CA1071211A - 4-(1-oxo-isoquinoline)-or 4-(1-oxo-1-isoindoline)-piperidines - Google Patents
4-(1-oxo-isoquinoline)-or 4-(1-oxo-1-isoindoline)-piperidinesInfo
- Publication number
- CA1071211A CA1071211A CA232,449A CA232449A CA1071211A CA 1071211 A CA1071211 A CA 1071211A CA 232449 A CA232449 A CA 232449A CA 1071211 A CA1071211 A CA 1071211A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- oxo
- formula
- piperidine
- hydroxypropyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 139
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 239000002253 acid Substances 0.000 claims abstract description 50
- -1 o-phenylene radical Chemical class 0.000 claims description 172
- 238000000034 method Methods 0.000 claims description 70
- 230000008569 process Effects 0.000 claims description 59
- 239000001257 hydrogen Substances 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 150000003254 radicals Chemical class 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 45
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 31
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 239000000126 substance Substances 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000004043 oxo group Chemical group O=* 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 150000005840 aryl radicals Chemical class 0.000 claims description 15
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- OPRUEOKLZSOCLC-UHFFFAOYSA-N 2-piperidin-4-yl-3,4-dihydroisoquinolin-1-one Chemical compound C1CC2=CC=CC=C2C(=O)N1C1CCNCC1 OPRUEOKLZSOCLC-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 230000003287 optical effect Effects 0.000 claims description 7
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 claims description 6
- RJNVSQLNEALZLC-UHFFFAOYSA-N 2-[(2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC=C1OCC1OC1 RJNVSQLNEALZLC-UHFFFAOYSA-N 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000006193 alkinyl group Chemical group 0.000 claims description 5
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- 150000003053 piperidines Chemical class 0.000 claims description 5
- 230000002829 reductive effect Effects 0.000 claims description 5
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 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
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 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 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- FZONULHLKBOHHY-UHFFFAOYSA-N 2-[(2-prop-2-enoxyphenoxy)methyl]oxirane Chemical compound C=CCOC1=CC=CC=C1OCC1OC1 FZONULHLKBOHHY-UHFFFAOYSA-N 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- CFPDZLJTWSBXLP-UHFFFAOYSA-N 2-[(4-chloro-2-methoxyphenoxy)methyl]oxirane Chemical compound COC1=CC(Cl)=CC=C1OCC1OC1 CFPDZLJTWSBXLP-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- BIJYXIOVXFBJEP-UHFFFAOYSA-N 2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound N#CC1=CC=CC=C1OCC1OC1 BIJYXIOVXFBJEP-UHFFFAOYSA-N 0.000 claims 2
- 125000004848 alkoxyethyl group Chemical group 0.000 claims 2
- 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 claims 2
- QYYCPWLLBSSFBW-UHFFFAOYSA-N 2-(naphthalen-1-yloxymethyl)oxirane Chemical compound C=1C=CC2=CC=CC=C2C=1OCC1CO1 QYYCPWLLBSSFBW-UHFFFAOYSA-N 0.000 claims 1
- YKZOSUVYYFTRKR-UHFFFAOYSA-N 2-[(2,3-dimethoxyphenoxy)methyl]oxirane Chemical compound COC1=CC=CC(OCC2OC2)=C1OC YKZOSUVYYFTRKR-UHFFFAOYSA-N 0.000 claims 1
- CFPYDAOUKFUDEY-UHFFFAOYSA-N 2-[(2-bromophenoxy)methyl]oxirane Chemical compound BrC1=CC=CC=C1OCC1OC1 CFPYDAOUKFUDEY-UHFFFAOYSA-N 0.000 claims 1
- DAGBZRAFMXTXNY-UHFFFAOYSA-N 2-[(2-chloro-5-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=C(Cl)C(OCC2OC2)=C1 DAGBZRAFMXTXNY-UHFFFAOYSA-N 0.000 claims 1
- RTWPGIYHLKEHAF-UHFFFAOYSA-N 2-[(2-cyclohexylphenoxy)methyl]oxirane Chemical compound C1OC1COC1=CC=CC=C1C1CCCCC1 RTWPGIYHLKEHAF-UHFFFAOYSA-N 0.000 claims 1
- KFUSXMDYOPXKKT-UHFFFAOYSA-N 2-[(2-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC=C1OCC1OC1 KFUSXMDYOPXKKT-UHFFFAOYSA-N 0.000 claims 1
- OCDHRUIARWXIBR-UHFFFAOYSA-N 2-[(2-prop-2-ynoxyphenoxy)methyl]oxirane Chemical compound C#CCOC1=CC=CC=C1OCC1OC1 OCDHRUIARWXIBR-UHFFFAOYSA-N 0.000 claims 1
- BQMIZBSDGSJXGW-UHFFFAOYSA-N 2-[1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperidin-4-yl]-3,4-dihydroisoquinolin-1-one;hydrochloride Chemical compound Cl.COC1=CC=CC=C1OCC(O)CN1CCC(N2C(C3=CC=CC=C3CC2)=O)CC1 BQMIZBSDGSJXGW-UHFFFAOYSA-N 0.000 claims 1
- YOXGJXRKLKRZRW-UHFFFAOYSA-N 2-[1-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperidin-4-yl]isoindole-1,3-dione Chemical compound COC1=CC=CC=C1OCC(O)CN1CCC(N2C(C3=CC=CC=C3C2=O)=O)CC1 YOXGJXRKLKRZRW-UHFFFAOYSA-N 0.000 claims 1
- VVDJWOBBCSRTOE-UHFFFAOYSA-N 2-[1-[2-hydroxy-3-(2-methylphenoxy)propyl]piperidin-4-yl]-3,4-dihydroisoquinolin-1-one Chemical compound CC1=CC=CC=C1OCC(O)CN1CCC(N2C(C3=CC=CC=C3CC2)=O)CC1 VVDJWOBBCSRTOE-UHFFFAOYSA-N 0.000 claims 1
- SOGKXLVYZZXFTN-UHFFFAOYSA-N 2-[4-(oxiran-2-ylmethoxy)phenyl]acetamide Chemical compound C1=CC(CC(=O)N)=CC=C1OCC1OC1 SOGKXLVYZZXFTN-UHFFFAOYSA-N 0.000 claims 1
- UEOWFGJMGUIGHC-UHFFFAOYSA-N 2-[[4-(2-methoxyethyl)phenoxy]methyl]oxirane Chemical compound C1=CC(CCOC)=CC=C1OCC1OC1 UEOWFGJMGUIGHC-UHFFFAOYSA-N 0.000 claims 1
- PRXIICMTEXYFQH-UHFFFAOYSA-N 2-piperidin-4-ylisoindole-1,3-dione;hydrochloride Chemical compound Cl.O=C1C2=CC=CC=C2C(=O)N1C1CCNCC1 PRXIICMTEXYFQH-UHFFFAOYSA-N 0.000 claims 1
- PEQJSBNIYFJZNM-UHFFFAOYSA-N [1-(2-methoxyphenoxy)-3-[4-(1-oxo-3,4-dihydroisoquinolin-2-yl)piperidin-1-yl]propan-2-yl] 2,2-dimethylpropanoate Chemical compound COC1=CC=CC=C1OCC(OC(=O)C(C)(C)C)CN1CCC(N2C(C3=CC=CC=C3CC2)=O)CC1 PEQJSBNIYFJZNM-UHFFFAOYSA-N 0.000 claims 1
- 125000005133 alkynyloxy group Chemical group 0.000 claims 1
- 150000004707 phenolate Chemical class 0.000 claims 1
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- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000005530 alkylenedioxy group Chemical group 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- HAVZTGSQJIEKPI-UHFFFAOYSA-N benzothiadiazine Chemical compound C1=CC=C2C=NNSC2=C1 HAVZTGSQJIEKPI-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000000332 continued effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- JGDFBJMWFLXCLJ-UHFFFAOYSA-N copper chromite Chemical compound [Cu]=O.[Cu]=O.O=[Cr]O[Cr]=O JGDFBJMWFLXCLJ-UHFFFAOYSA-N 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- HXCKCCRKGXHOBK-UHFFFAOYSA-N cycloheptane Chemical compound [CH]1CCCCCC1 HXCKCCRKGXHOBK-UHFFFAOYSA-N 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- KGBMIAYNJRCVGH-UHFFFAOYSA-N ethyl 2-(2-aminoethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCN KGBMIAYNJRCVGH-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 229960004979 fampridine Drugs 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000001435 haemodynamic effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 125000005358 mercaptoalkyl group Chemical group 0.000 description 1
- 210000003975 mesenteric artery Anatomy 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000000933 noradrenolytic effect Effects 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229960003975 potassium Drugs 0.000 description 1
- 235000007686 potassium Nutrition 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- DITHIFQMPPCBCU-UHFFFAOYSA-N propa-1,2-diene Chemical compound [CH]=C=C DITHIFQMPPCBCU-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000002577 pseudohalo group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000036647 reaction Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940100890 silver compound Drugs 0.000 description 1
- 150000003379 silver compounds Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 229960004799 tryptophan Drugs 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1058374A CH605914A5 (is") | 1974-07-31 | 1974-07-31 | |
| US05/533,107 US4000287A (en) | 1974-12-16 | 1974-12-16 | Isoindolinopiperidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071211A true CA1071211A (en) | 1980-02-05 |
Family
ID=25706951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA232,449A Expired CA1071211A (en) | 1974-07-31 | 1975-07-29 | 4-(1-oxo-isoquinoline)-or 4-(1-oxo-1-isoindoline)-piperidines |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5139676A (is") |
| AT (1) | AT355022B (is") |
| AU (1) | AU498555B2 (is") |
| CA (1) | CA1071211A (is") |
| DE (1) | DE2533567A1 (is") |
| DK (1) | DK141752B (is") |
| FR (1) | FR2280377A1 (is") |
| GB (1) | GB1505573A (is") |
| HK (1) | HK23581A (is") |
| MY (1) | MY8200004A (is") |
| NL (1) | NL7508589A (is") |
| SE (1) | SE7507931L (is") |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LU77856A1 (de) * | 1977-07-27 | 1979-03-26 | Ciba Geigy Ag | Verfahren zur herstellung von neuen piperidin-derivaten |
| US4304912A (en) | 1978-07-20 | 1981-12-08 | Ciba-Geigy Corporation | Piperidine derivatives |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| US5567718A (en) * | 1994-08-11 | 1996-10-22 | Hoechst Marion Roussel Inc. | 2,3-dihydro-1h-isoindole derivatives and their use as serotonin reuptake inhibitors |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH598251A5 (is") * | 1972-08-24 | 1978-04-28 | Ciba Geigy Ag |
-
1975
- 1975-07-09 DK DK311475AA patent/DK141752B/da unknown
- 1975-07-10 SE SE7507931A patent/SE7507931L/xx unknown
- 1975-07-17 NL NL7508589A patent/NL7508589A/xx not_active Application Discontinuation
- 1975-07-26 DE DE19752533567 patent/DE2533567A1/de not_active Withdrawn
- 1975-07-29 CA CA232,449A patent/CA1071211A/en not_active Expired
- 1975-07-29 FR FR7523618A patent/FR2280377A1/fr active Granted
- 1975-07-30 AU AU83521/75A patent/AU498555B2/en not_active Expired
- 1975-07-30 AT AT590475A patent/AT355022B/de not_active IP Right Cessation
- 1975-07-31 JP JP50092657A patent/JPS5139676A/ja active Pending
- 1975-07-31 GB GB32051/75A patent/GB1505573A/en not_active Expired
-
1981
- 1981-05-28 HK HK235/81A patent/HK23581A/xx unknown
-
1982
- 1982-12-30 MY MY4/82A patent/MY8200004A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK141752B (da) | 1980-06-09 |
| FR2280377A1 (fr) | 1976-02-27 |
| AU498555B2 (en) | 1979-03-15 |
| JPS5139676A (en) | 1976-04-02 |
| AU8352175A (en) | 1977-02-03 |
| MY8200004A (en) | 1982-12-31 |
| SE7507931L (sv) | 1976-02-02 |
| DK141752C (is") | 1980-11-03 |
| ATA590475A (de) | 1979-07-15 |
| DK311475A (is") | 1976-02-01 |
| DE2533567A1 (de) | 1976-02-19 |
| AT355022B (de) | 1980-02-11 |
| HK23581A (en) | 1981-06-05 |
| FR2280377B1 (is") | 1979-10-19 |
| GB1505573A (en) | 1978-03-30 |
| NL7508589A (nl) | 1976-02-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |