GB1412291A - 2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing them - Google Patents
2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing themInfo
- Publication number
- GB1412291A GB1412291A GB1330072*[A GB334872A GB1412291A GB 1412291 A GB1412291 A GB 1412291A GB 334872 A GB334872 A GB 334872A GB 1412291 A GB1412291 A GB 1412291A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- methyl
- compounds
- phenyl
- alkyl
- 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
- CJGMVHVKJXBIDT-UHFFFAOYSA-N 2-nitroindene-1,3-dione Chemical class C1=CC=C2C(=O)C([N+](=O)[O-])C(=O)C2=C1 CJGMVHVKJXBIDT-UHFFFAOYSA-N 0.000 title 1
- 230000003266 anti-allergic effect Effects 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- 238000006243 chemical reaction Methods 0.000 abstract 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000001246 bromo group Chemical group Br* 0.000 abstract 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 abstract 2
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 abstract 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 abstract 1
- 238000003512 Claisen condensation reaction Methods 0.000 abstract 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- -1 iso-propyloxy Chemical group 0.000 abstract 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 238000006396 nitration reaction Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/38—Unsaturated compounds containing keto groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
- C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
- C07C49/675—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having three rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
- C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/16—Benz[e]indenes; Hydrogenated benz[e]indenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (23)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1330072*[A GB1412291A (en) | 1972-01-25 | 1972-01-25 | 2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing them |
| ZA728749A ZA728749B (en) | 1972-01-25 | 1972-12-11 | Anti-allergic pharmaceutical compositions |
| SE7216376A SE401821B (sv) | 1972-01-25 | 1972-12-14 | Forfarande for framstellning av derivat av 2-nitroindan-1,3-dion, vilka derivat har antiallergiska egenskaper |
| AU50081/72A AU473725B2 (en) | 1972-01-25 | 1972-12-14 | Pharmaceutical compositions comprising 2-nitroindane-1, 3-diones and process for their preparation |
| CA159,009A CA1017757A (en) | 1972-01-25 | 1972-12-15 | 2-nitroindane-1,3-dione derivatives |
| DK629972AA DK137379B (da) | 1972-01-25 | 1972-12-15 | Analogifremgangsmåde til fremstilling af 2-nitroindan-1,3-dionderivater med anti-allergenisk virkning. |
| DE19722261568 DE2261568A1 (de) | 1972-01-25 | 1972-12-15 | 2-nitroindan-1,3-dion-verbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate |
| NL7217175A NL7217175A (enExample) | 1972-01-25 | 1972-12-15 | |
| CH1833772A CH592603A5 (enExample) | 1972-01-25 | 1972-12-15 | |
| NO4655/72A NO135632C (enExample) | 1972-01-25 | 1972-12-15 | |
| BE792867D BE792867A (fr) | 1972-01-25 | 1972-12-15 | Compositions pharmaceutiques anti-allergiques |
| ES409669A ES409669A1 (es) | 1972-01-25 | 1972-12-15 | Un procedimiento para la preparacion de nuevos derivados de2-nitroindan-1,3-diona. |
| US05/317,296 US3936504A (en) | 1972-01-25 | 1972-12-21 | Anti-allergic pharmaceutical compositions |
| FR7300713A FR2181661B1 (enExample) | 1972-01-25 | 1973-01-10 | |
| IN1196/CAL/73A IN138640B (enExample) | 1972-01-25 | 1973-05-22 | |
| US421239A US3925557A (en) | 1972-01-25 | 1973-12-03 | Anti-allergic pharmaceutical compositions |
| US05/549,869 US3988476A (en) | 1972-01-25 | 1975-02-14 | Pharmaceutical compositions and methods of treating allergic conditions utilizing 2-nitroindane-1,3-dione derivatives as the active agent |
| US05/556,861 US3978231A (en) | 1972-01-25 | 1975-03-10 | Pharmaceutical compositions and method of treating allergic conditions utilizing 2-nitroindane-1,3-dione derivatives as the active agents |
| ES437882A ES437882A1 (es) | 1972-01-25 | 1975-05-22 | Un procedimiento para la preparacion de 5,6-dimetilindan-1,3-diona y sus sales farmaceuticamente aceptables. |
| CA245,479A CA1017358A (en) | 1972-01-25 | 1976-02-11 | Preparation of 5,6-dimethylindane-1,3-dione |
| SE7610364A SE7610364L (sv) | 1972-01-25 | 1976-09-17 | Forening anvendbar som mellanprodukt vid framstellning av 5,6-dimetyl-2-nitroindan-1,3-dion |
| CA267,480A CA1021799A (en) | 1972-01-25 | 1976-12-09 | 5,6-dimethylindane-1,3-dione and its preparation |
| DK560577A DK560577A (da) | 1972-01-25 | 1977-12-15 | 5,6-dimethylindan-1,3-dion til anvendelse som mellemprodukt ved fremstilling af 5,6-dimethyl-2-nitrindan-1,3-dion med anti-allergenisk virkning samt en fremgangsmade til fremstilling af 5,6-dimethylindan-1,3-dion |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1330072*[A GB1412291A (en) | 1972-01-25 | 1972-01-25 | 2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing them |
| GB1330072 | 1972-03-22 | ||
| GB2870772 | 1972-06-20 | ||
| GB4802772 | 1972-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1412291A true GB1412291A (en) | 1975-11-05 |
Family
ID=27447285
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1330072*[A Expired GB1412291A (en) | 1972-01-25 | 1972-01-25 | 2-nitro-indan-1,3-diones methods for their preparation and anti-allergic compositions containing them |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3936504A (enExample) |
| BE (1) | BE792867A (enExample) |
| CA (2) | CA1017757A (enExample) |
| CH (1) | CH592603A5 (enExample) |
| DE (1) | DE2261568A1 (enExample) |
| DK (2) | DK137379B (enExample) |
| FR (1) | FR2181661B1 (enExample) |
| GB (1) | GB1412291A (enExample) |
| NL (1) | NL7217175A (enExample) |
| NO (1) | NO135632C (enExample) |
| SE (2) | SE401821B (enExample) |
-
1972
- 1972-01-25 GB GB1330072*[A patent/GB1412291A/en not_active Expired
- 1972-12-14 SE SE7216376A patent/SE401821B/xx unknown
- 1972-12-15 DK DK629972AA patent/DK137379B/da unknown
- 1972-12-15 DE DE19722261568 patent/DE2261568A1/de active Pending
- 1972-12-15 BE BE792867D patent/BE792867A/xx unknown
- 1972-12-15 NO NO4655/72A patent/NO135632C/no unknown
- 1972-12-15 NL NL7217175A patent/NL7217175A/xx not_active Application Discontinuation
- 1972-12-15 CA CA159,009A patent/CA1017757A/en not_active Expired
- 1972-12-15 CH CH1833772A patent/CH592603A5/xx not_active IP Right Cessation
- 1972-12-21 US US05/317,296 patent/US3936504A/en not_active Expired - Lifetime
-
1973
- 1973-01-10 FR FR7300713A patent/FR2181661B1/fr not_active Expired
-
1976
- 1976-09-17 SE SE7610364A patent/SE7610364L/xx unknown
- 1976-12-09 CA CA267,480A patent/CA1021799A/en not_active Expired
-
1977
- 1977-12-15 DK DK560577A patent/DK560577A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1017757A (en) | 1977-09-20 |
| NO135632C (enExample) | 1977-05-04 |
| NL7217175A (enExample) | 1973-07-27 |
| DE2261568A1 (de) | 1973-08-02 |
| CA1021799A (en) | 1977-11-29 |
| NO135632B (enExample) | 1977-01-24 |
| DK137379C (enExample) | 1978-08-07 |
| FR2181661A1 (enExample) | 1973-12-07 |
| US3936504A (en) | 1976-02-03 |
| BE792867A (fr) | 1973-06-15 |
| DK137379B (da) | 1978-02-27 |
| SE7610364L (sv) | 1976-09-17 |
| FR2181661B1 (enExample) | 1976-06-25 |
| DK560577A (da) | 1977-12-15 |
| SE401821B (sv) | 1978-05-29 |
| CH592603A5 (enExample) | 1977-10-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |