USRE40259E1 - Alpha-aminoamide derivatives useful as analgesic agents - Google Patents
Alpha-aminoamide derivatives useful as analgesic agents Download PDFInfo
- Publication number
- USRE40259E1 USRE40259E1 US11/359,982 US35998298A USRE40259E US RE40259 E1 USRE40259 E1 US RE40259E1 US 35998298 A US35998298 A US 35998298A US RE40259 E USRE40259 E US RE40259E
- Authority
- US
- United States
- Prior art keywords
- pain
- benzylamino
- propanamide
- hydrogen
- hydroxy
- 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.)
- Expired - Lifetime
Links
- 0 **C1=CC=C(CN([1*])C([2*])([3*])C)C=C1 Chemical compound **C1=CC=C(CN([1*])C([2*])([3*])C)C=C1 0.000 description 8
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/54—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and etherified hydroxy groups bound to the carbon skeleton
Definitions
- the present invention relates to novel and known alpha-aminoamide compounds, to a process for their preparation, to pharmaceutical composition containing them and to their use as therapeutic agents.
- the compounds of the present invention are endowed with analgesic properties and are particularly useful for the treatment and alleviation of chronic and neuropathic pain.
- Chronic and neuropathic pain are associated with prolonged tissue damage or injuries to the peripheral or central nervous system and result from a number of complex changes in nociceptive pathways.
- Clinical manifestations of chronic pain include a sensation of burning or electric shock, feelings of bodily distortion, allodynia and hyperpathia.
- the present invention is based on the finding that compounds known from the above-cited international applications and new ones, closely related thereto, have analgesic properties in mammals, including humans.
- one object of the present invention is to provide the use of a compound of formula (I) wherein:
- a —(CH 2 ) m —, —(CH 2 ) n — or —(CH 2 ) v — chain may be a branched or straight chain.
- Alkyl and alkoxy groups may be branched or straight groups. Representative examples of C 1 -C 4 alkyl groups include methyl, ethyl, n- and iso-propyl, n-, iso- sec- and tert-butyl.
- C 1 -C 4 alkoxy groups include methoxy and ethoxy.
- a C 3 -C 6 cycloalkyl group is for instance cyclopropyl, cyclopentyl or cyclohexyl, in particular cyclopentyl or cyclohexyl.
- a halogen atom is fluorine, bromine, chlorine or iodine, in particular, chlorine or fluorine.
- Pharmaceutically acceptable salts of the compounds of the invention include acid addition salts with inorganic, e.g. nitric, hydrochloric, hydrobromic, sulphuric, perchloric and phosphoric acids or organic, e.g. acetic, trifluoroacetic, propionic, glycolic, lactic, oxalic, malonic, malic, maleic, tartaric, citric, benzoic, cinnamic, mandelic and salicylic acids.
- inorganic e.g. nitric, hydrochloric, hydrobromic, sulphuric, perchloric and phosphoric acids
- organic e.g. acetic, trifluoroacetic, propionic, glycolic, lactic, oxalic, malonic, malic, maleic, tartaric, citric, benzoic, cinnamic, mandelic and salicylic acids.
- the compounds of formula (I) have asymmetric carbon atoms and therefore they can exist either as racemic mixtures or as individual optical isomers (enantiomers).
- the present invention also include within its scope all the possible isomers and their mixtures and both the metabolites and the pharmaceutically acceptable bioprecursors (otherwise known as pro-drugs) of the compounds of formula (I).
- Preferred compounds of formula (I) are those wherein
- An aspect of this invention relates to a pharmaceutically composition having analgesic activity, in particular against chronic and neuropathic pain, comprising a compound of formula (I), as herein defined, as an active agent and a pharmaceutically acceptable salt thereof.
- a further aspect of this invention relates to a method of treating a mammal, including humans, in need of an analgesic agent, said method comprising administering thereto an effective amount of a compound of formula (I) or a pharmaceutically acceptable salt thereof.
- Neuropathic and chronic pain conditions in a mammal can thus be alleviated and treated.
- Examples of pain conditions that can be treated by a compound of formula (I) include:
- Another object of the present invention are the novel compounds of formula (IA) wherein:
- preferred compounds of formula (IA) are those wherein
- the compounds of formula (I) and (IA) and the pharmaceutically acceptable salts thereof can be obtained by well known processes as described in the above cited international applications.
- a compound of formula (IA) and the salts thereof can be obtained by a process comprising:
- a compound of formula (IV) is a compound of formula (IA) in which R 1 is hydrogen.
- the reaction of a compound of formula (II) with a compound of formula (III) to give a compound of formula (IA) or (IV) is a reductive amination reaction which can be carried out according to well known methods. According to a preferred embodiment of the invention it may be performed under nitrogen atmosphere, in a suitable organic solvent, such as an alcohol, e.g. a lower alkanol, in particular methanol, or in acetonitrile, at a temperature ranging from about 0° C. to about 40° C., in the presence of a reducing agent, the most appropriate being sodium cyanoborohydride.
- a suitable organic solvent such as an alcohol, e.g. a lower alkanol, in particular methanol, or in acetonitrile
- the halogen W is preferably iodine.
- the alkylation reaction of a compound of formula (IV) with a compound of formula (V) can be carried out in a suitable organic solvent, such as an alcohol, e.g. methanol, ethanol or isopropanol, in particular in ethanol, at a temperature ranging from about 0° C. to about 50° C.
- the alkylation reaction of a compound of formula (IV) with an aldehyde of formula (VI) can be carried out in a suitable organic solvent, such as an alcohol, e.g. methanol, ethanol or acetonitrile in the presence of a suitable reducing agent, such as sodium cyanoborohydride, at a temperature ranging from about 0° C. to about 30° C.
- a suitable organic solvent such as an alcohol, e.g. methanol, ethanol or acetonitrile
- a suitable reducing agent such as sodium cyanoborohydride
- a compound of formula (IA) can be converted, as stated above, into another compound of formula (IA) by known methods.
- Process-variant b) above may be regarded as an example of optional conversion of a compound of formula (IA) into another compound of formula (IA).
- the compounds of formula (II) and (III), (V) and (VI) are known compounds or can be obtained by known methods.
- groups are present, which need to be protected before submitting them to the hereabove illustrated reactions, they may be protected before being reacted and then deprotected according to methods well known in organic chemistry.
- the compounds of the invention are active as analgesic agents, as proven for instance by the fact that they have been found to be active in the formalin test.
- Formalin test is a useful tool for obtaining neurogenic inflammation and continuous pain (Shibata et al, Pain, 38: 347-352, 1989).
- Formalin produces a distinct biphasic response.
- the early phase seems to be caused predominantly by C-fibre activation due to peripheral stimulus, while the late phase appears to be dependent on the combination of an inflammatory reaction in the peripheral tissue and functional changes in the dorsal horn of the spinal cord. This functional changes seem to be initiated by the C-fibre barrage during the early phase (Tjolsen et al. Pain 51, 5-17, 1992).
- Substance P and bradykinin participate in the early phase, while histamine, serotonin, prostaglandins and bradykinin are involved in the late phase.
- mice Male NMRI CD- 1 mice (22-25 g) were injected with 20 ml ⁇ l of 2.7% solution of formalin into the right hindpaw and placed immediately into observation chambers. The cumulative licking time of the injected paw was recorded in the acute phase (0-5 min) and in the chronic phase (30-40 min) of the nociceptive response of formalin.
- locomotor activity test lasted 15 min. Five minutes after testing locomotor activity, the mice were put on the rotarod for 2 min and the number of mice falling within this time were counted.
- the compounds of the invention are useful in mammals, including humans, as analgesic agents.
- they are useful in treating pain associated with damage or permanent alteration of the peripheral or central nervous system, for example peripheral neuropathies, such as trigeminal neuralgia, postherapeutic neuralgia, diabetic neuropathy, raticulopathy glossopharyngeal neuralgia, and neuropathy secondary to metastatic infiltration, adiposis dolorosa, and burn pain; and central pain conditions following stroke, thalamic lesions and multiple sclerosis.
- peripheral neuropathies such as trigeminal neuralgia, postherapeutic neuralgia, diabetic neuropathy, raticulopathy glossopharyngeal neuralgia, and neuropathy secondary to metastatic infiltration, adiposis dolorosa, and burn pain
- central pain conditions following stroke thalamic lesions and multiple sclerosis.
- the conditions of a patient in need of an analgesic agent may thus be improved.
- the compounds of the invention can be administered in a variety of dosage forms, e.g. orally, in the form of tablets, capsules, sugar or film coated tablets, liquid solutions or suspensions; rectally in the form of suppositories; parenterally, e.g. intramuscularly, or by intravenous injection or infusion.
- the dosage depends on the age, weight, conditions of the patient and on the administration route; for example, the dosage adopted for oral administration to adult humans e.g. for the representative compounds of the invention
- the invention includes pharmaceutical compositions comprising a compound of formula (IA), as an active principle, in association with a pharmaceutically acceptable excipient (which can be a carrier or a diluent).
- a pharmaceutically acceptable excipient which can be a carrier or a diluent.
- the pharmaceutical compositions containing the compounds of the invention are usually prepared following conventional methods and are administered in a pharmaceutically suitable form.
- the solid oral forms may contain, together with the active compound, diluents, e.g. lactose, destrose, saccharose, cellulose, corn starch or potato starch; lubricants, e.g. silica, talc, stearic acid, magnesium or calcium stearate, and/or polyethylene glycols; binding agents, e.g. starches, arabic gums, gelatin, methylcellulose, carboxymethylcellulose or polyvinyl pyrrolidone; desegregating agents, e.g.
- diluents e.g. lactose, destrose, saccharose, cellulose, corn starch or potato starch
- lubricants e.g. silica, talc, stearic acid, magnesium or calcium stearate, and/or polyethylene glycols
- binding agents e.g. starches, arabic gums, gelatin, methylcellulose, carboxymethylcellulose or polyvinyl pyrroli
- a starch alginic acid, alginates or sodium starch glycolate; effervescing mixtures; dyestuffs; sweeteners; wetting agents such as lecithin, polysorbates, laurylsulphates; and, in general, non-toxic and pharmacologically inactive substances used in pharmaceutical formulations.
- Said pharmaceutical preparations may be manufactured in known manner, for example, by means of mixing, granulating, tabletting, sugar-coating, or film-coating processes.
- the liquid dispersion for oral administration may be e.g. syrups, emulsions and suspension.
- the syrups may contain as carrier, for example, saccharose or saccharose with glycerine and/or mannitol and/or sorbitol.
- the suspension and the emulsion may contain as carrier, for example, a natural gum, agar, sodium alginate, pectin, methylcellulose, carboxymethylcellulose, or polyvinyl alcohol.
- the suspension or solutions for intramuscular injections may contain, together with the active compound, a pharmaceutically acceptable carrier, e.g. sterile water, olive oil, ethyl oleate, glycols, e.g. propylene glycol, and, if desired, a suitable amount of lidocaine hydrochloride.
- a pharmaceutically acceptable carrier e.g. sterile water, olive oil, ethyl oleate, glycols, e.g. propylene glycol, and, if desired, a suitable amount of lidocaine hydrochloride.
- the solutions for intravenous injections or infusion may contain as carrier, for example, sterile water or preferably they may be in the form of sterile, aqueous, isotonic saline solutions.
- the suppositories may contain together with the active compound a pharmaceutically acceptable carrier, e.g. cocoa butter, polyethylene glycol, a polyoxyethylene sorbitan fatty acid ester surfactant or lecithin.
- a pharmaceutically acceptable carrier e.g. cocoa butter, polyethylene glycol, a polyoxyethylene sorbitan fatty acid ester surfactant or lecithin.
- preparation can be made of capsules having the following composition:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9727523.4A GB9727523D0 (en) | 1997-12-31 | 1997-12-31 | Alpha-aminoamide derivatives useful as analgesic agents |
PCT/EP1998/008157 WO1999035125A1 (en) | 1997-12-31 | 1998-12-12 | Alpha-aminoamide derivatives useful as analgesic agents |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/582,198 Reissue US6306903B1 (en) | 1997-12-31 | 1998-12-12 | Alpha-aminoamide derivatives useful as analgesic agents |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE40259E1 true USRE40259E1 (en) | 2008-04-22 |
Family
ID=10824342
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/582,198 Ceased US6306903B1 (en) | 1997-12-31 | 1998-12-12 | Alpha-aminoamide derivatives useful as analgesic agents |
US11/359,982 Expired - Lifetime USRE40259E1 (en) | 1997-12-31 | 1998-12-12 | Alpha-aminoamide derivatives useful as analgesic agents |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/582,198 Ceased US6306903B1 (en) | 1997-12-31 | 1998-12-12 | Alpha-aminoamide derivatives useful as analgesic agents |
Country Status (19)
Country | Link |
---|---|
US (2) | US6306903B1 (ja) |
EP (1) | EP1045830B1 (ja) |
JP (1) | JP4410930B2 (ja) |
KR (1) | KR100525587B1 (ja) |
AT (1) | ATE238273T1 (ja) |
BR (1) | BR9814548A (ja) |
CA (1) | CA2316902C (ja) |
DE (1) | DE69813896T2 (ja) |
DK (1) | DK1045830T3 (ja) |
EA (1) | EA002763B1 (ja) |
ES (1) | ES2194392T3 (ja) |
GB (1) | GB9727523D0 (ja) |
HK (1) | HK1028020A1 (ja) |
HU (1) | HU228995B1 (ja) |
IL (2) | IL136734A0 (ja) |
NO (1) | NO327453B1 (ja) |
NZ (1) | NZ505440A (ja) |
PT (1) | PT1045830E (ja) |
WO (1) | WO1999035125A1 (ja) |
Cited By (5)
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US20040248978A1 (en) * | 2001-09-03 | 2004-12-09 | Patricia Salvati | Pharmaceutical composition comprising gabapentin or an analogue thereof and an aminoamide and its analgesic use |
US20060079570A1 (en) * | 2003-01-16 | 2006-04-13 | Patricia Salvati | Alpha-aminoamide derivatives useful as antimigraine agents |
US20080096965A1 (en) * | 2004-09-10 | 2008-04-24 | Newron Pharmaceuticals S.P.A. | (Halobenzyloxy) Benzylamino-Propanamides as Sodium and/or Calcium Channel Selective Modulators |
US20080319057A1 (en) * | 2005-12-22 | 2008-12-25 | Newron Pharmaceuticals S.P.A. | 2-Phenylethylamino Derivatives as Calcium and/or Sodium Channel Modulators |
US20100016440A1 (en) * | 2003-08-25 | 2010-01-21 | Newron Pharmaceuticals S.P.A. | Alpha-aminoamide derivatives useful as anti-inflammatory agents |
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CA2310664C (en) * | 1997-11-21 | 2008-03-11 | Euro-Celtique S.A. | Substituted 2-aminoacetamides and the use thereof |
JP2004517840A (ja) * | 2000-11-27 | 2004-06-17 | フアルマシア・イタリア・エツセ・ピー・アー | フェニルアセトアミド−ピラゾール誘導体およびそれの抗腫瘍薬としての使用 |
US6476068B1 (en) | 2001-12-06 | 2002-11-05 | Pharmacia Italia, S.P.A. | Platinum derivative pharmaceutical formulations |
WO2004087125A1 (en) * | 2003-04-02 | 2004-10-14 | Ionix Pharmaceuticals Limited | Amino acid derivatives as inhibitors of mammalian sodium channels |
AR044007A1 (es) | 2003-04-11 | 2005-08-24 | Newron Pharmaceuticals Inc | Metodos para el tratamiento de la enfermedad de parkinson |
WO2005000309A2 (en) * | 2003-06-27 | 2005-01-06 | Ionix Pharmaceuticals Limited | Chemical compounds |
EP1524267A1 (en) * | 2003-10-15 | 2005-04-20 | Newron Pharmaceuticals S.p.A. | Substituted benzylaminoalkylene heterocycles |
EP1533298A1 (en) | 2003-11-21 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | 3-aminopyrrolidone derivatives |
EP1533302A1 (en) * | 2003-11-21 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | Histidine derivatives |
EP1533295A1 (en) | 2003-11-24 | 2005-05-25 | Newron Pharmaceuticals S.p.A. | Cyclopentyl Derivatives |
EP1535908A1 (en) * | 2003-11-24 | 2005-06-01 | Newron Pharmaceuticals S.p.A. | N-acyl-N'-benzyl-alkylendiamino drivatives |
EP1557166A1 (en) * | 2004-01-21 | 2005-07-27 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of lower urinary tract disorders |
EP1588704A1 (en) | 2004-04-22 | 2005-10-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of restless legs syndrome and addictive disorders |
TW200728258A (en) | 2005-10-10 | 2007-08-01 | Glaxo Group Ltd | Novel compounds |
TW200730494A (en) | 2005-10-10 | 2007-08-16 | Glaxo Group Ltd | Novel compounds |
ATE472529T1 (de) * | 2005-10-10 | 2010-07-15 | Glaxo Group Ltd | Prolinamidderivate als natriumkanalmodulatoren |
EP1870097A1 (en) * | 2006-06-15 | 2007-12-26 | Newron Pharmaceuticals S.p.A. | Alpha-aminoamide derivatives useful in the treatment of cognitive disorders |
WO2007147491A1 (en) * | 2006-06-19 | 2007-12-27 | Newron Pharmaceuticals S.P.A. | Process for the production of 2- [4 - ( 3- and 2-flu0r0benzyl0xy) benzylamin0] propan amides |
EP2155663B1 (en) | 2007-06-15 | 2017-11-29 | Newron Pharmaceuticals S.p.A. | Substituted 2-[2-(phenyl)ethylamino]alkaneamide derivatives and their use as sodium and/or calcium channel modulators |
CN104523668B (zh) | 2007-12-11 | 2020-06-09 | 纽朗制药有限公司 | 高纯度的2-[4-(3-或2-氟苄氧基)苄氨基]丙酰胺类及其用途 |
EP2314569A1 (en) | 2009-10-22 | 2011-04-27 | Merck Patent GmbH | Novel polymorphic forms of (S)-2-[4-(3-Fluoro-benzyloxy)-benzylamino]-propionamide mesylate salt and processes of manufacturing thereof |
HUE030504T2 (en) | 2010-04-27 | 2017-05-29 | Newron Pharm Spa | Process for the preparation of ralfinamide methanesulfonate salts or their R-enantiomers |
SG11201500377UA (en) | 2012-09-10 | 2015-02-27 | Hoffmann La Roche | 6-amino acid heteroaryldihydropyrimidines for the treatment and prophylaxis of hepatitis b virus infection |
WO2015102390A1 (ko) * | 2013-12-30 | 2015-07-09 | 이화여자대학교 산학협력단 | 신규한 아미드 유도체 또는 이의 약학적으로 허용가능한 염, 이의 제조방법 및 이를 포함하는 통증의 예방 또는 치료용 약학적 조성물 |
ES2912881T3 (es) | 2014-12-23 | 2022-05-30 | Convergence Pharmaceuticals | Procedimiento para preparar derivados de alfa-carboxamida pirrolidina |
CN107522654B (zh) * | 2016-06-21 | 2020-09-01 | 中国人民解放军军事医学科学院毒物药物研究所 | 新的α-氨基酰胺衍生物及其医药用途 |
SG11202002706XA (en) | 2017-10-05 | 2020-04-29 | Biogen Inc | Process for preparing alpha-carboxamide pyrolidine derivatives |
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Also Published As
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ATE238273T1 (de) | 2003-05-15 |
IL136734A (en) | 2007-03-08 |
NZ505440A (en) | 2002-02-01 |
JP2002508302A (ja) | 2002-03-19 |
KR20010033706A (ko) | 2001-04-25 |
US6306903B1 (en) | 2001-10-23 |
PT1045830E (pt) | 2003-08-29 |
EA002763B1 (ru) | 2002-08-29 |
EP1045830A1 (en) | 2000-10-25 |
DE69813896T2 (de) | 2003-11-06 |
JP4410930B2 (ja) | 2010-02-10 |
NO20003399L (no) | 2000-08-02 |
CA2316902C (en) | 2006-06-06 |
EA200000731A1 (ru) | 2001-02-26 |
IL136734A0 (en) | 2001-06-14 |
DK1045830T3 (da) | 2003-08-04 |
HK1028020A1 (en) | 2001-02-02 |
GB9727523D0 (en) | 1998-02-25 |
ES2194392T3 (es) | 2003-11-16 |
WO1999035125A1 (en) | 1999-07-15 |
NO20003399D0 (no) | 2000-06-29 |
CA2316902A1 (en) | 1999-07-15 |
KR100525587B1 (ko) | 2005-11-03 |
HUP0100870A2 (hu) | 2001-07-30 |
EP1045830B1 (en) | 2003-04-23 |
HU228995B1 (en) | 2013-07-29 |
HUP0100870A3 (en) | 2002-11-28 |
NO327453B1 (no) | 2009-07-06 |
BR9814548A (pt) | 2000-10-10 |
DE69813896D1 (de) | 2003-05-28 |
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