IL100098A - תולדות 1,2,3,6-טטראהידרופירידין, הכנתן ותכשירי רוקחות המכילים אותן - Google Patents
תולדות 1,2,3,6-טטראהידרופירידין, הכנתן ותכשירי רוקחות המכילים אותןInfo
- Publication number
- IL100098A IL100098A IL10009891A IL10009891A IL100098A IL 100098 A IL100098 A IL 100098A IL 10009891 A IL10009891 A IL 10009891A IL 10009891 A IL10009891 A IL 10009891A IL 100098 A IL100098 A IL 100098A
- Authority
- IL
- Israel
- Prior art keywords
- phenyl
- acid addition
- tetrahydro
- addition salts
- pyridyl
- Prior art date
Links
- 150000008083 1,2,3,6-tetrahydropyridines Chemical class 0.000 title claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 239000004480 active ingredient Substances 0.000 claims abstract description 13
- 230000000141 anti-hypoxic effect Effects 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 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 claims abstract description 6
- 230000017531 blood circulation Effects 0.000 claims abstract description 6
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 4
- 150000007524 organic acids Chemical class 0.000 claims abstract description 4
- 239000003960 organic solvent Substances 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 3
- 239000011707 mineral Substances 0.000 claims abstract description 3
- 241001465754 Metazoa Species 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 15
- 206010021143 Hypoxia Diseases 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 230000007954 hypoxia Effects 0.000 claims description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- -1 aluminium alkoxide Chemical class 0.000 claims description 7
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 6
- 210000004556 brain Anatomy 0.000 claims description 6
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 206010027175 memory impairment Diseases 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- 229910052987 metal hydride Inorganic materials 0.000 claims description 3
- 150000004681 metal hydrides Chemical class 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 229940044613 1-propanol Drugs 0.000 claims 11
- 229960005335 propanol Drugs 0.000 claims 10
- FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical class C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims 6
- WKNLRSMHHZUYJS-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-1-[4-(4-chlorophenyl)phenyl]propan-1-ol Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(O)CCN(CC=1)CCC=1C1=CC=C(Cl)C=C1 WKNLRSMHHZUYJS-UHFFFAOYSA-N 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
- 230000004083 survival effect Effects 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- RXPRRQLKFXBCSJ-GIVPXCGWSA-N vincamine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C[C@](O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-GIVPXCGWSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 230000009467 reduction Effects 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 241000700159 Rattus Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- RXPRRQLKFXBCSJ-UHFFFAOYSA-N dl-Vincamin Natural products C1=CC=C2C(CCN3CCC4)=C5C3C4(CC)CC(O)(C(=O)OC)N5C2=C1 RXPRRQLKFXBCSJ-UHFFFAOYSA-N 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 230000029058 respiratory gaseous exchange Effects 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- 229960002726 vincamine Drugs 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- GMZVRMREEHBGGF-UHFFFAOYSA-N Piracetam Chemical compound NC(=O)CN1CCCC1=O GMZVRMREEHBGGF-UHFFFAOYSA-N 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 230000001631 hypertensive effect Effects 0.000 description 3
- 229940057948 magnesium stearate Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229960004526 piracetam Drugs 0.000 description 3
- 229940083608 sodium hydroxide Drugs 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- PGGZAZHZNVKDLG-UHFFFAOYSA-N 1,4-dioxane;hexane Chemical compound CCCCCC.C1COCCO1 PGGZAZHZNVKDLG-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 206010003497 Asphyxia Diseases 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000001828 Gelatine Substances 0.000 description 2
- 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 2
- 238000004458 analytical method Methods 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 230000004060 metabolic process Effects 0.000 description 2
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 2
- 229920001592 potato starch Polymers 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- FREKHJCGVUWODS-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)phenyl]-3-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]propan-1-ol Chemical compound C=1C=C(C=2C=CC(Cl)=CC=2)C=CC=1C(O)CCN(CC=1)CCC=1C1=CC=C(F)C=C1 FREKHJCGVUWODS-UHFFFAOYSA-N 0.000 description 1
- KYSHELRVTAFBNJ-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)methyl]phenyl]-3-[4-(4-fluorophenyl)-3,6-dihydro-2h-pyridin-1-yl]propan-1-ol Chemical compound C=1C=C(CC=2C=CC(Cl)=CC=2)C=CC=1C(O)CCN(CC=1)CCC=1C1=CC=C(F)C=C1 KYSHELRVTAFBNJ-UHFFFAOYSA-N 0.000 description 1
- OWBVCFWLDHDTFO-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-1-[4-(4-fluorophenyl)phenyl]propan-1-ol Chemical compound C=1C=C(C=2C=CC(F)=CC=2)C=CC=1C(O)CCN(CC=1)CCC=1C1=CC=C(Cl)C=C1 OWBVCFWLDHDTFO-UHFFFAOYSA-N 0.000 description 1
- JMMLTNMXVFSDRI-UHFFFAOYSA-N 3-[4-(4-chlorophenyl)-3,6-dihydro-2h-pyridin-1-yl]-1-[4-[(4-chlorophenyl)methyl]phenyl]propan-1-ol Chemical compound C=1C=C(CC=2C=CC(Cl)=CC=2)C=CC=1C(O)CCN(CC=1)CCC=1C1=CC=C(Cl)C=C1 JMMLTNMXVFSDRI-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- 238000003612 Meerwein-Ponndorf-Verley reduction reaction Methods 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 201000004810 Vascular dementia Diseases 0.000 description 1
- WKACQPMBGWZDMR-UHFFFAOYSA-N Vincamin Natural products CC=C1/CN2CCC34CC2C1C(=C3Nc5ccccc45)C=O WKACQPMBGWZDMR-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000001966 cerebroprotective effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 230000002438 mitochondrial effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 230000009543 pathological alteration Effects 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 239000000902 placebo Substances 0.000 description 1
- 229940068196 placebo Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical class CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- LMHHRCOWPQNFTF-UHFFFAOYSA-N s-propan-2-yl azepane-1-carbothioate Chemical compound CC(C)SC(=O)N1CCCCCC1 LMHHRCOWPQNFTF-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
-
- 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
- C07D211/68—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 one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—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 one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Luminescent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU908253A HU209573B (en) | 1990-12-13 | 1990-12-13 | Process for producing of 1,2,3,6-tetrahydropyridine derivatives and pharmaceutical compositions comprising these substances |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL100098A0 IL100098A0 (en) | 1992-08-18 |
| IL100098A true IL100098A (he) | 1995-07-31 |
Family
ID=10972493
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10009891A IL100098A (he) | 1990-12-13 | 1991-11-20 | תולדות 1,2,3,6-טטראהידרופירידין, הכנתן ותכשירי רוקחות המכילים אותן |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5225416A (he) |
| EP (1) | EP0490560B1 (he) |
| JP (1) | JPH04275272A (he) |
| KR (1) | KR920012033A (he) |
| AT (1) | ATE135689T1 (he) |
| AU (1) | AU647704B2 (he) |
| CA (1) | CA2056582A1 (he) |
| DE (1) | DE69118129T2 (he) |
| HU (1) | HU209573B (he) |
| IL (1) | IL100098A (he) |
| ZA (1) | ZA919338B (he) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU211019B (en) * | 1991-12-02 | 1995-09-28 | Richter Gedeon Vegyeszet | Process for producing new 1,2,3,6-tetrahydropyridine and piperidine derivatives substituted with n-(hydroxylalkyl) group and compositions comprising such compounds |
| WO2014140671A1 (en) | 2013-03-15 | 2014-09-18 | Institut De Recherche Pour Le Developpement | New arylaminoalcohol derivatives with antiplasmodial activity |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB984364A (en) * | 1961-07-28 | 1965-02-24 | May & Baker Ltd | Substituted piperidines and tetrahydropyridines |
| GB948071A (en) * | 1959-05-01 | 1964-01-29 | May & Baker Ltd | New heterocyclic compounds |
| US3426036A (en) * | 1966-08-04 | 1969-02-04 | Aldrich Chem Co Inc | N - (p - phenoxybenzoyl - lower alkyl)-4-phenyl-tetrahydropyridyl derivatives; the corresponding alcohol,carbamate and lower alkylene derivatives |
| DE2960612D1 (en) * | 1978-04-12 | 1981-11-12 | Ici Plc | Blood platelet aggregation inhibitory pyridine derivatives, pharmaceutical compositions thereof, and processes for their manufacture |
-
1990
- 1990-12-13 HU HU908253A patent/HU209573B/hu not_active IP Right Cessation
-
1991
- 1991-11-20 IL IL10009891A patent/IL100098A/he not_active IP Right Cessation
- 1991-11-26 ZA ZA919338A patent/ZA919338B/xx unknown
- 1991-11-28 CA CA002056582A patent/CA2056582A1/en not_active Abandoned
- 1991-12-03 EP EP91311257A patent/EP0490560B1/en not_active Expired - Lifetime
- 1991-12-03 DE DE69118129T patent/DE69118129T2/de not_active Expired - Fee Related
- 1991-12-03 AT AT91311257T patent/ATE135689T1/de active
- 1991-12-10 KR KR1019910022511A patent/KR920012033A/ko not_active Withdrawn
- 1991-12-10 US US07/805,861 patent/US5225416A/en not_active Expired - Fee Related
- 1991-12-12 AU AU89620/91A patent/AU647704B2/en not_active Ceased
- 1991-12-12 JP JP3328973A patent/JPH04275272A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| KR920012033A (ko) | 1992-07-25 |
| US5225416A (en) | 1993-07-06 |
| HU908253D0 (en) | 1991-06-28 |
| EP0490560B1 (en) | 1996-03-20 |
| HU209573B (en) | 1994-08-29 |
| DE69118129D1 (de) | 1996-04-25 |
| JPH04275272A (ja) | 1992-09-30 |
| EP0490560A1 (en) | 1992-06-17 |
| AU8962091A (en) | 1992-06-18 |
| ZA919338B (en) | 1992-09-30 |
| IL100098A0 (en) | 1992-08-18 |
| CA2056582A1 (en) | 1992-06-14 |
| AU647704B2 (en) | 1994-03-24 |
| HUT62269A (en) | 1993-04-28 |
| DE69118129T2 (de) | 1996-07-25 |
| ATE135689T1 (de) | 1996-04-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RH | Patent void |