FI62303C - Foerfarande foer framstaellning av en antilipolytiskt aktiv ny-6-klornikotinyl-d,1-homocystein-tiolakton - Google Patents
Foerfarande foer framstaellning av en antilipolytiskt aktiv ny-6-klornikotinyl-d,1-homocystein-tiolakton Download PDFInfo
- Publication number
- FI62303C FI62303C FI773001A FI773001A FI62303C FI 62303 C FI62303 C FI 62303C FI 773001 A FI773001 A FI 773001A FI 773001 A FI773001 A FI 773001A FI 62303 C FI62303 C FI 62303C
- Authority
- FI
- Finland
- Prior art keywords
- group
- thiolactone
- chloronicotinyl
- homocysteine
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- KIWQWJKWBHZMDT-UHFFFAOYSA-N homocysteine thiolactone Chemical compound NC1CCSC1=O KIWQWJKWBHZMDT-UHFFFAOYSA-N 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- ZHEXGKWVNRSSLH-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine;hydrochloride Chemical compound Cl.ClCC1=CC=C(Cl)N=C1 ZHEXGKWVNRSSLH-UHFFFAOYSA-N 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 241000700159 Rattus Species 0.000 description 16
- 241001465754 Metazoa Species 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 11
- 235000021588 free fatty acids Nutrition 0.000 description 11
- 150000003626 triacylglycerols Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- GGLZPLKKBSSKCX-UHFFFAOYSA-N S-ethylhomocysteine Chemical compound CCSCCC(N)C(O)=O GGLZPLKKBSSKCX-UHFFFAOYSA-N 0.000 description 6
- 229960002748 norepinephrine Drugs 0.000 description 6
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000004130 lipolysis Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- -1 with formic Chemical class 0.000 description 4
- 206010067125 Liver injury Diseases 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 231100000234 hepatic damage Toxicity 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 230000008818 liver damage Effects 0.000 description 3
- 235000001968 nicotinic acid Nutrition 0.000 description 3
- 239000011664 nicotinic acid Substances 0.000 description 3
- 229960003512 nicotinic acid Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 2
- GGLZPLKKBSSKCX-YFKPBYRVSA-N L-ethionine Chemical compound CCSCC[C@H](N)C(O)=O GGLZPLKKBSSKCX-YFKPBYRVSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 230000002440 hepatic effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 235000021590 normal diet Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- OROGUZVNAFJPHA-UHFFFAOYSA-N 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one Chemical compound CC1SC(=O)C(C)=C1O OROGUZVNAFJPHA-UHFFFAOYSA-N 0.000 description 1
- UAWMVMPAYRWUFX-UHFFFAOYSA-N 6-Chloronicotinic acid Chemical compound OC(=O)C1=CC=C(Cl)N=C1 UAWMVMPAYRWUFX-UHFFFAOYSA-N 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 208000004930 Fatty Liver Diseases 0.000 description 1
- 206010019708 Hepatic steatosis Diseases 0.000 description 1
- 206010021024 Hypolipidaemia Diseases 0.000 description 1
- KIWQWJKWBHZMDT-VKHMYHEASA-N L-homocysteine thiolactone Chemical compound N[C@H]1CCSC1=O KIWQWJKWBHZMDT-VKHMYHEASA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003243 anti-lipolytic effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- UKXSKSHDVLQNKG-UHFFFAOYSA-N benzilic acid Chemical compound C=1C=CC=CC=1C(O)(C(=O)O)C1=CC=CC=C1 UKXSKSHDVLQNKG-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000625 cyclamic acid and its Na and Ca salt Substances 0.000 description 1
- WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000674 effect on sodium Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 208000010706 fatty liver disease Diseases 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 230000002443 hepatoprotective effect Effects 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000012332 laboratory investigation Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 231100000240 steatosis hepatitis Toxicity 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT51734/76A IT1068217B (it) | 1976-10-14 | 1976-10-14 | Omocisteina tiolattone 6 cloro nicotinamide |
| IT5173476 | 1976-10-14 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI773001A7 FI773001A7 (fi) | 1978-04-15 |
| FI62303B FI62303B (fi) | 1982-08-31 |
| FI62303C true FI62303C (fi) | 1982-12-10 |
Family
ID=11275646
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI773001A FI62303C (fi) | 1976-10-14 | 1977-10-11 | Foerfarande foer framstaellning av en antilipolytiskt aktiv ny-6-klornikotinyl-d,1-homocystein-tiolakton |
Country Status (25)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1215238B (it) * | 1985-02-22 | 1990-01-31 | Chiesi Farma Spa | Derivati di omocisteina tiolattone,loro procedimento di preparazione e formulazioni farmaceutiche |
| WO1992000964A1 (en) * | 1990-07-05 | 1992-01-23 | Nippon Soda Co., Ltd. | Amine derivative |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1134683B (de) * | 1961-03-16 | 1962-08-16 | Degussa | Verfahren zur Herstellung von N-Acylhomocysteinthiolacton |
| US4021433A (en) * | 1973-03-08 | 1977-05-03 | Sigma-Tau Industrie Farmaceutiche Riunite S.P.A. | Derivative of nicotinic acid with amides |
| IT1056031B (it) * | 1973-03-08 | 1982-01-30 | Sigma Tau Ind Farmaceuti | Redivati ammidici dell acido nicotininico |
-
1976
- 1976-10-14 IT IT51734/76A patent/IT1068217B/it active
-
1977
- 1977-08-05 IE IE1645/77A patent/IE45365B1/en unknown
- 1977-08-09 IN IN1234/CAL/77A patent/IN145767B/en unknown
- 1977-08-12 AU AU27868/77A patent/AU506922B2/en not_active Expired
- 1977-08-30 AR AR268995A patent/AR214527A1/es active
- 1977-09-03 ES ES462110A patent/ES462110A1/es not_active Expired
- 1977-09-06 CA CA286,093A patent/CA1078388A/en not_active Expired
- 1977-09-06 BE BE180705A patent/BE858443A/xx not_active IP Right Cessation
- 1977-09-07 DE DE19772740345 patent/DE2740345A1/de not_active Ceased
- 1977-09-09 NL NL7709938A patent/NL7709938A/xx not_active Application Discontinuation
- 1977-09-19 CH CH1140877A patent/CH629201A5/it not_active IP Right Cessation
- 1977-09-19 AT AT670977A patent/AT361925B/de not_active IP Right Cessation
- 1977-09-21 FR FR7728396A patent/FR2367764A1/fr active Granted
- 1977-09-28 US US05/837,529 patent/US4167572A/en not_active Expired - Lifetime
- 1977-10-04 DK DK439277A patent/DK439277A/da not_active Application Discontinuation
- 1977-10-07 JP JP12135877A patent/JPS5350178A/ja active Pending
- 1977-10-09 EG EG583/77A patent/EG13219A/xx active
- 1977-10-10 SE SE7711347A patent/SE423545B/sv unknown
- 1977-10-11 FI FI773001A patent/FI62303C/fi not_active IP Right Cessation
- 1977-10-11 PH PH20325A patent/PH13068A/en unknown
- 1977-10-11 GR GR54549A patent/GR63598B/el unknown
- 1977-10-13 NO NO773506A patent/NO148714C/no unknown
- 1977-10-14 GB GB42890/77A patent/GB1587273A/en not_active Expired
- 1977-10-14 PT PT67155A patent/PT67155B/pt unknown
-
1978
- 1978-05-23 ZA ZA00776157A patent/ZA776157B/xx unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SIGMA-TAU INDUSTRIE FARMACEUTICHE |