DE2460891C2 - 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel - Google Patents
1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende ArzneimittelInfo
- Publication number
- DE2460891C2 DE2460891C2 DE2460891A DE2460891A DE2460891C2 DE 2460891 C2 DE2460891 C2 DE 2460891C2 DE 2460891 A DE2460891 A DE 2460891A DE 2460891 A DE2460891 A DE 2460891A DE 2460891 C2 DE2460891 C2 DE 2460891C2
- Authority
- DE
- Germany
- Prior art keywords
- aminomethyl
- acid
- acids
- general formula
- 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.)
- Expired
Links
- 239000002253 acid Substances 0.000 title claims description 18
- 150000007513 acids Chemical class 0.000 title claims description 10
- 150000002148 esters Chemical class 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 title description 22
- 238000000034 method Methods 0.000 title description 9
- 238000002360 preparation method Methods 0.000 title description 5
- 239000003814 drug Substances 0.000 title description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 239000000243 solution Substances 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 150000003839 salts Chemical class 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 150000001413 amino acids Chemical class 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 9
- -1 quaternary ammonium ions Chemical class 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 230000015556 catabolic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000006731 degradation reaction Methods 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- MXNASYICBPHSLF-UHFFFAOYSA-N 2-[1-(aminomethyl)cycloheptyl]acetic acid Chemical compound OC(=O)CC1(CN)CCCCCC1 MXNASYICBPHSLF-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 150000001540 azides Chemical class 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 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 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- 208000007101 Muscle Cramp Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- NIJJYAXOARWZEE-UHFFFAOYSA-N di-n-propyl-acetic acid Natural products CCCC(C(O)=O)CCC NIJJYAXOARWZEE-UHFFFAOYSA-N 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000001681 protective effect Effects 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- MSRILKIQRXUYCT-UHFFFAOYSA-M valproate semisodium Chemical compound [Na+].CCCC(C(O)=O)CCC.CCCC(C([O-])=O)CCC MSRILKIQRXUYCT-UHFFFAOYSA-M 0.000 description 3
- 229960000604 valproic acid Drugs 0.000 description 3
- MXOVZDDZXRYXLR-UHFFFAOYSA-N 2-[1-(2-methoxy-2-oxoethyl)cycloheptyl]acetic acid Chemical compound COC(=O)CC1(CC(O)=O)CCCCCC1 MXOVZDDZXRYXLR-UHFFFAOYSA-N 0.000 description 2
- VLFQWYHVTAGEQB-UHFFFAOYSA-N 2-[1-(2-methoxy-2-oxoethyl)cyclohexyl]acetic acid Chemical compound COC(=O)CC1(CC(O)=O)CCCCC1 VLFQWYHVTAGEQB-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 208000005392 Spasm Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 206010015037 epilepsy Diseases 0.000 description 2
- PQCNPWAMVMHDID-UHFFFAOYSA-N ethyl 2-[1-(aminomethyl)cyclohexyl]acetate Chemical compound CCOC(=O)CC1(CN)CCCCC1 PQCNPWAMVMHDID-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229920006158 high molecular weight polymer Polymers 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- SYKKFHNKTXXXCK-UHFFFAOYSA-N methyl 2-[1-(aminomethyl)cyclohexyl]acetate Chemical compound COC(=O)CC1(CN)CCCCC1 SYKKFHNKTXXXCK-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- 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
- TWQMSFCQNQMTPK-UHFFFAOYSA-N 2-[1-(aminomethyl)cyclopentyl]acetic acid;hydrochloride Chemical compound Cl.OC(=O)CC1(CN)CCCC1 TWQMSFCQNQMTPK-UHFFFAOYSA-N 0.000 description 1
- FWPVKDFOUXHOKQ-UHFFFAOYSA-N 2-[1-(carboxymethyl)cyclopentyl]acetic acid Chemical compound OC(=O)CC1(CC(O)=O)CCCC1 FWPVKDFOUXHOKQ-UHFFFAOYSA-N 0.000 description 1
- CGSIJCLRVFEHNY-UHFFFAOYSA-N 3-oxaspiro[5.6]dodecane-2,4-dione Chemical compound C1C(=O)OC(=O)CC21CCCCCC2 CGSIJCLRVFEHNY-UHFFFAOYSA-N 0.000 description 1
- GFWLMILMVMCJDI-UHFFFAOYSA-N 8-oxaspiro[4.5]decane-7,9-dione Chemical compound C1C(=O)OC(=O)CC11CCCC1 GFWLMILMVMCJDI-UHFFFAOYSA-N 0.000 description 1
- 229920001817 Agar Polymers 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000018152 Cerebral disease Diseases 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-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
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- GAIALLDIJVEQQA-UHFFFAOYSA-M NCC1(CCCCCC1)CC(=O)[O-].[Na+] Chemical compound NCC1(CCCCCC1)CC(=O)[O-].[Na+] GAIALLDIJVEQQA-UHFFFAOYSA-M 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 235000010419 agar Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- HJQOMCVHLXVRAK-UHFFFAOYSA-N butyl 2-[1-(aminomethyl)cycloheptyl]acetate Chemical compound CCCCOC(=O)CC1(CN)CCCCCC1 HJQOMCVHLXVRAK-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 229960001484 edetic acid Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- NJSUFZNXBBXAAC-UHFFFAOYSA-N ethanol;toluene Chemical compound CCO.CC1=CC=CC=C1 NJSUFZNXBBXAAC-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 230000000873 masking effect Effects 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2460891A DE2460891C2 (de) | 1974-12-21 | 1974-12-21 | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
| DE19752543821 DE2543821C2 (de) | 1974-12-21 | 1975-10-01 | Bestimmte Salze und Ester von 1-Aminomethyl-1-cycloalkanessigsäuren und diese Verbindungen enthaltende Arzneimittel |
| MX584775U MX4691E (es) | 1974-12-21 | 1975-12-11 | Procedimiento para la preparacion de aminoacidos ciclicos |
| MX584675U MX4721E (es) | 1974-12-21 | 1975-12-11 | Procedimiento para la preparacion de aminoacidos ciclicos |
| GB5119375A GB1465229A (en) | 1974-12-21 | 1975-12-15 | Cyclic amino acids |
| IE2736/75A IE42382B1 (en) | 1974-12-21 | 1975-12-15 | Cyclic amino acids |
| CH1645175A CH612664A5 (ref) | 1974-12-21 | 1975-12-18 | |
| FR7538818A FR2294697A1 (fr) | 1974-12-21 | 1975-12-18 | Nouveaux acides amino cycliques |
| CH430778A CH612665A5 (ref) | 1974-12-21 | 1975-12-18 | |
| CH430878A CH612666A5 (ref) | 1974-12-21 | 1975-12-18 | |
| BE6045299A BE836835A (fr) | 1974-12-21 | 1975-12-18 | Nouveaux acides amino cycliques |
| CA242,147A CA1052811A (en) | 1974-12-21 | 1975-12-19 | Cyclic amino-acids |
| SE7514442A SE423385B (sv) | 1974-12-21 | 1975-12-19 | Forfarande for framstellning av cykloalitatiska aminosyror och estrar derav |
| ES443723A ES443723A1 (es) | 1974-12-21 | 1975-12-19 | Procedimiento de preparacion de aminoacidos ciclicos. |
| FI753613A FI62282C (fi) | 1974-12-21 | 1975-12-19 | Foerfarande foer framstaellning av terapeutiskt anvaendbara cyliska aminosyror |
| AU87741/75A AU488009B2 (en) | 1974-12-21 | 1975-12-19 | Cyclic amino-acids |
| LU74058A LU74058A1 (ref) | 1974-12-21 | 1975-12-19 | |
| DK581475A DK147706C (da) | 1974-12-21 | 1975-12-19 | Analogifremgangsmaade til fremstilling af cycliske aminocarboxylsyrer eller farmakologisk acceptable salte deraf |
| NLAANVRAGE7514900,A NL181006C (nl) | 1974-12-21 | 1975-12-20 | Werkwijze voor de bereiding of vervaardiging van een geneesmiddel voor de behandeling van epilepsie, duizeligheid, hypokinesis, schedeltrauma en geriatrische ziekten, alsmede werkwijze voor de bereiding van een 4-aminoboterzuur derivaat. |
| AT975075A AT340892B (de) | 1974-12-21 | 1975-12-22 | Verfahren zur herstellung von neuen 1-aminomethyl-1-cycloalkanessigsauren und deren estern sowie salzen |
| JP15319475A JPS5324064B2 (ref) | 1974-12-21 | 1975-12-22 | |
| US05/645,724 US4024175A (en) | 1974-12-21 | 1975-12-31 | Cyclic amino acids |
| US05/791,677 US4087544A (en) | 1974-12-21 | 1977-04-28 | Treatment of cranial dysfunctions using novel cyclic amino acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2460891A DE2460891C2 (de) | 1974-12-21 | 1974-12-21 | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2460891A1 DE2460891A1 (de) | 1976-07-01 |
| DE2460891C2 true DE2460891C2 (de) | 1982-09-23 |
Family
ID=5934284
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2460891A Expired DE2460891C2 (de) | 1974-12-21 | 1974-12-21 | 1-Aminomethyl-1-cycloalkanessigsäuren und deren Ester, Verfahren zu deren Herstellung und diese Verbindungen enthaltende Arzneimittel |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4024175A (ref) |
| JP (1) | JPS5324064B2 (ref) |
| AT (1) | AT340892B (ref) |
| BE (1) | BE836835A (ref) |
| CA (1) | CA1052811A (ref) |
| CH (3) | CH612666A5 (ref) |
| DE (1) | DE2460891C2 (ref) |
| DK (1) | DK147706C (ref) |
| ES (1) | ES443723A1 (ref) |
| FI (1) | FI62282C (ref) |
| FR (1) | FR2294697A1 (ref) |
| GB (1) | GB1465229A (ref) |
| IE (1) | IE42382B1 (ref) |
| LU (1) | LU74058A1 (ref) |
| NL (1) | NL181006C (ref) |
| SE (1) | SE423385B (ref) |
Families Citing this family (221)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2611690A1 (de) * | 1976-03-19 | 1977-09-22 | Goedecke Ag | Cyclische sulfonyloxyimide |
| JPS5776189U (ref) * | 1980-10-28 | 1982-05-11 | ||
| JPS6152583U (ref) * | 1984-09-11 | 1986-04-09 | ||
| JPS61139881U (ref) * | 1985-02-21 | 1986-08-29 | ||
| US4876279A (en) * | 1986-05-05 | 1989-10-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| US4894476A (en) * | 1988-05-02 | 1990-01-16 | Warner-Lambert Company | Gabapentin monohydrate and a process for producing the same |
| US4960931A (en) * | 1988-05-02 | 1990-10-02 | Warner-Lambert Company | Gabapentin mohohydrate and a process for producing the same |
| YU162789A (en) * | 1988-09-01 | 1990-12-31 | Lonza Ag | 2-aza-4-(alcoxycarbonyl) spiro/4,5/decan-3-ones |
| US5319135A (en) * | 1989-08-25 | 1994-06-07 | Warner-Lambert Company | Process for cyclic amino acid anticonvulsant compounds |
| DE3928182A1 (de) * | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von gabapentin |
| DE3928183A1 (de) * | 1989-08-25 | 1991-02-28 | Goedecke Ag | Lactamfreie cyclische aminosaeuren |
| US5132451A (en) * | 1989-08-25 | 1992-07-21 | Warner-Lambert Company | Process for cyclic amino acid anticonvulsant compounds |
| DE3928184A1 (de) * | 1989-08-25 | 1991-02-28 | Goedecke Ag | Verfahren zur herstellung von cyclischen aminosaeurederivaten sowie zwischenprodukte |
| MY106864A (en) * | 1989-08-25 | 1995-08-30 | Warner Lambert Co | Improved process for cyclic amino acid anticonvulsant compounds. |
| US5260467A (en) * | 1989-11-16 | 1993-11-09 | Pfizer Inc. | Glutaric acid derivatives and preparation thereof |
| FI905584A7 (fi) * | 1989-11-16 | 1991-05-17 | Lonza Ag | Menetelmä 1-(aminometyyli)sykloheksaanietikkahapon valmistamiseksi |
| US5136091A (en) * | 1989-11-16 | 1992-08-04 | Lonza Ltd. | Process for the production of 1-(aminomethyl) cyclohexane acetic acid |
| GB8925933D0 (en) * | 1989-11-16 | 1990-01-04 | Pfizer Ltd | Glutaric acid derivatives and preparation thereof |
| US5157138A (en) * | 1989-11-16 | 1992-10-20 | Pfizer, Inc. | Glutaric acid derivatives and preparation thereof |
| US5149870A (en) * | 1989-11-16 | 1992-09-22 | Lonza Ltd. | Process for the production of 1-(aminomethyl)cyclohexane acetic acid |
| US5084479A (en) * | 1990-01-02 | 1992-01-28 | Warner-Lambert Company | Novel methods for treating neurodegenerative diseases |
| US5025035A (en) * | 1990-10-12 | 1991-06-18 | Warner-Lambert Company | Method of treating depression |
| US5792796A (en) * | 1994-07-27 | 1998-08-11 | Warner-Lambert Company | Methods for treating anxiety and panic |
| US5510381A (en) * | 1995-05-15 | 1996-04-23 | Warner-Lambert Company | Method of treatment of mania and bipolar disorder |
| HUP9901074A3 (en) * | 1996-02-07 | 2001-08-28 | Warner Lambert Co | Tetrahydropyrane and tetrahydrothiopyrane aminoacids and pharmaceutical compositions containing them |
| SK282848B6 (sk) * | 1996-03-14 | 2002-12-03 | Warner-Lambert Company | Premostené cyklické aminokyseliny, farmaceutická kompozícia obsahujúca tieto aminokyseliny |
| CZ293759B6 (cs) * | 1996-03-14 | 2004-07-14 | Warner-Lambert Company | Substituovaná cyklická aminokyselina, její použití a farmaceutický prostředek na její bázi |
| US6001876A (en) | 1996-07-24 | 1999-12-14 | Warner-Lambert Company | Isobutylgaba and its derivatives for the treatment of pain |
| NZ334898A (en) * | 1996-10-23 | 2000-09-29 | Warner Lambert Co | Substituted gamma aminobutyric acids as pharamceutical agents |
| IL119890A (en) * | 1996-12-24 | 2002-03-10 | Teva Pharma | Gabapentin form iii and preparation of gabapentin form ii |
| US6255526B1 (en) | 1996-12-24 | 2001-07-03 | Teva Pharmaceutical Industries Ltd. | Preparation of gabapentin |
| US6329429B1 (en) | 1997-06-25 | 2001-12-11 | Warner-Lambert Company | Use of GABA analogs such as Gabapentin in the manufacture of a medicament for treating inflammatory diseases |
| HRP980342A2 (en) * | 1997-06-25 | 1999-02-28 | Warner Lambert Co | Anti-inflammatory method |
| US6194459B1 (en) | 1997-08-19 | 2001-02-27 | Warner-Lambert Company | Methods for treating physiological conditions associated with the use, or sequelae of use, of cocaine or other psychomotors stimulants |
| EP1011658B1 (en) * | 1997-09-08 | 2005-12-07 | Warner-Lambert Company Llc | Analgesic compositions comprising anti-epileptic compounds and methods of using same |
| WO1999018063A2 (en) | 1997-10-07 | 1999-04-15 | Warner-Lambert Company | Process for preparing a cyclic amino acid anticonvulsant compound |
| KR100589066B1 (ko) * | 1997-10-27 | 2006-06-13 | 워너-램버트 캄파니 엘엘씨 | 약제로서 유용한 시클릭 아미노산 및 그의 유도체 |
| US6984659B2 (en) * | 1997-11-18 | 2006-01-10 | Klinikum Der Albert-Ludwigs Universitaet | 2-pyrrolidinone derivatives substituted at position 4 for reducing the extracellular glutamate level |
| 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 |
| KR20010033153A (ko) | 1997-12-16 | 2001-04-25 | 로즈 암스트롱, 크리스틴 에이. 트러트웨인 | 4(3)-치환-4(3)-아미노메틸-(티오)피란 또는 -피페리딘유도체(=가바펜틴 동족체), 그의 제법 및 신경 질환 치료용도 |
| ES2216338T3 (es) | 1997-12-16 | 2004-10-16 | Warner-Lambert Company Llc | Aminas novedosas como agentes farmaceuticos. |
| WO1999037296A1 (en) * | 1998-01-23 | 1999-07-29 | Warner-Lambert Company | Gabapentin and its derivatives for the treatment of muscular and skeletal pain |
| EP0974351A3 (en) * | 1998-04-24 | 2000-12-13 | Jouveinal | Medicament for preventing and treating gastrointestinal damage |
| IL139298A0 (en) | 1998-05-15 | 2001-11-25 | Warner Lambert Co | Stabilized pharmaceutical preparations of gamma-aminobutyric acid derivatives and process for preparing the same |
| PL205145B1 (pl) * | 1998-05-15 | 2010-03-31 | Warner Lambert Co | Trwała kompozycja stała zawierająca pochodną 4-amino-3-podstawionego kwasu butanowego oraz sposób jej wytwarzania |
| ES2137137B1 (es) * | 1998-05-25 | 2000-08-16 | Medichem Sa | Nuevo polimorfo de gabapentina no hidratada, su procedimiento de obtencion y su utilizacion para la obtencion de gabapentina de calidad farmaceutica. |
| EP1082306A1 (en) | 1998-05-26 | 2001-03-14 | Warner-Lambert Company | Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel |
| ITMI981535A1 (it) * | 1998-07-03 | 2000-01-03 | Zambon Spa | Processo per la preparazione di gabapentina |
| US20030045500A1 (en) * | 1998-07-09 | 2003-03-06 | Leslie Magnus | Pharmaceutical composition containing GABA analogs and an antiviral agent to treat shingles |
| FR2781793B1 (fr) | 1998-08-03 | 2001-07-20 | Prographarm Lab | Procede de fabrication de granules de gabapentine enrobes |
| HU225502B1 (en) * | 1998-12-29 | 2007-01-29 | Richter Gedeon Vegyeszet | Process for producing 1-(amino-metyl)-cyclohexene-acetic-acid and intermediates |
| IT1311984B1 (it) | 1999-03-26 | 2002-03-22 | Bioindustria Lab Italiano Medi | Procedimento per la preparzione di gabapentin. |
| WO2000061188A1 (en) * | 1999-04-09 | 2000-10-19 | Euro-Celtique S.A. | Sodium channel blocker compositions and the use thereof |
| AU4673200A (en) * | 1999-05-28 | 2000-12-18 | Warner-Lambert Company | 3-heteroarylalkyl substituted gaba analogs |
| US6710190B1 (en) * | 1999-05-28 | 2004-03-23 | Warner-Lambert Company | 3-heteroarylalkyl substituted gaba analogs |
| US7164034B2 (en) * | 1999-06-10 | 2007-01-16 | Pfizer Inc. | Alpha2delta ligands for fibromyalgia and other disorders |
| US20080207755A1 (en) * | 2000-05-31 | 2008-08-28 | Pfizer Inc | Alpha 2 Delta Ligands For Fibromyalgia and Other Disorders |
| CA2374755C (en) * | 1999-06-10 | 2010-03-30 | Warner-Lambert Company | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| US6294198B1 (en) | 1999-08-24 | 2001-09-25 | Purepac Pharmaceutical Co. | Pharmaceutical tablet formulation containing gabapentin with improved physical and chemical characteristics and method of making the same |
| HN2000000224A (es) * | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| GB2362646A (en) * | 2000-05-26 | 2001-11-28 | Warner Lambert Co | Cyclic amino acid derivatives useful as pharmaceutical agents |
| EP1289364B1 (en) | 2000-06-16 | 2003-12-10 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin containing more than 2o ppm of chlorine ion |
| EP1384473A1 (en) * | 2000-06-16 | 2004-01-28 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin containing more than 20 ppm of chlorine ion |
| AU2001266992B8 (en) * | 2000-06-16 | 2005-12-01 | Teva Pharmaceutical Industries Ltd. | Stable gabapentin having pH within a controlled range |
| ATE390133T1 (de) * | 2000-06-26 | 2008-04-15 | Warner Lambert Co | Gabapentinanaloga für schlafstörungen |
| GB2364049A (en) * | 2000-06-28 | 2002-01-16 | Warner Lambert Co | Cyclic ketones and their use in the synthesis of amino acids |
| ES2252310T3 (es) * | 2000-09-14 | 2006-05-16 | Grunenthal Gmbh | Beta-tioaminoacidos. |
| AU2002211863A1 (en) * | 2000-10-06 | 2002-04-15 | Xenoport, Inc. | Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration |
| EP1361847A2 (en) * | 2000-10-06 | 2003-11-19 | Xenoport, Inc. | Bile-acid conjugates for providing sustained systemic concentrations of drugs |
| US6620829B2 (en) * | 2000-10-17 | 2003-09-16 | Warner-Lambert Company | Method of treating noninflammatory cartilage damage |
| IT1319234B1 (it) * | 2000-10-23 | 2003-09-26 | Zambon Spa | Processo di preparazione di gabapentina. |
| GB2368579A (en) * | 2000-10-31 | 2002-05-08 | Parke Davis & Co Ltd | Azole pharmaceutical agents |
| CN1471507A (zh) * | 2000-11-02 | 2004-01-28 | ������ҩ��ҵ����˾ | 用于制备加巴喷丁中间体的改进方法 |
| IL155704A0 (en) * | 2000-11-30 | 2003-11-23 | Pfizer Prod Inc | Combination of gaba agonists and sorbitol dehydrogenase inhibitors |
| HRP20030419A2 (en) * | 2000-11-30 | 2004-08-31 | Pfizer Prod Inc | Combination of gaba agonists and aldose reductase inhibitors |
| IT1319674B1 (it) * | 2000-12-01 | 2003-10-23 | Erregierre Spa | Processo per la preparazione dell'acido1-(aminometil)cicloesanacetico. |
| JP2004524339A (ja) * | 2001-03-16 | 2004-08-12 | ソルケム イタリアーナ エス．ピー．エイ． | 環状アミノ酸の調製方法 |
| ITMI20011132A1 (it) | 2001-05-29 | 2002-11-29 | Procos Spa | Procedimento per la preparazione dell'acido 1-amminometil-1-cicloesanacetico |
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7232924B2 (en) * | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| MXPA03011566A (es) * | 2001-06-11 | 2004-10-28 | Xenoport Inc | Formas de dosificacion de profarmacos de analogos de gaba administrados oralmente que tienen toxicidad reducida. |
| US7420002B2 (en) * | 2001-06-11 | 2008-09-02 | Xenoport | Amino acid conjugates providing for sustained systemic concentrations of GABA analogues |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US6818787B2 (en) | 2001-06-11 | 2004-11-16 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| IL144066A0 (en) * | 2001-06-28 | 2002-04-21 | Bromine Compounds Ltd | Process for the preparation of 1,1-cyclohexane diacetic monoamide |
| ITMI20011772A1 (it) | 2001-08-10 | 2003-02-10 | A M S A Anonima Materie Sint E | Processo per la preparazione della 2,5-bis-(2,2,2-trifluoroetossi)-n-(2-piperidilmetil)-benzamide(flecainide) |
| SI1423168T1 (sl) | 2001-09-03 | 2006-06-30 | Newron Pharm Spa | Farmacevtski sestavek, ki vsebuje gabapentin ali njegov analog in alfa-aminoamid, in njegova analgetska uporaba |
| US6800782B2 (en) * | 2001-10-09 | 2004-10-05 | Warner-Lambert Co. | Anhydrous crystalline forms of gabapentin |
| US20070184104A1 (en) * | 2001-10-25 | 2007-08-09 | Depomed, Inc. | Gastric retentive gabapentin dosage forms and methods for using same |
| TWI312285B (en) * | 2001-10-25 | 2009-07-21 | Depomed Inc | Methods of treatment using a gastric retained gabapentin dosage |
| US20060159743A1 (en) * | 2001-10-25 | 2006-07-20 | Depomed, Inc. | Methods of treating non-nociceptive pain states with gastric retentive gabapentin |
| US7612112B2 (en) | 2001-10-25 | 2009-11-03 | Depomed, Inc. | Methods of treatment using a gastric retained gabapentin dosage |
| US20030119908A1 (en) * | 2001-12-21 | 2003-06-26 | Zambon Group S.P.A. | Stable gabapentin compositions |
| ITMI20012750A1 (it) | 2001-12-21 | 2003-06-21 | Procos Spa | Processo per la produzione dell'acido 1-(amminometil)-cicloesil-acetico in forma pura |
| EP1469841A1 (en) * | 2002-01-31 | 2004-10-27 | Warner-Lambert Company | Alpha 2 delta ligands to treat tinnitus |
| US6682759B2 (en) | 2002-02-01 | 2004-01-27 | Depomed, Inc. | Manufacture of oral dosage forms delivering both immediate-release and sustained-release drugs |
| US6927036B2 (en) * | 2002-02-19 | 2005-08-09 | Xero Port, Inc. | Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof |
| US7026351B2 (en) * | 2002-03-20 | 2006-04-11 | Xenoport, Inc. | Cyclic 1-(acyloxy)-alkyl prodrugs of GABA analogs, compositions and uses thereof |
| EP1494996A1 (en) * | 2002-04-16 | 2005-01-12 | Taro Pharmaceutical Industries Limited | Process for preparing gabapentin |
| WO2003094842A2 (en) * | 2002-05-07 | 2003-11-20 | A & D Bioscience, Inc. | Conjugates comprising central nervous system active drug |
| AU2003243180A1 (en) * | 2002-05-17 | 2003-12-12 | Xenoport, Inc. | Amino acid conjugates providing for sustained systemic concentrations of gaba analogues |
| EP1515709A2 (en) * | 2002-06-27 | 2005-03-23 | Warner-Lambert Company LLC | Use of an alpha2delta ligand such as gabapentin or pregabalin for treating attention deficit hyperactivity disorder |
| CA2395931A1 (en) * | 2002-08-07 | 2004-02-07 | Bernard Charles Sherman | Solid compositions comprising gabapentin having improved stability |
| US7053122B2 (en) * | 2002-08-09 | 2006-05-30 | Pfizer Inc | Therapeutic use of aryl amino acid derivatives |
| US7419981B2 (en) * | 2002-08-15 | 2008-09-02 | Pfizer Inc. | Synergistic combinations of an alpha-2-delta ligand and a cGMP phosphodieterse 5 inhibitor |
| US20040092591A1 (en) * | 2002-08-15 | 2004-05-13 | Blakemore David Clive | Therapeutic use of fused bicyclic or tricyclic amino acids |
| US20040092522A1 (en) * | 2002-08-15 | 2004-05-13 | Field Mark John | Synergistic combinations |
| US20040092498A1 (en) * | 2002-08-16 | 2004-05-13 | David Blakemore | Substituted glycine derivatives for use as medicaments |
| ITMI20022071A1 (it) * | 2002-10-01 | 2004-04-02 | Erregierre Spa | Processo di sintesi dell'acido 1-(aminometil)cicloesanacetico cloridato. |
| US7659305B2 (en) * | 2002-10-31 | 2010-02-09 | Pfizer Inc. | Therapeutic proline derivatives |
| ATE418535T1 (de) * | 2002-11-18 | 2009-01-15 | Nicholas Piramal India Ltd | Verbessertes verfahren zur herstellung von gabapentin |
| ES2334119T3 (es) * | 2002-11-20 | 2010-03-05 | Hikal Ltd. | Procedimiento mejorado para la fabricacion de gabalactama. |
| AU2003297909A1 (en) * | 2002-12-11 | 2004-06-30 | Xenoport, Inc. | Orally administered dosage forms of fused gaba analog prodrugs having reduced toxicity |
| US7060727B2 (en) * | 2002-12-11 | 2006-06-13 | Xenoport, Inc. | Prodrugs of fused GABA analogs, pharmaceutical compositions and uses thereof |
| US20040180958A1 (en) * | 2002-12-13 | 2004-09-16 | Taylor Charles Price | Method of treatment |
| AU2003283718A1 (en) * | 2002-12-13 | 2004-07-09 | Warner-Lambert Company Llc | Gabapentin analogues for fibromyalgia and other related disorders |
| CN101862317A (zh) * | 2002-12-13 | 2010-10-20 | 沃尼尔·朗伯有限责任公司 | 用于治疗纤维肌痛和其它疾病的普加巴林衍生物 |
| MXPA05006209A (es) * | 2002-12-13 | 2005-08-19 | Warner Lambert Co | Pregabalina y sus derivados para el tratamiento de fibromialgia y otros trastornos relacionados. |
| CA2451267A1 (en) * | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| DE60332387D1 (de) | 2002-12-13 | 2010-06-10 | Warner Lambert Co | Alpha-2-delta-ligand zur behandlung vonsymptomen der unteren harnwege |
| GB0301143D0 (en) * | 2003-01-17 | 2003-02-19 | Amedis Pharm Ltd | Compounds and their use |
| RU2312853C2 (ru) * | 2003-01-22 | 2007-12-20 | Уорнер-Ламберт Компани Ллс | ПРОИЗВОДНЫЕ ЦИКЛОПРОПИЛ-β-АМИНОКИСЛОТЫ |
| JP2006519831A (ja) * | 2003-03-07 | 2006-08-31 | ワーナー−ランバート カンパニー リミティド ライアビリティー カンパニー | テトラゾール及びオキサジアゾロン置換β−アミノ酸誘導体 |
| WO2004093866A1 (en) * | 2003-03-25 | 2004-11-04 | Kiel Laboratories, Inc. | Process for preparing phenolic acid salts of gabapentin |
| WO2004093827A2 (en) * | 2003-03-25 | 2004-11-04 | Kiel Laboratories, Inc. | Phenolic acid salts of gabapentin in solid dosage forms and methods of use |
| EP1628656B1 (en) * | 2003-03-25 | 2008-10-15 | Kiel Laboratories, Inc. | Gabapentin tannate in liquid and/or semi-solid dosage forms |
| MXPA05010515A (es) * | 2003-03-31 | 2006-03-10 | Xenoport Inc | Tratamiento o prevencion de sofocos calientes utilizando profarmacos de analogos de gaba. |
| WO2004091278A2 (en) * | 2003-04-11 | 2004-10-28 | Transform Pharmaceuticals, Inc. | Gabapentin compositions |
| ITMI20030825A1 (it) * | 2003-04-18 | 2004-10-19 | Farchemia Srl | Procedimento per la preparazione di gabapentin esente da |
| EP1615875A2 (en) * | 2003-04-21 | 2006-01-18 | Matrix Laboratories Limited | Process for the preparation of gabapentin form-ii |
| EP1633400A2 (en) * | 2003-05-16 | 2006-03-15 | Pfizer Products Inc. | Therapeutic combinations of atypical antipsychotics with gaba modulators, anticonvulsants or benzodiazapines |
| CA2528388A1 (en) * | 2003-06-19 | 2004-12-23 | Pfizer Products Inc. | Biocatalytic preparation of 1-cyanocyclohexaneacetic acid |
| US7169812B2 (en) * | 2003-07-01 | 2007-01-30 | Medtronic, Inc. | Process for producing injectable gabapentin compositions |
| CA2572324A1 (en) * | 2003-07-02 | 2005-01-13 | Warner-Lambert Company Llc | Combination of an allosteric inhibitor of matrix metalloproteinase-13 and a ligand to an alpha-2-delta receptor |
| US20050013863A1 (en) | 2003-07-18 | 2005-01-20 | Depomed, Inc., A Corporation Of The State Of California | Dual drug dosage forms with improved separation of drugs |
| WO2005046566A2 (en) * | 2003-08-04 | 2005-05-26 | Sun Pharmaceutical Industries Limited | Stable gabapentin containing composition |
| US20050043407A1 (en) * | 2003-08-22 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
| KR20060119971A (ko) * | 2003-09-11 | 2006-11-24 | 제노포트 인코포레이티드 | Ｇａｂａ 유사체의 전구약물을 이용한 요실금의 치료및/또는 예방 |
| DE602004024317D1 (de) | 2003-09-12 | 2010-01-07 | Pfizer | Kombinationen aus alpha-2-delta liganden und serotonin / noradrenalin-wiederaufnahmehemmern |
| KR20060087560A (ko) * | 2003-09-12 | 2006-08-02 | 워너-램버트 캄파니 엘엘씨 | 알파-2-델타 리간드 및 ｓｓｒｉ 및/또는 ｓｎｒｉ를포함하는 우울증 및 불안 장애 치료용 조합물 |
| WO2005027850A2 (en) * | 2003-09-17 | 2005-03-31 | Xenoport, Inc. | Treating or preventing restless legs syndrome using prodrugs of gaba analogs |
| MXPA06004088A (es) * | 2003-10-14 | 2006-06-27 | Xenoport Inc | Forma cristalina de un analogo del acido gamma-aminobutirico. |
| ITMI20032165A1 (it) * | 2003-11-11 | 2005-05-12 | Zambon Spa | Processo di preparazione di gabapentina |
| WO2005060968A1 (en) | 2003-12-11 | 2005-07-07 | Sepracor Inc. | Combination of a sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression |
| CA2553291A1 (en) * | 2004-01-29 | 2005-09-09 | Pfizer Products Inc. | Combination of .gamma.-aminobutyric acid modulators and 5-ht1b receptor antagonists |
| US20050187295A1 (en) * | 2004-02-19 | 2005-08-25 | Surendra Kalyan | Processes for the preparation of gabapentin |
| CA2570255A1 (en) * | 2004-03-17 | 2005-09-22 | Hikal Limited | 4-t-butylgabapentin and its synthesis |
| ITMI20040579A1 (it) * | 2004-03-25 | 2004-06-25 | Zambon Spa | Processo di preparazione di gabapentina |
| CA2567249A1 (en) * | 2004-04-19 | 2006-10-05 | Jds Pharmaceuticals, Llc | Lithium combinations, and uses related thereto |
| KR20070029740A (ko) * | 2004-06-09 | 2007-03-14 | 화이자 인코포레이티드 | 통증 치료를 위한 레복세틴의 용도 |
| GB0416228D0 (en) * | 2004-07-20 | 2004-08-25 | Sandoz Ind Products S A | Process for the preparation of gabapentin |
| GB0419849D0 (en) * | 2004-09-07 | 2004-10-13 | Pfizer Ltd | Pharmaceutical combination |
| US20080096965A1 (en) * | 2004-09-10 | 2008-04-24 | Newron Pharmaceuticals S.P.A. | (Halobenzyloxy) Benzylamino-Propanamides as Sodium and/or Calcium Channel Selective Modulators |
| EP1811986B1 (en) | 2004-11-04 | 2014-03-26 | XenoPort, Inc. | Gabapentin prodrug sustained release oral dosage forms |
| JP2009506069A (ja) | 2005-08-26 | 2009-02-12 | ブレインセルス，インコーポレイティド | ムスカリン性受容体調節による神経発生 |
| EP2258359A3 (en) | 2005-08-26 | 2011-04-06 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation with sabcomelin |
| US8378096B2 (en) * | 2005-09-23 | 2013-02-19 | Janssen Pharmaceutica N.V. | Hexahydro-cycloheptapyrazole cannabinoid modulators |
| US7825151B2 (en) * | 2005-09-23 | 2010-11-02 | Janssen Pharmaceutica Nv | Hexahydro-cyclooctyl pyrazole cannabinoid modulators |
| PL1931335T3 (pl) * | 2005-09-23 | 2010-07-30 | Janssen Pharmaceutica Nv | Modulatory heksahydrocyklooktylopirazolokannabinoidowe |
| HRP20120159T1 (hr) * | 2005-09-23 | 2012-03-31 | Janssen Pharmaceutica Nv | Modulatori heksahidro-cikloheptapirazol kanabinoida |
| US8378117B2 (en) * | 2005-09-23 | 2013-02-19 | Janssen Pharmaceutica N.V. | Hexahydro-cycloheptapyrazole cannabinoid modulators |
| US7790718B2 (en) * | 2005-09-23 | 2010-09-07 | Janssen Pharmaceutica Nv | Tetrahydro-cyclopentyl pyrazole cannabinoid modulators |
| US7985756B2 (en) | 2005-10-21 | 2011-07-26 | Braincells Inc. | Modulation of neurogenesis by PDE inhibition |
| WO2007053596A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20070117858A1 (en) * | 2005-11-23 | 2007-05-24 | Mingde Xia | Substituted 5-heteroaryl-1-phenyl-pyrazole cannabinoid modulators |
| US20090176882A1 (en) * | 2008-12-09 | 2009-07-09 | Depomed, Inc. | Gastric retentive gabapentin dosage forms and methods for using same |
| WO2007092456A2 (en) * | 2006-02-03 | 2007-08-16 | Rolls-Royce Corporation | Gas turbine engine fuel system with fuel metering valve |
| EP1820502A1 (en) | 2006-02-10 | 2007-08-22 | Laboratorios Del Dr. Esteve, S.A. | Active substance combination comprising azolylcarbinol compounds |
| WO2007095513A1 (en) * | 2006-02-14 | 2007-08-23 | Janssen Pharmaceutica, Nv | Tetrahydr0-2h-indaz0le derivatives for use as cannabinoid modulators |
| KR20080100284A (ko) * | 2006-03-06 | 2008-11-14 | 화이자 프로덕츠 인코포레이티드 | 비-회복성 수면을 위한 알파-2-델타 리간드 |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| US20070254911A1 (en) * | 2006-03-27 | 2007-11-01 | Mingde Xia | Tetrahydro-Pyrazolo[3,4-c]Pyridine Cannabinoid Modulators |
| US8012957B2 (en) * | 2006-03-27 | 2011-09-06 | Janssen Pharmaceutica Nv | Tetrahydro-1H-1,2,6-triaza-azulene cannabinoid modulators |
| WO2007134077A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| WO2007134136A2 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| US7442834B2 (en) * | 2006-06-12 | 2008-10-28 | Zhejiang Chiral Medicine Chemicals Co., Ltd. | Process suitable for industrial scale production of gabapentin |
| US8143443B2 (en) * | 2006-06-30 | 2012-03-27 | Zach System S.P.A. | Process for preparing gabapentin |
| EP2068872A1 (en) | 2006-09-08 | 2009-06-17 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| BRPI0720252A2 (pt) * | 2006-12-08 | 2014-01-07 | Xenoport Inc | Uso de pró-fármacos de análogos de gaba para tratar doenças |
| ATE511860T1 (de) | 2006-12-22 | 2011-06-15 | Recordati Ireland Ltd | Kombinationstherapie für erkrankungen der unteren harnwege mit 2 liganden und nsar |
| JP2010521453A (ja) * | 2007-03-15 | 2010-06-24 | サン・ファーマ・アドバンスド・リサーチ・カンパニー・リミテッド | 新規プロドラッグ |
| WO2008157408A2 (en) * | 2007-06-15 | 2008-12-24 | Xenoport, Inc. | Use of prodrugs of gaba analogs, antispasticity agents, and prodrugs of gaba b receptor agonists for treating spasticity |
| US7943653B2 (en) * | 2007-08-13 | 2011-05-17 | Janssen Pharmaceutica N.V. | Substituted 5-vinylphenyl-1-phenyl-pyrazole cannabinoid modulators |
| US20090062392A1 (en) * | 2007-08-29 | 2009-03-05 | Protia, Llc | Deuterium-enriched gabapentin |
| WO2009061934A1 (en) * | 2007-11-06 | 2009-05-14 | Xenoport, Inc. | Use of prodrugs of gaba b agonists for treating neuropathic and musculoskeletal pain |
| US7872046B2 (en) * | 2008-01-25 | 2011-01-18 | Xenoport, Inc. | Crystalline form of a (3S)-aminomethyl-5-methyl-hexanoic acid prodrug and methods of use |
| WO2009094577A2 (en) | 2008-01-25 | 2009-07-30 | Xenoport, Inc. | Mesophasic forms of (3s)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use |
| EP2250143B1 (en) * | 2008-01-25 | 2016-04-20 | XenoPort, Inc. | Method for the enzymatic kinetic resolution of acyloxyalkyl thiocarbonates used for the synthesis of acyloxyalkyl carbamates |
| EP2116539A1 (en) | 2008-04-25 | 2009-11-11 | Laboratorios Del. Dr. Esteve, S.A. | 1-aryl-3-aminoalkoxy-pyrazoles as sigma ligands enhancing analgesic effects of opioids and attenuating the dependency thereof |
| US20100190752A1 (en) * | 2008-09-05 | 2010-07-29 | Gruenenthal Gmbh | Pharmaceutical Combination |
| ES2589915T3 (es) | 2008-10-08 | 2016-11-17 | Xgene Pharmaceutical Inc | Conjugados de GABA y métodos de utilización de los mismos |
| WO2010099200A1 (en) | 2009-02-24 | 2010-09-02 | Nektar Therapeutics | Oligomer-amino acid conjugates |
| WO2010099217A1 (en) | 2009-02-25 | 2010-09-02 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| US20110124705A1 (en) * | 2009-11-24 | 2011-05-26 | Xenoport, Inc. | Prodrugs of alpha-2-delta ligands, pharmaceutical compositions and uses thereof |
| US20110130454A1 (en) * | 2009-11-24 | 2011-06-02 | Xenoport, Inc. | Prodrugs of gamma-amino acid, alpha-2-delta ligands, pharmaceutical compositions and uses thereof |
| EP2509596B1 (en) | 2009-12-08 | 2019-08-28 | Case Western Reserve University | Gamma aminoacids for treating ocular disorders |
| EP2353591A1 (en) | 2010-02-04 | 2011-08-10 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for potentiating the analgesic effect of opioids and opiates in post-operative pain and attenuating the dependency thereof |
| EP2368872A1 (en) | 2010-03-25 | 2011-09-28 | Serichim S.r.l. | Process for the preparation of Gabapentin |
| EP2388005A1 (en) | 2010-05-21 | 2011-11-23 | Laboratorios Del. Dr. Esteve, S.A. | Sigma ligands for the prevention and/or treatment of emesis induced by chemotherapy or radiotherapy |
| US20130078290A1 (en) | 2010-06-01 | 2013-03-28 | Rubicon Research Private Limited | Gastroretentive Dosage Forms Of GABA Analogs |
| US8431739B2 (en) | 2010-06-14 | 2013-04-30 | Divi's Laboratories, Ltd. | Process for the preparation of gabapentin |
| MX2013000946A (es) | 2010-07-30 | 2013-02-27 | Toray Industries | Agente terapeutico o agente profilactico para el dolor neuropatico. |
| EP2415471A1 (en) | 2010-08-03 | 2012-02-08 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in opioid-induced hyperalgesia |
| JP2013216580A (ja) * | 2010-08-06 | 2013-10-24 | Kyorin Pharmaceutical Co Ltd | ビシクロ［２．２．２］オクチルアミン誘導体の製造方法 |
| EP2524694A1 (en) | 2011-05-19 | 2012-11-21 | Laboratorios Del. Dr. Esteve, S.A. | Use of sigma ligands in diabetes type-2 associated pain |
| EP2530072A1 (en) | 2011-06-03 | 2012-12-05 | Lacer, S.A. | New compounds, synthesis and use thereof in the treatment of pain |
| US9066853B2 (en) | 2013-01-15 | 2015-06-30 | Warsaw Orthopedic, Inc. | Clonidine compounds in a biodegradable fiber |
| ITMI20131757A1 (it) | 2013-10-22 | 2015-04-23 | Zach System Spa | Processo di preparazione di gabapentina |
| JPWO2015064453A1 (ja) | 2013-11-01 | 2017-03-09 | 株式会社糖鎖工学研究所 | チオール基を有するｄ−体またはｌ−体アミノ酸誘導体の製造方法 |
| TW201607538A (zh) | 2013-12-17 | 2016-03-01 | 以斯提夫博士實驗室股份有限公司 | 血清素－去甲腎上腺素再攝取抑制劑（ＳＮＲＩＳ）和σ受體配體組合物 |
| CA2933057A1 (en) | 2013-12-17 | 2015-06-25 | Laboratorios Del Dr. Esteve, S.A. | Gabapentinoids and sigma receptor ligands combinations |
| WO2015144825A1 (en) | 2014-03-27 | 2015-10-01 | Sanovel Ilac Sanayi Ve Ticaret A.S. | Oral liquid pharmaceutical solution of gabapentin |
| LT3554490T (lt) | 2016-12-16 | 2022-04-25 | Idorsia Pharmaceuticals Ltd | Farmacinis derinys, apimantis t tipo kalcio kanalo blokatorių |
| MX384760B (es) | 2018-07-04 | 2025-03-14 | Federico Amezcua Amezcua | Combinación farmacéutica sinérgica del enantiómero activo s-ketorolaco y gabapentina para el tratamiento del dolor neuropático. |
| US10399926B1 (en) | 2018-08-01 | 2019-09-03 | Divi's Laboratories Ltd. | Process for the preparation of gabapentin |
| CN112839661A (zh) | 2018-10-11 | 2021-05-25 | 萨尼菲特治疗有限公司 | 用于治疗异位钙化的肌醇磷酸酯类 |
| AU2020370758B2 (en) * | 2019-10-25 | 2025-08-14 | Kyoto University | Preventative or therapeutic agent for tauopathy |
| MX2022010960A (es) | 2020-03-04 | 2022-11-16 | Pleopharma L L C | Métodos y composiciones para tratar el trastorno por uso de cannabis y mitigar la abstinencia de cannabinoides. |
| EP4015494A1 (en) | 2020-12-15 | 2022-06-22 | Sanifit Therapeutics S.A. | Processes for the preparation of soluble salts of inositol phosphates |
| GB2625579A (en) | 2022-12-21 | 2024-06-26 | Novumgen Ltd | An orally disintegrating tablet containing gabapentin or pharmaceutically acceptable salts thereof and the process of preparing the same |
-
1974
- 1974-12-21 DE DE2460891A patent/DE2460891C2/de not_active Expired
-
1975
- 1975-12-15 GB GB5119375A patent/GB1465229A/en not_active Expired
- 1975-12-15 IE IE2736/75A patent/IE42382B1/en unknown
- 1975-12-18 BE BE6045299A patent/BE836835A/xx not_active IP Right Cessation
- 1975-12-18 CH CH430878A patent/CH612666A5/xx active Protection Beyond IP Right Term
- 1975-12-18 FR FR7538818A patent/FR2294697A1/fr active Granted
- 1975-12-18 CH CH1645175A patent/CH612664A5/xx not_active IP Right Cessation
- 1975-12-18 CH CH430778A patent/CH612665A5/xx not_active IP Right Cessation
- 1975-12-19 SE SE7514442A patent/SE423385B/xx active Protection Beyond IP Right Term
- 1975-12-19 DK DK581475A patent/DK147706C/da not_active IP Right Cessation
- 1975-12-19 FI FI753613A patent/FI62282C/fi not_active IP Right Cessation
- 1975-12-19 LU LU74058A patent/LU74058A1/xx unknown
- 1975-12-19 ES ES443723A patent/ES443723A1/es not_active Expired
- 1975-12-19 CA CA242,147A patent/CA1052811A/en not_active Expired
- 1975-12-20 NL NLAANVRAGE7514900,A patent/NL181006C/xx not_active IP Right Cessation
- 1975-12-22 JP JP15319475A patent/JPS5324064B2/ja not_active Expired
- 1975-12-22 AT AT975075A patent/AT340892B/de active Protection Beyond IP Right Term
- 1975-12-31 US US05/645,724 patent/US4024175A/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| CH612664A5 (ref) | 1979-08-15 |
| FI62282B (fi) | 1982-08-31 |
| DK147706C (da) | 1985-05-13 |
| DK147706B (da) | 1984-11-19 |
| DK581475A (da) | 1976-01-22 |
| IE42382B1 (en) | 1980-07-30 |
| FR2294697B1 (ref) | 1978-07-28 |
| SE423385B (sv) | 1982-05-03 |
| CA1052811A (en) | 1979-04-17 |
| NL7514900A (nl) | 1976-06-23 |
| FI62282C (fi) | 1982-12-10 |
| DE2460891A1 (de) | 1976-07-01 |
| LU74058A1 (ref) | 1976-07-20 |
| AT340892B (de) | 1978-01-10 |
| FI753613A7 (ref) | 1976-06-22 |
| NL181006B (nl) | 1987-01-02 |
| US4024175A (en) | 1977-05-17 |
| ATA975075A (de) | 1977-05-15 |
| BE836835A (fr) | 1976-06-18 |
| AU8774175A (en) | 1977-06-23 |
| JPS5188940A (ref) | 1976-08-04 |
| CH612666A5 (ref) | 1979-08-15 |
| IE42382L (en) | 1976-06-21 |
| NL181006C (nl) | 1987-06-01 |
| CH612665A5 (ref) | 1979-08-15 |
| ES443723A1 (es) | 1977-04-16 |
| JPS5324064B2 (ref) | 1978-07-18 |
| GB1465229A (en) | 1977-02-23 |
| SE7514442L (sv) | 1976-06-22 |
| FR2294697A1 (fr) | 1976-07-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2460891A1 (de) | Cyclische aminosaeuren | |
| DE69409525T2 (de) | Acetamidderivate und ihre verwendung als modifizierungsmittel des verhaltens der verdauung | |
| DE965036C (de) | Verfahren zur Herstellung von p-(Bis-2-chloraethyl-amino)-ª-phenyl-alanin | |
| DE2228012B2 (de) | -Aminophenylacetamido] -penicülansäure und Verfahren zu seiner Herstellung | |
| DE3303112A1 (de) | Verfahren zur racemattrennung optisch aktiver bicyclischer imino-(alpha)-carbonsaeuren | |
| EP0109020A2 (de) | Neue Derivate tricyclischer Aminosäuren, Verfahren zu ihrer Herstellung, diese enthaltende Mittel und deren Verwendung, sowie neue bicyclische Aminosäuren als Zwischenstufen und Verfahren zu deren Herstellung | |
| EP0039844A2 (de) | Verfahren zur Herstellung von O-substituierten Derivaten des (+)-Cyanidan-3-ols | |
| EP0048911B1 (de) | O-substituierte alpha-Ketocarbonsäureoxime, Verfahren zu ihrer Herstellung, sowie Arzneimittel, die diese Verbindungen enthalten | |
| DE1645971A1 (de) | Verfahren zur Herstellung von therapeutisch wertvollen (Indazol-3-yl)-oxyalkansaeuren | |
| DE2221912A1 (de) | Penicillinester,deren Salze und Verfahren zu ihrer Herstellung | |
| EP0431371B1 (de) | 3-Aminopyrrole, Verfahren zu ihrer Herstellung und ihre Verwendung als Antikonvulsiva | |
| EP0094633B1 (de) | Spiro-2-aza-alkan-3-carbonitrile, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1620295C3 (de) | Isochinolo eckige Klammer auf 2,1-d eckige Klammer zu benzo eckige Klammer auf 1,4 eckige Klammer zu diazepin-6-one | |
| DE2543821C2 (de) | Bestimmte Salze und Ester von 1-Aminomethyl-1-cycloalkanessigsäuren und diese Verbindungen enthaltende Arzneimittel | |
| CH610330A5 (en) | Process for the preparation of novel ergopeptins | |
| DE2520131C3 (de) | 1,1,-Disubstituierte Octahydro-indolo[2,3-a]chinolizine und verfahren zu deren Herstellung | |
| CH649551A5 (de) | 3-substituierte-tetrahydro-pyrrolo(1,2-a)pyrimidine, verfahren zu ihrer herstellung sowie ihrer verwendung in pharmazeutischen praeparaten. | |
| DE2855853C2 (de) | N-(1-Benzyl-2-methyl-3-pyrrolidinyl)-5-chlor-2-methoxy-4-methylaminobenzamid dessen Säureadditionssalze, Verfahren zu deren Herstellung und ihre Verwendung | |
| AT390791B (de) | Verfahren zur herstellung neuer kondensierter as-triazinium-derivate sowie von deren isomeren | |
| DE2626467A1 (de) | Cyclische aminosaeure-derivate | |
| DE968561C (de) | Verfahren zur Herstellung von am Aminostickstoff substituierten Monoaminoacylaniliden | |
| DE1595891C3 (de) | 6-(ß-Dimethylaminopropyl)-pyrido- [2,3-b] [1, 5] benzodiazepin- (6H) -on-5, deren Salze und Verfahren zu ihrer Herstellung | |
| DE2331044A1 (de) | Diphenylmethan-derivate und verfahren zu deren herstellung | |
| DD246299A5 (de) | Verfahren zur herstellung n-substituierter anziridin-2-carbonsaeurederivaten | |
| DE2423725A1 (de) | 5-phenyl-4-oxo-delta hoch 2,alphathiazolidinessigsaeureester |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OD | Request for examination | ||
| AG | Has addition no. |
Ref country code: DE Ref document number: 2611690 Format of ref document f/p: P Ref country code: DE Ref document number: 2543821 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| AG | Has addition no. |
Ref country code: DE Ref document number: 2543821 Format of ref document f/p: P |
|
| AG | Has addition no. |
Ref country code: DE Ref document number: 2611690 Format of ref document f/p: P |