DE3300522A1 - 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend - Google Patents
3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltendInfo
- Publication number
- DE3300522A1 DE3300522A1 DE19833300522 DE3300522A DE3300522A1 DE 3300522 A1 DE3300522 A1 DE 3300522A1 DE 19833300522 DE19833300522 DE 19833300522 DE 3300522 A DE3300522 A DE 3300522A DE 3300522 A1 DE3300522 A1 DE 3300522A1
- Authority
- DE
- Germany
- Prior art keywords
- indoline
- formula
- carbon atoms
- acid addition
- indolines
- 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.)
- Granted
Links
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- 238000000034 method Methods 0.000 title claims description 24
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 35
- 150000002148 esters Chemical class 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000006239 protecting group Chemical group 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- JYGFTBXVXVMTGB-UHFFFAOYSA-N indolin-2-one Chemical class C1=CC=C2NC(=O)CC2=C1 JYGFTBXVXVMTGB-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 238000005661 deetherification reaction Methods 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- AYVGKVADTZHDDD-UHFFFAOYSA-N 5-ethoxy-3,3-dimethyl-1,2-dihydroindole Chemical compound CCOC1=CC=C2NCC(C)(C)C2=C1 AYVGKVADTZHDDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
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- 239000003814 drug Substances 0.000 claims description 3
- 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 description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
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- 230000015572 biosynthetic process Effects 0.000 description 3
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- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 3
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- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
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- LORFYXRHZOYYFN-UHFFFAOYSA-N 1-acetyl-5-methoxy-3h-indol-2-one Chemical compound COC1=CC=C2N(C(C)=O)C(=O)CC2=C1 LORFYXRHZOYYFN-UHFFFAOYSA-N 0.000 description 2
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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 description 2
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- 229910010082 LiAlH Inorganic materials 0.000 description 2
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- PCKPVGOLPKLUHR-UHFFFAOYSA-N OH-Indolxyl Natural products C1=CC=C2C(O)=CNC2=C1 PCKPVGOLPKLUHR-UHFFFAOYSA-N 0.000 description 2
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- 239000012730 sustained-release form Substances 0.000 description 1
- 150000003609 titanium compounds Chemical class 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
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 (2)
| Publication Number | Publication Date |
|---|---|
| DE3300522A1 true DE3300522A1 (de) | 1983-07-28 |
| DE3300522C2 DE3300522C2 (en, 2012) | 1992-01-09 |
Family
ID=25684383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19833300522 Granted DE3300522A1 (de) | 1982-01-21 | 1983-01-10 | 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend |
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 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2245159A1 (de) * | 1971-09-16 | 1973-03-22 | Kabi Ab | Stickstoffhaltige heterocyclische verbindungen |
| DE2442667A1 (de) * | 1973-09-10 | 1975-03-13 | Lepetit Spa | Neue indolderivate, ein verfahren zu ihrer herstellung sowie arzneimittel |
| DE2943192A1 (de) * | 1978-10-31 | 1980-05-14 | Ihara Chemical Ind Co | Verfahren zur herstellung von indolin-derivaten |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 | |||
| 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 |
| 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
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2245159A1 (de) * | 1971-09-16 | 1973-03-22 | Kabi Ab | Stickstoffhaltige heterocyclische verbindungen |
| DE2442667A1 (de) * | 1973-09-10 | 1975-03-13 | Lepetit Spa | Neue indolderivate, ein verfahren zu ihrer herstellung sowie arzneimittel |
| DE2943192A1 (de) * | 1978-10-31 | 1980-05-14 | Ihara Chemical Ind Co | Verfahren zur herstellung von indolin-derivaten |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |