IL104066A - Pyridyl derivatives their preparation and pharmaceutical compositions containing them - Google Patents

Pyridyl derivatives their preparation and pharmaceutical compositions containing them

Info

Publication number: IL104066A
Authority: IL; Israel
Prior art keywords: group; pyridyl; phenyl; hex; formula
Prior art date: 1991-12-14

Application number

IL10406692A

Other languages

English (en)

Other versions

IL104066A0 (en

Original Assignee

Thomae Gmbh Dr K

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.)

1991-12-14

Filing date

1992-12-11

Publication date

1996-07-23

1991-12-14 Priority claimed from DE4141377A external-priority patent/DE4141377A1/de

1992-12-11 Application filed by Thomae Gmbh Dr K filed Critical Thomae Gmbh Dr K

1993-05-13 Publication of IL104066A0 publication Critical patent/IL104066A0/xx

1996-07-23 Publication of IL104066A publication Critical patent/IL104066A/en

Links

125000004076 pyridyl group Chemical group 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims description 20
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 127
125000000217 alkyl group Chemical group 0.000 claims abstract description 25
125000003545 alkoxy group Chemical group 0.000 claims abstract description 23
239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 14
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 12
230000001404 mediated effect Effects 0.000 claims abstract description 11
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 10
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 claims abstract description 9
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 claims abstract description 8
229960002986 dinoprostone Drugs 0.000 claims abstract description 8
XEYBRNLFEZDVAW-UHFFFAOYSA-N prostaglandin E2 Natural products CCCCCC(O)C=CC1C(O)CC(=O)C1CC=CCCCC(O)=O XEYBRNLFEZDVAW-UHFFFAOYSA-N 0.000 claims abstract description 8
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 abstract description 7
238000004519 manufacturing process Methods 0.000 claims abstract description 7
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
-1 nitromethylene group Chemical group 0.000 claims description 222
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 126
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 61
150000003839 salts Chemical class 0.000 claims description 40
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
238000000034 method Methods 0.000 claims description 22
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
239000000126 substance Substances 0.000 claims description 14
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
125000004892 2-methylpropylamino group Chemical group CC(CN*)C 0.000 claims description 12
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
230000008569 process Effects 0.000 claims description 9
125000003831 tetrazolyl group Chemical group 0.000 claims description 9
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
229940099471 Phosphodiesterase inhibitor Drugs 0.000 claims description 8
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 8
125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
238000011282 treatment Methods 0.000 claims description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
230000002265 prevention Effects 0.000 claims description 7
125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 6
239000005977 Ethylene Substances 0.000 claims description 6
150000001412 amines Chemical class 0.000 claims description 6
230000032050 esterification Effects 0.000 claims description 6
238000005886 esterification reaction Methods 0.000 claims description 6
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
238000001727 in vivo Methods 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
125000006239 protecting group Chemical group 0.000 claims description 6
SWLNUQSMWKYMJE-UFFVCSGVSA-N (e)-6-[3-[[n-cyano-n'-(2-methylpropyl)carbamimidoyl]amino]phenyl]-6-pyridin-3-ylhex-5-enoic acid Chemical compound CC(C)C\N=C(\NC#N)NC1=CC=CC(C(=C/CCCC(O)=O)\C=2C=NC=CC=2)=C1 SWLNUQSMWKYMJE-UFFVCSGVSA-N 0.000 claims description 5
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 claims description 5
229930105110 Cyclosporin A Natural products 0.000 claims description 5
108010036949 Cyclosporine Proteins 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
206010027476 Metastases Diseases 0.000 claims description 5
206010052779 Transplant rejections Diseases 0.000 claims description 5
208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
208000006673 asthma Diseases 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
229960001265 ciclosporin Drugs 0.000 claims description 5
229930182912 cyclosporin Natural products 0.000 claims description 5
230000018044 dehydration Effects 0.000 claims description 5
238000006297 dehydration reaction Methods 0.000 claims description 5
230000010339 dilation Effects 0.000 claims description 5
208000035475 disorder Diseases 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
208000028867 ischemia Diseases 0.000 claims description 5
208000017169 kidney disease Diseases 0.000 claims description 5
230000002934 lysing effect Effects 0.000 claims description 5
231100000417 nephrotoxicity Toxicity 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
230000035939 shock Effects 0.000 claims description 5
230000009424 thromboembolic effect Effects 0.000 claims description 5
125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
125000004897 3-methylbutylamino group Chemical group CC(CCN*)C 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
206010020751 Hypersensitivity Diseases 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
230000007815 allergy Effects 0.000 claims description 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
229910052727 yttrium Inorganic materials 0.000 claims description 4
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
230000009435 amidation Effects 0.000 claims description 3
238000007112 amidation reaction Methods 0.000 claims description 3
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
201000010099 disease Diseases 0.000 claims description 3
239000003814 drug Substances 0.000 claims description 3
238000007327 hydrogenolysis reaction Methods 0.000 claims description 3
125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 3
150000007522 mineralic acids Chemical class 0.000 claims description 3
150000007524 organic acids Chemical class 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
238000007127 saponification reaction Methods 0.000 claims description 3
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 2
125000005236 alkanoylamino group Chemical group 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 claims description 2
208000030499 combat disease Diseases 0.000 claims description 2
125000004122 cyclic group Chemical group 0.000 claims description 2
ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
238000001149 thermolysis Methods 0.000 claims description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 claims 2
239000000969 carrier Substances 0.000 claims 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims 1
230000001225 therapeutic effect Effects 0.000 claims 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 12
230000000694 effects Effects 0.000 abstract description 9
230000002785 anti-thrombosis Effects 0.000 abstract description 4
230000000144 pharmacologic effect Effects 0.000 abstract description 4
230000015572 biosynthetic process Effects 0.000 abstract description 3
239000003112 inhibitor Substances 0.000 abstract description 3
PXGPLTODNUVGFL-BRIYLRKRSA-N (E,Z)-(1R,2R,3R,5S)-7-(3,5-Dihydroxy-2-((3S)-(3-hydroxy-1-octenyl))cyclopentyl)-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)C[C@H](O)[C@@H]1CC=CCCCC(O)=O PXGPLTODNUVGFL-BRIYLRKRSA-N 0.000 abstract description 2
102100029100 Hematopoietic prostaglandin D synthase Human genes 0.000 abstract description 2
101000988802 Homo sapiens Hematopoietic prostaglandin D synthase Proteins 0.000 abstract description 2
239000005557 antagonist Substances 0.000 abstract description 2
210000004072 lung Anatomy 0.000 abstract description 2
BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 abstract description 2
BHMBVRSPMRCCGG-UHFFFAOYSA-N prostaglandine D2 Natural products CCCCCC(O)C=CC1C(CC=CCCCC(O)=O)C(O)CC1=O BHMBVRSPMRCCGG-UHFFFAOYSA-N 0.000 abstract description 2
238000003786 synthesis reaction Methods 0.000 abstract description 2
XEYBRNLFEZDVAW-DODZYUBVSA-N 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]-5-heptenoic acid Chemical compound CCCCC[C@H](O)C=C[C@H]1[C@H](O)CC(=O)[C@@H]1CC=CCCCC(O)=O XEYBRNLFEZDVAW-DODZYUBVSA-N 0.000 abstract 1
239000000543 intermediate Substances 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 390
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 210
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 209
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 123
238000002844 melting Methods 0.000 description 108
230000008018 melting Effects 0.000 description 108
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 74
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 71
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 67
239000000741 silica gel Substances 0.000 description 58
229910002027 silica gel Inorganic materials 0.000 description 58
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 57
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 47
239000000243 solution Substances 0.000 description 43
239000011541 reaction mixture Substances 0.000 description 39
239000000203 mixture Substances 0.000 description 34
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
239000002904 solvent Substances 0.000 description 29
239000008346 aqueous phase Substances 0.000 description 26
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 24
239000003826 tablet Substances 0.000 description 22
239000013543 active substance Substances 0.000 description 21
235000015165 citric acid Nutrition 0.000 description 19
239000006260 foam Substances 0.000 description 19
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000003921 oil Substances 0.000 description 18
239000000284 extract Substances 0.000 description 17
239000002253 acid Substances 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
239000000725 suspension Substances 0.000 description 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 14
OMOVVBIIQSXZSZ-UHFFFAOYSA-N [6-(4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3h-pyrano[3,4-b]oxepin-5-yl)-5-formyloxy-3-(furan-3-yl)-3a-methyl-7-methylidene-1a,2,3,4,5,6-hexahydroindeno[1,7a-b]oxiren-4-yl] 2-hydroxy-3-methylpentanoate Chemical compound CC12C(OC(=O)C(O)C(C)CC)C(OC=O)C(C3(C)C(CC(=O)OC4(C)COC(=O)CC43)OC(C)=O)C(=C)C32OC3CC1C=1C=COC=1 OMOVVBIIQSXZSZ-UHFFFAOYSA-N 0.000 description 14
235000011167 hydrochloric acid Nutrition 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 13
IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 13
235000019359 magnesium stearate Nutrition 0.000 description 13
239000001117 sulphuric acid Substances 0.000 description 13
235000011149 sulphuric acid Nutrition 0.000 description 13
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 12
229960002768 dipyridamole Drugs 0.000 description 12
239000012074 organic phase Substances 0.000 description 12
239000001267 polyvinylpyrrolidone Substances 0.000 description 11
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 11
229920000036 polyvinylpyrrolidone Polymers 0.000 description 11
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
239000002585 base Substances 0.000 description 10
239000002775 capsule Substances 0.000 description 10
XUDOZULIAWNMIU-UHFFFAOYSA-N delta-hexenoic acid Chemical compound OC(=O)CCCC=C XUDOZULIAWNMIU-UHFFFAOYSA-N 0.000 description 10
239000008188 pellet Substances 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
229920002261 Corn starch Polymers 0.000 description 9
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000008120 corn starch Substances 0.000 description 9
229960004132 diethyl ether Drugs 0.000 description 9
239000007858 starting material Substances 0.000 description 9
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 8
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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BXNSEGZMAZFVIS-UHFFFAOYSA-N n-[3-[3-[2-[3-acetamido-5-(trifluoromethyl)phenyl]pyridine-3-carbonyl]pyridin-2-yl]-5-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC(NC(=O)C)=CC(C=2C(=CC=CN=2)C(=O)C=2C(=NC=CC=2)C=2C=C(C=C(NC(C)=O)C=2)C(F)(F)F)=C1 BXNSEGZMAZFVIS-UHFFFAOYSA-N 0.000 description 1
TZHCUELPVRNZOT-UHFFFAOYSA-N n-[5-[3-[2-(3-acetamido-4-methylphenyl)pyridine-3-carbonyl]pyridin-2-yl]-2-methylphenyl]acetamide Chemical compound C1=C(C)C(NC(=O)C)=CC(C=2C(=CC=CN=2)C(=O)C=2C(=NC=CC=2)C=2C=C(NC(C)=O)C(C)=CC=2)=C1 TZHCUELPVRNZOT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000006257 n-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
125000006256 n-propyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC(*)=O 0.000 description 1
150000006636 nicotinic acid Chemical class 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000002560 nitrile group Chemical group 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002905 orthoesters Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 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
239000008363 phosphate buffer Substances 0.000 description 1
229960002164 pimobendan Drugs 0.000 description 1
GLBJJMFZWDBELO-UHFFFAOYSA-N pimobendane Chemical compound C1=CC(OC)=CC=C1C1=NC2=CC=C(C=3C(CC(=O)NN=3)C)C=C2N1 GLBJJMFZWDBELO-UHFFFAOYSA-N 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
229940127126 plasminogen activator Drugs 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
208000002815 pulmonary hypertension Diseases 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000009467 reduction Effects 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
150000003509 tertiary alcohols Chemical class 0.000 description 1
150000003536 tetrazoles Chemical class 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
XNRNNGPBEPRNAR-JQBLCGNGSA-N thromboxane B2 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1OC(O)C[C@H](O)[C@@H]1C\C=C/CCCC(O)=O XNRNNGPBEPRNAR-JQBLCGNGSA-N 0.000 description 1
AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
238000002834 transmittance Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 1
229960002622 triacetin Drugs 0.000 description 1
210000000626 ureter Anatomy 0.000 description 1
239000007966 viscous suspension Substances 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
- A—HUMAN NECESSITIES
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Urology & Nephrology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Immunology (AREA)
Diabetes (AREA)
Vascular Medicine (AREA)
Oncology (AREA)
Endocrinology (AREA)
Reproductive Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyridine Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Electroluminescent Light Sources (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Silicon Polymers (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

IL10406692A 1991-12-14 1992-12-11 Pyridyl derivatives their preparation and pharmaceutical compositions containing them IL104066A (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
DE4141377A DE4141377A1 (de)	1991-12-14	1991-12-14	Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
DE4216364A DE4216364A1 (de)	1991-12-14	1992-05-18	Neue Pyridylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
DE4216829A DE4216829A1 (de)	1991-12-14	1992-05-21	Neue Pyridylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung

Publications (2)

Publication Number	Publication Date
IL104066A0 IL104066A0 (en)	1993-05-13
IL104066A true IL104066A (en)	1996-07-23

Family

ID=27203214

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10406692A IL104066A (en)	1991-12-14	1992-12-11	Pyridyl derivatives their preparation and pharmaceutical compositions containing them

Country Status (18)

Country	Link
US (1)	US5482948A (cs)
EP (1)	EP0547517B1 (cs)
JP (1)	JP2965425B2 (cs)
KR (1)	KR100227441B1 (cs)
AT (1)	ATE122658T1 (cs)
AU (1)	AU653455B2 (cs)
CA (1)	CA2085201C (cs)
DE (3)	DE4216364A1 (cs)
DK (1)	DK0547517T3 (cs)
ES (1)	ES2074323T3 (cs)
FI (1)	FI100882B (cs)
HU (3)	HU9203949D0 (cs)
IL (1)	IL104066A (cs)
NO (1)	NO179173C (cs)
NZ (1)	NZ245445A (cs)
PL (3)	PL171463B1 (cs)
RU (1)	RU2119915C1 (cs)
TW (1)	TW293816B (cs)

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RU2126001C1 (ru) *	1995-01-10	1999-02-10	Самдзин Фармасьютикал Ко., Лтд	Производные пиперазина и фармацевтическая композиция на их основе
SK282252B6 (sk) *	1995-01-11	2001-12-03	Samjin Pharmaceutical Co., Ltd.	Piperazínové deriváty a farmaceutický prostriedok s ich obsahom
EP0850222B1 (en) *	1996-06-29	2003-05-28	Samjin Pharmaceutical Co., Ltd.	Piperazine derivatives and process for the preparation thereof
CN1259119A (zh) *	1997-05-07	2000-07-05	诺沃挪第克公司	取代的3,3－二氨基－2－丙烯腈,它们的制备及用途
US5955548A (en) *	1997-05-07	1999-09-21	Novo Nordisk A/S	Substituted 3, 3-diamino-2-propenenitriles, their preparation and use
MXPA01009621A (es) *	1999-03-22	2003-07-21	Johnson & Johnson	Procedimiento para la preparacion de acido 3s-3-amino-3-aril propionico, y derivados del mismo.
GB0022215D0 (en) *	2000-09-11	2000-10-25	Boehringer Ingelheim Pharma	Method for the treatment of thromboembolic disorders in patients with aspirin« resistance
US10675280B2 (en)	2001-10-20	2020-06-09	Sprout Pharmaceuticals, Inc.	Treating sexual desire disorders with flibanserin
UA78974C2 (en)	2001-10-20	2007-05-10	Boehringer Ingelheim Pharma	Use of flibanserin for treating disorders of sexual desire
WO2003050261A2 (en) *	2001-12-10	2003-06-19	Bristol-Myers Squibb Company	(1-phenyl-2-heteroaryl)ethyl-guanidine compounds as inhibitors of mitochondrial f1f0 atp hydrolase
US20030181488A1 (en) *	2002-03-07	2003-09-25	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof
DE10209982A1 (de) *	2002-03-07	2003-09-25	Boehringer Ingelheim Pharma	Oral zu applizierende Darreichungsform für schwerlösliche basische Wirkstoffe
CA2617546C (en)	2005-08-03	2014-07-15	Boehringer Ingelheim International Gmbh	Use of flibanserin in the treatment of obesity
WO2008000760A1 (en)	2006-06-30	2008-01-03	Boehringer Ingelheim International Gmbh	Flibanserin for the treatment of urinary incontinence and related diseases
PE20091188A1 (es)	2007-09-12	2009-08-31	Boehringer Ingelheim Int	Compuesto 1-[2-(4-(3-trifluorometil-fenil)piperazin-1-il)etil]-2,3-dihidro-1h-benzimidazol-2-ona (flibanserina), sus sales de adicion y composiciones farmaceuticas que los contienen
EP2234608A2 (en)	2007-12-11	2010-10-06	Viamet Pharmaceuticals, Inc.	Metalloenzyme inhibitors using metal binding moieties in combination with targeting moieties
CA2686480A1 (en)	2008-12-15	2010-06-15	Boehringer Ingelheim International Gmbh	New salts
WO2014015157A2 (en)	2012-07-19	2014-01-23	Philadelphia Health & Education Corporation	Novel sigma receptor ligands and methods of modulating cellular protein homeostasis using same
US11117870B2 (en)	2017-11-01	2021-09-14	Drexel University	Compounds, compositions, and methods for treating diseases

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3932403A1 (de) *	1989-05-12	1991-04-11	Thomae Gmbh Dr K	Neue arylsulfonamide, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
IL94805A (en) *	1989-06-28	1994-04-12	Ciba Geigy Ag	(Arylsulfonamido- and pyridyl- or imidazolyl-)-substituted carboxylic acids, processfor their preparation and pharmaceutical compositions containing them
DE4037112A1 (de) *	1990-11-22	1992-05-27	Thomae Gmbh Dr K	Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung

1992
- 1992-05-18 DE DE4216364A patent/DE4216364A1/de not_active Withdrawn
- 1992-05-21 DE DE4216829A patent/DE4216829A1/de not_active Withdrawn
- 1992-11-05 TW TW081108864A patent/TW293816B/zh not_active IP Right Cessation
- 1992-12-09 PL PL92312869A patent/PL171463B1/pl not_active IP Right Cessation
- 1992-12-09 PL PL92312868A patent/PL171500B1/pl not_active IP Right Cessation
- 1992-12-09 PL PL92296896A patent/PL171512B1/pl not_active IP Right Cessation
- 1992-12-11 AU AU30058/92A patent/AU653455B2/en not_active Ceased
- 1992-12-11 AT AT92121126T patent/ATE122658T1/de active
- 1992-12-11 JP JP4331452A patent/JP2965425B2/ja not_active Expired - Fee Related
- 1992-12-11 HU HU9203949A patent/HU9203949D0/hu unknown
- 1992-12-11 HU HU9203949A patent/HUT68032A/hu unknown
- 1992-12-11 NZ NZ245445A patent/NZ245445A/en unknown
- 1992-12-11 EP EP92121126A patent/EP0547517B1/de not_active Expired - Lifetime
- 1992-12-11 DE DE59202241T patent/DE59202241D1/de not_active Expired - Lifetime
- 1992-12-11 NO NO924800A patent/NO179173C/no not_active IP Right Cessation
- 1992-12-11 CA CA002085201A patent/CA2085201C/en not_active Expired - Fee Related
- 1992-12-11 ES ES92121126T patent/ES2074323T3/es not_active Expired - Lifetime
- 1992-12-11 DK DK92121126.4T patent/DK0547517T3/da active
- 1992-12-11 IL IL10406692A patent/IL104066A/en not_active IP Right Cessation
- 1992-12-12 KR KR1019920024089A patent/KR100227441B1/ko not_active Expired - Fee Related
- 1992-12-14 FI FI925665A patent/FI100882B/fi not_active IP Right Cessation
- 1992-12-14 RU RU92004567A patent/RU2119915C1/ru not_active IP Right Cessation
1994
- 1994-07-05 US US08/270,615 patent/US5482948A/en not_active Expired - Lifetime
1995
- 1995-06-02 HU HU95P/P00160P patent/HU211230A9/hu unknown

Also Published As

Publication number	Publication date
JPH06199793A (ja)	1994-07-19
DK0547517T3 (da)	1995-09-04
NO179173C (no)	1996-08-21
HU211230A9 (en)	1995-11-28
DE4216364A1 (de)	1993-11-25
KR100227441B1 (ko)	1999-11-01
FI100882B (fi)	1998-03-13
DE4216829A1 (de)	1993-11-25
NO179173B (no)	1996-05-13
DE59202241D1 (de)	1995-06-22
HUT68032A (en)	1995-05-29
PL171500B1 (en)	1997-05-30
NZ245445A (en)	1995-06-27
PL171512B1 (pl)	1997-05-30
RU2119915C1 (ru)	1998-10-10
JP2965425B2 (ja)	1999-10-18
ATE122658T1 (de)	1995-06-15
EP0547517A1 (de)	1993-06-23
CA2085201C (en)	2004-07-06
PL296896A1 (en)	1993-11-29
FI925665A0 (fi)	1992-12-14
NO924800D0 (no)	1992-12-11
EP0547517B1 (de)	1995-05-17
HU9203949D0 (en)	1993-03-29
FI925665L (fi)	1993-06-15
NO924800L (no)	1993-06-15
TW293816B (cs)	1996-12-21
CA2085201A1 (en)	1993-06-15
IL104066A0 (en)	1993-05-13
PL171463B1 (pl)	1997-05-30
ES2074323T3 (es)	1995-09-01
AU653455B2 (en)	1994-09-29
AU3005892A (en)	1993-06-17
US5482948A (en)	1996-01-09

Legal Events

Date	Code	Title
1996-12-05	FF	Patent granted
1997-02-18	KB	Patent renewed
2003-02-12	KB	Patent renewed
2007-02-12	KB	Patent renewed
2010-12-30	KB	Patent renewed
2013-07-31	EXP	Patent expired

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US20030236244A1 (en)	2003-12-25	Inhibitors of JAK and CDK2 protein kinases
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US7855214B2 (en)	2010-12-21	Fused cyclic systems useful as inhibitors of TEC family protein kinases
JP2012012417A (ja)	2012-01-19	タンパク質キナーゼのインヒビターとして有用なアザインドール
US5286736A (en)	1994-02-15	Pyridyl compounds and pharmaceutical compositions containing these compounds
IE914048A1 (en)	1992-06-03	Pyridyl derivatives medicines containing these compounds and processes for their preparation
JPS62135475A (ja)	1987-06-18	２−置換−ｅ−融合−〔１，２，４〕トリアゾロ−〔１，５−Ｃ〕ピリミジン
KR101082227B1 (ko)	2011-11-09	피라졸로피리미딘 화합물의 메탄술폰산염, 그 결정 및 그제조 방법
DE4141377A1 (de)	1993-06-17	Neue pyridylderivate, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung
EP2243781A1 (en)	2010-10-27	Pyrazolopyridine derivatives as inhibitors of JAK and CDK2 protein kinases
JP2013064015A (ja)	2013-04-11	タンパク質キナーゼのインヒビターとして有用なアザインドール