DE19840611A1 - GABA-uptake-Inhibitoren mit Pyrrolidinstruktur - Google Patents
GABA-uptake-Inhibitoren mit PyrrolidinstrukturInfo
- Publication number
- DE19840611A1 DE19840611A1 DE19840611A DE19840611A DE19840611A1 DE 19840611 A1 DE19840611 A1 DE 19840611A1 DE 19840611 A DE19840611 A DE 19840611A DE 19840611 A DE19840611 A DE 19840611A DE 19840611 A1 DE19840611 A1 DE 19840611A1
- Authority
- DE
- Germany
- Prior art keywords
- mmol
- alkyl
- optionally substituted
- nch
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 229940091860 GABA uptake inhibitor Drugs 0.000 title abstract description 6
- 239000002843 gaba uptake inhibitor Substances 0.000 title abstract description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 64
- 201000010099 disease Diseases 0.000 claims abstract description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 238000000034 method Methods 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical class 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 229910052799 carbon Inorganic materials 0.000 claims description 18
- -1 3-methyl-2-thienyl Chemical group 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 16
- 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 14
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000007428 synaptic transmission, GABAergic Effects 0.000 claims description 5
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 4
- 229910052708 sodium Inorganic materials 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 230000004962 physiological condition Effects 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 206010015037 epilepsy Diseases 0.000 abstract description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 54
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 36
- 239000012230 colorless oil Substances 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
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- 239000000243 solution Substances 0.000 description 20
- 238000004440 column chromatography Methods 0.000 description 19
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 description 18
- 238000007126 N-alkylation reaction Methods 0.000 description 17
- 238000000746 purification Methods 0.000 description 17
- 230000004044 response Effects 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 238000001953 recrystallisation Methods 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 9
- 229910052731 fluorine Inorganic materials 0.000 description 8
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 229910052801 chlorine Inorganic materials 0.000 description 7
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 description 6
- 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 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical class [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 5
- 102100035254 Sodium- and chloride-dependent GABA transporter 3 Human genes 0.000 description 5
- 101710104417 Sodium- and chloride-dependent GABA transporter 3 Proteins 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 239000001961 anticonvulsive agent Substances 0.000 description 5
- XNYIZVPSGNHISO-CYBMUJFWSA-N benzyl (2r)-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate Chemical compound COC(=O)C[C@H]1CCCN1C(=O)OCC1=CC=CC=C1 XNYIZVPSGNHISO-CYBMUJFWSA-N 0.000 description 5
- 210000003169 central nervous system Anatomy 0.000 description 5
- GWCPTZNOWFHMER-UHFFFAOYSA-N (4-bromo-1-phenylbut-1-enyl)benzene Chemical compound C=1C=CC=CC=1C(=CCCBr)C1=CC=CC=C1 GWCPTZNOWFHMER-UHFFFAOYSA-N 0.000 description 4
- KRXSGXVUQKRSCK-UHFFFAOYSA-N 2-[4-bromo-1-(3-methylthiophen-2-yl)but-1-enyl]-3-methylthiophene Chemical compound C1=CSC(C(=CCCBr)C2=C(C=CS2)C)=C1C KRXSGXVUQKRSCK-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 101710104414 Sodium- and chloride-dependent GABA transporter 1 Proteins 0.000 description 4
- 102100033927 Sodium- and chloride-dependent GABA transporter 1 Human genes 0.000 description 4
- 230000003556 anti-epileptic effect Effects 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229940017219 methyl propionate Drugs 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 108090000623 proteins and genes Proteins 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HLPYFOKKJKJMLR-GJZGRUSLSA-N (1r,5s)-5-(2,5-dihydropyrrole-1-carbonyl)-1,8,8-trimethyl-3-oxabicyclo[3.2.1]octan-4-one Chemical compound O=C([C@]12CC[C@@](COC2=O)(C1(C)C)C)N1CC=CC1 HLPYFOKKJKJMLR-GJZGRUSLSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010078791 Carrier Proteins Proteins 0.000 description 3
- 102000014914 Carrier Proteins Human genes 0.000 description 3
- 101150065749 Churc1 gene Proteins 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- 102100038239 Protein Churchill Human genes 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
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- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
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- 238000004128 high performance liquid chromatography Methods 0.000 description 3
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- HQEIPVHJHZTMDP-NUBCRITNSA-N methyl (2r)-pyrrolidine-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)[C@H]1CCCN1 HQEIPVHJHZTMDP-NUBCRITNSA-N 0.000 description 3
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- FECAUVOXGVMVNH-RGMNGODLSA-N methyl 2-[(2s)-pyrrolidin-2-yl]acetate;hydrochloride Chemical compound Cl.COC(=O)C[C@@H]1CCCN1 FECAUVOXGVMVNH-RGMNGODLSA-N 0.000 description 3
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19840611A DE19840611A1 (de) | 1998-09-05 | 1998-09-05 | GABA-uptake-Inhibitoren mit Pyrrolidinstruktur |
| PCT/EP1999/006486 WO2000014064A2 (fr) | 1998-09-05 | 1999-09-03 | Inhibiteurs d'absorption de gaba a structure pyrrolidinique |
| JP2000568823A JP2002524443A (ja) | 1998-09-05 | 1999-09-03 | ピロリジン構造を有するｇａｂａ摂取阻害剤 |
| AU59726/99A AU5972699A (en) | 1998-09-05 | 1999-09-03 | Gaba uptake inhibitors having a pyrrolidine structure |
| CA002343531A CA2343531A1 (fr) | 1998-09-05 | 1999-09-03 | Inhibiteurs d'absorption de gaba a structure pyrrolidinique |
| EP99968664A EP1109783A2 (fr) | 1998-09-05 | 1999-09-03 | Inhibiteurs d'absorption de gaba a structure pyrrolidinique |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19840611A DE19840611A1 (de) | 1998-09-05 | 1998-09-05 | GABA-uptake-Inhibitoren mit Pyrrolidinstruktur |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19840611A1 true DE19840611A1 (de) | 2000-03-09 |
Family
ID=7879962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19840611A Withdrawn DE19840611A1 (de) | 1998-09-05 | 1998-09-05 | GABA-uptake-Inhibitoren mit Pyrrolidinstruktur |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1109783A2 (fr) |
| JP (1) | JP2002524443A (fr) |
| AU (1) | AU5972699A (fr) |
| CA (1) | CA2343531A1 (fr) |
| DE (1) | DE19840611A1 (fr) |
| WO (1) | WO2000014064A2 (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7189757B2 (en) | 2001-10-16 | 2007-03-13 | Hypnion, Inc. | Treatment of sleep disorders using CNS target modulators |
| AU2002347906A2 (en) | 2001-10-16 | 2003-04-28 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| CA2690091A1 (fr) * | 2007-06-05 | 2008-12-11 | Nsab, Filial Af Neurosearch Sweden Ab, Sverige | Nouvelles phenylpyrrolidines disubstituees en tant que modulateurs de la neurotransmission catecholaminergique corticale |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514414A (en) * | 1982-10-25 | 1985-04-30 | Smithkline Beckman Corporation | N-Substituted pyrrolidineacetic acids and their esters |
| US4610995A (en) * | 1984-07-27 | 1986-09-09 | Coker Geoffrey G | Certain 1,1-diaryl-propenyl-3-(1-pyrrolidino-2-carboxylic acids, derivatives thereof and their anti-histaminic properties |
| EP0231996A2 (fr) * | 1986-01-07 | 1987-08-12 | Novo Nordisk A/S | Dérivés d'amino-acides |
| EP0374801A2 (fr) * | 1988-12-19 | 1990-06-27 | Novo Nordisk A/S | Acides azahétérocycliques N-substitués |
| EP0236342B1 (fr) * | 1985-06-26 | 1991-09-11 | Novo Nordisk A/S | Derives d'acides amines |
| WO1997045115A1 (fr) * | 1996-05-31 | 1997-12-04 | Trophix Pharmaceuticals, Inc. | Produit pharmaceutique pour le traitement de troubles neurologiques et neuropsychiatriques |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4383999A (en) * | 1981-05-26 | 1983-05-17 | Smithkline Beckman Corporation | Inhibition of GABA uptake by N-substituted azaheterocyclic carboxylic acids and their esters |
| GB8320704D0 (en) * | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agents |
| US4910312A (en) * | 1985-11-08 | 1990-03-20 | Warner-Lambert Company | Various N-substituted 3-piperidine carboxylic acids or N-substituted 3-pyridinecarboxylic acids and derivatives thereof |
-
1998
- 1998-09-05 DE DE19840611A patent/DE19840611A1/de not_active Withdrawn
-
1999
- 1999-09-03 EP EP99968664A patent/EP1109783A2/fr not_active Withdrawn
- 1999-09-03 CA CA002343531A patent/CA2343531A1/fr not_active Abandoned
- 1999-09-03 JP JP2000568823A patent/JP2002524443A/ja active Pending
- 1999-09-03 AU AU59726/99A patent/AU5972699A/en not_active Abandoned
- 1999-09-03 WO PCT/EP1999/006486 patent/WO2000014064A2/fr not_active Ceased
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4514414A (en) * | 1982-10-25 | 1985-04-30 | Smithkline Beckman Corporation | N-Substituted pyrrolidineacetic acids and their esters |
| US4610995A (en) * | 1984-07-27 | 1986-09-09 | Coker Geoffrey G | Certain 1,1-diaryl-propenyl-3-(1-pyrrolidino-2-carboxylic acids, derivatives thereof and their anti-histaminic properties |
| EP0236342B1 (fr) * | 1985-06-26 | 1991-09-11 | Novo Nordisk A/S | Derives d'acides amines |
| EP0231996A2 (fr) * | 1986-01-07 | 1987-08-12 | Novo Nordisk A/S | Dérivés d'amino-acides |
| EP0374801A2 (fr) * | 1988-12-19 | 1990-06-27 | Novo Nordisk A/S | Acides azahétérocycliques N-substitués |
| WO1997045115A1 (fr) * | 1996-05-31 | 1997-12-04 | Trophix Pharmaceuticals, Inc. | Produit pharmaceutique pour le traitement de troubles neurologiques et neuropsychiatriques |
Non-Patent Citations (2)
| Title |
|---|
| ANDERSEN,Knud Erik, et.al.: The Synthesis of Novel GABA Uptake Inhibitors. 1. Elucidation of the Structure-Activity Studies Leading to the Choice of (R)-1-[4,4-Bis(3-methyl-2-thienyl) -3-butenyl]-3-piperidinecarboxylic Acid (Tiagabine) as an Anticonvulsant Drug Candidate. In: J. Med. Chem. 1993, 36, S.1716-1725 * |
| PAVIA,Michael R., et.al.: Structure-Activity Studies on Benzhydrol-Containing Nipecotic Acid and Guvacine Derivatives as Potent, Orally-Active Inhibitors of GABA Uptake. In: J. Med. Chem. 1992, 35, S.4238-4248 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU5972699A (en) | 2000-03-27 |
| WO2000014064A3 (fr) | 2000-07-20 |
| EP1109783A2 (fr) | 2001-06-27 |
| CA2343531A1 (fr) | 2000-03-16 |
| JP2002524443A (ja) | 2002-08-06 |
| WO2000014064A2 (fr) | 2000-03-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| OM8 | Search report available as to paragraph 43 lit. 1 sentence 1 patent law | ||
| 8139 | Disposal/non-payment of the annual fee |