DK141405B - Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. - Google Patents
Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. Download PDFInfo
- Publication number
- DK141405B DK141405B DK545577A DK545577A DK141405B DK 141405 B DK141405 B DK 141405B DK 545577 A DK545577 A DK 545577A DK 545577 A DK545577 A DK 545577A DK 141405 B DK141405 B DK 141405B
- Authority
- DK
- Denmark
- Prior art keywords
- group
- carbon atoms
- dihydro
- isoquinoline
- compound
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000003839 salts Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 40
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 12
- 230000004872 arterial blood pressure Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- -1 aminopyrazole isoquinolone derivative Chemical class 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- 229910052760 oxygen Inorganic materials 0.000 description 6
- 239000001301 oxygen Substances 0.000 description 6
- 210000005242 cardiac chamber Anatomy 0.000 description 5
- 230000000747 cardiac effect Effects 0.000 description 5
- 210000002216 heart Anatomy 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 210000004165 myocardium Anatomy 0.000 description 4
- 230000036284 oxygen consumption Effects 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 210000003748 coronary sinus Anatomy 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- 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
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- KFQTXYLBJPPYAI-UHFFFAOYSA-N isoquinoline dihydrate hydrochloride Chemical compound O.O.Cl.C1=NC=CC2=CC=CC=C12 KFQTXYLBJPPYAI-UHFFFAOYSA-N 0.000 description 2
- 238000006213 oxygenation reaction 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
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- 230000002861 ventricular Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- FYELSNVLZVIGTI-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-5-ethylpyrazol-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=1CC)CC(=O)N1CC2=C(CC1)NN=N2 FYELSNVLZVIGTI-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical class O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 description 1
- 241000282465 Canis Species 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
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 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
- 238000002474 experimental method Methods 0.000 description 1
- 239000012530 fluid Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 210000005240 left ventricle Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000004783 oxidative metabolism Effects 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
- 230000002572 peristaltic effect Effects 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK545577A DK141405B (da) | 1972-06-30 | 1977-12-08 | Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI1248A HU167240B (enExample) | 1972-06-30 | 1972-06-30 | |
| HUCI001248 | 1972-06-30 | ||
| DK357373AA DK141066B (da) | 1972-06-30 | 1973-06-28 | Analogifremgangsmåde til fremstilling af aminoimidazokinolinderivater. |
| DK357373 | 1973-06-28 | ||
| DK545577 | 1977-12-08 | ||
| DK545577A DK141405B (da) | 1972-06-30 | 1977-12-08 | Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK545577A DK545577A (enExample) | 1977-12-08 |
| DK141405B true DK141405B (da) | 1980-03-10 |
| DK141405C DK141405C (enExample) | 1980-09-08 |
Family
ID=27221817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK545577A DK141405B (da) | 1972-06-30 | 1977-12-08 | Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. |
Country Status (1)
| Country | Link |
|---|---|
| DK (1) | DK141405B (enExample) |
-
1977
- 1977-12-08 DK DK545577A patent/DK141405B/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK545577A (enExample) | 1977-12-08 |
| DK141405C (enExample) | 1980-09-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI60555B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara aromatiska karboxylamidderivat | |
| Cairns et al. | Synthesis and structure-activity relations of disodium cromoglycate and some related compounds | |
| JPH04217977A (ja) | 新規なベンゾオキサジン及びベンゾチアジン誘導体及びその製造方法 | |
| JP2000256259A (ja) | メイラード反応阻害剤 | |
| EP0357788A1 (en) | PYRIDAZINONE DERIVATIVES. | |
| SU1356962A3 (ru) | Способ получени производных карбостирила | |
| JPS6322082A (ja) | １―（ヒドロキシスチリル）―５ｈ―２，３―ベンゾジアゼピン誘導体およびその製造方法、並びに前記誘導体を含む薬剤 | |
| US3541097A (en) | Process for the production of coumarin derivatives | |
| CS195653B2 (en) | Method of producing new aminoalkoxyphenylderivatives | |
| FI58126C (fi) | Foerfarande foer framstaellning av kardiotona och blodtryckssaenkande 2-fenyl-1h-imidatso(4,5-b)pyridiner | |
| DK141405B (da) | Fremgangsmåde til fremstilling af aminopyrazolisokinolinderivater eller salte deraf. | |
| Rice et al. | Spiranes. III. 1a, b Azaspiranes and Intermediates1c | |
| EP0149543A1 (en) | Cardiotonic and antihypertensive oxadiazinone compounds | |
| FI61882C (fi) | Foerfarande foer framstaellning av antitrombotiskt verkande 3-iperazino-isokinoliner | |
| DK141066B (da) | Analogifremgangsmåde til fremstilling af aminoimidazokinolinderivater. | |
| FI57747C (fi) | Foerfarande foer framstaellning av nya isoindolin-1-on-derivat vilka aer anvaendbara saosom medel mot arytmi | |
| Gray | The Relative Basicities of α-, β-and γ-Carboline Anhydronium Bases | |
| PL131451B1 (en) | Method of obtaining new derivatives of 1,2,4-oxydiazolin-5-one | |
| DK141628B (da) | Analogifremgangsmåde til fremstilling af aminopyrazolisokinolinderivater. | |
| NO149314B (no) | Analogifremgangsmaate for fremstilling av fysiologisk aktive imidazoisokinolindioner | |
| SU1017171A3 (ru) | Способ получени производных пиразоло (1,5-с) хиназолина или их солей | |
| MXPA97004203A (en) | Use of theophylline derivatives for the treatment and prophylaxis of states of shock, new compounds of xanthina and procedure for its preparation | |
| FI62531B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbart 3-yan-n-(n n-dimetylamino-propyl)-iminobensyl och syraaddit iossalter daerav | |
| FI56383C (fi) | Foerfarande foer framstaellning av nya pao hjaertverksamheten verkande 2-amino-5,6-dihydro-8,9-dialkoxi-pyrazolo(5,1-a)isokinolin-derivat | |
| DK141067B (da) | Fremgangsmåde til fremstilling af aminoimidazolisokinolinderivater. |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed |