DE2362748A1 - Neue bis-basische ester von 9-substituierten phenanthrenen und deren verwandten oxa- und azaderivaten, verfahren zu ihrer herstellung sowie diese enthaltende pharmazeutische zusammensetzungen - Google Patents
Neue bis-basische ester von 9-substituierten phenanthrenen und deren verwandten oxa- und azaderivaten, verfahren zu ihrer herstellung sowie diese enthaltende pharmazeutische zusammensetzungenInfo
- Publication number
- DE2362748A1 DE2362748A1 DE2362748A DE2362748A DE2362748A1 DE 2362748 A1 DE2362748 A1 DE 2362748A1 DE 2362748 A DE2362748 A DE 2362748A DE 2362748 A DE2362748 A DE 2362748A DE 2362748 A1 DE2362748 A1 DE 2362748A1
- Authority
- DE
- Germany
- Prior art keywords
- bis
- dicarboxylic acid
- acid ester
- group
- pyran
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 12
- 230000008569 process Effects 0.000 title claims description 6
- 150000002987 phenanthrenes Chemical class 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 56
- 150000002148 esters Chemical class 0.000 claims description 46
- -1 9-substituted phenanthrenes Chemical class 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000002360 preparation method Methods 0.000 claims description 17
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004915 dibutylamino group Chemical group C(CCC)N(CCCC)* 0.000 claims description 11
- JUINSXZKUKVTMD-UHFFFAOYSA-N hydrogen azide Chemical compound N=[N+]=[N-] JUINSXZKUKVTMD-UHFFFAOYSA-N 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- 229910052760 oxygen Inorganic materials 0.000 claims description 2
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- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 11
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- 238000012360 testing method Methods 0.000 description 10
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
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- 230000000840 anti-viral effect Effects 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
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- 229940079322 interferon Drugs 0.000 description 6
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- DZKIUEHLEXLYKM-UHFFFAOYSA-N 9-phenanthrol Chemical compound C1=CC=C2C(O)=CC3=CC=CC=C3C2=C1 DZKIUEHLEXLYKM-UHFFFAOYSA-N 0.000 description 4
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- 239000007916 tablet composition Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 206010044325 trachoma Diseases 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 241000712461 unidentified influenza virus Species 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/04—Ortho- or peri-condensed ring systems
- C07D221/06—Ring systems of three rings
- C07D221/10—Aza-phenanthrenes
- C07D221/12—Phenanthridines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
-
- 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
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
-
- 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
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US317146A US3859312A (en) | 1972-12-21 | 1972-12-21 | 6h-dibenzo(b,d)pyran-6-ones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2362748A1 true DE2362748A1 (de) | 1974-06-27 |
Family
ID=23232309
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2362748A Withdrawn DE2362748A1 (de) | 1972-12-21 | 1973-12-17 | Neue bis-basische ester von 9-substituierten phenanthrenen und deren verwandten oxa- und azaderivaten, verfahren zu ihrer herstellung sowie diese enthaltende pharmazeutische zusammensetzungen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3859312A (enExample) |
| JP (1) | JPS4988848A (enExample) |
| AU (1) | AU476754B2 (enExample) |
| CA (1) | CA1042443A (enExample) |
| DE (1) | DE2362748A1 (enExample) |
| FR (1) | FR2211237B1 (enExample) |
| GB (1) | GB1421075A (enExample) |
| IL (1) | IL43669A (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4059702A (en) * | 1972-12-21 | 1977-11-22 | Richardson-Merrell Inc. | 3,8-Bis-basic ethers of 6H-dibenzo[b,d]pyran-6-one |
| WO1989008973A1 (en) * | 1988-03-11 | 1989-09-21 | Magellan Corporation (Australia) Pty. Ltd. | Inductive element and method of manufacture |
| EP2061765B1 (en) * | 2006-09-01 | 2014-10-22 | Senhwa Biosciences, Inc. | Serine-threonine protein kinase and PARP modulators |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE665214C (de) * | 1936-02-08 | 1938-09-21 | Geigy Ag J R | Bekaempfen und Vertreiben von Insekten und Insektenlarven |
-
1972
- 1972-12-21 US US317146A patent/US3859312A/en not_active Expired - Lifetime
-
1973
- 1973-10-26 AU AU61885/73A patent/AU476754B2/en not_active Expired
- 1973-10-29 CA CA184,536A patent/CA1042443A/en not_active Expired
- 1973-11-21 IL IL43669A patent/IL43669A/xx unknown
- 1973-12-17 GB GB5826173A patent/GB1421075A/en not_active Expired
- 1973-12-17 DE DE2362748A patent/DE2362748A1/de not_active Withdrawn
- 1973-12-19 FR FR7345513A patent/FR2211237B1/fr not_active Expired
- 1973-12-20 JP JP48141916A patent/JPS4988848A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| IL43669A (en) | 1978-08-31 |
| FR2211237A1 (enExample) | 1974-07-19 |
| AU6188573A (en) | 1975-05-01 |
| AU476754B2 (en) | 1976-09-30 |
| US3859312A (en) | 1975-01-07 |
| FR2211237B1 (enExample) | 1976-12-31 |
| IL43669A0 (en) | 1974-03-14 |
| GB1421075A (en) | 1976-01-14 |
| JPS4988848A (enExample) | 1974-08-24 |
| CA1042443A (en) | 1978-11-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| 8130 | Withdrawal |