NO763569L - - Google Patents

Info

Publication number: NO763569L
Authority: NO; Norway
Prior art keywords: mono; substituted; tri; halogen; phenylalkyl
Prior art date: 1975-10-28

Application number

NO763569A

Other languages

English (en)

Norwegian (no)

Inventor

A D Miller

Original Assignee

Ici America Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-10-28

Filing date

1976-10-19

Publication date

1977-04-29

1976-10-19 Application filed by Ici America Inc filed Critical Ici America Inc

1977-04-29 Publication of NO763569L publication Critical patent/NO763569L/no

Links

-1 carboxy- Chemical class 0.000 claims description 136
125000003884 phenylalkyl group Chemical group 0.000 claims description 52
150000001875 compounds Chemical class 0.000 claims description 48
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
238000006467 substitution reaction Methods 0.000 claims description 36
238000000034 method Methods 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 27
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
150000003254 radicals Chemical class 0.000 claims description 26
150000002367 halogens Chemical group 0.000 claims description 21
125000000217 alkyl group Chemical group 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 14
150000001540 azides Chemical class 0.000 claims description 10
150000003852 triazoles Chemical group 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
125000001188 haloalkyl group Chemical group 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
238000006114 decarboxylation reaction Methods 0.000 claims description 5
230000009467 reduction Effects 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000004965 peroxy acids Chemical class 0.000 claims description 4
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
229940042055 systemic antimycotics triazole derivative Drugs 0.000 claims description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
125000003236 benzoyl group Chemical class [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
230000007062 hydrolysis Effects 0.000 claims description 3
238000006460 hydrolysis reaction Methods 0.000 claims description 3
229910052740 iodine Inorganic materials 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
230000003647 oxidation Effects 0.000 claims description 3
238000007254 oxidation reaction Methods 0.000 claims description 3
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000000490 cinnamyl group Chemical class C(C=CC1=CC=CC=C1)* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical class C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
150000002118 epoxides Chemical class 0.000 claims description 2
ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000001326 naphthylalkyl group Chemical class 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
125000000547 substituted alkyl group Chemical group 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 203
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
239000007787 solid Substances 0.000 description 74
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
239000011541 reaction mixture Substances 0.000 description 52
239000000243 solution Substances 0.000 description 50
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 38
239000000706 filtrate Substances 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
239000000203 mixture Substances 0.000 description 28
238000010992 reflux Methods 0.000 description 28
239000007788 liquid Substances 0.000 description 26
239000002904 solvent Substances 0.000 description 25
UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 23
239000000047 product Substances 0.000 description 22
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 21
238000010438 heat treatment Methods 0.000 description 20
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 16
239000003085 diluting agent Substances 0.000 description 16
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 15
239000000377 silicon dioxide Substances 0.000 description 15
238000009835 boiling Methods 0.000 description 14
239000007858 starting material Substances 0.000 description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
239000011521 glass Substances 0.000 description 12
239000010410 layer Substances 0.000 description 12
239000003921 oil Substances 0.000 description 11
238000001953 recrystallisation Methods 0.000 description 10
JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 10
239000011780 sodium chloride Substances 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
241000699670 Mus sp. Species 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003814 drug Substances 0.000 description 9
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
241001465754 Metazoa Species 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
238000001816 cooling Methods 0.000 description 8
229940079593 drug Drugs 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
238000004587 chromatography analysis Methods 0.000 description 7
239000000463 material Substances 0.000 description 7
239000012044 organic layer Substances 0.000 description 7
235000012239 silicon dioxide Nutrition 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
FQSQOBFYKBWRMN-UHFFFAOYSA-N 1-(1-azidoethyl)-2-chlorobenzene Chemical compound [N-]=[N+]=NC(C)C1=CC=CC=C1Cl FQSQOBFYKBWRMN-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
230000016571 aggressive behavior Effects 0.000 description 6
239000003480 eluent Substances 0.000 description 6
239000003826 tablet Substances 0.000 description 6
230000037396 body weight Effects 0.000 description 5
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 5
239000002274 desiccant Substances 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
BOSNISRGGXSMHE-UHFFFAOYSA-N 1-(azidomethyl)-2-chlorobenzene Chemical compound ClC1=CC=CC=C1CN=[N+]=[N-] BOSNISRGGXSMHE-UHFFFAOYSA-N 0.000 description 4
ZRKPADHLWARFKN-UHFFFAOYSA-N 1-[(2-chlorophenyl)methyl]triazole Chemical compound ClC1=CC=CC=C1CN1N=NC=C1 ZRKPADHLWARFKN-UHFFFAOYSA-N 0.000 description 4
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 4
DQQNMIPXXNPGCV-UHFFFAOYSA-N 3-hexyne Chemical compound CCC#CCC DQQNMIPXXNPGCV-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
206010044565 Tremor Diseases 0.000 description 4
239000002775 capsule Substances 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
239000012535 impurity Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
230000004044 response Effects 0.000 description 4
230000001624 sedative effect Effects 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
238000003756 stirring Methods 0.000 description 4
239000000829 suppository Substances 0.000 description 4
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 description 3
DWRFKDJJQBRVMU-UHFFFAOYSA-N 1-(3-phenylpropyl)triazole-4,5-dicarboxylic acid Chemical compound OC(=O)C1=C(C(=O)O)N=NN1CCCC1=CC=CC=C1 DWRFKDJJQBRVMU-UHFFFAOYSA-N 0.000 description 3
206010001488 Aggression Diseases 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
208000012761 aggressive behavior Diseases 0.000 description 3
229940025084 amphetamine Drugs 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
238000003776 cleavage reaction Methods 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000004821 distillation Methods 0.000 description 3
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
239000004615 ingredient Substances 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
230000008569 process Effects 0.000 description 3
230000007017 scission Effects 0.000 description 3
230000035939 shock Effects 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
238000000859 sublimation Methods 0.000 description 3
230000008022 sublimation Effects 0.000 description 3
231100000820 toxicity test Toxicity 0.000 description 3
TVPJIIDMJBXAKJ-UHFFFAOYSA-N (2-acetyloxyphenyl)methyl-diazonioazanide Chemical compound CC(=O)OC1=CC=CC=C1CN=[N+]=[N-] TVPJIIDMJBXAKJ-UHFFFAOYSA-N 0.000 description 2
QMWHENPTTCYSCU-UHFFFAOYSA-N 1-[(2,3,6-trichlorophenyl)methyl]triazole Chemical compound ClC1=CC=C(Cl)C(CN2N=NC=C2)=C1Cl QMWHENPTTCYSCU-UHFFFAOYSA-N 0.000 description 2
COMGWFIHYRYSIO-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]triazole Chemical compound ClC1=CC=CC(Cl)=C1CN1N=NC=C1 COMGWFIHYRYSIO-UHFFFAOYSA-N 0.000 description 2
JEIXSOAGVIALIH-UHFFFAOYSA-N 1-[(2-iodophenyl)methyl]triazole Chemical compound IC1=CC=CC=C1CN1N=NC=C1 JEIXSOAGVIALIH-UHFFFAOYSA-N 0.000 description 2
CCYJJHRBIZJRRE-UHFFFAOYSA-N 1-[(3-bromophenyl)methyl]triazole Chemical compound BrC1=CC=CC(CN2N=NC=C2)=C1 CCYJJHRBIZJRRE-UHFFFAOYSA-N 0.000 description 2
GTNKGWCGZVQBGT-UHFFFAOYSA-N 1-chloro-2-(1-chloroethyl)benzene Chemical compound CC(Cl)C1=CC=CC=C1Cl GTNKGWCGZVQBGT-UHFFFAOYSA-N 0.000 description 2
QBRMMEUVTDBRHO-UHFFFAOYSA-N 1-hexyltriazole Chemical compound CCCCCCN1C=CN=N1 QBRMMEUVTDBRHO-UHFFFAOYSA-N 0.000 description 2
SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 2
LQGGVJAWOVGZIK-UHFFFAOYSA-N 2-(triazol-1-ylmethyl)phenol Chemical compound OC1=CC=CC=C1CN1N=NC=C1 LQGGVJAWOVGZIK-UHFFFAOYSA-N 0.000 description 2
SNSAJNZHXPUUGX-UHFFFAOYSA-N 2-[(4-bromophenyl)methyl]triazole Chemical compound C1=CC(Br)=CC=C1CN1N=CC=N1 SNSAJNZHXPUUGX-UHFFFAOYSA-N 0.000 description 2
BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 2
HMWVTNAPDLFAKS-UHFFFAOYSA-N 3-(2-azidoethyl)-1h-indole Chemical compound C1=CC=C2C(CCN=[N+]=[N-])=CNC2=C1 HMWVTNAPDLFAKS-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
BDRNYOMANBZFHL-UHFFFAOYSA-N [3-(bromomethyl)-4-chlorophenyl] acetate Chemical compound CC(=O)OC1=CC=C(Cl)C(CBr)=C1 BDRNYOMANBZFHL-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
235000011089 carbon dioxide Nutrition 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
125000006286 dichlorobenzyl group Chemical group 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
238000004090 dissolution Methods 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
239000008187 granular material Substances 0.000 description 2
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 2
238000002329 infrared spectrum Methods 0.000 description 2
239000007928 intraperitoneal injection Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
AMZORBZSQRUXNC-UHFFFAOYSA-N o-Tolyl acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 description 2
125000004344 phenylpropyl group Chemical group 0.000 description 2
UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 2
238000000746 purification Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012265 solid product Substances 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
235000020357 syrup Nutrition 0.000 description 2
239000006188 syrup Substances 0.000 description 2
238000001665 trituration Methods 0.000 description 2
238000002061 vacuum sublimation Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
LKKDOFSIQKPJLX-UHFFFAOYSA-N (4-chloro-3-methylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(Cl)C(C)=C1 LKKDOFSIQKPJLX-UHFFFAOYSA-N 0.000 description 1
150000000177 1,2,3-triazoles Chemical class 0.000 description 1
YZIFVWOCPGPNHB-UHFFFAOYSA-N 1,2-dichloro-4-(chloromethyl)benzene Chemical compound ClCC1=CC=C(Cl)C(Cl)=C1 YZIFVWOCPGPNHB-UHFFFAOYSA-N 0.000 description 1
NTSJGNVMDZAPJE-UHFFFAOYSA-N 1,2-dihydrotriazine Chemical compound N1NN=CC=C1 NTSJGNVMDZAPJE-UHFFFAOYSA-N 0.000 description 1
LBOBESSDSGODDD-UHFFFAOYSA-N 1,3-dichloro-2-(chloromethyl)benzene Chemical compound ClCC1=C(Cl)C=CC=C1Cl LBOBESSDSGODDD-UHFFFAOYSA-N 0.000 description 1
YRMNJICXVAFKAM-UHFFFAOYSA-N 1-(1-phenylethyl)triazole Chemical compound C1=CN=NN1C(C)C1=CC=CC=C1 YRMNJICXVAFKAM-UHFFFAOYSA-N 0.000 description 1
RHHWCAOVTWEDLM-UHFFFAOYSA-N 1-(2-chlorophenyl)triazole Chemical compound ClC1=CC=CC=C1N1N=NC=C1 RHHWCAOVTWEDLM-UHFFFAOYSA-N 0.000 description 1
TXVVVEUSVBLDED-UHFFFAOYSA-N 1-(bromomethyl)-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1CBr TXVVVEUSVBLDED-UHFFFAOYSA-N 0.000 description 1
GQFITODJWOIYPF-UHFFFAOYSA-N 1-(bromomethyl)-2-iodobenzene Chemical compound BrCC1=CC=CC=C1I GQFITODJWOIYPF-UHFFFAOYSA-N 0.000 description 1
LZBOHNCMCCSTJX-UHFFFAOYSA-N 1-(chloromethyl)-3-methylbenzene Chemical compound CC1=CC=CC(CCl)=C1 LZBOHNCMCCSTJX-UHFFFAOYSA-N 0.000 description 1
APGGSERFJKEWFG-UHFFFAOYSA-N 1-(chloromethyl)-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(CCl)=C1 APGGSERFJKEWFG-UHFFFAOYSA-N 0.000 description 1
YMXAYMSJCVGYEM-UHFFFAOYSA-N 1-Chloro-2-(chlorophenylmethyl)benzene Chemical compound C=1C=CC=C(Cl)C=1C(Cl)C1=CC=CC=C1 YMXAYMSJCVGYEM-UHFFFAOYSA-N 0.000 description 1
SQPKESMBCPOCIX-UHFFFAOYSA-N 1-[(2,6-dichlorophenyl)methyl]benzotriazole Chemical compound ClC1=CC=CC(Cl)=C1CN1C2=CC=CC=C2N=N1 SQPKESMBCPOCIX-UHFFFAOYSA-N 0.000 description 1
XCRWSJGCCFNKLD-UHFFFAOYSA-N 1-[(2-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC=C1CN1N=NC=C1 XCRWSJGCCFNKLD-UHFFFAOYSA-N 0.000 description 1
ARUSLMZOQGUENW-UHFFFAOYSA-N 1-[(3-methylphenyl)methyl]triazole Chemical compound CC1=CC=CC(CN2N=NC=C2)=C1 ARUSLMZOQGUENW-UHFFFAOYSA-N 0.000 description 1
IZVYBOAHMLOLBO-UHFFFAOYSA-N 1-[(3-nitrophenyl)methyl]triazole Chemical compound [O-][N+](=O)C1=CC=CC(CN2N=NC=C2)=C1 IZVYBOAHMLOLBO-UHFFFAOYSA-N 0.000 description 1
RRAMJZQFVIUTOQ-UHFFFAOYSA-N 1-[(4-chlorophenyl)methyl]triazole Chemical compound C1=CC(Cl)=CC=C1CN1N=NC=C1 RRAMJZQFVIUTOQ-UHFFFAOYSA-N 0.000 description 1
IOJRXKFGYUFTLK-UHFFFAOYSA-N 1-[[4-(trifluoromethyl)phenyl]methyl]triazole Chemical compound C1=CC(C(F)(F)F)=CC=C1CN1N=NC=C1 IOJRXKFGYUFTLK-UHFFFAOYSA-N 0.000 description 1
KOFFFKMEMKRWMT-UHFFFAOYSA-N 1-azidoethylbenzene Chemical compound [N-]=[N+]=NC(C)C1=CC=CC=C1 KOFFFKMEMKRWMT-UHFFFAOYSA-N 0.000 description 1
JAZPHKNDCIRCFX-UHFFFAOYSA-N 1-chloro-2-(3-chloroprop-1-enyl)benzene Chemical compound ClCC=CC1=CC=CC=C1Cl JAZPHKNDCIRCFX-UHFFFAOYSA-N 0.000 description 1
WCUGHCKAMJUCNH-UHFFFAOYSA-N 2-(azidomethyl)-1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C(CN=[N+]=[N-])=C1 WCUGHCKAMJUCNH-UHFFFAOYSA-N 0.000 description 1
JPMRGPPMXHGKRO-UHFFFAOYSA-N 2-(chloromethyl)pyridine hydrochloride Chemical compound Cl.ClCC1=CC=CC=N1 JPMRGPPMXHGKRO-UHFFFAOYSA-N 0.000 description 1
FUOHKPSBGLXIRL-UHFFFAOYSA-N 2-(chloromethyl)thiophene Chemical compound ClCC1=CC=CS1 FUOHKPSBGLXIRL-UHFFFAOYSA-N 0.000 description 1
PXKNAYJTZSJABW-UHFFFAOYSA-N 2-(triazol-1-yl)aniline Chemical compound NC1=CC=CC=C1N1N=NC=C1 PXKNAYJTZSJABW-UHFFFAOYSA-N 0.000 description 1
TXCAVMYJGYCFAK-UHFFFAOYSA-N 2-(triazol-2-ylmethyl)pyridine Chemical compound N1=CC=NN1CC1=CC=CC=N1 TXCAVMYJGYCFAK-UHFFFAOYSA-N 0.000 description 1
OWUUOJBKIIEHTJ-UHFFFAOYSA-N 2-[2-(bromomethyl)phenyl]acetic acid Chemical compound OC(=O)CC1=CC=CC=C1CBr OWUUOJBKIIEHTJ-UHFFFAOYSA-N 0.000 description 1
NDVCLYDTNQHQHQ-UHFFFAOYSA-N 2-[[2-(trifluoromethyl)phenyl]methyl]triazole Chemical compound FC(F)(F)C1=CC=CC=C1CN1N=CC=N1 NDVCLYDTNQHQHQ-UHFFFAOYSA-N 0.000 description 1
125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-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
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical compound BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
TZFOEYRGARRRGO-UHFFFAOYSA-N 2h-triazole-4,5-dicarboxylic acid Chemical compound OC(=O)C1=NNN=C1C(O)=O TZFOEYRGARRRGO-UHFFFAOYSA-N 0.000 description 1
JRASUUTVFCLPPO-UHFFFAOYSA-N 3-(2-chloroethyl)-1h-indole Chemical compound C1=CC=C2C(CCCl)=CNC2=C1 JRASUUTVFCLPPO-UHFFFAOYSA-N 0.000 description 1
KIBQFRHORJLKHM-UHFFFAOYSA-N 3-[2-(triazol-1-yl)ethyl]-1h-indole Chemical compound C=1NC2=CC=CC=C2C=1CCN1C=CN=N1 KIBQFRHORJLKHM-UHFFFAOYSA-N 0.000 description 1
FWMBBQJILJGRRI-UHFFFAOYSA-N 3-azidopropylbenzene Chemical compound [N-]=[N+]=NCCCC1=CC=CC=C1 FWMBBQJILJGRRI-UHFFFAOYSA-N 0.000 description 1
125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 description 1
ANLQHFYDQPMDJY-UHFFFAOYSA-N 3-oxo-3-piperidin-1-ylpropanenitrile Chemical compound N#CCC(=O)N1CCCCC1 ANLQHFYDQPMDJY-UHFFFAOYSA-N 0.000 description 1
125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 description 1
IAAUGSYGHOFWEW-UHFFFAOYSA-N 8-(bromomethyl)quinoline Chemical compound C1=CN=C2C(CBr)=CC=CC2=C1 IAAUGSYGHOFWEW-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
240000001592 Amaranthus caudatus Species 0.000 description 1
235000009328 Amaranthus caudatus Nutrition 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 1
229920005372 Plexiglas® Polymers 0.000 description 1
244000007021 Prunus avium Species 0.000 description 1
235000010401 Prunus avium Nutrition 0.000 description 1
235000014441 Prunus serotina Nutrition 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
RHZMCEFGRRLLAP-UHFFFAOYSA-N [2-(bromomethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1CBr RHZMCEFGRRLLAP-UHFFFAOYSA-N 0.000 description 1
QGRSHNKPXCGFFD-UHFFFAOYSA-N [5-amino-1-[(2-chlorophenyl)methyl]triazol-4-yl]-piperidin-1-ylmethanone Chemical compound NC1=C(N=NN1CC1=C(C=CC=C1)Cl)C(=O)N1CCCCC1 QGRSHNKPXCGFFD-UHFFFAOYSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
235000012735 amaranth Nutrition 0.000 description 1
239000004178 amaranth Substances 0.000 description 1
229940008238 amphetamine sulfate Drugs 0.000 description 1
PYHRZPFZZDCOPH-UHFFFAOYSA-N amphetamine sulfate Chemical compound OS(O)(=O)=O.CC(N)CC1=CC=CC=C1.CC(N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-UHFFFAOYSA-N 0.000 description 1
238000010171 animal model Methods 0.000 description 1
WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
LSOBPYSQSPIQJF-UHFFFAOYSA-N but-2-yne Chemical compound [CH2]C#CC LSOBPYSQSPIQJF-UHFFFAOYSA-N 0.000 description 1
DLDJFQGPPSQZKI-UHFFFAOYSA-N but-2-yne-1,4-diol Chemical compound OCC#CCO DLDJFQGPPSQZKI-UHFFFAOYSA-N 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
125000004803 chlorobenzyl group Chemical group 0.000 description 1
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000013058 crude material Substances 0.000 description 1
125000002946 cyanobenzyl group Chemical group 0.000 description 1
JEVCWSUVFOYBFI-UHFFFAOYSA-N cyanyl Chemical compound N#[C] JEVCWSUVFOYBFI-UHFFFAOYSA-N 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000001514 detection method Methods 0.000 description 1
NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
XNMQEEKYCVKGBD-UHFFFAOYSA-N dimethylacetylene Natural products CC#CC XNMQEEKYCVKGBD-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-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
UCSVJZQSZZAKLD-UHFFFAOYSA-N ethyl azide Chemical compound CCN=[N+]=[N-] UCSVJZQSZZAKLD-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
IYWCBYFJFZCCGV-UHFFFAOYSA-N formamide;hydrate Chemical compound O.NC=O IYWCBYFJFZCCGV-UHFFFAOYSA-N 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
239000005457 ice water Substances 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
239000007972 injectable composition Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
QKASDIPENBEWBU-UHFFFAOYSA-N methyl 2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CBr QKASDIPENBEWBU-UHFFFAOYSA-N 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
229920001778 nylon Polymers 0.000 description 1
239000004533 oil dispersion Substances 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012047 saturated solution Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
UYXAHRLPUPVSNJ-UHFFFAOYSA-N sodium;2h-triazole Chemical compound [Na].C=1C=NNN=1 UYXAHRLPUPVSNJ-UHFFFAOYSA-N 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
241000894007 species Species 0.000 description 1
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
230000007704 transition Effects 0.000 description 1
125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
230000007306 turnover Effects 0.000 description 1
238000005292 vacuum distillation Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- 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
- 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
- C07D249/04—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles
- C07D249/06—1,2,3-Triazoles; Hydrogenated 1,2,3-triazoles with aryl radicals directly attached to ring atoms
- 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
- C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
- C07D249/18—Benzotriazoles

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Anesthesiology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biomedical Technology (AREA)
Pharmacology & Pharmacy (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO763569A 1975-10-28 1976-10-19 NO763569L (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US62614075A	1975-10-28	1975-10-28

Publications (1)

Publication Number	Publication Date
NO763569L true NO763569L (fr)	1977-04-29

Family

ID=24509116

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO763569A NO763569L (fr)	1975-10-28	1976-10-19

Country Status (12)

Country	Link
JP (1)	JPS5253863A (fr)
AU (1)	AU1881176A (fr)
BE (1)	BE847480A (fr)
DE (1)	DE2648826A1 (fr)
DK (1)	DK478176A (fr)
FI (1)	FI763050A7 (fr)
FR (1)	FR2329275A1 (fr)
IL (1)	IL50699A0 (fr)
LU (1)	LU76062A1 (fr)
NL (1)	NL7611944A (fr)
NO (1)	NO763569L (fr)
SE (1)	SE7611884L (fr)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FI834666A7 (fi) *	1982-12-23	1984-06-24	Ciba Geigy Ag	Foerfarande foer framstaellning av nya aralkyltriazolfoereningar.
US4801594A (en) *	1984-06-18	1989-01-31	Eli Lilly And Company	Aromatase inhibitors
CA2015267A1 (fr) *	1989-05-26	1990-11-26	Rainer Seele	8-azolylmethylquinolines
DK1501809T3 (da)	2002-04-26	2008-05-13	Lilly Co Eli	Trizolderivater som tachykininreceptorantagonister
JP4895476B2 (ja)	2002-04-26	2012-03-14	イーライリリーアンドカンパニー	タキキニン受容体アンタゴニスト
US20060160794A1 (en) *	2003-06-12	2006-07-20	Amegadzie Albert K	Tachykinin receptor antagonists
CA3085116C (fr)	2012-01-26	2022-07-19	Vanda Pharmaceuticals Inc.	Traitement de troubles du rythme circadien
US11918557B2 (en)	2012-01-26	2024-03-05	Vanda Pharmaceuticals Inc.	Treatment of circadian rhythm disorders
KR102148990B1 (ko)	2012-12-18	2020-08-27	반다 파마슈티칼즈, 인코퍼레이티드.	일주기 리듬 장애의 치료
US10376487B2 (en)	2013-11-12	2019-08-13	Vanda Pharmaceuticals Inc.	Method of treatment
US11090285B2 (en)	2013-11-12	2021-08-17	Vanda Pharmaceuticals Inc	Treatment of circadian rhythm disorders
CN107406420B (zh)	2015-01-30	2020-11-06	纽罗克里生物科学有限公司	取代的三唑及与其相关的方法
US9771335B2 (en) *	2015-07-31	2017-09-26	The Johns Hopkins University	Derivatives of rufinamide and their use in inhibtion of the activation of human voltage-gated sodium channels
CN105801499A (zh) *	2016-04-15	2016-07-27	华东理工大学	烯酮制备新型有机oled试剂的设计及其应用
CN111196785B (zh) *	2020-01-21	2021-08-31	成都新朝阳作物科学股份有限公司	三氮唑衍生物及其制备方法和用途

1976
- 1976-10-18 IL IL50699A patent/IL50699A0/xx unknown
- 1976-10-19 AU AU18811/76A patent/AU1881176A/en not_active Expired
- 1976-10-19 NO NO763569A patent/NO763569L/no unknown
- 1976-10-20 BE BE171671A patent/BE847480A/fr unknown
- 1976-10-22 DK DK478176A patent/DK478176A/da unknown
- 1976-10-25 LU LU76062A patent/LU76062A1/xx unknown
- 1976-10-25 JP JP51128163A patent/JPS5253863A/ja active Pending
- 1976-10-25 FR FR7632136A patent/FR2329275A1/fr active Granted
- 1976-10-26 FI FI763050A patent/FI763050A7/fi not_active Application Discontinuation
- 1976-10-26 SE SE7611884A patent/SE7611884L/xx not_active Application Discontinuation
- 1976-10-27 DE DE19762648826 patent/DE2648826A1/de active Pending
- 1976-10-28 NL NL7611944A patent/NL7611944A/xx not_active Application Discontinuation

Also Published As

Publication number	Publication date
FI763050A7 (fr)	1977-04-29
DE2648826A1 (de)	1977-05-05
LU76062A1 (fr)	1977-05-18
FR2329275B1 (fr)	1978-12-15
AU1881176A (en)	1978-04-27
DK478176A (da)	1977-04-29
FR2329275A1 (fr)	1977-05-27
IL50699A0 (en)	1976-12-31
JPS5253863A (en)	1977-04-30
SE7611884L (sv)	1977-04-29
NL7611944A (nl)	1977-05-02
BE847480A (fr)	1977-04-20

Publication	Publication Date	Title
RU2114838C1 (ru)	1998-07-10	Триазольные производные, фармацевтическая композиция и промежуточные продукты
AU602638B2 (en)	1990-10-18	Triazole antifungal agents
EP0721455B9 (fr)	2005-04-20	Tetrahydropyridine-(ou 4-hydroxypiperidine) alkylazoles ayant une activite pour les recepteurs sigma et/ou 5ht1a
US4402968A (en)	1983-09-06	Antifungal benzofuranyl imidazole compounds
US4814344A (en)	1989-03-21	Indole derivatives
US5541203A (en)	1996-07-30	Triazole antifungal agents
NO156128B (no)	1987-04-21	Analogifremgangsmaate til fremstilling av et terapeutisk aktivt 1,3-bis-triazolyl-2-propanol derivat.
NO136793B (no)	1977-08-01	Analogifremgangsm}te til fremstilling av terapeutisk virksomme substituerte 1,2,4-triazolderivater.
NO176143B (no)	1994-10-31	Analogifremgangsmåte for fremstilling av terapeutisk aktive 3-[4(1-substituert 4-piperazinyl)butylÅ-4-tiazlidinoner
NO793674L (no)	1980-05-28	Hydroksyetyl-azoler, fremgangsmaate til deres fremstilling samt deres anvendelse som legemiddel
US4616026A (en)	1986-10-07	Antifungal 2-aryl-1,1-difluoro-3-(1H-1,2,4-triazol-1-yl)2-propanols
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DD213211A5 (de)	1984-09-05	Verfahren zur herstellung psychotherapeutisch wirksamer 1-phenyl-2(1h,3h)-indolone
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