HRP20000895A2 - 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives - Google Patents

2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives Download PDF

Info

Publication number: HRP20000895A2
Authority: HR; Croatia
Prior art keywords: ethylamino; tetrahydro; purin; furan; ethyl
Prior art date: 1998-06-23

Application number

HR20000895A

Other languages

English (en)

Croatian (hr)

Inventor

David George Allen

David Edmund Bays

Chuen Chan

Caroline Mary Coox

Richard Peter Charles Cousins

Brian Cox

Hazel Joan Dyke

Frank Ellis

Joana Victoria Geden

Heather Hobbs

Alison Judith Redgrave

Stephen Swanson

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.)

1998-06-23

Filing date

2000-12-21

Publication date

2001-10-31

2000-12-21 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2001-10-31 Publication of HRP20000895A2 publication Critical patent/HRP20000895A2/hr

Links

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 182
239000000203 mixture Substances 0.000 claims description 80
-1 ethyl-piperidin-1-yl Chemical group 0.000 claims description 39
238000000034 method Methods 0.000 claims description 35
238000002360 preparation method Methods 0.000 claims description 30
150000003839 salts Chemical class 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 23
238000006243 chemical reaction Methods 0.000 claims description 21
238000011282 treatment Methods 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
239000012453 solvate Chemical class 0.000 claims description 14
125000003118 aryl group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
239000003814 drug Substances 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
229910052717 sulfur Inorganic materials 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
125000002785 azepinyl group Chemical group 0.000 claims description 4
125000002393 azetidinyl group Chemical group 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 4
125000002757 morpholinyl group Chemical group 0.000 claims description 4
125000004193 piperazinyl group Chemical group 0.000 claims description 4
125000003386 piperidinyl group Chemical group 0.000 claims description 4
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
229910005965 SO 2 Inorganic materials 0.000 claims description 3
125000002877 alkyl aryl group Chemical group 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
239000000969 carrier Substances 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
KQYAZOONHVDJEU-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(5-ethyl-1,2,4-oxadiazol-3-yl)oxolane-3,4-diol Chemical compound O1C(CC)=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 KQYAZOONHVDJEU-CKXMCULTSA-N 0.000 claims 1
NOYRFHBSCWDJGK-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(5-ethyl-1h-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound N1C(CC)=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 NOYRFHBSCWDJGK-CKXMCULTSA-N 0.000 claims 1
GYOMGLACOXBHTA-KCIBBDPESA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(1-ethyl-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound CCN1C=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 GYOMGLACOXBHTA-KCIBBDPESA-N 0.000 claims 1
MWAFNAFZJUAOKP-KCIBBDPESA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(5-ethyl-1,2,4-oxadiazol-3-yl)oxolane-3,4-diol Chemical compound O1C(CC)=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 MWAFNAFZJUAOKP-KCIBBDPESA-N 0.000 claims 1
SBBAFENCIRVCTC-KCIBBDPESA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-pyridin-2-ylethylamino)purin-9-yl]-5-(1-ethyl-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound CCN1C=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CC=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 SBBAFENCIRVCTC-KCIBBDPESA-N 0.000 claims 1
NVHPRHDQZLXVMD-KCIBBDPESA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-pyridin-2-ylethylamino)purin-9-yl]-5-(5-ethyl-1h-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound N1C(CC)=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CC=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 NVHPRHDQZLXVMD-KCIBBDPESA-N 0.000 claims 1
KUUDGUNZYGRNCR-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-(2-pyrrolidin-1-ylethylamino)purin-9-yl]-5-(5-methyl-1h-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound N1C(C)=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCN4CCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 KUUDGUNZYGRNCR-OVDFTCDZSA-N 0.000 claims 1
ONRVDWDGXWNIJE-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(1-ethyl-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound CCN1C=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 ONRVDWDGXWNIJE-CKXMCULTSA-N 0.000 claims 1
VFTYMVGNRQUSLP-CKXMCULTSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(5-ethyl-1,2,4-oxadiazol-3-yl)oxolane-3,4-diol Chemical compound O1C(CC)=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 VFTYMVGNRQUSLP-CKXMCULTSA-N 0.000 claims 1
ABGLUDPUGYNORO-OVDFTCDZSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(5-methyl-1h-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound N1C(C)=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 ABGLUDPUGYNORO-OVDFTCDZSA-N 0.000 claims 1
FTTFQEJMJMISPK-UMHHXCEVSA-N (2r,3r,4s,5r)-2-[6-(2,2-diphenylethylamino)-2-[[(1r)-1-hydroxy-2-phenylethyl]amino]purin-9-yl]-5-(1-ethyl-1,2,4-triazol-3-yl)oxolane-3,4-diol Chemical compound CCN1C=NC([C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC(N[C@H](O)CC=4C=CC=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O)=N1 FTTFQEJMJMISPK-UMHHXCEVSA-N 0.000 claims 1
XOJTXESFIREACI-KKPNIWNPSA-N (2r,3r,4s,5s)-2-[2-(2-cyclohexylethylamino)-6-(pentan-3-ylamino)purin-9-yl]-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3OC(=NN=3)C3CC3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1CCCCC1 XOJTXESFIREACI-KKPNIWNPSA-N 0.000 claims 1
SMDOIHWEEKGWKA-DDOIHHOZSA-N (2r,3r,4s,5s)-2-[2-(cyclopentylamino)-6-(pentan-3-ylamino)purin-9-yl]-5-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3OC(=NN=3)C3CC3)O)C=NC=2C(NC(CC)CC)=NC=1NC1CCCC1 SMDOIHWEEKGWKA-DDOIHHOZSA-N 0.000 claims 1
LBMWOLNCFALFJL-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(5-ethyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound O1C(CC)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCN4CCOCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 LBMWOLNCFALFJL-CKXMCULTSA-N 0.000 claims 1
ARYQGKOGXSGCDO-KCIBBDPESA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(5-ethyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound O1C(CC)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 ARYQGKOGXSGCDO-KCIBBDPESA-N 0.000 claims 1
BDMOZOVOLGZNNS-CKXMCULTSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(5-methyl-1,3,4-thiadiazol-2-yl)oxolane-3,4-diol Chemical compound S1C(C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCN4CCCCC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 BDMOZOVOLGZNNS-CKXMCULTSA-N 0.000 claims 1
ZBWRIVJLEVKESA-KCIBBDPESA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-pyridin-2-ylethylamino)purin-9-yl]-5-(5-ethyl-1,3,4-oxadiazol-2-yl)oxolane-3,4-diol Chemical compound O1C(CC)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCC=4N=CC=CC=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 ZBWRIVJLEVKESA-KCIBBDPESA-N 0.000 claims 1
LTIWXZXNIPUQLP-OVDFTCDZSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(5-methyl-1,3,4-thiadiazol-2-yl)oxolane-3,4-diol Chemical compound S1C(C)=NN=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 LTIWXZXNIPUQLP-OVDFTCDZSA-N 0.000 claims 1
FWMSWNOTFXTHAH-IYXIZZNPSA-N (2r,3s,4r,5r)-2-(5-ethyl-1,2-oxazol-3-yl)-5-[6-(pentan-3-ylamino)-2-(2-piperidin-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=NOC(CC)=C3)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCCC1 FWMSWNOTFXTHAH-IYXIZZNPSA-N 0.000 claims 1
WWAGALBNJHQBSV-UAKAABGRSA-N (2s,3s,4r,5r)-2-(5-cyclopropyl-1,3,4-oxadiazol-2-yl)-5-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3OC(=NN=3)C3CC3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 WWAGALBNJHQBSV-UAKAABGRSA-N 0.000 claims 1
QXHRLRFYERUHFZ-LKPCVQNHSA-N N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN(C=N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN(C=N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 QXHRLRFYERUHFZ-LKPCVQNHSA-N 0.000 claims 1
AYHREVIVPMZMBX-DIFXNMBTSA-N N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)C(C)C)NCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)C(C)C)NCC(C1=CC=CC=C1)C1=CC=CC=C1 AYHREVIVPMZMBX-DIFXNMBTSA-N 0.000 claims 1
RADOIHHZEXMYJY-FJUNXPAFSA-N N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)C)NCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)C)NCC(C1=CC=CC=C1)C1=CC=CC=C1 RADOIHHZEXMYJY-FJUNXPAFSA-N 0.000 claims 1
MMVJRBFCIPIVJZ-CUCOOGOQSA-N N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NN=C(N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 MMVJRBFCIPIVJZ-CUCOOGOQSA-N 0.000 claims 1
PMPLSBZLYAIIHY-CUCOOGOQSA-N N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NOC(=N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound N[C@@H]1CC[C@H](CC1)NC1=NC(=C2N=CN(C2=N1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C1=NOC(=N1)CC)NCC(C1=CC=CC=C1)C1=CC=CC=C1 PMPLSBZLYAIIHY-CUCOOGOQSA-N 0.000 claims 1
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239000003085 diluting agent Substances 0.000 claims 1
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238000004108 freeze drying Methods 0.000 description 39
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- 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
- 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
- C07H1/00—Processes for the preparation of sugar derivatives

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General Health & Medical Sciences (AREA)
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Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
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Molecular Biology (AREA)
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Bioinformatics & Cheminformatics (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)

HR20000895A 1998-06-23 2000-12-21 2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives HRP20000895A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9813565.0A GB9813565D0 (en)	1998-06-23	1998-06-23	Chemical compounds
PCT/EP1999/004267 WO1999067264A1 (en)	1998-06-23	1999-06-23	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives

Publications (1)

Publication Number	Publication Date
HRP20000895A2 true HRP20000895A2 (en)	2001-10-31

Family

ID=10834254

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20000895A HRP20000895A2 (en)	1998-06-23	2000-12-21	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives

Country Status (26)

Country	Link
EP (1)	EP1090023B1 (de)
JP (1)	JP2002518511A (de)
KR (1)	KR20010071570A (de)
CN (1)	CN1313860A (de)
AP (1)	AP2000002013A0 (de)
AT (1)	ATE249474T1 (de)
AU (1)	AU758979B2 (de)
BR (1)	BR9911488A (de)
CA (1)	CA2335758A1 (de)
DE (1)	DE69911207D1 (de)
EA (1)	EA200001223A1 (de)
EE (1)	EE200000764A (de)
GB (1)	GB9813565D0 (de)
HR (1)	HRP20000895A2 (de)
HU (1)	HUP0102454A3 (de)
ID (1)	ID28219A (de)
IL (1)	IL140285A0 (de)
IS (1)	IS5774A (de)
NO (1)	NO20006521L (de)
NZ (1)	NZ508918A (de)
PL (1)	PL345097A1 (de)
SK (1)	SK19532000A3 (de)
TR (1)	TR200100411T2 (de)
WO (1)	WO1999067264A1 (de)
YU (1)	YU81000A (de)
ZA (1)	ZA200007515B (de)

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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
WO2006028618A1 (en)	2004-08-02	2006-03-16	University Of Virginia Patent Foundation	2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity
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GB0424284D0 (en)	2004-11-02	2004-12-01	Novartis Ag	Organic compounds
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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
AR058104A1 (es)	2005-10-21	2008-01-23	Novartis Ag	Compuestos organicos
GB0601951D0 (en)	2006-01-31	2006-03-15	Novartis Ag	Organic compounds
JP2010504933A (ja)	2006-09-29	2010-02-18	ノバルティスアーゲー	Ｐｉ３ｋ脂質キナーゼ阻害剤としてのピラゾロピリミジン
EP2089393A1 (de)	2006-10-30	2009-08-19	Novartis AG	Heterozyklische verbindungen als entzündungshemmende mittel
PL2231642T3 (pl)	2008-01-11	2014-04-30	Novartis Ag	Pirymidyny jako inhibitory kinazy
US20110281917A1 (en)	2009-01-29	2011-11-17	Darrin Stuart	Substituted Benzimidazoles for the Treatment of Astrocytomas
US8389526B2 (en)	2009-08-07	2013-03-05	Novartis Ag	3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
AU2010283806A1 (en)	2009-08-12	2012-03-01	Novartis Ag	Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation
SG178454A1 (en)	2009-08-17	2012-03-29	Intellikine Inc	Heterocyclic compounds and uses thereof
JP5775871B2 (ja)	2009-08-20	2015-09-09	ノバルティスアーゲー	ヘテロ環式オキシム化合物
UY33597A (es)	2010-09-09	2012-04-30	Irm Llc	Compuestos y composiciones como inhibidores de la trk
WO2012034095A1 (en)	2010-09-09	2012-03-15	Irm Llc	Compounds and compositions as trk inhibitors
WO2012107500A1 (en)	2011-02-10	2012-08-16	Novartis Ag	[1, 2, 4] triazolo [4, 3 -b] pyridazine compounds as inhibitors of the c-met tyrosine kinase
WO2012116237A2 (en)	2011-02-23	2012-08-30	Intellikine, Llc	Heterocyclic compounds and uses thereof
WO2012116217A1 (en)	2011-02-25	2012-08-30	Irm Llc	Compounds and compositions as trk inhibitors
JP5957526B2 (ja)	2011-09-15	2016-07-27	ノバルティスアーゲー	チロシンキナーゼとしての６−置換３−（キノリン−６−イルチオ）−［１，２，４］トリアゾロ［４，３−ａ］ピラジン
WO2013078440A2 (en)	2011-11-23	2013-05-30	Intellikine, Llc	Enhanced treatment regimens using mtor inhibitors
CN110507654A (zh)	2012-04-03	2019-11-29	诺华有限公司	有酪氨酸激酶抑制剂的组合产品和其应用
JP2016512835A (ja)	2013-03-15	2016-05-09	インテリカイン，エルエルシー	キナーゼ阻害剤の組み合わせ及びそれらの使用
TW201605450A (zh)	2013-12-03	2016-02-16	諾華公司	Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途
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US10195208B2 (en)	2014-07-31	2019-02-05	Novartis Ag	Combination therapy
TW202140550A (zh)	2020-01-29	2021-11-01	瑞士商諾華公司	使用抗ｔｓｌｐ抗體治療炎性或阻塞性氣道疾病之方法

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TW528755B (en) *	1996-12-24	2003-04-21	Glaxo Group Ltd	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
YU44900A (sh) *	1998-01-31	2003-01-31	Glaxo Group Limited	Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola
CO4990969A1 (es) *	1998-02-14	2000-12-26	Glaxo Group Ltd	Derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol

1998
- 1998-06-23 GB GBGB9813565.0A patent/GB9813565D0/en not_active Ceased
1999
- 1999-06-23 AP APAP/P/2000/002013A patent/AP2000002013A0/en unknown
- 1999-06-23 DE DE69911207T patent/DE69911207D1/de not_active Expired - Lifetime
- 1999-06-23 JP JP2000555915A patent/JP2002518511A/ja active Pending
- 1999-06-23 PL PL99345097A patent/PL345097A1/xx unknown
- 1999-06-23 EE EEP200000764A patent/EE200000764A/xx unknown
- 1999-06-23 EP EP99934530A patent/EP1090023B1/de not_active Expired - Lifetime
- 1999-06-23 CA CA002335758A patent/CA2335758A1/en not_active Abandoned
- 1999-06-23 EA EA200001223A patent/EA200001223A1/ru unknown
- 1999-06-23 AT AT99934530T patent/ATE249474T1/de not_active IP Right Cessation
- 1999-06-23 WO PCT/EP1999/004267 patent/WO1999067264A1/en not_active Application Discontinuation
- 1999-06-23 KR KR1020007014622A patent/KR20010071570A/ko not_active Application Discontinuation
- 1999-06-23 AU AU50281/99A patent/AU758979B2/en not_active Ceased
- 1999-06-23 CN CN99809865A patent/CN1313860A/zh active Pending
- 1999-06-23 NZ NZ508918A patent/NZ508918A/xx unknown
- 1999-06-23 ID IDW20010187A patent/ID28219A/id unknown
- 1999-06-23 HU HU0102454A patent/HUP0102454A3/hu unknown
- 1999-06-23 YU YU81000A patent/YU81000A/sh unknown
- 1999-06-23 BR BR9911488-7A patent/BR9911488A/pt not_active IP Right Cessation
- 1999-06-23 SK SK1953-2000A patent/SK19532000A3/sk unknown
- 1999-06-23 TR TR2001/00411T patent/TR200100411T2/xx unknown
- 1999-06-23 IL IL14028599A patent/IL140285A0/xx unknown
2000
- 2000-12-14 ZA ZA200007515A patent/ZA200007515B/xx unknown
- 2000-12-15 IS IS5774A patent/IS5774A/is unknown
- 2000-12-20 NO NO20006521A patent/NO20006521L/no not_active Application Discontinuation
- 2000-12-21 HR HR20000895A patent/HRP20000895A2/hr not_active Application Discontinuation

Also Published As

Publication number	Publication date
AU758979B2 (en)	2003-04-03
EA200001223A1 (ru)	2001-10-22
YU81000A (sh)	2003-10-31
KR20010071570A (ko)	2001-07-28
EP1090023A1 (de)	2001-04-11
ID28219A (id)	2001-05-10
TR200100411T2 (tr)	2001-07-23
NO20006521L (no)	2001-02-22
DE69911207D1 (de)	2003-10-16
ATE249474T1 (de)	2003-09-15
EE200000764A (et)	2002-04-15
ZA200007515B (en)	2001-12-14
CN1313860A (zh)	2001-09-19
GB9813565D0 (en)	1998-08-19
HUP0102454A3 (en)	2003-01-28
JP2002518511A (ja)	2002-06-25
BR9911488A (pt)	2001-03-20
NZ508918A (en)	2003-03-28
NO20006521D0 (no)	2000-12-20
HUP0102454A2 (hu)	2002-01-28
CA2335758A1 (en)	1999-12-29
AU5028199A (en)	2000-01-10
IS5774A (is)	2000-12-15
IL140285A0 (en)	2002-02-10
PL345097A1 (en)	2001-12-03
AP2000002013A0 (en)	2000-12-31
WO1999067264A1 (en)	1999-12-29
SK19532000A3 (sk)	2001-11-06
EP1090023B1 (de)	2003-09-10

Legal Events

Date	Code	Title	Description
2001-10-31	A1OB	Publication of a patent application
2002-02-11	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2003-04-23	ODRP	Renewal fee for the maintenance of a patent	Payment date: 20030423 Year of fee payment: 5
2008-11-17	OBST	Application withdrawn

Publication	Publication Date	Title
HRP20000895A2 (en)	2001-10-31	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
US6610665B1 (en)	2003-08-26	2-(purin-9-yl)-tetrahydrofuran-3, 4-diol derivatives
US6534486B1 (en)	2003-03-18	2-(purin-9-yl)-Tetrahydrofuran-3,4-diol derivatives
JP3933870B2 (ja)	2007-06-20	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
EP1090020B1 (de)	2003-11-05	2-(purin-9-yl)-tetrahydrofuran-3,4-diol-derivate
JP4156035B2 (ja)	2008-09-24	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
KR20010034473A (ko)	2001-04-25	2-(퓨린-9-일)-테트라히드로퓨란-3,4-디올 유도체
MXPA00012895A (en)	2001-09-07	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
CZ20004870A3 (cs)	2001-06-13	2 (Purin 9 yl) tetrahydrofuran 3,4 diolové deriváty
MXPA00007793A (en)	2001-11-21	2-(purin-9-yl) -tetrahydrofuran-3, 4-diol derivatives
MXPA00012926A (en)	2002-05-09	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
CZ20002787A3 (cs)	2001-04-11	2-(purin-9-yl)-tetrahydrofuran-3,4-diolové deriváty
CZ20002974A3 (cs)	2001-05-16	2-(purin-9-yl)-tetrahydrofuran-3,4-diolové deriváty