DE102004047254A1 - Carbonylverbindungen - Google Patents
Carbonylverbindungen Download PDFInfo
- Publication number
- DE102004047254A1 DE102004047254A1 DE102004047254A DE102004047254A DE102004047254A1 DE 102004047254 A1 DE102004047254 A1 DE 102004047254A1 DE 102004047254 A DE102004047254 A DE 102004047254A DE 102004047254 A DE102004047254 A DE 102004047254A DE 102004047254 A1 DE102004047254 A1 DE 102004047254A1
- Authority
- DE
- Germany
- Prior art keywords
- diyl
- atoms
- hal
- salts
- solvates
- Prior art date
- 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.)
- Withdrawn
Links
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 156
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 108010074860 Factor Xa Proteins 0.000 claims abstract description 14
- 230000009424 thromboembolic effect Effects 0.000 claims abstract description 11
- 239000003112 inhibitor Substances 0.000 claims abstract description 5
- -1 pyridine-diyl Chemical group 0.000 claims description 560
- 150000003839 salts Chemical class 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 70
- 125000004432 carbon atom Chemical group C* 0.000 claims description 66
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 57
- 239000012453 solvate Substances 0.000 claims description 55
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 31
- 125000004076 pyridyl group Chemical class 0.000 claims description 29
- 125000001544 thienyl group Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 24
- 208000007536 Thrombosis Diseases 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004434 sulfur atom Chemical group 0.000 claims description 19
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 17
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 16
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 14
- 125000002541 furyl group Chemical class 0.000 claims description 14
- 125000002883 imidazolyl group Chemical class 0.000 claims description 14
- 229940079593 drug Drugs 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 11
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000004956 cyclohexylene group Chemical group 0.000 claims description 10
- 229920002554 vinyl polymer Polymers 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000005336 allyloxy group Chemical group 0.000 claims description 9
- 208000035475 disorder Diseases 0.000 claims description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 9
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 9
- 108010054265 Factor VIIa Proteins 0.000 claims description 8
- 208000006011 Stroke Diseases 0.000 claims description 8
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 8
- 238000002399 angioplasty Methods 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
- 208000010125 myocardial infarction Diseases 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 206010002383 Angina Pectoris Diseases 0.000 claims description 7
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 7
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 206010022562 Intermittent claudication Diseases 0.000 claims description 7
- 206010027476 Metastases Diseases 0.000 claims description 7
- 208000009205 Tinnitus Diseases 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 7
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 208000037803 restenosis Diseases 0.000 claims description 7
- 238000001356 surgical procedure Methods 0.000 claims description 7
- 231100000886 tinnitus Toxicity 0.000 claims description 7
- 208000019695 Migraine disease Diseases 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 206010027599 migraine Diseases 0.000 claims description 6
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 6
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 206010020608 Hypercoagulation Diseases 0.000 claims description 5
- 208000026350 Inborn Genetic disease Diseases 0.000 claims description 5
- 206010040047 Sepsis Diseases 0.000 claims description 5
- 208000016361 genetic disease Diseases 0.000 claims description 5
- 125000005961 oxazepanyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 201000005665 thrombophilia Diseases 0.000 claims description 5
- 230000002792 vascular Effects 0.000 claims description 5
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 4
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 208000024980 claudication Diseases 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 208000021156 intermittent vascular claudication Diseases 0.000 claims description 3
- 210000000056 organ Anatomy 0.000 claims description 3
- 229910052727 yttrium Inorganic materials 0.000 claims description 3
- MZAGXDHQGXUDDX-JSRXJHBZSA-N (e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/C(N)=O MZAGXDHQGXUDDX-JSRXJHBZSA-N 0.000 claims description 2
- 230000003187 abdominal effect Effects 0.000 claims description 2
- 210000004351 coronary vessel Anatomy 0.000 claims description 2
- 210000003709 heart valve Anatomy 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000000399 orthopedic effect Effects 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 238000011477 surgical intervention Methods 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 210000000115 thoracic cavity Anatomy 0.000 claims description 2
- 229910052721 tungsten Inorganic materials 0.000 claims description 2
- 238000007631 vascular surgery Methods 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 9
- 238000011540 hip replacement Methods 0.000 claims 1
- 238000013150 knee replacement Methods 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 abstract description 3
- 235000002639 sodium chloride Nutrition 0.000 description 53
- 239000004480 active ingredient Substances 0.000 description 28
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 16
- XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 239000012442 inert solvent Substances 0.000 description 13
- 239000008194 pharmaceutical composition Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000003826 tablet Substances 0.000 description 12
- 230000005764 inhibitory process Effects 0.000 description 11
- 125000006239 protecting group Chemical group 0.000 description 11
- 238000000132 electrospray ionisation Methods 0.000 description 10
- 150000003254 radicals Chemical class 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical class 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 9
- 108090000190 Thrombin Proteins 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229960004072 thrombin Drugs 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 8
- 230000002785 anti-thrombosis Effects 0.000 description 8
- 239000003146 anticoagulant agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- BNRNXUUZRGQAQC-UHFFFAOYSA-N sildenafil Chemical compound CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 BNRNXUUZRGQAQC-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- HHDQVBSXYDRQGD-QWWZWVQMSA-N (2r,4r)-4-hydroxypyrrolidine-1,2-dicarboxylic acid Chemical compound O[C@@H]1C[C@H](C(O)=O)N(C(O)=O)C1 HHDQVBSXYDRQGD-QWWZWVQMSA-N 0.000 description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 7
- 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 description 7
- 125000002252 acyl group Chemical group 0.000 description 7
- 229910052791 calcium Inorganic materials 0.000 description 7
- 239000011575 calcium Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 235000015424 sodium Nutrition 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003513 alkali Substances 0.000 description 6
- 239000005557 antagonist Substances 0.000 description 6
- 229940127219 anticoagulant drug Drugs 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 125000006355 carbonyl methylene group Chemical group [H]C([H])([*:2])C([*:1])=O 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
- 229910052700 potassium Inorganic materials 0.000 description 6
- 239000011591 potassium Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 108010048049 Factor IXa Proteins 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001342 alkaline earth metals Chemical class 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 229940012414 factor viia Drugs 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- 229920000669 heparin Polymers 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 230000009021 linear effect Effects 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- SECKRCOLJRRGGV-UHFFFAOYSA-N Vardenafil Chemical compound CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 SECKRCOLJRRGGV-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 230000004913 activation Effects 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 4
- 230000023555 blood coagulation Effects 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 150000007530 organic bases Chemical class 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Surgery (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004047254A DE102004047254A1 (de) | 2004-09-29 | 2004-09-29 | Carbonylverbindungen |
| KR1020077007053A KR20070057878A (ko) | 2004-09-29 | 2005-09-01 | 응고 인자 ｘａ 저해제로서 사용가능한 카르보닐 화합물 |
| CA002581732A CA2581732A1 (en) | 2004-09-29 | 2005-09-01 | Carbonyl compounds usable as coagulation factor xa inhibitors |
| MX2007003470A MX2007003470A (es) | 2004-09-29 | 2005-09-01 | Compuestos de carbonilo los cuales pueden utilizarse como inhibidores del factor de coagulacion xa. |
| BRPI0515577-0A BRPI0515577A (pt) | 2004-09-29 | 2005-09-01 | compostos de carbonila que podem ser empregados como inibidores de fator xa de coagulação |
| RU2007116036/04A RU2007116036A (ru) | 2004-09-29 | 2005-09-01 | Карбонильные соединения, которые могут применяться в качестве ингибиторов фактора коагуляции ха |
| CNA2005800327898A CN101031561A (zh) | 2004-09-29 | 2005-09-01 | 可以用作凝血因子xa抑制剂的羰基化合物 |
| EP05790356A EP1797071A1 (de) | 2004-09-29 | 2005-09-01 | Carbonylverbindungen verwendbar als inhibitoren des koagulationsfaktors xa |
| US11/576,207 US20080081814A1 (en) | 2004-09-29 | 2005-09-01 | Carbonyl Compounds Which Can be Used as Inhibitors of Coagulation Factor Xa |
| JP2007533891A JP2008514655A (ja) | 2004-09-29 | 2005-09-01 | 凝固因子Ｘａの阻害剤として用いられるカルボニル化合物 |
| PCT/EP2005/009418 WO2006034769A1 (de) | 2004-09-29 | 2005-09-01 | Carbonylverbindungen verwendbar als inhibitoren des koagulationsfaktors xa |
| AU2005289164A AU2005289164A1 (en) | 2004-09-29 | 2005-09-01 | Carbonyl compounds usable as coagulation factor Xa inhibitors |
| ZA200703443A ZA200703443B (en) | 2004-09-29 | 2007-04-26 | Carbonyl compounds usable as coagulation factor Xa Inhibitors |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004047254A DE102004047254A1 (de) | 2004-09-29 | 2004-09-29 | Carbonylverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE102004047254A1 true DE102004047254A1 (de) | 2006-04-13 |
Family
ID=35395743
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE102004047254A Withdrawn DE102004047254A1 (de) | 2004-09-29 | 2004-09-29 | Carbonylverbindungen |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20080081814A1 (https=) |
| EP (1) | EP1797071A1 (https=) |
| JP (1) | JP2008514655A (https=) |
| KR (1) | KR20070057878A (https=) |
| CN (1) | CN101031561A (https=) |
| AU (1) | AU2005289164A1 (https=) |
| BR (1) | BRPI0515577A (https=) |
| CA (1) | CA2581732A1 (https=) |
| DE (1) | DE102004047254A1 (https=) |
| MX (1) | MX2007003470A (https=) |
| RU (1) | RU2007116036A (https=) |
| WO (1) | WO2006034769A1 (https=) |
| ZA (1) | ZA200703443B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE50453E1 (en) | 2006-04-07 | 2025-06-10 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| US10022352B2 (en) | 2006-04-07 | 2018-07-17 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US7645789B2 (en) | 2006-04-07 | 2010-01-12 | Vertex Pharmaceuticals Incorporated | Indole derivatives as CFTR modulators |
| EP2674428B1 (en) | 2006-04-07 | 2016-04-06 | Vertex Pharmaceuticals Incorporated | Modulators of ATP-binding cassette transporters |
| US8563573B2 (en) | 2007-11-02 | 2013-10-22 | Vertex Pharmaceuticals Incorporated | Azaindole derivatives as CFTR modulators |
| US8673920B2 (en) | 2009-05-06 | 2014-03-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US8802868B2 (en) | 2010-03-25 | 2014-08-12 | Vertex Pharmaceuticals Incorporated | Solid forms of (R)-1(2,2-difluorobenzo[D][1,3]dioxo1-5-yl)-N-(1-(2,3-dihydroxypropyl-6-fluoro-2-(1-hydroxy-2-methylpropan2-yl)-1H-Indol-5-yl)-Cyclopropanecarboxamide |
| MX353408B (es) | 2010-04-22 | 2018-01-11 | Vertex Pharma | Proceso para producir compuestos de cicloalquilcarboxamido-indol. |
| WO2012058116A1 (en) | 2010-10-27 | 2012-05-03 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2632464B1 (en) | 2010-10-29 | 2015-04-29 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| AU2012299227A1 (en) | 2011-08-19 | 2014-02-20 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2013039802A1 (en) | 2011-09-16 | 2013-03-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2771004B1 (en) | 2011-10-25 | 2016-05-18 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US8999990B2 (en) | 2011-10-25 | 2015-04-07 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2773206B1 (en) | 2011-10-31 | 2018-02-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2013066714A1 (en) | 2011-10-31 | 2013-05-10 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2773351B1 (en) | 2011-10-31 | 2017-08-23 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2790511B1 (en) | 2011-12-16 | 2016-09-14 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| JP5903499B2 (ja) | 2011-12-22 | 2016-04-13 | ノバルティス アーゲー | ジヒドロ−ベンゾ−オキサジンおよびジヒドロ−ピリド−オキサジン誘導体 |
| AR092857A1 (es) | 2012-07-16 | 2015-05-06 | Vertex Pharma | Composiciones farmaceuticas de (r)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-il)-n-(1-(2,3-dihidroxipropil)-6-fluoro-2-(1-hidroxi-2-metilpropan-2-il)-1h-indol-5-il)ciclopropancarboxamida y administracion de las mismas |
| AR092031A1 (es) | 2012-07-26 | 2015-03-18 | Merck Sharp & Dohme | Inhibidores del canal de potasio medular externo renal |
| EP2925322B1 (en) | 2012-11-29 | 2018-10-24 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| US9573961B2 (en) | 2012-12-19 | 2017-02-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| WO2014126944A2 (en) | 2013-02-18 | 2014-08-21 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP2968288B1 (en) | 2013-03-15 | 2018-07-04 | Merck Sharp & Dohme Corp. | Inhibitors of the renal outer medullary potassium channel |
| EP3027625B1 (en) | 2013-07-31 | 2018-05-30 | Merck Sharp & Dohme Corp. | Spiro-fused derivatives of piperidine useful for the treatment of inter alia hypertension and acute or chronic heart failure |
| RU2744460C2 (ru) | 2014-04-15 | 2021-03-09 | Вертекс Фармасьютикалз Инкорпорейтед | Фармацевтические композиции для лечения заболеваний, опосредованных муковисцидозным трансмембранным регулятором проводимости |
| WO2016127358A1 (en) | 2015-02-12 | 2016-08-18 | Merck Sharp & Dohme Corp. | Inhibitors of renal outer medullary potassium channel |
| US10669528B2 (en) | 2015-06-25 | 2020-06-02 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion, enrichment, and maintenance |
| WO2017161001A1 (en) | 2016-03-15 | 2017-09-21 | Children's Medical Center Corporation | Methods and compositions relating to hematopoietic stem cell expansion |
| CN106674200B (zh) * | 2016-12-21 | 2019-04-12 | 西安交通大学 | 一种含有l-脯氨酰胺片段的化合物及其制备方法和应用 |
| CN108997200A (zh) * | 2018-07-17 | 2018-12-14 | 成都睿智化学研究有限公司 | 一种5-氨甲基-哌啶-2-酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7030141B2 (en) * | 2001-11-29 | 2006-04-18 | Christopher Franklin Bigge | Inhibitors of factor Xa and other serine proteases involved in the coagulation cascade |
| PL377633A1 (pl) * | 2003-04-03 | 2006-02-06 | Merck Patent Gmbh | Związki karbonylowe |
| DE10329457A1 (de) * | 2003-04-03 | 2005-01-20 | Merck Patent Gmbh | Ethinylprolinderivate |
| DE102004045796A1 (de) * | 2004-09-22 | 2006-03-23 | Merck Patent Gmbh | Arzneimittel enthaltend Carbonylverbindungen sowie deren Verwendung |
-
2004
- 2004-09-29 DE DE102004047254A patent/DE102004047254A1/de not_active Withdrawn
-
2005
- 2005-09-01 CA CA002581732A patent/CA2581732A1/en not_active Abandoned
- 2005-09-01 MX MX2007003470A patent/MX2007003470A/es not_active Application Discontinuation
- 2005-09-01 CN CNA2005800327898A patent/CN101031561A/zh active Pending
- 2005-09-01 RU RU2007116036/04A patent/RU2007116036A/ru unknown
- 2005-09-01 BR BRPI0515577-0A patent/BRPI0515577A/pt not_active Application Discontinuation
- 2005-09-01 KR KR1020077007053A patent/KR20070057878A/ko not_active Withdrawn
- 2005-09-01 US US11/576,207 patent/US20080081814A1/en not_active Abandoned
- 2005-09-01 EP EP05790356A patent/EP1797071A1/de not_active Withdrawn
- 2005-09-01 JP JP2007533891A patent/JP2008514655A/ja active Pending
- 2005-09-01 WO PCT/EP2005/009418 patent/WO2006034769A1/de not_active Ceased
- 2005-09-01 AU AU2005289164A patent/AU2005289164A1/en not_active Abandoned
-
2007
- 2007-04-26 ZA ZA200703443A patent/ZA200703443B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20080081814A1 (en) | 2008-04-03 |
| AU2005289164A1 (en) | 2006-04-06 |
| CN101031561A (zh) | 2007-09-05 |
| MX2007003470A (es) | 2007-05-10 |
| ZA200703443B (en) | 2008-08-27 |
| WO2006034769A1 (de) | 2006-04-06 |
| KR20070057878A (ko) | 2007-06-07 |
| BRPI0515577A (pt) | 2008-07-29 |
| CA2581732A1 (en) | 2006-04-06 |
| EP1797071A1 (de) | 2007-06-20 |
| RU2007116036A (ru) | 2008-11-10 |
| JP2008514655A (ja) | 2008-05-08 |
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