DE3405329A1 - Novel allylamine derivatives, process for their preparation, and their use - Google Patents
Novel allylamine derivatives, process for their preparation, and their useInfo
- Publication number
- DE3405329A1 DE3405329A1 DE19843405329 DE3405329A DE3405329A1 DE 3405329 A1 DE3405329 A1 DE 3405329A1 DE 19843405329 DE19843405329 DE 19843405329 DE 3405329 A DE3405329 A DE 3405329A DE 3405329 A1 DE3405329 A1 DE 3405329A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- lower alkyl
- formula
- integer
- hydrogen
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 239000001301 oxygen Substances 0.000 claims abstract description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 2
- 239000005864 Sulphur Chemical group 0.000 abstract 3
- 239000003814 drug Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- RHPMSSCVPPONDM-UHFFFAOYSA-N n-methyl-3-phenylprop-2-en-1-amine Chemical compound CNCC=CC1=CC=CC=C1 RHPMSSCVPPONDM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002516 radical scavenger Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 241000700198 Cavia Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- -1 N-cinnamyl-N-methylnaphthalene-1-thiocarboxamide Chemical compound 0.000 description 1
- SBEMKRGMKCTYEE-UHFFFAOYSA-N N-methyl-N-(3-phenylprop-2-enyl)naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)N(C)CC=CC1=CC=CC=C1 SBEMKRGMKCTYEE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 206010067409 Trichophytosis Diseases 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Neue Allylaminderivate, Verfahren zu ihrer Herstellung und ihre Verwen-New allylamine derivatives, processes for their preparation and their use
dung Die Erfindung betrifft neue Allylaminderivate der Formel worin R1 für eine Gruppe der Formeln wobei R5 und R6 gleich oder verschieden sind und jeweils Wasserstoff, Halogen, die Trifluormethyl-, die Hydroxy-, die Nitro-, eine niedere Alkyl-oder niedere Alkoxygruppe bedeuten, R7 für eine niedere Alkyl-, die Hydroxy-, eine niedere Alkoxygruppe, Halogen oder Wasserstoff steht, n eine ganze Zahl von 3 bis 5 und m eine ganze Zahl von 2 bis 4 bedeuten, R2 für eine Cycloalkylalkyl, eine Alkyl-, eine Alkenyl- oder eine Alkinylgruppe, R3 für Wasserstoff oder eine niedere Alkylgruppe, X für Sauerstoff oder Schwefel, Y für Sauerstoff, Schwefel, eine N-R8-Gruppe, wobei Wasserstoff oder eine niedere Alkylgruppe bedeutet, oder eine (CH2)0-Gruppe, wobei o eine ganze Zahl von 1 bis 3 bedeutet, und R4 für einen aromatischen fünfgliedrigen Heterocyclus, der Sauerstoff, Schwefel und Stickstoff ein- oder mehrfach als Heteroatome enthalten und der gegebenenfalls durch Halogen, die Hydroxy-, eine niedere Alkyl- oder niedere Alkoxygruppe substituiert sein kann, oder für eine Gruppe der Formeln wobei R8 obige Bedeutung besitzt und R9 eine Alkyl-, Alkenyl-, Alkinyl-, Phenylalkyl-, Phenyl-, Cycloalkylalkyl-, Phenylalkoxy- oder Aminoalkylgruppe bedeutet, R10, R11 und R12 gleich oder verschieden sein können und je für Wasserstoff oder eine niedere Alkylgruppe stehen, p eine ganze Zahl von 0 bis 4, s eine ganze Zahl von 0 bis 3 und q eine ganze Zahl von 0 bis 5 bedeuten, R13 für eine niedere Alkyl-, eine niedere Alkoxycarbonyl-, eine Alkenyl-, eine Alkinyl-, eine Phenyl- oder eine Phenylalkylgruppe steht, r eine ganze Zahl von 0 bis 5 bedeutet, R14 und R15 gleich oder verschieden sein können und je für Wasserstoff oder eine niedere Alkylgruppe stehen, R16 und R17 gleich oder verschieden sind und jeweils Wasserstoff, Halogen, die Trifluormethyl-, die Hydroxy-, die Nitro-, eine niedere Alkyl- oder eine niedere Alkoxygruppe bedeuten, stehen, sowie Verfahren zu ihrer Herstellung und ihre Verwendung.The invention relates to new allylamine derivatives of the formula wherein R1 is a group of the formulas where R5 and R6 are identical or different and are each hydrogen, halogen, trifluoromethyl, hydroxy, nitro, a lower alkyl or lower alkoxy group, R7 is a lower alkyl, hydroxy, lower alkoxy group, Halogen or hydrogen, n is an integer from 3 to 5 and m is an integer from 2 to 4, R2 is a cycloalkylalkyl, an alkyl, an alkenyl or an alkynyl group, R3 is hydrogen or a lower alkyl group, X is Oxygen or sulfur, Y for oxygen, sulfur, an N-R8 group, where denotes hydrogen or a lower alkyl group, or a (CH2) 0 group, where o denotes an integer from 1 to 3, and R4 denotes an aromatic group five-membered heterocycle which contains oxygen, sulfur and nitrogen one or more times as heteroatoms and which can optionally be substituted by halogen, the hydroxyl, a lower alkyl or lower alkoxy group, or for a group of the formulas where R8 has the above meaning and R9 denotes an alkyl, alkenyl, alkynyl, phenylalkyl, phenyl, cycloalkylalkyl, phenylalkoxy or aminoalkyl group, R10, R11 and R12 can be identical or different and each represent hydrogen or a lower alkyl group stand, p is an integer from 0 to 4, s is an integer from 0 to 3 and q is an integer from 0 to 5, R13 is a lower alkyl, a lower alkoxycarbonyl, an alkenyl, an alkynyl, is a phenyl or a phenylalkyl group, r is an integer from 0 to 5, R14 and R15 can be identical or different and each represent hydrogen or a lower alkyl group, R16 and R17 are identical or different and are each hydrogen, halogen, the Trifluoromethyl, the hydroxy, the nitro, a lower alkyl or a lower alkoxy group mean, as well as processes for their preparation and their use.
Erfindungsgemäß gelangt man zu den Verbindungen der Formel 1, indem man a) eine Verbindung der Formel worin R1 und X obige Bedeutung besitzen und R18 für eine abspaltbare Gruppe steht, mit einer Verbindung der Formel worin R2, R3 und R4 obige Bedeutung besitzen, oder b) zur Herstellung einer Verbindung der Formel worin R1, R2, R3 und R4 obige Bedeutung besitzen, eine Verbindung der Formel worin R1, R2, R3 und R4 obige Bedeutung besitzen, mit P2S5 umsetzt.According to the invention, the compounds of the formula 1 are obtained by a) a compound of the formula in which R1 and X have the above meanings and R18 stands for a group which can be split off, with a compound of the formula in which R2, R3 and R4 have the above meanings, or b) for the preparation of a compound of the formula in which R1, R2, R3 and R4 have the above meanings, a compound of the formula in which R1, R2, R3 and R4 have the above meaning, reacts with P2S5.
Die erfindungsgemäße Variante a) kann nach an sich für Acylierungen bekannten Methoden durchgeführt werden, beispielsweise in einem unter den Reaktionsbedingungen inerten Lösungsmittel. Vorteilhafterweise setzt man dem Reaktionsgemisch einen Säurefänger zu oder verwendet ein Lösungsmittel, das gleichzeitig als Säurefänger fungiert, z.B. Pyridin. Die Reaktionstemperatur kann zwischen 0 und 1500 C liegen und beträgt vorzugsweise 0° bis Raumtemperatur.Variant a) according to the invention can per se be used for acylations known methods can be carried out, for example in one under the reaction conditions inert solvent. It is advantageous to add an acid scavenger to the reaction mixture to or used a Solvent that doubles as an acid scavenger acts, e.g. pyridine. The reaction temperature can be between 0 and 1500.degree and is preferably from 0 ° to room temperature.
Die Variante b) kann nach für die Umwandlung des amidischen Sauerstoffes in das Thioamid bekannten Methoden vor sich gehen. Beispielsweise löst oder suspendiert man eine Verbindung der Formel Ia in einem unter den Reaktionsbedingungen inerten Lösungsmittel wie Benzol oder Toluol, setzt nach Zugabe von Pyridin oder Picolin P255 zu und läßt bei Raumtemperatur bis 1500 C reagieren. Aus dem Reaktionsgemisch kann das Endprodukt nach an sich bekannten Methoden isoliert und gegebenenfalls gereinigt werden.Variant b) can be used for the conversion of the amidic oxygen methods known in the thioamide are going on. For example, dissolves or suspends a compound of the formula Ia is inert under the reaction conditions Solvents such as benzene or toluene set after adding pyridine or picoline P255 and allows to react at room temperature up to 1500 C. From the reaction mixture The end product can be isolated and, if appropriate, by methods known per se getting cleaned.
Gegebenenfalls erhaltene Isomerengemische können nach an sich bekannten Methoden aufgetrennt werden.Any isomer mixtures obtained can be prepared in accordance with known per se Methods are separated.
Die Verbindungen der Formel 1 besitzen vorteilhafte chemotherapeutische Eigenschaften, insbesondere zeigen sie bei lokaler oder oraler Anwendung eine antimykotische Wirkung. Diese Wirkung konnte durch Untersuchungen in vitro unter Verwendung verschiedener Gattungen und Arten von Myceten sowie in vivo am experimentellen Hautmykose-Modell am Meerschweinchen nachgewiesen werden. Die orale Wirksamkeit wurde in vivo am Meerschweinchen-Trichophytie-Modell in einem Dosisbereich ab ca. 100 bis 300 mg/kg Körpergewicht nachgewiesen.The compounds of formula 1 have advantageous chemotherapeutic properties Properties, especially when applied locally or orally, show an antifungal Effect. This effect was confirmed by in vitro studies using various Genera and species of mycetes as well as in vivo on the experimental skin mycosis model can be detected in guinea pigs. Oral efficacy was assessed in vivo using the guinea pig trichophytosis model detected in a dose range from about 100 to 300 mg / kg body weight.
Die Ausgangsverbindungen sind bekannt oder nach bekannten Verfahren herstellbar.The starting compounds are known or by known processes manufacturable.
In den nachfolgenden Beispielen, die die Erfindung näher erläutern, ihren Umfang aber in keiner Weise einschränken sollen, erfolgen alle Temperaturangaben in Celsiusgraden.In the following examples, which explain the invention in more detail, but are not intended to limit their scope in any way, all temperature data are given in degrees Celsius.
Beispiel 1: N-Cinnamyl-N-methylnaphthelin-1-carbonsäureamid: 7,7 g N-Methylcinnamylamin werden in Pyridin gelöst und unter Eiskühlung 10 g 1-Naphthoylchlorid in Äther zugetropft. Es wird eine Stunde bei Raumtemperatur gerührt, mit 1 N HCI angesäuert und das Produkt mit Essigester extrahiert. Die organische Phase wird getrocknet, einrotiert und der Rückstand aus Cyclohexan umkristallisiert. Fp: 69 - 710 Beispiel 2: N-Cinnamyl-N-methylnaphthalin-1-thiocarbonsäureamid: 4 9 N-Cinnamyl-N-methylnaphthalin-1-carbonsäureamid werden in einer Mischung von Picolin und Toluol (3:2) gelöst, mit 12 g P2S5 portionsweise versetzt und 12 Stunden auf 700 erwärmt. Die Lösung wird von unlöslichem Material abdekantiert und mit verdünnter CH3COOH-Lösung und H2 0 gewaschen. Das Rohprodukt wird nach üblicher Aufarbeitung über Kieselgel chromatographiert (Laufmittel: CHCl3). Man erhält ein Öl.Example 1: N-cinnamyl-N-methylnaphthelin-1-carboxamide: 7.7 g N-methylcinnamylamine are dissolved in pyridine and, with ice-cooling, 10 g of 1-naphthoyl chloride added dropwise in ether. It is stirred for one hour at room temperature with 1 N HCl acidified and the product extracted with ethyl acetate. The organic phase will dried, concentrated using a rotary evaporator and the residue was recrystallized from cyclohexane. Fp: 69 - 710 Example 2: N-cinnamyl-N-methylnaphthalene-1-thiocarboxamide: 4 9 N-cinnamyl-N-methylnaphthalene-1-carboxamide are dissolved in a mixture of picoline and toluene (3: 2), with 12 g of P2S5 in portions added and heated to 700 for 12 hours. The solution is made of insoluble material decanted off and washed with dilute CH3COOH solution and H2 0. The raw product after the usual work-up, it is chromatographed over silica gel (mobile phase: CHCl3). An oil is obtained.
NMR (CDCl3): 7.2-8.2 (12H arom.); 5.8-6.9 (m, 2-olef, H); 5.1 (d, 1H); 4.02 (m, 1H); 3.7 (s, 1,5H); 2.95 (s, 15H).NMR (CDCl3): 7.2-8.2 (12H arom.); 5.8-6.9 (m, 2-olef, H); 5.1 (d, 1H); 4.02 (m. 1H); 3.7 (s, 1.5H); 2.95 (s, 15H).
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843405329 DE3405329A1 (en) | 1984-02-15 | 1984-02-15 | Novel allylamine derivatives, process for their preparation, and their use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843405329 DE3405329A1 (en) | 1984-02-15 | 1984-02-15 | Novel allylamine derivatives, process for their preparation, and their use |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3405329A1 true DE3405329A1 (en) | 1985-08-22 |
Family
ID=6227753
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843405329 Withdrawn DE3405329A1 (en) | 1984-02-15 | 1984-02-15 | Novel allylamine derivatives, process for their preparation, and their use |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE3405329A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5550162A (en) * | 1994-02-03 | 1996-08-27 | Synthelabo | N-(-3-aminopropyl)-N-phenyl-5,6,7,8-tetrahydro-naphthalene-2-carboxamide derivatives, their preparation and their therapeutic use |
-
1984
- 1984-02-15 DE DE19843405329 patent/DE3405329A1/en not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5550162A (en) * | 1994-02-03 | 1996-08-27 | Synthelabo | N-(-3-aminopropyl)-N-phenyl-5,6,7,8-tetrahydro-naphthalene-2-carboxamide derivatives, their preparation and their therapeutic use |
| US5663183A (en) * | 1994-02-03 | 1997-09-02 | Synthelabo | N-(3-Aminopropyl)-N-phenyl-5,6,7,8-tetrahydronaphthalene-2-carboxamide derivatives, their preparation and their therapeutic use |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH446289A (en) | Process for the preparation of alkene derivatives | |
| EP0043788B1 (en) | Imidazole derivatives, process for their preparation and their pharmaceutical compositions | |
| DE1670772A1 (en) | Process for the preparation of benzoxazine derivatives | |
| DE3147977A1 (en) | NEW ORGANIC COMPOUNDS, METHOD FOR THEIR PRODUCTION AND THEIR USE | |
| DE69911430T2 (en) | METHOD FOR PRODUCING 1- (1H) -BENZOQUINOLIZIN-3-ON DERIVATIVES | |
| CH642352A5 (en) | MALEINIMIDE AND SUCCINIMIDE DERIVATIVES, METHOD FOR PRODUCING THE SAME AND HERBICIDES CONTAINING THESE DERIVATIVES. | |
| DE2509260B2 (en) | a- (23,4,5,6-Penta-O-acetyI-D-gluconyl-thioureido) benzyl penicillin | |
| EP0350437B1 (en) | 3,4-Disubstituted phenyl-heterocycles and their use | |
| DE3405329A1 (en) | Novel allylamine derivatives, process for their preparation, and their use | |
| EP0008071B1 (en) | 1-iminomethylene-2-(phenoxy-alkyl)-2-imidazoline derivatives, their preparation, compositions containing them as active components and their application as pesticides | |
| DE3302814C2 (en) | ||
| EP0074121B1 (en) | 2,3,4,5-tetrahydro-1-benzoxepine-3,5-dione derivatives and process for their preparation | |
| EP0008565A1 (en) | Bis-(phenoxy-alkyl-2-imidazoline)-1,1'-sulfides, process for their preparation, agents containing these sulfides as active components, and their use in combating pesticides | |
| DE2713586A1 (en) | NEW ORGANIC COMPOUNDS, METHODS OF MANUFACTURING AND USING THEM | |
| DE69108195T3 (en) | Astaxanthin intermediates. | |
| DE1445739A1 (en) | Process for the production of thiol- or thionothiolphosphorus - (- phosphon -, - phosphine -) - acid esters | |
| DE3405332A1 (en) | Novel allylamines, process for their preparation, and their use | |
| DE1931061A1 (en) | Pyrazole compounds, processes for their preparation and their use | |
| DE3405330A1 (en) | Novel allylamines, process for their preparation, and their use | |
| CH651838A5 (en) | 5-SILYL-PENT-2-EN-4-INYL-1-AMINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE. | |
| DE3442529A1 (en) | Novel homopropargylamine derivatives, process for their preparation and their use | |
| AT379807B (en) | METHOD FOR PRODUCING NEW THIADIAZOLE DERIVATIVES | |
| AT313913B (en) | Process for the production of new 1.2.3-trithiane compounds and their salts | |
| CH637114A5 (en) | 2- (N-CARBOALKOXYAMINO) -BENZOPHENONE, THEIR PRODUCTION AND USE. | |
| AT225356B (en) | Process for the preparation of new thiocolchicine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |