IL42613A - Amino-5,6-dihydro-8,9-dialkoxy-imidazo or pyrazolo(1,5-a)isoquinolines their preparation and pharmaceutical compositions containing them - Google Patents

Amino-5,6-dihydro-8,9-dialkoxy-imidazo or pyrazolo(1,5-a)isoquinolines their preparation and pharmaceutical compositions containing them

Info

Publication number: IL42613A
Authority: IL; Israel
Prior art keywords: dihydro; general formula; salts; amino; dimethoxy
Prior art date: 1972-06-30

Application number

IL42613A

Other languages

English (en)

Other versions

IL42613A0 (en

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.)

1972-06-30

Filing date

1973-06-26

Publication date

1977-05-31

1973-06-26 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1973-08-29 Publication of IL42613A0 publication Critical patent/IL42613A0/xx

1977-05-31 Publication of IL42613A publication Critical patent/IL42613A/en

Links

238000002360 preparation method Methods 0.000 title claims description 16
239000008194 pharmaceutical composition Substances 0.000 title claims description 4
150000002537 isoquinolines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 51
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 46
229910052739 hydrogen Inorganic materials 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
238000000034 method Methods 0.000 claims description 24
230000008569 process Effects 0.000 claims description 17
239000001257 hydrogen Substances 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
-1 alkaline earth metal salt Chemical class 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
230000000694 effects Effects 0.000 claims description 6
239000008096 xylene Substances 0.000 claims description 6
238000009835 boiling Methods 0.000 claims description 5
125000005518 carboxamido group Chemical group 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 4
239000000155 melt Substances 0.000 claims description 4
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims description 4
239000004480 active ingredient Substances 0.000 claims description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
159000000011 group IA salts Chemical class 0.000 claims description 2
229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
239000011707 mineral Substances 0.000 claims description 2
125000006682 monohaloalkyl group Chemical group 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
125000003884 phenylalkyl group Chemical group 0.000 claims description 2
230000002829 reductive effect Effects 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 claims 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 claims 1
125000002252 acyl group Chemical group 0.000 claims 1
238000006136 alcoholysis reaction Methods 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
150000008064 anhydrides Chemical class 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
HIIIEACVQVEWMR-UHFFFAOYSA-N imidazo[5,1-a]isoquinolin-3-amine Chemical class NC1=NC=C2N1C=CC1=CC=CC=C21 HIIIEACVQVEWMR-UHFFFAOYSA-N 0.000 claims 1
150000007522 mineralic acids Chemical class 0.000 claims 1
VXHPZUDEECSUNB-UHFFFAOYSA-N pyrazolo[5,1-a]isoquinoline Chemical class C12=CC=CC=C2C=CN2C1=CC=N2 VXHPZUDEECSUNB-UHFFFAOYSA-N 0.000 claims 1
239000000047 product Substances 0.000 description 39
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 37
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
239000000243 solution Substances 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000011541 reaction mixture Substances 0.000 description 19
239000000203 mixture Substances 0.000 description 16
238000001816 cooling Methods 0.000 description 13
238000010992 reflux Methods 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
229910052757 nitrogen Inorganic materials 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
230000010412 perfusion Effects 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
241000282472 Canis lupus familiaris Species 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
210000001308 heart ventricle Anatomy 0.000 description 6
238000003756 stirring Methods 0.000 description 6
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 5
230000036284 oxygen consumption Effects 0.000 description 5
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
230000007423 decrease Effects 0.000 description 4
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
DEPDDPLQZYCHOH-UHFFFAOYSA-N 1h-imidazol-2-amine Chemical class NC1=NC=CN1 DEPDDPLQZYCHOH-UHFFFAOYSA-N 0.000 description 3
JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
230000001476 alcoholic effect Effects 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
239000008280 blood Substances 0.000 description 3
210000004369 blood Anatomy 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
210000004165 myocardium Anatomy 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
238000012360 testing method Methods 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
QRZMXADUXZADTF-UHFFFAOYSA-N 4-aminoimidazole Chemical compound NC1=CNC=N1 QRZMXADUXZADTF-UHFFFAOYSA-N 0.000 description 2
MVXMNHYVCLMLDD-UHFFFAOYSA-N 4-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(OC)=CC=C(C=O)C2=C1 MVXMNHYVCLMLDD-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 2
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
230000010933 acylation Effects 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
238000011065 in-situ storage Methods 0.000 description 2
238000001802 infusion Methods 0.000 description 2
125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
WEVYAHXRMPXWCK-UHFFFAOYSA-N methyl cyanide Natural products CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
238000006213 oxygenation reaction Methods 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000006722 reduction reaction Methods 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-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
MUTDXQJNNJYAEG-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(dimethylamino)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)N(C)C MUTDXQJNNJYAEG-UHFFFAOYSA-N 0.000 description 1
PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical class O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 description 1
BIGWXAGEQONZGD-UHFFFAOYSA-N 2h-oxadiazol-5-one Chemical class O=C1C=NNO1 BIGWXAGEQONZGD-UHFFFAOYSA-N 0.000 description 1
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical class CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
101150040065 Actg2 gene Proteins 0.000 description 1
238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
101150039167 Bex3 gene Proteins 0.000 description 1
238000006407 Bischler-Napieralski reaction Methods 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
241001397173 Kali <angiosperm> Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000004075 alteration Effects 0.000 description 1
239000004004 anti-anginal agent Substances 0.000 description 1
229940124345 antianginal agent Drugs 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
230000000916 dilatatory effect Effects 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000004217 heart function Effects 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
210000005240 left ventricle Anatomy 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
238000001000 micrograph Methods 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
239000012454 non-polar solvent Substances 0.000 description 1
239000002674 ointment Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000002572 peristaltic effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000005932 reductive alkylation reaction Methods 0.000 description 1
238000012552 review Methods 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000005490 tosylate group Chemical group 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000002747 voluntary effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- 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
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J23/00—Details of transit-time tubes of the types covered by group H01J25/00
- H01J23/02—Electrodes; Magnetic control means; Screens
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J25/00—Transit-time tubes, e.g. klystrons, travelling-wave tubes, magnetrons
- H01J25/34—Travelling-wave tubes; Tubes in which a travelling wave is simulated at spaced gaps

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Microwave Tubes (AREA)

IL42613A 1972-06-30 1973-06-26 Amino-5,6-dihydro-8,9-dialkoxy-imidazo or pyrazolo(1,5-a)isoquinolines their preparation and pharmaceutical compositions containing them IL42613A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI1248A HU167240B (fi)	1972-06-30	1972-06-30

Publications (2)

Publication Number	Publication Date
IL42613A0 IL42613A0 (en)	1973-08-29
IL42613A true IL42613A (en)	1977-05-31

Family

ID=10994443

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL42613A IL42613A (en)	1972-06-30	1973-06-26	Amino-5,6-dihydro-8,9-dialkoxy-imidazo or pyrazolo(1,5-a)isoquinolines their preparation and pharmaceutical compositions containing them

Country Status (24)

Country	Link
JP (2)	JPS5336480B2 (fi)
AR (5)	AR208055A1 (fi)
AT (1)	AT329058B (fi)
BE (1)	BE801668A (fi)
CA (1)	CA1014559A (fi)
CH (6)	CH603639A5 (fi)
CS (1)	CS179024B1 (fi)
DD (1)	DD108090A1 (fi)
DE (1)	DE2332860C2 (fi)
DK (1)	DK141066B (fi)
EG (1)	EG11302A (fi)
ES (1)	ES416971A1 (fi)
FI (1)	FI55199C (fi)
FR (1)	FR2190458B1 (fi)
GB (1)	GB1438819A (fi)
HU (1)	HU167240B (fi)
IL (1)	IL42613A (fi)
IN (1)	IN139710B (fi)
NL (1)	NL177750C (fi)
NO (1)	NO138908C (fi)
PL (6)	PL93702B1 (fi)
SE (6)	SE405603B (fi)
SU (5)	SU584782A3 (fi)
YU (4)	YU36175B (fi)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH603643A5 (fi) *	1976-09-29	1978-08-31	Sandoz Ag
HU176214B (en) *	1977-05-18	1981-01-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives
CN1350539A (zh) *	1999-05-19	2002-05-22	宝洁公司	含咪唑并的杂环化合物,它们的组合物和应用
US6552033B1 (en)	2000-05-16	2003-04-22	The Procter & Gamble Co.	Imidazo-containing heterocyclic compounds, their compositions and uses
DK2573073T3 (en) *	2011-09-26	2015-01-19	Sanofi Sa	Pyrazolquinolinonderivater, their preparation and therapeutic use thereof

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH25A (de) *	1888-11-16	1889-04-05	Saurer & Soehne F	Maschine zum Einfädeln von Nadeln und zur Fadenverknotung

1972
- 1972-06-30 HU HUCI1248A patent/HU167240B/hu unknown
1973
- 1973-01-01 AR AR248881A patent/AR208055A1/es active
- 1973-06-26 IL IL42613A patent/IL42613A/en unknown
- 1973-06-26 SE SE7308998A patent/SE405603B/xx unknown
- 1973-06-27 FI FI2054/73A patent/FI55199C/fi active
- 1973-06-27 AT AT563773A patent/AT329058B/de not_active IP Right Cessation
- 1973-06-28 DE DE2332860A patent/DE2332860C2/de not_active Expired
- 1973-06-28 DK DK357373AA patent/DK141066B/da not_active IP Right Cessation
- 1973-06-28 ES ES416971A patent/ES416971A1/es not_active Expired
- 1973-06-29 SU SU7301941205A patent/SU584782A3/ru active
- 1973-06-29 PL PL1973163721A patent/PL93702B1/pl unknown
- 1973-06-29 CH CH952573A patent/CH603639A5/xx not_active IP Right Cessation
- 1973-06-29 JP JP7357473A patent/JPS5336480B2/ja not_active Expired
- 1973-06-29 FR FR7323956A patent/FR2190458B1/fr not_active Expired
- 1973-06-29 CH CH191877A patent/CH602730A5/xx not_active IP Right Cessation
- 1973-06-29 GB GB3117573A patent/GB1438819A/en not_active Expired
- 1973-06-29 PL PL1973193522A patent/PL96818B1/pl unknown
- 1973-06-29 NO NO732694A patent/NO138908C/no unknown
- 1973-06-29 PL PL1973184279A patent/PL94046B1/pl unknown
- 1973-06-29 NL NLAANVRAGE7309104,A patent/NL177750C/xx not_active IP Right Cessation
- 1973-06-29 CA CA175,341A patent/CA1014559A/en not_active Expired
- 1973-06-29 CH CH191777A patent/CH602729A5/xx not_active IP Right Cessation
- 1973-06-29 DD DD171938A patent/DD108090A1/xx unknown
- 1973-06-29 PL PL1973184281A patent/PL94060B1/pl unknown
- 1973-06-29 CH CH1359177A patent/CH610900A5/xx not_active IP Right Cessation
- 1973-06-29 CH CH191977A patent/CH602731A5/xx not_active IP Right Cessation
- 1973-06-29 PL PL1973184280A patent/PL94059B1/pl unknown
- 1973-06-29 CH CH1280677A patent/CH603647A5/xx not_active IP Right Cessation
- 1973-06-29 PL PL1973190223A patent/PL97544B1/pl unknown
- 1973-06-29 YU YU1796/73A patent/YU36175B/xx unknown
- 1973-06-29 BE BE132908A patent/BE801668A/xx not_active IP Right Cessation
- 1973-06-30 EG EG252/73A patent/EG11302A/xx active
- 1973-06-30 IN IN1533/CAL/73A patent/IN139710B/en unknown
- 1973-07-02 CS CS7300004783A patent/CS179024B1/cs unknown
1974
- 1974-12-23 AR AR257053A patent/AR210066A1/es active
1975
- 1975-11-21 AR AR261311A patent/AR209331A1/es active
- 1975-11-21 AR AR261310A patent/AR209330A1/es active
1976
- 1976-02-24 SU SU762325405A patent/SU587863A3/ru active
- 1976-02-24 SU SU762326052A patent/SU591148A3/ru active
- 1976-02-24 SU SU7602325957A patent/SU584783A3/ru active
- 1976-03-17 AR AR262581A patent/AR211857A1/es active
- 1976-09-14 SE SE7610170A patent/SE425314B/xx unknown
- 1976-09-14 SE SE7610171A patent/SE410190B/xx not_active IP Right Cessation
- 1976-09-14 SE SE7610169A patent/SE410189B/xx not_active IP Right Cessation
- 1976-10-26 SU SU762414099A patent/SU596170A3/ru active
1977
- 1977-07-29 JP JP9130377A patent/JPS5334799A/ja active Granted
1979
- 1979-12-10 YU YU2995/79A patent/YU36176B/xx unknown
- 1979-12-10 YU YU2994/79A patent/YU36300B/xx unknown
- 1979-12-10 YU YU2996/79A patent/YU36177B/xx unknown
1980
- 1980-01-11 SE SE8000253A patent/SE431455B/sv unknown
- 1980-04-02 SE SE8002538A patent/SE420968B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
AT329058B (de)	1976-04-26
SE405603B (sv)	1978-12-18
SE7610171L (sv)	1976-09-14
FI55199B (fi)	1979-02-28
CA1014559A (en)	1977-07-26
YU36176B (en)	1982-02-25
SU584783A3 (ru)	1977-12-15
YU299479A (en)	1981-08-31
JPS5740152B2 (fi)	1982-08-25
NL7309104A (fi)	1974-01-02
SU596170A3 (ru)	1978-02-28
CS179024B1 (en)	1977-10-31
DD108090A1 (fi)	1974-09-05
NO138908B (no)	1978-08-28
ES416971A1 (es)	1976-02-16
AR209330A1 (es)	1977-04-15
PL97544B1 (pl)	1978-03-30
CH603639A5 (fi)	1978-08-31
PL96818B1 (pl)	1978-01-31
NL177750C (nl)	1985-11-18
SE410190B (sv)	1979-10-01
SE7610169L (sv)	1976-09-14
JPS4942697A (fi)	1974-04-22
CH603647A5 (fi)	1978-08-31
CH610900A5 (en)	1979-05-15
AR209331A1 (es)	1977-04-15
YU36177B (en)	1982-02-25
NL177750B (nl)	1985-06-17
AR210066A1 (es)	1977-06-30
NO138908C (no)	1978-12-06
CH602731A5 (fi)	1978-07-31
FI55199C (fi)	1979-06-11
AR211857A1 (es)	1978-03-31
PL94059B1 (en)	1977-07-30
DK141066B (da)	1980-01-07
SE420968B (sv)	1981-11-09
YU299579A (en)	1981-06-30
IL42613A0 (en)	1973-08-29
PL93702B1 (en)	1977-06-30
DE2332860A1 (de)	1974-03-07
SU584782A3 (ru)	1977-12-15
CH602730A5 (fi)	1978-07-31
SE7308998L (sv)	1973-12-31
AR208055A1 (es)	1976-11-30
CH602729A5 (fi)	1978-07-31
FR2190458A1 (fi)	1974-02-01
IN139710B (fi)	1976-07-24
YU179673A (en)	1981-06-30
PL94060B1 (en)	1977-07-30
GB1438819A (en)	1976-06-09
JPS5334799A (en)	1978-03-31
SE431455B (sv)	1984-02-06
SE7610170L (sv)	1976-09-14
HU167240B (fi)	1975-09-27
FR2190458B1 (fi)	1977-04-15
SE410189B (sv)	1979-10-01
BE801668A (fr)	1973-10-15
YU36300B (en)	1982-06-18
YU299679A (en)	1981-06-30
SU587863A3 (ru)	1978-01-05
EG11302A (en)	1978-06-30
SU591148A3 (ru)	1978-01-30
SE8002538L (sv)	1981-10-03
JPS5336480B2 (fi)	1978-10-03
PL94046B1 (en)	1977-07-30
DE2332860C2 (de)	1982-12-02
DK141066C (fi)	1980-06-30
SE425314B (sv)	1982-09-20
YU36175B (en)	1982-02-25
ATA563773A (de)	1975-07-15

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US4372956A (en)	1983-02-08	5, 10-Dihydroimidazo[2,1-b]quinazolines and pharmaceutical compositions containing them
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