JP2004517920A5 - - Google Patents
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- JP2004517920A5 JP2004517920A5 JP2002559068A JP2002559068A JP2004517920A5 JP 2004517920 A5 JP2004517920 A5 JP 2004517920A5 JP 2002559068 A JP2002559068 A JP 2002559068A JP 2002559068 A JP2002559068 A JP 2002559068A JP 2004517920 A5 JP2004517920 A5 JP 2004517920A5
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- JP
- Japan
- Prior art keywords
- alkyl
- group
- aryl
- formula
- independently
- 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.)
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- 125000000217 alkyl group Chemical group 0.000 claims 123
- 125000003118 aryl group Chemical group 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 40
- 150000003839 salts Chemical class 0.000 claims 40
- 239000012453 solvate Substances 0.000 claims 40
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- -1 butyldimethylsilyloxymethyl Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 229940002612 prodrug Drugs 0.000 claims 20
- 239000000651 prodrug Substances 0.000 claims 20
- 125000001424 substituent group Chemical group 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 18
- 239000000203 mixture Substances 0.000 claims 17
- 239000003112 inhibitor Substances 0.000 claims 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 229930182558 Sterol Natural products 0.000 claims 13
- 125000001072 heteroaryl group Chemical class 0.000 claims 13
- 150000003432 sterols Chemical class 0.000 claims 13
- 235000003702 sterols Nutrition 0.000 claims 13
- 125000005843 halogen group Chemical class 0.000 claims 12
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 238000010521 absorption reaction Methods 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 239000008280 blood Substances 0.000 claims 9
- 210000004369 blood Anatomy 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001797 benzyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 239000003795 chemical substances by application Substances 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 5
- 239000003146 anticoagulant agent Substances 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 230000003750 conditioning effect Effects 0.000 claims 5
- 125000002541 furyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims 5
- 125000004076 pyridyl group Chemical group 0.000 claims 5
- 125000000168 pyrrolyl group Chemical group 0.000 claims 5
- 125000003003 spiro group Chemical group 0.000 claims 5
- 238000006467 substitution reaction Methods 0.000 claims 5
- 125000000335 thiazolyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 5
- 230000002792 vascular Effects 0.000 claims 5
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 claims 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 125000004450 alkenylene group Chemical group 0.000 claims 4
- 125000003282 alkyl amino group Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims 4
- 229920000669 heparin Polymers 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 229940082863 Factor VIIa inhibitor Drugs 0.000 claims 3
- 229940123583 Factor Xa inhibitor Drugs 0.000 claims 3
- 229920001499 Heparinoid Polymers 0.000 claims 3
- 208000008589 Obesity Diseases 0.000 claims 3
- 102100030951 Tissue factor pathway inhibitor Human genes 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical group O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 206010012601 diabetes mellitus Diseases 0.000 claims 3
- 239000002554 heparinoid Substances 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical class 0.000 claims 3
- 108010013555 lipoprotein-associated coagulation inhibitor Proteins 0.000 claims 3
- 229940127215 low-molecular weight heparin Drugs 0.000 claims 3
- 239000003607 modifier Substances 0.000 claims 3
- 125000001624 naphthyl group Chemical group 0.000 claims 3
- 235000020824 obesity Nutrition 0.000 claims 3
- 125000002971 oxazolyl group Chemical group 0.000 claims 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 3
- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 2
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 2
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 claims 2
- LMHIPJMTZHDKEW-XQYLJSSYSA-M Epoprostenol sodium Chemical compound [Na+].O1\C(=C/CCCC([O-])=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 LMHIPJMTZHDKEW-XQYLJSSYSA-M 0.000 claims 2
- 229960001138 acetylsalicylic acid Drugs 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 229940127219 anticoagulant drug Drugs 0.000 claims 2
- 229940127218 antiplatelet drug Drugs 0.000 claims 2
- 229960004676 antithrombotic agent Drugs 0.000 claims 2
- 125000004104 aryloxy group Chemical class 0.000 claims 2
- 150000001540 azides Chemical class 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000000051 benzyloxy group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
- 229960002890 beraprost Drugs 0.000 claims 2
- CTPOHARTNNSRSR-APJZLKAGSA-N beraprost Chemical compound O([C@H]1C[C@@H](O)[C@@H]([C@@H]21)/C=C/[C@@H](O)C(C)CC#CC)C1=C2C=CC=C1CCCC(O)=O CTPOHARTNNSRSR-APJZLKAGSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- OIRCOABEOLEUMC-GEJPAHFPSA-N bivalirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)CNC(=O)CNC(=O)CNC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](N)CC=1C=CC=CC=1)C1=CC=CC=C1 OIRCOABEOLEUMC-GEJPAHFPSA-N 0.000 claims 2
- 229960001500 bivalirudin Drugs 0.000 claims 2
- 108010055460 bivalirudin Proteins 0.000 claims 2
- 235000012000 cholesterol Nutrition 0.000 claims 2
- 229960004588 cilostazol Drugs 0.000 claims 2
- RRGUKTPIGVIEKM-UHFFFAOYSA-N cilostazol Chemical compound C=1C=C2NC(=O)CCC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 RRGUKTPIGVIEKM-UHFFFAOYSA-N 0.000 claims 2
- 229940018872 dalteparin sodium Drugs 0.000 claims 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims 2
- VJDOPFARMOLELX-ZDUSSCGKSA-N ethyl 3-[[(3s)-1-(4-carbamimidoylphenyl)-2-oxopyrrolidin-3-yl]carbamoylamino]propanoate Chemical compound O=C1[C@@H](NC(=O)NCCC(=O)OCC)CCN1C1=CC=C(C(N)=N)C=C1 VJDOPFARMOLELX-ZDUSSCGKSA-N 0.000 claims 2
- 239000002319 fibrinogen receptor antagonist Substances 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 2
- CGIGDMFJXJATDK-UHFFFAOYSA-N indomethacin Chemical compound CC1=C(CC(O)=O)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 CGIGDMFJXJATDK-UHFFFAOYSA-N 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- 239000003055 low molecular weight heparin Substances 0.000 claims 2
- 229950002383 orbofiban Drugs 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- 230000001225 therapeutic effect Effects 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- 229960003425 tirofiban Drugs 0.000 claims 2
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical compound C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 claims 2
- HSINOMROUCMIEA-FGVHQWLLSA-N (2s,4r)-4-[(3r,5s,6r,7r,8s,9s,10s,13r,14s,17r)-6-ethyl-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-methylpentanoic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)C[C@H](C)C(O)=O)CC[C@H]21 HSINOMROUCMIEA-FGVHQWLLSA-N 0.000 claims 1
- RCNHFUDTRRGRGW-UHFFFAOYSA-N 1,2-benzothiazin-4-one Chemical compound C1=CC=C2C(=O)C=NSC2=C1 RCNHFUDTRRGRGW-UHFFFAOYSA-N 0.000 claims 1
- ULNVBRUIKLYGDF-UHFFFAOYSA-N 1,3-bis(4-methylphenyl)thiourea Chemical group C1=CC(C)=CC=C1NC(=S)NC1=CC=C(C)C=C1 ULNVBRUIKLYGDF-UHFFFAOYSA-N 0.000 claims 1
- YETULFFXNIHQLK-UHFFFAOYSA-N 1-ethynyl-4-(2-fluorophenyl)benzene Chemical compound FC1=CC=CC=C1C1=CC=C(C#C)C=C1 YETULFFXNIHQLK-UHFFFAOYSA-N 0.000 claims 1
- OICPCODTYMAQOE-UHFFFAOYSA-N 1-phenyl-2,3-dihydropyrrole-5-carboximidamide Chemical compound NC(=N)C1=CCCN1C1=CC=CC=C1 OICPCODTYMAQOE-UHFFFAOYSA-N 0.000 claims 1
- CVJRRJMEMYTWRC-UHFFFAOYSA-N 1-phenylpyrrolidine-2-carboximidamide Chemical compound NC(=N)C1CCCN1C1=CC=CC=C1 CVJRRJMEMYTWRC-UHFFFAOYSA-N 0.000 claims 1
- NUNZGJKXTJMXGY-UHFFFAOYSA-N 1H-indole-2-carboximidamide Chemical compound C1=CC=C2NC(C(=N)N)=CC2=C1 NUNZGJKXTJMXGY-UHFFFAOYSA-N 0.000 claims 1
- FSUPKDUNLKQBCN-UHFFFAOYSA-N 1H-pyrrole-2-carboximidamide Chemical compound NC(=N)C1=CC=CN1 FSUPKDUNLKQBCN-UHFFFAOYSA-N 0.000 claims 1
- JKCHHDHEHOKKQP-UHFFFAOYSA-N 1h-imidazol-2-ylboronic acid Chemical compound OB(O)C1=NC=CN1 JKCHHDHEHOKKQP-UHFFFAOYSA-N 0.000 claims 1
- TWWNPUZQYVWXJY-UHFFFAOYSA-N 1h-quinazoline-4-thione Chemical compound C1=CC=C2C(S)=NC=NC2=C1 TWWNPUZQYVWXJY-UHFFFAOYSA-N 0.000 claims 1
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims 1
- BYDKEYCXCIVOOV-JTSKRJEESA-N 2-[[(2s)-4-[[(3s)-1-carbamimidoylpiperidin-3-yl]methylamino]-2-(naphthalen-2-ylsulfonylamino)-4-oxobutanoyl]-cyclopropylamino]acetic acid Chemical compound C1N(C(=N)N)CCC[C@H]1CNC(=O)C[C@@H](C(=O)N(CC(O)=O)C1CC1)NS(=O)(=O)C1=CC=C(C=CC=C2)C2=C1 BYDKEYCXCIVOOV-JTSKRJEESA-N 0.000 claims 1
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical compound C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 1
- ZBLJEMQEPGCCJA-UHFFFAOYSA-N 2-phenyl-1,2-oxazolidine-3-carboximidamide Chemical compound NC(=N)C1CCON1C1=CC=CC=C1 ZBLJEMQEPGCCJA-UHFFFAOYSA-N 0.000 claims 1
- FKMCYKOPRFRZDN-UHFFFAOYSA-N 3,1-benzoxazine-4-thione Chemical compound C1=CC=C2C(=S)OC=NC2=C1 FKMCYKOPRFRZDN-UHFFFAOYSA-N 0.000 claims 1
- HYTIPJFUWHYQON-UHFFFAOYSA-N 3,4-dihydro-1h-quinoxalin-2-one Chemical compound C1=CC=C2NC(=O)CNC2=C1 HYTIPJFUWHYQON-UHFFFAOYSA-N 0.000 claims 1
- RTRQQBHATOEIAF-UHFFFAOYSA-N AICA riboside Natural products NC1=C(C(=O)N)N=CN1C1C(O)C(O)C(CO)O1 RTRQQBHATOEIAF-UHFFFAOYSA-N 0.000 claims 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 101000783577 Dendroaspis angusticeps Thrombostatin Proteins 0.000 claims 1
- 101000783578 Dendroaspis jamesoni kaimosae Dendroaspin Proteins 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 1
- 241000257303 Hymenoptera Species 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 102000000853 LDL receptors Human genes 0.000 claims 1
- 108010001831 LDL receptors Proteins 0.000 claims 1
- 108090001030 Lipoproteins Proteins 0.000 claims 1
- 102000004895 Lipoproteins Human genes 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- LEZHMTGJGJTOBP-FQEVSTJZSA-N NN=CC=1C=C(CN2C([C@H](CC2)NS(=O)(=O)N2CC3=CC=CC=C3CC2)=O)C=CC1 Chemical compound NN=CC=1C=C(CN2C([C@H](CC2)NS(=O)(=O)N2CC3=CC=CC=C3CC2)=O)C=CC1 LEZHMTGJGJTOBP-FQEVSTJZSA-N 0.000 claims 1
- CMWTZPSULFXXJA-UHFFFAOYSA-N Naproxen Natural products C1=C(C(C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-UHFFFAOYSA-N 0.000 claims 1
- BYPFEZZEUUWMEJ-UHFFFAOYSA-N Pentoxifylline Chemical compound O=C1N(CCCCC(=O)C)C(=O)N(C)C2=C1N(C)C=N2 BYPFEZZEUUWMEJ-UHFFFAOYSA-N 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- WBNUCLPUOSXSNJ-ZDUSSCGKSA-N Sibrafiban Chemical compound C1CC(OCC(=O)OCC)CCN1C(=O)[C@H](C)NC(=O)C1=CC=C(C(=N)NO)C=C1 WBNUCLPUOSXSNJ-ZDUSSCGKSA-N 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- SRXKIZXIRHMPFW-UHFFFAOYSA-N [4-[6-[amino(azaniumylidene)methyl]naphthalen-2-yl]oxycarbonylphenyl]-(diaminomethylidene)azanium;methanesulfonate Chemical compound CS([O-])(=O)=O.CS([O-])(=O)=O.C1=CC(N=C([NH3+])N)=CC=C1C(=O)OC1=CC=C(C=C(C=C2)C([NH3+])=N)C2=C1 SRXKIZXIRHMPFW-UHFFFAOYSA-N 0.000 claims 1
- 229960003000 acadesine Drugs 0.000 claims 1
- RTRQQBHATOEIAF-UUOKFMHZSA-N acadesine Chemical group NC1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 RTRQQBHATOEIAF-UUOKFMHZSA-N 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims 1
- 125000000676 alkoxyimino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005336 allyloxy group Chemical group 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 229960003555 anagrelide hydrochloride Drugs 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- KXNPVXPOPUZYGB-XYVMCAHJSA-N argatroban Chemical compound OC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCN=C(N)N)NS(=O)(=O)C1=CC=CC2=C1NC[C@H](C)C2 KXNPVXPOPUZYGB-XYVMCAHJSA-N 0.000 claims 1
- 229960003856 argatroban Drugs 0.000 claims 1
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 1
- MXMZCLLIUQEKSN-UHFFFAOYSA-N benzimidazoline Chemical compound C1=CC=C2NCNC2=C1 MXMZCLLIUQEKSN-UHFFFAOYSA-N 0.000 claims 1
- 125000005605 benzo group Chemical class 0.000 claims 1
- 125000002047 benzodioxolyl group Chemical class O1OC(C2=C1C=CC=C2)* 0.000 claims 1
- 239000003613 bile acid Substances 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- GKTWGGQPFAXNFI-HNNXBMFYSA-N clopidogrel Chemical compound C1([C@H](N2CC=3C=CSC=3CC2)C(=O)OC)=CC=CC=C1Cl GKTWGGQPFAXNFI-HNNXBMFYSA-N 0.000 claims 1
- 229960003958 clopidogrel bisulfate Drugs 0.000 claims 1
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960004969 dalteparin Drugs 0.000 claims 1
- 229960003828 danaparoid Drugs 0.000 claims 1
- 229960004776 danaparoid sodium Drugs 0.000 claims 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 claims 1
- 229960001259 diclofenac Drugs 0.000 claims 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 claims 1
- 229960001912 dicoumarol Drugs 0.000 claims 1
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-
2002
- 2002-01-25 KR KR10-2003-7009794A patent/KR20040025890A/ko not_active Ceased
- 2002-01-25 HU HU0303917A patent/HUP0303917A2/hu unknown
- 2002-01-25 MX MXPA03006728A patent/MXPA03006728A/es active IP Right Grant
- 2002-01-25 NZ NZ542090A patent/NZ542090A/en unknown
- 2002-01-25 PL PL02364178A patent/PL364178A1/xx not_active Application Discontinuation
- 2002-01-25 SK SK950-2003A patent/SK9502003A3/sk not_active Application Discontinuation
- 2002-01-25 DK DK02704233T patent/DK1353694T3/da active
- 2002-01-25 PT PT02704233T patent/PT1353694E/pt unknown
- 2002-01-25 AU AU2002237927A patent/AU2002237927B2/en not_active Ceased
- 2002-01-25 WO PCT/US2002/002013 patent/WO2002058734A2/en not_active Ceased
- 2002-01-25 CZ CZ20032039A patent/CZ20032039A3/cs unknown
- 2002-01-25 KR KR1020087015928A patent/KR20080067717A/ko not_active Ceased
- 2002-01-25 US US10/056,680 patent/US20020147184A1/en not_active Abandoned
- 2002-01-25 JP JP2002559068A patent/JP2004517920A/ja active Pending
- 2002-01-25 EP EP07009475A patent/EP1810693A3/en not_active Withdrawn
- 2002-01-25 EP EP02704233A patent/EP1353694B1/en not_active Expired - Lifetime
- 2002-01-25 CA CA002434504A patent/CA2434504A1/en not_active Abandoned
- 2002-01-25 RU RU2003126185/15A patent/RU2314126C2/ru not_active IP Right Cessation
- 2002-01-25 SI SI200230652T patent/SI1353694T1/sl unknown
- 2002-01-25 ES ES02704233T patent/ES2296894T3/es not_active Expired - Lifetime
- 2002-01-25 CN CN028042204A patent/CN1658903A/zh active Pending
- 2002-01-25 IL IL15648802A patent/IL156488A0/xx unknown
- 2002-01-25 AR ARP020100271A patent/AR032403A1/es not_active Application Discontinuation
- 2002-01-25 DE DE60224163T patent/DE60224163T2/de not_active Expired - Fee Related
- 2002-01-25 AT AT02704233T patent/ATE381347T1/de not_active IP Right Cessation
- 2002-01-25 BR BR0206639-4A patent/BR0206639A/pt not_active IP Right Cessation
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2003
- 2003-07-25 NO NO20033357A patent/NO20033357L/no not_active Application Discontinuation
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2008
- 2008-02-04 CY CY20081100128T patent/CY1107174T1/el unknown
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