DE2244832A1 - Dihydro-2-aminoisochinoline und verfahren zu deren herstellung - Google Patents
Dihydro-2-aminoisochinoline und verfahren zu deren herstellungInfo
- Publication number
- DE2244832A1 DE2244832A1 DE2244832A DE2244832A DE2244832A1 DE 2244832 A1 DE2244832 A1 DE 2244832A1 DE 2244832 A DE2244832 A DE 2244832A DE 2244832 A DE2244832 A DE 2244832A DE 2244832 A1 DE2244832 A1 DE 2244832A1
- Authority
- DE
- Germany
- Prior art keywords
- aryl
- radical
- alkenyl
- amino
- dihydro
- 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 17
- -1 aryl-lower-alkenyl Chemical group 0.000 claims description 31
- 150000001875 compounds Chemical class 0.000 claims description 28
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 2
- 239000012433 hydrogen halide Substances 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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
- 241000700159 Rattus Species 0.000 description 6
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 206010018691 Granuloma Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000008188 pellet Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 2
- AVMHMVJVHYGDOO-NSCUHMNNSA-N (e)-1-bromobut-2-ene Chemical compound C\C=C\CBr AVMHMVJVHYGDOO-NSCUHMNNSA-N 0.000 description 2
- PNGKZNMGLJJYEI-UHFFFAOYSA-N 2-amino-3,4-dihydroisoquinolin-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)N(N)CCC2=C1 PNGKZNMGLJJYEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- IWTYTFSSTWXZFU-QPJJXVBHSA-N [(e)-3-chloroprop-1-enyl]benzene Chemical compound ClC\C=C\C1=CC=CC=C1 IWTYTFSSTWXZFU-QPJJXVBHSA-N 0.000 description 2
- 230000003110 anti-inflammatory effect Effects 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229940117916 cinnamic aldehyde Drugs 0.000 description 2
- KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 210000002784 stomach Anatomy 0.000 description 2
- 230000001562 ulcerogenic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LOYZVRIHVZEDMW-UHFFFAOYSA-N 1-bromo-3-methylbut-2-ene Chemical compound CC(C)=CCBr LOYZVRIHVZEDMW-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- SZKDBYQPAMGKAF-UHFFFAOYSA-N 3,4-dihydro-2h-isoquinolin-1-one;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NCCC2=C1 SZKDBYQPAMGKAF-UHFFFAOYSA-N 0.000 description 1
- USEGQJLHQSTGHW-UHFFFAOYSA-N 3-bromo-2-methylprop-1-ene Chemical compound CC(=C)CBr USEGQJLHQSTGHW-UHFFFAOYSA-N 0.000 description 1
- RUROFEVDCUGKHD-UHFFFAOYSA-N 3-bromoprop-1-enylbenzene Chemical compound BrCC=CC1=CC=CC=C1 RUROFEVDCUGKHD-UHFFFAOYSA-N 0.000 description 1
- 125000006041 3-hexenyl group Chemical group 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 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
- FDGVDPVWSQIWOA-UHFFFAOYSA-N C=CCCN(C(CC1=CC=CC=C11)N)C1=O Chemical compound C=CCCN(C(CC1=CC=CC=C11)N)C1=O FDGVDPVWSQIWOA-UHFFFAOYSA-N 0.000 description 1
- FAVIVVUSBFYAQC-UHFFFAOYSA-N CC=CCC(CC1=CC=CC=C1C1=O)N1N Chemical compound CC=CCC(CC1=CC=CC=C1C1=O)N1N FAVIVVUSBFYAQC-UHFFFAOYSA-N 0.000 description 1
- PYXIXQHRVMVIND-UHFFFAOYSA-N CCC(C=CC)N(C(CC1=CC=CC=C11)N)C1=O Chemical compound CCC(C=CC)N(C(CC1=CC=CC=C11)N)C1=O PYXIXQHRVMVIND-UHFFFAOYSA-N 0.000 description 1
- KSDVEFRCMDGDKX-UHFFFAOYSA-N Cl.C(C#C)NN1C(C2=CC=CC=C2CC1)=O Chemical compound Cl.C(C#C)NN1C(C2=CC=CC=C2CC1)=O KSDVEFRCMDGDKX-UHFFFAOYSA-N 0.000 description 1
- YNTGJZXKPFSTKY-UHFFFAOYSA-N NC(CC1=CC=CC=C11)N(C2C=CCCC2)C1=O Chemical compound NC(CC1=CC=CC=C11)N(C2C=CCCC2)C1=O YNTGJZXKPFSTKY-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000027418 Wounds and injury Diseases 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical class C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XGXLLJGLOMBYLY-UHFFFAOYSA-N n-(1-oxo-3,4-dihydroisoquinolin-2-yl)benzenesulfonamide Chemical compound C1CC2=CC=CC=C2C(=O)N1NS(=O)(=O)C1=CC=CC=C1 XGXLLJGLOMBYLY-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229960002895 phenylbutazone Drugs 0.000 description 1
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25549/72A IT1045206B (it) | 1972-06-12 | 1972-06-12 | Aminoisochinoline |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2244832A1 true DE2244832A1 (de) | 1974-01-10 |
Family
ID=11217059
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2244832A Pending DE2244832A1 (de) | 1972-06-12 | 1972-09-13 | Dihydro-2-aminoisochinoline und verfahren zu deren herstellung |
Country Status (16)
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3037984A (en) * | 1960-01-27 | 1962-06-05 | Lakeside Lab Inc | Derivatives of n-amino-1, 2, 3, 4-tetrahydroisoquinoline |
-
0
- BE BE788901D patent/BE788901R/xx active
-
1972
- 1972-01-01 AR AR244108A patent/AR204388A1/es active
- 1972-06-12 IT IT25549/72A patent/IT1045206B/it active
- 1972-09-07 GB GB4159372A patent/GB1380682A/en not_active Expired
- 1972-09-08 ZA ZA726158A patent/ZA726158B/xx unknown
- 1972-09-12 FI FI722500A patent/FI50974C/fi active
- 1972-09-13 DE DE2244832A patent/DE2244832A1/de active Pending
- 1972-09-14 PL PL1972157754A patent/PL89031B1/pl unknown
- 1972-09-15 AT AT793572A patent/AT325048B/de not_active IP Right Cessation
- 1972-09-15 HU HULE667A patent/HU165564B/hu unknown
- 1972-09-18 AU AU46767/72A patent/AU470823B2/en not_active Expired
- 1972-10-02 CH CH217174A patent/CH564535A5/xx not_active IP Right Cessation
- 1972-10-02 CH CH1436172A patent/CH562802A5/xx not_active IP Right Cessation
- 1972-10-30 NL NL7214650A patent/NL7214650A/xx unknown
- 1972-11-08 JP JP47111339A patent/JPS5037197B2/ja not_active Expired
- 1972-11-16 ES ES408635A patent/ES408635A1/es not_active Expired
- 1972-12-21 FR FR7245729A patent/FR2187329B2/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH564535A5 (enrdf_load_stackoverflow) | 1975-07-31 |
| AU4676772A (en) | 1974-03-28 |
| NL7214650A (enrdf_load_stackoverflow) | 1973-12-14 |
| FI50974B (enrdf_load_stackoverflow) | 1976-05-31 |
| PL89031B1 (enrdf_load_stackoverflow) | 1976-10-30 |
| HU165564B (enrdf_load_stackoverflow) | 1974-09-28 |
| ES408635A1 (es) | 1975-10-16 |
| JPS4930380A (enrdf_load_stackoverflow) | 1974-03-18 |
| FR2187329B2 (enrdf_load_stackoverflow) | 1976-03-05 |
| SU444365A3 (ru) | 1974-09-25 |
| IT1045206B (it) | 1980-05-10 |
| AU470823B2 (en) | 1976-04-01 |
| AT325048B (de) | 1975-09-25 |
| JPS5037197B2 (enrdf_load_stackoverflow) | 1975-12-01 |
| CH562802A5 (enrdf_load_stackoverflow) | 1975-06-13 |
| FR2187329A2 (enrdf_load_stackoverflow) | 1974-01-18 |
| ZA726158B (en) | 1973-06-27 |
| GB1380682A (en) | 1975-01-15 |
| FI50974C (fi) | 1976-09-10 |
| AR204388A1 (es) | 1976-02-06 |
| BE788901R (fr) | 1973-01-02 |
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