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 |
|---|---|---|---|
| DENDAT1249281D DE1249281B (US20040242566A1-20041202-C00134.png) | 1963-05-18 | ||
| GB1053063D GB1053063A (US20040242566A1-20041202-C00134.png) | 1963-05-18 | ||
| DEF39784A DE1231705B (de) | 1963-05-18 | 1963-05-18 | Verfahren zur Herstellung von 2, 3-substituierten Chinazolon-(4)-derivaten |
| US367568A US3322756A (en) | 1963-05-18 | 1964-05-14 | 2-aminoalkyl-3-hydrocarbon quinazolones-(4) |
| CH90567A CH447183A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von neuen Chinazolon-Verbindungen |
| CH90467A CH447182A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von neuen Chinazolon-Derivaten |
| SE5933/64A SE314074B (US20040242566A1-20041202-C00134.png) | 1963-05-18 | 1964-05-14 | |
| CH628164A CH447181A (de) | 1963-05-18 | 1964-05-14 | Verfahren zur Herstellung von Chinazolon-Verbindungen |
| 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 |
| 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 (US20040242566A1-20041202-C00134.png) | 1963-05-18 | 1964-05-15 | |
| DK531064AA DK105765C (da) | 1963-05-18 | 1964-05-15 | Fremgangsmåde til fremstilling af quinazolon-derivater eller syreadditionssalte deraf. |
| DK245564AA DK104409C (da) | 1963-05-18 | 1964-05-15 | Fremgangsmåde til fremstilling af quinazolonderivater eller syreadditionssalte deraf. |
| FR974901A FR1404524A (fr) | 1963-05-18 | 1964-05-19 | Nouvelles quinazolones et leur préparation |
| BE648093A BE648093A (US20040242566A1-20041202-C00134.png) | 1963-05-18 | 1964-05-19 | |
| FR985329A FR3806M (fr) | 1963-05-18 | 1964-08-17 | Médicament a base d'un dérivé de la quinazolone-(4). |
| SE1512565A SE314075B (US20040242566A1-20041202-C00134.png) | 1963-05-18 | 1965-11-23 | |
| SE1512665A SE314076B (US20040242566A1-20041202-C00134.png) | 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 (US20040242566A1-20041202-C00134.png) | 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 (US20040242566A1-20041202-C00134.png) | 1963-05-18 |
Country Status (10)
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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| GB8429739D0 (en) * | 1984-11-24 | 1985-01-03 | Fbc Ltd | Fungicides |
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| 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 |
| US6545004B1 (en) | 1999-10-27 | 2003-04-08 | Cytokinetics, Inc. | Methods and compositions utilizing quinazolinones |
| US7230000B1 (en) * | 1999-10-27 | 2007-06-12 | Cytokinetics, Incorporated | Methods and compositions utilizing quinazolinones |
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| US20040176361A1 (en) * | 2001-05-23 | 2004-09-09 | Masakazu Fujio | Fused heterocyclic compound and medicinal use thereof |
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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 |
| JP2007510652A (ja) * | 2003-11-03 | 2007-04-26 | サイトキネティクス・インコーポレーテッド | ピリミジン−４−オン化合物、組成物、および方法 |
| US20050148593A1 (en) * | 2003-11-07 | 2005-07-07 | Gustave Bergnes | Compounds, compositions, and methods |
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| JP2008500338A (ja) * | 2004-05-25 | 2008-01-10 | イコス・コーポレイション | 造血細胞の異常増殖を治療及び／又は予防する方法 |
| JP2008524331A (ja) | 2004-12-21 | 2008-07-10 | 武田薬品工業株式会社 | ジペプチジルペプチダーゼ阻害剤 |
| US20080287469A1 (en) * | 2005-02-17 | 2008-11-20 | Diacovo Thomas G | Phosphoinositide 3-Kinase Inhibitors for Inhibiting Leukocyte Accumulation |
| DE102005024017A1 (de) * | 2005-05-25 | 2006-11-30 | Merck Patent Gmbh | Chinazolinone |
| WO2007033265A1 (en) * | 2005-09-14 | 2007-03-22 | Takeda Pharmaceutical Company Limited | Dipeptidyl peptidase inhibitors for treating diabetis |
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| KR102062824B1 (ko) * | 2006-09-13 | 2020-01-07 | 다케다 야쿠힌 고교 가부시키가이샤 | 2-［6-(3-아미노-피페리딘-1-일)-3-메틸-2,4-디옥소-3,4-디하이드로-2ｈ-피리미딘-1-일메틸］-4-플루오로-벤조니트릴의 용도 |
| 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 |
| TW200838536A (en) * | 2006-11-29 | 2008-10-01 | Takeda Pharmaceutical | Polymorphs of succinate salt of 2-[6-(3-amino-piperidin-1-yl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-ylmethy]-4-fluor-benzonitrile and methods of use therefor |
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| US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
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| BRPI1012333A2 (pt) | 2009-03-24 | 2016-03-29 | Gilead Calistoga Llc | atropisômeros de derivados de 2-purinil-3-tolil-quinazolinonas e métodos de uso |
| US8546409B2 (en) * | 2009-04-20 | 2013-10-01 | Gilead Calistoga Llc | Methods of treatment for solid tumors |
| CN102647987A (zh) | 2009-07-21 | 2012-08-22 | 吉里德卡利斯托加公司 | 使用pi3k抑制剂治疗肝脏障碍 |
| CA2832822A1 (en) | 2011-04-10 | 2012-10-18 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| BR112014021935A2 (pt) | 2012-03-05 | 2019-09-24 | Gilead Calistoga Llc | formas polimórficas de (s)-2(l-(9h-purin-6-ilamino)propil)-5-fluoro-3-fenilquinazolina-4(3h)ona |
| 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 |
| BR112016028642A2 (pt) | 2014-06-13 | 2017-08-22 | Gilead Sciences Inc | composto, composição farmacêutica, método de tratamento de uma doença ou condição, método de inibição da atividade de um polipeptídeo de fosfatidilinositol 3-quinase, método de inibição de reações imunes ou crescimento excessivo ou destrutivo ou de proliferação de células cancerosas, kit, e, uso de um composto, de um sal, de um isômero ou de uma mistura farmaceuticamente aceitável do mesmo. |
-
0
- GB GB1053063D patent/GB1053063A/en active Active
- DE DENDAT1249281D patent/DE1249281B/de active Pending
-
1963
- 1963-05-18 DE DEF39784A patent/DE1231705B/de active Pending
-
1964
- 1964-05-14 CH CH90567A patent/CH447183A/de unknown
- 1964-05-14 CH CH90467A patent/CH447182A/de unknown
- 1964-05-14 US US367568A patent/US3322756A/en not_active Expired - Lifetime
- 1964-05-14 SE SE5933/64A patent/SE314074B/xx unknown
- 1964-05-14 CH CH628164A patent/CH447181A/de unknown
- 1964-05-15 AT AT427764A patent/AT254193B/de active
- 1964-05-15 AT AT774565A patent/AT258917B/de active
- 1964-05-15 DK DK531164AA patent/DK106039C/da active
- 1964-05-15 AT AT774665A patent/AT258918B/de active
- 1964-05-15 NL NL6405448A patent/NL6405448A/xx unknown
- 1964-05-15 DK DK245564AA patent/DK104409C/da active
- 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 SE1512565A patent/SE314075B/xx unknown
- 1965-11-23 SE SE1512665A patent/SE314076B/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 |
|---|---|
| AT254193B (de) | 1967-05-10 |
| GB1053063A (US20040242566A1-20041202-C00134.png) | |
| DK104409C (da) | 1966-05-16 |
| CH447182A (de) | 1967-11-30 |
| NL6405448A (US20040242566A1-20041202-C00134.png) | 1964-11-19 |
| BE648093A (US20040242566A1-20041202-C00134.png) | 1964-11-19 |
| AT258917B (de) | 1967-12-27 |
| DE1249281B (US20040242566A1-20041202-C00134.png) | |
| US3322756A (en) | 1967-05-30 |
| FR3806M (fr) | 1966-01-03 |
| SE314074B (US20040242566A1-20041202-C00134.png) | 1969-09-01 |
| AT258918B (de) | 1967-12-27 |
| CH447183A (de) | 1967-11-30 |
| SE314075B (US20040242566A1-20041202-C00134.png) | 1969-09-01 |
| DK106039C (da) | 1966-12-12 |
| SE314076B (US20040242566A1-20041202-C00134.png) | 1969-09-01 |
| CH447181A (de) | 1967-11-30 |
| DK105765C (da) | 1966-11-07 |
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