IL91411A - 2-aza-4(alkoxycarbonyl)-spiro(4,5)decan-3-one and processes for the preparation thereof - Google Patents
2-aza-4(alkoxycarbonyl)-spiro(4,5)decan-3-one and processes for the preparation thereofInfo
- Publication number
- IL91411A IL91411A IL9141189A IL9141189A IL91411A IL 91411 A IL91411 A IL 91411A IL 9141189 A IL9141189 A IL 9141189A IL 9141189 A IL9141189 A IL 9141189A IL 91411 A IL91411 A IL 91411A
- Authority
- IL
- Israel
- Prior art keywords
- aza
- formula
- decan
- acid
- spiro
- Prior art date
Links
- XJLDYKIEURAVBW-UHFFFAOYSA-N 3-decanone Chemical compound CCCCCCCC(=O)CC XJLDYKIEURAVBW-UHFFFAOYSA-N 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 60
- -1 alkali metal cyanide Chemical class 0.000 claims description 28
- 239000002253 acid Substances 0.000 claims description 19
- 229910052783 alkali metal Inorganic materials 0.000 claims description 18
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- GDJJXPHLLWAAFG-UHFFFAOYSA-N 2-(1-cyanocyclohexyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)C1(C#N)CCCCC1 GDJJXPHLLWAAFG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 229960002870 gabapentin Drugs 0.000 claims description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 claims description 3
- CDTSTGVGQBWKSI-UHFFFAOYSA-N methyl 3-oxo-2-azaspiro[4.5]decane-4-carboxylate Chemical compound COC(=O)C1C(=O)NCC11CCCCC1 CDTSTGVGQBWKSI-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 claims description 2
- SHQXEMUIENEWNG-UHFFFAOYSA-N ethyl 3-oxo-2-azaspiro[4.5]decane-4-carboxylate Chemical compound CCOC(=O)C1C(=O)NCC11CCCCC1 SHQXEMUIENEWNG-UHFFFAOYSA-N 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000007858 starting material Substances 0.000 description 9
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- VXAPUDWUMVBMHO-UHFFFAOYSA-N ethyl 2-cyano-2-(1-cyanocyclohexyl)acetate Chemical compound CCOC(=O)C(C#N)C1(C#N)CCCCC1 VXAPUDWUMVBMHO-UHFFFAOYSA-N 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 101150041968 CDC13 gene Proteins 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 3
- 239000007868 Raney catalyst Substances 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000001103 potassium chloride Substances 0.000 description 3
- 235000011164 potassium chloride Nutrition 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000001117 sulphuric acid Substances 0.000 description 3
- 235000011149 sulphuric acid Nutrition 0.000 description 3
- 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- CGWVBPMMLKULCR-UHFFFAOYSA-N acetic acid;cyclohexylmethanamine Chemical compound CC(O)=O.NCC1CCCCC1 CGWVBPMMLKULCR-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- RVQLJKLQQYFQSS-UHFFFAOYSA-N diethyl 2-(1-cyanocyclohexyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1(C#N)CCCCC1 RVQLJKLQQYFQSS-UHFFFAOYSA-N 0.000 description 2
- LXTCZMBVTOVRFJ-UHFFFAOYSA-N dimethyl 2-cyclohexylidenepropanedioate Chemical compound COC(=O)C(C(=O)OC)=C1CCCCC1 LXTCZMBVTOVRFJ-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- PZAJJZJKRVXKCS-UHFFFAOYSA-N ethyl 2-cyano-2-cyclohexylideneacetate Chemical compound CCOC(=O)C(C#N)=C1CCCCC1 PZAJJZJKRVXKCS-UHFFFAOYSA-N 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000011707 mineral Chemical class 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229940090181 propyl acetate Drugs 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- XBUDZAQEMFGLEU-UHFFFAOYSA-N 2-[1-(aminomethyl)cyclohexyl]acetic acid;hydron;chloride Chemical compound Cl.OC(=O)CC1(CN)CCCCC1 XBUDZAQEMFGLEU-UHFFFAOYSA-N 0.000 description 1
- MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical group [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 1
- SFTWDKIBFALMMG-UHFFFAOYSA-N 2-cyclohexylidene-3-ethoxy-3-oxopropanoic acid Chemical compound CCOC(=O)C(C(O)=O)=C1CCCCC1 SFTWDKIBFALMMG-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- NYQDCVLCJXRDSK-UHFFFAOYSA-N Bromofos Chemical compound COP(=S)(OC)OC1=CC(Cl)=C(Br)C=C1Cl NYQDCVLCJXRDSK-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 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 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 1
- MDNMCAOGOPOUTP-UHFFFAOYSA-N diethyl 2-cyclohexylidenepropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)=C1CCCCC1 MDNMCAOGOPOUTP-UHFFFAOYSA-N 0.000 description 1
- PVEIHNIYJYCWCP-UHFFFAOYSA-N dimethyl 2-(1-cyanocyclohexyl)propanedioate Chemical compound COC(=O)C(C(=O)OC)C1(C#N)CCCCC1 PVEIHNIYJYCWCP-UHFFFAOYSA-N 0.000 description 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 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
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- DJHRXBYWKVQDJY-UHFFFAOYSA-N spiro[4.5]decan-3-one Chemical class C1C(=O)CCC21CCCCC2 DJHRXBYWKVQDJY-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/28—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and containing rings
-
- 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
- C07D209/54—Spiro-condensed
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL10675889A IL106758A (en) | 1988-09-01 | 1989-08-24 | (1-cyanocyclohexyl)-malonic acid dialkyl esters and processes for their preparation |
| IL106758A IL106758A0 (en) | 1988-09-01 | 1993-08-22 | (1-cyanocyclohexyl)-malonic acid dialkyl esters and processes for their preparation |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH327288 | 1988-09-01 | ||
| CH138389 | 1989-04-12 | ||
| CH138289 | 1989-04-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL91411A0 IL91411A0 (en) | 1990-04-29 |
| IL91411A true IL91411A (en) | 1994-07-31 |
Family
ID=27172939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9141189A IL91411A (en) | 1988-09-01 | 1989-08-24 | 2-aza-4(alkoxycarbonyl)-spiro(4,5)decan-3-one and processes for the preparation thereof |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US4956473A (da) |
| EP (1) | EP0358092B1 (da) |
| JP (1) | JPH02115165A (da) |
| CA (1) | CA1337769C (da) |
| DE (1) | DE58900561D1 (da) |
| DK (2) | DK170974B1 (da) |
| ES (1) | ES2027057T3 (da) |
| FI (1) | FI90862C (da) |
| IL (1) | IL91411A (da) |
| NO (1) | NO173497C (da) |
| PT (1) | PT91612B (da) |
| YU (1) | YU162789A (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3928184A1 (de) * | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von cyclischen aminosaeurederivaten sowie zwischenprodukte |
| PH27359A (en) * | 1989-08-25 | 1993-06-21 | Warner Lambert Co | Process for cyclic amino acid anticonvulsant compounds |
| US5149870A (en) * | 1989-11-16 | 1992-09-22 | Lonza Ltd. | Process for the production of 1-(aminomethyl)cyclohexane acetic acid |
| US5136091A (en) * | 1989-11-16 | 1992-08-04 | Lonza Ltd. | Process for the production of 1-(aminomethyl) cyclohexane acetic acid |
| FI905584A7 (fi) * | 1989-11-16 | 1991-05-17 | Lonza Ag | Menetelmä 1-(aminometyyli)sykloheksaanietikkahapon valmistamiseksi |
| SK283295B6 (sk) * | 1996-03-14 | 2003-05-02 | Warner-Lambert Company | Substituovaná cyklická aminokyselina, jej použitie a farmaceutický prostriedok na jej báze |
| US6372792B1 (en) | 1996-04-26 | 2002-04-16 | Guy Chouinard | Method for treating anxiety, anxiety disorders and insomnia |
| USD386310S (en) * | 1996-10-08 | 1997-11-18 | Nepsco, Inc. | Shoulder carrying strap |
| US6294690B1 (en) | 1997-10-07 | 2001-09-25 | Warner-Lambert Company | Process for preparing a cyclic amino acid anticonvulsant compound |
| US20050148792A1 (en) * | 2004-01-02 | 2005-07-07 | Damodaragounder Gopal | Process for the preparation of gabapentin |
| US20050187295A1 (en) * | 2004-02-19 | 2005-08-25 | Surendra Kalyan | Processes for the preparation of gabapentin |
| CA2660769C (en) * | 2006-06-30 | 2013-12-03 | Zach System S.P.A. | Process for preparing gabapentin |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1350582A (en) * | 1970-07-24 | 1974-04-18 | Ucb Sa | Cerivatives of 2-pyrrolidinone |
| GB1415338A (en) * | 1971-12-16 | 1975-11-26 | American Home Prod | Amino acids and derivatives thereof |
| GB1385846A (en) * | 1973-05-18 | 1975-03-05 | Le G Venny Ped I Im A I Gertse | Chlorohydrate of beta-phenyl-ypsilon-amino butyric acid and process for producing same |
| DE2460891C2 (de) * | 1974-12-21 | 1982-09-23 | Gödecke AG, 1000 Berlin | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE2541855A1 (de) * | 1975-09-18 | 1977-03-31 | Schering Ag | 4-(polyalkoxy-phenyl)-2-pyrrolidone ii |
| DE2611690A1 (de) * | 1976-03-19 | 1977-09-22 | Goedecke Ag | Cyclische sulfonyloxyimide |
| DE3631414A1 (de) * | 1986-09-16 | 1988-03-24 | Basf Ag | Verfahren zur herstellung von (alpha)-pyrrolidonen, deren verwendung und neue (alpha)-pyrrolidone |
| JP2807277B2 (ja) * | 1988-08-31 | 1998-10-08 | 第一製薬株式会社 | スピロ化合物 |
-
1989
- 1989-08-21 YU YU01627/89A patent/YU162789A/xx unknown
- 1989-08-24 IL IL9141189A patent/IL91411A/en not_active IP Right Cessation
- 1989-08-28 JP JP1221377A patent/JPH02115165A/ja active Pending
- 1989-08-29 DE DE8989115938T patent/DE58900561D1/de not_active Expired - Lifetime
- 1989-08-29 ES ES198989115938T patent/ES2027057T3/es not_active Expired - Lifetime
- 1989-08-29 CA CA000609741A patent/CA1337769C/en not_active Expired - Fee Related
- 1989-08-29 EP EP89115938A patent/EP0358092B1/de not_active Expired - Lifetime
- 1989-08-30 US US07/400,820 patent/US4956473A/en not_active Expired - Fee Related
- 1989-08-31 DK DK430689A patent/DK170974B1/da not_active Application Discontinuation
- 1989-08-31 NO NO893491A patent/NO173497C/no unknown
- 1989-09-01 PT PT91612A patent/PT91612B/pt not_active IP Right Cessation
- 1989-09-01 FI FI894121A patent/FI90862C/fi not_active IP Right Cessation
-
1990
- 1990-01-08 US US07/461,973 patent/US4958044A/en not_active Expired - Fee Related
-
1995
- 1995-01-11 DK DK003095A patent/DK170929B1/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES2027057T3 (es) | 1992-05-16 |
| DK430689D0 (da) | 1989-08-31 |
| FI894121L (fi) | 1990-03-02 |
| JPH02115165A (ja) | 1990-04-27 |
| NO173497C (no) | 1993-12-22 |
| PT91612A (pt) | 1990-03-30 |
| EP0358092B1 (de) | 1991-12-11 |
| IL91411A0 (en) | 1990-04-29 |
| DK430689A (da) | 1990-03-02 |
| FI90862B (fi) | 1993-12-31 |
| US4958044A (en) | 1990-09-18 |
| US4956473A (en) | 1990-09-11 |
| YU162789A (en) | 1990-12-31 |
| DE58900561D1 (de) | 1992-01-23 |
| NO173497B (no) | 1993-09-13 |
| EP0358092A1 (de) | 1990-03-14 |
| CA1337769C (en) | 1995-12-19 |
| FI90862C (fi) | 1994-04-11 |
| DK170974B1 (da) | 1996-04-09 |
| DK3095A (da) | 1995-01-11 |
| NO893491L (no) | 1990-03-02 |
| DK170929B1 (da) | 1996-03-18 |
| FI894121A0 (fi) | 1989-09-01 |
| PT91612B (pt) | 1995-05-31 |
| NO893491D0 (no) | 1989-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |