FR2475540A1 - Ethers basiques de 4-hydroxy-benzophenones, leur preparation et leurs utilisations therapeutiques - Google Patents
Ethers basiques de 4-hydroxy-benzophenones, leur preparation et leurs utilisations therapeutiques Download PDFInfo
- Publication number
- FR2475540A1 FR2475540A1 FR8102669A FR8102669A FR2475540A1 FR 2475540 A1 FR2475540 A1 FR 2475540A1 FR 8102669 A FR8102669 A FR 8102669A FR 8102669 A FR8102669 A FR 8102669A FR 2475540 A1 FR2475540 A1 FR 2475540A1
- Authority
- FR
- France
- Prior art keywords
- formula
- hydroxy
- compound
- compounds
- benzophenones
- 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
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 230000001225 therapeutic effect Effects 0.000 title claims abstract description 5
- 239000012965 benzophenone Substances 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 150000002170 ethers Chemical class 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims abstract 3
- 150000007513 acids Chemical class 0.000 claims abstract 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 7
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical class C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000000144 pharmacologic effect Effects 0.000 claims description 4
- 239000002876 beta blocker Substances 0.000 claims description 3
- 229940097320 beta blocking agent Drugs 0.000 claims description 3
- 229910052801 chlorine Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000009826 distribution Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 238000001179 sorption measurement Methods 0.000 claims description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 239000013543 active substance Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000002547 new drug Substances 0.000 claims 1
- 150000002924 oxiranes Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- -1 naphthyl radical Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 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 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- ZFDLKXODHDEZEC-UHFFFAOYSA-N (4-chlorophenyl)-[4-(oxiran-2-ylmethoxy)phenyl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)C(C=C1)=CC=C1OCC1OC1 ZFDLKXODHDEZEC-UHFFFAOYSA-N 0.000 description 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- WONQRVASZHJNFS-UHFFFAOYSA-N 4-[2-hydroxy-3-(propan-2-ylazaniumyl)propoxy]benzoate Chemical compound CC(C)NCC(O)COC1=CC=C(C(O)=O)C=C1 WONQRVASZHJNFS-UHFFFAOYSA-N 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- VNJKIQCYNCQEOW-UHFFFAOYSA-N [2-(oxiran-2-ylmethoxy)phenyl]-phenylmethanone Chemical compound C=1C=CC=C(OCC2OC2)C=1C(=O)C1=CC=CC=C1 VNJKIQCYNCQEOW-UHFFFAOYSA-N 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT19887/80A IT1147311B (it) | 1980-02-13 | 1980-02-13 | Eteri basici di 4-idrossi-benzofenoni con attivita' quali agenti betabloccanti e relativi procedimento di preparazione |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2475540A1 true FR2475540A1 (fr) | 1981-08-14 |
| FR2475540B1 FR2475540B1 (enExample) | 1984-09-14 |
Family
ID=11162071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8102669A Granted FR2475540A1 (fr) | 1980-02-13 | 1981-02-11 | Ethers basiques de 4-hydroxy-benzophenones, leur preparation et leurs utilisations therapeutiques |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4376788A (enExample) |
| JP (1) | JPS6026381B2 (enExample) |
| AT (1) | AT374450B (enExample) |
| CA (1) | CA1138897A (enExample) |
| DE (1) | DE3104785A1 (enExample) |
| ES (1) | ES498846A0 (enExample) |
| FR (1) | FR2475540A1 (enExample) |
| GB (1) | GB2068963B (enExample) |
| IT (1) | IT1147311B (enExample) |
| ZA (1) | ZA81946B (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63208911A (ja) * | 1987-02-26 | 1988-08-30 | Atsugi Motor Parts Co Ltd | 圧力制御弁 |
| EP2459519B1 (en) * | 2009-07-30 | 2017-11-29 | Basf Se | Macrophotoinitiators |
| CN102762601B (zh) | 2010-02-23 | 2014-03-26 | 科洛普拉斯特公司 | 聚合物型光引发剂 |
| WO2011160638A1 (en) | 2010-06-22 | 2011-12-29 | Coloplast A/S | Hydrophilic gels from polyalkylether-based photoinitiators |
| SG186779A1 (en) | 2010-06-22 | 2013-02-28 | Coloplast As | Skin-friendly adhesives from polyalkylether-based photoinitiators |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2314711A1 (fr) * | 1975-06-20 | 1977-01-14 | May & Baker Ltd | Nouveaux derives de la benzophenone |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3102839A (en) * | 1960-03-04 | 1963-09-03 | West Laboratories Inc | Germicidal compositions |
| LU53667A1 (enExample) * | 1966-07-26 | 1968-11-29 | ||
| GB1185044A (en) * | 1966-11-03 | 1970-03-18 | Ici Ltd | Alkanolamine Derivatives |
| US3553332A (en) * | 1967-06-27 | 1971-01-05 | Hoffmann La Roche | Anti-tubercular benzophenone derivatives |
| SE372762B (enExample) * | 1969-05-21 | 1975-01-13 | Haessle Ab | |
| SE386892B (sv) * | 1972-07-06 | 1976-08-23 | Haessle Ab | Forfarande for framstellning av oxaminoforeningar |
| US4201790A (en) * | 1975-06-20 | 1980-05-06 | May & Baker Limited | Benzophenone derivatives |
| FR2330383A1 (fr) * | 1975-11-06 | 1977-06-03 | Synthelabo | Nouveaux ethers de phenols substitues, leurs sels, leur preparation et les medicaments qui les renferment |
-
1980
- 1980-02-13 IT IT19887/80A patent/IT1147311B/it active
-
1981
- 1981-01-27 ES ES498846A patent/ES498846A0/es active Granted
- 1981-02-10 JP JP56018891A patent/JPS6026381B2/ja not_active Expired
- 1981-02-11 FR FR8102669A patent/FR2475540A1/fr active Granted
- 1981-02-11 DE DE19813104785 patent/DE3104785A1/de not_active Withdrawn
- 1981-02-12 ZA ZA00810946A patent/ZA81946B/xx unknown
- 1981-02-12 CA CA000370708A patent/CA1138897A/en not_active Expired
- 1981-02-12 GB GB8104471A patent/GB2068963B/en not_active Expired
- 1981-02-12 US US06/233,948 patent/US4376788A/en not_active Expired - Fee Related
- 1981-02-13 AT AT0068781A patent/AT374450B/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2314711A1 (fr) * | 1975-06-20 | 1977-01-14 | May & Baker Ltd | Nouveaux derives de la benzophenone |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/73 * |
Also Published As
| Publication number | Publication date |
|---|---|
| IT8019887A0 (it) | 1980-02-13 |
| AT374450B (de) | 1984-04-25 |
| IT1147311B (it) | 1986-11-19 |
| FR2475540B1 (enExample) | 1984-09-14 |
| ES8201120A1 (es) | 1981-12-01 |
| ZA81946B (en) | 1982-03-31 |
| GB2068963B (en) | 1983-06-02 |
| CA1138897A (en) | 1983-01-04 |
| GB2068963A (en) | 1981-08-19 |
| ES498846A0 (es) | 1981-12-01 |
| JPS56128742A (en) | 1981-10-08 |
| JPS6026381B2 (ja) | 1985-06-24 |
| US4376788A (en) | 1983-03-15 |
| DE3104785A1 (de) | 1982-02-25 |
| ATA68781A (de) | 1983-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |