DK141727B - Analogifremgangsmåde til fremstilling af triazolobenzodiazepinderivater, eller farmaceutisk acceptable syreadditionssalte deraf. - Google Patents

Analogifremgangsmåde til fremstilling af triazolobenzodiazepinderivater, eller farmaceutisk acceptable syreadditionssalte deraf. Download PDF

Info

Publication number: DK141727B
Authority: DK; Denmark
Prior art keywords: compound; group; ethanol; ethyl; parts
Prior art date: 1973-02-19

Application number

DK79874AA

Other languages

Danish (da)

English (en)

Other versions

DK141727C (cs

Inventor

Kanji Meguro

Hiroyuki Tawada

Yutaka Kuwada

Original Assignee

Takeda Chemical Industries Ltd

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.)

1973-02-19

Filing date

1974-02-15

Publication date

1980-06-02

1974-02-15 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1980-06-02 Publication of DK141727B publication Critical patent/DK141727B/da

1980-10-27 Application granted granted Critical

1980-10-27 Publication of DK141727C publication Critical patent/DK141727C/da

Links

238000000034 method Methods 0.000 title claims description 20
239000002253 acid Substances 0.000 title claims description 12
150000003839 salts Chemical class 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 7
KYTREVLPRJOBEM-UHFFFAOYSA-N triazolo[4,5-i][1,2]benzodiazepine Chemical class C1=CC2=CC=CN=NC2=C2C1=NN=N2 KYTREVLPRJOBEM-UHFFFAOYSA-N 0.000 title claims description 4
150000001875 compounds Chemical class 0.000 claims description 73
-1 4-methyl-piperazinyl group Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 16
125000003545 alkoxy group Chemical group 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
IUHFWCGCSVTMPG-UHFFFAOYSA-N [C].[C] Chemical group [C].[C] IUHFWCGCSVTMPG-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 94
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 66
238000001953 recrystallisation Methods 0.000 description 36
239000002904 solvent Substances 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 26
239000013078 crystal Substances 0.000 description 24
239000000203 mixture Substances 0.000 description 24
235000019439 ethyl acetate Nutrition 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
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 description 13
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
150000001989 diazonium salts Chemical class 0.000 description 10
238000003756 stirring Methods 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
238000001816 cooling Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
229940031098 ethanolamine Drugs 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
238000001914 filtration Methods 0.000 description 6
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000001999 4-Methoxybenzoyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C(*)=O 0.000 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
230000001773 anti-convulsant effect Effects 0.000 description 5
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 5
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
239000012954 diazonium Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
239000007858 starting material Substances 0.000 description 5
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000001961 anticonvulsive agent Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
230000008602 contraction Effects 0.000 description 4
230000000694 effects Effects 0.000 description 4
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
239000000126 substance Substances 0.000 description 4
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
229960003965 antiepileptics Drugs 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
125000004122 cyclic group Chemical group 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
235000011056 potassium acetate Nutrition 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 2
SOYOCBJBBPMAQW-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 SOYOCBJBBPMAQW-UHFFFAOYSA-N 0.000 description 2
BDMLDWKLIAIPFN-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 BDMLDWKLIAIPFN-UHFFFAOYSA-N 0.000 description 2
WWOQTUNOMFBNDS-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-n-(2-hydroxyethyl)-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)NCCO)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WWOQTUNOMFBNDS-UHFFFAOYSA-N 0.000 description 2
VRTWPIHMODRFDS-UHFFFAOYSA-N 1-(2-benzoyl-4-methylphenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxamide Chemical compound C=1C(C)=CC=C(N2C(=NC(=N2)C(N)=O)CCl)C=1C(=O)C1=CC=CC=C1 VRTWPIHMODRFDS-UHFFFAOYSA-N 0.000 description 2
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical group CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 2
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
MJAXYZXQWWPJTF-UHFFFAOYSA-N ethyl 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 MJAXYZXQWWPJTF-UHFFFAOYSA-N 0.000 description 2
RYRALQYIMXDQBX-UHFFFAOYSA-N ethyl 2-[(2-benzoylphenyl)diazenyl]-2-chloroacetate Chemical compound CCOC(=O)C(Cl)N=NC1=CC=CC=C1C(=O)C1=CC=CC=C1 RYRALQYIMXDQBX-UHFFFAOYSA-N 0.000 description 2
PQWDDWRCEARMMC-UHFFFAOYSA-N ethyl 2-amino-2-[(2-benzoyl-4-chlorophenyl)diazenyl]acetate Chemical compound CCOC(=O)C(N)N=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 PQWDDWRCEARMMC-UHFFFAOYSA-N 0.000 description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
239000011630 iodine Substances 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
CQDGTJPVBWZJAZ-UHFFFAOYSA-N monoethyl carbonate Chemical compound CCOC(O)=O CQDGTJPVBWZJAZ-UHFFFAOYSA-N 0.000 description 2
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 2
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
239000000932 sedative agent Substances 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
241000894007 species Species 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
KWZYIAJRFJVQDO-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-chlorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl KWZYIAJRFJVQDO-UHFFFAOYSA-N 0.000 description 1
RXXPCWGVBLUFMF-UHFFFAOYSA-N (2-chloroacetyl) 2-aminoacetate Chemical compound NCC(=O)OC(=O)CCl RXXPCWGVBLUFMF-UHFFFAOYSA-N 0.000 description 1
ZEWJFUNFEABPGL-UHFFFAOYSA-N 1,2,4-triazole-3-carboxamide Chemical compound NC(=O)C=1N=CNN=1 ZEWJFUNFEABPGL-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
YPSLFRWHWICYGR-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-n,n-dimethyl-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N(C)C)N=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 YPSLFRWHWICYGR-UHFFFAOYSA-N 0.000 description 1
DOVAKSGIMSPSDW-UHFFFAOYSA-N 1-(2-benzoylphenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(CCl)N1C1=CC=CC=C1C(=O)C1=CC=CC=C1 DOVAKSGIMSPSDW-UHFFFAOYSA-N 0.000 description 1
MLKUHRRRGDIXQO-UHFFFAOYSA-N 1-[4-chloro-2-(4-methoxybenzoyl)phenyl]-5-(chloromethyl)-1,2,4-triazole-3-carboxylic acid;n,n-diethylethanamine Chemical compound CCN(CC)CC.C1=CC(OC)=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C(CCl)=NC(C(O)=O)=N1 MLKUHRRRGDIXQO-UHFFFAOYSA-N 0.000 description 1
HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
NXKGTKOENYKYPY-UHFFFAOYSA-N 1h-diazepine-7-carboxamide Chemical compound NC(=O)C1=CC=CC=NN1 NXKGTKOENYKYPY-UHFFFAOYSA-N 0.000 description 1
MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
DLDTUYIGYMNERN-UHFFFAOYSA-N 2-[(2-chloroacetyl)amino]acetic acid Chemical compound OC(=O)CNC(=O)CCl DLDTUYIGYMNERN-UHFFFAOYSA-N 0.000 description 1
VCBFAUSKNYAKJZ-UHFFFAOYSA-N 2-chloro-3-oxobutanoic acid Chemical compound CC(=O)C(Cl)C(O)=O VCBFAUSKNYAKJZ-UHFFFAOYSA-N 0.000 description 1
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
UCTNTYHJFWMUBD-UHFFFAOYSA-N 4-chloro-3-oxobutanoic acid Chemical compound OC(=O)CC(=O)CCl UCTNTYHJFWMUBD-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
DHMQDGOQFOQNFH-UHFFFAOYSA-M Aminoacetate Chemical compound NCC([O-])=O DHMQDGOQFOQNFH-UHFFFAOYSA-M 0.000 description 1
DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-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
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
LCNZUDCCDVINQV-UHFFFAOYSA-N [2-[5-(chloromethyl)-3-(4-methylpiperazine-1-carbonyl)-1,2,4-triazol-1-yl]phenyl]-phenylmethanone Chemical compound C1CN(C)CCN1C(=O)C1=NN(C=2C(=CC=CC=2)C(=O)C=2C=CC=CC=2)C(CCl)=N1 LCNZUDCCDVINQV-UHFFFAOYSA-N 0.000 description 1
FWHRUGSEKDUTDT-UHFFFAOYSA-N [5-chloro-2-[5-(chloromethyl)-3-(morpholine-4-carbonyl)-1,2,4-triazol-1-yl]phenyl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC(Cl)=CC=C1N1C(CCl)=NC(C(=O)N2CCOCC2)=N1 FWHRUGSEKDUTDT-UHFFFAOYSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000003377 acid catalyst Substances 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
230000002411 adverse Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
238000010171 animal model Methods 0.000 description 1
229940125681 anticonvulsant agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000002585 base Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
235000008429 bread Nutrition 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
KDPAWGWELVVRCH-UHFFFAOYSA-M bromoacetate Chemical compound [O-]C(=O)CBr KDPAWGWELVVRCH-UHFFFAOYSA-M 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000002775 capsule Substances 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
125000006165 cyclic alkyl group Chemical group 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
238000001514 detection method Methods 0.000 description 1
RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
XXQQUDQARDWTAK-UHFFFAOYSA-N ethyl 1-(2-benzoyl-4-methylphenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(CCl)N1C1=CC=C(C)C=C1C(=O)C1=CC=CC=C1 XXQQUDQARDWTAK-UHFFFAOYSA-N 0.000 description 1
ZNIBDCLPCAPPAC-UHFFFAOYSA-N ethyl 2-(2-benzoylphenyl)-5-(chloromethyl)-1h-1,2,4-triazole-5-carboxylate Chemical compound C1=NC(C(=O)OCC)(CCl)NN1C1=CC=CC=C1C(=O)C1=CC=CC=C1 ZNIBDCLPCAPPAC-UHFFFAOYSA-N 0.000 description 1
MCANVHHGDCRDOP-UHFFFAOYSA-N ethyl 2-[(2-benzoyl-4-chlorophenyl)diazenyl]-2-bromoacetate Chemical compound CCOC(=O)C(Br)N=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 MCANVHHGDCRDOP-UHFFFAOYSA-N 0.000 description 1
DKTMGFNJSPDNHV-UHFFFAOYSA-N ethyl 4-[(2-benzoyl-4-chlorophenyl)diazenyl]-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CN=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 DKTMGFNJSPDNHV-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000008187 granular material Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
125000002768 hydroxyalkyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
229940102253 isopropanolamine Drugs 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
231100000053 low toxicity Toxicity 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
150000002690 malonic acid derivatives Chemical class 0.000 description 1
229910001511 metal iodide Inorganic materials 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
CXHHBNMLPJOKQD-UHFFFAOYSA-N methyl hydrogen carbonate Chemical compound COC(O)=O CXHHBNMLPJOKQD-UHFFFAOYSA-N 0.000 description 1
229960005181 morphine Drugs 0.000 description 1
229960005195 morphine hydrochloride Drugs 0.000 description 1
XELXKCKNPPSFNN-BJWPBXOKSA-N morphine hydrochloride trihydrate Chemical compound O.O.O.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O XELXKCKNPPSFNN-BJWPBXOKSA-N 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
230000004526 pharmaceutical effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 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
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000002040 relaxant effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000007958 sleep Effects 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000012453 solvate Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 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
150000003852 triazoles Chemical class 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
210000001364 upper extremity Anatomy 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000008096 xylene Substances 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains three hetero rings
- C07D513/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Anesthesiology (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DK79874AA 1973-02-19 1974-02-15 Analogifremgangsmåde til fremstilling af triazolobenzodiazepinderivater, eller farmaceutisk acceptable syreadditionssalte deraf. DK141727B (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP1993073		1973-02-19
JP48019930A JPS5750797B2 (cs)	1973-02-19	1973-02-19

Publications (2)

Publication Number	Publication Date
DK141727B true DK141727B (da)	1980-06-02
DK141727C DK141727C (cs)	1980-10-27

Family

ID=12012923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK79874AA DK141727B (da)	1973-02-19	1974-02-15	Analogifremgangsmåde til fremstilling af triazolobenzodiazepinderivater, eller farmaceutisk acceptable syreadditionssalte deraf.

Country Status (15)

Country	Link
US (1)	US3947417A (cs)
JP (1)	JPS5750797B2 (cs)
AT (1)	AT336623B (cs)
BE (1)	BE811199A (cs)
CA (1)	CA1043783A (cs)
CH (1)	CH594678A5 (cs)
CS (1)	CS195269B2 (cs)
DE (1)	DE2407731A1 (cs)
DK (1)	DK141727B (cs)
FI (1)	FI56385C (cs)
FR (1)	FR2218339B1 (cs)
GB (1)	GB1424305A (cs)
HU (1)	HU168871B (cs)
NL (1)	NL7402220A (cs)
SE (1)	SE414498B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6156516A (ja) *	1984-07-23	1986-03-22	Nok Corp	アナログ・デジタル変換装置
US4596799A (en) *	1985-01-29	1986-06-24	Ciba-Geigy Corporation	9H-pyrrolo[2,1-c]-1,2,4-triazolo[4,3-a][1,4]benzodiazepines

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3755300A (en) *	1968-10-24	1973-08-28	Sankyo Co	Process for the preparation of benzodiazepine compounds
US3701782A (en) *	1972-02-10	1972-10-31	Upjohn Co	1-carbolower alkoxy - 6 - phenyl-4h-s-triazolo(1,4)benzodiazepine compounds

1973
- 1973-02-19 JP JP48019930A patent/JPS5750797B2/ja not_active Expired
1974
- 1974-02-15 CA CA192,697A patent/CA1043783A/en not_active Expired
- 1974-02-15 AT AT122274A patent/AT336623B/de not_active IP Right Cessation
- 1974-02-15 DK DK79874AA patent/DK141727B/da unknown
- 1974-02-18 BE BE141064A patent/BE811199A/xx unknown
- 1974-02-18 FR FR7405424A patent/FR2218339B1/fr not_active Expired
- 1974-02-18 NL NL7402220A patent/NL7402220A/xx not_active Application Discontinuation
- 1974-02-18 CS CS741158A patent/CS195269B2/cs unknown
- 1974-02-18 DE DE19742407731 patent/DE2407731A1/de not_active Withdrawn
- 1974-02-18 SE SE7402119A patent/SE414498B/xx unknown
- 1974-02-18 HU HUTA1291A patent/HU168871B/hu unknown
- 1974-02-19 GB GB747974A patent/GB1424305A/en not_active Expired
- 1974-02-19 CH CH230474A patent/CH594678A5/xx not_active IP Right Cessation
- 1974-02-19 FI FI476/74A patent/FI56385C/fi active
- 1974-02-19 US US05/443,528 patent/US3947417A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
FR2218339B1 (cs)	1980-01-18
DE2407731A1 (de)	1974-08-22
JPS49108099A (cs)	1974-10-14
CH594678A5 (cs)	1978-01-13
NL7402220A (cs)	1974-08-21
CS195269B2 (en)	1980-01-31
AU6554974A (en)	1975-08-14
DK141727C (cs)	1980-10-27
SE414498B (sv)	1980-08-04
FR2218339A1 (cs)	1974-09-13
US3947417A (en)	1976-03-30
HU168871B (cs)	1976-07-28
FI56385C (fi)	1980-01-10
BE811199A (fr)	1974-08-19
FI56385B (fi)	1979-09-28
JPS5750797B2 (cs)	1982-10-28
AT336623B (de)	1977-05-10
ATA122274A (de)	1976-09-15
GB1424305A (en)	1976-02-11
CA1043783A (en)	1978-12-05

Publication	Publication Date	Title
US3211731A (en)	1965-10-12	Pyrazolo-pyrimidines and process for preparing same
FI88504C (fi)	1993-05-25	Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-benzyl-1-(2H)-ftalazinonderivat
IE49993B1 (en)	1986-01-22	Pyrazoloquinolines,process for their manufacture,pharmaceutical preparations containing these compounds and their therapeutic application
DK145577B (da)	1982-12-13	Analogifremgangsmaade til fremstilling af s-triazolo(4,3-a)-(1,4)-benzodiazepiner eller 5n-oxyder eller syreadditionssalte deraf
HU178593B (en)	1982-05-28	Process for producing 3-hydroxy-6-phenyl-1,2,3,4-tetrahydro-1,5-benzodiazocine derivatives
DK143277B (da)	1981-08-03	Analogifremgangsmaade til fremstilling af s-triazolo(1,5-a)(1,4)benzodiazepinderivater eller 5-oxider eller syreadditionssalte deraf
DE2262653A1 (de)	1973-07-19	Neue 7-substituierte 3,5-dihydro-astriazino- eckige klammer auf 4,3-a eckige klammer zu eckige klammer auf 1,4 eckige klammer zu benzodiazepine, deren 6-oxyde und verfahren zu ihrer herstellung
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