BG61317B2 - 3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения - Google Patents

3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения Download PDF

Info

Publication number: BG61317B2
Authority: BG; Bulgaria
Prior art keywords: formula; compound; methoxy; preparation; come
Prior art date: 1987-03-26

Application number

BG098346A

Other languages

Bulgarian (bg)

English (en)

Inventor

Sidney Callander

Original Assignee

Beecham Group P.L.C.

Priority date (The priority date 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 date listed.)

1987-03-26

Filing date

1993-12-29

Publication date

1997-05-30

1993-12-29 Application filed by Beecham Group P.L.C. filed Critical Beecham Group P.L.C.

1997-05-30 Publication of BG61317B2 publication Critical patent/BG61317B2/bg

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims abstract description 12
238000002360 preparation method Methods 0.000 title claims abstract description 10
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 9
VZBLASFLFFMMCM-UHFFFAOYSA-N 6-methoxynaphthalene-2-carbaldehyde Chemical compound C1=C(C=O)C=CC2=CC(OC)=CC=C21 VZBLASFLFFMMCM-UHFFFAOYSA-N 0.000 claims abstract description 6
238000009833 condensation Methods 0.000 claims abstract description 6
230000005494 condensation Effects 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
230000006196 deacetylation Effects 0.000 claims abstract description 3
238000003381 deacetylation reaction Methods 0.000 claims abstract description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 4
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 description 3
238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
239000000047 product Substances 0.000 description 5
125000005594 diketone group Chemical group 0.000 description 4
238000001914 filtration Methods 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
238000010992 reflux Methods 0.000 description 2
230000003595 spectral effect Effects 0.000 description 2
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
206010062717 Increased upper airway secretion Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
206010003246 arthritis Diseases 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
241001233037 catfish Species 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000008014 freezing Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
-1 halogen hydrocarbon Chemical class 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
238000004811 liquid chromatography Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
208000026435 phlegm Diseases 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/12—Ketones containing more than one keto group
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/255—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
- 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
- C07C45/62—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 hydrogenation of carbon-to-carbon double or triple bonds
- 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
- C07C45/65—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 splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
- 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
- C07C45/68—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 increase in the number of carbon atoms
- 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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/72—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—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 increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Physical Or Chemical Processes And Apparatus (AREA)
Hydrogenated Pyridines (AREA)
Cleaning Or Drying Semiconductors (AREA)

BG098346A 1987-03-26 1993-12-29 3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения BG61317B2 (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878707200A GB8707200D0 (en)	1987-03-26	1987-03-26	Chemical process

Publications (1)

Publication Number	Publication Date
BG61317B2 true BG61317B2 (bg)	1997-05-30

Family

ID=10614672

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG098346A BG61317B2 (bg)	1987-03-26	1993-12-29	3-(6'метокси-2'-нафтилметил)-2,4 пентандион,метод за получаването му и междинни съединения

Country Status (16)

Country	Link
EP (1)	EP0288144B1 (de)
JP (1)	JP2598296B2 (de)
KR (1)	KR960009161B1 (de)
AT (1)	ATE89257T1 (de)
AU (1)	AU612352B2 (de)
BG (1)	BG61317B2 (de)
CA (1)	CA1310333C (de)
DE (1)	DE3880880T2 (de)
DK (1)	DK172560B1 (de)
ES (1)	ES2056912T3 (de)
GB (1)	GB8707200D0 (de)
HK (1)	HK1004545A1 (de)
IE (1)	IE61580B1 (de)
NZ (1)	NZ224006A (de)
PT (1)	PT87069B (de)
ZA (1)	ZA882101B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5202495A (en) *	1987-03-26	1993-04-13	Callander Sidney E	Chemical process

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4910664B1 (de) *	1969-07-21	1974-03-12
US4061779A (en) *	1973-09-11	1977-12-06	Beecham Group Limited	Naphthalene derivatives having anti-inflammatory activity
AT343103B (de) *	1975-01-08	1978-05-10	Beecham Group Ltd	Verfahren zur herstellung von neuen naphthalinderivaten
GB1504442A (en) *	1976-11-25	1978-03-22	Beecham Group Ltd	Naphthyl derivatives
DE2963747D1 (en) *	1978-11-23	1982-11-04	Beecham Group Plc	Naphthalene derivatives, a process for their preparation and their use in anti-inflammatory pharmaceutical compositions

1987
- 1987-03-26 GB GB878707200A patent/GB8707200D0/en active Pending
1988
- 1988-03-16 DE DE88302285T patent/DE3880880T2/de not_active Expired - Fee Related
- 1988-03-16 AT AT88302285T patent/ATE89257T1/de not_active IP Right Cessation
- 1988-03-16 EP EP88302285A patent/EP0288144B1/de not_active Expired - Lifetime
- 1988-03-16 ES ES88302285T patent/ES2056912T3/es not_active Expired - Lifetime
- 1988-03-24 NZ NZ224006A patent/NZ224006A/en unknown
- 1988-03-24 DK DK198801621A patent/DK172560B1/da not_active IP Right Cessation
- 1988-03-24 PT PT87069A patent/PT87069B/pt not_active IP Right Cessation
- 1988-03-24 IE IE89288A patent/IE61580B1/en not_active IP Right Cessation
- 1988-03-24 ZA ZA882101A patent/ZA882101B/xx unknown
- 1988-03-24 CA CA000562375A patent/CA1310333C/en not_active Expired - Fee Related
- 1988-03-24 AU AU13704/88A patent/AU612352B2/en not_active Ceased
- 1988-03-25 KR KR1019880003253A patent/KR960009161B1/ko not_active Expired - Fee Related
- 1988-03-25 JP JP63071699A patent/JP2598296B2/ja not_active Expired - Fee Related
1993
- 1993-12-29 BG BG098346A patent/BG61317B2/bg unknown
1998
- 1998-04-28 HK HK98103615A patent/HK1004545A1/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE89257T1 (de)	1993-05-15
EP0288144A2 (de)	1988-10-26
PT87069B (pt)	1992-07-31
EP0288144A3 (en)	1990-02-14
IE61580B1 (en)	1994-11-16
DK172560B1 (da)	1999-01-18
CA1310333C (en)	1992-11-17
NZ224006A (en)	1991-05-28
GB8707200D0 (en)	1987-04-29
ZA882101B (en)	1989-09-27
PT87069A (pt)	1988-04-01
KR880011062A (ko)	1988-10-26
IE880892L (en)	1988-09-26
AU612352B2 (en)	1991-07-11
JP2598296B2 (ja)	1997-04-09
KR960009161B1 (ko)	1996-07-16
DK162188A (da)	1988-09-27
DE3880880D1 (de)	1993-06-17
EP0288144B1 (de)	1993-05-12
ES2056912T3 (es)	1994-10-16
DK162188D0 (da)	1988-03-24
HK1004545A1 (en)	1998-11-27
JPS63255243A (ja)	1988-10-21
AU1370488A (en)	1988-09-29
DE3880880T2 (de)	1993-10-07

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