CA1287626C - Derives de substitution en n de 2-oxo-indole-1- carboxamides, utiles comme produits intermediaires pour la preparation d'analgesiques et d'anti-inflammatoires - Google Patents

Derives de substitution en n de 2-oxo-indole-1- carboxamides, utiles comme produits intermediaires pour la preparation d'analgesiques et d'anti-inflammatoires

Info

Publication number: CA1287626C
Authority: CA; Canada
Prior art keywords: oxindole; phenyl; thienyl; chloro; formula
Prior art date: 1984-05-04
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 - Lifetime

Application number

CA000592245A

Other languages

English (en)

Inventor

Saul Bernard Kadin

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.)

Pfizer Ltd Great Britain

Original Assignee

Pfizer Ltd Great Britain

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.)

1984-05-04

Filing date

1989-02-28

Publication date

1991-08-13

1985-03-22 Priority claimed from US06/714,012 external-priority patent/US4569942A/en

1989-02-28 Application filed by Pfizer Ltd Great Britain filed Critical Pfizer Ltd Great Britain

1991-08-13 Application granted granted Critical

1991-08-13 Publication of CA1287626C publication Critical patent/CA1287626C/fr

2008-08-13 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

230000000202 analgesic effect Effects 0.000 title abstract description 10
239000000730 antalgic agent Substances 0.000 title abstract description 5
239000002260 anti-inflammatory agent Substances 0.000 title abstract description 4
229940121363 anti-inflammatory agent Drugs 0.000 title abstract description 4
239000000543 intermediate Substances 0.000 title abstract description 3
125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 25
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 23
239000001257 hydrogen Substances 0.000 claims abstract description 22
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims abstract description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
JNYLMODTPLSLIF-UHFFFAOYSA-N 6-(trifluoromethyl)pyridine-3-carboxylic acid Chemical group OC(=O)C1=CC=C(C(F)(F)F)N=C1 JNYLMODTPLSLIF-UHFFFAOYSA-N 0.000 claims abstract description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
150000002431 hydrogen Chemical class 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 86
238000000034 method Methods 0.000 claims description 47
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 39
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
239000012948 isocyanate Substances 0.000 claims description 8
150000002513 isocyanates Chemical class 0.000 claims description 8
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 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
UYINJAQCJCYCGO-UHFFFAOYSA-N 2-oxo-3h-indole-1-carboxamide Chemical group C1=CC=C2N(C(=O)N)C(=O)CC2=C1 UYINJAQCJCYCGO-UHFFFAOYSA-N 0.000 abstract description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 4
229910052757 nitrogen Inorganic materials 0.000 abstract description 2
125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 abstract 1
-1 N-substituted 2-oxindole-1-carboxamides Chemical class 0.000 description 174
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
239000000243 solution Substances 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 33
238000006243 chemical reaction Methods 0.000 description 32
239000007787 solid Substances 0.000 description 31
239000000203 mixture Substances 0.000 description 30
238000001914 filtration Methods 0.000 description 28
239000011541 reaction mixture Substances 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
238000003756 stirring Methods 0.000 description 21
238000002360 preparation method Methods 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
235000011167 hydrochloric acid Nutrition 0.000 description 17
229960000443 hydrochloric acid Drugs 0.000 description 17
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
239000000047 product Substances 0.000 description 15
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 12
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000002253 acid Substances 0.000 description 12
JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 10
150000003839 salts Chemical class 0.000 description 10
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 9
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 9
208000002193 Pain Diseases 0.000 description 9
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
239000002244 precipitate Substances 0.000 description 9
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
239000002002 slurry Substances 0.000 description 7
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 6
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
HSYFISNDMZKGRS-UHFFFAOYSA-N 4-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=CC2=C1C(=O)C(=O)N2 HSYFISNDMZKGRS-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
241000699670 Mus sp. Species 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 5
229960002327 chloral hydrate Drugs 0.000 description 5
239000013078 crystal Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
150000005623 oxindoles Chemical class 0.000 description 5
239000000376 reactant Substances 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
239000000126 substance Substances 0.000 description 5
125000001424 substituent group Chemical group 0.000 description 5
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 4
JARRYVQFBQVOBE-UHFFFAOYSA-N 6-bromo-1,3-dihydroindol-2-one Chemical compound BrC1=CC=C2CC(=O)NC2=C1 JARRYVQFBQVOBE-UHFFFAOYSA-N 0.000 description 4
RVXLBLSGEPQBIO-UHFFFAOYSA-N 6-chloro-1h-indole-2,3-dione Chemical compound ClC1=CC=C2C(=O)C(=O)NC2=C1 RVXLBLSGEPQBIO-UHFFFAOYSA-N 0.000 description 4
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 4
241000124008 Mammalia Species 0.000 description 4
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
230000003187 abdominal effect Effects 0.000 description 4
230000001154 acute effect Effects 0.000 description 4
229910052783 alkali metal Inorganic materials 0.000 description 4
239000002585 base Substances 0.000 description 4
125000005605 benzo group Chemical group 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000012429 reaction media Substances 0.000 description 4
230000035484 reaction time Effects 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
239000011734 sodium Substances 0.000 description 4
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
238000005303 weighing Methods 0.000 description 4
QRBAXYYNPFDZAX-UHFFFAOYSA-N 1-tert-butyl-2,3-dimethylbenzene Chemical group CC1=CC=CC(C(C)(C)C)=C1C QRBAXYYNPFDZAX-UHFFFAOYSA-N 0.000 description 3
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 3
XNSPDJAXCBZCRV-UHFFFAOYSA-N 4-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=CC2=C1CC(=O)N2 XNSPDJAXCBZCRV-UHFFFAOYSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
CENVPIZOTHULGJ-UHFFFAOYSA-N 6-chloro-1,3-dihydroindol-2-one Chemical compound ClC1=CC=C2CC(=O)NC2=C1 CENVPIZOTHULGJ-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010061218 Inflammation Diseases 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229910052784 alkaline earth metal Inorganic materials 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
125000001246 bromo group Chemical group Br* 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
230000001684 chronic effect Effects 0.000 description 3
CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
125000004494 ethyl ester group Chemical group 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
230000004054 inflammatory process Effects 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000000463 material Substances 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
OPVVMXVNHRTMAK-UHFFFAOYSA-N n-tert-butyl-6-chloro-2-oxo-3-(thiophene-2-carbonyl)-3h-indole-1-carboxamide Chemical compound C12=CC=C(Cl)C=C2N(C(=O)NC(C)(C)C)C(=O)C1C(=O)C1=CC=CS1 OPVVMXVNHRTMAK-UHFFFAOYSA-N 0.000 description 3
239000008194 pharmaceutical composition Substances 0.000 description 3
239000012071 phase Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
230000004044 response Effects 0.000 description 3
238000007363 ring formation reaction Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
208000024891 symptom Diseases 0.000 description 3
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
125000003944 tolyl group Chemical group 0.000 description 3
239000008096 xylene Substances 0.000 description 3
FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
DJPAQYXQRCWKEH-UHFFFAOYSA-N 2-chloro-n-(3-chloro-4-fluorophenyl)acetamide Chemical compound FC1=CC=C(NC(=O)CCl)C=C1Cl DJPAQYXQRCWKEH-UHFFFAOYSA-N 0.000 description 2
DCWSRBDYLSWXIS-UHFFFAOYSA-N 4,5-dimethyl-1,3-dihydroindol-2-one Chemical compound CC1=CC=C2NC(=O)CC2=C1C DCWSRBDYLSWXIS-UHFFFAOYSA-N 0.000 description 2
WPXZFSQTAFULLU-UHFFFAOYSA-N 4-chloro-3-hydrazinylindol-2-one Chemical compound C1=CC(Cl)=C2C(=NN)C(=O)NC2=C1 WPXZFSQTAFULLU-UHFFFAOYSA-N 0.000 description 2
BXMRWUIRVNVUBM-UHFFFAOYSA-N 4-ethoxy-2-methyl-1-nitrobenzene Chemical compound CCOC1=CC=C([N+]([O-])=O)C(C)=C1 BXMRWUIRVNVUBM-UHFFFAOYSA-N 0.000 description 2
BRWIXNVFRUVHEU-UHFFFAOYSA-N 5,6-dimethyl-1h-indole-2,3-dione Chemical compound C1=C(C)C(C)=CC2=C1C(=O)C(=O)N2 BRWIXNVFRUVHEU-UHFFFAOYSA-N 0.000 description 2
WIEJKTTWCGNQHH-UHFFFAOYSA-N 5-butyl-1h-indole-2,3-dione Chemical compound CCCCC1=CC=C2NC(=O)C(=O)C2=C1 WIEJKTTWCGNQHH-UHFFFAOYSA-N 0.000 description 2
UKNVMAPOVWLHAP-UHFFFAOYSA-N 5-cycloheptyl-1h-indole-2,3-dione Chemical compound C1=C2C(=O)C(=O)NC2=CC=C1C1CCCCCC1 UKNVMAPOVWLHAP-UHFFFAOYSA-N 0.000 description 2
FYGKPUITCUFXLV-UHFFFAOYSA-N 5-cyclopropyl-1h-indole-2,3-dione Chemical compound C1=C2C(=O)C(=O)NC2=CC=C1C1CC1 FYGKPUITCUFXLV-UHFFFAOYSA-N 0.000 description 2
DDIIYGHHUMKDGI-UHFFFAOYSA-N 5-fluoro-1,3-dihydroindol-2-one Chemical compound FC1=CC=C2NC(=O)CC2=C1 DDIIYGHHUMKDGI-UHFFFAOYSA-N 0.000 description 2
QDUXBJGXHPPFJG-UHFFFAOYSA-N 6-chloro-5-fluoro-1,3-dihydroindol-2-one Chemical compound C1=C(Cl)C(F)=CC2=C1NC(=O)C2 QDUXBJGXHPPFJG-UHFFFAOYSA-N 0.000 description 2
BRTXRFCARXOWJV-UHFFFAOYSA-N 6-phenyl-1,3-dihydroindol-2-one Chemical compound C1=C2NC(=O)CC2=CC=C1C1=CC=CC=C1 BRTXRFCARXOWJV-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
208000017667 Chronic Disease Diseases 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
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239000000314 lubricant Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
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KHXUTOLCCFWPDH-UHFFFAOYSA-N methyl 2-(4-bromo-2-nitrophenyl)acetate Chemical compound COC(=O)CC1=CC=C(Br)C=C1[N+]([O-])=O KHXUTOLCCFWPDH-UHFFFAOYSA-N 0.000 description 1
125000006178 methyl benzyl group Chemical group 0.000 description 1
YPCRTQSPZPUZBW-UHFFFAOYSA-N n-(2-oxo-1,3-dihydroindol-5-yl)benzamide Chemical compound C=1C=C2NC(=O)CC2=CC=1NC(=O)C1=CC=CC=C1 YPCRTQSPZPUZBW-UHFFFAOYSA-N 0.000 description 1
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125000001624 naphthyl group Chemical group 0.000 description 1
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BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
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DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
230000001629 suppression Effects 0.000 description 1
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239000000375 suspending agent Substances 0.000 description 1
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239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
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 description 1
238000012360 testing method Methods 0.000 description 1
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
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238000011200 topical administration Methods 0.000 description 1
230000008733 trauma Effects 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA000592245A 1984-05-04 1989-02-28 Derives de substitution en n de 2-oxo-indole-1- carboxamides, utiles comme produits intermediaires pour la preparation d'analgesiques et d'anti-inflammatoires Expired - Lifetime CA1287626C (fr)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date	Title
US60735684A	1984-05-04	1984-05-04
US607,356		1984-05-04
US714,012		1985-03-22
US06/714,012 US4569942A (en)	1984-05-04	1985-03-22	N,3-Disubstituted 2-oxindole-1-carboxamides as analgesic and antiinflammatory agents
CA000480573A CA1255658A (fr)	1984-05-04	1985-05-02	Derives de disubstitution en n,3 de 2-oxindole-1- carboxamides, agents analgesiques et anti-inflammatoires

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000480573A Division CA1255658A (fr)	1984-05-04	1985-05-02	Derives de disubstitution en n,3 de 2-oxindole-1- carboxamides, agents analgesiques et anti-inflammatoires

Publications (1)

Publication Number	Publication Date
CA1287626C true CA1287626C (fr)	1991-08-13

Family

ID=27167518

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000592245A Expired - Lifetime CA1287626C (fr)	1984-05-04	1989-02-28	Derives de substitution en n de 2-oxo-indole-1- carboxamides, utiles comme produits intermediaires pour la preparation d'analgesiques et d'anti-inflammatoires

Country Status (1)

Country	Link
CA (1)	CA1287626C (fr)

1989
- 1989-02-28 CA CA000592245A patent/CA1287626C/fr not_active Expired - Lifetime

Legal Events

Date	Code	Title	Description
2006-08-14	MKLA	Lapsed

Publication	Publication Date	Title
CA1255658A (fr)	1989-06-13	Derives de disubstitution en n,3 de 2-oxindole-1- carboxamides, agents analgesiques et anti-inflammatoires
EP0156603B1 (fr)	1989-08-23	1-Carboxamide-2-oxindols-3-substitués utilisés comme agents analgésiques et anti-inflammatoires
EP0175551B1 (fr)	1989-05-10	Composés analgésiques et anti-inflammatoires dérivés du 1,3-diacyl 2-oxindole
EP0208510B1 (fr)	1991-09-11	Oxindole-3-carboxamines substituées utilisées analgésiques et anti-inflammatoires
US4721712A (en)	1988-01-26	1,3-disubstituted 2-oxindoles as analgesic and anti-inflammatory agents
US4658037A (en)	1987-04-14	Intermediates for 1,3-disubstituted 2-oxindoles as analgesic and antiinflammatory agents
EP0153818B1 (fr)	1989-03-15	2-Oxindoles 1,3-disubstitués et leur utilisation comme agents analgésiques et anti-inflammatoires
EP0155828B1 (fr)	1990-09-19	Procédé de préparation de 2-oxindole-1-carboxamides et leurs intermédiaires
US4665194A (en)	1987-05-12	Process for making 2-oxindole-1-carboxamides and intermediates therefor
CA1287626C (fr)	1991-08-13	Derives de substitution en n de 2-oxo-indole-1- carboxamides, utiles comme produits intermediaires pour la preparation d'analgesiques et d'anti-inflammatoires
US4808601A (en)	1989-02-28	Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
US4752609A (en)	1988-06-21	Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds
DD232039A5 (de)	1986-01-15	Verfahren zur herstellung einer 2-oxinidol-1-carboxamid-verbindung
US4652658A (en)	1987-03-24	Process for making 2-oxindole-1-carboxamides and intermediates therefor
US4730004A (en)	1988-03-08	Analgesic and anti-inflammatory 1-acyl-2-oxindole-3-carboxamides
US4791131A (en)	1988-12-13	Analgesic and antiinflammatory 1-acyl-2-oxindole-3-carboxamides
CA1289556C (fr)	1991-09-24	Intermediaires de 2-indoles monosubstitues en 1 ou 3, utiles pour la production d'analgesiques ou d'anti-inflammatoires
FI80016B (fi)	1989-12-29	N,3-disubstituerade 2-oxindol-1 -karboxiamider saosom smaertstillande och antiinflammatoriska medel.
CA1255657A (fr)	1989-06-13	Derives de substitution en 1,3 de 2-oxindoles, agents analgesiques et anti-inflammatoires
CA1253490A (fr)	1989-05-02	Procede de production de 2-oxindole-1-carboxamides
IE850288L (en)	1985-08-07	Analgesic oxindoles.
BG60375B2 (bg)	1995-02-28	Заместени на 3-то място 2-оксиндол-1-карбоксамиди като аналгетични и противовъзпалителни вещества