SK286471B6 - Deriváty 2-fenylpyran-4-ónu, spôsob ich prípravy,farmaceutické kompozície s ich obsahom a ich použitie - Google Patents
Deriváty 2-fenylpyran-4-ónu, spôsob ich prípravy,farmaceutické kompozície s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK286471B6 SK286471B6 SK370-2001A SK3702001A SK286471B6 SK 286471 B6 SK286471 B6 SK 286471B6 SK 3702001 A SK3702001 A SK 3702001A SK 286471 B6 SK286471 B6 SK 286471B6
- Authority
- SK
- Slovakia
- Prior art keywords
- group
- methanesulfonylphenyl
- methylpyran
- alkyl
- methyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims description 17
- UFECLJRYNAOWOI-UHFFFAOYSA-N 2-phenylpyran-4-one Chemical class O=C1C=COC(C=2C=CC=CC=2)=C1 UFECLJRYNAOWOI-UHFFFAOYSA-N 0.000 title abstract description 18
- -1 methylthio, amino Chemical group 0.000 claims abstract description 36
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract description 6
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 5
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 5
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 150000002825 nitriles Chemical class 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 84
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 241001465754 Metazoa Species 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- GPURLOFCRUSYCW-UHFFFAOYSA-N 3-(2,4-difluorophenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1C1=CC=C(F)C=C1F GPURLOFCRUSYCW-UHFFFAOYSA-N 0.000 claims description 5
- RVXUQYKMAOJXAP-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1C1=CC=C(Cl)C=C1 RVXUQYKMAOJXAP-UHFFFAOYSA-N 0.000 claims description 5
- 208000002193 Pain Diseases 0.000 claims description 5
- 206010037660 Pyrexia Diseases 0.000 claims description 5
- WOBUKGPQDSRSPN-UHFFFAOYSA-N 3-(2,4-difluorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(F)C=C1F WOBUKGPQDSRSPN-UHFFFAOYSA-N 0.000 claims description 4
- JFVGUQHTGVPGKP-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(difluoromethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C1=C(C=2C=CC(Cl)=CC=2)C(=O)C=C(C(F)F)O1 JFVGUQHTGVPGKP-UHFFFAOYSA-N 0.000 claims description 4
- WHZQULKJHFNVJF-UHFFFAOYSA-N 3-(4-chlorophenyl)-6-(methoxymethyl)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(COC)=CC(=O)C=1C1=CC=C(Cl)C=C1 WHZQULKJHFNVJF-UHFFFAOYSA-N 0.000 claims description 4
- RQVVYXPUTAFVJV-UHFFFAOYSA-N 3-(4-fluorophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(F)C=C1 RQVVYXPUTAFVJV-UHFFFAOYSA-N 0.000 claims description 4
- WJMZUULFKISOCN-UHFFFAOYSA-N 3-(4-fluorophenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1C1=CC=C(F)C=C1 WJMZUULFKISOCN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
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- 150000003814 prostanoids Chemical class 0.000 claims description 4
- 230000016160 smooth muscle contraction Effects 0.000 claims description 4
- ZGQDYDMRFRTLDT-UHFFFAOYSA-N 3-(2-fluorophenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1C1=CC=CC=C1F ZGQDYDMRFRTLDT-UHFFFAOYSA-N 0.000 claims description 3
- IFAPESKQRSIUFT-UHFFFAOYSA-N 3-(4-bromophenoxy)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Br)C=C1 IFAPESKQRSIUFT-UHFFFAOYSA-N 0.000 claims description 3
- XRHLSOYDPVRXAE-UHFFFAOYSA-N 6-methyl-2-(4-methylsulfonylphenyl)-3-phenoxypyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1 XRHLSOYDPVRXAE-UHFFFAOYSA-N 0.000 claims description 3
- RDDACGGTEDFKEE-UHFFFAOYSA-N 6-methyl-3-(4-methylphenoxy)-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C1=CC(C)=CC=C1OC1=C(C=2C=CC(=CC=2)S(C)(=O)=O)OC(C)=CC1=O RDDACGGTEDFKEE-UHFFFAOYSA-N 0.000 claims description 3
- 238000006264 debenzylation reaction Methods 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
- UOUHUNXQGPPJIS-UHFFFAOYSA-N 3-(2,5-difluorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC(F)=CC=C1F UOUHUNXQGPPJIS-UHFFFAOYSA-N 0.000 claims description 2
- ZGYXDCGAOVKCQH-UHFFFAOYSA-N 3-(2-chlorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1Cl ZGYXDCGAOVKCQH-UHFFFAOYSA-N 0.000 claims description 2
- YRCBOEDYXNRZGI-UHFFFAOYSA-N 3-(2-fluorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=CC=C1F YRCBOEDYXNRZGI-UHFFFAOYSA-N 0.000 claims description 2
- SVAIEEBVIUQQQM-UHFFFAOYSA-N 3-(3-chloro-4-methylphenyl)-6-methyl-2-(4-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=C(S(C)(=O)=O)C=CC=1C=1OC(C)=CC(=O)C=1C1=CC=C(C)C(Cl)=C1 SVAIEEBVIUQQQM-UHFFFAOYSA-N 0.000 claims description 2
- XWKIRCKDFSBMOU-UHFFFAOYSA-N 3-(4-chlorophenoxy)-6-methyl-2-(2-methylsulfonylphenyl)pyran-4-one Chemical compound C=1C=CC=C(S(C)(=O)=O)C=1C=1OC(C)=CC(=O)C=1OC1=CC=C(Cl)C=C1 XWKIRCKDFSBMOU-UHFFFAOYSA-N 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
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- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 19
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/24—Sulfones; Sulfoxides having sulfone or sulfoxide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/40—Oxygen atoms attached in positions 3 and 4, e.g. maltol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES9802011A ES2154561B1 (es) | 1998-09-25 | 1998-09-25 | Derivados de 2-fenilpiran-4-ona. |
| ES009900619A ES2168895A1 (es) | 1999-03-26 | 1999-03-26 | Derivados de 2-fenilpiran-4-ona. |
| PCT/EP1999/006873 WO2000018753A1 (en) | 1998-09-25 | 1999-09-16 | 2-phenylpyran-4-one derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK3702001A3 SK3702001A3 (en) | 2001-12-03 |
| SK286471B6 true SK286471B6 (sk) | 2008-11-06 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK370-2001A SK286471B6 (sk) | 1998-09-25 | 1999-09-16 | Deriváty 2-fenylpyran-4-ónu, spôsob ich prípravy,farmaceutické kompozície s ich obsahom a ich použitie |
Country Status (33)
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|---|---|
| US (1) | US6518303B2 (cs) |
| EP (1) | EP1115716B1 (cs) |
| JP (1) | JP4717211B2 (cs) |
| KR (1) | KR100806684B1 (cs) |
| CN (1) | CN1202104C (cs) |
| AR (1) | AR021826A1 (cs) |
| AT (1) | ATE230405T1 (cs) |
| AU (1) | AU765653B2 (cs) |
| BG (1) | BG65308B1 (cs) |
| BR (1) | BR9913939A (cs) |
| CA (1) | CA2345069C (cs) |
| CO (1) | CO5140127A1 (cs) |
| CZ (1) | CZ300357B6 (cs) |
| DE (1) | DE69904738T2 (cs) |
| DK (1) | DK1115716T3 (cs) |
| EE (1) | EE04812B1 (cs) |
| EG (1) | EG23802A (cs) |
| ES (1) | ES2190252T3 (cs) |
| HU (1) | HUP0104620A3 (cs) |
| ID (1) | ID28624A (cs) |
| IL (1) | IL142087A0 (cs) |
| MX (1) | MXPA01003069A (cs) |
| MY (1) | MY121793A (cs) |
| NO (1) | NO327987B1 (cs) |
| NZ (1) | NZ510625A (cs) |
| PE (1) | PE20001067A1 (cs) |
| PL (1) | PL346895A1 (cs) |
| RU (1) | RU2232158C2 (cs) |
| SI (1) | SI1115716T1 (cs) |
| SK (1) | SK286471B6 (cs) |
| TR (1) | TR200100852T2 (cs) |
| TW (1) | TW587079B (cs) |
| WO (1) | WO2000018753A1 (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE283048T1 (de) | 1999-12-08 | 2004-12-15 | Pharmacia Corp | Cyclooxygenase-2 hemmer enthaltende zusammensetzungen mit schnellem wirkungseintritt |
| PE20011333A1 (es) | 2000-03-16 | 2002-01-16 | Almirall Prodesfarma Ag | Derivados de 2-fenilpiran-4-ona como inhibidores de ciclooxigenasa 2 |
| US20040147581A1 (en) * | 2002-11-18 | 2004-07-29 | Pharmacia Corporation | Method of using a Cox-2 inhibitor and a 5-HT1A receptor modulator as a combination therapy |
| ES2214130B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 2-3'-bipiridinas. |
| ES2213485B1 (es) | 2003-02-13 | 2005-12-16 | Almirall Prodesfarma, S.A. | Derivados de la 2-fenilpiran-4-ona. |
| ES2214129B1 (es) * | 2003-02-13 | 2005-12-01 | Almirall Prodesfarma, S.A. | 3-fenilfuran-2-onas. |
| US20040220155A1 (en) * | 2003-03-28 | 2004-11-04 | Pharmacia Corporation | Method of providing a steroid-sparing benefit with a cyclooxygenase-2 inhibitor and compositions therewith |
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| ES490122A0 (es) | 1979-04-05 | 1981-04-01 | Lilly Industries Ltd | Procedimiento para preparar piranonas 5-sustituidas |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20110916 |