PL131162B1 - Process for preparing novel derivatives of 4h-pyrido /1,2-a/ pyrimidin-4-one - Google Patents

Process for preparing novel derivatives of 4h-pyrido /1,2-a/ pyrimidin-4-one Download PDF

Info

Publication number: PL131162B1
Authority: PL; Poland
Prior art keywords: formula; alk; group; pyrido; hydrogen atom
Prior art date: 1980-03-28

Application number

PL1981233902A

Other languages

English (en)

Polish (pl)

Other versions

PL233902A1 (de

Original Assignee

Janssen Pharmaceutica Nv

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.)

1980-03-28

Filing date

1981-03-27

Publication date

1984-10-31

1981-03-27 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1982-07-19 Publication of PL233902A1 publication Critical patent/PL233902A1/xx

1984-10-31 Publication of PL131162B1 publication Critical patent/PL131162B1/pl

Links

DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title 1
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
-1 sulfonyloxy group Chemical group 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
238000010992 reflux Methods 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 3
238000009833 condensation Methods 0.000 claims description 3
230000005494 condensation Effects 0.000 claims description 3
125000004185 ester group Chemical group 0.000 claims description 3
125000001475 halogen functional group Chemical group 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims description 2
238000009835 boiling Methods 0.000 claims 1
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 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
241000700159 Rattus Species 0.000 description 12
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 8
230000003902 lesion Effects 0.000 description 7
239000000243 solution Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
239000007924 injection Substances 0.000 description 6
238000002347 injection Methods 0.000 description 6
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
229940076279 serotonin Drugs 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
210000001367 artery Anatomy 0.000 description 5
230000008602 contraction Effects 0.000 description 5
201000010099 disease Diseases 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
210000002784 stomach Anatomy 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
239000002585 base Substances 0.000 description 4
229920002055 compound 48/80 Polymers 0.000 description 4
230000002496 gastric effect Effects 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
239000003826 tablet Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000035939 shock Effects 0.000 description 3
239000007858 starting material Substances 0.000 description 3
NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
206010011703 Cyanosis Diseases 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
230000003042 antagnostic effect Effects 0.000 description 2
229940082988 antihypertensives serotonin antagonists Drugs 0.000 description 2
239000003420 antiserotonin agent Substances 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229960001701 chloroform Drugs 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
210000005069 ears Anatomy 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000000762 glandular Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
239000006187 pill Substances 0.000 description 2
150000003053 piperidines Chemical class 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
150000003930 2-aminopyridines Chemical class 0.000 description 1
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 description 1
QGKGASXQTBQINX-UHFFFAOYSA-N 3,4-dihydro-1h-pyrimidin-2-one Chemical class O=C1NCC=CN1 QGKGASXQTBQINX-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
244000144725 Amygdalus communis Species 0.000 description 1
235000011437 Amygdalus communis Nutrition 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
241000283707 Capra Species 0.000 description 1
235000005979 Citrus limon Nutrition 0.000 description 1
244000131522 Citrus pyriformis Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
206010020565 Hyperaemia Diseases 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
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
UEQUQVLFIPOEMF-UHFFFAOYSA-N Mianserin Chemical compound C1C2=CC=CC=C2N2CCN(C)CC2C2=CC=CC=C21 UEQUQVLFIPOEMF-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
206010046996 Varicose vein Diseases 0.000 description 1
241000212749 Zesius chrysomallus Species 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000000556 agonist Substances 0.000 description 1
125000002723 alicyclic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
235000020224 almond Nutrition 0.000 description 1
ICSNLGPSRYBMBD-UHFFFAOYSA-N alpha-aminopyridine Natural products NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000017531 blood circulation Effects 0.000 description 1
210000004204 blood vessel Anatomy 0.000 description 1
210000000748 cardiovascular system Anatomy 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
RSUVYMGADVXGOU-BUHFOSPRSA-N cinanserin Chemical compound CN(C)CCCSC1=CC=CC=C1NC(=O)\C=C\C1=CC=CC=C1 RSUVYMGADVXGOU-BUHFOSPRSA-N 0.000 description 1
229950001684 cinanserin Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
201000006549 dyspepsia Diseases 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
235000013305 food Nutrition 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
229960004275 glycolic acid Drugs 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
208000014617 hemorrhoid Diseases 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
229910001511 metal iodide Inorganic materials 0.000 description 1
WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
229960004650 metergoline Drugs 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
229960003955 mianserin Drugs 0.000 description 1
238000002156 mixing Methods 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012057 packaged powder Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
FIADGNVRKBPQEU-UHFFFAOYSA-N pizotifen Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2CCC2=C1C=CS2 FIADGNVRKBPQEU-UHFFFAOYSA-N 0.000 description 1
229960004572 pizotifen Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
230000028327 secretion Effects 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
208000027185 varicose disease Diseases 0.000 description 1
208000019553 vascular disease Diseases 0.000 description 1
210000003462 vein Anatomy 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

PL1981233902A 1980-03-28 1981-03-27 Process for preparing novel derivatives of 4h-pyrido /1,2-a/ pyrimidin-4-one PL131162B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US13484580A	1980-03-28	1980-03-28

Publications (2)

Publication Number	Publication Date
PL233902A1 PL233902A1 (de)	1982-07-19
PL131162B1 true PL131162B1 (en)	1984-10-31

Family

ID=22465278

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
PL1981230364A PL132428B1 (en)	1980-03-28	1981-03-27	Proces for preparing novel derivatives of 3-/1-piperidinalkyl/-nh-pyrido-/1,2-a/-pyrimidin-4-one
PL1981233902A PL131162B1 (en)	1980-03-28	1981-03-27	Process for preparing novel derivatives of 4h-pyrido /1,2-a/ pyrimidin-4-one

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
PL1981230364A PL132428B1 (en)	1980-03-28	1981-03-27	Proces for preparing novel derivatives of 3-/1-piperidinalkyl/-nh-pyrido-/1,2-a/-pyrimidin-4-one

Country Status (5)

Country	Link
JP (1)	JPS56150091A (de)
KR (2)	KR850000412B1 (de)
PL (2)	PL132428B1 (de)
SU (1)	SU1093251A3 (de)
ZA (1)	ZA812085B (de)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
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JPH0615529B2 (ja) *	1985-04-01	1994-03-02	エーザイ株式会社	新規ピペリジン誘導体
DE68926473T2 (de) *	1988-03-28	1996-10-02	Janssen Pharmaceutica Nv	Mittel zur Konservierung oder Wiederherstellung der gesunden Haut
CN101970427A (zh)	2008-02-29	2011-02-09	Vm生物医药公司	治疗疼痛症状及其它失调的方法
EP2812004B1 (de) *	2012-02-10	2018-06-27	PTC Therapeutics, Inc.	Verbindungen zur behandlung von spinaler muskelatrophie
US10668171B2 (en)	2015-05-30	2020-06-02	Ptc Therapeutics, Inc.	Methods for modulating RNA splicing
EA201800367A1 (ru)	2015-12-10	2019-02-28	ПиТиСи ТЕРАПЬЮТИКС, ИНК.	Способы лечения болезни хантингтона
JP2019535789A (ja)	2016-11-28	2019-12-12	ピーティーシーセラピューティクス，インコーポレーテッド	Ｒｎａスプライシングを調節する方法
EP3634953B1 (de)	2017-06-05	2024-01-03	PTC Therapeutics, Inc.	Verbindungen zur behandlung von morbus huntington
JP2020523365A (ja)	2017-06-14	2020-08-06	ピーティーシーセラピューティクス，インコーポレーテッド	Ｒｎａスプライシングを改変する方法
MX2019015580A (es)	2017-06-28	2020-07-28	Ptc Therapeutics Inc	Metodos para tratar la enfermedad de huntington.
CN111182898B (zh)	2017-06-28	2024-04-16	Ptc医疗公司	用于治疗亨廷顿氏病的方法
EA202092001A1 (ru)	2018-03-27	2021-01-29	ПиТиСи ТЕРАПЬЮТИКС, ИНК.	Соединения для лечения болезни гентингтона
WO2020005877A1 (en)	2018-06-27	2020-01-02	Ptc Therapeutics, Inc.	Heteroaryl compounds for treating huntington's disease
HRP20240935T1 (hr)	2018-06-27	2024-11-22	Ptc Therapeutics, Inc.	Heterociklični i heteroaril spojevi za liječenje huntingtonove bolesti
EP3814360B8 (de)	2018-06-27	2024-11-06	PTC Therapeutics, Inc.	Heteroaryl verbindungen zur behandlung von morbus huntington

1981
- 1981-03-25 JP JP4260581A patent/JPS56150091A/ja active Granted
- 1981-03-27 PL PL1981230364A patent/PL132428B1/pl unknown
- 1981-03-27 PL PL1981233902A patent/PL131162B1/pl unknown
- 1981-03-27 ZA ZA00812085A patent/ZA812085B/xx unknown
- 1981-04-11 KR KR1019810001233A patent/KR850000412B1/ko not_active Expired
1982
- 1982-01-12 SU SU823372597A patent/SU1093251A3/ru active
1984
- 1984-08-27 KR KR1019840005210A patent/KR850000413B1/ko not_active Expired

Also Published As

Publication number	Publication date
PL233902A1 (de)	1982-07-19
PL230364A1 (de)	1982-03-29
JPS56150091A (en)	1981-11-20
PL132428B1 (en)	1985-03-30
JPH0215550B2 (de)	1990-04-12
KR830005220A (ko)	1983-08-03
KR850000413B1 (ko)	1985-03-26
SU1093251A3 (ru)	1984-05-15
ZA812085B (en)	1982-11-24
KR850000412B1 (ko)	1985-03-26

Publication	Publication Date	Title
PL131162B1 (en)	1984-10-31	Process for preparing novel derivatives of 4h-pyrido /1,2-a/ pyrimidin-4-one
EP0236930B1 (de)	1990-10-31	Aromatische 2-Aminoalkyl-1,2-benzoisothiazol-3-(2H)-on-1,1-dioxydderivate
SK31793A3 (en)	1993-09-08	Pyridine and pyridine n-oxide derivatives of diaryl methyl piperidines and piperazines and compositions and methods of use thereof
EP0086422B1 (de)	1987-09-30	Pharmakologisch aktive Pyrazolo (4,3-c)pyridine
US4636563A (en)	1987-01-13	Antipsychotic γ-carbolines
HU201553B (en)	1990-11-28	Process for producing tetrahydrofuro- and -thieno(2,3-c)pyridines and pharmaceutical compositions comprising same
Abou-Gharbia et al.	1987	Antipsychotic activity of substituted. gamma.-carbolines
US4138494A (en)	1979-02-06	3-Phenylindolines
US4672117A (en)	1987-06-09	Antipsychotic gamma-carbolines
Cain et al.	1976	Potential antitumor agents. 19. Multiply substituted 4'-(9-acridinylamino) methanesulfonanilides
US4663456A (en)	1987-05-05	2-(substituted piperazinylalkyl)β-carbolines useful in treatment of psychological disorders
EP0273176A2 (de)	1988-07-06	Kondensierte heterocyclische Tetrahydroaminochinolinole und verwandte Verbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
Cain et al.	1976	Potential antitumor agents. 20. Structure-activity-site relations for the 4'-(9-acridinylamino) alkanesulfonanilides
JPH0686435B2 (ja)	1994-11-02	ベンズアゼピン誘導体
US4012373A (en)	1977-03-15	Pyrazolo[3',4'-2,3]pyrido[4,5-e]b-benzo-1,5-diazepinones
PL170889B1 (pl)	1997-02-28	S posób wytwarzania nowej (7S,9aS)-2-(benzo[d]izoksazoliio-3) perhydro-7-{2-[(2aS)-2a- hydroksy-3,3- czterometylenogluta-rimido]etyio}-1H-pirydo[1,2-a] pirazyny i nowej(7S,9aS)-2-(benzo[d]izoksazolilo-3) perhydro-7-{2[(2aR)-2a-hydroksy-3,3- czterometylenoglutarimido]-etylo}-1 H-pirydo[1,2-a] pirazyny PL PL
JPS61254585A (ja)	1986-11-12	三環式誘導体
US3654290A (en)	1972-04-04	Intermediates for 5-(pyridylalkyl) pyridoindole derivatives
NZ201642A (en)	1985-01-31	1-phenylindazol-3-one derivatives and pharmaceutical compositions
EP0025603B1 (de)	1983-11-02	Triazolo (4,3-a)pyridin-3-(2H)-one, Verfahren zu ihrer Herstellung und sie enthaltende pharmazeutische Zusammensetzungen
US4789676A (en)	1988-12-06	Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)one-1,1-dioxide derivatives, usefull as anxiolytic agents
JPH02233682A (ja)	1990-09-17	８，９―アヌレーション化―１，２，３，４―テトラヒドロ―β―カルボリン誘導体
JPH03148284A (ja)	1991-06-25	ジヒドロピリミドチアジン誘導体、それを主成分とする抗炎症剤等製剤組成物、その製造の際の中間体、およびそれらの製造方法
US4920118A (en)	1990-04-24	Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3-(2H)one-1,1-dioxide and their use as anxiolytic and anti-hypertensive agents
US4857526A (en)	1989-08-15	Aromatic 2-aminoalkyl-1,2-benzoisothiazol-3(2H)-one-1,1-dioxide