DK141628B - Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. - Google Patents
Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. Download PDFInfo
- Publication number
- DK141628B DK141628B DK545777A DK545777A DK141628B DK 141628 B DK141628 B DK 141628B DK 545777 A DK545777 A DK 545777A DK 545777 A DK545777 A DK 545777A DK 141628 B DK141628 B DK 141628B
- Authority
- DK
- Denmark
- Prior art keywords
- group
- isoquinoline
- dihydro
- carbon atoms
- dimethoxypyrazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims 1
- -1 4-toluenesulfonylamino Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- JLYGWGAMSDFMIR-UHFFFAOYSA-N isoquinoline;1h-pyrazol-5-amine Chemical class NC=1C=CNN=1.C1=NC=CC2=CC=CC=C21 JLYGWGAMSDFMIR-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000004872 arterial blood pressure Effects 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 210000005242 cardiac chamber Anatomy 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 210000002216 heart Anatomy 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- SQCICHPABTVAFF-UHFFFAOYSA-N 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-methyl-5-phenyl-3H-1,2,4-oxadiazole Chemical compound COC=1C=C2CCN=C(C2=CC=1OC)C1N(OC(=N1)C1=CC=CC=C1)C SQCICHPABTVAFF-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 210000004165 myocardium Anatomy 0.000 description 3
- 230000036284 oxygen consumption Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- STCQKKWVPZJEBN-UHFFFAOYSA-N 8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-amine Chemical compound NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 STCQKKWVPZJEBN-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 210000003748 coronary sinus Anatomy 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- VPSXHKGJZJCWLV-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(1-ethylpiperidin-4-yl)oxypyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)OC1CCN(CC1)CC VPSXHKGJZJCWLV-UHFFFAOYSA-N 0.000 description 1
- ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 ZRPAUEVGEGEPFQ-UHFFFAOYSA-N 0.000 description 1
- FMQQYJCCZKFNAH-UHFFFAOYSA-N 3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-methyl-5-propyl-3H-1,2,4-oxadiazole Chemical compound COC=1C=C2CCN=C(C2=CC=1OC)C1N(OC(=N1)CCC)C FMQQYJCCZKFNAH-UHFFFAOYSA-N 0.000 description 1
- UOAZKAFCBJMATH-UHFFFAOYSA-N 5-benzyl-3-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)-2-methyl-3H-1,2,4-oxadiazole Chemical compound COC=1C=C2CCN=C(C2=CC=1OC)C1N(OC(=N1)CC1=CC=CC=C1)C UOAZKAFCBJMATH-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 102000001554 Hemoglobins Human genes 0.000 description 1
- 108010054147 Hemoglobins Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- TUYJRDRUWULTPZ-UHFFFAOYSA-N N-(8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-yl)acetamide Chemical compound C(C)(=O)NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 TUYJRDRUWULTPZ-UHFFFAOYSA-N 0.000 description 1
- YTAWSJZNTJSRDH-UHFFFAOYSA-N N-(8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-yl)benzamide Chemical compound C(C1=CC=CC=C1)(=O)NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 YTAWSJZNTJSRDH-UHFFFAOYSA-N 0.000 description 1
- RWRNWINLPRLICF-UHFFFAOYSA-N N-benzyl-8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-amine Chemical compound C(C1=CC=CC=C1)NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 RWRNWINLPRLICF-UHFFFAOYSA-N 0.000 description 1
- JGTBNQNXOFRNGG-UHFFFAOYSA-N N-ethyl-8,9-dimethoxy-5,6-dihydropyrazolo[5,1-a]isoquinolin-2-amine Chemical compound C(C)NC1=NN2C(C3=CC(=C(C=C3CC2)OC)OC)=C1 JGTBNQNXOFRNGG-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- IYRMNDOLPONSCJ-UHFFFAOYSA-N isoquinolin-2-ium;chloride Chemical compound Cl.C1=NC=CC2=CC=CC=C21 IYRMNDOLPONSCJ-UHFFFAOYSA-N 0.000 description 1
- KFQTXYLBJPPYAI-UHFFFAOYSA-N isoquinoline dihydrate hydrochloride Chemical compound O.O.Cl.C1=NC=CC2=CC=CC=C12 KFQTXYLBJPPYAI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 230000004783 oxidative metabolism Effects 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK545777A DK141628B (da) | 1972-06-30 | 1977-12-08 | Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1248A HU167240B (enrdf_load_stackoverflow) | 1972-06-30 | 1972-06-30 | |
| HUCI001248 | 1972-06-30 | ||
| DK357373 | 1973-06-28 | ||
| DK357373AA DK141066B (da) | 1972-06-30 | 1973-06-28 | Analogifremgangsmåde til fremstilling af aminoimidazokinolinderivater. |
| DK545777A DK141628B (da) | 1972-06-30 | 1977-12-08 | Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. |
| DK545777 | 1977-12-08 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK545777A DK545777A (enrdf_load_stackoverflow) | 1977-12-08 |
| DK141628B true DK141628B (da) | 1980-05-12 |
| DK141628C DK141628C (enrdf_load_stackoverflow) | 1980-10-13 |
Family
ID=27221819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK545777A DK141628B (da) | 1972-06-30 | 1977-12-08 | Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. |
Country Status (1)
| Country | Link |
|---|---|
| DK (1) | DK141628B (enrdf_load_stackoverflow) |
-
1977
- 1977-12-08 DK DK545777A patent/DK141628B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK545777A (enrdf_load_stackoverflow) | 1977-12-08 |
| DK141628C (enrdf_load_stackoverflow) | 1980-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |