CA1042442A - N,n-dioxides of bis-basic cyclic ketones - Google Patents
N,n-dioxides of bis-basic cyclic ketonesInfo
- Publication number
- CA1042442A CA1042442A CA219,649A CA219649A CA1042442A CA 1042442 A CA1042442 A CA 1042442A CA 219649 A CA219649 A CA 219649A CA 1042442 A CA1042442 A CA 1042442A
- Authority
- CA
- Canada
- Prior art keywords
- bis
- dioxide
- piperidino
- butyryl
- group
- 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
- 150000003997 cyclic ketones Chemical class 0.000 title claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 239000002253 acid Substances 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract 2
- 239000000243 solution Substances 0.000 claims description 32
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical class OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 9
- KQKCWHPANDHXPN-UHFFFAOYSA-N 4-piperidin-1-yl-1-[7-(4-piperidin-1-ylbutanoyl)-9h-fluoren-2-yl]butan-1-one Chemical compound C=1C=C(C2=CC=C(C=C2C2)C(=O)CCCN3CCCCC3)C2=CC=1C(=O)CCCN1CCCCC1 KQKCWHPANDHXPN-UHFFFAOYSA-N 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
- ZNDNZBVYMDSTJN-UHFFFAOYSA-N 2,7-bis(4-piperidin-1-ylbutanoyl)fluoren-9-one Chemical compound C=1C=C2C3=CC=C(C(=O)CCCN4CCCCC4)C=C3C(=O)C2=CC=1C(=O)CCCN1CCCCC1 ZNDNZBVYMDSTJN-UHFFFAOYSA-N 0.000 claims description 6
- 150000004965 peroxy acids Chemical class 0.000 claims description 6
- GCIPCERDYIFYNF-UHFFFAOYSA-N 4-piperidin-1-yl-1-[4-(4-piperidin-1-ylbutanoyl)fluoranthen-8-yl]butan-1-one Chemical compound C=1C=C(C=2C=CC=C3C(C(=O)CCCN4CCCCC4)=CC=C4C=23)C4=CC=1C(=O)CCCN1CCCCC1 GCIPCERDYIFYNF-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims description 3
- 125000001442 methylidyne group Chemical group [H]C#[*] 0.000 claims description 2
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical compound C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 abstract description 43
- 230000009385 viral infection Effects 0.000 abstract description 12
- 230000005764 inhibitory process Effects 0.000 abstract 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 abstract description 3
- 230000002265 prevention Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 description 36
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthene Chemical compound C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 33
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 241001465754 Metazoa Species 0.000 description 29
- 241000700605 Viruses Species 0.000 description 29
- 239000004480 active ingredient Substances 0.000 description 27
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 27
- 150000002576 ketones Chemical class 0.000 description 25
- -1 2,6-bis[2-(dimethylamino)propionyl]fluorene Chemical compound 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 208000015181 infectious disease Diseases 0.000 description 16
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000005755 formation reaction Methods 0.000 description 14
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- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 description 12
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
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- 238000007254 oxidation reaction Methods 0.000 description 11
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- 239000002585 base Substances 0.000 description 9
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
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- 241000699670 Mus sp. Species 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 210000001519 tissue Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- 239000003443 antiviral agent Substances 0.000 description 5
- 206010022000 influenza Diseases 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 5
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- 229960005486 vaccine Drugs 0.000 description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 4
- DZZNWQDCOZGSMJ-UHFFFAOYSA-N 5-(dimethylamino)-1-[7-[5-(dimethylamino)pentanoyl]-9h-fluoren-2-yl]pentan-1-one Chemical compound CN(C)CCCCC(=O)C1=CC=C2C3=CC=C(C(=O)CCCCN(C)C)C=C3CC2=C1 DZZNWQDCOZGSMJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 102000014150 Interferons Human genes 0.000 description 4
- 108010050904 Interferons Proteins 0.000 description 4
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- 239000004264 Petrolatum Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical group 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 229940079322 interferon Drugs 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
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- YLZJXKRNYXKCOV-UHFFFAOYSA-N 4-piperidin-1-yl-1-[7-(4-piperidin-1-ylbutanoyl)-9h-xanthen-2-yl]butan-1-one Chemical compound C=1C=C2OC3=CC=C(C(=O)CCCN4CCCCC4)C=C3CC2=CC=1C(=O)CCCN1CCCCC1 YLZJXKRNYXKCOV-UHFFFAOYSA-N 0.000 description 3
- LUVLHVJJTLGAFU-UHFFFAOYSA-N 5-(diethylamino)-1-[7-[5-(diethylamino)pentanoyl]-9h-fluoren-2-yl]pentan-1-one Chemical compound CCN(CC)CCCCC(=O)C1=CC=C2C3=CC=C(C(=O)CCCCN(CC)CC)C=C3CC2=C1 LUVLHVJJTLGAFU-UHFFFAOYSA-N 0.000 description 3
- IYHHYVDCCCZJOZ-UHFFFAOYSA-N 5-(dimethylamino)-1-[7-[5-(dimethylamino)pentanoyl]-9h-xanthen-2-yl]pentan-1-one Chemical compound C1=C(C(=O)CCCCN(C)C)C=C2CC3=CC(C(=O)CCCCN(C)C)=CC=C3OC2=C1 IYHHYVDCCCZJOZ-UHFFFAOYSA-N 0.000 description 3
- XHRMNOLFVKFLJK-UHFFFAOYSA-N 5-chloro-1-[7-(5-chloropentanoyl)-9h-xanthen-2-yl]pentan-1-one Chemical compound C1=C(C(=O)CCCCCl)C=C2CC3=CC(C(=O)CCCCCl)=CC=C3OC2=C1 XHRMNOLFVKFLJK-UHFFFAOYSA-N 0.000 description 3
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- 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/24—Oxygen atoms
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- 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
- C07D295/10—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 doubly bound oxygen or sulphur atoms
- C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
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- 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
- C07D311/82—Xanthenes
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- 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
- C07D311/82—Xanthenes
- C07D311/84—Xanthenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 9
- C07D311/86—Oxygen atoms, e.g. xanthones
-
- 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
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
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)
- Pyrane Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US449225A US3890328A (en) | 1974-03-08 | 1974-03-08 | N,N-dioxides of bis-basic cyclic ketones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1042442A true CA1042442A (en) | 1978-11-14 |
Family
ID=23783388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA219,649A Expired CA1042442A (en) | 1974-03-08 | 1975-02-07 | N,n-dioxides of bis-basic cyclic ketones |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3890328A (OSRAM) |
| JP (1) | JPS50121258A (OSRAM) |
| BE (1) | BE826427A (OSRAM) |
| CA (1) | CA1042442A (OSRAM) |
| CH (1) | CH612927A5 (OSRAM) |
| DE (1) | DE2508225A1 (OSRAM) |
| FR (1) | FR2262969B1 (OSRAM) |
| GB (1) | GB1447023A (OSRAM) |
| IL (1) | IL46663A (OSRAM) |
| NL (1) | NL7502207A (OSRAM) |
| SE (1) | SE7502604L (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60241244A (ja) * | 1984-05-16 | 1985-11-30 | Hitachi Micro Comput Eng Ltd | ピングリッドアレイ型半導体装置の製造方法 |
| US4696936A (en) * | 1984-11-09 | 1987-09-29 | American Cyanamid Company | 3,6-bis (substituted) acridine N-oxides and N,N-dioxides and methods of restoring, stimulating or enhancing the immune system with them |
| US6635786B2 (en) * | 2001-01-16 | 2003-10-21 | Guilford Pharmaceuticals, Inc. | Symmetrically disubstituted aromatic compounds and pharmaceutical compositions for inhibiting poly (ADP-ribose) glycohydrolase, and methods for their use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3576865A (en) * | 1968-10-11 | 1971-04-27 | Richardson Merrell Inc | Fluorenone-,fluorenol-,and fluorenebis-basic carboxamides |
| US3531489A (en) * | 1968-10-18 | 1970-09-29 | Richardson Merrell Inc | Bis-basic esters and thioesters of fluoranthene |
| IL33573A (en) * | 1968-12-30 | 1973-10-25 | Richardson Merrell Inc | Bis-basic ethers and thioethers of fluorenone,fluorenol and fluorene |
| US3647860A (en) * | 1969-01-09 | 1972-03-07 | Richardson Merrell Inc | Fluorene bis-basic esters |
| US3707471A (en) * | 1970-04-27 | 1972-12-26 | Richardson Merrell Inc | Fluoranthene bis-basic ethers and thioethers |
-
1974
- 1974-03-08 US US449225A patent/US3890328A/en not_active Expired - Lifetime
-
1975
- 1975-02-07 CA CA219,649A patent/CA1042442A/en not_active Expired
- 1975-02-13 GB GB608575A patent/GB1447023A/en not_active Expired
- 1975-02-19 IL IL46663A patent/IL46663A/xx unknown
- 1975-02-25 NL NL7502207A patent/NL7502207A/xx not_active Application Discontinuation
- 1975-02-26 DE DE19752508225 patent/DE2508225A1/de not_active Withdrawn
- 1975-03-04 CH CH269875A patent/CH612927A5/xx not_active IP Right Cessation
- 1975-03-06 FR FR7507029A patent/FR2262969B1/fr not_active Expired
- 1975-03-07 SE SE7502604A patent/SE7502604L/xx unknown
- 1975-03-07 BE BE154125A patent/BE826427A/xx unknown
- 1975-03-07 JP JP50027253A patent/JPS50121258A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50121258A (OSRAM) | 1975-09-23 |
| AU7824875A (en) | 1976-08-19 |
| GB1447023A (en) | 1976-08-25 |
| US3890328A (en) | 1975-06-17 |
| FR2262969A1 (OSRAM) | 1975-10-03 |
| IL46663A0 (en) | 1975-04-25 |
| DE2508225A1 (de) | 1975-09-18 |
| BE826427A (fr) | 1975-06-30 |
| CH612927A5 (OSRAM) | 1979-08-31 |
| IL46663A (en) | 1978-09-29 |
| SE7502604L (OSRAM) | 1975-09-09 |
| NL7502207A (nl) | 1975-09-10 |
| FR2262969B1 (OSRAM) | 1978-07-28 |
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