CH578555A5 - 7-heterocyclyl amino-indazoles - with hypotensive activity - Google Patents
7-heterocyclyl amino-indazoles - with hypotensive activityInfo
- Publication number
- CH578555A5 CH578555A5 CH1489372A CH1489372A CH578555A5 CH 578555 A5 CH578555 A5 CH 578555A5 CH 1489372 A CH1489372 A CH 1489372A CH 1489372 A CH1489372 A CH 1489372A CH 578555 A5 CH578555 A5 CH 578555A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- compounds
- alkyl
- hydrogen
- carbon atoms
- Prior art date
Links
- 230000001077 hypotensive effect Effects 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 150000002367 halogens Chemical class 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims description 2
- 235000013312 flour Nutrition 0.000 claims 1
- 125000003453 indazolyl group Chemical class N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 208000007530 Essential hypertension Diseases 0.000 abstract description 2
- 206010038464 renal hypertension Diseases 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 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
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- FROTZMQAGCEETR-UHFFFAOYSA-N ClC=1C=C2C=NN(C2=C(C1)[N+](=O)[O-])C Chemical compound ClC=1C=C2C=NN(C2=C(C1)[N+](=O)[O-])C FROTZMQAGCEETR-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-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
- 239000002585 base Substances 0.000 description 2
- 150000007514 bases Chemical class 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002431 hydrogen Chemical group 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
- SZQXHDWOBFSIRH-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-1h-indazol-7-amine Chemical compound N1CCN=C1NC1=CC=CC2=C1NN=C2 SZQXHDWOBFSIRH-UHFFFAOYSA-N 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
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- OTFFCAGPSWJBDK-UHFFFAOYSA-N 1h-indazol-7-amine Chemical compound NC1=CC=CC2=C1NN=C2 OTFFCAGPSWJBDK-UHFFFAOYSA-N 0.000 description 1
- ZVGCIMVMXFUSDB-UHFFFAOYSA-N 2-methyl-1-nitro-1-nitrosoguanidine Chemical compound CN=C(N)N(N=O)[N+]([O-])=O ZVGCIMVMXFUSDB-UHFFFAOYSA-N 0.000 description 1
- RQBVJZZEOGQSGY-UHFFFAOYSA-N 5-chloro-1-methylindazol-7-amine Chemical compound ClC1=CC(N)=C2N(C)N=CC2=C1 RQBVJZZEOGQSGY-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UGTSRPWMLTWCRE-UHFFFAOYSA-N CN1N=CC2=CC(Cl)=CC(NC3=NCCN3)=C12 Chemical compound CN1N=CC2=CC(Cl)=CC(NC3=NCCN3)=C12 UGTSRPWMLTWCRE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ALCVXWSSZVZKQV-UHFFFAOYSA-N ClC1=CC2=CN(N=C2C(=C1)[N+](=O)[O-])C Chemical compound ClC1=CC2=CN(N=C2C(=C1)[N+](=O)[O-])C ALCVXWSSZVZKQV-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 241000124008 Mammalia 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
- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 229960000583 acetic acid Drugs 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
- 150000008044 alkali metal hydroxides Chemical class 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
- 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- DBWAFSOUGKJFPC-UHFFFAOYSA-N chloroform;ethanol;heptane Chemical compound CCO.ClC(Cl)Cl.CCCCCCC DBWAFSOUGKJFPC-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 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
- 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
- 239000000706 filtrate Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000005984 hydrogenation reaction Methods 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
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 150000002473 indoazoles Chemical class 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 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
- 230000007170 pathology Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 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
- 239000007787 solid Substances 0.000 description 1
- -1 sulfuric Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE792078D BE792078A (fr) | 1971-12-01 | Nouveaux derives de l'indazole, leur preparation et leur application comme medicaments | |
| CH1489372A CH578555A5 (en) | 1972-10-12 | 1972-10-12 | 7-heterocyclyl amino-indazoles - with hypotensive activity |
| DK584172AA DK130212B (da) | 1971-12-01 | 1972-11-22 | Analogifremgangsmåde til fremstilling af 7-aminoindazolderivater. |
| NL7216043A NL7216043A (OSRAM) | 1971-12-01 | 1972-11-27 | |
| GB5487172A GB1411625A (en) | 1971-12-01 | 1972-11-28 | 7-amino-indazole derivatives |
| HUWA268A HU165771B (OSRAM) | 1971-12-01 | 1972-11-29 | |
| ES409104A ES409104A1 (es) | 1971-12-01 | 1972-11-29 | Procedimiento para la obtencion de derivados de 7-amino-indazol. |
| PL1972159176A PL82659B1 (en) | 1971-12-01 | 1972-11-29 | 7-(imidazolinyl-(2)-amino)-indazoles[us3847934a] |
| DE19722258318 DE2258318A1 (de) | 1971-12-01 | 1972-11-29 | Neue organische verbindungen und verfahren zu deren herstellung |
| US00310204A US3847934A (en) | 1971-12-01 | 1972-11-29 | 7-(imidazolinyl-(2)-amino)-indazoles |
| DD167173A DD102145A5 (OSRAM) | 1971-12-01 | 1972-11-29 | |
| PL17592972A PL91800B1 (OSRAM) | 1972-10-12 | 1972-11-29 | |
| JP47119469A JPS4862759A (OSRAM) | 1971-12-01 | 1972-11-30 | |
| AT1020172A AT333273B (de) | 1971-12-01 | 1972-11-30 | Verfahren zur herstellung von neuen indazolderivaten und ihren salzen |
| SU1852157A SU512702A3 (ru) | 1971-12-01 | 1972-11-30 | Способ получени производных индазола |
| FR7242715A FR2162138B1 (OSRAM) | 1971-12-01 | 1972-12-01 | |
| SU2008954A SU497773A3 (ru) | 1972-10-12 | 1974-03-28 | Способ получени производных индазола |
| SU2009439A SU498906A3 (ru) | 1972-10-12 | 1974-03-28 | Способ получени производных индазола |
| AT106875A ATA106875A (de) | 1972-10-12 | 1975-02-13 | Verfahren zur herstellung von neuen indazolderivaten und ihren salzen |
| AT106975A ATA106975A (de) | 1972-10-12 | 1975-02-13 | Verfahren zur herstellung von neuen indazolderivaten und ihren salzen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1489372A CH578555A5 (en) | 1972-10-12 | 1972-10-12 | 7-heterocyclyl amino-indazoles - with hypotensive activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH578555A5 true CH578555A5 (en) | 1976-08-13 |
Family
ID=4404623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1489372A CH578555A5 (en) | 1971-12-01 | 1972-10-12 | 7-heterocyclyl amino-indazoles - with hypotensive activity |
Country Status (3)
| Country | Link |
|---|---|
| CH (1) | CH578555A5 (OSRAM) |
| PL (1) | PL91800B1 (OSRAM) |
| SU (2) | SU498906A3 (OSRAM) |
-
1972
- 1972-10-12 CH CH1489372A patent/CH578555A5/de not_active IP Right Cessation
- 1972-11-29 PL PL17592972A patent/PL91800B1/pl unknown
-
1974
- 1974-03-28 SU SU2009439A patent/SU498906A3/ru active
- 1974-03-28 SU SU2008954A patent/SU497773A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| SU497773A3 (ru) | 1975-12-30 |
| SU498906A3 (ru) | 1976-01-05 |
| PL91800B1 (OSRAM) | 1977-03-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |