GB2323594A - 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines - Google Patents
2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/24—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and acyclic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/22—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton containing at least two amino groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07C229/30—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 unsaturated
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
There are disclosed 2-amino-alkanoic and alkenoic acid derivatives, amino alcohols and diamines represented by the general formula (I), (II), (III) respectively and the corresponding products resulting from the hydrogenation of the double bond(s), wherein R<SP>1</SP>, R<SP>2</SP> = H, amino protective groups such as benzyl, tert-butoxycarbonyl, benzyloxycarbonyl, fluorenylmethoxycarbonyl; wherein R<SP>3</SP> = aromatic, heterocyclic, carbocyclic, linear or branched saturated chain, alkyl carbonyl, alkoxy carbonyl and nitrile; wherein R<SP>4</SP> = H, alkyl; wherein R<SP>5</SP> = H, OH, alkyl, alkoxy, NH 2 , N-alkyl, or acyl groups; wherein m # 1; n # 0; o # 1; p # 0; q # 0; their geometrical isomers, their enantiomeric forms, their pharmacologically and immunologically acceptable salts and their uses. An amino-protected form of methyl 2-amino-eicos-5(z)-enoate was prepared and reduced to the corresponding alcohol and converted to the diamine. The compounds of formula I, II and III are stated to have pharmacological activity for a wide and diverse range of conditions.
Description
2-AMINO-ALKANOIC ACID DERIVATIVES, 2-AMINO ALCOHOLS AND
DIAMINES, THE PROCESSES FOR THEIR PREPARATION AND THEIR
USES
The present invention relates to 2-amino-alkanoic and alkenoic acid derivatives represented by the general formula (I):
wherein Rl, R2 = H, amino protective groups such as benzyl, tert-butoxycarbonyl, benzyloxycarbonyl, fluorenylmethoxycarbonyl; wherein R3 = aromatic, heterocyclic, carbocyclic, linear or branched saturated chain, alkyl carbonyl, alkoxy carbonyl and nitrile; wherein R4 = H, alkyl; wherein R5 = H, OH, alkyl,alkoxy, NH2, N-alkyl, or acyl groups; whereinm > l;n > 0;o > 1;p > 0;q20.
The invention extends to the following aspects of compounds of formula (I): (a) their hydrogenated products (resulting from the hydrogenation of the double bonds); (b) their geometrical isomers: (c) their enantiomeric forms; (d) their pharmacologically and immunologically acceptable salts; (e) the processes for their preperation; and (f) the key intermediates for their preparation.
The present invention also relates to 2-amino alcohols and other amino alcohols (and ethers) and 1,2- and 1,3-diamines represented by the general formulae (II) and (III) respectively:
wherein Rl, R2, R3,R4, m, n, o, p, q are as defined for formula (I); wherein R6 = OH, alkoxy group.
The invention extends to the following aspects of compounds of formulae (II) and (III): (a) their hydrogenated products (resulting from the hydrogenation of the double bonds); (b) their geometrical isomers: (c) their enantiomeric forms; (d) their pharmacologically and immunologically acceptable salts; (e) the processes for their preperation; and (f) the key intermediates for their preparation.
Preferred salts of compounds of formulae (I), (II), (III), are : chloride, acetate, sulfate, tartrate, citrate.
USES
The above compounds exhibit a wide range of biological actions associated with their unique structures and physico-chemical characteristics. Essentially, all resemble natural lipids in being amphipathic, being surfactants, forming monolayers and aggregates. Their biological, chemical and physico-chemical uses are therefore closely linked with these properties. Particularly important is the fact that they are multi-functional possessing a variety of fatty acid (or lipidic or hydrophobic) structures combined with one or more of the common polar groups found in synthetic and natural products and biopolymers (proteins, nucleic acids, sugars and lipids).
A major use therefore is found as agents which have therapeutic properties and immunological properties. Since this is attributable to their structural resemblance to nature's molecules, they should act as inhibitors of membrane processes, particularly all signalling/signal transduction and ion-channel gating and blocking. Examples may be lipid metabolising enzymes such as phospholipases A1, A2, C, D, and the corresponding ether and sphingolipid degrading enzyrnes, lipases, fatty acid synthetases, lipid methylases and carboxylases, cyclo-oxygenases, lipoxygenases and sterol metabolising enzymes. Conditions associated with the action of these and other enzymes include diabetes, obesity, appetite control, cardiovascular conditions, lipidemias, immunodisorders, inflammation, analgesia, ageing, diseases associated with abnormal cell growth and differentiation.
Apart from the possibility that they will affect the above biosystems and have therapeutic potential in their own right, some of the amino fatty acids (and analogues and derivatives) can have other uses. The latter are due to their biocompatibility, their adhesion to cell surfaces and membranes and to lipid binding proteins (e.g. albumin). In fact, lipidisation is an established method of increasing bioavailability, delivery and stability of therapeutic substances. Many of the substances depicted are useful in these respects and, additionally, can increase biological lifetimes, cell adhesion and delivery across natural barriers such as skin, gut and blood-brain.
A third possible use involves the properties of aggregation or of mixed aggregation.
Many of the above compounds can form liposomes, niosomes or mixed liposomes or mixed niosomes. They can also form the emulsions, lotions, creams, niosomes etc that are useful in the pharmaceuticaL immunological and cosmetic industries. Of particular interest is their use in developing novel slow release, microcapsules and other entities.
Their structural resemblance to natural fatty acids (straight chain, branched and unsaturated), lends confidence to their use as pharmaceuticals. In particular, the analogues of the essntial fatty acids (EFAs) may have a range of possible medical use.
2-Amino alcohols (u) and diamines (III) present antiinflamatory activity in paw edema test, analgesic activity in acetic acid test and cytotoxic activity in MTT test.
SYNTHETIC METHODS
A new method has been developed for the preparation of 2-ammo alkanoic and 2amino-alkenoic acids. Derivatives (IV) of aspartic and glutamic acid were prepared by the known methods of peptide chemistry (M. Bodanc7ky and A. BodansAy, The
Practice of Pepdde Synthesis, Spinger-Verlag, Berlin, 1984).
Key intermediate derivatives of glutamic and aspartic acid semialdehydes of the general formula (V), wherein R', R2, p, q are as defined for formula (I);
wherein R7 = alkyl; wherein r > 1 can be prepared by reduction of ('V) with DIBAL (di-isobutyl aluminium hydride), at temperatures lower than -70 OC in non protic solvents. The double bond nearest to the 2-amino acid moiety of formula (I) is formed by reacting (V) under Wittig conditions.
Ylides were generated using K+ bases, preferable KN(TMS)2, in non-protic solvents.
The saturated compounds were obtained from those with the double bond(s) under standard hydrogenation conditions.
The protective groups R', R2, R7 of (I) can be removed by the known methods of peptide chemistry (M. Bodans:k:y and k BodansAcy, The Practice of Peptide
Synthesis, Spinger-Verlag, Berlin, 1984) at the end of the synthesis resulting in salts of 2-amino-alcanoic and 2-amino-alkenoic acids.
N-protected 2-arnino-alcanoic and 2-amino alkenoic acids (I) can be converted to amino alcohols (II) and diamines (III) by known procedure [(i) G. Kokotos and C.
Noula, J. Org Chem. 1996, 61, 6996; (ii) G. Kokotos and V. Constantinou, J. Chem.
Res. 1992, 391(S); (iii) V. Constantinou and G. Kokotos, Org Prep. Proc. Int., 1994, 26, 599].
Examples:
Preparation of Methyl (S)-2-(Di-tert-Butoyearbonyl-amino)-5-oxo-pentanoate.
To a stirred solution of dimethyl N,N-Boc2-L-glutamate (10 g, 27 mmol) in dry ether (270 mL) was added dropwise DIBAL (30 mL, 1.0 M in hexane, 30 mmol) at -780C.
The reaction mixture was stirred for 5 min. It was then quenched with H20 (4 mL) and allowed to warm at rt. The mixture was stirred for 30 min, dried over MgSO4 and filtered through a pad of celite. The solvent was evaporated and the residue was purified by silica gel column chromatography to yield methyl (S)-2-(di-tert butoxycarbonyl-amino)-5-oxo-pentanoate (7.90 g, 85% yield) as an oil : [a]o-35.3 (c 2.25, CHCI3); 'H NMR (CDCI3) 6: 1.48 (s, 18 H), 2.16 (m, 1 H), 2.52 (m, 2 H), 2.59 (m, 1 H), 3.71 (s, 3 H), 4.87 (dd, J = 9.6, 5.2 Hz, 1 H), 9.76 (s, 1 H); 13C NMR (CDCl3) : 22.5 (t), 27.9 (q), 40.5 (t), 52.2 (q), 57.3 (d), 83.4 (s), 152.0 (s), 170.7 (s), 200.9 (d); IR (CHCl3) (cm1) 3028, 2984, 1789, 1743, 1699, 1370, 1231, 1144, 1121; MS m/z (relative intensity) 302 (M - 43) (1), 206 (15), 189 (10), 174 (37), 162 (35), 144 (31), 128 (100), 102 (26), 86 (35). Anal. Calcd. for C16H27NO7: C, 55.64; H, 7.88; N, 4.06.
Found: C, 55.45; H, 8.10; N, 4.09.
Preparation of Methyl (2S)-2-N,N-Boc2-eicos-5(Z)-enoate. To a stirred suspension of n-pentadecyl-triphenyl-phosphonium bromide (3.85 g, 7 mmol) in dry toluene (40 mL) at 0 C was added dropwise KHMDS (12.8 mL, 0.5 M in toluene, 6.4 mmol). The reaction mixture was stirred for 15 min and then cooled to -780C. After 10 min (S)-2 (di-tert-butoxycarbonyl-amino)-5-oxo-pentanoic acid methyl ester (2 g, 5.8 mmol) dissolved in toluene (5 mL) was added dropwise and the reaction mixture was allowed to warm to room temperature. The mixture was stirred until TLC showed complete conversion. The reaction was quenched with saturated NH4Cl (50 mL) solution and extracted with Et20 (3 x 10 mL). The combined organic phases were washed with brine (50 mL), dried over MgSO4, filtered, evaporated and purified by silica gel column chromatography, to yield methyl (S)-2-N,N-Boc2-eicos-5(Z)-enoate (2.7 g, 87% yield) as an oil: [a]D-26.2 (c 2.25, CHCl3); lH NMR (CDC13) : 0.88 (t, J = 6.8 Hz, 3 H), 1.25 (br s, 24 H), 1.49 (s, 18 H), 1.90 (m, 1 H), 2.00 (dd, J = 13.6, 6.8 Hz, 2 H), 108 (dd, J = 14, 7.2 Hz, 2 H), 2.15 (m, 1 H), 3.71 (s, 3 H), 4.86 (dd, J = 8.8, 4.8Hz, 1 H), 5.38 (m, 2 H); 13C NMR (CDC13) 8 14.1 (q), 22.7 (t), 24.0 (t), 27.3 (t), 27.7 (t), 27.8 (t), 27.9 (t), 28.0 (q), 29.3 (t), 29.4 (t), 29.5 (t), 29.6 (t), 29.6 (t), 29.7 (t), 30.1 (t), 31.9 (t), 52.1 (q), 57.7 (d), 83.0 (s), 128.1 (d), 131.3 (d), 152.1 (s), 171.4 (s); IR (CHC13) (cm~l) 2928, 2855, 1787, 1787, 1742, 1698, 1458, 1370, 1144; MS m/z (relative intensity) 382 (M - 157)+ (4), 366 (9), 339 (30), 280 (83), 156 (10), 143 (25), 133 (100), 106 (24). Anal. Calcd. for C31H57NO6: C, 68.96; H, 10.65; N, 2.60. Found: C, 68.67; H, 10.88; N, 2.65.
Preparation of 2-amino-eicos-5(Z)-en-i-oL To a stirred solution of 2-(N-tertbutoxycarbonylamino)-eicos-5(Z)-enoic acid (0.42 g, 1 nunol) in CHUCK (3 mL), kept under a N2 atmosphere, pyridine (80 L, 1 mmol) and cyanuric fluoride (180 L, 2 mmol) were added at -15 OC. The mixture was stirred at -15 C for 1h and then cold water and CHUCK were added. The organic layer was washed with water, dried (Na2SO4) and concentrated to a small volume. Sodium borohydride (76 mg, 2 mmol) was added in one portion, followed by dropwise addition of MeOH (2 mL) over a period of 15 min at room temperature. The reaction mixture was neutralized and the organic solvents were removed. EtOAc and water were added, the organic layer was seperated, washed with 1N H2SO4 (5 mL) and H20 (2 x 5 mL) and dried (Na2SO4).
The solvent was removed and the residue was purified by column chromatography using CHC13 as eluent.
The tert-butoxycarbonyl group was removed by treatment with 4N HC1 in tetrahydrofuran (12 mL) for 30 min at room temperature: 0.24g, 71% yield; m.p. 5758 OC; [a]D -2.2 (c 0.5, CHCl3); 1H NMR (CDCl3) 8 : 0.85 (t, J = 7 Hz, 3 H), 1.25 (br s, 24 H), 1.65 (m, 2 H), 2.10 (m, 4 H), 3.45 (m, 1 H), 3.75 (m, 1 H), 3.95 (m, 1 H), 5.38 (m, 2 H); FAB MS m/z (relative intensity) 312 (M+H) (100), 280 (7). Anal. Calcd.
for C20H42NOCl: C, 69.03; H, 12.16; N, 4.02. Found: C, 69.04; H, 12.28; N, 4.21.
Preparation of i,2-eicos-5(Z)-enediamine. To a stirred solution of 2-(N-tertbutoxycarbonylamino)-eicos-5(Z)-en-1-ol (0.41 g, 1 mmol) in CH2C12 (2.5 mL), triethylamine (0.21 mL, 1.5 mmol) and methanesulfonyl chloride (0.12 mL, 1.5 mmol) were added portionwise. The inbare was stirred at 0 C for 30 min at room temperature. The organic phase was washed consecutively with brine, 1N H2 SO4, brine, 5% aq. NaHCO3, brine, dried (Na2SO4) and the solvent was removed.
The mesylate was dissolved in DMF (2 mL). Sodium azide (0.20 g, 3 mmol) was added and the mixture heated at 600C for 6h. The solvent was removed and the residue was taken up in EtOAc (3 x 10 mL). The organic phase was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by silica gel chromatograhy using
EtOAc / petroleum ether (1 : 9) as eluent.
To a stirred mixture of the azide and Pd/C (40 mg) in tetrahydrofuran (4 mL), through which N2 had been passed for 5 min, was added NaBH4 (0.11 g, 3 mmol) and MeOH (8 mL) dropwise. After stirring for 20 min, the catalyst was filtered, the solution was neutralized and the organic solvent was removed. The aqueous phase was extracted with EtOAc (2 x 15 mL) and the organic phase was dried (Na2SO4) and evaporated.
The tert-butoxycarbonyl group was removed by treatment with 4N HCI in tetrahydrofiuan (12 mL) for 30 min at room temperature : 0.18 g, 48% overall yield; rump. decomp.; [a]D -12.0 (c 0.5, MeOH); 1 H NMR (CD3OD) # : 0.85 (t, J = 7 Hz, 3
H), 1.25 (br s, 24 H), 1.65 (m, 2 H), 2.10 (m, 4 H), 3.22 (m, 1 H), 3.51 (m, 1 H), 5.38 (m, 2 H); FAB MS m/z (relative intensity) 311 (M+H) (24), 280 (17). Anal. Called. for C204N2Ck: C, 62.64; H, 11.56; N, 7.30. Found : C, 62.61; H, 11.60; N, 7.18.
Claims (5)
1. 2-Amino-aNcanoic and alkenoic acid derivatives of general formula (I):
wherein R', R2 = H, amino protective groups such as benzyl, tert-butoxycarbonyl, benzyloxycarbonyl, fluorenylmethoxycarbonyl; wherein R3 = aromatic, heterocyclic, carbocyclic, linear or branched saturated chain, alkyl carbonyl, alkoxy carbonyl and nitrile; wherein R4 = H, alkyl; wherein RS = H, OH, alkyl,alkoxy, NH2, N-alkyl, or acyl groups; whereinm2 l;n20;o2 l;p20;q20; their salts and processes for their preparation through Wittig type reactions on compounds of general formula (V)
2. Aldehydes of general formula (V) and processes for their preparation through reduction of compound of general formula (IV)
wherein Rl, R2, p, q are as defined for formula (I); wherein R7 = alkyl; wherein 1.
3. 2-Amino alcohols of general formula (II) and diamines of general formula (m),
wherein Rl, R2, R3,R4, m, n, o, p, q are as defined for formula (I); wherein R6 = OH, alkoxy group, and their salts.
4. Compounds according to any of claims 1,2,3 for use in therapy and, in particular, for,: i) their action on the central and peripheral nervous system, inluding analgesia, anaesthesia, sleep disorders, anxiety, depresion and as anti-convulsants; ii) the treatment of infiaminatory diseases including arthritis and asthma; iii) the treatment of abnormal cell growth and differentiation, inluding cancer and generative diseases; iv) diseases of the cardiovascular system; v) diabetes, obesity, appetite controL
5. Compounds according to any of claims 1,2,3 for use as liposomes, niosomes, microcapsules, lotions, emulsions, creams or other entities used in the pharmaceutical, personal care or cosmetic industries.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9706130A GB2323594A (en) | 1997-03-25 | 1997-03-25 | 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9706130A GB2323594A (en) | 1997-03-25 | 1997-03-25 | 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9706130D0 GB9706130D0 (en) | 1997-05-14 |
| GB2323594A true GB2323594A (en) | 1998-09-30 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9706130A Withdrawn GB2323594A (en) | 1997-03-25 | 1997-03-25 | 2-amino-alkanoic acid derivatives, 2-amino alcohols and diamines |
Country Status (1)
| Country | Link |
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| GB (1) | GB2323594A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000053568A1 (en) * | 1999-03-09 | 2000-09-14 | Cosmoferm B.V. | Sphingoid base derivatives and uses thereof |
| DE10048714A1 (en) * | 2000-09-30 | 2002-04-11 | Gruenenthal Gmbh | 5-amino-1-penlen-3-ol derivatives |
| US7064147B2 (en) | 2002-03-28 | 2006-06-20 | Warner-Lambert Company | Amino acids with affinity for the α-2-delta-protein |
| US7491835B2 (en) | 2003-09-25 | 2009-02-17 | Pfizer Inc | Prodrugs of amino acids with affinity for the α2δ-protein |
| JP2013512255A (en) * | 2009-11-25 | 2013-04-11 | サイトメティックス、インコーポレイテッド | Arachidonic acid analogs and analgesic treatment thereby |
| US8618165B2 (en) | 2005-05-04 | 2013-12-31 | Pronova Biopharma Norge As | Compounds |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4868061A (en) * | 1988-05-19 | 1989-09-19 | The Standard Oil Company | Olefinic aryl oxime derivatives of hydantoins |
-
1997
- 1997-03-25 GB GB9706130A patent/GB2323594A/en not_active Withdrawn
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4868061A (en) * | 1988-05-19 | 1989-09-19 | The Standard Oil Company | Olefinic aryl oxime derivatives of hydantoins |
Non-Patent Citations (4)
| Title |
|---|
| CHEM ABS 105: 79318 & TETRAHEDRON LETT., 27(1), 23-6, (1986) * |
| CHEM ABS 122:315057 & J. ORG. CHEM., 60(7), 2210-15, (1995) * |
| CHEM ABS. 109:473862 & TETRAHEDRON, 43(19), 4297-308, (1987) * |
| CHEM ABS. 110:8600 & SYNTHESIS, (3), 173-5, (1988) * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000053568A1 (en) * | 1999-03-09 | 2000-09-14 | Cosmoferm B.V. | Sphingoid base derivatives and uses thereof |
| DE10048714A1 (en) * | 2000-09-30 | 2002-04-11 | Gruenenthal Gmbh | 5-amino-1-penlen-3-ol derivatives |
| US6815443B2 (en) | 2000-09-30 | 2004-11-09 | Gruenenthal Gmbh | 5-Amino-1-pentene-3-ol substituted derivatives |
| US7064147B2 (en) | 2002-03-28 | 2006-06-20 | Warner-Lambert Company | Amino acids with affinity for the α-2-delta-protein |
| US7517909B2 (en) | 2002-03-28 | 2009-04-14 | Pfizer Inc | Amino acids with affinity for the α2δ-protein |
| US7491835B2 (en) | 2003-09-25 | 2009-02-17 | Pfizer Inc | Prodrugs of amino acids with affinity for the α2δ-protein |
| US8618165B2 (en) | 2005-05-04 | 2013-12-31 | Pronova Biopharma Norge As | Compounds |
| JP2013512255A (en) * | 2009-11-25 | 2013-04-11 | サイトメティックス、インコーポレイテッド | Arachidonic acid analogs and analgesic treatment thereby |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9706130D0 (en) | 1997-05-14 |
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