NL7907983A - Werkwijze ter bereiding van een derivaat van 8-chloor-7-hydroxycumarine. - Google Patents

Werkwijze ter bereiding van een derivaat van 8-chloor-7-hydroxycumarine. Download PDF

Info

Publication number: NL7907983A
Authority: NL; Netherlands
Prior art keywords: formula; chloro; scheme; cooc2h5; product
Prior art date: 1978-11-06

Application number

NL7907983A

Other languages

English (en)

Dutch (nl)

Original Assignee

Fidia Spa

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.)

1978-11-06

Filing date

1979-10-31

Publication date

1980-05-08

1979-10-31 Application filed by Fidia Spa filed Critical Fidia Spa

1980-05-08 Publication of NL7907983A publication Critical patent/NL7907983A/nl

Links

KMCJAWATIYENHL-UHFFFAOYSA-N 8-chloro-7-hydroxychromen-2-one Chemical class C1=CC(=O)OC2=C(Cl)C(O)=CC=C21 KMCJAWATIYENHL-UHFFFAOYSA-N 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
150000001875 compounds Chemical class 0.000 claims description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
SWZVJOLLQTWFCW-UHFFFAOYSA-N 2-chlorobenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1Cl SWZVJOLLQTWFCW-UHFFFAOYSA-N 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 2
241000722985 Fidia Species 0.000 claims 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
239000000203 mixture Substances 0.000 description 5
125000005843 halogen group Chemical group 0.000 description 4
-1 3- (-diethylaminoethyl} -4-methyl-7-ethoxycarbonyl-methoxycoumarin hydrochloride Chemical compound 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
KLOIYEQEVSIOOO-UHFFFAOYSA-N carbocromen Chemical class CC1=C(CCN(CC)CC)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 KLOIYEQEVSIOOO-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
125000005999 2-bromoethyl group Chemical group 0.000 description 1
CUANAQIXJDGRCE-UHFFFAOYSA-N C1=C(C)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 Chemical compound C1=C(C)C(=O)OC2=CC(OCC(=O)OCC)=CC=C21 CUANAQIXJDGRCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229960005003 carbocromen Drugs 0.000 description 1
125000004181 carboxyalkyl group Chemical group 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
238000001816 cooling Methods 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
229960000956 coumarin Drugs 0.000 description 1
235000001671 coumarin Nutrition 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229960001755 resorcinol Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1

Classifications

- 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
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/16—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted in position 7

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Saccharide Compounds (AREA)

NL7907983A 1978-11-06 1979-10-31 Werkwijze ter bereiding van een derivaat van 8-chloor-7-hydroxycumarine. NL7907983A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IT2946678		1978-11-06
IT29466/78A IT1100069B (it)	1978-11-06	1978-11-06	Procedimento selettivo per la preparazione di derivati della 7-idrossicumarina

Publications (1)

Publication Number	Publication Date
NL7907983A true NL7907983A (nl)	1980-05-08

Family

ID=11227039

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7907983A NL7907983A (nl)	1978-11-06	1979-10-31	Werkwijze ter bereiding van een derivaat van 8-chloor-7-hydroxycumarine.

Country Status (16)

Country	Link
JP (1)	JPS5569575A (de)
AT (1)	AT372380B (de)
BE (1)	BE879821A (de)
CA (1)	CA1113948A (de)
CH (1)	CH641796A5 (de)
DE (1)	DE2944376A1 (de)
ES (1)	ES485745A1 (de)
FI (1)	FI793400A7 (de)
FR (1)	FR2440948A1 (de)
GB (1)	GB2036017B (de)
GR (1)	GR68055B (de)
IT (1)	IT1100069B (de)
NL (1)	NL7907983A (de)
PT (1)	PT70412A (de)
YU (1)	YU40580B (de)
ZA (1)	ZA795805B (de)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5484951A (en) *	1990-10-19	1996-01-16	Octamer, Incorporated	5-iodo-6-amino-6-nitroso-1,2-benzopyrones useful as cytostatic and antiviral agents
US5877185A (en) *	1991-10-22	1999-03-02	Octamer, Inc.	Synergistic compositions useful as anti-tumor agents
US5482975A (en) *	1991-10-22	1996-01-09	Octamer, Inc.	Adenosine diphosphoribose polymerase binding nitroso aromatic compounds useful as retroviral inactivating agents, anti-retroviral agents and anti-tumor agents
US5783599A (en) *	1993-02-24	1998-07-21	Octamer Inc	Methods of treating cancer and viral infections with 5-iodo-6-amino-and 5-iodo-6-nitroso-1 2-benzopyrones

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2361M (fr) *	1961-08-12	1964-02-24	Cassella Farbwerke Mainkur Ag	Médicament coronaro-dilatateur renfermant un dérivé de la 7-hydroxy-coumarine.
DE2039867A1 (de) *	1970-08-11	1972-02-17	Troponwerke Dinklage & Co	Pharmakologisch wirksame Coumarin-Drivate und Verfahren zu ihrer Darstellung
IT1088554B (it) *	1977-11-17	1985-06-10	F I D I A Spa	Procedimento sellettivo per la preparazione di derivati della 7-indrossi cumarina

1978
- 1978-11-06 IT IT29466/78A patent/IT1100069B/it active
1979
- 1979-10-30 ZA ZA00795805A patent/ZA795805B/xx unknown
- 1979-10-31 CH CH975079A patent/CH641796A5/it not_active IP Right Cessation
- 1979-10-31 FI FI793400A patent/FI793400A7/fi not_active Application Discontinuation
- 1979-10-31 NL NL7907983A patent/NL7907983A/nl not_active Application Discontinuation
- 1979-11-02 DE DE19792944376 patent/DE2944376A1/de not_active Withdrawn
- 1979-11-05 PT PT70412A patent/PT70412A/pt unknown
- 1979-11-05 YU YU2696/79A patent/YU40580B/xx unknown
- 1979-11-05 JP JP14376579A patent/JPS5569575A/ja active Pending
- 1979-11-05 BE BE0/197963A patent/BE879821A/fr not_active IP Right Cessation
- 1979-11-05 GR GR60422A patent/GR68055B/el unknown
- 1979-11-05 GB GB7938197A patent/GB2036017B/en not_active Expired
- 1979-11-05 CA CA339,137A patent/CA1113948A/en not_active Expired
- 1979-11-06 FR FR7927350A patent/FR2440948A1/fr active Granted
- 1979-11-06 ES ES485745A patent/ES485745A1/es not_active Expired
- 1979-11-06 AT AT0712979A patent/AT372380B/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2036017A (en)	1980-06-25
CA1113948A (en)	1981-12-08
IT1100069B (it)	1985-09-28
FR2440948A1 (fr)	1980-06-06
CH641796A5 (it)	1984-03-15
IT7829466A0 (it)	1978-11-06
YU40580B (en)	1986-02-28
ZA795805B (en)	1980-10-29
AT372380B (de)	1983-09-26
YU269679A (en)	1983-01-21
ES485745A1 (es)	1980-07-01
DE2944376A1 (de)	1980-05-14
GB2036017B (en)	1983-03-23
PT70412A (en)	1979-12-01
ATA712979A (de)	1983-02-15
JPS5569575A (en)	1980-05-26
FR2440948B1 (de)	1983-06-24
FI793400A7 (fi)	1981-01-01
GR68055B (de)	1981-10-29
BE879821A (fr)	1980-03-03

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-01-02	BV	The patent application has lapsed

Publication	Publication Date	Title
JPS5834474B2 (ja)	1983-07-27	チアゾリジン誘導体の製造法
CZ279830B6 (cs)	1995-07-12	Způsob výroby pyrazolů
EP3481200A1 (de)	2019-05-15	Verfahren zur herstellung von 4-alkoxy-3-(acyl oder alkyl)oxypicolinamiden
Akiba et al.	1979	Direct synthesis of 2, 2-diaryl-3-methyl-2, 3-dihydrobenzothiazoles from 3-methyl-2, 3-dihydrobenzothiazole-2-thione and some mechanistic aspects.
FI61310C (fi)	1982-07-12	Nytt foerfarande foer framstaellning av saosom ett laekemedel anvaendbar 5-metyl-1-fenyl-1,3,4,6-tetrahydro-5h-bens(f)-2,5-oxazocin
Kella et al.	2020	A novel class of 1, 4-disubstituted 1, 2, 3-triazoles: Regioselective synthesis, antimicrobial activity and molecular docking studies
CA1113948A (en)	1981-12-08	Selective process for the preparation of 7-hydroxycoumarin derivatives
JPH04297461A (ja)	1992-10-21	２−チオヒダントイン誘導体
Gunda et al.	1997	2-Amino-1-phenyl-propan-1, 3-diol as chiral auxiliary. Application in the synthesis of cis 3-Phthalimido-4-styryl-2-azetidinones
US5633386A (en)	1997-05-27	Commercial process for the manufacture of fluconazole and intermediates useful in the manufacture thereof
JP2002534516A (ja)	2002-10-15	血中脂質低下活性および抗酸化活性を有するモルホリン誘導体
JPS5857373A (ja)	1983-04-05	Ｌ−アスコルビン酸誘導体の製法
CA2922210A1 (en)	2015-03-12	Stereoselective synthesis of diols and triols by mannich reaction and their use in the synthesis of carfilzomib
JP2002534516A5 (de)	2007-03-15
JPH0639465B2 (ja)	1994-05-25	置換チアモルホリノン誘導体
FI59595C (fi)	1981-09-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara 5 eller 6-trifluormetyl 3-(4-alkylpiperazin-1-yl)karbonyloxi-2-(1,8-naftyridin-2-yl)isoindolin-1-oner
US4299968A (en)	1981-11-10	Novel thiophene compounds
CA1197511A (fr)	1985-12-03	Haloalkyl-8-4h-¬1\|-benzopyran-4-ones, et procede de preparation
US4360681A (en)	1982-11-23	Novel thiophene compounds
SU656511A3 (ru)	1979-04-05	Способ получени производных гексагидро-4-индолинола или их солей
Molchanov et al.	2002	Reactions of aliphatic diazo compounds: IV. Reaction of diphenyldiazomethane with substituted Imides of maleic and itaconic acids
Babjaková et al.	2014	Conformational dimorphism of isochroman-1-ones in the solid state
CH680733A5 (de)	1992-10-30
JPS639516B2 (de)	1988-02-29
JPS6245877B2 (de)	1987-09-29