NO742929L - - Google Patents
Info
- Publication number
- NO742929L NO742929L NO742929A NO742929A NO742929L NO 742929 L NO742929 L NO 742929L NO 742929 A NO742929 A NO 742929A NO 742929 A NO742929 A NO 742929A NO 742929 L NO742929 L NO 742929L
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- hydrogen
- phenyl
- substituted
- halogen
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 51
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- -1 phenylcarbamyl Chemical group 0.000 claims description 30
- 125000003545 alkoxy group Chemical group 0.000 claims description 27
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 150000002475 indoles Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 7
- 125000005544 phthalimido group Chemical group 0.000 claims description 7
- 229940054051 antipsychotic indole derivative Drugs 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 3
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000000908 ammonium hydroxide Substances 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 150000001805 chlorine compounds Chemical class 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 2
- 239000012346 acetyl chloride Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 150000001559 benzoic acids Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- VSWLXYAZJZQIKA-UHFFFAOYSA-N tetrachloromethane;triphenylphosphane Chemical compound ClC(Cl)(Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 VSWLXYAZJZQIKA-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- NWARKHJKTSHGQT-UHFFFAOYSA-N 1-methyl-3-phenylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=CC=C1 NWARKHJKTSHGQT-UHFFFAOYSA-N 0.000 description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010030113 Oedema Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- DCNZSGBRAXNERP-UHFFFAOYSA-N 3-(4-aminophenyl)-1-methylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=C(N)C=C1 DCNZSGBRAXNERP-UHFFFAOYSA-N 0.000 description 2
- DVKBLSXIKZHQAL-UHFFFAOYSA-N 3-(4-chlorophenyl)-1-methylindol-2-amine;hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=C(Cl)C=C1 DVKBLSXIKZHQAL-UHFFFAOYSA-N 0.000 description 2
- YNHPYHUPVRPMSL-UHFFFAOYSA-N N'-methyl-4-morpholin-4-yl-N'-phenylbutanehydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)CCCN1CCOCC1 YNHPYHUPVRPMSL-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000003599 food sweetener Nutrition 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
- 239000012074 organic phase Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- QAZNMUUOFRDDNM-UHFFFAOYSA-N (4-chlorophenyl)-(3,3-dimethyl-2-methyliminoindol-1-yl)methanone Chemical compound C12=CC=CC=C2C(C)(C)C(=NC)N1C(=O)C1=CC=C(Cl)C=C1 QAZNMUUOFRDDNM-UHFFFAOYSA-N 0.000 description 1
- JMBQPDSQCFZTTI-UHFFFAOYSA-N 1,3,3-trimethylindol-2-imine hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=N)C(C)(C)C2=C1 JMBQPDSQCFZTTI-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MWOODERJGVWYJE-UHFFFAOYSA-N 1-methyl-1-phenylhydrazine Chemical compound CN(N)C1=CC=CC=C1 MWOODERJGVWYJE-UHFFFAOYSA-N 0.000 description 1
- IXPNQXFRVYWDDI-UHFFFAOYSA-N 1-methyl-2,4-dioxo-1,3-diazinane-5-carboximidamide Chemical compound CN1CC(C(N)=N)C(=O)NC1=O IXPNQXFRVYWDDI-UHFFFAOYSA-N 0.000 description 1
- JTZBXAVOJYMKOU-UHFFFAOYSA-N 1-methyl-3-(2-morpholin-4-ylethyl)-3H-indol-2-imine dihydrochloride Chemical compound Cl.Cl.C12=CC=CC=C2N(C)C(=N)C1CCN1CCOCC1 JTZBXAVOJYMKOU-UHFFFAOYSA-N 0.000 description 1
- ZXHHNORIQIOSHG-UHFFFAOYSA-N 1-methyl-3-(4-nitrophenyl)indol-2-amine Chemical compound C12=CC=CC=C2N(C)C(N)=C1C1=CC=C([N+]([O-])=O)C=C1 ZXHHNORIQIOSHG-UHFFFAOYSA-N 0.000 description 1
- OCGDDEWVWMZYBO-UHFFFAOYSA-N 1-methyl-3-(4-nitrophenyl)indol-2-amine hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(N)=C1C1=CC=C([N+]([O-])=O)C=C1 OCGDDEWVWMZYBO-UHFFFAOYSA-N 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- IHWDSEPNZDYMNF-UHFFFAOYSA-N 1H-indol-2-amine Chemical class C1=CC=C2NC(N)=CC2=C1 IHWDSEPNZDYMNF-UHFFFAOYSA-N 0.000 description 1
- WOSJKENLZHUUMC-UHFFFAOYSA-N 2-(1-methylindol-2-yl)acetic acid Chemical compound C1=CC=C2N(C)C(CC(O)=O)=CC2=C1 WOSJKENLZHUUMC-UHFFFAOYSA-N 0.000 description 1
- FDIRJLPPOVBXEK-UHFFFAOYSA-N 2-(2-imino-3,3-dimethylindol-1-yl)acetamide Chemical compound C1=CC=C2C(C)(C)C(=N)N(CC(N)=O)C2=C1 FDIRJLPPOVBXEK-UHFFFAOYSA-N 0.000 description 1
- NKBOMTAPIABVHC-UHFFFAOYSA-N 2-(2-imino-3,3-dimethylindol-1-yl)acetic acid Chemical compound C1=CC=C2C(C)(C)C(=N)N(CC(O)=O)C2=C1 NKBOMTAPIABVHC-UHFFFAOYSA-N 0.000 description 1
- DMLQXJKJPCITDP-UHFFFAOYSA-N 2-(2-imino-3-methyl-3-phenylindol-1-yl)acetic acid Chemical compound N=C1N(CC(O)=O)C2=CC=CC=C2C1(C)C1=CC=CC=C1 DMLQXJKJPCITDP-UHFFFAOYSA-N 0.000 description 1
- YBEQRRUFDRYAHU-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n'-methyl-n'-phenylacetohydrazide Chemical compound COC1=CC=CC(CC(=O)NN(C)C=2C=CC=CC=2)=C1 YBEQRRUFDRYAHU-UHFFFAOYSA-N 0.000 description 1
- CDIQGLMKGDHIJL-UHFFFAOYSA-N 2-(4-chlorophenyl)-n'-methyl-n'-phenylacetohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)CC1=CC=C(Cl)C=C1 CDIQGLMKGDHIJL-UHFFFAOYSA-N 0.000 description 1
- VSVUEADPAMCORP-UHFFFAOYSA-N 2-(4-methoxyphenyl)-n'-methyl-n'-phenylacetohydrazide Chemical compound C1=CC(OC)=CC=C1CC(=O)NN(C)C1=CC=CC=C1 VSVUEADPAMCORP-UHFFFAOYSA-N 0.000 description 1
- ZKNSRWTWOSCAOS-UHFFFAOYSA-N 2-[2-(2-imino-1-methyl-3H-indol-3-yl)ethyl]isoindole-1,3-dione hydrochloride Chemical compound Cl.C12=CC=CC=C2N(C)C(=N)C1CCN1C(=O)C2=CC=CC=C2C1=O ZKNSRWTWOSCAOS-UHFFFAOYSA-N 0.000 description 1
- GHWDSNAHIDOFEB-UHFFFAOYSA-N 2-methyl-n',n'-diphenylpropanehydrazide Chemical compound C=1C=CC=CC=1N(NC(=O)C(C)C)C1=CC=CC=C1 GHWDSNAHIDOFEB-UHFFFAOYSA-N 0.000 description 1
- GXODGNJAXAMIBT-UHFFFAOYSA-N 3-(3-chloropropyl)-1-methyl-3H-indol-2-imine hydrochloride Chemical compound Cl.C1=CC=C2N(C)C(=N)C(CCCCl)C2=C1 GXODGNJAXAMIBT-UHFFFAOYSA-N 0.000 description 1
- NWODAXPUBLHDFV-UHFFFAOYSA-N 3-[(4-methoxyphenyl)methyl]-1-methylindol-2-amine hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC1=C(N)N(C)C2=CC=CC=C12 NWODAXPUBLHDFV-UHFFFAOYSA-N 0.000 description 1
- FWNNKDOSGRZAPP-UHFFFAOYSA-N 3-phenyl-1h-indol-2-amine Chemical compound NC=1NC2=CC=CC=C2C=1C1=CC=CC=C1 FWNNKDOSGRZAPP-UHFFFAOYSA-N 0.000 description 1
- RMIKIHFUTWNTGU-UHFFFAOYSA-N 4-(1,3-dioxoisoindol-2-yl)-n'-methyl-n'-phenylbutanehydrazide Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCC(=O)NN(C)C1=CC=CC=C1 RMIKIHFUTWNTGU-UHFFFAOYSA-N 0.000 description 1
- NVXIDTSLUKAQGV-UHFFFAOYSA-N 4-(dimethylamino)-N'-methyl-N'-phenylbutanehydrazide hydrochloride Chemical compound Cl.CN(C)CCCC(=O)NN(C)C1=CC=CC=C1 NVXIDTSLUKAQGV-UHFFFAOYSA-N 0.000 description 1
- BSWXXYLZNBZSCV-UHFFFAOYSA-N 4-chloro-N-(1-methyl-3-phenylindol-2-yl)benzamide Chemical compound C=1C=CC=CC=1C=1C2=CC=CC=C2N(C)C=1NC(=O)C1=CC=C(Cl)C=C1 BSWXXYLZNBZSCV-UHFFFAOYSA-N 0.000 description 1
- HUUSQHJKYSKZBO-UHFFFAOYSA-N 4-chloro-n'-methyl-n'-phenylbutanehydrazide Chemical compound ClCCCC(=O)NN(C)C1=CC=CC=C1 HUUSQHJKYSKZBO-UHFFFAOYSA-N 0.000 description 1
- VLQMALVLALLSDP-UHFFFAOYSA-N 4-chloro-n-(1,3,3-trimethylindol-2-ylidene)benzamide Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=NC(=O)C1=CC=C(Cl)C=C1 VLQMALVLALLSDP-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- OIJPQRSDDCVVRX-UHFFFAOYSA-N N',2-dimethyl-N'-phenylbutanehydrazide Chemical compound CCC(C)C(=O)NN(C)C1=CC=CC=C1 OIJPQRSDDCVVRX-UHFFFAOYSA-N 0.000 description 1
- SBHQOQUYENQEAK-UHFFFAOYSA-N N',2-dimethyl-N'-phenylpropanehydrazide Chemical compound CC(C)C(=O)NN(C)C1=CC=CC=C1 SBHQOQUYENQEAK-UHFFFAOYSA-N 0.000 description 1
- BEGZKWQRNIKAGH-UHFFFAOYSA-N N'-(4-methoxyphenyl)-N',2-dimethylpropanehydrazide Chemical compound COC1=CC=C(N(C)NC(=O)C(C)C)C=C1 BEGZKWQRNIKAGH-UHFFFAOYSA-N 0.000 description 1
- UHSOISZNRILFHU-UHFFFAOYSA-N N'-benzyl-N,2-dimethyl-N'-phenylpropanehydrazide Chemical compound C=1C=CC=CC=1N(N(C)C(=O)C(C)C)CC1=CC=CC=C1 UHSOISZNRILFHU-UHFFFAOYSA-N 0.000 description 1
- XGAANLRKMYPZTC-UHFFFAOYSA-N N'-methyl-N',2-diphenylpropanehydrazide Chemical compound C=1C=CC=CC=1C(C)C(=O)NN(C)C1=CC=CC=C1 XGAANLRKMYPZTC-UHFFFAOYSA-N 0.000 description 1
- FWKVPJOWSDLJEI-UHFFFAOYSA-N N'-methyl-N'-phenylcyclopropanecarbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C1CC1 FWKVPJOWSDLJEI-UHFFFAOYSA-N 0.000 description 1
- WALNOTFCIYFZCG-UHFFFAOYSA-N N,2-dimethyl-N'-phenylpropanehydrazide Chemical compound CC(C)C(=O)N(C)NC1=CC=CC=C1 WALNOTFCIYFZCG-UHFFFAOYSA-N 0.000 description 1
- XLQXTFNTEGTSFY-UHFFFAOYSA-N N-(1,3,3-trimethylindol-2-ylidene)benzamide Chemical compound CC1(C)C2=CC=CC=C2N(C)C1=NC(=O)C1=CC=CC=C1 XLQXTFNTEGTSFY-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
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- 208000002193 Pain Diseases 0.000 description 1
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
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- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
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- ZMAHGXRCVYCCBM-UHFFFAOYSA-N ethyl 2-(2-imino-3,3-dimethylindol-1-yl)acetate;hydrochloride Chemical compound Cl.C1=CC=C2N(CC(=O)OCC)C(=N)C(C)(C)C2=C1 ZMAHGXRCVYCCBM-UHFFFAOYSA-N 0.000 description 1
- NDRMAFGLEDWYOI-UHFFFAOYSA-N ethyl 2-(N-(2-methylpropanoylamino)anilino)acetate Chemical compound CCOC(=O)CN(NC(=O)C(C)C)C1=CC=CC=C1 NDRMAFGLEDWYOI-UHFFFAOYSA-N 0.000 description 1
- UAWHBQYQCABYTC-UHFFFAOYSA-N ethyl 2-(N-[[2-(4-methoxyphenyl)acetyl]amino]anilino)acetate Chemical compound C=1C=CC=CC=1N(CC(=O)OCC)NC(=O)CC1=CC=C(OC)C=C1 UAWHBQYQCABYTC-UHFFFAOYSA-N 0.000 description 1
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- ATHQJYUTWFKUSV-UHFFFAOYSA-N ethyl 2-[2-amino-3-[(4-methoxyphenyl)methyl]indol-1-yl]acetate hydrochloride Chemical compound Cl.C12=CC=CC=C2N(CC(=O)OCC)C(N)=C1CC1=CC=C(OC)C=C1 ATHQJYUTWFKUSV-UHFFFAOYSA-N 0.000 description 1
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
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- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
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- 238000005984 hydrogenation reaction Methods 0.000 description 1
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- JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- CBCXNCJLSIJWID-UHFFFAOYSA-N methyl 2-(1-methylindol-2-yl)acetate Chemical compound C1=CC=C2N(C)C(CC(=O)OC)=CC2=C1 CBCXNCJLSIJWID-UHFFFAOYSA-N 0.000 description 1
- JQQXRXXOVANQKM-UHFFFAOYSA-N methyl 2-(2-amino-1-methylindol-3-yl)acetate hydrochloride Chemical compound Cl.C1=CC=C2C(CC(=O)OC)=C(N)N(C)C2=C1 JQQXRXXOVANQKM-UHFFFAOYSA-N 0.000 description 1
- IKAODZFUGSSWRP-UHFFFAOYSA-N methyl 2-(2-imino-1-methyl-3H-indol-3-yl)acetate hydrochloride Chemical compound Cl.C1=CC=C2C(CC(=O)OC)C(=N)N(C)C2=C1 IKAODZFUGSSWRP-UHFFFAOYSA-N 0.000 description 1
- IXTRLBISDZVKAL-UHFFFAOYSA-N methyl 3-(2-amino-5-methoxy-1-methylindol-3-yl)propanoate hydrochloride Chemical compound Cl.C1=C(OC)C=C2C(CCC(=O)OC)=C(N)N(C)C2=C1 IXTRLBISDZVKAL-UHFFFAOYSA-N 0.000 description 1
- QTMIYDZAJLAIHN-UHFFFAOYSA-N methyl 4-(2-methyl-2-phenylhydrazinyl)-4-oxobutanoate Chemical compound COC(=O)CCC(=O)NN(C)C1=CC=CC=C1 QTMIYDZAJLAIHN-UHFFFAOYSA-N 0.000 description 1
- QYWLNZAGWAGGHE-UHFFFAOYSA-N methyl 5-(2-benzyl-2-phenylhydrazinyl)-5-oxopentanoate Chemical compound C=1C=CC=CC=1N(NC(=O)CCCC(=O)OC)CC1=CC=CC=C1 QYWLNZAGWAGGHE-UHFFFAOYSA-N 0.000 description 1
- LMYWFUNMUZMDPO-UHFFFAOYSA-N methyl 5-(2-methyl-2-phenylhydrazinyl)-5-oxopentanoate Chemical compound COC(=O)CCCC(=O)NN(C)C1=CC=CC=C1 LMYWFUNMUZMDPO-UHFFFAOYSA-N 0.000 description 1
- BJENKHROTVUQEW-UHFFFAOYSA-N methyl 5-[2-(4-methoxyphenyl)-2-methylhydrazinyl]-5-oxopentanoate Chemical compound COC(=O)CCCC(=O)NN(C)C1=CC=C(OC)C=C1 BJENKHROTVUQEW-UHFFFAOYSA-N 0.000 description 1
- VQVKYVYHBVRVCB-UHFFFAOYSA-N methyl 6-(2-methyl-2-phenylhydrazinyl)-6-oxohexanoate Chemical compound COC(=O)CCCCC(=O)NN(C)C1=CC=CC=C1 VQVKYVYHBVRVCB-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
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- 239000011707 mineral Substances 0.000 description 1
- DTMDLXYEHKWXEJ-UHFFFAOYSA-N n'-benzyl-2-methyl-n'-phenylpropanehydrazide Chemical compound C=1C=CC=CC=1N(NC(=O)C(C)C)CC1=CC=CC=C1 DTMDLXYEHKWXEJ-UHFFFAOYSA-N 0.000 description 1
- XBERUWZZONUACE-UHFFFAOYSA-N n'-methyl-4-nitro-n'-phenylbenzohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C1=CC=C([N+]([O-])=O)C=C1 XBERUWZZONUACE-UHFFFAOYSA-N 0.000 description 1
- LBUGCANJPIOMRJ-UHFFFAOYSA-N n'-methyl-n'-phenylacetohydrazide Chemical compound CC(=O)NN(C)C1=CC=CC=C1 LBUGCANJPIOMRJ-UHFFFAOYSA-N 0.000 description 1
- NDESQFBTCOJXCM-UHFFFAOYSA-N n'-methyl-n'-phenylcyclohexanecarbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C1CCCCC1 NDESQFBTCOJXCM-UHFFFAOYSA-N 0.000 description 1
- RTLVCEQPSSIXTN-UHFFFAOYSA-N n'-methyl-n'-phenylcyclopentanecarbohydrazide Chemical compound C=1C=CC=CC=1N(C)NC(=O)C1CCCC1 RTLVCEQPSSIXTN-UHFFFAOYSA-N 0.000 description 1
- NHZSLPPKFGOQCU-UHFFFAOYSA-N n'-methyl-n'-phenylpropanehydrazide Chemical compound CCC(=O)NN(C)C1=CC=CC=C1 NHZSLPPKFGOQCU-UHFFFAOYSA-N 0.000 description 1
- VRNGZYPIECCIDH-UHFFFAOYSA-N n,n',2-trimethyl-n'-phenylpropanehydrazide Chemical compound CC(C)C(=O)N(C)N(C)C1=CC=CC=C1 VRNGZYPIECCIDH-UHFFFAOYSA-N 0.000 description 1
- FOOBGINUBYBOAI-UHFFFAOYSA-N n-(1-methyl-3-phenylindol-2-yl)benzamide Chemical compound C=1C=CC=CC=1C=1C2=CC=CC=C2N(C)C=1NC(=O)C1=CC=CC=C1 FOOBGINUBYBOAI-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- 230000037040 pain threshold Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 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
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/36—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/40—Nitrogen atoms, not forming part of a nitro radical, e.g. isatin semicarbazone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4236773A GB1437804A (en) | 1973-09-10 | 1973-09-10 | Indole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO742929L true NO742929L (de) | 1975-04-07 |
Family
ID=10424107
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO742929A NO742929L (de) | 1973-09-10 | 1974-08-14 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3984563A (de) |
| JP (1) | JPS5070360A (de) |
| AU (1) | AU7315174A (de) |
| BE (1) | BE819738A (de) |
| DD (1) | DD114074A5 (de) |
| DE (1) | DE2442667A1 (de) |
| DK (1) | DK474974A (de) |
| FI (1) | FI253974A (de) |
| FR (1) | FR2245353B1 (de) |
| GB (1) | GB1437804A (de) |
| HU (1) | HU170294B (de) |
| IL (1) | IL45499A0 (de) |
| IN (1) | IN140088B (de) |
| LU (1) | LU70876A1 (de) |
| NL (1) | NL7411445A (de) |
| NO (1) | NO742929L (de) |
| RO (1) | RO63505A (de) |
| SE (1) | SE7411377L (de) |
| SU (1) | SU543345A3 (de) |
| ZA (1) | ZA745246B (de) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261894A (en) * | 1978-12-04 | 1981-04-14 | Sandoz, Inc. | Process for the preparation of optionally substituted 2,3-indolinediones |
| DE3300522A1 (de) * | 1982-01-21 | 1983-07-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend |
| FR2752575B1 (fr) * | 1996-08-23 | 1998-10-02 | Oreal | Compositions de teinture des fibres keratiniques contenant des derives 2-iminoindoliniques, nouveaux derives, leur procede de synthese, et procede de teinture |
| FR2752574B1 (fr) | 1996-08-23 | 1998-10-02 | Oreal | Derives de 2-imino-2,3-dihydro-1h-indoles, procedes de preparation, utilisations en cosmetique et dermatologie, compositions les mettant en oeuvre, procedes de teinture |
| FR2752578B1 (fr) * | 1996-08-23 | 1998-09-25 | Oreal | Produit derives de 2-imino-2,3-dihydro-1h-indoles, procedes de preparation, utilisation en cosmetique et compositions cosmetiques les mettant en oeuvre |
| DE19933857A1 (de) * | 1999-07-23 | 2001-02-01 | Cognis Deutschland Gmbh | Kosmetische Mittel mit Pflanzenextrakten |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL236636A (de) * | 1958-03-03 | |||
| US3320278A (en) * | 1965-06-30 | 1967-05-16 | Merck & Co Inc | Alpha-(2-amino)-3-indolyl lower aliphatic acid derivatives |
| US3869471A (en) * | 1971-07-22 | 1975-03-04 | Velsicol Chemical Corp | Alpha-thiocyanoacetamides |
-
1973
- 1973-09-10 GB GB4236773A patent/GB1437804A/en not_active Expired
-
1974
- 1974-08-14 NO NO742929A patent/NO742929L/no unknown
- 1974-08-15 ZA ZA00745246A patent/ZA745246B/xx unknown
- 1974-08-19 IL IL45499A patent/IL45499A0/xx unknown
- 1974-08-20 IN IN1865/CAL/74A patent/IN140088B/en unknown
- 1974-08-28 NL NL7411445A patent/NL7411445A/xx unknown
- 1974-08-29 FI FI2539/74A patent/FI253974A/fi unknown
- 1974-09-05 JP JP49102492A patent/JPS5070360A/ja active Pending
- 1974-09-06 DE DE2442667A patent/DE2442667A1/de active Pending
- 1974-09-09 LU LU70876A patent/LU70876A1/xx unknown
- 1974-09-09 US US05/504,205 patent/US3984563A/en not_active Expired - Lifetime
- 1974-09-09 DD DD180987A patent/DD114074A5/xx unknown
- 1974-09-09 SU SU2057508A patent/SU543345A3/ru active
- 1974-09-09 SE SE7411377A patent/SE7411377L/xx not_active Application Discontinuation
- 1974-09-09 DK DK474974A patent/DK474974A/da unknown
- 1974-09-10 AU AU73151/74A patent/AU7315174A/en not_active Expired
- 1974-09-10 RO RO7400079946A patent/RO63505A/ro unknown
- 1974-09-10 FR FR7430635A patent/FR2245353B1/fr not_active Expired
- 1974-09-10 BE BE148378A patent/BE819738A/xx unknown
- 1974-09-10 HU HULE755A patent/HU170294B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IN140088B (de) | 1976-09-11 |
| US3984563A (en) | 1976-10-05 |
| IL45499A0 (en) | 1974-11-29 |
| SU543345A3 (ru) | 1977-01-15 |
| FR2245353A1 (de) | 1975-04-25 |
| ZA745246B (en) | 1975-08-27 |
| RO63505A (fr) | 1978-10-15 |
| FR2245353B1 (de) | 1978-07-07 |
| LU70876A1 (de) | 1975-01-02 |
| NL7411445A (nl) | 1975-03-12 |
| DD114074A5 (de) | 1975-07-12 |
| SE7411377L (de) | 1975-03-11 |
| DK474974A (de) | 1975-05-12 |
| BE819738A (fr) | 1974-12-31 |
| HU170294B (de) | 1977-05-28 |
| FI253974A (de) | 1975-03-11 |
| GB1437804A (en) | 1976-06-03 |
| DE2442667A1 (de) | 1975-03-13 |
| AU7315174A (en) | 1976-03-18 |
| JPS5070360A (de) | 1975-06-11 |
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