CA1048496A - Synthese d'oxo-2 tetrahydro-1,2,3,4pyrido (2,3-d) pyrimidines - Google Patents

Synthese d'oxo-2 tetrahydro-1,2,3,4pyrido (2,3-d) pyrimidines

Info

Publication number: CA1048496A
Authority: CA; Canada
Prior art keywords: lower alkyl; oxo; group; ether; tetrahydropyrido
Prior art date: 1974-07-05
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA75230890A

Other languages

English (en)

Inventor

Kanji Noda

Akira Nakagawa

Toshiharu Motomura

Satoru Miyata

Hiroyuki Ide

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hisamitsu Pharmaceutical Co Inc

Original Assignee

Hisamitsu Pharmaceutical Co Inc

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.)

1974-07-05

Filing date

1975-07-07

Publication date

1979-02-13

1974-07-05 Priority claimed from JP49080367A external-priority patent/JPS58428B2/ja

1974-08-07 Priority claimed from JP49091202A external-priority patent/JPS58429B2/ja

1975-07-07 Application filed by Hisamitsu Pharmaceutical Co Inc filed Critical Hisamitsu Pharmaceutical Co Inc

1979-02-13 Application granted granted Critical

1979-02-13 Publication of CA1048496A publication Critical patent/CA1048496A/fr

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 4
XISPDDYROWQPHI-UHFFFAOYSA-N 3,4-dihydro-1h-pyrido[2,3-d]pyrimidin-2-one Chemical class C1=CN=C2NC(=O)NCC2=C1 XISPDDYROWQPHI-UHFFFAOYSA-N 0.000 title claims abstract 3
150000001875 compounds Chemical class 0.000 claims abstract description 39
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
-1 dihalophenyl Chemical group 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000005059 halophenyl group Chemical group 0.000 claims description 2
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
125000006501 nitrophenyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002130 sulfonic acid ester group Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 abstract description 7
239000001257 hydrogen Substances 0.000 abstract description 7
238000000034 method Methods 0.000 abstract description 6
230000000202 analgesic effect Effects 0.000 abstract description 5
125000003710 aryl alkyl group Chemical group 0.000 abstract description 5
210000003169 central nervous system Anatomy 0.000 abstract description 5
230000003110 anti-inflammatory effect Effects 0.000 abstract description 3
230000003001 depressive effect Effects 0.000 abstract description 3
229940035676 analgesics Drugs 0.000 abstract description 2
239000002260 anti-inflammatory agent Substances 0.000 abstract description 2
229940121363 anti-inflammatory agent Drugs 0.000 abstract description 2
230000000144 pharmacologic effect Effects 0.000 abstract description 2
230000001387 anti-histamine Effects 0.000 abstract 1
230000001754 anti-pyretic effect Effects 0.000 abstract 1
230000000767 anti-ulcer Effects 0.000 abstract 1
239000000739 antihistaminic agent Substances 0.000 abstract 1
239000002221 antipyretic Substances 0.000 abstract 1
239000003874 central nervous system depressant Substances 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 26
239000000203 mixture Substances 0.000 description 18
238000002844 melting Methods 0.000 description 14
230000008018 melting Effects 0.000 description 14
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
230000000694 effects Effects 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
125000004432 carbon atom Chemical group C* 0.000 description 8
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
125000003545 alkoxy group Chemical group 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
230000001154 acute effect Effects 0.000 description 4
238000004821 distillation Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000003513 alkali Substances 0.000 description 3
239000004202 carbamide Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
150000002431 hydrogen Chemical class 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
238000000746 purification Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 0.000 description 3
238000000926 separation method Methods 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
125000002883 imidazolyl group Chemical group 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
229910000765 intermetallic Inorganic materials 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000000047 product Substances 0.000 description 2
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 2
230000011514 reflex Effects 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000005270 trialkylamine group Chemical group 0.000 description 2
WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
IQPOOTCWZFNUJR-UHFFFAOYSA-N (2-anilinopyridin-3-yl)methanol Chemical class OCC1=CC=CN=C1NC1=CC=CC=C1 IQPOOTCWZFNUJR-UHFFFAOYSA-N 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 1
NRVCOPLQQUFWSN-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-methyl-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1N(C)CC2=CC=CN=C2N1C1=CC=CC(F)=C1 NRVCOPLQQUFWSN-UHFFFAOYSA-N 0.000 description 1
WJHWFJKKHQQAPX-UHFFFAOYSA-N 1-phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1NCC2=CC=CN=C2N1C1=CC=CC=C1 WJHWFJKKHQQAPX-UHFFFAOYSA-N 0.000 description 1
XSVAGKPFNAMYNE-UHFFFAOYSA-N 1-phenyl-3-propan-2-yl-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1N(C(C)C)CC2=CC=CN=C2N1C1=CC=CC=C1 XSVAGKPFNAMYNE-UHFFFAOYSA-N 0.000 description 1
IGKCQDUYZULGBM-UHFFFAOYSA-N 2,2,2-trifluoroethyl 4-methylbenzenesulfonate Chemical compound CC1=CC=C(S(=O)(=O)OCC(F)(F)F)C=C1 IGKCQDUYZULGBM-UHFFFAOYSA-N 0.000 description 1
LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 1
ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
URHKIGVUNHZPHP-UHFFFAOYSA-N 3-(aminomethyl)-n-(3-iodophenyl)pyridin-2-amine Chemical compound NCC1=CC=CN=C1NC1=CC=CC(I)=C1 URHKIGVUNHZPHP-UHFFFAOYSA-N 0.000 description 1
YTPQXRWASMUWHU-UHFFFAOYSA-N 3-(aminomethyl)-n-(3-methylphenyl)pyridin-2-amine Chemical compound CC1=CC=CC(NC=2C(=CC=CN=2)CN)=C1 YTPQXRWASMUWHU-UHFFFAOYSA-N 0.000 description 1
WYZLWPPMLGTKNP-UHFFFAOYSA-N 3-(ethylaminomethyl)-n-[3-(trifluoromethyl)phenyl]pyridin-2-amine Chemical compound CCNCC1=CC=CN=C1NC1=CC=CC(C(F)(F)F)=C1 WYZLWPPMLGTKNP-UHFFFAOYSA-N 0.000 description 1
125000004080 3-carboxypropanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C(O[H])=O 0.000 description 1
IROIHLLORYOBMJ-UHFFFAOYSA-N 3-ethyl-1-[3-(trifluoromethyl)phenyl]-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1N(CC)CC2=CC=CN=C2N1C1=CC=CC(C(F)(F)F)=C1 IROIHLLORYOBMJ-UHFFFAOYSA-N 0.000 description 1
BMXKUUFFBIHLJG-UHFFFAOYSA-N 3-methyl-1-[3-(trifluoromethyl)phenyl]-4h-pyrido[2,3-d]pyrimidin-2-one Chemical compound O=C1N(C)CC2=CC=CN=C2N1C1=CC=CC(C(F)(F)F)=C1 BMXKUUFFBIHLJG-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
229910018507 Al—Ni Inorganic materials 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
JEYCTXHKTXCGPB-UHFFFAOYSA-N Methaqualone Chemical compound CC1=CC=CC=C1N1C(=O)C2=CC=CC=C2N=C1C JEYCTXHKTXCGPB-UHFFFAOYSA-N 0.000 description 1
ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
101100327795 Penaeus monodon CHH3 gene Proteins 0.000 description 1
241000700159 Rattus Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000003213 activating effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
229910045601 alloy Inorganic materials 0.000 description 1
239000000956 alloy Substances 0.000 description 1
229940037003 alum Drugs 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000000730 antalgic agent Substances 0.000 description 1
OSOHBQZPFDDOMK-UHFFFAOYSA-N azane;propan-2-one Chemical compound N.CC(C)=O OSOHBQZPFDDOMK-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
UYUUZBHQMVKRPE-UHFFFAOYSA-N carbonyl dichloride;tetrachloromethane Chemical compound ClC(Cl)=O.ClC(Cl)(Cl)Cl UYUUZBHQMVKRPE-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000001721 carboxyacetyl group Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
GPUADMRJQVPIAS-QCVDVZFFSA-M cerivastatin sodium Chemical compound [Na+].COCC1=C(C(C)C)N=C(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 GPUADMRJQVPIAS-QCVDVZFFSA-M 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 1
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
BDUPRNVPXOHWIL-UHFFFAOYSA-N dimethyl sulfite Chemical compound COS(=O)OC BDUPRNVPXOHWIL-UHFFFAOYSA-N 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
125000004031 fumaroyl group Chemical group C(\C=C\C(=O)*)(=O)* 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
125000003099 maleoyl group Chemical group C(\C=C/C(=O)*)(=O)* 0.000 description 1
229960002803 methaqualone Drugs 0.000 description 1
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 1
XOZZATXWQMOVHL-UHFFFAOYSA-N n,n-dimethyl-1,1-di(propan-2-yloxy)methanamine Chemical compound CC(C)OC(N(C)C)OC(C)C XOZZATXWQMOVHL-UHFFFAOYSA-N 0.000 description 1
MPMQNXVIUFUDEP-UHFFFAOYSA-N n,n-dimethyl-1,3-dioxolan-2-amine Chemical compound CN(C)C1OCCO1 MPMQNXVIUFUDEP-UHFFFAOYSA-N 0.000 description 1
NPZXSSPSMGNHQD-UHFFFAOYSA-N n-(3-fluorophenyl)-3-(methylaminomethyl)pyridin-2-amine Chemical compound CNCC1=CC=CN=C1NC1=CC=CC(F)=C1 NPZXSSPSMGNHQD-UHFFFAOYSA-N 0.000 description 1
210000000653 nervous system Anatomy 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000003431 oxalo group Chemical group 0.000 description 1
229960002895 phenylbutazone Drugs 0.000 description 1
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
SDQCGKJCBWXRMK-UHFFFAOYSA-N propan-2-yl 4-methylbenzenesulfonate Chemical compound CC(C)OS(=O)(=O)C1=CC=C(C)C=C1 SDQCGKJCBWXRMK-UHFFFAOYSA-N 0.000 description 1
230000001047 pyretic effect Effects 0.000 description 1
239000000376 reactant Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
125000004385 trihaloalkyl group Chemical group 0.000 description 1
125000005023 xylyl group Chemical group 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)

CA75230890A 1974-07-05 1975-07-07 Synthese d'oxo-2 tetrahydro-1,2,3,4pyrido (2,3-d) pyrimidines Expired CA1048496A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP49080367A JPS58428B2 (ja)	1974-07-05	1974-07-05	シンキナ２− オキソ −１，２，３，４− テトラヒドロピリド（２，３−ｄ）ピリミジンユウドウタイノセイゾウホウ
JP49091202A JPS58429B2 (ja)	1974-08-07	1974-08-07	シンキナ２− オキソ −１，２，３，４− テトラヒドロピリド（２，３−ｄ）ピリミジンユウドウタイオヨビソノサンフカエンノセイゾウホウ

Publications (1)

Publication Number	Publication Date
CA1048496A true CA1048496A (fr)	1979-02-13

Family

ID=26421388

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA75230890A Expired CA1048496A (fr)	1974-07-05	1975-07-07	Synthese d'oxo-2 tetrahydro-1,2,3,4pyrido (2,3-d) pyrimidines

Country Status (3)

Country	Link
CA (1)	CA1048496A (fr)
CH (1)	CH614207A5 (fr)
SE (1)	SE420609B (fr)

1975
- 1975-06-09 SE SE7506575A patent/SE420609B/xx unknown
- 1975-06-24 CH CH815975A patent/CH614207A5/fr not_active IP Right Cessation
- 1975-07-07 CA CA75230890A patent/CA1048496A/fr not_active Expired

Also Published As

Publication number	Publication date
CH614207A5 (en)	1979-11-15
SE420609B (sv)	1981-10-19
SE7506575L (sv)	1976-01-07

Publication	Publication Date	Title
EP0040639B1 (fr)	1984-05-30	Derives isoxazoles
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EP0104522B1 (fr)	1991-05-29	Dérivés de la pyrazolo(3,4-b)pyridine et leur procédé de préparation
US4075342A (en)	1978-02-21	Antireproductive imidazo[2,1-a]isoquinoline compounds
US4774249A (en)	1988-09-27	Pyrimidine derivatives for treating malaria
US4166117A (en)	1979-08-28	1-(Aralkyl)-4-(4-oxo[3H]quinazolin-3-yl)piperidines
US4820819A (en)	1989-04-11	5-phenyl-3[2H]-pyridazinone derivatives
DK166584B1 (da)	1993-06-14	Substituerede 4-benzyl-1h-imidazoler, fremgangsmaade til deres fremstilling samt farmaceutiske praeparater indeholdende dem
US4021552A (en)	1977-05-03	10-[ω-(BENZOYLPIPERIDINYL)ALKYL]PHENOTHIAZINES
US4007276A (en)	1977-02-08	Triazolo isoindole derivatives
SU474134A3 (ru)	1975-06-14	Способ получени замещенных оксикротоновых кислот
CA1048496A (fr)	1979-02-13	Synthese d'oxo-2 tetrahydro-1,2,3,4pyrido (2,3-d) pyrimidines
US3632605A (en)	1972-01-04	Pyrroline derivatives
US4198514A (en)	1980-04-15	Lactam compounds
US3971814A (en)	1976-07-27	Benzo(b)thiophene derivatives
US3125583A (en)	1964-03-17	Hjnc oxchaxohxchc o oh
US4265903A (en)	1981-05-05	Aryl-substituted furnaces
US4009166A (en)	1977-02-22	Pyrido(2,3-d) pyrimidinones
US2783232A (en)	1957-02-26	Pyridazone compounds and their
US4018793A (en)	1977-04-19	Benzo (b) thiophene derivatives
DK156391B (da)	1989-08-14	Analogifremgangsmaade til fremstilling af 3-aminopyrrolderivater
US4056526A (en)	1977-11-01	Benzo(b)thiophene derivatives
US4082770A (en)	1978-04-04	Benzo(b)thiophene derivatives
US4055644A (en)	1977-10-25	Hydroxyalkyl substituted-4,5-dihydropyridazin(2H)-3-ones
US3497509A (en)	1970-02-24	Imino ester method for producing 1,4,5,6-tetrahydro-as-triazine