OA11447A - 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: OA11447A
Authority: OA; OAPI
Prior art keywords: ethyl; tetrahydro; purin; furan; isoxazol
Prior art date: 1998-01-31

Application number

OA1200000211A

Other languages

English (en)

Inventor

Chuen Chan

Brian Cox

Richard Peter Charles Cousins

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.)

1998-01-31

Filing date

2000-07-21

Publication date

2004-04-29

1998-01-31 Priority claimed from GBGB9802066.2A external-priority patent/GB9802066D0/en

1998-06-23 Priority claimed from GBGB9813528.8A external-priority patent/GB9813528D0/en

2000-07-21 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2004-04-29 Publication of OA11447A publication Critical patent/OA11447A/en

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 description 3
150000001875 compounds Chemical class 0.000 claims abstract description 223
238000000034 method Methods 0.000 claims abstract description 33
230000008569 process Effects 0.000 claims abstract description 21
238000011282 treatment Methods 0.000 claims abstract description 20
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 64
-1 cyclopropylmethyl,cyclopropenylmethyl Chemical group 0.000 claims description 63
229910052757 nitrogen Inorganic materials 0.000 claims description 34
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 21
229910052739 hydrogen Inorganic materials 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
201000010099 disease Diseases 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000003386 piperidinyl group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000002431 hydrogen Chemical class 0.000 claims description 7
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
125000002785 azepinyl group Chemical group 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 5
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
125000002393 azetidinyl group Chemical group 0.000 claims description 3
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 3
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
NNPKMJTZHWAPAC-RBOWJBJUSA-N (2r,3r,4s,5s)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[6-(2-phenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@H]1[C@H](O)[C@H](O)[C@@H](N2C3=NC(NCCN4CCCCC4)=NC(NCCC=4C=CC=CC=4)=C3N=C2)O1 NNPKMJTZHWAPAC-RBOWJBJUSA-N 0.000 claims description 2
BYZVGFPGQNGQMM-ZOJNDGCKSA-N (2r,3r,4s,5s)-2-[6-(2-cyclohexylethylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCCC4CCCCC4)=C3N=C2)O1 BYZVGFPGQNGQMM-ZOJNDGCKSA-N 0.000 claims description 2
YKOWBJJOJNGCAD-SHYZEUOFSA-N [(2r,3s,5r)-3-hydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl dihydrogen phosphate Chemical compound O=C1N=C(NO)C=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)C1 YKOWBJJOJNGCAD-SHYZEUOFSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 claims description 2
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 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
SNVLJLYUUXKWOJ-UHFFFAOYSA-N methylidenecarbene Chemical group C=[C] SNVLJLYUUXKWOJ-UHFFFAOYSA-N 0.000 claims description 2
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 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
AXQZJJVCWCQUBA-KXEAFHOWSA-N (2r,3r,4s,5s)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[2-(2-pyridin-2-ylethylamino)-6-(thian-4-ylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@H]1[C@H](O)[C@H](O)[C@@H](N2C3=NC(NCCC=4N=CC=CC=4)=NC(NC4CCSCC4)=C3N=C2)O1 AXQZJJVCWCQUBA-KXEAFHOWSA-N 0.000 claims 1
BXDLHXBCFBMFTQ-JZJXAQOMSA-N (2r,3r,4s,5s)-2-[2-(ethylamino)-6-[(3-iodophenyl)methylamino]purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound C=12N=CN([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(CC)C=3)O)C2=NC(NCC)=NC=1NCC1=CC=CC(I)=C1 BXDLHXBCFBMFTQ-JZJXAQOMSA-N 0.000 claims 1
DUCYCKTXLKUXGG-IYXIZZNPSA-N (2r,3r,4s,5s)-2-[2-[2-(1-methylimidazol-4-yl)ethylamino]-6-(pentan-3-ylamino)purin-9-yl]-5-(3-propyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CCC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NC(CC)CC)=C3N=C2)O1 DUCYCKTXLKUXGG-IYXIZZNPSA-N 0.000 claims 1
HZOHMZGMBDIMIM-CFNUTJGKSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-morpholin-4-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=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 HZOHMZGMBDIMIM-CFNUTJGKSA-N 0.000 claims 1
SHAGTVNCZUBUCI-IMNMKIORSA-N (2r,3r,4s,5s)-2-[6-(2,2-diphenylethylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=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 SHAGTVNCZUBUCI-IMNMKIORSA-N 0.000 claims 1
VLMXBVLPRDNRNB-FBHSLPMESA-N (2r,3r,4s,5s)-2-[6-(3,3-dimethylbutylamino)-2-[2-(1-methylimidazol-4-yl)ethylamino]purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCC=4N=CN(C)C=4)=NC(NCCC(C)(C)C)=C3N=C2)O1 VLMXBVLPRDNRNB-FBHSLPMESA-N 0.000 claims 1
RNQYQBVATFEYLI-ZOJNDGCKSA-N (2r,3r,4s,5s)-2-[6-(benzylamino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCN4CCCCC4)=NC(NCC=4C=CC=CC=4)=C3N=C2)O1 RNQYQBVATFEYLI-ZOJNDGCKSA-N 0.000 claims 1
NZSQLZFWQKBZMV-NZCWTCFWSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[6-(3-fluoro-4-hydroxyanilino)-2-(2-piperidin-1-ylethylamino)purin-9-yl]oxolane-3,4-diol Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(NCCN4CCCCC4)=NC(NC=4C=C(F)C(O)=CC=4)=C3N=C2)O1 NZSQLZFWQKBZMV-NZCWTCFWSA-N 0.000 claims 1
HMLLMVCTYDJEND-IYXIZZNPSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2-oxazol-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)C=3ON=C(CC)C=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CC=CC=N1 HMLLMVCTYDJEND-IYXIZZNPSA-N 0.000 claims 1
MHMPVSSENUALGN-IYXIZZNPSA-N (2s,3s,4r,5r)-2-(3-ethyl-1,2-oxazol-5-yl)-5-[6-(pentan-3-ylamino)-2-[2-(pyridin-2-ylamino)ethylamino]purin-9-yl]oxolane-3,4-diol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@H](O3)C=3ON=C(CC)C=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCNC1=CC=CC=N1 MHMPVSSENUALGN-IYXIZZNPSA-N 0.000 claims 1
SJSHNUZYLVMPBM-FBHSLPMESA-N (2s,3s,4r,5r)-2-(3-methyl-1,2-oxazol-5-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)C=3ON=C(C)C=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCCC1 SJSHNUZYLVMPBM-FBHSLPMESA-N 0.000 claims 1
ZTLVAAPXAFHNKC-ULEBWLSVSA-N (2s,3s,4r,5r)-2-[3-(1-hydroxyethyl)-1,2-oxazol-5-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=3ON=C(C=3)C(C)O)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 ZTLVAAPXAFHNKC-ULEBWLSVSA-N 0.000 claims 1
OYJCZWPBQRKWGQ-DZCCDHAISA-N (2s,3s,4r,5r)-2-[3-(hydroxymethyl)-1,2-oxazol-5-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=3ON=C(CO)C=3)O)C=NC=2C(NC(CC)CC)=NC=1NCCC1=CN(C)C=N1 OYJCZWPBQRKWGQ-DZCCDHAISA-N 0.000 claims 1
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
RKWULRTUQLOHPU-DBFFLLMJSA-N O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 Chemical compound O1N=C(CC)C=C1[C@@H]1[C@@H](O)[C@@H](O)[C@H](N2C3=NC(N[C@@H]4CC[C@@H](N)CC4)=NC(NCC(C=4C=CC=CC=4)C=4C=CC=CC=4)=C3N=C2)O1 RKWULRTUQLOHPU-DBFFLLMJSA-N 0.000 claims 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 claims 1
229940125758 compound 15 Drugs 0.000 claims 1
ULYSABNRLLVZCE-UHFFFAOYSA-N furan-3,4-diol Chemical compound OC1=COC=C1O ULYSABNRLLVZCE-UHFFFAOYSA-N 0.000 claims 1
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125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 9
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VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
HWWVAHCWJLGKLW-UHFFFAOYSA-N n,n-dimethylhydroxylamine;hydron;chloride Chemical compound Cl.CN(C)O HWWVAHCWJLGKLW-UHFFFAOYSA-N 0.000 description 1
PEECTLLHENGOKU-UHFFFAOYSA-N n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=CC=NC=C1.CN(C)C1=CC=NC=C1 PEECTLLHENGOKU-UHFFFAOYSA-N 0.000 description 1
ZHAQIJMDYKBLOR-UHFFFAOYSA-N n-ethylmorpholin-2-amine Chemical compound CCNC1CNCCO1 ZHAQIJMDYKBLOR-UHFFFAOYSA-N 0.000 description 1
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125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
210000001672 ovary Anatomy 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
244000045947 parasite Species 0.000 description 1
230000008782 phagocytosis Effects 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
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UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
108010031345 placental alkaline phosphatase Proteins 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000770 proinflammatory effect Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000003380 propellant Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
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235000020374 simple syrup Nutrition 0.000 description 1
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159000000000 sodium salts Chemical class 0.000 description 1
229940080313 sodium starch Drugs 0.000 description 1
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000001593 sorbitan monooleate Substances 0.000 description 1
235000011069 sorbitan monooleate Nutrition 0.000 description 1
229940035049 sorbitan monooleate Drugs 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
208000018556 stomach disease Diseases 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
229960000195 terbutaline Drugs 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
RPIXOLUIHUFDOY-UHFFFAOYSA-N thian-4-amine Chemical compound NC1CCSCC1 RPIXOLUIHUFDOY-UHFFFAOYSA-N 0.000 description 1
230000008719 thickening Effects 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
208000037816 tissue injury Diseases 0.000 description 1
230000017423 tissue regeneration Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
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
229960002117 triamcinolone acetonide Drugs 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
229940029284 trichlorofluoromethane Drugs 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
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239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Pulmonology (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Pain & Pain Management (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)

OA1200000211A 1998-01-31 2000-07-21 2-(Purin-9-yl)-tetrahydrofuran-3,4-diol derivatives. OA11447A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9802066.2A GB9802066D0 (en)	1998-01-31	1998-01-31	Chemical compounds
GBGB9813528.8A GB9813528D0 (en)	1998-06-23	1998-06-23	Chemical compounds

Publications (1)

Publication Number	Publication Date
OA11447A true OA11447A (en)	2004-04-29

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ID=26313042

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Application Number	Title	Priority Date	Filing Date
OA1200000211A OA11447A (en)	1998-01-31	2000-07-21	2-(Purin-9-yl)-tetrahydrofuran-3,4-diol derivatives.

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US (1)	US6762170B1 (id)
EP (1)	EP1051425B1 (id)
JP (1)	JP2002501928A (id)
KR (1)	KR20010034473A (id)
CN (1)	CN1289338A (id)
AP (1)	AP2000001875A0 (id)
AR (1)	AR014508A1 (id)
AT (1)	ATE226957T1 (id)
AU (1)	AU757183B2 (id)
BG (1)	BG63783B1 (id)
BR (1)	BR9907270A (id)
CA (1)	CA2318278A1 (id)
CO (1)	CO4980872A1 (id)
DE (1)	DE69903708T2 (id)
DK (1)	DK1051425T3 (id)
EA (1)	EA003194B1 (id)
EE (1)	EE200000441A (id)
ES (1)	ES2186330T3 (id)
GE (1)	GEP20022839B (id)
HR (1)	HRP20000511A2 (id)
HU (1)	HUP0101305A3 (id)
ID (1)	ID26326A (id)
IL (1)	IL137042A0 (id)
IS (1)	IS5550A (id)
MA (1)	MA26601A1 (id)
NO (1)	NO20003867L (id)
NZ (1)	NZ505452A (id)
OA (1)	OA11447A (id)
PE (1)	PE20000280A1 (id)
PL (1)	PL342670A1 (id)
PT (1)	PT1051425E (id)
SI (1)	SI1051425T1 (id)
SK (1)	SK11192000A3 (id)
SV (1)	SV1999000009A (id)
TR (1)	TR200002218T2 (id)
TW (1)	TW434250B (id)
WO (1)	WO1999038877A2 (id)
YU (1)	YU44900A (id)

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GB0514809D0 (en)	2005-07-19	2005-08-24	Glaxo Group Ltd	Compounds
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RU2009115954A (ru)	2006-09-29	2010-11-10	Новартис АГ (CH)	Пиразолопиримидины в качестве ингибиторов липидной киназы р13к
JP2010508315A (ja)	2006-10-30	2010-03-18	ノバルティスアーゲー	抗炎症剤としてのヘテロ環式化合物
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CA2770873A1 (en)	2009-08-12	2011-02-17	Novartis Ag	Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation
GEP201706639B (en)	2009-08-17	2017-03-27	Intellikine Llc	Heterocyclic compounds and uses thereof
CA2771432A1 (en)	2009-08-20	2011-02-24	Novartis Ag	Heterocyclic oxime compounds
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JP2014505088A (ja)	2011-02-10	2014-02-27	ノバルティスアーゲー	Ｃ−ＭＥＴチロシンキナーゼ阻害剤としての［１，２，４］トリアゾロ［４，３−ｂ］ピリダジン化合物
JP5808826B2 (ja)	2011-02-23	2015-11-10	インテリカイン，エルエルシー	複素環化合物およびその使用
KR20140014184A (ko)	2011-02-25	2014-02-05	아이알엠 엘엘씨	Trk 억제제로서의 화합물 및 조성물
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1998
- 1998-01-31 YU YU44900A patent/YU44900A/sh unknown
1999
- 1999-01-28 CO CO99004721A patent/CO4980872A1/es unknown
- 1999-01-28 AR ARP990100336A patent/AR014508A1/es not_active Application Discontinuation
- 1999-01-28 PE PE1999000060A patent/PE20000280A1/es not_active Application Discontinuation
- 1999-01-29 EA EA200000723A patent/EA003194B1/ru not_active IP Right Cessation
- 1999-01-29 JP JP2000529344A patent/JP2002501928A/ja active Pending
- 1999-01-29 HR HR20000511A patent/HRP20000511A2/hr not_active Application Discontinuation
- 1999-01-29 AT AT99907427T patent/ATE226957T1/de not_active IP Right Cessation
- 1999-01-29 SI SI9930187T patent/SI1051425T1/xx unknown
- 1999-01-29 EE EEP200000441A patent/EE200000441A/xx unknown
- 1999-01-29 ES ES99907427T patent/ES2186330T3/es not_active Expired - Lifetime
- 1999-01-29 HU HU0101305A patent/HUP0101305A3/hu unknown
- 1999-01-29 BR BR9907270-0A patent/BR9907270A/pt not_active IP Right Cessation
- 1999-01-29 AU AU27197/99A patent/AU757183B2/en not_active Ceased
- 1999-01-29 DE DE69903708T patent/DE69903708T2/de not_active Expired - Lifetime
- 1999-01-29 KR KR1020007008297A patent/KR20010034473A/ko not_active Withdrawn
- 1999-01-29 ID IDW20001467A patent/ID26326A/id unknown
- 1999-01-29 PT PT99907427T patent/PT1051425E/pt unknown
- 1999-01-29 MA MA25443A patent/MA26601A1/fr unknown
- 1999-01-29 GE GEAP19995495A patent/GEP20022839B/en unknown
- 1999-01-29 EP EP99907427A patent/EP1051425B1/en not_active Expired - Lifetime
- 1999-01-29 NZ NZ505452A patent/NZ505452A/xx unknown
- 1999-01-29 TR TR2000/02218T patent/TR200002218T2/xx unknown
- 1999-01-29 CA CA002318278A patent/CA2318278A1/en not_active Abandoned
- 1999-01-29 CN CN99802548A patent/CN1289338A/zh active Pending
- 1999-01-29 US US09/601,301 patent/US6762170B1/en not_active Expired - Lifetime
- 1999-01-29 IL IL13704299A patent/IL137042A0/xx unknown
- 1999-01-29 SK SK1119-2000A patent/SK11192000A3/sk unknown
- 1999-01-29 DK DK99907427T patent/DK1051425T3/da active
- 1999-01-29 AP APAP/P/2000/001875A patent/AP2000001875A0/en unknown
- 1999-01-29 SV SV1999000009A patent/SV1999000009A/es unknown
- 1999-01-29 TW TW088101391A patent/TW434250B/zh active
- 1999-01-29 WO PCT/EP1999/000503 patent/WO1999038877A2/en not_active Ceased
- 1999-01-29 PL PL99342670A patent/PL342670A1/xx unknown
2000
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Also Published As

Publication number	Publication date
PE20000280A1 (es)	2000-03-28
HRP20000511A2 (en)	2000-12-31
BG104729A (en)	2001-04-30
EP1051425B1 (en)	2002-10-30
CN1289338A (zh)	2001-03-28
ID26326A (id)	2000-12-14
KR20010034473A (ko)	2001-04-25
JP2002501928A (ja)	2002-01-22
HUP0101305A3 (en)	2002-08-28
YU44900A (sh)	2003-01-31
DK1051425T3 (da)	2003-03-03
AR014508A1 (es)	2001-02-28
NO20003867D0 (no)	2000-07-28
SI1051425T1 (en)	2003-04-30
NO20003867L (no)	2000-07-28
CA2318278A1 (en)	1999-08-05
EA200000723A1 (ru)	2001-04-23
GEP20022839B (en)	2002-11-25
PT1051425E (pt)	2003-03-31
AU757183B2 (en)	2003-02-06
MA26601A1 (fr)	2004-12-20
BR9907270A (pt)	2000-10-24
WO1999038877A3 (en)	1999-09-30
EP1051425A2 (en)	2000-11-15
DE69903708D1 (de)	2002-12-05
EA003194B1 (ru)	2003-02-27
ATE226957T1 (de)	2002-11-15
WO1999038877A2 (en)	1999-08-05
AP2000001875A0 (en)	2000-09-30
NZ505452A (en)	2003-01-31
AU2719799A (en)	1999-08-16
EE200000441A (et)	2001-12-17
DE69903708T2 (de)	2003-07-03
HUP0101305A2 (hu)	2002-04-29
IL137042A0 (en)	2001-06-14
IS5550A (is)	2000-06-27
ES2186330T3 (es)	2003-05-01
SV1999000009A (es)	2000-09-05
HK1030611A1 (en)	2001-05-11
CO4980872A1 (es)	2000-11-27
SK11192000A3 (sk)	2001-06-11
US6762170B1 (en)	2004-07-13
TR200002218T2 (tr)	2000-12-21
BG63783B1 (bg)	2002-12-29
TW434250B (en)	2001-05-16
PL342670A1 (en)	2001-07-02

Publication	Publication Date	Title
EP1051425B1 (en)	2002-10-30	2-(PURIN-9-yl)-TETRAHYDROFURAN-3,4-DIOL DERIVATIVES
US6426337B1 (en)	2002-07-30	2-(Purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
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EP1090022B1 (en)	2003-08-06	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090021B1 (en)	2003-09-10	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
EP1090023B1 (en)	2003-09-10	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
US6610665B1 (en)	2003-08-26	2-(purin-9-yl)-tetrahydrofuran-3, 4-diol derivatives
HK1030611B (en)	2003-07-04	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
HK1032062B (en)	2003-06-20	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA00012926A (en)	2002-05-09	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA99005888A (en)	2000-01-01	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives