FI70896C - Foerfarande foer framstaellning av terapeutiskt anvaendbara diydro-as-triazino/5,6-c/kinolinderivat - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara diydro-as-triazino/5,6-c/kinolinderivat Download PDFInfo
- Publication number
- FI70896C FI70896C FI811193A FI811193A FI70896C FI 70896 C FI70896 C FI 70896C FI 811193 A FI811193 A FI 811193A FI 811193 A FI811193 A FI 811193A FI 70896 C FI70896 C FI 70896C
- Authority
- FI
- Finland
- Prior art keywords
- triazino
- dihydro
- quinoline
- acid addition
- general formula
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 239000002253 acid Substances 0.000 claims abstract description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 6
- -1 diacetyl compound Chemical class 0.000 claims description 5
- 125000002943 quinolinyl group Chemical class N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 5
- 150000002431 hydrogen Chemical group 0.000 abstract description 4
- 150000007522 mineralic acids Chemical class 0.000 abstract description 2
- 150000007524 organic acids Chemical class 0.000 abstract description 2
- 235000005985 organic acids Nutrition 0.000 abstract description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 4
- 230000021736 acetylation Effects 0.000 abstract 3
- 238000006640 acetylation reaction Methods 0.000 abstract 3
- 239000000126 substance Substances 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 51
- 150000001875 compounds Chemical class 0.000 description 38
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 26
- 241001465754 Metazoa Species 0.000 description 13
- 238000012360 testing method Methods 0.000 description 12
- 230000003110 anti-inflammatory effect Effects 0.000 description 9
- 231100001274 therapeutic index Toxicity 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- IRYJRGCIQBGHIV-UHFFFAOYSA-N trimethadione Chemical compound CN1C(=O)OC(C)(C)C1=O IRYJRGCIQBGHIV-UHFFFAOYSA-N 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 229960004453 trimethadione Drugs 0.000 description 6
- 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 5
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000000202 analgesic effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical group O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229960005333 tetrabenazine Drugs 0.000 description 5
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical group NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 4
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 4
- 208000005392 Spasm Diseases 0.000 description 4
- 230000003444 anaesthetic effect Effects 0.000 description 4
- 230000001773 anti-convulsant effect Effects 0.000 description 4
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 4
- 230000005764 inhibitory process Effects 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003248 quinolines Chemical class 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 3
- 229960000836 amitriptyline Drugs 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 210000003141 lower extremity Anatomy 0.000 description 3
- 229960004815 meprobamate Drugs 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229960005489 paracetamol Drugs 0.000 description 3
- 229940127557 pharmaceutical product Drugs 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 2
- 239000000679 carrageenan Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229940113118 carrageenan Drugs 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 235000010356 sorbitol Nutrition 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 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
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 2
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 1
- UPCDRADNFUWGIY-UHFFFAOYSA-N 5-methylidenetetrazole Chemical compound C=C1N=NN=N1 UPCDRADNFUWGIY-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 230000002082 anti-convulsion Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 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
- 229910052799 carbon Inorganic materials 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 210000000744 eyelid Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004054 inflammatory process 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
- 239000008101 lactose Substances 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
- 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
- 238000002156 mixing Methods 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
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000004622 sleep time Effects 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 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
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- 239000003981 vehicle Substances 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU93980 | 1980-04-18 | ||
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| FI811193L FI811193L (fi) | 1981-10-19 |
| FI70896B FI70896B (fi) | 1986-07-18 |
| FI70896C true FI70896C (fi) | 1986-10-27 |
Family
ID=10952123
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI811193A FI70896C (fi) | 1980-04-18 | 1981-04-16 | Foerfarande foer framstaellning av terapeutiskt anvaendbara diydro-as-triazino/5,6-c/kinolinderivat |
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)
| 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 |
| HU165677B (cs) * | 1972-05-05 | 1974-10-28 | ||
| HU165678B (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 ES ES502078A patent/ES502078A0/es active Granted
- 1981-04-15 EP EP81102906A patent/EP0038528B1/de not_active Expired
- 1981-04-15 AT AT81102906T patent/ATE8893T1/de active
- 1981-04-15 DE DE8181102906T patent/DE3165346D1/de not_active Expired
- 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
- 1981-04-16 AU AU69645/81A patent/AU540758B2/en not_active Ceased
- 1981-04-17 JP JP5727081A patent/JPS56166190A/ja active Pending
- 1981-04-17 GR GR64727A patent/GR74516B/el unknown
- 1981-04-17 SU SU813273760A patent/SU1014475A3/ru active
- 1981-04-17 CS CS812952A patent/CS221293B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI70896B (fi) | 1986-07-18 |
| GR74516B (cs) | 1984-06-29 |
| EP0038528B1 (de) | 1984-08-08 |
| JPS56166190A (en) | 1981-12-21 |
| YU100981A (en) | 1983-10-31 |
| DD158399A5 (de) | 1983-01-12 |
| US4342766A (en) | 1982-08-03 |
| ES8203369A1 (es) | 1982-04-01 |
| AU6964581A (en) | 1981-10-22 |
| ES502078A0 (es) | 1982-04-01 |
| DK170581A (da) | 1981-10-19 |
| AU540758B2 (en) | 1984-12-06 |
| EP0038528A1 (de) | 1981-10-28 |
| SU1014475A3 (ru) | 1983-04-23 |
| FI811193L (fi) | 1981-10-19 |
| ATE8893T1 (de) | 1984-08-15 |
| DE3165346D1 (en) | 1984-09-13 |
| CS221293B2 (en) | 1983-04-29 |
| HU181689B (en) | 1983-11-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4404206A (en) | Substituted iminoacid derivatives, process for preparing them and their use as enzyme inhibitors | |
| JP5199079B2 (ja) | アンドロゲン受容体モジュレーター化合物および方法 | |
| US20080234287A1 (en) | Sulfur-containing naphthalimide derivatives | |
| WO2007005887A2 (en) | Androgen receptor modulator compounds, compositions and uses thereof | |
| BR112021014079A2 (pt) | Ácidos carboxílicos policíclicos substituídos, análogos dos mesmos e métodos usando os mesmos | |
| DE69215965T2 (de) | Pyrazolopyridinverbindungen und Verfahren zu ihrer Herstellung | |
| JPS6049192B2 (ja) | 新規置換ベンズアミド、その製造方法及びこれを有効成分とする向精神薬 | |
| JPH09505030A (ja) | ヒドロイソキノリン誘導体 | |
| EP0232328A1 (en) | AMPHOTERIC BICYCLIC COMPOUNDS AND THEIR SALTS, SOLVATES, HYDRATES AND ESTERS. | |
| IE56520B1 (en) | Disubstituted proline derivatives,a process for their preparation and their use | |
| US5527910A (en) | Pyridone carboxylic acid compounds and their uses for treating infectious diseases caused by bacteria | |
| US5342960A (en) | Azomethines agonist compounds of the histamine H3 receptor for therapeutic use, pharmaceutical compositions acting as agonists of the said receptor and preparation process | |
| US6723736B2 (en) | Tricyclic compounds and uses thereof | |
| SK61793A3 (en) | New 3,4-dihydroisoquinoline derivatives and new pharmaceutical use of carbocyclically and heterocyclically annulated dihydropyridines | |
| FI70896C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara diydro-as-triazino/5,6-c/kinolinderivat | |
| WO1994011375A1 (fr) | Compose tricyclique | |
| EP0700914A1 (en) | Camptothecin derivatives, preparations thereof and antitumor agents | |
| KR0163186B1 (ko) | (1,2,3,4-테트라하이드로-9-아크리딘이미노)사이클로헥산 카복실산 및 관련 화합물, 이들의 제조방법 및 약제로서의 용도 | |
| DK171299B1 (da) | 4-Amino-6,7-dimethoxy-2-(1,2,3,4-tetrahydroisoquinolin-2-yl)quinolin-forbindelser, farmaceutiske præparater indeholdende disse og deres anvendelse til fremstilling af antiarytmiske lægemidler | |
| US4511569A (en) | Tricyclic lactams and derivatives useful in increasing cardiac contractility | |
| EP0736526B1 (en) | Pyrazolidine derivative, radical scavenger, brain-infarction depressant, and brain-edema depressant | |
| FI60863B (fi) | Foerfarande foer framstaellning av nya bentshydryloxialkylaminderivat med foerlaengd antihistamineffekt | |
| US4994448A (en) | Condensed quinolinium and isoquinolinium derivatives | |
| KR0150218B1 (ko) | 오르가노실란 유도체, 이를 함유하는 약제학적 조성물 및 이의 제조방법 | |
| FI58119C (fi) | Foerfarande foer framstaellning av dibensylglykolsyraderivat med terapeutisk verkan |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: E GY T GYOGYSZERVEGYESZETI GYOER |