TWI376377B - Heteroaryl-carboxylic acid (sulfamoyl alkyl) amide-derivatives as factor xa inhibitors - Google Patents

Info

Publication number

TWI376377B

TWI376377B TW095117566A TW95117566A TWI376377B TW I376377 B TWI376377 B TW I376377B TW 095117566 A TW095117566 A TW 095117566A TW 95117566 A TW95117566 A TW 95117566A TW I376377 B TWI376377 B TW I376377B

Authority

TW

Taiwan

Prior art keywords

isopropyl

ethyl

group

acid

amine

Prior art date

2005-05-20

Links

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• 229940123583 Factor Xa inhibitor Drugs 0.000 title 1
• -1 chloro, methyl Chemical group 0.000 claims description 171
• 150000001875 compounds Chemical class 0.000 claims description 131
• 239000002253 acid Substances 0.000 claims description 91
• 125000000623 heterocyclic group Chemical group 0.000 claims description 80
• 238000000034 method Methods 0.000 claims description 79
• 125000000217 alkyl group Chemical group 0.000 claims description 54
• QZLSBOVWPHXCLT-UHFFFAOYSA-N 5-chlorothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Cl)S1 QZLSBOVWPHXCLT-UHFFFAOYSA-N 0.000 claims description 45
• 150000003839 salts Chemical class 0.000 claims description 42
• 150000001412 amines Chemical class 0.000 claims description 36
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 29
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 24
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 21
• 108010074860 Factor Xa Proteins 0.000 claims description 20
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
• 125000004429 atom Chemical group 0.000 claims description 15
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 125000006239 protecting group Chemical group 0.000 claims description 15
• MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 12
• 229910052801 chlorine Inorganic materials 0.000 claims description 12
• 239000002243 precursor Substances 0.000 claims description 12
• 125000001544 thienyl group Chemical group 0.000 claims description 12
• 239000000460 chlorine Substances 0.000 claims description 11
• 229960005181 morphine Drugs 0.000 claims description 11
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 10
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 9
• 230000015271 coagulation Effects 0.000 claims description 9
• 238000005345 coagulation Methods 0.000 claims description 9
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
• 230000002792 vascular Effects 0.000 claims description 9
• 239000003814 drug Substances 0.000 claims description 8
• 208000037803 restenosis Diseases 0.000 claims description 8
• 208000007536 Thrombosis Diseases 0.000 claims description 7
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
• KXIXHISTUVHOCY-UHFFFAOYSA-N 1-propan-2-ylpiperidine Chemical compound CC(C)N1CCCCC1 KXIXHISTUVHOCY-UHFFFAOYSA-N 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 125000000335 thiazolyl group Chemical group 0.000 claims description 6
• OLMLHCRNIJACTN-UHFFFAOYSA-N C1=CC(=O)SC1C(=O)O Chemical compound C1=CC(=O)SC1C(=O)O OLMLHCRNIJACTN-UHFFFAOYSA-N 0.000 claims description 5
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 125000002757 morpholinyl group Chemical group 0.000 claims description 5
• 230000009467 reduction Effects 0.000 claims description 5
• 238000001356 surgical procedure Methods 0.000 claims description 5
• 210000003462 vein Anatomy 0.000 claims description 5
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• 230000001154 acute effect Effects 0.000 claims description 4
• 238000002399 angioplasty Methods 0.000 claims description 4
• 239000003146 anticoagulant agent Substances 0.000 claims description 4
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• 238000007887 coronary angioplasty Methods 0.000 claims description 4
• 230000020764 fibrinolysis Effects 0.000 claims description 4
• 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 4
• YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 4
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
• 230000001732 thrombotic effect Effects 0.000 claims description 4
• 208000005189 Embolism Diseases 0.000 claims description 3
• 101100258328 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) crc-2 gene Proteins 0.000 claims description 3
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• 238000004519 manufacturing process Methods 0.000 claims description 3
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• 206010002383 Angina Pectoris Diseases 0.000 claims description 2
• 206010053567 Coagulopathies Diseases 0.000 claims description 2
• 206010010904 Convulsion Diseases 0.000 claims description 2
• 208000034486 Multi-organ failure Diseases 0.000 claims description 2
• 208000010718 Multiple Organ Failure Diseases 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• 206010040070 Septic Shock Diseases 0.000 claims description 2
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• 238000001631 haemodialysis Methods 0.000 claims description 2
• 230000000322 hemodialysis Effects 0.000 claims description 2
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
• 230000028709 inflammatory response Effects 0.000 claims description 2
• 238000003780 insertion Methods 0.000 claims description 2
• 230000037431 insertion Effects 0.000 claims description 2
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• 210000003141 lower extremity Anatomy 0.000 claims description 2
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• 208000029744 multiple organ dysfunction syndrome Diseases 0.000 claims description 2
• 208000010125 myocardial infarction Diseases 0.000 claims description 2
• 230000001575 pathological effect Effects 0.000 claims description 2
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
• 239000011347 resin Substances 0.000 claims description 2
• 229920005989 resin Polymers 0.000 claims description 2
• 230000036303 septic shock Effects 0.000 claims description 2
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• 208000021331 vascular occlusion disease Diseases 0.000 claims description 2
• 238000007891 venous angioplasty Methods 0.000 claims description 2
• 230000009385 viral infection Effects 0.000 claims description 2
• XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims 1
• QFYIOPNFPBCPIQ-UHFFFAOYSA-N 1-propan-2-yl-n-(1,3-thiazol-2-ylmethyl)piperidin-4-amine Chemical compound C1CN(C(C)C)CCC1NCC1=NC=CS1 QFYIOPNFPBCPIQ-UHFFFAOYSA-N 0.000 claims 1
• LIXSUPLQPDAHLO-UHFFFAOYSA-N 10-thiophen-2-yldecanoic acid Chemical compound OC(=O)CCCCCCCCCC1=CC=CS1 LIXSUPLQPDAHLO-UHFFFAOYSA-N 0.000 claims 1
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
• HIYWOHBEPVGIQN-UHFFFAOYSA-N 1h-benzo[g]indole Chemical compound C1=CC=CC2=C(NC=C3)C3=CC=C21 HIYWOHBEPVGIQN-UHFFFAOYSA-N 0.000 claims 1
• QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
• 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 1
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims 1
• 208000024172 Cardiovascular disease Diseases 0.000 claims 1
• 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 1
• 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 1
• 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 1
• 230000002146 bilateral effect Effects 0.000 claims 1
• 210000004351 coronary vessel Anatomy 0.000 claims 1
• 239000003937 drug carrier Substances 0.000 claims 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• 230000014508 negative regulation of coagulation Effects 0.000 claims 1
• FWWQKRXKHIRPJY-UHFFFAOYSA-N octadecyl aldehyde Natural products CCCCCCCCCCCCCCCCCC=O FWWQKRXKHIRPJY-UHFFFAOYSA-N 0.000 claims 1
• 229940105131 stearamine Drugs 0.000 claims 1
• AJZGFFKDLABHDD-UHFFFAOYSA-N thiazinane Chemical compound C1CCSNC1 AJZGFFKDLABHDD-UHFFFAOYSA-N 0.000 claims 1
• 239000002585 base Substances 0.000 description 94
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 71
• 239000000203 mixture Substances 0.000 description 65
• 239000000243 solution Substances 0.000 description 55
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 54
• 239000007789 gas Substances 0.000 description 49
• 230000008569 process Effects 0.000 description 47
• 239000007858 starting material Substances 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 43
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
• 230000002829 reductive effect Effects 0.000 description 34
• 239000012043 crude product Substances 0.000 description 33
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 31
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 30
• 125000003118 aryl group Chemical group 0.000 description 30
• 238000004007 reversed phase HPLC Methods 0.000 description 30
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 29
• 239000000463 material Substances 0.000 description 28
• 239000011541 reaction mixture Substances 0.000 description 28
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
• 239000000047 product Substances 0.000 description 26
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
• 229910052740 iodine Inorganic materials 0.000 description 25
• 239000000651 prodrug Substances 0.000 description 25
• 229940002612 prodrug Drugs 0.000 description 25
• 229910052736 halogen Inorganic materials 0.000 description 23
• 150000002367 halogens Chemical class 0.000 description 23
• 125000003396 thiol group Chemical group [H]S* 0.000 description 23
• 229910052799 carbon Inorganic materials 0.000 description 21
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 20
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 20
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 20
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
• 239000012074 organic phase Substances 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• 239000003153 chemical reaction reagent Substances 0.000 description 15
• 238000003786 synthesis reaction Methods 0.000 description 15
• XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical compound NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 15
• 150000001721 carbon Chemical group 0.000 description 14
• VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 14
• 229920006395 saturated elastomer Polymers 0.000 description 14
• 239000003921 oil Substances 0.000 description 13
• 235000019198 oils Nutrition 0.000 description 13
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
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• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
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• 125000000753 cycloalkyl group Chemical group 0.000 description 12
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• 239000001257 hydrogen Substances 0.000 description 12
• 229910052739 hydrogen Inorganic materials 0.000 description 12
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• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 11
• 229910052717 sulfur Inorganic materials 0.000 description 11
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• BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
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• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
• 229910052786 argon Inorganic materials 0.000 description 10
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 10
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• 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
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• FJJCIZWZNKZHII-UHFFFAOYSA-N [4,6-bis(cyanoamino)-1,3,5-triazin-2-yl]cyanamide Chemical compound N#CNC1=NC(NC#N)=NC(NC#N)=N1 FJJCIZWZNKZHII-UHFFFAOYSA-N 0.000 description 5
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