HRP20090412T1 - 3-(2-(dimetlamino)metil-(cikloheks-1-il))fenol-maleat i njegovi kristalni oblici - Google Patents
3-(2-(dimetlamino)metil-(cikloheks-1-il))fenol-maleat i njegovi kristalni oblici Download PDFInfo
- Publication number
- HRP20090412T1 HRP20090412T1 HR20090412T HRP20090412T HRP20090412T1 HR P20090412 T1 HRP20090412 T1 HR P20090412T1 HR 20090412 T HR20090412 T HR 20090412T HR P20090412 T HRP20090412 T HR P20090412T HR P20090412 T1 HRP20090412 T1 HR P20090412T1
- Authority
- HR
- Croatia
- Prior art keywords
- salt
- present
- crystalline form
- cyclohex
- dimethylamino
- Prior art date
Links
- ARKPCUWVXCOCEC-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.CN(C1C(CCCC1)(C=1C=C(C=CC1)O)C)C Chemical compound C(C=C/C(=O)O)(=O)O.CN(C1C(CCCC1)(C=1C=C(C=CC1)O)C)C ARKPCUWVXCOCEC-UHFFFAOYSA-N 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 claims abstract 29
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract 5
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims abstract 5
- 239000011976 maleic acid Substances 0.000 claims abstract 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims abstract 5
- JIRYWFYYBBRJAN-UHFFFAOYSA-N 3-[2-[(dimethylamino)methyl]cyclohexyl]phenol Chemical class CN(C)CC1CCCCC1C1=CC=CC(O)=C1 JIRYWFYYBBRJAN-UHFFFAOYSA-N 0.000 claims abstract 4
- DYUBYVPYECCFFH-BTJKTKAUSA-N (z)-but-2-enedioic acid;3-[2-[(dimethylamino)methyl]cyclohexyl]phenol Chemical compound OC(=O)\C=C/C(O)=O.CN(C)CC1CCCCC1C1=CC=CC(O)=C1 DYUBYVPYECCFFH-BTJKTKAUSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 4
- 239000000843 powder Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 3
- 238000001237 Raman spectrum Methods 0.000 claims 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 2
- 238000002441 X-ray diffraction Methods 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229940124531 pharmaceutical excipient Drugs 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/64—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with rings other than six-membered aromatic rings being part of the carbon skeleton
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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]
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
Abstract
Soli maleinske kiseline i 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenola formule IPatent sadrži još 23 patentna zahtjeva.
Claims (24)
1. Soli maleinske kiseline i 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenola formule I
[image]
2. Soli prema zahtjevu 1, naznačene time da je spoj formule I prisutan kao dijastereomer ili kao smjesa enantiomernih dijastereomera s transkonfiguracijom fenilnog prstena i dimetilaminometilne skupine (1 R,2R ili 1 S,2S konfiguracija).
3. Soli prema zahtjevu 1 ili 2, naznačene time da je spoj prisutan kao enantiomer apsolutne konfiguracije (1 R,2R).
4. Metoda proizvodnje 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleata formule I prema zahtjevu 1-3, naznačena time da sadrži spajanje komponenti 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenola i maleinske kiseline.
5. Metoda prema zahtjevu 4 za proizvodnju 3-[2-(dimetilamino)-metil-(cikloheks-1-il)]-fenol maleata formule I prema zahtjevu 1, naznačena time da sadrži korake
a) otapanja 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenola u otapalu,
b) miješanja otopine s maleinskom kiselinom ili otopine maleinske kiseline, i
c) izolacije spoja formule I.
6. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku A, koja sadrži karakteristični rendgenski difrakcijski uzorak u rasponu od 2° do 35° 2θ� s karakterističnim izraženim linijama, izraženim u d vrijednostima (Å): 9.4 (veoma jak intenzitet, u daljnjem tekstu „vs“), 6.8 (srednji intenzitet, u daljnjem tekstu „m“), 5.56 (jak intenzitet, u daljnjem tekstu „s“), 5.30 (s), 5.22 (s), 4.71 (s), 4.66 (s), 4.24 (m), 4.12 (m), 4.03 (m), 3.98 (s) 3.76 (m), 3.27 (m).
7. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku A, naznačena time da difraktogram praha sadrži jednu ili više sljedećih refleksija: 9.38, 9.94 i 10.35 (u svakom slučaju + 0.5 u 2 theta).
8. Sol prema zahtjevu 7, gdje je sol prisutna u kristalnom obliku A, naznačena time da difraktogram praha nadalje sadrži jednu ili više od sljedećih refleksija: 12.76, 15.94, 17.54, 19.28, 28.68 i 31.99 (u svakom slučaju + 0.2 u 2 theta).
9. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku A, naznačena time da Ramanov spektar sadrži jednu ili više sljedećih vrpci, u svakom slučaju izraženih u valnim brojevima (cm-1): 118 (vs), 188 (slab intenzitet, u daljnjem tekstu „w“), 400 (w), 676 (w), 2812 (w), 2879 (m).
10. Sol prema zahtjevu 9, naznačena time da sadrži jednu ili više sljedećih vrpci: 118 (vs), 188 (w), 292 (m), 328 (m), 359 (w), 400 (w), 486 (veoma slab intenzitet, u daljnjem tekstu „vw“), 676 (w), 901 (w), 1025 (w), 1273 (m), 1351 (m), 1412 (w), 1569 (vw), 1601 (m), 1690 (m), 2812 (w), 2879 (m), 2986 (m), 3060 (m).
11. Sol, sol prisutna u kristalnom obliku A, prema jednom ili više zahtjeva 6-10, naznačena time da je 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleat prisutan u konfiguraciji (1 R,2R).
12. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku B, koja sadrži karakteristični rendgenski difrakcijski uzorak u rasponu od 2° do 35° 2θ� s karakterističnim izraženim linijama, izraženim u d vrijednostima (Å): 10.6 (m), 7.5 (m), 7.3 (m), 6.1 (s), 5.29 (s) 4.88 (m), 4.72 (m), 4.47 (vs), 4.43 (m), 4.26 (m), 4.24 (m), 3.99 (s), 3.71(m), 3.52 (m), 3.30 (s).
13. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku B, naznačena time da difraktogram praha sadrži jednu ili više sljedećih refleksija: 8.36, 14.5 i 14.83 (u svakom slučaju + 0.5 u 2 theta).
14. Sol prema zahtjevu 13, gdje je sol prisutna u kristalnom obliku B, naznačena time da difraktogram praha nadalje sadrži jednu ili više od sljedećih refleksija: 11.85, 12.19, 18.16, 22.85, 29.1 i 29.41 (u svakom slučaju + 0.2 u 2 theta).
15. Sol prema zahtjevu 1-3, gdje je sol prisutna u kristalnom obliku B, naznačena time da Ramanov spektar sadrži jednu ili više sljedećih vrpci, u svakom slučaju izraženih u valnim brojevima (cm- 1): 229 (m), 875 (m) i 2829 (m).
16. Sol, sol prisutna u kristalnom obliku B, prema zahtjevu 15, naznačena time da sadrži jednu ili više sljedećih vrpci: 229 (m), 307 (w), 372 (w), 605 (vw), 875 (m), 890 (w), 1010 (w), 1197 (m), 1401 (vw), 1480 (vw), 1583 (m), 1703(s), 2829 (m), 2953 (s).
17. Metoda proizvodnje kristalnog oblika B 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleata, naznačena time da je 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleat otopljen u smjesi tetrahidrofurana i vode u volumnom odnosu 0.8:1.2 do 1.2:0.8, nakon čega se smjesa otapala potpuno uklonila (a) na sobnoj temperaturi od barem 80°C, ili (b) na sobnoj temperaturi u otvorenoj posudi u otvorenoj atmosferi u kontaktu s atmosferskom vlagom, ili (c) suspenzija 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleata je miješana u otapalu kao nosaču na temperaturi od barem 120°C dok se tvorba kristalnog oblika B ne dovrši.
18. Sol, sol prisutna u kristalnom obliku B, koja se može dobiti metodom prema zahtjevu 17.
19. Sol, sol prisutna u kristalnom obliku B, prema jednom ili više zahtjeva 12-16 i 18, naznačena time da je 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleat prisutan u konfiguraciji (1R,2R).
20. Farmaceutski sastav koji sadrži aktivnu količinu 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleata formule I prema zahtjevu 1-19 i farmaceutski ekscipijent ili farmaceutski razrjeđivač.
21. Sastav prema zahtjevu 20, u kojem je spoj formule I prisutan u kristalnom obliku A, kristalnom obliku B ili u smjesi oblika A i B.
22. Sastav prema zahtjevu 21, u kojem je spoj formule I sadržan kao kristalni oblik A.
23. Upotreba 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleata formule I prema zahtjevu 1-22 za proizvodnju farmaceutskog sastava za liječenje boli.
24. 3-[2-(dimetilamino)metil-(cikloheks-1-il)]-fenol maleat formule I prema zahtjevu 1-22 za liječenje boli.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005034974A DE102005034974A1 (de) | 2005-07-22 | 2005-07-22 | Salz von Dimethylaminomethyl-phenyl-cyclohexan und dessen kristalline Formen |
| PCT/EP2006/007160 WO2007009792A1 (de) | 2005-07-22 | 2006-07-20 | 3-(2-(dimethylamino)methyl-(cyclohex-1-yl))phenol-maleat und dessen kristalline formen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20090412T1 true HRP20090412T1 (hr) | 2009-09-30 |
Family
ID=37084866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20090412T HRP20090412T1 (hr) | 2005-07-22 | 2009-07-24 | 3-(2-(dimetlamino)metil-(cikloheks-1-il))fenol-maleat i njegovi kristalni oblici |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP1881956B1 (hr) |
| JP (1) | JP5205259B2 (hr) |
| KR (1) | KR20080033436A (hr) |
| CN (1) | CN101228110A (hr) |
| AR (1) | AR057674A1 (hr) |
| AT (1) | ATE431332T1 (hr) |
| AU (1) | AU2006271856B2 (hr) |
| BR (1) | BRPI0614057A2 (hr) |
| CA (1) | CA2615926A1 (hr) |
| CY (1) | CY1109208T1 (hr) |
| DE (2) | DE102005034974A1 (hr) |
| DK (1) | DK1881956T3 (hr) |
| EC (1) | ECSP088088A (hr) |
| ES (1) | ES2326493T3 (hr) |
| HK (1) | HK1112612A1 (hr) |
| HR (1) | HRP20090412T1 (hr) |
| IL (1) | IL188897A (hr) |
| MX (1) | MX2008000743A (hr) |
| NO (1) | NO20080826L (hr) |
| PE (1) | PE20070368A1 (hr) |
| PL (1) | PL1881956T3 (hr) |
| PT (1) | PT1881956E (hr) |
| RU (1) | RU2434845C2 (hr) |
| SI (1) | SI1881956T1 (hr) |
| WO (1) | WO2007009792A1 (hr) |
| ZA (1) | ZA200801703B (hr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI384986B (zh) * | 2007-01-17 | 2013-02-11 | Lg Life Sciences Ltd | 抗病毒劑之順丁烯二酸單鹽以及含有該單鹽之醫藥組成物 |
| ES2764451T3 (es) * | 2007-12-07 | 2020-06-03 | Gruenenthal Gmbh | Modificaciones cristalinas del (1R,2R)-3-(3-dimetilamino-1-etil-2-metilpropil)fenol |
| EP2085081A1 (de) | 2008-02-04 | 2009-08-05 | Grünenthal GmbH | 3-(2-Dimethylaminomethyl-cyclohexyl)-phenol gegen polyneuropathischen Schmerz |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19525137C2 (de) * | 1995-07-11 | 2003-02-27 | Gruenenthal Gmbh | 6-Dimethylaminomethyl-1-phenyl-cyclohexanverbin -dungen als Zwischenprodukte zur Herstellung pharmazeutischer Wirkstoffe |
| DE10218862A1 (de) * | 2002-04-26 | 2003-11-06 | Gruenenthal Gmbh | Verfahren zur Chlorierung tertiärer Alkohole |
| DE10356362A1 (de) * | 2003-11-28 | 2005-06-23 | Grünenthal GmbH | Verwendung von 1-Phenyl-3-dimethylamino-propanverbindungen zur Therapie von Angststörungen |
-
2005
- 2005-07-22 DE DE102005034974A patent/DE102005034974A1/de not_active Withdrawn
-
2006
- 2006-07-20 PL PL06776325T patent/PL1881956T3/pl unknown
- 2006-07-20 JP JP2008521894A patent/JP5205259B2/ja not_active Expired - Fee Related
- 2006-07-20 DK DK06776325T patent/DK1881956T3/da active
- 2006-07-20 BR BRPI0614057-2A patent/BRPI0614057A2/pt not_active IP Right Cessation
- 2006-07-20 MX MX2008000743A patent/MX2008000743A/es active IP Right Grant
- 2006-07-20 DE DE502006003728T patent/DE502006003728D1/de active Active
- 2006-07-20 RU RU2008106455/04A patent/RU2434845C2/ru not_active IP Right Cessation
- 2006-07-20 CA CA002615926A patent/CA2615926A1/en not_active Abandoned
- 2006-07-20 AU AU2006271856A patent/AU2006271856B2/en not_active Ceased
- 2006-07-20 CN CNA2006800267177A patent/CN101228110A/zh active Pending
- 2006-07-20 KR KR1020087004229A patent/KR20080033436A/ko active IP Right Grant
- 2006-07-20 WO PCT/EP2006/007160 patent/WO2007009792A1/de active Application Filing
- 2006-07-20 SI SI200630355T patent/SI1881956T1/sl unknown
- 2006-07-20 AT AT06776325T patent/ATE431332T1/de active
- 2006-07-20 PT PT06776325T patent/PT1881956E/pt unknown
- 2006-07-20 PE PE2006000873A patent/PE20070368A1/es not_active Application Discontinuation
- 2006-07-20 ES ES06776325T patent/ES2326493T3/es active Active
- 2006-07-20 EP EP06776325A patent/EP1881956B1/de active Active
- 2006-07-21 AR ARP060103155A patent/AR057674A1/es not_active Application Discontinuation
-
2008
- 2008-01-08 EC EC2008008088A patent/ECSP088088A/es unknown
- 2008-01-21 IL IL188897A patent/IL188897A/en not_active IP Right Cessation
- 2008-02-15 NO NO20080826A patent/NO20080826L/no not_active Application Discontinuation
- 2008-02-21 ZA ZA200801703A patent/ZA200801703B/xx unknown
- 2008-07-08 HK HK08107521.5A patent/HK1112612A1/xx not_active IP Right Cessation
-
2009
- 2009-07-03 CY CY20091100706T patent/CY1109208T1/el unknown
- 2009-07-24 HR HR20090412T patent/HRP20090412T1/hr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL1881956T3 (pl) | 2009-10-30 |
| CY1109208T1 (el) | 2014-07-02 |
| JP2009502757A (ja) | 2009-01-29 |
| MX2008000743A (es) | 2008-03-10 |
| HK1112612A1 (en) | 2008-09-12 |
| AU2006271856A1 (en) | 2007-01-25 |
| PT1881956E (pt) | 2009-06-26 |
| JP5205259B2 (ja) | 2013-06-05 |
| ATE431332T1 (de) | 2009-05-15 |
| AR057674A1 (es) | 2007-12-12 |
| AU2006271856B2 (en) | 2012-03-01 |
| IL188897A (en) | 2012-12-31 |
| CN101228110A (zh) | 2008-07-23 |
| RU2008106455A (ru) | 2009-08-27 |
| DK1881956T3 (da) | 2009-09-07 |
| WO2007009792A1 (de) | 2007-01-25 |
| KR20080033436A (ko) | 2008-04-16 |
| NO20080826L (no) | 2008-02-20 |
| ECSP088088A (es) | 2008-02-20 |
| EP1881956A1 (de) | 2008-01-30 |
| CA2615926A1 (en) | 2007-01-25 |
| EP1881956B1 (de) | 2009-05-13 |
| ZA200801703B (en) | 2009-08-26 |
| RU2434845C2 (ru) | 2011-11-27 |
| PE20070368A1 (es) | 2007-05-12 |
| ES2326493T3 (es) | 2009-10-13 |
| SI1881956T1 (sl) | 2009-10-31 |
| DE102005034974A1 (de) | 2007-04-19 |
| BRPI0614057A2 (pt) | 2012-12-11 |
| DE502006003728D1 (de) | 2009-06-25 |
| IL188897A0 (en) | 2008-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2009001020A (es) | Proceso quimico para preparacion de esteres y amidas de ciclopropano aromaticos. | |
| TNSN08170A1 (en) | 3-alkyl-5- (4-alkyl-5-oxo-tetrahydrofutran-2-yl) pyrrolidin-2-one derivatives as intermediates in the synthesis of renin inhibitors | |
| JP2009528333A (ja) | 選択的アンドロゲン受容体モジュレーター | |
| CN103261187A (zh) | 制备四唑取代的邻氨基苯甲酰胺衍生物的方法以及这些衍生物的新的晶体多形体 | |
| HRP20090412T1 (hr) | 3-(2-(dimetlamino)metil-(cikloheks-1-il))fenol-maleat i njegovi kristalni oblici | |
| RU2544989C2 (ru) | Способ получения производных пропионовой кислоты | |
| JPS62289553A (ja) | 多置換酪酸およびそのエステルのトレオ立体異性体 | |
| CN102911136B (zh) | 一种茶尺蠖性信息素的立体选择性合成方法 | |
| CN103980233B (zh) | 一种高丝氨酸内酯类衍生物、其制备方法和用途 | |
| CN102633741B (zh) | 噻唑类化合物在淡水藻杀藻方面的应用 | |
| US20200317627A1 (en) | Catalytic systems for stereoselective synthesis of chiral amines by enantiodivergent radical c-h amination | |
| JP2018058895A (ja) | （２ｓ，５ｒ）−７−オキソ−６−スルホオキシ−２−［（（３ｒ）−ピロリジン−３−カルボニル）−ヒドラジノカルボニル］−１，６−ジアザ−ビシクロ［３．２．１］オクタン | |
| EA200601569A1 (ru) | 5,6-диалкил-7-амино-триазолопиримидины, способ их получения и их применение для борьбы с патогенными растениями, а также содержащие их средства | |
| CN1408703A (zh) | 具有β2－受体兴奋作用的新型苯乙醇胺类化合物及其制法 | |
| AU2018254463B2 (en) | Methods of preparing indolinobenzodiazepine derivatives | |
| RU2018111482A (ru) | Кристаллические формы бедаквилин фумарата и способы их получения | |
| NO162154B (no) | Analogifremgangsmaate for fremstilling av ureaderivater. | |
| ES2257959B1 (es) | Procedimiento de preparacion del acido (1r, 2s) -1. 2-epoxipropilfosfonico. | |
| CA2615742A1 (en) | Hcl polymorphs of 3-[2-(dimethylamino)methyl(cyclohex-1-yl)]phenol | |
| CN105017126B (zh) | 全氟烷基吡咯衍生物及其合成方法 | |
| CN107474018A (zh) | 一种高活性腈菌唑的制备方法 | |
| EP1317427A1 (de) | Verfahren zur herstellung chiraler verbindungen | |
| JP2008222600A (ja) | 光学活性１，２−アミノアルコール化合物の製造方法及び光学活性触媒 | |
| JP2007145752A (ja) | 光学活性なα−トリフルオロメチルケトン化合物の製造方法 | |
| JP2017014149A (ja) | ストライガ発芽調節剤 |