AU755800B2 - Cyclic amino acids and derivatives thereof useful as pharmaceutical agents - Google Patents
Cyclic amino acids and derivatives thereof useful as pharmaceutical agents Download PDFInfo
- Publication number
- AU755800B2 AU755800B2 AU96638/98A AU9663898A AU755800B2 AU 755800 B2 AU755800 B2 AU 755800B2 AU 96638/98 A AU96638/98 A AU 96638/98A AU 9663898 A AU9663898 A AU 9663898A AU 755800 B2 AU755800 B2 AU 755800B2
- Authority
- AU
- Australia
- Prior art keywords
- acetic acid
- aminomethyl
- cyclopentyl
- methyl
- ethyl
- 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.)
- Ceased
Links
- 229940093740 amino acid and derivative Drugs 0.000 title description 2
- 125000004122 cyclic group Chemical group 0.000 title description 2
- 239000008177 pharmaceutical agent Substances 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 581
- 150000001875 compounds Chemical class 0.000 claims description 102
- -1 hydroxy, hydroxymethyl Chemical group 0.000 claims description 74
- 239000002253 acid Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 42
- 239000003814 drug Substances 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 27
- QLHNVWKVWDIVIG-RKDXNWHRSA-N ethyl 2-[(3r,4r)-3,4-dimethylcyclopentylidene]acetate Chemical compound CCOC(=O)C=C1C[C@@H](C)[C@H](C)C1 QLHNVWKVWDIVIG-RKDXNWHRSA-N 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 241000124008 Mammalia Species 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 208000019901 Anxiety disease Diseases 0.000 claims description 10
- 230000036506 anxiety Effects 0.000 claims description 10
- 206010015037 epilepsy Diseases 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 230000036407 pain Effects 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- 208000002193 Pain Diseases 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 7
- CNCRBAYWBZGPBZ-HTQZYQBOSA-N (7r,8r)-7,8-dimethyl-2-azaspiro[4.4]nonan-3-one Chemical compound C1[C@@H](C)[C@H](C)CC11CC(=O)NC1 CNCRBAYWBZGPBZ-HTQZYQBOSA-N 0.000 claims description 6
- 208000006083 Hypokinesia Diseases 0.000 claims description 6
- 208000002173 dizziness Diseases 0.000 claims description 6
- 230000003483 hypokinetic effect Effects 0.000 claims description 6
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 6
- 206010061218 Inflammation Diseases 0.000 claims description 5
- 230000004054 inflammatory process Effects 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000002981 neuropathic effect Effects 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- OVCCKUOTVGFWJQ-UHFFFAOYSA-N ethyl 2-(3-benzylcyclobutylidene)acetate Chemical compound C1C(=CC(=O)OCC)CC1CC1=CC=CC=C1 OVCCKUOTVGFWJQ-UHFFFAOYSA-N 0.000 claims description 3
- UDBYYPDEHJNWBE-UHFFFAOYSA-N ethyl 2-[1-(nitromethyl)cyclobutyl]acetate Chemical compound CCOC(=O)CC1(C[N+]([O-])=O)CCC1 UDBYYPDEHJNWBE-UHFFFAOYSA-N 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- CNCRBAYWBZGPBZ-YUMQZZPRSA-N (7s,8s)-7,8-dimethyl-2-azaspiro[4.4]nonan-3-one Chemical compound C1[C@H](C)[C@@H](C)CC11CC(=O)NC1 CNCRBAYWBZGPBZ-YUMQZZPRSA-N 0.000 claims description 2
- WVFKRUXAEOXLHW-HTQZYQBOSA-N 2-[(3r,4r)-3,4-dimethyl-1-(nitromethyl)cyclopentyl]acetic acid Chemical compound C[C@@H]1CC(CC(O)=O)(C[N+]([O-])=O)C[C@H]1C WVFKRUXAEOXLHW-HTQZYQBOSA-N 0.000 claims description 2
- XRAYXEBZNYLCBY-UHFFFAOYSA-N 2-[1-(aminomethyl)-2,2,4,4-tetramethylcyclobutyl]acetic acid Chemical compound CC1(C)CC(C)(C)C1(CN)CC(O)=O XRAYXEBZNYLCBY-UHFFFAOYSA-N 0.000 claims description 2
- UWYKQWDIAKQCEJ-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-di(propan-2-yl)cyclobutyl]acetic acid Chemical compound CC(C)C1(C(C)C)CC(CN)(CC(O)=O)C1 UWYKQWDIAKQCEJ-UHFFFAOYSA-N 0.000 claims description 2
- SRLZVTNHASZZSM-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-dibenzylcyclobutyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC1(CC=1C=CC=CC=1)CC1=CC=CC=C1 SRLZVTNHASZZSM-UHFFFAOYSA-N 0.000 claims description 2
- FUDBUFIPBPLPHY-UHFFFAOYSA-N 2-[1-(aminomethyl)-3,3-diphenylcyclobutyl]acetic acid Chemical compound C1C(CN)(CC(O)=O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 FUDBUFIPBPLPHY-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims 222
- KOPGUPUTANQKJY-NXEZZACHSA-N 2-[(3r,4r)-1-(aminomethyl)-3,4-diethylcyclopentyl]acetic acid Chemical compound CC[C@@H]1CC(CN)(CC(O)=O)C[C@H]1CC KOPGUPUTANQKJY-NXEZZACHSA-N 0.000 claims 1
- ZKPYVRKWQDIKJF-UHFFFAOYSA-N 2-[1-(aminomethyl)-2,2,3,3,4,4-hexamethylcyclobutyl]acetic acid Chemical compound CC1(C)C(C)(C)C(CN)(CC(O)=O)C1(C)C ZKPYVRKWQDIKJF-UHFFFAOYSA-N 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 98
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 80
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 40
- 230000015572 biosynthetic process Effects 0.000 description 31
- 238000003786 synthesis reaction Methods 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 27
- 239000003921 oil Substances 0.000 description 27
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
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- GGUBFICZYGKNTD-UHFFFAOYSA-N triethyl phosphonoacetate Chemical compound CCOC(=O)CP(=O)(OCC)OCC GGUBFICZYGKNTD-UHFFFAOYSA-N 0.000 description 13
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Classifications
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
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- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/51—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/50—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/53—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
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- 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
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- C07—ORGANIC CHEMISTRY
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- 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
- C07C229/34—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 containing six-membered aromatic rings
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- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/608—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a ring other than a six-membered aromatic ring in the acid moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/50—Spiro compounds
Landscapes
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- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (5)
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| US6364497P | 1997-10-27 | 1997-10-27 | |
| US60/063644 | 1997-10-27 | ||
| US9768598P | 1998-08-24 | 1998-08-24 | |
| US60/097685 | 1998-08-24 | ||
| PCT/US1998/019876 WO1999021824A1 (en) | 1997-10-27 | 1998-09-23 | Cyclic amino acids and derivatives thereof useful as pharmaceutical agents |
Publications (2)
| Publication Number | Publication Date |
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| AU9663898A AU9663898A (en) | 1999-05-17 |
| AU755800B2 true AU755800B2 (en) | 2002-12-19 |
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| AU96638/98A Ceased AU755800B2 (en) | 1997-10-27 | 1998-09-23 | Cyclic amino acids and derivatives thereof useful as pharmaceutical agents |
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| HU225502B1 (en) | 1998-12-29 | 2007-01-29 | Richter Gedeon Vegyeszet | Process for producing 1-(amino-metyl)-cyclohexene-acetic-acid and intermediates |
| MXPA01011955A (es) * | 1999-05-26 | 2003-09-04 | Warner Lambert Co | Aminoacidos policiclicos, fusionados, como agentes farmaceuticos. |
| EP1840117A1 (en) * | 1999-06-10 | 2007-10-03 | Warner-Lambert Company LLC | Mono- and disubstituted 3-propyl gamma-aminobutyric acids |
| DE60041256D1 (de) * | 1999-06-10 | 2009-02-12 | Warner Lambert Co | Mono-substituierte 3-propyl-gamma-aminobuttersäure |
| US6642398B2 (en) | 1999-06-10 | 2003-11-04 | Warner-Lambert Company | Mono-and disubstituted 3-propyl gamma-aminobutyric acids |
| US7164034B2 (en) | 1999-06-10 | 2007-01-16 | Pfizer Inc. | Alpha2delta ligands for fibromyalgia and other disorders |
| HN2000000224A (es) | 1999-10-20 | 2001-04-11 | Warner Lambert Co | Aminoacidos biciclicos como agentes farmaceuticos |
| US6864390B2 (en) | 1999-12-08 | 2005-03-08 | Warner-Lambert Company | Method for the stereoselective synthesis of cyclic amino acids |
| DE60028076T2 (de) * | 1999-12-08 | 2006-11-02 | Warner-Lambert Co. Llc | Verfahren zur stereoselektiven synthese zyklischer aminosäuren |
| GB2362646A (en) * | 2000-05-26 | 2001-11-28 | Warner Lambert Co | Cyclic amino acid derivatives useful as pharmaceutical agents |
| NZ522480A (en) * | 2000-06-26 | 2005-06-24 | Warner Lambert Co | Gabapentin analogues for sleep disorders |
| GB2364049A (en) * | 2000-06-28 | 2002-01-16 | Warner Lambert Co | Cyclic ketones and their use in the synthesis of amino acids |
| EP1343805A4 (en) | 2000-10-06 | 2005-07-20 | Xenoport Inc | COMPOUNDS DERIVED FROM GALLENIC ACIDS FOR THE PROVISION OF CONTINUING SYSTEMIC CONCENTRATIONS OF MEDICINAL PRODUCTS AFTER ORAL ADMINISTRATION |
| WO2002032376A2 (en) | 2000-10-06 | 2002-04-25 | Xenoport, Inc. | Bile-acid conjugates for providing sustained systemic concentrations of drugs |
| EP1226820A1 (en) * | 2001-01-26 | 2002-07-31 | Warner-Lambert Company | Use of bicyclic amino acids for preventing and treating visceral pain and gastrointestinal disorders |
| GB2374595A (en) * | 2001-04-19 | 2002-10-23 | Warner Lambert Co | Fused bicyclic or tricyclic amino acids |
| SK12822003A3 (sk) | 2001-04-19 | 2004-04-06 | Warner - Lambert Company Llc | Fúzne bicyklické alebo tricyklické aminokyseliny |
| 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 |
| US7232924B2 (en) | 2001-06-11 | 2007-06-19 | Xenoport, Inc. | Methods for synthesis of acyloxyalkyl derivatives of GABA analogs |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| EP1404324B2 (en) | 2001-06-11 | 2011-04-06 | 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 |
| US6927036B2 (en) | 2002-02-19 | 2005-08-09 | Xero Port, Inc. | Methods for synthesis of prodrugs from 1-acyl-alkyl derivatives and compositions thereof |
| US7026351B2 (en) | 2002-03-20 | 2006-04-11 | Xenoport, Inc. | Cyclic 1-(acyloxy)-alkyl prodrugs of GABA analogs, compositions and uses thereof |
| WO2003099338A2 (en) | 2002-05-17 | 2003-12-04 | Xenoport, Inc. | Amino acid conjugates providing for sustained systemic concentrations of gaba analogues |
| GB0223072D0 (en) | 2002-10-04 | 2002-11-13 | Pfizer Ltd | Cyclic nitromethyl acetic acid derivatives |
| US7018818B2 (en) | 2002-10-04 | 2006-03-28 | Pfizer Inc. | Intermediates in the preparation of therapeutic fused bicyclic amino acids |
| US7025745B2 (en) * | 2002-10-07 | 2006-04-11 | Advanced Cardiovascular Systems, Inc. | Method of making a catheter balloon using a tapered mandrel |
| AU2003297927A1 (en) | 2002-12-11 | 2004-06-30 | Xenoport, Inc. | Prodrugs of fused gaba analogs, pharmaceutical compositions and uses thereof |
| KR20050085636A (ko) | 2002-12-13 | 2005-08-29 | 워너-램버트 캄파니 엘엘씨 | 섬유근육통 및 기타 질환의 치료를 위한 프레가발린 유도체 |
| EP1572184A1 (en) * | 2002-12-13 | 2005-09-14 | Warner-Lambert Company | Gabapentin analogues for fibromyalgia and other related disorders |
| CA2451267A1 (en) | 2002-12-13 | 2004-06-13 | Warner-Lambert Company Llc | Pharmaceutical uses for alpha2delta ligands |
| DE60332387D1 (de) | 2002-12-13 | 2010-06-10 | Warner Lambert Co | Alpha-2-delta-ligand zur behandlung vonsymptomen der unteren harnwege |
| WO2005002585A1 (en) * | 2003-07-02 | 2005-01-13 | Warner-Lambert Company Llc | Combination of an allosteric inhibitor of matrix metalloproteinase-13 and a ligand to an alpha-2-delta receptor |
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| CA2538802C (en) | 2003-09-17 | 2015-01-27 | Xenoport, Inc. | Treating or preventing restless legs syndrome using prodrugs of gaba analogs |
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