SK8032003A3 - Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives - Google Patents

Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives Download PDF

Info

Publication number: SK8032003A3
Authority: SK; Slovakia
Prior art keywords: pyrimidin; pharmaceutical composition; group; hal; acid
Prior art date: 2000-12-19

Application number

SK803-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Hans-Michael Eggenweiler

Volker Eiermann

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.)

2000-12-19

Filing date

2001-11-28

Publication date

2003-11-04

2000-12-19 Priority claimed from DE10063221A external-priority patent/DE10063221A1/de

2000-12-21 Priority claimed from DE2000163884 external-priority patent/DE10063884A1/de

2000-12-23 Priority claimed from DE2000164991 external-priority patent/DE10064991A1/de

2001-11-28 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2003-11-04 Publication of SK8032003A3 publication Critical patent/SK8032003A3/sk

Links

150000003180 prostaglandins Chemical class 0.000 title claims abstract description 78
239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 66
229940127291 Calcium channel antagonist Drugs 0.000 title claims abstract description 41
230000002785 anti-thrombosis Effects 0.000 title claims abstract description 30
229960004676 antithrombotic agent Drugs 0.000 title claims description 9
229940094443 oxytocics prostaglandins Drugs 0.000 title description 5
150000001875 compounds Chemical group 0.000 claims abstract description 104
150000003839 salts Chemical class 0.000 claims abstract description 63
239000012453 solvate Substances 0.000 claims abstract description 48
239000003146 anticoagulant agent Substances 0.000 claims abstract description 32
239000000480 calcium channel blocker Substances 0.000 claims abstract description 31
206010019280 Heart failures Diseases 0.000 claims abstract description 20
239000003814 drug Substances 0.000 claims abstract description 17
206010007559 Cardiac failure congestive Diseases 0.000 claims abstract description 14
208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract description 10
206010039163 Right ventricular failure Diseases 0.000 claims abstract description 9
208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 9
206010002383 Angina Pectoris Diseases 0.000 claims abstract description 5
206010028980 Neoplasm Diseases 0.000 claims abstract description 5
208000001647 Renal Insufficiency Diseases 0.000 claims abstract description 5
208000023819 chronic asthma Diseases 0.000 claims abstract description 5
208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 5
201000006370 kidney failure Diseases 0.000 claims abstract description 5
208000010412 Glaucoma Diseases 0.000 claims abstract description 4
201000009961 allergic asthma Diseases 0.000 claims abstract description 4
208000006673 asthma Diseases 0.000 claims abstract description 4
206010006451 bronchitis Diseases 0.000 claims abstract description 4
208000002551 irritable bowel syndrome Diseases 0.000 claims abstract description 4
206010020772 Hypertension Diseases 0.000 claims abstract description 3
206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 3
201000010105 allergic rhinitis Diseases 0.000 claims abstract description 3
-1 COOA Chemical group 0.000 claims description 108
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 62
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 61
125000004432 carbon atom Chemical group C* 0.000 claims description 45
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 45
239000000460 chlorine Substances 0.000 claims description 42
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 41
229910052731 fluorine Inorganic materials 0.000 claims description 40
229910052801 chlorine Inorganic materials 0.000 claims description 39
229910052794 bromium Inorganic materials 0.000 claims description 36
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 35
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 35
239000011737 fluorine Substances 0.000 claims description 35
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 29
239000002253 acid Substances 0.000 claims description 29
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 29
229910052740 iodine Inorganic materials 0.000 claims description 29
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
125000002947 alkylene group Chemical group 0.000 claims description 25
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 19
150000002169 ethanolamines Chemical class 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000005605 benzo group Chemical group 0.000 claims description 15
KJJPAVCZQWWWMM-UHFFFAOYSA-N 4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(C2CCC(CC2)C(O)=O)=NC2=C1C1=CC=CC=C1S2 KJJPAVCZQWWWMM-UHFFFAOYSA-N 0.000 claims description 13
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
125000000753 cycloalkyl group Chemical group 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims description 11
208000019693 Lung disease Diseases 0.000 claims description 10
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 10
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 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 claims description 9
206010020880 Hypertrophy Diseases 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
229960001123 epoprostenol Drugs 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 8
DEXVZSUFJVAVML-UHFFFAOYSA-N 2-aminoethanol;4-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]cyclohexane-1-carboxylic acid Chemical compound NCCO.C1=C(Cl)C(OC)=CC=C1CNC1=NC(C2CCC(CC2)C(O)=O)=NC2=C1C1=CC=CC=C1S2 DEXVZSUFJVAVML-UHFFFAOYSA-N 0.000 claims description 6
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 6
239000011575 calcium Substances 0.000 claims description 6
229910052791 calcium Inorganic materials 0.000 claims description 6
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
239000002590 phosphodiesterase V inhibitor Substances 0.000 claims description 6
AWQSAIIDOMEEOD-UHFFFAOYSA-N 5,5-Dimethyl-4-(3-oxobutyl)dihydro-2(3H)-furanone Chemical compound CC(=O)CCC1CC(=O)OC1(C)C AWQSAIIDOMEEOD-UHFFFAOYSA-N 0.000 claims description 5
102000004190 Enzymes Human genes 0.000 claims description 5
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239000005557 antagonist Substances 0.000 claims description 5
229940127218 antiplatelet drug Drugs 0.000 claims description 5
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229940088598 enzyme Drugs 0.000 claims description 5
239000000106 platelet aggregation inhibitor Substances 0.000 claims description 5
GMVPRGQOIOIIMI-UHFFFAOYSA-N (8R,11R,12R,13E,15S)-11,15-Dihydroxy-9-oxo-13-prostenoic acid Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CCCCCCC(O)=O GMVPRGQOIOIIMI-UHFFFAOYSA-N 0.000 claims description 4
QVHPHQZZUULWAS-UHFFFAOYSA-N 7-[4-(1,3-benzodioxol-5-ylmethylamino)-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1=CC=C2C3=C(NCC=4C=C5OCOC5=CC=4)N=C(CCCCCCC(=O)O)N=C3SC2=C1 QVHPHQZZUULWAS-UHFFFAOYSA-N 0.000 claims description 4
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
229960000711 alprostadil Drugs 0.000 claims description 4
150000007657 benzothiazepines Chemical class 0.000 claims description 4
229960001342 dinoprost Drugs 0.000 claims description 4
229960002986 dinoprostone Drugs 0.000 claims description 4
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims description 4
FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 claims description 4
229960002240 iloprost Drugs 0.000 claims description 4
HIFJCPQKFCZDDL-ACWOEMLNSA-N iloprost Chemical compound C1\C(=C/CCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)C(C)CC#CC)[C@H](O)C[C@@H]21 HIFJCPQKFCZDDL-ACWOEMLNSA-N 0.000 claims description 4
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims description 4
PXGPLTODNUVGFL-YNNPMVKQSA-N prostaglandin F2alpha Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O PXGPLTODNUVGFL-YNNPMVKQSA-N 0.000 claims description 4
229940085239 selective calcium channel blockers with direct cardiac effects phenylalkylamine derivative Drugs 0.000 claims description 4
229940005605 valeric acid Drugs 0.000 claims description 4
229940019333 vitamin k antagonists Drugs 0.000 claims description 4
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 3
YKNCNWFUQFZYCW-UHFFFAOYSA-N 3-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]propanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCC(O)=O)=NC2=C1C1=CC=CC=C1S2 YKNCNWFUQFZYCW-UHFFFAOYSA-N 0.000 claims description 3
VXCPPJWBHMZOCM-UHFFFAOYSA-N 5-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]pentanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCC(O)=O)=NC2=C1C1=CC=CC=C1S2 VXCPPJWBHMZOCM-UHFFFAOYSA-N 0.000 claims description 3
OGMKXSIWCDVZCH-UHFFFAOYSA-N 7-[4-[(3-chloro-4-methoxyphenyl)methylamino]-[1]benzothiolo[2,3-d]pyrimidin-2-yl]heptanoic acid Chemical compound C1=C(Cl)C(OC)=CC=C1CNC1=NC(CCCCCCC(O)=O)=NC2=C1C1=CC=CC=C1S2 OGMKXSIWCDVZCH-UHFFFAOYSA-N 0.000 claims description 3
201000001320 Atherosclerosis Diseases 0.000 claims description 3
239000005711 Benzoic acid Substances 0.000 claims description 3
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 description 3
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KYBOHGVERHWSSV-VNIVIJDLSA-N gemeprost Chemical compound CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCC\C=C\C(=O)OC KYBOHGVERHWSSV-VNIVIJDLSA-N 0.000 claims description 3
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 claims description 3
GGXICVAJURFBLW-CEYXHVGTSA-N latanoprost Chemical compound CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 GGXICVAJURFBLW-CEYXHVGTSA-N 0.000 claims description 3
229960001160 latanoprost Drugs 0.000 claims description 3
235000019260 propionic acid Nutrition 0.000 claims description 3
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 3
239000011734 sodium Substances 0.000 claims description 3
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UQZVCDCIMBLVNR-TWYODKAFSA-N sulprostone Chemical compound O[C@@H]1CC(=O)[C@H](C\C=C/CCCC(=O)NS(=O)(=O)C)[C@H]1\C=C\[C@@H](O)COC1=CC=CC=C1 UQZVCDCIMBLVNR-TWYODKAFSA-N 0.000 claims description 3
HMJIYCCIJYRONP-UHFFFAOYSA-N (+-)-Isradipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC2=NON=C12 HMJIYCCIJYRONP-UHFFFAOYSA-N 0.000 claims description 2
PVHUJELLJLJGLN-INIZCTEOSA-N (S)-nitrendipine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC([N+]([O-])=O)=C1 PVHUJELLJLJGLN-INIZCTEOSA-N 0.000 claims description 2
FYBFDIIAPRHIQS-KKBLUXBBSA-N (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-thiophen-3-yloxybut-1-enyl]cyclopentyl]hept-5-enoic acid Chemical compound C([C@H](O)\C=C\[C@@H]1[C@H]([C@@H](O)C[C@H]1O)C\C=C/CCCC(O)=O)OC=1C=CSC=1 FYBFDIIAPRHIQS-KKBLUXBBSA-N 0.000 claims description 2
SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 claims description 2
ZBIAKUMOEKILTF-UHFFFAOYSA-N 2-[4-[4,4-bis(4-fluorophenyl)butyl]-1-piperazinyl]-N-(2,6-dimethylphenyl)acetamide Chemical compound CC1=CC=CC(C)=C1NC(=O)CN1CCN(CCCC(C=2C=CC(F)=CC=2)C=2C=CC(F)=CC=2)CC1 ZBIAKUMOEKILTF-UHFFFAOYSA-N 0.000 claims description 2
NMKSAYKQLCHXDK-UHFFFAOYSA-N 3,3-diphenyl-N-(1-phenylethyl)-1-propanamine Chemical compound C=1C=CC=CC=1C(C)NCCC(C=1C=CC=CC=1)C1=CC=CC=C1 NMKSAYKQLCHXDK-UHFFFAOYSA-N 0.000 claims description 2
UIAGMCDKSXEBJQ-IBGZPJMESA-N 3-o-(2-methoxyethyl) 5-o-propan-2-yl (4s)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound COCCOC(=O)C1=C(C)NC(C)=C(C(=O)OC(C)C)[C@H]1C1=CC=CC([N+]([O-])=O)=C1 UIAGMCDKSXEBJQ-IBGZPJMESA-N 0.000 claims description 2
ABYGSZMCWVXFCQ-UHFFFAOYSA-N 4-propylheptane Chemical compound CCCC(CCC)CCC ABYGSZMCWVXFCQ-UHFFFAOYSA-N 0.000 claims description 2
RZTAMFZIAATZDJ-HNNXBMFYSA-N 5-o-ethyl 3-o-methyl (4s)-4-(2,3-dichlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OC)[C@@H]1C1=CC=CC(Cl)=C1Cl RZTAMFZIAATZDJ-HNNXBMFYSA-N 0.000 claims description 2
108010058207 Anistreplase Proteins 0.000 claims description 2
239000005528 B01AC05 - Ticlopidine Substances 0.000 claims description 2
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JYGLAHSAISAEAL-UHFFFAOYSA-N Diphenadione Chemical compound O=C1C2=CC=CC=C2C(=O)C1C(=O)C(C=1C=CC=CC=1)C1=CC=CC=C1 JYGLAHSAISAEAL-UHFFFAOYSA-N 0.000 claims description 2
229940082863 Factor VIIa inhibitor Drugs 0.000 claims description 2
108010088842 Fibrinolysin Proteins 0.000 claims description 2
XQLWNAFCTODIRK-UHFFFAOYSA-N Gallopamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC(OC)=C(OC)C(OC)=C1 XQLWNAFCTODIRK-UHFFFAOYSA-N 0.000 claims description 2
HBNPJJILLOYFJU-VMPREFPWSA-N Mibefradil Chemical group C1CC2=CC(F)=CC=C2[C@H](C(C)C)[C@@]1(OC(=O)COC)CCN(C)CCCC1=NC2=CC=CC=C2N1 HBNPJJILLOYFJU-VMPREFPWSA-N 0.000 claims description 2
ZBBHBTPTTSWHBA-UHFFFAOYSA-N Nicardipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OCCN(C)CC=2C=CC=CC=2)C1C1=CC=CC([N+]([O-])=O)=C1 ZBBHBTPTTSWHBA-UHFFFAOYSA-N 0.000 claims description 2
FAIIFDPAEUKBEP-UHFFFAOYSA-N Nilvadipine Chemical compound COC(=O)C1=C(C#N)NC(C)=C(C(=O)OC(C)C)C1C1=CC=CC([N+]([O-])=O)=C1 FAIIFDPAEUKBEP-UHFFFAOYSA-N 0.000 claims description 2
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102000003978 Tissue Plasminogen Activator Human genes 0.000 claims description 2
108090000435 Urokinase-type plasminogen activator Proteins 0.000 claims description 2
102000003990 Urokinase-type plasminogen activator Human genes 0.000 claims description 2
JNWFIPVDEINBAI-UHFFFAOYSA-N [5-hydroxy-4-[4-(1-methylindol-5-yl)-5-oxo-1H-1,2,4-triazol-3-yl]-2-propan-2-ylphenyl] dihydrogen phosphate Chemical compound C1=C(OP(O)(O)=O)C(C(C)C)=CC(C=2N(C(=O)NN=2)C=2C=C3C=CN(C)C3=CC=2)=C1O JNWFIPVDEINBAI-UHFFFAOYSA-N 0.000 claims description 2
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HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical compound CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims description 2
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VXMOONUMYLCFJD-DHLKQENFSA-N barnidipine Chemical compound C1([C@@H]2C(=C(C)NC(C)=C2C(=O)OC)C(=O)O[C@@H]2CN(CC=3C=CC=CC=3)CC2)=CC=CC([N+]([O-])=O)=C1 VXMOONUMYLCFJD-DHLKQENFSA-N 0.000 claims description 2
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UIEATEWHFDRYRU-UHFFFAOYSA-N bepridil Chemical compound C1CCCN1C(COCC(C)C)CN(C=1C=CC=CC=1)CC1=CC=CC=C1 UIEATEWHFDRYRU-UHFFFAOYSA-N 0.000 claims description 2
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DLJKPYFALUEJCK-MRVZPHNRSA-N carboprost Chemical compound CCCCC[C@](C)(O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(O)=O DLJKPYFALUEJCK-MRVZPHNRSA-N 0.000 claims description 2
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239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000000542 sulfonic acid group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical class S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000003577 thiophenes Chemical class 0.000 description 1
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 description 1
229960003425 tirofiban Drugs 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
230000001196 vasorelaxation Effects 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
229930003231 vitamin Natural products 0.000 description 1
239000011782 vitamin Substances 0.000 description 1
229940088594 vitamin Drugs 0.000 description 1
235000013343 vitamin Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A—HUMAN NECESSITIES
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- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
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- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
- A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- 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
- 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
- A61P9/12—Antihypertensives
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers

Landscapes

Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Epidemiology (AREA)
Pulmonology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Vascular Medicine (AREA)
Ophthalmology & Optometry (AREA)
Hematology (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Gynecology & Obstetrics (AREA)
Rheumatology (AREA)
Obesity (AREA)
Pregnancy & Childbirth (AREA)
Immunology (AREA)
Hospice & Palliative Care (AREA)
Otolaryngology (AREA)
Gastroenterology & Hepatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

SK803-2003A 2000-12-19 2001-11-28 Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives SK8032003A3 (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
DE10063221A DE10063221A1 (de)	2000-12-19	2000-12-19	Pharmazeutische Formulierung enthaltend Thienopyrimidine und Antithrombotica (2)
DE2000163884 DE10063884A1 (de)	2000-12-21	2000-12-21	Pharmazeutische Formulierung enthaltend Thienopyrimidine und Calcium-Antagonisten (2)
DE2000164991 DE10064991A1 (de)	2000-12-23	2000-12-23	Pharmazeutische Formulierung enthaltend Thienopyrimidine und Prostaglandine oder Prostaglandinderivate (2)
PCT/EP2001/013913 WO2002049649A2 (de)	2000-12-19	2001-11-28	Pharmazeutische formulierung enthaltend thienopyrimidine und antithrombotica, calcium-antagonisten, prostaglandine oder prostaglandinderivate (2)

Publications (1)

Publication Number	Publication Date
SK8032003A3 true SK8032003A3 (en)	2003-11-04

Family

ID=27214206

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK803-2003A SK8032003A3 (en)	2000-12-19	2001-11-28	Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives

Country Status (16)

Country	Link
US (1)	US20040058940A1 (cs)
EP (1)	EP1347762A2 (cs)
JP (1)	JP2004516268A (cs)
KR (1)	KR20030059350A (cs)
CN (1)	CN1481243A (cs)
AR (1)	AR035675A1 (cs)
AU (1)	AU2002226362A1 (cs)
BR (1)	BR0116247A (cs)
CA (1)	CA2431147A1 (cs)
CZ (1)	CZ20031722A3 (cs)
HU (1)	HUP0401368A2 (cs)
MX (1)	MXPA03005441A (cs)
NO (1)	NO20032771L (cs)
PL (1)	PL361812A1 (cs)
SK (1)	SK8032003A3 (cs)
WO (1)	WO2002049649A2 (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20050107394A1 (en) *	2001-12-17	2005-05-19	Ardeschir Ghofrani	Novel use of selective pde5 inhibitors
KR20090028819A (ko) *	2006-07-11	2009-03-19	얀센 파마슈티카 엔.브이.	히스타민 ｈ４ 수용체의 벤조푸로- 및 벤조티에노피리미딘 조절제
WO2018160625A1 (en) *	2017-02-28	2018-09-07	Vanderbilt University	Prostacyclin, prostacyclin analogs, and methods of treating or preventing rejection of solid organ transplants

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2353285A1 (fr) *	1975-09-17	1977-12-30	Doms Laboratoires	Medicament vasodilatateur coronarien perfectionne
JPS5459266A (en) *	1977-10-14	1979-05-12	Ono Pharmaceut Co Ltd	Prostaglandin i2 analogs and their preparation
FR2568774B2 (fr) *	1984-05-30	1989-05-19	Choay Sa	Medicaments favorisant les proprietes d'ecoulement du sang et leur utilisation en therapeutique
FR2672601B1 (fr) *	1991-02-08	1994-10-14	Synthelabo	Derives de benzo-1,5-thiazepine, leur preparation et leur application en therapeutique.
US6143746A (en) *	1994-01-21	2000-11-07	Icos Corporation	Tetracyclic cyclic GMP-specific phosphodiesterase inhibitors, process of preparation and use
US6156753A (en) *	1997-10-28	2000-12-05	Vivus, Inc.	Local administration of type III phosphodiesterase inhibitors for the treatment of erectile dysfunction
JP2003525845A (ja) *	1997-10-28	2003-09-02	ヴィヴァス・インコーポレイテッド	勃起機能不全の処置のためのホスホジエステラーゼインヒビターの局所投与
DE19819023A1 (de) *	1998-04-29	1999-11-04	Merck Patent Gmbh	Thienopyrimidine
DE19943815A1 (de) *	1999-09-14	2001-03-15	Merck Patent Gmbh	Verwendung von Thienopyrimidinen

2001
- 2001-11-28 EP EP01995677A patent/EP1347762A2/de not_active Withdrawn
- 2001-11-28 WO PCT/EP2001/013913 patent/WO2002049649A2/de not_active Ceased
- 2001-11-28 CZ CZ20031722A patent/CZ20031722A3/cs unknown
- 2001-11-28 US US10/451,025 patent/US20040058940A1/en not_active Abandoned
- 2001-11-28 SK SK803-2003A patent/SK8032003A3/sk unknown
- 2001-11-28 MX MXPA03005441A patent/MXPA03005441A/es unknown
- 2001-11-28 CN CNA018208215A patent/CN1481243A/zh active Pending
- 2001-11-28 PL PL01361812A patent/PL361812A1/xx unknown
- 2001-11-28 HU HU0401368A patent/HUP0401368A2/hu unknown
- 2001-11-28 BR BR0116247-0A patent/BR0116247A/pt not_active Application Discontinuation
- 2001-11-28 JP JP2002550989A patent/JP2004516268A/ja active Pending
- 2001-11-28 AU AU2002226362A patent/AU2002226362A1/en not_active Abandoned
- 2001-11-28 KR KR10-2003-7008137A patent/KR20030059350A/ko not_active Withdrawn
- 2001-11-28 CA CA002431147A patent/CA2431147A1/en not_active Abandoned
- 2001-12-19 AR ARP010105886A patent/AR035675A1/es unknown
2003
- 2003-06-18 NO NO20032771A patent/NO20032771L/no unknown

Also Published As

Publication number	Publication date
KR20030059350A (ko)	2003-07-07
MXPA03005441A (es)	2003-09-10
PL361812A1 (en)	2004-10-04
JP2004516268A (ja)	2004-06-03
CN1481243A (zh)	2004-03-10
BR0116247A (pt)	2003-11-04
WO2002049649A3 (de)	2002-11-21
CZ20031722A3 (cs)	2003-09-17
HUP0401368A2 (hu)	2004-10-28
WO2002049649A2 (de)	2002-06-27
US20040058940A1 (en)	2004-03-25
NO20032771D0 (no)	2003-06-18
NO20032771L (no)	2003-06-18
AU2002226362A1 (en)	2002-07-01
EP1347762A2 (de)	2003-10-01
CA2431147A1 (en)	2002-06-27
AR035675A1 (es)	2004-06-23

Publication	Publication Date	Title
SK8192003A3 (en)	2003-10-07	Pharmaceutical formulation containing pyrazolo[4,3-d]pyrimidines and antithrombotic agents, calcium-antagonists, prostaglandins or prostaglandin derivatives
US20040034040A1 (en)	2004-02-19	Use of thienopyrimidines
ES2303564T3 (es)	2008-08-16	Derivados de pirimidina.
CA2432582C (en)	2011-01-25	Sulfamidothienopyrimidines
US20040072846A1 (en)	2004-04-15	Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives
SK8032003A3 (en)	2003-11-04	Pharmaceutical formulation containing thienopyrimidines and antithrombotics, calcium antagonists, prostaglandins or prostaglandin derivatives
US20040077664A1 (en)	2004-04-22	Pharmaceutical formulation comprising pyrazolo[4,3-d]pyrimidine and nitrates or thienopyrimidines and nitrates
US20030022906A1 (en)	2003-01-30	Use of pde v inhibitors
ZA200302513B (en)	2004-08-24	Thienopyrimidines.
ZA200305548B (en)	2005-01-26	Pharmaceutical formulation containing thienopyrimidines and antithrombotics calcium antagonists prostaglandins or prostaglandin derivatives (2)
KR20020026011A (ko)	2002-04-04	티에노피리미딘의 용도
ZA200305542B (en)	2005-01-26	Pharmaceutical formulation containing pyrazole [4,3-d]pymidines and antithrombotic agents calcium antagonists prostaglandins or prostaglandin derivatives
MXPA04003049A (es)	2004-07-05	Derivados de pirimidina.