DE1793488A1 - Aminobenzocycloalkylnitrile - Google Patents
AminobenzocycloalkylnitrileInfo
- Publication number
- DE1793488A1 DE1793488A1 DE19681793488 DE1793488A DE1793488A1 DE 1793488 A1 DE1793488 A1 DE 1793488A1 DE 19681793488 DE19681793488 DE 19681793488 DE 1793488 A DE1793488 A DE 1793488A DE 1793488 A1 DE1793488 A1 DE 1793488A1
- Authority
- DE
- Germany
- Prior art keywords
- isopropyl
- cyano
- amino
- dimethoxytetralin
- ethyl
- 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
- 150000002825 nitriles Chemical class 0.000 title claims 2
- 239000000126 substance Substances 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 13
- -1 3-trifluoromethylphenyl Chemical group 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- DYZOFLWNJVIOHA-UHFFFAOYSA-N 6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-1-amine Chemical compound C1CCC(N)C2=C1C=C(OC)C(OC)=C2 DYZOFLWNJVIOHA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000007363 ring formation reaction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 150000002366 halogen compounds Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000002048 spasmolytic effect Effects 0.000 description 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- LCTYNCUYLJJXPB-UHFFFAOYSA-N 2,2-diethoxypentanenitrile Chemical compound C(C)OC(C#N)(CCC)OCC LCTYNCUYLJJXPB-UHFFFAOYSA-N 0.000 description 1
- XJEVHMGJSYVQBQ-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-amine Chemical compound C1=CC=C2C(N)CCC2=C1 XJEVHMGJSYVQBQ-UHFFFAOYSA-N 0.000 description 1
- BGEONUMCBIQUTQ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine;hydron;chloride Chemical compound Cl.CNCCC1=CC=C(OC)C(OC)=C1 BGEONUMCBIQUTQ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 150000007962 benzene acetonitriles Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- ZLSVALLKHLKICA-UHFFFAOYSA-N hexan-1-amine;hydrobromide Chemical compound [Br-].CCCCCC[NH3+] ZLSVALLKHLKICA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002889 sympathetic effect Effects 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681793488 DE1793488A1 (de) | 1968-09-25 | 1968-09-25 | Aminobenzocycloalkylnitrile |
| US858513A US3657258A (en) | 1968-09-25 | 1969-09-16 | Aminobenzylcycloalkylnitriles |
| GB1233130D GB1233130A (enExample) | 1968-09-25 | 1969-09-17 | |
| CH1429869A CH513131A (de) | 1968-09-25 | 1969-09-22 | Verfahren zur Herstellung neuer Aminobenzocycloalkylnitrile |
| AT904969A AT289092B (de) | 1968-09-25 | 1969-09-24 | Verfahren zur Herstellung von neuen Aminobenzocycloalkylnitrilen und deren Salzen |
| SE13152/69A SE344586B (enExample) | 1968-09-25 | 1969-09-24 | |
| IL33043A IL33043A (en) | 1968-09-25 | 1969-09-24 | Aminobenzocycloalkylnitriles |
| BE739315D BE739315A (enExample) | 1968-09-25 | 1969-09-24 | |
| NL6914551A NL6914551A (enExample) | 1968-09-25 | 1969-09-25 | |
| FR696932797A FR2018875B1 (enExample) | 1968-09-25 | 1969-09-25 | |
| BR212717/69A BR6912717D0 (pt) | 1968-09-25 | 1969-09-25 | Processo para a producao de aminobenzocicloalquilonitrila |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681793488 DE1793488A1 (de) | 1968-09-25 | 1968-09-25 | Aminobenzocycloalkylnitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1793488A1 true DE1793488A1 (de) | 1972-02-24 |
Family
ID=5707727
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19681793488 Pending DE1793488A1 (de) | 1968-09-25 | 1968-09-25 | Aminobenzocycloalkylnitrile |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3657258A (enExample) |
| AT (1) | AT289092B (enExample) |
| BE (1) | BE739315A (enExample) |
| BR (1) | BR6912717D0 (enExample) |
| CH (1) | CH513131A (enExample) |
| DE (1) | DE1793488A1 (enExample) |
| FR (1) | FR2018875B1 (enExample) |
| GB (1) | GB1233130A (enExample) |
| IL (1) | IL33043A (enExample) |
| NL (1) | NL6914551A (enExample) |
| SE (1) | SE344586B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8628644D0 (en) * | 1986-12-01 | 1987-01-07 | Lunbeck A S H | Intermediates |
| AR066162A1 (es) * | 2007-07-31 | 2009-07-29 | Bayer Cropscience Sa | Derivados fungicidas de n- cicloalquil -n- carboxamida- biciclica |
-
1968
- 1968-09-25 DE DE19681793488 patent/DE1793488A1/de active Pending
-
1969
- 1969-09-16 US US858513A patent/US3657258A/en not_active Expired - Lifetime
- 1969-09-17 GB GB1233130D patent/GB1233130A/en not_active Expired
- 1969-09-22 CH CH1429869A patent/CH513131A/de not_active IP Right Cessation
- 1969-09-24 BE BE739315D patent/BE739315A/xx unknown
- 1969-09-24 AT AT904969A patent/AT289092B/de not_active IP Right Cessation
- 1969-09-24 IL IL33043A patent/IL33043A/xx unknown
- 1969-09-24 SE SE13152/69A patent/SE344586B/xx unknown
- 1969-09-25 NL NL6914551A patent/NL6914551A/xx unknown
- 1969-09-25 BR BR212717/69A patent/BR6912717D0/pt unknown
- 1969-09-25 FR FR696932797A patent/FR2018875B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE344586B (enExample) | 1972-04-24 |
| US3657258A (en) | 1972-04-18 |
| FR2018875B1 (enExample) | 1973-04-06 |
| FR2018875A1 (enExample) | 1970-06-26 |
| AT289092B (de) | 1971-04-13 |
| IL33043A0 (en) | 1969-11-30 |
| BR6912717D0 (pt) | 1973-04-26 |
| GB1233130A (enExample) | 1971-05-26 |
| BE739315A (enExample) | 1970-03-24 |
| IL33043A (en) | 1972-08-30 |
| CH513131A (de) | 1971-09-30 |
| NL6914551A (enExample) | 1970-03-31 |
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