NO124253B - - Google Patents

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Info

Publication number: NO124253B
Authority: NO; Norway
Prior art keywords: formula; acid; pyridyl; oxadiazole; amidoxime
Prior art date: 1968-04-26

Application number

NO1733/69A

Other languages

English (en)

Norwegian (no)

Inventor

K Harsanyi

L Tardos

C Vertesy

E Bako

G Leszkovszky

C Goenczi

K Takacs

J Reiter

D Korbonits

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.)

1968-04-26

Filing date

1969-04-25

Publication date

1972-03-27

1969-04-25 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1972-03-27 Publication of NO124253B publication Critical patent/NO124253B/no

Links

LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 12
-1 amino, hydroxy Chemical group 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
150000001350 alkyl halides Chemical class 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 4
150000002367 halogens Chemical group 0.000 claims description 4
ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
125000004076 pyridyl group Chemical group 0.000 claims description 3
238000000197 pyrolysis Methods 0.000 claims description 2
150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
238000000354 decomposition reaction Methods 0.000 claims 2
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
239000000047 product Substances 0.000 description 27
238000006243 chemical reaction Methods 0.000 description 16
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 16
206010010904 Convulsion Diseases 0.000 description 13
241000699670 Mus sp. Species 0.000 description 13
230000036461 convulsion Effects 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
241001279009 Strychnos toxifera Species 0.000 description 8
230000000694 effects Effects 0.000 description 8
229960005453 strychnine Drugs 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 7
241000700159 Rattus Species 0.000 description 6
230000009471 action Effects 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
210000003205 muscle Anatomy 0.000 description 5
229960002715 nicotine Drugs 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
238000009835 boiling Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 4
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 4
230000011514 reflex Effects 0.000 description 4
238000010992 reflux Methods 0.000 description 4
238000006798 ring closing metathesis reaction Methods 0.000 description 4
239000002904 solvent Substances 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
206010068887 Tobacco poisoning Diseases 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
239000012876 carrier material Substances 0.000 description 3
TZFWDZFKRBELIQ-UHFFFAOYSA-N chlorzoxazone Chemical compound ClC1=CC=C2OC(O)=NC2=C1 TZFWDZFKRBELIQ-UHFFFAOYSA-N 0.000 description 3
229960003633 chlorzoxazone Drugs 0.000 description 3
239000013078 crystal Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
235000011121 sodium hydroxide Nutrition 0.000 description 3
239000000725 suspension Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical group C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
239000013543 active substance Substances 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
229910000147 aluminium phosphate Inorganic materials 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000011260 aqueous acid Substances 0.000 description 2
238000010533 azeotropic distillation Methods 0.000 description 2
239000002585 base Substances 0.000 description 2
230000008901 benefit Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229910000019 calcium carbonate Inorganic materials 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
229910000042 hydrogen bromide Inorganic materials 0.000 description 2
230000035873 hypermotility Effects 0.000 description 2
239000004310 lactic acid Substances 0.000 description 2
235000014655 lactic acid Nutrition 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
150000007522 mineralic acids Chemical class 0.000 description 2
238000002156 mixing Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
229960005181 morphine Drugs 0.000 description 2
239000003158 myorelaxant agent Substances 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 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
OLENANGIJWDOPG-UHFFFAOYSA-N (2-chlorobenzoyl) 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1Cl OLENANGIJWDOPG-UHFFFAOYSA-N 0.000 description 1
OOBHFESNSZDWIU-GXSJLCMTSA-N (2s,3s)-3-methyl-2-phenylmorpholine Chemical compound C[C@@H]1NCCO[C@H]1C1=CC=CC=C1 OOBHFESNSZDWIU-GXSJLCMTSA-N 0.000 description 1
BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
FPYUJUBAXZAQNL-UHFFFAOYSA-N 2-chlorobenzaldehyde Chemical compound ClC1=CC=CC=C1C=O FPYUJUBAXZAQNL-UHFFFAOYSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
JKNSMBZZZFGYCB-UHFFFAOYSA-N 4,5-dihydrooxadiazole Chemical class C1CN=NO1 JKNSMBZZZFGYCB-UHFFFAOYSA-N 0.000 description 1
NGKWCJCCZGCLID-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC=C1C1=NC(C=2N=CC=CC=2)=NO1 NGKWCJCCZGCLID-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
206010049816 Muscle tightness Diseases 0.000 description 1
238000000297 Sandmeyer reaction Methods 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
150000008041 alkali metal carbonates Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
239000002269 analeptic agent Substances 0.000 description 1
230000003555 analeptic effect Effects 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000000954 anitussive effect Effects 0.000 description 1
229940124584 antitussives Drugs 0.000 description 1
239000002249 anxiolytic agent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
XKXCGXSHUNVFCT-UHFFFAOYSA-N chembl3263490 Chemical compound ON=C(N)C1=CC=CC=N1 XKXCGXSHUNVFCT-UHFFFAOYSA-N 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
239000000812 cholinergic antagonist Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
229960003920 ***e Drugs 0.000 description 1
239000012043 crude product Substances 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical class [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
PCHPORCSPXIHLZ-UHFFFAOYSA-N diphenhydramine hydrochloride Chemical compound [Cl-].C=1C=CC=CC=1C(OCC[NH+](C)C)C1=CC=CC=C1 PCHPORCSPXIHLZ-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
239000008298 dragée Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RETLCWPMLJPOTP-UHFFFAOYSA-N ethyl 2-chlorobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1Cl RETLCWPMLJPOTP-UHFFFAOYSA-N 0.000 description 1
229960003750 ethyl chloride Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000945 filler Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000005187 foaming Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 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
BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000004899 motility Effects 0.000 description 1
229940035363 muscle relaxants Drugs 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
150000004866 oxadiazoles Chemical class 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229960003209 phenmetrazine Drugs 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000008569 process Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000002040 relaxant effect Effects 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
230000002048 spasmolytic effect Effects 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000011044 succinic acid Nutrition 0.000 description 1
239000000829 suppository Substances 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
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Pyridine Compounds (AREA)

NO1733/69A 1968-04-26 1969-04-25 NO124253B (bg)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI000796		1968-04-26

Publications (1)

Publication Number	Publication Date
NO124253B true NO124253B (bg)	1972-03-27

Family

ID=10994349

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO1733/69A NO124253B (bg)	1968-04-26	1969-04-25

Country Status (15)

Country	Link
US (1)	US3647809A (bg)
JP (1)	JPS4824394B1 (bg)
AT (2)	AT292728B (bg)
BE (1)	BE732131A (bg)
BR (1)	BR6908381D0 (bg)
CA (1)	CA954858A (bg)
CH (2)	CH540925A (bg)
DE (1)	DE1920037A1 (bg)
FR (1)	FR2007529B1 (bg)
GB (1)	GB1271302A (bg)
IL (1)	IL31990A (bg)
NL (1)	NL6906401A (bg)
NO (1)	NO124253B (bg)
PL (1)	PL79435B1 (bg)
SE (1)	SE368576B (bg)

Families Citing this family (39)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3853893A (en) *	1973-04-02	1974-12-10	Squibb & Sons Inc	Anthelmintic 5-(pyridyl)-3-(isothiocyanophenyl) oxadiazoles
HU177086B (en) *	1975-06-09	1981-07-28	Eszakmagyar Vegyimuevek	Herbicide and fungicide preparation containing substituted 1,2,4-oxadiazolidin-3-one derivatives
JPS58150576A (ja) *	1982-03-03	1983-09-07	Sumitomo Chem Co Ltd	新規な１，２，４−オキサジアゾ−ル誘導体
DE3247118A1 (de) *	1982-12-20	1984-06-20	Cassella Ag, 6000 Frankfurt	Neue substituierte 1,4-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
US6660753B2 (en) *	1999-08-19	2003-12-09	Nps Pharmaceuticals, Inc.	Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
EP1582519A3 (en) *	1999-08-19	2005-12-21	Nps Pharmaceuticals, Inc.	Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
BR0013427A (pt) *	1999-08-19	2002-07-30	Nps Pharma Inc	Compostos heteropolicìclicos e seus usos como antagonistas no receptor de glutamato metabotrópico
PL369598A1 (en) *	2001-02-21	2005-05-02	Nps Pharmaceuticals, Inc.	Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
AU2003264018A1 (en)	2002-08-09	2004-02-25	Astrazeneca Ab	Compounds having an activity at metabotropic glutamate receptors
EP1611123B8 (en) *	2003-04-09	2013-11-13	Exelixis, Inc.	Tie-2 modulators and methods of use
JP2006528980A (ja) *	2003-05-15	2006-12-28	メルク　エンド　カムパニー　インコーポレーテッド	Ｓ１ｐ受容体作働薬としての３−（２−アミノ−１−アザシクロ）−５−アリール−１，２，４−オキサジアゾール類
US20060189661A1 (en) *	2003-11-03	2006-08-24	Wagenen Bradford V	Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
WO2005060961A2 (en) *	2003-12-18	2005-07-07	Astrazeneca Ab	Treatment of transient lower esophageal sphincter relaxations (tlesrs) and gastro-esophageal reflux disease (gerd)
WO2005061489A1 (en) *	2003-12-24	2005-07-07	Prosidion Limited	Heterocyclic derivatives as gpcr receptor agonists
WO2005077368A2 (en) *	2004-02-03	2005-08-25	Astrazeneca Ab	Treatment of gastro-esophageal reflux disease (gerd)
AU2006239418A1 (en)	2005-04-26	2006-11-02	Neurosearch A/S	Novel oxadiazole derivatives and their medical use
IL169855A (en) *	2005-07-25	2014-05-28	Elta Systems Ltd	A system and method for locating a receiver location
BRPI0613859B8 (pt)	2005-07-26	2021-05-25	Bial Portela & Ca Sa	inibidores da comt, seus usos, e composição farmacêutica
EP1845097A1 (en)	2006-04-10	2007-10-17	Portela & Ca., S.A.	Oxadiazole derivatives as COMT inhibitors
MX2009002233A (es) *	2006-09-07	2009-03-16	Actelion Pharmaceuticals Ltd	Derivados de piridin-4-il como agentes inmunomoduladores.
EP2069335B1 (en) *	2006-09-08	2012-12-26	Actelion Pharmaceuticals Ltd.	Pyridin-3-yl derivatives as immunomodulating agents
EP2124947B1 (en)	2007-01-31	2017-07-19	BIAL - Portela & Ca., S.A.	Dosage regimen for comt inhibitors
ES2450750T3 (es) *	2007-03-16	2014-03-25	Actelion Pharmaceuticals Ltd.	Derivados de amino-piridina como agonistas del receptor S1P1/EDG1
ES2361463T3 (es) *	2007-08-17	2011-06-17	Actelion Pharmaceuticals Ltd.	Derivados de piridina como moduladores del receptor s1p1/edg1.
MX2010009043A (es) *	2008-02-28	2010-10-25	Bial Portela & Ca Sa	Composicion farmaceutica para farmacos poco solubles.
EP2262799B1 (en) *	2008-03-06	2012-07-04	Actelion Pharmaceuticals Ltd.	Pyridine compounds
US8575200B2 (en) *	2008-03-07	2013-11-05	Actelion Pharmaceuticals Ltd	Pyridin-2-yl derivatives as immunomodulating agents
CA2718772C (en)	2008-03-17	2017-05-02	David Alexander Learmonth	Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol
MY156381A (en) *	2008-05-14	2016-02-15	Scripps Research Inst	Novel modulators of sphingosine phosphate receptors
WO2010093650A2 (en)	2009-02-10	2010-08-19	Divergence, Inc.	Compositions and methods for controlling nematodes
CN105878242A (zh) *	2009-04-01	2016-08-24	巴尔-波特拉及康邦亚股份有限公司	包括硝基儿茶酚衍生物的药物制剂及其制备方法
CN102438595B (zh) *	2009-04-01	2016-04-27	巴尔-波特拉及康邦亚股份有限公司	包括硝基儿茶酚衍生物的药物制剂及其制备方法
AR077413A1 (es)	2009-07-16	2011-08-24	Actelion Pharmaceuticals Ltd	Derivados piridin-4-ilo
DK2665720T3 (en)	2011-01-19	2015-07-13	Actelion Pharmaceuticals Ltd	2-methoxy-pyridin-4-yl-yl derivatives
US20140045900A1 (en)	2011-02-11	2014-02-13	Bial-Portela & Ca, S.A.	Administration regime for nitrocatechols
PT3604299T (pt)	2011-12-13	2023-10-31	Bial Portela & Ca Sa	Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase
UY35327A (es)	2013-02-15	2014-09-30	Monsanto Technology Llc	?4,5-dihidro-1,2,4-oxadiazoles disustituidos en 3,5 y composiciones y métodos para controlar plagas de nematodos?.
WO2016083863A1 (en)	2014-11-28	2016-06-02	Bial - Portela & Ca, S.A.	Medicaments for slowing parkinson's disease
HUE047646T2 (hu)	2015-05-20	2020-05-28	Idorsia Pharmaceuticals Ltd	Az (S)-3-{4-[5-(2-ciklopentil-6-metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metil-fenoxi} -propán-1,2-diol vegyület kristályformája

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL120029C (bg) *	1959-09-29
US3227725A (en) *	1962-04-17	1966-01-04	Union Carbide Corp	Certain 3,5-disubstituted 1,2,4-oxadiazole compounds

1969
- 1969-04-08 US US815520A patent/US3647809A/en not_active Expired - Lifetime
- 1969-04-08 IL IL31990A patent/IL31990A/xx unknown
- 1969-04-14 GB GB09047/69A patent/GB1271302A/en not_active Expired
- 1969-04-18 AT AT815670A patent/AT292728B/de not_active IP Right Cessation
- 1969-04-18 AT AT375469A patent/AT292727B/de not_active IP Right Cessation
- 1969-04-19 DE DE19691920037 patent/DE1920037A1/de active Pending
- 1969-04-24 FR FR696912994A patent/FR2007529B1/fr not_active Expired
- 1969-04-24 CH CH627569A patent/CH540925A/de not_active IP Right Cessation
- 1969-04-24 CH CH1476972A patent/CH542232A/de not_active IP Right Cessation
- 1969-04-25 JP JP44032259A patent/JPS4824394B1/ja active Pending
- 1969-04-25 NL NL6906401A patent/NL6906401A/xx unknown
- 1969-04-25 CA CA049,755A patent/CA954858A/en not_active Expired
- 1969-04-25 SE SE05909/69A patent/SE368576B/xx unknown
- 1969-04-25 NO NO1733/69A patent/NO124253B/no unknown
- 1969-04-25 BE BE732131D patent/BE732131A/xx unknown
- 1969-04-25 PL PL1969133199A patent/PL79435B1/pl unknown
- 1969-04-25 BR BR208381/69A patent/BR6908381D0/pt unknown

Also Published As

Publication number	Publication date
DE1920037A1 (de)	1970-11-12
NL6906401A (bg)	1969-10-28
PL79435B1 (en)	1975-06-30
BR6908381D0 (pt)	1973-02-08
BE732131A (bg)	1969-10-01
JPS4824394B1 (bg)	1973-07-20
GB1271302A (en)	1972-04-19
CH542232A (de)	1973-11-15
CH540925A (de)	1973-08-31
AT292727B (de)	1971-09-10
IL31990A (en)	1974-05-16
FR2007529B1 (bg)	1973-03-16
US3647809A (en)	1972-03-07
FR2007529A1 (bg)	1970-01-09
SE368576B (bg)	1974-07-08
AT292728B (de)	1971-09-10
IL31990A0 (en)	1969-06-25
CA954858A (en)	1974-09-17

Publication	Publication Date	Title
NO124253B (bg)	1972-03-27
US4711890A (en)	1987-12-08	Pharmaceutical compositions containing azanaphthalene-carboxamide derivatives, azanaphthalene-carboxamide derivatives and process for their use
DE3888821T2 (de)	1994-08-11	Tricyclische Verbindungen.
JPS6172751A (ja)	1986-04-14	カルボニル化合物、その製造方法及び該化合物を含む医薬製剤
US3600394A (en)	1971-08-17	2-aminoalkyl-3-arylisocarbostyrils
US4216216A (en)	1980-08-05	Aromatic piperazinyl substituted dihydrouracils
RU2281282C2 (ru)	2006-08-10	Производное пиридин-1-оксида и способы его преобразования в фармацевтически эффективные соединения
CS241549B2 (en)	1986-03-13	Method of 1,4-dihydropyridines production
US3280122A (en)	1966-10-18	Diphenylalkyloxadiazoles
US4497808A (en)	1985-02-05	N-Oxide compounds useful in the treatment of cardiovascular ailments
NO166323B (no)	1991-03-25	Analogifremgangsmaate for fremstilling av terapeutisk aktive oxadiazolalkylpurinderivater.
NO802326L (no)	1981-02-04	Fremgangsmaate ved fremstilling av substituerte tetraazatricyklen
US3408353A (en)	1968-10-29	1, 3, 4, 9b-tetrahydro-2h-indeno(1, 2-c)pyridine derivatives
US4442102A (en)	1984-04-10	1,5-Diphenylpyrazolin-3-one compounds, process and intermediates for preparation thereof and pharmaceutical compositions containing same
US3959286A (en)	1976-05-25	N-(1-(1,3-Dihydro-1,3-dioxo-2H-benz(de)-isoquinolin-2-yl)alkyl)-4-N-piperidinyl)-n-phenylalkylamides
US3636041A (en)	1972-01-18	4 5-dihydro-7h-thieno(2 3-c)thiopyrans
WO1999033840A2 (en)	1999-07-08	Pyrrolothiazine and pyrrolothiazepine compounds having serotonin-2 receptor antagonistic and alpha1-blocking action
US4129738A (en)	1978-12-12	5-Phenylpyrazolo[1,5-a]pyrimidin-7(1H)-ones
US3810905A (en)	1974-05-14	Pyrazolo(3,4-b)pyridine-5-carboxamides
US3936459A (en)	1976-02-03	1',4'-Dihydro-1-methyl-spiro [piperidine and pyrrolidine-2,3'(2'H)quinoline]-2'-one compounds
US2910479A (en)	1959-10-27	Certain 4-pyridyl thiazoline-2-ones and process
US4808603A (en)	1989-02-28	3,5-diacyl-2,6-dialkyl-4-aryl-1,4-dihydropyridines, their use, and pharmaceutical compositions thereof
US6166034A (en)	2000-12-26	Spiro piperidine derivatives as 5HT1D receptor antagonists
US3963740A (en)	1976-06-15	Benzo and benzothiopyranoindazole N-oxides
WO1999033841A2 (en)	1999-07-08	Pyrrolothiazine and pyrrolothiazepine compounds having serotonin-2 receptor antagonistic and alpha-1-blocking action