DD158399A5 - Verfahren zur herstellung von neuen dihydro-as-triazino 5, 6-cichinolinderivaten - Google Patents

Verfahren zur herstellung von neuen dihydro-as-triazino 5, 6-cichinolinderivaten Download PDF

Info

Publication number: DD158399A5
Authority: DD; German Democratic Republic
Prior art keywords: triazino; dihydro; quinoline; general formula; acid addition
Prior art date: 1980-04-18

Application number

DD81229303A

Other languages

German (de)

English (en)

Inventor

Edit Berenyi

Peter Goeroeg

Katalin Grasser

Ibolya Kosoczky

Agnes Kovacs

Lujza Petoecz

Original Assignee

Egyt Gyogyszervegyeszeti Gyar

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.)

1980-04-18

Filing date

1981-04-16

Publication date

1983-01-12

1981-04-16 Application filed by Egyt Gyogyszervegyeszeti Gyar filed Critical Egyt Gyogyszervegyeszeti Gyar

1983-01-12 Publication of DD158399A5 publication Critical patent/DD158399A5/de

Links

238000000034 method Methods 0.000 title claims description 28
238000002360 preparation method Methods 0.000 title claims description 7
239000002253 acid Substances 0.000 claims abstract description 32
150000003839 salts Chemical class 0.000 claims abstract description 27
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
239000000126 substance Substances 0.000 claims abstract description 12
150000007522 mineralic acids Chemical class 0.000 claims abstract description 5
150000007524 organic acids Chemical class 0.000 claims abstract description 5
235000005985 organic acids Nutrition 0.000 claims abstract description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 93
150000001875 compounds Chemical class 0.000 claims description 31
125000002252 acyl group Chemical group 0.000 claims description 12
150000003248 quinolines Chemical class 0.000 claims description 10
238000005917 acylation reaction Methods 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 9
230000010933 acylation Effects 0.000 claims description 8
229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 claims description 8
125000003710 aryl alkyl group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
230000029936 alkylation Effects 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract description 18
238000004519 manufacturing process Methods 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 abstract 8
239000001257 hydrogen Substances 0.000 abstract 8
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
230000021736 acetylation Effects 0.000 abstract 3
238000006640 acetylation reaction Methods 0.000 abstract 3
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 2
239000012345 acetylating agent Substances 0.000 abstract 2
150000002431 hydrogen Chemical group 0.000 abstract 2
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 73
238000002844 melting Methods 0.000 description 48
230000008018 melting Effects 0.000 description 48
-1 n -tentyl Chemical group 0.000 description 27
241001465754 Metazoa Species 0.000 description 13
PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 12
230000001225 therapeutic effect Effects 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
241000699670 Mus sp. Species 0.000 description 8
239000013078 crystal Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 7
239000000725 suspension Substances 0.000 description 7
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 6
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
229960002895 phenylbutazone Drugs 0.000 description 6
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000825 pharmaceutical preparation Substances 0.000 description 5
239000007858 starting material Substances 0.000 description 5
229960004453 trimethadione Drugs 0.000 description 5
IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 4
229960000836 amitriptyline Drugs 0.000 description 4
230000001773 anti-convulsant effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
230000005764 inhibitory process Effects 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
229960005489 paracetamol Drugs 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 3
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000000202 analgesic effect Effects 0.000 description 3
230000003110 anti-inflammatory effect Effects 0.000 description 3
239000001961 anticonvulsive agent Substances 0.000 description 3
229960003965 antiepileptics Drugs 0.000 description 3
238000009835 boiling Methods 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 3
230000002265 prevention Effects 0.000 description 3
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
235000017557 sodium bicarbonate Nutrition 0.000 description 3
229960005333 tetrabenazine Drugs 0.000 description 3
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
108010010803 Gelatin Proteins 0.000 description 2
NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ARFYZKAYDRJATN-UHFFFAOYSA-N [1,2,4]triazino[5,6-c]quinoline Chemical compound C1=NN=C2C3=CC=CC=C3N=CC2=N1 ARFYZKAYDRJATN-UHFFFAOYSA-N 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000036461 convulsion Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229920000159 gelatin Polymers 0.000 description 2
239000008273 gelatin Substances 0.000 description 2
235000019322 gelatine Nutrition 0.000 description 2
235000011852 gelatine desserts Nutrition 0.000 description 2
229960002456 hexobarbital Drugs 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 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
229960004815 meprobamate Drugs 0.000 description 2
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
230000001624 sedative effect Effects 0.000 description 2
239000000600 sorbitol Substances 0.000 description 2
235000010356 sorbitol Nutrition 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
230000001256 tonic 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
UTQNKKSJPHTPBS-UHFFFAOYSA-N 2,2,2-trichloroethanone Chemical group ClC(Cl)(Cl)[C]=O UTQNKKSJPHTPBS-UHFFFAOYSA-N 0.000 description 1
UNBPKAKPNOMMQM-UHFFFAOYSA-N 4-butyl-1,2-diphenylpyrazolidine Chemical compound C1C(CCCC)CN(C=2C=CC=CC=2)N1C1=CC=CC=C1 UNBPKAKPNOMMQM-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
241000238557 Decapoda Species 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 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
208000007101 Muscle Cramp Diseases 0.000 description 1
206010030113 Oedema Diseases 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 description 1
TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 description 1
150000004075 acetic anhydrides Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
230000002082 anti-convulsion Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
229910000389 calcium phosphate Inorganic materials 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
239000000969 carrier Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
210000000744 eyelid Anatomy 0.000 description 1
239000000945 filler Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000003193 general anesthetic agent Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002757 inflammatory effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000003141 lower extremity Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
229910052753 mercury Inorganic materials 0.000 description 1
229940095102 methyl benzoate Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
239000003921 oil Substances 0.000 description 1
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
OEBIHOVSAMBXIB-SJKOYZFVSA-N selitrectinib Chemical compound C[C@@H]1CCC2=NC=C(F)C=C2[C@H]2CCCN2C2=NC3=C(C=NN3C=C2)C(=O)N1 OEBIHOVSAMBXIB-SJKOYZFVSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000012239 silicon dioxide Nutrition 0.000 description 1
230000004617 sleep duration Effects 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000375 suspending agent 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
231100001274 therapeutic index Toxicity 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
230000001960 triggered effect Effects 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P23/00—Anaesthetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pain & Pain Management (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Anesthesiology (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD81229303A 1980-04-18 1981-04-16 Verfahren zur herstellung von neuen dihydro-as-triazino 5, 6-cichinolinderivaten DD158399A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU80939A HU181689B (en)	1980-04-18	1980-04-18	Process for producing new dihydro-as-triazino-square bracket-5,6-c-square bracket closed-quinoline derivatives

Publications (1)

Publication Number	Publication Date
DD158399A5 true DD158399A5 (de)	1983-01-12

Family

ID=10952123

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD81229303A DD158399A5 (de)	1980-04-18	1981-04-16	Verfahren zur herstellung von neuen dihydro-as-triazino 5, 6-cichinolinderivaten

Country Status (15)

Country	Link
US (1)	US4342766A (cs)
EP (1)	EP0038528B1 (cs)
JP (1)	JPS56166190A (cs)
AT (1)	ATE8893T1 (cs)
AU (1)	AU540758B2 (cs)
CS (1)	CS221293B2 (cs)
DD (1)	DD158399A5 (cs)
DE (1)	DE3165346D1 (cs)
DK (1)	DK170581A (cs)
ES (1)	ES502078A0 (cs)
FI (1)	FI70896C (cs)
GR (1)	GR74516B (cs)
HU (1)	HU181689B (cs)
SU (1)	SU1014475A3 (cs)
YU (1)	YU100981A (cs)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3721670A (en) *	1971-04-05	1973-03-20	Morton Norwich Products Inc	3-substituted-as-triazino(5,6-c)quinolines
HU165678B (cs) *	1972-05-05	1974-10-28
HU165677B (cs) *	1972-05-05	1974-10-28
HU165520B (cs) *	1972-05-05	1974-09-28

1980
- 1980-04-18 HU HU80939A patent/HU181689B/hu not_active IP Right Cessation
1981
- 1981-04-14 DK DK170581A patent/DK170581A/da active IP Right Grant
- 1981-04-15 DE DE8181102906T patent/DE3165346D1/de not_active Expired
- 1981-04-15 EP EP81102906A patent/EP0038528B1/de not_active Expired
- 1981-04-15 AT AT81102906T patent/ATE8893T1/de active
- 1981-04-15 ES ES502078A patent/ES502078A0/es active Granted
- 1981-04-16 AU AU69645/81A patent/AU540758B2/en not_active Ceased
- 1981-04-16 FI FI811193A patent/FI70896C/fi not_active IP Right Cessation
- 1981-04-16 US US06/254,763 patent/US4342766A/en not_active Expired - Lifetime
- 1981-04-16 DD DD81229303A patent/DD158399A5/de unknown
- 1981-04-16 YU YU01009/81A patent/YU100981A/xx unknown
- 1981-04-17 CS CS812952A patent/CS221293B2/cs unknown
- 1981-04-17 SU SU813273760A patent/SU1014475A3/ru active
- 1981-04-17 GR GR64727A patent/GR74516B/el unknown
- 1981-04-17 JP JP5727081A patent/JPS56166190A/ja active Pending

Also Published As

Publication number	Publication date
YU100981A (en)	1983-10-31
ES8203369A1 (es)	1982-04-01
ES502078A0 (es)	1982-04-01
ATE8893T1 (de)	1984-08-15
FI811193L (fi)	1981-10-19
FI70896B (fi)	1986-07-18
FI70896C (fi)	1986-10-27
DE3165346D1 (en)	1984-09-13
DK170581A (da)	1981-10-19
AU540758B2 (en)	1984-12-06
AU6964581A (en)	1981-10-22
SU1014475A3 (ru)	1983-04-23
CS221293B2 (en)	1983-04-29
US4342766A (en)	1982-08-03
HU181689B (en)	1983-11-28
JPS56166190A (en)	1981-12-21
EP0038528A1 (de)	1981-10-28
EP0038528B1 (de)	1984-08-08
GR74516B (cs)	1984-06-29

Publication	Publication Date	Title
DE4338770A1 (de)	1995-05-18	Indol-2-alkansäuren und ihre Derivate als Hemmstoffe der Phospholipase A¶2¶
DD246995A5 (de)	1987-06-24	Verfahren zur herstellung von neuen schwefelhaltigen 5-substituierten benzimidazol-derivaten
EP0764647A1 (de)	1997-03-26	Substituierte Xanthine
DE3685604T2 (de)	1993-01-28	1,7-naphthyridinderivate und diese enthaltende arzneimittel.
EP0116360B1 (de)	1987-07-01	1-Phenyl-2-aminocarbonylindol-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0089028B1 (de)	1988-05-25	Neue Theophyllin-Derivate und Verfahren zu ihrer Herstellung
EP0217372A2 (de)	1987-04-08	Neue polyoxygenierte Labdan-Derivate, Verfahren zu ihrer Herstellung und ihre Anwendung als Medikamente
DD201903A5 (de)	1983-08-17	Verfahren zur herstellung von derivaten des thienopyridonons
EP0201094A2 (de)	1986-12-17	Neue Derivate von Thieno[2,3-d]-imidazolen und Verfahren zu ihrer Herstellung
DE69028355T2 (de)	1997-02-20	4,5-Dihydro-6H-imidazo[4,5,1-ij]chinolin-6-on-6-oxim-O-sulfonsäurederivate
EP0170861B1 (de)	1988-03-09	3-Aminocarbonylmethoxy-5-phenylpyrazol-Verbindungen sowie Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2007345A1 (de)	1970-09-17	Neue substituierte Hexahydroimidazochinoline und deren Säureanlagerungssalze
DE2522314A1 (de)	1975-12-04	In 2-stellung substituierte dimethoxyindazole
DE4039559A1 (de)	1992-06-11	Funktionalisierte vinylazole, verfahren zu deren herstellung, pharmazeutische praeparate die diese vinylazole enthalten sowie deren verwendung zur herstellung von arzneimitteln
DD277071A5 (de)	1990-03-21	Hydrozimtsaeurederivate
CH634848A5 (de)	1983-02-28	Verfahren zur herstellung neuer 7-(n-substituierter 2-phenylglycinamido)-3-substituierte-3-cephem-4-carbonsaeuren.
DE2550163C2 (de)	1984-11-22	Neue Derivate des [1,4]Oxathiino[2,3-c]pyrrols, deren Herstellung und diese enthaltende Zusammensetzungen
AT390615B (de)	1990-06-11	Verfahren zur herstellung von neuen, 3-substituierten 2-oxo-hexahydro-pyrimido (1,2-a)azepinen sowie von deren pharmazeutisch geeigneten salzen
EP0457716A1 (de)	1991-11-21	Naphthalinderivate
EP0038528B1 (de)	1984-08-08	Dihydro-as-triazino(5,6-c)chinolinderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
EP0110298A1 (de)	1984-06-13	Acridanon-Derivate
DE2167258C2 (de)	1986-05-22	s-Triazolyl-benzophenon-Derivate
DE3447730A1 (de)	1985-07-04	Pyrazolopyridinderivate
AT384221B (de)	1987-10-12	Verfahren zur herstellung von neuen 3-substituierten tetrahydro-pyrrolo(1,2-a) pyrimidin-derivaten sowie von deren saeureadditions- und quaternaeren salzen
DE3833615A1 (de)	1989-04-13	As-triazino(2,3-a)chinolinium- beziehungsweise as-triazino(3,2-a)isochinoliniumderivate, verfahren und zwischenprodukte zu ihrer herstellung und die ersteren enthaltende arzneimittel