NL8005586A - 1,2,4-oxadiazolin-5-on-derivaten, werkwijze ter bereiding daarvan en farmaceutische preparaten, die deze verbindingen bevatten. - Google Patents

1,2,4-oxadiazolin-5-on-derivaten, werkwijze ter bereiding daarvan en farmaceutische preparaten, die deze verbindingen bevatten. Download PDF

Info

Publication number: NL8005586A
Authority: NL; Netherlands
Prior art keywords: carbon atoms; phenyl; alkoxy; alkyl; general formula
Prior art date: 1979-10-11

Application number

NL8005586A

Other languages

English (en)

Dutch (nl)

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

1980-10-09

Publication date

1981-04-14

1980-10-09 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1981-04-14 Publication of NL8005586A publication Critical patent/NL8005586A/nl

Links

150000001875 compounds Chemical class 0.000 title claims description 42
238000000034 method Methods 0.000 title claims description 38
239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 40
-1 cyano, phenyl Chemical group 0.000 claims description 35
125000000217 alkyl group Chemical group 0.000 claims description 26
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 18
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 claims description 15
150000003839 salts Chemical class 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000005843 halogen group Chemical group 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
PCJFEVUKVKQSSL-UHFFFAOYSA-N 2h-1,2,4-oxadiazol-5-one Chemical class O=C1N=CNO1 PCJFEVUKVKQSSL-UHFFFAOYSA-N 0.000 claims description 5
239000000203 mixture Substances 0.000 claims description 5
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 2
125000004429 atom Chemical group 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
239000000969 carrier Substances 0.000 claims description 2
231100000252 nontoxic Toxicity 0.000 claims description 2
230000003000 nontoxic effect Effects 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 2
229910052783 alkali metal Inorganic materials 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
239000003814 drug Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
238000002844 melting Methods 0.000 description 20
230000008018 melting Effects 0.000 description 20
238000001953 recrystallisation Methods 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
239000000047 product Substances 0.000 description 11
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 10
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical class C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
241000282472 Canis lupus familiaris Species 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
239000002585 base Substances 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
125000005956 isoquinolyl group Chemical group 0.000 description 4
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound 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 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 3
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 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
230000003288 anthiarrhythmic effect Effects 0.000 description 2
230000003257 anti-anginal effect Effects 0.000 description 2
230000004872 arterial blood pressure Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
206010061592 cardiac fibrillation Diseases 0.000 description 2
210000001715 carotid artery Anatomy 0.000 description 2
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 2
238000007796 conventional method Methods 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
230000002600 fibrillogenic effect Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229960004194 lidocaine Drugs 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
239000011976 maleic acid Substances 0.000 description 2
239000000155 melt Substances 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
229960001789 papaverine Drugs 0.000 description 2
230000002093 peripheral effect Effects 0.000 description 2
230000036581 peripheral resistance Effects 0.000 description 2
229960001404 quinidine Drugs 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
230000000304 vasodilatating effect Effects 0.000 description 2
CTQPPUPWHLGKOB-UHFFFAOYSA-N 4h-oxadiazol-5-one Chemical compound O=C1CN=NO1 CTQPPUPWHLGKOB-UHFFFAOYSA-N 0.000 description 1
HMYJLVDKPJHJCF-UHFFFAOYSA-N 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline Chemical compound C1CNC(C)C2=C1C=C(OC)C(OC)=C2 HMYJLVDKPJHJCF-UHFFFAOYSA-N 0.000 description 1
206010002383 Angina Pectoris Diseases 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
CEIXWJHURKEBMQ-UHFFFAOYSA-N Heliamine Chemical compound C1CNCC2=C1C=C(OC)C(OC)=C2 CEIXWJHURKEBMQ-UHFFFAOYSA-N 0.000 description 1
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 1
241000700159 Rattus Species 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
230000001476 alcoholic effect Effects 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
210000000709 aorta Anatomy 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical compound [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
230000004087 circulation Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
208000035475 disorder Diseases 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
239000000945 filler Substances 0.000 description 1
230000004217 heart function Effects 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 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
239000007787 solid Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 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
- 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
- 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

Landscapes

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)

NL8005586A 1979-10-11 1980-10-09 1,2,4-oxadiazolin-5-on-derivaten, werkwijze ter bereiding daarvan en farmaceutische preparaten, die deze verbindingen bevatten. NL8005586A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HUCI001973		1979-10-11
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 (1)

Publication Number	Publication Date
NL8005586A true NL8005586A (nl)	1981-04-14

Family

ID=10994764

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8005586A NL8005586A (nl)	1979-10-11	1980-10-09	1,2,4-oxadiazolin-5-on-derivaten, werkwijze ter bereiding daarvan en farmaceutische preparaten, die deze verbindingen bevatten.

Country Status (23)

Country	Link
US (1)	US4365064A (cs)
JP (1)	JPS5661375A (cs)
AT (1)	AT375369B (cs)
BE (1)	BE885633A (cs)
CA (1)	CA1154019A (cs)
CH (1)	CH649547A5 (cs)
CS (1)	CS241032B2 (cs)
DD (1)	DD153550A5 (cs)
DE (1)	DE3037432A1 (cs)
DK (1)	DK149854C (cs)
ES (1)	ES8106725A1 (cs)
FI (2)	FI71932C (cs)
FR (1)	FR2467203A1 (cs)
GB (1)	GB2059967B (cs)
HU (1)	HU179951B (cs)
IL (1)	IL61175A (cs)
IT (1)	IT1129305B (cs)
NL (1)	NL8005586A (cs)
NO (1)	NO154795C (cs)
PL (3)	PL132131B1 (cs)
SE (1)	SE452158B (cs)
SU (1)	SU1087519A1 (cs)
YU (1)	YU41738B (cs)

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
JP2003528073A (ja) *	2000-03-20	2003-09-24	エヌ・ジーンリサーチラボラトリーズインコーポレイテッド	プロペンカルボン酸アミドキシム誘導体、その製法、及びこの誘導体を含有する医薬組成物
US9604930B2 (en)	2012-12-21	2017-03-28	Epizyme, Inc.	Tetrahydro- and dihydro-isoquinoline PRMT5 inhibitors and uses thereof
US10118918B2 (en)	2012-12-21	2018-11-06	Epizyme, Inc.	PRMT5 inhibitors 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
JP2016505002A (ja)	2012-12-21	2016-02-18	エピザイム，インコーポレイティド	ジヒドロイソキノリンまたはテトラヒドロイソキノリンを含有するｐｒｍｔ５阻害剤およびその使用
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 (cs) *	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 IT IT68555/80A patent/IT1129305B/it active
- 1980-10-09 NL NL8005586A patent/NL8005586A/nl not_active Application Discontinuation
- 1980-10-09 FR FR8021624A patent/FR2467203A1/fr active Granted
- 1980-10-09 JP JP14066880A patent/JPS5661375A/ja active Pending
- 1980-10-09 AT AT0501380A patent/AT375369B/de not_active IP Right Cessation
- 1980-10-10 GB GB8032828A patent/GB2059967B/en not_active Expired
- 1980-10-10 SU SU802993201A patent/SU1087519A1/ru active
- 1980-10-10 BE BE0/202406A patent/BE885633A/fr not_active IP Right Cessation
- 1980-10-10 DD DD80224478A patent/DD153550A5/de not_active IP Right Cessation
- 1980-10-10 ES ES495819A patent/ES8106725A1/es not_active Expired
- 1980-10-10 YU YU2594/80A patent/YU41738B/xx unknown
- 1980-10-10 PL PL1980232293A patent/PL132131B1/pl unknown
- 1980-10-10 PL PL1980232292A patent/PL131451B1/pl unknown
- 1980-10-10 NO NO803044A patent/NO154795C/no unknown
- 1980-10-10 FI FI803220A patent/FI71932C/fi not_active IP Right Cessation
- 1980-10-10 DK DK429780A patent/DK149854C/da not_active IP Right Cessation
- 1980-10-10 CH CH7599/80A patent/CH649547A5/de not_active IP Right Cessation
- 1980-10-10 CA CA000362217A patent/CA1154019A/en not_active Expired
- 1980-10-10 PL PL1980227209A patent/PL131375B1/pl unknown
- 1980-10-10 FI FI803219A patent/FI71318C/fi not_active IP Right Cessation
- 1980-10-14 US US06/196,583 patent/US4365064A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
PL131375B1 (en)	1984-11-30
CS241032B2 (en)	1986-03-13
DK429780A (da)	1981-04-12
IT8068555A0 (it)	1980-10-09
AT375369B (de)	1984-07-25
FR2467203B1 (cs)	1985-03-22
YU41738B (en)	1987-12-31
IL61175A (en)	1984-08-31
PL132131B1 (en)	1985-02-28
FI71318C (fi)	1986-12-19
PL232292A1 (cs)	1982-04-26
DK149854B (da)	1986-10-13
GB2059967A (en)	1981-04-29
NO803044L (no)	1981-04-13
CA1154019A (en)	1983-09-20
FI71932C (fi)	1987-03-09
ES495819A0 (es)	1981-09-16
JPS5661375A (en)	1981-05-26
DK149854C (da)	1987-04-21
FR2467203A1 (fr)	1981-04-17
PL232293A1 (cs)	1982-04-26
DD153550A5 (de)	1982-01-13
SU1087519A1 (ru)	1984-04-23
CH649547A5 (de)	1985-05-31
FI71318B (fi)	1986-09-09
IL61175A0 (en)	1980-11-30
FI803219L (fi)	1981-04-12
US4365064A (en)	1982-12-21
ES8106725A1 (es)	1981-09-16
PL227209A1 (cs)	1981-12-11
GB2059967B (en)	1983-06-02
HU179951B (en)	1983-01-28
CS673780A2 (en)	1985-06-13
FI803220L (fi)	1981-04-12
PL131451B1 (en)	1984-11-30
NO154795C (no)	1986-12-29
SE8007025L (sv)	1981-04-12
YU259480A (en)	1984-02-29
IT1129305B (it)	1986-06-04
NO154795B (no)	1986-09-15
ATA501380A (de)	1983-12-15
BE885633A (fr)	1981-02-02
FI71932B (fi)	1986-11-28
SE452158B (sv)	1987-11-16
DE3037432A1 (de)	1981-05-27

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1987-12-01	BV	The patent application has lapsed

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US4365064A (en)	1982-12-21	1,2,4-Oxadiazolin-5-one derivatives, process for their preparation and pharmaceutical compositions containing them
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