DE2258318A1 - Neue organische verbindungen und verfahren zu deren herstellung - Google Patents
Neue organische verbindungen und verfahren zu deren herstellungInfo
- Publication number
- DE2258318A1 DE2258318A1 DE19722258318 DE2258318A DE2258318A1 DE 2258318 A1 DE2258318 A1 DE 2258318A1 DE 19722258318 DE19722258318 DE 19722258318 DE 2258318 A DE2258318 A DE 2258318A DE 2258318 A1 DE2258318 A1 DE 2258318A1
- Authority
- DE
- Germany
- Prior art keywords
- compounds
- formula
- carbon atoms
- hydrogen
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 14
- 150000002894 organic compounds Chemical class 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 48
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 239000007921 spray Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 44
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000002244 precipitate Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000009835 boiling Methods 0.000 description 19
- 239000000203 mixture Substances 0.000 description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000007858 starting material Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- -1 potassium hydroxide Chemical class 0.000 description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000007514 bases Chemical class 0.000 description 3
- 229940046892 lead acetate Drugs 0.000 description 3
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 3
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 3
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 2
- HBQPUOQPZPUNEJ-UHFFFAOYSA-N 3-ethyl-2h-indazole Chemical compound C1=CC=C2C(CC)=NNC2=C1 HBQPUOQPZPUNEJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- POFNXYKXIXYHEG-UHFFFAOYSA-N 1-ethyl-7-nitroindazole Chemical compound C(C)N1N=CC2=CC=CC(=C12)[N+](=O)[O-] POFNXYKXIXYHEG-UHFFFAOYSA-N 0.000 description 1
- FKQDTYKVWIDGNT-UHFFFAOYSA-N 1-methylindazol-7-amine Chemical compound C1=CC(N)=C2N(C)N=CC2=C1 FKQDTYKVWIDGNT-UHFFFAOYSA-N 0.000 description 1
- OTFFCAGPSWJBDK-UHFFFAOYSA-N 1h-indazol-7-amine Chemical compound NC1=CC=CC2=C1NN=C2 OTFFCAGPSWJBDK-UHFFFAOYSA-N 0.000 description 1
- AHYDTWBRZSGJCV-UHFFFAOYSA-N 2-ethyl-7-nitroindazole Chemical compound C1=CC=C([N+]([O-])=O)C2=NN(CC)C=C21 AHYDTWBRZSGJCV-UHFFFAOYSA-N 0.000 description 1
- ANWQWNSLIXJXOF-UHFFFAOYSA-N 5-chloro-1-methylindazole Chemical compound ClC1=CC=C2N(C)N=CC2=C1 ANWQWNSLIXJXOF-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- KQHCCQUSXVZFIZ-UHFFFAOYSA-N 5-chloro-7-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC(Cl)=CC2=C1NN=C2 KQHCCQUSXVZFIZ-UHFFFAOYSA-N 0.000 description 1
- SZXXXCUWPQQOOW-UHFFFAOYSA-N 6-chloro-2-methyl-7-nitroindazole Chemical compound ClC=1C=CC2=CN(N=C2C1[N+](=O)[O-])C SZXXXCUWPQQOOW-UHFFFAOYSA-N 0.000 description 1
- JJILFDHWWZQMCL-UHFFFAOYSA-N 6-chloro-7-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=C(Cl)C=CC2=C1NN=C2 JJILFDHWWZQMCL-UHFFFAOYSA-N 0.000 description 1
- PQCAUHUKTBHUSA-UHFFFAOYSA-N 7-nitro-1h-indazole Chemical compound [O-][N+](=O)C1=CC=CC2=C1NN=C2 PQCAUHUKTBHUSA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MDZDNLCDVWXJBC-UHFFFAOYSA-N ClC1=CC=C2C=NN(C2=C1[N+](=O)[O-])C Chemical compound ClC1=CC=C2C=NN(C2=C1[N+](=O)[O-])C MDZDNLCDVWXJBC-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001024304 Mino Species 0.000 description 1
- HLGYFEXSPFFXMJ-UHFFFAOYSA-N N1C(=NCC1)NC=1C=CC=C2C=NN(C=12)C Chemical compound N1C(=NCC1)NC=1C=CC=C2C=NN(C=12)C HLGYFEXSPFFXMJ-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- DBWAFSOUGKJFPC-UHFFFAOYSA-N chloroform;ethanol;heptane Chemical compound CCO.ClC(Cl)Cl.CCCCCCC DBWAFSOUGKJFPC-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003009 desulfurizing effect Effects 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 229940008406 diethyl sulfate Drugs 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- KRZGKJJPEOUIBI-UHFFFAOYSA-N hydron;thiourea;iodide Chemical compound I.NC(S)=N KRZGKJJPEOUIBI-UHFFFAOYSA-N 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000001055 magnesium Nutrition 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 206010038464 renal hypertension Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 125000005500 uronium group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1745371A CH573424A5 (en) | 1971-12-01 | 1971-12-01 | 7-heterocyclyl amino-indazoles - with hypotensive activity |
| CH1489372A CH578555A5 (en) | 1972-10-12 | 1972-10-12 | 7-heterocyclyl amino-indazoles - with hypotensive activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2258318A1 true DE2258318A1 (de) | 1973-06-07 |
Family
ID=25715292
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722258318 Pending DE2258318A1 (de) | 1971-12-01 | 1972-11-29 | Neue organische verbindungen und verfahren zu deren herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3847934A (OSRAM) |
| JP (1) | JPS4862759A (OSRAM) |
| AT (1) | AT333273B (OSRAM) |
| BE (1) | BE792078A (OSRAM) |
| DD (1) | DD102145A5 (OSRAM) |
| DE (1) | DE2258318A1 (OSRAM) |
| DK (1) | DK130212B (OSRAM) |
| ES (1) | ES409104A1 (OSRAM) |
| FR (1) | FR2162138B1 (OSRAM) |
| GB (1) | GB1411625A (OSRAM) |
| HU (1) | HU165771B (OSRAM) |
| NL (1) | NL7216043A (OSRAM) |
| PL (1) | PL82659B1 (OSRAM) |
| SU (1) | SU512702A3 (OSRAM) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036976A (en) * | 1973-04-05 | 1977-07-19 | Sandoz, Inc. | Substituted imidazolinylamino-indazoles |
| EP0047328B1 (de) * | 1980-09-05 | 1984-05-09 | Siegfried Aktiengesellschaft | 1H- und 2H-Indazolderivate und diese enthaltendes Arzneimittel |
| WO2009071906A1 (en) * | 2007-12-05 | 2009-06-11 | Imperial Innovations Limited | Derivatives of 1-[(imidazolidin-2-yl)imino)]indazole |
| EP2178870A4 (en) * | 2007-08-17 | 2012-04-11 | Lg Life Sciences Ltd | INDOL AND INDAZONE COMPOUNDS AS AN INHIBITORS OF CELL NECROSIS |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH632268A5 (de) * | 1977-01-14 | 1982-09-30 | Sandoz Ag | Verfahren zur herstellung von neuen heterocyclylaminoderivaten. |
| TW397812B (en) * | 1995-02-11 | 2000-07-11 | Astra Ab | Bicyclic isothiourea derivatives useful in therapy |
| GB2361425B (en) * | 2000-04-17 | 2004-03-31 | Sorex Ltd | Rodenticidal thiourea compounds |
| US20040242560A1 (en) * | 2003-05-22 | 2004-12-02 | Aventis Pharma Deutschland Gmbh | Process for synthesizing heterocyclic compounds |
| KR101098583B1 (ko) * | 2008-01-04 | 2011-12-26 | 주식회사 엘지생명과학 | 세포, 조직 및 장기 보존 효과를 갖는 인돌 및 인다졸 유도체 |
-
0
- BE BE792078D patent/BE792078A/xx unknown
-
1972
- 1972-11-22 DK DK584172AA patent/DK130212B/da unknown
- 1972-11-27 NL NL7216043A patent/NL7216043A/xx unknown
- 1972-11-28 GB GB5487172A patent/GB1411625A/en not_active Expired
- 1972-11-29 HU HUWA268A patent/HU165771B/hu unknown
- 1972-11-29 PL PL1972159176A patent/PL82659B1/pl unknown
- 1972-11-29 US US00310204A patent/US3847934A/en not_active Expired - Lifetime
- 1972-11-29 DE DE19722258318 patent/DE2258318A1/de active Pending
- 1972-11-29 ES ES409104A patent/ES409104A1/es not_active Expired
- 1972-11-29 DD DD167173A patent/DD102145A5/xx unknown
- 1972-11-30 JP JP47119469A patent/JPS4862759A/ja active Pending
- 1972-11-30 AT AT1020172A patent/AT333273B/de not_active IP Right Cessation
- 1972-11-30 SU SU1852157A patent/SU512702A3/ru active
- 1972-12-01 FR FR7242715A patent/FR2162138B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4036976A (en) * | 1973-04-05 | 1977-07-19 | Sandoz, Inc. | Substituted imidazolinylamino-indazoles |
| EP0047328B1 (de) * | 1980-09-05 | 1984-05-09 | Siegfried Aktiengesellschaft | 1H- und 2H-Indazolderivate und diese enthaltendes Arzneimittel |
| EP2178870A4 (en) * | 2007-08-17 | 2012-04-11 | Lg Life Sciences Ltd | INDOL AND INDAZONE COMPOUNDS AS AN INHIBITORS OF CELL NECROSIS |
| WO2009071906A1 (en) * | 2007-12-05 | 2009-06-11 | Imperial Innovations Limited | Derivatives of 1-[(imidazolidin-2-yl)imino)]indazole |
Also Published As
| Publication number | Publication date |
|---|---|
| DD102145A5 (OSRAM) | 1973-12-05 |
| SU512702A3 (ru) | 1976-04-30 |
| ATA1020172A (de) | 1976-03-15 |
| NL7216043A (OSRAM) | 1973-06-05 |
| GB1411625A (en) | 1975-10-29 |
| HU165771B (OSRAM) | 1974-10-28 |
| ES409104A1 (es) | 1976-03-01 |
| AT333273B (de) | 1976-11-10 |
| DK130212B (da) | 1975-01-20 |
| FR2162138A1 (OSRAM) | 1973-07-13 |
| PL82659B1 (en) | 1975-10-31 |
| FR2162138B1 (OSRAM) | 1976-07-02 |
| JPS4862759A (OSRAM) | 1973-09-01 |
| DK130212C (OSRAM) | 1975-06-16 |
| US3847934A (en) | 1974-11-12 |
| BE792078A (fr) | 1973-05-29 |
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