CA2011107A1 - Derives de lactam - Google Patents

Derives de lactam

Info

Publication number: CA2011107A1
Authority: CA; Canada
Prior art keywords: group; formula; compound; compounds; methyl
Prior art date: 1990-02-28
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.): Abandoned

Application number

CA 2011107

Other languages

English (en)

Inventor

David E. Bays

Ian H. Coates

Alexander W. Oxford

Peter C. North

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.)

Glaxo Group Ltd

Original Assignee

Glaxo Group 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.)

1990-02-28

Filing date

1990-02-28

Publication date

1991-08-31

1990-02-28 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

1990-02-28 Priority to CA 2011107 priority Critical patent/CA2011107A1/fr

1991-08-31 Publication of CA2011107A1 publication Critical patent/CA2011107A1/fr

Status Abandoned legal-status Critical Current

Links

150000003951 lactams Chemical class 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 91
-1 C3-6alkenyl Chemical group 0.000 claims abstract description 30
150000003839 salts Chemical class 0.000 claims abstract description 24
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
239000012453 solvate Substances 0.000 claims abstract description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 6
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 3
239000001301 oxygen Substances 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 30
238000000034 method Methods 0.000 claims description 17
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 7
238000007796 conventional method Methods 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
230000008569 process Effects 0.000 claims description 5
125000006239 protecting group Chemical group 0.000 claims description 5
239000012458 free base Substances 0.000 claims description 4
239000000546 pharmaceutical excipient Substances 0.000 claims description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
229940124597 therapeutic agent Drugs 0.000 claims description 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
YLFVJXBIBUPDJB-UHFFFAOYSA-N 12-[(5-methyl-1H-imidazol-4-yl)methyl]-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8,10(15)-tetraen-11-one Chemical compound N1C=NC(CN2C(C3=C(N4CCCC=5C=CC=C3C4=5)CC2)=O)=C1C YLFVJXBIBUPDJB-UHFFFAOYSA-N 0.000 claims 1
XDARXGWDDQMPSI-UHFFFAOYSA-N 4-[(5-methyl-1H-imidazol-4-yl)methyl]-4,9-diazatetracyclo[7.6.1.02,8.012,16]hexadeca-1(15),2(8),12(16),13-tetraen-3-one Chemical compound N1C=NC(CN2C(C3=C(N4CCC=5C=CC=C3C4=5)CCC2)=O)=C1C XDARXGWDDQMPSI-UHFFFAOYSA-N 0.000 claims 1
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 abstract description 18
102000035037 5-HT3 receptors Human genes 0.000 abstract description 6
108091005477 5-HT3 receptors Proteins 0.000 abstract description 6
206010047700 Vomiting Diseases 0.000 abstract description 5
239000005557 antagonist Substances 0.000 abstract description 4
230000003389 potentiating effect Effects 0.000 abstract description 4
208000019901 Anxiety disease Diseases 0.000 abstract description 3
208000028017 Psychotic disease Diseases 0.000 abstract description 3
230000036506 anxiety Effects 0.000 abstract description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000243 solution Substances 0.000 description 25
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
239000007787 solid Substances 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
239000003826 tablet Substances 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 11
238000003818 flash chromatography Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
239000000284 extract Substances 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
239000004480 active ingredient Substances 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000003921 oil Substances 0.000 description 6
235000019198 oils Nutrition 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
230000008570 general process Effects 0.000 description 5
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003377 acid catalyst Substances 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000002585 base Substances 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
239000001257 hydrogen Substances 0.000 description 4
229910052739 hydrogen Inorganic materials 0.000 description 4
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
239000000463 material Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
AHHFSTCSFJWTEF-UHFFFAOYSA-N 4-(chloromethyl)-5-methyl-1-tritylimidazole Chemical compound CC1=C(CCl)N=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 AHHFSTCSFJWTEF-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
206010021518 Impaired gastric emptying Diseases 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
235000019700 dicalcium phosphate Nutrition 0.000 description 3
238000007907 direct compression Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000009472 formulation Methods 0.000 description 3
230000007160 gastrointestinal dysfunction Effects 0.000 description 3
208000001288 gastroparesis Diseases 0.000 description 3
238000005984 hydrogenation reaction Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
VIQCLHMWQFBHJP-UHFFFAOYSA-N 1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5(16),6,8,10(15)-tetraen-11-one Chemical compound C1=2C3=CC=CC=2CCCN1C1=C3C(=O)NCC1 VIQCLHMWQFBHJP-UHFFFAOYSA-N 0.000 description 2
BUPKCWNOAVVEKJ-UHFFFAOYSA-N 3-(2,3-dihydroindol-1-yl)cyclohex-2-en-1-one Chemical compound O=C1CCCC(N2C3=CC=CC=C3CC2)=C1 BUPKCWNOAVVEKJ-UHFFFAOYSA-N 0.000 description 2
RIXYGYXMTCHYLX-UHFFFAOYSA-N 4,5,7,8-tetrahydropyrido[4,3-b]pyrrolo[3,2,1-hi]indol-10(9h)-one Chemical compound O=C1NCCC2=C1C1=CC=CC3=C1N2CC3 RIXYGYXMTCHYLX-UHFFFAOYSA-N 0.000 description 2
ASOHOIBXYIVYRP-UHFFFAOYSA-N 4,5,8,9-tetrahydropyrrolo[3,2,1-jk]carbazol-10(7h)-one oxime Chemical compound ON=C1CCCC2=C1C1=CC=CC3=C1N2CC3 ASOHOIBXYIVYRP-UHFFFAOYSA-N 0.000 description 2
208000032841 Bulimia Diseases 0.000 description 2
206010006550 Bulimia nervosa Diseases 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920002785 Croscarmellose sodium Polymers 0.000 description 2
206010012289 Dementia Diseases 0.000 description 2
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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 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
206010026749 Mania Diseases 0.000 description 2
208000019695 Migraine disease Diseases 0.000 description 2
208000008589 Obesity Diseases 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
208000008469 Peptic Ulcer Diseases 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
239000000337 buffer salt Substances 0.000 description 2
239000002775 capsule Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000007906 compression Methods 0.000 description 2
230000006835 compression Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
229960001681 croscarmellose sodium Drugs 0.000 description 2
235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
208000035475 disorder Diseases 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
201000006549 dyspepsia Diseases 0.000 description 2
239000000839 emulsion Substances 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
206010016766 flatulence Diseases 0.000 description 2
239000007789 gas Substances 0.000 description 2
208000021302 gastroesophageal reflux disease Diseases 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
208000002551 irritable bowel syndrome Diseases 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
206010027599 migraine Diseases 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
235000020824 obesity Nutrition 0.000 description 2
208000011906 peptic ulcer disease Diseases 0.000 description 2
RDNZDMDLRIQQAX-UHFFFAOYSA-N piperidine-2,4-dione Chemical compound O=C1CCNC(=O)C1 RDNZDMDLRIQQAX-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
201000000980 schizophrenia Diseases 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000001117 sulphuric acid Substances 0.000 description 2
235000011149 sulphuric acid Nutrition 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
XGKHUHWWPFOKMN-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinolin-2-amine Chemical compound C1=CC=C2NC(N)CCC2=C1 XGKHUHWWPFOKMN-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
NZYXMYZEQMXRSF-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxazin-4-amine Chemical compound C1=CC=C2N(N)CCOC2=C1 NZYXMYZEQMXRSF-UHFFFAOYSA-N 0.000 description 1
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 1
YRLORWPBJZEGBX-UHFFFAOYSA-N 3,4-dihydro-2h-1,4-benzoxazine Chemical compound C1=CC=C2NCCOC2=C1 YRLORWPBJZEGBX-UHFFFAOYSA-N 0.000 description 1
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
AFTGLNZYSYCFGK-UHFFFAOYSA-N 4,5,8,9-tetrahydropyrrolo[3,2,1-jk]carbazol-10(7h)-one Chemical compound O=C1CCCC2=C1C1=CC=CC3=C1N2CC3 AFTGLNZYSYCFGK-UHFFFAOYSA-N 0.000 description 1
CALSPATYCOEJGW-UHFFFAOYSA-N 4-oxa-1,12-diazatetracyclo[7.6.1.05,16.010,15]hexadeca-5,7,9(16),10(15),11-pentaene Chemical compound C1COC2=C3N1C1=C(C3=CC=C2)C=NCC1 CALSPATYCOEJGW-UHFFFAOYSA-N 0.000 description 1
102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 1
108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 1
SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
235000019489 Almond oil Nutrition 0.000 description 1
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
229940122204 Cyclooxygenase inhibitor Drugs 0.000 description 1
239000004338 Dichlorodifluoromethane Substances 0.000 description 1
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
239000004150 EU approved colour Substances 0.000 description 1
241000792859 Enema Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
229940122957 Histamine H2 receptor antagonist Drugs 0.000 description 1
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
239000002841 Lewis acid Substances 0.000 description 1
235000019759 Maize starch Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
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150000003892 tartrate salts Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
230000009466 transformation Effects 0.000 description 1
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CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
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229910052727 yttrium Inorganic materials 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA 2011107 1990-02-28 1990-02-28 Derives de lactam Abandoned CA2011107A1 (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA 2011107 CA2011107A1 (fr)	1990-02-28	1990-02-28	Derives de lactam

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA 2011107 CA2011107A1 (fr)	1990-02-28	1990-02-28	Derives de lactam

Publications (1)

Publication Number	Publication Date
CA2011107A1 true CA2011107A1 (fr)	1991-08-31

Family

ID=4144406

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2011107 Abandoned CA2011107A1 (fr)	1990-02-28	1990-02-28	Derives de lactam

Country Status (1)

Country	Link
CA (1)	CA2011107A1 (fr)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6548493B1 (en)	1999-06-15	2003-04-15	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US6699852B2 (en)	2000-12-20	2004-03-02	Bristol-Myers Squibb Pharma Company	Substituted pyridoindoles as serotonin agonists and antagonists
US6713471B1 (en)	1999-06-15	2004-03-30	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US6849619B2 (en)	2000-12-20	2005-02-01	Bristol-Myers Squibb Company	Substituted pyridoindoles as serotonin agonists and antagonists
US7071186B2 (en)	1999-06-15	2006-07-04	Bristol-Myers Squibb Pharma Co.	Substituted heterocycle fused gamma-carbolines

1990
- 1990-02-28 CA CA 2011107 patent/CA2011107A1/fr not_active Abandoned

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6548493B1 (en)	1999-06-15	2003-04-15	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US6552017B1 (en)	1999-06-15	2003-04-22	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US6713471B1 (en)	1999-06-15	2004-03-30	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US7071186B2 (en)	1999-06-15	2006-07-04	Bristol-Myers Squibb Pharma Co.	Substituted heterocycle fused gamma-carbolines
US7183282B2 (en)	1999-06-15	2007-02-27	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused γ-carbolines
USRE39680E1 (en)	1999-06-15	2007-06-05	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
USRE39679E1 (en)	1999-06-15	2007-06-05	Bristol-Myers Squibb Pharma Company	Substituted heterocycle fused gamma-carbolines
US6699852B2 (en)	2000-12-20	2004-03-02	Bristol-Myers Squibb Pharma Company	Substituted pyridoindoles as serotonin agonists and antagonists
US6849619B2 (en)	2000-12-20	2005-02-01	Bristol-Myers Squibb Company	Substituted pyridoindoles as serotonin agonists and antagonists

Legal Events

Date	Code	Title	Description
1992-09-01	FZDE	Dead

Publication	Publication Date	Title
US4997831A (en)	1991-03-05	Lactam derivatives
AU613662B2 (en)	1991-08-08	Lactam derivatives
US5045545A (en)	1991-09-03	[(Imidazol-4(and 5)-yl)methyl] tetracyclic ketones having 5-HT3 antagonist activity
US4985422A (en)	1991-01-15	Lactam derivatives
CA1336906C (fr)	1995-09-05	Derives du lactame
EP0385722B1 (fr)	1995-04-19	Dérivés de tricyclique lactame et les compositions pharmaceutiques qui les contiennent
US4950681A (en)	1990-08-21	Ketone derivatives
US5006544A (en)	1991-04-09	Imidazole derivatives and pharmaceutical use thereof
US5116984A (en)	1992-05-26	Imidazole derivatives
EP0291172B1 (fr)	1992-11-19	Dérivés de cétone
US5183820A (en)	1993-02-02	Lactam derivatives
US5008272A (en)	1991-04-16	Lactam derivatives
US4963546A (en)	1990-10-16	Ketone derivatives which are antagonists of 5-HT at 5-HT3 receptors, compositions containing them, and method of use
CA2011107A1 (fr)	1991-08-31	Derives de lactam
US4939144A (en)	1990-07-03	Tricyclic ketone derivatives as 5-HT antagonists
EP0276163B1 (fr)	1992-07-15	Dérivés d'indole
RU2067980C1 (ru)	1996-10-20	Производные лактама и фармацевтическая композиция, являющаяся антагонистом 5-окситраптамина /5-нт/ на 5- нт3 -рецепторах или их физиологически приемлемые соли и соловаты
IE900723A1 (en)	1991-08-28	Lactam derivatives
EP0345956B1 (fr)	1994-03-16	Cétones tricycliques
US5114950A (en)	1992-05-19	5,6-dihydro-N-[(imidazol-4(or 5)-yl)methyl]-4H-pyrrolo[3,2,1-IJ]quinoline-1-carboxamides having 5-HT.sub. antagonist activity
RU2081117C1 (ru)	1997-06-10	Производные лактама или их физиологические приемлемые соли или сольваты
NZ232598A (en)	1992-07-28	Imidazolylmethyl tetracyclic lactam derivatives and pharmaceutical compositions
HU207318B (en)	1993-03-29	Process for producing lactame derivatives and pharmaceutical compositions containing them
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