JP4205559B2 - イソインドリン誘導体 - Google Patents

イソインドリン誘導体 Download PDF

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Publication number: JP4205559B2
Authority: JP; Japan
Prior art keywords: group; dimethyl; compound; formula; carbon atoms
Prior art date: 2002-11-26
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

JP2003393809A

Other languages

English (en)

Japanese (ja)

Other versions

JP2004189733A5 (2

JP2004189733A (ja

Inventor

康平豊岡

範昌金光

昌和吉村

晴夫栗山

隆田村

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Maruishi Pharmaceutical Co Ltd

Original Assignee

Maruishi Pharmaceutical Co 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.)

2002-11-26

Filing date

2003-11-25

Publication date

2009-01-07

2003-11-25 Application filed by Maruishi Pharmaceutical Co Ltd filed Critical Maruishi Pharmaceutical Co Ltd

2003-11-25 Priority to JP2003393809A priority Critical patent/JP4205559B2/ja

2004-07-08 Publication of JP2004189733A publication Critical patent/JP2004189733A/ja

2007-01-18 Publication of JP2004189733A5 publication Critical patent/JP2004189733A5/ja

2009-01-07 Application granted granted Critical

2009-01-07 Publication of JP4205559B2 publication Critical patent/JP4205559B2/ja

2023-11-25 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical class C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 title claims description 14
150000001875 compounds Chemical class 0.000 claims description 152
-1 methylpiperazinyl Chemical group 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 43
239000000203 mixture Substances 0.000 claims description 40
125000004432 carbon atom Chemical group C* 0.000 claims description 35
230000003444 anaesthetic effect Effects 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 18
229910052717 sulfur Inorganic materials 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
239000001301 oxygen Substances 0.000 claims description 15
230000001624 sedative effect Effects 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
235000019000 fluorine Nutrition 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
239000011593 sulfur Substances 0.000 claims description 13
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
239000000932 sedative agent Substances 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
125000001153 fluoro group Chemical group F* 0.000 claims description 11
241000124008 Mammalia Species 0.000 claims description 10
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
229920006395 saturated elastomer Polymers 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 7
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
238000001990 intravenous administration Methods 0.000 claims description 7
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
125000004434 sulfur atom Chemical group 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical class 0.000 claims description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 5
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 4
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000005842 heteroatom Chemical group 0.000 claims description 3
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
229910052757 nitrogen Inorganic materials 0.000 claims description 3
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 3
239000003937 drug carrier Substances 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 114
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 54
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 50
238000005160 1H NMR spectroscopy Methods 0.000 description 43
239000000243 solution Substances 0.000 description 41
229910052799 carbon Inorganic materials 0.000 description 38
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
238000006243 chemical reaction Methods 0.000 description 26
239000000047 product Substances 0.000 description 24
239000011541 reaction mixture Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
238000010898 silica gel chromatography Methods 0.000 description 20
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
238000001914 filtration Methods 0.000 description 18
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 17
239000013078 crystal Substances 0.000 description 17
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
206010002091 Anaesthesia Diseases 0.000 description 14
230000037005 anaesthesia Effects 0.000 description 14
239000002904 solvent Substances 0.000 description 14
0 *N(C(c1cc(I)c(*)cc11)I)C1=C Chemical compound *N(C(c1cc(I)c(*)cc11)I)C1=C 0.000 description 12
238000010438 heat treatment Methods 0.000 description 12
238000000034 method Methods 0.000 description 12
238000010992 reflux Methods 0.000 description 12
GSCXPNAZEUKIRW-UHFFFAOYSA-N 2-(5,6-dimethyl-3-oxo-2-pyridin-3-yl-1h-isoindol-1-yl)acetic acid Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(CC(O)=O)N1C1=CC=CN=C1 GSCXPNAZEUKIRW-UHFFFAOYSA-N 0.000 description 11
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 10
239000007864 aqueous solution Substances 0.000 description 9
239000012300 argon atmosphere Substances 0.000 description 8
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
239000007924 injection Substances 0.000 description 8
238000002347 injection Methods 0.000 description 8
238000003756 stirring Methods 0.000 description 8
239000002253 acid Substances 0.000 description 7
238000001816 cooling Methods 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000004519 manufacturing process Methods 0.000 description 7
HGHNFTPDMNDNAT-UHFFFAOYSA-N propyl 2-(5,6-dimethyl-3-oxo-2-pyridin-3-yl-1h-isoindol-1-yl)acetate Chemical compound O=C1C2=CC(C)=C(C)C=C2C(CC(=O)OCCC)N1C1=CC=CN=C1 HGHNFTPDMNDNAT-UHFFFAOYSA-N 0.000 description 7
YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 7
239000007858 starting material Substances 0.000 description 7
125000001424 substituent group Chemical group 0.000 description 7
238000012360 testing method Methods 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
CMQYISATYUYSAC-UHFFFAOYSA-N 5,6-dimethyl-2-benzofuran-1,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)OC2=O CMQYISATYUYSAC-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
229940079593 drug Drugs 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
239000005457 ice water Substances 0.000 description 6
GNXKPDYSMXCAOA-UHFFFAOYSA-N 2-(5,6-dimethyl-3-oxo-2-pyridin-3-yl-1h-isoindol-1-yl)ethyl methanesulfonate Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(CCOS(C)(=O)=O)N1C1=CC=CN=C1 GNXKPDYSMXCAOA-UHFFFAOYSA-N 0.000 description 5
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
231100000111 LD50 Toxicity 0.000 description 5
206010039897 Sedation Diseases 0.000 description 5
239000012044 organic layer Substances 0.000 description 5
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 5
230000011514 reflex Effects 0.000 description 5
230000036280 sedation Effects 0.000 description 5
239000012279 sodium borohydride Substances 0.000 description 5
229910000033 sodium borohydride Inorganic materials 0.000 description 5
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 4
PJHANGBPMQJFQQ-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-1h-isoindol-1-yl]acetic acid Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(CC(O)=O)N1C1=CC=C(F)C=C1 PJHANGBPMQJFQQ-UHFFFAOYSA-N 0.000 description 4
SKBDLRWFSRLIPP-UHFFFAOYSA-N 4,5-Dimethoxy-1,2-benzenedicarboxylic acid Chemical compound COC1=CC(C(O)=O)=C(C(O)=O)C=C1OC SKBDLRWFSRLIPP-UHFFFAOYSA-N 0.000 description 4
AOAQTWFVCRFMNZ-UHFFFAOYSA-N 5,6-diethyl-2-benzofuran-1,3-dione Chemical compound C1=C(CC)C(CC)=CC2=C1C(=O)OC2=O AOAQTWFVCRFMNZ-UHFFFAOYSA-N 0.000 description 4
IMSDRBDUANUSRL-UHFFFAOYSA-N 5,6-dimethoxy-2-benzofuran-1,3-dione Chemical compound C1=C(OC)C(OC)=CC2=C1C(=O)OC2=O IMSDRBDUANUSRL-UHFFFAOYSA-N 0.000 description 4
NKJKYAYKHJZPFZ-UHFFFAOYSA-N 6,7-dihydro-5h-cyclopenta[f][2]benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1CCC2 NKJKYAYKHJZPFZ-UHFFFAOYSA-N 0.000 description 4
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
239000003193 general anesthetic agent Substances 0.000 description 4
239000002869 intravenous anesthetic agent Substances 0.000 description 4
239000002504 physiological saline solution Substances 0.000 description 4
235000019260 propionic acid Nutrition 0.000 description 4
OLBCVFGFOZPWHH-UHFFFAOYSA-N propofol Chemical compound CC(C)C1=CC=CC(C(C)C)=C1O OLBCVFGFOZPWHH-UHFFFAOYSA-N 0.000 description 4
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
ABQVNNFQKQQAAV-KGENOOAVSA-N (3e)-2-(4-fluorophenyl)-5,6-dimethyl-3-[2-(4-methylpiperazin-1-yl)-2-oxoethylidene]isoindol-1-one Chemical compound C1CN(C)CCN1C(=O)\C=C\1C2=CC(C)=C(C)C=C2C(=O)N/1C1=CC=C(F)C=C1 ABQVNNFQKQQAAV-KGENOOAVSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 3
OIXKTTOZKMRRJL-UHFFFAOYSA-N 2-(3-fluorophenyl)-5,6-dimethyl-3-oxo-1h-isoindole-1-carbonitrile Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(C#N)N1C1=CC=CC(F)=C1 OIXKTTOZKMRRJL-UHFFFAOYSA-N 0.000 description 3
SCNRSSJYBCTXRS-UHFFFAOYSA-N 2-(3-fluorophenyl)-5,6-dimethyl-3-oxo-1h-isoindole-1-carboxylic acid Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(C(O)=O)N1C1=CC=CC(F)=C1 SCNRSSJYBCTXRS-UHFFFAOYSA-N 0.000 description 3
GZDVRHDRMZHOMX-UHFFFAOYSA-N 3-(2-hydroxyethyl)-5,6-dimethyl-2-pyridin-3-yl-3h-isoindol-1-one Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(CCO)N1C1=CC=CN=C1 GZDVRHDRMZHOMX-UHFFFAOYSA-N 0.000 description 3
RWMNFFVEAGSLDW-UHFFFAOYSA-N 3-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-1h-isoindol-1-yl]propanoic acid Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(CCC(O)=O)N1C1=CC=C(F)C=C1 RWMNFFVEAGSLDW-UHFFFAOYSA-N 0.000 description 3
XWOZJTCSFMCOBZ-UHFFFAOYSA-N 3-hexyl-5,6-dimethyl-2-pyridin-3-yl-3h-isoindol-1-one Chemical compound O=C1C2=CC(C)=C(C)C=C2C(CCCCCC)N1C1=CC=CN=C1 XWOZJTCSFMCOBZ-UHFFFAOYSA-N 0.000 description 3
PLFXUMVRDDKJDH-UHFFFAOYSA-N 5,6-dimethyl-2-pyridin-3-ylisoindole-1,3-dione Chemical compound O=C1C=2C=C(C)C(C)=CC=2C(=O)N1C1=CC=CN=C1 PLFXUMVRDDKJDH-UHFFFAOYSA-N 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
239000012359 Methanesulfonyl chloride Substances 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
229940035674 anesthetics Drugs 0.000 description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
229910052794 bromium Inorganic materials 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
KPFOHKBCRCNQET-UHFFFAOYSA-N ethyl 2-(5,6-dimethyl-3-oxo-2-pyridin-3-yl-1h-isoindol-1-yl)acetate Chemical compound O=C1C2=CC(C)=C(C)C=C2C(CC(=O)OCC)N1C1=CC=CN=C1 KPFOHKBCRCNQET-UHFFFAOYSA-N 0.000 description 3
KCHNCQINIRYRBS-UHFFFAOYSA-N ethyl 2-[2-(4-fluorophenyl)-5,6-dimethyl-3-oxo-1h-isoindol-1-yl]acetate Chemical compound O=C1C2=CC(C)=C(C)C=C2C(CC(=O)OCC)N1C1=CC=C(F)C=C1 KCHNCQINIRYRBS-UHFFFAOYSA-N 0.000 description 3
239000007789 gas Substances 0.000 description 3
238000002695 general anesthesia Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 3
230000006698 induction Effects 0.000 description 3
239000002198 insoluble material Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000012423 maintenance Methods 0.000 description 3
FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
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235000013337 tricalcium citrate Nutrition 0.000 description 1
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210000003462 vein Anatomy 0.000 description 1
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239000008215 water for injection Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

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Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)

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