DE3042636A1 - Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellung - Google Patents
Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellungInfo
- Publication number
- DE3042636A1 DE3042636A1 DE19803042636 DE3042636A DE3042636A1 DE 3042636 A1 DE3042636 A1 DE 3042636A1 DE 19803042636 DE19803042636 DE 19803042636 DE 3042636 A DE3042636 A DE 3042636A DE 3042636 A1 DE3042636 A1 DE 3042636A1
- Authority
- DE
- Germany
- Prior art keywords
- methylphenyl
- dibromo
- general formula
- acid
- imidazo
- 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.)
- Withdrawn
Links
- 239000002253 acid Substances 0.000 title claims description 12
- -1 2,6-DIBROM-4-METHYLPHENYL Chemical class 0.000 title claims description 11
- 238000000034 method Methods 0.000 title claims description 11
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 5
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- VZPAWRZFNSXUOS-UHFFFAOYSA-N 7-(2,6-dibromo-4-methylphenyl)-2,3-dihydroimidazo[1,2-a]imidazole Chemical class BrC1=CC(C)=CC(Br)=C1N1C2=NCCN2C=C1 VZPAWRZFNSXUOS-UHFFFAOYSA-N 0.000 claims description 3
- 230000000694 effects Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 208000029078 coronary artery disease Diseases 0.000 claims description 2
- 239000007884 disintegrant Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 239000000314 lubricant Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- ROYYTESGJKJHTH-UHFFFAOYSA-N 2,3,5,6-tetrahydro-1h-imidazo[1,2-a]imidazole Chemical compound C1CN=C2NCCN21 ROYYTESGJKJHTH-UHFFFAOYSA-N 0.000 claims 1
- FVXNNUSYQWSJJD-UHFFFAOYSA-N 2-(2,6-dibromo-4-methylphenyl)-2,5-dihydro-1H-imidazol-4-amine Chemical compound BrC1=C(C(=CC(=C1)C)Br)C1NCC(N1)=N FVXNNUSYQWSJJD-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- DZHUQIOYWZHKQP-UHFFFAOYSA-N n-(2,6-dibromo-4-methylphenyl)-4,5-dihydro-1h-imidazol-2-amine Chemical compound BrC1=CC(C)=CC(Br)=C1N=C1NCCN1 DZHUQIOYWZHKQP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-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
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 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
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000003826 tablet Substances 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
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- OIMRLHCSLQUXLL-UHFFFAOYSA-N 3-chlorobutan-2-one Chemical compound CC(Cl)C(C)=O OIMRLHCSLQUXLL-UHFFFAOYSA-N 0.000 description 1
- XDADYJOYIMVXTH-UHFFFAOYSA-N 3h-imidazo[1,2-a]imidazole Chemical compound C1=CN2CC=NC2=N1 XDADYJOYIMVXTH-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000000059 bradycardiac effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 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
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- GATNOFPXSDHULC-UHFFFAOYSA-N ethylphosphonic acid Chemical compound CCP(O)(O)=O GATNOFPXSDHULC-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 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
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 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
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 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
- 229940005605 valeric acid Drugs 0.000 description 1
- 238000005303 weighing Methods 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803042636 DE3042636A1 (de) | 1980-11-12 | 1980-11-12 | Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellung |
| EP81109106A EP0051809A1 (de) | 1980-11-12 | 1981-10-28 | Neue 7-(2,6-Dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung |
| IL64242A IL64242A (en) | 1980-11-12 | 1981-11-09 | 7-(2,6-dibromo-4-methylphenyl)-2,3-dihydro-7 h-imidazo(1,2-a)imidazoles and acid addition salts thereof,their preparation and pharmaceutical compositions containing them |
| AR287379A AR228376A1 (es) | 1980-11-12 | 1981-11-09 | Procedimiento para producir nuevos 7-(2,6-dibromo-4-metilfenil)-2,3-dihidro-imidazo(1,2-a)imidazoles |
| GR66489A GR81331B (enExample) | 1980-11-12 | 1981-11-10 | |
| CS818256A CS223848B2 (en) | 1980-11-12 | 1981-11-10 | Method of making the 7-/2,6-dibrom-4-methylphenyl/-2,3-dihydroimidazo/1,2-a/imidazole |
| DD81234740A DD208154A5 (de) | 1980-11-12 | 1981-11-10 | Verfahren zur herstellung von 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazol/1,2-a/-imidazolen |
| FI813562A FI71561C (fi) | 1980-11-12 | 1981-11-10 | Foerfarande foer framstaellning av terapeutiskt verksamma 7-(2,6-dibrom-4-metylfenyl)-2,3-dihydro-imidazo /1,2-a/imidazoler och deras syraadditionssalter. |
| CA000389832A CA1171090A (en) | 1980-11-12 | 1981-11-10 | 7-(2,6-dibromo-4-methylphenyl)-2,3-dihydro- imidazo[1,2-a]imidazoles, the acid addition salts thereof, pharmaceutical compositions containing them and processes for the preparation thereof |
| HU813374A HU182413B (en) | 1980-11-12 | 1981-11-11 | Process for preparing 7-/2.6-dibromo-4-methyl-phenyl/-2,3-dihydro-imidazo/1,2-a/imidazoles |
| KR1019810004323A KR880000851B1 (ko) | 1980-11-12 | 1981-11-11 | 7-(2,6-디브로모-4-메틸페닐)-2,3-디하이드로-이미다조[1,2-a]이미다졸 유도체의 제조방법. |
| DK499381A DK153151C (da) | 1980-11-12 | 1981-11-11 | Analogifremgangsmaade til fremstilling af 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazooe1,2-aaaimidazoler eller deres syreaddtionssalte |
| ZA817788A ZA817788B (en) | 1980-11-12 | 1981-11-11 | Imidazole derivatives,their preparation,and pharmaceutical formulation thereof |
| IE2641/81A IE53482B1 (en) | 1980-11-12 | 1981-11-11 | Imidazole derivatives |
| GB8134005A GB2086900B (en) | 1980-11-12 | 1981-11-11 | Imidazole derivatives |
| NZ198940A NZ198940A (en) | 1980-11-12 | 1981-11-11 | Gamma-(2,6-dibromo-4-methylphenyl)-5-methyl or 5,6-dimethyl-2,3-dihydroimidazo(1,2-a)imidazole |
| NO813822A NO156691C (no) | 1980-11-12 | 1981-11-11 | Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazoimidazol-derivater. |
| AU77391/81A AU548784B2 (en) | 1980-11-12 | 1981-11-11 | Imidazo(1,2-a)imidazole derivatives |
| PL1981233772A PL133210B1 (en) | 1980-11-12 | 1981-11-11 | Process for preparing novel 7-/2,6-dibromo-4-methylphenyl/-2,3-dihydro-imidazo /1,2-a/-imidazoles |
| PT73971A PT73971B (de) | 1980-11-12 | 1981-11-11 | Neue 7-(2,6-dibrom-4-methylphenyl-2,3-dihydro-imidazo <1,2-a> imidazole deren saeureadditions salze diese enthaltende arzneimittel und verfahren zu deren herstellung |
| JP56180924A JPS57109788A (en) | 1980-11-12 | 1981-11-11 | Imidazoimidazole derivative |
| ES507016A ES8301991A1 (es) | 1980-11-12 | 1981-11-11 | Procedimiento para la preparacion de 7-(2,6-dibromo-4-metil-fenil)-2,3-dihidro-imidazo 1,2-a, imidazoles. |
| US06/404,538 US4409235A (en) | 1980-11-12 | 1982-08-02 | Substituted 7-(2,6-dibromo-4-methyl-phenyl)-2,3-dihydro-imidazo[1,2-a]imidazoles, compositions and use |
| PH28957A PH18610A (en) | 1980-11-12 | 1983-05-25 | Substituted 7-(2,6-dihromo-4-methyl-phenyl)-2,3 dihydroimidazo 1,2-a imidazoles,compositions and use |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19803042636 DE3042636A1 (de) | 1980-11-12 | 1980-11-12 | Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3042636A1 true DE3042636A1 (de) | 1982-06-16 |
Family
ID=6116582
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803042636 Withdrawn DE3042636A1 (de) | 1980-11-12 | 1980-11-12 | Neue 7-(2,6-dibrom-4-methylphenyl)-2,3-dihydro-imidazo(1,2-a)imidazole, deren saeureadditionssalze, diese enhthaltende arzneimittel und verfahren zu deren herstellung |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4409235A (enExample) |
| EP (1) | EP0051809A1 (enExample) |
| JP (1) | JPS57109788A (enExample) |
| KR (1) | KR880000851B1 (enExample) |
| AR (1) | AR228376A1 (enExample) |
| AU (1) | AU548784B2 (enExample) |
| CA (1) | CA1171090A (enExample) |
| CS (1) | CS223848B2 (enExample) |
| DD (1) | DD208154A5 (enExample) |
| DE (1) | DE3042636A1 (enExample) |
| DK (1) | DK153151C (enExample) |
| ES (1) | ES8301991A1 (enExample) |
| FI (1) | FI71561C (enExample) |
| GB (1) | GB2086900B (enExample) |
| GR (1) | GR81331B (enExample) |
| HU (1) | HU182413B (enExample) |
| IE (1) | IE53482B1 (enExample) |
| IL (1) | IL64242A (enExample) |
| NO (1) | NO156691C (enExample) |
| NZ (1) | NZ198940A (enExample) |
| PH (1) | PH18610A (enExample) |
| PL (1) | PL133210B1 (enExample) |
| PT (1) | PT73971B (enExample) |
| ZA (1) | ZA817788B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL248267B1 (pl) * | 2023-04-13 | 2025-11-17 | Univ Medyczny W Lublinie | 1-arylo-6-hydroksyimino-5(1H)okso-2,3-dihydroimidazo[1,2-a] imidazole oraz sposób ich wytwarzania oraz ich zastosowanie |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2118261A1 (de) * | 1971-04-15 | 1972-11-02 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue N-haltige Bicyclen, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
| DE2361188A1 (de) * | 1972-12-08 | 1974-06-12 | Janssen Pharmaceutica Nv | Bicyclische imidazole und pyrimidine, verfahren zu ihrer herstellung und arzneimittel |
| DE2827617A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Sohn Ingelheim | Neue imidazo eckige klammer auf 1,2- alpha eckige klammer zu imidazole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
-
1980
- 1980-11-12 DE DE19803042636 patent/DE3042636A1/de not_active Withdrawn
-
1981
- 1981-10-28 EP EP81109106A patent/EP0051809A1/de not_active Ceased
- 1981-11-09 IL IL64242A patent/IL64242A/xx unknown
- 1981-11-09 AR AR287379A patent/AR228376A1/es active
- 1981-11-10 CA CA000389832A patent/CA1171090A/en not_active Expired
- 1981-11-10 FI FI813562A patent/FI71561C/fi not_active IP Right Cessation
- 1981-11-10 DD DD81234740A patent/DD208154A5/de unknown
- 1981-11-10 CS CS818256A patent/CS223848B2/cs unknown
- 1981-11-10 GR GR66489A patent/GR81331B/el unknown
- 1981-11-11 IE IE2641/81A patent/IE53482B1/en unknown
- 1981-11-11 PL PL1981233772A patent/PL133210B1/pl unknown
- 1981-11-11 ZA ZA817788A patent/ZA817788B/xx unknown
- 1981-11-11 AU AU77391/81A patent/AU548784B2/en not_active Ceased
- 1981-11-11 KR KR1019810004323A patent/KR880000851B1/ko not_active Expired
- 1981-11-11 JP JP56180924A patent/JPS57109788A/ja active Pending
- 1981-11-11 PT PT73971A patent/PT73971B/pt unknown
- 1981-11-11 NO NO813822A patent/NO156691C/no unknown
- 1981-11-11 NZ NZ198940A patent/NZ198940A/en unknown
- 1981-11-11 HU HU813374A patent/HU182413B/hu not_active IP Right Cessation
- 1981-11-11 GB GB8134005A patent/GB2086900B/en not_active Expired
- 1981-11-11 DK DK499381A patent/DK153151C/da not_active IP Right Cessation
- 1981-11-11 ES ES507016A patent/ES8301991A1/es not_active Expired
-
1982
- 1982-08-02 US US06/404,538 patent/US4409235A/en not_active Expired - Fee Related
-
1983
- 1983-05-25 PH PH28957A patent/PH18610A/en unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2118261A1 (de) * | 1971-04-15 | 1972-11-02 | C.H. Boehringer Sohn, 6507 Ingelheim | Neue N-haltige Bicyclen, deren Säureadditionssalze sowie Verfahren zu deren Herstellung |
| DE2361188A1 (de) * | 1972-12-08 | 1974-06-12 | Janssen Pharmaceutica Nv | Bicyclische imidazole und pyrimidine, verfahren zu ihrer herstellung und arzneimittel |
| DE2827617A1 (de) * | 1978-06-23 | 1980-01-10 | Boehringer Sohn Ingelheim | Neue imidazo eckige klammer auf 1,2- alpha eckige klammer zu imidazole, deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zu deren herstellung |
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