CS241032B2 - Method of 1,2,4-oxadiazoline-5-on's new derivatives production - Google Patents

Method of 1,2,4-oxadiazoline-5-on's new derivatives production Download PDF

Info

Publication number: CS241032B2
Authority: CS; Czechoslovakia
Prior art keywords: carbon atoms; phenyl; hydroxypropyl; alkoxy; oxadiazolin
Prior art date: 1979-10-11

Application number

CS806737A

Other languages

Czech (cs)

English (en)

Other versions

CS673780A2 (en

Inventor

Kalman Takacs

Ilona Kiss

Antal Simay

Nagy P Literati

Maria Hetyey

Marian Ecsery

Laszlo Szekeres

Gyula Papp

Sandor Viragh

Eva Udvardy

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1979-10-11

Filing date

1980-10-06

Publication date

1986-03-13

1980-10-06 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1985-06-13 Publication of CS673780A2 publication Critical patent/CS673780A2/cs

1986-03-13 Publication of CS241032B2 publication Critical patent/CS241032B2/cs

Links

238000000034 method Methods 0.000 title claims abstract description 28
PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical compound O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 title description 19
238000004519 manufacturing process Methods 0.000 title description 4
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 47
-1 cyano, phenyl Chemical group 0.000 claims abstract description 37
150000001875 compounds Chemical class 0.000 claims abstract description 29
150000003839 salts Chemical group 0.000 claims abstract description 14
239000001257 hydrogen Substances 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 8
239000002253 acid Substances 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
239000003960 organic solvent Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 abstract description 9
125000000217 alkyl group Chemical group 0.000 abstract description 7
230000000694 effects Effects 0.000 abstract description 7
125000003545 alkoxy group Chemical group 0.000 abstract description 6
230000017531 blood circulation Effects 0.000 abstract description 4
230000002349 favourable effect Effects 0.000 abstract description 3
230000004217 heart function Effects 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
125000004432 carbon atom Chemical group C* 0.000 abstract 12
229910052736 halogen Inorganic materials 0.000 abstract 4
150000002367 halogens Chemical class 0.000 abstract 4
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
239000008194 pharmaceutical composition Substances 0.000 abstract 1
229940124549 vasodilator Drugs 0.000 abstract 1
239000003071 vasodilator agent Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 12
125000002774 3,4-dimethoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
239000011541 reaction mixture Substances 0.000 description 10
125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 description 9
229910001868 water Inorganic materials 0.000 description 7
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
241000282472 Canis lupus familiaris Species 0.000 description 5
239000002585 base Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
238000003756 stirring Methods 0.000 description 4
ZUZKDVHENRTHMH-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one;hydrochloride Chemical compound Cl.O=C1N=CNO1 ZUZKDVHENRTHMH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
210000004351 coronary vessel Anatomy 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
UVGYAOQHGGLHHV-UHFFFAOYSA-N 2-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)acetonitrile Chemical compound C1CNC(CC#N)C2=C1C=C(OC)C(OC)=C2 UVGYAOQHGGLHHV-UHFFFAOYSA-N 0.000 description 2
125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
239000013543 active substance Substances 0.000 description 2
210000002159 anterior chamber Anatomy 0.000 description 2
230000003288 anthiarrhythmic effect Effects 0.000 description 2
210000005242 cardiac chamber Anatomy 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
239000003814 drug Substances 0.000 description 2
210000003128 head Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
239000011976 maleic acid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
229960001789 papaverine Drugs 0.000 description 2
230000036581 peripheral resistance Effects 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
MVJZWRRXDKDIIG-UHFFFAOYSA-N 1,1-dimethoxy-3,4-dihydro-2h-isoquinoline Chemical compound C1=CC=C2C(OC)(OC)NCCC2=C1 MVJZWRRXDKDIIG-UHFFFAOYSA-N 0.000 description 1
FWWOWPGPERBCNJ-UHFFFAOYSA-N 2-hydroxy-4-(2-hydroxyethoxy)-4-oxobutanoic acid Chemical compound OCCOC(=O)CC(O)C(O)=O FWWOWPGPERBCNJ-UHFFFAOYSA-N 0.000 description 1
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 1
RZDWFRQCHUHRDD-UHFFFAOYSA-N 4H-oxadiazol-5-one hydrochloride Chemical compound Cl.O1N=NCC1=O RZDWFRQCHUHRDD-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 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
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
RMKWBDXFDHTOBV-UHFFFAOYSA-N O.Cl.O1N=CNC1=O Chemical compound O.Cl.O1N=CNC1=O RMKWBDXFDHTOBV-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-LHHVKLHASA-N Quinidine Natural products 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-LHHVKLHASA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000001772 anti-angiogenic effect Effects 0.000 description 1
239000003416 antiarrhythmic agent Substances 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
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 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000007423 decrease Effects 0.000 description 1
150000004683 dihydrates Chemical class 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229960004194 lidocaine Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
230000003836 peripheral circulation Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
230000002792 vascular Effects 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/475—Quinolines; Isoquinolines having an indole ring, e.g. yohimbine, reserpine, strychnine, vinblastine
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
- C07D273/04—Six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

CS806737A 1979-10-11 1980-10-06 Method of 1,2,4-oxadiazoline-5-on's new derivatives production CS241032B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79CI1973A HU179951B (en)	1979-10-11	1979-10-11	Process for preparing 1,2,4-oxadiazolin-5-one derivatives and pharmaceutical compositions containing thereof

Publications (2)

Publication Number	Publication Date
CS673780A2 CS673780A2 (en)	1985-06-13
CS241032B2 true CS241032B2 (en)	1986-03-13

Family

ID=10994764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS806737A CS241032B2 (en)	1979-10-11	1980-10-06	Method of 1,2,4-oxadiazoline-5-on's new derivatives production

Country Status (23)

Country	Link
US (1)	US4365064A (es)
JP (1)	JPS5661375A (es)
AT (1)	AT375369B (es)
BE (1)	BE885633A (es)
CA (1)	CA1154019A (es)
CH (1)	CH649547A5 (es)
CS (1)	CS241032B2 (es)
DD (1)	DD153550A5 (es)
DE (1)	DE3037432A1 (es)
DK (1)	DK149854C (es)
ES (1)	ES495819A0 (es)
FI (2)	FI71318C (es)
FR (1)	FR2467203A1 (es)
GB (1)	GB2059967B (es)
HU (1)	HU179951B (es)
IL (1)	IL61175A (es)
IT (1)	IT1129305B (es)
NL (1)	NL8005586A (es)
NO (1)	NO154795C (es)
PL (3)	PL131451B1 (es)
SE (1)	SE452158B (es)
SU (1)	SU1087519A1 (es)
YU (1)	YU41738B (es)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU180708B (en) *	1979-10-11	1983-04-29	Chinoin Gyogyszer Es Vegyeszet	Process for preparing new 1,2,4-oxadiazine derivatives
NZ521792A (en) *	2000-03-20	2004-06-25	N Gene Res Lab Inc	Propenecarboxylic acid amidoxime derivatives, a process for the preparation thereof, and use in treating conditions connected with oxygen deficiency
SI2935222T1 (sl)	2012-12-21	2019-02-28	Epizyme Inc.	Inhibitorji PRMT5 in njihove uporabe
EP3406607A1 (en)	2012-12-21	2018-11-28	Epizyme, Inc.	Prmt5 inhibitors containing a dihydro- or tetrahydroisoquinoline and uses thereof
US9365555B2 (en) *	2012-12-21	2016-06-14	Epizyme, Inc.	PRMT5 inhibitors and uses thereof
US9908887B2 (en)	2012-12-21	2018-03-06	Epizyme, Inc.	PRMT5 inhibitors and uses thereof
EP2935247B1 (en)	2012-12-21	2019-08-28	Epizyme, Inc.	Prmt5 inhibitors and uses thereof
AU2015301196A1 (en)	2014-08-04	2017-01-12	Epizyme, Inc.	PRMT5 inhibitors and uses thereof

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1529700A (fr) *	1967-04-11	1968-06-21	Dausse Sa Lab	Tertioaminoalcoyl oxadiazolinones et leur procédé de préparation
FR1575552A (es) *	1967-12-07	1969-07-25
US4038279A (en) *	1972-12-23	1977-07-26	Boehringer Ingelheim Gmbh	N-aryl-n'-(phenyl-or phenoxy-alkyl)-piperazines and salts thereof
US3994891A (en) *	1974-12-20	1976-11-30	Armour Pharmaceutical Company	Tetrahydroisoquinoline compounds
US4187220A (en) *	1977-08-30	1980-02-05	Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara R.T.	New O-(3-amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same
HU180708B (en) *	1979-10-11	1983-04-29	Chinoin Gyogyszer Es Vegyeszet	Process for preparing new 1,2,4-oxadiazine derivatives

1979
- 1979-10-11 HU HU79CI1973A patent/HU179951B/hu not_active IP Right Cessation
1980
- 1980-09-30 IL IL61175A patent/IL61175A/xx unknown
- 1980-10-03 DE DE19803037432 patent/DE3037432A1/de not_active Withdrawn
- 1980-10-06 CS CS806737A patent/CS241032B2/cs unknown
- 1980-10-07 SE SE8007025A patent/SE452158B/sv not_active IP Right Cessation
- 1980-10-09 JP JP14066880A patent/JPS5661375A/ja active Pending
- 1980-10-09 FR FR8021624A patent/FR2467203A1/fr active Granted
- 1980-10-09 AT AT0501380A patent/AT375369B/de not_active IP Right Cessation
- 1980-10-09 NL NL8005586A patent/NL8005586A/nl not_active Application Discontinuation
- 1980-10-09 IT IT68555/80A patent/IT1129305B/it active
- 1980-10-10 FI FI803219A patent/FI71318C/fi not_active IP Right Cessation
- 1980-10-10 CH CH7599/80A patent/CH649547A5/de not_active IP Right Cessation
- 1980-10-10 YU YU2594/80A patent/YU41738B/xx unknown
- 1980-10-10 GB GB8032828A patent/GB2059967B/en not_active Expired
- 1980-10-10 BE BE0/202406A patent/BE885633A/fr not_active IP Right Cessation
- 1980-10-10 PL PL1980232292A patent/PL131451B1/pl unknown
- 1980-10-10 FI FI803220A patent/FI71932C/fi not_active IP Right Cessation
- 1980-10-10 PL PL1980232293A patent/PL132131B1/pl unknown
- 1980-10-10 DD DD80224478A patent/DD153550A5/de not_active IP Right Cessation
- 1980-10-10 ES ES495819A patent/ES495819A0/es active Granted
- 1980-10-10 CA CA000362217A patent/CA1154019A/en not_active Expired
- 1980-10-10 DK DK429780A patent/DK149854C/da not_active IP Right Cessation
- 1980-10-10 SU SU802993201A patent/SU1087519A1/ru active
- 1980-10-10 NO NO803044A patent/NO154795C/no unknown
- 1980-10-10 PL PL1980227209A patent/PL131375B1/pl unknown
- 1980-10-14 US US06/196,583 patent/US4365064A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
ES8106725A1 (es)	1981-09-16
PL232292A1 (es)	1982-04-26
CS673780A2 (en)	1985-06-13
DK429780A (da)	1981-04-12
YU259480A (en)	1984-02-29
US4365064A (en)	1982-12-21
CA1154019A (en)	1983-09-20
FI71932C (fi)	1987-03-09
BE885633A (fr)	1981-02-02
FR2467203A1 (fr)	1981-04-17
FI71932B (fi)	1986-11-28
PL232293A1 (es)	1982-04-26
IL61175A (en)	1984-08-31
FI803220L (fi)	1981-04-12
FI71318C (fi)	1986-12-19
DK149854B (da)	1986-10-13
ATA501380A (de)	1983-12-15
JPS5661375A (en)	1981-05-26
GB2059967A (en)	1981-04-29
ES495819A0 (es)	1981-09-16
AT375369B (de)	1984-07-25
FR2467203B1 (es)	1985-03-22
IT1129305B (it)	1986-06-04
PL131451B1 (en)	1984-11-30
SE8007025L (sv)	1981-04-12
IL61175A0 (en)	1980-11-30
FI803219L (fi)	1981-04-12
PL131375B1 (en)	1984-11-30
DD153550A5 (de)	1982-01-13
PL227209A1 (es)	1981-12-11
HU179951B (en)	1983-01-28
GB2059967B (en)	1983-06-02
DK149854C (da)	1987-04-21
YU41738B (en)	1987-12-31
SU1087519A1 (ru)	1984-04-23
PL132131B1 (en)	1985-02-28
IT8068555A0 (it)	1980-10-09
NO154795C (no)	1986-12-29
NL8005586A (nl)	1981-04-14
DE3037432A1 (de)	1981-05-27
CH649547A5 (de)	1985-05-31
FI71318B (fi)	1986-09-09
NO803044L (no)	1981-04-13
NO154795B (no)	1986-09-15
SE452158B (sv)	1987-11-16

Publication	Publication Date	Title
EP0094159B1 (en)	1990-03-14	Dihydropyridine derivatives, their production and use
US4154839A (en)	1979-05-15	2,6-Dimethyl-3-carboxymethoxy-4-(2-nitrophenyl)-5-carbisobutoxy-1,4-dihydropyridine
JP2651043B2 (ja)	1997-09-10	ジフェニルメチルピペラジン誘導体
EP0060674A1 (en)	1982-09-22	Dihydropyridine anti-ischaemic and antihypertensive agents, processes for their production, and pharmaceutical compositions containing them
EP0424525B1 (en)	1994-12-21	Novel amines and their use
EP0116769B1 (en)	1987-03-25	Dihydropyridines
JPH04230681A (ja)	1992-08-19	１，４‐ベンゾチアゼピン誘導体
EP0106462B1 (en)	1988-12-07	Dihydropyridines
NO156525B (no)	1987-06-29	Analogifremgangsmaate ved fremstilling av terapeutisk aktive (3-aminopropoksy)bibenzylderivater.
RU2036922C1 (ru)	1995-06-09	Производные 1,4-дигидропиридина или их гидрохлориды, обладающие антагонистическими свойствами по отношению к ионам кальция
US4535073A (en)	1985-08-13	Antihypertensive phosphono derivatives of hantzsch dihydropyridines
US4992447A (en)	1991-02-12	Certain oxo-pyrrolo 1,4-dihydropyridines as antiallergy and antiinflammatory agents
CS241032B2 (en)	1986-03-13	Method of 1,2,4-oxadiazoline-5-on's new derivatives production
JPH0794417B2 (ja)	1995-10-11	Ｎ−アミノブチル−ｎ−フェニルアリールアミド誘導体
US4560686A (en)	1985-12-24	Method for treating circulatory diseases by using (2-lower alkoxyphenyl)piperazine derivatives
US4950818A (en)	1990-08-21	Method for treating ulcer
JPH0641464B2 (ja)	1994-06-01	ジヒドロピリジン類
US5064850A (en)	1991-11-12	Dihydro-3,3-diphenyl-5-(1H-pyrazol-1-ylmethyl-2(3H)-furanone and dihydro-5-((substituted-1H-pyrazol-1-yl)methyl)-3,3-diphenyl-2(3H)-furanone derivatives
JPS6256474A (ja)	1987-03-12	ジヒドロピリジン−２−ヒドロキシアミン類
US4638003A (en)	1987-01-20	1-(4-alkylthiophenyl)-2-(substituted or unsubstituted piperazine-1-yl)-1,3-propanediol, pharmaceutical compositions containing them useful as antiarrhythmic and vasodilating agents
JPH05271208A (ja)	1993-10-19	１，４‐ベンゾチアゼピン誘導体
US5116851A (en)	1992-05-26	Pharmaceutical composition and method for treating cardiovascular diseases using substituted anilides and sulfonamides
JP2834506B2 (ja)	1998-12-09	新規チエニルオキシ‐アルキルアミン誘導体、その製法及びこの化合物を含有する医薬
US3989708A (en)	1976-11-02	2-Amino-1,4-dihydropyridine derivatives
US4891373A (en)	1990-01-02	Aminopropanol derivatives of 1,4:3,6-dianhydrohexitol nitrates, processes for their preparation and their use as medicaments