JP2000511877A - 医薬としての新規な環状アミノ酸 - Google Patents

医薬としての新規な環状アミノ酸

Info

Publication number: JP2000511877A
Authority: JP; Japan
Prior art keywords: compound; benzyl; carbon atoms; treatment; mammal
Prior art date: 1996-02-07
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.): Abandoned

Application number

JP09528505A

Other languages

English (en)

Japanese (ja)

Other versions

JP2000511877A5 (2

Inventor

ホーウエル，デイビツド・シー

ブライアンズ，ジヤステイン・エス

ニーン，クレア・オー

ラトクリフ，ジヤイルズ・エス

Original Assignee

ワーナー―ランバート・コンパニー

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.)

1996-02-07

Filing date

1997-01-02

Publication date

2000-09-12

1997-01-02 Application filed by ワーナー―ランバート・コンパニー filed Critical ワーナー―ランバート・コンパニー

2000-09-12 Publication of JP2000511877A publication Critical patent/JP2000511877A/ja

2004-11-11 Publication of JP2000511877A5 publication Critical patent/JP2000511877A5/ja

Status Abandoned legal-status Critical Current

Links

-1 cyclic amino acids Chemical class 0.000 title abstract description 19
239000003814 drug Substances 0.000 title abstract description 11
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
201000010099 disease Diseases 0.000 claims abstract description 16
208000019901 Anxiety disease Diseases 0.000 claims abstract description 7
230000036506 anxiety Effects 0.000 claims abstract description 7
208000002193 Pain Diseases 0.000 claims abstract description 6
230000004770 neurodegeneration Effects 0.000 claims abstract description 6
208000015122 neurodegenerative disease Diseases 0.000 claims abstract description 6
230000036407 pain Effects 0.000 claims abstract description 6
206010015037 epilepsy Diseases 0.000 claims abstract description 5
206010042772 syncope Diseases 0.000 claims abstract description 4
208000006083 Hypokinesia Diseases 0.000 claims abstract description 3
230000003483 hypokinetic effect Effects 0.000 claims abstract description 3
230000002981 neuropathic effect Effects 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 24
238000000034 method Methods 0.000 claims description 20
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000004432 carbon atom Chemical group C* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
229910052717 sulfur Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
DMBZPJRQJHDESH-UHFFFAOYSA-N 2-[4-(aminomethyl)oxan-4-yl]acetic acid Chemical compound OC(=O)CC1(CN)CCOCC1 DMBZPJRQJHDESH-UHFFFAOYSA-N 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical class 0.000 claims description 4
206010010904 Convulsion Diseases 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
230000001225 therapeutic effect Effects 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
241000124008 Mammalia Species 0.000 claims 8
238000002360 preparation method Methods 0.000 abstract description 9
229940079593 drug Drugs 0.000 abstract description 8
239000000543 intermediate Substances 0.000 abstract description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
239000000203 mixture Substances 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 10
238000012360 testing method Methods 0.000 description 9
241000700159 Rattus Species 0.000 description 8
239000000243 solution Substances 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
208000006011 Stroke Diseases 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000002775 capsule Substances 0.000 description 6
230000002490 cerebral effect Effects 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
ZIUSEGSNTOUIPT-UHFFFAOYSA-N ethyl 2-cyanoacetate Chemical compound CCOC(=O)CC#N ZIUSEGSNTOUIPT-UHFFFAOYSA-N 0.000 description 5
238000009472 formulation Methods 0.000 description 5
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000036651 mood Effects 0.000 description 5
239000000126 substance Substances 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
208000020401 Depressive disease Diseases 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000006870 function Effects 0.000 description 4
229960002870 gabapentin Drugs 0.000 description 4
229960003692 gamma aminobutyric acid Drugs 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
208000014674 injury Diseases 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
239000011573 trace mineral Substances 0.000 description 4
235000013619 trace mineral Nutrition 0.000 description 4
206010021143 Hypoxia Diseases 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000000949 anxiolytic effect Effects 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
238000003745 diagnosis Methods 0.000 description 3
239000000796 flavoring agent Substances 0.000 description 3
235000019634 flavors Nutrition 0.000 description 3
125000005843 halogen group Chemical group 0.000 description 3
239000007937 lozenge Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
230000000144 pharmacologic effect Effects 0.000 description 3
125000003884 phenylalkyl group Chemical group 0.000 description 3
239000006187 pill Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
BCKRPDOWCLBAJM-UHFFFAOYSA-N 2-[4-(aminomethyl)thian-4-yl]acetic acid Chemical compound OC(=O)CC1(CN)CCSCC1 BCKRPDOWCLBAJM-UHFFFAOYSA-N 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-M 2-cyanoacetate Chemical compound [O-]C(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-M 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
241000288950 Callithrix jacchus Species 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
206010019196 Head injury Diseases 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
241000699666 Mus <mouse, genus> Species 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
208000027418 Wounds and injury Diseases 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 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
230000001174 ascending effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003086 colorant Substances 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
150000001916 cyano esters Chemical class 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
230000006378 damage Effects 0.000 description 2
230000000994 depressogenic effect Effects 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000007789 gas Substances 0.000 description 2
230000007954 hypoxia Effects 0.000 description 2
PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
239000008297 liquid dosage form Substances 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
241001515942 marmosets Species 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000004430 oxygen atom Chemical group O* 0.000 description 2
238000005192 partition Methods 0.000 description 2
230000036544 posture Effects 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
230000035939 shock Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 2
239000007909 solid dosage form Substances 0.000 description 2
239000003381 stabilizer Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
125000004434 sulfur atom Chemical group 0.000 description 2
239000013589 supplement Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000000946 synaptic effect Effects 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000002562 thickening agent Substances 0.000 description 2
230000008733 trauma Effects 0.000 description 2
230000002792 vascular Effects 0.000 description 2
208000019553 vascular disease Diseases 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
JUXAVSAMVBLDKO-UHFFFAOYSA-N 1-(1-azabicyclo[2.2.2]octan-3-yl)-3-[3-(1h-indol-3-yl)-1-oxo-1-spiro[1,2-dihydroindene-3,4'-piperidine]-1'-ylpropan-2-yl]urea Chemical compound C1N(CC2)CCC2C1NC(=O)NC(C(=O)N1CCC2(C3=CC=CC=C3CC2)CC1)CC1=CNC2=CC=CC=C12 JUXAVSAMVBLDKO-UHFFFAOYSA-N 0.000 description 1
AIAIJTBGSWGMGV-UHFFFAOYSA-N 2-hydroxypropanoic acid;oxalic acid Chemical compound CC(O)C(O)=O.OC(=O)C(O)=O AIAIJTBGSWGMGV-UHFFFAOYSA-N 0.000 description 1
239000003477 4 aminobutyric acid receptor stimulating agent Substances 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
102000005862 Angiotensin II Human genes 0.000 description 1
101800000733 Angiotensin-2 Proteins 0.000 description 1
206010002660 Anoxia Diseases 0.000 description 1
241000976983 Anoxia Species 0.000 description 1
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Natural products OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 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
208000020925 Bipolar disease Diseases 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
208000014644 Brain disease Diseases 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
206010008120 Cerebral ischaemia Diseases 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
238000006969 Curtius rearrangement reaction Methods 0.000 description 1
206010011953 Decreased activity Diseases 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
241001631030 Explorator Species 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
101000896080 Homo sapiens E3 ubiquitin-protein ligase BRE1B Proteins 0.000 description 1
208000023105 Huntington disease Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 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
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
206010026749 Mania Diseases 0.000 description 1
206010027951 Mood swings Diseases 0.000 description 1
208000008238 Muscle Spasticity Diseases 0.000 description 1
206010028923 Neonatal asphyxia Diseases 0.000 description 1
208000037212 Neonatal hypoxic and ischemic brain injury Diseases 0.000 description 1
241000750004 Nestor meridionalis Species 0.000 description 1
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
206010034912 Phobia Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
238000000692 Student's t-test Methods 0.000 description 1
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
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 1
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 1
229960001171 acetohydroxamic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000556 agonist Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005466 alkylenyl group Chemical group 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
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
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 1
229950006323 angiotensin ii Drugs 0.000 description 1
238000010171 animal model Methods 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
229960003965 antiepileptics 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
235000010323 ascorbic acid Nutrition 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
230000003925 brain function Effects 0.000 description 1
208000029028 brain injury Diseases 0.000 description 1
239000000872 buffer Substances 0.000 description 1
244000240602 cacao Species 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 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
208000026106 cerebrovascular disease 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
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000007906 compression Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
230000002920 convulsive effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000002405 diagnostic procedure Methods 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
238000012377 drug delivery Methods 0.000 description 1
210000001198 duodenum Anatomy 0.000 description 1
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
239000003480 eluent Substances 0.000 description 1
230000001037 epileptic effect Effects 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
239000000706 filtrate Substances 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
235000013305 food Nutrition 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
239000012362 glacial acetic acid Substances 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229940093915 gynecological organic acid Drugs 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
102000046656 human RNF40 Human genes 0.000 description 1
BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
206010022437 insomnia Diseases 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical class OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 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
235000014380 magnesium carbonate Nutrition 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
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
150000007522 mineralic acids Chemical class 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
BNZBMEIFAOYZEA-UHFFFAOYSA-N n-cyanoacetamide Chemical compound CC(=O)NC#N BNZBMEIFAOYZEA-UHFFFAOYSA-N 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
235000021096 natural sweeteners Nutrition 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
238000001543 one-way ANOVA Methods 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000001301 oxygen Substances 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
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
230000035515 penetration Effects 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
229920001223 polyethylene glycol Polymers 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
102220240796 rs553605556 Human genes 0.000 description 1
229960004889 salicylic acid Drugs 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
239000000377 silicon dioxide Substances 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
208000018198 spasticity Diseases 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000001356 surgical procedure Methods 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
239000007885 tablet disintegrant Substances 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
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
OVRJVKCZJCNSOW-UHFFFAOYSA-N thian-4-one Chemical compound O=C1CCSCC1 OVRJVKCZJCNSOW-UHFFFAOYSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
239000012485 toluene extract Substances 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
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 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
238000007631 vascular surgery Methods 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
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/06—Antimigraine agents
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms

Landscapes

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

JP09528505A 1996-02-07 1997-01-02 医薬としての新規な環状アミノ酸 Abandoned JP2000511877A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US1127896P	1996-02-07	1996-02-07
US60/011,278		1996-02-07
PCT/US1997/000255 WO1997029101A1 (en)	1996-02-07	1997-01-02	Novel cyclic amino acids as pharmaceutical agents

Publications (2)

Publication Number	Publication Date
JP2000511877A true JP2000511877A (ja)	2000-09-12
JP2000511877A5 JP2000511877A5 (2)	2004-11-11

Family

ID=21749660

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP09528505A Abandoned JP2000511877A (ja)	1996-02-07	1997-01-02	医薬としての新規な環状アミノ酸

Country Status (22)

Country	Link
US (1)	US5929088A (2)
EP (1)	EP0888325B1 (2)
JP (1)	JP2000511877A (2)
KR (1)	KR19990082349A (2)
AT (1)	ATE218135T1 (2)
AU (1)	AU720628B2 (2)
BR (1)	BR9707366A (2)
CA (1)	CA2244708A1 (2)
CZ (1)	CZ296052B6 (2)
DE (1)	DE69712877T2 (2)
DK (1)	DK0888325T3 (2)
EA (1)	EA001534B1 (2)
ES (1)	ES2176668T3 (2)
HU (1)	HUP9901074A3 (2)
IL (1)	IL125562A (2)
NO (1)	NO983612L (2)
NZ (1)	NZ326669A (2)
PL (1)	PL328432A1 (2)
PT (1)	PT888325E (2)
SK (1)	SK282665B6 (2)
WO (1)	WO1997029101A1 (2)
ZA (1)	ZA97991B (2)

Families Citing this family (38)

* 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
JP3878809B2 (ja) *	1997-09-18	2007-02-07	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	ガバペンチン類似体を製造するための新規な立体選択的方法
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
CA2304967C (en) *	1997-12-16	2005-06-14	Warner-Lambert Company	4(3)substituted-4(3)-aminomethyl-(thio)pyran or -piperidine derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
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
EP1361847A2 (en)	2000-10-06	2003-11-19	Xenoport, Inc.	Bile-acid conjugates for providing sustained systemic concentrations of drugs
WO2002028881A1 (en)	2000-10-06	2002-04-11	Xenoport, Inc.	Bile-acid derived compounds for providing sustained systemic concentrations of drugs after oral administration
GB2368579A (en) *	2000-10-31	2002-05-08	Parke Davis & Co Ltd	Azole pharmaceutical agents
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
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
ATE540678T1 (de)	2001-06-11	2012-01-15	Xenoport Inc	Prodrugs aus gaba-analoga, zusammensetzungen und ihre verwendungen
US7186855B2 (en)	2001-06-11	2007-03-06	Xenoport, Inc.	Prodrugs of GABA analogs, compositions and uses thereof
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
WO2003099338A2 (en)	2002-05-17	2003-12-04	Xenoport, Inc.	Amino acid conjugates providing for sustained systemic concentrations of gaba analogues
US20040092498A1 (en) *	2002-08-16	2004-05-13	David Blakemore	Substituted glycine derivatives for use as medicaments
WO2004052360A1 (en)	2002-12-11	2004-06-24	Xenoport, Inc.	Prodrugs of fused gaba analogs, pharmaceutical compositions and uses thereof
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
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
CA2584338C (en)	2004-11-04	2013-08-06	Xenoport, Inc.	Gabapentin prodrug sustained release oral dosage forms
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
WO2009024615A1 (en) *	2007-08-23	2009-02-26	Novartis Ag	Aminobenzyl-substituted cyclic sulfones useful as bace inhibitors
CA2706575C (en)	2008-01-25	2015-07-14	Xenoport, Inc.	Enantiomerically resolving acyloxyalkyl thiocarbonates used in synthesizing acyloxyalkyl carbamate prodrugs
US7868043B2 (en)	2008-01-25	2011-01-11	Xenoport, Inc.	Mesophasic forms of (3S)-aminomethyl-5-methyl-hexanoic acid prodrugs and methods of use
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
CN105330603A (zh)	2008-10-08	2016-02-17	凯飞药业公司	Gaba偶联物及其使用方法
WO2010084797A1 (ja) *	2009-01-21	2010-07-29	第一三共株式会社	含ヘテロ原子化合物
US9066853B2 (en)	2013-01-15	2015-06-30	Warsaw Orthopedic, Inc.	Clonidine compounds in a biodegradable fiber
CA2903000C (en)	2013-01-28	2021-10-12	Hector L. Lopez	Methods of improving tolerability, pharmacodynamics, and efficacy of .beta.-alanine and use therefor
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 (9)

* 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
US4087544A (en) *	1974-12-21	1978-05-02	Warner-Lambert Company	Treatment of cranial dysfunctions using novel cyclic amino acids
US5270317A (en) *	1990-03-20	1993-12-14	Elf Sanofi	N-substituted heterocyclic derivatives, their preparation and the pharmaceutical compositions in which they are present
AU663330B2 (en) *	1991-07-09	1995-10-05	Nippon Soda Co., Ltd.	Heterocyclic cyclohexanedione derivative, production thereof, and herbicide
US5514801A (en) *	1992-12-29	1996-05-07	Monsanto Company	Cyclic sulfone containing retroviral protease inhibitors
GB9314758D0 (en) *	1993-07-16	1993-08-25	Wyeth John & Brother Ltd	Heterocyclic derivatives
US5527194A (en) *	1994-02-02	1996-06-18	Brunswick Corporation	Thrust sensor for marine drives
US5491152A (en) *	1994-03-23	1996-02-13	The Du Pont Merck Pharmaceutical Company	Derivatives of cyclic ethers and sulfides for the treatment of atherosclerosis
US5760006A (en) *	1997-06-23	1998-06-02	Ortho Pharmaceutical Corporation	Anticonvulsant derivatives useful in treating psoriasis

1997
- 1997-01-02 EP EP97901385A patent/EP0888325B1/en not_active Expired - Lifetime
- 1997-01-02 US US09/077,053 patent/US5929088A/en not_active Expired - Fee Related
- 1997-01-02 DE DE69712877T patent/DE69712877T2/de not_active Expired - Fee Related
- 1997-01-02 HU HU9901074A patent/HUP9901074A3/hu unknown
- 1997-01-02 AU AU15295/97A patent/AU720628B2/en not_active Ceased
- 1997-01-02 EA EA199800682A patent/EA001534B1/ru not_active IP Right Cessation
- 1997-01-02 IL IL12556297A patent/IL125562A/en not_active IP Right Cessation
- 1997-01-02 CZ CZ19982452A patent/CZ296052B6/cs not_active IP Right Cessation
- 1997-01-02 NZ NZ326669A patent/NZ326669A/en unknown
- 1997-01-02 PL PL97328432A patent/PL328432A1/xx unknown
- 1997-01-02 AT AT97901385T patent/ATE218135T1/de not_active IP Right Cessation
- 1997-01-02 BR BR9707366A patent/BR9707366A/pt not_active Application Discontinuation
- 1997-01-02 ES ES97901385T patent/ES2176668T3/es not_active Expired - Lifetime
- 1997-01-02 KR KR1019980706079A patent/KR19990082349A/ko not_active Ceased
- 1997-01-02 CA CA002244708A patent/CA2244708A1/en not_active Abandoned
- 1997-01-02 WO PCT/US1997/000255 patent/WO1997029101A1/en not_active Ceased
- 1997-01-02 DK DK97901385T patent/DK0888325T3/da active
- 1997-01-02 SK SK1067-98A patent/SK282665B6/sk unknown
- 1997-01-02 PT PT97901385T patent/PT888325E/pt unknown
- 1997-01-02 JP JP09528505A patent/JP2000511877A/ja not_active Abandoned
- 1997-02-06 ZA ZA9700991A patent/ZA97991B/xx unknown
1998
- 1998-08-06 NO NO983612A patent/NO983612L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU720628B2 (en)	2000-06-08
HUP9901074A3 (en)	2001-08-28
CZ296052B6 (cs)	2005-12-14
DE69712877T2 (de)	2002-11-14
NZ326669A (en)	2001-05-25
WO1997029101A1 (en)	1997-08-14
NO983612L (no)	1998-10-06
ATE218135T1 (de)	2002-06-15
CA2244708A1 (en)	1997-08-14
HUP9901074A2 (hu)	2001-04-28
EA199800682A1 (ru)	1999-02-25
ES2176668T3 (es)	2002-12-01
PT888325E (pt)	2002-10-31
IL125562A (en)	2001-08-08
AU1529597A (en)	1997-08-28
PL328432A1 (en)	1999-02-01
CZ245298A3 (cs)	1998-11-11
DE69712877D1 (de)	2002-07-04
NO983612D0 (no)	1998-08-06
IL125562A0 (en)	1999-03-12
ZA97991B (en)	1997-08-15
EP0888325A1 (en)	1999-01-07
SK106798A3 (en)	1999-07-12
EA001534B1 (ru)	2001-04-23
DK0888325T3 (da)	2002-09-16
SK282665B6 (sk)	2002-11-06
KR19990082349A (ko)	1999-11-25
BR9707366A (pt)	1999-07-20
US5929088A (en)	1999-07-27
EP0888325B1 (en)	2002-05-29

Legal Events

Date	Code	Title	Description
2004-01-22	A521	Request for written amendment filed	Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20031226
2004-01-22	A621	Written request for application examination	Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20031226
2006-10-19	A72	Notification of change in name of applicant	Free format text: JAPANESE INTERMEDIATE CODE: A721 Effective date: 20060927
2006-10-19	A762	Written abandonment of application	Free format text: JAPANESE INTERMEDIATE CODE: A762 Effective date: 20060927

Publication	Publication Date	Title
JP2000511877A (ja)	2000-09-12	医薬としての新規な環状アミノ酸
KR100487032B1 (ko)	2005-12-21	약제로서신규한브리지된시클릭아미노산
KR100512506B1 (ko)	2005-12-21	제약제제로서신규한치환시클릭아미노산
JP4263717B2 (ja)	2009-05-13	医薬として有用な環状アミノ酸およびその誘導体
EP1047678B1 (en)	2004-09-08	1-substituted-1-aminomethyl-cycloalkane derivatives (=gabapentin analogues), their preparation and their use in the treatment of neurological disorders
JP2002524551A (ja)	2002-08-06	分枝鎖アルキルピロリジン−３−カルボン酸
JP2002514187A (ja)	2002-05-14	薬剤としての置換γ―アミノ酪酸
JP2002508352A (ja)	2002-03-19	４（３）置換−４（３）−アミノメチル−（チオ）ピラン又はピペリジン誘導体（＝ガバペンチン類似体）、それらの製法および神経病理学的疾患の治療における使用
EP0109020A2 (de)	1984-05-23	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
JP2003525207A (ja)	2003-08-26	薬剤として有用なアミノ複素環
JP2003500486A (ja)	2003-01-07	３−ヘテロアリールアルキル置換ｇａｂａ類似体
JPWO2019026994A1 (ja)	2020-10-08	アダマンチルメチルアミン誘導体およびその医薬としての使用
JPH06500097A (ja)	1994-01-06	５−（２−クロロ−１−ヒドロキシエチル）−４−メチルチアゾール含有の医薬製剤
US3639457A (en)	1972-02-01	N-substituted-beta-oxybutyramide semisuccinate and its salt having effects of increasing paradoxical sleep and tranquillizing
CA2245647C (en)	2006-03-21	Novel bridged cyclic amino acids as pharmaceutical agents