ES8604544A1 - Procedimiento para preparar nuevos derivados de acidos feni-laceticos - Google Patents

Procedimiento para preparar nuevos derivados de acidos feni-laceticos

Info

Publication number
ES8604544A1
ES8604544A1 ES545879A ES545879A ES8604544A1 ES 8604544 A1 ES8604544 A1 ES 8604544A1 ES 545879 A ES545879 A ES 545879A ES 545879 A ES545879 A ES 545879A ES 8604544 A1 ES8604544 A1 ES 8604544A1
Authority
ES
Spain
Prior art keywords
group
general formula
methyl
compound
piperidino
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
Application number
ES545879A
Other languages
English (en)
Other versions
ES545879A0 (es
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of ES8604544A1 publication Critical patent/ES8604544A1/es
Publication of ES545879A0 publication Critical patent/ES545879A0/es
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
    • C07D211/14—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • 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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • 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

Abstract

PROCEDIMIENTO PARA LA PREPARACION DE DERIVADOS DE ACIDOS FENILACETICOS, DE FORMULA GENERAL (I), EN LA QUE R1 SIGNIFICA UN GRUPO ALQUILENIMINO CON 4 A 6 ATOMOS DE CARBONO, NO RAMIFICADO; R2 SIGNIFICA UN ATOMO DE HIDROGENO O HALOGENO O UN GRUPO METILO O METOXI; R3 SIGNIFICA UN ATOMO DE HIDROGENO O UN GRUPO ALQUILO CON 1 A 7 ATOMOS DE CARBONO; Y R4 SIGNIFICA UN ATOMO DE HIDROGENO O UN GRUPO ALQUILO CON 1 A 3 ATOMOS DE CARBONO, Y SUS ENANTIOMEROS Y SUS SALES FARMACEUTICAMENTE ACEPTABLES. CONSISTE EN TRANSFORMAR UN GRUPO A EN UN GRUPO CARBOXI, EN UN COMPUESTO DE FORMULA GENERAL (II), MEDIANTE UN PROCESO DE HIDROLISIS, TERMOLISIS O HIDROGENOLISIS. DE APLICACION EN EL TRATAMIENTO DE LA DIABETES MELLITUS.
ES545879A 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos Expired ES8604544A1 (es)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19833347565 DE3347565A1 (de) 1983-12-30 1983-12-30 Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE19853522604 DE3522604A1 (de) 1983-12-30 1985-06-25 Neue feste formen von 2-(gamma)thoxy-4-(n-(1-(2-piperidino-phenyl)-3-methyl-1-butyl)-aminocarbonylmethyl)-benzoesaeure, diese formen enthaltende arzneimittel und verfahren zu ihrer herstellung

Publications (2)

Publication Number Publication Date
ES8604544A1 true ES8604544A1 (es) 1986-02-01
ES545879A0 ES545879A0 (es) 1986-02-01

Family

ID=37847099

Family Applications (7)

Application Number Title Priority Date Filing Date
ES539078A Expired ES8605500A1 (es) 1983-12-30 1984-12-27 Procedimiento para preparar derivados de acidos fenilaceticos.
ES545881A Expired ES8604546A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545880A Expired ES8604545A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545883A Expired ES8604548A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545882A Expired ES8604547A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545879A Expired ES8604544A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES556495A Expired ES8802145A1 (es) 1983-12-30 1986-06-24 Procedimiento para preparar dos nuevas formas solidas de acido 2-etoxi-4-(n-(1-(2-piperidino-fenil)-3-metil-1-butil)-aminocarbonilmetil)-benzoico

Family Applications Before (5)

Application Number Title Priority Date Filing Date
ES539078A Expired ES8605500A1 (es) 1983-12-30 1984-12-27 Procedimiento para preparar derivados de acidos fenilaceticos.
ES545881A Expired ES8604546A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545880A Expired ES8604545A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545883A Expired ES8604548A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos
ES545882A Expired ES8604547A1 (es) 1983-12-30 1985-08-05 Procedimiento para preparar nuevos derivados de acidos feni-laceticos

Family Applications After (1)

Application Number Title Priority Date Filing Date
ES556495A Expired ES8802145A1 (es) 1983-12-30 1986-06-24 Procedimiento para preparar dos nuevas formas solidas de acido 2-etoxi-4-(n-(1-(2-piperidino-fenil)-3-metil-1-butil)-aminocarbonilmetil)-benzoico

Country Status (26)

Country Link
EP (2) EP0147850B1 (es)
JP (2) JPH0623200B2 (es)
KR (1) KR900005320B1 (es)
AT (1) ATE44027T1 (es)
AU (2) AU577815B2 (es)
BG (1) BG61519B2 (es)
CA (2) CA1225398A (es)
CS (1) CS409791A3 (es)
DD (1) DD231348A5 (es)
DE (4) DE3347565A1 (es)
DK (2) DK167439B1 (es)
ES (7) ES8605500A1 (es)
FI (2) FI80447C (es)
GR (2) GR82614B (es)
HK (1) HK87492A (es)
HU (1) HU194548B (es)
IE (1) IE57700B1 (es)
IL (2) IL73963A (es)
LU (1) LU90301I2 (es)
MX (1) MX9202772A (es)
NL (1) NL980034I1 (es)
NO (3) NO162819C (es)
NZ (2) NZ210657A (es)
PT (2) PT79772B (es)
SG (1) SG55492G (es)
ZA (2) ZA8410103B (es)

Families Citing this family (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3523466A1 (de) * 1985-07-01 1987-01-08 Thomae Gmbh Dr K Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3347565A1 (de) * 1983-12-30 1985-07-11 Thomae Gmbh Dr K Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP0965591B1 (de) * 1991-06-21 2002-09-04 Boehringer Ingelheim Pharma KG Verfahren zur Herstellung von (S)-3-Methyl-1-(2-piperidino-phenyl)-1-butylamin
AU660930B2 (en) * 1991-06-21 1995-07-13 Novo Nordisk A/S (S)(+)-2-ethoxy-4-(N-(1-(2-piperidinophenyl)-3-methyl-1- butyl)aminocarbonylmethyl)benzoic acid
FR2763590B1 (fr) * 1997-05-22 2000-03-24 Synthelabo Derives d'acides[[[(arylmethyl)amino]carbonyl] alkyl]- aromatiques, leur preparation et leur application en therapeutique
DK1248604T4 (da) 2000-01-21 2012-05-21 Novartis Ag Kombinationer indeholdende dipeptidylpeptidase-IV-inhibitorer og antidiabetiske midler
AU2003260078A1 (en) * 2002-08-23 2004-03-11 Dr. Reddy's Laboratories Limited Crystalline and amorphous forms of (s) -repaglinide and the processes for preparation thereof
EP1636199A2 (de) * 2003-05-14 2006-03-22 Cilag AG Verfahren zur herstellung von phenylessig derivaten
WO2004103983A1 (en) * 2003-05-26 2004-12-02 Biocon Limited Process for the preparation of s(+)-2-ethoxy-4-[n-{1-(2-piperidinophelyl)-3-methyl-1- butyl} aminocarbonylmethyl]benzoic acid derivatives
WO2004108673A2 (en) * 2003-06-09 2004-12-16 Boehringer Ingelheim International Gmbh Inhibitors of papilloma virus
FR2875805B1 (fr) * 2004-09-27 2006-12-29 Genfit S A Composes derives de n-(benzyl) phenylacetamide substitues, preparation et utilisations
CN1305863C (zh) * 2004-12-27 2007-03-21 浙江大学 (s)－异丙基－(2－哌啶)苯基－甲基胺的合成方法
GT200600381A (es) 2005-08-25 2007-03-28 Compuestos organicos
MY159522A (en) 2005-09-14 2017-01-13 Takeda Pharmaceuticals Co Administration of dipeptidyl peptidase inhibitors
EP2177221A1 (en) 2008-10-20 2010-04-21 Krka Tovarna Zdravil, D.D., Novo Mesto Process for the preparation of substantially optically pure Repaglinide and precursors thereof
ES2459468T3 (es) 2009-05-15 2014-05-09 Novartis Ag Arilpiridinas como inhibidores de aldosterona sintasa
CA2761853A1 (en) 2009-05-15 2010-11-18 Novartis Ag Benzoxazolone derivatives as aldosterone synthase inhibitors
CN102448928B (zh) 2009-05-28 2014-10-01 诺华股份有限公司 作为中性溶酶(neprilysin)抑制剂的取代的氨基丁酸衍生物
ES2602902T3 (es) 2009-05-28 2017-02-22 Novartis Ag Derivados aminopropiónicos sustituidos como inhibidores de neprilisina
WO2011041293A1 (en) 2009-09-30 2011-04-07 Takeda Pharmaceutical Company Limited Pyrazolo [1, 5-a] pyrimidine derivatives as apoptosis signal-regulating kinase 1 inhibitors
ES2663351T3 (es) 2009-11-17 2018-04-12 Novartis Ag Derivados de aril-piridina como inhibidores de la aldosterona sintasa
JO2967B1 (en) 2009-11-20 2016-03-15 نوفارتس ايه جي Acetic acid derivatives of carbamoyl methyl amino are substituted as new NEP inhibitors
US8575160B2 (en) 2009-11-30 2013-11-05 Novartis Ag Imidazole derivatives as aldosterone synthase inhibitors
RS53176B (en) 2010-02-03 2014-06-30 Takeda Pharmaceutical Company Limited KINASE INHIBITORS 1 REGULATING SIGNALS IN APOPTOSIS
US8877815B2 (en) 2010-11-16 2014-11-04 Novartis Ag Substituted carbamoylcycloalkyl acetic acid derivatives as NEP
US8673974B2 (en) 2010-11-16 2014-03-18 Novartis Ag Substituted amino bisphenyl pentanoic acid derivatives as NEP inhibitors
WO2012095548A2 (es) 2011-01-13 2012-07-19 Centro De Investigación Biomédica En Red De Enfermedades Neurodegenerativas (Ciberned) Compuestos para el tratamiento de enfermedades neurodegenerativas
UY35144A (es) 2012-11-20 2014-06-30 Novartis Ag Miméticos lineales sintéticos de apelina para el tratamiento de insuficiencia cardiaca
PE20151666A1 (es) 2013-02-14 2015-11-19 Novartis Ag Derivados sustituidos del acido bisfenil butanoico fosfonico como inhibidores de la nep
MX2016001021A (es) 2013-07-25 2016-08-03 Novartis Ag Bioconjugados de polipeptidos de apelina sinteticos.
TW201536814A (zh) 2013-07-25 2015-10-01 Novartis Ag 用於治療心臟衰竭之合成環狀多肽
BR112017014194A2 (pt) 2015-01-23 2018-01-09 Novartis Ag conjugados de ácido graxo de apelina sintéticos com meia-vida melhorada
UY38072A (es) 2018-02-07 2019-10-01 Novartis Ag Compuestos derivados de éster butanoico sustituido con bisfenilo como inhibidores de nep, composiciones y combinaciones de los mismos

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3100575A1 (de) * 1981-01-10 1982-09-02 Dr. Karl Thomae Gmbh, 7950 Biberach "neue benzoesaeuren, ihre herstellung und ihre verwendung als arzneimittel"
DE3100535A1 (de) * 1981-01-10 1982-08-12 Dr. Karl Thomae Gmbh, 7950 Biberach "neue carbonsaeure-derivate, ihre herstellung und ihre verwendung als arzneimittel"
DE3375783D1 (en) * 1982-07-06 1988-04-07 Thomae Gmbh Dr K Phenyl-acetic-acid derivatives, their preparation and pharmaceutical compostions containing them
FR2554875B1 (fr) * 1983-11-10 1986-02-28 Dba Amplificateur hydraulique de freinage
DE3523466A1 (de) * 1985-07-01 1987-01-08 Thomae Gmbh Dr K Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE3347565A1 (de) * 1983-12-30 1985-07-11 Thomae Gmbh Dr K Neue phenylessigsaeurederivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

Also Published As

Publication number Publication date
DE3478682D1 (en) 1989-07-20
EP0147850B1 (de) 1989-06-14
FI82689B (fi) 1990-12-31
BG61519B2 (bg) 1997-10-31
AU3721084A (en) 1985-08-01
ES8604548A1 (es) 1986-02-01
ES545880A0 (es) 1986-02-01
AU5913986A (en) 1987-01-08
DE19875044I2 (de) 2002-07-18
GR82614B (en) 1985-05-02
NO862532D0 (no) 1986-06-24
KR900005320B1 (ko) 1990-07-27
NO862532L (no) 1986-12-29
EP0207331A1 (de) 1987-01-07
DK167573B1 (da) 1993-11-22
HUT37773A (en) 1986-02-28
DK296686A (da) 1986-12-26
IL73963A (en) 1989-01-31
JPS60158171A (ja) 1985-08-19
JPS62474A (ja) 1987-01-06
IE843349L (en) 1985-06-30
SG55492G (en) 1992-10-02
PT82832B (pt) 1988-12-15
JPH0623200B2 (ja) 1994-03-30
NO162819C (no) 1990-02-21
NO168302C (no) 1992-02-05
NO845282L (no) 1985-07-01
CA1225398A (en) 1987-08-11
PT79772A (de) 1985-01-01
JPH0739405B2 (ja) 1995-05-01
GR861558B (en) 1986-10-17
LU90301I2 (fr) 1998-12-21
CA1292000C (en) 1991-11-12
ES8604547A1 (es) 1986-02-01
NO162819B (no) 1989-11-13
AU577815B2 (en) 1988-10-06
EP0147850A3 (en) 1985-08-07
IL79217A0 (en) 1986-09-30
ZA864695B (en) 1988-02-24
ZA8410103B (en) 1986-09-24
DK613184D0 (da) 1984-12-20
HU194548B (en) 1988-02-29
FI80447C (fi) 1990-06-11
AU583631B2 (en) 1989-05-04
PT79772B (de) 1987-01-05
NO168302B (no) 1991-10-28
FI845145L (fi) 1985-07-01
ES539078A0 (es) 1986-03-16
IL79217A (en) 1991-01-31
EP0207331B1 (de) 1990-05-23
ES8604546A1 (es) 1986-02-01
KR850004590A (ko) 1985-07-25
FI845145A0 (fi) 1984-12-28
FI862650A0 (fi) 1986-06-23
FI80447B (fi) 1990-02-28
IL73963A0 (en) 1985-03-31
DE3347565A1 (de) 1985-07-11
NL980034I1 (nl) 1999-02-01
DD231348A5 (de) 1985-12-24
ATE44027T1 (de) 1989-06-15
DK296686D0 (da) 1986-06-24
HK87492A (en) 1992-11-13
FI862650A (fi) 1986-12-26
CS409791A3 (en) 1992-07-15
ES545883A0 (es) 1986-02-01
DK167439B1 (da) 1993-11-01
MX9202772A (es) 1992-06-30
ES545881A0 (es) 1986-02-01
DE3522604A1 (de) 1987-01-08
FI82689C (fi) 1991-04-10
ES556495A0 (es) 1988-04-01
EP0147850A2 (de) 1985-07-10
ES8604545A1 (es) 1986-02-01
ES8802145A1 (es) 1988-04-01
ES545879A0 (es) 1986-02-01
PT82832A (de) 1986-07-01
NZ216640A (en) 1989-02-24
IE57700B1 (en) 1993-03-10
NO1999016I1 (no) 1999-07-20
ES545882A0 (es) 1986-02-01
ES8605500A1 (es) 1986-03-16
NZ210657A (en) 1988-10-28
DK613184A (da) 1985-07-01

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Legal Events

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PC1A Transfer granted
SPCF Request for supplementary protection certificate filed

Free format text: REPAGLINIDA (NOVONORM)

Spc suppl protection certif: C9900006

Filing date: 19990216

SPCG Supplementary protection certificate granted

Free format text: REPAGLINIDA (NOVONORM)

Spc suppl protection certif: C9900006

Filing date: 19990216

Expiry date: 20101126

Effective date: 20021119

FD1A Patent lapsed

Effective date: 20100528