CH644108A5 - Anti-inflammatory imidazoles and processes for their preparation - Google Patents

Anti-inflammatory imidazoles and processes for their preparation Download PDF

Info

Publication number: CH644108A5
Authority: CH; Switzerland
Prior art keywords: thienyl; formula; compounds; imidazole; hydrogen
Prior art date: 1977-02-09

Application number

CH147478A

Other languages

German (de)

English (en)

Inventor

Saul Carl Cherkofsky

Thomas Ray Sharpe

Original Assignee

Du Pont

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.)

1977-02-09

Filing date

1978-02-09

Publication date

1984-07-13

1978-01-05 Priority claimed from US05/865,832 external-priority patent/US4159338A/en

1978-02-09 Application filed by Du Pont filed Critical Du Pont

1984-07-13 Publication of CH644108A5 publication Critical patent/CH644108A5/de

Links

238000000034 method Methods 0.000 title claims description 16
230000008569 process Effects 0.000 title claims description 11
230000003110 anti-inflammatory effect Effects 0.000 title claims description 9
238000002360 preparation method Methods 0.000 title claims description 8
150000002460 imidazoles Chemical class 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims description 66
-1 3-pyridyl-N-> oxide Chemical group 0.000 claims description 42
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 24
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 19
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
150000002431 hydrogen Chemical class 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 7
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 6
229910052794 bromium Inorganic materials 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
239000002168 alkylating agent Substances 0.000 claims description 4
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125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
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239000002184 metal Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
PEPARVGCRJOCSI-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-(1,1,2,2-tetrafluoroethylsulfonyl)-5-thiophen-2-yl-1h-imidazole Chemical compound N1C(S(=O)(=O)C(F)(F)C(F)F)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=CS1 PEPARVGCRJOCSI-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
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125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
XVHGGUCYYQBBHJ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-5-thiophen-2-yl-2-(trifluoromethylsulfonyl)-1h-imidazole Chemical compound C1=CC(OC)=CC=C1C1=C(C=2SC=CC=2)NC(S(=O)(=O)C(F)(F)F)=N1 XVHGGUCYYQBBHJ-UHFFFAOYSA-N 0.000 claims description 2
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125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims description 2
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239000002671 adjuvant Substances 0.000 description 5
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/22—Radicals substituted by doubly bound hetero atoms, or by two hetero atoms other than halogen singly bound to the same carbon atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
- C07D213/46—Oxygen atoms
- C07D213/50—Ketonic radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members 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
- C07D233/84—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH147478A 1977-02-09 1978-02-09 Anti-inflammatory imidazoles and processes for their preparation CH644108A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US76722077A	1977-02-09	1977-02-09
US05/865,832 US4159338A (en)	1977-02-09	1978-01-05	Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones

Publications (1)

Publication Number	Publication Date
CH644108A5 true CH644108A5 (en)	1984-07-13

Family

ID=27117879

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH147478A CH644108A5 (en)	1977-02-09	1978-02-09	Anti-inflammatory imidazoles and processes for their preparation

Country Status (26)

Country	Link
JP (1)	JPS53130664A (da)
AR (1)	AR219310A1 (da)
AT (1)	AT361470B (da)
AU (1)	AU517028B2 (da)
CA (1)	CA1105024A (da)
CH (1)	CH644108A5 (da)
DE (1)	DE2805167A1 (da)
DK (1)	DK16778A (da)
ES (1)	ES466794A1 (da)
FI (1)	FI69462C (da)
FR (1)	FR2380275A1 (da)
GB (1)	GB1564184A (da)
GR (1)	GR64142B (da)
HU (1)	HU178211B (da)
IE (1)	IE46187B1 (da)
IL (1)	IL53995A (da)
IT (1)	IT1092588B (da)
LU (1)	LU79024A1 (da)
MX (1)	MX5933E (da)
NL (1)	NL7801453A (da)
NO (1)	NO148265C (da)
NZ (1)	NZ186410A (da)
PH (1)	PH13852A (da)
PT (1)	PT67626B (da)
SE (1)	SE7801467L (da)
YU (1)	YU28878A (da)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0004648B1 (de) *	1978-04-11	1982-08-25	Ciba-Geigy Ag	Neue Mercaptoimidazolderivate, Verfahren zu deren Herstellung, Mercaptoimidazolderivate zur Behandlung entzündlicher Erkrankungen und diese enthaltende pharmazeutische Präparate
US4199592A (en) *	1978-08-29	1980-04-22	E. I. Du Pont De Nemours And Company	Antiinflammatory 4,5-diaryl-2-nitroimidazoles
DK337779A (da) *	1978-10-02	1980-04-03	Du Pont	Fremgangsmaade til fremstilling af antiinflammatoriske 2-substituerede 1h-phenantro (9,10)-imidazoler
AT374198B (de) *	1979-04-10	1984-03-26	Ciba Geigy Ag	Verfahren zur herstellung neuer 2-substituierter mercaptoimidazolderivate, ihrer n-oxyde und ihrer salze
FI850995L (fi) *	1984-03-16	1985-09-17	Ciba Geigy Ag	Foerfarande foer framstaellning av nya 3-merkapto-1,2,4-triazacykloalkadienderivat.
CA2295021A1 (en) *	1997-06-30	1999-01-28	Ortho-Mcneil Pharmaceutical, Inc.	2-substituted imidazoles useful in the treatment of inflammatory diseases
DE10107683A1 (de)	2001-02-19	2002-08-29	Merckle Gmbh Chem Pharm Fabrik	2-Thio-substituierte Imidazolderivate und ihre Verwendung in der Pharmazie

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2981739A (en) *	1958-01-27	1961-04-25	Diamond Alkali Co	Certain alpha-haloaldehyde addition products of ethylenethioureas and process
US3714179A (en) *	1970-09-08	1973-01-30	Searle & Co	1-alkyl-2-furfurylthioimidazoles and congeners
JPS5343958B2 (da) *	1972-07-29	1978-11-24
SE428686B (sv) *	1975-08-11	1983-07-18	Du Pont	Forfarande for framstellning av antiinflammatoriskt aktiva imidazoler

1978
- 1978-01-13 DK DK16778A patent/DK16778A/da not_active Application Discontinuation
- 1978-02-06 PT PT67626A patent/PT67626B/pt unknown
- 1978-02-07 IT IT7820078A patent/IT1092588B/it active
- 1978-02-07 CA CA296,606A patent/CA1105024A/en not_active Expired
- 1978-02-08 MX MX786829U patent/MX5933E/es unknown
- 1978-02-08 SE SE7801467A patent/SE7801467L/xx unknown
- 1978-02-08 DE DE19782805167 patent/DE2805167A1/de not_active Withdrawn
- 1978-02-08 IL IL53995A patent/IL53995A/xx unknown
- 1978-02-08 NO NO780433A patent/NO148265C/no unknown
- 1978-02-08 NZ NZ186410A patent/NZ186410A/xx unknown
- 1978-02-08 NL NL7801453A patent/NL7801453A/xx not_active Application Discontinuation
- 1978-02-08 AT AT86978A patent/AT361470B/de not_active IP Right Cessation
- 1978-02-08 AU AU33096/78A patent/AU517028B2/en not_active Expired
- 1978-02-08 ES ES466794A patent/ES466794A1/es not_active Expired
- 1978-02-08 FR FR7803518A patent/FR2380275A1/fr active Granted
- 1978-02-08 YU YU00288/78A patent/YU28878A/xx unknown
- 1978-02-08 GB GB5098/78A patent/GB1564184A/en not_active Expired
- 1978-02-08 IE IE279/78A patent/IE46187B1/en unknown
- 1978-02-08 LU LU79024A patent/LU79024A1/xx unknown
- 1978-02-09 JP JP1304678A patent/JPS53130664A/ja active Pending
- 1978-02-09 AR AR271048A patent/AR219310A1/es active
- 1978-02-09 HU HU78DU279A patent/HU178211B/hu unknown
- 1978-02-09 FI FI780428A patent/FI69462C/fi not_active IP Right Cessation
- 1978-02-09 GR GR55396A patent/GR64142B/el unknown
- 1978-02-09 PH PH20771A patent/PH13852A/en unknown
- 1978-02-09 CH CH147478A patent/CH644108A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
ES466794A1 (es)	1979-08-01
FR2380275B1 (da)	1982-01-08
IT1092588B (it)	1985-07-12
PT67626B (en)	1979-07-17
JPS53130664A (en)	1978-11-14
FI69462C (fi)	1986-02-10
FR2380275A1 (fr)	1978-09-08
FI780428A7 (fi)	1978-08-10
YU28878A (en)	1983-01-21
AR219310A1 (es)	1980-08-15
SE7801467L (sv)	1978-08-10
FI69462B (fi)	1985-10-31
IT7820078A0 (it)	1978-02-07
NL7801453A (nl)	1978-08-11
NO780433L (no)	1978-08-10
AU517028B2 (en)	1981-07-02
NO148265B (no)	1983-05-30
GR64142B (en)	1980-01-28
HU178211B (en)	1982-03-28
AU3309678A (en)	1979-08-16
GB1564184A (en)	1980-04-02
IL53995A (en)	1982-02-28
NO148265C (no)	1983-09-07
AT361470B (de)	1981-03-10
NZ186410A (en)	1979-12-11
IL53995A0 (en)	1978-04-30
MX5933E (es)	1984-08-30
CA1105024A (en)	1981-07-14
IE780279L (en)	1978-08-09
DK16778A (da)	1978-08-10
DE2805167A1 (de)	1978-08-10
ATA86978A (de)	1980-08-15
PT67626A (en)	1978-03-01
PH13852A (en)	1980-10-22
LU79024A1 (fr)	1979-05-25
IE46187B1 (en)	1983-03-23

Legal Events

Date	Code	Title	Description
1986-10-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE3873127T2 (de)	1992-12-03	Therapeutische praeparate.
DE2805166A1 (de)	1978-08-10	Neue entzuendungshemmende imidazolverbindungen, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE2061489A1 (de)	1971-07-29	Anti Gichtmittel und anti hyperurikami sehe Mittel, enthaltend 4(5) Tnfluormethyl imidazole
DE2634903C2 (de)	1985-08-14	Tetrahydrothieno-[3,2-c]-pyridin-Derivate und sie enthaltende Arzneimittel
US4159338A (en)	1979-06-26	Antiinflammatory-4,5-dicyclic-2-(substituted thio)-imidazoles and their corresponding sulfoxides and sulfones
DD149217A5 (de)	1981-07-01	Verfahren zur herstellung von pyrimidonderivaten
CH644108A5 (en)	1984-07-13	Anti-inflammatory imidazoles and processes for their preparation
DE2112349A1 (de)	1971-10-14	Di- und tri-substituierte Imidazole
DE2635876A1 (de)	1977-03-03	Imidazolderivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
EP0214479A2 (de)	1987-03-18	Benzimidazol-2-yl-pyridiniumverbindungen
DE3509333A1 (de)	1986-09-18	Substituierte benzimidazolderivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer
DE2321518C2 (de)	1986-07-31	Sulfamylbenzoesäuren und deren Derivate, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Mittel
DE1914571B2 (de)	1978-01-12	L-3hydroxy-6-oxomorphinan-verbindungen
CH617701A5 (da)	1980-06-13
EP0103142B1 (de)	1987-04-22	Thieno(2,3-e)-1,2-thiazin-Derivate
AT400845B (de)	1996-03-25	Neue thienothiazinderivate, ein verfahren zu ihrer herstellung und ihre verwendung
DE2550959C3 (de)	1980-12-04	Tetrazolyl-imidazole und Tetrazolyl--benzimidazole, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
DE1909110A1 (de)	1969-10-16	Verfahren zur Herstellung neuer heterocyclischer Verbindungen
DD144916A5 (de)	1980-11-12	Verfahren zur herstellung von pyrimidinverbindungen und ihren salzen
DE69503364T2 (de)	1999-04-15	Verfahren zur herstellung von polymorphe b und c von 1-(2,4-dichloro-beta-((7-chloro-benzo(b)thien-3-yl)methoxy)phenethyl) imidazol-mononitrat
DE2106038C3 (de)	1980-06-19	2-Imidazolin-2-ylamino-benzo [b] thiophene und diese enthaltende pharmazeutische Präparate
DE68919512T2 (de)	1995-04-20	Chinoxalin-Derivate und antiulzerierendes Mittel.
EP0018542B1 (de)	1983-03-02	Phenothiazinderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung
EP0045521B1 (de)	1984-06-27	Pyrazolobenzazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE69123168T2 (de)	1997-06-12	Piperidinderivate und diese enthaltende Antiulcer-Präparate