NO312840B1 - 2-(purin-9-yl)-tetrahydrofuran-3,4-diolderivater, farmasöytisk blanding samt anvendelse og fremstilling derav - Google Patents

2-(purin-9-yl)-tetrahydrofuran-3,4-diolderivater, farmasöytisk blanding samt anvendelse og fremstilling derav Download PDF

Info

Publication number: NO312840B1
Authority: NO; Norway
Prior art keywords: diol; tetrazol; tetrahydro; furan; ethyl
Prior art date: 1996-12-24

Application number

NO19993114A

Other languages

English (en)

Norwegian (no)

Other versions

NO993114L (no

NO993114D0 (no

Inventor

David George Allen

Michael David Barker

Brian Cox

Joanna Victoria Geden

Heather Hobbs

Suzanne Elaine Keeling

Alison Judith Redgrave

Iv Thomas Davis Roper

Original Assignee

Glaxo Group Ltd

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.)

1996-12-24

Filing date

1999-06-23

Publication date

2002-07-08

1996-12-24 Priority claimed from GBGB9626845.3A external-priority patent/GB9626845D0/en

1996-12-24 Priority claimed from GBGB9626852.9A external-priority patent/GB9626852D0/en

1996-12-24 Priority claimed from GBGB9626846.1A external-priority patent/GB9626846D0/en

1997-09-27 Priority claimed from GBGB9720536.3A external-priority patent/GB9720536D0/en

1997-10-29 Priority claimed from GBGB9722730.0A external-priority patent/GB9722730D0/en

1999-06-23 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1999-06-23 Publication of NO993114D0 publication Critical patent/NO993114D0/no

1999-08-23 Publication of NO993114L publication Critical patent/NO993114L/no

2002-07-08 Publication of NO312840B1 publication Critical patent/NO312840B1/no

Links

238000002360 preparation method Methods 0.000 title claims description 10
239000008194 pharmaceutical composition Substances 0.000 title description 3
YQUJSBYIKMQCIT-UHFFFAOYSA-N 2-purin-9-yloxolane-3,4-diol Chemical class OC1C(O)COC1N1C2=NC=NC=C2N=C1 YQUJSBYIKMQCIT-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 267
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 216
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 104
239000000203 mixture Substances 0.000 claims description 88
-1 amino, methoxy, hydroxy Chemical group 0.000 claims description 78
229910052757 nitrogen Inorganic materials 0.000 claims description 52
238000006243 chemical reaction Methods 0.000 claims description 44
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002367 halogens Chemical group 0.000 claims description 38
238000000034 method Methods 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
238000011282 treatment Methods 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 8
101150065749 Churc1 gene Proteins 0.000 claims description 8
102100038239 Protein Churchill Human genes 0.000 claims description 8
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
238000010511 deprotection reaction Methods 0.000 claims description 6
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230000008569 process Effects 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
239000012453 solvate Substances 0.000 claims description 6
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
229910006074 SO2NH2 Inorganic materials 0.000 claims description 5
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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
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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 5
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
125000005322 morpholin-1-yl group Chemical group 0.000 claims description 4
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VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
239000000969 carrier Substances 0.000 claims description 3
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
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229910052717 sulfur Inorganic materials 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 3
LCFFJOYIXJKWRM-UHFFFAOYSA-N 2-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC(C2C(C(O)CO2)O)=N1 LCFFJOYIXJKWRM-UHFFFAOYSA-N 0.000 claims 2
SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims 2
125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims 2
CCYUSUQOSHABQD-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCOCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 CCYUSUQOSHABQD-OVDFTCDZSA-N 0.000 claims 1
NTGVVIJCALQADM-MMSSMPOCSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(pyrrolidin-3-ylamino)purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NC4CNCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 NTGVVIJCALQADM-MMSSMPOCSA-N 0.000 claims 1
CMJVPOARTDAFBV-RQXXJAGISA-N (2r,3r,4s,5r)-2-[6-(3,3-dimethylbutylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(2-ethyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CCN1N=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCCC(C)(C)C)=C3N=C2)O)=N1 CMJVPOARTDAFBV-RQXXJAGISA-N 0.000 claims 1
VLFNMYSVSZTCML-RQXXJAGISA-N (2r,3r,4s,5r)-2-[6-amino-2-[2-(3,4-dimethoxyphenyl)ethylamino]purin-9-yl]-5-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound C1=C(OC)C(OC)=CC=C1CCNC1=NC(N)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(N=N3)C(C)C)O)C2=N1 VLFNMYSVSZTCML-RQXXJAGISA-N 0.000 claims 1
XYHKLPLXXLUDKV-RQXXJAGISA-N (2r,3s,4r,5r)-2-(2-methyltetrazol-5-yl)-5-[6-(pentan-3-ylamino)-2-(2-pyridin-2-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(C)N=N3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CC=CC=N1 XYHKLPLXXLUDKV-RQXXJAGISA-N 0.000 claims 1
AWKWFPJUWHYSGJ-GRXQJBFDSA-N (2r,3s,4r,5r)-2-(2-methyltetrazol-5-yl)-5-[6-(pentan-3-ylamino)-2-(2-pyrrolidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C3=NN(C)N=N3)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCC1 AWKWFPJUWHYSGJ-GRXQJBFDSA-N 0.000 claims 1
HIUJHNNCBNJKGX-UHFFFAOYSA-N 2-(2-methyltetrazol-5-yl)oxolane-3,4-diol Chemical compound CN1N=NC(C2C(C(O)CO2)O)=N1 HIUJHNNCBNJKGX-UHFFFAOYSA-N 0.000 claims 1
BKJJATGKMNJRBW-UHFFFAOYSA-N 2-(2-propan-2-yltetrazol-5-yl)oxolane-3,4-diol Chemical compound CC(C)N1N=NC(C2C(C(O)CO2)O)=N1 BKJJATGKMNJRBW-UHFFFAOYSA-N 0.000 claims 1
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
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QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 description 1
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RPIXOLUIHUFDOY-UHFFFAOYSA-N thian-4-amine Chemical compound NC1CCSCC1 RPIXOLUIHUFDOY-UHFFFAOYSA-N 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
230000017423 tissue regeneration Effects 0.000 description 1
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125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
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YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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Classifications

- 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
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Pulmonology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biochemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Medicines Containing Plant Substances (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

NO19993114A 1996-12-24 1999-06-23 2-(purin-9-yl)-tetrahydrofuran-3,4-diolderivater, farmasöytisk blanding samt anvendelse og fremstilling derav NO312840B1 (no)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
GBGB9626845.3A GB9626845D0 (en)	1996-12-24	1996-12-24	Chemical compounds
GBGB9626852.9A GB9626852D0 (en)	1996-12-24	1996-12-24	Chemical compounds
GBGB9626846.1A GB9626846D0 (en)	1996-12-24	1996-12-24	Chemical compounds
GBGB9720536.3A GB9720536D0 (en)	1997-09-27	1997-09-27	Chemical compounds
GBGB9722730.0A GB9722730D0 (en)	1997-10-29	1997-10-29	Chemical compounds
PCT/EP1997/007197 WO1998028319A1 (en)	1996-12-24	1997-12-22	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives

Publications (3)

Publication Number	Publication Date
NO993114D0 NO993114D0 (no)	1999-06-23
NO993114L NO993114L (no)	1999-08-23
NO312840B1 true NO312840B1 (no)	2002-07-08

Family

ID=27517393

Family Applications (1)

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NO19993114A NO312840B1 (no)	1996-12-24	1999-06-23	2-(purin-9-yl)-tetrahydrofuran-3,4-diolderivater, farmasöytisk blanding samt anvendelse og fremstilling derav

Country Status (36)

Country	Link
US (2)	US6426337B1 (is)
EP (1)	EP0948509B1 (is)
JP (1)	JP4156035B2 (is)
KR (1)	KR20000069682A (is)
CN (1)	CN1246124A (is)
AP (1)	AP1105A (is)
AR (1)	AR011044A1 (is)
AT (1)	ATE226212T1 (is)
AU (1)	AU733684B2 (is)
BG (1)	BG63310B1 (is)
BR (1)	BR9714082A (is)
CA (1)	CA2275271A1 (is)
CO (1)	CO4940488A1 (is)
CZ (1)	CZ230999A3 (is)
DE (1)	DE69716468T2 (is)
DK (1)	DK0948509T3 (is)
EA (1)	EA001714B1 (is)
EE (1)	EE04019B1 (is)
ES (1)	ES2186015T3 (is)
GE (1)	GEP20022656B (is)
HU (1)	HUP0000673A3 (is)
ID (1)	ID22271A (is)
IL (1)	IL130547A0 (is)
IS (1)	IS5089A (is)
NO (1)	NO312840B1 (is)
NZ (1)	NZ336332A (is)
OA (1)	OA11071A (is)
PE (1)	PE27499A1 (is)
PL (1)	PL334218A1 (is)
PT (1)	PT948509E (is)
SI (1)	SI0948509T1 (is)
SK (1)	SK86599A3 (is)
TR (1)	TR199901905T2 (is)
TW (1)	TW528755B (is)
WO (1)	WO1998028319A1 (is)
YU (1)	YU29099A (is)

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YU44900A (sh)	1998-01-31	2003-01-31	Glaxo Group Limited	Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola
AR017457A1 (es)	1998-02-14	2001-09-05	Glaxo Group Ltd	Compuestos derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol, procesos para su preparacion, composiciones que los contienen y su uso en terapia para el tratamiento de enfermedades inflamatorias.
US7045519B2 (en)	1998-06-19	2006-05-16	Chiron Corporation	Inhibitors of glycogen synthase kinase 3
GB9813554D0 (en)	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
GB9813565D0 (en) *	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
JP3933870B2 (ja) *	1998-06-23	2007-06-20	グラクソグループリミテッド	２−（プリン−９−イル）−テトラヒドロフラン−３，４−ジオール誘導体
GB9813540D0 (en) *	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
GB9930082D0 (en) *	1999-12-20	2000-02-09	Glaxo Group Ltd	Medicaments
US6667300B2 (en) *	2000-04-25	2003-12-23	Icos Corporation	Inhibitors of human phosphatidylinositol 3-kinase delta
GB0022695D0 (en)	2000-09-15	2000-11-01	Pfizer Ltd	Purine Derivatives
GB0104555D0 (en) *	2001-02-23	2001-04-11	Glaxo Group Ltd	New Therapeutic method
WO2002072067A2 (en) *	2001-03-12	2002-09-19	Glaxo Group Limited	Pharmaceutical aerosol formulation
JP2002338593A (ja) *	2001-05-22	2002-11-27	Ajinomoto Co Inc	β−Ｄ−リボフラノース誘導体又はその光学異性体の製造方法
PE20030008A1 (es) *	2001-06-19	2003-01-22	Bristol Myers Squibb Co	Inhibidores duales de pde 7 y pde 4
AR044519A1 (es)	2003-05-02	2005-09-14	Novartis Ag	Derivados de piridin-tiazol amina y de pirimidin-tiazol amina
GB0401334D0 (en)	2004-01-21	2004-02-25	Novartis Ag	Organic compounds
TWI346109B (en) *	2004-04-30	2011-08-01	Otsuka Pharma Co Ltd	4-amino-5-cyanopyrimidine derivatives
WO2005113556A1 (en)	2004-05-13	2005-12-01	Icos Corporation	Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta
GB0411056D0 (en)	2004-05-18	2004-06-23	Novartis Ag	Organic compounds
PE20060272A1 (es)	2004-05-24	2006-05-22	Glaxo Group Ltd	(2r,3r,4s,5r,2'r,3'r,4's,5's)-2,2'-{trans-1,4-ciclohexanodiilbis-[imino(2-{[2-(1-metil-1h-imidazol-4-il)etil]amino}-9h-purin-6,9-diil)]}bis[5-(2-etil-2h-tetrazol-5-il)tetrahidro-3,4-furanodiol] como agonista a2a
WO2005117910A2 (en) *	2004-05-26	2005-12-15	Inotek Pharmaceuticals Corporation	Purine derivatives as adenosine a1 receptor agonists and methods of use thereof
MX2007003271A (es) *	2004-09-20	2007-06-05	Inotek Pharmaceuticals Corp	Derivados de purina y metodos de uso de los mismos.
GB0424284D0 (en)	2004-11-02	2004-12-01	Novartis Ag	Organic compounds
GB0426164D0 (en)	2004-11-29	2004-12-29	Novartis Ag	Organic compounds
GB0500785D0 (en) *	2005-01-14	2005-02-23	Novartis Ag	Organic compounds
GB0510390D0 (en)	2005-05-20	2005-06-29	Novartis Ag	Organic compounds
GB0514809D0 (en) *	2005-07-19	2005-08-24	Glaxo Group Ltd	Compounds
WO2007045477A2 (en)	2005-10-21	2007-04-26	Novartis Ag	Human antibodies against il-13 and therapeutic uses
GB0523845D0 (en) *	2005-11-23	2006-01-04	Glaxo Group Ltd	Novel salts
EA015683B1 (ru) *	2005-11-30	2011-10-31	Инотек Фармасьютикалз Корпорейшн	Производные пурина и способы их применения
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Publication number	Publication date
EP0948509B1 (en)	2002-10-16
NZ336332A (en)	2000-12-22
US6426337B1 (en)	2002-07-30
NO993114L (no)	1999-08-23
BG63310B1 (bg)	2001-09-28
PT948509E (pt)	2003-03-31
CO4940488A1 (es)	2000-07-24
BG103518A (en)	2000-01-31
NO993114D0 (no)	1999-06-23
AP1105A (en)	2002-09-04
PE27499A1 (es)	1999-03-30
AP9901572A0 (en)	1999-06-30
EE9900312A (et)	2000-02-15
GEP20022656B (en)	2002-03-25
JP4156035B2 (ja)	2008-09-24
PL334218A1 (en)	2000-02-14
EA199900494A1 (ru)	2000-02-28
EE04019B1 (et)	2003-04-15
ID22271A (id)	1999-09-23
IL130547A0 (en)	2000-06-01
YU29099A (sh)	2002-06-19
WO1998028319A1 (en)	1998-07-02
US20020086850A1 (en)	2002-07-04
DE69716468D1 (de)	2002-11-21
ES2186015T3 (es)	2003-05-01
BR9714082A (pt)	2000-05-09
ATE226212T1 (de)	2002-11-15
AR011044A1 (es)	2000-08-02
HUP0000673A2 (hu)	2001-06-28
DK0948509T3 (da)	2003-02-24
HUP0000673A3 (en)	2003-01-28
SI0948509T1 (en)	2003-06-30
CA2275271A1 (en)	1998-07-02
US6528494B2 (en)	2003-03-04
JP2001506668A (ja)	2001-05-22
DE69716468T2 (de)	2003-05-28
AU5762298A (en)	1998-07-17
TR199901905T2 (xx)	1999-10-21
EP0948509A1 (en)	1999-10-13
EA001714B1 (ru)	2001-08-27
OA11071A (en)	2002-11-18
KR20000069682A (ko)	2000-11-25
AU733684B2 (en)	2001-05-24
SK86599A3 (en)	2000-05-16
CN1246124A (zh)	2000-03-01
CZ230999A3 (cs)	1999-12-15
TW528755B (en)	2003-04-21
IS5089A (is)	1999-06-22

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