LT3316B - Process for preparing pyrimidinetrione derivatives - Google Patents
Process for preparing pyrimidinetrione derivatives Download PDFInfo
- Publication number
- LT3316B LT3316B LTIP612A LTIP612A LT3316B LT 3316 B LT3316 B LT 3316B LT IP612 A LTIP612 A LT IP612A LT IP612 A LTIP612 A LT IP612A LT 3316 B LT3316 B LT 3316B
- Authority
- LT
- Lithuania
- Prior art keywords
- formula
- compound
- iii
- chch
- process according
- Prior art date
Links
- SOFSSZFBVOGIKD-UHFFFAOYSA-N pyrimidine-2,4,5-trione Chemical class O=C1NC(=O)C(=O)C=N1 SOFSSZFBVOGIKD-UHFFFAOYSA-N 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title description 3
- 238000000034 method Methods 0.000 claims abstract description 20
- 230000008569 process Effects 0.000 claims abstract description 14
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- 101150065749 Churc1 gene Proteins 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 5
- 150000007530 organic bases Chemical class 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 150000002894 organic compounds Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- FAAYXVRRJFCFOR-UHFFFAOYSA-N (2,4,5-trioxo-1,3-diazinan-1-yl)phosphonic acid Chemical class OP(O)(=O)N1CC(=O)C(=O)NC1=O FAAYXVRRJFCFOR-UHFFFAOYSA-N 0.000 abstract 1
- 229940002612 prodrug Drugs 0.000 abstract 1
- 239000000651 prodrug Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 49
- 239000000243 solution Substances 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000543 intermediate Substances 0.000 description 12
- QHZQILHUJDRDAI-UHFFFAOYSA-N febarbamate Chemical compound O=C1N(CC(COCCCC)OC(N)=O)C(=O)NC(=O)C1(CC)C1=CC=CC=C1 QHZQILHUJDRDAI-UHFFFAOYSA-N 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 229960005182 febarbamate Drugs 0.000 description 10
- 239000012044 organic layer Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- -1 N'-mono-substituted 5,5-disubstituted pyrimidine Chemical class 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical class O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 3
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 3
- 229960002695 phenobarbital Drugs 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- KXLGRPUTQDZSAE-UHFFFAOYSA-N 1-(3-butoxy-2-hydroxypropyl)-5-ethyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1N(CC(O)COCCCC)C(=O)NC(=O)C1(CC)C1=CC=CC=C1 KXLGRPUTQDZSAE-UHFFFAOYSA-N 0.000 description 2
- YSUQLAYJZDEMOT-UHFFFAOYSA-N 2-(butoxymethyl)oxirane Chemical compound CCCCOCC1CO1 YSUQLAYJZDEMOT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- QKPIQPBNFUNZSJ-UHFFFAOYSA-N dichlorophosphorylimino(oxo)methane Chemical compound ClP(Cl)(=O)N=C=O QKPIQPBNFUNZSJ-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- KFDFYCRDUBAKHD-UHFFFAOYSA-M sodium;carbamate Chemical compound [Na+].NC([O-])=O KFDFYCRDUBAKHD-UHFFFAOYSA-M 0.000 description 2
- RSEQDQIMVQFBSZ-UHFFFAOYSA-N 1,3-dipropyl-1,3-diazinane-2,4,6-trione Chemical compound CCCN1C(=O)CC(=O)N(CCC)C1=O RSEQDQIMVQFBSZ-UHFFFAOYSA-N 0.000 description 1
- DKAKITCMBOHHQU-UHFFFAOYSA-N 2-butoxypropan-2-ol Chemical compound CCCCOC(C)(C)O DKAKITCMBOHHQU-UHFFFAOYSA-N 0.000 description 1
- OJMCNMCTVBXZMN-UHFFFAOYSA-N 3,4-dichloro-2-isocyanatophosphinine Chemical compound ClC1=CC=PC(N=C=O)=C1Cl OJMCNMCTVBXZMN-UHFFFAOYSA-N 0.000 description 1
- LBVMJCZEGXWFIO-UHFFFAOYSA-N C1N=CC=CN1P(=O)(O)O Chemical compound C1N=CC=CN1P(=O)(O)O LBVMJCZEGXWFIO-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-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
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- MBSBKSGPSFPSLQ-UHFFFAOYSA-N [1-butoxy-3-(2,4,6-trioxo-5,5-dipropyl-1,3-diazinan-1-yl)propan-2-yl] carbamate Chemical compound CCCCOCC(OC(N)=O)CN1C(=O)NC(=O)C(CCC)(CCC)C1=O MBSBKSGPSFPSLQ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000008512 pyrimidinediones Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/60—Three or more oxygen or sulfur atoms
- C07D239/62—Barbituric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/6512—Six-membered rings having the nitrogen atoms in positions 1 and 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Dental Preparations (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909002890A GB9002890D0 (en) | 1990-02-08 | 1990-02-08 | Process for preparing pyrimidinetrione derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| LTIP612A LTIP612A (en) | 1994-12-25 |
| LT3316B true LT3316B (en) | 1995-06-26 |
Family
ID=10670669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LTIP612A LT3316B (en) | 1990-02-08 | 1993-06-03 | Process for preparing pyrimidinetrione derivatives |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US5262402A (bg) |
| EP (1) | EP0466887B1 (bg) |
| JP (1) | JPH04505460A (bg) |
| KR (1) | KR920701173A (bg) |
| CN (2) | CN1034806C (bg) |
| AT (1) | ATE113589T1 (bg) |
| BG (1) | BG60269B2 (bg) |
| CA (1) | CA2049991A1 (bg) |
| CS (1) | CS31191A3 (bg) |
| DE (1) | DE69104920T2 (bg) |
| DK (1) | DK0466887T3 (bg) |
| ES (1) | ES2065002T3 (bg) |
| GB (1) | GB9002890D0 (bg) |
| GE (1) | GEP19970892B (bg) |
| HR (1) | HRP950155A2 (bg) |
| HU (2) | HUT64077A (bg) |
| IE (1) | IE62606B1 (bg) |
| LT (1) | LT3316B (bg) |
| LV (1) | LV10259B (bg) |
| PL (2) | PL168051B1 (bg) |
| PT (1) | PT96694B (bg) |
| RO (1) | RO109334B1 (bg) |
| RU (1) | RU2050353C1 (bg) |
| TW (1) | TW216792B (bg) |
| WO (1) | WO1991012244A1 (bg) |
| YU (1) | YU47836B (bg) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2107064A1 (de) * | 2008-04-02 | 2009-10-07 | Basf Se | Verfahren zur Herstellung von Triamiden aus Ammoniak und Amido-Dichloriden |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1581834A (en) | 1976-11-01 | 1980-12-31 | Sapos Sa | Complexes of barbituric acid derivatives |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2161212A (en) * | 1939-06-06 | Substituted barbituric acids con | ||
| US2876225A (en) * | 1959-03-03 | Manufacture of therapeutic substances | ||
| US2051846A (en) * | 1936-08-25 | Production of barbituric acid | ||
| US814496A (en) * | 1904-11-08 | 1906-03-06 | Firm Of E Merck | Process of making barbituric acids. |
| FR2424262A1 (fr) * | 1978-04-24 | 1979-11-23 | Sapos Sa | Nouveaux complexes tetrameres de derives de la malonyl-uree a action psychotrope et procede de preparation |
| GB8309813D0 (en) * | 1983-04-12 | 1983-05-18 | Sapos Sa | Pyrimidinetrione derivatives |
-
1990
- 1990-02-08 HU HU93285A patent/HUT64077A/hu unknown
- 1990-02-08 GB GB909002890A patent/GB9002890D0/en active Pending
-
1991
- 1991-02-05 AT AT91903577T patent/ATE113589T1/de not_active IP Right Cessation
- 1991-02-05 RU SU915001934A patent/RU2050353C1/ru active
- 1991-02-05 JP JP3503730A patent/JPH04505460A/ja active Pending
- 1991-02-05 HU HU913183A patent/HU207722B/hu not_active IP Right Cessation
- 1991-02-05 PL PL91304151A patent/PL168051B1/pl unknown
- 1991-02-05 PL PL91292559A patent/PL165990B1/pl unknown
- 1991-02-05 ES ES91903577T patent/ES2065002T3/es not_active Expired - Lifetime
- 1991-02-05 US US07/768,852 patent/US5262402A/en not_active Expired - Fee Related
- 1991-02-05 DE DE69104920T patent/DE69104920T2/de not_active Expired - Fee Related
- 1991-02-05 WO PCT/EP1991/000253 patent/WO1991012244A1/en active IP Right Grant
- 1991-02-05 RO RO148583A patent/RO109334B1/ro unknown
- 1991-02-05 CA CA002049991A patent/CA2049991A1/en not_active Abandoned
- 1991-02-05 TW TW080100904A patent/TW216792B/zh active
- 1991-02-05 KR KR1019910701274A patent/KR920701173A/ko not_active Application Discontinuation
- 1991-02-05 EP EP91903577A patent/EP0466887B1/en not_active Expired - Lifetime
- 1991-02-05 DK DK91903577.4T patent/DK0466887T3/da active
- 1991-02-07 PT PT96694A patent/PT96694B/pt not_active IP Right Cessation
- 1991-02-07 YU YU21791A patent/YU47836B/sh unknown
- 1991-02-07 IE IE40991A patent/IE62606B1/en not_active IP Right Cessation
- 1991-02-08 CS CS91311A patent/CS31191A3/cs unknown
- 1991-02-08 CN CN91101394A patent/CN1034806C/zh not_active Expired - Fee Related
- 1991-11-07 BG BG95434A patent/BG60269B2/bg unknown
-
1992
- 1992-12-09 LV LVP-92-273A patent/LV10259B/en unknown
-
1993
- 1993-06-03 LT LTIP612A patent/LT3316B/lt not_active IP Right Cessation
- 1993-07-27 GE GEAP19931231A patent/GEP19970892B/en unknown
-
1995
- 1995-03-28 HR HR950155A patent/HRP950155A2/xx not_active Application Discontinuation
- 1995-05-12 CN CN95106059A patent/CN1121070A/zh active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1581834A (en) | 1976-11-01 | 1980-12-31 | Sapos Sa | Complexes of barbituric acid derivatives |
Non-Patent Citations (1)
| Title |
|---|
| HÄRING M.: "Synthese neuer lokalanästhetisch wirksamer ortho-substituierter Benzoesäure- und Carbaminsäureester 3. Mitteilung über Lokalanästhetika", HELVETICA CHIMICA ACTA, 1960, pages 105 - 113 |
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