DE3019019C2 - - Google Patents
Info
- Publication number
- DE3019019C2 DE3019019C2 DE3019019A DE3019019A DE3019019C2 DE 3019019 C2 DE3019019 C2 DE 3019019C2 DE 3019019 A DE3019019 A DE 3019019A DE 3019019 A DE3019019 A DE 3019019A DE 3019019 C2 DE3019019 C2 DE 3019019C2
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- pyrazolo
- quinazoline derivatives
- quinazoline
- radical
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 36
- ONCMJWSDNCJMLL-UHFFFAOYSA-N pyrazolo[1,5-c]quinazoline Chemical class C12=CC=CC=C2N=CN2C1=CC=N2 ONCMJWSDNCJMLL-UHFFFAOYSA-N 0.000 claims description 24
- 239000000126 substance Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- -1 carboxylic acid halides Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 4
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims 2
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Chemical class CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- 238000002844 melting Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- QIDNDPFRZNLDQS-UHFFFAOYSA-N 1-nitropyrazolo[1,5-c]quinazoline Chemical class C1=CC=C2C3=C([N+](=O)[O-])C=NN3C=NC2=C1 QIDNDPFRZNLDQS-UHFFFAOYSA-N 0.000 description 9
- 230000000202 analgesic effect Effects 0.000 description 9
- 229910052799 carbon Inorganic materials 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SHENZVZJIWAEGR-UHFFFAOYSA-N n-pyrazolo[1,5-c]quinazolin-1-ylacetamide Chemical class C1=CC=C2C3=C(NC(=O)C)C=NN3C=NC2=C1 SHENZVZJIWAEGR-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 5
- 125000003226 pyrazolyl group Chemical group 0.000 description 5
- QMHRIMOYNIMBCT-UHFFFAOYSA-N 1-(5,5-dimethyl-1-nitropyrazolo[1,5-c]quinazolin-6-yl)ethanone Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(C)(C)N(C(=O)C)C2=C1 QMHRIMOYNIMBCT-UHFFFAOYSA-N 0.000 description 4
- WSUMACMTWKPAJN-UHFFFAOYSA-N 1-(5-methyl-1-nitro-5h-pyrazolo[1,5-c]quinazolin-6-yl)ethanone Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(C)N(C(C)=O)C2=C1 WSUMACMTWKPAJN-UHFFFAOYSA-N 0.000 description 4
- ZRSKJGSWNQLLMK-UHFFFAOYSA-N 5,5-dimethyl-1-nitro-6H-pyrazolo[1,5-c]quinazoline Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(C)(C)NC2=C1 ZRSKJGSWNQLLMK-UHFFFAOYSA-N 0.000 description 4
- DQPHTZBRMSFAEV-UHFFFAOYSA-N 5-methyl-1-nitropyrazolo[1,5-c]quinazoline Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(C)=NC2=C1 DQPHTZBRMSFAEV-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000539 anti-peristaltic effect Effects 0.000 description 4
- 229940125898 compound 5 Drugs 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000027119 gastric acid secretion Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- QBEOFZZJONHXDR-UHFFFAOYSA-N 1-(1-amino-5-methyl-5h-pyrazolo[1,5-c]quinazolin-6-yl)ethanone Chemical compound C1=CC=C2C3=C(N)C=NN3C(C)N(C(C)=O)C2=C1 QBEOFZZJONHXDR-UHFFFAOYSA-N 0.000 description 3
- ZMNSHKCYIZWYRJ-UHFFFAOYSA-N 5-methyl-1-nitro-5,6-dihydropyrazolo[1,5-c]quinazoline Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(C)NC2=C1 ZMNSHKCYIZWYRJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000003266 anti-allergic 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
- 238000001816 cooling Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000968 intestinal effect Effects 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- JTIDKHDQCMBOEG-UHFFFAOYSA-N n-(5-methylpyrazolo[1,5-c]quinazolin-1-yl)acetamide Chemical compound C1=CC=C2C3=C(NC(=O)C)C=NN3C(C)=NC2=C1 JTIDKHDQCMBOEG-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XUTPDXWQYSTOSG-UHFFFAOYSA-N pyrazolo[1,5-c]quinazolin-1-amine Chemical compound C1=CC=C2C3=C(N)C=NN3C=NC2=C1 XUTPDXWQYSTOSG-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 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 2
- KXZDPXQOYQDKSH-UHFFFAOYSA-N 1-nitro-5,6-dihydropyrazolo[1,5-c]quinazoline Chemical compound C1=CC=C2C3=C([N+](=O)[O-])C=NN3CNC2=C1 KXZDPXQOYQDKSH-UHFFFAOYSA-N 0.000 description 2
- SGXSRGNEKOJZCC-UHFFFAOYSA-N 1-nitro-5-phenyl-5,6-dihydropyrazolo[1,5-c]quinazoline Chemical compound N1C2=CC=CC=C2C2=C([N+](=O)[O-])C=NN2C1C1=CC=CC=C1 SGXSRGNEKOJZCC-UHFFFAOYSA-N 0.000 description 2
- UTLYCSUYULARDE-UHFFFAOYSA-N 2-(4-chlorobenzoyl)-6H-pyrazolo[1,5-c]quinazolin-5-one Chemical compound ClC1=CC=C(C(=O)C2=NN3C(NC=4C=CC=CC4C3=C2)=O)C=C1 UTLYCSUYULARDE-UHFFFAOYSA-N 0.000 description 2
- ZRFUZDDJSQVQBY-UHFFFAOYSA-N 4-chloro-3-nitroquinoline Chemical compound C1=CC=CC2=C(Cl)C([N+](=O)[O-])=CN=C21 ZRFUZDDJSQVQBY-UHFFFAOYSA-N 0.000 description 2
- FVEMFYWCCPYHGN-UHFFFAOYSA-N 5,5-diethyl-1-nitro-6H-pyrazolo[1,5-c]quinazoline Chemical compound C1=CC=C2C3=C([N+]([O-])=O)C=NN3C(CC)(CC)NC2=C1 FVEMFYWCCPYHGN-UHFFFAOYSA-N 0.000 description 2
- VGXQZOHTBJLENW-UHFFFAOYSA-N 5,5-dimethyl-6H-pyrazolo[1,5-c]quinazolin-1-amine Chemical compound C1=CC=C2C3=C(N)C=NN3C(C)(C)NC2=C1 VGXQZOHTBJLENW-UHFFFAOYSA-N 0.000 description 2
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 229930003347 Atropine Natural products 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-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
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- 241001465754 Metazoa Species 0.000 description 2
- FGWZGLLFWVRENW-UHFFFAOYSA-N N-(5,5-dimethyl-6H-pyrazolo[1,5-c]quinazolin-1-yl)acetamide Chemical compound C1=CC=C2NC(C)(C)N3N=CC(NC(=O)C)=C3C2=C1 FGWZGLLFWVRENW-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 2
- 229960000396 atropine Drugs 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- CCGSUNCLSOWKJO-UHFFFAOYSA-N cimetidine Chemical compound N#CNC(=N/C)\NCCSCC1=NC=N[C]1C CCGSUNCLSOWKJO-UHFFFAOYSA-N 0.000 description 2
- 229960001380 cimetidine Drugs 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002168 ethanoic acid esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VLTPBTDVOTUSNC-UHFFFAOYSA-N n-(6-acetyl-5,5-dimethylpyrazolo[1,5-c]quinazolin-1-yl)acetamide Chemical compound C1=CC=C2N(C(C)=O)C(C)(C)N3N=CC(NC(=O)C)=C3C2=C1 VLTPBTDVOTUSNC-UHFFFAOYSA-N 0.000 description 2
- JRYCOAHCIXVSFO-UHFFFAOYSA-N n-(6-acetyl-5-methyl-5h-pyrazolo[1,5-c]quinazolin-1-yl)acetamide Chemical compound C1=CC=C2C3=C(NC(C)=O)C=NN3C(C)N(C(C)=O)C2=C1 JRYCOAHCIXVSFO-UHFFFAOYSA-N 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229960003857 proglumide Drugs 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
- 229960004793 sucrose Drugs 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BICSQKWXCFDCFL-UHFFFAOYSA-N 1-(1-amino-5,5-dimethylpyrazolo[1,5-c]quinazolin-6-yl)ethanone Chemical compound C1=CC=C2C3=C(N)C=NN3C(C)(C)N(C(=O)C)C2=C1 BICSQKWXCFDCFL-UHFFFAOYSA-N 0.000 description 1
- KTOQRRDVVIDEAA-UHFFFAOYSA-N 2-methylpropane Chemical compound [CH2]C(C)C KTOQRRDVVIDEAA-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- XORHNJQEWQGXCN-UHFFFAOYSA-N 4-nitro-1h-pyrazole Chemical compound [O-][N+](=O)C=1C=NNC=1 XORHNJQEWQGXCN-UHFFFAOYSA-N 0.000 description 1
- DICVODJQRGZQBM-UHFFFAOYSA-N 5-methylpyrazolo[1,5-c]quinazolin-1-amine Chemical compound C1=CC=C2C3=C(N)C=NN3C(C)=NC2=C1 DICVODJQRGZQBM-UHFFFAOYSA-N 0.000 description 1
- XVYVWBCXJZGTJV-UHFFFAOYSA-N 6H-pyrazolo[1,5-c]quinazolin-5-one Chemical compound C1=CC=C2C3=CC=NN3C(=O)NC2=C1 XVYVWBCXJZGTJV-UHFFFAOYSA-N 0.000 description 1
- WHXDLJOHWHFXJR-UHFFFAOYSA-N CC(=O)NC1=CC=C(O)C=C1.CC(=O)NC1=CC=C(O)C=C1 Chemical compound CC(=O)NC1=CC=C(O)C=C1.CC(=O)NC1=CC=C(O)C=C1 WHXDLJOHWHFXJR-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 230000000947 anti-immunosuppressive effect Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- LOEZZXJJMKOHOO-UHFFFAOYSA-N pyrazolo[1,5-c]quinazolin-5-amine Chemical class C1=CC=C2C3=CC=NN3C(N)=NC2=C1 LOEZZXJJMKOHOO-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D231/16—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2663A HU178523B (en) | 1979-05-18 | 1979-05-18 | Process for preparing new pyrazolo-quinazoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3019019A1 DE3019019A1 (de) | 1980-11-27 |
| DE3019019C2 true DE3019019C2 (en, 2012) | 1988-12-01 |
Family
ID=10995850
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803019019 Granted DE3019019A1 (de) | 1979-05-18 | 1980-05-19 | Pyrazolo eckige klammer auf 1,5-c eckige klammer zu chinazolinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4303660A (en, 2012) |
| JP (1) | JPS55154974A (en, 2012) |
| AT (1) | AT375941B (en, 2012) |
| AU (1) | AU528013B2 (en, 2012) |
| BE (1) | BE883204A (en, 2012) |
| CH (1) | CH646170A5 (en, 2012) |
| CS (1) | CS241026B2 (en, 2012) |
| DD (1) | DD150897A5 (en, 2012) |
| DE (1) | DE3019019A1 (en, 2012) |
| ES (1) | ES8105319A1 (en, 2012) |
| FR (1) | FR2456744A1 (en, 2012) |
| GB (1) | GB2051054B (en, 2012) |
| GR (1) | GR68462B (en, 2012) |
| HU (1) | HU178523B (en, 2012) |
| IT (1) | IT1149882B (en, 2012) |
| NL (1) | NL8002853A (en, 2012) |
| SU (3) | SU978731A3 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4469868A (en) * | 1982-05-24 | 1984-09-04 | Warner-Lambert Company | Alkylimidazo[1,2-c]pyrazolo[3,4-e]pyrimidines |
| DE3942357A1 (de) * | 1989-12-21 | 1991-06-27 | Boehringer Mannheim Gmbh | 3-aminopyrazolo-heterocyclen, deren verwendung zur bestimmung von wasserstoffperoxid, wasserstoffperoxid-bildenden systemen, peroxidase, peroxidatisch wirksamen substanzen oder von elektronenreichen aromatischen verbindungen, entsprechende bestimmungsverfahren und hierfuer geeignete mittel |
| JP2002537397A (ja) * | 1999-02-22 | 2002-11-05 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | 抗炎症剤としての多環ヘテロ環式誘導体 |
| GB2453116B (en) * | 2007-09-25 | 2010-03-17 | Medical & Pharm Ind Tech & Dev | Uses of 2-[piperidinyl]methy1-2,3-dihydroimidazo[1,2-c]quinazolin-5(6H)-one in providing an analgesic effect |
| CN103130810B (zh) * | 2013-03-11 | 2015-02-25 | 河南师范大学 | 一种吡唑并[1,5-c]喹唑啉类化合物的合成方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3313815A (en) * | 1964-05-04 | 1967-04-11 | Sterling Drug Inc | 8-chloropyrazolo-[1, 5-c]quinazoline derivatives and methods of preparing same |
| US3531482A (en) * | 1966-10-13 | 1970-09-29 | Sandoz Ag | Pyrazolo(1,5-c)quinazolines |
| US3897434A (en) * | 1974-04-12 | 1975-07-29 | Lilly Co Eli | Pyrazolo{8 1,5-c{9 quinazolin-5(6H)-ones |
| US4076818A (en) * | 1976-07-02 | 1978-02-28 | E. R. Squibb & Sons, Inc. | Pyrazolo [1,5-C]quinazoline derivatives and related compounds |
| US4110452A (en) * | 1977-10-17 | 1978-08-29 | E. R. Squibb & Sons, Inc. | Pyrazolo (1,5-c) quinazoline derivatives and related compounds |
| US4112098A (en) * | 1977-10-17 | 1978-09-05 | E. R. Squibb & Sons, Inc. | Pyrazolo[1,5-c]quinazoline derivatives and related compounds |
| US4198412A (en) * | 1978-12-13 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Pyrazolo [1,5-C] quinazoline derivatives and their use in treating allergic conditions |
-
1979
- 1979-05-18 HU HU79EE2663A patent/HU178523B/hu not_active IP Right Cessation
-
1980
- 1980-05-09 BE BE1/9814A patent/BE883204A/fr not_active IP Right Cessation
- 1980-05-12 FR FR8010562A patent/FR2456744A1/fr active Granted
- 1980-05-13 GB GB8015781A patent/GB2051054B/en not_active Expired
- 1980-05-16 SU SU802924054A patent/SU978731A3/ru active
- 1980-05-16 DD DD80221164A patent/DD150897A5/de not_active IP Right Cessation
- 1980-05-16 GR GR61970A patent/GR68462B/el unknown
- 1980-05-16 CH CH382280A patent/CH646170A5/de not_active IP Right Cessation
- 1980-05-16 AT AT0262580A patent/AT375941B/de not_active IP Right Cessation
- 1980-05-16 JP JP6420580A patent/JPS55154974A/ja active Granted
- 1980-05-16 NL NL8002853A patent/NL8002853A/nl not_active Application Discontinuation
- 1980-05-16 IT IT22111/80A patent/IT1149882B/it active
- 1980-05-16 AU AU58485/80A patent/AU528013B2/en not_active Ceased
- 1980-05-16 CS CS803407A patent/CS241026B2/cs unknown
- 1980-05-16 US US06/150,349 patent/US4303660A/en not_active Expired - Lifetime
- 1980-05-19 ES ES491608A patent/ES8105319A1/es not_active Expired
- 1980-05-19 DE DE19803019019 patent/DE3019019A1/de active Granted
-
1981
- 1981-05-26 SU SU813287153A patent/SU1017171A3/ru active
- 1981-05-26 SU SU813287448A patent/SU1015828A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| IT1149882B (it) | 1986-12-10 |
| SU1015828A3 (ru) | 1983-04-30 |
| CS340780A2 (en) | 1985-06-13 |
| IT8022111A0 (it) | 1980-05-16 |
| HU178523B (en) | 1982-05-28 |
| NL8002853A (nl) | 1980-11-20 |
| SU1017171A3 (ru) | 1983-05-07 |
| DD150897A5 (de) | 1981-09-23 |
| JPS55154974A (en) | 1980-12-02 |
| GR68462B (en, 2012) | 1981-12-30 |
| ES491608A0 (es) | 1981-05-16 |
| BE883204A (fr) | 1980-11-10 |
| FR2456744A1 (fr) | 1980-12-12 |
| ES8105319A1 (es) | 1981-05-16 |
| AT375941B (de) | 1984-09-25 |
| ATA262580A (de) | 1984-02-15 |
| US4303660A (en) | 1981-12-01 |
| JPH0227356B2 (en, 2012) | 1990-06-15 |
| CS241026B2 (en) | 1986-03-13 |
| SU978731A3 (ru) | 1982-11-30 |
| GB2051054B (en) | 1983-05-18 |
| GB2051054A (en) | 1981-01-14 |
| AU528013B2 (en) | 1983-03-31 |
| CH646170A5 (de) | 1984-11-15 |
| FR2456744B1 (en, 2012) | 1983-06-17 |
| DE3019019A1 (de) | 1980-11-27 |
| AU5848580A (en) | 1980-11-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8101 | Request for examination as to novelty | ||
| 8105 | Search report available | ||
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |