ZA200301868B - 4-pyrimidinamine derivatives, pharmaceutical compositions and related methods. - Google Patents

4-pyrimidinamine derivatives, pharmaceutical compositions and related methods. Download PDF

Info

Publication number: ZA200301868B
Authority: ZA; South Africa
Prior art keywords: compound; alkyl; group; cell; pharmaceutical composition
Prior art date: 2000-08-08

Application number

ZA200301868A

Other languages

English (en)

Inventor

Elfrida R Grant

Robert Allan Zivin

Zhong Zhong

Allen B Reitz

Frank K Brown

Michael Mcmillian

Malcolm Scott

Tina Morgan Ross

Original Assignee

Ortho Mcneil Pharm Inc

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.)

2000-08-08

Filing date

2003-03-06

Publication date

2004-06-25

2003-03-06 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2004-06-25 Publication of ZA200301868B publication Critical patent/ZA200301868B/en

Links

238000000034 method Methods 0.000 title claims description 105
239000008194 pharmaceutical composition Substances 0.000 title claims description 77
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical class NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims description 214
125000000217 alkyl group Chemical group 0.000 claims description 186
210000004027 cell Anatomy 0.000 claims description 130
-1 benzo[b]thien-2-yl Chemical group 0.000 claims description 123
210000002569 neuron Anatomy 0.000 claims description 78
125000003545 alkoxy group Chemical group 0.000 claims description 58
230000000472 traumatic effect Effects 0.000 claims description 58
125000003118 aryl group Chemical group 0.000 claims description 51
125000003710 aryl alkyl group Chemical group 0.000 claims description 48
229910052739 hydrogen Inorganic materials 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 45
239000000126 substance Substances 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 43
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 42
229910052736 halogen Inorganic materials 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 38
125000003282 alkyl amino group Chemical group 0.000 claims description 36
150000002367 halogens Chemical group 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 33
230000034994 death Effects 0.000 claims description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000004663 dialkyl amino group Chemical group 0.000 claims description 28
208000014674 injury Diseases 0.000 claims description 28
150000003839 salts Chemical class 0.000 claims description 27
230000008733 trauma Effects 0.000 claims description 27
230000000302 ischemic effect Effects 0.000 claims description 26
150000002431 hydrogen Chemical class 0.000 claims description 25
230000016273 neuron death Effects 0.000 claims description 25
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
125000004093 cyano group Chemical group *C#N 0.000 claims description 20
229910052757 nitrogen Inorganic materials 0.000 claims description 20
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 19
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 19
230000008569 process Effects 0.000 claims description 19
239000003937 drug carrier Substances 0.000 claims description 17
125000000751 azo group Chemical group [*]N=N[*] 0.000 claims description 16
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 16
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
125000004414 alkyl thio group Chemical group 0.000 claims description 14
125000005129 aryl carbonyl group Chemical group 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 14
125000004076 pyridyl group Chemical group 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
238000001727 in vivo Methods 0.000 claims description 13
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
125000002071 phenylalkoxy group Chemical group 0.000 claims description 12
125000004193 piperazinyl group Chemical group 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
125000001769 aryl amino group Chemical group 0.000 claims description 10
125000004104 aryloxy group Chemical group 0.000 claims description 10
239000004305 biphenyl Substances 0.000 claims description 10
125000001624 naphthyl group Chemical group 0.000 claims description 10
235000010290 biphenyl Nutrition 0.000 claims description 9
125000004966 cyanoalkyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
210000002950 fibroblast Anatomy 0.000 claims description 8
125000002541 furyl group Chemical group 0.000 claims description 8
210000002064 heart cell Anatomy 0.000 claims description 8
238000000338 in vitro Methods 0.000 claims description 8
210000004698 lymphocyte Anatomy 0.000 claims description 8
210000002540 macrophage Anatomy 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
238000002156 mixing Methods 0.000 claims description 8
210000004498 neuroglial cell Anatomy 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 7
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 6
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 6
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
150000003973 alkyl amines Chemical class 0.000 claims description 6
125000001691 aryl alkyl amino group Chemical group 0.000 claims description 6
125000005265 dialkylamine group Chemical group 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 claims description 5
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
125000005110 aryl thio group Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
230000000069 prophylactic effect Effects 0.000 claims description 4
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 claims description 3
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
125000006494 2-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
125000006482 3-iodobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(I)=C1[H])C([H])([H])* 0.000 claims description 2
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
IBEMEXYAUSJOKL-UHFFFAOYSA-N 4-n,4-n-dimethyl-1-n-[6-(4-phenylmethoxyphenyl)pyrimidin-4-yl]benzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=NC=N1 IBEMEXYAUSJOKL-UHFFFAOYSA-N 0.000 claims description 2
125000001318 4-trifluoromethylbenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])*)C(F)(F)F 0.000 claims description 2
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 2
125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
125000004103 aminoalkyl group Chemical group 0.000 claims description 2
125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 2
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 2
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
SYRZNUNAMKMHQF-UHFFFAOYSA-N 1-n-[6-[3,5-bis(trifluoromethyl)phenyl]pyrimidin-4-yl]-4-n,4-n-dimethylbenzene-1,4-diamine Chemical compound C1=CC(N(C)C)=CC=C1NC1=CC(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=NC=N1 SYRZNUNAMKMHQF-UHFFFAOYSA-N 0.000 claims 1
VFVMMRBVGXAIQI-UHFFFAOYSA-N 2-[2-[4-[[6-(3-phenylphenyl)pyrimidin-4-yl]amino]phenyl]ethylamino]ethanol Chemical compound C1=CC(CCNCCO)=CC=C1NC1=CC(C=2C=C(C=CC=2)C=2C=CC=CC=2)=NC=N1 VFVMMRBVGXAIQI-UHFFFAOYSA-N 0.000 claims 1
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
240000007594 Oryza sativa Species 0.000 claims 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
238000002560 therapeutic procedure Methods 0.000 claims 1
125000001701 trimethoxybenzyl group Chemical group 0.000 claims 1
229930195712 glutamate Natural products 0.000 description 62
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 61
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108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 32
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
239000004471 Glycine Substances 0.000 description 20
QLTXKCWMEZIHBJ-PJGJYSAQSA-N dizocilpine maleate Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 QLTXKCWMEZIHBJ-PJGJYSAQSA-N 0.000 description 20
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Classifications

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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
- 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
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms directly attached in position 2
- C07D239/12—Nitrogen atoms not forming part of a nitro radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Hospice & Palliative Care (AREA)
Psychiatry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

ZA200301868A 2000-08-08 2003-03-06 4-pyrimidinamine derivatives, pharmaceutical compositions and related methods. ZA200301868B (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US22379100P	2000-08-08	2000-08-08

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ZA200301868B true ZA200301868B (en)	2004-06-25

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Country Status (16)

Country	Link
US (3)	US20030008883A1 (fr)
EP (1)	EP1313713B1 (fr)
JP (1)	JP2004505952A (fr)
CN (1)	CN1468225A (fr)
AR (1)	AR031601A1 (fr)
AT (1)	ATE398109T1 (fr)
AU (1)	AU2001281120A1 (fr)
BR (1)	BR0113165A (fr)
CA (1)	CA2419030A1 (fr)
DE (1)	DE60134414D1 (fr)
HK (1)	HK1054033A1 (fr)
IL (1)	IL154240A0 (fr)
MX (1)	MXPA03001226A (fr)
NZ (1)	NZ524100A (fr)
WO (1)	WO2002012198A2 (fr)
ZA (1)	ZA200301868B (fr)

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CA2531490A1 (fr) *	2003-07-15	2005-02-03	Neurogen Corporation	Analogues de pyrimidine-4-ylamine substitues constituant des ligands des recepteurs vanilloides
WO2005009980A1 (fr) *	2003-07-22	2005-02-03	Neurogen Corporation	Analogues de pyridin-2-ylamine substitues
AU2004295050A1 (en)	2003-11-24	2005-06-16	F.Hoffmann-La Roche Ag	Pyrazolyl and imidazolyl pyrimidines
AU2005212438A1 (en) *	2004-02-11	2005-08-25	Amgen Inc.	Vanilloid receptor ligands and their use in treatments
CA2564355C (fr)	2004-05-07	2012-07-03	Amgen Inc.	Modulateurs de proteines kinases et procede d'utilisation
EP1763526B1 (fr)	2004-06-28	2009-06-24	Bayer Schering Pharma AG	Pyrimidines 4,6-disubstituees et leur utilisation comme inhibiteurs des proteines kinases
EP1807418A2 (fr) *	2004-10-22	2007-07-18	Amgen, Inc	Heterocycles azotes substitues comme ligands du recepteur vanilloide et leur utilisation comme medicaments
HU0900798D0 (en)	2009-12-21	2010-03-01	Vichem Chemie Kutato Kft	4-phenylamino-pyrimidine derivatives having protein kinase inhibitor activity
EP2554163A4 (fr) *	2010-03-26	2013-07-17	Univ Hokkaido Nat Univ Corp	Agent de traitement thérapeutique de maladies neurodégénératives
BR112015003655A2 (pt) *	2012-08-23	2017-07-04	Virostatics Srl	composto; uso de um composto; e composição farmacêutica
AU2014362231B2 (en) *	2013-12-11	2019-04-04	Biogen Ma Inc.	Biaryl compounds useful for the treatment of human diseases in oncology, neurology and immunology
AU2018352701A1 (en) *	2017-10-17	2020-06-04	Merck Patent Gmbh	Pyrimidine ΤΒΚ/ΙΚΚE inhibitor compounds and uses thereof

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US5506231A (en) *	1989-03-31	1996-04-09	The Children's Medical Center Corporation	Treatment of aids dementia, myelopathy and blindness
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2001
- 2001-08-06 WO PCT/US2001/024659 patent/WO2002012198A2/fr not_active Ceased
- 2001-08-06 BR BR0113165-6A patent/BR0113165A/pt not_active IP Right Cessation
- 2001-08-06 HK HK03106375.9A patent/HK1054033A1/zh unknown
- 2001-08-06 US US09/922,874 patent/US20030008883A1/en not_active Abandoned
- 2001-08-06 EP EP01959581A patent/EP1313713B1/fr not_active Expired - Lifetime
- 2001-08-06 CA CA002419030A patent/CA2419030A1/fr not_active Abandoned
- 2001-08-06 CN CNA018166938A patent/CN1468225A/zh active Pending
- 2001-08-06 AT AT01959581T patent/ATE398109T1/de not_active IP Right Cessation
- 2001-08-06 AU AU2001281120A patent/AU2001281120A1/en not_active Abandoned
- 2001-08-06 NZ NZ524100A patent/NZ524100A/en not_active Application Discontinuation
- 2001-08-06 IL IL15424001A patent/IL154240A0/xx unknown
- 2001-08-06 JP JP2002518176A patent/JP2004505952A/ja active Pending
- 2001-08-06 DE DE60134414T patent/DE60134414D1/de not_active Expired - Lifetime
- 2001-08-06 MX MXPA03001226A patent/MXPA03001226A/es active IP Right Grant
- 2001-08-08 AR ARP010103803A patent/AR031601A1/es unknown
2003
- 2003-03-06 ZA ZA200301868A patent/ZA200301868B/en unknown
- 2003-03-25 US US10/396,158 patent/US20030212079A1/en not_active Abandoned
- 2003-03-25 US US10/395,971 patent/US20040006094A1/en not_active Abandoned

Also Published As

Publication number	Publication date
MXPA03001226A (es)	2004-09-10
EP1313713B1 (fr)	2008-06-11
ATE398109T1 (de)	2008-07-15
HK1054033A1 (zh)	2003-11-14
US20040006094A1 (en)	2004-01-08
DE60134414D1 (de)	2008-07-24
IL154240A0 (en)	2003-07-31
JP2004505952A (ja)	2004-02-26
AU2001281120A1 (en)	2002-02-18
BR0113165A (pt)	2003-07-15
AR031601A1 (es)	2003-09-24
WO2002012198A2 (fr)	2002-02-14
US20030008883A1 (en)	2003-01-09
WO2002012198A3 (fr)	2002-06-06
CN1468225A (zh)	2004-01-14
US20030212079A1 (en)	2003-11-13
EP1313713A2 (fr)	2003-05-28
NZ524100A (en)	2005-01-28
CA2419030A1 (fr)	2002-02-14

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