CH638206A5 - 5,6-Dihydroimidazo[5,1-a]isoquinoline derivatives and processes for their preparation - Google Patents

5,6-Dihydroimidazo[5,1-a]isoquinoline derivatives and processes for their preparation Download PDF

Info

Publication number: CH638206A5
Authority: CH; Switzerland
Prior art keywords: general formula; compound; dihydro; meaning given; isoquinoline
Prior art date: 1977-05-18

Application number

CH535878A

Other languages

German (de)

English (en)

Inventor

Kalman Harsanyi

Matyas Szentivanyi

Judit Varga-Szeredi

Gyoergy Leszkovszky

Csaba Vertesi

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-05-18

Filing date

1978-05-17

Publication date

1983-09-15

1978-05-17 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1983-09-15 Publication of CH638206A5 publication Critical patent/CH638206A5/de

Links

238000000034 method Methods 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 16
WBZLGNODHLEZLU-UHFFFAOYSA-N 5,6-dihydroimidazo[5,1-a]isoquinoline Chemical class C12=CC=CC=C2CCN2C1=CN=C2 WBZLGNODHLEZLU-UHFFFAOYSA-N 0.000 title claims 3
150000001875 compounds Chemical class 0.000 claims description 72
229910052739 hydrogen Inorganic materials 0.000 claims description 36
150000003839 salts Chemical class 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 14
-1 aminophenyl Chemical group 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
230000000694 effects Effects 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
229910052760 oxygen Inorganic materials 0.000 claims description 8
239000001301 oxygen Substances 0.000 claims description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002560 nitrile group Chemical group 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 4
150000002430 hydrocarbons Chemical class 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
239000004215 Carbon black (E152) Substances 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
238000005661 deetherification reaction Methods 0.000 claims description 3
125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 5
125000004430 oxygen atom Chemical group O* 0.000 claims 2
QIVSNULLVVJTPW-UHFFFAOYSA-N 8,9-dimethoxy-3-oxo-5,6-dihydro-2H-imidazo[5,1-a]isoquinoline-1-carbonitrile Chemical compound C(#N)C=1NC(N2C1C1=CC(=C(C=C1CC2)OC)OC)=O QIVSNULLVVJTPW-UHFFFAOYSA-N 0.000 claims 1
239000003377 acid catalyst Substances 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
150000008282 halocarbons Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
239000000047 product Substances 0.000 description 36
229910052757 nitrogen Inorganic materials 0.000 description 31
238000002844 melting Methods 0.000 description 29
230000008018 melting Effects 0.000 description 29
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
239000000243 solution Substances 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 20
239000000203 mixture Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 11
238000009835 boiling Methods 0.000 description 10
238000001914 filtration Methods 0.000 description 10
239000002244 precipitate Substances 0.000 description 10
RZIAABRFQASVSW-UHFFFAOYSA-N Isoquinoline N-oxide Chemical compound C1=CC=CC2=C[N+]([O-])=CC=C21 RZIAABRFQASVSW-UHFFFAOYSA-N 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 6
239000007858 starting material Substances 0.000 description 6
GYPOFOQUZZUVQL-UHFFFAOYSA-N 2h-isoquinolin-3-one Chemical compound C1=CC=C2C=NC(O)=CC2=C1 GYPOFOQUZZUVQL-UHFFFAOYSA-N 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
239000012043 crude product Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
239000008098 formaldehyde solution Substances 0.000 description 4
SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 3
241000700199 Cavia porcellus Species 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
210000004165 myocardium Anatomy 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
150000002905 orthoesters Chemical class 0.000 description 3
210000003540 papillary muscle Anatomy 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
230000029058 respiratory gaseous exchange Effects 0.000 description 3
229960000195 terbutaline Drugs 0.000 description 3
NSLJVQUDZCZJLK-UHFFFAOYSA-N 6,7-dimethoxy-3,4-dihydroisoquinoline Chemical compound C1CN=CC2=C1C=C(OC)C(OC)=C2 NSLJVQUDZCZJLK-UHFFFAOYSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000004202 carbamide Substances 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000010411 cooking Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000005187 foaming Methods 0.000 description 2
HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
239000012452 mother liquor Substances 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 description 1
KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 description 1
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
AOFCBOIXXIMDFJ-UHFFFAOYSA-N 3-(2-chlorophenyl)-8,9-dimethoxy-2-oxido-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium-1-carbonitrile Chemical compound C(#N)C=1[N+](=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)C1=C(C=CC=C1)Cl)[O-] AOFCBOIXXIMDFJ-UHFFFAOYSA-N 0.000 description 1
AVPPEKWDRJIUDC-UHFFFAOYSA-N 3-[4-(dimethylamino)phenyl]-8,9-dimethoxy-2-oxido-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium-1-carbonitrile Chemical compound C(#N)C=1[N+](=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)C1=CC=C(C=C1)N(C)C)[O-] AVPPEKWDRJIUDC-UHFFFAOYSA-N 0.000 description 1
BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 description 1
YWSORDNFWOTSFG-UHFFFAOYSA-N 8,9-dihydroxy-5,6-dihydroimidazo[5,1-a]isoquinoline-1-carbonitrile Chemical compound C(#N)C=1N=CN2C=1C1=CC(=C(C=C1CC2)O)O YWSORDNFWOTSFG-UHFFFAOYSA-N 0.000 description 1
UOOLPGRBSLDUDK-UHFFFAOYSA-N 8,9-dimethoxy-2-oxido-3-propyl-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium-1-carbonitrile Chemical compound C(#N)C=1[N+](=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)CCC)[O-] UOOLPGRBSLDUDK-UHFFFAOYSA-N 0.000 description 1
MLAPVTIJSZSMPM-UHFFFAOYSA-N 8,9-dimethoxy-3-(4-methoxyphenyl)-2-oxido-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium-1-carbonitrile Chemical group C(#N)C=1[N+](=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)C1=CC=C(C=C1)OC)[O-] MLAPVTIJSZSMPM-UHFFFAOYSA-N 0.000 description 1
BIOYYGSNFRACOL-UHFFFAOYSA-N 8,9-dimethoxy-3-(5-nitrofuran-2-yl)-2-oxido-5,6-dihydroimidazo[5,1-a]isoquinolin-2-ium-1-carbonitrile Chemical compound C(#N)C=1[N+](=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)C=1OC(=CC=1)[N+](=O)[O-])[O-] BIOYYGSNFRACOL-UHFFFAOYSA-N 0.000 description 1
YVCQRICCXSNTEG-UHFFFAOYSA-N 8,9-dimethoxy-3-methyl-5,6-dihydroimidazo[5,1-a]isoquinoline-1-carbonitrile Chemical compound C(#N)C=1N=C(N2C=1C1=CC(=C(C=C1CC2)OC)OC)C YVCQRICCXSNTEG-UHFFFAOYSA-N 0.000 description 1
MCHWNVQDGPNPKM-UHFFFAOYSA-N 8,9-dimethoxy-3-propyl-5,6-dihydroimidazo[5,1-a]isoquinoline-1-carbonitrile Chemical compound C(#N)C=1N=C(N2C1C1=CC(=C(C=C1CC2)OC)OC)CCC MCHWNVQDGPNPKM-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
238000005684 Liebig rearrangement reaction Methods 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
230000001088 anti-asthma Effects 0.000 description 1
239000000924 antiasthmatic agent Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000000621 bronchi Anatomy 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
230000001813 broncholytic effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940117916 cinnamic aldehyde Drugs 0.000 description 1
KJPRLNWUNMBNBZ-UHFFFAOYSA-N cinnamic aldehyde Natural products O=CC=CC1=CC=CC=C1 KJPRLNWUNMBNBZ-UHFFFAOYSA-N 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
VCSZKSHWUBFOOE-UHFFFAOYSA-N dioxidanium;sulfate Chemical compound O.O.OS(O)(=O)=O VCSZKSHWUBFOOE-UHFFFAOYSA-N 0.000 description 1
GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
210000002599 gastric fundus Anatomy 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
229910052736 halogen Chemical group 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
230000036571 hydration Effects 0.000 description 1
238000006703 hydration reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
210000003405 ileum Anatomy 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002537 isoquinolines Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000003951 lactams Chemical group 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical class OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
229920000137 polyphosphoric acid Polymers 0.000 description 1
230000009090 positive inotropic effect Effects 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
238000001256 steam distillation Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000003437 trachea Anatomy 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
- C12M23/00—Constructional details, e.g. recesses, hinges
- C12M23/02—Form or structure of the vessel
- C12M23/04—Flat or tray type, drawers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12M—APPARATUS FOR ENZYMOLOGY OR MICROBIOLOGY; APPARATUS FOR CULTURING MICROORGANISMS FOR PRODUCING BIOMASS, FOR GROWING CELLS OR FOR OBTAINING FERMENTATION OR METABOLIC PRODUCTS, i.e. BIOREACTORS OR FERMENTERS
- C12M29/00—Means for introduction, extraction or recirculation of materials, e.g. pumps
- C12M29/26—Conditioning fluids entering or exiting the reaction vessel
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/44—Polycarboxylic acids
- C12P7/48—Tricarboxylic acids, e.g. citric acid
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/80—Elimination or reduction of contamination by undersired ferments, e.g. aseptic cultivation

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Wood Science & Technology (AREA)
Bioinformatics & Cheminformatics (AREA)
Zoology (AREA)
General Health & Medical Sciences (AREA)
Microbiology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
General Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Sustainable Development (AREA)
Biomedical Technology (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pulmonology (AREA)
Medicinal Chemistry (AREA)
Clinical Laboratory Science (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

CH535878A 1977-05-18 1978-05-17 5,6-Dihydroimidazo[5,1-a]isoquinoline derivatives and processes for their preparation CH638206A5 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU77CI1739A HU176214B (en)	1977-05-18	1977-05-18	Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives

Publications (1)

Publication Number	Publication Date
CH638206A5 true CH638206A5 (en)	1983-09-15

Family

ID=10994651

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH535878A CH638206A5 (en)	1977-05-18	1978-05-17	5,6-Dihydroimidazo[5,1-a]isoquinoline derivatives and processes for their preparation

Country Status (11)

Country	Link
JP (1)	JPS53147094A (pl)
AT (1)	AT363476B (pl)
CH (1)	CH638206A5 (pl)
DD (1)	DD136138A5 (pl)
DE (1)	DE2821226A1 (pl)
ES (1)	ES469999A1 (pl)
FR (1)	FR2391213A1 (pl)
GB (1)	GB1594907A (pl)
HU (1)	HU176214B (pl)
PL (1)	PL117925B1 (pl)
SU (1)	SU852173A3 (pl)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0198227A3 (de) *	1985-03-20	1988-01-13	Boehringer Ingelheim Kg	Imidazo-Isochinoline und Imidazo-Thienopyridin-Verbindungen, Arzneimittel enthaltend diese Verbindungen und Verfahren zu ihrer Herstellung
CN101166740B (zh) *	2005-04-25	2010-12-29	诺瓦提斯公司	用作肽脱甲酰基酶(pdf)抑制剂的咪唑并[1,2-a]吡啶衍生物
DE102005019181A1 (de) *	2005-04-25	2006-10-26	Novartis Ag	Peptid-Deformylase (PDF) Inhibitoren 1
CL2008000973A1 (es) *	2007-04-05	2009-01-02	Astrazeneca Ab	Compuestos derivados de 1-oxo-isoquinolina; procedimiento de preparación; composición farmacéutica; y su uso en el tratamiento de enfermedades pulmonares obstructvas crónicas (epoc) y asma.

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU167240B (pl) *	1972-06-30	1975-09-27

1977
- 1977-05-18 HU HU77CI1739A patent/HU176214B/hu unknown
1978
- 1978-05-16 DE DE19782821226 patent/DE2821226A1/de not_active Withdrawn
- 1978-05-17 CH CH535878A patent/CH638206A5/de not_active IP Right Cessation
- 1978-05-17 SU SU782617907A patent/SU852173A3/ru active
- 1978-05-17 GB GB20204/78A patent/GB1594907A/en not_active Expired
- 1978-05-18 FR FR7814743A patent/FR2391213A1/fr active Granted
- 1978-05-18 AT AT0359778A patent/AT363476B/de not_active IP Right Cessation
- 1978-05-18 JP JP5836378A patent/JPS53147094A/ja active Pending
- 1978-05-18 PL PL1978206901A patent/PL117925B1/pl unknown
- 1978-05-18 ES ES469999A patent/ES469999A1/es not_active Expired
- 1978-05-18 DD DD78205458A patent/DD136138A5/xx unknown

Also Published As

Publication number	Publication date
HU176214B (en)	1981-01-28
JPS53147094A (en)	1978-12-21
PL206901A1 (pl)	1979-09-10
ES469999A1 (es)	1979-09-16
DE2821226A1 (de)	1978-11-30
GB1594907A (en)	1981-08-05
FR2391213A1 (fr)	1978-12-15
PL117925B1 (en)	1981-09-30
DD136138A5 (de)	1979-06-20
FR2391213B1 (pl)	1981-09-04
ATA359778A (de)	1981-01-15
SU852173A3 (ru)	1981-07-30
AT363476B (de)	1981-08-10

Legal Events

Date	Code	Title	Description
1987-01-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2419970C3 (de)	1980-06-12	3-<l-Pyrrolidinyl)-4-phenoxy-5sulfamoylbenzoesäure und Verfahren zu ihrer Herstellung
CH381706A (de)	1964-09-15	Verfahren zur Herstellung von Sulfamylanthranilsäuren
DE2824905A1 (de)	1979-01-04	Neue 1, 2, 3, 4, 6, 7-hexahydro-11 balphah-benzo(a)chinolizin-derivate und verfahren zur herstellung derselben
DE2302821A1 (de)	1973-08-02	Verfahren zur herstellung von desaethyleburnamoninen
EP0056956A2 (de)	1982-08-04	Neue Indanyl-Derivate, ihre Herstellung und Verwendung
DE1804691A1 (de)	1969-07-31	Sulfonsaeure-Produkte
CH620899A5 (pl)	1980-12-31
DE2722416A1 (de)	1978-11-30	Neue thiazolo-pyridine
CH619952A5 (pl)	1980-10-31
DE2821226A1 (de)	1978-11-30	Neue 5,6-dihydro-imidazo (5,1-a) isochinolin derivate und verfahren zu deren herstellung
DE2539867C2 (de)	1982-05-19	14,15-Dihydro-3&beta; ,16&alpha; -eburnameninderivate
DE2512673A1 (de)	1975-10-02	7-(hydroxyphenyl)pyrido eckige klammer auf 3,4-d eckige klammer zu pyridazine und verfahren zu ihrer herstellung
CH635342A5 (de)	1983-03-31	Verfahren zur herstellung von neuen octahydro-indolo(2,3-a)-chinolizinen.
DE2024049C3 (de)	1978-07-20	a-(3,4-Dihydroxyphenyl)-a- (2-piperidinyl)methanol
DE2745280C2 (de)	1986-02-06	3-Cyano-10,11-dihydro-5H-dibenz[b,f]azepin
DE2162563C3 (de)	1979-06-07	l-(3',4'3'-Trimethoxybenzyl)-6-hydroxy-l,23,4-tetrahydroisochinoun
CH624954A5 (pl)	1981-08-31
DE1645988B2 (de)	1977-02-10	2,3-dihydro-1h-pyrido eckige klammer auf 2,3-b eckige klammer zu eckige klammer auf 1,4 eckige klammer zu -thiazine und verfahren zu deren herstellung
CH627156A5 (pl)	1981-12-31
DE2330218C2 (de)	1982-11-18	Verfahren zur Herstellung von 2H-3- Isochinolonen
CH523884A (de)	1972-06-15	Verfahren zur Herstellung neuer Indol-Derivate
AT269886B (de)	1969-04-10	Verfahren zur Herstellung neuer Benzomorphanderivate und ihrer Salze
DE1445895C (de)	1973-04-05	Verfahren zur Herstellung von 2 Dehydroemetinderivaten
AT165073B (de)	1950-01-10	Verfahren zur Darstellung substituierten Piperido-octahydrophenanthrenen
DE2701629C2 (pl)	1987-08-20