HRP20190729T1 - Metoda proizvodnje derivata tienopirimidina - Google Patents
Metoda proizvodnje derivata tienopirimidina Download PDFInfo
- Publication number
- HRP20190729T1 HRP20190729T1 HRP20190729TT HRP20190729T HRP20190729T1 HR P20190729 T1 HRP20190729 T1 HR P20190729T1 HR P20190729T T HRP20190729T T HR P20190729TT HR P20190729 T HRP20190729 T HR P20190729T HR P20190729 T1 HRP20190729 T1 HR P20190729T1
- Authority
- HR
- Croatia
- Prior art keywords
- salt
- difluorobenzyl
- dimethylaminomethyl
- salts
- nitrophenyl
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims 2
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical class C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims 28
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 10
- JDUWYIGQOJMHAI-UHFFFAOYSA-N 6-(4-aminophenyl)-1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1=NC(OC)=CC=C1N1C(=O)C(C(CN(C)C)=C(S2)C=3C=CC(N)=CC=3)=C2N(CC=2C(=CC=CC=2F)F)C1=O JDUWYIGQOJMHAI-UHFFFAOYSA-N 0.000 claims 4
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 4
- PAQZWJGSJMLPMG-UHFFFAOYSA-N 2,4,6-tripropyl-1,3,5,2$l^{5},4$l^{5},6$l^{5}-trioxatriphosphinane 2,4,6-trioxide Chemical compound CCCP1(=O)OP(=O)(CCC)OP(=O)(CCC)O1 PAQZWJGSJMLPMG-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- VFWMXMJJWKJIQM-UHFFFAOYSA-N 1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-6-(4-nitrophenyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound N1=NC(OC)=CC=C1N1C(=O)C(C(CN(C)C)=C(S2)C=3C=CC(=CC=3)[N+]([O-])=O)=C2N(CC=2C(=CC=CC=2F)F)C1=O VFWMXMJJWKJIQM-UHFFFAOYSA-N 0.000 claims 2
- SJWDECZIPJCSDZ-UHFFFAOYSA-N 2-[3-(2,6-difluorophenyl)propoxycarbonylamino]-4-[(dimethylamino)methyl]-5-(4-nitrophenyl)thiophene-3-carboxylic acid Chemical compound FC1=C(CCCOC(=O)NC=2SC(=C(C2C(=O)O)CN(C)C)C2=CC=C(C=C2)[N+](=O)[O-])C(=CC=C1)F SJWDECZIPJCSDZ-UHFFFAOYSA-N 0.000 claims 2
- YPWBPONDYDVMLX-UHFFFAOYSA-N 6-methoxypyridazin-3-amine Chemical compound COC1=CC=C(N)N=N1 YPWBPONDYDVMLX-UHFFFAOYSA-N 0.000 claims 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- FVQXAXOOQBNQRL-UHFFFAOYSA-N ethyl N-[(2,6-difluorophenyl)methyl]-N-[4-[(dimethylamino)methyl]-3-[(6-methoxypyridazin-3-yl)carbamoyl]-5-(4-nitrophenyl)thiophen-2-yl]carbamate Chemical compound FC1=C(CN(C(OCC)=O)C=2SC(=C(C2C(NC=2N=NC(=CC2)OC)=O)CN(C)C)C2=CC=C(C=C2)[N+](=O)[O-])C(=CC=C1)F FVQXAXOOQBNQRL-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 238000006722 reduction reaction Methods 0.000 claims 2
- 238000007363 ring formation reaction Methods 0.000 claims 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 claims 1
- AOMXMOCNKJTRQP-UHFFFAOYSA-N 1-[4-[1-[(2,6-difluorophenyl)methyl]-5-[(dimethylamino)methyl]-3-(6-methoxypyridazin-3-yl)-2,4-dioxothieno[2,3-d]pyrimidin-6-yl]phenyl]-3-methoxyurea Chemical compound C1=CC(NC(=O)NOC)=CC=C1C1=C(CN(C)C)C(C(=O)N(C=2N=NC(OC)=CC=2)C(=O)N2CC=3C(=CC=CC=3F)F)=C2S1 AOMXMOCNKJTRQP-UHFFFAOYSA-N 0.000 claims 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 claims 1
- VGOJOYBYWRRWQL-UHFFFAOYSA-N BrCC=1C(=C(SC1C1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OCCCC1=C(C=CC=C1F)F)C(=O)OCC Chemical compound BrCC=1C(=C(SC1C1=CC=C(C=C1)[N+](=O)[O-])NC(=O)OCCCC1=C(C=CC=C1F)F)C(=O)OCC VGOJOYBYWRRWQL-UHFFFAOYSA-N 0.000 claims 1
- RTWACZJOZGORQQ-UHFFFAOYSA-N FC1=C(CCCOC(=O)NC=2SC(=C(C2C(=O)OCC)CN(C)C)C2=CC=C(C=C2)[N+](=O)[O-])C(=CC=C1)F Chemical compound FC1=C(CCCOC(=O)NC=2SC(=C(C2C(=O)OCC)CN(C)C)C2=CC=C(C=C2)[N+](=O)[O-])C(=CC=C1)F RTWACZJOZGORQQ-UHFFFAOYSA-N 0.000 claims 1
- KXWJHFGQSSBAFO-UHFFFAOYSA-N ethyl 2-[3-(2,6-difluorophenyl)propoxycarbonylamino]-4-methyl-5-(4-nitrophenyl)thiophene-3-carboxylate Chemical compound FC1=C(CCCOC(=O)NC=2SC(=C(C2C(=O)OCC)C)C2=CC=C(C=C2)[N+](=O)[O-])C(=CC=C1)F KXWJHFGQSSBAFO-UHFFFAOYSA-N 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Claims (6)
1. Metoda proizvodnje 1-{4-[1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)-2,4-diokso-1,2,3,4-tetrahidrotieno[2,3-d]pirimidin-6-il]fenil}-3-metoksiuree ili njene soli, koja obuhvaća reagiranje 6-(4-aminofenil)-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)tieno[2,3-d]pirimidin-2,4(1H,3H)-diona ili njegove soli, 1,1’-karbonildiimidazola ili njegove soli i metoksiamina ili njegove soli, gdje se 1,1’-karbonildiimidazol ili njegova sol koristi u količini od 1.6 do 2.5 ekvivalenata u odnosu na 6-(4- aminofenil)-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)tieno[2,3-d]pirimidin-2,4(1H,3H)-dion ili njegovu sol, i metoksiamin ili njegova sol se koristi u količini od 1.0 do 1.5 ekvivalenata u odnosu na1,1’-karbonildiimidazol ili njegovu sol.
2. Metoda iz patentnog zahtjeva 1, koja dalje obuhvaća reagiranje 2-[(2,6-difluorobenzil)etoksikarbonilamino]-4-dimetilaminometil-5-(4-nitrofenil)tiofen-3-karboksilne kiseline ili njene soli sa 3-amino-6-metoksipiridazinom ili njegovom soli u prisustvu anhidrida propilfosfonske kiseline i baze,
podvrgavanje dobivenog etil (2,6-difluorobenzil)-[4-dimetilaminometil-3-(6-metoksipiridazin-3-ilkarbamoil)-5-(4-nitrofenil)tiofen-2-il]karbamata ili njegove soli reakciji ciklizacije, i podvrgavanje dobivenog 1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)-6-(4-nitrofenil)tieno[2,3-d]pirimidin-2,4(1H,3H)-diona ili njegove soli reakciji redukcije, prije reagiranja dobivenog 6-(4-aminofenil)-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)tieno[2,3-d]pirimidin-2,4(1H,3H)-diona ili njegove soli, 1,1’-karbonildiimidazola ili njegove soli i metoksiamina ili njegove soli.
3. Metoda iz patentnog zahtjeva 1, koja dalje obuhvaća reagiranje etil 2-[(2,6-difluorobenzil)etoksikarbonilamino]-4-metil-5-(4-nitrofenil)tiofen-3-karboksilata ili njegove soli sa N-bromosukcinimidom u prisustvu 2,2’-azobis(2,4-dimetilvaleronitrila) i trifluorometilbenzena, reagiranje dobivenog etil 4-bromometil-2-[(2,6-difluorobenzil)etoksikarbonilamino]-5-(4-nitrofenil)tiofen-3-karboksilata ili njegove soli sa dimetilaminom ili njegovom soli,
podvrgavanje dobivenog etil 2-[(2,6-difluorobenzil)etoksikarbonilamino]-4-dimetilaminometil-5-(4-nitrofenil)tiofen-3-karboksilata hidrolizi, reagiranje dobivene 2-[(2,6-difluorobenzil)etoksikarbonilamino]-4-dimetilaminometil-5-(4-nitrofenil)tiofen-3-karboksilne kiseline ili njene soli sa 3-amino-6-metoksipiridazinom ili njegovom soli u prisustvu anhidrida propilfosfonske kiseline i baze,
podvrgavanje dobivenog etil (2,6-difluorobenzil)-[4-dimetilaminometil-3-(6-metoksipiridazin-3-ilkarbamoil)-5-(4-nitrofenil)tiofen-2-il]karbamata ili njegove soli reakciji ciklizacije, i podvrgavanje dobivenog 1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)-6-(4-nitrofenil)tieno[2,3-d]pirimidin-2,4(1H,3H)-diona ili njegove soli reakciji redukcije, prije reagiranja dobivenog 6-(4-aminofenil)-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)tieno[2,3-d]pirimidin-2,4(1H,3H)-diona ili njegove soli, 1,1’-karbonildiimidazola ili njegove soli i metoksiamina ili njegove soli.
4. Spoj predstavljen formulom (II):
gdje R2 je nitro grupa ili amino grupa,
ili njegova sol.
5. Spoj iz patentnog zahtjeva 4, gdje R2 je nitro grupa, ili njegova sol.
6. Spoj iz patentnog zahtjeva 4, gdje R2 je amino grupa, ili njegova sol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2012217679 | 2012-09-28 | ||
| EP13779938.3A EP2900675B1 (en) | 2012-09-28 | 2013-09-27 | Production method of thienopyrimidine derivative |
| PCT/JP2013/077013 WO2014051164A2 (en) | 2012-09-28 | 2013-09-27 | Production method of thienopyrimidine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20190729T1 true HRP20190729T1 (hr) | 2019-06-14 |
Family
ID=49448235
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220622TT HRP20220622T1 (hr) | 2012-09-28 | 2013-09-27 | Kristalni oblik 1-(4-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)-2,4-diokso-1,2,3,4-tetrahidrotieno(2,3-d)-pirimidin-6il)fenil)-3-metoksiurea |
| HRP20190729TT HRP20190729T1 (hr) | 2012-09-28 | 2019-04-17 | Metoda proizvodnje derivata tienopirimidina |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20220622TT HRP20220622T1 (hr) | 2012-09-28 | 2013-09-27 | Kristalni oblik 1-(4-1-(2,6-difluorobenzil)-5-dimetilaminometil-3-(6-metoksipiridazin-3-il)-2,4-diokso-1,2,3,4-tetrahidrotieno(2,3-d)-pirimidin-6il)fenil)-3-metoksiurea |
Country Status (20)
| Country | Link |
|---|---|
| US (8) | US9758528B2 (hr) |
| EP (3) | EP2900675B1 (hr) |
| JP (1) | JP6250564B2 (hr) |
| CN (3) | CN104703992B (hr) |
| AR (1) | AR092707A1 (hr) |
| CA (1) | CA2881132C (hr) |
| CY (1) | CY1121641T1 (hr) |
| DK (2) | DK3415517T3 (hr) |
| ES (2) | ES2724206T3 (hr) |
| HR (2) | HRP20220622T1 (hr) |
| HU (2) | HUE059077T2 (hr) |
| LT (2) | LT2900675T (hr) |
| PL (2) | PL3415517T3 (hr) |
| PT (2) | PT2900675T (hr) |
| RS (2) | RS63199B1 (hr) |
| SI (2) | SI2900675T1 (hr) |
| TR (1) | TR201906318T4 (hr) |
| TW (3) | TWI641611B (hr) |
| UY (1) | UY35058A (hr) |
| WO (1) | WO2014051164A2 (hr) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2900675T1 (sl) | 2012-09-28 | 2019-06-28 | Takeda Pharmaceutical Company Limited | Postopek za pridobivanje tienopirimidin derivata |
| MY180680A (en) | 2015-02-26 | 2020-12-06 | Takeda Pharmaceuticals Co | Solid preparation |
| CN110312512B (zh) | 2016-09-30 | 2023-05-09 | 梦欧文科学有限责任公司 | 用于治疗子宫肌瘤和子宫内膜异位症的方法 |
| WO2018060463A2 (en) | 2016-09-30 | 2018-04-05 | Myovant Sciences Gmbh | Treatment of prostate cancer |
| US10787451B2 (en) * | 2016-11-14 | 2020-09-29 | Jiangsu Hengrui Medicine Co., Ltd. | Crystalline form of GnRH receptor antagonist and preparation method therefor |
| KR20200027481A (ko) | 2017-06-05 | 2020-03-12 | 옵스에파 에스에이 | 자궁내막증의 치료를 위한 고나도트로핀 방출호르몬 길항제 투약요법 |
| CN107188855A (zh) * | 2017-07-14 | 2017-09-22 | 常州工程职业技术学院 | 一种3‑氨基‑6甲氧基哒嗪的制备方法 |
| US11306104B2 (en) | 2018-03-14 | 2022-04-19 | Teva Pharmaceuticals International Gmbh | Solid state forms of Relugolix |
| EP3666776A1 (en) | 2018-12-11 | 2020-06-17 | Sandoz AG | Hydrate of a gonadotropin-releasing hormone receptor antagonist |
| EP3969455A4 (en) * | 2019-05-15 | 2023-07-05 | Dr. Reddy's Laboratories Limited | AMORPHOUS AND CRYSTALLINE FORMS OF RELUGOLIX |
| CN110194776B (zh) * | 2019-06-27 | 2021-05-28 | 四川伊诺达博医药科技有限公司 | 一种瑞卢戈利的合成方法 |
| EP4004001A4 (en) * | 2019-07-29 | 2023-08-30 | Sunshine Lake Pharma Co., Ltd. | SUBSTITUTED PYRIMIDINEONE COMPOUNDS AND USES THEREOF |
| JP2022542159A (ja) * | 2019-08-02 | 2022-09-29 | ジョンソン、マッセイ、パブリック、リミテッド、カンパニー | 固体形態レルゴリクス（Ｒｅｌｕｇｏｌｉｘ） |
| CN112321602A (zh) * | 2019-08-05 | 2021-02-05 | 苏州鹏旭医药科技有限公司 | 一种瑞卢戈利药物中间体的制备方法 |
| CN112390812A (zh) * | 2019-08-14 | 2021-02-23 | 苏州鹏旭医药科技有限公司 | 瑞卢戈利化合物的晶型和无定型固体及其制备方法 |
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| JP2022551316A (ja) * | 2019-10-10 | 2022-12-08 | ミオバント サイエンシズ ゲーエムベーハー | Ｎ－（４－（１－（２，６－ジフルオロベンジル）－５－（（ジメチルアミノ）メチル）－３－（６－メトキシ－３－ピリダジニル）－２，４－ジオキソ－１，２，３，４－テトラヒドロチエノ［２，３－ｄ］ピリミジン－６－イル）フェニル）－Ｎ’－メトキシ尿素の結晶形 |
| WO2021069700A1 (en) * | 2019-10-10 | 2021-04-15 | Myovant Sciences Gmbh | Crystalline solvated forms of n-(4-(1-(2,6-difluorobenzyl)-5- ((dimethylamino)methyl)-3-(6-methoxy-3-pyridazinyl)-2,4-dioxo-1,2,3,4- tetrahydrothieno[2,3-d]pyrimidin-6-yl)phenyl)-n'-methoxyurea |
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