FI57586C - Foerfarande foer framstaellning av terapeutiskt anvaendbart 1-(2-(beta-naftyloxi)-etyl)-3-metyl-pyrazolon-(5) - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbart 1-(2-(beta-naftyloxi)-etyl)-3-metyl-pyrazolon-(5) Download PDFInfo
- Publication number
- FI57586C FI57586C FI751654A FI751654A FI57586C FI 57586 C FI57586 C FI 57586C FI 751654 A FI751654 A FI 751654A FI 751654 A FI751654 A FI 751654A FI 57586 C FI57586 C FI 57586C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- naphthyloxy
- ethyl
- optionally
- ethylhydrazine
- Prior art date
Links
- -1 2- (BETA-NAPHTHYLOXY) -ETHYL Chemical class 0.000 title claims abstract description 22
- 230000001225 therapeutic effect Effects 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 239000012442 inert solvent Substances 0.000 claims description 7
- 150000007529 inorganic bases Chemical class 0.000 claims description 7
- 150000007530 organic bases Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- LUEHNHVFDCZTGL-UHFFFAOYSA-N but-2-ynoic acid Chemical class CC#CC(O)=O LUEHNHVFDCZTGL-UHFFFAOYSA-N 0.000 claims description 6
- 150000001242 acetic acid derivatives Chemical class 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 claims description 2
- WGAWXQBEUKRBAD-UHFFFAOYSA-N 1-ethyl-1-naphthalen-2-yloxyhydrazine Chemical compound C1=C(C=CC2=CC=CC=C12)ON(N)CC WGAWXQBEUKRBAD-UHFFFAOYSA-N 0.000 claims 1
- 101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims 1
- 241000277284 Salvelinus fontinalis Species 0.000 claims 1
- BORMNCXGATVZMD-UHFFFAOYSA-N 2-naphthalen-2-yloxyethylhydrazine Chemical compound C1=CC=CC2=CC(OCCNN)=CC=C21 BORMNCXGATVZMD-UHFFFAOYSA-N 0.000 abstract description 7
- WGVHNCAJPFIFCR-UHFFFAOYSA-N 5-methyl-1,2-dihydropyrazol-3-one Chemical compound CC1=CC(O)=NN1 WGVHNCAJPFIFCR-UHFFFAOYSA-N 0.000 abstract description 7
- 230000002537 thrombolytic effect Effects 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 239000003146 anticoagulant agent Substances 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 230000002785 anti-thrombosis Effects 0.000 abstract description 2
- INCLABAHEPQBCG-UHFFFAOYSA-N 5-methyl-2-(2-naphthalen-2-yloxyethyl)-1h-pyrazol-3-one Chemical compound N1C(C)=CC(=O)N1CCOC1=CC=C(C=CC=C2)C2=C1 INCLABAHEPQBCG-UHFFFAOYSA-N 0.000 abstract 1
- WOFAGNLBCJWEOE-UHFFFAOYSA-N Benzyl acetoacetate Chemical compound CC(=O)CC(=O)OCC1=CC=CC=C1 WOFAGNLBCJWEOE-UHFFFAOYSA-N 0.000 abstract 1
- 150000003385 sodium Chemical class 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003085 diluting agent Substances 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 108010023197 Streptokinase Proteins 0.000 description 5
- 208000007536 Thrombosis Diseases 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229960005202 streptokinase Drugs 0.000 description 5
- JRQMRDBHOIOIIL-UHFFFAOYSA-N 3-methyl-1,5-dihydropyrazol-4-one Chemical compound CC1=NNCC1=O JRQMRDBHOIOIIL-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 230000002792 vascular Effects 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 210000004731 jugular vein Anatomy 0.000 description 2
- UJQCANQILFWSDJ-UHFFFAOYSA-N methyl but-2-ynoate Chemical compound COC(=O)C#CC UJQCANQILFWSDJ-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OBGFJKNQKBMXBM-UHFFFAOYSA-N 1-(2-bromoethoxy)naphthalene Chemical compound C1=CC=C2C(OCCBr)=CC=CC2=C1 OBGFJKNQKBMXBM-UHFFFAOYSA-N 0.000 description 1
- WOSQDGSCRQAGMB-UHFFFAOYSA-N 2-(2-chloroethoxy)naphthalene Chemical compound C1=CC=CC2=CC(OCCCl)=CC=C21 WOSQDGSCRQAGMB-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- WHNQTHDJEZTVHS-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)propanoic acid Chemical compound C1=CC=C2SC(CCC(=O)O)=NC2=C1 WHNQTHDJEZTVHS-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 108090000435 Urokinase-type plasminogen activator Proteins 0.000 description 1
- 102000003990 Urokinase-type plasminogen activator Human genes 0.000 description 1
- 206010047249 Venous thrombosis Diseases 0.000 description 1
- RRURKIKMGJOPTH-UHFFFAOYSA-N acetic acid;hexanoic acid Chemical compound CC(O)=O.CCCCCC(O)=O RRURKIKMGJOPTH-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- YBCVMFKXIKNREZ-UHFFFAOYSA-N acoh acetic acid Chemical compound CC(O)=O.CC(O)=O YBCVMFKXIKNREZ-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000002429 anti-coagulating effect Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 0.000 description 1
- 229940127217 antithrombotic drug Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000007905 drug manufacturing Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- FCJJZKCJURDYNF-UHFFFAOYSA-N ethyl but-2-ynoate Chemical compound CCOC(=O)C#CC FCJJZKCJURDYNF-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical group CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229960005356 urokinase Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2427272 | 1974-06-06 | ||
| DE2427272A DE2427272C3 (de) | 1974-06-06 | 1974-06-06 | 1-(2-(β-Naphthyloxy)-äthyl)-3-methyl -pyrazolon-(5), Verfahren sowie Verwendung als Antithrombotikum |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI751654A FI751654A (da) | 1975-12-07 |
| FI57586B FI57586B (fi) | 1980-05-30 |
| FI57586C true FI57586C (fi) | 1980-09-10 |
Family
ID=5917444
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI751654A FI57586C (fi) | 1974-06-06 | 1975-06-04 | Foerfarande foer framstaellning av terapeutiskt anvaendbart 1-(2-(beta-naftyloxi)-etyl)-3-metyl-pyrazolon-(5) |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US4053621A (da) |
| JP (1) | JPS5840544B2 (da) |
| AR (3) | AR207177A1 (da) |
| AT (1) | AT342584B (da) |
| BE (1) | BE829850A (da) |
| BG (3) | BG24410A3 (da) |
| CA (1) | CA1051001A (da) |
| CH (3) | CH612672A5 (da) |
| CS (1) | CS193513B2 (da) |
| DD (1) | DD123886A5 (da) |
| DE (1) | DE2427272C3 (da) |
| DK (1) | DK134753C (da) |
| EG (1) | EG11950A (da) |
| ES (2) | ES454281A1 (da) |
| FI (1) | FI57586C (da) |
| FR (1) | FR2273535A1 (da) |
| GB (1) | GB1454733A (da) |
| HK (1) | HK26877A (da) |
| HU (1) | HU169651B (da) |
| IE (1) | IE41256B1 (da) |
| IL (1) | IL47411A (da) |
| KE (1) | KE2991A (da) |
| LU (1) | LU72645A1 (da) |
| NL (1) | NL181803C (da) |
| NO (1) | NO141757C (da) |
| PH (2) | PH12446A (da) |
| PL (3) | PL96609B1 (da) |
| RO (3) | RO73053A (da) |
| SE (1) | SE414766B (da) |
| SU (3) | SU544373A3 (da) |
| YU (3) | YU141575A (da) |
| ZA (1) | ZA753644B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL8201321A (nl) * | 1981-04-07 | 1982-11-01 | Bayer Ag | Werkwijze voor de behandeling van metastase en de groei van tumorcellen. |
| ATE21391T1 (de) * | 1981-05-06 | 1986-08-15 | Alcusal Inc Pty Ltd | Heterocyclische kupferkomplexe. |
| US4540707A (en) * | 1983-01-28 | 1985-09-10 | Bayer Aktiengesellschaft | Nafazatrom as a lipoxygenase inhibitor |
| DK143684A (da) * | 1983-03-12 | 1984-09-13 | Bayer Ag | Anvendelse af pyrazolonderivater som lipoxygenasehaemmer ved terapi af isaer ischaemi og hjerterytmeforstyrrelser |
| DK169672B1 (da) * | 1985-05-20 | 1995-01-09 | Mitsubishi Chem Ind | Farmaceutiske præparater indeholdende pyrazolonderivater som aktiv bestanddel og anvendelsen af pyrazolonderivater til fremstilling af farmaceutiske præparater |
| USRE35801E (en) * | 1985-05-20 | 1998-05-19 | Mitsubishi Chemical Corporation | Prophylactic and therapeutic composition for circulatory disorders and method of treatment |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2376380A (en) * | 1945-05-22 | Preparation of amino pyrazolones | ||
| US2476986A (en) * | 1949-07-26 | Elmobe louis martin | ||
| GB599919A (en) | 1944-12-11 | 1948-03-24 | Kodak Ltd | Improvements in the manufacture of aminopyrazolones and their use as colour couplers |
| US2476987A (en) * | 1949-07-26 | S-acyloxy pyrazqles and method foe | ||
| US3147276A (en) * | 1964-09-01 | Pyrazolones | ||
| GB636988A (en) * | 1947-12-24 | 1950-05-10 | Gevaert Photo Producten Naamlo | Improvements in and relating to the production of colour photographic images |
| US2511231A (en) * | 1949-03-26 | 1950-06-13 | Eastman Kodak Co | 1-cyanophenyl-3-acylamino-5-pyrazolone couplers for color photography |
| US2600788A (en) * | 1949-06-07 | 1952-06-17 | Eastman Kodak Co | Halogen-substituted pyrazolone couplers for color photography |
| IT476454A (da) * | 1949-08-22 | |||
| US2672417A (en) * | 1949-12-31 | 1954-03-16 | Gevaert Photo Prod Nv | Production of color photographic images |
| GB779703A (en) | 1953-07-06 | 1957-07-24 | Hoechst Ag | Pyrazolone compounds and a process for making them |
| US2848446A (en) * | 1954-02-23 | 1958-08-19 | Saul & Co | Azo dyestuffs |
| US3014916A (en) * | 1959-01-22 | 1961-12-26 | May & Baker Ltd | Pyrazole derivatives |
| GB935538A (en) * | 1959-04-06 | 1963-08-28 | Stop Motion Devices Corp | Stop-motion head for use on knitting machines |
| GB961037A (en) | 1960-08-23 | 1964-06-17 | Smith & Nephew | Pyrazolones and processes for their preparation |
| NL121416C (da) * | 1961-05-31 | |||
| US3190888A (en) * | 1963-08-22 | 1965-06-22 | American Home Prod | Aryloxyalkylpyrazole |
| DE1670529C3 (de) * | 1966-07-13 | 1974-01-10 | Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler, 6000 Frankfurt | Substituierte s-Triazine |
| GB1190914A (en) * | 1966-09-26 | 1970-05-06 | Agfa Gevaert Nv | 2-Pyrazolin-5-Ones and the use thereof as Colour Couplers |
| FR1558513A (da) * | 1968-01-04 | 1969-02-28 | ||
| GB1247688A (en) | 1968-02-26 | 1971-09-29 | Agfa Gevaert | Monomeric and polymeric 2-pyrazoline-5-one colour couplers |
| JPS4818858B1 (da) * | 1969-04-07 | 1973-06-08 | ||
| FR2068413A1 (en) | 1969-10-22 | 1971-08-27 | Synthelabo | 1-alkyl-3-alkylamino-5-aryl-pyrazolines hypo-and hypertensives |
| US3615506A (en) * | 1970-02-09 | 1971-10-26 | Eastman Kodak Co | Silver halide emulsions containing 3-cyclicamino-5-pyrazolone color couplers |
| US3694456A (en) * | 1970-05-08 | 1972-09-26 | Takeda Chemical Industries Ltd | 1-disubstituted aminopyrazoles |
| FR2101060B1 (da) * | 1970-08-14 | 1974-02-01 | Roussel Uclaf | |
| JPS548689B1 (da) * | 1970-12-04 | 1979-04-18 | ||
| JPS5417772B1 (da) * | 1970-12-04 | 1979-07-03 | ||
| DE2319278C2 (de) | 1973-04-17 | 1986-02-20 | Bayer Ag, 5090 Leverkusen | Pharmazeutisches Mittel |
| AR207445A1 (es) * | 1973-04-17 | 1976-10-08 | Bayer Ag | Procedimiento de preparacion de nuevos derivados de pirazolonas-(5)-1-substituidas |
| DE2319281A1 (de) * | 1973-04-17 | 1974-11-07 | Bayer Ag | Diuretisches und antihypertensives mittel |
-
1974
- 1974-06-06 DE DE2427272A patent/DE2427272C3/de not_active Expired
-
1975
- 1975-01-01 AR AR261807A patent/AR207177A1/es active
- 1975-01-01 AR AR259115A patent/AR207044A1/es active
- 1975-01-01 AR AR261806A patent/AR207176A1/es active
- 1975-04-05 RO RO7591324A patent/RO73053A/ro unknown
- 1975-05-06 GB GB1897075A patent/GB1454733A/en not_active Expired
- 1975-05-23 NO NO751846A patent/NO141757C/no unknown
- 1975-05-24 EG EG75308A patent/EG11950A/xx active
- 1975-05-26 BG BG030936A patent/BG24410A3/xx unknown
- 1975-05-26 BG BG030937A patent/BG23005A3/xx unknown
- 1975-05-28 SU SU2138693A patent/SU544373A3/ru active
- 1975-06-02 US US05/582,773 patent/US4053621A/en not_active Expired - Lifetime
- 1975-06-02 BG BG030159A patent/BG23899A3/xx unknown
- 1975-06-02 YU YU01415/75A patent/YU141575A/xx unknown
- 1975-06-03 PH PH17223A patent/PH12446A/en unknown
- 1975-06-03 IL IL7547411A patent/IL47411A/xx unknown
- 1975-06-04 DK DK253475A patent/DK134753C/da not_active IP Right Cessation
- 1975-06-04 PL PL1975193711A patent/PL96609B1/pl unknown
- 1975-06-04 AT AT424875A patent/AT342584B/de not_active IP Right Cessation
- 1975-06-04 CH CH136979A patent/CH612672A5/xx not_active IP Right Cessation
- 1975-06-04 JP JP50066633A patent/JPS5840544B2/ja not_active Expired
- 1975-06-04 PL PL1975180895A patent/PL93913B1/pl unknown
- 1975-06-04 DD DD186449A patent/DD123886A5/xx unknown
- 1975-06-04 BE BE157016A patent/BE829850A/xx not_active IP Right Cessation
- 1975-06-04 CH CH720675A patent/CH611889A5/xx not_active IP Right Cessation
- 1975-06-04 FI FI751654A patent/FI57586C/fi not_active IP Right Cessation
- 1975-06-04 LU LU72645A patent/LU72645A1/xx unknown
- 1975-06-04 PL PL1975193710A patent/PL96608B1/pl unknown
- 1975-06-04 CH CH137079A patent/CH612673A5/xx not_active IP Right Cessation
- 1975-06-05 RO RO7582444A patent/RO79056A/ro unknown
- 1975-06-05 SE SE7506435A patent/SE414766B/xx not_active IP Right Cessation
- 1975-06-05 IE IE1269/75A patent/IE41256B1/xx unknown
- 1975-06-05 CS CS753956A patent/CS193513B2/cs unknown
- 1975-06-05 ZA ZA00753644A patent/ZA753644B/xx unknown
- 1975-06-05 RO RO7591325A patent/RO73054A/ro unknown
- 1975-06-06 HU HUBA3276A patent/HU169651B/hu unknown
- 1975-06-06 CA CA228,726A patent/CA1051001A/en not_active Expired
- 1975-06-06 FR FR7517765A patent/FR2273535A1/fr active Granted
- 1975-06-06 NL NLAANVRAGE7506765,A patent/NL181803C/xx not_active IP Right Cessation
- 1975-12-16 ES ES454281A patent/ES454281A1/es not_active Expired
-
1976
- 1976-03-12 SU SU762331907A patent/SU588917A3/ru active
- 1976-03-12 SU SU762331906A patent/SU586839A3/ru active
- 1976-10-19 PH PH19016A patent/PH14053A/en unknown
- 1976-12-16 ES ES454280A patent/ES454280A1/es not_active Expired
-
1977
- 1977-06-02 HK HK268/77A patent/HK26877A/xx unknown
-
1979
- 1979-09-11 KE KE2991A patent/KE2991A/xx unknown
-
1981
- 1981-07-08 YU YU01692/81A patent/YU169281A/xx unknown
- 1981-07-08 YU YU01691/81A patent/YU169181A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0253503B1 (en) | Substituted anilides having antiandrogenic properties | |
| KR920005815B1 (ko) | 퀴논 유도체 및 약리학적 이용 | |
| US4174397A (en) | Thiazolidine derivatives | |
| JPS6089474A (ja) | モルフイナン誘導体，その製造方法，及び該化合物を含有する抗腫瘍剤 | |
| US4196292A (en) | 6-Substituted amiloride derivatives | |
| FI57586C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbart 1-(2-(beta-naftyloxi)-etyl)-3-metyl-pyrazolon-(5) | |
| US4247706A (en) | Dibenzothiepin derivatives and a process for producing the same | |
| HU195193B (en) | Process for producing tricyclic dihydropyridazinone derivatives and pharmaceutical preparations comprising the same as active substance | |
| JP2707936B2 (ja) | β−オキソ−β−ベンゼンプロパンチオアミド誘導体 | |
| US4097441A (en) | 5,6-Dihydro-4-oxo-4H-thieno 2,3-b!thiopyran-5-carboxamides | |
| CS256400B2 (cs) | Způsob výroby nových pyridylmethyllsulfinylthieno(2.3-d)imi<lazolových derivátů | |
| KR20040010779A (ko) | 발기부전 치료를 위한 신규한 화합물 | |
| US4569945A (en) | Diarylindane-1,3-diones, their preparation and use | |
| JPH0246035B2 (da) | ||
| HU193274B (en) | Process for preparing phenthiazines | |
| US4009172A (en) | 2,3,3A,6,7,7A-Hexahydro-thieno[3,2-b]pyridin-(4H)5-ones | |
| US4223146A (en) | 4,5,6,7-Tetrahydroimidazo-[4,5-c]-pyridine derivatives | |
| KR840001034B1 (ko) | 디하이드로니코틴산 유도체의 제조방법 | |
| NZ205469A (en) | Sulfamoylbenzophenone derivatives and pharmaceutical compositions | |
| US4755523A (en) | Abietamide derivatives | |
| US5003090A (en) | Process for the preparation of benzopyrans | |
| US4247715A (en) | 2-Alkynyl-5-indanyloxyacetic acids | |
| US4879404A (en) | Novel salicylates, their salts, pharmaceutical compositions containing them and process for preparing same | |
| HU199116B (en) | Process for production of derivatives of benzolsulphamid and medical compositions containing them | |
| EP0329691B1 (en) | Cardiotonic imidazolylphenylpyrrol-2-ones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BAYER AKTIENGESELLSCHAFT |