DD248362A5 - Verfahren zur herstellung neuer pyridazinone - Google Patents

Verfahren zur herstellung neuer pyridazinone Download PDF

Info

Publication number: DD248362A5
Authority: DD; German Democratic Republic
Prior art keywords: group; methyl; pyridazinone; dihydro; atom
Prior art date: 1985-03-27

Application number

DD86288285A

Other languages

German (de)

English (en)

Inventor

Norbert Hauel

Berthold Narr

Klaus Noll

Andreas Bomhard

Joachim Heider

Manfred Psiorz

Willi Diederen

Jacques Van Meel

Original Assignee

��K@��@��@��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.)

1985-03-27

Filing date

1986-03-25

Publication date

1987-08-05

1986-03-25 Application filed by ��K@��@��@��k�� filed Critical ��K@��@��@��k��

1987-08-05 Publication of DD248362A5 publication Critical patent/DD248362A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 19
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 14
238000002360 preparation method Methods 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 43
239000002253 acid Substances 0.000 claims abstract description 27
150000003839 salts Chemical class 0.000 claims abstract description 16
150000007524 organic acids Chemical class 0.000 claims abstract description 6
235000005985 organic acids Nutrition 0.000 claims abstract description 6
150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
-1 morpholino, thiomorpholino, 1-oxidothiomorpholino Chemical group 0.000 claims description 114
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
125000000217 alkyl group Chemical group 0.000 claims description 27
229910052799 carbon Inorganic materials 0.000 claims description 21
229910052757 nitrogen Inorganic materials 0.000 claims description 21
238000006243 chemical reaction Methods 0.000 claims description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims description 19
150000001721 carbon Chemical group 0.000 claims description 18
125000001841 imino group Chemical group [H]N=* 0.000 claims description 18
229960000583 acetic acid Drugs 0.000 claims description 16
229910052717 sulfur Inorganic materials 0.000 claims description 16
125000004434 sulfur atom Chemical group 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 14
239000012362 glacial acetic acid Substances 0.000 claims description 14
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 14
229920000137 polyphosphoric acid Polymers 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
239000000460 chlorine Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000001072 heteroaryl group Chemical group 0.000 claims description 7
238000005984 hydrogenation reaction Methods 0.000 claims description 7
125000003884 phenylalkyl group Chemical group 0.000 claims description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
239000011541 reaction mixture Substances 0.000 claims description 7
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
229940093915 gynecological organic acid Drugs 0.000 claims description 5
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
125000005236 alkanoylamino group Chemical group 0.000 claims description 4
125000003277 amino group Chemical group 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
229920006395 saturated elastomer Polymers 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 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 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
238000005695 dehalogenation reaction Methods 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000005277 alkyl imino group Chemical group 0.000 claims description 2
125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
230000000269 nucleophilic effect Effects 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
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 2
125000003373 pyrazinyl group Chemical group 0.000 claims description 2
150000003217 pyrazoles Chemical class 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000001589 carboacyl group Chemical group 0.000 claims 1
125000002541 furyl group Chemical group 0.000 claims 1
125000002971 oxazolyl group Chemical group 0.000 claims 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
230000000144 pharmacologic effect Effects 0.000 abstract description 5
206010002383 Angina Pectoris Diseases 0.000 abstract description 2
208000031104 Arterial Occlusive disease Diseases 0.000 abstract description 2
206010007558 Cardiac failure chronic Diseases 0.000 abstract description 2
238000011321 prophylaxis Methods 0.000 abstract description 2
238000011282 treatment Methods 0.000 abstract description 2
206010014513 Embolism arterial Diseases 0.000 abstract 1
238000002844 melting Methods 0.000 description 73
230000008018 melting Effects 0.000 description 73
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 16
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEJXNMVJEXBSQF-UHFFFAOYSA-N 4-methyl-3-(2-methylsulfanyl-1,3-benzoxazol-6-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C2OC(SC)=NC2=CC=C1C1=NNC(=O)CC1C WEJXNMVJEXBSQF-UHFFFAOYSA-N 0.000 description 10
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
XHFMZTGMZOPLPG-UHFFFAOYSA-N 3-(2-methylsulfanyl-1,3-benzoxazol-6-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C1=C2OC(SC)=NC2=CC=C1C1=NNC(=O)CC1 XHFMZTGMZOPLPG-UHFFFAOYSA-N 0.000 description 8
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 8
ORSUMIZRRGPJBR-UHFFFAOYSA-N 4,5-dihydro-1h-pyridazin-6-one Chemical compound O=C1CCC=NN1 ORSUMIZRRGPJBR-UHFFFAOYSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000004587 chromatography analysis Methods 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
UHYVTWWKARNAPE-UHFFFAOYSA-N 4-methyl-3-(2-methylsulfanyl-1,3-benzoxazol-5-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound C=1C=C2OC(SC)=NC2=CC=1C1=NNC(=O)CC1C UHYVTWWKARNAPE-UHFFFAOYSA-N 0.000 description 5
125000004539 5-benzimidazolyl group Chemical group N1=CNC2=C1C=CC(=C2)* 0.000 description 5
150000002148 esters Chemical class 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
238000001816 cooling Methods 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
238000002329 infrared spectrum Methods 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
JVDKSRXXEBKANQ-UHFFFAOYSA-N 3-(2-imidazol-1-yl-3h-benzimidazol-5-yl)-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N=C(N2)N3C=NC=C3)C2=C1 JVDKSRXXEBKANQ-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
102000008186 Collagen Human genes 0.000 description 3
108010035532 Collagen Proteins 0.000 description 3
241000282326 Felis catus Species 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000003177 cardiotonic effect Effects 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
229920001436 collagen Polymers 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000155 melt Substances 0.000 description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 description 2
YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 description 2
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
OQFWEYYPGHWIHY-UHFFFAOYSA-N 3-(2-methylsulfanyl-1,3-benzoxazol-5-yl)-4-propyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CCCC1CC(=O)NN=C1C1=CC=C(OC(SC)=N2)C2=C1 OQFWEYYPGHWIHY-UHFFFAOYSA-N 0.000 description 2
DPWPMUSGLLXNQL-UHFFFAOYSA-N 3-[2-(2,6-dichloropyridin-3-yl)-1,3-benzoxazol-6-yl]-4-methyl-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N=C(O2)C=3C(=NC(Cl)=CC=3)Cl)C2=C1 DPWPMUSGLLXNQL-UHFFFAOYSA-N 0.000 description 2
KOYZLXFXQWUVFN-UHFFFAOYSA-N 3-[2-(2,6-dichloropyridin-4-yl)-3h-benzimidazol-5-yl]-4,5-dihydro-1h-pyridazin-6-one Chemical compound ClC1=NC(Cl)=CC(C=2NC3=CC(=CC=C3N=2)C=2CCC(=O)NN=2)=C1 KOYZLXFXQWUVFN-UHFFFAOYSA-N 0.000 description 2
RMLXSVHNVQIFTQ-UHFFFAOYSA-N 4-methyl-3-(2-pyrrolidin-1-yl-3h-benzimidazol-5-yl)-4,5-dihydro-1h-pyridazin-6-one Chemical compound CC1CC(=O)NN=C1C1=CC=C(N=C(N2)N3CCCC3)C2=C1 RMLXSVHNVQIFTQ-UHFFFAOYSA-N 0.000 description 2
KMQLIDDEQAJAGJ-UHFFFAOYSA-N 4-oxo-4-phenylbutyric acid Chemical class OC(=O)CCC(=O)C1=CC=CC=C1 KMQLIDDEQAJAGJ-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
OQAGVSWESNCJJT-UHFFFAOYSA-N Methyl 3-methylbutanoate Chemical compound COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000002776 aggregation Effects 0.000 description 2
238000004220 aggregation Methods 0.000 description 2
230000002785 anti-thrombosis Effects 0.000 description 2
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
LNOQURRKNJKKBU-UHFFFAOYSA-N ethyl piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCNCC1 LNOQURRKNJKKBU-UHFFFAOYSA-N 0.000 description 2
208000021822 hypotensive Diseases 0.000 description 2
230000001077 hypotensive effect Effects 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
DCDYNCXCJUOYCO-UHFFFAOYSA-N methyl 4-(2-chloro-3H-benzimidazol-5-yl)-3-methyl-4-oxobutanoate Chemical compound COC(CC(C(=O)C1=CC2=C(N=C(N2)Cl)C=C1)C)=O DCDYNCXCJUOYCO-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000011570 nicotinamide Substances 0.000 description 2
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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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- 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
- C07D401/14—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 three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyridine Compounds (AREA)

DD86288285A 1985-03-27 1986-03-25 Verfahren zur herstellung neuer pyridazinone DD248362A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853511110 DE3511110A1 (de)	1985-03-27	1985-03-27	Neue pyridazinone, ihre herstellung und diese verbindungen enthaltende arzneimittel

Publications (1)

Publication Number	Publication Date
DD248362A5 true DD248362A5 (de)	1987-08-05

Family

ID=6266489

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86288285A DD248362A5 (de)	1985-03-27	1986-03-25	Verfahren zur herstellung neuer pyridazinone

Country Status (18)

Country	Link
EP (1)	EP0196005B1 (fr)
JP (1)	JPS61227582A (fr)
KR (1)	KR860007253A (fr)
AT (1)	ATE48841T1 (fr)
AU (1)	AU5530386A (fr)
CA (1)	CA1257588A (fr)
DD (1)	DD248362A5 (fr)
DE (2)	DE3511110A1 (fr)
DK (1)	DK131886A (fr)
ES (4)	ES8705882A1 (fr)
FI (1)	FI861288A7 (fr)
GR (1)	GR860801B (fr)
HU (1)	HUT42085A (fr)
IL (1)	IL78251A0 (fr)
NO (1)	NO861266L (fr)
NZ (1)	NZ215616A (fr)
PT (1)	PT82272B (fr)
ZA (1)	ZA862248B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0350990A1 (fr) *	1988-07-11	1990-01-17	Akzo Nobel N.V.	Dérivés de pyridazinone

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3505609A1 (de) *	1985-02-19	1986-08-21	Merck Patent Gmbh, 6100 Darmstadt	Benzimidazolyl-pyridazinone
US4725686A (en) *	1985-11-22	1988-02-16	William H. Rorer, Inc.	Benzodiazinone-pyridazinone and hydroxy-pyrazolyl compounds, cardiotonic compositions including the same, and their uses
DE3611343A1 (de) *	1986-04-04	1987-10-08	Boehringer Mannheim Gmbh	Heterocyclisch substituierte benzimidazole, verfahren zu ihrer herstellung, arzneimittel sowie zwischenprodukte
DE3734083A1 (de) *	1987-10-08	1989-04-20	Heumann Pharma Gmbh & Co	Benzimidazole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE3735207A1 (de) *	1987-10-17	1989-04-27	Basf Ag	Mittel auf der basis von phenylpyridazinon-derivaten zur wachstumsfoerderung und fettreduktion bei tieren
FR2643903A1 (fr) *	1989-03-03	1990-09-07	Union Pharma Scient Appl	Nouveaux derives de benzimidazole, leurs procedes de preparation, intermediaires de synthese, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et des ulceres duodenaux
DE4237656A1 (de) *	1992-06-13	1993-12-16	Merck Patent Gmbh	Benzimidazolderivate
FR2806093B1 (fr) *	2000-03-08	2002-05-03	Inst Francais Du Petrole	Procede d'hydrogenation selective comprenant une separation partielle d'hydrogene par membrane en amont d'une colonne reactive
CN101410385B (zh)	2006-03-28	2011-08-24	高点制药有限责任公司	具有组胺h3受体活性的苯并噻唑类
JP5794297B2 (ja) *	2010-05-07	2015-10-14	ベーリンガーインゲルハイムインターナショナルゲゼルシャフトミットベシュレンクテルハフツング	Ｇｐｒ１１９アゴニストとしてのピリダジノン
CA2834548C (fr)	2011-04-28	2021-06-01	The Broad Institute, Inc.	Inhibiteurs de l'histone desacetylase
EP2877444B1 (fr)	2012-07-27	2020-09-02	The Broad Institute, Inc.	Inhibiteurs d'histone-désacétylases
US9914717B2 (en)	2012-12-20	2018-03-13	The Broad Institute, Inc.	Cycloalkenyl hydroxamic acid derivatives and their use as histone deacetylase inhibitors
WO2018086703A1 (fr)	2016-11-11	2018-05-17	Bayer Pharma Aktiengesellschaft	Dihydropyridazinones substituées par des phénylurées
EP3737362B1 (fr)	2018-01-12	2025-10-15	Kdac Therapeutics, Inc.	Combinaison d'un inhibiteur sélectif de désacétylase d'histone 3 (hdac3) et d'un agent d'immunothérapie pour le traitement du cancer
EP3746079A1 (fr)	2018-01-31	2020-12-09	Bayer Aktiengesellschaft	Conjugués anticorps-médicament (adc) avec des inhibiteurs de nampt
WO2021013693A1 (fr)	2019-07-23	2021-01-28	Bayer Pharma Aktiengesellschaft	Conjugués anticorps-médicament (adc) avec des inhibiteurs de nampt
WO2023003468A1 (fr)	2021-07-23	2023-01-26	Rijksuniversiteit Groningen	Nouveaux inhibiteurs de l'histone désacétylase (hdac), procédés, compositions et utilisations s'y rapportant

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ES8101067A1 (es) *	1978-08-25	1980-12-01	Thomae Gmbh Dr K	Procedimiento para la preparacion de nuevos bencimidazoles sustituidos en posicion 5 o 6 con un anillo de piridazinona
DE3129447A1 (de) *	1981-07-25	1983-02-10	Dr. Karl Thomae Gmbh, 7950 Biberach	"neue benztriazole, ihre herstellung und ihre verwendung als arzneimittel"
DE3505609A1 (de) *	1985-02-19	1986-08-21	Merck Patent Gmbh, 6100 Darmstadt	Benzimidazolyl-pyridazinone

1985
- 1985-03-27 DE DE19853511110 patent/DE3511110A1/de not_active Withdrawn
1986
- 1986-03-18 AT AT86103687T patent/ATE48841T1/de not_active IP Right Cessation
- 1986-03-18 EP EP86103687A patent/EP0196005B1/fr not_active Expired
- 1986-03-18 DE DE8686103687T patent/DE3667664D1/de not_active Expired - Lifetime
- 1986-03-21 DK DK131886A patent/DK131886A/da not_active Application Discontinuation
- 1986-03-25 IL IL78251A patent/IL78251A0/xx unknown
- 1986-03-25 DD DD86288285A patent/DD248362A5/de unknown
- 1986-03-25 CA CA000505012A patent/CA1257588A/fr not_active Expired
- 1986-03-26 GR GR860801A patent/GR860801B/el unknown
- 1986-03-26 AU AU55303/86A patent/AU5530386A/en not_active Abandoned
- 1986-03-26 ZA ZA862248A patent/ZA862248B/xx unknown
- 1986-03-26 PT PT82272A patent/PT82272B/pt unknown
- 1986-03-26 NZ NZ215616A patent/NZ215616A/en unknown
- 1986-03-26 JP JP61068255A patent/JPS61227582A/ja active Pending
- 1986-03-26 FI FI861288A patent/FI861288A7/fi not_active IP Right Cessation
- 1986-03-26 NO NO861266A patent/NO861266L/no unknown
- 1986-03-26 HU HU861275A patent/HUT42085A/hu unknown
- 1986-03-26 ES ES553463A patent/ES8705882A1/es not_active Expired
- 1986-03-26 KR KR1019860002262A patent/KR860007253A/ko not_active Withdrawn
- 1986-11-21 ES ES557218A patent/ES8705883A1/es not_active Expired
- 1986-11-21 ES ES557220A patent/ES8705885A1/es not_active Expired
- 1986-11-21 ES ES557219A patent/ES8705884A1/es not_active Expired

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0350990A1 (fr) *	1988-07-11	1990-01-17	Akzo Nobel N.V.	Dérivés de pyridazinone

Also Published As

Publication number	Publication date
NZ215616A (en)	1990-01-29
ATE48841T1 (de)	1990-01-15
DK131886A (da)	1986-09-28
FI861288A7 (fi)	1986-09-28
EP0196005B1 (fr)	1989-12-20
FI861288A0 (fi)	1986-03-26
ZA862248B (en)	1987-11-25
ES557219A0 (es)	1987-05-16
PT82272B (de)	1988-01-06
DK131886D0 (da)	1986-03-21
ES8705883A1 (es)	1987-05-16
CA1257588A (fr)	1989-07-18
ES553463A0 (es)	1987-05-16
KR860007253A (ko)	1986-10-10
DE3511110A1 (de)	1986-10-02
ES8705882A1 (es)	1987-05-16
IL78251A0 (en)	1986-07-31
DE3667664D1 (de)	1990-01-25
ES8705884A1 (es)	1987-05-16
ES8705885A1 (es)	1987-05-16
ES557218A0 (es)	1987-05-16
NO861266L (no)	1986-09-29
HUT42085A (en)	1987-06-29
GR860801B (en)	1986-07-21
PT82272A (de)	1986-04-01
EP0196005A1 (fr)	1986-10-01
JPS61227582A (ja)	1986-10-09
AU5530386A (en)	1986-10-02
ES557220A0 (es)	1987-05-16

Publication	Publication Date	Title
DD248362A5 (de)	1987-08-05	Verfahren zur herstellung neuer pyridazinone
DE69013601T2 (de)	1995-03-02	Heteroaryl Piperazine als antipsychotische Mittel.
DE60203263T2 (de)	2006-02-09	Pyrazolderivate gegen tgf überexprimierung
EP0877744B1 (fr)	2004-08-11	Composes aza- et diazacycloheptane et -cyclo-octane substitues et leur utilisation
DD258229A5 (de)	1988-07-13	Verfahren zur herstellung von neuen heterocyclisch substituierten indolderivaten
EP1363904A1 (fr)	2003-11-26	Pyrazoles utilises comme inhibiteurs du tgf
EP0263352A1 (fr)	1988-04-13	Imidazo-benzoxazinones, leur préparation et médicaments contenant ces composés
DE69713255T2 (de)	2002-11-07	Pharmazeutische Pyridin-Derivate, ihre Herstellungsverfahren und Zwischenprodukte dafür
EP0193013A2 (fr)	1986-09-03	Benzimidazolyl-pyridazinones
AU640302B2 (en)	1993-08-19	Pyridine compounds
CH638202A5 (de)	1983-09-15	3-(pyrazol-1-yl)-pyridazin-derivate, deren salze und verfahren zu ihrer herstellung.
DE2845220A1 (de)	1980-04-30	Pyridazinon-derivate, ihre salze mit saeuren, verfahren zu ihrer herstellung und ihre verwendung bei der behandlung von thrombosen und hypertonie
NZ207914A (en)	1986-08-08	Indeno-pyridazinones and pharmaceutical compositions
WO2004055024A1 (fr)	2004-07-01	Derives de 3,4-dihydro-thieno[2,3-d]pyrimidin-4-one 3-substitues, leur preparation et leur utilisation
WO1996002505A1 (fr)	1996-02-01	Composes de thiopyridyle utiles pour combattre des bacteries helicobacter
US4584297A (en)	1986-04-22	Pyrrolo[1,2-c]-1,3-thiazines
EP0128502B1 (fr)	1988-08-31	(Thiényl-2)-6 2H-pyridazinones-3 substituées et procédés pour leur préparation
NO841439L (no)	1984-10-19	Fremgangsmaate for fremstilling av terapeutisk aktive triazin-derivater
EP0175187A1 (fr)	1986-03-26	Dihydro-3,4 (1H)-pyridones-2 et (1H)-pyridones-2 contenant un groupe imidazole, procédé pour leur préparation et médicaments les contenant
US3250769A (en)	1966-05-10	4:6-dialkyl-pyrazolo [3:4-b] pyridines
Archibald et al.	1974	Benzamidopiperidines. 2. Heterocyclic compounds related to indoramin
US5684006A (en)	1997-11-04	Isoxazole and pyrazole derivatives as dopamine receptor subtype ligands
DE68913167T2 (de)	1994-09-01	Indol-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Präparate.
EP0255704A2 (fr)	1988-02-10	Dérivés de pyridazinone, procédé pour leur préparation et leur utilisation comme médicament
CS235976B2 (en)	1985-05-15	Method of pyrimidine derivatives production

DD248362A5 - Verfahren zur herstellung neuer pyridazinone - Google Patents

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Applications Claiming Priority (1)

Publications (1)

Family

ID=6266489

Family Applications (1)

Country Status (18)

Cited By (1)

Families Citing this family (18)

Family Cites Families (3)

Cited By (1)

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