CY1431A - 3,3-dialkyl-and,3,3-alkylene-indoline derivatives,processes for their production and pharmaceutical compositions,comprising them - Google Patents
3,3-dialkyl-and,3,3-alkylene-indoline derivatives,processes for their production and pharmaceutical compositions,comprising them Download PDFInfo
- Publication number
- CY1431A CY1431A CY1431A CY143188A CY1431A CY 1431 A CY1431 A CY 1431A CY 1431 A CY1431 A CY 1431A CY 143188 A CY143188 A CY 143188A CY 1431 A CY1431 A CY 1431A
- Authority
- CY
- Cyprus
- Prior art keywords
- indoline
- dimethyl
- hydroxy
- indolin
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 30
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 40
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- 239000012458 free base Substances 0.000 claims description 27
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- 150000002148 esters Chemical class 0.000 claims description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 22
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical compound C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 12
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- 125000002252 acyl group Chemical group 0.000 claims description 6
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- QWHYSBHTCJIXPO-UHFFFAOYSA-N 5-methoxy-3,3-dimethyl-1h-indol-2-one Chemical compound COC1=CC=C2NC(=O)C(C)(C)C2=C1 QWHYSBHTCJIXPO-UHFFFAOYSA-N 0.000 claims description 3
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- UZGAUBROKVHOFS-UHFFFAOYSA-N (1-acetyl-2-oxo-3h-indol-4-yl) acetate Chemical compound CC(=O)OC1=CC=CC2=C1CC(=O)N2C(C)=O UZGAUBROKVHOFS-UHFFFAOYSA-N 0.000 claims description 2
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- OCEMCBBMNJBAJI-UHFFFAOYSA-N 4-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=CC2=C1C(C)(C)CN2 OCEMCBBMNJBAJI-UHFFFAOYSA-N 0.000 claims description 2
- GQXQTKBIKOHVDS-UHFFFAOYSA-N 4-ethoxy-3,3-dimethyl-1h-indol-2-one Chemical compound CCOC1=CC=CC2=C1C(C)(C)C(=O)N2 GQXQTKBIKOHVDS-UHFFFAOYSA-N 0.000 claims description 2
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- IYNJZTHCVZTRNV-UHFFFAOYSA-N 6-ethoxy-3,3,5-trimethyl-1,2-dihydroindole Chemical compound C1=C(C)C(OCC)=CC2=C1C(C)(C)CN2 IYNJZTHCVZTRNV-UHFFFAOYSA-N 0.000 claims description 2
- LTQXKFWKDLQHPY-UHFFFAOYSA-N 6-ethoxy-3,3,5-trimethyl-1h-indol-2-one Chemical compound C1=C(C)C(OCC)=CC2=C1C(C)(C)C(=O)N2 LTQXKFWKDLQHPY-UHFFFAOYSA-N 0.000 claims description 2
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- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- XEWDCQVTGOZKNH-UHFFFAOYSA-N 1-(3,3-dimethyl-5-propan-2-yloxy-2h-indol-1-yl)ethanone Chemical compound CC(C)OC1=CC=C2N(C(C)=O)CC(C)(C)C2=C1 XEWDCQVTGOZKNH-UHFFFAOYSA-N 0.000 claims 1
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- CNYMFJWCSOZAFV-UHFFFAOYSA-N 3,3-dimethyl-5-propan-2-yloxy-1,2-dihydroindole Chemical compound CC(C)OC1=CC=C2NCC(C)(C)C2=C1 CNYMFJWCSOZAFV-UHFFFAOYSA-N 0.000 claims 1
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- ZDLJMUHGWNWHCS-UHFFFAOYSA-N 4-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound C1=CC(O)=C2C(C)(C)C(=O)NC2=C1 ZDLJMUHGWNWHCS-UHFFFAOYSA-N 0.000 claims 1
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- IVMYKLYNZCWHTC-UHFFFAOYSA-N 5-hydroxy-3,3-dimethyl-1h-indol-2-one Chemical compound C1=C(O)C=C2C(C)(C)C(=O)NC2=C1 IVMYKLYNZCWHTC-UHFFFAOYSA-N 0.000 claims 1
- KKXRYAPPQOIPCX-UHFFFAOYSA-N 5-methoxy-3,3,7-trimethyl-1,2-dihydroindole Chemical compound CC1=CC(OC)=CC2=C1NCC2(C)C KKXRYAPPQOIPCX-UHFFFAOYSA-N 0.000 claims 1
- XHKJBYFKLWRGFP-UHFFFAOYSA-N 5-methoxy-3,3,7-trimethyl-1h-indol-2-one Chemical compound CC1=CC(OC)=CC2=C1NC(=O)C2(C)C XHKJBYFKLWRGFP-UHFFFAOYSA-N 0.000 claims 1
- JYWXNYIUDFMBCL-UHFFFAOYSA-N 5-methoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound COC1=CC=C2NCC(C)(C)C2=C1 JYWXNYIUDFMBCL-UHFFFAOYSA-N 0.000 claims 1
- ITLRQEKXUKZTPG-UHFFFAOYSA-N 6-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=C2C(C)(C)CNC2=C1 ITLRQEKXUKZTPG-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 230000037452 priming Effects 0.000 claims 1
- 239000000047 product Substances 0.000 description 29
- 239000007858 starting material Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 150000002476 indolines Chemical class 0.000 description 17
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- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000011514 reflex Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005690 transetherification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH37382 | 1982-01-21 | ||
| CH374582 | 1982-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1431A true CY1431A (en) | 1988-09-02 |
Family
ID=25684383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1431A CY1431A (en) | 1982-01-21 | 1988-09-02 | 3,3-dialkyl-and,3,3-alkylene-indoline derivatives,processes for their production and pharmaceutical compositions,comprising them |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US4622336A (en, 2012) |
| AT (1) | AT381490B (en, 2012) |
| AU (1) | AU565538B2 (en, 2012) |
| CA (1) | CA1191857A (en, 2012) |
| CH (1) | CH657848A5 (en, 2012) |
| CY (1) | CY1431A (en, 2012) |
| DE (1) | DE3300522A1 (en, 2012) |
| DK (1) | DK161071C (en, 2012) |
| ES (1) | ES519108A0 (en, 2012) |
| FI (1) | FI79098C (en, 2012) |
| FR (1) | FR2519982B1 (en, 2012) |
| GB (1) | GB2113682B (en, 2012) |
| HK (1) | HK56888A (en, 2012) |
| HU (1) | HU189215B (en, 2012) |
| IE (1) | IE54878B1 (en, 2012) |
| IL (1) | IL67715A (en, 2012) |
| IT (1) | IT1197546B (en, 2012) |
| KE (1) | KE3813A (en, 2012) |
| MY (1) | MY8600467A (en, 2012) |
| NL (1) | NL8300159A (en, 2012) |
| NZ (1) | NZ203056A (en, 2012) |
| PH (1) | PH22848A (en, 2012) |
| PT (1) | PT76110B (en, 2012) |
| SE (1) | SE453293B (en, 2012) |
| SG (1) | SG22688G (en, 2012) |
| WO (1) | WO1983002610A1 (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4690943A (en) * | 1984-09-19 | 1987-09-01 | Pfizer Inc. | Analgesic and antiinflammatory 1,3-diacyl-2-oxindole compounds |
| US4803217A (en) * | 1986-12-24 | 1989-02-07 | Merck & Co., Inc. | Hapalindolinone compounds as vassopressin antagonists |
| GB8723157D0 (en) * | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
| GB9108965D0 (en) * | 1991-04-26 | 1991-06-12 | Sandoz Ltd | Improvements in or relating to organic compounds |
| FR2708606B1 (fr) * | 1993-07-30 | 1995-10-27 | Sanofi Sa | Dérivés du N-phénylalkylindol-2-one, leur préparation, les compositions pharmaceutiques en contenant. |
| WO2016179157A1 (en) | 2015-05-05 | 2016-11-10 | Carafe Drug Innovation, Llc | Substituted 5-hydroxyoxindoles and their use as analgesics and fever reducers |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE368009B (en, 2012) * | 1971-09-16 | 1974-06-17 | Kabi Ab | |
| AT311332B (de) * | 1971-12-06 | 1973-11-12 | Pierrel Spa | Verfahren zur Herstellung eines neuen Esters von 3,3-Bis(p-hydroxyphenyl)-2-indolinon und dessen Salzen |
| BE524637A (en, 2012) * | 1972-05-17 | |||
| GB1437804A (en) * | 1973-09-10 | 1976-06-03 | Lepetit Spa | Indole derivatives |
| AT346841B (de) * | 1976-11-30 | 1978-11-27 | Delmar Chem | Verfahren zur herstellung von neuen 3- phenylindolinen und ihren salzen |
| FI59246C (fi) * | 1974-06-24 | 1981-07-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av benscykloamidderivat anvaendbara vid trombos- och emboliterapin |
| JPS597699B2 (ja) * | 1977-02-04 | 1984-02-20 | イハラケミカル工業株式会社 | インドリン類の製造方法 |
| DE2816380A1 (de) * | 1977-04-21 | 1978-12-07 | Hoechst Ag | Spiro eckige klammer auf indolin- 3,4'-piperidine eckige klammer zu und verwandte verbindungen |
| DE2805620A1 (de) * | 1978-02-10 | 1979-08-23 | Basf Ag | Verfahren zur herstellung von indoleninen |
| US4307235A (en) * | 1978-08-23 | 1981-12-22 | American Hoechst Corporation | Spiro[indoline-3,4'-piperidine]s |
| JPS597700B2 (ja) * | 1978-10-31 | 1984-02-20 | イハラケミカル工業株式会社 | インドリン類の製造方法 |
| US4408050A (en) * | 1980-02-15 | 1983-10-04 | American Hoechst Corporation | Spiro(indoline-3,4'-piperidine) and related compounds |
| US4345081A (en) * | 1980-02-15 | 1982-08-17 | American Hoechst Corporation | Spiro[indoline-3,4'-piperidine]s |
| DE3143327A1 (de) * | 1980-11-12 | 1982-06-09 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue indolinone, ihre herstellung und ihre verwendung als arzneimittel" |
| IT1143242B (it) * | 1980-11-18 | 1986-10-22 | Upjohn Co | 1,2,8,ba-ciclopropa(c)-benzo(1,2-b-4,3-b)dipirrol-4(5h)-one antibatte ricamente attivo e relativo metodo di preparazione |
-
1983
- 1983-01-10 DE DE19833300522 patent/DE3300522A1/de active Granted
- 1983-01-12 FR FR8300497A patent/FR2519982B1/fr not_active Expired
- 1983-01-14 FI FI830137A patent/FI79098C/fi not_active IP Right Cessation
- 1983-01-17 NL NL8300159A patent/NL8300159A/nl not_active Application Discontinuation
- 1983-01-19 NZ NZ203056A patent/NZ203056A/en unknown
- 1983-01-19 ES ES519108A patent/ES519108A0/es active Granted
- 1983-01-19 CH CH5162/83A patent/CH657848A5/de not_active IP Right Cessation
- 1983-01-19 PT PT76110A patent/PT76110B/pt not_active IP Right Cessation
- 1983-01-19 IL IL67715A patent/IL67715A/xx not_active IP Right Cessation
- 1983-01-19 AU AU10611/83A patent/AU565538B2/en not_active Ceased
- 1983-01-19 GB GB08301383A patent/GB2113682B/en not_active Expired
- 1983-01-19 DK DK020983A patent/DK161071C/da not_active IP Right Cessation
- 1983-01-19 WO PCT/CH1983/000008 patent/WO1983002610A1/en unknown
- 1983-01-20 HU HU83189A patent/HU189215B/hu not_active IP Right Cessation
- 1983-01-20 IE IE115/83A patent/IE54878B1/en not_active IP Right Cessation
- 1983-01-20 IT IT47588/83A patent/IT1197546B/it active
- 1983-01-20 CA CA000419841A patent/CA1191857A/en not_active Expired
- 1983-01-20 SE SE8300289A patent/SE453293B/sv not_active IP Right Cessation
- 1983-01-20 AT AT0017483A patent/AT381490B/de not_active IP Right Cessation
-
1985
- 1985-01-17 US US06/458,443 patent/US4622336A/en not_active Expired - Fee Related
-
1986
- 1986-01-11 PH PH28376A patent/PH22848A/en unknown
- 1986-12-30 MY MY467/86A patent/MY8600467A/xx unknown
-
1988
- 1988-04-05 SG SG226/88A patent/SG22688G/en unknown
- 1988-04-27 KE KE3813A patent/KE3813A/xx unknown
- 1988-07-28 HK HK568/88A patent/HK56888A/xx unknown
- 1988-09-02 CY CY1431A patent/CY1431A/en unknown
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