DE1231705B - Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivaten - Google Patents
Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivatenInfo
- Publication number
- DE1231705B DE1231705B DEF39784A DEF0039784A DE1231705B DE 1231705 B DE1231705 B DE 1231705B DE F39784 A DEF39784 A DE F39784A DE F0039784 A DEF0039784 A DE F0039784A DE 1231705 B DE1231705 B DE 1231705B
- Authority
- DE
- Germany
- Prior art keywords
- compound
- general formula
- vol
- methyl
- chlorine
- Prior art date
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 4
- -1 methylimino group Chemical group 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000010438 heat treatment Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000006254 arylation reaction Methods 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 2
- 150000001722 carbon compounds Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 32
- 229910052801 chlorine Inorganic materials 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000000155 melt Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002585 base Substances 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 8
- 230000000202 analgesic effect Effects 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000002560 therapeutic procedure Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-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
- 150000001408 amides Chemical class 0.000 description 2
- 150000001409 amidines Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 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
- 239000000284 extract Substances 0.000 description 2
- 150000002463 imidates Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- BWRNWWSQZROEOA-UHFFFAOYSA-N 2-morpholin-4-ylacetamide Chemical compound NC(=O)CN1CCOCC1 BWRNWWSQZROEOA-UHFFFAOYSA-N 0.000 description 1
- OFILXYRUXDYLLS-UHFFFAOYSA-N 2-piperidin-1-ylacetamide Chemical compound NC(=O)CN1CCCCC1 OFILXYRUXDYLLS-UHFFFAOYSA-N 0.000 description 1
- LBTUTDYXOOUODJ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetamide Chemical compound NC(=O)CN1CCCC1 LBTUTDYXOOUODJ-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
- ZMDWVDOBEGZQJC-UHFFFAOYSA-N 3-piperidin-1-ylpropanamide Chemical compound NC(=O)CCN1CCCCC1 ZMDWVDOBEGZQJC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LPABBDDDFWWAFH-UHFFFAOYSA-N CCOC(CN1CCNCC1)=NC Chemical compound CCOC(CN1CCNCC1)=NC LPABBDDDFWWAFH-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-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
- 101100028689 Drosophila melanogaster rho-7 gene Proteins 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OKJIRPAQVSHGFK-UHFFFAOYSA-N N-acetylglycine Chemical compound CC(=O)NCC(O)=O OKJIRPAQVSHGFK-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 206010039897 Sedation Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HPQVBLVZLGTSAG-UHFFFAOYSA-N ethyl 2-morpholin-4-ylethanimidate Chemical compound CCOC(=N)CN1CCOCC1 HPQVBLVZLGTSAG-UHFFFAOYSA-N 0.000 description 1
- SQYUNSLEGJKXGT-UHFFFAOYSA-N ethyl 2-piperidin-1-ylethanimidate Chemical compound CCOC(=N)CN1CCCCC1 SQYUNSLEGJKXGT-UHFFFAOYSA-N 0.000 description 1
- XGVQZXFFBYLGCN-UHFFFAOYSA-N ethyl 2-pyrrolidin-1-ylethanimidate Chemical compound CCOC(=N)CN1CCCC1 XGVQZXFFBYLGCN-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid 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
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N mono-n-propyl amine Natural products CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 150000002780 morpholines Chemical class 0.000 description 1
- 125000001064 morpholinomethyl group Chemical group [H]C([H])(*)N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- SOTHHBNFPDRYCM-UHFFFAOYSA-N n-methyl-2-piperazin-1-ylacetamide Chemical compound CNC(=O)CN1CCNCC1 SOTHHBNFPDRYCM-UHFFFAOYSA-N 0.000 description 1
- NCCHARWOCKOHIH-UHFFFAOYSA-N n-methylbenzamide Chemical compound CNC(=O)C1=CC=CC=C1 NCCHARWOCKOHIH-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- 229960004889 salicylic acid Drugs 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/90—Oxygen atoms with acyclic radicals attached in position 2 or 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1053063D GB1053063A (en:Method) | 1963-05-18 | ||
| DENDAT1249281D DE1249281B (en:Method) | 1963-05-18 | ||
| DEF39784A DE1231705B (de) | 1963-05-18 | 1963-05-18 | Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivaten |
| CH90467A CH447182A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von neuen Chinazolon-Derivaten |
| CH628164A CH447181A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von Chinazolon-Verbindungen |
| CH90567A CH447183A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von neuen Chinazolon-Verbindungen |
| SE5933/64A SE314074B (en:Method) | 1963-05-18 | 1964-05-14 | |
| US367568A US3322756A (en) | 1963-05-18 | 1964-05-14 | 2-aminoalkyl-3-hydrocarbon quinazolones-(4) |
| AT427764A AT254193B (de) | 1963-05-18 | 1964-05-15 | Verfahren zur Herstellung von neuen Chinazolon-Derivaten |
| AT774665A AT258918B (de) | 1963-05-18 | 1964-05-15 | Verfahren zur Herstellung von neuen Chinazolon-Verbindungen |
| DK531064AA DK105765C (da) | 1963-05-18 | 1964-05-15 | Fremgangsmåde til fremstilling af quinazolon-derivater eller syreadditionssalte deraf. |
| AT774565A AT258917B (de) | 1963-05-18 | 1964-05-15 | Verfahren zur Herstellung von neuen Chinazolon-Derivaten |
| DK531164AA DK106039C (da) | 1963-05-18 | 1964-05-15 | Fremgangsmåde til fremstilling af quinazolon-derivater eller syreadditionssalte deraf. |
| NL6405448A NL6405448A (en:Method) | 1963-05-18 | 1964-05-15 | |
| DK245564AA DK104409C (da) | 1963-05-18 | 1964-05-15 | Fremgangsmåde til fremstilling af quinazolonderivater eller syreadditionssalte deraf. |
| BE648093A BE648093A (en:Method) | 1963-05-18 | 1964-05-19 | |
| FR974901A FR1404524A (fr) | 1963-05-18 | 1964-05-19 | Nouvelles quinazolones et leur préparation |
| FR985329A FR3806M (fr) | 1963-05-18 | 1964-08-17 | Médicament a base d'un dérivé de la quinazolone-(4). |
| SE1512565A SE314075B (en:Method) | 1963-05-18 | 1965-11-23 | |
| SE1512665A SE314076B (en:Method) | 1963-05-18 | 1965-11-23 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF39784A DE1231705B (de) | 1963-05-18 | 1963-05-18 | Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivaten |
| DEF0042147 | 1964-02-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1231705B true DE1231705B (de) | 1967-01-05 |
Family
ID=25975761
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1249281D Pending DE1249281B (en:Method) | 1963-05-18 | ||
| DEF39784A Pending DE1231705B (de) | 1963-05-18 | 1963-05-18 | Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivaten |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1249281D Pending DE1249281B (en:Method) | 1963-05-18 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3322756A (en:Method) |
| AT (3) | AT258917B (en:Method) |
| BE (1) | BE648093A (en:Method) |
| CH (3) | CH447181A (en:Method) |
| DE (2) | DE1231705B (en:Method) |
| DK (3) | DK104409C (en:Method) |
| FR (1) | FR3806M (en:Method) |
| GB (1) | GB1053063A (en:Method) |
| NL (1) | NL6405448A (en:Method) |
| SE (3) | SE314074B (en:Method) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984555A (en) * | 1970-06-05 | 1976-10-05 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft Mit Beschrankter Haftung | Therapeutic piperazinylalkyl-quinazolone-(4)-derivatives |
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| US3900476A (en) * | 1973-05-17 | 1975-08-19 | Upjohn Co | 2(2'-pyrimidylamino)quinazolines and their preparation |
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| US3936453A (en) * | 1974-01-28 | 1976-02-03 | Sandoz, Inc. | 1-Substituted-2-disubstituted aminoquin azolin-4(1h)-ones |
| US4113637A (en) * | 1974-09-10 | 1978-09-12 | Institut Francais Du Petrole | Alkyl-guanidino-heterocyclic compounds, their manufacture and use as additives for fuels and lubricants |
| GB8429739D0 (en) * | 1984-11-24 | 1985-01-03 | Fbc Ltd | Fungicides |
| US5756502A (en) * | 1994-08-08 | 1998-05-26 | Warner-Lambert Company | Quinazolinone derivatives as cholyecystokinin (CCK) ligands |
| WO1997010221A1 (en) * | 1995-09-15 | 1997-03-20 | Torrey Pines Institute For Molecular Studies | Synthesis of quinazolinone libraries |
| US6258819B1 (en) * | 1999-08-05 | 2001-07-10 | Syntex (U.S.A.) Llc | Substituted 2(4-piperidyl)-4(3H)-quinazolinones and 2-(4-piperidyl)-4(3H)-azaquinazolinones |
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| AU2003262747A1 (en) * | 2002-08-21 | 2004-03-11 | Cytokinetics, Inc. | Compounds, compositions, and methods |
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| JP2007505121A (ja) * | 2003-09-08 | 2007-03-08 | 武田薬品工業株式会社 | ジペプチジルぺプチダーゼ阻害剤 |
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| WO2005041888A2 (en) * | 2003-11-03 | 2005-05-12 | Cytokinetics, Inc. | Pyrimidin-4-one compounds, compositions and methods |
| US20050148593A1 (en) * | 2003-11-07 | 2005-07-07 | Gustave Bergnes | Compounds, compositions, and methods |
| JP2007513154A (ja) * | 2003-12-08 | 2007-05-24 | サイトキネティクス・インコーポレーテッド | 化合物、組成物及び方法 |
| EA013427B1 (ru) * | 2004-03-15 | 2010-04-30 | Такеда Фармасьютикал Компани Лимитед | Ингибиторы дипептидилпептидазы |
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| EP1828192B1 (en) | 2004-12-21 | 2014-12-03 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors |
| WO2006089106A2 (en) * | 2005-02-17 | 2006-08-24 | Icos Corporation | Phosphoinositide 3-kinase inhibitors for inhibiting leukocyte accumulation |
| DE102005024017A1 (de) * | 2005-05-25 | 2006-11-30 | Merck Patent Gmbh | Chinazolinone |
| EP2073810B1 (en) * | 2006-09-13 | 2011-08-31 | Takeda Pharmaceutical Company Limited | Use of 2-6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2h-pyrimidin-1-ylmethyl-4-fluoro-benzonitrile for treating diabetes, cancer, autoimmune disorders and hiv infection |
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| US8324383B2 (en) | 2006-09-13 | 2012-12-04 | Takeda Pharmaceutical Company Limited | Methods of making polymorphs of benzoate salt of 2-[[6-[(3R)-3-amino-1-piperidinyl]-3,4-dihydro-3-methyl-2,4-dioxo-1(2H)-pyrimidinyl]methyl]-benzonitrile |
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| KR20160091440A (ko) | 2008-11-13 | 2016-08-02 | 길리아드 칼리스토가 엘엘씨 | 혈액 종양에 대한 요법 |
| US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
| CA2756347A1 (en) | 2009-03-24 | 2010-09-30 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
| SG175259A1 (en) * | 2009-04-20 | 2011-11-28 | Gilead Calistoga Llc | Methods of treatment for solid tumors |
| AU2010276160A1 (en) | 2009-07-21 | 2012-02-09 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
| WO2012140642A1 (en) | 2011-04-10 | 2012-10-18 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| EA025407B1 (ru) | 2012-03-05 | 2016-12-30 | Джилид Калистога Ллс | Полиморфная форма i (s)-2-(1-(9h-пурин-6-иламино)пропил)-5-фтор-3-фенилхиназолин-4(3h)-она |
| WO2015095605A1 (en) | 2013-12-20 | 2015-06-25 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (s) -2-(9h-purin-6-ylamino) propyl) -5-fluoro-3-phenylquinazolin-4 (3h) -one |
| NZ720867A (en) | 2013-12-20 | 2018-01-26 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
| JP6455995B2 (ja) | 2014-06-13 | 2019-01-23 | ギリアード サイエンシーズ， インコーポレイテッド | ホスファチジルイノシトール３−キナーゼ阻害剤 |
-
0
- DE DENDAT1249281D patent/DE1249281B/de active Pending
- GB GB1053063D patent/GB1053063A/en active Active
-
1963
- 1963-05-18 DE DEF39784A patent/DE1231705B/de active Pending
-
1964
- 1964-05-14 SE SE5933/64A patent/SE314074B/xx unknown
- 1964-05-14 US US367568A patent/US3322756A/en not_active Expired - Lifetime
- 1964-05-14 CH CH628164A patent/CH447181A/de unknown
- 1964-05-14 CH CH90467A patent/CH447182A/de unknown
- 1964-05-14 CH CH90567A patent/CH447183A/de unknown
- 1964-05-15 DK DK245564AA patent/DK104409C/da active
- 1964-05-15 AT AT774565A patent/AT258917B/de active
- 1964-05-15 AT AT774665A patent/AT258918B/de active
- 1964-05-15 AT AT427764A patent/AT254193B/de active
- 1964-05-15 DK DK531164AA patent/DK106039C/da active
- 1964-05-15 NL NL6405448A patent/NL6405448A/xx unknown
- 1964-05-15 DK DK531064AA patent/DK105765C/da active
- 1964-05-19 BE BE648093A patent/BE648093A/xx unknown
- 1964-08-17 FR FR985329A patent/FR3806M/fr active Active
-
1965
- 1965-11-23 SE SE1512665A patent/SE314076B/xx unknown
- 1965-11-23 SE SE1512565A patent/SE314075B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984555A (en) * | 1970-06-05 | 1976-10-05 | Byk Gulden Lomberg Chemische Fabrik Gesellschaft Mit Beschrankter Haftung | Therapeutic piperazinylalkyl-quinazolone-(4)-derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| CH447181A (de) | 1967-11-30 |
| CH447182A (de) | 1967-11-30 |
| SE314076B (en:Method) | 1969-09-01 |
| AT258918B (de) | 1967-12-27 |
| DK104409C (da) | 1966-05-16 |
| SE314075B (en:Method) | 1969-09-01 |
| US3322756A (en) | 1967-05-30 |
| BE648093A (en:Method) | 1964-11-19 |
| DK105765C (da) | 1966-11-07 |
| NL6405448A (en:Method) | 1964-11-19 |
| GB1053063A (en:Method) | |
| AT258917B (de) | 1967-12-27 |
| DK106039C (da) | 1966-12-12 |
| DE1249281B (en:Method) | |
| FR3806M (fr) | 1966-01-03 |
| CH447183A (de) | 1967-11-30 |
| SE314074B (en:Method) | 1969-09-01 |
| AT254193B (de) | 1967-05-10 |
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