IE43841B1 - Triazolylbenzophenone derivatives and preparation thereof - Google Patents
Triazolylbenzophenone derivatives and preparation thereofInfo
- Publication number
- IE43841B1 IE43841B1 IE2215/76A IE221576A IE43841B1 IE 43841 B1 IE43841 B1 IE 43841B1 IE 2215/76 A IE2215/76 A IE 2215/76A IE 221576 A IE221576 A IE 221576A IE 43841 B1 IE43841 B1 IE 43841B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- alkyl
- benzophenone
- triazol
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 55
- -1 spasmolytics Substances 0.000 claims abstract description 40
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- 230000000949 anxiolytic effect Effects 0.000 claims abstract description 6
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- 239000000932 sedative agent Substances 0.000 claims abstract description 6
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- 238000000034 method Methods 0.000 claims description 63
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 239000000203 mixture Substances 0.000 claims description 34
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- 239000001257 hydrogen Substances 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 19
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- 239000002253 acid Substances 0.000 claims description 18
- 239000012442 inert solvent Substances 0.000 claims description 15
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 14
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- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
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- 238000009472 formulation Methods 0.000 claims description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 6
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 claims description 5
- 125000005335 azido alkyl group Chemical group 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical group C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims description 4
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- 230000001430 anti-depressive effect Effects 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 238000010792 warming Methods 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 3
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- 230000001939 inductive effect Effects 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
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- 239000000843 powder Substances 0.000 claims description 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 3
- 230000001737 promoting effect Effects 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 230000001624 sedative effect Effects 0.000 claims description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 claims description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 claims description 2
- AUUTXOKCFQTKPL-UHFFFAOYSA-N 2-oxopropanoyl chloride Chemical compound CC(=O)C(Cl)=O AUUTXOKCFQTKPL-UHFFFAOYSA-N 0.000 claims description 2
- 239000005711 Benzoic acid Substances 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 2
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- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims description 2
- 239000007868 Raney catalyst Substances 0.000 claims description 2
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 235000004279 alanine Nutrition 0.000 claims description 2
- 125000000266 alpha-aminoacyl group Chemical group 0.000 claims description 2
- 229960003965 antiepileptics Drugs 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 235000010233 benzoic acid Nutrition 0.000 claims description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 2
- QAWBXZYPFCFQLA-UHFFFAOYSA-N butanoyl bromide Chemical compound CCCC(Br)=O QAWBXZYPFCFQLA-UHFFFAOYSA-N 0.000 claims description 2
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 244000144972 livestock Species 0.000 claims description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 2
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- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 claims description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 7
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
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- 239000007858 starting material Substances 0.000 abstract description 3
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- 125000001424 substituent group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 162
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- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 18
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- RHZBRCQIKQUQHQ-UHFFFAOYSA-N 2-(1,3-dioxoisoindol-2-yl)acetyl chloride Chemical compound C1=CC=C2C(=O)N(CC(=O)Cl)C(=O)C2=C1 RHZBRCQIKQUQHQ-UHFFFAOYSA-N 0.000 description 6
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- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- OIDJYOPWVMATJN-UHFFFAOYSA-N n-[2-(aminomethyl)-4-bromo-6-chloro-4-(2-chlorophenyl)quinazolin-3-yl]acetamide;dihydrate;dihydrobromide Chemical compound O.O.Br.Br.CC(=O)NN1C(CN)=NC2=CC=C(Cl)C=C2C1(Br)C1=CC=CC=C1Cl OIDJYOPWVMATJN-UHFFFAOYSA-N 0.000 description 1
- MHQAHXKEGYRYRS-UHFFFAOYSA-N n-[[3-acetamido-6-chloro-4-(2-chlorophenyl)-4-hydroxyquinazolin-2-yl]methyl]-2-(1,3-dioxoisoindol-2-yl)acetamide Chemical compound CC(=O)NN1C(CNC(=O)CN2C(C3=CC=CC=C3C2=O)=O)=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1Cl MHQAHXKEGYRYRS-UHFFFAOYSA-N 0.000 description 1
- UHYBLUPZCIIYHO-UHFFFAOYSA-N n-[[3-acetamido-6-chloro-4-(2-chlorophenyl)-4-hydroxyquinazolin-2-yl]methyl]-2-chloroacetamide Chemical compound CC(=O)NN1C(CNC(=O)CCl)=NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1Cl UHYBLUPZCIIYHO-UHFFFAOYSA-N 0.000 description 1
- YSGXUVIUTPVEHZ-UHFFFAOYSA-N n-[[4-(2-benzoyl-4-chlorophenyl)-5-(chloromethyl)-1,2,4-triazol-3-yl]methyl]acetamide Chemical compound CC(=O)NCC1=NN=C(CCl)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 YSGXUVIUTPVEHZ-UHFFFAOYSA-N 0.000 description 1
- GTWCKWCSXJWGNQ-UHFFFAOYSA-N n-[[4-[3-chloro-5-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]-2-oxopropanamide Chemical compound CC(=O)C(=O)NCC1=NN=C(C)N1C1=CC(Cl)=CC(C(=O)C=2C(=CC=CC=2)Cl)=C1 GTWCKWCSXJWGNQ-UHFFFAOYSA-N 0.000 description 1
- GNKQIFLHDAOGRN-UHFFFAOYSA-N n-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCC1=NN=C(C)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl GNKQIFLHDAOGRN-UHFFFAOYSA-N 0.000 description 1
- XFIUGDCZXKBLQC-UHFFFAOYSA-N n-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]-2-oxopropanamide Chemical compound CC(=O)C(=O)NCC1=NN=C(C)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl XFIUGDCZXKBLQC-UHFFFAOYSA-N 0.000 description 1
- NOXRREWCNAJHHJ-UHFFFAOYSA-N n-[[4-[4-chloro-2-(2-chlorobenzoyl)phenyl]-5-methyl-1,2,4-triazol-3-yl]methyl]propanamide Chemical compound CCC(=O)NCC1=NN=C(C)N1C1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1Cl NOXRREWCNAJHHJ-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- ZDYUUBIMAGBMPY-UHFFFAOYSA-N oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O ZDYUUBIMAGBMPY-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229960005152 pentetrazol Drugs 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000405 phenylalanyl group Chemical group 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 125000005543 phthalimide group Chemical group 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- FYRHIOVKTDQVFC-UHFFFAOYSA-M potassium phthalimide Chemical compound [K+].C1=CC=C2C(=O)[N-]C(=O)C2=C1 FYRHIOVKTDQVFC-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229940107700 pyruvic acid Drugs 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
- 229940071536 silver acetate Drugs 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000340 thiopental sodium Drugs 0.000 description 1
- AWLILQARPMWUHA-UHFFFAOYSA-M thiopental sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC([S-])=NC1=O AWLILQARPMWUHA-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—Oxygen atoms
- C07D239/92—Oxygen atoms with hetero atoms directly attached to nitrogen atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
- C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06008—Dipeptides with the first amino acid being neutral
- C07K5/06078—Dipeptides with the first amino acid being neutral and aromatic or cycloaliphatic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Anesthesiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB53224/75A GB1531980A (en) | 1975-12-30 | 1975-12-30 | Triazolylbenzophenone derivatives and preparation thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43841L IE43841L (en) | 1977-06-30 |
| IE43841B1 true IE43841B1 (en) | 1981-06-03 |
Family
ID=10467048
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2215/76A IE43841B1 (en) | 1975-12-30 | 1976-10-07 | Triazolylbenzophenone derivatives and preparation thereof |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS5283469A (enExample) |
| AR (2) | AR218613A1 (enExample) |
| AT (1) | AT350052B (enExample) |
| AU (1) | AU498113B2 (enExample) |
| BE (1) | BE846410A (enExample) |
| CA (1) | CA1126274A (enExample) |
| CH (1) | CH623315A5 (enExample) |
| DE (1) | DE2641164A1 (enExample) |
| DK (1) | DK393576A (enExample) |
| ES (3) | ES451896A1 (enExample) |
| FR (1) | FR2336930A1 (enExample) |
| GB (1) | GB1531980A (enExample) |
| HU (1) | HU172539B (enExample) |
| IE (1) | IE43841B1 (enExample) |
| IL (1) | IL50664A (enExample) |
| NL (1) | NL7610799A (enExample) |
| NZ (1) | NZ181958A (enExample) |
| SE (1) | SE7609813L (enExample) |
| ZA (1) | ZA765851B (enExample) |
-
1975
- 1975-12-30 GB GB53224/75A patent/GB1531980A/en not_active Expired
-
1976
- 1976-08-31 DK DK393576A patent/DK393576A/da not_active Application Discontinuation
- 1976-09-02 CA CA260,438A patent/CA1126274A/en not_active Expired
- 1976-09-06 AU AU17498/76A patent/AU498113B2/en not_active Expired
- 1976-09-06 SE SE7609813A patent/SE7609813L/xx not_active Application Discontinuation
- 1976-09-07 NZ NZ181958A patent/NZ181958A/xx unknown
- 1976-09-08 HU HU76SI00001538A patent/HU172539B/hu unknown
- 1976-09-13 DE DE19762641164 patent/DE2641164A1/de not_active Withdrawn
- 1976-09-15 AT AT684276A patent/AT350052B/de not_active IP Right Cessation
- 1976-09-17 AR AR264755A patent/AR218613A1/es active
- 1976-09-21 BE BE170796A patent/BE846410A/xx unknown
- 1976-09-21 CH CH1193976A patent/CH623315A5/de not_active IP Right Cessation
- 1976-09-27 ES ES451896A patent/ES451896A1/es not_active Expired
- 1976-09-29 NL NL7610799A patent/NL7610799A/xx not_active Application Discontinuation
- 1976-09-29 ZA ZA765851A patent/ZA765851B/xx unknown
- 1976-10-06 FR FR7630125A patent/FR2336930A1/fr active Granted
- 1976-10-06 JP JP12081576A patent/JPS5283469A/ja active Pending
- 1976-10-07 IE IE2215/76A patent/IE43841B1/en unknown
- 1976-10-11 IL IL50664A patent/IL50664A/xx unknown
-
1977
- 1977-06-30 AR AR268275A patent/AR220519A1/es active
- 1977-09-09 ES ES462244A patent/ES462244A1/es not_active Expired
- 1977-09-09 ES ES462243A patent/ES462243A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH623315A5 (en) | 1981-05-29 |
| NZ181958A (en) | 1979-03-28 |
| AU1749876A (en) | 1978-03-16 |
| ES462244A1 (es) | 1978-06-01 |
| IL50664A0 (en) | 1976-12-31 |
| GB1531980A (en) | 1978-11-15 |
| SE7609813L (sv) | 1977-07-01 |
| AU498113B2 (en) | 1979-02-08 |
| HU172539B (hu) | 1978-09-28 |
| AR220519A1 (es) | 1980-11-14 |
| ATA684276A (de) | 1978-10-15 |
| FR2336930B1 (enExample) | 1978-12-22 |
| IL50664A (en) | 1983-09-30 |
| DE2641164A1 (de) | 1977-07-14 |
| AT350052B (de) | 1979-05-10 |
| ES462243A1 (es) | 1978-06-01 |
| ES451896A1 (es) | 1978-01-16 |
| FR2336930A1 (fr) | 1977-07-29 |
| DK393576A (da) | 1977-07-01 |
| ZA765851B (en) | 1977-09-28 |
| NL7610799A (nl) | 1977-07-04 |
| BE846410A (fr) | 1977-01-17 |
| IE43841L (en) | 1977-06-30 |
| JPS5283469A (en) | 1977-07-12 |
| CA1126274A (en) | 1982-06-22 |
| AR218613A1 (es) | 1980-06-30 |
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