UA79460C2 - Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds - Google Patents

Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds Download PDF

Info

Publication number: UA79460C2
Authority: UA; Ukraine
Prior art keywords: oxo; piperidin; monosubstituted; optionally; oxazin
Prior art date: 2002-04-09

Application number

UA20041109155A

Other languages

English (en)

Ukrainian (uk)

Inventor

Jover Antoni Torrens

Castrillo Perez Aurelio

Constansa Jordi Frigola

Prio Josep Mas

Zueras Alberto Dordal

Fisas Escasany Angeles

Original Assignee

Esteve Labor Dr

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.)

2002-04-09

Filing date

2003-08-04

Publication date

2007-06-25

2003-08-04 Application filed by Esteve Labor Dr filed Critical Esteve Labor Dr

2007-06-25 Publication of UA79460C2 publication Critical patent/UA79460C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 74
238000000034 method Methods 0.000 title claims abstract description 34
HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 title claims abstract description 22
238000002360 preparation method Methods 0.000 title abstract description 10
239000003814 drug Substances 0.000 title abstract description 7
-1 monosubstituted aliphatic radical Chemical class 0.000 claims description 257
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 141
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 116
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 113
229920006395 saturated elastomer Polymers 0.000 claims description 109
150000003254 radicals Chemical class 0.000 claims description 86
229910052739 hydrogen Inorganic materials 0.000 claims description 70
239000000203 mixture Substances 0.000 claims description 70
125000005842 heteroatom Chemical group 0.000 claims description 69
125000002950 monocyclic group Chemical group 0.000 claims description 67
125000001424 substituent group Chemical group 0.000 claims description 59
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 43
239000001257 hydrogen Substances 0.000 claims description 39
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 claims description 38
150000002431 hydrogen Chemical class 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
125000004093 cyano group Chemical group *C#N 0.000 claims description 35
125000002947 alkylene group Chemical group 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 33
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CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 27
125000005418 aryl aryl group Chemical group 0.000 claims description 27
239000012453 solvate Substances 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 22
RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims description 21
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 18
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
125000003118 aryl group Chemical group 0.000 claims description 16
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NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
239000005711 Benzoic acid Substances 0.000 claims description 9
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239000012752 auxiliary agent Substances 0.000 claims description 6
210000003169 central nervous system Anatomy 0.000 claims description 6
KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims description 5
208000024172 Cardiovascular disease Diseases 0.000 claims description 5
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125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
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PNWCRHPBZXISGC-UHFFFAOYSA-N 7-fluoro-1-piperidin-4-yl-4h-3,1-benzoxazin-2-one Chemical compound C12=CC(F)=CC=C2COC(=O)N1C1CCNCC1 PNWCRHPBZXISGC-UHFFFAOYSA-N 0.000 claims description 3
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PCLKOZKDKZHSPM-UHFFFAOYSA-N 5-chloro-1-piperidin-4-yl-4h-3,1-benzoxazin-2-one Chemical compound O=C1OCC=2C(Cl)=CC=CC=2N1C1CCNCC1 PCLKOZKDKZHSPM-UHFFFAOYSA-N 0.000 claims description 2
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IRXZOQHJCAGFFA-UHFFFAOYSA-N 8-chloro-1-piperidin-4-yl-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(Cl)=CC=CC=2COC(=O)N1C1CCNCC1 IRXZOQHJCAGFFA-UHFFFAOYSA-N 0.000 claims description 2
HXKYPFVUMOWPOZ-UHFFFAOYSA-N 8-hydroxy-1-piperidin-4-yl-4h-3,1-benzoxazin-2-one Chemical compound C1=2C(O)=CC=CC=2COC(=O)N1C1CCNCC1 HXKYPFVUMOWPOZ-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
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150000005840 aryl radicals Chemical class 0.000 claims description 2
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125000004122 cyclic group Chemical group 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
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WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical class [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 2
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VHWJSJBTUWUEAL-UHFFFAOYSA-N propanamide;hydrochloride Chemical compound Cl.CCC(N)=O VHWJSJBTUWUEAL-UHFFFAOYSA-N 0.000 claims description 2
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BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims 2
JVTRZJXFAOQMRA-UHFFFAOYSA-N 1,3-oxazin-2-one Chemical compound O=C1N=CC=CO1 JVTRZJXFAOQMRA-UHFFFAOYSA-N 0.000 claims 1
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125000003545 alkoxy group Chemical group 0.000 claims 1
METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 1
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HAGVWBQWCRHRRA-UHFFFAOYSA-N piperidin-1-yl acetate Chemical compound CC(=O)ON1CCCCC1 HAGVWBQWCRHRRA-UHFFFAOYSA-N 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
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PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
RIVIDPPYRINTTH-UHFFFAOYSA-N n-ethylpropan-2-amine Chemical compound CCNC(C)C RIVIDPPYRINTTH-UHFFFAOYSA-N 0.000 description 1
229910052754 neon Inorganic materials 0.000 description 1
GKAOGPIIYCISHV-UHFFFAOYSA-N neon atom Chemical compound [Ne] GKAOGPIIYCISHV-UHFFFAOYSA-N 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
NOUWNNABOUGTDQ-UHFFFAOYSA-N octane Chemical compound CCCCCCC[CH2+] NOUWNNABOUGTDQ-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008014 pharmaceutical binder Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000006187 pill Substances 0.000 description 1
235000013550 pizza Nutrition 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
210000001747 pupil Anatomy 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical class C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
PIDHNVVHJDBAAL-UHFFFAOYSA-N tert-butyl 4-(6-chloro-2-oxo-4h-3,1-benzoxazin-1-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1N1C2=CC=C(Cl)C=C2COC1=O PIDHNVVHJDBAAL-UHFFFAOYSA-N 0.000 description 1
ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000002268 wool Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K31/536—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines ortho- or peri-condensed with carbocyclic ring systems
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (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)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Pain & Pain Management (AREA)
Hematology (AREA)
Obesity (AREA)
Rheumatology (AREA)
Cardiology (AREA)
Immunology (AREA)
Heart & Thoracic Surgery (AREA)
Psychiatry (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Hospice & Palliative Care (AREA)
Vascular Medicine (AREA)
Child & Adolescent Psychology (AREA)
Nutrition Science (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

UA20041109155A 2002-04-09 2003-08-04 Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds UA79460C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
ES200200813A ES2193875B2 (es)	2002-04-09	2002-04-09	Derivados de benzoxazinona, su preparacion y su aplicacion como medicamentos.
PCT/EP2003/003629 WO2003084952A1 (en)	2002-04-09	2003-04-08	Benzoxazinone-derived compounds, their preparation und use as medicaments

Publications (1)

Publication Number	Publication Date
UA79460C2 true UA79460C2 (en)	2007-06-25

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UA20041109155A UA79460C2 (en)	2002-04-09	2003-08-04	Benzoxazinone derived compounds, method for their preparation, intermediate, medicaments containing these compounds

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US (3)	US7056914B2 (is)
EP (2)	EP1497285B1 (is)
JP (1)	JP2005529866A (is)
KR (1)	KR20050008679A (is)
CN (1)	CN1659164A (is)
AR (2)	AR039256A1 (is)
AT (2)	ATE489382T1 (is)
AU (2)	AU2003222804A1 (is)
BR (1)	BR0309083A (is)
CA (1)	CA2481701A1 (is)
DE (2)	DE60335094D1 (is)
DK (1)	DK1500654T3 (is)
EC (1)	ECSP045353A (is)
ES (3)	ES2193875B2 (is)
HR (1)	HRP20040919A2 (is)
IL (1)	IL164442A0 (is)
IS (1)	IS7491A (is)
MA (1)	MA27692A1 (is)
MX (1)	MXPA04009889A (is)
NO (1)	NO20044322L (is)
NZ (1)	NZ536167A (is)
PL (1)	PL372537A1 (is)
PT (1)	PT1500654E (is)
RU (1)	RU2004133041A (is)
TN (1)	TNSN04203A1 (is)
UA (1)	UA79460C2 (is)
WO (2)	WO2003084952A1 (is)
ZA (1)	ZA200408275B (is)

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ATE427935T1 (de) *	2001-08-07	2009-04-15	Banyu Pharma Co Ltd	Spiro isobenzofurane als neuropeptid y rezeptor antagonisten
ES2193875B2 (es) *	2002-04-09	2005-03-01	Laboratorios Del Dr. Esteve, S.A.	Derivados de benzoxazinona, su preparacion y su aplicacion como medicamentos.

2002
- 2002-04-09 ES ES200200813A patent/ES2193875B2/es not_active Expired - Fee Related
2003
- 2003-04-04 US US10/407,343 patent/US7056914B2/en not_active Expired - Fee Related
- 2003-04-04 AR ARP030101184A patent/AR039256A1/es not_active Application Discontinuation
- 2003-04-08 WO PCT/EP2003/003629 patent/WO2003084952A1/en not_active Ceased
- 2003-04-08 AT AT03718741T patent/ATE489382T1/de not_active IP Right Cessation
- 2003-04-08 MX MXPA04009889A patent/MXPA04009889A/es active IP Right Grant
- 2003-04-08 ES ES03718741T patent/ES2356815T3/es not_active Expired - Lifetime
- 2003-04-08 AR ARP030101235A patent/AR048567A1/es not_active Application Discontinuation
- 2003-04-08 EP EP03718741A patent/EP1497285B1/en not_active Expired - Lifetime
- 2003-04-08 DE DE60335094T patent/DE60335094D1/de not_active Expired - Lifetime
- 2003-04-08 US US10/409,235 patent/US7041665B2/en not_active Expired - Fee Related
- 2003-04-08 JP JP2003582149A patent/JP2005529866A/ja active Pending
- 2003-04-08 PL PL03372537A patent/PL372537A1/xx not_active Application Discontinuation
- 2003-04-08 KR KR10-2004-7016130A patent/KR20050008679A/ko not_active Withdrawn
- 2003-04-08 IL IL16444203A patent/IL164442A0/xx unknown
- 2003-04-08 CN CN038128853A patent/CN1659164A/zh active Pending
- 2003-04-08 HR HR20040919A patent/HRP20040919A2/hr not_active Application Discontinuation
- 2003-04-08 CA CA002481701A patent/CA2481701A1/en not_active Abandoned
- 2003-04-08 RU RU2004133041/04A patent/RU2004133041A/ru not_active Application Discontinuation
- 2003-04-08 NZ NZ536167A patent/NZ536167A/en unknown
- 2003-04-08 AU AU2003222804A patent/AU2003222804A1/en not_active Abandoned
- 2003-04-08 BR BR0309083-3A patent/BR0309083A/pt not_active IP Right Cessation
- 2003-04-09 DE DE60303440T patent/DE60303440T2/de not_active Expired - Lifetime
- 2003-04-09 EP EP03712152A patent/EP1500654B1/en not_active Expired - Lifetime
- 2003-04-09 PT PT03712152T patent/PT1500654E/pt unknown
- 2003-04-09 AT AT03712152T patent/ATE316966T1/de not_active IP Right Cessation
- 2003-04-09 WO PCT/ES2003/000162 patent/WO2003084939A1/es not_active Ceased
- 2003-04-09 AU AU2003216934A patent/AU2003216934A1/en not_active Abandoned
- 2003-04-09 ES ES03712152T patent/ES2258219T3/es not_active Expired - Lifetime
- 2003-04-09 DK DK03712152T patent/DK1500654T3/da active
- 2003-08-04 UA UA20041109155A patent/UA79460C2/uk unknown
2004
- 2004-10-06 IS IS7491A patent/IS7491A/is unknown
- 2004-10-08 MA MA27902A patent/MA27692A1/fr unknown
- 2004-10-08 TN TNP2004000203A patent/TNSN04203A1/en unknown
- 2004-10-08 EC EC2004005353A patent/ECSP045353A/es unknown
- 2004-10-12 NO NO20044322A patent/NO20044322L/no not_active Application Discontinuation
- 2004-10-13 ZA ZA200408275A patent/ZA200408275B/en unknown
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Also Published As

Publication number	Publication date
AU2003216934A1 (en)	2003-10-20
DE60303440D1 (de)	2006-04-13
MA27692A1 (fr)	2006-01-02
US7056914B2 (en)	2006-06-06
KR20050008679A (ko)	2005-01-21
US7041665B2 (en)	2006-05-09
ZA200408275B (en)	2006-04-26
ATE316966T1 (de)	2006-02-15
PL372537A1 (en)	2005-07-25
ATE489382T1 (de)	2010-12-15
TNSN04203A1 (en)	2007-03-12
EP1500654A1 (en)	2005-01-26
IL164442A0 (en)	2005-12-18
EP1497285B1 (en)	2010-11-24
ES2258219T3 (es)	2006-08-16
DK1500654T3 (da)	2006-06-06
HRP20040919A2 (en)	2005-04-30
DE60335094D1 (de)	2011-01-05
EP1500654B1 (en)	2006-02-01
DE60303440T2 (de)	2006-10-26
NO20044322L (no)	2004-10-12
WO2003084952A1 (en)	2003-10-16
AR048567A1 (es)	2006-05-10
US7514429B2 (en)	2009-04-07
EP1497285A1 (en)	2005-01-19
ECSP045353A (es)	2005-01-28
CN1659164A (zh)	2005-08-24
BR0309083A (pt)	2005-04-19
ES2356815T3 (es)	2011-04-13
HK1069820A1 (en)	2005-06-03
NZ536167A (en)	2006-06-30
RU2004133041A (ru)	2005-09-10
US20040067941A1 (en)	2004-04-08
US20060128701A1 (en)	2006-06-15
IS7491A (is)	2004-10-06
PT1500654E (pt)	2006-06-30
MXPA04009889A (es)	2005-08-16
ES2193875B2 (es)	2005-03-01
AR039256A1 (es)	2005-02-16
AU2003222804A1 (en)	2003-10-20
US20040058920A1 (en)	2004-03-25
CA2481701A1 (en)	2003-10-16
WO2003084939A1 (es)	2003-10-16
JP2005529866A (ja)	2005-10-06
ES2193875A1 (es)	2003-11-01

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