IE772446L - 5-(substituted phenyl)-oxazolidinones and sulphur analogues - Google Patents
5-(substituted phenyl)-oxazolidinones and sulphur analoguesInfo
- Publication number
- IE772446L IE772446L IE772446A IE244677A IE772446L IE 772446 L IE772446 L IE 772446L IE 772446 A IE772446 A IE 772446A IE 244677 A IE244677 A IE 244677A IE 772446 L IE772446 L IE 772446L
- Authority
- IE
- Ireland
- Prior art keywords
- oxazolidinones
- phenyl
- general formula
- acid derivative
- novel
- Prior art date
Links
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 title abstract 2
- -1 5-(substituted phenyl)-oxazolidinones Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 1
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 1
- 230000002082 anti-convulsion Effects 0.000 abstract 1
- 230000001090 anti-dopaminergic effect Effects 0.000 abstract 1
- 230000003502 anti-nociceptive effect Effects 0.000 abstract 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 abstract 1
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical class OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000010261 cell growth Effects 0.000 abstract 1
- 210000003169 central nervous system Anatomy 0.000 abstract 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 abstract 1
- 229960001076 chlorpromazine Drugs 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 230000000994 depressogenic effect Effects 0.000 abstract 1
- 229960003878 haloperidol Drugs 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 230000003463 hyperproliferative effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- 239000003176 neuroleptic agent Substances 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/14—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D277/16—Sulfur atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Dermatology (AREA)
- Pulmonology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Novel 5-(subst. phenyl)-oxazolidinones and their sulphur analogs of the general formula I <IMAGE> in which the substituents are defined in Claim 1, are obtained by reacting 2-amino-1(3,4-disubst. phenyl)-ethanols with a carbonic acid derivative or a thiocarbonic acid derivative in an inert solvent while heating in the presence of a basic catalyst. The novel compounds of the general formula I possess valuable pharmacological properties. They exhibit antidopaminergic, antinociceptive and anticonvulsive effects and have a depressant action on the central nervous system and thus have a certain similarity to neuroleptic agents such as chlorpromazine or haloperidol. In addition, the novel compounds possess strong phosphodiesterase-inhibiting properties and thus affect the metabolism of cyclic nucleotides. The compounds are also suitable for treating hyperproliferative diseases and diseases associated with uncontrolled cell growth.
[GB1588639A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762655369 DE2655369A1 (en) | 1976-12-03 | 1976-12-03 | 5- (SUBST. PHENYL) -OXAZOLIDINONE AND THEIR SULFUR ANALOGS AND PROCESS FOR THEIR PRODUCTION |
| DE19772745320 DE2745320A1 (en) | 1977-10-05 | 1977-10-05 | 5-Alkoxyphenyl-oxazolidine-2-one and sulphur analogues - useful as neuroleptics and phospho-di:esterase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE772446L true IE772446L (en) | 1978-06-03 |
| IE46435B1 IE46435B1 (en) | 1983-06-15 |
Family
ID=25771221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2446/77A IE46435B1 (en) | 1976-12-03 | 1977-12-02 | 5-(substituted phenyl)-oxazolidinones and sulphur analogues thereof and also a process for their production |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5382777A (en) |
| AT (1) | AT357529B (en) |
| AU (1) | AU519994B2 (en) |
| CA (1) | CA1097657A (en) |
| CH (1) | CH635578A5 (en) |
| CS (1) | CS199694B2 (en) |
| DD (1) | DD133667A5 (en) |
| DK (1) | DK149850C (en) |
| FR (1) | FR2372814A1 (en) |
| GB (1) | GB1588639A (en) |
| GR (1) | GR64964B (en) |
| HU (1) | HU175676B (en) |
| IE (1) | IE46435B1 (en) |
| IL (1) | IL53520A (en) |
| IT (1) | IT1089341B (en) |
| LU (1) | LU78616A1 (en) |
| NL (1) | NL7713153A (en) |
| SE (1) | SE441446B (en) |
| SU (1) | SU888821A3 (en) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2701215C2 (en) * | 1977-01-13 | 1982-10-14 | Bayer Ag, 5090 Leverkusen | Process for the preparation of thiazoline-2-thiones |
| US4348393A (en) * | 1978-06-09 | 1982-09-07 | Delalande S.A. | N-Aryl oxazolidinones, oxazolidinethiones, pyrrolidinones, pyrrolidines and thiazolidinones |
| DE3438839A1 (en) * | 1984-10-19 | 1986-04-24 | Schering AG, 1000 Berlin und 4709 Bergkamen | PHARMACEUTICAL PREPARATIONS |
| US5459145A (en) * | 1988-01-19 | 1995-10-17 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| WO1987006576A1 (en) * | 1986-04-29 | 1987-11-05 | Pfizer Inc. | Calcium independent camp phosphodiesterase inhibitor antidepressant |
| JPH01135098U (en) * | 1988-03-11 | 1989-09-14 | ||
| WO1991007177A1 (en) * | 1989-11-13 | 1991-05-30 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| US5461056A (en) * | 1992-05-08 | 1995-10-24 | Pfizer Inc. | Pyrimidone derivatives and analogs in the treatment of asthma or certain skin disorders |
| GB9212673D0 (en) * | 1992-06-15 | 1992-07-29 | Celltech Ltd | Chemical compounds |
| GB9222253D0 (en) * | 1992-10-23 | 1992-12-09 | Celltech Ltd | Chemical compounds |
| GB9226830D0 (en) * | 1992-12-23 | 1993-02-17 | Celltech Ltd | Chemical compounds |
| US5622977A (en) * | 1992-12-23 | 1997-04-22 | Celltech Therapeutics Limited | Tri-substituted (aryl or heteroaryl) derivatives and pharmaceutical compositions containing the same |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| GB9304920D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| ATE260911T1 (en) * | 1993-12-22 | 2004-03-15 | Celltech R&D Ltd | TRISUBSUTITUTED PHENYL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS PHOSPHODIESTERASE (TYPE IV) INHIBITORS |
| GB9326173D0 (en) * | 1993-12-22 | 1994-02-23 | Celltech Ltd | Chemical compounds and process |
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| US5786354A (en) * | 1994-06-21 | 1998-07-28 | Celltech Therapeutics, Limited | Tri-substituted phenyl derivatives and processes for their preparation |
| GB9412573D0 (en) * | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412571D0 (en) | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9412672D0 (en) * | 1994-06-23 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526246D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9526245D0 (en) * | 1995-12-21 | 1996-02-21 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9608435D0 (en) * | 1996-04-24 | 1996-06-26 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9619284D0 (en) * | 1996-09-16 | 1996-10-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9622363D0 (en) | 1996-10-28 | 1997-01-08 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9625184D0 (en) * | 1996-12-04 | 1997-01-22 | Celltech Therapeutics Ltd | Chemical compounds |
| WO1998028281A1 (en) | 1996-12-23 | 1998-07-02 | Celltech Therapeutics Limited | Fused polycyclic 2-aminopyrimidine derivatives, their preparation and their use as protein tyrosine kinase inhibitors |
| GB9705361D0 (en) * | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9713087D0 (en) * | 1997-06-20 | 1997-08-27 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| GB9924862D0 (en) | 1999-10-20 | 1999-12-22 | Celltech Therapeutics Ltd | Chemical compounds |
-
1977
- 1977-11-28 SU SU772546252A patent/SU888821A3/en active
- 1977-11-29 NL NL7713153A patent/NL7713153A/en not_active Application Discontinuation
- 1977-12-01 DD DD7700202354A patent/DD133667A5/en unknown
- 1977-12-01 LU LU78616A patent/LU78616A1/xx unknown
- 1977-12-01 IT IT30254/77A patent/IT1089341B/en active
- 1977-12-01 SE SE7713635A patent/SE441446B/en not_active IP Right Cessation
- 1977-12-02 IE IE2446/77A patent/IE46435B1/en not_active IP Right Cessation
- 1977-12-02 CA CA292,273A patent/CA1097657A/en not_active Expired
- 1977-12-02 CH CH1477977A patent/CH635578A5/en not_active IP Right Cessation
- 1977-12-02 IL IL53520A patent/IL53520A/en unknown
- 1977-12-02 DK DK536677A patent/DK149850C/en not_active IP Right Cessation
- 1977-12-02 HU HU77SCHE632A patent/HU175676B/en not_active IP Right Cessation
- 1977-12-02 GB GB50350/77A patent/GB1588639A/en not_active Expired
- 1977-12-02 AU AU31175/77A patent/AU519994B2/en not_active Expired
- 1977-12-02 JP JP14492277A patent/JPS5382777A/en active Granted
- 1977-12-02 GR GR54913A patent/GR64964B/en unknown
- 1977-12-05 AT AT868677A patent/AT357529B/en not_active IP Right Cessation
- 1977-12-05 CS CS778086A patent/CS199694B2/en unknown
- 1977-12-05 FR FR7736525A patent/FR2372814A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2372814A1 (en) | 1978-06-30 |
| JPS6154792B2 (en) | 1986-11-25 |
| SE7713635L (en) | 1978-06-04 |
| IL53520A (en) | 1981-07-31 |
| GB1588639A (en) | 1981-04-29 |
| AU519994B2 (en) | 1982-01-07 |
| HU175676B (en) | 1980-09-28 |
| DK149850B (en) | 1986-10-13 |
| IE46435B1 (en) | 1983-06-15 |
| CA1097657A (en) | 1981-03-17 |
| FR2372814B1 (en) | 1980-10-10 |
| DD133667A5 (en) | 1979-01-17 |
| IT1089341B (en) | 1985-06-18 |
| LU78616A1 (en) | 1978-04-20 |
| ATA868677A (en) | 1979-12-15 |
| AU3117577A (en) | 1979-06-07 |
| AT357529B (en) | 1980-07-10 |
| IL53520A0 (en) | 1978-03-10 |
| CS199694B2 (en) | 1980-07-31 |
| SE441446B (en) | 1985-10-07 |
| GR64964B (en) | 1980-06-10 |
| JPS5382777A (en) | 1978-07-21 |
| DK149850C (en) | 1987-04-27 |
| CH635578A5 (en) | 1983-04-15 |
| DK536677A (en) | 1978-06-04 |
| NL7713153A (en) | 1978-06-06 |
| SU888821A3 (en) | 1981-12-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |