SK281140B6 - (2r,3s)-beta-fenylizoserín, jeho soli, spôsob jeho prípravy a jeho použitie - Google Patents
(2r,3s)-beta-fenylizoserín, jeho soli, spôsob jeho prípravy a jeho použitie Download PDFInfo
- Publication number
- SK281140B6 SK281140B6 SK746-93A SK74693A SK281140B6 SK 281140 B6 SK281140 B6 SK 281140B6 SK 74693 A SK74693 A SK 74693A SK 281140 B6 SK281140 B6 SK 281140B6
- Authority
- SK
- Slovakia
- Prior art keywords
- beta
- liters
- toluene
- ammonia
- phenylisoserine
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- RZARFIRJROUVLM-JGVFFNPUSA-N (2r,3s)-3-azaniumyl-2-hydroxy-3-phenylpropanoate Chemical compound [O-]C(=O)[C@H](O)[C@@H]([NH3+])C1=CC=CC=C1 RZARFIRJROUVLM-JGVFFNPUSA-N 0.000 title claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 34
- 229910021529 ammonia Inorganic materials 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 claims abstract description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical compound CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000003863 ammonium salts Chemical class 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 4
- 239000011780 sodium chloride Substances 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 claims description 3
- 229910000013 Ammonium bicarbonate Inorganic materials 0.000 claims description 3
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 3
- 235000012538 ammonium bicarbonate Nutrition 0.000 claims description 3
- 239000001099 ammonium carbonate Substances 0.000 claims description 3
- 235000019270 ammonium chloride Nutrition 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- DGFLAADCAIFVIB-KZYPOYLOSA-N [Na].OC(=O)[C@H](O)[C@@H](N)C1=CC=CC=C1 Chemical compound [Na].OC(=O)[C@H](O)[C@@H](N)C1=CC=CC=C1 DGFLAADCAIFVIB-KZYPOYLOSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 239000008346 aqueous phase Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 3
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims 2
- 239000012071 phase Substances 0.000 claims 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- 238000010908 decantation Methods 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims 1
- FWYUNPCLBUSRTG-KZYPOYLOSA-M sodium;(2r,3s)-3-amino-2-hydroxy-3-phenylpropanoate Chemical compound [Na+].[O-]C(=O)[C@H](O)[C@@H](N)C1=CC=CC=C1 FWYUNPCLBUSRTG-KZYPOYLOSA-M 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000012485 toluene extract Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 abstract description 4
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YWLXLRUDGLRYDR-ZHPRIASZSA-N 5beta,20-epoxy-1,7beta,10beta,13alpha-tetrahydroxy-9-oxotax-11-ene-2alpha,4alpha-diyl 4-acetate 2-benzoate Chemical compound O([C@H]1[C@H]2[C@@](C([C@H](O)C3=C(C)[C@@H](O)C[C@]1(O)C3(C)C)=O)(C)[C@@H](O)C[C@H]1OC[C@]12OC(=O)C)C(=O)C1=CC=CC=C1 YWLXLRUDGLRYDR-ZHPRIASZSA-N 0.000 description 4
- OVMSOCFBDVBLFW-VHLOTGQHSA-N 5beta,20-epoxy-1,7beta,13alpha-trihydroxy-9-oxotax-11-ene-2alpha,4alpha,10beta-triyl 4,10-diacetate 2-benzoate Chemical compound O([C@@H]1[C@@]2(C[C@H](O)C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)O)C(=O)C1=CC=CC=C1 OVMSOCFBDVBLFW-VHLOTGQHSA-N 0.000 description 4
- -1 alkaline earth metal salt Chemical class 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- RZARFIRJROUVLM-GVHYBUMESA-N (3r)-3-amino-2-hydroxy-3-phenylpropanoic acid Chemical class OC(=O)C(O)[C@H](N)C1=CC=CC=C1 RZARFIRJROUVLM-GVHYBUMESA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229930014667 baccatin III Natural products 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- HALONVPKHYIEQU-UHFFFAOYSA-N 3-phenyloxirane-2-carboxylic acid Chemical compound OC(=O)C1OC1C1=CC=CC=C1 HALONVPKHYIEQU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052757 nitrogen Chemical class 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Epoxy Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cephalosporin Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9100491A FR2671799B1 (fr) | 1991-01-17 | 1991-01-17 | La b-phenylisoserine-(2r, 3s), ses sels, sa preparation et son emploi. |
| PCT/FR1992/000032 WO1992012958A1 (fr) | 1991-01-17 | 1992-01-16 | LA β-PHENYLISOSERINE-(2R,3S), SES SELS, SA PREPARATION ET SON EMPLOI |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK74693A3 SK74693A3 (en) | 1994-03-09 |
| SK281140B6 true SK281140B6 (sk) | 2000-12-11 |
Family
ID=9408773
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK746-93A SK281140B6 (sk) | 1991-01-17 | 1992-01-16 | (2r,3s)-beta-fenylizoserín, jeho soli, spôsob jeho prípravy a jeho použitie |
Country Status (25)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646176A (en) * | 1992-12-24 | 1997-07-08 | Bristol-Myers Squibb Company | Phosphonooxymethyl ethers of taxane derivatives |
| TW467896B (en) * | 1993-03-19 | 2001-12-11 | Bristol Myers Squibb Co | Novel β-lactams, methods for the preparation of taxanes and sidechain-bearing taxanes |
| IL161372A0 (en) | 2001-11-30 | 2004-09-27 | Bristol Myers Squibb Co | Crystalline solvates of paclitaxel |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2629818B1 (fr) † | 1988-04-06 | 1990-11-16 | Centre Nat Rech Scient | Procede de preparation du taxol |
| FR2629819B1 (fr) † | 1988-04-06 | 1990-11-16 | Rhone Poulenc Sante | Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii |
| CA2023645C (fr) † | 1989-08-23 | 2002-03-26 | Jean-Noel Denis | Procede pour la preparation enantioselective de derives de la phenylisoserine |
-
1991
- 1991-01-17 FR FR9100491A patent/FR2671799B1/fr not_active Expired - Lifetime
-
1992
- 1992-01-15 NZ NZ241312A patent/NZ241312A/en not_active IP Right Cessation
- 1992-01-16 EP EP92904034A patent/EP0603176B2/fr not_active Expired - Lifetime
- 1992-01-16 CA CA002099783A patent/CA2099783C/fr not_active Expired - Lifetime
- 1992-01-16 EP EP92400112A patent/EP0495718A1/fr active Pending
- 1992-01-16 DK DK92904034T patent/DK0603176T4/da active
- 1992-01-16 TW TW081100266A patent/TW221413B/zh not_active IP Right Cessation
- 1992-01-16 CZ CS931390A patent/CZ281266B6/cs not_active IP Right Cessation
- 1992-01-16 RU RU9293051781A patent/RU2090551C1/ru active
- 1992-01-16 AU AU12237/92A patent/AU651669B2/en not_active Expired
- 1992-01-16 SK SK746-93A patent/SK281140B6/sk not_active IP Right Cessation
- 1992-01-16 PL PL92299833A patent/PL167676B1/pl unknown
- 1992-01-16 JP JP50400792A patent/JP3233632B2/ja not_active Expired - Fee Related
- 1992-01-16 MX MX9200181A patent/MX9200181A/es active IP Right Grant
- 1992-01-16 ZA ZA92317A patent/ZA92317B/xx unknown
- 1992-01-16 DE DE69221733T patent/DE69221733T3/de not_active Expired - Lifetime
- 1992-01-16 ES ES92904034T patent/ES2104895T5/es not_active Expired - Lifetime
- 1992-01-16 WO PCT/FR1992/000032 patent/WO1992012958A1/fr active IP Right Grant
- 1992-01-16 AT AT92904034T patent/ATE157081T1/de not_active IP Right Cessation
- 1992-01-16 HU HU9302064A patent/HU213616B/hu unknown
- 1992-01-16 IE IE012792A patent/IE920127A1/en not_active IP Right Cessation
- 1992-01-16 KR KR1019930702148A patent/KR100235372B1/ko not_active Expired - Lifetime
- 1992-01-17 YU YU5492A patent/YU48153B/sh unknown
-
1993
- 1993-07-06 NO NO932458A patent/NO303539B1/no not_active IP Right Cessation
- 1993-07-16 FI FI933249A patent/FI113641B/fi active
-
1997
- 1997-08-26 GR GR960402650T patent/GR3024533T3/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4A | Patent expired |
Expiry date: 20120116 |