ES2410793T3 - Nuevo procedimiento para la preparación de derivados de 2-imino-tiazolidin-4-ona - Google Patents
Nuevo procedimiento para la preparación de derivados de 2-imino-tiazolidin-4-ona Download PDFInfo
- Publication number
- ES2410793T3 ES2410793T3 ES07849225T ES07849225T ES2410793T3 ES 2410793 T3 ES2410793 T3 ES 2410793T3 ES 07849225 T ES07849225 T ES 07849225T ES 07849225 T ES07849225 T ES 07849225T ES 2410793 T3 ES2410793 T3 ES 2410793T3
- Authority
- ES
- Spain
- Prior art keywords
- thiazolidin
- formula
- hydroxy
- iliden
- benc
- Prior art date
- Legal status (The legal status 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 status listed.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 82
- 238000002360 preparation method Methods 0.000 title claims abstract 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 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 33
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- YKSNHLNTLVRITE-UHFFFAOYSA-N [Br].CC(Br)=O Chemical compound [Br].CC(Br)=O YKSNHLNTLVRITE-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000002955 isolation Methods 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- TXKYJCYKCWRQQX-UHFFFAOYSA-N 3-phenyl-2-propylimino-1,3-thiazolidin-4-one Chemical compound CCCN=C1SCC(=O)N1C1=CC=CC=C1 TXKYJCYKCWRQQX-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- ZBINHKVUAGKHME-SEYXRHQNSA-N CC(C)\N=C1/SCC(=O)N1C1=CC=CC=C1 Chemical compound CC(C)\N=C1/SCC(=O)N1C1=CC=CC=C1 ZBINHKVUAGKHME-SEYXRHQNSA-N 0.000 claims description 3
- 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 3
- 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 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LSTRKXWIZZZYAS-UHFFFAOYSA-N 2-bromoacetyl bromide Chemical compound BrCC(Br)=O LSTRKXWIZZZYAS-UHFFFAOYSA-N 0.000 abstract description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 72
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 25
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 19
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 12
- 229910052805 deuterium Inorganic materials 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000543 intermediate Substances 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
- 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
- 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
- -1 alkyl tosylate Chemical compound 0.000 description 3
- 150000002431 hydrogen Chemical group 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
- 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
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 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
- NOLHRFLIXVQPSZ-UHFFFAOYSA-N 1,3-thiazolidin-4-one Chemical class O=C1CSCN1 NOLHRFLIXVQPSZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction 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
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- UJNKPILYEWVUNG-UHFFFAOYSA-L cesium;sodium;carbonate Chemical compound [Na+].[Cs+].[O-]C([O-])=O UJNKPILYEWVUNG-UHFFFAOYSA-L 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 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
- CETRZFQIITUQQL-UHFFFAOYSA-N dmso dimethylsulfoxide Chemical compound CS(C)=O.CS(C)=O CETRZFQIITUQQL-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 229940125721 immunosuppressive 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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 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
- 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000004886 process control Methods 0.000 description 1
- 150000003839 salts Chemical class 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
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (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)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IB2006054409 | 2006-11-23 | ||
| WOPCT/IB2006/054409 | 2006-11-23 | ||
| PCT/IB2007/054752 WO2008062376A2 (en) | 2006-11-23 | 2007-11-22 | New process for the preparation of 2-imino-thiazolidin-4-one derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2410793T3 true ES2410793T3 (es) | 2013-07-03 |
Family
ID=39316391
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07849225T Active ES2410793T3 (es) | 2006-11-23 | 2007-11-22 | Nuevo procedimiento para la preparación de derivados de 2-imino-tiazolidin-4-ona |
| ES12000613.5T Active ES2523401T3 (es) | 2006-11-23 | 2007-11-22 | Intermedios de un nuevo procedimiento para la preparación de derivados de 5-benciliden-2-alquilimino-3- feniltiazolidin-4-ona |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES12000613.5T Active ES2523401T3 (es) | 2006-11-23 | 2007-11-22 | Intermedios de un nuevo procedimiento para la preparación de derivados de 5-benciliden-2-alquilimino-3- feniltiazolidin-4-ona |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8263780B2 (enExample) |
| EP (2) | EP2094676B1 (enExample) |
| JP (1) | JP4669564B2 (enExample) |
| KR (1) | KR101255879B1 (enExample) |
| CN (2) | CN103087004A (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 (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE43833E1 (en) | 2003-11-21 | 2012-11-27 | Actelion Pharmaceuticals Ltd. | Thiazolidin-4-one derivatives |
| AU2004295047B2 (en) | 2003-11-21 | 2011-03-10 | Laboratoires Juvise Pharmaceuticals | 5-(benz- (Z) -ylidene) -thiazolidin-4-one derivatives as immunosuppressant agents |
| US8912340B2 (en) | 2006-11-23 | 2014-12-16 | Actelion Pharmaceuticals Ltd. | Process for the preparation of 2-imino-thiazolidin-4-one derivatives |
| DK2278960T4 (da) * | 2008-03-17 | 2020-01-27 | Actelion Pharmaceuticals Ltd | Dosisregimen til en selektiv sip1 receptoragonist |
| GB0819182D0 (en) | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
| HRP20200883T1 (hr) | 2012-08-17 | 2020-09-04 | Actelion Pharmaceuticals Ltd. | Postupak za pripremanje (2z,5z)-5-(3-kloro-4-((r)-2,3-dihidroksipropoksi)benziliden)-2-(propilimino)-3-(o-tolil)tiazolidin-4-ona i međuproizvodi koji se koriste u navedenom postupku |
| EA036075B1 (ru) | 2014-12-11 | 2020-09-23 | Актелион Фармасьютиклз Лтд | Схема дозирования для селективного агониста рецептора s1p1 |
| MA41139B1 (fr) | 2014-12-11 | 2026-02-27 | Laboratoires Juvise Pharmaceuticals | Combinaison pharmaceutique comprenant du ponesimod et son utilisation dans le traitement de la sclérose en plaque |
| 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 |
| US11014897B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms comprising a thiazolidinone compound, compositions and methods of use thereof |
| US11014940B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Thiazolidinone and oxazolidinone compounds and formulations |
| US11013723B1 (en) | 2018-10-16 | 2021-05-25 | Celgene Corporation | Solid forms of a thiazolidinone compound, compositions and methods of use thereof |
| US11186556B1 (en) | 2018-10-16 | 2021-11-30 | Celgene Corporation | Salts of a thiazolidinone compound, solid forms, compositions and methods of use thereof |
| EP3997076A1 (de) * | 2019-07-10 | 2022-05-18 | Bayer Aktiengesellschaft | Verfahren zur herstellung von 2-(phenylimino)-1,3-thiazolidin-4-onen |
| KR20220034818A (ko) * | 2019-07-10 | 2022-03-18 | 바이엘 악티엔게젤샤프트 | 2-(페닐이미노)-1,3-티아졸리딘-4-온의 제조 방법 |
| WO2021084068A1 (en) | 2019-10-31 | 2021-05-06 | Idorsia Pharmaceuticals Ltd | Combination of a cxcr7 antagonist with an s1p1 receptor modulator |
| KR20200019639A (ko) | 2020-01-30 | 2020-02-24 | 전대연 | 만남의 스마트 도착시스템 |
| JP2023513623A (ja) * | 2020-02-18 | 2023-03-31 | バイエル・アクチエンゲゼルシヤフト | ２－（フェニルイミノ）－３－アルキル－１，３－チアゾリジン－４－オン類の製造方法 |
| EP4387960A1 (en) | 2021-08-17 | 2024-06-26 | 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 |
| CN117924210A (zh) * | 2024-01-22 | 2024-04-26 | 赣南师范大学 | 一种2-亚氨基噻唑烷-4-酮类化合物的制备方法 |
Family Cites Families (20)
| 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. |
| PL166269B1 (pl) | 1990-04-27 | 1995-04-28 | Orion Yh Tyma Oy | Sposób wytwarzania nowych farmakologicznie aktywnych pochodnych katecholul PL PL PL PL PL |
| TW221689B (enExample) * | 1991-08-27 | 1994-03-11 | Otsuka Pharma Co Ltd | |
| DE69429641T2 (de) * | 1993-02-26 | 2002-08-29 | Otsuka Pharmaceutical 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 |
| DE60038687T2 (de) | 1999-09-14 | 2009-05-28 | Shionogi & Co., Ltd. | 2-imino-1,3-thiazin-derivate |
| AU767923C (en) * | 1999-11-12 | 2005-03-24 | Fujimoto Co., Ltd. | Novel 2-(N-cyanoimino)thiazolidin-4-one derivatives |
| US20050019825A9 (en) * | 2002-03-15 | 2005-01-27 | Qing Dong | Common ligand mimics: pseudothiohydantoins |
| AU2003255528B2 (en) | 2002-07-10 | 2009-07-16 | Merck Serono Sa | Azolidinone-vinyl fused-benzene derivatives |
| GB0217152D0 (en) | 2002-07-24 | 2002-09-04 | Novartis Ag | Organic compounds |
| EP1567112B1 (en) * | 2002-11-22 | 2008-10-15 | Smithkline Beecham Corporation | THIAZOLIDIN-4-ONES FOR INHIBITING hYAK3 PROTEINS |
| US20040167192A1 (en) * | 2003-01-16 | 2004-08-26 | David Solow-Cordero | Methods of treating conditions associated with an Edg-7 receptor |
| AU2004295047B2 (en) * | 2003-11-21 | 2011-03-10 | Laboratoires Juvise Pharmaceuticals | 5-(benz- (Z) -ylidene) -thiazolidin-4-one derivatives as immunosuppressant agents |
| EP1718642A4 (en) * | 2004-02-25 | 2010-11-24 | Glaxosmithkline Llc | NEW CHEMICAL COMPOUNDS |
| WO2006094233A1 (en) * | 2005-03-03 | 2006-09-08 | Sirtris Pharmaceuticals, Inc. | N,n'-dicyclic isothiourea sirtuin modulators |
| DK2278960T4 (da) * | 2008-03-17 | 2020-01-27 | Actelion Pharmaceuticals Ltd | Dosisregimen til en selektiv sip1 receptoragonist |
| GB0819182D0 (en) * | 2008-10-20 | 2008-11-26 | Actelion Pharmaceuticals Ltd | Crystalline forms |
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2007
- 2007-11-22 DK DK12000613.5T patent/DK2489662T3/da active
- 2007-11-22 EP EP07849225.3A patent/EP2094676B1/en active Active
- 2007-11-22 TW TW096144311A patent/TWI460166B/zh active
- 2007-11-22 MX MX2009005048A patent/MX2009005048A/es active IP Right Grant
- 2007-11-22 JP JP2009537744A patent/JP4669564B2/ja active Active
- 2007-11-22 CN CN2012105461683A patent/CN103087004A/zh active Pending
- 2007-11-22 DK DK07849225.3T patent/DK2094676T3/da active
- 2007-11-22 US US12/516,055 patent/US8263780B2/en active Active
- 2007-11-22 EP EP12000613.5A patent/EP2489662B1/en active Active
- 2007-11-22 KR KR1020097011745A patent/KR101255879B1/ko active Active
- 2007-11-22 CA CA2669069A patent/CA2669069C/en active Active
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2094676A2 (en) | 2009-09-02 |
| DK2489662T3 (da) | 2014-10-20 |
| CN103087004A (zh) | 2013-05-08 |
| BRPI0718986A2 (pt) | 2014-02-11 |
| US20100317867A1 (en) | 2010-12-16 |
| IL198847A (en) | 2015-07-30 |
| WO2008062376A2 (en) | 2008-05-29 |
| CA2669069A1 (en) | 2008-05-29 |
| EP2489662A1 (en) | 2012-08-22 |
| US20110201821A2 (en) | 2011-08-18 |
| IL198847A0 (en) | 2010-02-17 |
| JP2010510976A (ja) | 2010-04-08 |
| AU2007323042B2 (en) | 2012-12-20 |
| US8263780B2 (en) | 2012-09-11 |
| DK2094676T3 (da) | 2013-06-10 |
| KR20090081009A (ko) | 2009-07-27 |
| CA2669069C (en) | 2015-02-17 |
| WO2008062376A3 (en) | 2008-07-10 |
| CN101541772B (zh) | 2013-04-17 |
| CN101541772A (zh) | 2009-09-23 |
| TWI460166B (zh) | 2014-11-11 |
| MX2009005048A (es) | 2009-05-25 |
| TW200831474A (en) | 2008-08-01 |
| KR101255879B1 (ko) | 2013-04-17 |
| EP2094676B1 (en) | 2013-04-10 |
| JP4669564B2 (ja) | 2011-04-13 |
| AU2007323042A1 (en) | 2008-05-29 |
| EP2489662B1 (en) | 2014-08-06 |
| ES2523401T3 (es) | 2014-11-25 |
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