FI77247C - Foerfarande foer framstaellning av sorbinil eller dess salt och i foerfarandet anvaendbar mellanprodukt. - Google Patents
Foerfarande foer framstaellning av sorbinil eller dess salt och i foerfarandet anvaendbar mellanprodukt. Download PDFInfo
- Publication number
- FI77247C FI77247C FI834088A FI834088A FI77247C FI 77247 C FI77247 C FI 77247C FI 834088 A FI834088 A FI 834088A FI 834088 A FI834088 A FI 834088A FI 77247 C FI77247 C FI 77247C
- Authority
- FI
- Finland
- Prior art keywords
- sorbinil
- salt
- aminomethylpinane
- methanol
- pharmaceutically acceptable
- 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 37
- 229950004311 sorbinil Drugs 0.000 title claims description 35
- 238000000034 method Methods 0.000 title claims description 14
- 150000003839 salts Chemical class 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 15
- 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 13
- 239000000203 mixture Substances 0.000 claims description 6
- 125000002091 cationic group Chemical group 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 238000011084 recovery Methods 0.000 claims description 3
- 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 2
- 238000001816 cooling Methods 0.000 claims description 2
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 2
- 229940091173 hydantoin Drugs 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- -1 cationic salt Chemical class 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000010410 layer Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000010561 standard procedure Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000002253 acid Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- WISAATKICNHAIR-UHFFFAOYSA-N 6-fluorospiro[2,3-dihydrochromene-4,4'-imidazolidine] Chemical compound C12=CC(F)=CC=C2OCCC21CNCN2 WISAATKICNHAIR-UHFFFAOYSA-N 0.000 description 1
- SXRDEMXRIYIIJX-UHFFFAOYSA-N 6-fluorospiro[chromene-4,5'-imidazolidine]-2',4'-dione Chemical compound C12=CC(F)=CC=C2OC=CC21NC(=O)NC2=O SXRDEMXRIYIIJX-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 229940118148 Aldose reductase inhibitor Drugs 0.000 description 1
- NMPRWGNTOHVZKX-UHFFFAOYSA-N CC1(C2CC1C(C(C2)N)(C)C)C Chemical compound CC1(C2CC1C(C(C2)N)(C)C)C NMPRWGNTOHVZKX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003288 aldose reductase inhibitor Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012267 brine 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
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 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 |
|---|---|---|---|
| FI880465A FI880465A7 (fi) | 1982-11-10 | 1983-11-08 | Menetelmä kiteisen S-6-fluori-4-ureido-kromaani-4-karboksyylihapposuolan valmistamiseksi. |
| FI880466A FI880466L (fi) | 1982-11-10 | 1983-11-08 | Foerfarande foer regenerering av renat 6-fluor-4-kromanon. |
Applications Claiming Priority (6)
| 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 |
| US44064182 | 1982-11-10 | ||
| US44065782 | 1982-11-10 | ||
| US44068682 | 1982-11-10 | ||
| 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 (4)
| Publication Number | Publication Date |
|---|---|
| FI834088A0 FI834088A0 (fi) | 1983-11-08 |
| FI834088L FI834088L (fi) | 1984-05-11 |
| FI77247B FI77247B (fi) | 1988-10-31 |
| FI77247C true FI77247C (fi) | 1989-02-10 |
Family
ID=27412063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI834088A FI77247C (fi) | 1982-11-10 | 1983-11-08 | Foerfarande foer framstaellning av sorbinil eller dess salt och i foerfarandet anvaendbar mellanprodukt. |
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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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: PFIZER INC. |