HU212494B - Process for producing new tetraline derivatives and pharmaceutical compositions containing them as active components - Google Patents
Process for producing new tetraline derivatives and pharmaceutical compositions containing them as active components Download PDFInfo
- Publication number
- HU212494B HU212494B HU9068A HU6890A HU212494B HU 212494 B HU212494 B HU 212494B HU 9068 A HU9068 A HU 9068A HU 6890 A HU6890 A HU 6890A HU 212494 B HU212494 B HU 212494B
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- Prior art keywords
- acid
- formula
- compounds
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- pharmaceutical compositions
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- 238000000034 method Methods 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 3
- 125000005329 tetralinyl group Chemical class C1(CCCC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims 2
- 239000005711 Benzoic acid Substances 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 235000010233 benzoic acid Nutrition 0.000 claims 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 claims 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- 150000007522 mineralic acids Chemical class 0.000 claims 2
- 150000007524 organic acids Chemical class 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 claims 1
- FUPIVZHYVSCYLX-UHFFFAOYSA-N 1,4-dihydronaphthalene Chemical compound C1=CC=C2CC=CCC2=C1 FUPIVZHYVSCYLX-UHFFFAOYSA-N 0.000 claims 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 238000006027 Birch reduction reaction Methods 0.000 claims 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 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 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 239000000654 additive Substances 0.000 claims 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 1
- 235000010323 ascorbic acid Nutrition 0.000 claims 1
- 239000011668 ascorbic acid Substances 0.000 claims 1
- 229960005070 ascorbic acid Drugs 0.000 claims 1
- 229960004365 benzoic acid Drugs 0.000 claims 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 235000015165 citric acid Nutrition 0.000 claims 1
- 150000001991 dicarboxylic acids Chemical class 0.000 claims 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- 235000011087 fumaric acid Nutrition 0.000 claims 1
- 229940093915 gynecological organic acid Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000004310 lactic acid Substances 0.000 claims 1
- 235000014655 lactic acid Nutrition 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 239000001630 malic acid Substances 0.000 claims 1
- 235000011090 malic acid Nutrition 0.000 claims 1
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims 1
- CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 claims 1
- 229910000343 potassium bisulfate Inorganic materials 0.000 claims 1
- 229940107700 pyruvic acid Drugs 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 150000003460 sulfonic acids Chemical class 0.000 claims 1
- 239000011975 tartaric acid Substances 0.000 claims 1
- 235000002906 tartaric acid Nutrition 0.000 claims 1
- 150000003628 tricarboxylic acids Chemical class 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HIDFZUFPYUQYQX-UHFFFAOYSA-N 3-amino-1h-naphthalen-2-one Chemical class C1=CC=C2CC(=O)C(N)=CC2=C1 HIDFZUFPYUQYQX-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical class C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/02—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton
- C07C225/04—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated
- C07C225/08—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings
- C07C225/12—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being saturated and containing rings with doubly-bound oxygen atoms bound to carbon atoms being part of rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/60—Naphthoxazoles; Hydrogenated naphthoxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/01—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms
- C07C205/03—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C205/04—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/28—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton
- C07C205/31—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/20—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/41—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
tartalmazó gyógyszerkészítmények előállítására
| (57) KIVONAT | |
| A találmány tárgya eljárás új (I) általános képletű | valamint enantiomer formáik, keverékeik és gyógyá- |
| vegyületek - ahol | szatilag elfogadható sóik előállítására. |
| Rj és R2 jelentése hidrogén- vagy fluoratom; | Az (I) általános képletű vegyületek immunmodulá- |
| Rg, R7, Rg és R9 jelentése hidrogénatom, 1-6 szénato- | ló és fájdalomcsillapító készítmények hatóanyagaként |
| mos alkilcsoport vagy Rg és R7, R7 és R8 vagy R8 | alkalmazhatók. |
| és Rg a hozzájuk kapcsolódó szénatomokkal együtt egy benzolgyűrűt képeznek -, | |
| I9 | Ra Rí |
| ril | |
| AJ | \ J— NH? |
| ^7 1 *6 | |
| (1) |
HU 212 494 B
A leírás terjedelme: 22 oldal (ezen belül 9 lap ábra)
HU 212 494 Β
A találmány tárgya eljárás új, (I) általános képletű tetralin-származékok, valamint ezeket a vegyületeket hatóanyagként tartalmazó aminopeptid inhibitorként alkalmazható gyógyszerkészítmények előállítására.
A találmány tárgya közelebbről eljárás (I) általános képletű 3-amino-naftaIin-2-on-származékok - ahol a képletben
Rj és R2 jelentése hidrogén- vagy fluoratom;
Re, R7, Rg és Rg jelentése hidrogénatom, 1-6 szénatomos alkilcsoport vagy Re és R7, R7 és Rgvagy R8 és
Rg a hozzájuk kapcsolódó szénatomokkal együtt egy benzolgyűrűt képeznek, valamint enantiomer formáik, keverékeik és gyógyászatilag elfogadható sóik előállítására, melynek során
a) egy (XXIX) képletű vegyületről hidrolízissel vagy hidrogenolízissel lehasítjuk a védőcsoportot, vagy b egy (XXX) képletű vegyületet oxidálunk, majd az aminovédő-csoportot kémiai úton, valamely szokásos védőcsoport-lehasítási módszerrel eltávolítjuk, vagy
c) egy (XVI) vagy (XIX) képletű vegyületet valamely savval, előnyösen visszafolyatási hőmérsékleten reagáltatunk, és kívánt esetben az (I) képletű vegyületet sóvá alakítjuk.
A leírásban és az igénypontokban az „1-6 szén-
Claims (2)
- ágazó láncú molekularészt, előnyösen metil- vagy etilcsoportot jelent. Általában, ha Rg és R7, R7 és Rg vagy Rg és Rg egy további gyűrűt képez, akkor ez előnyösen egy fenantrenon molekularész, különösen az Rg-R7, és az Rg-R9 pozícióban.A „gyógyászatilag elfogadható savaddíciós sók” kifejezés az (I) általános képletű vegyület bármely szerves vagy szervetlen savval képzett, nem toxikus sóját jelenti. E célra megfelelő szervetlen savak például a sósav, hidrogénbromid, kénsav, foszforsav és a savas fémsók, mint például a nátrium-monohidrogén-ortofoszfát és a kálium-hidrogén-szulfát. Szerves savként alkalmazhatunk mono-, di- vagy trikarbonsavakat. Ilyenek például az ecetsav, glikolsav, tejsav, piroszőlősav, malonsav, borostyánkősav, glutársav, fumársav, almasav, borkősav, citromsav, aszkorbinsav, maleinsav, hidroxi-maleinsav, benzoesav, hidroxi-benzoesav, fenil-ecetsav, fahéjsav, szalicilsav, 2-fenoxi-benzoesav és szulfonsavak, mint például metán- és 2 hidroxi-etánszulfonsav. Képezhetünk mono- vagy dikarbonsavas sókat, s ezek lehetnek hidratáltak vagy gyakorlatilag vízmentesek. A találmány szerinti eljárással előállított vegyületek savaddíciós sói általában oldhatók vízben és különböző hidrofil szerves oldószerekben, olvadáspontjuk általában magasabb és kémiailag stabilabbak, mint szabad bázisos formáik.Az enantiomerek racém keverékei a szakmában ismert módszerekkel - például frakcionált kristályosítással, kromatográfiás eljárásokkal vagy királis adalékanyagok alkalmazásával - választhatók szét.Az (I) általános képletű vegyületek találmány szerinti eljárással történő előállítása során egy (XXIX) képletű vegyületről hidrolízissel vagy hidrogenolízissel a védőcsoportokat lehasítjuk, vagy egy (XXX) képletű vegyületet oxidálunk majd a védőcsoportokat lehasítjuk, vagy egy (XVI) képletű vagy (XIX) képletű vegyületet savval kezelünk. A módszer kiválasztása függ a vegyület szubsztituenseinek típusától és számától, a kiindulási anyagok kereskedelmi hozzáférhetőségétől és más hasonló - a szakmában jártasak által jól ismert tényezőktől.Ha Rj, R2, Rg, R7, Rg és Rg jelentése hidrogénatom, akkor naftalinból [(E) képlet] indulunk ki, ezt Birch-féle redukcióval 1,4-dihidronaftalin-származékká [(ΙΠ) képlet] alakítjuk át, majd a kapott vegyületet acetonitrilben m-klór-perbenzoesavval epoxidáljuk, és az így kapott
- 2.3- epoxi-l,2,3,4-tetrahidronaftalint ammónia vizes ol-
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP89400056A EP0381902A1 (en) | 1989-01-09 | 1989-01-09 | Tetralin derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU900068D0 HU900068D0 (en) | 1990-03-28 |
| HUT58271A HUT58271A (en) | 1992-02-28 |
| HU212494B true HU212494B (en) | 1996-07-29 |
Family
ID=8202914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9068A HU212494B (en) | 1989-01-09 | 1990-01-08 | Process for producing new tetraline derivatives and pharmaceutical compositions containing them as active components |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5041673A (hu) |
| EP (2) | EP0381902A1 (hu) |
| JP (1) | JP2761955B2 (hu) |
| KR (1) | KR0177805B1 (hu) |
| CN (1) | CN1022319C (hu) |
| AR (1) | AR247722A1 (hu) |
| AT (1) | ATE94533T1 (hu) |
| AU (1) | AU620676B2 (hu) |
| CA (1) | CA2007261C (hu) |
| DE (1) | DE69003257T2 (hu) |
| DK (1) | DK0378456T3 (hu) |
| ES (1) | ES2060076T3 (hu) |
| FI (1) | FI100799B (hu) |
| HU (1) | HU212494B (hu) |
| IE (1) | IE62997B1 (hu) |
| IL (1) | IL92986A (hu) |
| NO (1) | NO171722C (hu) |
| NZ (1) | NZ232031A (hu) |
| PH (1) | PH27288A (hu) |
| PT (1) | PT92808B (hu) |
| ZA (1) | ZA9034B (hu) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5071875A (en) * | 1989-09-25 | 1991-12-10 | Northwestern University | Substituted 2-amidotetralins as melatonin agonists and antagonists |
| GB9509156D0 (en) | 1995-05-05 | 1995-06-28 | Sandoz Ltd | Organic compounds |
| AU2134900A (en) * | 1998-12-22 | 2000-07-12 | Astra Pharma Inc. | Novel oxo-aminotetralin compounds useful in pain management |
| US6844368B1 (en) | 1998-12-22 | 2005-01-18 | Edward Roberts | Compounds useful in pain management |
| PL207809B1 (pl) | 2003-11-20 | 2011-02-28 | Invento Społka Z Ograniczoną Odpowiedzialnością | Preforma pojemnika z tworzywa sztucznego, zwłaszcza do środków spożywczych |
| CN102631664B (zh) * | 2011-01-28 | 2014-10-01 | 上海来益生物药物研究开发中心有限责任公司 | 3-氨基-2-羟基-4-苯基-缬氨酰-异亮氨酸的应用 |
| CN118812481A (zh) | 2019-08-23 | 2024-10-22 | 持田制药株式会社 | 杂环亚基乙酰胺衍生物的制造方法 |
| WO2021039023A1 (ja) * | 2019-08-23 | 2021-03-04 | 持田製薬株式会社 | ヘテロシクリデンアセトアミド誘導体の製造方法 |
| HUE068289T2 (hu) * | 2019-08-23 | 2024-12-28 | Mochida Pharm Co Ltd | Eljárás heterociklidén-acetamid származékok elõállítására |
| CN112275147B (zh) * | 2020-09-01 | 2021-08-13 | 中国科学院山西煤炭化学研究所 | 一种自聚微孔聚酰亚胺气体分离膜及其制备方法和应用 |
| WO2023154896A2 (en) * | 2022-02-11 | 2023-08-17 | Adarx Pharmaceuticals, Inc. | Trkb ligand conjugated compounds and uses thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4267373A (en) * | 1972-07-03 | 1981-05-12 | E. R. Squibb & Sons, Inc. | 5,6,7,8-Tetrahydronaphthalene hypotensive agents |
| JPS561305B2 (hu) * | 1972-12-18 | 1981-01-13 | ||
| US3993677A (en) * | 1975-11-03 | 1976-11-23 | American Cyanamid Company | 1,2,3,4-Tetrahydro-4-oxo-1-naphthylisocyanate |
| US4049717A (en) * | 1976-05-13 | 1977-09-20 | American Cyanamid Company | Novel 1,2,3,4-tetrahydro-4-oxo-(oxy)-1-naphthylamines and method of preparation thereof |
| US4041070A (en) * | 1976-07-14 | 1977-08-09 | American Cyanamid Company | Tetrahydro-4-imino-1-naphthylureas |
| US4051183A (en) * | 1976-09-02 | 1977-09-27 | American Cyanamid Company | 1-benzoyl-3-(1,2,3,4-tetrahydro-4-oxo-1-naphthyl)-urea, a novel and useful intermediate for the preparation of animal growth promoting agents |
| JPS6045179B2 (ja) * | 1977-06-08 | 1985-10-08 | フナイ薬品工業株式会社 | 新規環状アミノアルコ−ル類およびその製造法 |
-
1989
- 1989-01-09 EP EP89400056A patent/EP0381902A1/en not_active Withdrawn
-
1990
- 1990-01-03 ZA ZA9034A patent/ZA9034B/xx unknown
- 1990-01-04 US US07/460,693 patent/US5041673A/en not_active Expired - Fee Related
- 1990-01-05 DE DE90400031T patent/DE69003257T2/de not_active Expired - Fee Related
- 1990-01-05 ES ES90400031T patent/ES2060076T3/es not_active Expired - Lifetime
- 1990-01-05 NZ NZ232031A patent/NZ232031A/en unknown
- 1990-01-05 AT AT90400031T patent/ATE94533T1/de not_active IP Right Cessation
- 1990-01-05 IL IL9298690A patent/IL92986A/en not_active IP Right Cessation
- 1990-01-05 DK DK90400031.2T patent/DK0378456T3/da active
- 1990-01-05 CA CA002007261A patent/CA2007261C/en not_active Expired - Fee Related
- 1990-01-05 EP EP90400031A patent/EP0378456B1/en not_active Expired - Lifetime
- 1990-01-08 NO NO900074A patent/NO171722C/no unknown
- 1990-01-08 AR AR90315899A patent/AR247722A1/es active
- 1990-01-08 HU HU9068A patent/HU212494B/hu not_active IP Right Cessation
- 1990-01-08 IE IE6790A patent/IE62997B1/en not_active IP Right Cessation
- 1990-01-08 FI FI900083A patent/FI100799B/fi not_active IP Right Cessation
- 1990-01-08 KR KR1019900000190A patent/KR0177805B1/ko not_active Expired - Fee Related
- 1990-01-08 PT PT92808A patent/PT92808B/pt not_active IP Right Cessation
- 1990-01-09 PH PH39864A patent/PH27288A/en unknown
- 1990-01-09 JP JP2001124A patent/JP2761955B2/ja not_active Expired - Lifetime
- 1990-01-09 AU AU47827/90A patent/AU620676B2/en not_active Ceased
- 1990-01-09 CN CN90100092A patent/CN1022319C/zh not_active Expired - Fee Related
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