DE2137276A1 - N-substituierte 1-aminomethylindane - Google Patents
N-substituierte 1-aminomethylindaneInfo
- Publication number
- DE2137276A1 DE2137276A1 DE2137276A DE2137276A DE2137276A1 DE 2137276 A1 DE2137276 A1 DE 2137276A1 DE 2137276 A DE2137276 A DE 2137276A DE 2137276 A DE2137276 A DE 2137276A DE 2137276 A1 DE2137276 A1 DE 2137276A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- hydrogen
- alkoxyl
- compound according
- cycloalkyl
- 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
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- QBHALBZXAXQBOY-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-ylmethanamine Chemical class C1=CC=C2C(CN)CCC2=C1 QBHALBZXAXQBOY-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 230000036772 blood pressure Effects 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 2
- 235000021190 leftovers Nutrition 0.000 claims 2
- 150000002825 nitriles Chemical class 0.000 claims 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- 238000006798 ring closing metathesis reaction Methods 0.000 claims 1
- 150000003335 secondary amines Chemical class 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 47
- -1 nitrogen 1-aminomethylindanes Chemical class 0.000 description 24
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- CMKDJMDGRSJZIS-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carbaldehyde Chemical compound C1=CC=C2C(C=O)CCC2=C1 CMKDJMDGRSJZIS-UHFFFAOYSA-N 0.000 description 7
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 150000002081 enamines Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- JUXVVEHQFXNKJN-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-ylmethyl)piperidine Chemical compound C1CC2=CC=CC=C2C1CN1CCCCC1 JUXVVEHQFXNKJN-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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 230000003276 anti-hypertensive effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- UYOFJPBVHUOLKL-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)-n-methylmethanamine Chemical compound C1=CC=C2C(CNC)CCC2=C1 UYOFJPBVHUOLKL-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000005194 fractionation Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- DZGMFITYAJIDHR-UHFFFAOYSA-N 2,3-dihydro-1h-indene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)CCC2=C1 DZGMFITYAJIDHR-UHFFFAOYSA-N 0.000 description 1
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
- NNWUEBIEOFQMSS-UHFFFAOYSA-N 2-Methylpiperidine Chemical compound CC1CCCCN1 NNWUEBIEOFQMSS-UHFFFAOYSA-N 0.000 description 1
- FWPFXBANOKKNBR-UHFFFAOYSA-N 2-[2-(cyanomethyl)phenyl]acetonitrile Chemical compound N#CCC1=CC=CC=C1CC#N FWPFXBANOKKNBR-UHFFFAOYSA-N 0.000 description 1
- HREMGZQEPGHZNC-UHFFFAOYSA-N 2-cycloheptylazepane Chemical compound C1CCCCCC1C1NCCCCC1 HREMGZQEPGHZNC-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
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- DSBOHBZVJVNQRR-UHFFFAOYSA-N 3-methylazepane Chemical compound CC1CCCCNC1 DSBOHBZVJVNQRR-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 241000009298 Trigla lyra Species 0.000 description 1
- 238000003833 Wallach reaction Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N benzocyclopentane Natural products C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 229910002090 carbon oxide Inorganic materials 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000003454 indenyl group Chemical class C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 210000004731 jugular vein Anatomy 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- KFWOBUUEKPGOBJ-UHFFFAOYSA-N n-(2,3-dihydro-1h-inden-1-ylmethyl)-n-propylpropan-1-amine Chemical compound C1=CC=C2C(CN(CCC)CCC)CCC2=C1 KFWOBUUEKPGOBJ-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- SWELZOZIOHGSPA-UHFFFAOYSA-N palladium silver Chemical compound [Pd].[Ag] SWELZOZIOHGSPA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000004804 winding Methods 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE786748D BE786748A (fr) | 1971-07-26 | 1-aminomethyl-indanes-n-substitues | |
| DE2137276A DE2137276A1 (de) | 1971-07-26 | 1971-07-26 | N-substituierte 1-aminomethylindane |
| NL7209802A NL7209802A (enExample) | 1971-07-26 | 1972-07-14 | |
| US273456A US3886168A (en) | 1971-07-26 | 1972-07-20 | N-substituted 1-aminomethylindanes |
| CH1092372A CH583169A5 (enExample) | 1971-07-26 | 1972-07-21 | |
| SE7209669A SE411755B (sv) | 1971-07-26 | 1972-07-24 | Forfarande for framstellning av n-substituerade 1-aminometylindaner |
| JP47073910A JPS5824433B1 (enExample) | 1971-07-26 | 1972-07-25 | |
| CA147,926A CA978184A (en) | 1971-07-26 | 1972-07-25 | N-substituted 1-aminomethylindanes |
| AT637972A AT316534B (de) | 1971-07-26 | 1972-07-25 | Verfahren zur Herstellung von neuen N-substituierten 1-Aminomethylindanen |
| GB3468972A GB1394859A (en) | 1971-07-26 | 1972-07-25 | N-substituted 1-aminomethylindans |
| FR7226884A FR2147209B1 (enExample) | 1971-07-26 | 1972-07-26 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2137276A DE2137276A1 (de) | 1971-07-26 | 1971-07-26 | N-substituierte 1-aminomethylindane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2137276A1 true DE2137276A1 (de) | 1973-02-08 |
Family
ID=5814830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2137276A Pending DE2137276A1 (de) | 1971-07-26 | 1971-07-26 | N-substituierte 1-aminomethylindane |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3886168A (enExample) |
| JP (1) | JPS5824433B1 (enExample) |
| AT (1) | AT316534B (enExample) |
| BE (1) | BE786748A (enExample) |
| CA (1) | CA978184A (enExample) |
| CH (1) | CH583169A5 (enExample) |
| DE (1) | DE2137276A1 (enExample) |
| FR (1) | FR2147209B1 (enExample) |
| GB (1) | GB1394859A (enExample) |
| NL (1) | NL7209802A (enExample) |
| SE (1) | SE411755B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000896A3 (en) * | 1977-08-19 | 1979-05-30 | Sandoz Ag | Propenyl amines, processes for their production and pharmaceutical compositions containing them |
| EP0325963A1 (en) * | 1988-01-15 | 1989-08-02 | Abbott Laboratories | 1-Aminomethyl-1,2,3,4-tetrahydronaphthalenes and -indanes |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4005093A (en) * | 1975-01-20 | 1977-01-25 | Sterling Drug Inc. | 2-Naphthyl-lower-alkylamines |
| US4130646A (en) * | 1975-07-25 | 1978-12-19 | E. R. Squibb & Sons, Inc. | 1,2,3,4-Tetrahydro-2-((4-(phenyl)-1-piperazinyl)methyl)-1-naphthalenols and derivatives and analogs thereof |
| JPS52133993A (en) * | 1976-04-29 | 1977-11-09 | Takeda Chem Ind Ltd | 1.2-dihydronaphthalene derivatives and method of preparing the same |
| US5334628A (en) * | 1984-06-09 | 1994-08-02 | Kaken Pharmaceutical Co., Ltd. | Amine derivatives, processes for preparing the same and fungicides containing the same |
| JPS6145A (ja) * | 1984-06-09 | 1986-01-06 | Kaken Pharmaceut Co Ltd | Ｎ‐（４‐ｔｅｒｔ‐ブチルベンジル）‐Ｎ‐メチル‐１‐ナフチルメチルアミンおよびそれを有効成分とする抗真菌剤 |
| GB8704572D0 (en) * | 1987-02-26 | 1987-04-01 | Lundbeck & Co As H | Organic compounds |
| EP0361577B1 (en) * | 1988-09-19 | 1993-05-05 | Akzo N.V. | Tetrahydronaphthalene and indane derivatives |
| WO1995018617A1 (en) * | 1994-01-10 | 1995-07-13 | Teva Pharmaceutical Industries Ltd. | 1-aminoindan derivatives and compositions thereof |
| US5914349A (en) | 1994-01-10 | 1999-06-22 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using 1-aminoindan and derivatives thereof and process for preparing optically active 1-aminoindan derivatives |
| PT966435E (pt) | 1996-12-18 | 2005-06-30 | Yissum Res Dev Co | Derivados aminoindano |
| US6737547B1 (en) | 1998-12-31 | 2004-05-18 | Teva Pharmaceutical Industries, Ltd. | Compositions containing and methods of using N-acyl-1H-aminoindenes |
| WO2001030339A1 (en) * | 1999-10-27 | 2001-05-03 | Teva Pharmaceutical Industries, Ltd. | Use of 1-aminoindan derivatives for treatment of mania in bipolar mood disorder |
| US20040010038A1 (en) * | 2002-02-27 | 2004-01-15 | Eran Blaugrund | Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors |
| US20070135518A1 (en) * | 2005-12-09 | 2007-06-14 | Marta Weinstock-Rosin | Use of low-dose ladostigil for neuroprotection |
| EP1956904B1 (en) * | 2005-12-09 | 2017-04-12 | Yissum Research Development Company of the Hebrew University of Jerusalem Ltd. | Low-dose ladostigil for the treatment of mild cognitive impairment |
| TW200744576A (en) * | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3706756A (en) * | 1969-02-03 | 1972-12-19 | Ciba Geigy Corp | Aminoalkyl-spirocycloalkanes |
| BE757408A (fr) * | 1969-10-13 | 1971-04-13 | Thomae Gmbh Dr K | Nouveaux butanols tertiaires a constituants basiques |
| US3704323A (en) * | 1969-12-23 | 1972-11-28 | Squibb & Sons Inc | Indane derivatives |
| US3725412A (en) * | 1969-12-29 | 1973-04-03 | Sandoz Ag | Substituted {60 ,{60 ,{65 -triphenyl-aminopropanols |
-
0
- BE BE786748D patent/BE786748A/xx unknown
-
1971
- 1971-07-26 DE DE2137276A patent/DE2137276A1/de active Pending
-
1972
- 1972-07-14 NL NL7209802A patent/NL7209802A/xx not_active Application Discontinuation
- 1972-07-20 US US273456A patent/US3886168A/en not_active Expired - Lifetime
- 1972-07-21 CH CH1092372A patent/CH583169A5/xx not_active IP Right Cessation
- 1972-07-24 SE SE7209669A patent/SE411755B/xx unknown
- 1972-07-25 CA CA147,926A patent/CA978184A/en not_active Expired
- 1972-07-25 AT AT637972A patent/AT316534B/de not_active IP Right Cessation
- 1972-07-25 GB GB3468972A patent/GB1394859A/en not_active Expired
- 1972-07-25 JP JP47073910A patent/JPS5824433B1/ja active Granted
- 1972-07-26 FR FR7226884A patent/FR2147209B1/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000896A3 (en) * | 1977-08-19 | 1979-05-30 | Sandoz Ag | Propenyl amines, processes for their production and pharmaceutical compositions containing them |
| EP0325963A1 (en) * | 1988-01-15 | 1989-08-02 | Abbott Laboratories | 1-Aminomethyl-1,2,3,4-tetrahydronaphthalenes and -indanes |
| EP0395734A4 (en) * | 1988-01-15 | 1991-01-02 | Abbott Laboratories | 1-aminomethyl-1,2,3,4-tetrahydronaphthalenes |
Also Published As
| Publication number | Publication date |
|---|---|
| SE411755B (sv) | 1980-02-04 |
| CA978184A (en) | 1975-11-18 |
| CH583169A5 (enExample) | 1976-12-31 |
| BE786748A (fr) | 1973-01-26 |
| US3886168A (en) | 1975-05-27 |
| GB1394859A (en) | 1975-05-21 |
| AT316534B (de) | 1974-07-10 |
| FR2147209B1 (enExample) | 1975-10-17 |
| NL7209802A (enExample) | 1973-01-30 |
| FR2147209A1 (enExample) | 1973-03-09 |
| JPS5824433B1 (enExample) | 1983-05-20 |
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| OHA | Expiration of time for request for examination |