AP746A - Process for preparing dioxoazabicyclohexanes. - Google Patents
Process for preparing dioxoazabicyclohexanes. Download PDFInfo
- Publication number
- AP746A AP746A APAP/P/1996/000885A AP9600885A AP746A AP 746 A AP746 A AP 746A AP 9600885 A AP9600885 A AP 9600885A AP 746 A AP746 A AP 746A
- Authority
- AP
- ARIPO
- Prior art keywords
- organic solvent
- process according
- base
- compound
- mixture
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 8
- HGCBTXNRSHFSOF-UHFFFAOYSA-N 1-cyclohexylpiperidine-2,3-dione Chemical class O=C1C(=O)CCCN1C1CCCCC1 HGCBTXNRSHFSOF-UHFFFAOYSA-N 0.000 title description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 57
- 239000003960 organic solvent Substances 0.000 claims abstract description 40
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 229910000027 potassium carbonate Inorganic materials 0.000 claims abstract description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims abstract description 14
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 claims abstract description 12
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims abstract description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000011541 reaction mixture Substances 0.000 claims abstract description 8
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims abstract description 7
- 229910000024 caesium carbonate Inorganic materials 0.000 claims abstract description 7
- 238000011084 recovery Methods 0.000 claims abstract description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 claims abstract description 7
- 239000001488 sodium phosphate Substances 0.000 claims abstract description 7
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims abstract description 7
- 229910000406 trisodium phosphate Inorganic materials 0.000 claims abstract description 7
- 235000019801 trisodium phosphate Nutrition 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 239000011698 potassium fluoride Substances 0.000 claims abstract description 6
- 235000003270 potassium fluoride Nutrition 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000001475 halogen functional group Chemical group 0.000 claims abstract 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 30
- DNPRVXJGNANVCZ-UHFFFAOYSA-N bromo(nitro)methane Chemical compound [O-][N+](=O)CBr DNPRVXJGNANVCZ-UHFFFAOYSA-N 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- 238000001914 filtration Methods 0.000 claims description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 238000006386 neutralization reaction Methods 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 2
- CGKPGVZMSKVVOF-UHFFFAOYSA-N chloro(nitro)methane Chemical group [O-][N+](=O)CCl CGKPGVZMSKVVOF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011877 solvent mixture Substances 0.000 claims description 2
- 230000003019 stabilising effect Effects 0.000 claims 1
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 238000011065 in-situ storage Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002002 slurry Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- -1 dimethyiacetamide Chemical compound 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 2
- 229910052792 caesium Inorganic materials 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- ZFDWWDZLRKHULH-UHFFFAOYSA-N 1,2-dimethyl-5,6-dihydro-4h-pyrimidine Chemical compound CN1CCCN=C1C ZFDWWDZLRKHULH-UHFFFAOYSA-N 0.000 description 1
- 102100034741 Cyclin-dependent kinase 20 Human genes 0.000 description 1
- OTUKPXUUYJTFFJ-UHFFFAOYSA-N F.CC(C)=O Chemical compound F.CC(C)=O OTUKPXUUYJTFFJ-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 101000874141 Homo sapiens Probable ATP-dependent RNA helicase DDX43 Proteins 0.000 description 1
- 101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- 101100074988 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-1 gene Proteins 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 102100035724 Probable ATP-dependent RNA helicase DDX43 Human genes 0.000 description 1
- ZIYVAZASIRJRHP-UHFFFAOYSA-N acetonitrile;hydron;fluoride Chemical compound F.CC#N ZIYVAZASIRJRHP-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- UGQFBHVUOLHZJK-UHFFFAOYSA-L dicesium propan-2-one carbonate Chemical compound C([O-])([O-])=O.[Cs+].CC(=O)C.[Cs+] UGQFBHVUOLHZJK-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000000825 ultraviolet detection Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9524466.1A GB9524466D0 (en) | 1995-11-30 | 1995-11-30 | Process |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP9600885A0 AP9600885A0 (en) | 1997-01-31 |
| AP746A true AP746A (en) | 1999-04-29 |
Family
ID=10784676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1996/000885A AP746A (en) | 1995-11-30 | 1996-11-28 | Process for preparing dioxoazabicyclohexanes. |
Country Status (40)
| Country | Link |
|---|---|
| EP (1) | EP0863874B1 (zh) |
| JP (1) | JP2000507919A (zh) |
| KR (1) | KR100286157B1 (zh) |
| CN (1) | CN1203588A (zh) |
| AP (1) | AP746A (zh) |
| AR (1) | AR004766A1 (zh) |
| AT (1) | ATE198325T1 (zh) |
| AU (1) | AU707221B2 (zh) |
| BG (1) | BG102484A (zh) |
| BR (1) | BR9611833A (zh) |
| CA (1) | CA2231590A1 (zh) |
| CO (1) | CO4480102A1 (zh) |
| CZ (1) | CZ162298A3 (zh) |
| DE (1) | DE69611380T2 (zh) |
| DK (1) | DK0863874T3 (zh) |
| ES (1) | ES2152571T3 (zh) |
| GB (1) | GB9524466D0 (zh) |
| GR (1) | GR3035341T3 (zh) |
| HR (1) | HRP960555A2 (zh) |
| HU (1) | HUP9903571A3 (zh) |
| IL (1) | IL123561A0 (zh) |
| IS (1) | IS4707A (zh) |
| MA (1) | MA24015A1 (zh) |
| MX (1) | MX9804311A (zh) |
| MY (1) | MY132595A (zh) |
| NO (1) | NO982503L (zh) |
| NZ (1) | NZ321968A (zh) |
| OA (1) | OA10692A (zh) |
| PE (1) | PE24898A1 (zh) |
| PL (1) | PL326978A1 (zh) |
| PT (1) | PT863874E (zh) |
| RU (1) | RU2156238C2 (zh) |
| SK (1) | SK70798A3 (zh) |
| TN (1) | TNSN96145A1 (zh) |
| TR (1) | TR199800957T2 (zh) |
| TW (1) | TW401397B (zh) |
| UY (1) | UY24379A1 (zh) |
| WO (1) | WO1997019921A1 (zh) |
| YU (1) | YU63196A (zh) |
| ZA (1) | ZA9610053B (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH1087617A (ja) * | 1996-07-09 | 1998-04-07 | Pfizer Inc | キノリン系抗生物質の合成に有用な中間体の製法 |
| HN1998000106A (es) | 1997-08-01 | 1999-01-08 | Pfizer Prod Inc | Composiciones parenterales de alatroflaxacino |
| US7019142B2 (en) | 1998-01-16 | 2006-03-28 | Pfizer Inc. | Process for preparing naphthyridones and intermediates |
| AU2002246295A1 (en) * | 2002-03-25 | 2003-10-08 | Council Of Scientific And Industrial Research | Protein profiling of hyper acidic plants |
| NL2000192C2 (nl) * | 2006-08-23 | 2008-02-26 | Veenvoort B V De | Stabiel bitumenschuim en de bereiding en het gebruik ervan. |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018001A1 (en) * | 1992-03-02 | 1993-09-16 | Pfizer Inc. | Preparation of intermediates in the synthesis of quinoline antibiotics |
| WO1995019361A1 (en) * | 1994-01-18 | 1995-07-20 | Pfizer Inc. | Process and intermediates for preparing naphthyridonecarboxylic acid salts |
-
1995
- 1995-11-30 GB GBGB9524466.1A patent/GB9524466D0/en active Pending
-
1996
- 1996-10-21 TW TW085112856A patent/TW401397B/zh not_active IP Right Cessation
- 1996-10-31 DK DK96938058T patent/DK0863874T3/da active
- 1996-10-31 IL IL12356196A patent/IL123561A0/xx unknown
- 1996-10-31 PT PT96938058T patent/PT863874E/pt unknown
- 1996-10-31 KR KR1019980703892A patent/KR100286157B1/ko not_active Expired - Fee Related
- 1996-10-31 AU AU75629/96A patent/AU707221B2/en not_active Ceased
- 1996-10-31 ES ES96938058T patent/ES2152571T3/es not_active Expired - Lifetime
- 1996-10-31 RU RU98112016/04A patent/RU2156238C2/ru active
- 1996-10-31 NZ NZ321968A patent/NZ321968A/xx unknown
- 1996-10-31 EP EP96938058A patent/EP0863874B1/en not_active Expired - Lifetime
- 1996-10-31 CA CA002231590A patent/CA2231590A1/en not_active Abandoned
- 1996-10-31 DE DE69611380T patent/DE69611380T2/de not_active Expired - Fee Related
- 1996-10-31 WO PCT/EP1996/004782 patent/WO1997019921A1/en not_active Ceased
- 1996-10-31 JP JP9520100A patent/JP2000507919A/ja active Pending
- 1996-10-31 TR TR1998/00957T patent/TR199800957T2/xx unknown
- 1996-10-31 SK SK707-98A patent/SK70798A3/sk unknown
- 1996-10-31 CZ CZ981622A patent/CZ162298A3/cs unknown
- 1996-10-31 HU HU9903571A patent/HUP9903571A3/hu unknown
- 1996-10-31 AT AT96938058T patent/ATE198325T1/de not_active IP Right Cessation
- 1996-10-31 CN CN96198667A patent/CN1203588A/zh active Pending
- 1996-10-31 PL PL96326978A patent/PL326978A1/xx unknown
- 1996-10-31 BR BR9611833A patent/BR9611833A/pt not_active Application Discontinuation
- 1996-11-21 HR HR9524466.1A patent/HRP960555A2/hr not_active Application Discontinuation
- 1996-11-27 PE PE1996000850A patent/PE24898A1/es not_active Application Discontinuation
- 1996-11-27 TN TNTNSN96145A patent/TNSN96145A1/fr unknown
- 1996-11-27 AR ARP960105343A patent/AR004766A1/es unknown
- 1996-11-27 MA MA24403A patent/MA24015A1/fr unknown
- 1996-11-27 UY UY24379A patent/UY24379A1/es not_active IP Right Cessation
- 1996-11-28 YU YU63196A patent/YU63196A/sh unknown
- 1996-11-28 CO CO96062767A patent/CO4480102A1/es unknown
- 1996-11-28 AP APAP/P/1996/000885A patent/AP746A/en active
- 1996-11-29 ZA ZA9610053A patent/ZA9610053B/xx unknown
- 1996-11-29 MY MYPI96005005A patent/MY132595A/en unknown
-
1998
- 1998-03-31 IS IS4707A patent/IS4707A/is unknown
- 1998-05-25 BG BG102484A patent/BG102484A/xx unknown
- 1998-05-29 OA OA9800068A patent/OA10692A/en unknown
- 1998-05-29 MX MX9804311A patent/MX9804311A/es unknown
- 1998-06-02 NO NO982503A patent/NO982503L/no not_active Application Discontinuation
-
2001
- 2001-02-01 GR GR20010400166T patent/GR3035341T3/el not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993018001A1 (en) * | 1992-03-02 | 1993-09-16 | Pfizer Inc. | Preparation of intermediates in the synthesis of quinoline antibiotics |
| WO1995019361A1 (en) * | 1994-01-18 | 1995-07-20 | Pfizer Inc. | Process and intermediates for preparing naphthyridonecarboxylic acid salts |
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