SK8572000A3 - Benzamine derivatives - Google Patents

Benzamine derivatives Download PDF

Info

Publication number: SK8572000A3
Authority: SK; Slovakia
Prior art keywords: methyl; ylmethyl; phenyl; piperazin; oxadiazol
Prior art date: 1997-12-12

Application number

SK857-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Dieter Dorsch

Horst Juraszyk

Hanns Wurziger

Joachim Gante

Werner Mederski

Hans-Peter Buchstaller

Soheila Anzali

Sabine Bernotat-Danielowski

Guido Melzer

Original Assignee

Merck Patent Gmbh

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.)

1997-12-12

Filing date

1998-11-27

Publication date

2001-07-10

1998-11-27 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2001-07-10 Publication of SK8572000A3 publication Critical patent/SK8572000A3/sk

Links

PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title description 11
150000001875 compounds Chemical class 0.000 claims abstract description 121
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
229910052757 nitrogen Inorganic materials 0.000 claims description 37
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
238000000034 method Methods 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 18
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
238000002360 preparation method Methods 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 12
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
238000007327 hydrogenolysis reaction Methods 0.000 claims description 11
125000001624 naphthyl group Chemical group 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 9
239000003795 chemical substances by application Substances 0.000 claims description 9
238000003797 solvolysis reaction Methods 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
150000003937 benzamidines Chemical class 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000001153 fluoro group Chemical group F* 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
150000004866 oxadiazoles Chemical class 0.000 claims description 3
YZEPMQXUPCJOCY-UHFFFAOYSA-N 3-[[3-(4-carbamimidoylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methoxy]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1N1C(=O)OC(COC=2C=C(C=CC=2)C(N)=N)C1 YZEPMQXUPCJOCY-UHFFFAOYSA-N 0.000 claims description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000011593 sulfur Chemical group 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
QROCYRVGCHDDLR-UHFFFAOYSA-N 4-[[2-hydroxy-3-[(4-propan-2-ylphenyl)sulfonylmethylamino]propyl]amino]benzenecarboximidamide Chemical compound C(C)(C)C1=CC=C(C=C1)S(=O)(=O)CNCC(CNC1=CC=C(C(=N)N)C=C1)O QROCYRVGCHDDLR-UHFFFAOYSA-N 0.000 claims 1
BTLRKVDLMIGGOS-UHFFFAOYSA-N 4-[[2-hydroxy-3-[4-(2-naphthalen-1-ylphenyl)sulfonylpiperazin-1-yl]propyl]amino]benzenecarboximidamide Chemical compound C1=CC(C(=N)N)=CC=C1NCC(O)CN1CCN(S(=O)(=O)C=2C(=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)CC1 BTLRKVDLMIGGOS-UHFFFAOYSA-N 0.000 claims 1
CWJXCAVJQCBDSD-UHFFFAOYSA-N 4-[[3-[4-(2,6-dichloro-4-methoxyphenyl)sulfonylpiperazin-1-yl]-2-hydroxypropyl]amino]benzenecarboximidamide Chemical compound ClC1=CC(OC)=CC(Cl)=C1S(=O)(=O)N1CCN(CC(O)CNC=2C=CC(=CC=2)C(N)=N)CC1 CWJXCAVJQCBDSD-UHFFFAOYSA-N 0.000 claims 1
239000003153 chemical reaction reagent Substances 0.000 claims 1
125000004122 cyclic group Chemical group 0.000 claims 1
108010074860 Factor Xa Proteins 0.000 abstract description 13
208000001435 Thromboembolism Diseases 0.000 abstract description 6
229910052727 yttrium Inorganic materials 0.000 abstract description 3
239000003112 inhibitor Substances 0.000 abstract description 2
238000011321 prophylaxis Methods 0.000 abstract 1
238000002560 therapeutic procedure Methods 0.000 abstract 1
-1 Aromatic amidine Chemical class 0.000 description 385
238000010265 fast atom bombardment Methods 0.000 description 223
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 46
238000006243 chemical reaction Methods 0.000 description 41
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 34
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
238000005984 hydrogenation reaction Methods 0.000 description 28
239000000243 solution Substances 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
239000002904 solvent Substances 0.000 description 12
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
239000002253 acid Substances 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
239000007858 starting material Substances 0.000 description 10
238000010626 work up procedure Methods 0.000 description 10
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
108090000190 Thrombin Proteins 0.000 description 9
125000002252 acyl group Chemical group 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
229960004072 thrombin Drugs 0.000 description 9
IYFIYGSJZIICOZ-UHFFFAOYSA-N 6-chloronaphthalene-2-sulfonyl chloride Chemical compound C1=C(S(Cl)(=O)=O)C=CC2=CC(Cl)=CC=C21 IYFIYGSJZIICOZ-UHFFFAOYSA-N 0.000 description 8
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
208000007536 Thrombosis Diseases 0.000 description 8
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 8
238000003776 cleavage reaction Methods 0.000 description 8
230000007017 scission Effects 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 7
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
239000004480 active ingredient Substances 0.000 description 7
230000015572 biosynthetic process Effects 0.000 description 7
WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 7
229910052740 iodine Inorganic materials 0.000 description 7
239000011630 iodine Substances 0.000 description 7
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 7
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 7
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
XKDBKBMAWNBNRE-UHFFFAOYSA-N [amino(phenyl)methylidene]azanium;acetate Chemical compound CC(O)=O.NC(=N)C1=CC=CC=C1 XKDBKBMAWNBNRE-UHFFFAOYSA-N 0.000 description 6
125000003277 amino group Chemical group 0.000 description 6
229940012414 factor viia Drugs 0.000 description 6
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 6
125000006308 propyl amino group Chemical group 0.000 description 6
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
RGTBLCLLSZPOKR-UHFFFAOYSA-N 5-methyl-1,2,4-oxadiazole Chemical compound CC1=NC=NO1 RGTBLCLLSZPOKR-UHFFFAOYSA-N 0.000 description 5
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000002585 base Substances 0.000 description 5
JWOCZCVIXWLBNG-UHFFFAOYSA-N benzenecarboximidamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NC(=N)C1=CC=CC=C1 JWOCZCVIXWLBNG-UHFFFAOYSA-N 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
125000004093 cyano group Chemical group *C#N 0.000 description 5
239000003814 drug Substances 0.000 description 5
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 5
239000008194 pharmaceutical composition Substances 0.000 description 5
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
235000017557 sodium bicarbonate Nutrition 0.000 description 5
238000003756 stirring Methods 0.000 description 5
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 5
239000003826 tablet Substances 0.000 description 5
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 description 5
ONWRSBMOCIQLRK-UHFFFAOYSA-N 2-phenylethenesulfonyl chloride Chemical compound ClS(=O)(=O)C=CC1=CC=CC=C1 ONWRSBMOCIQLRK-UHFFFAOYSA-N 0.000 description 4
ONCAZCNPWWQQMW-UHFFFAOYSA-N 3-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=CC(S(Cl)(=O)=O)=C1 ONCAZCNPWWQQMW-UHFFFAOYSA-N 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
ALBQXDHCMLLQMB-UHFFFAOYSA-N 4-phenylbenzenesulfonyl chloride Chemical compound C1=CC(S(=O)(=O)Cl)=CC=C1C1=CC=CC=C1 ALBQXDHCMLLQMB-UHFFFAOYSA-N 0.000 description 4
LEFGAGRZHLNPLS-UHFFFAOYSA-N 4-propylbenzenesulfonyl chloride Chemical compound CCCC1=CC=C(S(Cl)(=O)=O)C=C1 LEFGAGRZHLNPLS-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
108010054265 Factor VIIa Proteins 0.000 description 4
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
150000001298 alcohols Chemical class 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
230000002785 anti-thrombosis Effects 0.000 description 4
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 4
OVIZSQRQYWEGON-UHFFFAOYSA-N butane-1-sulfonamide Chemical compound CCCCS(N)(=O)=O OVIZSQRQYWEGON-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule Substances 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
HJJPIFMUUQYUON-UHFFFAOYSA-N methyl [3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methanesulfonate Chemical compound O=C1OC(CS(=O)(=O)OC)CN1C1=CC=C(C=2N=C(C)ON=2)C=C1 HJJPIFMUUQYUON-UHFFFAOYSA-N 0.000 description 4
150000002825 nitriles Chemical class 0.000 description 4
125000004430 oxygen atom Chemical group O* 0.000 description 4
238000010422 painting Methods 0.000 description 4
150000003254 radicals Chemical class 0.000 description 4
239000011347 resin Substances 0.000 description 4
229920005989 resin Polymers 0.000 description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 4
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 4
WHJAQKAAIOHCGN-UHFFFAOYSA-N 2,4,6-trichlorobenzenesulfonyl chloride Chemical compound ClC1=CC(Cl)=C(S(Cl)(=O)=O)C(Cl)=C1 WHJAQKAAIOHCGN-UHFFFAOYSA-N 0.000 description 3
FSGLUBQENACWCC-UHFFFAOYSA-N 3,4-difluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1F FSGLUBQENACWCC-UHFFFAOYSA-N 0.000 description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-UHFFFAOYSA-N 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
GWFXDFBDCKOFSR-UHFFFAOYSA-N 5-[[4-(3,4-difluorophenyl)sulfonylpiperazin-1-yl]methyl]-3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2C(OC(CN3CCN(CC3)S(=O)(=O)C=3C=C(F)C(F)=CC=3)C2)=O)=N1 GWFXDFBDCKOFSR-UHFFFAOYSA-N 0.000 description 3
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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 1
125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
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230000003301 hydrolyzing effect Effects 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
150000002463 imidates Chemical class 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
239000007943 implant Substances 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
LQIVVUILGDRRHE-UHFFFAOYSA-N methyl 4-methoxythiophene-3-carboxylate Chemical compound COC(=O)C1=CSC=C1OC LQIVVUILGDRRHE-UHFFFAOYSA-N 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
239000000178 monomer Substances 0.000 description 1
125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 description 1
125000004572 morpholin-3-yl group Chemical group N1C(COCC1)* 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
HMCGHKOMCAWGFT-UHFFFAOYSA-N n'-hydroxy-3-[2-hydroxy-3-[3-(n'-hydroxycarbamimidoyl)phenoxy]propoxy]benzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC(OCC(O)COC=2C=C(C=CC=2)C(N)=NO)=C1 HMCGHKOMCAWGFT-UHFFFAOYSA-N 0.000 description 1
KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
ILQILQZPPNYFEX-UHFFFAOYSA-N n-(4-chlorophenyl)-4-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazine-1-carboxamide Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2C(OC(CN3CCN(CC3)C(=O)NC=3C=CC(Cl)=CC=3)C2)=O)=N1 ILQILQZPPNYFEX-UHFFFAOYSA-N 0.000 description 1
DLQKYQYYWYJVDD-UHFFFAOYSA-N n-(4-methoxyphenyl)-4-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1NC(=O)N1CCN(CC2OC(=O)N(C2)C=2C=CC(=CC=2)C=2N=C(C)ON=2)CC1 DLQKYQYYWYJVDD-UHFFFAOYSA-N 0.000 description 1
FMIKGBBCAQOMTL-UHFFFAOYSA-N n-[1-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidin-4-yl]-4-phenylbenzenesulfonamide Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2C(OC(CN3CCC(CC3)NS(=O)(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)C2)=O)=N1 FMIKGBBCAQOMTL-UHFFFAOYSA-N 0.000 description 1
KLVDWPHJEDVNMU-UHFFFAOYSA-N n-[2-hydroxy-3-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCC(O)COC1=CC=CC(C=2N=C(C)ON=2)=C1 KLVDWPHJEDVNMU-UHFFFAOYSA-N 0.000 description 1
PUOYTLCONFTZBW-UHFFFAOYSA-N n-[4-methyl-5-[4-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazin-1-yl]sulfonyl-1,3-thiazol-2-yl]acetamide Chemical compound S1C(NC(=O)C)=NC(C)=C1S(=O)(=O)N1CCN(CC2OC(=O)N(C2)C=2C=CC(=CC=2)C=2N=C(C)ON=2)CC1 PUOYTLCONFTZBW-UHFFFAOYSA-N 0.000 description 1
KIUDUUSECLXVOB-UHFFFAOYSA-N n-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]propane-2-sulfonamide Chemical compound O=C1OC(CNS(=O)(=O)C(C)C)CN1C1=CC=C(C=2N=C(C)ON=2)C=C1 KIUDUUSECLXVOB-UHFFFAOYSA-N 0.000 description 1
HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
KFPKLZWRODRZSX-UHFFFAOYSA-N n-butyl-4-[[3-(4-carbamimidoylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C(N)=N)C1 KFPKLZWRODRZSX-UHFFFAOYSA-N 0.000 description 1
XLQCWZLTISPBKV-UHFFFAOYSA-N n-butyl-4-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCCC)CCN1CC1OC(=O)N(C=2C=CC(=CC=2)C=2N=C(C)ON=2)C1 XLQCWZLTISPBKV-UHFFFAOYSA-N 0.000 description 1
DFVWEOUMPPAUSG-UHFFFAOYSA-N n-butyl-6-chloro-n-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]naphthalene-2-sulfonamide Chemical compound C=1C=C2C=C(Cl)C=CC2=CC=1S(=O)(=O)N(CCCC)CC(OC1=O)CN1C(C=C1)=CC=C1C1=NOC(C)=N1 DFVWEOUMPPAUSG-UHFFFAOYSA-N 0.000 description 1
OMRRJBMCKHAQIE-UHFFFAOYSA-N n-cyclohexyl-4-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperazine-1-carboxamide Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2C(OC(CN3CCN(CC3)C(=O)NC3CCCCC3)C2)=O)=N1 OMRRJBMCKHAQIE-UHFFFAOYSA-N 0.000 description 1
XGWFBFQJOMBSOC-UHFFFAOYSA-N n-methyl-n-[2-[methyl-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]amino]ethyl]-4-phenylbenzenesulfonamide Chemical compound C1N(C=2C=CC(=CC=2)C=2N=C(C)ON=2)C(=O)OC1CN(C)CCN(C)S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XGWFBFQJOMBSOC-UHFFFAOYSA-N 0.000 description 1
QGIUFLLGMLDGHA-UHFFFAOYSA-N n-methyl-n-[2-[methyl-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]amino]ethyl]naphthalene-1-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)N(C)CCN(C)CC(OC1=O)CN1C(C=C1)=CC=C1C1=NOC(C)=N1 QGIUFLLGMLDGHA-UHFFFAOYSA-N 0.000 description 1
AILOZFNMQMWTJF-UHFFFAOYSA-N n-methyl-n-[2-[methyl-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]amino]ethyl]naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C)CCN(C)CC(OC1=O)CN1C(C=C1)=CC=C1C1=NOC(C)=N1 AILOZFNMQMWTJF-UHFFFAOYSA-N 0.000 description 1
CAORFJXBXLLMSY-UHFFFAOYSA-N n-methyl-n-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]-4-propan-2-ylbenzenesulfonamide Chemical compound C1=CC(C(C)C)=CC=C1S(=O)(=O)N(C)CC1OC(=O)N(C=2C=CC(=CC=2)C=2N=C(C)ON=2)C1 CAORFJXBXLLMSY-UHFFFAOYSA-N 0.000 description 1
ZIZCXZNDJVUPOR-UHFFFAOYSA-N n-methyl-n-[[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]naphthalene-2-sulfonamide Chemical compound C=1C=C2C=CC=CC2=CC=1S(=O)(=O)N(C)CC(OC1=O)CN1C(C=C1)=CC=C1C1=NOC(C)=N1 ZIZCXZNDJVUPOR-UHFFFAOYSA-N 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
ABOYDMHGKWRPFD-UHFFFAOYSA-N phenylmethanesulfonamide Chemical compound NS(=O)(=O)CC1=CC=CC=C1 ABOYDMHGKWRPFD-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000000047 product Substances 0.000 description 1
239000001294 propane Substances 0.000 description 1
DRINJBFRTLBHNF-UHFFFAOYSA-N propane-2-sulfonyl chloride Chemical compound CC(C)S(Cl)(=O)=O DRINJBFRTLBHNF-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
229940039716 prothrombin Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 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
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
150000003354 serine derivatives Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
235000007586 terpenes Nutrition 0.000 description 1
SRYJAVNLPWWPKO-UHFFFAOYSA-N tert-butyl 1-[amino-[3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]piperidine-4-carboxylate Chemical compound O1C(C)=NC(C=2C=CC(=CC=2)N2C(OC(C2)C(N)N2CCC(CC2)C(=O)OC(C)(C)C)=O)=N1 SRYJAVNLPWWPKO-UHFFFAOYSA-N 0.000 description 1
GLHUOPIDSYXUGA-UHFFFAOYSA-N tert-butyl 4-[2-acetyloxy-3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(OC(=O)C)COC(C=C1)=CC=C1C1=NOC(C)=N1 GLHUOPIDSYXUGA-UHFFFAOYSA-N 0.000 description 1
ISENRXYNTDDWKI-UHFFFAOYSA-N tert-butyl 4-[2-hydroxy-3-[4-[(z)-n'-hydroxycarbamimidoyl]phenoxy]propyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CC(O)COC1=CC=C(C(\N)=N\O)C=C1 ISENRXYNTDDWKI-UHFFFAOYSA-N 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000005425 toluyl group Chemical group 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
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235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
- C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
- C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
- 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
- C07D413/10—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 carbon chain containing aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Vascular Medicine (AREA)
Cardiology (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Heart & Thoracic Surgery (AREA)
Diabetes (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Pain & Pain Management (AREA)
Neurosurgery (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Thiazole And Isothizaole Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

SK857-2000A 1997-12-12 1998-11-27 Benzamine derivatives SK8572000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19755268A DE19755268A1 (de)	1997-12-12	1997-12-12	Benzamidinderivate
PCT/EP1998/007673 WO1999031092A1 (fr)	1997-12-12	1998-11-27	DERIVES DE BENZAMIDINE UTILISES COMME INHIBITEURS DU FACTEUR DE COAGULATION Xa

Publications (1)

Publication Number	Publication Date
SK8572000A3 true SK8572000A3 (en)	2001-07-10

Family

ID=7851688

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK857-2000A SK8572000A3 (en)	1997-12-12	1998-11-27	Benzamine derivatives

Country Status (16)

Country	Link
EP (1)	EP1056743A1 (fr)
JP (1)	JP2002508370A (fr)
KR (1)	KR20010032963A (fr)
CN (1)	CN1281451A (fr)
AR (1)	AR017844A1 (fr)
AU (1)	AU744002B2 (fr)
BR (1)	BR9813477A (fr)
CA (1)	CA2313651A1 (fr)
DE (1)	DE19755268A1 (fr)
HU (1)	HUP0004353A3 (fr)
NO (1)	NO20002958L (fr)
PL (1)	PL341008A1 (fr)
RU (1)	RU2203897C2 (fr)
SK (1)	SK8572000A3 (fr)
WO (1)	WO1999031092A1 (fr)
ZA (1)	ZA9811339B (fr)

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GB0107228D0 (en)	2001-03-22	2001-05-16	Astrazeneca Ab	Chemical compounds
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DE10355461A1 (de)	2003-11-27	2005-06-23	Bayer Healthcare Ag	Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung
EP1685841A1 (fr)	2005-01-31	2006-08-02	Bayer Health Care Aktiengesellschaft	Prevention et traitement de troubles thromboemboliques
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DE102005045518A1 (de)	2005-09-23	2007-03-29	Bayer Healthcare Ag	2-Aminoethoxyessigsäure-Derivate und ihre Verwendung
DE102005047561A1 (de)	2005-10-04	2007-04-05	Bayer Healthcare Ag	Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung
MY145616A (en)	2005-10-04	2012-03-15	Bayer Schering Pharma Ag	Novel polymorphous form and the amorphous form of 5-chloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidine-5-yl}-methyl)-2-thiophene carboxamide
ES2369634T3 (es) *	2006-01-31	2011-12-02	Dong Wha Pharmaceutical Co., Ltd.	Derivados de benzamidina novedosos, procedimiento para la preparación de los mismos y composición farmacéutica que comprende los mismos.
DE102007018662A1 (de)	2007-04-20	2008-10-23	Bayer Healthcare Ag	Oxazolidinone zur Behandlung und Prophylaxe von pulmonaler Hypertonie
KR101009594B1 (ko)	2007-05-09	2011-01-20	주식회사 레고켐 바이오사이언스	Ｐ4 위치에 사이클릭 아미딘을 가지는 ＦＸａ 저해제, 이의유도체, 제조방법 및 이를 함유하는 의약 조성물
WO2008140220A1 (fr) *	2007-05-09	2008-11-20	Legochem Bioscience Ltd.	Inhibiteurs du facteur xa comprenant des amidines cycliques en tant que sous-unité p4, leurs procédés de préparation, et compositions pharmaceutiques et dérivés de ceux-ci
DE102007028318A1 (de)	2007-06-20	2008-12-24	Bayer Healthcare Ag	Oxazolidinone zur Behandlung und Prophylaxe von Sepsis
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1997
- 1997-12-12 DE DE19755268A patent/DE19755268A1/de not_active Withdrawn
1998
- 1998-11-27 KR KR1020007006310A patent/KR20010032963A/ko not_active Withdrawn
- 1998-11-27 HU HU0004353A patent/HUP0004353A3/hu unknown
- 1998-11-27 CA CA002313651A patent/CA2313651A1/fr not_active Abandoned
- 1998-11-27 WO PCT/EP1998/007673 patent/WO1999031092A1/fr not_active Ceased
- 1998-11-27 BR BR9813477-9A patent/BR9813477A/pt not_active IP Right Cessation
- 1998-11-27 JP JP2000539016A patent/JP2002508370A/ja active Pending
- 1998-11-27 AU AU19647/99A patent/AU744002B2/en not_active Ceased
- 1998-11-27 PL PL98341008A patent/PL341008A1/xx unknown
- 1998-11-27 SK SK857-2000A patent/SK8572000A3/sk unknown
- 1998-11-27 RU RU2000118792/04A patent/RU2203897C2/ru not_active IP Right Cessation
- 1998-11-27 CN CN98812087A patent/CN1281451A/zh active Pending
- 1998-11-27 EP EP98964455A patent/EP1056743A1/fr not_active Withdrawn
- 1998-12-10 ZA ZA9811339A patent/ZA9811339B/xx unknown
- 1998-12-11 AR ARP980106293A patent/AR017844A1/es not_active Application Discontinuation
2000
- 2000-06-09 NO NO20002958A patent/NO20002958L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
AR017844A1 (es)	2001-10-24
KR20010032963A (ko)	2001-04-25
ZA9811339B (en)	1999-07-08
HUP0004353A3 (en)	2002-04-29
AU744002B2 (en)	2002-02-14
HUP0004353A2 (hu)	2002-03-28
WO1999031092A1 (fr)	1999-06-24
PL341008A1 (en)	2001-03-12
AU1964799A (en)	1999-07-05
JP2002508370A (ja)	2002-03-19
NO20002958D0 (no)	2000-06-09
CN1281451A (zh)	2001-01-24
NO20002958L (no)	2000-08-11
DE19755268A1 (de)	1999-06-17
EP1056743A1 (fr)	2000-12-06
CA2313651A1 (fr)	1999-06-24
RU2203897C2 (ru)	2003-05-10
BR9813477A (pt)	2000-10-24

Publication	Publication Date	Title
SK8572000A3 (en)	2001-07-10	Benzamine derivatives
SK4472000A3 (en)	2000-11-07	Benzamidine derivatives as factor xa inhibitors, process for their preparation, the use thereof and pharmaceutical composition containing the same
SK12152001A3 (sk)	2002-03-05	Derivát pyrazol-3-ónu ako faktor Xa inhibítorov, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje
AU2002363366B2 (en)	2007-11-22	Derivatives of phenoxy-N- 4-(isothiazolidin-1,1-dioxid-2YL)pheny!-valerian- acid amide and other compounds as inhibitors of the coagulation factor XA in the treatment of thromboembolic diseases and tumors
AU2004205354B2 (en)	2009-12-10	Carboxamide derivatives and their use as factor Xa inhibitors
US20030166694A1 (en)	2003-09-04	Glycinamides
CZ2003338A3 (cs)	2003-05-14	Derivát N-substituované 1-amino-1, 1-dialkylkarboxylové kyseliny, způsob jeho přípravy, jeho použití a farmaceutický prostředek, který ho obsahuje
CZ20002126A3 (cs)	2000-09-13	Řešení se týká nosného tělesa (1) pro uspořádání elektrických kontaktů, které obsahuje elektricky nevodivé základní těleso, ve kterémjsou uspořádány elektrické kontakty (3). Nosné těleso (1) má modulovou konstrukci, sestávající z jednotlivých samostatných prvků (2,4), které mohou být spolu vzájemně sestaveny a spojeny. Jednotlivé samostatné prvky (2,4) mohou nebo nemusejí být opatřeny kontakty (3).
CZ20001183A3 (cs)	2000-07-12	Derivát benzamidinu jako inhibitor faktoru XA, způsob jeho přípravy, jeho použití a farmaceutický prostředek, který ho obsahuje
MXPA00003094A (en)	2001-07-09	Benzamidine derivatives as factor xa inhibitors
US20030187037A1 (en)	2003-10-02	Acetamide derivatives and the use thereof as inhibitors of coagulation factors xa and viia
US20030199698A1 (en)	2003-10-23	Carbamic acid esters as inhibitors of factor xa
SK1992003A3 (en)	2003-06-03	Urethane derivative, method for its preparation, its use and pharmaceutical composition comprising same
MXPA04008479A (es)	2004-12-06	Derivados de semicarbazida.