JP2007508396A5 - - Google Patents
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- Publication number
- JP2007508396A5 JP2007508396A5 JP2006535673A JP2006535673A JP2007508396A5 JP 2007508396 A5 JP2007508396 A5 JP 2007508396A5 JP 2006535673 A JP2006535673 A JP 2006535673A JP 2006535673 A JP2006535673 A JP 2006535673A JP 2007508396 A5 JP2007508396 A5 JP 2007508396A5
- Authority
- JP
- Japan
- Prior art keywords
- aminomethyl
- carbonyl
- isobutanoyloxyethoxy
- crystalline
- cyclohexaneacetic acid
- 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.)
- Granted
Links
- TZDUHAJSIBHXDL-UHFFFAOYSA-N gabapentin enacarbil Chemical compound CC(C)C(=O)OC(C)OC(=O)NCC1(CC(O)=O)CCCCC1 TZDUHAJSIBHXDL-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 31
- 239000008194 pharmaceutical composition Substances 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 18
- 208000004296 neuralgia Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 208000020016 psychiatric disease Diseases 0.000 claims description 14
- 208000019901 Anxiety disease Diseases 0.000 claims description 13
- 206010006002 Bone pain Diseases 0.000 claims description 13
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 13
- 208000033830 Hot Flashes Diseases 0.000 claims description 13
- 206010060800 Hot flush Diseases 0.000 claims description 13
- 208000000112 Myalgia Diseases 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 13
- 208000005793 Restless legs syndrome Diseases 0.000 claims description 13
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 claims description 13
- 206010046543 Urinary incontinence Diseases 0.000 claims description 13
- 230000036506 anxiety Effects 0.000 claims description 13
- 206010003246 arthritis Diseases 0.000 claims description 13
- 206010015037 epilepsy Diseases 0.000 claims description 13
- 208000027866 inflammatory disease Diseases 0.000 claims description 13
- 206010022437 insomnia Diseases 0.000 claims description 13
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 13
- 208000035475 disorder Diseases 0.000 claims description 12
- 230000004770 neurodegeneration Effects 0.000 claims description 10
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 8
- 208000010643 digestive system disease Diseases 0.000 claims description 8
- 208000018685 gastrointestinal system disease Diseases 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 239000013078 crystal Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- 238000002844 melting Methods 0.000 claims 6
- 230000008018 melting Effects 0.000 claims 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 239000012296 anti-solvent Substances 0.000 claims 3
- 238000010438 heat treatment Methods 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 claims 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims 2
- 230000006735 deficit Effects 0.000 claims 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 claims 1
- 229940093475 2-ethoxyethanol Drugs 0.000 claims 1
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims 1
- NNBZCPXTIHJBJL-AOOOYVTPSA-N cis-decalin Chemical compound C1CCC[C@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-AOOOYVTPSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 238000010586 diagram Methods 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims 1
- 229940011051 isopropyl acetate Drugs 0.000 claims 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 229940078552 o-xylene Drugs 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 235000013772 propylene glycol Nutrition 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- NNBZCPXTIHJBJL-UHFFFAOYSA-N trans-decahydronaphthalene Natural products C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims 1
- NNBZCPXTIHJBJL-MGCOHNPYSA-N trans-decalin Chemical compound C1CCC[C@@H]2CCCC[C@H]21 NNBZCPXTIHJBJL-MGCOHNPYSA-N 0.000 claims 1
- 239000008096 xylene Substances 0.000 claims 1
- UGJMXCAKCUNAIE-UHFFFAOYSA-N Gabapentin Chemical compound OC(=O)CC1(CN)CCCCC1 UGJMXCAKCUNAIE-UHFFFAOYSA-N 0.000 description 24
- 229960002870 gabapentin Drugs 0.000 description 12
- 206010061296 Motor dysfunction Diseases 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 208000013465 muscle pain Diseases 0.000 description 7
- 206010036376 Postherpetic Neuralgia Diseases 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 208000022148 skull disease Diseases 0.000 description 4
- 238000013268 sustained release Methods 0.000 description 4
- 239000012730 sustained-release form Substances 0.000 description 4
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical class NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 description 3
- 208000003532 hypothyroidism Diseases 0.000 description 3
- 230000002989 hypothyroidism Effects 0.000 description 3
- 230000007659 motor function Effects 0.000 description 3
- 208000021722 neuropathic pain Diseases 0.000 description 3
- 208000001573 Cataplexy Diseases 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 244000186140 Asperula odorata Species 0.000 description 1
- 235000008526 Galium odoratum Nutrition 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 230000006806 disease prevention Effects 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 229960003692 gamma aminobutyric acid Drugs 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
- -1 α-isobutanoyloxyethoxy Chemical group 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51128703P | 2003-10-14 | 2003-10-14 | |
| PCT/US2004/033979 WO2005037784A2 (en) | 2003-10-14 | 2004-10-14 | Crystalline form of gamma-aminobutyric acid analog |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008325914A Division JP4913796B2 (ja) | 2003-10-14 | 2008-12-22 | γ−アミノ酪酸アナログの結晶形 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007508396A JP2007508396A (ja) | 2007-04-05 |
| JP2007508396A5 true JP2007508396A5 (https=) | 2007-08-09 |
| JP4308263B2 JP4308263B2 (ja) | 2009-08-05 |
Family
ID=34465215
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006535673A Expired - Lifetime JP4308263B2 (ja) | 2003-10-14 | 2004-10-14 | γ−アミノ酪酸アナログの結晶形 |
| JP2008325914A Expired - Lifetime JP4913796B2 (ja) | 2003-10-14 | 2008-12-22 | γ−アミノ酪酸アナログの結晶形 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008325914A Expired - Lifetime JP4913796B2 (ja) | 2003-10-14 | 2008-12-22 | γ−アミノ酪酸アナログの結晶形 |
Country Status (22)
| Country | Link |
|---|---|
| US (10) | US8026279B2 (https=) |
| EP (1) | EP1677767B1 (https=) |
| JP (2) | JP4308263B2 (https=) |
| KR (1) | KR101096480B1 (https=) |
| CN (1) | CN1867322B (https=) |
| AT (1) | ATE516801T1 (https=) |
| AU (1) | AU2004282192B2 (https=) |
| BR (1) | BRPI0415288B8 (https=) |
| CA (1) | CA2541752C (https=) |
| DK (1) | DK1677767T3 (https=) |
| ES (1) | ES2368916T3 (https=) |
| IL (2) | IL174600A (https=) |
| MX (1) | MXPA06004088A (https=) |
| NO (1) | NO338275B1 (https=) |
| NZ (1) | NZ546381A (https=) |
| PL (1) | PL1677767T3 (https=) |
| PT (1) | PT1677767E (https=) |
| RU (1) | RU2412162C2 (https=) |
| SG (1) | SG147437A1 (https=) |
| SI (1) | SI1677767T1 (https=) |
| WO (1) | WO2005037784A2 (https=) |
| ZA (1) | ZA200602722B (https=) |
Families Citing this family (76)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8048917B2 (en) | 2005-04-06 | 2011-11-01 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7186855B2 (en) | 2001-06-11 | 2007-03-06 | Xenoport, Inc. | Prodrugs of GABA analogs, compositions and uses thereof |
| US7025745B2 (en) * | 2002-10-07 | 2006-04-11 | Advanced Cardiovascular Systems, Inc. | Method of making a catheter balloon using a tapered mandrel |
| KR20060119971A (ko) * | 2003-09-11 | 2006-11-24 | 제노포트 인코포레이티드 | Ｇａｂａ 유사체의 전구약물을 이용한 요실금의 치료및/또는 예방 |
| NZ579515A (en) * | 2003-09-17 | 2011-09-30 | Xenoport Inc | Treating or preventing restless legs syndrome using prodrugs of gaba analogs |
| SG147437A1 (en) | 2003-10-14 | 2008-11-28 | Xenoport Inc | Crystalline form of gamma-aminobutyric acid analog |
| US20050209319A1 (en) * | 2004-03-18 | 2005-09-22 | Xenoport, Inc. | Treatment of local pain |
| MX2007005306A (es) | 2004-11-04 | 2007-06-11 | Xenoport Inc | Formas de dosis oral de liberacion sostenida de la prodroga gabapentina. |
| US7351740B2 (en) * | 2005-06-20 | 2008-04-01 | Xenoport, Inc. | Acyloxyalkyl carbamate prodrugs of tranexamic acid, methods of synthesis and use |
| US20080161393A1 (en) * | 2006-12-08 | 2008-07-03 | Barrett Ronald W | Use of prodrugs of GABA analogs for treating disease |
| TWI369982B (en) * | 2007-01-11 | 2012-08-11 | Xenoport Inc | Sustained release oral dosage forms of a prodrug of r-baclofen and methods of treatment |
| US20090118365A1 (en) * | 2007-11-06 | 2009-05-07 | Xenoport, Inc | Use of Prodrugs of GABA B Agonists for Treating Neuropathic and Musculoskeletal Pain |
| US20090318728A1 (en) * | 2008-06-24 | 2009-12-24 | Teva Pharmaceutical Industries Ltd. | Processes for preparing prodrugs of gabapentin and intermediates thereof |
| WO2010003046A2 (en) * | 2008-07-02 | 2010-01-07 | Teva Pharmaceutical Industries Ltd. | Gabapentin enacarbil salts and processes for their preparation |
| US7989641B2 (en) | 2008-08-07 | 2011-08-02 | Xenoport, Inc. | Methods of synthesizing N-hydroxysuccinimidyl carbonates |
| US8299291B2 (en) * | 2008-08-07 | 2012-10-30 | Xenoport, Inc. | Methods of synthesizing 1-(acyloxy)-alkyl carbamate prodrugs |
| US8283487B2 (en) * | 2008-11-26 | 2012-10-09 | Teva Pharmaceutical Industries Ltd. | Processes for the preparation and purification of gabapentin enacarbil |
| US20100160666A1 (en) * | 2008-12-23 | 2010-06-24 | Teva Pharmaceutical Industries Ltd. | Preparation of gabapentin enacarbil intermediate |
| WO2010101115A1 (ja) * | 2009-03-02 | 2010-09-10 | アステラス製薬株式会社 | 固形製剤の包装体 |
| KR20110117216A (ko) * | 2009-03-03 | 2011-10-26 | 제노포트 인코포레이티드 | Ｒ-바클로펜 전구약물의 서방형 경구 투약 형태 |
| JP5580345B2 (ja) | 2009-03-06 | 2014-08-27 | ゼノポート，インコーポレイティド | 高充填量のガバペンチンプロドラッグを有する経口剤形 |
| WO2011028234A1 (en) * | 2009-09-04 | 2011-03-10 | Xenoport, Inc. | Uses of acyloxyalkyl carbamate prodrugs of tranexamic acid |
| WO2011091164A1 (en) | 2010-01-22 | 2011-07-28 | Xenoport, Inc. | Oral dosage forms having a high loading of a tranexamic acid prodrug |
| US20110263701A1 (en) * | 2010-04-21 | 2011-10-27 | Sigal Blau | Gabapentin enacarbil compositions |
| WO2013008182A1 (en) * | 2011-07-10 | 2013-01-17 | Mahesh Kandula | Prodrugs of gaba analogs |
| WO2014037832A2 (en) | 2012-09-06 | 2014-03-13 | Mahesh Kandula | Compositions and methods for the treatment of epilepsy and neurological diseases |
| WO2013167985A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological disorders |
| WO2013168021A1 (en) | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neuromuscular disorders and neurodegenerative disorders |
| WO2013168019A1 (en) * | 2012-05-07 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neuropathic pain |
| US9399634B2 (en) | 2012-05-07 | 2016-07-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of depression |
| WO2013168025A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of blood clotting disorders |
| WO2013168023A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of parkinson's disease |
| US9522884B2 (en) | 2012-05-08 | 2016-12-20 | Cellix Bio Private Limited | Compositions and methods for the treatment of metabolic disorders |
| WO2013167992A1 (en) | 2012-05-08 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of inflammatory disorders |
| US9434704B2 (en) | 2012-05-08 | 2016-09-06 | Cellix Bio Private Limited | Compositions and methods for the treatment of neurological degenerative disorders |
| WO2013168002A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of neurological conditions |
| WO2013168033A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for treatment of neurologic diseases |
| WO2013168015A1 (en) | 2012-05-10 | 2013-11-14 | Mahesh Kandula | Compositions and methods for the treatment of asthma and allergy |
| US9321775B2 (en) | 2012-05-10 | 2016-04-26 | Cellix Bio Private Limited | Compositions and methods for the treatment of moderate to severe pain |
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