TWI460166B - 製備２-亞胺基-四氫噻唑-４-酮衍生物之新穎方法 - Google Patents
製備２-亞胺基-四氫噻唑-４-酮衍生物之新穎方法 Download PDFInfo
- Publication number
- TWI460166B TWI460166B TW096144311A TW96144311A TWI460166B TW I460166 B TWI460166 B TW I460166B TW 096144311 A TW096144311 A TW 096144311A TW 96144311 A TW96144311 A TW 96144311A TW I460166 B TWI460166 B TW I460166B
- Authority
- TW
- Taiwan
- Prior art keywords
- tetrahydrothiazol
- hydroxy
- benzyl
- group
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 76
- 238000002360 preparation method Methods 0.000 title claims description 19
- HYMJHROUVPWYNQ-UHFFFAOYSA-N 2-amino-1,3-thiazol-4-one Chemical class NC1=NC(=O)CS1 HYMJHROUVPWYNQ-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 82
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- IYCUJNUUHOQRRS-UHFFFAOYSA-N NC(CBr)=N.Br Chemical compound NC(CBr)=N.Br IYCUJNUUHOQRRS-UHFFFAOYSA-N 0.000 claims description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- -1 3-phenyl-2-[(Z)-propylimino]-tetrahydrothiazole Chemical compound 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- KWHSAFDHCJEIBQ-YPKPFQOOSA-N CCCC\N=C1/SCC(=O)N1C1=CC=CC=C1 Chemical compound CCCC\N=C1/SCC(=O)N1C1=CC=CC=C1 KWHSAFDHCJEIBQ-YPKPFQOOSA-N 0.000 claims description 4
- OYBHACSOBWDLDC-YPKPFQOOSA-N CCC\N=C1/SCC(=O)N1C1=CC=CC=C1C Chemical compound CCC\N=C1/SCC(=O)N1C1=CC=CC=C1C OYBHACSOBWDLDC-YPKPFQOOSA-N 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- AUMLCWGHDDYHMK-YPKPFQOOSA-N CC(C)\N=C1/SCC(=O)N1C1=CC=CC=C1C Chemical compound CC(C)\N=C1/SCC(=O)N1C1=CC=CC=C1C AUMLCWGHDDYHMK-YPKPFQOOSA-N 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- ANIMNLDOXXHVJC-UHFFFAOYSA-N 3-(2-methylphenyl)-1,3-thiazolidin-4-one Chemical compound CC1=CC=CC=C1N1C(=O)CSC1 ANIMNLDOXXHVJC-UHFFFAOYSA-N 0.000 claims 1
- RRNZCBCXCGGYFL-UHFFFAOYSA-N 3-phenyl-1,3-thiazolidin-4-one Chemical compound O=C1CSCN1C1=CC=CC=C1 RRNZCBCXCGGYFL-UHFFFAOYSA-N 0.000 claims 1
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 1
- SUCNSVQGABWGJV-OWBHPGMISA-N CC(C)\N=C1/SCC(=O)N1C1=CC=CC(Cl)=C1 Chemical compound CC(C)\N=C1/SCC(=O)N1C1=CC=CC(Cl)=C1 SUCNSVQGABWGJV-OWBHPGMISA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 46
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 20
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000001632 sodium acetate Substances 0.000 description 6
- 235000017281 sodium acetate Nutrition 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- TXKYJCYKCWRQQX-SEYXRHQNSA-N CCC\N=C1/SCC(=O)N1C1=CC=CC=C1 Chemical compound CCC\N=C1/SCC(=O)N1C1=CC=CC=C1 TXKYJCYKCWRQQX-SEYXRHQNSA-N 0.000 description 2
- 238000012369 In process control Methods 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000010965 in-process control Methods 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 description 1
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical class O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- LRIYFYUQOIQGQV-UHFFFAOYSA-N 2-amino-1,3-thiazolidin-4-one Chemical compound NC1NC(=O)CS1 LRIYFYUQOIQGQV-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- 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
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Immunology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2006054409 | 2006-11-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200831474A TW200831474A (en) | 2008-08-01 |
| TWI460166B true TWI460166B (zh) | 2014-11-11 |
Family
ID=39316391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW096144311A TWI460166B (zh) | 2006-11-23 | 2007-11-22 | 製備２-亞胺基-四氫噻唑-４-酮衍生物之新穎方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8263780B2 (enExample) |
| EP (2) | EP2489662B1 (enExample) |
| JP (1) | JP4669564B2 (enExample) |
| KR (1) | KR101255879B1 (enExample) |
| CN (2) | CN101541772B (enExample) |
| AU (1) | AU2007323042B2 (enExample) |
| CA (1) | CA2669069C (enExample) |
| DK (2) | DK2489662T3 (enExample) |
| ES (2) | ES2410793T3 (enExample) |
| IL (1) | IL198847A (enExample) |
| MX (1) | MX2009005048A (enExample) |
| TW (1) | TWI460166B (enExample) |
| WO (1) | WO2008062376A2 (enExample) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE43833E1 (en) | 2003-11-21 | 2012-11-27 | Actelion Pharmaceuticals Ltd. | Thiazolidin-4-one derivatives |
| US7435828B2 (en) | 2003-11-21 | 2008-10-14 | Actelion Pharmaceuticals Ltd. | Thiazolidin-4-one derivatives |
| US8912340B2 (en) | 2006-11-23 | 2014-12-16 | Actelion Pharmaceuticals Ltd. | Process for the preparation of 2-imino-thiazolidin-4-one derivatives |
| HRP20170246T4 (hr) | 2008-03-17 | 2020-02-07 | Actelion Pharmaceuticals Ltd. | Režim doziranja za selektivni agonist s1p1-receptora |
| GB0819182D0 (en) * | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
| EP2885266B1 (en) | 2012-08-17 | 2020-03-18 | Actelion Pharmaceuticals Ltd | Process for the preparation of (2z,5z)-5-(3-chloro-4-((r)-2,3-dihydroxypropoxy)benzylidene)-2-(propylimino)-3-(o-tolyl)thiazolidin-4-one and intermediate used in said process |
| KR102590068B1 (ko) | 2014-12-11 | 2023-10-16 | 액테리온 파마슈티칼 리미티드 | 선택적 s1p1 수용체 효능제에 대한 투약 섭생 |
| MA41139A (fr) | 2014-12-11 | 2017-10-17 | Actelion Pharmaceuticals Ltd | Combinaison pharmaceutique comportant un agoniste sélectif du récepteur sip1 |
| JOP20190207A1 (ar) | 2017-03-14 | 2019-09-10 | Actelion Pharmaceuticals Ltd | تركيبة صيدلانية تشتمل على بونيسيمود |
| WO2019060147A1 (en) * | 2017-09-19 | 2019-03-28 | Teva Pharmaceuticals Usa, Inc. | NEW CRYSTALLINE POLYMORPHE FROM PONESIMOD |
| US11014940B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Thiazolidinone and oxazolidinone compounds and formulations |
| US11186556B1 (en) | 2018-10-16 | 2021-11-30 | Celgene Corporation | Salts of a thiazolidinone compound, solid forms, compositions and methods of use thereof |
| US11013723B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms of a thiazolidinone compound, compositions and methods of use thereof |
| US11014897B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms comprising a thiazolidinone compound, compositions and methods of use thereof |
| US20220315545A1 (en) * | 2019-07-10 | 2022-10-06 | Bayer Aktiengesellschaft | Process of preparing 2-(phenylimino)-1,3-thiazolidin-4-ones |
| EP3997076A1 (de) * | 2019-07-10 | 2022-05-18 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 2-(phenylimino)-1,3-thiazolidin-4-onen |
| MX2022005014A (es) | 2019-10-31 | 2022-05-16 | Idorsia Pharmaceuticals Ltd | Combinacion de un antagonista de cxcr7 con un modulador del receptor s1p1. |
| KR20200019639A (ko) | 2020-01-30 | 2020-02-24 | 전대연 | 만남의 스마트 도착시스템 |
| BR112022014704A2 (pt) * | 2020-02-18 | 2022-10-11 | Bayer Ag | Processo para a preparação de 2-(fenilimino)-3-alquil-1,3-tiazolidin-4-onas |
| US20240368094A1 (en) | 2021-08-17 | 2024-11-07 | Teva Czech Industries S.R.O | Polymorphs of ponesimod |
| EP4212156A1 (en) | 2022-01-13 | 2023-07-19 | Abivax | Combination of 8-chloro-n-(4-(trifluoromethoxy)phenyl)quinolin-2-amine and its derivatives with a s1p receptor modulator |
| WO2023152691A1 (en) * | 2022-02-10 | 2023-08-17 | Metrochem Api Pvt Ltd | Process for the preparation of ponesimod and its intermediates thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050019825A9 (en) * | 2002-03-15 | 2005-01-27 | Qing Dong | Common ligand mimics: pseudothiohydantoins |
| WO2005054215A1 (en) * | 2003-11-21 | 2005-06-16 | Actelion Pharmaceuticals Ltd | 5-(benz- (z) -ylidene) -thiazolidin-4-one derivatives as immunosuppressant agents |
| WO2006094233A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | N,n'-dicyclic isothiourea sirtuin modulators |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3077402A (en) * | 1954-12-06 | 1963-02-12 | Polaroid Corp | Photographic color processes, products, and compositions |
| NL270002A (enExample) | 1960-10-08 | |||
| OA03835A (fr) | 1970-07-17 | 1971-12-24 | Rhone Poulenc Sa | Nouveaux dérivés de la thiazolidine, leur préparation et les compositions qui les contiennent. |
| US5362733A (en) | 1990-04-27 | 1994-11-08 | Orion-Yhtyma Oy | Pharmacologically active catechol derivatives |
| TW221689B (enExample) * | 1991-08-27 | 1994-03-11 | Otsuka Pharma Co Ltd | |
| ATE212018T1 (de) * | 1993-02-26 | 2002-02-15 | Otsuka Pharma Co Ltd | Thiazole oder imidazole derivate als maillard reaktion inhibitoren |
| KR960022486A (ko) | 1994-12-29 | 1996-07-18 | 김준웅 | 신규 티아졸리딘-4-온 유도체 |
| US6353006B1 (en) * | 1999-01-14 | 2002-03-05 | Bayer Corporation | Substituted 2-arylimino heterocycles and compositions containing them, for use as progesterone receptor binding agents |
| WO2001019807A1 (en) | 1999-09-14 | 2001-03-22 | Shionogi & Co., Ltd. | 2-imino-1,3-thiazine derivatives |
| KR100608416B1 (ko) * | 1999-11-12 | 2006-08-02 | 후지모토 쿄다이 가부시키가이샤 | 2-(ｎ-시아노이미노)티아졸리딘-4-온 유도체 |
| CA2493843C (en) | 2002-07-10 | 2012-04-17 | Applied Research Systems Ars Holding N.V. | Azolidinone-vinyl fused-benzene derivatives |
| GB0217152D0 (en) | 2002-07-24 | 2002-09-04 | Novartis Ag | Organic compounds |
| UA80572C2 (en) * | 2002-11-22 | 2007-10-10 | Smithkline Beecham Corp | THIAZOLIDINE DERIVATIVES AS hYAK3 INHIBITORS |
| US20040167192A1 (en) * | 2003-01-16 | 2004-08-26 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| WO2005082901A1 (en) * | 2004-02-25 | 2005-09-09 | Smithkline Beecham Corporation | Novel chemical compounds |
| HRP20170246T4 (hr) * | 2008-03-17 | 2020-02-07 | Actelion Pharmaceuticals Ltd. | Režim doziranja za selektivni agonist s1p1-receptora |
| GB0819182D0 (en) * | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
-
2007
- 2007-11-22 ES ES07849225T patent/ES2410793T3/es active Active
- 2007-11-22 EP EP12000613.5A patent/EP2489662B1/en active Active
- 2007-11-22 US US12/516,055 patent/US8263780B2/en active Active
- 2007-11-22 CN CN2007800431941A patent/CN101541772B/zh active Active
- 2007-11-22 WO PCT/IB2007/054752 patent/WO2008062376A2/en not_active Ceased
- 2007-11-22 JP JP2009537744A patent/JP4669564B2/ja active Active
- 2007-11-22 MX MX2009005048A patent/MX2009005048A/es active IP Right Grant
- 2007-11-22 CN CN2012105461683A patent/CN103087004A/zh active Pending
- 2007-11-22 AU AU2007323042A patent/AU2007323042B2/en active Active
- 2007-11-22 DK DK12000613.5T patent/DK2489662T3/da active
- 2007-11-22 EP EP07849225.3A patent/EP2094676B1/en active Active
- 2007-11-22 ES ES12000613.5T patent/ES2523401T3/es active Active
- 2007-11-22 DK DK07849225.3T patent/DK2094676T3/da active
- 2007-11-22 KR KR1020097011745A patent/KR101255879B1/ko active Active
- 2007-11-22 TW TW096144311A patent/TWI460166B/zh active
- 2007-11-22 CA CA2669069A patent/CA2669069C/en active Active
-
2009
- 2009-05-20 IL IL198847A patent/IL198847A/en active IP Right Grant
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20050019825A9 (en) * | 2002-03-15 | 2005-01-27 | Qing Dong | Common ligand mimics: pseudothiohydantoins |
| WO2005054215A1 (en) * | 2003-11-21 | 2005-06-16 | Actelion Pharmaceuticals Ltd | 5-(benz- (z) -ylidene) -thiazolidin-4-one derivatives as immunosuppressant agents |
| WO2006094233A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | N,n'-dicyclic isothiourea sirtuin modulators |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2010510976A (ja) | 2010-04-08 |
| WO2008062376A3 (en) | 2008-07-10 |
| BRPI0718986A2 (pt) | 2014-02-11 |
| CA2669069C (en) | 2015-02-17 |
| DK2094676T3 (da) | 2013-06-10 |
| EP2094676B1 (en) | 2013-04-10 |
| KR101255879B1 (ko) | 2013-04-17 |
| AU2007323042A1 (en) | 2008-05-29 |
| ES2523401T3 (es) | 2014-11-25 |
| TW200831474A (en) | 2008-08-01 |
| KR20090081009A (ko) | 2009-07-27 |
| US20110201821A2 (en) | 2011-08-18 |
| IL198847A (en) | 2015-07-30 |
| EP2094676A2 (en) | 2009-09-02 |
| US20100317867A1 (en) | 2010-12-16 |
| CN101541772A (zh) | 2009-09-23 |
| EP2489662B1 (en) | 2014-08-06 |
| EP2489662A1 (en) | 2012-08-22 |
| DK2489662T3 (da) | 2014-10-20 |
| MX2009005048A (es) | 2009-05-25 |
| WO2008062376A2 (en) | 2008-05-29 |
| US8263780B2 (en) | 2012-09-11 |
| CA2669069A1 (en) | 2008-05-29 |
| ES2410793T3 (es) | 2013-07-03 |
| IL198847A0 (en) | 2010-02-17 |
| CN103087004A (zh) | 2013-05-08 |
| AU2007323042B2 (en) | 2012-12-20 |
| JP4669564B2 (ja) | 2011-04-13 |
| CN101541772B (zh) | 2013-04-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| TWI460166B (zh) | 製備２-亞胺基-四氫噻唑-４-酮衍生物之新穎方法 | |
| US8912340B2 (en) | Process for the preparation of 2-imino-thiazolidin-4-one derivatives | |
| JP6633539B2 (ja) | ２−（２，４−ジフルオロフェニル）−１，１−ジフルオロ−１−（５−置換−ピリジン−２−イル）−３−（１ｈ−テトラゾール−１−イル）プロパン−２−オールおよびその調製工程 | |
| JPH04234864A (ja) | ２−クロロチアゾール類の製造方法 | |
| EP2266966A1 (en) | A process for the preparation of febuxostat | |
| US11046648B2 (en) | Transition metal-catalyzed protodecarboxylation of α-halo-acrylic acid derivatives | |
| SK3092003A3 (en) | Process for the preparation of mesylates of piperazine derivatives | |
| US6803463B2 (en) | Process for the preparation of pyrazolopyridine derivatives | |
| CN101456862B (zh) | 含有吡唑并嘧啶酮的苯基胍衍生物、其药物组合物及其制备方法和用途 | |
| JP2001064282A (ja) | イミダゾリン化合物、その中間体、およびそれらの製造方法、並びにアゼピン化合物およびその塩の製造方法 | |
| JP7474754B2 (ja) | ジアミノピリミジン誘導体またはその酸付加塩の新規な製造方法 | |
| JPH10218844A (ja) | ２−フェノキシアニリン誘導体 | |
| JPH02289563A (ja) | ｏ―カルボキシピリジル―およびｏ―カルボキシキノリルイミダゾリノンの改良製造法 | |
| JP6961595B2 (ja) | ４−アルコキシ−３−トリフルオロメチルベンジルアルコールの製造方法 | |
| JP4144223B2 (ja) | クロモン誘導体の製造方法 | |
| TW201700458A (zh) | 二羧酸化合物之製法 | |
| JP2004250340A (ja) | ４−ヒドラジノテトラヒドロピラン化合物又はその酸塩の製法 | |
| JPH1077270A (ja) | ２−（１−クロロビニル）ピリジン誘導体およびその製造方法 | |
| JPWO2001004088A1 (ja) | アニリン誘導体の製造方法 |