TW201311B - - Google Patents

Info

Publication number

TW201311B

TW201311B TW081103807A TW81103807A TW201311B TW 201311 B TW201311 B TW 201311B TW 081103807 A TW081103807 A TW 081103807A TW 81103807 A TW81103807 A TW 81103807A TW 201311 B TW201311 B TW 201311B

Authority

TW

Taiwan

Prior art keywords

benzodiazepine

triazole

imidazole

fluoro

patent application

Prior art date

1991-06-17

Links

• Espacenet
• Global Dossier
• Discuss

• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 277
• NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 139
• -1 benzyloxy, phenoxy, pyridyloxy Chemical group 0.000 claims description 131
• 150000001875 compounds Chemical class 0.000 claims description 103
• 229940049706 benzodiazepine Drugs 0.000 claims description 88
• SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 83
• 238000000034 method Methods 0.000 claims description 72
• GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 58
• 238000006243 chemical reaction Methods 0.000 claims description 49
• 239000002253 acid Substances 0.000 claims description 41
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 34
• 229910052757 nitrogen Inorganic materials 0.000 claims description 34
• 229920006395 saturated elastomer Chemical group 0.000 claims description 34
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 150000001412 amines Chemical class 0.000 claims description 27
• 229910052799 carbon Inorganic materials 0.000 claims description 27
• 150000002923 oximes Chemical class 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 23
• 239000002585 base Substances 0.000 claims description 21
• 229910052736 halogen Inorganic materials 0.000 claims description 20
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 238000011049 filling Methods 0.000 claims description 17
• 229910052739 hydrogen Inorganic materials 0.000 claims description 17
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
• 239000001257 hydrogen Substances 0.000 claims description 14
• 125000003118 aryl group Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 230000000694 effects Effects 0.000 claims description 10
• 150000003839 salts Chemical class 0.000 claims description 10
• 239000003513 alkali Substances 0.000 claims description 9
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 9
• 150000007514 bases Chemical class 0.000 claims description 7
• 150000001557 benzodiazepines Chemical class 0.000 claims description 7
• 239000003795 chemical substances by application Substances 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 7
• 239000001301 oxygen Substances 0.000 claims description 7
• 229910052760 oxygen Inorganic materials 0.000 claims description 7
• 238000006467 substitution reaction Methods 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
• 150000001721 carbon Chemical group 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 239000013543 active substance Substances 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 5
• 125000002947 alkylene group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 230000036506 anxiety Effects 0.000 claims description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 4
• 206010029216 Nervousness Diseases 0.000 claims description 4
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
• 239000000460 chlorine Chemical group 0.000 claims description 4
• 229910052801 chlorine Chemical group 0.000 claims description 4
• 230000000698 schizophrenic effect Effects 0.000 claims description 4
• 208000019116 sleep disease Diseases 0.000 claims description 4
• 208000024891 symptom Diseases 0.000 claims description 4
• 206010012289 Dementia Diseases 0.000 claims description 3
• 241000196324 Embryophyta Species 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000011737 fluorine Chemical group 0.000 claims description 3
• 238000012856 packing Methods 0.000 claims description 3
• 229910052717 sulfur Inorganic materials 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 208000024827 Alzheimer disease Diseases 0.000 claims description 2
• 206010002091 Anaesthesia Diseases 0.000 claims description 2
• 206010010904 Convulsion Diseases 0.000 claims description 2
• 230000009471 action Effects 0.000 claims description 2
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 2
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 2
• 230000037005 anaesthesia Effects 0.000 claims description 2
• 230000008485 antagonism Effects 0.000 claims description 2
• 238000004891 communication Methods 0.000 claims description 2
• 238000005336 cracking Methods 0.000 claims description 2
• 150000002825 nitriles Chemical class 0.000 claims description 2
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
• 208000022925 sleep disturbance Diseases 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 238000002560 therapeutic procedure Methods 0.000 claims description 2
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 7
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 6
• 125000000623 heterocyclic group Chemical group 0.000 claims 5
• 208000007386 hepatic encephalopathy Diseases 0.000 claims 3
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
• 241000790917 Dioxys <bee> Species 0.000 claims 1
• 102000004300 GABA-A Receptors Human genes 0.000 claims 1
• 108090000839 GABA-A Receptors Proteins 0.000 claims 1
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
• 125000003277 amino group Chemical group 0.000 claims 1
• 125000005128 aryl amino alkyl group Chemical group 0.000 claims 1
• OKTCJUNXOQMLRW-UHFFFAOYSA-N benzene 1H-1,2-benzodiazepine Chemical compound C1=CC=CC=C1.N1N=CC=CC2=C1C=CC=C2 OKTCJUNXOQMLRW-UHFFFAOYSA-N 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• 125000004122 cyclic group Chemical group 0.000 claims 1
• CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 claims 1
• 239000003193 general anesthetic agent Substances 0.000 claims 1
• 125000002757 morpholinyl group Chemical class 0.000 claims 1
• 102000005962 receptors Human genes 0.000 claims 1
• 108020003175 receptors Proteins 0.000 claims 1
• 238000007127 saponification reaction Methods 0.000 claims 1
• 125000004434 sulfur atom Chemical group 0.000 claims 1
• 229910052714 tellurium Inorganic materials 0.000 claims 1
• PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 221
• 238000002844 melting Methods 0.000 description 181
• 230000008018 melting Effects 0.000 description 180
• 150000003852 triazoles Chemical class 0.000 description 127
• 239000000203 mixture Substances 0.000 description 125
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 123
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 110
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 106
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 105
• 239000000243 solution Substances 0.000 description 100
• 239000007864 aqueous solution Substances 0.000 description 64
• 238000003756 stirring Methods 0.000 description 55
• 239000010985 leather Substances 0.000 description 54
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 52
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 49
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
• 230000033228 biological regulation Effects 0.000 description 46
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
• 239000013078 crystal Substances 0.000 description 45
• KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 44
• 239000007789 gas Substances 0.000 description 41
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 38
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
• 240000004808 Saccharomyces cerevisiae Species 0.000 description 33
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 33
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 239000000047 product Substances 0.000 description 33
• 239000011541 reaction mixture Substances 0.000 description 33
• 239000000853 adhesive Substances 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000000284 extract Substances 0.000 description 29
• 229930192474 thiophene Natural products 0.000 description 26
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 25
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 25
• IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 24
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 24
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 24
• 235000017557 sodium bicarbonate Nutrition 0.000 description 24
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
• 239000008346 aqueous phase Substances 0.000 description 23
• VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 23
• 238000012360 testing method Methods 0.000 description 23
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 22
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 18
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 18
• 239000000706 filtrate Substances 0.000 description 17
• 239000007788 liquid Substances 0.000 description 17
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• 239000000725 suspension Substances 0.000 description 17
• 238000000354 decomposition reaction Methods 0.000 description 16
• 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 15
• 239000011734 sodium Substances 0.000 description 15
• 229910052708 sodium Inorganic materials 0.000 description 15
• GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 15
• PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 14
• 238000001914 filtration Methods 0.000 description 14
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• 239000000741 silica gel Substances 0.000 description 14
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• 238000000855 fermentation Methods 0.000 description 13
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 12
• 125000005605 benzo group Chemical group 0.000 description 12
• 239000012071 phase Substances 0.000 description 12
• 239000011780 sodium chloride Substances 0.000 description 12
• QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 12
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
• 238000000605 extraction Methods 0.000 description 11
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• DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 10
• 239000002244 precipitate Substances 0.000 description 10
• 230000008569 process Effects 0.000 description 10
• MZHUTGQZAZLFKW-UHFFFAOYSA-N 1H-1,2-benzodiazepine-3-carboxylic acid Chemical compound C1=CC(C(=O)O)=NNC2=CC=CC=C21 MZHUTGQZAZLFKW-UHFFFAOYSA-N 0.000 description 9
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 9
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• 229910052786 argon Inorganic materials 0.000 description 9
• 238000001816 cooling Methods 0.000 description 9
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• BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 8
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 8
• JOZNXHMSEPHUCI-UHFFFAOYSA-N 9h-1,2-benzodiazepine-8-carboxylic acid Chemical compound C1=CC=NN=C2CC(C(=O)O)=CC=C21 JOZNXHMSEPHUCI-UHFFFAOYSA-N 0.000 description 7
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 7
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• 239000012298 atmosphere Substances 0.000 description 7
• 238000010438 heat treatment Methods 0.000 description 7
• 238000003973 irrigation Methods 0.000 description 7
• 230000002262 irrigation Effects 0.000 description 7
• 239000011591 potassium Substances 0.000 description 7
• 229910052700 potassium Inorganic materials 0.000 description 7
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
• NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 6
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• BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
• 239000004215 Carbon black (E152) Substances 0.000 description 6
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
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• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
• 241000700159 Rattus Species 0.000 description 6
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 6
• 238000004458 analytical method Methods 0.000 description 6
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
• 230000008859 change Effects 0.000 description 6
• HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 6
• 238000002425 crystallisation Methods 0.000 description 6
• 230000008025 crystallization Effects 0.000 description 6
• 229960003750 ethyl chloride Drugs 0.000 description 6
• IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 6
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• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 6
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• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 6
• 239000002480 mineral oil Substances 0.000 description 6
• 235000010446 mineral oil Nutrition 0.000 description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
• 238000007639 printing Methods 0.000 description 6
• 235000019260 propionic acid Nutrition 0.000 description 6
• 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 6
• BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 6
• 239000002904 solvent Substances 0.000 description 6
• 239000000829 suppository Substances 0.000 description 6
• YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 5
• 239000002026 chloroform extract Substances 0.000 description 5
• 230000018044 dehydration Effects 0.000 description 5
• 238000006297 dehydration reaction Methods 0.000 description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
• WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 5
• 150000002430 hydrocarbons Chemical class 0.000 description 5
• 239000000463 material Substances 0.000 description 5
• VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 5
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