HRP20191146T1 - Postupak za proizvodnju 2-[4-(ciklopropankarbonil)fenil]-2-metil-propan nitrila - Google Patents
Postupak za proizvodnju 2-[4-(ciklopropankarbonil)fenil]-2-metil-propan nitrila Download PDFInfo
- Publication number
- HRP20191146T1 HRP20191146T1 HRP20191146TT HRP20191146T HRP20191146T1 HR P20191146 T1 HRP20191146 T1 HR P20191146T1 HR P20191146T T HRP20191146T T HR P20191146TT HR P20191146 T HRP20191146 T HR P20191146T HR P20191146 T1 HRP20191146 T1 HR P20191146T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound
- formula
- alkyl
- phenyl
- added
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 18
- OEGDIOHJCJQYBA-UHFFFAOYSA-N 2-[4-(cyclopropanecarbonyl)phenyl]-2-methylpropanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1C(=O)C1CC1 OEGDIOHJCJQYBA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 11
- -1 -CH2-phenyl Chemical group 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims 4
- 239000002202 Polyethylene glycol Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 229920001223 polyethylene glycol Polymers 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 229920001451 polypropylene glycol Polymers 0.000 claims 2
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical group [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 239000000412 dendrimer Substances 0.000 claims 1
- 229920000736 dendritic polymer Polymers 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 claims 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (16)
1. Postupak za pripravu spoja formule I
naznačen time što sadrži reakciju spoja formule XX
pri čemu R1 je fluoro ili kloro,
s izobutironitrilom s formulom XXI
u prisutnosti baze, pri čemu je baza kalijev heksametildisilazan (KHMDS), natrijev heksametildisilazan (NaHMDS) ili natrijev amid.
2. Postupak prema zahtjevu 1, naznačen time što se dodaje spoj koji sadrži barem 3 jedinice strukture -CH2-CH(R7)-O-, pri čemu R7 je H ili CH3.
3. Postupak prema zahtjevu 2, naznačen time što spoj koji se dodaje je polietilen glikol (PEG) ili polipropilen glikol (PPG) s formulom HO(CH2-CH(R7)-O)nH, ili njihova smjesa, koji je nesupstituiran ili supstituirana na jednom ili na oba kraja.
4. Postupak prema zahtjevu 2 ili 3, naznačen time što se dodaje spoj formule XXVIII
pri čemu
n je 3 - 200 000,
R6 i R8 su, međusobno neovisno, H, (C1-C18)alkil, (C3-C18) alkenil, fenil, -CH2-fenil, 2-aminopropil, 3-sulfopropil, glicidil ili C(=O)R9,
R7 je, neovisno za svaku jedinicu, H ili CH3, i
R9 je (C1-C17)alkil, (C2-C17) alkenil, ili fenil,
pri čemu je fenil nesupstituiran ili supstituiran s jednom ili dvije skupine neovisno odabrane od (C1-C12)alkil i halogena.
5. Postupak prema bilo kojem od zahtjeva 2 do 4, naznačen time što R7 je H.
6. Postupak prema bilo kojem od zahtjeva 2 do 4, naznačen time što R7 je CH3.
7. Postupak prema bilo kojem od zahtjeva 4 do 6, naznačen time što R6 i R8, međusobno neovisno, su H, (C1-C18)alkil, (C3-C18)alkenil ili 2-aminopropil.
8. Postupak prema bilo kojem od patentnih zahtjeva 4 do 7, naznačen time što R6 i R8, međusobno neovisno, su H ili (C1-C18)alkil.
9. Postupak prema bilo kojem od zahtjeva 4 do 8, naznačen time što R6 i R8 su (C1-C18)alkil.
10. Postupak prema bilo kojem od zahtjeva 4 do 8, naznačen time što R6 i R8 su H.
11. Postupak prema bilo kojem od zahtjeva 4 do 10, naznačen time što R9 je (C1-C17)alkil, vinil, 2-propenil, heptadek-8-enil ili fenil.
12. Postupak prema zahtjevu 2, naznačen time što se dodaje ciklički polietilen glikol (CPG) s formulom XXXXII
pri čemu
n je 4-8,
jedna ili više skupina CH2-CH2 može biti zamijenjena s fenilom ili cikloheksilom.
13. Postupak prema zahtjevu 2, naznačen time što se dodaje spoj koji ima opću formulu
pri čemu
n je 0, 1 ili 2, m je 0,1,2
Rx i Ry su, međusobno neovisno, H, (C1-C8)alkil ili benzil, ili
Rx i Ry zajedno su -(CH2CH2-O)z-CH2CH2- uz z = 1, 2.
14. Postupak prema zahtjevu 2, naznačen time što se -CH2-CH(R7)-O- jedinice sadržane u dendrimernom spoju sastoje od jezgre i imaju nekoliko grana koje sadrže -CH2-CH(R7)-O jedinice.
15. Postupak prema bilo kojem od patentnih zahtjeva 2 do 14, naznačen time što se spoj dodaje u rasponu od 0.02 do 0.50 masenih ekvivalenata u odnosu na spoj formule XX.
16. Postupak za pripravu spoja formule II
naznačen time što postupak obuhvaća pripremanje spoja formule I prema bilo kojem od patentnih zahtjeva 1- 15 i pretvaranje spoja formule I u spoj formule II.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP15152101 | 2015-01-22 | ||
| PCT/EP2016/051223 WO2016116555A1 (en) | 2015-01-22 | 2016-01-21 | Process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile |
| EP16701157.6A EP3247699B1 (en) | 2015-01-22 | 2016-01-21 | Process for the production of 2-[4-(cyclopropanecarbonyl)phenyl]-2-methyl-propanenitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20191146T1 true HRP20191146T1 (hr) | 2019-10-04 |
Family
ID=52394944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20191146TT HRP20191146T1 (hr) | 2015-01-22 | 2019-06-24 | Postupak za proizvodnju 2-[4-(ciklopropankarbonil)fenil]-2-metil-propan nitrila |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10336698B2 (hr) |
| EP (1) | EP3247699B1 (hr) |
| CN (1) | CN107428678B (hr) |
| CA (1) | CA2974449C (hr) |
| DK (1) | DK3247699T3 (hr) |
| ES (1) | ES2738630T3 (hr) |
| HR (1) | HRP20191146T1 (hr) |
| HU (1) | HUE044642T2 (hr) |
| PL (1) | PL3247699T3 (hr) |
| PT (1) | PT3247699T (hr) |
| RS (1) | RS58961B1 (hr) |
| WO (1) | WO2016116555A1 (hr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3002425C (en) * | 2015-10-22 | 2023-10-17 | Sanofi-Aventis Deutschland Gmbh | Process for the preparation of fexofenadine and of intermediates used therein |
| WO2019232294A1 (en) * | 2018-06-01 | 2019-12-05 | Cornell University | Metal-chelating compositions and their use in methods of removing or inhibiting barium scale |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4254129A (en) | 1979-04-10 | 1981-03-03 | Richardson-Merrell Inc. | Piperidine derivatives |
| JPS60130561A (ja) | 1983-12-16 | 1985-07-12 | Torii Yakuhin Kk | アミジン誘導体およびそれを含む強心剤 |
| DE3839170A1 (de) | 1988-11-19 | 1990-05-31 | Bayer Ag | Cyclopropyl-substituierte azolylmethylcarbinole, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| CN1168717C (zh) | 1993-06-25 | 2004-09-29 | 默里尔药物公司 | 用于制备抗组胺哌啶衍生物的新中间体 |
| US5420322A (en) | 1994-08-31 | 1995-05-30 | Mine Safety Appliances Company | Preparation of alkali-metal hexamethydisilazanes |
| US6303782B1 (en) | 1999-04-20 | 2001-10-16 | Pfizer Inc | Process for preparing benzylnitriles |
| GB0018691D0 (en) | 2000-07-28 | 2000-09-20 | Rolabo Sl | Process |
| US20050222154A1 (en) | 2004-04-05 | 2005-10-06 | Hartmut Rehwinkel | Multiply-substituted tetrahydronaphthalene derivatives, process for their production and their use as anti-inflammatory agents |
| DE602005011132D1 (de) | 2004-05-18 | 2009-01-02 | Hoffmann La Roche | Neuartige cis-imidazoline |
| JP2008540337A (ja) | 2005-04-29 | 2008-11-20 | ワイス | ３，３−二置換オキシインドールおよびチオ−オキシインドールを調製する方法 |
| DE102005045132A1 (de) | 2005-09-22 | 2007-03-29 | Archimica Gmbh | Verfahren zur Herstellung von 2-Arylcarbonylverbindungen, 2-Arylestern und 2-Arylnitrilen sowie ihrer heteroaromatischen Analoga |
| GB0705656D0 (en) | 2007-03-23 | 2007-05-02 | Addex Pharmaceuticals Sa | Novel compounds E1 |
| WO2009001127A1 (en) | 2007-06-26 | 2008-12-31 | Astrazeneca Ab | Cyanocyclopropylcarboxamides as cathepsin inhibitors |
| JP5409968B2 (ja) | 2010-08-05 | 2014-02-05 | ゾエティス・エルエルシー | 駆虫剤としてのイソオキサゾリン誘導体 |
| JP5823616B2 (ja) | 2011-08-17 | 2015-11-25 | エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ | ブルトンチロシンキナーゼインヒビター |
| RU2015122218A (ru) | 2012-11-30 | 2017-01-10 | Ф. Хоффманн-Ля Рош Аг | Ингибиторы тирозинкиназы брутона |
-
2016
- 2016-01-21 CN CN201680016895.5A patent/CN107428678B/zh active Active
- 2016-01-21 HU HUE16701157 patent/HUE044642T2/hu unknown
- 2016-01-21 WO PCT/EP2016/051223 patent/WO2016116555A1/en active Application Filing
- 2016-01-21 US US15/544,493 patent/US10336698B2/en active Active
- 2016-01-21 DK DK16701157.6T patent/DK3247699T3/da active
- 2016-01-21 CA CA2974449A patent/CA2974449C/en active Active
- 2016-01-21 EP EP16701157.6A patent/EP3247699B1/en active Active
- 2016-01-21 RS RS20190866A patent/RS58961B1/sr unknown
- 2016-01-21 PL PL16701157T patent/PL3247699T3/pl unknown
- 2016-01-21 PT PT16701157T patent/PT3247699T/pt unknown
- 2016-01-21 ES ES16701157T patent/ES2738630T3/es active Active
-
2019
- 2019-06-24 HR HRP20191146TT patent/HRP20191146T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL3247699T3 (pl) | 2019-11-29 |
| RS58961B1 (sr) | 2019-08-30 |
| EP3247699B1 (en) | 2019-05-15 |
| EP3247699A1 (en) | 2017-11-29 |
| US10336698B2 (en) | 2019-07-02 |
| ES2738630T3 (es) | 2020-01-24 |
| DK3247699T3 (da) | 2019-08-12 |
| PT3247699T (pt) | 2019-08-06 |
| US20170369440A1 (en) | 2017-12-28 |
| WO2016116555A1 (en) | 2016-07-28 |
| CA2974449A1 (en) | 2016-07-28 |
| HUE044642T2 (hu) | 2019-11-28 |
| CN107428678A (zh) | 2017-12-01 |
| CN107428678B (zh) | 2021-01-01 |
| CA2974449C (en) | 2023-08-29 |
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