CH574434A5 - - Google Patents
Info
- Publication number
- CH574434A5 CH574434A5 CH440072A CH440072A CH574434A5 CH 574434 A5 CH574434 A5 CH 574434A5 CH 440072 A CH440072 A CH 440072A CH 440072 A CH440072 A CH 440072A CH 574434 A5 CH574434 A5 CH 574434A5
- Authority
- CH
- Switzerland
- Prior art keywords
- imine
- dibenzo
- dihydro
- dimethylamino
- cyclohepten
- Prior art date
Links
- -1 ethylene, vinylene, oxamethylene Chemical group 0.000 claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 15
- 150000002466 imines Chemical class 0.000 claims description 14
- NYIODHFKZFKMSU-UHFFFAOYSA-N n,n-bis(methylamino)ethanamine Chemical compound CCN(NC)NC NYIODHFKZFKMSU-UHFFFAOYSA-N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- GUSNZJMMSRJLMC-UHFFFAOYSA-N C1=CC=CC=2C(C3=C(CCC21)C=CC=C3)=N Chemical compound C1=CC=CC=2C(C3=C(CCC21)C=CC=C3)=N GUSNZJMMSRJLMC-UHFFFAOYSA-N 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- WUKMXVXFFIHIFW-UHFFFAOYSA-N cyclohept-4-en-1-imine Chemical compound N=C1CCC=CCC1 WUKMXVXFFIHIFW-UHFFFAOYSA-N 0.000 description 32
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 31
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 230000001078 anti-cholinergic effect Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- BGCQURJQCRIOFH-UHFFFAOYSA-N 2-[(2-chloro-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=CC=C(Cl)C=C2C(=NCCN(C)C)C2=CC=CC=C21 BGCQURJQCRIOFH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 208000027089 Parkinsonian disease Diseases 0.000 description 2
- 206010034010 Parkinsonism Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000001430 anti-depressive effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- PFJOTFSIBVZGPK-UHFFFAOYSA-N 1-ethyl-2-methylhydrazine Chemical compound CCNNC PFJOTFSIBVZGPK-UHFFFAOYSA-N 0.000 description 1
- HXOBQRZIXMCOLZ-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)-n,n-diethylethanamine Chemical compound C1CC2=CC=CC=C2C(=NCCN(CC)CC)C2=CC=CC=C21 HXOBQRZIXMCOLZ-UHFFFAOYSA-N 0.000 description 1
- WLMACKDAAQMPOY-UHFFFAOYSA-N 2-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)-n,n-dimethylethanamine Chemical compound C1CC2=CC=CC=C2C(=NCCN(C)C)C2=CC=CC=C21 WLMACKDAAQMPOY-UHFFFAOYSA-N 0.000 description 1
- SYGVEAINKHSXQM-UHFFFAOYSA-N 2-[(2,4-dichloro-5,6-dihydrodibenzo[2,1-b:4',1'-f][7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=C(Cl)C=C(Cl)C=C2C(=NCCN(C)C)C2=CC=CC=C21 SYGVEAINKHSXQM-UHFFFAOYSA-N 0.000 description 1
- MEUUWSHBMGASRD-UHFFFAOYSA-N 2-[(2-bromo-5,6-dihydrodibenzo[3,1-[7]annulen-11-ylidene)amino]-n,n-dimethylethanamine Chemical compound C1CC2=CC=C(Br)C=C2C(=NCCN(C)C)C2=CC=CC=C21 MEUUWSHBMGASRD-UHFFFAOYSA-N 0.000 description 1
- QBXSOWYAYREWCZ-UHFFFAOYSA-N 2-[(4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-ylidene)amino]-n-methylethanamine Chemical compound C1CC2=C(Cl)C=CC=C2C(=NCCNC)C2=CC=CC=C21 QBXSOWYAYREWCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- VDERCYDMZRHAQB-UHFFFAOYSA-N 2-bromo-6,11-dihydro-5h-dibenzo[3,2-[7]annulene Chemical compound C1CC2=CC=CC=C2CC2=CC(Br)=CC=C21 VDERCYDMZRHAQB-UHFFFAOYSA-N 0.000 description 1
- FUVPAVYZJYUINB-UHFFFAOYSA-N 2-chloro-6,11-dihydro-5h-dibenzo[3,2-[7]annulene Chemical compound C1CC2=CC=CC=C2CC2=CC(Cl)=CC=C21 FUVPAVYZJYUINB-UHFFFAOYSA-N 0.000 description 1
- NBOTVTKJRBAJLU-UHFFFAOYSA-N 3-(5,6-dihydrodibenzo[2,1-b:2',1'-f][7]annulen-11-ylideneamino)-n,n-dimethylpropan-1-amine Chemical compound C1CC2=CC=CC=C2C(=NCCCN(C)C)C2=CC=CC=C21 NBOTVTKJRBAJLU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- UARWLAOATPMYKK-UHFFFAOYSA-N 4-chloro-5,6-dihydrodibenzo[2,1-b:3',2'-f][7]annulen-11-one Chemical compound C1CC2=CC=CC=C2C(=O)C2=C1C(Cl)=CC=C2 UARWLAOATPMYKK-UHFFFAOYSA-N 0.000 description 1
- HCHARTNRNLMAMF-UHFFFAOYSA-N 7-fluorotricyclo[9.4.0.03,8]pentadeca-1(15),3(8),4,6,11,13-hexaene Chemical compound Fc1cccc2Cc3ccccc3CCc12 HCHARTNRNLMAMF-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- JNNJTHXRTXNEDI-UHFFFAOYSA-N CN(CCC1=CC=CC=2C(C3=C(CCC=21)C=CC=C3)=N)C Chemical compound CN(CCC1=CC=CC=2C(C3=C(CCC=21)C=CC=C3)=N)C JNNJTHXRTXNEDI-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000000954 anitussive effect Effects 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940124584 antitussives Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 208000030499 combat disease Diseases 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 description 1
- PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- YPLIFKZBNCNJJN-UHFFFAOYSA-N n,n-bis(ethylamino)ethanamine Chemical compound CCNN(CC)NCC YPLIFKZBNCNJJN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000001953 recrystallisation Methods 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
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BISQTCXKVNCDDA-UHFFFAOYSA-N thiepine Chemical compound S1C=CC=CC=C1 BISQTCXKVNCDDA-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D337/00—Heterocyclic compounds containing rings of more than six members having one sulfur atom as the only ring hetero atom
- C07D337/02—Seven-membered rings
- C07D337/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D337/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D337/12—[b,e]-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
- C07D313/10—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D313/12—[b,e]-condensed
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)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH440072A CH574434A5 (enrdf_load_stackoverflow) | 1972-03-24 | 1972-03-24 | |
| DD169100A DD106033A5 (enrdf_load_stackoverflow) | 1972-03-24 | 1973-02-27 | |
| JP48033069A JPS4911869A (enrdf_load_stackoverflow) | 1972-03-24 | 1973-03-22 | |
| SU1898680A SU508181A3 (ru) | 1972-03-24 | 1973-03-22 | Способ получени трициклических иминов |
| CA166,862A CA1013348A (en) | 1972-03-24 | 1973-03-23 | Tricyclic imines |
| AT260473A AT322532B (de) | 1972-03-24 | 1973-03-23 | Verfahren zur herstellung von neuen tricyclischen iminen |
| KR7300469A KR780000158B1 (en) | 1972-03-24 | 1973-03-23 | Method for preparing tricyclic imines |
| HUHO1555A HU164908B (enrdf_load_stackoverflow) | 1972-03-24 | 1973-03-23 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH440072A CH574434A5 (enrdf_load_stackoverflow) | 1972-03-24 | 1972-03-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH574434A5 true CH574434A5 (enrdf_load_stackoverflow) | 1976-04-15 |
Family
ID=4275427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH440072A CH574434A5 (enrdf_load_stackoverflow) | 1972-03-24 | 1972-03-24 |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4911869A (enrdf_load_stackoverflow) |
| KR (1) | KR780000158B1 (enrdf_load_stackoverflow) |
| AT (1) | AT322532B (enrdf_load_stackoverflow) |
| CA (1) | CA1013348A (enrdf_load_stackoverflow) |
| CH (1) | CH574434A5 (enrdf_load_stackoverflow) |
| DD (1) | DD106033A5 (enrdf_load_stackoverflow) |
| HU (1) | HU164908B (enrdf_load_stackoverflow) |
| SU (1) | SU508181A3 (enrdf_load_stackoverflow) |
-
1972
- 1972-03-24 CH CH440072A patent/CH574434A5/de not_active IP Right Cessation
-
1973
- 1973-02-27 DD DD169100A patent/DD106033A5/xx unknown
- 1973-03-22 JP JP48033069A patent/JPS4911869A/ja active Pending
- 1973-03-22 SU SU1898680A patent/SU508181A3/ru active
- 1973-03-23 KR KR7300469A patent/KR780000158B1/ko not_active Expired
- 1973-03-23 AT AT260473A patent/AT322532B/de not_active IP Right Cessation
- 1973-03-23 HU HUHO1555A patent/HU164908B/hu unknown
- 1973-03-23 CA CA166,862A patent/CA1013348A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT322532B (de) | 1975-05-26 |
| HU164908B (enrdf_load_stackoverflow) | 1974-05-28 |
| JPS4911869A (enrdf_load_stackoverflow) | 1974-02-01 |
| CA1013348A (en) | 1977-07-05 |
| DD106033A5 (enrdf_load_stackoverflow) | 1974-05-20 |
| SU508181A3 (ru) | 1976-03-25 |
| KR780000158B1 (en) | 1978-05-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |