SK9182002A3 - Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same - Google Patents
Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same Download PDFInfo
- Publication number
- SK9182002A3 SK9182002A3 SK918-2002A SK9182002A SK9182002A3 SK 9182002 A3 SK9182002 A3 SK 9182002A3 SK 9182002 A SK9182002 A SK 9182002A SK 9182002 A3 SK9182002 A3 SK 9182002A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- compound
- pyridyl
- group
- het
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 238000004519 manufacturing process Methods 0.000 title claims 3
- RWIUQKWSQMMBQD-UHFFFAOYSA-N dithiol-3-imine Chemical class N=C1C=CSS1 RWIUQKWSQMMBQD-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000002253 acid Substances 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 239000003814 drug Substances 0.000 claims abstract 2
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 10
- -1 4,6-dimethyl-2-pyridyl Chemical group 0.000 claims description 7
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- MPPYZMRXIFDUOU-UHFFFAOYSA-N n-(4,6-dimethylpyridin-2-yl)-5-pyridin-3-yldithiol-3-imine Chemical compound CC1=CC(C)=NC(N=C2SSC(=C2)C=2C=NC=CC=2)=C1 MPPYZMRXIFDUOU-UHFFFAOYSA-N 0.000 claims description 7
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 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 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 125000001841 imino group Chemical group [H]N=* 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
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- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 2
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
- MIHADVKEHAFNPG-UHFFFAOYSA-N 2-Amino-5-nitrothiazole Chemical compound NC1=NC=C([N+]([O-])=O)S1 MIHADVKEHAFNPG-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- BRBUBVKGJRPRRD-UHFFFAOYSA-N 4,6-dimethylpyridin-2-amine Chemical compound CC1=CC(C)=NC(N)=C1 BRBUBVKGJRPRRD-UHFFFAOYSA-N 0.000 description 1
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- RWWDMPKLJVARBW-UHFFFAOYSA-N 5-(5-methylthiophen-2-yl)-n-(5-nitro-1,3-thiazol-2-yl)dithiol-3-imine Chemical compound S1C(C)=CC=C1C(SS1)=CC1=NC1=NC=C([N+]([O-])=O)S1 RWWDMPKLJVARBW-UHFFFAOYSA-N 0.000 description 1
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- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
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- 229930003316 Vitamin D Natural products 0.000 description 1
- QYSXJUFSXHHAJI-XFEUOLMDSA-N Vitamin D3 Natural products C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C/C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-XFEUOLMDSA-N 0.000 description 1
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- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
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- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
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- NEPZGUGQLAOODR-UHFFFAOYSA-N methyl 5-methylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(C)S1 NEPZGUGQLAOODR-UHFFFAOYSA-N 0.000 description 1
- TWIIRMSFZNYMQE-UHFFFAOYSA-N methyl pyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=CC=N1 TWIIRMSFZNYMQE-UHFFFAOYSA-N 0.000 description 1
- OLXYLDUSSBULGU-UHFFFAOYSA-N methyl pyridine-4-carboxylate Chemical compound COC(=O)C1=CC=NC=C1 OLXYLDUSSBULGU-UHFFFAOYSA-N 0.000 description 1
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- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
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Classifications
-
- 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
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- A61P17/06—Antipsoriatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (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)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9916194A FR2802926B1 (fr) | 1999-12-22 | 1999-12-22 | Nouveaux derives de 3-imino-1,2-dithioles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| PCT/FR2000/003632 WO2001046180A2 (fr) | 1999-12-22 | 2000-12-21 | Nouveaux derives de 3-imino-1,2-dithioles, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK9182002A3 true SK9182002A3 (en) | 2002-11-06 |
Family
ID=9553587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK918-2002A SK9182002A3 (en) | 1999-12-22 | 2000-12-21 | Novel derivatives of 3-imino-1,2-dithioles, method for producing them and pharmaceutical compositions containing the same |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US6686378B2 (pt) |
| EP (1) | EP1240162B1 (pt) |
| JP (1) | JP2003518113A (pt) |
| KR (1) | KR20020062370A (pt) |
| CN (1) | CN1413208A (pt) |
| AT (1) | ATE240322T1 (pt) |
| AU (1) | AU774563B2 (pt) |
| BR (1) | BR0016568A (pt) |
| CA (1) | CA2394139A1 (pt) |
| CZ (1) | CZ20022159A3 (pt) |
| DE (1) | DE60002759T2 (pt) |
| DK (1) | DK1240162T3 (pt) |
| EA (1) | EA004291B1 (pt) |
| ES (1) | ES2199190T3 (pt) |
| FR (1) | FR2802926B1 (pt) |
| HU (1) | HUP0203643A2 (pt) |
| MX (1) | MXPA02006075A (pt) |
| NO (1) | NO20023023L (pt) |
| NZ (1) | NZ519144A (pt) |
| PL (1) | PL355763A1 (pt) |
| PT (1) | PT1240162E (pt) |
| SK (1) | SK9182002A3 (pt) |
| WO (1) | WO2001046180A2 (pt) |
| ZA (1) | ZA200203964B (pt) |
-
1999
- 1999-12-22 FR FR9916194A patent/FR2802926B1/fr not_active Expired - Fee Related
-
2000
- 2000-12-21 DE DE60002759T patent/DE60002759T2/de not_active Expired - Fee Related
- 2000-12-21 US US10/168,875 patent/US6686378B2/en not_active Expired - Fee Related
- 2000-12-21 CN CN00817648A patent/CN1413208A/zh active Pending
- 2000-12-21 EP EP00990091A patent/EP1240162B1/fr not_active Expired - Lifetime
- 2000-12-21 NZ NZ519144A patent/NZ519144A/en unknown
- 2000-12-21 JP JP2001547090A patent/JP2003518113A/ja active Pending
- 2000-12-21 ES ES00990091T patent/ES2199190T3/es not_active Expired - Lifetime
- 2000-12-21 PT PT00990091T patent/PT1240162E/pt unknown
- 2000-12-21 EA EA200200636A patent/EA004291B1/ru not_active IP Right Cessation
- 2000-12-21 AT AT00990091T patent/ATE240322T1/de not_active IP Right Cessation
- 2000-12-21 WO PCT/FR2000/003632 patent/WO2001046180A2/fr active IP Right Grant
- 2000-12-21 MX MXPA02006075A patent/MXPA02006075A/es not_active Application Discontinuation
- 2000-12-21 AU AU26890/01A patent/AU774563B2/en not_active Ceased
- 2000-12-21 SK SK918-2002A patent/SK9182002A3/sk unknown
- 2000-12-21 CA CA002394139A patent/CA2394139A1/fr not_active Abandoned
- 2000-12-21 CZ CZ20022159A patent/CZ20022159A3/cs unknown
- 2000-12-21 KR KR1020027008061A patent/KR20020062370A/ko not_active Application Discontinuation
- 2000-12-21 DK DK00990091T patent/DK1240162T3/da active
- 2000-12-21 HU HU0203643A patent/HUP0203643A2/hu unknown
- 2000-12-21 PL PL00355763A patent/PL355763A1/xx not_active Application Discontinuation
- 2000-12-21 BR BR0016568-9A patent/BR0016568A/pt not_active IP Right Cessation
-
2002
- 2002-05-17 ZA ZA200203964A patent/ZA200203964B/en unknown
- 2002-06-21 NO NO20023023A patent/NO20023023L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2802926A1 (fr) | 2001-06-29 |
| WO2001046180A2 (fr) | 2001-06-28 |
| US20030013742A1 (en) | 2003-01-16 |
| NO20023023D0 (no) | 2002-06-21 |
| JP2003518113A (ja) | 2003-06-03 |
| DE60002759D1 (de) | 2003-06-18 |
| HUP0203643A2 (hu) | 2003-03-28 |
| PT1240162E (pt) | 2003-08-29 |
| WO2001046180A3 (fr) | 2002-05-16 |
| NO20023023L (no) | 2002-06-21 |
| CZ20022159A3 (cs) | 2002-09-11 |
| ES2199190T3 (es) | 2004-02-16 |
| FR2802926B1 (fr) | 2002-02-01 |
| EP1240162A2 (fr) | 2002-09-18 |
| KR20020062370A (ko) | 2002-07-25 |
| EA200200636A1 (ru) | 2002-12-26 |
| PL355763A1 (en) | 2004-05-17 |
| AU774563B2 (en) | 2004-07-01 |
| DE60002759T2 (de) | 2004-04-29 |
| ZA200203964B (en) | 2003-05-19 |
| NZ519144A (en) | 2003-10-31 |
| WO2001046180A8 (fr) | 2001-07-26 |
| ATE240322T1 (de) | 2003-05-15 |
| BR0016568A (pt) | 2002-10-01 |
| EA004291B1 (ru) | 2004-02-26 |
| AU2689001A (en) | 2001-07-03 |
| EP1240162B1 (fr) | 2003-05-14 |
| CN1413208A (zh) | 2003-04-23 |
| MXPA02006075A (es) | 2002-12-05 |
| DK1240162T3 (da) | 2003-08-11 |
| US6686378B2 (en) | 2004-02-03 |
| CA2394139A1 (fr) | 2001-06-28 |
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