CS274432B2 - Method of hydroxamic acid's aryl derivatives preparation - Google Patents

Method of hydroxamic acid's aryl derivatives preparation Download PDF

Info

Publication number: CS274432B2
Authority: CS; Czechoslovakia
Prior art keywords: group; mixture; compounds; formula; acid
Prior art date: 1987-07-15

Application number

CS508488A

Other languages

Czech (cs)

English (en)

Other versions

CS508488A2 (en

Inventor

John A Salmon

William P Jackson

Original Assignee

Wellcome Found

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.)

1987-07-15

Filing date

1988-07-14

Publication date

1991-04-11

1988-07-14 Application filed by Wellcome Found filed Critical Wellcome Found

1990-08-14 Publication of CS508488A2 publication Critical patent/CS508488A2/cs

1991-04-11 Publication of CS274432B2 publication Critical patent/CS274432B2/cs

Links

238000000034 method Methods 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 34
239000002253 acid Substances 0.000 title claims description 18
125000003118 aryl group Chemical group 0.000 title description 2
NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical compound C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 89
-1 aryl hydroxamic Chemical compound 0.000 claims description 36
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
125000001424 substituent group Chemical group 0.000 claims description 17
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000006239 protecting group Chemical group 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
239000003795 chemical substances by application Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
125000005843 halogen group Chemical group 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 claims description 2
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
125000004423 acyloxy group Chemical group 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000000203 mixture Substances 0.000 description 158
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
239000000243 solution Substances 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
239000004480 active ingredient Substances 0.000 description 40
239000000047 product Substances 0.000 description 40
150000003839 salts Chemical class 0.000 description 35
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
229960001171 acetohydroxamic acid Drugs 0.000 description 29
RRUDCFGSUDOHDG-UHFFFAOYSA-N acetohydroxamic acid Chemical compound CC(O)=NO RRUDCFGSUDOHDG-UHFFFAOYSA-N 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 26
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 25
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
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229910000027 potassium carbonate Inorganic materials 0.000 description 7
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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 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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230000000172 allergic effect Effects 0.000 description 6
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 6
208000006673 asthma Diseases 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
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238000003786 synthesis reaction Methods 0.000 description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 5
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150000007530 organic bases Chemical class 0.000 description 1
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125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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239000002689 soil Substances 0.000 description 1
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229960000391 sorbitan trioleate Drugs 0.000 description 1
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238000007910 systemic administration Methods 0.000 description 1
DRDVJQOGFWAVLH-UHFFFAOYSA-N tert-butyl n-hydroxycarbamate Chemical compound CC(C)(C)OC(=O)NO DRDVJQOGFWAVLH-UHFFFAOYSA-N 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
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ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
239000007762 w/o emulsion Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS508488A 1987-07-15 1988-07-14 Method of hydroxamic acid's aryl derivatives preparation CS274432B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878716640A GB8716640D0 (en)	1987-07-15	1987-07-15	Aryl derivatives

Publications (2)

Publication Number	Publication Date
CS508488A2 CS508488A2 (en)	1990-08-14
CS274432B2 true CS274432B2 (en)	1991-04-11

Family

ID=10620673

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS508488A CS274432B2 (en)	1987-07-15	1988-07-14	Method of hydroxamic acid's aryl derivatives preparation

Country Status (5)

Country	Link
CS (1)	CS274432B2 (de)
DD (1)	DD281804A5 (de)
GB (1)	GB8716640D0 (de)
SU (1)	SU1709904A3 (de)
ZA (1)	ZA885103B (de)

1987
- 1987-07-15 GB GB878716640A patent/GB8716640D0/en active Pending
1988
- 1988-07-14 DD DD31794088A patent/DD281804A5/de not_active IP Right Cessation
- 1988-07-14 CS CS508488A patent/CS274432B2/cs unknown
- 1988-07-14 SU SU884356229A patent/SU1709904A3/ru active
- 1988-07-14 ZA ZA885103A patent/ZA885103B/xx unknown

Also Published As

Publication number	Publication date
CS508488A2 (en)	1990-08-14
SU1709904A3 (ru)	1992-01-30
ZA885103B (en)	1990-03-28
DD281804A5 (de)	1990-08-22
GB8716640D0 (en)	1987-08-19

Publication	Publication Date	Title
EP0196184B1 (de)	1992-09-16	Aryl-Derivate
EP0299761B1 (de)	1991-12-18	Entzündungshemmende Arylderivate
US4738986A (en)	1988-04-19	N-(3-phenoxycinnamyl)acetohydroxamic acid
FR2623810A2 (fr)	1989-06-02	Sels de l'alpha-(tetrahydro-4,5,6,7 thieno(3,2-c) pyridyl-5) (chloro-2 phenyl) -acetate de methyle dextrogyre et compositions pharmaceutiques en contenant
US5036157A (en)	1991-07-30	Aryl derivatives
FR2502153A1 (fr)	1982-09-24	Acides (2-oxo-3-tetrahydrothienylcarbamoyl)-alkylthio) acetiques, leurs sels et leurs esters, leur procede de preparation et les compositions pharmaceutiques en contenant
EP0091749A2 (de)	1983-10-19	Ethanolamin-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzungen
WO1987004152A1 (en)	1987-07-16	New aryl derivatives
HU189569B (en)	1986-07-28	Process for preparing 2-substituted phenyl/-benzoic acids and pharmaceutical compositons containing such compounds as active substances
US4977188A (en)	1990-12-11	Method of treating inflammation
US4602044A (en)	1986-07-22	β-phenethanolamine antiobesity agents
MC1744A1 (fr)	1987-02-26	Derives de phenylethanolamines
EP0351214A1 (de)	1990-01-17	Entzündungshemmende Arylderivate
CS274432B2 (en)	1991-04-11	Method of hydroxamic acid's aryl derivatives preparation
MC2105A1 (fr)	1991-03-11	Derives de tetrahydronaphtalene
MC2108A1 (fr)	1991-03-11	Derives de quinoleine
FR2763847A1 (fr)	1998-12-04	Utilisation de tetrahydropyridines 4-substituees pour fabriquer des medicaments agissant sur le tgf-beta-1
KR910003637B1 (ko)	1991-06-07	히드록삼산 아릴 유도체의 제조방법
FR2479820A1 (fr)	1981-10-09	Compose du type 4-(4-chlorophenyl)-2-(4-acyloxy- ou hydroxyphenyl)-thiazole-5-acetique ou acetate, procede pour sa preparation et son application comme medicament
FR2540107A1 (fr)	1984-08-03	Nouveaux derives d'halogenobenzophenone-oxime, utilisation en therapeutique et procede de preparation
JP3857428B2 (ja)	2006-12-13	抗真菌剤
RU2002738C1 (ru)	1993-11-15	Способ получени производных N-гидроксимочевин в виде R- или S-энантиомерных форм или их смеси, или их фармацевтически приемлемых солей с щелочным металлом
DD267978A5 (de)	1989-05-17	Verfahren zur herstellung von hydroxamsaeure-arylderivaten
JPH0226628B2 (de)	1990-06-12
PT89857A (pt)	1990-08-31	Processo para a preparacao de novos derivados do acido hidroxamico e de composicoes farmaceuticas que os contem