DE2821584C2 - - Google Patents
Info
- Publication number
- DE2821584C2 DE2821584C2 DE2821584A DE2821584A DE2821584C2 DE 2821584 C2 DE2821584 C2 DE 2821584C2 DE 2821584 A DE2821584 A DE 2821584A DE 2821584 A DE2821584 A DE 2821584A DE 2821584 C2 DE2821584 C2 DE 2821584C2
- Authority
- DE
- Germany
- Prior art keywords
- tetrahydro
- methoxy
- ethyl
- naphthylamine
- dimethoxybenzoyloxy
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 36
- LCGFVWKNXLRFIF-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine Chemical class C1=CC=C2CC(N)CCC2=C1 LCGFVWKNXLRFIF-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- XIFULPNNLTUXAU-UHFFFAOYSA-N 4-[(6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-ethylamino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=C(OC)C=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 XIFULPNNLTUXAU-UHFFFAOYSA-N 0.000 claims description 3
- XHLYJQSVUFVAEL-UHFFFAOYSA-N 6-[ethyl(1,2,3,4-tetrahydronaphthalen-2-yl)amino]hexyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CC1N(CC)CCCCCCOC(=O)C1=CC=C(OC)C(OC)=C1 XHLYJQSVUFVAEL-UHFFFAOYSA-N 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- RNKHBJYAZIFNQW-UHFFFAOYSA-N 6-[(6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-ethylamino]hexyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=C(OC)C=C2CC1N(CC)CCCCCCOC(=O)C1=CC=C(OC)C(OC)=C1 RNKHBJYAZIFNQW-UHFFFAOYSA-N 0.000 claims description 2
- RUXQBTGYPSDBJF-UHFFFAOYSA-N 6-[ethyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]hexyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(CC)CCCCCCOC(=O)C1=CC=C(OC)C(OC)=C1 RUXQBTGYPSDBJF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- BADKYUCRLXZRBF-UHFFFAOYSA-N 4-[cyclohexyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(C1CCCCC1)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 BADKYUCRLXZRBF-UHFFFAOYSA-N 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 69
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 36
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 34
- 239000013078 crystal Substances 0.000 description 33
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 32
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 32
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 238000004458 analytical method Methods 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- -1 ester compounds Chemical class 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 229910000029 sodium carbonate Inorganic materials 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 235000009518 sodium iodide Nutrition 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 238000010992 reflux Methods 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- 239000012280 lithium aluminium hydride Substances 0.000 description 8
- VDKIZIBOFDIQRW-UHFFFAOYSA-N 4-chlorobutyl 3,4-dimethoxybenzoate Chemical compound COC1=CC=C(C(=O)OCCCCCl)C=C1OC VDKIZIBOFDIQRW-UHFFFAOYSA-N 0.000 description 7
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 7
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 7
- 229910003446 platinum oxide Inorganic materials 0.000 description 7
- UZVBZJPHNHFSTI-UHFFFAOYSA-N 4-iodobutyl 3,4-dimethoxybenzoate Chemical compound COC1=CC=C(C(=O)OCCCCI)C=C1OC UZVBZJPHNHFSTI-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000008602 contraction Effects 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- DAUAQNGYDSHRET-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1OC DAUAQNGYDSHRET-UHFFFAOYSA-N 0.000 description 5
- 241000282472 Canis lupus familiaris Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- GPVDHNVGGIAOQT-UHFFFAOYSA-N Veratric acid Natural products COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- VYVKHNNGDFVQGA-UHFFFAOYSA-N 3,4-dimethoxybenzoic acid 4-[ethyl-[1-(4-methoxyphenyl)propan-2-yl]amino]butyl ester Chemical compound C=1C=C(OC)C=CC=1CC(C)N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 VYVKHNNGDFVQGA-UHFFFAOYSA-N 0.000 description 4
- DYSSJBAGXQBWNT-UHFFFAOYSA-N 6-chlorohexyl 3,4-dimethoxybenzoate Chemical compound COC1=CC=C(C(=O)OCCCCCCCl)C=C1OC DYSSJBAGXQBWNT-UHFFFAOYSA-N 0.000 description 4
- RMRKDYNVZWKAFP-UHFFFAOYSA-N 6-methoxy-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1C(=O)CCC2=CC(OC)=CC=C21 RMRKDYNVZWKAFP-UHFFFAOYSA-N 0.000 description 4
- 230000001773 anti-convulsant effect Effects 0.000 description 4
- 210000001072 colon Anatomy 0.000 description 4
- 230000004600 colonic motility Effects 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- AWYNYGDVTNSMIS-UHFFFAOYSA-N ethanamine;ethanol Chemical compound CCN.CCO AWYNYGDVTNSMIS-UHFFFAOYSA-N 0.000 description 4
- 210000001035 gastrointestinal tract Anatomy 0.000 description 4
- 229960003577 mebeverine Drugs 0.000 description 4
- 210000005036 nerve Anatomy 0.000 description 4
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 210000002784 stomach Anatomy 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- CDPDVJDJEFXECI-UHFFFAOYSA-N 4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-propan-2-ylamino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(C(C)C)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 CDPDVJDJEFXECI-UHFFFAOYSA-N 0.000 description 3
- SDWHFWOBCIITOQ-UHFFFAOYSA-N 4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-propylamino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(CCC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 SDWHFWOBCIITOQ-UHFFFAOYSA-N 0.000 description 3
- OUTUENSFVXPYBP-UHFFFAOYSA-N 6-methoxy-n-propan-2-yl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1C(NC(C)C)CCC2=CC(OC)=CC=C21 OUTUENSFVXPYBP-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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 210000001015 abdomen Anatomy 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000460 chlorine Substances 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
- 229920001971 elastomer Polymers 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- SRXOJMOGPYFZKC-UHFFFAOYSA-N methyl 4-chloro-4-oxobutanoate Chemical compound COC(=O)CCC(Cl)=O SRXOJMOGPYFZKC-UHFFFAOYSA-N 0.000 description 3
- CKXFPBHAUKEBBF-UHFFFAOYSA-N n-ethyl-5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2CC(NCC)CCC2=C1OC CKXFPBHAUKEBBF-UHFFFAOYSA-N 0.000 description 3
- XSHYYYOTFANHSV-UHFFFAOYSA-N n-ethyl-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=C(OC)C=C2CC(NCC)CCC2=C1 XSHYYYOTFANHSV-UHFFFAOYSA-N 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- FJQOAYUXVCSSQR-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound [Cl-].C1=CC=C2CC([NH3+])CCC2=C1 FJQOAYUXVCSSQR-UHFFFAOYSA-N 0.000 description 2
- ZVVWZNFSMIFGEP-UHFFFAOYSA-N 2-(4-ethoxyphenyl)acetic acid Chemical compound CCOC1=CC=C(CC(O)=O)C=C1 ZVVWZNFSMIFGEP-UHFFFAOYSA-N 0.000 description 2
- VIOBGCWEHLRBEP-UHFFFAOYSA-N 3,4-dimethoxybenzoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1OC VIOBGCWEHLRBEP-UHFFFAOYSA-N 0.000 description 2
- NTNIZPLCUMAJFS-UHFFFAOYSA-N 4-[(5,8-dimethoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-ethylamino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=C(OC)C=CC(OC)=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 NTNIZPLCUMAJFS-UHFFFAOYSA-N 0.000 description 2
- UZFIPYZHEMCHDA-UHFFFAOYSA-N 4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-methylamino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(C)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 UZFIPYZHEMCHDA-UHFFFAOYSA-N 0.000 description 2
- HXGWJZGQZVLUSH-UHFFFAOYSA-N 4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-propylamino]butan-1-ol Chemical compound COC1=CC=C2CC(N(CCCCO)CCC)CCC2=C1 HXGWJZGQZVLUSH-UHFFFAOYSA-N 0.000 description 2
- YZTWYVMLJTUIAN-UHFFFAOYSA-N 4-[(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1NCCCCOC(=O)C1=CC=C(OC)C(OC)=C1 YZTWYVMLJTUIAN-UHFFFAOYSA-N 0.000 description 2
- ZVUJXGWVQLQRGH-UHFFFAOYSA-N 4-[cyclohexyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butan-1-ol Chemical compound C1CC2=CC(OC)=CC=C2CC1N(CCCCO)C1CCCCC1 ZVUJXGWVQLQRGH-UHFFFAOYSA-N 0.000 description 2
- OQHOEWAVHOSGBN-UHFFFAOYSA-N 4-[ethyl(1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC=CC=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 OQHOEWAVHOSGBN-UHFFFAOYSA-N 0.000 description 2
- KKGHOHWLJHDYMH-UHFFFAOYSA-N 4-[ethyl-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC(C(=CC=C2)OC)=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 KKGHOHWLJHDYMH-UHFFFAOYSA-N 0.000 description 2
- FIVSQMBVXQDIGG-UHFFFAOYSA-N 4-[ethyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butan-1-ol Chemical compound COC1=CC=C2CC(N(CCCCO)CC)CCC2=C1 FIVSQMBVXQDIGG-UHFFFAOYSA-N 0.000 description 2
- OZZNKVQJEMSOSF-UHFFFAOYSA-N 4-[ethyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate Chemical compound C1CC2=CC(OC)=CC=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 OZZNKVQJEMSOSF-UHFFFAOYSA-N 0.000 description 2
- UPMYHICLIINOMI-UHFFFAOYSA-N 4-[ethyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OC)=CC=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 UPMYHICLIINOMI-UHFFFAOYSA-N 0.000 description 2
- QRMTVBQFQRCWHA-UHFFFAOYSA-N 4-[ethyl-(6-propoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC(OCCC)=CC=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 QRMTVBQFQRCWHA-UHFFFAOYSA-N 0.000 description 2
- PFCHIFOYOFVFLJ-UHFFFAOYSA-N 4-[ethyl-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC=C(OC)C=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 PFCHIFOYOFVFLJ-UHFFFAOYSA-N 0.000 description 2
- QPVVSLPICGVFSK-UHFFFAOYSA-N 4-[ethyl-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]butyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC=CC(OC)=C2CC1N(CC)CCCCOC(=O)C1=CC=C(OC)C(OC)=C1 QPVVSLPICGVFSK-UHFFFAOYSA-N 0.000 description 2
- FOAMCKQEKSLNSA-UHFFFAOYSA-N 6-[ethyl-(6-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]hexan-1-ol Chemical compound COC1=CC=C2CC(N(CCCCCCO)CC)CCC2=C1 FOAMCKQEKSLNSA-UHFFFAOYSA-N 0.000 description 2
- GGHHUTCAJBOQMK-UHFFFAOYSA-N 6-[ethyl-(8-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amino]hexyl 3,4-dimethoxybenzoate;hydrochloride Chemical compound Cl.C1CC2=CC=CC(OC)=C2CC1N(CC)CCCCCCOC(=O)C1=CC=C(OC)C(OC)=C1 GGHHUTCAJBOQMK-UHFFFAOYSA-N 0.000 description 2
- NSWLRLBIDKLUOM-UHFFFAOYSA-N 6-ethoxy-3,4-dihydro-1h-naphthalen-2-one Chemical compound C1C(=O)CCC2=CC(OCC)=CC=C21 NSWLRLBIDKLUOM-UHFFFAOYSA-N 0.000 description 2
- WWTLHXARGZOMBV-UHFFFAOYSA-N 6-ethoxy-n-ethyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.CCOC1=CC=C2CC(NCC)CCC2=C1 WWTLHXARGZOMBV-UHFFFAOYSA-N 0.000 description 2
- WASIYUSITZITPW-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1C(N)CCC2=CC(OC)=CC=C21 WASIYUSITZITPW-UHFFFAOYSA-N 0.000 description 2
- BZJPCRWKAXOBTN-UHFFFAOYSA-N 6-methoxy-n-propyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C2CC(NCCC)CCC2=C1 BZJPCRWKAXOBTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 210000000436 anus Anatomy 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000112 colonic effect Effects 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
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- RDDGNJSHYAVRDT-UHFFFAOYSA-N n-ethyl-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC=C2CC(NCC)CCC2=C1 RDDGNJSHYAVRDT-UHFFFAOYSA-N 0.000 description 1
- WNGRQQJJZJFYSB-UHFFFAOYSA-N n-ethyl-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2CC(NCC)CCC2=C1 WNGRQQJJZJFYSB-UHFFFAOYSA-N 0.000 description 1
- VUUQVYBJOPHHHP-UHFFFAOYSA-N n-ethyl-5-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC=C(OC)C2=C1CC(NCC)CC2 VUUQVYBJOPHHHP-UHFFFAOYSA-N 0.000 description 1
- KCXSWWMGBSTHLT-UHFFFAOYSA-N n-ethyl-6-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.COC1=CC=C2CC(NCC)CCC2=C1 KCXSWWMGBSTHLT-UHFFFAOYSA-N 0.000 description 1
- SFSMWTFQYYQTKK-UHFFFAOYSA-N n-ethyl-6-propoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1C(NCC)CCC2=CC(OCCC)=CC=C21 SFSMWTFQYYQTKK-UHFFFAOYSA-N 0.000 description 1
- MDWURTNZMROBEV-UHFFFAOYSA-N n-ethyl-7-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=C(OC)C=C2CC(NCC)CCC2=C1 MDWURTNZMROBEV-UHFFFAOYSA-N 0.000 description 1
- BOGGTGDIOROWLJ-UHFFFAOYSA-N n-ethyl-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine Chemical compound C1=CC(OC)=C2CC(NCC)CCC2=C1 BOGGTGDIOROWLJ-UHFFFAOYSA-N 0.000 description 1
- IKPQPNYOTDTQAN-UHFFFAOYSA-N n-ethyl-8-methoxy-1,2,3,4-tetrahydronaphthalen-2-amine;hydrochloride Chemical compound Cl.C1=CC(OC)=C2CC(NCC)CCC2=C1 IKPQPNYOTDTQAN-UHFFFAOYSA-N 0.000 description 1
- FOKKJVHTXPJHEN-UHFFFAOYSA-N naphthalen-1-ylazanium;chloride Chemical compound Cl.C1=CC=C2C(N)=CC=CC2=C1 FOKKJVHTXPJHEN-UHFFFAOYSA-N 0.000 description 1
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- 229910017604 nitric acid Inorganic materials 0.000 description 1
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- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP52056837A JPS6045180B2 (ja) | 1977-05-17 | 1977-05-17 | ２−アミノテトラリン誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2821584A1 DE2821584A1 (de) | 1978-11-30 |
| DE2821584C2 true DE2821584C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-01-02 |
Family
ID=13038499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782821584 Granted DE2821584A1 (de) | 1977-05-17 | 1978-05-17 | Neue, pharmazeutisch wirksame verbindungen, verfahren zu ihrer herstellung und arzneimittel |
Country Status (9)
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|---|---|---|---|---|
| DE3718317A1 (de) * | 1986-12-10 | 1988-06-16 | Bayer Ag | Substituierte basische 2-aminotetraline |
| US5153225A (en) * | 1986-12-10 | 1992-10-06 | Bayer Aktiengesellschaft | Substituted basic 2-aminotetralin in pharmaceuticals |
| HUT61719A (en) * | 1989-05-31 | 1993-03-01 | Upjohn Co | Process for producing 2-aminotetraline derivatives and pharmaceutical compositions comprising such compounds |
| US5545755A (en) * | 1989-05-31 | 1996-08-13 | The Upjohn Company | Therapeutically useful 2-aminotetralin derivatives |
| US5071875A (en) * | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| MX2023014630A (es) | 2021-06-08 | 2024-01-30 | Atai Therapeutics Inc | Activadores de dimetoxifenilalquilamina de receptores de serotonina. |
| US11827580B2 (en) * | 2021-12-27 | 2023-11-28 | ATAI Life Sciences AG | Aminotetraline activators of serotonin receptors |
| US12343319B2 (en) | 2023-05-01 | 2025-07-01 | Atai Therapeutics, Inc. | Compositions and methods for treatment of diseases and disorders |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2112899A (en) * | 1935-03-09 | 1938-04-05 | Squibb & Sons Inc | Derivatives of ac-tetrahydro-betanaphthylamine |
| DE1126889B (de) * | 1957-11-23 | 1962-04-05 | Philips Nv | Verfahren zur Herstellung neuer, in ihrer Wirkung modifizierter, eine Vereinfachung des Reserpinmolekuels darstellender, substituierter Amine mit blutdrucksenkender und spasmolytischer Wirkung |
| DE1225662B (de) * | 1962-05-11 | 1966-09-29 | Egyt Gyogyszervegyeszeti Gyar | Verfahren zur Herstellung von basischen 3,5-Dimethoxy-4-alkoxy-benzoesaeureestern und deren Saeureadditionssalzen |
| FR2051486B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1969-05-29 | 1973-06-08 | Orsymonde |
-
1977
- 1977-05-17 JP JP52056837A patent/JPS6045180B2/ja not_active Expired
-
1978
- 1978-05-12 MX MX787094U patent/MX5315E/es unknown
- 1978-05-16 GB GB19754/78A patent/GB1594687A/en not_active Expired
- 1978-05-16 IT IT49382/78A patent/IT1115077B/it active
- 1978-05-16 CH CH530878A patent/CH642941A5/de not_active IP Right Cessation
- 1978-05-16 US US05/906,510 patent/US4239903A/en not_active Expired - Lifetime
- 1978-05-17 FR FR7814616A patent/FR2391189A1/fr active Granted
- 1978-05-17 DE DE19782821584 patent/DE2821584A1/de active Granted
- 1978-05-17 NL NL7805309A patent/NL7805309A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IT1115077B (it) | 1986-02-03 |
| NL7805309A (nl) | 1978-11-21 |
| US4239903A (en) | 1980-12-16 |
| GB1594687A (en) | 1981-08-05 |
| CH642941A5 (de) | 1984-05-15 |
| DE2821584A1 (de) | 1978-11-30 |
| JPS6045180B2 (ja) | 1985-10-08 |
| IT7849382A0 (it) | 1978-05-16 |
| JPS53141254A (en) | 1978-12-08 |
| FR2391189B1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-07-17 |
| FR2391189A1 (fr) | 1978-12-15 |
| MX5315E (es) | 1983-06-17 |
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| 8110 | Request for examination paragraph 44 | ||
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| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |