RU2017125261A - Способ и промежуточные соединения для получения прегабалина - Google Patents
Способ и промежуточные соединения для получения прегабалина Download PDFInfo
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- RU2017125261A RU2017125261A RU2017125261A RU2017125261A RU2017125261A RU 2017125261 A RU2017125261 A RU 2017125261A RU 2017125261 A RU2017125261 A RU 2017125261A RU 2017125261 A RU2017125261 A RU 2017125261A RU 2017125261 A RU2017125261 A RU 2017125261A
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- Prior art keywords
- seq
- serine
- glutamine
- alanine
- transaminase enzyme
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- AYXYPKUFHZROOJ-ZETCQYMHSA-N pregabalin Chemical compound CC(C)C[C@H](CN)CC(O)=O AYXYPKUFHZROOJ-ZETCQYMHSA-N 0.000 title claims 2
- 239000000543 intermediate Substances 0.000 title 1
- 229960001233 pregabalin Drugs 0.000 title 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 5
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 4
- 102000003929 Transaminases Human genes 0.000 claims 4
- 108090000340 Transaminases Proteins 0.000 claims 4
- 235000004279 alanine Nutrition 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 3
- 239000004471 Glycine Substances 0.000 claims 3
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 3
- 235000013922 glutamic acid Nutrition 0.000 claims 3
- 239000004220 glutamic acid Substances 0.000 claims 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 3
- 229930182817 methionine Natural products 0.000 claims 3
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 150000001413 amino acids Chemical group 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- FWMNVWWHGCHHJJ-SKKKGAJSSA-N 4-amino-1-[(2r)-6-amino-2-[[(2r)-2-[[(2r)-2-[[(2r)-2-amino-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]hexanoyl]piperidine-4-carboxylic acid Chemical compound C([C@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@H](CCCCN)C(=O)N1CCC(N)(CC1)C(O)=O)NC(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 FWMNVWWHGCHHJJ-SKKKGAJSSA-N 0.000 claims 1
- QNHBGZSPSCOCLM-UHFFFAOYSA-N 5-hydroxy-4-(2-methylpropyl)oxolan-2-one Chemical compound CC(C)CC1CC(=O)OC1O QNHBGZSPSCOCLM-UHFFFAOYSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 235000018417 cysteine Nutrition 0.000 claims 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 1
- 229960000310 isoleucine Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 1
- 239000004474 valine Substances 0.000 claims 1
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- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/001—Amines; Imines
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- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B53/00—Asymmetric syntheses
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- C07C227/12—Formation of amino and carboxyl groups
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- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/66—Nitrogen atoms
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
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- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/04—Oxygen as only ring hetero atoms containing a five-membered hetero ring, e.g. griseofulvin, vitamin C
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- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
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- C07C229/04—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 acyclic and saturated
- C07C229/06—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 acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—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 acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
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- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Claims (48)
1. Фермент трансаминаза, имеющий аминокислотную последовательность SEQ ID NO: 1:
MNKPQSWEARAETYSLYGFTDMPSLHX27RGTVVVTHGEGPYX41VDVX45
GRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQT
VMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKR
KILTRX147NAYHGVTAVSASMTGX163PX165NSVFGLPLPGFVHLX180CPHY
WRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIP
PAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSK
NLTAGFFPVGAVILGPELX304KRLETAIEAIEEFPHGFTAX324GHPVGCAIA
LKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEA
VKDKASKTPFDGNLSVSX401RIANTCX408DLGLICX415X416X417GQSVILX424
PPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 1),
где:
X27 выбран из глутамина (Q) и глутаминовой кислоты (E);
X41 выбран из изолейцина (I) и валина (V);
X45 выбран из аспарагина (N) и гистидина (H);
X147 выбран из аспарагина (N) и глутамина (Q);
X163 выбран из лейцина (L) и метионина (M);
X165 выбран из тирозина (Y) и гистидина (H);
X180 выбран из треонина (T); глицина (G) и серина (S);
X304 выбран из аланина (A) и серина (S);
X324 выбран из глицина (G) и серина (S);
X401 выбран из лизина (K) и глутаминовой кислоты (E);
X408 выбран из треонина (T) и глутамина (Q);
X415 выбран из серина (S) и аланина (A);
X416 выбран из пролина (P) и аланина (A);
X417 выбран из лейцина (L) и метионина (M); и
X424 выбран из цистеина (C) и серина (S).
2. Фермент трансаминаза по п. 1, где:
X27 представляет собой глутаминовую кислоту (E);
X147 представляет собой глутамин (Q);
X165 представляет собой гистидин (H);
X304 представляет собой серин (S);
X324 представляет собой глицин (G);
X401 представляет собой лизин (K);
X408 представляет собой глутамин (Q);
X416 представляет собой аланин (A);
X417 представляет собой метионин (M); и
X424 представляет собой серин (S).
3. Фермент трансаминаза по п. 1, имеющий аминокислотную последовательность, выбранную из:
MNKPQSWEARAETYSLYGFTDMPSLHQRGTVVVTHGEGPYIVDVNGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRNNAYHGVTAVSASMTGLPYNSVFGLPLPGFVHLTCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPELAKRLETAIEAIEEFPHGFTASGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSERIANTCTDLGLICSPMGQSVILCPPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 2);
MNKPQSWEARAETYSLYGFTDMPSLHERGTVVVTHGEGPYIVDVNGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRNNAYHGVTAVSASMTGLPYNSVFGLPLPGFVHLTCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPELSKRLETAIEAIEEFPHGFTAGGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSKRIANTCQDLGLICSALGQSVILCPPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 3);
MNKPQSWEARAETYSLYGFTDMPSLHERGTVVVTHGEGPYVVDVNGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRQNAYHGVTAVSASMTGLPHNSVFGLPLPGFVHLTCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPELSKRLETAIEAIEEFPHGFTAGGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSKRIANTCQDLGLICSALGQSVILSPPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 4);
MNKPQSWEARAETYSLYGFTDMPSLHERGTVVVTHGEGPYIVDVNGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRQNAYHGVTAVSASMTGMPHNSVFGLPLPGFVHLTCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPALSKRLETAIEAIEEFPHGFTAGGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSKRIANTCQDLGLICSAMGQSVILSPPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 5);
MNKPQSWEARAETYSLYGFTDMPSLHERGTVVVTHGEGPYVVDVNGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRQNAYHGVTAVSASMTGLPHNSVFGLPLPGFVHLGCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPELSKRLETAIEAIEEFPHGFTAGGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSKRIANTCQDLGLICAAMGQSVILSPPFILTEAQMDEMFDKLEKALDKVFAEVA(SEQ ID NO: 6); и
MNKPQSWEARAETYSLYGFTDMPSLHERGTVVVTHGEGPYIVDVHGRRYLDANSGLYNMVAGFDHKGLIDAAKAQYERFPGYHSFFGRMSDQTVMLSEKLVEVSPFDSGRVFYTNSGSEANDTMVKMLWFLHAAEGKPQKRKILTRQNAYHGVTAVSASMTGLPHNSVFGLPLPGFVHLSCPHYWRYGEEGETEEQFVARLARELEETIQREGADTIAGFFAEPVMGAGGVIPPAKGYFQAILPILRKYDIPVISDEVICGFGRTGNTWGCVTYDFTPDAIISSKNLTAGFFPVGAVILGPELSKRLETAIEAIEEFPHGFTAGGHPVGCAIALKAIDVVMNEGLAENVRRLAPRFEERLKHIAERPNIGEYRGIGFMWALEAVKDKASKTPFDGNLSVSKRIANTCQDLGLICSAMGQSVILSPPFILTEAQMDEMFDKLEKALDKVFAEVA (SEQ ID NO: 7).
4. Способ получения (S)-3-аминометил-5-метилгексановой кислоты ((S)-II):
или ее фармацевтически приемлемой соли, включающий стадию обработки 5-гидрокси-4-(2-метилпропил)-3,4-дигидро-5H-2-фуранона (IA) и амина ферментом трансаминазой по любому из пп. 1-3.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361805786P | 2013-03-27 | 2013-03-27 | |
| US61/805,786 | 2013-03-27 |
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| RU2015138545A Division RU2628298C2 (ru) | 2013-03-27 | 2014-03-25 | Способ и промежуточные соединения для получения прегабалина |
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| RU2017125261A true RU2017125261A (ru) | 2019-01-31 |
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| RU2017125261A RU2017125261A (ru) | 2013-03-27 | 2014-03-25 | Способ и промежуточные соединения для получения прегабалина |
| RU2015138545A RU2628298C2 (ru) | 2013-03-27 | 2014-03-25 | Способ и промежуточные соединения для получения прегабалина |
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| RU2015138545A RU2628298C2 (ru) | 2013-03-27 | 2014-03-25 | Способ и промежуточные соединения для получения прегабалина |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US20160024540A1 (ru) |
| EP (2) | EP3216863A1 (ru) |
| JP (1) | JP2016516744A (ru) |
| KR (1) | KR20150121202A (ru) |
| CN (3) | CN105051022B (ru) |
| AU (2) | AU2014240833B2 (ru) |
| BR (2) | BR122017006144A2 (ru) |
| CA (1) | CA2905411A1 (ru) |
| CY (1) | CY1118945T1 (ru) |
| DK (1) | DK2978748T3 (ru) |
| ES (1) | ES2630128T3 (ru) |
| HU (1) | HUE034834T2 (ru) |
| IL (1) | IL241438A0 (ru) |
| MX (1) | MX2015013589A (ru) |
| PL (1) | PL2978748T3 (ru) |
| PT (1) | PT2978748T (ru) |
| RU (2) | RU2017125261A (ru) |
| SG (1) | SG11201506998XA (ru) |
| SI (1) | SI2978748T1 (ru) |
| WO (1) | WO2014155291A1 (ru) |
| ZA (1) | ZA201506798B (ru) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010081053A2 (en) | 2009-01-08 | 2010-07-15 | Codexis, Inc. | Transaminase polypeptides |
| WO2016075082A1 (en) | 2014-11-10 | 2016-05-19 | Sandoz Ag | Stereoselective reductive amination of alpha-chiral aldehydes using omega-transaminases for the synthesis of precursors of pregabalin and brivaracetam |
| WO2016140799A1 (en) * | 2015-03-03 | 2016-09-09 | Ark Diagnostics, Inc. | Pregabalin immunoassays |
| EP3638688A4 (en) * | 2017-06-14 | 2021-07-07 | Codexis, Inc. | MODIFIED TRANSAMINASE POLYPEPTIDES INTENDED FOR INDUSTRIAL BIOCATALYSIS |
| KR20210030399A (ko) | 2018-07-09 | 2021-03-17 | 머크 샤프 앤드 돔 코포레이션 | 4'-에티닐 뉴클레오시드 유사체의 효소적 합성 |
| CN111004102B (zh) * | 2019-12-23 | 2022-11-04 | 万华化学集团股份有限公司 | 一种制备光学活性香茅醛的方法及用于该方法的催化剂 |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB834100A (en) | 1957-10-26 | 1960-05-04 | Eastman Kodak Co | Improvements in the preparation of mixed aldols |
| US4239636A (en) * | 1978-10-23 | 1980-12-16 | Exxon Research & Engineering Co. | Thio-bis-(alkyl lactone acid esters) and thio-bis-(hydrocarbyl diacid esters) are useful additives for lubricating compositions |
| US6197819B1 (en) | 1990-11-27 | 2001-03-06 | Northwestern University | Gamma amino butyric acid analogs and optical isomers |
| JPH06107597A (ja) * | 1992-03-12 | 1994-04-19 | Noguchi Kenkyusho | （Ｒ）−α−ヒドロキシ−β，γ−不飽和エステルの製造法 |
| US5268387A (en) * | 1992-04-24 | 1993-12-07 | Allergan, Inc. | Pharmaceutical compositions and method for administering 3 and 4-substituted 2(5H)-furanones to a mammal for inhibiting bone loss |
| DE69613387T2 (de) * | 1995-11-07 | 2002-02-14 | Minnesota Mining And Mfg. Co., Saint Paul | Initiator system und klebstoff zusammensetzung diesen enthaltend |
| ES2200184T7 (es) | 1996-07-24 | 2015-02-10 | Warner-Lambert Company Llc | Isobutilgaba y sus derivados para el tratamiento del dolor |
| SE9801992D0 (sv) * | 1998-06-04 | 1998-06-04 | Astra Ab | New 3-aryl-2-hydroxypropionic acid derivative I |
| US20030225149A1 (en) * | 2002-04-30 | 2003-12-04 | Blazecka Peter G. | Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids |
| EP1768950A2 (en) * | 2005-04-11 | 2007-04-04 | Teva Pharmaceutical Industries Ltd. | Process for making (s)-pregabalin |
| AU2006279810B2 (en) * | 2005-08-11 | 2011-10-27 | Vertex Pharmaceuticals Incorporated | Modulators of cystic fibrosis transmembrane conductance regulator |
| WO2008127646A2 (en) * | 2007-04-11 | 2008-10-23 | Dsm Ip Assets B.V. | Transaminase-based processes for preparation of pregabalin |
| KR100846419B1 (ko) * | 2007-08-10 | 2008-07-15 | 한국과학기술원 | 프레가발린의 신규한 제조 방법 |
| CN101362696A (zh) * | 2008-09-27 | 2009-02-11 | 开原亨泰精细化工厂 | 3-氨甲基-5-甲基己酸即混旋普瑞巴林的制备新方法 |
| WO2010081053A2 (en) * | 2009-01-08 | 2010-07-15 | Codexis, Inc. | Transaminase polypeptides |
| WO2011086565A1 (en) * | 2010-01-15 | 2011-07-21 | Lupin Limited | Method for preparation of enantiomerically enriched and/or racemic gamma-amino acids |
-
2014
- 2014-03-25 AU AU2014240833A patent/AU2014240833B2/en not_active Ceased
- 2014-03-25 MX MX2015013589A patent/MX2015013589A/es unknown
- 2014-03-25 ES ES14717080.7T patent/ES2630128T3/es active Active
- 2014-03-25 RU RU2017125261A patent/RU2017125261A/ru not_active Application Discontinuation
- 2014-03-25 PL PL14717080T patent/PL2978748T3/pl unknown
- 2014-03-25 PT PT147170807T patent/PT2978748T/pt unknown
- 2014-03-25 EP EP17162642.7A patent/EP3216863A1/en not_active Withdrawn
- 2014-03-25 SG SG11201506998XA patent/SG11201506998XA/en unknown
- 2014-03-25 BR BR122017006144A patent/BR122017006144A2/pt not_active IP Right Cessation
- 2014-03-25 CN CN201480018083.5A patent/CN105051022B/zh not_active Expired - Fee Related
- 2014-03-25 SI SI201430236A patent/SI2978748T1/sl unknown
- 2014-03-25 WO PCT/IB2014/060140 patent/WO2014155291A1/en active Application Filing
- 2014-03-25 DK DK14717080.7T patent/DK2978748T3/en active
- 2014-03-25 RU RU2015138545A patent/RU2628298C2/ru not_active IP Right Cessation
- 2014-03-25 BR BR112015024859A patent/BR112015024859A2/pt not_active IP Right Cessation
- 2014-03-25 EP EP14717080.7A patent/EP2978748B1/en not_active Not-in-force
- 2014-03-25 US US14/775,979 patent/US20160024540A1/en not_active Abandoned
- 2014-03-25 HU HUE14717080A patent/HUE034834T2/en unknown
- 2014-03-25 KR KR1020157026688A patent/KR20150121202A/ko not_active Abandoned
- 2014-03-25 CN CN201710882572.0A patent/CN107746834A/zh active Pending
- 2014-03-25 CN CN201710882505.9A patent/CN107556273A/zh active Pending
- 2014-03-25 CA CA2905411A patent/CA2905411A1/en not_active Abandoned
- 2014-03-25 JP JP2016504807A patent/JP2016516744A/ja active Pending
-
2015
- 2015-09-10 IL IL241438A patent/IL241438A0/en unknown
- 2015-09-14 ZA ZA2015/06798A patent/ZA201506798B/en unknown
-
2016
- 2016-06-07 AU AU2016203782A patent/AU2016203782B2/en not_active Ceased
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2017
- 2017-06-13 CY CY20171100622T patent/CY1118945T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RU2628298C2 (ru) | 2017-08-15 |
| EP3216863A1 (en) | 2017-09-13 |
| CN107556273A (zh) | 2018-01-09 |
| ES2630128T3 (es) | 2017-08-18 |
| AU2014240833A1 (en) | 2015-10-01 |
| DK2978748T3 (en) | 2017-07-24 |
| MX2015013589A (es) | 2016-06-23 |
| CA2905411A1 (en) | 2014-10-02 |
| PT2978748T (pt) | 2017-07-06 |
| EP2978748B1 (en) | 2017-05-10 |
| CN105051022B (zh) | 2017-10-27 |
| IL241438A0 (en) | 2015-11-30 |
| BR112015024859A2 (pt) | 2017-10-10 |
| PL2978748T3 (pl) | 2017-09-29 |
| ZA201506798B (en) | 2019-05-29 |
| CN107746834A (zh) | 2018-03-02 |
| BR122017006144A2 (pt) | 2019-09-03 |
| CY1118945T1 (el) | 2018-01-10 |
| EP2978748A1 (en) | 2016-02-03 |
| CN105051022A (zh) | 2015-11-11 |
| AU2014240833B2 (en) | 2016-07-07 |
| AU2016203782A1 (en) | 2016-06-23 |
| US20160024540A1 (en) | 2016-01-28 |
| RU2015138545A (ru) | 2017-05-03 |
| AU2016203782B2 (en) | 2017-06-01 |
| KR20150121202A (ko) | 2015-10-28 |
| HK1213882A1 (zh) | 2016-07-15 |
| SI2978748T1 (sl) | 2017-07-31 |
| JP2016516744A (ja) | 2016-06-09 |
| SG11201506998XA (en) | 2015-10-29 |
| HUE034834T2 (en) | 2018-03-28 |
| WO2014155291A1 (en) | 2014-10-02 |
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