HRP20131106T1 - Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]-azetidin-3-karboksilne kiseline - Google Patents
Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]-azetidin-3-karboksilne kiseline Download PDFInfo
- Publication number
- HRP20131106T1 HRP20131106T1 HRP20131106AT HRP20131106T HRP20131106T1 HR P20131106 T1 HRP20131106 T1 HR P20131106T1 HR P20131106A T HRP20131106A T HR P20131106AT HR P20131106 T HRP20131106 T HR P20131106T HR P20131106 T1 HRP20131106 T1 HR P20131106T1
- Authority
- HR
- Croatia
- Prior art keywords
- ethyl
- benzyloxyimino
- azetidine
- trifluoromethyl
- cyclohexyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims 25
- KIHYPELVXPAIDH-UHFFFAOYSA-N 1-[[4-[n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(C)=NOCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 KIHYPELVXPAIDH-UHFFFAOYSA-N 0.000 title 1
- KIHYPELVXPAIDH-HNSNBQBZSA-N 1-[[4-[(e)-n-[[4-cyclohexyl-3-(trifluoromethyl)phenyl]methoxy]-c-methylcarbonimidoyl]-2-ethylphenyl]methyl]azetidine-3-carboxylic acid Chemical compound CCC1=CC(C(\C)=N\OCC=2C=C(C(C3CCCCC3)=CC=2)C(F)(F)F)=CC=C1CN1CC(C(O)=O)C1 KIHYPELVXPAIDH-HNSNBQBZSA-N 0.000 claims 22
- 239000013078 crystal Substances 0.000 claims 18
- 238000000634 powder X-ray diffraction Methods 0.000 claims 14
- 238000005079 FT-Raman Methods 0.000 claims 5
- 238000001228 spectrum Methods 0.000 claims 5
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/397—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having four-membered rings, e.g. azetidine
-
- 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
- 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
-
- 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
-
- 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
-
- 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
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
-
- 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
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C07C57/15—Fumaric acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Claims (22)
1. Hemifumaratna sol, naznačena time, da je od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline.
2. Hemifumaratna sol od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema zahtjevu 1, naznačena time, da spomenuta sol ima stupanj kristaliniteta veći od oko 20%.
3. Hemifumaratna sol od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema zahtjevu 1, naznačena time, da spomenuta sol ima stupanj kristaliniteta veći od oko 90%.
4. Kristalni oblik A, naznačen time, da je od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, pri čemu kristalni oblik ima uzorak difrakcije praha X-zraka s barem jednom specifičnom vršnom vrijednosti na oko 2-theta = 6,9°, 10,1°, 10,6°, 12,1°, 17,5°, 18,1° ili 20,7°.
5. Kristalni oblik A, naznačen time, da je od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, pri čemu kristalni oblik ima uzorak difrakcije praha X-zraka s barem jednom specifičnom vršnom vrijednosti na oko 2-theta = 6,9°, 17,5°, 18,1° ili 20,7°.
6. Kristalni oblik A, naznačen time, da je od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, pri čemu kristalni oblik ima uzorak difrakcije praha X-zraka sa specifičnim vršnim vrijednostima na oko 2-theta = 6,9°, 17,5°, 18,1° ili 20,7°.
7. Kristalni oblik A od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima barem jednu specifičnu vršnu vrijednost na oko 2-theta = 20,7°.
8. Kristalni oblik A od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka sa specifičnim vršnim vrijednostima na oko 2-theta = 6,9°, 17,5°, 18,1°, 20,4 ili 20,7°.
9. Kristalni oblik A od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema bilo kojem zahtjevu od 4 do 8, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka sa specifičnim vršnim vrijednostima nabrojanima u Tablici 1:
Tablica 1
2-theta u stupnjevima d-vrijednost (Angstrom) intenzitet
6,9 12,780 srednji
10,1 8,711 srednji
10,6 8,315 srednji
12,1 7,280 srednji
15,7 5,641 srednji
16,2 5,471 niski
17,5 5,053 srednji
18,1 4,895 srednji
20,4 4,357 srednji
20,7 4,278 jaki
22,1 4,028 srednji
24,0 3,713 srednji
27,3 3,268 srednji
10. Kristalni oblik A od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema bilo kojem zahtjevu od 4 do 8, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka uglavnom isti kao što je uzorak difrakcije praha X-zraka prikazan na donjoj Slici 1:
[image]
11. Kristalni oblik A od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da ima sljedeći FT-Raman spektar:
[image]
12. Kristalni oblik B od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima specifičnu vršnu vrijednost na oko 2-theta = 2,7°.
13. Kristalni oblik B od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, prema zahtjevu 12, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka samo onaj koji ima specifičnu vršnu vrijednost na oko 2-theta = 2,7°.
14. Kristalni oblik B od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da ima sljedeći FT-Raman spektar:
[image]
15. Kristalni oblik C od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima barem jednu specifičnu vršnu vrijednost na oko 2-theta = 7° ili 21,4°.
16. Kristalni oblik C od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema zahtjevu 15, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima barem specifične vršne vrijednosti na oko 2-theta = 7°, 9,5°, 12,5°, 15,2° i 21,4°.
17. Kristalni oblik C od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da ima sljedeći FT-Raman spektar:
[image]
18. Kristalni oblik D od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima barem jednu specifičnu vršnu vrijednost na oko 2-theta = 10,7° ili 21,5°.
19. Kristalni oblik D od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da kristalni oblik ima uzorak difrakcije praha X-zraka koji ima barem specifične vršne vrijednosti na oko 2-theta = 7,1°, 10,7° ili 21,5°.
20. Kristalni oblik D od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da ima sljedeći FT-Raman spektar:
[image]
21. Kristalni oblik E od hemifumaratne soli od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline, naznačen time, da ima sljedeći FT-Raman spektar:
[image]
22. Farmaceutski sastav, naznačen time, da obuhvaća hemifumaratnu sol od 1-(4-{1-[(E)-4-cikloheksil-3-trifluorometil-benziloksiimino]-etil}-2-etil-benzil)-azetidin-3-karboksilne kiseline prema bilo kojem zahtjevu od 1 do 21 u smjesi s farmaceutski prihvatljivim pomoćnim sredstvom, razrjeđivačem ili nosačem.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US20305308P | 2008-12-18 | 2008-12-18 | |
| PCT/US2009/068143 WO2010080409A1 (en) | 2008-12-18 | 2009-12-16 | Hemifumarate salt of 1- [4- [1- ( 4 -cyclohexyl-3 -trifluoromethyl-benzyloxyimino ) -ethyl] -2 -ethyl-benzyl] -a zetidine-3-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20131106T1 true HRP20131106T1 (hr) | 2013-12-20 |
Family
ID=42236293
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20131106AT HRP20131106T1 (hr) | 2008-12-18 | 2013-11-20 | Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]-azetidin-3-karboksilne kiseline |
| HRP20170916TT HRP20170916T1 (hr) | 2008-12-18 | 2017-06-14 | Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]azetidin-3-karboksilne kiseline za uporabu u liječenju bolesti posredovanih limfocitima |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20170916TT HRP20170916T1 (hr) | 2008-12-18 | 2017-06-14 | Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]azetidin-3-karboksilne kiseline za uporabu u liječenju bolesti posredovanih limfocitima |
Country Status (36)
| Country | Link |
|---|---|
| US (6) | US20120115840A1 (hr) |
| EP (2) | EP2676953B1 (hr) |
| JP (1) | JP5627597B2 (hr) |
| KR (5) | KR20170062554A (hr) |
| CN (2) | CN104803902A (hr) |
| AR (3) | AR074694A1 (hr) |
| AU (1) | AU2009335924B2 (hr) |
| BR (1) | BRPI0923176B8 (hr) |
| CA (2) | CA2747437C (hr) |
| CL (1) | CL2011001490A1 (hr) |
| CO (1) | CO6390104A2 (hr) |
| CY (2) | CY1114662T1 (hr) |
| DK (2) | DK2379497T3 (hr) |
| EC (1) | ECSP11011210A (hr) |
| ES (2) | ES2436197T3 (hr) |
| HK (1) | HK1159631A1 (hr) |
| HR (2) | HRP20131106T1 (hr) |
| HU (1) | HUE034819T2 (hr) |
| IL (3) | IL294514A (hr) |
| JO (1) | JO2894B1 (hr) |
| LT (1) | LT2676953T (hr) |
| MA (1) | MA32961B1 (hr) |
| MX (1) | MX2011006609A (hr) |
| MY (1) | MY152669A (hr) |
| NZ (1) | NZ593061A (hr) |
| PE (2) | PE20120336A1 (hr) |
| PL (2) | PL2676953T3 (hr) |
| PT (2) | PT2379497E (hr) |
| RS (2) | RS53041B (hr) |
| RU (1) | RU2518114C3 (hr) |
| SG (1) | SG171785A1 (hr) |
| SI (2) | SI2379497T1 (hr) |
| TW (2) | TWI500603B (hr) |
| UY (1) | UY32330A (hr) |
| WO (1) | WO2010080409A1 (hr) |
| ZA (1) | ZA201103709B (hr) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2661261T (pt) * | 2011-01-07 | 2019-10-25 | Novartis Ag | Formulações imunossupressoras. |
| WO2012095853A1 (en) | 2011-01-10 | 2012-07-19 | Novartis Pharma Ag | Modified release formulations comprising sip receptor modulators |
| PT3129006T (pt) | 2014-04-10 | 2021-04-09 | Novartis Ag | Formulação imunossupressora |
| EP4074312A1 (en) * | 2014-04-10 | 2022-10-19 | Novartis AG | Siponimod immediate release dosage regimen for treating autoimmune diseases |
| US20180042895A1 (en) | 2015-02-26 | 2018-02-15 | Novartis Ag | Treatment of autoimmune disease in a patient receiving additionally a beta-blocker |
| EP3400211A1 (en) | 2016-01-04 | 2018-11-14 | Auspex Pharmaceuticals, Inc. | Azetidine modulators of the sphingosine 1-phosphate receptor |
| US11958805B2 (en) * | 2017-03-09 | 2024-04-16 | Novartis Ag | Solid forms comprising an oxime ether compound, compositions and methods of use thereof |
| US11629124B2 (en) | 2017-03-09 | 2023-04-18 | Novartis Ag | Solid forms comprising an oxime ether compound, compositions and methods of use thereof |
| CN111405897A (zh) | 2017-09-27 | 2020-07-10 | 雷迪博士实验室有限公司 | 辛波莫德、其盐及其固态形式的制备方法 |
| WO2019064185A1 (en) * | 2017-09-27 | 2019-04-04 | Novartis Ag | PARENTERAL FORMULATION COMPRISING SITOMOD |
| RU2020114750A (ru) | 2017-09-29 | 2021-10-29 | Новартис Аг | Схема введения доз сипонимода |
| CN111132677A (zh) * | 2017-09-29 | 2020-05-08 | 诺华股份有限公司 | 西尼莫德的给药方案 |
| EP3743405B1 (en) * | 2018-01-22 | 2023-11-15 | Teva Pharmaceuticals International GmbH | Crystalline siponimod fumaric acid and polymorphs thereof |
| CN110776450B (zh) * | 2018-07-27 | 2022-09-27 | 广东东阳光药业有限公司 | 一种辛波莫德晶型及其制备方法 |
| CN111484434A (zh) * | 2019-01-29 | 2020-08-04 | 东莞市东阳光仿制药研发有限公司 | 一种辛波莫德晶型及其制备方法 |
| WO2020161632A1 (en) * | 2019-02-07 | 2020-08-13 | Dr. Reddy’S Laboratories Limited | Crystalline solid forms of siponimod |
| WO2020174408A1 (en) * | 2019-02-27 | 2020-09-03 | Dr. Reddy's Laboratories Limited | Solid state forms of siponimod |
| EP3972954A1 (en) | 2019-05-21 | 2022-03-30 | Synthon B.V. | Siponimod maleic acid and fumaric acid salt |
| CA3156298A1 (en) | 2019-10-31 | 2021-05-06 | Laetitia POUZOL | Combination of a cxcr7 antagonist with an s1p1 receptor modulator |
| US20230212115A1 (en) * | 2020-05-29 | 2023-07-06 | Cipla Limited | Methods for the preparation of sphingosine 1-phosphate receptor modulators and solid forme thereof |
| EP4217341A1 (en) | 2020-09-25 | 2023-08-02 | Synthon B.V. | Siponimod salts and cocrystals |
| CN112402610A (zh) * | 2020-11-20 | 2021-02-26 | 睿阜隆(杭州)生物医药有限公司 | 1-磷酸鞘氨醇受体调节剂在制备治疗糖尿病的药物中的新用途 |
| WO2022127863A1 (zh) * | 2020-12-16 | 2022-06-23 | 苏州晶云药物科技股份有限公司 | 一种羧酸类化合物半富马酸盐的晶型及其制备方法 |
| US20240150282A1 (en) | 2021-03-26 | 2024-05-09 | Olon S.P.A. | Novel crystalline compound of siponimod hemifumarate |
| 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 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL86632A0 (en) | 1987-06-15 | 1988-11-30 | Ciba Geigy Ag | Derivatives substituted at methyl-amino nitrogen |
| DE69203164T2 (de) * | 1991-06-04 | 1995-11-02 | Fujisawa Pharmaceutical Co | Vorbeugende/therapeutische Zusammensetzung für die Pleuropneumonie des Schweins. |
| NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
| GB9300059D0 (en) | 1992-01-20 | 1993-03-03 | Zeneca Ltd | Quinazoline derivatives |
| TW225528B (hr) | 1992-04-03 | 1994-06-21 | Ciba Geigy Ag | |
| ATE348110T1 (de) | 1992-10-28 | 2007-01-15 | Genentech Inc | Hvegf rezeptor als vegf antagonist |
| EP0716863B1 (en) * | 1993-06-08 | 2002-05-08 | Hisamitsu Pharmaceutical Co., Inc. | Iontophoresis system |
| GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
| US5362718A (en) | 1994-04-18 | 1994-11-08 | American Home Products Corporation | Rapamycin hydroxyesters |
| EP0817775B1 (en) | 1995-03-30 | 2001-09-12 | Pfizer Inc. | Quinazoline derivatives |
| GB9508538D0 (en) | 1995-04-27 | 1995-06-14 | Zeneca Ltd | Quinazoline derivatives |
| US5747498A (en) | 1996-05-28 | 1998-05-05 | Pfizer Inc. | Alkynyl and azido-substituted 4-anilinoquinazolines |
| US5880141A (en) | 1995-06-07 | 1999-03-09 | Sugen, Inc. | Benzylidene-Z-indoline compounds for the treatment of disease |
| MX9800215A (es) | 1995-07-06 | 1998-03-31 | Novartis Ag | Pirrolopirimidas y procesos para su preparacion. |
| US5760041A (en) | 1996-02-05 | 1998-06-02 | American Cyanamid Company | 4-aminoquinazoline EGFR Inhibitors |
| GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
| WO1997037970A1 (fr) * | 1996-04-04 | 1997-10-16 | Sankyo Company, Limited | Derives d'acide phenylalkylcarboxylique |
| DE69710712T3 (de) | 1996-04-12 | 2010-12-23 | Warner-Lambert Co. Llc | Umkehrbare inhibitoren von tyrosin kinasen |
| US5795909A (en) * | 1996-05-22 | 1998-08-18 | Neuromedica, Inc. | DHA-pharmaceutical agent conjugates of taxanes |
| CA2258548C (en) | 1996-06-24 | 2005-07-26 | Pfizer Inc. | Phenylamino-substituted tricyclic derivatives for treatment of hyperproliferative diseases |
| EP0937082A2 (en) | 1996-07-12 | 1999-08-25 | Ariad Pharmaceuticals, Inc. | Materials and method for treating or preventing pathogenic fungal infection |
| DE19638745C2 (de) | 1996-09-11 | 2001-05-10 | Schering Ag | Monoklonale Antikörper gegen die extrazelluläre Domäne des menschlichen VEGF - Rezeptorproteins (KDR) |
| AU4342997A (en) | 1996-09-13 | 1998-04-02 | Sugen, Inc. | Use of quinazoline derivatives for the manufacture of a medicament in the reatment of hyperproliferative skin disorders |
| EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
| CO4950519A1 (es) | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| CO4940418A1 (es) | 1997-07-18 | 2000-07-24 | Novartis Ag | Modificacion de cristal de un derivado de n-fenil-2- pirimidinamina, procesos para su fabricacion y su uso |
| TW557297B (en) | 1997-09-26 | 2003-10-11 | Abbott Lab | Rapamycin analogs having immunomodulatory activity, and pharmaceutical compositions containing same |
| GB9721069D0 (en) | 1997-10-03 | 1997-12-03 | Pharmacia & Upjohn Spa | Polymeric derivatives of camptothecin |
| EP1107964B8 (en) | 1998-08-11 | 2010-04-07 | Novartis AG | Isoquinoline derivatives with angiogenesis inhibiting activity |
| GB9824579D0 (en) | 1998-11-10 | 1999-01-06 | Novartis Ag | Organic compounds |
| UA71587C2 (uk) | 1998-11-10 | 2004-12-15 | Шерінг Акцієнгезелльшафт | Аміди антранілової кислоти та їхнє застосування як лікарських засобів |
| DE69926536T3 (de) | 1998-12-22 | 2013-09-12 | Genentech, Inc. | Antagonisten von vaskular-endothelialen zellwachstumsfaktoren und ihre anwendung |
| ES2265929T3 (es) | 1999-03-30 | 2007-03-01 | Novartis Ag | Derivados de ftalazina para el tratamiento de enfermedades inflamatorias. |
| CA2433181C (en) * | 2000-12-29 | 2005-11-22 | Pfizer Limited | Amlodipine hemifumarate |
| US7927613B2 (en) * | 2002-02-15 | 2011-04-19 | University Of South Florida | Pharmaceutical co-crystal compositions |
| US20030216376A1 (en) * | 2002-03-20 | 2003-11-20 | Revital Lifshitz-Liron | Crystalline forms of quetiapine hemifumarate |
| US6900206B2 (en) * | 2002-06-20 | 2005-05-31 | Bristol-Myers Squibb Company | Indole, azaindole and related heterocyclic sulfonylureido piperazine derivatives |
| DE10315917A1 (de) * | 2003-04-08 | 2004-11-18 | Schwarz Pharma Ag | Hochreine Basen von 3,3-Diphenylpropylaminmonoestern |
| MY150088A (en) * | 2003-05-19 | 2013-11-29 | Irm Llc | Immunosuppressant compounds and compositions |
| WO2004110330A1 (en) | 2003-06-13 | 2004-12-23 | Stephen Dichiera | Adjustable bed support and bed |
| AR051444A1 (es) * | 2004-09-24 | 2007-01-17 | Centocor Inc | Proteinas derivadas de inmunoglobulina especifica de il-23p40, composiciones, epitopos, metodos y usos |
| JP2008521827A (ja) * | 2004-11-29 | 2008-06-26 | ノバルティス アクチエンゲゼルシャフト | Ｓ１ｐ受容体アゴニストの投与レジメン |
| JP2009503108A (ja) * | 2005-08-04 | 2009-01-29 | ノバルティス アクチエンゲゼルシャフト | ビルダグリプチン塩 |
| GT200600350A (es) * | 2005-08-09 | 2007-03-28 | Formulaciones líquidas | |
| US20060223820A1 (en) * | 2006-03-21 | 2006-10-05 | Chemagis Ltd. | Crystalline aripiprazole salts and processes for preparation and purification thereof |
| GB0612721D0 (en) * | 2006-06-27 | 2006-08-09 | Novartis Ag | Organic compounds |
| WO2008061622A1 (en) * | 2006-11-07 | 2008-05-29 | Novartis Ag | Crystalline forms of aliskiren hemifumarate |
-
2009
- 2009-12-16 KR KR1020177014691A patent/KR20170062554A/ko not_active Application Discontinuation
- 2009-12-16 KR KR1020167030350A patent/KR20160129915A/ko active Application Filing
- 2009-12-16 CN CN201510102280.1A patent/CN104803902A/zh active Pending
- 2009-12-16 MY MYPI20112413 patent/MY152669A/en unknown
- 2009-12-16 PT PT97934137T patent/PT2379497E/pt unknown
- 2009-12-16 HU HUE13177190A patent/HUE034819T2/en unknown
- 2009-12-16 ES ES09793413T patent/ES2436197T3/es active Active
- 2009-12-16 LT LTEP13177190.9T patent/LT2676953T/lt unknown
- 2009-12-16 AU AU2009335924A patent/AU2009335924B2/en active Active
- 2009-12-16 CA CA2747437A patent/CA2747437C/en active Active
- 2009-12-16 RS RS20130510A patent/RS53041B/en unknown
- 2009-12-16 MA MA34008A patent/MA32961B1/fr unknown
- 2009-12-16 DK DK09793413.7T patent/DK2379497T3/da active
- 2009-12-16 KR KR1020117016548A patent/KR20110096584A/ko not_active Application Discontinuation
- 2009-12-16 CA CA2951479A patent/CA2951479A1/en not_active Abandoned
- 2009-12-16 RU RU2011129222A patent/RU2518114C3/ru active Protection Beyond IP Right Term
- 2009-12-16 PT PT131771909T patent/PT2676953T/pt unknown
- 2009-12-16 WO PCT/US2009/068143 patent/WO2010080409A1/en active Application Filing
- 2009-12-16 KR KR1020187000381A patent/KR101885052B1/ko active IP Right Grant
- 2009-12-16 MX MX2011006609A patent/MX2011006609A/es active IP Right Grant
- 2009-12-16 US US13/140,478 patent/US20120115840A1/en not_active Abandoned
- 2009-12-16 SI SI200930750T patent/SI2379497T1/sl unknown
- 2009-12-16 EP EP13177190.9A patent/EP2676953B1/en active Active
- 2009-12-16 IL IL294514A patent/IL294514A/en unknown
- 2009-12-16 ES ES13177190.9T patent/ES2631203T3/es active Active
- 2009-12-16 SG SG2011036886A patent/SG171785A1/en unknown
- 2009-12-16 PL PL13177190T patent/PL2676953T3/pl unknown
- 2009-12-16 EP EP09793413.7A patent/EP2379497B1/en active Active
- 2009-12-16 UY UY0001032330A patent/UY32330A/es not_active Application Discontinuation
- 2009-12-16 PL PL09793413T patent/PL2379497T3/pl unknown
- 2009-12-16 IL IL253845A patent/IL253845B/en unknown
- 2009-12-16 BR BRPI0923176A patent/BRPI0923176B8/pt active IP Right Grant
- 2009-12-16 JP JP2011542351A patent/JP5627597B2/ja active Active
- 2009-12-16 SI SI200931675A patent/SI2676953T1/sl unknown
- 2009-12-16 PE PE2011001226A patent/PE20120336A1/es not_active Application Discontinuation
- 2009-12-16 RS RS20170599A patent/RS56110B1/sr unknown
- 2009-12-16 NZ NZ593061A patent/NZ593061A/xx unknown
- 2009-12-16 PE PE2014001111A patent/PE20142374A1/es not_active Application Discontinuation
- 2009-12-16 KR KR1020167013818A patent/KR20160064245A/ko not_active Application Discontinuation
- 2009-12-16 CN CN2009801512748A patent/CN102256943A/zh active Pending
- 2009-12-16 DK DK13177190.9T patent/DK2676953T3/en active
- 2009-12-16 AR ARP090104917A patent/AR074694A1/es not_active Application Discontinuation
- 2009-12-17 JO JO2009488A patent/JO2894B1/en active
- 2009-12-17 TW TW098143443A patent/TWI500603B/zh active
- 2009-12-17 TW TW103142662A patent/TWI591055B/zh active
-
2011
- 2011-05-20 ZA ZA2011/03709A patent/ZA201103709B/en unknown
- 2011-05-23 IL IL213071A patent/IL213071A0/en unknown
- 2011-06-17 CL CL2011001490A patent/CL2011001490A1/es unknown
- 2011-06-23 CO CO11079284A patent/CO6390104A2/es not_active Application Discontinuation
- 2011-07-15 EC EC2011011210A patent/ECSP11011210A/es unknown
-
2012
- 2012-01-09 HK HK12100216.4A patent/HK1159631A1/xx unknown
-
2013
- 2013-06-12 US US13/915,941 patent/US20140005162A1/en not_active Abandoned
- 2013-11-20 CY CY20131101026T patent/CY1114662T1/el unknown
- 2013-11-20 HR HRP20131106AT patent/HRP20131106T1/hr unknown
-
2015
- 2015-03-03 US US14/636,248 patent/US20150175536A1/en not_active Abandoned
-
2017
- 2017-06-14 HR HRP20170916TT patent/HRP20170916T1/hr unknown
- 2017-06-22 CY CY20171100669T patent/CY1119037T1/el unknown
- 2017-10-31 US US15/799,235 patent/US20180118678A1/en not_active Abandoned
-
2018
- 2018-07-10 AR ARP180101916 patent/AR112227A2/es unknown
-
2020
- 2020-11-11 US US17/095,052 patent/US20210323915A1/en not_active Abandoned
-
2021
- 2021-03-22 AR ARP210100712A patent/AR121635A2/es unknown
-
2022
- 2022-08-10 US US17/818,889 patent/US20230357142A9/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20131106T1 (hr) | Hemifumaratna sol od 1-[4-[1-(4-cikloheksil-3-trifluorometil-benziloksiimino)-etil]-2-etil-benzil]-azetidin-3-karboksilne kiseline | |
| HRP20211766T1 (hr) | Formulacija i postupak izravne kompresije | |
| ES2573957T3 (es) | Sal de piperazina y procedimiento de preparación de la misma | |
| TW200720190A (en) | Aluminium oxide dispersion | |
| EP2543669A3 (en) | Trihydrochloride forms of a dihydropteridinone derivative and processes for preparation | |
| CO6280489A2 (es) | (r)-2-(4-ciclopropansulfonil-fenil)-n-pirazin-2-il-3-(tetrahidropiran-4-il)-propionamida cristalina | |
| WO2005105043A3 (en) | Pharmaceutical compositions | |
| TW200724589A (en) | Method for producing crystal nucleating agent composition and crystalline polymer composition | |
| WO2008077612A3 (de) | Dünne aluminiumpigmente mit enger dickenverteilung, verfahren zur herstellung derselben und verwendung der aluminiumpigmente | |
| WO2008139235A8 (en) | Novel piperazine salts as d3/d2 antagonists | |
| EP1757664A3 (de) | Paste aus nanoskaligem Pulver und Dispergiermittel | |
| CA2533365A1 (en) | Submerged arc flux | |
| TW200715632A (en) | Inorganic compounds | |
| IL186042A0 (en) | Benzoic acid ester compounds, compositions, uses and methods related thereto | |
| RS53866B1 (en) | PHARMACEUTICAL FORMULATIONS CONTAINING DOPAMINE RECEPTOR LIGANDS | |
| MY158125A (en) | Additives for a hydraulic binder based on belite-calcium-sulphoaluminate-ferrite clinker | |
| IL207994A0 (en) | (e)-n-(2-amino-phenyl)-3-{1-[4-(1-methyl-1h-pyrazol-4-yl)-benzenesulfonyl]-1h-pyrrol-3-yl}-acrylamide salts, compositions comprising the same and uses thereof | |
| UA100476C2 (en) | New crystalline form vi of agomelatine, preparation method and application thereof | |
| EP1939688A4 (en) | COMPOSITION FOR THE FORMATION OF ANTIREFLECTIVE FILM, COMPRISING A PRODUCT OF THE REACTION BETWEEN AN ISOCYANURIC ACID COMPOUND AND A BENZOIC ACID COMPOUND | |
| WO2012001276A3 (fr) | Compositions acides pour l'élimination des oxalates | |
| PE20100085A1 (es) | Formas solidas de (1r,2s,3r)-1-(2-(isoxazol-3-il)-1h-imidazol-4-il)butano-1,2,3,4-tetraol y metodos de uso | |
| WO2007146202A3 (en) | Succinate salts of 6-methoxy-8-[4-(1-(5-fluoro)-quinolin-8-yl-piperidin-4-yl)-piperazin-1-yl]-quinoline and crystalline forms thereof | |
| ES2489467T3 (es) | Polimorfo novedoso del clorhidrato del éster (6-dimetilaminometil-2-naftalenílico) del ácido (4-hidroxicarbamoilfenil)-carbámico | |
| TW200637854A (en) | Crystalline forms | |
| CN205413984U (zh) | 一种用于轧机卷取机的活塞杆旋紧装置 |