IL125544A - Transformed cyclic amino acids and pharmaceutical preparations containing them - Google Patents

Transformed cyclic amino acids and pharmaceutical preparations containing them

Info

Publication number: IL125544A
Authority: IL; Israel
Prior art keywords: compound according; methyl; compound; treating; cyclohexyl
Prior art date: 1996-03-14

Application number

IL12554497A

Other languages

English (en)

Hebrew (he)

Other versions

IL125544A0 (en

Original Assignee

Warner Lambert Co

Priority date (The priority date 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 date listed.)

1996-03-14

Filing date

1997-02-18

Publication date

2002-03-10

1997-02-18 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

1999-03-12 Publication of IL125544A0 publication Critical patent/IL125544A0/xx

2002-03-10 Publication of IL125544A publication Critical patent/IL125544A/en

Links

239000008194 pharmaceutical composition Chemical class 0.000 title claims description 13
-1 cyclic amino acids Chemical class 0.000 title abstract description 19
150000001875 compounds Chemical class 0.000 claims abstract description 70
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
150000003839 salts Chemical class 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
239000001257 hydrogen Substances 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
239000000651 prodrug Substances 0.000 claims abstract description 5
229940002612 prodrug Drugs 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
125000001424 substituent group Chemical group 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 30
239000003814 drug Substances 0.000 claims description 15
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
208000019901 Anxiety disease Diseases 0.000 claims description 8
230000036506 anxiety Effects 0.000 claims description 8
208000035475 disorder Diseases 0.000 claims description 8
206010015037 epilepsy Diseases 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
208000015122 neurodegenerative disease Diseases 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
230000036407 pain Effects 0.000 claims description 5
UOPIILYKLVDKTK-UHFFFAOYSA-N 2-[1-(aminomethyl)-3-methylcyclohexyl]acetic acid Chemical compound CC1CCCC(CN)(CC(O)=O)C1 UOPIILYKLVDKTK-UHFFFAOYSA-N 0.000 claims description 4
208000006083 Hypokinesia Diseases 0.000 claims description 4
208000002193 Pain Diseases 0.000 claims description 4
208000002173 dizziness Diseases 0.000 claims description 4
230000003483 hypokinetic effect Effects 0.000 claims description 4
ZMQXNOCRKMCKKX-UHFFFAOYSA-N 2-[1-(aminomethyl)-4-methylcyclohexyl]acetic acid Chemical compound CC1CCC(CN)(CC(O)=O)CC1 ZMQXNOCRKMCKKX-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
230000002981 neuropathic effect Effects 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
XZDWGABABFGFDB-UHFFFAOYSA-N 2-[1-(acetamidomethyl)-3-methylcyclohexyl]acetic acid Chemical compound CC1CCCC(CNC(C)=O)(CC(O)=O)C1 XZDWGABABFGFDB-UHFFFAOYSA-N 0.000 claims description 2
GLARDDUAAVSVRX-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-dimethylcyclohexyl]acetic acid Chemical compound CC1(C)CCCC(CN)(CC(O)=O)C1 GLARDDUAAVSVRX-UHFFFAOYSA-N 0.000 claims description 2
SBTHXYKNKAOGFH-UHFFFAOYSA-N 2-[[2-[1-(aminomethyl)-3-methylcyclohexyl]acetyl]amino]acetic acid;hydrochloride Chemical compound Cl.CC1CCCC(CN)(CC(=O)NCC(O)=O)C1 SBTHXYKNKAOGFH-UHFFFAOYSA-N 0.000 claims description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
FDOZSFMPSARACP-UHFFFAOYSA-N methyl 2-[1-(aminomethyl)-3-methylcyclohexyl]acetate;hydrochloride Chemical compound Cl.COC(=O)CC1(CN)CCCC(C)C1 FDOZSFMPSARACP-UHFFFAOYSA-N 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 8
125000003545 alkoxy group Chemical group 0.000 abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 72
229910001868 water Inorganic materials 0.000 description 63
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 60
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
239000007787 solid Substances 0.000 description 53
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
239000000203 mixture Substances 0.000 description 43
239000000243 solution Substances 0.000 description 43
238000004452 microanalysis Methods 0.000 description 39
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 34
239000002904 solvent Substances 0.000 description 34
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 33
238000005481 NMR spectroscopy Methods 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 24
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 21
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
235000019439 ethyl acetate Nutrition 0.000 description 20
229940093499 ethyl acetate Drugs 0.000 description 19
238000007429 general method Methods 0.000 description 18
239000003921 oil Substances 0.000 description 18
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
239000010408 film Substances 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 14
238000000034 method Methods 0.000 description 13
238000002360 preparation method Methods 0.000 description 13
150000003951 lactams Chemical class 0.000 description 12
229910052943 magnesium sulfate Inorganic materials 0.000 description 12
239000010409 thin film Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
238000010992 reflux Methods 0.000 description 11
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 11
241000700159 Rattus Species 0.000 description 10
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 10
229960002870 gabapentin Drugs 0.000 description 10
238000012360 testing method Methods 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 9
239000007788 liquid Substances 0.000 description 9
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
239000007868 Raney catalyst Substances 0.000 description 8
229910000564 Raney nickel Inorganic materials 0.000 description 8
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000010410 layer Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
230000002490 cerebral effect Effects 0.000 description 7
229910000069 nitrogen hydride Inorganic materials 0.000 description 7
239000003826 tablet Substances 0.000 description 7
MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 6
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
238000007792 addition Methods 0.000 description 6
239000002775 capsule Substances 0.000 description 6
229940079593 drug Drugs 0.000 description 6
230000036651 mood Effects 0.000 description 6
239000000843 powder Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000005695 Ammonium acetate Substances 0.000 description 5
208000006011 Stroke Diseases 0.000 description 5
229940043376 ammonium acetate Drugs 0.000 description 5
235000019257 ammonium acetate Nutrition 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
238000004440 column chromatography Methods 0.000 description 5
238000004821 distillation Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 5
229960003692 gamma aminobutyric acid Drugs 0.000 description 5
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
HNMWIKVFYHYBKX-UHFFFAOYSA-N tert-butyl 3-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC11CC(=O)NC1 HNMWIKVFYHYBKX-UHFFFAOYSA-N 0.000 description 5
VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000012267 brine Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000010779 crude oil Substances 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000003818 flash chromatography Methods 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
208000014674 injury Diseases 0.000 description 4
235000019341 magnesium sulphate Nutrition 0.000 description 4
241001515942 marmosets Species 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
229940072228 neurontin Drugs 0.000 description 4
230000003040 nociceptive effect Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
230000002792 vascular Effects 0.000 description 4
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
208000020401 Depressive disease Diseases 0.000 description 3
206010021143 Hypoxia Diseases 0.000 description 3
238000000023 Kugelrohr distillation Methods 0.000 description 3
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000000949 anxiolytic effect Effects 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
150000001916 cyano esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000013305 food Nutrition 0.000 description 3
210000002683 foot Anatomy 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
239000007937 lozenge Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 3
230000036544 posture Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
238000010792 warming Methods 0.000 description 3
UJBOOUHRTQVGRU-ZCFIWIBFSA-N (3r)-3-methylcyclohexan-1-one Chemical compound C[C@@H]1CCCC(=O)C1 UJBOOUHRTQVGRU-ZCFIWIBFSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
241000288950 Callithrix jacchus Species 0.000 description 2
206010019196 Head injury Diseases 0.000 description 2
208000004454 Hyperalgesia Diseases 0.000 description 2
208000035154 Hyperesthesia Diseases 0.000 description 2
101500028027 Mus musculus Cathelin-related antimicrobial peptide Proteins 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
206010043994 Tonic convulsion Diseases 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
230000004075 alteration Effects 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000005349 anion exchange Methods 0.000 description 2
239000002249 anxiolytic agent Substances 0.000 description 2
ZXVOCOLRQJZVBW-UHFFFAOYSA-N azane;ethanol Chemical compound N.CCO ZXVOCOLRQJZVBW-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010418 carrageenan Nutrition 0.000 description 2
229920001525 carrageenan Polymers 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
229940110456 cocoa butter Drugs 0.000 description 2
235000019868 cocoa butter Nutrition 0.000 description 2
239000003086 colorant Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000003745 diagnosis Methods 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
235000019634 flavors Nutrition 0.000 description 2
239000007789 gas Substances 0.000 description 2
210000000548 hind-foot Anatomy 0.000 description 2
230000007954 hypoxia Effects 0.000 description 2
239000012280 lithium aluminium hydride Substances 0.000 description 2
UJBOOUHRTQVGRU-UHFFFAOYSA-N m-methylcyclohexanone Natural products CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 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
238000005259 measurement Methods 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
238000005192 partition Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000006187 pill Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
238000007920 subcutaneous administration Methods 0.000 description 2
239000000829 suppository Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
230000000946 synaptic effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
239000012485 toluene extract Substances 0.000 description 2
230000008733 trauma Effects 0.000 description 2
MSANHHHQJYQEOK-KNVOCYPGSA-N (3r,5s)-3,5-dimethylcyclohexan-1-one Chemical compound C[C@H]1C[C@@H](C)CC(=O)C1 MSANHHHQJYQEOK-KNVOCYPGSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
XBNGYFFABRKICK-UHFFFAOYSA-N 2,3,4,5,6-pentafluorophenol Chemical compound OC1=C(F)C(F)=C(F)C(F)=C1F XBNGYFFABRKICK-UHFFFAOYSA-N 0.000 description 1
VRSDDSCAGYMHDB-UHFFFAOYSA-N 2-[1-(aminomethyl)-2-methylcyclohexyl]acetic acid Chemical compound CC1CCCCC1(CN)CC(O)=O VRSDDSCAGYMHDB-UHFFFAOYSA-N 0.000 description 1
CSJQXOUMYNIPCU-UHFFFAOYSA-N 2-[1-(aminomethyl)-4-propan-2-ylcyclohexyl]acetic acid Chemical compound CC(C)C1CCC(CN)(CC(O)=O)CC1 CSJQXOUMYNIPCU-UHFFFAOYSA-N 0.000 description 1
SDDWVDGIHSCXOM-UHFFFAOYSA-N 2-[1-(aminomethyl)-4-tert-butylcyclohexyl]acetic acid Chemical compound CC(C)(C)C1CCC(CN)(CC(O)=O)CC1 SDDWVDGIHSCXOM-UHFFFAOYSA-N 0.000 description 1
ZVJQBBYAVPAFLX-UHFFFAOYSA-N 3,3-dimethylcyclohexan-1-one Chemical compound CC1(C)CCCC(=O)C1 ZVJQBBYAVPAFLX-UHFFFAOYSA-N 0.000 description 1
IITQJMYAYSNIMI-UHFFFAOYSA-N 3-Methyl-2-cyclohexen-1-one Chemical compound CC1=CC(=O)CCC1 IITQJMYAYSNIMI-UHFFFAOYSA-N 0.000 description 1
239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
FPKISACHVIIMRA-UHFFFAOYSA-N 4-propan-2-ylcyclohexan-1-one Chemical compound CC(C)C1CCC(=O)CC1 FPKISACHVIIMRA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000349731 Afzelia bipindensis Species 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 1
206010002660 Anoxia Diseases 0.000 description 1
241000976983 Anoxia Species 0.000 description 1
206010003497 Asphyxia Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
JXYACYYPACQCDM-UHFFFAOYSA-N Benzyl glycinate Chemical compound NCC(=O)OCC1=CC=CC=C1 JXYACYYPACQCDM-UHFFFAOYSA-N 0.000 description 1
208000020925 Bipolar disease Diseases 0.000 description 1
201000006474 Brain Ischemia Diseases 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
108090000312 Calcium Channels Proteins 0.000 description 1
102000003922 Calcium Channels Human genes 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
208000018152 Cerebral disease Diseases 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
238000006969 Curtius rearrangement reaction Methods 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
206010014498 Embolic stroke Diseases 0.000 description 1
241000400611 Eucalyptus deanei Species 0.000 description 1
206010016374 Feelings of worthlessness Diseases 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010018985 Haemorrhage intracranial Diseases 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
208000013016 Hypoglycemia Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
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 1
208000008574 Intracranial Hemorrhages 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
206010026749 Mania Diseases 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
101100370002 Mus musculus Tnfsf14 gene Proteins 0.000 description 1
206010028923 Neonatal asphyxia Diseases 0.000 description 1
208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 description 1
208000018737 Parkinson disease Diseases 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
241000269800 Percidae Species 0.000 description 1
206010034912 Phobia Diseases 0.000 description 1
206010035039 Piloerection Diseases 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
241000283984 Rodentia Species 0.000 description 1
108091006463 SLC25A24 Proteins 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
208000027520 Somatoform disease Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
241000287181 Sturnus vulgaris Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000000556 agonist Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
102000015007 alpha-adrenergic receptor activity proteins Human genes 0.000 description 1
108040006816 alpha-adrenergic receptor activity proteins Proteins 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
230000000202 analgesic effect Effects 0.000 description 1
230000007953 anoxia Effects 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000001430 anti-depressive effect Effects 0.000 description 1
239000001961 anticonvulsive agent Substances 0.000 description 1
239000000935 antidepressant agent Substances 0.000 description 1
229940005513 antidepressants Drugs 0.000 description 1
230000000338 anxiogenic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
235000021311 artificial sweeteners Nutrition 0.000 description 1
238000003556 assay Methods 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
210000005013 brain tissue Anatomy 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
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
238000013172 carotid endarterectomy Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
238000002585 cerebral angiography Methods 0.000 description 1
206010008118 cerebral infarction Diseases 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
229910052801 chlorine Inorganic materials 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000000306 component Substances 0.000 description 1
230000000985 convulsing effect Effects 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
CCGKOQOJPYTBIH-UHFFFAOYSA-N ethenone Chemical compound C=C=O CCGKOQOJPYTBIH-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
210000004744 fore-foot Anatomy 0.000 description 1
238000009472 formulation Methods 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
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000008240 homogeneous mixture Substances 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
230000002218 hypoglycaemic effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
IHLVCKWPAMTVTG-UHFFFAOYSA-N lithium;carbanide Chemical compound [Li+].[CH3-] IHLVCKWPAMTVTG-UHFFFAOYSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
150000002739 metals Chemical class 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
238000001543 one-way ANOVA Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
208000027753 pain disease Diseases 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachloro-phenol Natural products OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 1
229960005152 pentetrazol Drugs 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
208000033300 perinatal asphyxia Diseases 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
208000019899 phobic disease Diseases 0.000 description 1
230000005371 pilomotor reflex Effects 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
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000011002 quantification Methods 0.000 description 1
238000003653 radioligand binding assay Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000009738 saturating Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
238000013222 sprague-dawley male rat Methods 0.000 description 1
230000000087 stabilizing effect Effects 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
208000005809 status epilepticus Diseases 0.000 description 1
239000000126 substance Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
238000012353 t test Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000000451 tissue damage Effects 0.000 description 1
231100000827 tissue damage Toxicity 0.000 description 1
230000001256 tonic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
238000012549 training Methods 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
238000010200 validation analysis Methods 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
- 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
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- A61P25/12—Antiepileptics; Anticonvulsants for grand-mal
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- 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
- A61P25/22—Anxiolytics
- 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
- A61P25/24—Antidepressants
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- 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
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
General Chemical & Material Sciences (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)

IL12554497A 1996-03-14 1997-02-18 Transformed cyclic amino acids and pharmaceutical preparations containing them IL125544A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US1343296P	1996-03-14	1996-03-14
PCT/US1997/002295 WO1997033858A1 (en)	1996-03-14	1997-02-18	Novel substituted cyclic amino acids as pharmaceutical agents

Publications (2)

Publication Number	Publication Date
IL125544A0 IL125544A0 (en)	1999-03-12
IL125544A true IL125544A (en)	2002-03-10

Family

ID=21759938

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL12554497A IL125544A (en)	1996-03-14	1997-02-18	Transformed cyclic amino acids and pharmaceutical preparations containing them

Country Status (29)

Country	Link
US (1)	US6103932A (2)
EP (1)	EP0888286B1 (2)
JP (1)	JP2000506861A (2)
KR (1)	KR100512506B1 (2)
AT (1)	ATE207878T1 (2)
AU (1)	AU734173B2 (2)
BG (1)	BG63662B1 (2)
BR (1)	BR9708200A (2)
CA (1)	CA2244912C (2)
CZ (1)	CZ293759B6 (2)
DE (1)	DE69707842T2 (2)
DK (2)	DK0888286T3 (2)
EA (1)	EA002765B1 (2)
EE (1)	EE9800309A (2)
ES (1)	ES2167717T3 (2)
GE (1)	GEP20012413B (2)
HU (1)	HU224720B1 (2)
IL (1)	IL125544A (2)
IS (1)	IS1990B (2)
MX (1)	MX9806069A (2)
NO (1)	NO984205L (2)
NZ (1)	NZ331143A (2)
PL (1)	PL185991B1 (2)
PT (1)	PT888286E (2)
SK (1)	SK283295B6 (2)
TR (1)	TR199801807T2 (2)
UA (1)	UA49011C2 (2)
WO (1)	WO1997033858A1 (2)
ZA (1)	ZA972200B (2)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IL126999A (en)	1996-07-24	2002-03-10	Warner Lambert Co	Pharmaceutical preparations containing isobutylgaba and its history for use in the treatment of pain
ATE323067T1 (de)	1997-10-27	2006-04-15	Warner Lambert Co	Zyklische aminosäuren und deren derivate als arzneimittel
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
DE19751062A1 (de) *	1997-11-18	1999-07-08	Univ Ludwigs Albert	An 4-Stellung substituierte 2-Pyrrolidinon-Derivate zur Verringerung des extrazellulären Glutamat-Spiegels
CN1131855C (zh) *	1997-12-16	2003-12-24	沃尼尔·朗伯公司	1－取代－1－氨基甲基－环烷衍生物(=加巴喷丁类似物)、其制备及其在治疗神经病方面的用途
EP1094817A1 (en) *	1998-07-09	2001-05-02	Warner-Lambert Company	Compositions comprising gaba analogs and caffeine
EP1031350A1 (en) *	1999-02-23	2000-08-30	Warner-Lambert Company	Use of a gabapentin-analog for the manufacture of a medicament for preventing and treating visceral pain
US6992109B1 (en) *	1999-04-08	2006-01-31	Segal Catherine A	Method for the treatment of incontinence
WO2001042191A1 (en) *	1999-12-08	2001-06-14	Warner-Lambert Company	Branched chain amino acid-dependent aminotransferase inhibitors and their use in the treatment of diabetic retinopathy
WO2001072311A1 (en) *	2000-03-28	2001-10-04	Delorenzo Robert J	Inhibition of a novel calcium injury current that forms in neurons during injury prevents neuronal cell death
GB2362646A (en) *	2000-05-26	2001-11-28	Warner Lambert Co	Cyclic amino acid derivatives useful as pharmaceutical agents
DE10048715A1 (de) *	2000-09-30	2004-05-19	Grünenthal GmbH	Verwendung von Aminosäure zur Behandlung von Schmerz
WO2002028881A1 (en) *	2000-10-06	2002-04-11	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
US6683112B2 (en) *	2000-10-24	2004-01-27	Andrx Corporation	Gabapentin prodrugs and formulations
GB2368579A (en) *	2000-10-31	2002-05-08	Parke Davis & Co Ltd	Azole pharmaceutical agents
DE01981893T1 (de) *	2000-11-02	2004-05-19	Teva Pharmaceutical Industries Ltd.	Verbessertes verfahren zur herstellung eines gabapentin-zwischenprodukts
US20040063994A1 (en) *	2001-03-16	2004-04-01	Paolo Rossi	Process for the preparation of cyclic amino acids
US8048917B2 (en)	2005-04-06	2011-11-01	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
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
US7232924B2 (en) *	2001-06-11	2007-06-19	Xenoport, Inc.	Methods for synthesis of acyloxyalkyl derivatives of GABA analogs
ATE540678T1 (de)	2001-06-11	2012-01-15	Xenoport Inc	Prodrugs aus gaba-analoga, zusammensetzungen und ihre verwendungen
EP1471909A4 (en) *	2002-01-16	2007-07-25	Endo Pharmaceuticals Inc	PHARMACEUTICAL COMPOSITION AND METHOD FOR THE TREATMENT OF DISEASES OF THE CENTRAL NERVOUS SYSTEM
WO2003077902A1 (en)	2002-02-19	2003-09-25	Xenoport, Inc.	Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof
AU2003222033A1 (en) *	2002-03-20	2003-10-08	Xenoport	Cyclic 1-(acyloxy)-alkyl prodrugs of gaba analogs, compositions and uses thereof
WO2003094842A2 (en) *	2002-05-07	2003-11-20	A & D Bioscience, Inc.	Conjugates comprising central nervous system active drug
WO2003099338A2 (en) *	2002-05-17	2003-12-04	Xenoport, Inc.	Amino acid conjugates providing for sustained systemic concentrations of gaba analogues
WO2004052360A1 (en) *	2002-12-11	2004-06-24	Xenoport, Inc.	Prodrugs of fused gaba analogs, pharmaceutical compositions and uses thereof
WO2004053192A1 (en) *	2002-12-11	2004-06-24	Xenoport, Inc.	Orally administered dosage forms of fused gaba analog prodrugs having reduced toxicity
WO2004054560A1 (en)	2002-12-13	2004-07-01	Warner-Lambert Company Llc	Alpha-2-delta ligand to treat lower urinary tract symptoms
CA2451267A1 (en)	2002-12-13	2004-06-13	Warner-Lambert Company Llc	Pharmaceutical uses for alpha2delta ligands
GB0301143D0 (en) *	2003-01-17	2003-02-19	Amedis Pharm Ltd	Compounds and their use
JP2006522146A (ja) *	2003-03-31	2006-09-28	ゼノポート，インコーポレイティド	Ｇａｂａ類似体のプロドラッグを使用するのぼせの治療または予防
KR20060119971A (ko)	2003-09-11	2006-11-24	제노포트 인코포레이티드	Ｇａｂａ 유사체의 전구약물을 이용한 요실금의 치료및/또는 예방
NZ545494A (en)	2003-09-12	2009-10-30	Pfizer	Combinations comprising alpha-2-delta ligands and serotonin / noradrenaline re-uptake inhibitors
AU2004274002B2 (en) *	2003-09-17	2011-04-28	Arbor Pharmaceuticals, Llc	Treating or preventing restless legs syndrome using prodrugs of GABA analogs
PT1677767E (pt)	2003-10-14	2011-10-13	Xenoport Inc	Forma cristalina de análogo de ácido gama-aminobutírico
US20050176680A1 (en)	2003-12-11	2005-08-11	Sepracor, Inc.	Combination of sedative and a neurotransmitter modulator, and methods for improving sleep quality and treating depression
US20050209332A1 (en) *	2004-03-17	2005-09-22	Hikal Limited	Gabapentin analogues and process thereof
US7632864B2 (en) *	2004-03-17	2009-12-15	Hikal Ltd.	Gabapentin analogues and process thereof
CA2570255A1 (en)	2004-03-17	2005-09-22	Hikal Limited	4-t-butylgabapentin and its synthesis
CA2584338C (en)	2004-11-04	2013-08-06	Xenoport, Inc.	Gabapentin prodrug sustained release oral dosage forms
WO2008073257A1 (en) *	2006-12-08	2008-06-19	Xenoport, Inc.	Use of prodrugs of gaba analogs for treating diseases
CA2673545A1 (en)	2006-12-22	2008-07-03	Recordati Ireland Limited	Combination therapy of lower urinary tract disorders with .alpha.2.delta. ligands and nsaids
WO2008103319A2 (en)	2007-02-16	2008-08-28	Ark Diagnostics, Inc.	Compounds and methods for use in detecting gabapentin
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
US20090118365A1 (en) *	2007-11-06	2009-05-07	Xenoport, Inc	Use of Prodrugs of GABA B Agonists for Treating Neuropathic and Musculoskeletal Pain
CA2706575C (en)	2008-01-25	2015-07-14	Xenoport, Inc.	Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs
EP2250148B1 (en)	2008-01-25	2016-08-17	XenoPort, Inc.	Crystalline form of calcium-salts of (3s)-aminomethyl-5-methyl-hexanoic acids and methods of use
US7868043B2 (en)	2008-01-25	2011-01-11	Xenoport, Inc.	Mesophasic forms of (3S)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use
CN105330603A (zh)	2008-10-08	2016-02-17	凯飞药业公司	Gaba偶联物及其使用方法
EP2349335B1 (en)	2008-10-24	2013-08-07	ARK Diagnostics, Inc.	Levetiracetam immunoassays
US9192681B2 (en)	2009-02-24	2015-11-24	Nektar Therapeutics	Oligomer-amino acid conjugates
US20110130454A1 (en) *	2009-11-24	2011-06-02	Xenoport, Inc.	Prodrugs of gamma-amino acid, alpha-2-delta ligands, pharmaceutical compositions and uses thereof
US20110124705A1 (en) *	2009-11-24	2011-05-26	Xenoport, Inc.	Prodrugs of alpha-2-delta ligands, pharmaceutical compositions and uses thereof
US9066853B2 (en)	2013-01-15	2015-06-30	Warsaw Orthopedic, Inc.	Clonidine compounds in a biodegradable fiber
EP2945942B1 (en)	2013-01-18	2018-05-09	ARK Diagnostics, Inc.	Voriconazole immunoassays
CA2903000C (en)	2013-01-28	2021-10-12	Hector L. Lopez	Methods of improving tolerability, pharmacodynamics, and efficacy of .beta.-alanine and use therefor
US9920136B2 (en)	2013-02-13	2018-03-20	Ark Diagnostics, Inc.	Posaconazole immunoassays
CN112424158A (zh)	2018-05-14	2021-02-26	昌郁医药公司	萘普生和普瑞巴林的1-(酰氧基)-烷基氨基甲酸酯药物缀合物的结晶形式

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
DE2543821C2 (de) *	1974-12-21	1984-10-18	Gödecke AG, 1000 Berlin	Bestimmte Salze und Ester von 1-Aminomethyl-1-cycloalkanessigsäuren und diese Verbindungen enthaltende Arzneimittel
US4087544A (en) *	1974-12-21	1978-05-02	Warner-Lambert Company	Treatment of cranial dysfunctions using novel cyclic amino acids
DE2611690A1 (de) *	1976-03-19	1977-09-22	Goedecke Ag	Cyclische sulfonyloxyimide
DE2626467C2 (de) *	1976-06-12	1984-11-22	Gödecke AG, 1000 Berlin	1-(N-Isopropylaminomethyl)-cyclohexanessigsäure, Verfahren zu deren Herstellung und diese Verbindung enthaltende Arzneimittel
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
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
DE3928182A1 (de) *	1989-08-25	1991-02-28	Goedecke Ag	Verfahren zur herstellung von gabapentin
DE3928184A1 (de) *	1989-08-25	1991-02-28	Goedecke Ag	Verfahren zur herstellung von cyclischen aminosaeurederivaten sowie zwischenprodukte
US5319135A (en) *	1989-08-25	1994-06-07	Warner-Lambert Company	Process for cyclic amino acid anticonvulsant compounds
US5098931A (en) *	1989-08-31	1992-03-24	Merck & Co., Inc.	7-substituted HMG-CoA reductase inhibitors
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
FI905584L (fi) *	1989-11-16	1991-05-17	Lonza Ag	Foerfarande foer framstaellning av 1-(aminometyl)cyklohexanaettikssyra.
US5084479A (en) *	1990-01-02	1992-01-28	Warner-Lambert Company	Novel methods for treating neurodegenerative diseases
TW201738B (2) *	1990-03-20	1993-03-11	Sanofi Co
EP0458751A1 (en) *	1990-05-25	1991-11-27	Warner-Lambert Company	Delivery system for cyclic amino acids with improved taste, texture and compressibility
US5025035A (en) *	1990-10-12	1991-06-18	Warner-Lambert Company	Method of treating depression
FR2691146B1 (fr) *	1992-05-15	1998-01-02	Adir	Nouveaux derives d'acides alcenecarboxyliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
ATE166650T1 (de) *	1993-03-04	1998-06-15	Pfizer	Spiroazacyclischderivate als substanz p antagonisten
US5792796A (en) *	1994-07-27	1998-08-11	Warner-Lambert Company	Methods for treating anxiety and panic

1997
- 1997-02-18 HU HU9902136A patent/HU224720B1/hu not_active IP Right Cessation
- 1997-02-18 JP JP9532601A patent/JP2000506861A/ja not_active Ceased
- 1997-02-18 US US09/068,874 patent/US6103932A/en not_active Expired - Fee Related
- 1997-02-18 WO PCT/US1997/002295 patent/WO1997033858A1/en not_active Ceased
- 1997-02-18 UA UA98105386A patent/UA49011C2/uk unknown
- 1997-02-18 SK SK1238-98A patent/SK283295B6/sk unknown
- 1997-02-18 EE EE9800309A patent/EE9800309A/xx unknown
- 1997-02-18 KR KR10-1998-0707229A patent/KR100512506B1/ko not_active Expired - Fee Related
- 1997-02-18 CA CA002244912A patent/CA2244912C/en not_active Expired - Fee Related
- 1997-02-18 BR BR9708200A patent/BR9708200A/pt not_active Application Discontinuation
- 1997-02-18 GE GEAP19974526A patent/GEP20012413B/en unknown
- 1997-02-18 IL IL12554497A patent/IL125544A/en not_active IP Right Cessation
- 1997-02-18 TR TR1998/01807T patent/TR199801807T2/xx unknown
- 1997-02-18 NZ NZ331143A patent/NZ331143A/en unknown
- 1997-02-18 PT PT97908655T patent/PT888286E/pt unknown
- 1997-02-18 EP EP97908655A patent/EP0888286B1/en not_active Expired - Lifetime
- 1997-02-18 DK DK97908655T patent/DK0888286T3/da active
- 1997-02-18 PL PL97328816A patent/PL185991B1/pl not_active IP Right Cessation
- 1997-02-18 DK DK97906630T patent/DK0888285T3/da active
- 1997-02-18 CZ CZ19982863A patent/CZ293759B6/cs not_active IP Right Cessation
- 1997-02-18 EA EA199800798A patent/EA002765B1/ru unknown
- 1997-02-18 ES ES97908655T patent/ES2167717T3/es not_active Expired - Lifetime
- 1997-02-18 AU AU20511/97A patent/AU734173B2/en not_active Ceased
- 1997-02-18 DE DE69707842T patent/DE69707842T2/de not_active Expired - Fee Related
- 1997-02-18 AT AT97908655T patent/ATE207878T1/de not_active IP Right Cessation
- 1997-03-13 ZA ZA9702200A patent/ZA972200B/xx unknown
1998
- 1998-07-28 MX MX9806069A patent/MX9806069A/es active IP Right Grant
- 1998-08-10 IS IS4819A patent/IS1990B/is unknown
- 1998-08-28 BG BG102733A patent/BG63662B1/bg unknown
- 1998-09-11 NO NO984205A patent/NO984205L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IS1990B (is)	2005-02-15
SK283295B6 (sk)	2003-05-02
DE69707842T2 (de)	2002-05-16
CZ286398A3 (cs)	1999-03-17
GEP20012413B (en)	2001-04-25
SK123898A3 (en)	2000-04-10
HU224720B1 (en)	2006-01-30
IS4819A (is)	1998-08-10
ATE207878T1 (de)	2001-11-15
HUP9902136A3 (en)	2000-03-28
TR199801807T2 (xx)	1998-12-21
EP0888286A1 (en)	1999-01-07
AU2051197A (en)	1997-10-01
BG102733A (en)	1999-04-30
CZ293759B6 (cs)	2004-07-14
IL125544A0 (en)	1999-03-12
EA002765B1 (ru)	2002-08-29
JP2000506861A (ja)	2000-06-06
EE9800309A (et)	1999-02-15
BR9708200A (pt)	1999-07-27
HUP9902136A2 (hu)	1999-10-28
MX9806069A (es)	1998-11-30
DE69707842D1 (de)	2001-12-06
AU734173B2 (en)	2001-06-07
CA2244912C (en)	2005-07-12
NZ331143A (en)	2001-06-29
UA49011C2 (uk)	2002-09-16
WO1997033858A1 (en)	1997-09-18
KR19990087756A (ko)	1999-12-27
EP0888286B1 (en)	2001-10-31
EA199800798A1 (ru)	1999-04-29
ZA972200B (en)	1997-09-17
US6103932A (en)	2000-08-15
ES2167717T3 (es)	2002-05-16
NO984205D0 (no)	1998-09-11
DK0888285T3 (da)	2002-04-08
KR100512506B1 (ko)	2005-12-21
DK0888286T3 (da)	2002-02-18
CA2244912A1 (en)	1997-09-18
PL328816A1 (en)	1999-02-15
BG63662B1 (bg)	2002-08-30
PL185991B1 (pl)	2003-09-30
NO984205L (no)	1998-09-14
PT888286E (pt)	2002-04-29

Legal Events

Date	Code	Title
2002-08-14	FF	Patent granted
2002-08-14	KB	Patent renewed
2003-04-10	KB	Patent renewed
2007-05-21	KB	Patent renewed
2011-09-27	MM9K	Patent not in force due to non-payment of renewal fees

Publication	Publication Date	Title
EP0888286B1 (en)	2001-10-31	Novel substituted cyclic amino acids as pharmaceutical agents
AU731279B2 (en)	2001-03-29	Novel bridged cyclic amino acids as pharmaceutical agents
AU733896B2 (en)	2001-05-31	Substituted gamma aminobutyric acids as pharmaceutical agents
AU720628B2 (en)	2000-06-08	Novel cyclic amino acids as pharmaceutical agents
EP1032555B1 (en)	2006-04-12	Cyclic amino acids and derivatives thereof useful as pharmaceutical agents
AU759619B2 (en)	2003-04-17	Novel amines as pharmaceutical agents
EP1082306A1 (en)	2001-03-14	Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel
CA2245647C (en)	2006-03-21	Novel bridged cyclic amino acids as pharmaceutical agents
PT888285E (pt)	2002-04-29	Novos amino acidos ciclicos em ponte como agentes farmaceuticos
MXPA00009494A (en)	2001-07-09	Conformationally constrained amino acid compounds having affinity for the alpha2delta subunit of a calcium channel