DE2108395A1 - Substituierte Phenoxyathylamine, ihre Verwendung und Verfahren zur Herstellung derselben - Google Patents
Substituierte Phenoxyathylamine, ihre Verwendung und Verfahren zur Herstellung derselbenInfo
- Publication number
- DE2108395A1 DE2108395A1 DE19712108395 DE2108395A DE2108395A1 DE 2108395 A1 DE2108395 A1 DE 2108395A1 DE 19712108395 DE19712108395 DE 19712108395 DE 2108395 A DE2108395 A DE 2108395A DE 2108395 A1 DE2108395 A1 DE 2108395A1
- Authority
- DE
- Germany
- Prior art keywords
- ether
- formula
- alcohol
- compounds according
- fibrillation
- 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 7
- IMLAIXAZMVDRGA-UHFFFAOYSA-N 2-phenoxyethanamine Chemical class NCCOC1=CC=CC=C1 IMLAIXAZMVDRGA-UHFFFAOYSA-N 0.000 title claims description 6
- 239000000460 chlorine Substances 0.000 claims description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 13
- 206010061592 cardiac fibrillation Diseases 0.000 claims description 12
- 230000002600 fibrillogenic effect Effects 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003071 vasodilator agent Substances 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006413 ring segment Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 210000003298 dental enamel Anatomy 0.000 description 9
- KLKFAASOGCDTDT-UHFFFAOYSA-N ethoxymethoxyethane Chemical compound CCOCOCC KLKFAASOGCDTDT-UHFFFAOYSA-N 0.000 description 9
- 210000003608 fece Anatomy 0.000 description 7
- 239000010871 livestock manure Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 230000001476 alcoholic effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 230000000304 vasodilatating effect Effects 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- -1 alkyl radicals Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- GJHKWLSRHNWTAN-UHFFFAOYSA-N 1-ethoxy-4-(4-pentylcyclohexyl)benzene Chemical compound C1CC(CCCCC)CCC1C1=CC=C(OCC)C=C1 GJHKWLSRHNWTAN-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000010412 perfusion Effects 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229960004482 quinidine sulfate Drugs 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229940124549 vasodilator Drugs 0.000 description 2
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- RAGSWDIQBBZLLL-UHFFFAOYSA-N 2-chloroethyl(diethyl)azanium;chloride Chemical compound Cl.CCN(CC)CCCl RAGSWDIQBBZLLL-UHFFFAOYSA-N 0.000 description 1
- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 1
- LCHYEKKJCUJAKN-UHFFFAOYSA-N 2-propylphenol Chemical compound CCCC1=CC=CC=C1O LCHYEKKJCUJAKN-UHFFFAOYSA-N 0.000 description 1
- ZAPMTSHEXFEPSD-UHFFFAOYSA-N 4-(2-chloroethyl)morpholine Chemical compound ClCCN1CCOCC1 ZAPMTSHEXFEPSD-UHFFFAOYSA-N 0.000 description 1
- LHNIWOPTIYFVDY-UHFFFAOYSA-N 5-chloro-2-propylphenol Chemical compound CCCC1=CC=C(Cl)C=C1O LHNIWOPTIYFVDY-UHFFFAOYSA-N 0.000 description 1
- JAFJYTWXUSVNMX-UHFFFAOYSA-N Cl.C1(=CC=CC=C1)CCCCC Chemical compound Cl.C1(=CC=CC=C1)CCCCC JAFJYTWXUSVNMX-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000700159 Rattus Species 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
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- RDUHXGIIUDVSHR-UHFFFAOYSA-N bamethan Chemical compound CCCCNCC(O)C1=CC=C(O)C=C1 RDUHXGIIUDVSHR-UHFFFAOYSA-N 0.000 description 1
- 229960004162 bamethan Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- IDDGKAPFCRVXIT-UHFFFAOYSA-N butylbenzene hydrochloride Chemical compound Cl.C1(=CC=CC=C1)CCCC IDDGKAPFCRVXIT-UHFFFAOYSA-N 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- SPTYHKZRPFATHJ-HYZXJONISA-N dT6 Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)COP(O)(=O)O[C@@H]2[C@H](O[C@H](C2)N2C(NC(=O)C(C)=C2)=O)CO)[C@@H](O)C1 SPTYHKZRPFATHJ-HYZXJONISA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 230000000763 evoking effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- 229960002312 tolazoline Drugs 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2333170 | 1970-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2108395A1 true DE2108395A1 (de) | 1971-11-04 |
Family
ID=11206135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712108395 Pending DE2108395A1 (de) | 1970-04-15 | 1971-02-22 | Substituierte Phenoxyathylamine, ihre Verwendung und Verfahren zur Herstellung derselben |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT307387B (enExample) |
| BE (1) | BE761623A (enExample) |
| CA (1) | CA935162A (enExample) |
| CH (1) | CH518257A (enExample) |
| DE (1) | DE2108395A1 (enExample) |
| DK (1) | DK127501B (enExample) |
| ES (1) | ES388464A1 (enExample) |
| FR (1) | FR2086070B1 (enExample) |
| GB (1) | GB1325795A (enExample) |
| IL (1) | IL36235A0 (enExample) |
| NL (1) | NL7101057A (enExample) |
| SU (1) | SU374815A3 (enExample) |
| ZA (1) | ZA711626B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0288647B1 (fr) * | 1987-04-30 | 1992-04-08 | INSTITUT DE RECHERCHES CHIMIQUES ET BIOLOGIQUES APPLIQUEES (I.R.C.E.B.A.) Société à responsabilité limitée dite: | Dérivés du [(pyrrolidinyl-1)-2éthoxy]-5 p-cymène, le procédé de préparation desdits dérivés et les médicaments contenant lesdits dérivés |
| DK368687A (da) * | 1986-11-21 | 1988-05-22 | Cheminova As | Aminoalkylerede hydroxyforbindelser og deres anvendelse som fungicider |
| WO2013074965A1 (en) * | 2011-11-16 | 2013-05-23 | Microbiotix, Inc. | Aminoalkyl phenol ether inhibitors of influenza a virus |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3205136A (en) * | 1962-12-24 | 1965-09-07 | Smith Kline French Lab | Antidepressant phenyloxyalkylamines |
-
1971
- 1971-01-15 BE BE761623A patent/BE761623A/xx unknown
- 1971-01-22 FR FR7102190A patent/FR2086070B1/fr not_active Expired
- 1971-01-27 NL NL7101057A patent/NL7101057A/xx unknown
- 1971-01-27 CH CH118371A patent/CH518257A/fr not_active IP Right Cessation
- 1971-02-02 SU SU1618525A patent/SU374815A3/ru active
- 1971-02-15 DK DK66171AA patent/DK127501B/da unknown
- 1971-02-19 IL IL36235A patent/IL36235A0/xx unknown
- 1971-02-20 ES ES388464A patent/ES388464A1/es not_active Expired
- 1971-02-22 DE DE19712108395 patent/DE2108395A1/de active Pending
- 1971-03-10 AT AT206971A patent/AT307387B/de active
- 1971-03-12 ZA ZA711626A patent/ZA711626B/xx unknown
- 1971-04-14 CA CA110325A patent/CA935162A/en not_active Expired
- 1971-04-19 GB GB2513571*A patent/GB1325795A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU374815A3 (enExample) | 1973-03-20 |
| ES388464A1 (es) | 1973-05-01 |
| CA935162A (en) | 1973-10-09 |
| AT307387B (de) | 1973-05-25 |
| NL7101057A (enExample) | 1971-10-19 |
| CH518257A (fr) | 1972-01-31 |
| BE761623A (fr) | 1971-06-16 |
| DK127501B (da) | 1973-11-19 |
| FR2086070B1 (enExample) | 1974-08-02 |
| FR2086070A1 (enExample) | 1971-12-31 |
| IL36235A0 (en) | 1971-04-28 |
| ZA711626B (en) | 1971-12-29 |
| GB1325795A (en) | 1973-08-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2341753C2 (de) | α-(3-tert.Butylamino-α-hydroxy-propylthio)- Thiazolderivate, Verfahren zu deren Herstellung und dieselben enthaltende pharmazeutische Zubereitung | |
| DE1670048C3 (de) | Neue Norscopolaminderivate | |
| DE1906527B2 (de) | Thioninderivate, Verfahren zu deren Herstellung und pharmazeutische Präparate, welche diese enthalten | |
| DE2065312C3 (de) | Aminoäthansulfonylderivate und Verfahren zu ihrer Herstellung | |
| DE2108395A1 (de) | Substituierte Phenoxyathylamine, ihre Verwendung und Verfahren zur Herstellung derselben | |
| DE2166270C3 (de) | Nicotinoylaminoäthansulfonyl-2amino-thiazol | |
| DE2717001A1 (de) | Arzneimittel mit antithrombotischer wirkung | |
| DE2167181B1 (de) | Methyl-N-acetyl-6,7-aziridino-6-desamino-7-desoxy-2,3,4-tri-0-acetyl-alpha-thiolincosaminid und Verfahren zu dessen Herstellung | |
| DE1518337A1 (de) | Neue Roentgenkontrastmittel und Verfahren zur Herstellung derselben | |
| DE2528194C2 (de) | Benzhydryloxyäthylamin-Derivate, deren Salze, Verfahren zur Herstellung derselben und solche enthaltende Arzneimittel | |
| DE1620747C3 (de) | Carbothiamin sowie dessen nichttoxische organische oder anorganische Säureadditionssalze sowie Verfahren zur Herstellung dieser Verbindungen | |
| DE2065333A1 (de) | N-substituierte 3,4-dihydro-3-oxo-2h1,2-benzothiazin-s-dioxydderivate, ihre verwendung und verfahren zur herstellung derselben | |
| DE2106705A1 (de) | Esterderivate von Tetrahydrocanna binolen | |
| DE1645901C3 (de) | gamma-(4-Alkylp!peridino)-p-fluorbutyrophenone und Verfahren zu ihrer Herstellung | |
| DE2225762C3 (de) | Substituierte Fusarsäuren und Derivate derselben sowie Verfahren zur Herstellung derselben und Arzneimittel mit einem Gehalt derselben | |
| DE2355917C3 (de) | 1,3-Bis(β-äthylhexyl)-5-nitro-5-methyl-hexahydropyrimidin-naphthalin-1,5-disulfonat und Verfahren zu seiner Herstellung | |
| DE2215169A1 (de) | N-disubstituierte Aminoäthylester der 11-Methoxyraubasinsäure und Verfahren zur Herstellung derselben | |
| DE949232C (de) | Verfahren zur Herstellung therapeutisch wertvoller basischer substituierter Essigsaeureester | |
| DE1770669C3 (de) | 1 -Acyl-4-oxo-i ,2,3,4-tetrahydrochinazoline und Verfahren zu ihrer Herstellung | |
| DE1226570B (de) | Verfahren zur Herstellung von Kampferderivaten | |
| DE2559558C3 (de) | Apovincaminsäureamide, deren Salze mit Säuren, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1695796C3 (de) | N,N'-Alkylen-bis- eckige Klammer auf dibenzobicyclooctanpyrrolidin eckige Klammer zu -Verbindungen | |
| DE1795153A1 (de) | Neue N-substituierte Piperidinspiroverbindungen,ihre Verwendung und Herstellung | |
| DE1695580C (de) | Quaternare Verbindungen des Benzil saure beta piperidino athylesters und ein Verfahren zu ihrer Herstellung | |
| DE181287C (enExample) |