GB931556A - Dibenzocycloheptatriene derivatives - Google Patents
Dibenzocycloheptatriene derivativesInfo
- Publication number
- GB931556A GB931556A GB7308/63A GB730863A GB931556A GB 931556 A GB931556 A GB 931556A GB 7308/63 A GB7308/63 A GB 7308/63A GB 730863 A GB730863 A GB 730863A GB 931556 A GB931556 A GB 931556A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- dihydro
- alkyl
- cycloheptatrien
- general formula
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/10—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms
- C07D211/12—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with radicals containing only carbon and hydrogen atoms attached to ring carbon atoms with only hydrogen atoms attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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 to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0931556/IV(a)/1> and their 10,11-dihydro analogues, in which X and X1 are hydrogen, halogen, trifluoromethyl, C1-4-alkyl, C1-4-alkoxy or mononuclear aryl, there being one or more such atom or group attached to each benzene ring, and R is C1-4-alkyl and derivatives of such compounds alkylated in one or more of positions 2, 3, 5 and 6 of the piperidine ring provided that the total number of carbon atoms in all such substituent alkyl groups does not exceed 4, their acid addition salts and N-oxides and the preparation thereof which comprises reacting a compound of the general formula <FORM:0931556/IV(a)/2> or its 10,11-dihydro analogue with a Grignard reagent having the general formula <FORM:0931556/IV(a)/3> or an appropriate alkyl substituted derivative thereof and hydrolysing the Grignard adduct. 3-Chlorodibenzo [a,e] cycloheptatrien-5-one is prepared by reacting p-chlorophenylacetic acid and phthalic anhydride to form 3-(b -chlorobenzylidene)-phthalide, reducing this with phosphorus and hydriodic acid to 2-(p-chlorophenethyl) benzoic acid and cyclizing the last named acid with polyphosphonic acid. Similary are prepared 4-methyl-10,11-dihydro-5-dibenzo [a,e] cycloheptatrien-5-one, 3(p-isopropylbenzylidene)phthalide, 2-(p-isopropylphenethyl)-4,5-dimethylbenzoic acid, 10,11-dihydro- 2,3-dimethyl- 7-isopropyl-5-dibenzo [a,e] cycloheptatrien-5-one, and 10-11-dihydro-2,3-dichloro-7-methyldibenzo [a,e] cycloheptatrien-5-one. The Grignard reagents, 1-alkyl-4-piperidyl magnesium halides, are prepared from 1-alkyl-4-halopiperidines and magnesium in tetrahydrofuran.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US76380958A | 1958-09-29 | 1958-09-29 | |
US826493A US3014911A (en) | 1958-09-29 | 1959-07-13 | Derivatives of dibenzo[a, e]cycloheptatriene |
Publications (1)
Publication Number | Publication Date |
---|---|
GB931556A true GB931556A (en) | 1963-07-17 |
Family
ID=27117345
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB7308/63A Expired GB931556A (en) | 1958-09-29 | 1959-08-28 | Dibenzocycloheptatriene derivatives |
GB29490/59A Expired GB931555A (en) | 1958-09-29 | 1959-08-28 | Dibenzocycloheptatriene derivatives |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB29490/59A Expired GB931555A (en) | 1958-09-29 | 1959-08-28 | Dibenzocycloheptatriene derivatives |
Country Status (8)
Country | Link |
---|---|
US (1) | US3014911A (en) |
BE (1) | BE582220A (en) |
CH (1) | CH387037A (en) |
DE (1) | DE1420072C3 (en) |
FR (1) | FR490M (en) |
GB (2) | GB931556A (en) |
MY (1) | MY6400051A (en) |
OA (1) | OA00998A (en) |
Families Citing this family (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL237664A (en) * | 1959-04-01 | |||
GB999879A (en) * | 1960-11-09 | 1965-07-28 | Sandoz Ag | Improvements in or relating to dibenzocycloheptane derivatives |
NL122808C (en) * | 1961-09-29 | |||
BE626236A (en) * | 1961-12-18 | |||
US3133935A (en) * | 1962-01-08 | 1964-05-19 | American Home Prod | Dibenzo [a, d] [1, 4] cyclooctadienes |
US3231468A (en) * | 1962-07-02 | 1966-01-25 | Merck & Co Inc | Dexamethasone-cyproheptadine oral antiflammatory compositions |
NL130095C (en) * | 1962-08-31 | |||
US3152135A (en) * | 1962-11-02 | 1964-10-06 | Warner Lambert Pharmaceutical | Heterocyclic substituted indazole compounds and process therefor |
US3419565A (en) * | 1963-04-24 | 1968-12-31 | Schering Corp | Aza-dibenzocycloheptenes |
NL132137C (en) * | 1963-04-24 | |||
US3324138A (en) * | 1963-12-03 | 1967-06-06 | Koninklijke Pharma Fab Nv | Quinuclidin-3-yl-ester of 10, 11-dihydro-5h-dibenzo[a, d]cyclohepten-5-yl-acetic acid |
US3491103A (en) * | 1963-12-19 | 1970-01-20 | Sandoz Ag | Certain 4h-benzo(4,5)cyclohepta-(1,2-b) thiophenes |
US3420848A (en) * | 1964-05-18 | 1969-01-07 | Sandoz Ag | Dibenzocycloheptane derivatives |
GB1091910A (en) * | 1964-08-18 | 1967-11-22 | Koninklijke Pharma Fab Nv | New dibenzocycloheptenylamines |
GB1127683A (en) * | 1965-03-15 | 1968-09-18 | Merck & Co Inc | Anthelmintic compositions |
US3484520A (en) * | 1965-05-17 | 1969-12-16 | Merck & Co Inc | Compositions and methods for treating helminthiasis comprising combinations of organo-phosphates and certain dibenzocycloheptenes |
US3352869A (en) * | 1965-05-18 | 1967-11-14 | Merck & Co Inc | Substituted and unsubstituted 4-(5h-dibenzo[a, d] cyclohepten-5-ylidene)-1-(amino ornitroso) piperidines |
US3391143A (en) * | 1966-05-16 | 1968-07-02 | Smith Kline French Lab | 9-piperidyl and 9-piperidylidene derivatives of acridan |
US3919321A (en) * | 1966-11-08 | 1975-11-11 | Hoffmann La Roche | Halo-substituted-5H-dibenzo{8 a,d{9 cyclohepten-5-ones |
US3458522A (en) * | 1967-05-17 | 1969-07-29 | Sandoz Ag | 4-piperidine substituted benzocycloheptaoxazoles and benzocycloheptathiazoles |
US3475438A (en) * | 1967-08-24 | 1969-10-28 | Merck & Co Inc | Piperidine derivatives of dibenzobicyclo(5.1.0)octane |
GB1273823A (en) * | 1968-10-22 | 1972-05-10 | Soc Ind Fab Antibiotiques Sifa | New tropane derivatives their salts and process for preparation thereof |
US3968115A (en) * | 1970-02-05 | 1976-07-06 | Merck & Co., Inc. | 1-Alkyl-4-(10 and/or 11)-bromo-10,11-dihydro-5H-dibenzo[a,d]-cyclohepten-5-ylidene piperidine compounds |
US3960872A (en) * | 1970-02-05 | 1976-06-01 | Merck & Co., Inc. | 1 Alkyl-4-(10:oxo or hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidine compounds |
US3981876A (en) * | 1970-02-05 | 1976-09-21 | Merck & Co., Inc. | 1-Alkyl-4-(10[1-piperidyl]-5H-dibenzo-[a,d]cyclohepten-5-ylidene)piperidine compounds |
US3988342A (en) * | 1972-08-14 | 1976-10-26 | Merck & Co., Inc. | Piperidylidene derivatives of cyano-5H-dibenzo[a,d]cycloheptene |
US3981877A (en) * | 1972-08-14 | 1976-09-21 | Merck & Co., Inc. | Piperidylidene derivatives of carboxy-5H-dibenzo[a,d]cycloheptene |
US4072756A (en) * | 1973-05-17 | 1978-02-07 | Sandoz Ltd. | Tricyclo piperidino ketones and soporific compositions thereof |
GB1435054A (en) * | 1974-02-04 | 1976-05-12 | Ici Ltd | Dihydroanthracene derivatives |
US4089864A (en) * | 1974-03-25 | 1978-05-16 | Merck & Co., Inc. | 4-(10,11-Dihydro-cis and trans-10,11-dihydroxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-piperidines |
US3974285A (en) * | 1974-04-10 | 1976-08-10 | Merck & Co., Inc. | 10,11-Furo-derivatives of cyproheptadine |
HU169186B (en) * | 1974-06-13 | 1976-10-28 | ||
US3992547A (en) * | 1974-11-20 | 1976-11-16 | Merck & Co., Inc. | 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-methylpiperidine-N-oxide isomer |
US4044143A (en) * | 1975-01-30 | 1977-08-23 | Merck & Co., Inc. | 10,11-Bis-(hydroxyalkyl) derivatives of cyproheptadine |
US4022902A (en) * | 1975-08-29 | 1977-05-10 | Merck & Co., Inc. | 10,11-Dihydro-3-carboxycyproheptadien-N-oxide |
US4160031A (en) * | 1975-03-28 | 1979-07-03 | Merck & Co., Inc. | Antihistaminic and appetite stimulating 10,11-dihydro-3-carboxycyproheptadine |
US4112112A (en) * | 1976-06-29 | 1978-09-05 | Merck & Co., Inc. | Pyrrolo[2,1-b] [3]benzazepines useful for producing a skeletal muscle relaxing or tranquilizing effect |
US4104398A (en) * | 1976-08-12 | 1978-08-01 | Merck & Co., Inc. | 3-Lower alkoxycyproheptadines as serotonin inhibitors |
US4148903A (en) * | 1977-07-28 | 1979-04-10 | Merck & Co., Inc. | Antipsychotic, antiserotonin and antihistaminic pyrrolo[2,1-b][3]benzazepines |
US4132796A (en) * | 1977-12-01 | 1979-01-02 | Merck & Co., Inc. | Antipsychotic 3-trifluoromethylsulfinyl analogs of cyproheptadine |
US4195091A (en) * | 1978-11-15 | 1980-03-25 | Merck & Co., Inc. | Appetite stimulating pyrrolo[2,1-b][3]benzazepines |
ATE3150T1 (en) * | 1979-01-02 | 1983-05-15 | Merck & Co. Inc. | LEFT AND RIGHT HAND ROTARY ENANTIOMERS OF 3HALOCYPROHEPTADINES, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITION CONTAINING THEM. |
US4212871A (en) * | 1979-03-02 | 1980-07-15 | Merck & Co., Inc. | Appetite stimulating and antihistaminic 3-hydroxymethylcyproheptadine and analogs |
US4220651A (en) * | 1979-05-21 | 1980-09-02 | Merck & Co., Inc. | Antipsychotic levorotatory enantiomers of 3-halocyproheptadines, analogs and derivatives |
EP0019797A1 (en) * | 1979-05-21 | 1980-12-10 | Merck & Co. Inc. | Levorotatory and dextrorotatory enantiomers of 3-methoxycyproheptadine and analogs thereof, process for their preparation and antipsychotic pharmaceutical compositions |
US4275070A (en) * | 1979-05-21 | 1981-06-23 | Merck & Co., Inc. | Antipsychotic pharmaceutical compositions of the levorotatory enantiomers of 3-methoxycyproheptadine and an analog thereof |
US4356184A (en) * | 1980-06-04 | 1982-10-26 | G. D. Searle & Co. | Anti-allergic or antihypertensive 1-piperidinylmethyl benzenamines |
US4412999A (en) * | 1982-04-14 | 1983-11-01 | Merck & Co., Inc. | Anti-emetic esters of cyproheptadine-3-carboxylic acid and structurally related compounds |
US4590202A (en) * | 1984-01-19 | 1986-05-20 | Merck & Co., Inc. | N-(2-imidazolidinylidene)-5H-dibenzo[a,d]cyclohepten-5-amine compounds and α2 -adrenergic antagonistic uses thereof |
US4626542A (en) * | 1984-04-05 | 1986-12-02 | Merck & Co., Inc. | 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds, pharmaceutical compositions and methods |
US4758577A (en) * | 1984-04-05 | 1988-07-19 | Merck & Co., Inc. | 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds for treating cardiovascular disorders |
FR2618151B1 (en) * | 1987-07-16 | 1991-01-11 | Synthelabo | PIPERIDINE DERIVATIVES, THEIR PREPARATION AND THEIR THERAPEUTIC APPLICATION |
US5250681A (en) * | 1988-06-02 | 1993-10-05 | Ajinomoto Co., Inc. | Piperidine derivatives and hypotensives containing the same |
US4912222A (en) * | 1988-06-17 | 1990-03-27 | Fisons Corporation | Antihistamines related to cyproheptadine |
EP0347123A3 (en) * | 1988-06-17 | 1991-07-03 | Fisons Corporation | Dibenzo-cycloheptenyl, -cycloheptyl and -oxepinyl amines having antihistaminic properties |
CA2004211A1 (en) * | 1988-11-30 | 1990-05-31 | Masataka Syoji | Piperidine derivatives and hyportensives containing the same |
US5021426A (en) * | 1990-02-26 | 1991-06-04 | Merck & Co., Inc. | Method of traeting malaria with cyproheptadine derivatives |
SE509618C2 (en) | 1997-03-06 | 1999-02-15 | Goeran Blomqvist | Pharmaceutical composition for the treatment of so-called restless legs |
US6880501B2 (en) | 2001-07-30 | 2005-04-19 | Massachusetts Institute Of Technology | Internal combustion engine |
US10398687B2 (en) | 2010-09-14 | 2019-09-03 | David Reed Helton | Use of cyproheptadine to treat organophosphate exposure |
CN110407737B (en) * | 2019-07-30 | 2021-03-23 | 广州普星药业有限公司 | Preparation method of cyproheptadine hydrochloride |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA535142A (en) * | 1957-01-01 | W. Weston Arthur | Pipecolyl carbinol compounds | |
DE925468C (en) * | 1941-08-13 | 1955-03-21 | Hoechst Ag | Process for the preparation of ª †, ª † -Diaryl-propyl-amines |
US2498431A (en) * | 1945-06-13 | 1950-02-21 | Hoffmann La Roche | 2-and 4-homocyclyl substituted piperidines |
US2599364A (en) * | 1949-01-26 | 1952-06-03 | Hoffmann La Roche | 1-alkyl-3-benzohydryl piperidines |
NL88063C (en) * | 1950-12-05 | |||
US2985660A (en) * | 1960-04-29 | 1961-05-23 | Lakeside Lab Inc | 5-heterocyclic-5h-dibenzo [a, d] cycloheptenes |
-
1959
- 1959-07-13 US US826493A patent/US3014911A/en not_active Expired - Lifetime
- 1959-08-28 GB GB7308/63A patent/GB931556A/en not_active Expired
- 1959-08-28 GB GB29490/59A patent/GB931555A/en not_active Expired
- 1959-09-01 BE BE582220A patent/BE582220A/en unknown
- 1959-09-03 DE DE1420072A patent/DE1420072C3/en not_active Expired
- 1959-09-29 CH CH7878959A patent/CH387037A/en unknown
-
1960
- 1960-08-30 FR FR837257A patent/FR490M/fr active Active
-
1964
- 1964-12-29 OA OA51101A patent/OA00998A/en unknown
- 1964-12-30 MY MY51/64A patent/MY6400051A/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE582220A (en) | 1960-03-01 |
GB931555A (en) | 1963-07-17 |
MY6400051A (en) | 1964-12-31 |
DE1420072C3 (en) | 1974-08-08 |
DE1420072B2 (en) | 1974-01-03 |
OA00998A (en) | 1968-08-07 |
DE1420072A1 (en) | 1968-10-03 |
CH387037A (en) | 1965-01-31 |
US3014911A (en) | 1961-12-26 |
FR490M (en) | 1961-05-08 |
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