NZ206189A - Preparation of sorbinil by selective crystallisation of certain amine salts of racemic 6-fluoro-2,3-dihydro-spiro (4h-1-benzopyran -4,4'- imidazolidine) -2',5'- dione - Google Patents
Preparation of sorbinil by selective crystallisation of certain amine salts of racemic 6-fluoro-2,3-dihydro-spiro (4h-1-benzopyran -4,4'- imidazolidine) -2',5'- dioneInfo
- Publication number
- NZ206189A NZ206189A NZ206189A NZ20618983A NZ206189A NZ 206189 A NZ206189 A NZ 206189A NZ 206189 A NZ206189 A NZ 206189A NZ 20618983 A NZ20618983 A NZ 20618983A NZ 206189 A NZ206189 A NZ 206189A
- Authority
- NZ
- New Zealand
- Prior art keywords
- sorbinil
- salt
- aminomethylpinane
- fluoro
- racemic
- Prior art date
Links
- LXANPKRCLVQAOG-NSHDSACASA-N sorbinil Chemical compound C12=CC(F)=CC=C2OCC[C@@]21NC(=O)NC2=O LXANPKRCLVQAOG-NSHDSACASA-N 0.000 title claims description 78
- 229950004311 sorbinil Drugs 0.000 title claims description 74
- -1 amine salts Chemical class 0.000 title claims description 6
- 238000002425 crystallisation Methods 0.000 title description 4
- LXANPKRCLVQAOG-UHFFFAOYSA-N 6-fluorospiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2OCCC21NC(=O)NC2=O LXANPKRCLVQAOG-UHFFFAOYSA-N 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical class C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 17
- MUOITVAMHSVXLO-UHFFFAOYSA-N (4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl)methanamine Chemical class C1C(CN)C(C)C2C(C)(C)C1C2 MUOITVAMHSVXLO-UHFFFAOYSA-N 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000012141 concentrate Substances 0.000 claims description 10
- 239000012452 mother liquor Substances 0.000 claims description 7
- 125000002091 cationic group Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- WXEJLHJZGPUQHN-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptan-5-amine Chemical class CC1CCC2C(C)(C)C1(N)C2 WXEJLHJZGPUQHN-UHFFFAOYSA-N 0.000 claims description 4
- 235000001258 Cinchona calisaya Nutrition 0.000 claims description 4
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 claims description 4
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 4
- 229940091173 hydantoin Drugs 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229960000948 quinine Drugs 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 238000001914 filtration Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- SWBBIJZMIGAZHW-UHFFFAOYSA-N 6-fluoro-2,3-dihydrochromen-4-one Chemical compound O1CCC(=O)C2=CC(F)=CC=C21 SWBBIJZMIGAZHW-UHFFFAOYSA-N 0.000 description 8
- 239000002002 slurry Substances 0.000 description 8
- 229910001868 water Inorganic materials 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000012267 brine Substances 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VUTSCRNPMNTQSK-UHFFFAOYSA-N 6-fluoro-3,4-dihydrochromen-2-one Chemical compound O1C(=O)CCC2=CC(F)=CC=C21 VUTSCRNPMNTQSK-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JOYYZHWCUDYZKJ-UHFFFAOYSA-N n-chloro-6-fluoro-2,3-dihydrochromen-4-imine Chemical compound O1CCC(=NCl)C2=CC(F)=CC=C21 JOYYZHWCUDYZKJ-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010583 slow cooling Methods 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- IWQRUIJDSONCFG-UHFFFAOYSA-N 4,5,6,6-tetramethylbicyclo[3.1.1]heptane Chemical compound CC1CCC2C(C)(C)C1(C)C2 IWQRUIJDSONCFG-UHFFFAOYSA-N 0.000 description 1
- 229940118148 Aldose reductase inhibitor Drugs 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000003288 aldose reductase inhibitor Substances 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RRKTZKIUPZVBMF-IBTVXLQLSA-N brucine Chemical compound O([C@@H]1[C@H]([C@H]2C3)[C@@H]4N(C(C1)=O)C=1C=C(C(=CC=11)OC)OC)CC=C2CN2[C@@H]3[C@]41CC2 RRKTZKIUPZVBMF-IBTVXLQLSA-N 0.000 description 1
- RRKTZKIUPZVBMF-UHFFFAOYSA-N brucine Natural products C1=2C=C(OC)C(OC)=CC=2N(C(C2)=O)C3C(C4C5)C2OCC=C4CN2C5C31CC2 RRKTZKIUPZVBMF-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003048 pinane derivatives Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
- YEGZRRJAGUJLDV-UHFFFAOYSA-N spiro[2,3-dihydrochromene-4,5'-imidazolidine]-2',4'-dione Chemical compound N1C(=O)NC(=O)C11C2=CC=CC=C2OCC1 YEGZRRJAGUJLDV-UHFFFAOYSA-N 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Hydrogenated Pyridines (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ216928A NZ216928A (en) | 1982-11-10 | 1983-11-08 | Sorbinil by optical resolution of precursor 6- fluoro -4- ureidochroman -4-ylcarboxylic acid and certain amine salts of this precursor acid |
| NZ21692983A NZ216929A (en) | 1982-11-10 | 1983-11-08 | Regeneration of 6-fluorochroman -4-one from by-products from synthesis of sorbinil |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44068682A | 1982-11-10 | 1982-11-10 | |
| US06/440,641 US4435578A (en) | 1982-11-10 | 1982-11-10 | Sorbinil by optical resolution of precursor 6-fluoro-4-ureidochroman-4-carboxylic acid |
| US06/440,657 US4431828A (en) | 1982-11-10 | 1982-11-10 | Regeneration of 6-fluoro-4-chromanone from by-products in the synthesis of sorbinil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ206189A true NZ206189A (en) | 1987-06-30 |
Family
ID=27412063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ206189A NZ206189A (en) | 1982-11-10 | 1983-11-08 | Preparation of sorbinil by selective crystallisation of certain amine salts of racemic 6-fluoro-2,3-dihydro-spiro (4h-1-benzopyran -4,4'- imidazolidine) -2',5'- dione |
Country Status (16)
-
1983
- 1983-11-07 PT PT77617A patent/PT77617B/pt not_active IP Right Cessation
- 1983-11-07 YU YU2203/83A patent/YU44867B/xx unknown
- 1983-11-07 GR GR72904A patent/GR79017B/el unknown
- 1983-11-08 ES ES527118A patent/ES8506040A1/es not_active Expired
- 1983-11-08 FI FI834088A patent/FI77247C/fi not_active IP Right Cessation
- 1983-11-08 DD DD83256455A patent/DD213924A5/de not_active IP Right Cessation
- 1983-11-08 PL PL1983244460A patent/PL139713B1/pl unknown
- 1983-11-08 IL IL70165A patent/IL70165A/xx unknown
- 1983-11-08 KR KR1019830005294A patent/KR870000867B1/ko not_active Expired
- 1983-11-08 NZ NZ206189A patent/NZ206189A/en unknown
- 1983-11-09 DK DK512683A patent/DK512683A/da not_active Application Discontinuation
- 1983-11-09 BG BG062988A patent/BG44206A3/xx unknown
- 1983-11-09 NO NO834086A patent/NO161916C/no unknown
- 1983-11-09 AU AU21105/83A patent/AU540399B2/en not_active Ceased
- 1983-11-09 SU SU833659625A patent/SU1209030A3/ru active
- 1983-11-09 CS CS838271A patent/CS266560B2/cs unknown
-
1984
- 1984-08-06 ES ES534921A patent/ES8505988A1/es not_active Expired
- 1984-08-06 ES ES534920A patent/ES534920A0/es active Granted
-
1985
- 1985-09-09 YU YU1409/85A patent/YU43883B/xx unknown
-
1987
- 1987-02-23 IL IL81648A patent/IL81648A0/xx not_active IP Right Cessation
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