CA2595882A1 - Composes de thieno [2,3-d] pyrimidine utilises comme inhibiteurs d'agregation de plaquettes induits par adp - Google Patents

Info

Publication number

CA2595882A1

CA2595882A1 CA002595882A CA2595882A CA2595882A1 CA 2595882 A1 CA2595882 A1 CA 2595882A1 CA 002595882 A CA002595882 A CA 002595882A CA 2595882 A CA2595882 A CA 2595882A CA 2595882 A1 CA2595882 A1 CA 2595882A1

Authority

CA

Canada

Prior art keywords

alkyl

group

aryl

heterocyclyl

cycloalkyl

Prior art date

2005-01-26

Legal status (The legal status 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 status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• CIPO
• Discuss

• 230000001404 mediated effect Effects 0.000 title description 7
• 239000003112 inhibitor Substances 0.000 title description 6
• DDWBRNXDKNIQDY-UHFFFAOYSA-N thieno[2,3-d]pyrimidine Chemical class N1=CN=C2SC=CC2=C1 DDWBRNXDKNIQDY-UHFFFAOYSA-N 0.000 title description 6
• 230000002776 aggregation Effects 0.000 title description 3
• 238000004220 aggregation Methods 0.000 title description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 356
• 150000003839 salts Chemical class 0.000 claims abstract description 37
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 16
• -1 -SH Chemical group 0.000 claims description 856
• 125000000217 alkyl group Chemical group 0.000 claims description 243
• 239000000203 mixture Substances 0.000 claims description 243
• 125000001424 substituent group Chemical group 0.000 claims description 235
• 125000003118 aryl group Chemical group 0.000 claims description 168
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 159
• 239000001257 hydrogen Substances 0.000 claims description 124
• 229910052739 hydrogen Inorganic materials 0.000 claims description 124
• 125000003342 alkenyl group Chemical group 0.000 claims description 115
• 125000000623 heterocyclic group Chemical group 0.000 claims description 111
• 125000000304 alkynyl group Chemical group 0.000 claims description 109
• 229910052736 halogen Inorganic materials 0.000 claims description 99
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 97
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 89
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 84
• 125000005843 halogen group Chemical group 0.000 claims description 73
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 66
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 62
• 125000001188 haloalkyl group Chemical group 0.000 claims description 57
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
• 150000002367 halogens Chemical group 0.000 claims description 40
• 125000003545 alkoxy group Chemical group 0.000 claims description 36
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 33
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 29
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
• 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 27
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 22
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
• 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
• 125000001246 bromo group Chemical group Br* 0.000 claims description 18
• 239000003814 drug Substances 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 16
• 208000007536 Thrombosis Diseases 0.000 claims description 15
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 125000003282 alkyl amino group Chemical group 0.000 claims description 13
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 230000001419 dependent effect Effects 0.000 claims description 11
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 11
• 125000004043 oxo group Chemical group O=* 0.000 claims description 11
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 10
• 125000000278 alkyl amino alkyl group Chemical group 0.000 claims description 10
• 125000005418 aryl aryl group Chemical group 0.000 claims description 10
• 125000004350 aryl cycloalkyl group Chemical group 0.000 claims description 10
• 125000005325 aryloxy aryl group Chemical group 0.000 claims description 10
• 125000004367 cycloalkylaryl group Chemical group 0.000 claims description 10
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 10
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 10
• 208000010125 myocardial infarction Diseases 0.000 claims description 10
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
• 125000005097 aminocarbonylalkyl group Chemical group 0.000 claims description 9
• 125000004181 carboxyalkyl group Chemical group 0.000 claims description 9
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 8
• 230000001732 thrombotic effect Effects 0.000 claims description 8
• 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 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 238000001356 surgical procedure Methods 0.000 claims description 7
• 125000006223 tetrahydrofuranylmethyl group Chemical group 0.000 claims description 7
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 6
• 208000004476 Acute Coronary Syndrome Diseases 0.000 claims description 6
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims description 6
• 206010038563 Reocclusion Diseases 0.000 claims description 6
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
• 125000005188 oxoalkyl group Chemical group 0.000 claims description 6
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• 206010003658 Atrial Fibrillation Diseases 0.000 claims description 5
• 208000032382 Ischaemic stroke Diseases 0.000 claims description 5
• 206010000891 acute myocardial infarction Diseases 0.000 claims description 5
• 125000004689 alkyl amino carbonyl alkyl group Chemical group 0.000 claims description 5
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 125000001041 indolyl group Chemical group 0.000 claims description 5
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 5
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 238000001631 haemodialysis Methods 0.000 claims description 4
• 210000003709 heart valve Anatomy 0.000 claims description 4
• 230000000322 hemodialysis Effects 0.000 claims description 4
• 125000002632 imidazolidinyl group Chemical group 0.000 claims description 4
• 210000003141 lower extremity Anatomy 0.000 claims description 4
• 125000002757 morpholinyl group Chemical group 0.000 claims description 4
• 125000001624 naphthyl group Chemical group 0.000 claims description 4
• 125000004193 piperazinyl group Chemical group 0.000 claims description 4
• 125000003386 piperidinyl group Chemical group 0.000 claims description 4
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
• 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
• 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000001422 pyrrolinyl group Chemical group 0.000 claims description 4
• 125000004306 triazinyl group Chemical group 0.000 claims description 4
• 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 3
• 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 claims description 3
• 206010002388 Angina unstable Diseases 0.000 claims description 3
• 206010028851 Necrosis Diseases 0.000 claims description 3
• 206010043647 Thrombotic Stroke Diseases 0.000 claims description 3
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 3
• 208000007814 Unstable Angina Diseases 0.000 claims description 3
• 206010047249 Venous thrombosis Diseases 0.000 claims description 3
• 238000002399 angioplasty Methods 0.000 claims description 3
• 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 3
• 125000005352 carboxycycloalkyl group Chemical group 0.000 claims description 3
• 238000013172 carotid endarterectomy Methods 0.000 claims description 3
• 125000005879 dioxolanyl group Chemical group 0.000 claims description 3
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims description 3
• 238000003780 insertion Methods 0.000 claims description 3
• 230000037431 insertion Effects 0.000 claims description 3
• 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 230000017074 necrotic cell death Effects 0.000 claims description 3
• 238000013146 percutaneous coronary intervention Methods 0.000 claims description 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 3
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 3
• 230000002792 vascular Effects 0.000 claims description 3
• 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
• 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 2
• 125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 2
• 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 2
• 125000000532 dioxanyl group Chemical group 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 26
• 230000006441 vascular event Effects 0.000 claims 5
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims 4
• 206010051055 Deep vein thrombosis Diseases 0.000 claims 2
• 208000018262 Peripheral vascular disease Diseases 0.000 claims 2
• 208000010378 Pulmonary Embolism Diseases 0.000 claims 2
• 206010037549 Purpura Diseases 0.000 claims 2
• 241001672981 Purpura Species 0.000 claims 2
• 208000007718 Stable Angina Diseases 0.000 claims 2
• 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 2
• 208000029078 coronary artery disease Diseases 0.000 claims 2
• 208000002296 eclampsia Diseases 0.000 claims 2
• 230000003073 embolic effect Effects 0.000 claims 2
• 208000028867 ischemia Diseases 0.000 claims 2
• 201000011461 pre-eclampsia Diseases 0.000 claims 2
• 125000005113 hydroxyalkoxy group Chemical group 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 39
• 238000011282 treatment Methods 0.000 abstract description 22
• 238000003786 synthesis reaction Methods 0.000 abstract description 10
• 239000000543 intermediate Substances 0.000 abstract description 8
• 230000015572 biosynthetic process Effects 0.000 abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 311
• 235000019439 ethyl acetate Nutrition 0.000 description 102
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 99
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
• SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 96
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 91
• 239000012267 brine Substances 0.000 description 84
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 84
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 75
• 238000005481 NMR spectroscopy Methods 0.000 description 73
• 239000012044 organic layer Substances 0.000 description 68
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 63
• 239000010410 layer Substances 0.000 description 62
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 51
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 50
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 46
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 43
• 230000002829 reductive effect Effects 0.000 description 41
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 32
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 32
• 239000002585 base Substances 0.000 description 32
• 239000000741 silica gel Substances 0.000 description 32
• 229910002027 silica gel Inorganic materials 0.000 description 32
• 239000007787 solid Substances 0.000 description 32
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 31
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 31
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 29
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 27
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• 239000003153 chemical reaction reagent Substances 0.000 description 26
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 26
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 23
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 23
• 235000019341 magnesium sulphate Nutrition 0.000 description 22
• RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 description 22
• 125000006239 protecting group Chemical group 0.000 description 21
• 229910052757 nitrogen Inorganic materials 0.000 description 20
• 239000002904 solvent Substances 0.000 description 20
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 18
• 125000004432 carbon atom Chemical group C* 0.000 description 18
• 229910000104 sodium hydride Inorganic materials 0.000 description 17
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
• 229910052799 carbon Inorganic materials 0.000 description 14
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 14
• 229960004063 propylene glycol Drugs 0.000 description 14
• 235000013772 propylene glycol Nutrition 0.000 description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
• 239000007821 HATU Substances 0.000 description 13
• 239000004146 Propane-1,2-diol Substances 0.000 description 13
• 239000002253 acid Substances 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 12
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 12
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 12
• 239000012312 sodium hydride Substances 0.000 description 12
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• 239000000460 chlorine Substances 0.000 description 11
• 239000003480 eluent Substances 0.000 description 11
• 238000002360 preparation method Methods 0.000 description 11
• 238000010898 silica gel chromatography Methods 0.000 description 11
• 239000000243 solution Substances 0.000 description 11
• 229940086542 triethylamine Drugs 0.000 description 11
• 150000007942 carboxylates Chemical class 0.000 description 10
• 238000009472 formulation Methods 0.000 description 10
• 125000001072 heteroaryl group Chemical group 0.000 description 10
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
• 125000006413 ring segment Chemical group 0.000 description 10
• 208000010110 spontaneous platelet aggregation Diseases 0.000 description 10
• 229910052717 sulfur Inorganic materials 0.000 description 10
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 9
• 229910052783 alkali metal Inorganic materials 0.000 description 9
• 229910052801 chlorine Inorganic materials 0.000 description 9
• 125000001153 fluoro group Chemical group F* 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 229910000404 tripotassium phosphate Inorganic materials 0.000 description 9
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
• 150000002009 diols Chemical class 0.000 description 8
• 229910052731 fluorine Inorganic materials 0.000 description 8
• 239000007789 gas Substances 0.000 description 8
• 229920000669 heparin Polymers 0.000 description 8
• 239000012442 inert solvent Substances 0.000 description 8
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 239000002480 mineral oil Substances 0.000 description 8
• 235000010446 mineral oil Nutrition 0.000 description 8
• 229940002612 prodrug Drugs 0.000 description 8
• 239000000651 prodrug Substances 0.000 description 8
• 239000011593 sulfur Chemical group 0.000 description 8
• 125000005270 trialkylamine group Chemical group 0.000 description 8
• JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 7
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical group [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 7
• 150000001412 amines Chemical class 0.000 description 7
• 239000004202 carbamide Substances 0.000 description 7
• 239000006196 drop Substances 0.000 description 7
• 229940079593 drug Drugs 0.000 description 7
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
• COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 7
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
• 239000005552 B01AC04 - Clopidogrel Substances 0.000 description 6
• OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 6
• LKJPYSCBVHEWIU-UHFFFAOYSA-N N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(4-fluorophenyl)sulfonyl]-2-hydroxy-2-methylpropanamide Chemical compound C=1C=C(C#N)C(C(F)(F)F)=CC=1NC(=O)C(O)(C)CS(=O)(=O)C1=CC=C(F)C=C1 LKJPYSCBVHEWIU-UHFFFAOYSA-N 0.000 description 6
• 229910052794 bromium Inorganic materials 0.000 description 6
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