NO852670L - Fremgangsmaate for fremstilling av terapeutisk virksomme pyridin-derivater. - Google Patents
Fremgangsmaate for fremstilling av terapeutisk virksomme pyridin-derivater.Info
- Publication number
- NO852670L NO852670L NO852670A NO852670A NO852670L NO 852670 L NO852670 L NO 852670L NO 852670 A NO852670 A NO 852670A NO 852670 A NO852670 A NO 852670A NO 852670 L NO852670 L NO 852670L
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- compound
- formula
- fluoromethyl
- dihydro
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 20
- 238000002360 preparation method Methods 0.000 title claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- -1 cyano, methyl Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- HLMGQHPHHWHHAE-UHFFFAOYSA-N 3-o-methyl 5-o-propan-2-yl 4-(3-cyanophenyl)-2-(fluoromethyl)-1,6-dimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CF)N(C)C(C)=C(C(=O)OC(C)C)C1C1=CC=CC(C#N)=C1 HLMGQHPHHWHHAE-UHFFFAOYSA-N 0.000 claims description 2
- PAKFOAVFQFMTPZ-UHFFFAOYSA-N 3-o-methyl 5-o-propan-2-yl 4-[3-chloro-6-fluoro-2-(trifluoromethyl)phenyl]-2-(fluoromethyl)-1,6-dimethyl-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CF)N(C)C(C)=C(C(=O)OC(C)C)C1C1=C(F)C=CC(Cl)=C1C(F)(F)F PAKFOAVFQFMTPZ-UHFFFAOYSA-N 0.000 claims description 2
- YDDHUZUDCGRBCV-UHFFFAOYSA-N 5-o-cyclopentyl 3-o-methyl 2-(fluoromethyl)-1,6-dimethyl-4-(2-methyl-3-nitrophenyl)-4h-pyridine-3,5-dicarboxylate Chemical compound COC(=O)C1=C(CF)N(C)C(C)=C(C(=O)OC2CCCC2)C1C1=CC=CC([N+]([O-])=O)=C1C YDDHUZUDCGRBCV-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
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- 239000003085 diluting agent Substances 0.000 description 8
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- 210000003205 muscle Anatomy 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- HYIMSNHJOBLJNT-UHFFFAOYSA-N nifedipine Chemical compound COC(=O)C1=C(C)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1[N+]([O-])=O HYIMSNHJOBLJNT-UHFFFAOYSA-N 0.000 description 1
- 229960001597 nifedipine Drugs 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 210000003200 peritoneal cavity Anatomy 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- YCKAGGHNUHZKCL-UHFFFAOYSA-N propan-2-yl 3-aminobut-2-enoate Chemical compound CC(C)OC(=O)C=C(C)N YCKAGGHNUHZKCL-UHFFFAOYSA-N 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000006104 solid solution Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000024535 susceptibility to myocardial infarction Diseases 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000003451 thiazide diuretic agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848418127A GB8418127D0 (en) | 1984-07-17 | 1984-07-17 | Biologically active nitrogen heterocycles |
GB848420840A GB8420840D0 (en) | 1984-08-16 | 1984-08-16 | Biologically active nitrogen heterocycle |
Publications (1)
Publication Number | Publication Date |
---|---|
NO852670L true NO852670L (no) | 1986-01-20 |
Family
ID=26287992
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO852670A NO852670L (no) | 1984-07-17 | 1985-07-03 | Fremgangsmaate for fremstilling av terapeutisk virksomme pyridin-derivater. |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0169009A3 (fi) |
AU (1) | AU4489085A (fi) |
DK (1) | DK321985A (fi) |
FI (1) | FI852768L (fi) |
IL (1) | IL75814A0 (fi) |
NO (1) | NO852670L (fi) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1215298B (it) * | 1985-08-06 | 1990-01-31 | Boehringer Biochemia Srl | 2-(eteroalchil)-1,4-diidropiridine ed un processo per la loro produzione. |
EP0225175A3 (en) * | 1985-11-28 | 1988-12-28 | FISONS plc | Dihydropyridine derivatives, processes for their preparation and pharmaceutical compositions thereof |
JPH02501736A (ja) * | 1986-12-24 | 1990-06-14 | ベリンガー マンハイム イタリア エッセ ピ ア | 新規なアラルキル‐1,4‐ジヒドロピリジンおよびその製造法、ならびにそれを含有する製薬組成物 |
IT1213440B (it) * | 1986-12-24 | 1989-12-20 | Boehringer Biochemia Srl | 2-ditioalchil-diidropiridine, un metodo per la loro preparazione e composizioni farmaceutiche chele contengono. |
DE4328884A1 (de) * | 1993-08-27 | 1995-03-02 | Bayer Ag | Verwendung von N-alkylierten 1,4-Dihydropyridincarbonsäureestern als Arzneimittel |
US6784165B1 (en) | 1999-11-23 | 2004-08-31 | Aderis Pharmaceuticals, Inc. | Treatment of heart rhythm disturbances with N6-substituted-5′-(N-substituted) carboxamidoadenosines |
NZ518861A (en) * | 1999-11-23 | 2004-11-26 | Aderis Pharmaceuticals Inc | Treatment of heart rhythm distubances with N6-substituted-5'-(N-substituted) carboxamidoadenosines |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2841667A1 (de) * | 1978-09-25 | 1980-04-10 | Bayer Ag | Fluorhaltige 1,4-dihydropyridine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
1985
- 1985-07-02 EP EP85304728A patent/EP0169009A3/en not_active Withdrawn
- 1985-07-03 NO NO852670A patent/NO852670L/no unknown
- 1985-07-15 AU AU44890/85A patent/AU4489085A/en not_active Withdrawn
- 1985-07-15 IL IL75814A patent/IL75814A0/xx unknown
- 1985-07-15 FI FI852768A patent/FI852768L/fi not_active Application Discontinuation
- 1985-07-15 DK DK321985A patent/DK321985A/da not_active Application Discontinuation
Also Published As
Publication number | Publication date |
---|---|
DK321985A (da) | 1986-01-18 |
EP0169009A3 (en) | 1988-08-31 |
DK321985D0 (da) | 1985-07-15 |
AU4489085A (en) | 1986-01-23 |
EP0169009A2 (en) | 1986-01-22 |
FI852768L (fi) | 1986-01-18 |
FI852768A0 (fi) | 1985-07-15 |
IL75814A0 (en) | 1985-11-29 |
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