SK4742002A3 - Purine derivatives - Google Patents

Purine derivatives Download PDF

Info

Publication number: SK4742002A3
Authority: SK; Slovakia
Prior art keywords: formula; phenyl; alkyl; amino; compound
Prior art date: 1999-10-14

Application number

SK474-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Sandra Marina Monaghan

Original Assignee

Pfizer

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.)

1999-10-14

Filing date

2000-10-06

Publication date

2003-05-02

2000-10-06 Application filed by Pfizer filed Critical Pfizer

2003-05-02 Publication of SK4742002A3 publication Critical patent/SK4742002A3/sk

Links

229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 3
125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 181
238000000034 method Methods 0.000 claims abstract description 106
239000000203 mixture Substances 0.000 claims abstract description 100
150000003839 salts Chemical class 0.000 claims abstract description 58
239000012453 solvate Substances 0.000 claims abstract description 41
230000008569 process Effects 0.000 claims abstract description 18
238000002360 preparation method Methods 0.000 claims abstract description 15
-1 -OR 3 Chemical group 0.000 claims description 95
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 38
239000001257 hydrogen Substances 0.000 claims description 31
125000006239 protecting group Chemical group 0.000 claims description 31
125000004432 carbon atom Chemical group C* 0.000 claims description 26
125000001624 naphthyl group Chemical group 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
125000004093 cyano group Chemical group *C#N 0.000 claims description 19
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 17
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical class 0.000 claims description 16
241000124008 Mammalia Species 0.000 claims description 15
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000001931 aliphatic group Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 13
125000002733 (C1-C6) fluoroalkyl group Chemical group 0.000 claims description 12
239000003814 drug Substances 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
206010006451 bronchitis Diseases 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
238000004519 manufacturing process Methods 0.000 claims description 11
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
125000000217 alkyl group Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
208000010668 atopic eczema Diseases 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
208000007882 Gastritis Diseases 0.000 claims description 9
150000002431 hydrogen Chemical class 0.000 claims description 9
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
101150051188 Adora2a gene Proteins 0.000 claims description 8
125000001589 carboacyl group Chemical group 0.000 claims description 8
229910052799 carbon Inorganic materials 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 7
241000590002 Helicobacter pylori Species 0.000 claims description 7
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 7
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 7
201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 7
208000006673 asthma Diseases 0.000 claims description 7
229940037467 helicobacter pylori Drugs 0.000 claims description 7
229940044601 receptor agonist Drugs 0.000 claims description 7
239000000018 receptor agonist Substances 0.000 claims description 7
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
206010006458 Bronchitis chronic Diseases 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
208000007451 chronic bronchitis Diseases 0.000 claims description 6
125000004122 cyclic group Chemical group 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
206010009137 Chronic sinusitis Diseases 0.000 claims description 5
201000003883 Cystic fibrosis Diseases 0.000 claims description 5
201000004624 Dermatitis Diseases 0.000 claims description 5
206010012434 Dermatitis allergic Diseases 0.000 claims description 5
206010014561 Emphysema Diseases 0.000 claims description 5
208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
206010020772 Hypertension Diseases 0.000 claims description 5
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
206010063837 Reperfusion injury Diseases 0.000 claims description 5
206010040070 Septic Shock Diseases 0.000 claims description 5
208000006011 Stroke Diseases 0.000 claims description 5
201000008937 atopic dermatitis Diseases 0.000 claims description 5
201000009267 bronchiectasis Diseases 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
208000027157 chronic rhinosinusitis Diseases 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
206010015037 epilepsy Diseases 0.000 claims description 5
201000001881 impotence Diseases 0.000 claims description 5
201000006417 multiple sclerosis Diseases 0.000 claims description 5
230000002093 peripheral effect Effects 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
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 5
206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
230000036303 septic shock Effects 0.000 claims description 5
208000019553 vascular disease Diseases 0.000 claims description 5
201000006474 Brain Ischemia Diseases 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
206010009900 Colitis ulcerative Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
208000028017 Psychotic disease Diseases 0.000 claims description 4
201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
239000002260 anti-inflammatory agent Substances 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
206010008118 cerebral infarction Diseases 0.000 claims description 4
201000009151 chronic rhinitis Diseases 0.000 claims description 4
229940079593 drug Drugs 0.000 claims description 4
230000002496 gastric effect Effects 0.000 claims description 4
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
208000023504 respiratory system disease Diseases 0.000 claims description 4
206010039083 rhinitis Diseases 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 3
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
230000006378 damage Effects 0.000 claims description 3
125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004434 sulfur atom Chemical group 0.000 claims description 3
125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
125000000335 thiazolyl group Chemical group 0.000 claims description 3
125000001544 thienyl group Chemical group 0.000 claims description 3
125000001425 triazolyl group Chemical group 0.000 claims description 3
230000029663 wound healing Effects 0.000 claims description 3
ISOQCNKPHOXVSA-KCIBBDPESA-N (2s,3s,4r,5r)-5-[2-(benzenesulfonamidomethyl)-6-(2,2-diphenylethylamino)purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(=O)(=O)C=3C=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 ISOQCNKPHOXVSA-KCIBBDPESA-N 0.000 claims description 2
NQMRDPMYCWRHEZ-CTMYTVLESA-N (2s,3s,4r,5r)-5-[2-[(benzylsulfonylamino)methyl]-6-(2,2-diphenylethylamino)purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(=O)(=O)CC=3C=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 NQMRDPMYCWRHEZ-CTMYTVLESA-N 0.000 claims description 2
RVHLVGBXHUEWKG-OVDFTCDZSA-N (2s,3s,4r,5r)-5-[6-(2,2-diphenylethylamino)-2-[(2-methylpropylsulfonylamino)methyl]purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(=O)(=O)CC(C)C)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 RVHLVGBXHUEWKG-OVDFTCDZSA-N 0.000 claims description 2
LZRHRGQVGKWSPT-DEGFIOCKSA-N (2s,3s,4r,5r)-5-[6-(2,2-diphenylethylamino)-2-[(naphthalen-2-ylsulfonylamino)methyl]purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(=O)(=O)C=3C=C4C=CC=CC4=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 LZRHRGQVGKWSPT-DEGFIOCKSA-N 0.000 claims description 2
XKRBVOAEAYVDPF-YRIIQKNPSA-N (2s,3s,4r,5r)-5-[6-(2,2-diphenylethylamino)-2-[(propan-2-ylsulfonylamino)methyl]purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(=O)(=O)C(C)C)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 XKRBVOAEAYVDPF-YRIIQKNPSA-N 0.000 claims description 2
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
230000001154 acute effect Effects 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
208000027866 inflammatory disease Diseases 0.000 claims description 2
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
125000003386 piperidinyl group Chemical group 0.000 claims 2
LSEPVPQDSNUYKF-NLJXWPIHSA-N (2s,3s,4r,5r)-5-[6-(2,2-diphenylethylamino)-2-(methanesulfonamidomethyl)purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(CNS(C)(=O)=O)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 LSEPVPQDSNUYKF-NLJXWPIHSA-N 0.000 claims 1
230000000172 allergic effect Effects 0.000 claims 1
125000004103 aminoalkyl group Chemical group 0.000 claims 1
125000002393 azetidinyl group Chemical group 0.000 claims 1
150000001721 carbon Chemical group 0.000 claims 1
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125000004428 fluoroalkoxy group Chemical group 0.000 claims 1
125000002883 imidazolyl group Chemical group 0.000 claims 1
230000000968 intestinal effect Effects 0.000 claims 1
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125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
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239000002465 adenosine A2a receptor agonist Substances 0.000 abstract description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 252
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 138
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239000000243 solution Substances 0.000 description 90
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239000002904 solvent Substances 0.000 description 57
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
238000005481 NMR spectroscopy Methods 0.000 description 37
239000007787 solid Substances 0.000 description 35
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
239000000706 filtrate Substances 0.000 description 16
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IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
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JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
PRQROPMIIGLWRP-UHFFFAOYSA-N N-formyl-methionyl-leucyl-phenylalanin Chemical class CSCCC(NC=O)C(=O)NC(CC(C)C)C(=O)NC(C(O)=O)CC1=CC=CC=C1 PRQROPMIIGLWRP-UHFFFAOYSA-N 0.000 description 4
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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SK474-2002A 1999-10-14 2000-10-06 Purine derivatives SK4742002A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9924361.0A GB9924361D0 (en)	1999-10-14	1999-10-14	Purine derivatives
PCT/IB2000/001446 WO2001027131A1 (en)	1999-10-14	2000-10-06	Purine derivatives

Publications (1)

Publication Number	Publication Date
SK4742002A3 true SK4742002A3 (en)	2003-05-02

Family

ID=10862758

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK474-2002A SK4742002A3 (en)	1999-10-14	2000-10-06	Purine derivatives

Country Status (43)

Country	Link
US (1)	US6448236B1 (pl)
EP (1)	EP1220862B1 (pl)
JP (1)	JP3994008B2 (pl)
KR (1)	KR20030022758A (pl)
CN (1)	CN1166678C (pl)
AP (1)	AP2002002480A0 (pl)
AR (1)	AR026052A1 (pl)
AT (1)	ATE321065T1 (pl)
AU (1)	AU771531B2 (pl)
BG (1)	BG106567A (pl)
BR (1)	BR0014760A (pl)
CA (1)	CA2387533C (pl)
CO (1)	CO5261621A1 (pl)
CR (1)	CR6607A (pl)
CZ (1)	CZ20021179A3 (pl)
DE (1)	DE60026861T2 (pl)
EA (1)	EA004985B1 (pl)
EC (1)	ECSP003713A (pl)
EE (1)	EE200200194A (pl)
ES (1)	ES2257317T3 (pl)
GB (1)	GB9924361D0 (pl)
GE (1)	GEP20043324B (pl)
GT (2)	GT200000170A (pl)
HK (1)	HK1047942B (pl)
HR (1)	HRP20020325A2 (pl)
HU (1)	HUP0203485A3 (pl)
IL (1)	IL148331A0 (pl)
IS (1)	IS6287A (pl)
MA (1)	MA26829A1 (pl)
MX (1)	MXPA02003750A (pl)
MY (1)	MY141512A (pl)
NO (1)	NO20021751L (pl)
NZ (1)	NZ517294A (pl)
OA (1)	OA12060A (pl)
PA (1)	PA8503601A1 (pl)
PE (1)	PE20010753A1 (pl)
PL (1)	PL354880A1 (pl)
SK (1)	SK4742002A3 (pl)
SV (1)	SV2002000199A (pl)
TN (1)	TNSN00203A1 (pl)
TR (1)	TR200201001T2 (pl)
WO (1)	WO2001027131A1 (pl)
ZA (1)	ZA200202725B (pl)

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PE20091156A1 (es)	2007-12-17	2009-09-03	Astrazeneca Ab	Sales de (3-{[[3-(6-amino-2-butoxi-8-oxo-7,8-dihidro-9h-purin-9-il)propil](3-morfolin-4-ilpropil)amino]metil}fenil)acetato de metilo
AU2009203693B2 (en)	2008-01-11	2012-06-07	Novartis Ag	Pyrimidines as kinase inhibitors
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WO2009091032A1 (ja)	2008-01-17	2009-07-23	Dainippon Sumitomo Pharma Co., Ltd.	アデニン化合物の製造方法
PL2391366T3 (pl)	2009-01-29	2013-04-30	Novartis Ag	Podstawione benzimidazole do leczenia gwiaździaków
US8389526B2 (en)	2009-08-07	2013-03-05	Novartis Ag	3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
EA201200260A1 (ru)	2009-08-12	2012-09-28	Новартис Аг	Гетероциклические гидразоны и их применение для лечения рака и воспаления
NZ598220A (en)	2009-08-17	2014-02-28	Intellikine Llc	Heterocyclic compounds and uses thereof
CA2771432A1 (en)	2009-08-20	2011-02-24	Novartis Ag	Heterocyclic oxime compounds
JP2013512859A (ja) *	2009-12-03	2013-04-18	大日本住友製薬株式会社	トール様受容体（ｔｌｒ）を介して作用するイミダゾキノリン
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EA201290958A1 (ru)	2010-03-26	2013-04-30	Инотек Фармасьютикалз Корпорейшн	Способ снижения внутриглазного давления у людей с применением n6-циклопентиладенозина (cpa), производных cpa или их пролекарств
WO2012034095A1 (en)	2010-09-09	2012-03-15	Irm Llc	Compounds and compositions as trk inhibitors
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CN103370317B (zh)	2010-12-16	2015-10-07	阿斯利康(瑞典)有限公司	可用于治疗的咪唑并[4,5-c]喹啉-1-基衍生物
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MA34969B1 (fr)	2011-02-25	2014-03-01	Irm Llc	Composes et compositions en tant qu inibiteurs de trk
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JP6130391B2 (ja)	2011-11-23	2017-05-17	インテリカイン，エルエルシー	Ｍｔｏｒ阻害剤を使用する強化された治療レジメン
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1999
- 1999-10-14 GB GBGB9924361.0A patent/GB9924361D0/en not_active Ceased
2000
- 2000-09-26 PA PA20008503601A patent/PA8503601A1/es unknown
- 2000-10-06 CN CNB008141762A patent/CN1166678C/zh not_active Expired - Fee Related
- 2000-10-06 NZ NZ517294A patent/NZ517294A/en unknown
- 2000-10-06 JP JP2001530349A patent/JP3994008B2/ja not_active Expired - Fee Related
- 2000-10-06 AU AU74412/00A patent/AU771531B2/en not_active Ceased
- 2000-10-06 EP EP00962773A patent/EP1220862B1/en not_active Expired - Lifetime
- 2000-10-06 KR KR1020027004766A patent/KR20030022758A/ko not_active Abandoned
- 2000-10-06 HK HK03100163.8A patent/HK1047942B/zh not_active IP Right Cessation
- 2000-10-06 DE DE60026861T patent/DE60026861T2/de not_active Expired - Fee Related
- 2000-10-06 SK SK474-2002A patent/SK4742002A3/sk unknown
- 2000-10-06 TR TR2002/01001T patent/TR200201001T2/xx unknown
- 2000-10-06 EA EA200200360A patent/EA004985B1/ru not_active IP Right Cessation
- 2000-10-06 HR HR20020325A patent/HRP20020325A2/xx not_active Application Discontinuation
- 2000-10-06 HU HU0203485A patent/HUP0203485A3/hu unknown
- 2000-10-06 CZ CZ20021179A patent/CZ20021179A3/cs unknown
- 2000-10-06 AP APAP/P/2002/002480A patent/AP2002002480A0/en unknown
- 2000-10-06 BR BR0014760-5A patent/BR0014760A/pt not_active IP Right Cessation
- 2000-10-06 WO PCT/IB2000/001446 patent/WO2001027131A1/en not_active Ceased
- 2000-10-06 OA OA1200200103A patent/OA12060A/en unknown
- 2000-10-06 AT AT00962773T patent/ATE321065T1/de not_active IP Right Cessation
- 2000-10-06 GE GE4727A patent/GEP20043324B/en unknown
- 2000-10-06 PL PL00354880A patent/PL354880A1/pl not_active Application Discontinuation
- 2000-10-06 MX MXPA02003750A patent/MXPA02003750A/es active IP Right Grant
- 2000-10-06 CA CA002387533A patent/CA2387533C/en not_active Expired - Fee Related
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- 2000-10-06 EE EEP200200194A patent/EE200200194A/xx unknown
- 2000-10-06 ES ES00962773T patent/ES2257317T3/es not_active Expired - Lifetime
- 2000-10-10 GT GT200000170A patent/GT200000170A/es unknown
- 2000-10-12 MY MYPI20004789A patent/MY141512A/en unknown
- 2000-10-12 CO CO00077983A patent/CO5261621A1/es not_active Application Discontinuation
- 2000-10-12 GT GT200000173A patent/GT200000173A/es unknown
- 2000-10-12 EC EC2000003713A patent/ECSP003713A/es unknown
- 2000-10-13 SV SV2000000199A patent/SV2002000199A/es unknown
- 2000-10-13 TN TNTNSN00203A patent/TNSN00203A1/fr unknown
- 2000-10-13 PE PE2000001099A patent/PE20010753A1/es not_active Application Discontinuation
- 2000-10-13 AR ARP000105422A patent/AR026052A1/es unknown
- 2000-10-16 US US09/688,497 patent/US6448236B1/en not_active Expired - Fee Related
2002
- 2002-02-26 IS IS6287A patent/IS6287A/is unknown
- 2002-03-11 CR CR6607A patent/CR6607A/es not_active Application Discontinuation
- 2002-04-02 BG BG106567A patent/BG106567A/xx unknown
- 2002-04-08 ZA ZA200202725A patent/ZA200202725B/en unknown
- 2002-04-09 MA MA26591A patent/MA26829A1/fr unknown
- 2002-04-12 NO NO20021751A patent/NO20021751L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
PE20010753A1 (es)	2001-07-17
GEP20043324B (en)	2004-04-13
GT200000173A (es)	2002-04-05
BG106567A (en)	2002-12-29
MA26829A1 (fr)	2004-12-20
EP1220862A1 (en)	2002-07-10
DE60026861T2 (de)	2006-09-21
IL148331A0 (en)	2002-09-12
HUP0203485A3 (en)	2005-02-28
CN1378551A (zh)	2002-11-06
CO5261621A1 (es)	2003-03-31
ES2257317T3 (es)	2006-08-01
EP1220862B1 (en)	2006-03-22
TR200201001T2 (tr)	2002-09-23
MXPA02003750A (es)	2003-10-14
EE200200194A (et)	2003-06-16
CR6607A (es)	2003-11-25
CZ20021179A3 (cs)	2003-04-16
PA8503601A1 (es)	2002-02-21
CN1166678C (zh)	2004-09-15
JP3994008B2 (ja)	2007-10-17
HUP0203485A2 (hu)	2003-03-28
EA004985B1 (ru)	2004-10-28
AP2002002480A0 (en)	2002-06-30
CA2387533A1 (en)	2001-04-19
AR026052A1 (es)	2002-12-26
AU7441200A (en)	2001-04-23
GT200000170A (es)	2002-04-03
HK1047942B (zh)	2005-04-01
KR20030022758A (ko)	2003-03-17
DE60026861D1 (de)	2006-05-11
JP2003511460A (ja)	2003-03-25
ZA200202725B (en)	2003-04-08
HRP20020325A2 (en)	2004-04-30
NZ517294A (en)	2004-03-26
US6448236B1 (en)	2002-09-10
SV2002000199A (es)	2002-02-05
ATE321065T1 (de)	2006-04-15
TNSN00203A1 (fr)	2002-05-30
CA2387533C (en)	2007-03-13
NO20021751D0 (no)	2002-04-12
OA12060A (en)	2006-05-03
EA200200360A1 (ru)	2002-10-31
WO2001027131A1 (en)	2001-04-19
NO20021751L (no)	2002-06-13
ECSP003713A (es)	2002-05-23
IS6287A (is)	2002-02-26
PL354880A1 (pl)	2004-03-22
GB9924361D0 (en)	1999-12-15
MY141512A (en)	2010-05-14
BR0014760A (pt)	2002-07-02
AU771531B2 (en)	2004-03-25
HK1047942A1 (zh)	2003-03-14

Publication	Publication Date	Title
SK4742002A3 (en)	2003-05-02	Purine derivatives
AU768308B2 (en)	2003-12-04	Purine derivatives
US6525032B2 (en)	2003-02-25	Purine derivatives
AU2001260537B2 (en)	2006-05-25	2-aminocarbonyl-9H-purine derivatives
SK18192001A3 (sk)	2003-04-01	Deriváty purínu
SK17332002A3 (sk)	2004-03-02	Purínové deriváty