FR2475044A1 - Derives de nitro-2 naphtofurannes, leur preparation et leur application notamment comme regulateurs de la croissance cellulaire - Google Patents
Derives de nitro-2 naphtofurannes, leur preparation et leur application notamment comme regulateurs de la croissance cellulaire Download PDFInfo
- Publication number
- FR2475044A1 FR2475044A1 FR8002354A FR8002354A FR2475044A1 FR 2475044 A1 FR2475044 A1 FR 2475044A1 FR 8002354 A FR8002354 A FR 8002354A FR 8002354 A FR8002354 A FR 8002354A FR 2475044 A1 FR2475044 A1 FR 2475044A1
- Authority
- FR
- France
- Prior art keywords
- naphthalene
- nitro
- methoxy
- formula
- formyl
- 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
- 230000010261 cell growth Effects 0.000 title claims abstract description 4
- 238000002360 preparation method Methods 0.000 title claims description 7
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- HXRMBVOCHDEAQH-UHFFFAOYSA-N 2-nitrobenzo[e][1]benzofuran Chemical class C1=CC=C2C(C=C(O3)[N+](=O)[O-])=C3C=CC2=C1 HXRMBVOCHDEAQH-UHFFFAOYSA-N 0.000 claims abstract description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 20
- 150000001299 aldehydes Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 238000009833 condensation Methods 0.000 claims description 5
- 230000005494 condensation Effects 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003630 growth substance Substances 0.000 abstract 1
- 150000002790 naphthalenes Chemical class 0.000 abstract 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 238000009835 boiling Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- VTUMHIXLEZHVEJ-UHFFFAOYSA-N 2,3-dimethoxynaphthalene-1-carbaldehyde Chemical class C1=CC=C2C(C=O)=C(OC)C(OC)=CC2=C1 VTUMHIXLEZHVEJ-UHFFFAOYSA-N 0.000 description 2
- SZKBFOWEOKWEDD-UHFFFAOYSA-N 2,6-dimethoxynaphthalene-1-carbaldehyde Chemical compound O=CC1=C(OC)C=CC2=CC(OC)=CC=C21 SZKBFOWEOKWEDD-UHFFFAOYSA-N 0.000 description 2
- PTTJQHKRNJYUGV-UHFFFAOYSA-N 2,7-dimethoxynaphthalene-1-carbaldehyde Chemical compound C1=CC(OC)=C(C=O)C2=CC(OC)=CC=C21 PTTJQHKRNJYUGV-UHFFFAOYSA-N 0.000 description 2
- OTNKCGQLSHSABI-UHFFFAOYSA-N 2-hydroxy-6-methoxynaphthalene-1-carbaldehyde Chemical compound O=CC1=C(O)C=CC2=CC(OC)=CC=C21 OTNKCGQLSHSABI-UHFFFAOYSA-N 0.000 description 2
- SSXGLTBMLLIRCN-UHFFFAOYSA-N 3-hydroxy-5-methoxynaphthalene-2-carbaldehyde Chemical compound O=CC1=C(O)C=C2C(OC)=CC=CC2=C1 SSXGLTBMLLIRCN-UHFFFAOYSA-N 0.000 description 2
- SJTNTIRIRIPZDV-UHFFFAOYSA-N 3-methoxynaphthalen-2-ol Chemical compound C1=CC=C2C=C(O)C(OC)=CC2=C1 SJTNTIRIRIPZDV-UHFFFAOYSA-N 0.000 description 2
- FTCRRHMDEKNDHP-UHFFFAOYSA-N 4-chloro-1-hydroxynaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C(O)=C(C=O)C=C(Cl)C2=C1 FTCRRHMDEKNDHP-UHFFFAOYSA-N 0.000 description 2
- LVSPDZAGCBEQAV-UHFFFAOYSA-N 4-chloronaphthalen-1-ol Chemical compound C1=CC=C2C(O)=CC=C(Cl)C2=C1 LVSPDZAGCBEQAV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- -1 OCH3 Compound Chemical class 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 230000017858 demethylation Effects 0.000 description 2
- 238000010520 demethylation reaction Methods 0.000 description 2
- GRTGGSXWHGKRSB-UHFFFAOYSA-N dichloromethyl methyl ether Chemical compound COC(Cl)Cl GRTGGSXWHGKRSB-UHFFFAOYSA-N 0.000 description 2
- 239000003471 mutagenic agent Substances 0.000 description 2
- 231100000707 mutagenic chemical Toxicity 0.000 description 2
- 230000003505 mutagenic effect Effects 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical compound C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 description 1
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 1
- JHQLIHCBBWWVDY-UHFFFAOYSA-N 2-hydroxy-3-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC=C2C(C=O)=C(O)C(OC)=CC2=C1 JHQLIHCBBWWVDY-UHFFFAOYSA-N 0.000 description 1
- WQGADZACBGKOHW-UHFFFAOYSA-N 2-hydroxy-7-methoxynaphthalene-1-carbaldehyde Chemical compound C1=CC(O)=C(C=O)C2=CC(OC)=CC=C21 WQGADZACBGKOHW-UHFFFAOYSA-N 0.000 description 1
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 1
- RAWBFWIHQDOJLK-UHFFFAOYSA-N 3,5-dimethoxynaphthalene-2-carbaldehyde Chemical compound C1=CC=C2C=C(C=O)C(OC)=CC2=C1OC RAWBFWIHQDOJLK-UHFFFAOYSA-N 0.000 description 1
- RCUCQCSUVXIHON-UHFFFAOYSA-N 4-methoxy-2-nitronaphthalen-1-ol Chemical compound [N+](=O)([O-])C1=C(C2=CC=CC=C2C(=C1)OC)O RCUCQCSUVXIHON-UHFFFAOYSA-N 0.000 description 1
- YLDFTMJPQJXGSS-UHFFFAOYSA-N 6-bromo-2-naphthol Chemical compound C1=C(Br)C=CC2=CC(O)=CC=C21 YLDFTMJPQJXGSS-UHFFFAOYSA-N 0.000 description 1
- VBVIYUGENXSHQJ-UHFFFAOYSA-N 8-methoxy-2-nitrobenzo[f][1]benzofuran Chemical compound C1=C2C(OC)=CC=CC2=CC2=C1OC([N+]([O-])=O)=C2 VBVIYUGENXSHQJ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- LMEMIKWTNPWYMI-UHFFFAOYSA-N acridine half-mustard dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C=CC2=C(NCCCNCCCl)C3=CC(OC)=CC=C3N=C21 LMEMIKWTNPWYMI-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 230000022244 formylation Effects 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 231100000219 mutagenic Toxicity 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 231100000299 mutagenicity Toxicity 0.000 description 1
- 230000007886 mutagenicity Effects 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
- C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
- C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
- C07C45/513—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being an etherified hydroxyl 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
- C07C47/57—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N15/00—Mutation or genetic engineering; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification; Use of hosts therefor
- C12N15/01—Preparation of mutants without inserting foreign genetic material therein; Screening processes therefor
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Plant Pathology (AREA)
- Biophysics (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002354A FR2475044A1 (fr) | 1980-02-04 | 1980-02-04 | Derives de nitro-2 naphtofurannes, leur preparation et leur application notamment comme regulateurs de la croissance cellulaire |
| US06/229,860 US4341794A (en) | 1980-02-04 | 1981-01-30 | 2-Nitronaphtofuran derivatives and use as cell growth regulators |
| CA000369944A CA1154028A (en) | 1980-02-04 | 1981-02-03 | 2-nitronaphtofuran derivatives, their production and use as cell growth regulators |
| JP1556381A JPS56138179A (en) | 1980-02-04 | 1981-02-03 | 2-nitronaphthofuran derivative, manufacture and cell growth regulant containing same |
| EP81400156A EP0033702B1 (fr) | 1980-02-04 | 1981-02-03 | Dérivés de nitro-2 naphtofurannes, leur préparation et leur application notamment comme régulateurs de la croissance cellulaire |
| DE8181400156T DE3161814D1 (en) | 1980-02-04 | 1981-02-03 | 2-nitronaphthofurane derivatives, their preparation and their use, in particular as cell-growth regulators |
| AT81400156T ATE5775T1 (de) | 1980-02-04 | 1981-02-03 | 2-nitronaphtofuranderivate, ihre herstellung und ihre verwendung, insbesondere als zellenwachstumsregulatoren. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8002354A FR2475044A1 (fr) | 1980-02-04 | 1980-02-04 | Derives de nitro-2 naphtofurannes, leur preparation et leur application notamment comme regulateurs de la croissance cellulaire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475044A1 true FR2475044A1 (fr) | 1981-08-07 |
| FR2475044B1 FR2475044B1 (enExample) | 1983-04-01 |
Family
ID=9238167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8002354A Granted FR2475044A1 (fr) | 1980-02-04 | 1980-02-04 | Derives de nitro-2 naphtofurannes, leur preparation et leur application notamment comme regulateurs de la croissance cellulaire |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4341794A (enExample) |
| EP (1) | EP0033702B1 (enExample) |
| JP (1) | JPS56138179A (enExample) |
| AT (1) | ATE5775T1 (enExample) |
| CA (1) | CA1154028A (enExample) |
| DE (1) | DE3161814D1 (enExample) |
| FR (1) | FR2475044A1 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2963784A1 (en) | 2007-06-08 | 2008-12-18 | Mannkind Corporation | Ire-1.alpha. inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128659A (en) * | 1977-12-19 | 1978-12-05 | Riker Laboratories, Inc. | Antimicrobial polycyclic nitrofurans |
| FR2424266A1 (fr) * | 1978-04-24 | 1979-11-23 | Anvar | Derives nitres de naphtofurannes, leur preparation et leur application comme medicaments |
-
1980
- 1980-02-04 FR FR8002354A patent/FR2475044A1/fr active Granted
-
1981
- 1981-01-30 US US06/229,860 patent/US4341794A/en not_active Expired - Fee Related
- 1981-02-03 JP JP1556381A patent/JPS56138179A/ja active Pending
- 1981-02-03 DE DE8181400156T patent/DE3161814D1/de not_active Expired
- 1981-02-03 AT AT81400156T patent/ATE5775T1/de not_active IP Right Cessation
- 1981-02-03 EP EP81400156A patent/EP0033702B1/fr not_active Expired
- 1981-02-03 CA CA000369944A patent/CA1154028A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4128659A (en) * | 1977-12-19 | 1978-12-05 | Riker Laboratories, Inc. | Antimicrobial polycyclic nitrofurans |
| FR2424266A1 (fr) * | 1978-04-24 | 1979-11-23 | Anvar | Derives nitres de naphtofurannes, leur preparation et leur application comme medicaments |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/78 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1154028A (en) | 1983-09-20 |
| FR2475044B1 (enExample) | 1983-04-01 |
| EP0033702B1 (fr) | 1984-01-04 |
| US4341794A (en) | 1982-07-27 |
| JPS56138179A (en) | 1981-10-28 |
| EP0033702A2 (fr) | 1981-08-12 |
| DE3161814D1 (en) | 1984-02-09 |
| ATE5775T1 (de) | 1984-01-15 |
| EP0033702A3 (en) | 1981-08-19 |
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