NO793537L - Pyrimido-(6,1-a)-isochinolin-4-on, nye ved deres fremstilling anvendte mellomprodukter, samt fremgangsmaate til deres fremstilling - Google Patents

Pyrimido-(6,1-a)-isochinolin-4-on, nye ved deres fremstilling anvendte mellomprodukter, samt fremgangsmaate til deres fremstilling

Info

Publication number: NO793537L
Authority: NO; Norway
Prior art keywords: formula; alkyl; compound; meaning; pyrimido
Prior art date: 1978-11-03

Application number

NO793537A

Other languages

English (en)

Norwegian (no)

Inventor

Bansi Lal

Sa Adolf D

Horst Dornauer

Noel John De Souza

Original Assignee

Hoechst Ag

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.)

1978-11-03

Filing date

1979-11-02

Publication date

1980-05-06

1979-11-02 Application filed by Hoechst Ag filed Critical Hoechst Ag

1980-05-06 Publication of NO793537L publication Critical patent/NO793537L/no

Links

238000000034 method Methods 0.000 title claims abstract description 13
238000002360 preparation method Methods 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title claims description 4
CIVQDIGHVMGTPD-UHFFFAOYSA-N pyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=CC=C2C=CN3C(=O)N=CC=C3C2=C1 CIVQDIGHVMGTPD-UHFFFAOYSA-N 0.000 title abstract description 12
239000000543 intermediate Substances 0.000 title abstract description 7
150000001875 compounds Chemical class 0.000 claims abstract description 21
229910052736 halogen Chemical group 0.000 claims abstract description 12
150000002367 halogens Chemical group 0.000 claims abstract description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
239000001301 oxygen Substances 0.000 claims abstract description 7
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 5
-1 methylenedioxy Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 19
125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 8
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
229910052740 iodine Inorganic materials 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
239000005864 Sulphur Substances 0.000 claims description 4
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
239000002585 base Substances 0.000 claims description 4
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
150000003839 salts Chemical class 0.000 claims description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
229910052783 alkali metal Inorganic materials 0.000 claims description 3
150000001340 alkali metals Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
DNZPLHRZXUJATK-UHFFFAOYSA-N 2-sulfanylidene-5-[[5-[2-(trifluoromethyl)phenyl]furan-2-yl]methyl]-1,3-diazinane-4,6-dione Chemical compound FC(F)(F)C1=CC=CC=C1C(O1)=CC=C1CC1C(=O)NC(=S)NC1=O DNZPLHRZXUJATK-UHFFFAOYSA-N 0.000 claims description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 2
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
125000003107 substituted aryl group Chemical group 0.000 claims description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
239000003814 drug Substances 0.000 claims 2
125000006559 (C1-C3) alkylamino group Chemical group 0.000 claims 1
125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 1
238000006482 condensation reaction Methods 0.000 claims 1
125000000753 cycloalkyl group Chemical group 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
150000002829 nitrogen Chemical group 0.000 claims 1
125000004433 nitrogen atom Chemical group N* 0.000 claims 1
229910052698 phosphorus Inorganic materials 0.000 claims 1
239000011574 phosphorus Substances 0.000 claims 1
239000003381 stabilizer Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract 1
239000011593 sulfur Chemical group 0.000 abstract 1
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
239000013543 active substance Substances 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
229910052801 chlorine Inorganic materials 0.000 description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
XADOJCGJGFXLAH-UHFFFAOYSA-N 1-[2-(3,4-dimethoxyphenyl)ethyl]-1,3-diazinane-2,4,6-trione Chemical compound C1=C(OC)C(OC)=CC=C1CCN1C(=O)NC(=O)CC1=O XADOJCGJGFXLAH-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
150000007656 barbituric acids Chemical class 0.000 description 4
238000009835 boiling Methods 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
125000003282 alkyl amino group Chemical group 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
238000011282 treatment Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
HLTDPZGESWXQLF-UHFFFAOYSA-N 9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinoline-2,4-dione Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(=O)NC2=O HLTDPZGESWXQLF-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
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 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000003266 anti-allergic effect Effects 0.000 description 2
150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
125000003435 aroyl group Chemical group 0.000 description 2
150000005840 aryl radicals Chemical class 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
230000004531 blood pressure lowering effect Effects 0.000 description 2
230000003182 bronchodilatating effect Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
125000004663 dialkyl amino group Chemical group 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
125000001188 haloalkyl group Chemical group 0.000 description 2
229910001502 inorganic halide Inorganic materials 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical class IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
238000011321 prophylaxis Methods 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
QHOOBPAPZHMEFH-UHFFFAOYSA-N 1-[2-(1,3-benzodioxol-5-yl)ethyl]-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)CC(=O)N1CCC1=CC=C(OCO2)C2=C1 QHOOBPAPZHMEFH-UHFFFAOYSA-N 0.000 description 1
DXMVYTFUFSYIBK-UHFFFAOYSA-N 2-(2,4-dimethylanilino)-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(N=2)=O)C1=CC=2NC1=CC=C(C)C=C1C DXMVYTFUFSYIBK-UHFFFAOYSA-N 0.000 description 1
XBQVXGZOLPBCEM-UHFFFAOYSA-N 2-(2,6-dimethylanilino)-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN(C(N=2)=O)C1=CC=2NC1=C(C)C=CC=C1C XBQVXGZOLPBCEM-UHFFFAOYSA-N 0.000 description 1
AGWGKICLZGPZRH-UHFFFAOYSA-N 2-(butan-2-ylamino)-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one;hydrochloride Chemical compound Cl.C12=CC(OC)=C(OC)C=C2CCN2C1=CC(NC(C)CC)=NC2=O AGWGKICLZGPZRH-UHFFFAOYSA-N 0.000 description 1
VOJKMWAQJKZEIT-UHFFFAOYSA-N 2-(tert-butylamino)-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one;hydrochloride Chemical compound Cl.C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(NC(C)(C)C)=NC2=O VOJKMWAQJKZEIT-UHFFFAOYSA-N 0.000 description 1
BIJWXQNMLKVZJM-UHFFFAOYSA-N 2-chloro-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(Cl)=NC2=O BIJWXQNMLKVZJM-UHFFFAOYSA-N 0.000 description 1
NHSSCHXBGADITM-UHFFFAOYSA-N 9,10-dimethoxy-2-(2,4,6-trimethylanilino)-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one;dihydrate;hydrochloride Chemical compound O.O.Cl.C1=2C=C(OC)C(OC)=CC=2CCN(C(N=2)=O)C1=CC=2NC1=C(C)C=C(C)C=C1C NHSSCHXBGADITM-UHFFFAOYSA-N 0.000 description 1
IPTRQPHDOAZCRH-UHFFFAOYSA-N 9,10-dimethoxy-3-methyl-6,7-dihydropyrimido[6,1-a]isoquinoline-2,4-dione Chemical compound C1=2C=C(OC)C(OC)=CC=2CCN2C1=CC(=O)N(C)C2=O IPTRQPHDOAZCRH-UHFFFAOYSA-N 0.000 description 1
LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
206010006458 Bronchitis chronic Diseases 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
206010014561 Emphysema Diseases 0.000 description 1
208000007530 Essential hypertension Diseases 0.000 description 1
206010019280 Heart failures Diseases 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
206010020751 Hypersensitivity Diseases 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
206010039085 Rhinitis allergic Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
208000024780 Urticaria Diseases 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
201000009961 allergic asthma Diseases 0.000 description 1
201000010105 allergic rhinitis Diseases 0.000 description 1
230000007815 allergy Effects 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
230000003288 anthiarrhythmic effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000002371 cardiac agent Substances 0.000 description 1
208000007451 chronic bronchitis Diseases 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
239000003246 corticosteroid Substances 0.000 description 1
229960001334 corticosteroids Drugs 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
229940030606 diuretics Drugs 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000012458 free base Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
208000021760 high fever Diseases 0.000 description 1
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
230000000055 hyoplipidemic effect Effects 0.000 description 1
208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
229940083747 low-ceiling diuretics xanthine derivative Drugs 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
201000005857 malignant hypertension Diseases 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
230000003836 peripheral circulation Effects 0.000 description 1
230000003285 pharmacodynamic effect Effects 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
210000002345 respiratory system Anatomy 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings

Landscapes

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

NO793537A 1978-11-03 1979-11-02 Pyrimido-(6,1-a)-isochinolin-4-on, nye ved deres fremstilling anvendte mellomprodukter, samt fremgangsmaate til deres fremstilling NO793537L (no)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19782847693 DE2847693A1 (de)	1978-11-03	1978-11-03	Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen

Publications (1)

Publication Number	Publication Date
NO793537L true NO793537L (no)	1980-05-06

Family

ID=6053766

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO793537A NO793537L (no)	1978-11-03	1979-11-02	Pyrimido-(6,1-a)-isochinolin-4-on, nye ved deres fremstilling anvendte mellomprodukter, samt fremgangsmaate til deres fremstilling

Country Status (18)

Country	Link
US (1)	US4400506A (fr)
EP (1)	EP0010759B1 (fr)
JP (1)	JPS5564587A (fr)
AT (1)	ATE21104T1 (fr)
AU (1)	AU538039B2 (fr)
CA (1)	CA1123434A (fr)
DE (2)	DE2847693A1 (fr)
DK (1)	DK465879A (fr)
ES (2)	ES485489A0 (fr)
FI (1)	FI66865C (fr)
GR (1)	GR74082B (fr)
HU (1)	HU181884B (fr)
IL (1)	IL58609A0 (fr)
NO (1)	NO793537L (fr)
NZ (1)	NZ191994A (fr)
PH (1)	PH15281A (fr)
PT (1)	PT70401A (fr)
ZA (1)	ZA795888B (fr)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI64370C (fi) *	1977-05-05	1983-11-10	Hoechst Ag	Foerfarande foer framstaellning av terapeutiskt anvaendbara pyimido-(6,1-a)isokinolin-2-imino-4-onderivat
DE2847693A1 (de)	1978-11-03	1980-05-22	Hoechst Ag	Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen
FR2470130A2 (fr) *	1979-11-21	1981-05-29	Hoechst Ag	Derives de pyrimido (6,1-a) isoquinoleine-4-one, leur procede de preparation et leur application en therapeutique
DE3126837A1 (de) *	1981-07-08	1983-01-27	Hoechst Ag, 6000 Frankfurt	Triazino-(2,1-a)isochinolinderivate
DE3135831A1 (de) *	1981-09-10	1983-04-28	Hoechst Ag, 6230 Frankfurt	9,10-substituierte 2-mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2h-pyrimido(6,1-a)isochinolin-4-one, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US4612376A (en) *	1983-03-25	1986-09-16	Fujisawa Pharmaceutical Co., Ltd.	Substituted-3,4-dihydro-4-(2,4,6-trimethoxyphenylimino)-2(1H)-pyrimidones useful as cardiotonic, antihypertensive, cerebrovascular vasodilator and anti-platelet agent
CA1237429A (fr) *	1983-05-05	1988-05-31	Frank Kienzle	Derives de pyrimidone
CN100415743C (zh) *	1999-03-31	2008-09-03	韦尔纳利斯有限公司	嘧啶并[6,1-a] 异喹啉-4-酮衍生物
CZ302882B6 (cs) *	1999-08-21	2012-01-04	Nycomed Gmbh	Farmaceutický prostredek
TWI347845B (en) *	2002-03-06	2011-09-01	Nycomed Gmbh	Pharmaceutical compositions,combinations,and kits for the treatment of respiratory diseases and use of the same
US7772188B2 (en)	2003-01-28	2010-08-10	Ironwood Pharmaceuticals, Inc.	Methods and compositions for the treatment of gastrointestinal disorders
MX354786B (es)	2007-06-04	2018-03-21	Synergy Pharmaceuticals Inc	Agonistas de guanilato ciclasa utiles para el tratamiento de trastornos gastrointestinales, inflamacion, cancer y otros trastornos.
US8969514B2 (en)	2007-06-04	2015-03-03	Synergy Pharmaceuticals, Inc.	Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
CA2726917C (fr)	2008-06-04	2018-06-26	Synergy Pharmaceuticals Inc.	Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles
EP2321341B1 (fr)	2008-07-16	2017-02-22	Synergy Pharmaceuticals Inc.	Agonistes de guanylate cyclase utiles pour le traitement de troubles gastro-intestinaux, inflammatoires, cancéreux et autres
US9616097B2 (en)	2010-09-15	2017-04-11	Synergy Pharmaceuticals, Inc.	Formulations of guanylate cyclase C agonists and methods of use
EA201391254A1 (ru)	2011-03-01	2014-02-28	Синерджи Фармасьютикалз Инк.	Способ получения агонистов гуанилатциклазы c
JP6499591B2 (ja)	2013-02-25	2019-04-10	シナジーファーマシューティカルズインコーポレイテッド	結腸洗浄において用いるためのグアニル酸シクラーゼ受容体アゴニスト
WO2014151200A2 (fr)	2013-03-15	2014-09-25	Synergy Pharmaceuticals Inc.	Compositions utiles pour le traitement de troubles gastro-intestinaux
JP2016514671A (ja)	2013-03-15	2016-05-23	シナジーファーマシューティカルズインコーポレイテッド	グアニル酸シクラーゼのアゴニストおよびその使用
CN105764916B (zh)	2013-06-05	2021-05-18	博士医疗爱尔兰有限公司	鸟苷酸环化酶c的超纯激动剂、制备和使用所述激动剂的方法
EP3492106B1 (fr)	2013-08-09	2021-02-17	Ardelyx, Inc.	Composés et procédés d'inhibition du transport de phosphate
GB201613054D0 (en)	2016-07-28	2016-09-14	Verona Pharma Plc	New compound and process
EP3972599B1 (fr)	2019-05-21	2025-10-22	Ardelyx, Inc.	Combinaison pour baisser le phosphate sérique chez un patient
GB202202297D0 (en)	2022-02-21	2022-04-06	Verona Pharma Plc	Formulation production process
TW202506117A (zh)	2023-06-26	2025-02-16	英商維羅納製藥Ｐｌｃ公司	顆粒組成物

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE590405A (fr) *	1959-05-02
US3081306A (en) *	1959-11-04	1963-03-12	Pfizer & Co C	2, 4-dioxo-3-aralkylaza-9, 10-di(lower alkoxy)-1, 2, 3, 4, 6, 7-hexahydro-11b-h-benzopyridocolines
GB1062357A (en) *	1965-03-23	1967-03-22	Pfizer & Co C	Quinazolone derivatives
US3476755A (en) *	1967-01-17	1969-11-04	Edward C Taylor	8,13-diazasteroids
US3594379A (en) *	1968-09-16	1971-07-20	Sandoz Ag	2,3-dihydroimidazo(1,2-c)quinazolines
US3876788A (en) *	1970-08-27	1975-04-08	Burroughs Wellcome Co	Heterocyclic compounds in the treatment of inflammatory of arthritic conditions
IN147624B (fr)	1976-12-10	1980-05-03	Hoechst Pharma
DE2720085A1 (de) *	1977-05-05	1978-11-16	Hoechst Ag	Pyrimido(6,1-a)isochinolin-2-on- derivate
FI64370C (fi) *	1977-05-05	1983-11-10	Hoechst Ag	Foerfarande foer framstaellning av terapeutiskt anvaendbara pyimido-(6,1-a)isokinolin-2-imino-4-onderivat
DE2847693A1 (de)	1978-11-03	1980-05-22	Hoechst Ag	Verfahren zur herstellung von pyrimido-(6,1-a)-isochinolin-2-onen

1978
- 1978-11-03 DE DE19782847693 patent/DE2847693A1/de not_active Withdrawn
1979
- 1979-10-29 ES ES485489A patent/ES485489A0/es active Granted
- 1979-10-31 EP EP79104238A patent/EP0010759B1/fr not_active Expired
- 1979-10-31 DE DE7979104238T patent/DE2967610D1/de not_active Expired
- 1979-10-31 AT AT79104238T patent/ATE21104T1/de not_active IP Right Cessation
- 1979-11-01 NZ NZ191994A patent/NZ191994A/xx unknown
- 1979-11-01 GR GR60383A patent/GR74082B/el unknown
- 1979-11-01 JP JP14053279A patent/JPS5564587A/ja active Pending
- 1979-11-01 IL IL58609A patent/IL58609A0/xx unknown
- 1979-11-01 FI FI793430A patent/FI66865C/fi not_active IP Right Cessation
- 1979-11-02 HU HU79HO2195A patent/HU181884B/hu unknown
- 1979-11-02 AU AU52453/79A patent/AU538039B2/en not_active Ceased
- 1979-11-02 NO NO793537A patent/NO793537L/no unknown
- 1979-11-02 CA CA339,089A patent/CA1123434A/fr not_active Expired
- 1979-11-02 DK DK465879A patent/DK465879A/da not_active Application Discontinuation
- 1979-11-02 ZA ZA00795888A patent/ZA795888B/xx unknown
- 1979-11-02 PT PT70401A patent/PT70401A/pt unknown
- 1979-11-05 PH PH23245A patent/PH15281A/en unknown
1980
- 1980-07-01 ES ES493011A patent/ES8103083A1/es not_active Expired
1981
- 1981-10-26 US US06/314,994 patent/US4400506A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
PT70401A (de)	1979-12-01
AU538039B2 (en)	1984-07-26
DE2967610D1 (en)	1986-09-04
ES493011A0 (es)	1981-02-16
ATE21104T1 (de)	1986-08-15
PH15281A (en)	1982-11-02
EP0010759A2 (fr)	1980-05-14
CA1123434A (fr)	1982-05-11
IL58609A0 (en)	1980-02-29
DK465879A (da)	1980-05-04
EP0010759A3 (en)	1981-08-19
FI66865B (fi)	1984-08-31
ZA795888B (en)	1980-10-29
FI793430A7 (fi)	1980-05-04
ES8103083A1 (es)	1981-02-16
GR74082B (fr)	1984-06-06
EP0010759B1 (fr)	1986-07-30
US4400506A (en)	1983-08-23
JPS5564587A (en)	1980-05-15
ES8102125A1 (es)	1980-12-16
NZ191994A (en)	1982-09-07
HU181884B (en)	1983-11-28
AU5245379A (en)	1980-05-08
FI66865C (fi)	1984-12-10
DE2847693A1 (de)	1980-05-22
ES485489A0 (es)	1980-12-16

Publication	Publication Date	Title
NO793537L (no)	1980-05-06	Pyrimido-(6,1-a)-isochinolin-4-on, nye ved deres fremstilling anvendte mellomprodukter, samt fremgangsmaate til deres fremstilling
US4675319A (en)	1987-06-23	Antianaphylactic and antibronchospastic piperazinyl-(N-substituted phenyl)carboxamides, compositions and use
NO821266L (no)	1978-11-07	Pyrimido(6,1-a)isokinolin-4-on-derivater
NO162965B (no)	1989-12-04	Analogifremgangsmaate for fremstilling av terapeutisk aktive alfa-(2-okso-2,4,5,6,7,7a-heksahydrotieno-(3,2-c)-5-pyridyl)-fenyl-eddiksyre-derivater.
EP0006506B1 (fr)	1981-09-16	Dérivés de la dihydro-1.2-oxo-2-quinoléine, procédés pour leur préparation et médicaments les contenant
US5574039A (en)	1996-11-12	Antiproliferative compounds having nitrogen-containing tricyclic ring systems and phenyl substituents
CA2209422C (fr)	2001-09-11	Derives 4-amino-3-acylnaphtyridine
US2681910A (en)	1954-06-22	Halogenated quinolinol compounds
NZ227149A (en)	1990-04-26	(2-piperazinyl)-2-oxoethylene-substituted flavonoid derivatives and pharmaceutical compositions
US4086347A (en)	1978-04-25	9-[3-(4-Phenoxymethylpiperidino)-propyl]-adenines
EP0964865B1 (fr)	2003-03-05	Amines tricycliques pharmaceutiquement actives
JPS63192778A (ja)	1988-08-10	β−アドレナリン受容体遮断薬としてのピペラジニルピリミジン類
JPH07215973A (ja)	1995-08-15	置換キノリン誘導体
US5229392A (en)	1993-07-20	2-aminopyrimidine-4-carboxamide derivatives, their preparaton and their application in therapy
GB1597717A (en)	1981-09-09	Pyrimido (6,1-a) isoquinolin-4-one derivatives
NO128773B (fr)	1974-01-07
US4048184A (en)	1977-09-13	6-Phenyl-2H-pyrazolo[3,4-b]pyridines
NO793578L (no)	1980-05-08	Analogifremgangsmaate for fremstilling av fysiologisk aktive trifenylalkenderivater
IE55377B1 (en)	1990-08-29	1,5-diphenylpyrazolin-3-one compounds,method for preparing them,and pharmaceutical compositions containing these compounds
US3898230A (en)	1975-08-05	Sydnone imine compounds
US5981530A (en)	1999-11-09	Piperazine derivative
KR830002078B1 (ko)	1983-10-11	피리미도(6,1-a) 이소퀴놀린-4-온류의 제조방법
PT617027E (pt)	2000-09-29	Novos compostos de n-benzil-piperazina processo para a sua preparacao e as composicoes farmaceuticas que os contem
EP0022481A1 (fr)	1981-01-21	Dérivés de la 5,6-alcoylènepyrimidine, procédés pour leur préparation et préparations pharmaceutiques
US3712893A (en)	1973-01-23	Butyl-piperazine derivatives