BG63783B1 - 2-(пурин-9-ил)-тетрахидрофуран-3,4-диолови производни - Google Patents

2-(пурин-9-ил)-тетрахидрофуран-3,4-диолови производни Download PDF

Info

Publication number: BG63783B1
Authority: BG; Bulgaria
Prior art keywords: ethyl; tetrahydro; purin; ethylamino; diol
Prior art date: 1998-01-31

Application number

BG104729A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG104729A (en

Inventor

Chuen Chan

Richard COUSINS

Brian Cox

Original Assignee

Glaxo Group Limited

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

2000-08-29

Publication date

2002-12-29

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

2000-08-29 Application filed by Glaxo Group Limited filed Critical Glaxo Group Limited

2001-04-30 Publication of BG104729A publication Critical patent/BG104729A/xx

2002-12-29 Publication of BG63783B1 publication Critical patent/BG63783B1/bg

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 abstract description 251
238000000034 method Methods 0.000 claims abstract description 32
238000011282 treatment Methods 0.000 claims abstract description 23
230000008569 process Effects 0.000 claims abstract description 21
208000027866 inflammatory disease Diseases 0.000 claims abstract description 7
-1 -CH = CH 2 Chemical group 0.000 claims description 208
125000000217 alkyl group Chemical group 0.000 claims description 37
229910052757 nitrogen Inorganic materials 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 31
125000004899 1-ethylpropylamino group Chemical group C(C)C(CC)N* 0.000 claims description 26
125000003118 aryl group Chemical group 0.000 claims description 23
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
229910052739 hydrogen Inorganic materials 0.000 claims description 22
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
239000012453 solvate Substances 0.000 claims description 17
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 11
101150065749 Churc1 gene Proteins 0.000 claims description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
102100038239 Protein Churchill Human genes 0.000 claims description 11
150000002431 hydrogen Chemical class 0.000 claims description 11
125000002757 morpholinyl group Chemical group 0.000 claims description 11
SSYDTHANSGMJTP-UHFFFAOYSA-N oxolane-3,4-diol Chemical compound OC1COCC1O SSYDTHANSGMJTP-UHFFFAOYSA-N 0.000 claims description 11
125000003386 piperidinyl group Chemical group 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
239000008194 pharmaceutical composition Substances 0.000 claims description 8
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 8
239000003814 drug Substances 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
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000002785 azepinyl group Chemical group 0.000 claims description 6
125000002393 azetidinyl group Chemical group 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000006552 (C3-C8) cycloalkyl 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 5
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 5
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 5
125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
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
239000000969 carrier Substances 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
238000004519 manufacturing process Methods 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 3
125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 2
125000004911 3,3-dimethylbutylamino group Chemical group CC(CCN*)(C)C 0.000 claims description 2
125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 claims description 2
125000001188 haloalkyl group Chemical group 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
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 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
AFMDDGRTVDNVIN-XVOBZGQLSA-N (2r,3r,4s,5s)-2-[2-(n-ethyl-3,4-dimethoxyanilino)-6-(pentan-3-ylamino)purin-9-yl]-5-(3-ethyl-1,2-oxazol-5-yl)oxolane-3,4-diol Chemical compound C1([C@H]2O[C@H]([C@@H]([C@@H]2O)O)N2C=3N=C(N=C(C=3N=C2)NC(CC)CC)N(CC)C=2C=C(OC)C(OC)=CC=2)=CC(CC)=NO1 AFMDDGRTVDNVIN-XVOBZGQLSA-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
PIQFBJZCVVGYDL-UHFFFAOYSA-N 1-ethynylpyrrolidine Chemical compound C#CN1CCCC1 PIQFBJZCVVGYDL-UHFFFAOYSA-N 0.000 claims 1
MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims 1
SEPUSXFGVHNDNU-PHDFWJEJSA-N 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=1N[C@H]1CC[C@H](N)CC1 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=1N[C@H]1CC[C@H](N)CC1 SEPUSXFGVHNDNU-PHDFWJEJSA-N 0.000 claims 1
OPIZUXVPELWOJO-UHFFFAOYSA-N O1N=C(C=C1)C=NO Chemical compound O1N=C(C=C1)C=NO OPIZUXVPELWOJO-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
239000003085 diluting agent Substances 0.000 claims 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229940127557 pharmaceutical product Drugs 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 108
238000009472 formulation Methods 0.000 abstract description 2
238000002560 therapeutic procedure Methods 0.000 abstract description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
239000000543 intermediate Substances 0.000 description 119
239000007787 solid Substances 0.000 description 103
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
238000004108 freeze drying Methods 0.000 description 74
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 67
239000000243 solution Substances 0.000 description 66
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 55
235000019439 ethyl acetate Nutrition 0.000 description 53
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 48
239000002904 solvent Substances 0.000 description 43
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 37
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 29
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
238000004809 thin layer chromatography Methods 0.000 description 27
239000011541 reaction mixture Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 23
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 20
239000003708 ampul Substances 0.000 description 20
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 20
238000003818 flash chromatography Methods 0.000 description 19
CJNRGSHEMCMUOE-UHFFFAOYSA-N 2-piperidin-1-ylethanamine Chemical compound NCCN1CCCCC1 CJNRGSHEMCMUOE-UHFFFAOYSA-N 0.000 description 18
239000003153 chemical reaction reagent Substances 0.000 description 18
239000006260 foam Substances 0.000 description 18
210000000265 leukocyte Anatomy 0.000 description 18
239000012299 nitrogen atmosphere Substances 0.000 description 18
238000000746 purification Methods 0.000 description 18
238000004128 high performance liquid chromatography Methods 0.000 description 17
239000000047 product Substances 0.000 description 16
235000017557 sodium bicarbonate Nutrition 0.000 description 16
229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
239000012043 crude product Substances 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
239000000460 chlorine Substances 0.000 description 14
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
239000003039 volatile agent Substances 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
229910004298 SiO 2 Inorganic materials 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
238000001704 evaporation Methods 0.000 description 12
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
239000003921 oil Substances 0.000 description 12
235000019198 oils Nutrition 0.000 description 12
239000000377 silicon dioxide Substances 0.000 description 11
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 10
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 10
239000002126 C01EB10 - Adenosine Substances 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 10
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
FHQDWPCFSJMNCT-UHFFFAOYSA-N N(tele)-methylhistamine Chemical compound CN1C=NC(CCN)=C1 FHQDWPCFSJMNCT-UHFFFAOYSA-N 0.000 description 10
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
229960005305 adenosine Drugs 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
235000019253 formic acid Nutrition 0.000 description 10
108020003175 receptors Proteins 0.000 description 10
102000005962 receptors Human genes 0.000 description 10
229920006395 saturated elastomer Polymers 0.000 description 10
241000400611 Eucalyptus deanei Species 0.000 description 9
229910052796 boron Inorganic materials 0.000 description 9
230000000694 effects Effects 0.000 description 9
230000008020 evaporation Effects 0.000 description 9
238000003756 stirring Methods 0.000 description 9
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 8
PQPFFKCJENSZKL-UHFFFAOYSA-N pentan-3-amine Chemical compound CCC(N)CC PQPFFKCJENSZKL-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
238000002953 preparative HPLC Methods 0.000 description 8
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
239000006071 cream Substances 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
238000010438 heat treatment Methods 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
239000000443 aerosol Substances 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 6
239000011609 ammonium molybdate Substances 0.000 description 6
235000018660 ammonium molybdate Nutrition 0.000 description 6
229940010552 ammonium molybdate Drugs 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 6
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 6
125000006239 protecting group Chemical group 0.000 description 6
230000000451 tissue damage Effects 0.000 description 6
231100000827 tissue damage Toxicity 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 5
230000004913 activation Effects 0.000 description 5
239000000556 agonist Substances 0.000 description 5
229910052681 coesite Inorganic materials 0.000 description 5
229910052906 cristobalite Inorganic materials 0.000 description 5
VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 5
230000007812 deficiency Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 5
239000000284 extract Substances 0.000 description 5
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 5
239000012442 inert solvent Substances 0.000 description 5
AHVQYHFYQWKUKB-UHFFFAOYSA-N oxan-4-amine Chemical compound NC1CCOCC1 AHVQYHFYQWKUKB-UHFFFAOYSA-N 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
238000010992 reflux Methods 0.000 description 5
239000007921 spray Substances 0.000 description 5
229910052682 stishovite Inorganic materials 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
229910052905 tridymite Inorganic materials 0.000 description 5
GWEATQMXNIFWCP-UHFFFAOYSA-N 1H-pyrazole-5-carboximidamide hydrochloride Chemical compound Cl.NC(=N)C=1C=CNN=1 GWEATQMXNIFWCP-UHFFFAOYSA-N 0.000 description 4
XPQIPUZPSLAZDV-UHFFFAOYSA-N 2-pyridylethylamine Chemical compound NCCC1=CC=CC=N1 XPQIPUZPSLAZDV-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
206010061218 Inflammation Diseases 0.000 description 4
STVVMTBJNDTZBF-VIFPVBQESA-N L-phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 description 4
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
230000008901 benefit Effects 0.000 description 4
KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical group CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 4
238000007796 conventional method Methods 0.000 description 4
238000010828 elution Methods 0.000 description 4
210000003979 eosinophil Anatomy 0.000 description 4
150000002148 esters Chemical group 0.000 description 4
238000000605 extraction Methods 0.000 description 4
229910052731 fluorine Inorganic materials 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
230000004968 inflammatory condition Effects 0.000 description 4
230000004054 inflammatory process Effects 0.000 description 4
239000007788 liquid Substances 0.000 description 4
CCERQOYLJJULMD-UHFFFAOYSA-M magnesium;carbanide;chloride Chemical compound [CH3-].[Mg+2].[Cl-] CCERQOYLJJULMD-UHFFFAOYSA-M 0.000 description 4
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
239000011734 sodium Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 4
RPIXOLUIHUFDOY-UHFFFAOYSA-N thian-4-amine Chemical compound NC1CCSCC1 RPIXOLUIHUFDOY-UHFFFAOYSA-N 0.000 description 4
239000002562 thickening agent Substances 0.000 description 4
WBNQTEKLVXXLQW-MATHAZKKSA-N (3s,4r,5r)-5-(6-aminopurin-9-yl)-2,2-bis(hydroxymethyl)oxolane-3,4-diol Chemical class C1=NC=2C(N)=NC=NC=2N1[C@@H]1OC(CO)(CO)[C@@H](O)[C@H]1O WBNQTEKLVXXLQW-MATHAZKKSA-N 0.000 description 3
MYHRJLDFVDLYDW-UHFFFAOYSA-N (4-formyloxyoxolan-3-yl) formate Chemical compound O=COC1COCC1OC=O MYHRJLDFVDLYDW-UHFFFAOYSA-N 0.000 description 3
BNMNQUBPZZSXQU-UHFFFAOYSA-N 1,3-dioxole-4-carboxylic acid Chemical compound OC(=O)C1=COCO1 BNMNQUBPZZSXQU-UHFFFAOYSA-N 0.000 description 3
NLHBHVGPMMXWIM-UHFFFAOYSA-N 1-(4-aminopiperidin-1-yl)ethanone Chemical compound CC(=O)N1CCC(N)CC1 NLHBHVGPMMXWIM-UHFFFAOYSA-N 0.000 description 3
RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 3
RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical group N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 3
108050000203 Adenosine receptors Proteins 0.000 description 3
102000009346 Adenosine receptors Human genes 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
239000005695 Ammonium acetate Substances 0.000 description 3
241000700198 Cavia Species 0.000 description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
108010010803 Gelatin Proteins 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 3
150000003835 adenosine derivatives Chemical class 0.000 description 3
235000019257 ammonium acetate Nutrition 0.000 description 3
229940043376 ammonium acetate Drugs 0.000 description 3
235000019270 ammonium chloride Nutrition 0.000 description 3
239000002260 anti-inflammatory agent Substances 0.000 description 3
229940121363 anti-inflammatory agent Drugs 0.000 description 3
239000004599 antimicrobial Substances 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
235000019846 buffering salt Nutrition 0.000 description 3
239000002775 capsule Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000003246 corticosteroid Substances 0.000 description 3
238000000132 electrospray ionisation Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
150000002168 ethanoic acid esters Chemical class 0.000 description 3
229940014259 gelatin Drugs 0.000 description 3
229920000159 gelatin Polymers 0.000 description 3
239000008273 gelatin Substances 0.000 description 3
235000019322 gelatine Nutrition 0.000 description 3
235000011852 gelatine desserts Nutrition 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
239000008101 lactose Substances 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
230000014759 maintenance of location Effects 0.000 description 3
238000001819 mass spectrum Methods 0.000 description 3
230000001404 mediated effect Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 3
TYHXIJJQIJKFSO-UHFFFAOYSA-N n'-pyridin-2-ylethane-1,2-diamine Chemical compound NCCNC1=CC=CC=N1 TYHXIJJQIJKFSO-UHFFFAOYSA-N 0.000 description 3
KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 3
238000006386 neutralization reaction Methods 0.000 description 3
230000003472 neutralizing effect Effects 0.000 description 3
210000000440 neutrophil Anatomy 0.000 description 3
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 3
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
238000011160 research Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000008107 starch Substances 0.000 description 3
229940032147 starch Drugs 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 2
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 2
NALZTFARIYUCBY-UHFFFAOYSA-N 1-nitrobutane Chemical compound CCCC[N+]([O-])=O NALZTFARIYUCBY-UHFFFAOYSA-N 0.000 description 2
XDLJIIILKATPAQ-UHFFFAOYSA-N 2,8-dichloro-7h-purine Chemical class ClC1=NC=C2NC(Cl)=NC2=N1 XDLJIIILKATPAQ-UHFFFAOYSA-N 0.000 description 2
KQDXRRAVDLIMGM-UHFFFAOYSA-N 2-(2-nitroethoxy)oxane Chemical compound [O-][N+](=O)CCOC1CCCCO1 KQDXRRAVDLIMGM-UHFFFAOYSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
HFACYWDPMNWMIW-UHFFFAOYSA-N 2-cyclohexylethanamine Chemical compound NCCC1CCCCC1 HFACYWDPMNWMIW-UHFFFAOYSA-N 0.000 description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 2
GPWHFPWZAPOYNO-UHFFFAOYSA-N 3,3-dimethylbutan-1-amine Chemical compound CC(C)(C)CCN GPWHFPWZAPOYNO-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
101150051188 Adora2a gene Proteins 0.000 description 2
208000023275 Autoimmune disease Diseases 0.000 description 2
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
108090000695 Cytokines Proteins 0.000 description 2
102000004127 Cytokines Human genes 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 2
208000018522 Gastrointestinal disease Diseases 0.000 description 2
241000282412 Homo Species 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
206010020751 Hypersensitivity Diseases 0.000 description 2
235000010643 Leucaena leucocephala Nutrition 0.000 description 2
240000007472 Leucaena leucocephala Species 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910019093 NaOCl Inorganic materials 0.000 description 2
108010058846 Ovalbumin Proteins 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 2
PGDRRVMJVNBQLV-UHFFFAOYSA-N [H]OC=O.[H]OC=O.[H]C([H])N Chemical compound [H]OC=O.[H]OC=O.[H]C([H])N PGDRRVMJVNBQLV-UHFFFAOYSA-N 0.000 description 2
238000009825 accumulation Methods 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
230000009471 action Effects 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
125000002877 alkyl aryl group Chemical group 0.000 description 2
CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 2
229940063655 aluminum stearate Drugs 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000003963 antioxidant agent Substances 0.000 description 2
239000008135 aqueous vehicle Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
208000010668 atopic eczema Diseases 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000012267 brine Substances 0.000 description 2
206010006451 bronchitis Diseases 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
229960001334 corticosteroids Drugs 0.000 description 2
125000000753 cycloalkyl group Chemical group 0.000 description 2
NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
230000006378 damage Effects 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
UXOLDCOJRAMLTQ-UHFFFAOYSA-N ethyl 2-chloro-2-hydroxyiminoacetate Chemical compound CCOC(=O)C(Cl)=NO UXOLDCOJRAMLTQ-UHFFFAOYSA-N 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
230000036541 health Effects 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
230000002757 inflammatory effect Effects 0.000 description 2
238000001802 infusion Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
UEXQBEVWFZKHNB-UHFFFAOYSA-N intermediate 29 Natural products C1=CC(N)=CC=C1NC1=NC=CC=N1 UEXQBEVWFZKHNB-UHFFFAOYSA-N 0.000 description 2
230000000968 intestinal effect Effects 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000011630 iodine Substances 0.000 description 2
239000007951 isotonicity adjuster Substances 0.000 description 2
125000000842 isoxazolyl group Chemical group 0.000 description 2
239000010410 layer Substances 0.000 description 2
239000006210 lotion Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
210000004698 lymphocyte Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
239000000463 material Substances 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
125000002950 monocyclic group Chemical group 0.000 description 2
AWBKQZSYNWLCMW-UHFFFAOYSA-N n-(dibromomethylidene)hydroxylamine Chemical compound ON=C(Br)Br AWBKQZSYNWLCMW-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
239000002687 nonaqueous vehicle Substances 0.000 description 2
239000002674 ointment Substances 0.000 description 2
125000002971 oxazolyl group Chemical group 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
229940117803 phenethylamine Drugs 0.000 description 2
RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 2
229920001223 polyethylene glycol Polymers 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000001737 promoting effect Effects 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000009467 reduction Effects 0.000 description 2
230000008439 repair process Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
230000029058 respiratory gaseous exchange Effects 0.000 description 2
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
239000006188 syrup Substances 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000003536 tetrazoles Chemical class 0.000 description 2
229940124597 therapeutic agent Drugs 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
238000011200 topical administration Methods 0.000 description 2
CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
KQCFQSMHNZFZCQ-MCDZGGTQSA-N (2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol N-ethylformamide Chemical compound CCNC=O.C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O KQCFQSMHNZFZCQ-MCDZGGTQSA-N 0.000 description 1
YIJRBFFHGMMYQP-IDTAVKCVSA-N (2r,3r,4s,5r)-2-[2-chloro-6-(pentan-3-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=NC=2C(NC(CC)CC)=NC(Cl)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YIJRBFFHGMMYQP-IDTAVKCVSA-N 0.000 description 1
FQBKNNBFHAYPCZ-OLWIJOGUSA-N (2s,3s,4r,5r)-2-[3-(1-hydroxyethyl)-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=3)C(C)O)O)C=NC=2C(NC(CC)CC)=NC=1NCCN1CCCCC1 FQBKNNBFHAYPCZ-OLWIJOGUSA-N 0.000 description 1
LQLOGZQVKUNBRX-UHFFFAOYSA-N (3-iodophenyl)methanamine Chemical compound NCC1=CC=CC(I)=C1 LQLOGZQVKUNBRX-UHFFFAOYSA-N 0.000 description 1
NGXSWUFDCSEIOO-SCSAIBSYSA-N (3r)-pyrrolidin-3-amine Chemical compound N[C@@H]1CCNC1 NGXSWUFDCSEIOO-SCSAIBSYSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000006648 (C1-C8) haloalkyl group Chemical group 0.000 description 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
MLCJWRIUYXIWNU-OWOJBTEDSA-N (e)-ethene-1,2-diamine Chemical compound N\C=C\N MLCJWRIUYXIWNU-OWOJBTEDSA-N 0.000 description 1
YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-N 0.000 description 1
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
GBCAGXLDCTZCCT-UHFFFAOYSA-N 1,2-oxazol-3-ylmethanol Chemical compound OCC=1C=CON=1 GBCAGXLDCTZCCT-UHFFFAOYSA-N 0.000 description 1
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
JIKZRWFMSWZOLP-UHFFFAOYSA-N 1,3-dioxole-2-carboxylic acid Chemical compound OC(=O)C1OC=CO1 JIKZRWFMSWZOLP-UHFFFAOYSA-N 0.000 description 1
KDISMIMTGUMORD-UHFFFAOYSA-N 1-acetylpiperidine Chemical compound CC(=O)N1CCCCC1 KDISMIMTGUMORD-UHFFFAOYSA-N 0.000 description 1
JSZOAYXJRCEYSX-UHFFFAOYSA-N 1-nitropropane Chemical compound CCC[N+]([O-])=O JSZOAYXJRCEYSX-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
QEJGPUMQWGIHPH-UHFFFAOYSA-N 2-amino-n-methylethanesulfonamide Chemical compound CNS(=O)(=O)CCN QEJGPUMQWGIHPH-UHFFFAOYSA-N 0.000 description 1
ONXCBJOMYNPZNI-UHFFFAOYSA-N 2-bromo-3,7-dihydropurin-6-one Chemical compound N1C(Br)=NC(=O)C2=C1N=CN2 ONXCBJOMYNPZNI-UHFFFAOYSA-N 0.000 description 1
IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 1
ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 description 1
LTUABJAYJRTHEH-UHFFFAOYSA-N 3-ethyl-1,2-oxazole Chemical compound CCC=1C=CON=1 LTUABJAYJRTHEH-UHFFFAOYSA-N 0.000 description 1
FXNSVEQMUYPYJS-UHFFFAOYSA-N 4-(2-aminoethyl)benzenesulfonamide Chemical compound NCCC1=CC=C(S(N)(=O)=O)C=C1 FXNSVEQMUYPYJS-UHFFFAOYSA-N 0.000 description 1
MXJQJURZHQZLNN-UHFFFAOYSA-N 4-amino-2-fluorophenol Chemical compound NC1=CC=C(O)C(F)=C1 MXJQJURZHQZLNN-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
LSLYOANBFKQKPT-DIFFPNOSSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]benzene-1,3-diol Chemical compound C([C@@H](C)NC[C@H](O)C=1C=C(O)C=C(O)C=1)C1=CC=C(O)C=C1 LSLYOANBFKQKPT-DIFFPNOSSA-N 0.000 description 1
GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical class NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 1
102000007471 Adenosine A2A receptor Human genes 0.000 description 1
108010085277 Adenosine A2A receptor Proteins 0.000 description 1
108010060261 Adenosine A3 Receptor Proteins 0.000 description 1
102000008161 Adenosine A3 Receptor Human genes 0.000 description 1
101150078577 Adora2b gene Proteins 0.000 description 1
108010088751 Albumins Proteins 0.000 description 1
102000009027 Albumins Human genes 0.000 description 1
102100024321 Alkaline phosphatase, placental type Human genes 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
208000024827 Alzheimer disease Diseases 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000894006 Bacteria Species 0.000 description 1
KUVIULQEHSCUHY-XYWKZLDCSA-N Beclometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(=O)CC)(OC(=O)CC)[C@@]1(C)C[C@@H]2O KUVIULQEHSCUHY-XYWKZLDCSA-N 0.000 description 1
201000006474 Brain Ischemia Diseases 0.000 description 1
208000009079 Bronchial Spasm Diseases 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
206010006482 Bronchospasm Diseases 0.000 description 1
IDGYZTWYKGGDAW-UHFFFAOYSA-N C(=O)O.C(C)C1=NOC(=C1)C1OCC(C1O)O Chemical compound C(=O)O.C(C)C1=NOC(=C1)C1OCC(C1O)O IDGYZTWYKGGDAW-UHFFFAOYSA-N 0.000 description 1
QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 1
PAOANWZGLPPROA-RQXXJAGISA-N CGS-21680 Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(O)=O)=CC=3)=NC(N)=C2N=C1 PAOANWZGLPPROA-RQXXJAGISA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
206010008120 Cerebral ischaemia Diseases 0.000 description 1
UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
206010010099 Combined immunodeficiency Diseases 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000699802 Cricetulus griseus Species 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
229920002785 Croscarmellose sodium Polymers 0.000 description 1
IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
206010012289 Dementia Diseases 0.000 description 1
SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 1
206010012434 Dermatitis allergic Diseases 0.000 description 1
206010051392 Diapedesis Diseases 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
244000166102 Eucalyptus leucoxylon Species 0.000 description 1
235000004694 Eucalyptus leucoxylon Nutrition 0.000 description 1
208000012895 Gastric disease Diseases 0.000 description 1
208000007882 Gastritis Diseases 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000007818 Grignard reagent Substances 0.000 description 1
241000590002 Helicobacter pylori Species 0.000 description 1
206010048643 Hypereosinophilic syndrome Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 0.000 description 1
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
101150101095 Mmp12 gene Proteins 0.000 description 1
108010008211 N-Formylmethionine Leucyl-Phenylalanine Proteins 0.000 description 1
HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
PRQROPMIIGLWRP-UHFFFAOYSA-N N-formyl-methionyl-leucyl-phenylalanin Chemical compound 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 1
101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
108700020962 Peroxidase Proteins 0.000 description 1
102000003992 Peroxidases Human genes 0.000 description 1
206010057249 Phagocytosis Diseases 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
239000004365 Protease Substances 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
206010063837 Reperfusion injury Diseases 0.000 description 1
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
GIIZNNXWQWCKIB-UHFFFAOYSA-N Serevent Chemical compound C1=C(O)C(CO)=CC(C(O)CNCCCCCCOCCCCC=2C=CC=CC=2)=C1 GIIZNNXWQWCKIB-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
DMXHSJIVAPMXIZ-UHFFFAOYSA-N [5-(3-ethyl-1,2-oxazol-5-yl)-4-formyloxyoxolan-3-yl] formate Chemical compound C(=O)OC1C(OCC1OC=O)C1=CC(=NO1)CC DMXHSJIVAPMXIZ-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000000654 additive Substances 0.000 description 1
UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 description 1
201000009628 adenosine deaminase deficiency Diseases 0.000 description 1
239000003121 adenosine kinase inhibitor Substances 0.000 description 1
LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 description 1
210000001789 adipocyte Anatomy 0.000 description 1
239000000464 adrenergic agent Substances 0.000 description 1
230000001270 agonistic effect Effects 0.000 description 1
NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005257 alkyl acyl group Chemical group 0.000 description 1
239000013566 allergen Substances 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
239000008168 almond oil Substances 0.000 description 1
HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
125000006242 amine protecting group Chemical group 0.000 description 1
230000002052 anaphylactic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
230000002924 anti-infective effect Effects 0.000 description 1
229940124599 anti-inflammatory drug Drugs 0.000 description 1
238000011861 anti-inflammatory therapy Methods 0.000 description 1
230000002253 anti-ischaemic effect Effects 0.000 description 1
230000003243 anti-lipolytic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000000427 antigen Substances 0.000 description 1
108091007433 antigens Proteins 0.000 description 1
102000036639 antigens Human genes 0.000 description 1
229960005475 antiinfective agent Drugs 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000010936 aqueous wash Methods 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
201000008937 atopic dermatitis Diseases 0.000 description 1
208000036556 autosomal recessive T cell-negative B cell-negative NK cell-negative due to adenosine deaminase deficiency severe combined immunodeficiency Diseases 0.000 description 1
210000003651 basophil Anatomy 0.000 description 1
229950000210 beclometasone dipropionate Drugs 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
ZYGJOOODSHXSQU-UHFFFAOYSA-N benzenesulfonamide;formic acid Chemical compound OC=O.NS(=O)(=O)C1=CC=CC=C1 ZYGJOOODSHXSQU-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000002527 bicyclic carbocyclic group Chemical group 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
230000003293 cardioprotective effect Effects 0.000 description 1
230000005792 cardiovascular activity Effects 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
206010008118 cerebral infarction Diseases 0.000 description 1
229940082500 cetostearyl alcohol Drugs 0.000 description 1
BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 1
239000002975 chemoattractant Substances 0.000 description 1
210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003240 coconut oil Substances 0.000 description 1
235000019864 coconut oil Nutrition 0.000 description 1
OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000004040 coloring Methods 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
229960001681 croscarmellose sodium Drugs 0.000 description 1
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 1
229940095074 cyclic amp Drugs 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
229940042935 dichlorodifluoromethane Drugs 0.000 description 1
229940087091 dichlorotetrafluoroethane Drugs 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000009977 dual effect Effects 0.000 description 1
239000008157 edible vegetable oil Substances 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
210000003038 endothelium Anatomy 0.000 description 1
206010015037 epilepsy Diseases 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
229940012356 eye drops Drugs 0.000 description 1
239000003925 fat Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
229960001022 fenoterol Drugs 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
229960000289 fluticasone propionate Drugs 0.000 description 1
WMWTYOKRWGGJOA-CENSZEJFSA-N fluticasone propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(OC(=O)CC)[C@@]2(C)C[C@@H]1O WMWTYOKRWGGJOA-CENSZEJFSA-N 0.000 description 1
239000011888 foil Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
150000004675 formic acid derivatives Chemical class 0.000 description 1
BAONHUZQTANSBI-UHFFFAOYSA-N formic acid;methanamine Chemical compound [NH3+]C.[O-]C=O BAONHUZQTANSBI-UHFFFAOYSA-N 0.000 description 1
BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 1
229960002848 formoterol Drugs 0.000 description 1
239000012458 free base Substances 0.000 description 1
ULYSABNRLLVZCE-UHFFFAOYSA-N furan-3,4-diol Chemical compound OC1=COC=C1O ULYSABNRLLVZCE-UHFFFAOYSA-N 0.000 description 1
MZUZVRHTPRROKN-UHFFFAOYSA-N furo[3,4-d][1,3]dioxole Chemical compound O1C=C2OCOC2=C1 MZUZVRHTPRROKN-UHFFFAOYSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
230000004927 fusion Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000004795 grignard reagents Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
208000019622 heart disease Diseases 0.000 description 1
229940037467 helicobacter pylori Drugs 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
UBHWBODXJBSFLH-UHFFFAOYSA-N hexadecan-1-ol;octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO.CCCCCCCCCCCCCCCCCCO UBHWBODXJBSFLH-UHFFFAOYSA-N 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
PYFDZOCGFHIRST-UHFFFAOYSA-N hydron;(3-iodophenyl)methanamine;chloride Chemical compound Cl.NCC1=CC=CC(I)=C1 PYFDZOCGFHIRST-UHFFFAOYSA-N 0.000 description 1
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
229920003063 hydroxymethyl cellulose Polymers 0.000 description 1
229940031574 hydroxymethyl cellulose Drugs 0.000 description 1
230000009610 hypersensitivity Effects 0.000 description 1
208000024364 idiopathic hypereosinophilic syndrome Diseases 0.000 description 1
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 description 1
230000036039 immunity Effects 0.000 description 1
239000003018 immunosuppressive agent Substances 0.000 description 1
229940125721 immunosuppressive agent Drugs 0.000 description 1
239000012535 impurity Substances 0.000 description 1
210000004969 inflammatory cell Anatomy 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
230000009545 invasion Effects 0.000 description 1
NWYYWIJOWOLJNR-RXMQYKEDSA-N l-valinol Chemical compound CC(C)[C@H](N)CO NWYYWIJOWOLJNR-RXMQYKEDSA-N 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000000787 lecithin Substances 0.000 description 1
229940067606 lecithin Drugs 0.000 description 1
230000023404 leukocyte cell-cell adhesion Effects 0.000 description 1
150000007517 lewis acids Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
229940057995 liquid paraffin Drugs 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000007937 lozenge Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
JUWPVXZFRLXXTM-UHFFFAOYSA-M magnesium;but-1-yne;chloride Chemical compound [Mg+2].[Cl-].CCC#[C-] JUWPVXZFRLXXTM-UHFFFAOYSA-M 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
YECBIJXISLIIDS-UHFFFAOYSA-N mepyramine Chemical compound C1=CC(OC)=CC=C1CN(CCN(C)C)C1=CC=CC=N1 YECBIJXISLIIDS-UHFFFAOYSA-N 0.000 description 1
229960000582 mepyramine Drugs 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
239000004200 microcrystalline wax Substances 0.000 description 1
235000019808 microcrystalline wax Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000003020 moisturizing effect Effects 0.000 description 1
WOFMFGQZHJDGCX-ZULDAHANSA-N mometasone furoate Chemical compound O([C@]1([C@@]2(C)C[C@H](O)[C@]3(Cl)[C@@]4(C)C=CC(=O)C=C4CC[C@H]3[C@@H]2C[C@H]1C)C(=O)CCl)C(=O)C1=CC=CO1 WOFMFGQZHJDGCX-ZULDAHANSA-N 0.000 description 1
229960002744 mometasone furoate Drugs 0.000 description 1
210000001616 monocyte Anatomy 0.000 description 1
201000006417 multiple sclerosis Diseases 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
208000031225 myocardial ischemia Diseases 0.000 description 1
OKDQKPLMQBXTNH-UHFFFAOYSA-N n,n-dimethyl-2h-pyridin-1-amine Chemical compound CN(C)N1CC=CC=C1 OKDQKPLMQBXTNH-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
WQZXJTWTIYVJLT-UHFFFAOYSA-N n-ethylpiperidin-1-amine Chemical compound CCNN1CCCCC1 WQZXJTWTIYVJLT-UHFFFAOYSA-N 0.000 description 1
KCMDLQKACKNGMB-UHFFFAOYSA-N n-hydroxy-2-oxopropanimidoyl chloride Chemical compound CC(=O)C(Cl)=NO KCMDLQKACKNGMB-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229940100662 nasal drops Drugs 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
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
230000002611 ovarian Effects 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229940056211 paraffin Drugs 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
244000045947 parasite Species 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
230000008782 phagocytosis Effects 0.000 description 1
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
PJPOCNJHYFUPCE-UHFFFAOYSA-N picen-1-ol Chemical compound C1=CC=CC2=C(C=CC=3C4=CC=C5C=CC=C(C=35)O)C4=CC=C21 PJPOCNJHYFUPCE-UHFFFAOYSA-N 0.000 description 1
108010031345 placental alkaline phosphatase Proteins 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229940068917 polyethylene glycols Drugs 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
238000011176 pooling Methods 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
229940116317 potato starch Drugs 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
239000003380 propellant Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 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
230000002685 pulmonary effect Effects 0.000 description 1
239000003379 purinergic P1 receptor agonist Substances 0.000 description 1
150000003212 purines Chemical class 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
239000012429 reaction media Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
208000023504 respiratory system disease Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
150000003290 ribose derivatives Chemical class 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
229960002052 salbutamol Drugs 0.000 description 1
229960004017 salmeterol Drugs 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
239000010802 sludge Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 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
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
208000018556 stomach disease Diseases 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000002511 suppository base Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229960000195 terbutaline Drugs 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 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
125000001544 thienyl group Chemical group 0.000 description 1
230000017423 tissue regeneration Effects 0.000 description 1
230000000699 topical effect Effects 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
238000001665 trituration Methods 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
238000005406 washing Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1
230000029663 wound healing Effects 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 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)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

BG104729A 1998-01-31 2000-08-29 2-(пурин-9-ил)-тетрахидрофуран-3,4-диолови производни BG63783B1 (bg)

Applications Claiming Priority (3)

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
PCT/EP1999/000503 WO1999038877A2 (en)	1998-01-31	1999-01-29	2-(PURIN-9-yl)-TETRAHYDROFURAN-3,4-DIOL DERIVATIVES

Publications (2)

Publication Number	Publication Date
BG104729A BG104729A (en)	2001-04-30
BG63783B1 true BG63783B1 (bg)	2002-12-29

Family

ID=26313042

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104729A BG63783B1 (bg)	1998-01-31	2000-08-29	2-(пурин-9-ил)-тетрахидрофуран-3,4-диолови производни

Country Status (38)

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

Families Citing this family (55)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6514949B1 (en)	1994-07-11	2003-02-04	University Of Virginia Patent Foundation	Method compositions for treating the inflammatory response
YU44900A (sh)	1998-01-31	2003-01-31	Glaxo Group Limited	Derivati 2-(purin-9-il)tetrahidrofuran-3,4-diola
GB9813565D0 (en) *	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
GB9813554D0 (en)	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
CN1313861A (zh)	1998-06-23	2001-09-19	葛兰素集团有限公司	2－(嘌呤－9－基)－四氢呋喃－3,4－二醇衍生物
GB9813540D0 (en) *	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
US6232297B1 (en)	1999-02-01	2001-05-15	University Of Virginia Patent Foundation	Methods and compositions for treating inflammatory response
US7427606B2 (en)	1999-02-01	2008-09-23	University Of Virginia Patent Foundation	Method to reduce inflammatory response in transplanted tissue
US7378400B2 (en)	1999-02-01	2008-05-27	University Of Virginia Patent Foundation	Method to reduce an inflammatory response from arthritis
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
GB2372742A (en)	2001-03-03	2002-09-04	Univ Leiden	C2,5'-Disubstituted and N6,C2,5'-trisubstituted adenosine derivatives and their different uses
US20040162422A1 (en) *	2001-03-20	2004-08-19	Adrian Hall	Chemical compounds
NZ532062A (en)	2001-10-01	2006-09-29	Univ Virginia	2-propynyl adenosine analogues having A2 adenosine recepter agonist activity and compositions thereof to treat inflammatory responses
GB0206655D0 (en) *	2002-03-21	2002-05-01	Glaxo Group Ltd	Novel process
GB0206657D0 (en) *	2002-03-21	2002-05-01	Glaxo Group Ltd	Novel intermediate and process
AR044519A1 (es)	2003-05-02	2005-09-14	Novartis Ag	Derivados de piridin-tiazol amina y de pirimidin-tiazol amina
WO2005063246A1 (en) *	2003-12-29	2005-07-14	Can-Fite Biopharma Ltd.	Method for treatment of multiple sclerosis
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
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
WO2006023272A1 (en)	2004-08-02	2006-03-02	University Of Virginia Patent Foundation	2-polycyclic propynyl adenosine analogs having a2a agonist activity
SG155182A1 (en)	2004-08-02	2009-09-30	Univ Virginia	2-propynyl adenosine analogs with modified 5æ-ribose groups having a2a agonist activity
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
GB0424284D0 (en)	2004-11-02	2004-12-01	Novartis Ag	Organic compounds
GB0426164D0 (en)	2004-11-29	2004-12-29	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
MY144906A (en)	2005-10-21	2011-11-30	Novartis Ag	Human antibodies against il13 and therapeutic uses
GB0601951D0 (en)	2006-01-31	2006-03-15	Novartis Ag	Organic compounds
RU2457209C2 (ru) *	2006-04-21	2012-07-27	Новартис Аг	Производные пурина, предназначенные для применения в качестве агонистов аденозинового рецептора а2а
EP1889846A1 (en) *	2006-07-13	2008-02-20	Novartis AG	Purine derivatives as A2a agonists
MX2009003185A (es)	2006-09-29	2009-04-03	Novartis Ag	Pirazolopirimidinas como inhibidores de lipido cinasa pi3k.
AU2007315234A1 (en)	2006-10-30	2008-05-08	Novartis Ag	Heterocyclic compounds as antiinflammatory agents
CN101910153B (zh)	2008-01-11	2014-01-22	诺华股份有限公司	作为激酶抑制剂的嘧啶类
PT2391366E (pt)	2009-01-29	2013-02-05	Novartis Ag	Benzimidazoles substituídos para o tratamento de astrocitomas
US8389526B2 (en)	2009-08-07	2013-03-05	Novartis Ag	3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
BR112012003262A8 (pt)	2009-08-12	2016-05-17	Novartis Ag	compostos de hidrazona heterocíclica e seus usos para tratar câncer e inflamação
PE20121148A1 (es)	2009-08-17	2012-09-07	Intellikine Llc	Compuestos heterociclicos y usos de los mismos
BR112012008061A2 (pt)	2009-08-20	2016-03-01	Novartis Ag	compostos de oxima heterocíclica
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
EP2673277A1 (en)	2011-02-10	2013-12-18	Novartis AG	[1, 2, 4]triazolo [4, 3 -b]pyridazine compounds as inhibitors of the c-met tyrosine kinase
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
BR112013021638A2 (pt)	2011-02-25	2016-08-02	Irm Llc	"compostos inibidores de trk, seu uso e composições que os compreendem"
EP2755976B1 (en)	2011-09-15	2018-07-18	Novartis AG	6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyridines as c-met tyrosine kinase inhibitors
US20130209543A1 (en)	2011-11-23	2013-08-15	Intellikine Llc	Enhanced treatment regimens using mtor inhibitors
JP2015512425A (ja)	2012-04-03	2015-04-27	ノバルティスアーゲー	チロシンキナーゼ阻害剤との組合せ製品及びそれらの使用
WO2014151147A1 (en)	2013-03-15	2014-09-25	Intellikine, Llc	Combination of kinase inhibitors and uses thereof
WO2015084804A1 (en)	2013-12-03	2015-06-11	Novartis Ag	Combination of mdm2 inhibitor and braf inhibitor and their use
EP3116876A4 (en) *	2014-03-13	2017-10-25	Agency For Science, Technology And Research	Fused pyrimidine-based hydroxamate derivatives
WO2016011658A1 (en)	2014-07-25	2016-01-28	Novartis Ag	Combination therapy
AU2015294889B2 (en)	2014-07-31	2018-03-15	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

Family Cites Families (66)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE768925A (fr)	1970-06-30	1971-11-03	Takeda Chemical Industries Ltd	Derives d'adenosine et procede de preparation
DE2034785A1 (de)	1970-07-14	1972-01-20	Boehnnger Mannheim GmbH, 6800 Mann heim Waldhof	Adenosin 5 carbonsäurederivate
US4224438A (en)	1970-07-14	1980-09-23	Boehringer Mannheim Gmbh	Adenosine-5'-carboxylic acid amides
CA1019727A (en)	1971-03-18	1977-10-25	Abbott Laboratories	Adenosine-5'-carboxylic acid amides
BE789773A (fr)	1971-10-08	1973-04-06	Schering Ag	Adenosines n6 -substituees et leur procede de
US3864483A (en)	1972-03-22	1975-02-04	Abbott Lab	Adenosine-5{40 -carboxylic acid amides
CA1082695A (en)	1972-04-10	1980-07-29	Francis E. Fischer	Process for preparing adenosine-5'-carboxamides
US3966917A (en)	1974-07-30	1976-06-29	Abbott Laboratories	Platelet aggregation inhibitors
US4146715A (en)	1975-08-27	1979-03-27	Burroughs Wellcome Co.	2-amido-9-(2-acyloxyethoxymethyl)hypoxanthines
DE2621470A1 (de)	1976-05-14	1977-12-01	Pharma Waldhof Gmbh & Co	Nucleosidcarbonsaeurenitrile und ihre derivate, und verfahren zu ihrer herstellung
US4167565A (en)	1976-11-08	1979-09-11	Abbott Laboratories	Adenosine-5'-carboxamides and method of use
AU8379182A (en)	1981-06-04	1982-12-09	Procter & Gamble Company, The	Composition of salicylates and purine derivatives
JPS58167599A (ja)	1982-03-29	1983-10-03	Tanabe Seiyaku Co Ltd	アデノシン誘導体及びその製法
JPS58174322A (ja)	1982-04-07	1983-10-13	Tanabe Seiyaku Co Ltd	線溶促進剤
CA1239397A (en)	1983-08-01	1988-07-19	James A. Bristol	N.sup.6-substituted adenosines
DE3406533A1 (de)	1984-02-23	1985-08-29	Boehringer Mannheim Gmbh, 6800 Mannheim	Verwendung von adenosin-derivaten als antiallergica und arzneimittel, die diese enthalten
US4496643A (en)	1984-03-23	1985-01-29	Eastman Kodak Company	Two-component dry electrostatic developer composition containing onium charge control agent
AU582359B2 (en)	1984-04-18	1989-03-23	Nelson Research & Development Company	N-6 substituted adenosine derivatives as cardiac vasodilators
US5310731A (en)	1984-06-28	1994-05-10	Whitby Research, Inc.	N-6 substituted-5'-(N-substitutedcarboxamido)adenosines as cardiac vasodilators and antihypertensive agents
AU575438B2 (en)	1984-10-26	1988-07-28	Warner-Lambert Company	N6 - substituted deoxyribose analogues of adenosines
US4663313A (en)	1984-10-26	1987-05-05	Warner-Lambert Company	N6 -tricyclic adenosines for treating hypertension
US5258380A (en)	1985-06-24	1993-11-02	Janssen Pharmaceutica N.V.	(4-piperidinylmethyl and -hetero)purines
US4738954A (en)	1985-11-06	1988-04-19	Warner-Lambert Company	Novel N6 -substituted-5'-oxidized adenosine analogs
US4755594A (en)	1986-01-31	1988-07-05	Warner-Lambert Company	N6 -substituted adenosines
US5106837A (en)	1988-03-16	1992-04-21	The Scripps Research Institute	Adenosine derivatives with therapeutic activity
JPH0696534B2 (ja)	1986-04-25	1994-11-30	ヘキストジヤパン株式会社	抗痴呆剤
US4767747A (en)	1986-08-28	1988-08-30	Warner-Lambert Company	Method for treating congestive heart failure with N6 -acenaphthyl adenosine
AU8274187A (en)	1986-10-31	1988-05-25	Warner-Lambert Company	Heteroaromatic derivatives of adenosine
WO1988003147A1 (en)	1986-10-31	1988-05-05	Warner-Lambert Company	Selected n6-substituted adenosines having selective a2 binding activity
HU198950B (en)	1986-12-15	1989-12-28	Sandoz Ag	Process for producing new furanuronic acid derivatives and pharmaceutical compositions comprising such compounds
US4968697A (en)	1987-02-04	1990-11-06	Ciba-Geigy Corporation	2-substituted adenosine 5'-carboxamides as antihypertensive agents
PT86660B (pt)	1987-02-04	1992-02-28	Ciba Geigy Ag	Processo para a preparacao de derivados de adenosina-5'-carboxamida
US4962194A (en)	1987-04-02	1990-10-09	Warner-Lambert Company	Method of preparing 51,N6-disubstituted adenosines from inosines
US5219840A (en)	1987-04-06	1993-06-15	Sandoz Ltd.	Antihypertensive 9-(2,N6 -disubstituted adenyl) ribofuranuronic acid derivatives
LU87181A1 (fr)	1987-04-06	1988-11-17	Sandoz Sa	Nouveaux derives de l'acide furannuronique,leur preparation et leur utilisation comme medicaments
US5021574A (en)	1988-03-03	1991-06-04	Ortho Pharmaceutical Corporation	6-substituted purinyl piperazine derivatives
JPH0725785B2 (ja)	1989-01-11	1995-03-22	日本臓器製薬株式会社	アデノシン誘導体及び該化合物を有効成分として含有する医薬組成物
GB8920534D0 (en)	1989-09-11	1989-10-25	Wellcome Found	Antiviral compounds
US5506347A (en)	1993-02-03	1996-04-09	Gensia, Inc.	Lyxofuranosyl analogues of adenosine
IE903747A1 (en)	1989-10-19	1991-04-24	Searle & Co	Method of treating gastrointestinal motility disorders
US5055569A (en)	1989-10-19	1991-10-08	G. D. Searle & Co.	N-(6)-substituted adenosine compounds
MY104575A (en)	1989-12-22	1994-04-30	The Wellcome Foundation Ltd	Therapeutic nucleosides.
US5140015A (en)	1990-02-20	1992-08-18	Whitby Research, Inc.	2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents
US5280015A (en)	1990-09-05	1994-01-18	The United States Of America As Represented By The Department Of Health And Human Services	2-substituted adenosines and 2-substituted adenosine 5'-carboxamides
EP0550631B1 (en)	1990-09-25	1997-01-02	Rhone-Poulenc Rorer International (Holdings) Inc.	Compounds having antihypertensive and anti-ischemic properties
ZA923641B (en)	1991-05-21	1993-02-24	Iaf Biochem Int	Processes for the diastereoselective synthesis of nucleosides
FR2685918B1 (fr)	1992-01-08	1995-06-23	Union Pharma Scient Appl	Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant.
FR2687678B1 (fr)	1992-01-31	1995-03-31	Union Pharma Scient Appl	Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant.
IT1254915B (it)	1992-04-24	1995-10-11	Gloria Cristalli	Derivati di adenosina ad attivita' a2 agonista
US5424297A (en)	1992-04-27	1995-06-13	University Of Virginia Alumni Patents Foundation	Adenosine dextran conjugates
WO1994002497A1 (en)	1992-07-15	1994-02-03	The United States Of America, Represented By The Secretary, Department Of Health And Human Services	Sulfo-derivatives of adenosine
GB9301000D0 (en)	1993-01-20	1993-03-10	Glaxo Group Ltd	Chemical compounds
US5773423A (en)	1993-07-13	1998-06-30	The United States Of America As Represented By The Department Of Health And Human Services	A3 adenosine receptor agonists
US5446046A (en)	1993-10-28	1995-08-29	University Of Florida Research Foundation	A1 adenosine receptor agonists and antagonists as diuretics
WO1995018817A1 (fr)	1994-01-07	1995-07-13	Laboratoires Upsa	Nouveaux derives de l'adenosine, leurs procedes de preparation, compositions pharmaceutiques les contenant
GB9414208D0 (en)	1994-07-14	1994-08-31	Glaxo Group Ltd	Compounds
GB9414193D0 (en)	1994-07-14	1994-08-31	Glaxo Group Ltd	Compounds
WO1998001459A1 (en) *	1996-07-05	1998-01-15	Novo Nordisk A/S	Novel n-alkoxyadenine derivatives acting as cytokine inhibitors
UA51716C2 (uk)	1996-07-08	2002-12-16	Авентіс Фармасьютікалз Продактс Інк.	Сполуки, що мають гіпотензивну, кардіопротекторну, анти-ішемічну та антиліполітичну властивості, фармацевтична композиція та способи лікування
AU4377397A (en)	1996-10-14	1998-05-11	Novo Nordisk A/S	Novel therapeutically active adenosine derivatives
FR2757518B1 (fr)	1996-12-23	1999-06-11	Hoechst Marion Roussel Inc	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
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
PE20000270A1 (es) *	1998-02-14	2000-05-20	Glaxo Group Ltd	Derivados de 2-(purin-9-il)-tetrahidrofuran-3,4-diol
GB9813535D0 (en)	1998-06-23	1998-08-19	Glaxo Group Ltd	Chemical compounds
CN1313861A (zh)	1998-06-23	2001-09-19	葛兰素集团有限公司	2－(嘌呤－9－基)－四氢呋喃－3,4－二醇衍生物

1998
- 1998-01-31 YU YU44900A patent/YU44900A/sh unknown
1999
- 1999-01-28 AR ARP990100336A patent/AR014508A1/es not_active Application Discontinuation
- 1999-01-28 CO CO99004721A patent/CO4980872A1/es unknown
- 1999-01-28 PE PE1999000060A patent/PE20000280A1/es not_active Application Discontinuation
- 1999-01-29 ID IDW20001467A patent/ID26326A/id unknown
- 1999-01-29 EE EEP200000441A patent/EE200000441A/xx unknown
- 1999-01-29 HU HU0101305A patent/HUP0101305A3/hu unknown
- 1999-01-29 EP EP99907427A patent/EP1051425B1/en not_active Expired - Lifetime
- 1999-01-29 TW TW088101391A patent/TW434250B/zh active
- 1999-01-29 TR TR2000/02218T patent/TR200002218T2/xx unknown
- 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 KR KR1020007008297A patent/KR20010034473A/ko not_active Withdrawn
- 1999-01-29 EA EA200000723A patent/EA003194B1/ru not_active IP Right Cessation
- 1999-01-29 ES ES99907427T patent/ES2186330T3/es not_active Expired - Lifetime
- 1999-01-29 BR BR9907270-0A patent/BR9907270A/pt not_active IP Right Cessation
- 1999-01-29 AT AT99907427T patent/ATE226957T1/de not_active IP Right Cessation
- 1999-01-29 DE DE69903708T patent/DE69903708T2/de not_active Expired - Lifetime
- 1999-01-29 SK SK1119-2000A patent/SK11192000A3/sk unknown
- 1999-01-29 GE GEAP19995495A patent/GEP20022839B/en unknown
- 1999-01-29 AP APAP/P/2000/001875A patent/AP2000001875A0/en unknown
- 1999-01-29 PL PL99342670A patent/PL342670A1/xx unknown
- 1999-01-29 DK DK99907427T patent/DK1051425T3/da active
- 1999-01-29 NZ NZ505452A patent/NZ505452A/xx unknown
- 1999-01-29 PT PT99907427T patent/PT1051425E/pt unknown
- 1999-01-29 MA MA25443A patent/MA26601A1/fr unknown
- 1999-01-29 SV SV1999000009A patent/SV1999000009A/es unknown
- 1999-01-29 SI SI9930187T patent/SI1051425T1/xx unknown
- 1999-01-29 JP JP2000529344A patent/JP2002501928A/ja active Pending
- 1999-01-29 AU AU27197/99A patent/AU757183B2/en not_active Ceased
- 1999-01-29 CN CN99802548A patent/CN1289338A/zh active Pending
- 1999-01-29 HR HR20000511A patent/HRP20000511A2/hr not_active Application Discontinuation
- 1999-01-29 CA CA002318278A patent/CA2318278A1/en not_active Abandoned
- 1999-01-29 WO PCT/EP1999/000503 patent/WO1999038877A2/en not_active Ceased
2000
- 2000-06-27 IS IS5550A patent/IS5550A/is unknown
- 2000-07-21 OA OA1200000211A patent/OA11447A/en unknown
- 2000-07-28 NO NO20003867A patent/NO20003867L/no unknown
- 2000-08-29 BG BG104729A patent/BG63783B1/bg unknown

Also Published As

Publication number	Publication date
HUP0101305A2 (hu)	2002-04-29
CA2318278A1 (en)	1999-08-05
EA200000723A1 (ru)	2001-04-23
HUP0101305A3 (en)	2002-08-28
PL342670A1 (en)	2001-07-02
US6762170B1 (en)	2004-07-13
WO1999038877A3 (en)	1999-09-30
OA11447A (en)	2004-04-29
SK11192000A3 (sk)	2001-06-11
SV1999000009A (es)	2000-09-05
PE20000280A1 (es)	2000-03-28
KR20010034473A (ko)	2001-04-25
EE200000441A (et)	2001-12-17
BR9907270A (pt)	2000-10-24
WO1999038877A2 (en)	1999-08-05
CN1289338A (zh)	2001-03-28
CO4980872A1 (es)	2000-11-27
NO20003867D0 (no)	2000-07-28
EA003194B1 (ru)	2003-02-27
ES2186330T3 (es)	2003-05-01
HRP20000511A2 (en)	2000-12-31
EP1051425A2 (en)	2000-11-15
AU757183B2 (en)	2003-02-06
IL137042A0 (en)	2001-06-14
JP2002501928A (ja)	2002-01-22
YU44900A (sh)	2003-01-31
NZ505452A (en)	2003-01-31
MA26601A1 (fr)	2004-12-20
BG104729A (en)	2001-04-30
SI1051425T1 (en)	2003-04-30
TR200002218T2 (tr)	2000-12-21
AU2719799A (en)	1999-08-16
GEP20022839B (en)	2002-11-25
ATE226957T1 (de)	2002-11-15
AR014508A1 (es)	2001-02-28
TW434250B (en)	2001-05-16
EP1051425B1 (en)	2002-10-30
AP2000001875A0 (en)	2000-09-30
IS5550A (is)	2000-06-27
DE69903708T2 (de)	2003-07-03
HK1030611A1 (en)	2001-05-11
PT1051425E (pt)	2003-03-31
DE69903708D1 (de)	2002-12-05
DK1051425T3 (da)	2003-03-03
ID26326A (id)	2000-12-14
NO20003867L (no)	2000-07-28

Publication	Publication Date	Title
BG63783B1 (bg)	2002-12-29	2-(пурин-9-ил)-тетрахидрофуран-3,4-диолови производни
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
US6495528B1 (en)	2002-12-17	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
EP1090020B1 (en)	2003-11-05	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
KR20010071570A (ko)	2001-07-28	2-(푸린-9-일)-테트라히드로푸란-3,4-디올 유도체
MXPA99005888A (en)	2000-01-01	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA00012926A (en)	2002-05-09	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA00012895A (en)	2001-09-07	2-(purin-9-yl)-tetrahydrofuran-3,4-diol derivatives
MXPA00007793A (en)	2001-11-21	2-(purin-9-yl) -tetrahydrofuran-3, 4-diol derivatives
CZ20002787A3 (cs)	2001-04-11	2-(purin-9-yl)-tetrahydrofuran-3,4-diolové deriváty