CH639656A5 - Stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung. - Google Patents
Stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung. Download PDFInfo
- Publication number
- CH639656A5 CH639656A5 CH361679A CH361679A CH639656A5 CH 639656 A5 CH639656 A5 CH 639656A5 CH 361679 A CH361679 A CH 361679A CH 361679 A CH361679 A CH 361679A CH 639656 A5 CH639656 A5 CH 639656A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid addition
- compounds
- general formula
- group
- addition salts
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- -1 Nitrogen-containing heterocyclic compounds Chemical class 0.000 claims description 5
- NKWOXRUJRCMCBH-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine Chemical compound C1=CC=C2CN(N)CC2=C1 NKWOXRUJRCMCBH-UHFFFAOYSA-N 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- LVJKWHCQSJWZFK-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-1,3-dihydroisoindol-2-amine Chemical compound N1CCN=C1NN1CC2=CC=CC=C2C1 LVJKWHCQSJWZFK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000007514 bases Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000007981 azolines Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 4
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- PZZRSEUDGCFXIH-UHFFFAOYSA-N 2-methylsulfanyl-4,5-dihydro-1h-imidazol-1-ium;iodide Chemical compound I.CSC1=NCCN1 PZZRSEUDGCFXIH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- SRTVEAIOGLPJGL-UHFFFAOYSA-N 1-[2-(1,3-dihydroisoindol-2-ylamino)-4,5-dihydroimidazol-1-yl]ethanone Chemical compound CC(=O)N1CCN=C1NN1CC2=CC=CC=C2C1 SRTVEAIOGLPJGL-UHFFFAOYSA-N 0.000 description 2
- OYLPBTPLAUXYTB-UHFFFAOYSA-N 4-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-1,3-dihydroisoindol-2-amine Chemical compound C1C=2C(Cl)=CC=CC=2CN1NC1=NCCN1 OYLPBTPLAUXYTB-UHFFFAOYSA-N 0.000 description 2
- LNYXTVUGSBRSIX-UHFFFAOYSA-N 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-1,3-dihydroisoindol-2-amine Chemical compound C1C2=CC(Cl)=CC=C2CN1NC1=NCCN1 LNYXTVUGSBRSIX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910019213 POCl3 Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- XBQIKUVBLLRHCB-UHFFFAOYSA-N n-(1,3-dihydroisoindol-2-yl)-4,5-dihydro-1,3-oxazol-2-amine Chemical compound O1CCN=C1NN1CC2=CC=CC=C2C1 XBQIKUVBLLRHCB-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MJWQKIONDNPIRS-UHFFFAOYSA-N 1,2,4,5-tetrahydro-3-benzazepin-3-amine Chemical compound C1CN(N)CCC2=CC=CC=C21 MJWQKIONDNPIRS-UHFFFAOYSA-N 0.000 description 1
- HMTJXSDKWOSNNA-UHFFFAOYSA-N 1,3,4,5-tetrahydro-2-benzazepin-2-amine Chemical compound C1N(N)CCCC2=CC=CC=C21 HMTJXSDKWOSNNA-UHFFFAOYSA-N 0.000 description 1
- AIKFLHOJAHSLAY-UHFFFAOYSA-N 1,3-dihydroisoindol-2-amine;hydrochloride Chemical compound Cl.C1=CC=C2CN(N)CC2=C1 AIKFLHOJAHSLAY-UHFFFAOYSA-N 0.000 description 1
- QWEVGYHMFWWSMB-UHFFFAOYSA-N 1-(2-chloroethyl)-3-(1,3-dihydroisoindol-2-yl)urea Chemical compound C1=CC=C2CN(NC(=O)NCCCl)CC2=C1 QWEVGYHMFWWSMB-UHFFFAOYSA-N 0.000 description 1
- BCMYXYHEMGPZJN-UHFFFAOYSA-N 1-chloro-2-isocyanatoethane Chemical compound ClCCN=C=O BCMYXYHEMGPZJN-UHFFFAOYSA-N 0.000 description 1
- ZUWFBQUHBOUPFK-UHFFFAOYSA-N 1-chloro-2-isothiocyanatoethane Chemical compound ClCCN=C=S ZUWFBQUHBOUPFK-UHFFFAOYSA-N 0.000 description 1
- ZGFOBQSQLJDLKV-UHFFFAOYSA-N 1-chloro-3-isothiocyanatopropane Chemical compound ClCCCN=C=S ZGFOBQSQLJDLKV-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- QISOBCMNUJQOJU-UHFFFAOYSA-N 4-bromo-1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1NN=CC=1Br QISOBCMNUJQOJU-UHFFFAOYSA-N 0.000 description 1
- WANXQLAUEMUFPA-UHFFFAOYSA-N 4-chloro-1,3-dihydroisoindol-2-amine;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2CN(N)CC2=C1 WANXQLAUEMUFPA-UHFFFAOYSA-N 0.000 description 1
- GLWUDZZJGFTIAY-UHFFFAOYSA-N 5-chloro-1,3-dihydroisoindol-2-amine Chemical compound C1=C(Cl)C=C2CN(N)CC2=C1 GLWUDZZJGFTIAY-UHFFFAOYSA-N 0.000 description 1
- YNTUHDRALXNDEQ-UHFFFAOYSA-N 6-methoxy-2,3,4,5-tetrahydropyridine Chemical compound COC1=NCCCC1 YNTUHDRALXNDEQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002463 imidates Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- GGBJFKPJVFPXLE-UHFFFAOYSA-N n-(1,3-dihydroisoindol-2-yl)-4,5-dihydro-1,3-thiazol-2-amine Chemical compound S1CCN=C1NN1CC2=CC=CC=C2C1 GGBJFKPJVFPXLE-UHFFFAOYSA-N 0.000 description 1
- IZOZFSKJWPKZBB-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-1,2,4,5-tetrahydro-3-benzazepin-3-amine Chemical compound N1CCN=C1NN1CCC2=CC=CC=C2CC1 IZOZFSKJWPKZBB-UHFFFAOYSA-N 0.000 description 1
- LCRYDWXFJJQDPZ-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-1,3,4,5-tetrahydro-2-benzazepin-2-amine Chemical compound N1CCN=C1NN1CC2=CC=CC=C2CCC1 LCRYDWXFJJQDPZ-UHFFFAOYSA-N 0.000 description 1
- JAQWXZPGECEVDQ-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-5,6-dimethoxy-1,3-dihydroisoindol-2-amine Chemical compound C1C=2C=C(OC)C(OC)=CC=2CN1NC1=NCCN1 JAQWXZPGECEVDQ-UHFFFAOYSA-N 0.000 description 1
- GTLFMTKDIQVGMI-UHFFFAOYSA-N n-(4,5-dihydro-1h-imidazol-2-yl)-5,6-dimethyl-1,3-dihydroisoindol-2-amine Chemical compound C1C=2C=C(C)C(C)=CC=2CN1NC1=NCCN1 GTLFMTKDIQVGMI-UHFFFAOYSA-N 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- 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
- C07D417/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782816627 DE2816627A1 (de) | 1978-04-17 | 1978-04-17 | 2-(n-amino-isoindolinyl)-imidazolin und verfahren zu seiner herstellung |
| DE19792905501 DE2905501A1 (de) | 1979-02-14 | 1979-02-14 | Neue kondensierte, stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639656A5 true CH639656A5 (de) | 1983-11-30 |
Family
ID=25774265
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH361679A CH639656A5 (de) | 1978-04-17 | 1979-04-17 | Stickstoffhaltige heterocyclische verbindungen und verfahren zu deren herstellung. |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US4221798A (en, 2012) |
| JP (1) | JPS54151990A (en, 2012) |
| CH (1) | CH639656A5 (en, 2012) |
| FR (1) | FR2423491A1 (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3133302A1 (de) * | 1981-08-22 | 1983-03-03 | Beiersdorf Ag, 2000 Hamburg | Isoindolin-2-yl-amino-imidazoline und isoindolin-2-yl-guanidine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| FR2573120B1 (fr) * | 1984-11-14 | 1990-06-22 | Jamison Timothy | Dispositif antivol, en particulier pour cintre de support d'un article vestimentaire. |
| DE3545206A1 (de) * | 1985-12-20 | 1987-06-25 | Beiersdorf Ag | Substituierte 4-fluor-isoindoline, verfahren zu ihrer herstellung und ihre verwendung sowie diese verbindungen enthaltende zubereitungen |
| GB8610909D0 (en) * | 1986-05-03 | 1986-06-11 | Beecham Group Plc | Compounds |
| US5677321A (en) * | 1996-02-29 | 1997-10-14 | Synaptic Pharmaceutical Corporation | 5- and 6-(2-imidazolin-2-ylamino) and -(2-thiazolin-2-ylamino)-benzothiazoles as alpha-2 adrenergic ligands |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB806060A (en) * | 1955-12-19 | 1958-12-17 | Wander Ag Dr A | New imidazoline salts and a process for the production thereof |
| BE704683A (en, 2012) * | 1966-11-07 | 1968-02-15 | ||
| DE1670184A1 (de) * | 1967-01-20 | 1971-01-21 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung heterocyclisch substituierter Hydrazino-imidazoline-(2) |
| US3509170A (en) * | 1967-06-12 | 1970-04-28 | Du Pont | Heterocyclic amino-oxazolines |
| BE757879A (fr) * | 1969-10-24 | 1971-04-22 | Sandoz Sa | Derives du benzo(cd)indole, leur preparation et medicaments contenant ces derives |
| US3666767A (en) * | 1970-01-28 | 1972-05-30 | Warner Lambert Co | 2-amino-1-(2-imidazolin-2-yl)-2-imidazolines |
| US3846412A (en) * | 1971-03-18 | 1974-11-05 | Lepetit Spa | Dihydro-2-amino-isoquinolines and their derivatives |
| DE2220906A1 (de) * | 1972-04-28 | 1973-11-15 | Boehringer Sohn Ingelheim | Neue substituierte 2-phenylaminoimidazoline-(2), deren saeureadditionssalze sowie verfahren zu deren herstellung |
| DE2314985A1 (de) * | 1973-03-26 | 1974-10-17 | Hoechst Ag | 1-(imidazol-1-yl)-isochinoline und verfahren zu ihrer herstellung |
-
1979
- 1979-04-12 JP JP4370179A patent/JPS54151990A/ja active Granted
- 1979-04-13 FR FR7909420A patent/FR2423491A1/fr active Granted
- 1979-04-16 US US06/030,405 patent/US4221798A/en not_active Expired - Lifetime
- 1979-04-17 CH CH361679A patent/CH639656A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2423491B1 (en, 2012) | 1981-09-18 |
| JPS54151990A (en) | 1979-11-29 |
| JPS6340190B2 (en, 2012) | 1988-08-10 |
| FR2423491A1 (fr) | 1979-11-16 |
| US4221798A (en) | 1980-09-09 |
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| PL | Patent ceased | ||
| PL | Patent ceased |