DE2212245A1 - Neue organische Verbindungen und Verfahren zu deren Herstellung - Google Patents
Neue organische Verbindungen und Verfahren zu deren HerstellungInfo
- Publication number
- DE2212245A1 DE2212245A1 DE19722212245 DE2212245A DE2212245A1 DE 2212245 A1 DE2212245 A1 DE 2212245A1 DE 19722212245 DE19722212245 DE 19722212245 DE 2212245 A DE2212245 A DE 2212245A DE 2212245 A1 DE2212245 A1 DE 2212245A1
- Authority
- DE
- Germany
- Prior art keywords
- amino
- thiadiazole
- chloride
- thiosemicarbazide
- formula
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 23
- 150000002894 organic compounds Chemical class 0.000 title claims 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000002841 Lewis acid Substances 0.000 claims description 6
- 150000007517 lewis acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 101150018711 AASS gene Proteins 0.000 claims 1
- OXNGKCPRVRBHPO-XLMUYGLTSA-N alpha-L-Fucp-(1->2)-beta-D-Galp-(1->3)-[alpha-L-Fucp-(1->4)]-beta-D-GlcpNAc Chemical class O[C@H]1[C@H](O)[C@H](O)[C@H](C)O[C@H]1O[C@H]1[C@H](O[C@H]2[C@@H]([C@@H](CO)O[C@@H](O)[C@@H]2NC(C)=O)O[C@H]2[C@H]([C@H](O)[C@H](O)[C@H](C)O2)O)O[C@H](CO)[C@H](O)[C@@H]1O OXNGKCPRVRBHPO-XLMUYGLTSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- -1 (4- [phenylbutyl]) thiadiazole Chemical compound 0.000 description 29
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- VSHULXBTMXBAAP-UHFFFAOYSA-N 5-phenylpentanoyl chloride Chemical compound ClC(=O)CCCCC1=CC=CC=C1 VSHULXBTMXBAAP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- FRDAMOQWGGGQRM-UHFFFAOYSA-N 4-phenylbutanehydrazide Chemical compound NNC(=O)CCCC1=CC=CC=C1 FRDAMOQWGGGQRM-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 4
- VQDQISMDUHBUFF-UHFFFAOYSA-N 4-phenylbutanoyl chloride Chemical compound ClC(=O)CCCC1=CC=CC=C1 VQDQISMDUHBUFF-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- NONOKGVFTBWRLD-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane Chemical compound O=C=NSN=C=O NONOKGVFTBWRLD-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- AAQKHRQYDFNPSG-UHFFFAOYSA-N (4-phenylbutanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCC1=CC=CC=C1 AAQKHRQYDFNPSG-UHFFFAOYSA-N 0.000 description 2
- RYXAJKPGHHNCSO-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1Cl RYXAJKPGHHNCSO-UHFFFAOYSA-N 0.000 description 2
- VFRDBQGBQYINBH-UHFFFAOYSA-N 2-(2,6-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC=C1Cl VFRDBQGBQYINBH-UHFFFAOYSA-N 0.000 description 2
- WIHSAOYVGKVRJX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1Cl WIHSAOYVGKVRJX-UHFFFAOYSA-N 0.000 description 2
- KUMKNGTWQNSAQW-UHFFFAOYSA-N 2-(2-fluorophenyl)acetyl chloride Chemical compound FC1=CC=CC=C1CC(Cl)=O KUMKNGTWQNSAQW-UHFFFAOYSA-N 0.000 description 2
- FKMIBYMTHOJWCY-UHFFFAOYSA-N 2-(2-methylphenyl)acetyl chloride Chemical compound CC1=CC=CC=C1CC(Cl)=O FKMIBYMTHOJWCY-UHFFFAOYSA-N 0.000 description 2
- PYPMKORNJLTHGP-UHFFFAOYSA-N 2-(3-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=CC(Cl)=C1 PYPMKORNJLTHGP-UHFFFAOYSA-N 0.000 description 2
- BGGKEDDFKBVTDK-UHFFFAOYSA-N 2-(3-methylphenyl)acetyl chloride Chemical compound CC1=CC=CC(CC(Cl)=O)=C1 BGGKEDDFKBVTDK-UHFFFAOYSA-N 0.000 description 2
- UMQUIRYNOVNYPA-UHFFFAOYSA-N 2-(4-chlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C=C1 UMQUIRYNOVNYPA-UHFFFAOYSA-N 0.000 description 2
- SIOJFYRPBYGHOO-UHFFFAOYSA-N 2-(4-fluorophenyl)acetyl chloride Chemical compound FC1=CC=C(CC(Cl)=O)C=C1 SIOJFYRPBYGHOO-UHFFFAOYSA-N 0.000 description 2
- QDZAWVLWIMOXJT-UHFFFAOYSA-N 2-(4-methylphenyl)acetyl chloride Chemical compound CC1=CC=C(CC(Cl)=O)C=C1 QDZAWVLWIMOXJT-UHFFFAOYSA-N 0.000 description 2
- PUPIOOXFPITOGF-UHFFFAOYSA-N 2-methyl-4-phenylbutanoyl chloride Chemical compound ClC(=O)C(C)CCC1=CC=CC=C1 PUPIOOXFPITOGF-UHFFFAOYSA-N 0.000 description 2
- LGYLVAGSJRQWMD-UHFFFAOYSA-N 2-methyl-8-phenyloctanoyl chloride Chemical compound ClC(=O)C(C)CCCCCCC1=CC=CC=C1 LGYLVAGSJRQWMD-UHFFFAOYSA-N 0.000 description 2
- FBSLKAVDKNAZSK-UHFFFAOYSA-N 2-methyl-9-phenylnonanoyl chloride Chemical compound ClC(=O)C(C)CCCCCCCC1=CC=CC=C1 FBSLKAVDKNAZSK-UHFFFAOYSA-N 0.000 description 2
- FOTITZRWZUAVPH-UHFFFAOYSA-N 2-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)C1=CC=CC=C1 FOTITZRWZUAVPH-UHFFFAOYSA-N 0.000 description 2
- XCAXRFFRVJOHMX-UHFFFAOYSA-N 3-phenylbutanoyl chloride Chemical compound ClC(=O)CC(C)C1=CC=CC=C1 XCAXRFFRVJOHMX-UHFFFAOYSA-N 0.000 description 2
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 2
- ZGWDGLXJNLDRIX-UHFFFAOYSA-N 4-phenylpentanoyl chloride Chemical compound ClC(=O)CCC(C)C1=CC=CC=C1 ZGWDGLXJNLDRIX-UHFFFAOYSA-N 0.000 description 2
- LAHMQYDXYCJZOP-UHFFFAOYSA-N 5-(10-phenyldecan-3-yl)-3h-thiadiazol-2-amine Chemical compound C=1NN(N)SC=1C(CC)CCCCCCCC1=CC=CC=C1 LAHMQYDXYCJZOP-UHFFFAOYSA-N 0.000 description 2
- HPKCWMSOMVTZAI-UHFFFAOYSA-N 5-(2,6-dimethylphenyl)-2-methylpentanoyl chloride Chemical compound ClC(=O)C(C)CCCC1=C(C)C=CC=C1C HPKCWMSOMVTZAI-UHFFFAOYSA-N 0.000 description 2
- CGCUEMKRWHPBBJ-UHFFFAOYSA-N 5-(2,6-dimethylphenyl)hexanoyl chloride Chemical compound ClC(=O)CCCC(C)C1=C(C)C=CC=C1C CGCUEMKRWHPBBJ-UHFFFAOYSA-N 0.000 description 2
- BDATVYQYUNICTC-UHFFFAOYSA-N 5-(3-phenylbutyl)-3h-thiadiazol-2-amine Chemical compound C=1C=CC=CC=1C(C)CCC1=CNN(N)S1 BDATVYQYUNICTC-UHFFFAOYSA-N 0.000 description 2
- UXDJNQQVKGVJRV-UHFFFAOYSA-N 5-(4-chlorophenyl)pentanoyl chloride Chemical compound ClC(=O)CCCCC1=CC=C(Cl)C=C1 UXDJNQQVKGVJRV-UHFFFAOYSA-N 0.000 description 2
- VIYFCMLSFZMFEL-UHFFFAOYSA-N 5-(4-methoxyphenyl)pentanoyl chloride Chemical compound COC1=CC=C(CCCCC(Cl)=O)C=C1 VIYFCMLSFZMFEL-UHFFFAOYSA-N 0.000 description 2
- XVLBFTGLYLNLCW-UHFFFAOYSA-N 5-(6-phenylhexyl)-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CCCCCCC1=CC=CC=C1 XVLBFTGLYLNLCW-UHFFFAOYSA-N 0.000 description 2
- KBNHEPWSHDZYSE-UHFFFAOYSA-N 5-(7-phenylheptyl)-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CCCCCCCC1=CC=CC=C1 KBNHEPWSHDZYSE-UHFFFAOYSA-N 0.000 description 2
- SQNOEFWRHYMIEP-UHFFFAOYSA-N 5-(7-phenyloctyl)-3h-thiadiazol-2-amine Chemical compound C=1C=CC=CC=1C(C)CCCCCCC1=CNN(N)S1 SQNOEFWRHYMIEP-UHFFFAOYSA-N 0.000 description 2
- BUECYAJDDFCPPL-UHFFFAOYSA-N 5-(8-phenyloctan-2-yl)-3h-thiadiazol-2-amine Chemical compound C=1NN(N)SC=1C(C)CCCCCCC1=CC=CC=C1 BUECYAJDDFCPPL-UHFFFAOYSA-N 0.000 description 2
- WVBMXFGLRRIYFB-UHFFFAOYSA-N 5-(8-phenyloctyl)-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CCCCCCCCC1=CC=CC=C1 WVBMXFGLRRIYFB-UHFFFAOYSA-N 0.000 description 2
- XVNDAGVJONCAJH-UHFFFAOYSA-N 5-[(2,3,6-trichlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=C(Cl)C=CC(Cl)=C1Cl XVNDAGVJONCAJH-UHFFFAOYSA-N 0.000 description 2
- CMNQLPNQBHLHLK-UHFFFAOYSA-N 5-[(3,4-dichlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=C(Cl)C(Cl)=C1 CMNQLPNQBHLHLK-UHFFFAOYSA-N 0.000 description 2
- CRPVWLYTROXSAH-UHFFFAOYSA-N 5-[(3-chlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=CC(Cl)=C1 CRPVWLYTROXSAH-UHFFFAOYSA-N 0.000 description 2
- HQCVJWIANXBLLB-UHFFFAOYSA-N 5-[(4-chlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=C(Cl)C=C1 HQCVJWIANXBLLB-UHFFFAOYSA-N 0.000 description 2
- RFSRLGKZVHPFDB-UHFFFAOYSA-N 5-[(4-fluorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=C(F)C=C1 RFSRLGKZVHPFDB-UHFFFAOYSA-N 0.000 description 2
- QZGDCPDBCYAZRI-UHFFFAOYSA-N 5-[5-(2,6-dichlorophenyl)hexyl]-3h-thiadiazol-2-amine Chemical compound ClC=1C=CC=C(Cl)C=1C(C)CCCCC1=CNN(N)S1 QZGDCPDBCYAZRI-UHFFFAOYSA-N 0.000 description 2
- NNZYOSGLARBGJT-UHFFFAOYSA-N 6-(2,6-dimethylphenyl)hexanoyl chloride Chemical compound CC1=CC=CC(C)=C1CCCCCC(Cl)=O NNZYOSGLARBGJT-UHFFFAOYSA-N 0.000 description 2
- BWOCDJBMOYTZLN-UHFFFAOYSA-N 6-phenylhexanoyl chloride Chemical compound ClC(=O)CCCCCC1=CC=CC=C1 BWOCDJBMOYTZLN-UHFFFAOYSA-N 0.000 description 2
- YBRKOQFSSXELQT-UHFFFAOYSA-N 7-(2,6-dichlorophenyl)heptanoyl chloride Chemical compound ClC(=O)CCCCCCC1=C(Cl)C=CC=C1Cl YBRKOQFSSXELQT-UHFFFAOYSA-N 0.000 description 2
- DWUOFSBDTAJUIX-UHFFFAOYSA-N 7-(4-methoxyphenyl)-2-methylheptanoyl chloride Chemical compound COC1=CC=C(CCCCCC(C)C(Cl)=O)C=C1 DWUOFSBDTAJUIX-UHFFFAOYSA-N 0.000 description 2
- ZHLNYUTWJGXKIK-UHFFFAOYSA-N 7-(4-methoxyphenyl)octanoyl chloride Chemical compound COC1=CC=C(C(C)CCCCCC(Cl)=O)C=C1 ZHLNYUTWJGXKIK-UHFFFAOYSA-N 0.000 description 2
- IIWAGNNALINQLK-UHFFFAOYSA-N 7-phenylheptanoyl chloride Chemical compound ClC(=O)CCCCCCC1=CC=CC=C1 IIWAGNNALINQLK-UHFFFAOYSA-N 0.000 description 2
- OQKHLUROUVPCBC-UHFFFAOYSA-N 8-phenylnonanoyl chloride Chemical compound ClC(=O)CCCCCCC(C)C1=CC=CC=C1 OQKHLUROUVPCBC-UHFFFAOYSA-N 0.000 description 2
- APHSLJHSEAOVNC-UHFFFAOYSA-N 8-phenyloctanoyl chloride Chemical compound ClC(=O)CCCCCCCC1=CC=CC=C1 APHSLJHSEAOVNC-UHFFFAOYSA-N 0.000 description 2
- OJFLZBORLZAOFG-UHFFFAOYSA-N 9-phenylnonanoyl chloride Chemical compound ClC(=O)CCCCCCCCC1=CC=CC=C1 OJFLZBORLZAOFG-UHFFFAOYSA-N 0.000 description 2
- MLPDCSULLPAMQF-UHFFFAOYSA-N 9-phenylundecanoyl chloride Chemical compound ClC(=O)CCCCCCCC(CC)C1=CC=CC=C1 MLPDCSULLPAMQF-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 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
- 230000004799 sedative–hypnotic effect Effects 0.000 description 2
- KVNRWHDPLXVHPO-UHFFFAOYSA-N (3-phenylbutanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CC(C)C1=CC=CC=C1 KVNRWHDPLXVHPO-UHFFFAOYSA-N 0.000 description 1
- LSZLWFQBTYXDJR-UHFFFAOYSA-N (4-phenylpentanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCC(C)C1=CC=CC=C1 LSZLWFQBTYXDJR-UHFFFAOYSA-N 0.000 description 1
- MDWPKIWOJVOOHY-UHFFFAOYSA-N (5-phenylpentanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCCC1=CC=CC=C1 MDWPKIWOJVOOHY-UHFFFAOYSA-N 0.000 description 1
- JSEVSMUSFYFQAT-UHFFFAOYSA-N (6-phenylhexanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCCCC1=CC=CC=C1 JSEVSMUSFYFQAT-UHFFFAOYSA-N 0.000 description 1
- JNHQRLNQSXAOTI-UHFFFAOYSA-N (8-phenylnonanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCCCCC(C)C1=CC=CC=C1 JNHQRLNQSXAOTI-UHFFFAOYSA-N 0.000 description 1
- CITQCHBRGFELBF-UHFFFAOYSA-N (8-phenyloctanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCCCCCC1=CC=CC=C1 CITQCHBRGFELBF-UHFFFAOYSA-N 0.000 description 1
- OQACIPJKZHFXKD-UHFFFAOYSA-N (9-phenylnonanoylamino)thiourea Chemical compound NC(=S)NNC(=O)CCCCCCCCC1=CC=CC=C1 OQACIPJKZHFXKD-UHFFFAOYSA-N 0.000 description 1
- PZGNBMQOQAMXQP-UHFFFAOYSA-N 2-(2,3,6-trichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl PZGNBMQOQAMXQP-UHFFFAOYSA-N 0.000 description 1
- CJJURHKDGQSBLE-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)acetyl chloride Chemical compound ClC(=O)CC1=CC=C(Cl)C(Cl)=C1 CJJURHKDGQSBLE-UHFFFAOYSA-N 0.000 description 1
- SKOMBKMLOHIBTF-UHFFFAOYSA-N 2-(3-fluorophenyl)acetyl chloride Chemical compound FC1=CC=CC(CC(Cl)=O)=C1 SKOMBKMLOHIBTF-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- OWAWAFKVPTWIBP-UHFFFAOYSA-N 2-methyl-3-phenylpropanoyl chloride Chemical compound ClC(=O)C(C)CC1=CC=CC=C1 OWAWAFKVPTWIBP-UHFFFAOYSA-N 0.000 description 1
- APTZAZNLKGGYFK-UHFFFAOYSA-N 5-(2-phenylpropyl)-3h-thiadiazol-2-amine Chemical compound C=1C=CC=CC=1C(C)CC1=CNN(N)S1 APTZAZNLKGGYFK-UHFFFAOYSA-N 0.000 description 1
- YYBHXFCIVMAVTJ-UHFFFAOYSA-N 5-(4-phenylbutan-2-yl)-3h-thiadiazol-2-amine Chemical class C=1NN(N)SC=1C(C)CCC1=CC=CC=C1 YYBHXFCIVMAVTJ-UHFFFAOYSA-N 0.000 description 1
- PEDVINPLBDMMEP-UHFFFAOYSA-N 5-(8-phenyldecyl)-3h-thiadiazol-2-amine Chemical compound C=1C=CC=CC=1C(CC)CCCCCCCC1=CNN(N)S1 PEDVINPLBDMMEP-UHFFFAOYSA-N 0.000 description 1
- QRHPAUULXNTTQR-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=C(Cl)C=C1Cl QRHPAUULXNTTQR-UHFFFAOYSA-N 0.000 description 1
- WHZNQFMOOPXRPW-UHFFFAOYSA-N 5-[(2,6-dichlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=C(Cl)C=CC=C1Cl WHZNQFMOOPXRPW-UHFFFAOYSA-N 0.000 description 1
- PNBPLQCLIKIIOU-UHFFFAOYSA-N 5-[(2-chlorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=CC=C1Cl PNBPLQCLIKIIOU-UHFFFAOYSA-N 0.000 description 1
- UZDKAYPAAUSIMO-UHFFFAOYSA-N 5-[(2-fluorophenyl)methyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CC1=CC=CC=C1F UZDKAYPAAUSIMO-UHFFFAOYSA-N 0.000 description 1
- HKGFRJSQIMIOTP-UHFFFAOYSA-N 5-[4-(2,6-dimethylphenyl)pentyl]-3h-thiadiazol-2-amine Chemical compound CC=1C=CC=C(C)C=1C(C)CCCC1=CNN(N)S1 HKGFRJSQIMIOTP-UHFFFAOYSA-N 0.000 description 1
- LPDOKFKCORHOMX-UHFFFAOYSA-N 5-[4-(4-chlorophenyl)butyl]-3h-thiadiazol-2-amine Chemical compound S1N(N)NC=C1CCCCC1=CC=C(Cl)C=C1 LPDOKFKCORHOMX-UHFFFAOYSA-N 0.000 description 1
- PRLGTJDJKFPPJK-UHFFFAOYSA-N 5-[5-(2,6-dimethylphenyl)pentan-2-yl]-3h-thiadiazol-2-amine Chemical compound C=1NN(N)SC=1C(C)CCCC1=C(C)C=CC=C1C PRLGTJDJKFPPJK-UHFFFAOYSA-N 0.000 description 1
- VNNZWALCNMPKSW-UHFFFAOYSA-N 5-[6-(2,6-dichlorophenyl)hexan-2-yl]-3h-thiadiazol-2-amine Chemical compound C=1NN(N)SC=1C(C)CCCCC1=C(Cl)C=CC=C1Cl VNNZWALCNMPKSW-UHFFFAOYSA-N 0.000 description 1
- FRBTYFIHKKHOMK-UHFFFAOYSA-N 5-[6-(4-methoxyphenyl)heptyl]-3h-thiadiazol-2-amine Chemical compound C1=CC(OC)=CC=C1C(C)CCCCCC1=CNN(N)S1 FRBTYFIHKKHOMK-UHFFFAOYSA-N 0.000 description 1
- HBDKVLFRIRVKLJ-UHFFFAOYSA-N 5-[7-(4-methoxyphenyl)heptan-2-yl]-3h-thiadiazol-2-amine Chemical compound C1=CC(OC)=CC=C1CCCCCC(C)C1=CNN(N)S1 HBDKVLFRIRVKLJ-UHFFFAOYSA-N 0.000 description 1
- ZPKJNYTWYGBBJC-UHFFFAOYSA-N 6-(2,6-dichlorophenyl)-2-methylhexanoyl chloride Chemical compound ClC(=O)C(C)CCCCC1=C(Cl)C=CC=C1Cl ZPKJNYTWYGBBJC-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 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 1
- GGFNXKFGVQQNRV-UHFFFAOYSA-N Ethyl 4-phenylbutanoate Chemical compound CCOC(=O)CCCC1=CC=CC=C1 GGFNXKFGVQQNRV-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- IRZCWXBHPVQRMR-UHFFFAOYSA-N [(2-methyl-8-phenyloctanoyl)amino]thiourea Chemical compound NC(=S)NNC(=O)C(C)CCCCCCC1=CC=CC=C1 IRZCWXBHPVQRMR-UHFFFAOYSA-N 0.000 description 1
- KVEUPTYKVAYZBN-UHFFFAOYSA-N [(2-methyl-9-phenylnonanoyl)amino]thiourea Chemical compound NC(=S)NNC(=O)C(C)CCCCCCCC1=CC=CC=C1 KVEUPTYKVAYZBN-UHFFFAOYSA-N 0.000 description 1
- VMEADUISCGKFQM-UHFFFAOYSA-N [5-(4-chlorophenyl)pentanoylamino]thiourea Chemical compound NC(=S)NNC(=O)CCCCC1=CC=C(Cl)C=C1 VMEADUISCGKFQM-UHFFFAOYSA-N 0.000 description 1
- PYAKMCCQTGWEIZ-UHFFFAOYSA-N [6-(2,6-dimethylphenyl)hexanoylamino]thiourea Chemical compound CC1=CC=CC(C)=C1CCCCCC(=O)NNC(N)=S PYAKMCCQTGWEIZ-UHFFFAOYSA-N 0.000 description 1
- DMIGFAGVVRPWNX-UHFFFAOYSA-N [7-(2,6-dichlorophenyl)heptanoylamino]thiourea Chemical compound NC(=S)NNC(=O)CCCCCCC1=C(Cl)C=CC=C1Cl DMIGFAGVVRPWNX-UHFFFAOYSA-N 0.000 description 1
- WPEWKNDKLPVSNS-UHFFFAOYSA-N [[2-(2,3,6-trichlorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=C(Cl)C=CC(Cl)=C1Cl WPEWKNDKLPVSNS-UHFFFAOYSA-N 0.000 description 1
- NAXVOTUWGOCGOK-UHFFFAOYSA-N [[2-(2-chlorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC=C1Cl NAXVOTUWGOCGOK-UHFFFAOYSA-N 0.000 description 1
- QSEJDYIHOUSBNO-UHFFFAOYSA-N [[2-(2-fluorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC=C1F QSEJDYIHOUSBNO-UHFFFAOYSA-N 0.000 description 1
- GOLPDXBNNPWBMX-UHFFFAOYSA-N [[2-(3-chlorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC(Cl)=C1 GOLPDXBNNPWBMX-UHFFFAOYSA-N 0.000 description 1
- KKVLDTSJKNCMOP-UHFFFAOYSA-N [[2-(3-fluorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=CC(F)=C1 KKVLDTSJKNCMOP-UHFFFAOYSA-N 0.000 description 1
- GXVASXSADQCXLZ-UHFFFAOYSA-N [[2-(4-fluorophenyl)acetyl]amino]thiourea Chemical compound NC(=S)NNC(=O)CC1=CC=C(F)C=C1 GXVASXSADQCXLZ-UHFFFAOYSA-N 0.000 description 1
- SSWXMEVHPWZQLP-UHFFFAOYSA-N [[2-(4-methylphenyl)acetyl]amino]thiourea Chemical compound CC1=CC=C(CC(=O)NNC(N)=S)C=C1 SSWXMEVHPWZQLP-UHFFFAOYSA-N 0.000 description 1
- FLLSRGNTJGYTBJ-UHFFFAOYSA-N [[7-(4-methoxyphenyl)-2-methylheptanoyl]amino]thiourea Chemical compound COC1=CC=C(CCCCCC(C)C(=O)NNC(N)=S)C=C1 FLLSRGNTJGYTBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 229940099112 cornstarch Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- UCVODTZQZHMTPN-UHFFFAOYSA-N heptanoyl chloride Chemical compound CCCCCCC(Cl)=O UCVODTZQZHMTPN-UHFFFAOYSA-N 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- UPWZMUOZQIVEES-UHFFFAOYSA-N isocyanatosulfanylimino(oxo)methane;sodium Chemical compound [Na].O=C=NSN=C=O UPWZMUOZQIVEES-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
- 229940068968 polysorbate 80 Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C243/30—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton
- C07C243/32—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US12448971A | 1971-03-15 | 1971-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2212245A1 true DE2212245A1 (de) | 1972-09-28 |
Family
ID=22415177
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722212245 Pending DE2212245A1 (de) | 1971-03-15 | 1972-03-14 | Neue organische Verbindungen und Verfahren zu deren Herstellung |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | ATA212072A (enrdf_load_stackoverflow) |
| AU (1) | AU467915B2 (enrdf_load_stackoverflow) |
| BE (1) | BE780618A (enrdf_load_stackoverflow) |
| DD (1) | DD100259A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2212245A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2130233B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1380136A (enrdf_load_stackoverflow) |
| HU (1) | HU163329B (enrdf_load_stackoverflow) |
| NL (1) | NL7203192A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1380977A (en) * | 1972-07-18 | 1975-01-22 | May & Baker Ltd | Thiadiazole derivatives |
-
1972
- 1972-03-10 GB GB1125872A patent/GB1380136A/en not_active Expired
- 1972-03-10 NL NL7203192A patent/NL7203192A/xx unknown
- 1972-03-13 BE BE780618A patent/BE780618A/xx unknown
- 1972-03-14 HU HUSA002323 patent/HU163329B/hu unknown
- 1972-03-14 DE DE19722212245 patent/DE2212245A1/de active Pending
- 1972-03-14 DD DD16155272A patent/DD100259A5/xx unknown
- 1972-03-14 AT AT212072A patent/ATA212072A/de not_active Application Discontinuation
- 1972-03-15 AU AU40030/72A patent/AU467915B2/en not_active Expired
- 1972-03-15 FR FR7208917A patent/FR2130233B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7203192A (enrdf_load_stackoverflow) | 1972-09-19 |
| AU4003072A (en) | 1973-09-20 |
| AU467915B2 (en) | 1973-09-20 |
| GB1380136A (en) | 1975-01-08 |
| HU163329B (enrdf_load_stackoverflow) | 1973-07-28 |
| DD100259A5 (enrdf_load_stackoverflow) | 1973-09-12 |
| FR2130233B1 (enrdf_load_stackoverflow) | 1975-12-26 |
| ATA212072A (de) | 1975-05-15 |
| FR2130233A1 (enrdf_load_stackoverflow) | 1972-11-03 |
| BE780618A (fr) | 1972-09-13 |
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