it active
- 1979-03-06 GR GR58529A patent/GR68031B/el unknown
- 1979-03-07 IL IL56816A patent/IL56816A0/xx unknown
- 1979-03-09 AU AU44968/79A patent/AU4496879A/en not_active Abandoned
- 1979-03-09 FI FI790820A patent/FI790820A7/fi not_active Application Discontinuation
- 1979-03-12 LU LU81027A patent/LU81027A1/xx unknown
- 1979-03-13 JP JP2834079A patent/JPS54128555A/ja active Pending
- 1979-03-13 DE DE19792909742 patent/DE2909742A1/de not_active Withdrawn
- 1979-03-13 PT PT69344A patent/PT69344A/pt unknown
- 1979-03-13 CS CS791654A patent/CS207785B2/cs unknown
- 1979-03-13 NZ NZ189896A patent/NZ189896A/xx unknown
- 1979-03-14 SU SU792739505A patent/SU755193A3/ru active
- 1979-03-14 SE SE7902302A patent/SE7902302L/xx not_active Application Discontinuation
- 1979-03-14 BE BE0/194024A patent/BE874843A/xx unknown
- 1979-03-14 AT AT0193279A patent/ATA193279A/de not_active IP Right Cessation
- 1979-03-14 NL NL7902008A patent/NL7902008A/xx active Search and Examination
- 1979-03-14 US US06/020,358 patent/US4223039A/en not_active Expired - Lifetime
- 1979-03-15 PL PL21414379A patent/PL214143A1/xx unknown
- 1979-03-15 GB GB7909119A patent/GB2016448A/en not_active Withdrawn
- 1979-03-15 ES ES478643A patent/ES478643A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IT1113449B (it) | 1986-01-20 |
| IT7920786A0 (it) | 1979-03-06 |
| SU755193A3 (en) | 1980-08-07 |
| FR2419928A1 (fr) | 1979-10-12 |
| ES478643A1 (es) | 1979-11-16 |
| NZ189896A (en) | 1980-05-27 |
| SE7902302L (sv) | 1979-09-16 |
| ATA193279A (de) | 1981-08-15 |
| ZA791043B (en) | 1980-03-26 |
| JPS54128555A (en) | 1979-10-05 |
| GB2016448A (en) | 1979-09-26 |
| BE874843A (fr) | 1979-09-14 |
| LU81027A1 (fr) | 1979-10-30 |
| DE2909742A1 (de) | 1979-09-27 |
| PL214143A1 (it) | 1979-11-05 |
| NL7902008A (nl) | 1979-09-18 |
| AU4496879A (en) | 1979-09-20 |
| FI790820A7 (fi) | 1979-09-16 |
| PT69344A (fr) | 1979-04-01 |
| GR68031B (it) | 1981-10-27 |
| US4223039A (en) | 1980-09-16 |
| FR2419928B1 (it) | 1981-07-24 |
| IL56816A0 (en) | 1979-05-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3342826A (en) | Heterocyclic aminoalkyl benzamides | |
| US4277497A (en) | Analgesic 2-(M-benzoylphenoxy)-propionic acid derivatives | |
| US5604261A (en) | Arylalkyl (thio)amides | |
| NO125672B (it) | ||
| US3957850A (en) | Phenylacetic acid derivatives | |
| JPS638935B2 (it) | ||
| US4365076A (en) | Process for the preparation of cycloalkylidenemethylphenylacetic acid derivatives | |
| JPS637542B2 (it) | ||
| SU1156593A3 (ru) | Способ получени производных бензамида или их кислотно-аддитивных солей,или оптических изомеров | |
| US4431663A (en) | Treatment of psychosis with meta-sulfonamido-benzamide derivatives | |
| CS207785B2 (en) | Method of making the derivatives of the n-phenylalanine or n-phenylglycine | |
| NL8903132A (nl) | Capsaicinederivaten, werkwijzen voor hun bereiding, farmaceutische preparaten die ze bevatten en hun toepassing als farmaceutica. | |
| GB2206347A (en) | Thiourea derivatives | |
| US3579529A (en) | Heterocyclic compounds | |
| KR0181945B1 (ko) | N,n'-비스(알콕시알킬)-피리딘-2,4-디카복실산 디아미드, 이의 제조방법 및 이를 함유하는 약제학적 조성물 | |
| US3644479A (en) | 1-indancarboxylic acids and derivatives | |
| PT100216B (pt) | N-{{4,5-di-hidroxi- e 4,5,8-tri-hidroxi-9,10-di-hidro-9,10-dioxo-2-antracentil} carbonil}-aminoacidos uteis na terapia de afeccoes osteoarticulares, processo para a sua preparacao e composicoes farmaceuticas que os contem | |
| JPS6399057A (ja) | グリシン誘導体 | |
| US3637804A (en) | Phenylalanine derivatives and preparation thereof | |
| JPH0455188B2 (it) | ||
| US3775479A (en) | Amine compounds | |
| US5449826A (en) | 5-amino-2-phenoxysulfonanilide compound | |
| US4446151A (en) | Decarboxylase-inhibiting fluorinated pentane diamine derivatives | |
| JPS6056130B2 (ja) | 新規なサリチル酸誘導体 | |
| US4568690A (en) | 1-Methyl-5-p-methylbenzoylpyrrole-2-acetamidoacetanilides with antiinflammatory, analgesic, antipyretic and anti-platelet aggregant activity |