SA96170272B1 - مثبطات لتجمع الصفائح الدموية - Google Patents

مثبطات لتجمع الصفائح الدموية Download PDF

Info

Publication number: SA96170272B1
Authority: SA; Saudi Arabia
Prior art keywords: beta; triazolo; pyrimidin; alpha; compound
Prior art date: 1995-07-11

Application number

SA96170272A

Other languages

Arabic (ar)

English (en)

Inventor

انتوني انجال

بول ويلز

دفيد كوكس

Original Assignee

استرازينيكا ايه بي

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.)

1995-07-11

Filing date

1996-08-28

Publication date

2006-06-04

1995-07-11 Priority claimed from GBGB9514074.5A external-priority patent/GB9514074D0/en

1995-10-05 Priority claimed from GBGB9520311.3A external-priority patent/GB9520311D0/en

1995-11-08 Priority claimed from GBGB9522837.5A external-priority patent/GB9522837D0/en

1996-08-28 Application filed by استرازينيكا ايه بي filed Critical استرازينيكا ايه بي

2006-06-04 Publication of SA96170272B1 publication Critical patent/SA96170272B1/ar

Links

230000002776 aggregation Effects 0.000 title claims description 9
238000004220 aggregation Methods 0.000 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 245
150000003839 salts Chemical class 0.000 claims abstract description 46
125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 41
125000000217 alkyl group Chemical group 0.000 claims abstract description 30
229910052736 halogen Inorganic materials 0.000 claims abstract description 23
150000002367 halogens Chemical class 0.000 claims abstract description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
208000010110 spontaneous platelet aggregation Diseases 0.000 claims abstract description 13
238000006467 substitution reaction Methods 0.000 claims abstract description 8
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
229940079593 drug Drugs 0.000 claims abstract description 3
239000003814 drug Substances 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 104
239000002253 acid Substances 0.000 claims description 77
229960005261 aspartic acid Drugs 0.000 claims description 34
159000000000 sodium salts Chemical class 0.000 claims description 27
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 21
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
208000035475 disorder Diseases 0.000 claims description 11
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 11
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
239000011734 sodium Substances 0.000 claims description 8
229910052708 sodium Inorganic materials 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 6
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
206010002388 Angina unstable Diseases 0.000 claims description 5
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 5
208000007814 Unstable Angina Diseases 0.000 claims description 5
238000007887 coronary angioplasty Methods 0.000 claims description 5
201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
210000004369 blood Anatomy 0.000 claims description 4
239000008280 blood Substances 0.000 claims description 4
208000010125 myocardial infarction Diseases 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 3
229940002612 prodrug Drugs 0.000 claims description 3
239000000651 prodrug Substances 0.000 claims description 3
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 claims description 2
230000015572 biosynthetic process Effects 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
238000003786 synthesis reaction Methods 0.000 claims description 2
208000013544 Platelet disease Diseases 0.000 claims 4
235000003704 aspartic acid Nutrition 0.000 claims 4
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 4
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 claims 2
OBMZMSLWNNWEJA-XNCRXQDQSA-N C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 Chemical compound C1=CC=2C(C[C@@H]3NC(=O)[C@@H](NC(=O)[C@H](NC(=O)N(CC#CCN(CCCC[C@H](NC(=O)[C@@H](CC4=CC=CC=C4)NC3=O)C(=O)N)CC=C)NC(=O)[C@@H](N)C)CC3=CNC4=C3C=CC=C4)C)=CNC=2C=C1 OBMZMSLWNNWEJA-XNCRXQDQSA-N 0.000 claims 1
101710176384 Peptide 1 Proteins 0.000 claims 1
125000004432 carbon atom Chemical group C* 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
UYDJAHJCGZTTHB-UHFFFAOYSA-N cyclopentane-1,1-diol Chemical compound OC1(O)CCCC1 UYDJAHJCGZTTHB-UHFFFAOYSA-N 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
229960004717 insulin aspart Drugs 0.000 claims 1
-1 5-tetrazolyl Chemical group 0.000 abstract description 31
239000000543 intermediate Substances 0.000 abstract description 4
239000008194 pharmaceutical composition Substances 0.000 abstract description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 82
239000000243 solution Substances 0.000 description 78
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 59
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 51
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 43
239000002904 solvent Substances 0.000 description 37
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
239000011541 reaction mixture Substances 0.000 description 32
238000006243 chemical reaction Methods 0.000 description 29
125000006239 protecting group Chemical group 0.000 description 29
239000000047 product Substances 0.000 description 28
239000000203 mixture Substances 0.000 description 26
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 18
150000002148 esters Chemical class 0.000 description 18
238000004587 chromatography analysis Methods 0.000 description 17
239000000463 material Substances 0.000 description 17
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 16
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 16
238000010992 reflux Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 15
229960000583 acetic acid Drugs 0.000 description 14
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 12
125000004494 ethyl ester group Chemical group 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
230000002378 acidificating effect Effects 0.000 description 10
239000003054 catalyst Substances 0.000 description 10
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 10
238000012163 sequencing technique Methods 0.000 description 10
238000003756 stirring Methods 0.000 description 10
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 9
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
125000000446 sulfanediyl group Chemical group *S* 0.000 description 9
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
239000003146 anticoagulant agent Substances 0.000 description 8
239000012298 atmosphere Substances 0.000 description 8
229960004132 diethyl ether Drugs 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
239000000725 suspension Substances 0.000 description 8
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
229910052500 inorganic mineral Inorganic materials 0.000 description 7
235000010755 mineral Nutrition 0.000 description 7
239000011707 mineral Substances 0.000 description 7
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
230000002265 prevention Effects 0.000 description 6
239000012312 sodium hydride Substances 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
229910052723 transition metal Inorganic materials 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000002252 acyl group Chemical group 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
229910052751 metal Inorganic materials 0.000 description 5
239000002184 metal Substances 0.000 description 5
230000003647 oxidation Effects 0.000 description 5
238000007254 oxidation reaction Methods 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
150000003624 transition metals Chemical class 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
239000005557 antagonist Substances 0.000 description 4
230000000702 anti-platelet effect Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
229910052763 palladium Inorganic materials 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
238000000926 separation method Methods 0.000 description 4
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
208000032843 Hemorrhage Diseases 0.000 description 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
229960001138 acetylsalicylic acid Drugs 0.000 description 3
UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
230000029936 alkylation Effects 0.000 description 3
238000005804 alkylation reaction Methods 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
230000000740 bleeding effect Effects 0.000 description 3
239000012267 brine Substances 0.000 description 3
239000011575 calcium Substances 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
239000003610 charcoal Substances 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
238000001035 drying Methods 0.000 description 3
238000007590 electrostatic spraying Methods 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
239000000284 extract Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical group [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000001802 infusion Methods 0.000 description 3
OWFXIOWLTKNBAP-UHFFFAOYSA-N isoamyl nitrite Chemical compound CC(C)CCON=O OWFXIOWLTKNBAP-UHFFFAOYSA-N 0.000 description 3
239000006166 lysate Substances 0.000 description 3
235000006408 oxalic acid Nutrition 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
210000004623 platelet-rich plasma Anatomy 0.000 description 3
230000008569 process Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
102000005962 receptors Human genes 0.000 description 3
108020003175 receptors Proteins 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007921 spray Substances 0.000 description 3
238000012360 testing method Methods 0.000 description 3
229940055764 triaz Drugs 0.000 description 3
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 2
HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 2
LXJSJIXZOAMHTG-UHFFFAOYSA-N 4-(1,3-dimethyl-2,6-dioxo-7h-purin-8-yl)benzenesulfonic acid Chemical compound N1C=2C(=O)N(C)C(=O)N(C)C=2N=C1C1=CC=C(S(O)(=O)=O)C=C1 LXJSJIXZOAMHTG-UHFFFAOYSA-N 0.000 description 2
IQGYCVKWCYGVBK-UHFFFAOYSA-N 5,6-diamino-1h-pyrimidine-2,4-dithione Chemical compound NC=1NC(=S)NC(=S)C=1N IQGYCVKWCYGVBK-UHFFFAOYSA-N 0.000 description 2
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
102100034534 Adenomatous polyposis coli protein 2 Human genes 0.000 description 2
206010003178 Arterial thrombosis Diseases 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
125000000824 D-ribofuranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@]1([H])O[H] 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
102000009123 Fibrin Human genes 0.000 description 2
108010073385 Fibrin Proteins 0.000 description 2
BWGVNKXGVNDBDI-UHFFFAOYSA-N Fibrin monomer Chemical compound CNC(=O)CNC(=O)CN BWGVNKXGVNDBDI-UHFFFAOYSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 2
101000924579 Homo sapiens Adenomatous polyposis coli protein 2 Proteins 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
102100026933 Myelin-associated neurite-outgrowth inhibitor Human genes 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
238000003527 Peterson olefination reaction Methods 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
238000006859 Swern oxidation reaction Methods 0.000 description 2
ZWZUFQPXYVYAFO-UHFFFAOYSA-N Tert-butyl (triphenylphosphoranylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC(C)(C)C)C1=CC=CC=C1 ZWZUFQPXYVYAFO-UHFFFAOYSA-N 0.000 description 2
108090000190 Thrombin Proteins 0.000 description 2
208000007536 Thrombosis Diseases 0.000 description 2
206010047249 Venous thrombosis Diseases 0.000 description 2
238000002835 absorbance Methods 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
239000002671 adjuvant Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
150000004703 alkoxides Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
229940127090 anticoagulant agent Drugs 0.000 description 2
229940127219 anticoagulant drug Drugs 0.000 description 2
229940127218 antiplatelet drug Drugs 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
150000001540 azides Chemical class 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
125000002837 carbocyclic group Chemical group 0.000 description 2
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
150000003857 carboxamides Chemical class 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000004087 circulation Effects 0.000 description 2
239000000701 coagulant Substances 0.000 description 2
239000007822 coupling agent Substances 0.000 description 2
230000009089 cytolysis Effects 0.000 description 2
230000006378 damage Effects 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 2
125000003720 ethoxymethylidene group Chemical group [H]C(=*)OC([H])([H])C([H])([H])[H] 0.000 description 2
229950003499 fibrin Drugs 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
229960002897 heparin Drugs 0.000 description 2
229920000669 heparin Polymers 0.000 description 2
150000004679 hydroxides Chemical class 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
230000003993 interaction Effects 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000003456 ion exchange resin Substances 0.000 description 2
229920003303 ion-exchange polymer Polymers 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000008101 lactose Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
239000003921 oil Substances 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
230000010118 platelet activation Effects 0.000 description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000011946 reduction process Methods 0.000 description 2
230000004044 response Effects 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
238000001356 surgical procedure Methods 0.000 description 2
229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 2
229960004072 thrombin Drugs 0.000 description 2
230000009424 thromboembolic effect Effects 0.000 description 2
230000001732 thrombotic effect Effects 0.000 description 2
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-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
229910052727 yttrium Inorganic materials 0.000 description 2
AGOSFZUJVNKTHO-UHFFFAOYSA-N 1,1,1-trifluoro-3-$l^{1}-sulfanylpropane Chemical group FC(F)(F)CC[S] AGOSFZUJVNKTHO-UHFFFAOYSA-N 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
UGRVYFQFDZRNMQ-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonohydrazide Chemical compound CC(C)C1=CC(C(C)C)=C(S(=O)(=O)NN)C(C(C)C)=C1 UGRVYFQFDZRNMQ-UHFFFAOYSA-N 0.000 description 1
SODVEDDQLXKHHZ-UHFFFAOYSA-N 2,6-bis(propylsulfanyl)pyrimidine-4,5-diamine Chemical compound CCCSC1=NC(N)=C(N)C(SCCC)=N1 SODVEDDQLXKHHZ-UHFFFAOYSA-N 0.000 description 1
ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 2-(6-amino-1h-indol-3-yl)acetonitrile Chemical compound NC1=CC=C2C(CC#N)=CNC2=C1 ZSDQQJHSRVEGTJ-UHFFFAOYSA-N 0.000 description 1
MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
RCGLWQFNUOBKRT-UHFFFAOYSA-N 2-pentylsulfanyl-1h-pyrimidine-4,6-dione Chemical compound CCCCCSC1=NC(=O)CC(=O)N1 RCGLWQFNUOBKRT-UHFFFAOYSA-N 0.000 description 1
JHUUPUMBZGWODW-UHFFFAOYSA-N 3,6-dihydro-1,2-dioxine Chemical compound C1OOCC=C1 JHUUPUMBZGWODW-UHFFFAOYSA-N 0.000 description 1
GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
DDEDQHVHVPJFAC-UHFFFAOYSA-N 4,6-dichloro-5-nitro-2-propylsulfanylpyrimidine Chemical compound CCCSC1=NC(Cl)=C([N+]([O-])=O)C(Cl)=N1 DDEDQHVHVPJFAC-UHFFFAOYSA-N 0.000 description 1
XTCGLTVNRHPGDH-UHFFFAOYSA-N 5,6-dihydroxy-3-azabicyclo[2.2.1]heptan-2-one Chemical compound C1C2C(O)C(O)C1C(=O)N2 XTCGLTVNRHPGDH-UHFFFAOYSA-N 0.000 description 1
IJIBRSFAXRFPPN-UHFFFAOYSA-N 5-bromo-2-methoxybenzaldehyde Chemical compound COC1=CC=C(Br)C=C1C=O IJIBRSFAXRFPPN-UHFFFAOYSA-N 0.000 description 1
STUQITWXBMZUGY-UHFFFAOYSA-N 6-hydroxy-2-sulfanylidene-1h-pyrimidin-4-one Chemical compound OC1=CC(O)=NC(S)=N1 STUQITWXBMZUGY-UHFFFAOYSA-N 0.000 description 1
KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
208000003343 Antiphospholipid Syndrome Diseases 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
208000037157 Azotemia Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241001124532 Bubalus depressicornis Species 0.000 description 1
101100309447 Caenorhabditis elegans sad-1 gene Proteins 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
PTHCMJGKKRQCBF-UHFFFAOYSA-N Cellulose, microcrystalline Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC)C(CO)O1 PTHCMJGKKRQCBF-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-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
CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
206010051055 Deep vein thrombosis Diseases 0.000 description 1
208000000059 Dyspnea Diseases 0.000 description 1
206010013975 Dyspnoeas Diseases 0.000 description 1
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
206010018364 Glomerulonephritis 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
102000003886 Glycoproteins Human genes 0.000 description 1
108090000288 Glycoproteins Proteins 0.000 description 1
102000007625 Hirudins Human genes 0.000 description 1
108010007267 Hirudins Proteins 0.000 description 1
238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 1
XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
206010061216 Infarction Diseases 0.000 description 1
206010061218 Inflammation Diseases 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-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
206010073734 Microembolism Diseases 0.000 description 1
208000019695 Migraine disease Diseases 0.000 description 1
101100185402 Mus musculus Mug1 gene Proteins 0.000 description 1
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
208000018262 Peripheral vascular disease Diseases 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
102000001708 Protein Isoforms Human genes 0.000 description 1
108010029485 Protein Isoforms Proteins 0.000 description 1
102000000033 Purinergic Receptors Human genes 0.000 description 1
108010080192 Purinergic Receptors Proteins 0.000 description 1
206010037549 Purpura Diseases 0.000 description 1
241001672981 Purpura Species 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
206010040047 Sepsis Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229940122388 Thrombin inhibitor Drugs 0.000 description 1
206010047115 Vasculitis Diseases 0.000 description 1
241000700605 Viruses Species 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
101150095244 ac gene Proteins 0.000 description 1
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 description 1
ZLNLCABJIUILTH-UHFFFAOYSA-N acetyl chloride;n,n-diethylethanamine Chemical compound CC(Cl)=O.CCN(CC)CC ZLNLCABJIUILTH-UHFFFAOYSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000011360 adjunctive therapy Methods 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 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
229940043376 ammonium acetate Drugs 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000002399 angioplasty Methods 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000004019 antithrombin Substances 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
206010003230 arteritis Diseases 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000003143 atherosclerotic effect Effects 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000008901 benefit Effects 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
MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
238000012925 biological evaluation Methods 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
210000000481 breast Anatomy 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000007853 buffer solution Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
239000001913 cellulose Substances 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
230000008859 change Effects 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
239000013256 coordination polymer Substances 0.000 description 1
238000004132 cross linking Methods 0.000 description 1
CSGIROCFQXHTKS-UHFFFAOYSA-N ctk8h6437 Chemical compound O=C1NC2CC1C1C2OC(C)(C)O1 CSGIROCFQXHTKS-UHFFFAOYSA-N 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
150000001923 cyclic compounds Chemical class 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000007257 deesterification reaction Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 1
238000000502 dialysis Methods 0.000 description 1
RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
229910000071 diazene Inorganic materials 0.000 description 1
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 description 1
ZFXYCNXMFIGKTJ-UHFFFAOYSA-N dichloromethane urea Chemical compound ClCCl.NC(=O)N ZFXYCNXMFIGKTJ-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
GVLZIMQSYQDAHB-QRPNPIFTSA-N ditert-butyl (2s)-2-aminobutanedioate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)C[C@H](N)C(=O)OC(C)(C)C GVLZIMQSYQDAHB-QRPNPIFTSA-N 0.000 description 1
208000002296 eclampsia Diseases 0.000 description 1
238000007787 electrohydrodynamic spraying Methods 0.000 description 1
238000001962 electrophoresis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 1
229960001123 epoprostenol Drugs 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000013265 extended release Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229960002442 glucosamine Drugs 0.000 description 1
150000002337 glycosamines Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
230000002949 hemolytic effect Effects 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
229940006607 hirudin Drugs 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 1
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
230000007574 infarction Effects 0.000 description 1
230000004054 inflammatory process Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000003951 lactams Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 description 1
235000018977 lysine Nutrition 0.000 description 1
150000002669 lysines Chemical class 0.000 description 1
230000002934 lysing effect Effects 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
USSBDBZGEDUBHE-UHFFFAOYSA-L magnesium;2-oxidooxycarbonylbenzoate Chemical compound [Mg+2].[O-]OC(=O)C1=CC=CC=C1C([O-])=O USSBDBZGEDUBHE-UHFFFAOYSA-L 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
102000006240 membrane receptors Human genes 0.000 description 1
108020004084 membrane receptors Proteins 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
150000004681 metal hydrides Chemical class 0.000 description 1
229910000000 metal hydroxide Inorganic materials 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
ZZZBVPGKGDEHGL-UHFFFAOYSA-N morpholine piperidine Chemical compound C1CCNCC1.C1COCCN1.C1COCCN1 ZZZBVPGKGDEHGL-UHFFFAOYSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
HNBDRPTVWVGKBR-UHFFFAOYSA-N n-pentanoic acid methyl ester Natural products CCCCC(=O)OC HNBDRPTVWVGKBR-UHFFFAOYSA-N 0.000 description 1
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000002826 nitrites Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
231100000956 nontoxicity Toxicity 0.000 description 1
239000012038 nucleophile Substances 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
125000003835 nucleoside group Chemical group 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
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000006772 olefination reaction Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
230000000399 orthopedic effect Effects 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
QJPQVXSHYBGQGM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
230000037361 pathway Effects 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
239000000106 platelet aggregation inhibitor Substances 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
201000011461 pre-eclampsia Diseases 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
239000008213 purified water Substances 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
235000008001 rakum palm Nutrition 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000002271 resection Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical group CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000035939 shock Effects 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
229940001584 sodium metabisulfite Drugs 0.000 description 1
235000010262 sodium metabisulphite Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
125000004299 tetrazol-5-yl group Chemical group [H]N1N=NC(*)=N1 0.000 description 1
239000003868 thrombin inhibitor Substances 0.000 description 1
239000003634 thrombocyte concentrate Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000003852 triazoles Chemical group 0.000 description 1
SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
229940038773 trisodium citrate Drugs 0.000 description 1
241001529453 unidentified herpesvirus Species 0.000 description 1
208000009852 uremia Diseases 0.000 description 1
238000007631 vascular surgery Methods 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
208000020854 vein disease Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Biotechnology (AREA)
Heart & Thoracic Surgery (AREA)
Genetics & Genomics (AREA)
Cardiology (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SA96170272A 1995-07-11 1996-08-28 مثبطات لتجمع الصفائح الدموية SA96170272B1 (ar)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GBGB9514074.5A GB9514074D0 (en)	1995-07-11	1995-07-11	Compounds
GBGB9520311.3A GB9520311D0 (en)	1995-10-05	1995-10-05	Compounds
GBGB9522837.5A GB9522837D0 (en)	1995-11-08	1995-11-08	Compounds

Publications (1)

Publication Number	Publication Date
SA96170272B1 true SA96170272B1 (ar)	2006-06-04

Family

ID=27267806

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SA96170272A SA96170272B1 (ar)	1995-07-11	1996-08-28	مثبطات لتجمع الصفائح الدموية

Country Status (25)

Country	Link
US (1)	US5747496A (2)
EP (1)	EP0840740B1 (2)
JP (1)	JP4084415B2 (2)
KR (1)	KR100444123B1 (2)
CN (1)	CN1069321C (2)
AR (1)	AR003453A1 (2)
AT (1)	ATE217010T1 (2)
AU (1)	AU699034B2 (2)
BR (1)	BR9609467A (2)
CA (1)	CA2226758A1 (2)
CZ (1)	CZ297200B6 (2)
DE (1)	DE69621021T2 (2)
EE (1)	EE03616B1 (2)
HU (1)	HU221880B1 (2)
IL (1)	IL122814A (2)
IS (1)	IS1790B (2)
MY (1)	MY116542A (2)
NO (1)	NO310624B1 (2)
NZ (1)	NZ312258A (2)
PL (1)	PL182680B1 (2)
SA (1)	SA96170272B1 (2)
SK (1)	SK283206B6 (2)
TR (1)	TR199800019T1 (2)
TW (1)	TW427996B (2)
WO (1)	WO1997003084A1 (2)

Families Citing this family (47)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6297232B1 (en) *	1996-12-20	2001-10-02	Astrazeneca Ab	Triazolo[4,5-D]pyrimidinyl derivatives and their use as medicaments
SE9702773D0 (sv) *	1997-07-22	1997-07-22	Astra Pharma Prod	Novel compounds
SE9702774D0 (sv) *	1997-07-22	1997-07-22	Astra Pharma Prod	Novel compounds
AR017014A1 (es) *	1997-07-22	2001-08-22	Astrazeneca Ab	Compuestos de triazolo [4,5-d]pirimidina, composiciones farmaceuticas, uso de los mismos para preparar medicamentos y procesos para la preparacionde dichos compuestos
SE9702772D0 (sv) *	1997-07-22	1997-07-22	Astra Pharma Prod	Novel compounds
MXPA00007634A (es) *	1998-02-17	2003-09-10	Astrazeneca Uk Ltd	Nuevos compuestos de triazol (4,5-d) pirimidina.
SE9802574D0 (sv) *	1998-07-17	1998-07-17	Astra Pharma Prod	Novel compounds
TWI229674B (en)	1998-12-04	2005-03-21	Astra Pharma Prod	Novel triazolo[4,5-d]pyrimidine compounds, pharmaceutical composition containing the same, their process for preparation and uses
SE9904128D0 (sv) *	1999-11-15	1999-11-15	Astra Pharma Prod	Novel compounds
SE9904129D0 (sv) *	1999-11-15	1999-11-15	Astra Pharma Prod	Novel compounds
SE9904377D0 (sv) *	1999-12-01	1999-12-01	Astra Pharma Prod	Pharmaceutical combinations
GB0013407D0 (en) *	2000-06-02	2000-07-26	Astrazeneca Ab	Forms of a chemical compound
GB0013488D0 (en)	2000-06-02	2000-07-26	Astrazeneca Ab	Chemical compound
AR039558A1 (es) *	2000-08-21	2005-02-23	Inspire Pharmaceuticals Inc	Composiciones y metodo para el tratamiento de glaucoma o hipertension ocular
US7132408B2 (en)	2000-08-21	2006-11-07	Inspire Pharmaceuticals, Inc.	Composition and method for inhibiting platelet aggregation
US6897201B2 (en) *	2000-08-21	2005-05-24	Inspire Pharmaceuticals, Inc.	Compositions and methods for the treatment of glaucoma or ocular hypertension
US7115585B2 (en)	2000-08-21	2006-10-03	Inspire Pharmaceuticals, Inc.	Compositions for treating epithelial and retinal tissue diseases
US7452870B2 (en)	2000-08-21	2008-11-18	Inspire Pharmaceuticals, Inc.	Drug-eluting stents coated with P2Y12 receptor antagonist compound
US7018985B1 (en)	2000-08-21	2006-03-28	Inspire Pharmaceuticals, Inc.	Composition and method for inhibiting platelet aggregation
GB0100624D0 (en) *	2001-01-10	2001-02-21	Vernalis Res Ltd	Chemical compounds VII
SE0101932D0 (sv) *	2001-05-31	2001-05-31	Astrazeneca Ab	Pharmaceutical combinations
US20020169730A1 (en) *	2001-08-29	2002-11-14	Emmanuel Lazaridis	Methods for classifying objects and identifying latent classes
US7435724B2 (en)	2002-02-27	2008-10-14	Inspire Pharmaceutical, Inc.	Degradation-resistant mononucleoside phosphate compounds
EP1618109A2 (en) *	2003-04-09	2006-01-25	Biogen Idec MA Inc.	Triazolo[1,5-c]pyrimidines and pyrazolo[1,5-c]pyrimidines useful as a2a adenosine receptor antagonists
WO2004092170A2 (en) *	2003-04-09	2004-10-28	Biogen Idec Ma Inc.	Triazolotriazines and pyrazolotriazines useful as a2a adenosine receptor antagon ists
EP1633756B1 (en) *	2003-04-09	2008-12-24	Biogen Idec MA Inc.	A2a adenosine receptor antagonists
EP1615931A1 (en) *	2003-04-09	2006-01-18	Biogen Idec MA Inc.	Triazolopyrazines and methods of making and using the same
WO2004092171A2 (en) *	2003-04-09	2004-10-28	Biogen Idec Ma Inc.	Triazolo[1,5-a]pyrimidines and pyrazolo[1,5-a]pyrimidines useful as a2a adenosin e receptor antagonists
JP2007509180A (ja) *	2003-10-21	2007-04-12	インスパイアーファーマシューティカルズ，インコーポレイティド	疼痛を治療するための、非ヌクレオチド組成物および方法
DE602004027409D1 (de) *	2003-10-21	2010-07-08	Inspire Pharmaceuticals Inc	Tetrahydrofuroä3,4-düdioxolverbindungen und zusammensetzungen und verfahren zur inhibierung der trombozytenaggregation
US7335648B2 (en) *	2003-10-21	2008-02-26	Inspire Pharmaceuticals, Inc.	Non-nucleotide composition and method for inhibiting platelet aggregation
US7504497B2 (en) *	2003-10-21	2009-03-17	Inspire Pharmaceuticals, Inc.	Orally bioavailable compounds and methods for inhibiting platelet aggregation
US7749981B2 (en) *	2003-10-21	2010-07-06	Inspire Pharmaceuticals, Inc.	Drug-eluting stents coated with non-nucleotide P2Y12 receptor antagonist compound
US7932376B2 (en) *	2005-05-05	2011-04-26	Inspire Pharmaceuticals, Inc.	Pyrimidine-based non-nucleotide composition and method for inhibiting platelet aggregation
JP2010508350A (ja) *	2006-10-31	2010-03-18	ヤンセンファーマシューティカエヌ．ベー．	Ａｄｐｐ２ｙ１２レセプターアンタゴニストとしてのトリアゾロピリミジン誘導体
UA100864C2 (uk) *	2007-12-03	2013-02-11	Астразенека Аб	Спосіб лікування або запобігання аневризмі черевної аорти
GB0906579D0 (en)	2009-04-16	2009-05-20	Vernalis R&D Ltd	Pharmaceuticals, compositions and methods of making and using the same
US8470834B2 (en) *	2008-08-20	2013-06-25	Merck Sharp & Dohme Corp.	AZO-substituted pyridine and pyrimidine derivatives and their use in treating viral infections
WO2011101740A1 (en)	2010-02-16	2011-08-25	Actavis Group Ptc Ehf	Improved processes for preparing ticagrelor intermediate, 4,6-dichloro-5-nitro-2-(propylthio)pyrimidine
JP2015500219A (ja)	2011-11-30	2015-01-05	アクタビス・グループ・ピーティーシー・イーエイチエフ	新規な結晶形を有するチカグレロル及びその調製方法
WO2014083139A1 (en)	2012-11-29	2014-06-05	Actavis Group Ptc Ehf	Novel amorphous form of ticagrelor
WO2014206187A1 (zh)	2013-06-24	2014-12-31	苏州明锐医药科技有限公司	替卡格雷及其中间体的制备方法
WO2014206188A1 (zh) *	2013-06-27	2014-12-31	苏州明锐医药科技有限公司	替格瑞洛的制备方法
CN105061431B (zh) *	2015-07-28	2017-03-29	山东百诺医药股份有限公司	6‑n‑（2‑（甲硫基）乙基）‑2‑（（3,3,3‑三氟丙基）硫代）‑9h‑嘌呤及其制备方法和应用
CN112876485A (zh) *	2021-01-25	2021-06-01	郭丽伟	一种用于治疗子宫平滑肌高频率强直性收缩相关疾病的化合物
CN112915063B (zh) *	2021-01-25	2022-12-20	刘红枚	一种用于治疗子宫平滑肌高频率强直性收缩相关疾病的化合物
RU2770405C1 (ru) *	2021-07-05	2022-04-15	федеральное государственное бюджетное образовательное учреждение высшего образования "Башкирский государственный медицинский университет" Министерства здравоохранения Российской Федерации	Производные триазола, проявляющие антиагрегационную активность

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4742064A (en) *	1985-09-10	1988-05-03	Regents Of The University Of Minnesota	Antiviral carbocyclic analogs of xylofuranosylpurines
GB8826205D0 (en) *	1988-11-09	1988-12-14	Wellcome Found	Heterocyclic compounds
JP2619710B2 (ja) *	1989-02-27	1997-06-11	日本製紙株式会社	２′，３′−ジデオキシプリンヌクレオシド類の製造方法
WO1994018215A1 (en) *	1993-02-03	1994-08-18	Gensia, Inc.	Adenosine kinase inhibitors comprising lyxofuranosyl derivatives
IL108523A0 (en) *	1993-02-03	1994-05-30	Gensia Inc	Pharmaceutical compositions containing adenosine kinase inhibitors for preventing or treating conditions involving inflammatory responses and pain

1996
- 1996-07-04 WO PCT/SE1996/000911 patent/WO1997003084A1/en not_active Ceased
- 1996-07-04 CA CA002226758A patent/CA2226758A1/en not_active Abandoned
- 1996-07-04 AT AT96923160T patent/ATE217010T1/de not_active IP Right Cessation
- 1996-07-04 TW TW085108062A patent/TW427996B/zh not_active IP Right Cessation
- 1996-07-04 TR TR1998/00019T patent/TR199800019T1/xx unknown
- 1996-07-04 DE DE69621021T patent/DE69621021T2/de not_active Expired - Fee Related
- 1996-07-04 JP JP50574897A patent/JP4084415B2/ja not_active Expired - Fee Related
- 1996-07-04 CZ CZ0002598A patent/CZ297200B6/cs not_active IP Right Cessation
- 1996-07-04 NZ NZ312258A patent/NZ312258A/xx unknown
- 1996-07-04 IL IL12281496A patent/IL122814A/en not_active IP Right Cessation
- 1996-07-04 EP EP96923160A patent/EP0840740B1/en not_active Expired - Lifetime
- 1996-07-04 KR KR10-1998-0700187A patent/KR100444123B1/ko not_active Expired - Fee Related
- 1996-07-04 SK SK23-98A patent/SK283206B6/sk unknown
- 1996-07-04 PL PL96324396A patent/PL182680B1/pl not_active IP Right Cessation
- 1996-07-04 HU HU9802448A patent/HU221880B1/hu active IP Right Grant
- 1996-07-04 US US08/737,005 patent/US5747496A/en not_active Expired - Fee Related
- 1996-07-04 CN CN96196720A patent/CN1069321C/zh not_active Expired - Fee Related
- 1996-07-04 BR BR9609467A patent/BR9609467A/pt active Search and Examination
- 1996-07-04 EE EE9800026A patent/EE03616B1/xx not_active IP Right Cessation
- 1996-07-04 AU AU63751/96A patent/AU699034B2/en not_active Ceased
- 1996-07-11 MY MYPI96002866A patent/MY116542A/en unknown
- 1996-07-11 AR ARP960103538A patent/AR003453A1/es active IP Right Grant
- 1996-08-28 SA SA96170272A patent/SA96170272B1/ar unknown
1998
- 1998-01-08 NO NO19980080A patent/NO310624B1/no unknown
- 1998-01-08 IS IS4647A patent/IS1790B/is unknown

Also Published As

Publication number	Publication date
HUP9802448A2 (hu)	1999-05-28
JPH11508914A (ja)	1999-08-03
AU6375196A (en)	1997-02-10
CN1069321C (zh)	2001-08-08
AR003453A1 (es)	1998-08-05
IL122814A (en)	2001-04-30
NZ312258A (en)	1999-08-30
SK2398A3 (en)	1999-01-11
HUP9802448A3 (en)	2000-03-28
SK283206B6 (sk)	2003-03-04
CZ297200B6 (cs)	2006-09-13
EE9800026A (et)	1998-08-17
JP4084415B2 (ja)	2008-04-30
MY116542A (en)	2004-02-28
EP0840740A1 (en)	1998-05-13
KR100444123B1 (ko)	2004-10-14
CN1195353A (zh)	1998-10-07
AU699034B2 (en)	1998-11-19
PL182680B1 (pl)	2002-02-28
CA2226758A1 (en)	1997-01-30
DE69621021T2 (de)	2002-10-31
CZ2598A3 (cs)	1998-08-12
ATE217010T1 (de)	2002-05-15
HU221880B1 (hu)	2003-02-28
IS4647A (is)	1998-01-08
NO310624B1 (no)	2001-07-30
EP0840740B1 (en)	2002-05-02
NO980080L (no)	1998-03-06
KR19990028885A (ko)	1999-04-15
BR9609467A (pt)	1999-03-02
EE03616B1 (et)	2002-02-15
IS1790B (is)	2001-11-28
TW427996B (en)	2001-04-01
NO980080D0 (no)	1998-01-08
MX9800308A (es)	1998-09-30
US5747496A (en)	1998-05-05
WO1997003084A1 (en)	1997-01-30
IL122814A0 (en)	1998-08-16
TR199800019T1 (xx)	1998-05-21
PL324396A1 (en)	1998-05-25
DE69621021D1 (de)	2002-06-06

Publication	Publication Date	Title
JP4084415B2 (ja)	2008-04-30	新しい血小板凝集抑制剤
US4381344A (en)	1983-04-26	Process for producing deoxyribosides using bacterial phosphorylase
DK168323B1 (da)	1994-03-14	Anvendelse af visse pyrimidinnucleosider til fremstilling af et lægemiddel mod VZV-infektioner; hidtil ukendte pyrimidinnucleosider, sådanne forbindelser til anvendelse i human terapi samt fremgangsmåde til fremstilling af forbindelserne
US5206244A (en)	1993-04-27	Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines
JPS60231661A (ja)	1985-11-18	抗ビールス性化合物
US4851519A (en)	1989-07-25	Pyrimidine derivatives
US6069132A (en)	2000-05-30	Phosphazole compounds
KR20030061792A (ko)	2003-07-22	뉴클레오시드 유도체
AU3155199A (en)	1999-10-18	Cyclin dependent kinase inhibitors
US5414000A (en)	1995-05-09	Antiviral pyrinyl substituted tetrahydropyrans
US4396623A (en)	1983-08-02	Carbocyclic analogs of uracil nucleosides as antiviral agents
Hsu et al.	1992	Synthesis of anti-restricted pyrimidine acyclic nucleosides
Knutsen et al.	1985	Synthesis of imidazo-fused bridgehead-nitrogen 2′-deoxyribo-c-nucleosides: Coupling-elimination reactions of 2, 5-anhydro-3, 4, 6-tri-o-benzoyl-d-allonic acid
US4060616A (en)	1977-11-29	Purine derivatives with repeating unit
US4481197A (en)	1984-11-06	Anti-inflammatory deoxyribosides
CA1168608A (en)	1984-06-05	Pharmaceutical compounds
US5340816A (en)	1994-08-23	Hydroxymethyl(methylenecyclopentyl) purines and pyrimidines
Silamkoti et al.	2005	Synthesis and biological activity of 2-fluoro adenine and 6-methyl purine nucleoside analogs as prodrugs for suicide gene therapy of cancer
Anderson et al.	1986	Synthesis of certain 3‐alkoxy‐1‐β‐D‐ribofuranosylpyrazolo [3, 4‐d] pyrimidines structurally related to adenosine, inosine and guanosine
RU2174518C2 (ru)	2001-10-10	Производные 3-н-1,2,3-триазоло-[4,5-d]пиримидина, фармацевтическая композиция и способ их получения
AU673259B2 (en)	1996-10-31	3-hydroxy-4-hydroxymethyl-2-methylenecyclopentyl purines and pyrimidines
US5231174A (en)	1993-07-27	2'isodideoxy-β-D-nucleosides as stable antiviral agents
Berry et al.	1994	Synthesis and Biological Activity of 4-Amino-1-(β-D-ribofuranosyl) imidazo [4, 5-d] pyridazin-7-one
Wang et al.	1994	Acyclic nucleosides: synthesis of 1-[(1-hydroxy-2-propoxy) methyl] thymine, 6-azathymine, uracil, and 6-azauracil as potential antiviral agents
Chupakhin et al.	0	Full Text HTML