DE2246728A1 - Neue substituierte aethylendiamine, verfahren zu ihrer herstellung und solche diamine enthaltende arzneipraeparate - Google Patents
Neue substituierte aethylendiamine, verfahren zu ihrer herstellung und solche diamine enthaltende arzneipraeparateInfo
- Publication number
- DE2246728A1 DE2246728A1 DE19722246728 DE2246728A DE2246728A1 DE 2246728 A1 DE2246728 A1 DE 2246728A1 DE 19722246728 DE19722246728 DE 19722246728 DE 2246728 A DE2246728 A DE 2246728A DE 2246728 A1 DE2246728 A1 DE 2246728A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- methyl
- hydrogen
- groups
- solution
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 66
- 238000002360 preparation method Methods 0.000 title claims description 55
- 238000000034 method Methods 0.000 title claims description 9
- 150000004985 diamines Chemical class 0.000 title description 3
- 229940066765 systemic antihistamines substituted ethylene diamines Drugs 0.000 title description 3
- -1 alkyl radical Chemical class 0.000 claims description 107
- 150000001875 compounds Chemical class 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 53
- 239000001257 hydrogen Substances 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000007788 liquid Substances 0.000 claims description 30
- 125000002252 acyl group Chemical group 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 150000001412 amines Chemical class 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 125000005219 aminonitrile group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 150000002466 imines Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
- 150000003141 primary amines Chemical class 0.000 claims description 5
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000005840 aryl radicals Chemical class 0.000 claims description 3
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000005936 piperidyl group Chemical group 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000002775 capsule Substances 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 claims 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 claims 1
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 1
- 210000004081 cilia Anatomy 0.000 claims 1
- 238000009826 distribution Methods 0.000 claims 1
- 210000003608 fece Anatomy 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 316
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 266
- 239000000243 solution Substances 0.000 description 175
- 239000000203 mixture Substances 0.000 description 133
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 108
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 105
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 62
- 239000003921 oil Substances 0.000 description 62
- 235000019198 oils Nutrition 0.000 description 62
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- 239000000725 suspension Substances 0.000 description 43
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 42
- 239000013078 crystal Substances 0.000 description 38
- 239000012280 lithium aluminium hydride Substances 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000011734 sodium Substances 0.000 description 33
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 32
- 238000001816 cooling Methods 0.000 description 25
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 24
- 239000003208 petroleum Substances 0.000 description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 21
- 238000001953 recrystallisation Methods 0.000 description 21
- 238000010992 reflux Methods 0.000 description 20
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 19
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 16
- 239000012230 colorless oil Substances 0.000 description 16
- 150000002431 hydrogen Chemical class 0.000 description 15
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 15
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000002026 chloroform extract Substances 0.000 description 14
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 14
- 239000012259 ether extract Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000012265 solid product Substances 0.000 description 12
- 235000019253 formic acid Nutrition 0.000 description 11
- 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 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 238000000354 decomposition reaction Methods 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- 239000005457 ice water Substances 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- SNIABFMMCKVXSY-UHFFFAOYSA-N benzoylazanium;chloride Chemical compound Cl.NC(=O)C1=CC=CC=C1 SNIABFMMCKVXSY-UHFFFAOYSA-N 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VTXNOVCTHUBABW-UHFFFAOYSA-N 3,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C(Cl)=C1 VTXNOVCTHUBABW-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000011049 filling Methods 0.000 description 5
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 5
- 235000006408 oxalic acid Nutrition 0.000 description 5
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- TYMAJBZHTKCAJJ-UHFFFAOYSA-N 1-(aminomethyl)-n,n-dimethylcyclohexan-1-amine Chemical compound CN(C)C1(CN)CCCCC1 TYMAJBZHTKCAJJ-UHFFFAOYSA-N 0.000 description 4
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 description 4
- WXZYJVGQZNZIRC-UHFFFAOYSA-N 2-n,2-n,2-trimethylpropane-1,2-diamine;dihydrochloride Chemical compound Cl.Cl.CN(C)C(C)(C)CN WXZYJVGQZNZIRC-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 4
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
- 229910052740 iodine Inorganic materials 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- OPSUSMMZNXNXKD-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropanamide Chemical compound CN(C)C(C)(C)C(N)=O OPSUSMMZNXNXKD-UHFFFAOYSA-N 0.000 description 3
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910003480 inorganic solid Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 description 3
- MUEYPOABQOGIKY-UHFFFAOYSA-N 2-(dimethylamino)-2-methylhexanenitrile Chemical compound CCCCC(C)(C#N)N(C)C MUEYPOABQOGIKY-UHFFFAOYSA-N 0.000 description 2
- RIDGSEGTBIWFTK-UHFFFAOYSA-N 2-(dimethylamino)-2-methylpropanenitrile Chemical compound CN(C)C(C)(C)C#N RIDGSEGTBIWFTK-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- NKQVYJRZBVRXRU-UHFFFAOYSA-N 2-methyl-2-(methylamino)propanenitrile Chemical compound CNC(C)(C)C#N NKQVYJRZBVRXRU-UHFFFAOYSA-N 0.000 description 2
- SSORUHAKVDLSAD-UHFFFAOYSA-N 2-methyl-2-n-(2-phenylethyl)propane-1,2-diamine Chemical compound NCC(C)(C)NCCC1=CC=CC=C1 SSORUHAKVDLSAD-UHFFFAOYSA-N 0.000 description 2
- KDYNEXUMMFHRKY-UHFFFAOYSA-N 2-n,2-n,2-trimethylhexane-1,2-diamine Chemical compound CCCCC(C)(CN)N(C)C KDYNEXUMMFHRKY-UHFFFAOYSA-N 0.000 description 2
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- JVUTULSYUBFRCR-UHFFFAOYSA-N [1-(4-methylpiperazin-1-yl)cyclohexyl]methanamine Chemical compound C1CN(C)CCN1C1(CN)CCCCC1 JVUTULSYUBFRCR-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 2
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 2
- 239000003637 basic solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000022244 formylation Effects 0.000 description 2
- 238000006170 formylation reaction Methods 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
- MUEHXYATBXJVCP-UHFFFAOYSA-N n-[2-[cyclohexyl(methyl)amino]ethyl]acetamide Chemical compound CC(=O)NCCN(C)C1CCCCC1 MUEHXYATBXJVCP-UHFFFAOYSA-N 0.000 description 2
- XBRUOBNCHXVHQM-UHFFFAOYSA-N n-[[1-(dimethylamino)cyclohexyl]methyl]-n-methylformamide Chemical compound O=CN(C)CC1(N(C)C)CCCCC1 XBRUOBNCHXVHQM-UHFFFAOYSA-N 0.000 description 2
- CICWYTSNYPMNIL-UHFFFAOYSA-N n-[[cyclohexylmethyl(methyl)amino]methyl]formamide Chemical compound O=CNCN(C)CC1CCCCC1 CICWYTSNYPMNIL-UHFFFAOYSA-N 0.000 description 2
- GVWISOJSERXQBM-UHFFFAOYSA-N n-methylpropan-1-amine Chemical compound CCCNC GVWISOJSERXQBM-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
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- 241000009298 Trigla lyra Species 0.000 description 1
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- 125000003545 alkoxy group Chemical group 0.000 description 1
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- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 150000004645 aluminates Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
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- 239000012298 atmosphere Substances 0.000 description 1
- 230000002238 attenuated effect Effects 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- ZUDYPQRUOYEARG-UHFFFAOYSA-L barium(2+);dihydroxide;octahydrate Chemical compound O.O.O.O.O.O.O.O.[OH-].[OH-].[Ba+2] ZUDYPQRUOYEARG-UHFFFAOYSA-L 0.000 description 1
- CECGBBNIUDXSHK-UHFFFAOYSA-N benzamide;oxalic acid Chemical compound OC(=O)C(O)=O.NC(=O)C1=CC=CC=C1 CECGBBNIUDXSHK-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- REJPDMLLCDXIOV-UHFFFAOYSA-N but-2-ynal Chemical compound CC#CC=O REJPDMLLCDXIOV-UHFFFAOYSA-N 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Chemical group 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- PNZXMIKHJXIPEK-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1CCCCC1 PNZXMIKHJXIPEK-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940096118 ella Drugs 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- CHVWXAHWVABFQG-UHFFFAOYSA-N ethyl carbamate;hydrochloride Chemical compound Cl.CCOC(N)=O CHVWXAHWVABFQG-UHFFFAOYSA-N 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 1
- 150000002171 ethylene diamines Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 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
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
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- 229910021432 inorganic complex Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 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
- 210000005053 lamin Anatomy 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- OETHQSJEHLVLGH-UHFFFAOYSA-N metformin hydrochloride Chemical compound Cl.CN(C)C(=N)N=C(N)N OETHQSJEHLVLGH-UHFFFAOYSA-N 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- APHIKOCDGDGHIL-UHFFFAOYSA-N n'-cyclohexyl-n,n'-dimethylethane-1,2-diamine Chemical compound CNCCN(C)C1CCCCC1 APHIKOCDGDGHIL-UHFFFAOYSA-N 0.000 description 1
- ZZPSWDZXWOPXGB-UHFFFAOYSA-N n,3-dimethylbut-2-en-1-amine Chemical class CNCC=C(C)C ZZPSWDZXWOPXGB-UHFFFAOYSA-N 0.000 description 1
- RPPOBIUFOBIWBN-UHFFFAOYSA-N n,n,1,2-tetramethylcyclohexan-1-amine Chemical compound CC1CCCCC1(C)N(C)C RPPOBIUFOBIWBN-UHFFFAOYSA-N 0.000 description 1
- PXHKDIOGWIBMLD-UHFFFAOYSA-N n-(2,3-dichloro-6-methylphenyl)-1-(dimethylamino)cyclohexane-1-carboxamide;hydrochloride Chemical compound Cl.CC=1C=CC(Cl)=C(Cl)C=1NC(=O)C1(N(C)C)CCCCC1 PXHKDIOGWIBMLD-UHFFFAOYSA-N 0.000 description 1
- XCVNDBIXFPGMIW-UHFFFAOYSA-N n-ethylpropan-1-amine Chemical compound CCCNCC XCVNDBIXFPGMIW-UHFFFAOYSA-N 0.000 description 1
- YVTRGSINXCANDK-UHFFFAOYSA-N n-methyl-1-(1-piperidin-1-ylcyclohexyl)methanamine Chemical compound C1CCCCN1C1(CNC)CCCCC1 YVTRGSINXCANDK-UHFFFAOYSA-N 0.000 description 1
- HHGZTIZUMKCUGM-UHFFFAOYSA-N n-methyl-1-[1-(4-methylpiperazin-1-yl)cyclohexyl]methanamine Chemical compound C1CN(C)CCN1C1(CNC)CCCCC1 HHGZTIZUMKCUGM-UHFFFAOYSA-N 0.000 description 1
- UUMDXVAJBXUBAV-UHFFFAOYSA-N n-methyl-n-[(1-piperidin-1-ylcyclohexyl)methyl]formamide Chemical compound C1CCCCN1C1(CN(C)C=O)CCCCC1 UUMDXVAJBXUBAV-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- OHEDMAIVEXQCOZ-UHFFFAOYSA-N piperidine;dihydrochloride Chemical compound Cl.Cl.C1CCNCC1 OHEDMAIVEXQCOZ-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/20—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by nitrogen atoms not being part of nitro or nitroso groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB756771A GB1410011A (en) | 1971-09-23 | 1971-09-23 | Ethylene diamine derivatives |
| GB2624872 | 1972-06-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2246728A1 true DE2246728A1 (de) | 1973-05-03 |
Family
ID=26241518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722246728 Pending DE2246728A1 (de) | 1971-09-23 | 1972-09-22 | Neue substituierte aethylendiamine, verfahren zu ihrer herstellung und solche diamine enthaltende arzneipraeparate |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS4839409A (enrdf_load_stackoverflow) |
| BE (1) | BE789025A (enrdf_load_stackoverflow) |
| CA (1) | CA995220A (enrdf_load_stackoverflow) |
| CH (1) | CH597153A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2246728A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2154559B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1410011A (enrdf_load_stackoverflow) |
| IL (1) | IL40397A (enrdf_load_stackoverflow) |
| NL (1) | NL7212967A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999031075A1 (en) * | 1997-12-16 | 1999-06-24 | Warner-Lambert Company | 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5319654B2 (enrdf_load_stackoverflow) | 1974-03-14 | 1978-06-22 | ||
| JPS5547977Y2 (enrdf_load_stackoverflow) * | 1975-07-18 | 1980-11-10 | ||
| JPS5253328A (en) * | 1975-10-27 | 1977-04-28 | Mazda Motor Corp | Engine rotation control of car having power steering |
| JPH0723348B2 (ja) * | 1986-08-27 | 1995-03-15 | 花王株式会社 | 新規なアシル化エチレンジアミン誘導体とその製造方法および用途 |
| PE20061156A1 (es) | 2004-12-23 | 2006-12-16 | Glaxo Group Ltd | Derivados de benzamida como agentes inhibidores del transportador de glicina |
| JP2008525398A (ja) * | 2004-12-23 | 2008-07-17 | グラクソ グループ リミテッド | グリシン輸送阻害剤 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2692265A (en) * | 1951-01-23 | 1954-10-19 | American Home Prod | Substituted glycinamides |
| US2993068A (en) * | 1958-07-01 | 1961-07-18 | Ethicon Inc | 1-aminomethyl-1-aminocyclohexanes |
| CH397684A (fr) * | 1961-05-02 | 1965-08-31 | Kuhlmann Ets | Procédé de la préparation de la pyrrolidide de l'acide triméthoxy-3',4',5' benzoylamino-acétique |
| US3258489A (en) * | 1963-06-14 | 1966-06-28 | Monsanto Co | N-(1-aminocyclohexylmethyl)anilines and n-(1-nitrocyclohexylmethyl)an-ilines |
| GB1058002A (en) * | 1964-07-07 | 1967-02-08 | Farmochimica Cutolo Calosi S P | Aryl-amino-acylamides |
| SE337810B (enrdf_load_stackoverflow) * | 1966-05-13 | 1971-08-23 | Tanabe Seiyaku Co | |
| AT273969B (de) * | 1966-08-01 | 1969-09-10 | Miles Lab | Verfahren zur Herstellung von neuen N-Aminoalkyl-N-benzylamiden und ihrer Salze |
| US3510492A (en) * | 1968-05-13 | 1970-05-05 | Upjohn Co | 2-anilino and 2-anilinomethyl cycloalkylamines |
-
0
- BE BE789025D patent/BE789025A/xx unknown
-
1971
- 1971-09-23 GB GB756771A patent/GB1410011A/en not_active Expired
-
1972
- 1972-09-15 CA CA152,009A patent/CA995220A/en not_active Expired
- 1972-09-20 IL IL40397A patent/IL40397A/en unknown
- 1972-09-21 JP JP47095039A patent/JPS4839409A/ja active Pending
- 1972-09-22 CH CH1388472A patent/CH597153A5/xx not_active IP Right Cessation
- 1972-09-22 FR FR7233698A patent/FR2154559B1/fr not_active Expired
- 1972-09-22 DE DE19722246728 patent/DE2246728A1/de active Pending
- 1972-09-25 NL NL7212967A patent/NL7212967A/xx not_active Application Discontinuation
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999031075A1 (en) * | 1997-12-16 | 1999-06-24 | Warner-Lambert Company | 1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
| EP1475371A1 (en) * | 1997-12-16 | 2004-11-10 | Warner-Lambert Company LLC | 1-substituted-1-aminomethyl-cycloalkane derivatives (= gabapentin analogues), their preparation and their use in the treatment of neurological disorders |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2154559A1 (enrdf_load_stackoverflow) | 1973-05-11 |
| CA995220A (en) | 1976-08-17 |
| NL7212967A (enrdf_load_stackoverflow) | 1973-03-27 |
| JPS4839409A (enrdf_load_stackoverflow) | 1973-06-09 |
| BE789025A (fr) | 1973-03-20 |
| CH597153A5 (enrdf_load_stackoverflow) | 1978-03-31 |
| GB1410011A (en) | 1975-10-15 |
| FR2154559B1 (enrdf_load_stackoverflow) | 1976-08-20 |
| IL40397A (en) | 1977-06-30 |
| IL40397A0 (en) | 1972-11-28 |
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| OHA | Expiration of time for request for examination |