HU183048B - Process for producing bracket-2s,3r-bracket closed-, bracket-2s,3s-bracket closed-, bracket-2rs,3r-bracket closed- or bracket-2rs,3rs-bracket closed-3-amino-2-hydroxy-propionyl-glycine derivatives - Google Patents
Process for producing bracket-2s,3r-bracket closed-, bracket-2s,3s-bracket closed-, bracket-2rs,3r-bracket closed- or bracket-2rs,3rs-bracket closed-3-amino-2-hydroxy-propionyl-glycine derivatives Download PDFInfo
- Publication number
- HU183048B HU183048B HU76ZA395A HUZA000395A HU183048B HU 183048 B HU183048 B HU 183048B HU 76ZA395 A HU76ZA395 A HU 76ZA395A HU ZA000395 A HUZA000395 A HU ZA000395A HU 183048 B HU183048 B HU 183048B
- Authority
- HU
- Hungary
- Prior art keywords
- priority
- compound
- bracket
- formula
- tetrahydroquinazolinone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- 239000011593 sulfur Substances 0.000 claims description 15
- 229910052717 sulfur Inorganic materials 0.000 claims description 15
- -1 tetrahydroquinazolinone compound Chemical class 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 150000002736 metal compounds Chemical class 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- ZWOUXWWGKJBAHQ-UHFFFAOYSA-N fluproquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=C(F)C=C1 ZWOUXWWGKJBAHQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- JTIGKVIOEQASGT-UHFFFAOYSA-N proquazone Chemical compound N=1C(=O)N(C(C)C)C2=CC(C)=CC=C2C=1C1=CC=CC=C1 JTIGKVIOEQASGT-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 229910052742 iron Inorganic materials 0.000 claims description 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 239000011133 lead Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 4
- TYNNEEKKMHSZMO-UHFFFAOYSA-N 3,4,4a,5-tetrahydro-1h-quinazolin-2-one Chemical compound C1C=CC=C2NC(=O)NCC21 TYNNEEKKMHSZMO-UHFFFAOYSA-N 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- LIKBJVNGSGBSGK-UHFFFAOYSA-N iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Fe+3].[Fe+3] LIKBJVNGSGBSGK-UHFFFAOYSA-N 0.000 claims 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 abstract description 4
- 108010006654 Bleomycin Proteins 0.000 abstract 2
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 abstract 2
- SERHXTVXHNVDKA-UHFFFAOYSA-N pantolactone Chemical compound CC1(C)COC(=O)C1O SERHXTVXHNVDKA-UHFFFAOYSA-N 0.000 abstract 2
- VGGGPCQERPFHOB-MCIONIFRSA-N Bestatin Chemical class CC(C)C[C@H](C(O)=O)NC(=O)[C@@H](O)[C@H](N)CC1=CC=CC=C1 VGGGPCQERPFHOB-MCIONIFRSA-N 0.000 abstract 1
- 102000004190 Enzymes Human genes 0.000 abstract 1
- 108090000790 Enzymes Proteins 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 150000001576 beta-amino acids Chemical class 0.000 abstract 1
- 229960001561 bleomycin Drugs 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 125000000524 functional group Chemical group 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000010410 layer Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 239000011787 zinc oxide Substances 0.000 description 3
- BNHGVULTSGNVIX-UHFFFAOYSA-N 1-(2-ethoxyethoxy)ethanol Chemical compound CCOCCOC(C)O BNHGVULTSGNVIX-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NOJAJMMKDHHEGC-UHFFFAOYSA-N 4-(4-fluorophenyl)-7-methyl-1-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C=2CC(C)CCC=2C=1C1=CC=C(F)C=C1 NOJAJMMKDHHEGC-UHFFFAOYSA-N 0.000 description 1
- YKFXBRUJMZNBAN-UHFFFAOYSA-N 7-methyl-4-phenyl-1-propan-2-yl-5,6,7,8-tetrahydroquinazolin-2-one Chemical compound N=1C(=O)N(C(C)C)C=2CC(C)CCC=2C=1C1=CC=CC=C1 YKFXBRUJMZNBAN-UHFFFAOYSA-N 0.000 description 1
- NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical class C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 1
- CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229910052976 metal sulfide Inorganic materials 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- 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
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB30632/75A GB1510477A (en) | 1975-07-22 | 1975-07-22 | Peptides and to amino acid intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU183048B true HU183048B (en) | 1984-04-28 |
Family
ID=10310676
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU76ZA395A HU183048B (en) | 1975-07-22 | 1976-07-22 | Process for producing bracket-2s,3r-bracket closed-, bracket-2s,3s-bracket closed-, bracket-2rs,3r-bracket closed- or bracket-2rs,3rs-bracket closed-3-amino-2-hydroxy-propionyl-glycine derivatives |
Country Status (12)
| Country | Link |
|---|---|
| JP (2) | JPS52136118A (cs) |
| AU (1) | AU506003B2 (cs) |
| CA (1) | CA1104156A (cs) |
| CH (1) | CH630892A5 (cs) |
| CS (2) | CS201034B2 (cs) |
| DE (2) | DE2632396C2 (cs) |
| DK (1) | DK149110C (cs) |
| FR (1) | FR2318863A1 (cs) |
| GB (1) | GB1510477A (cs) |
| HU (1) | HU183048B (cs) |
| NL (1) | NL7608064A (cs) |
| SE (3) | SE431642B (cs) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2725732C2 (de) | 1977-06-07 | 1983-01-05 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai, Tokyo | Bestatin-Analoga, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Präparate |
| DE2760007C2 (cs) * | 1977-06-07 | 1988-10-06 | Microbial Chem Res Found | |
| JPS6026099B2 (ja) * | 1977-09-21 | 1985-06-21 | 財団法人微生物化学研究会 | ペプチド、その酸附加塩およびその製造法 |
| DE2954076C2 (cs) * | 1978-11-25 | 1988-02-25 | Nippon Kayaku K.K., Tokio/Tokyo, Jp | |
| US4370318A (en) * | 1980-07-07 | 1983-01-25 | Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai | Bestatin-related compounds as immunopotentiator |
| JPS5767516A (en) * | 1980-09-24 | 1982-04-24 | Microbial Chem Res Found | Novel analgesic agent |
| JPH0810855Y2 (ja) * | 1989-07-20 | 1996-03-29 | タナシン電機株式会社 | オートリバース式テープレコーダ |
| DE69420524T2 (de) * | 1993-06-29 | 2000-02-17 | Kaneka Corp., Osaka | Verfahren zur herstellung von derivaten von 3-amin-2-hydroxy-4-phenylbuttersäure und 1-nitro-4-phenyl-2-butanol zwischenprodukte |
| CA2236117C (en) * | 1996-02-08 | 2004-11-16 | Nippon Kayaku Kabushiki Kaisha | Process for producing optically active cyanohydrins |
| BR9910092A (pt) * | 1998-05-01 | 2002-01-22 | Abbott Lab | Inibidores de beta-aminoácido substituìdo de metionina aminopeptidase-2 |
| US6242494B1 (en) | 1998-05-01 | 2001-06-05 | Abbott Laboratories | Substituted β-amino acid inhibitors of methionine aminopeptidase-2 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5439477B2 (cs) * | 1974-07-01 | 1979-11-28 |
-
1975
- 1975-07-22 GB GB30632/75A patent/GB1510477A/en not_active Expired
-
1976
- 1976-06-14 SE SE7606736A patent/SE431642B/xx not_active IP Right Cessation
- 1976-07-15 AU AU15912/76A patent/AU506003B2/en not_active Expired
- 1976-07-16 CS CS793519A patent/CS201034B2/cs unknown
- 1976-07-16 CS CS764736A patent/CS201033B2/cs unknown
- 1976-07-19 DE DE2632396A patent/DE2632396C2/de not_active Expired
- 1976-07-19 DE DE2660626A patent/DE2660626C2/de not_active Expired
- 1976-07-20 CA CA257,393A patent/CA1104156A/en not_active Expired
- 1976-07-21 FR FR7622279A patent/FR2318863A1/fr active Granted
- 1976-07-21 CH CH933676A patent/CH630892A5/de not_active IP Right Cessation
- 1976-07-21 NL NL7608064A patent/NL7608064A/xx not_active Application Discontinuation
- 1976-07-21 JP JP8599276A patent/JPS52136118A/ja active Granted
- 1976-07-22 HU HU76ZA395A patent/HU183048B/hu unknown
- 1976-07-22 DK DK331276A patent/DK149110C/da not_active IP Right Cessation
-
1980
- 1980-03-13 SE SE8001959A patent/SE452318B/sv unknown
-
1982
- 1982-04-22 JP JP57066233A patent/JPS6050780B2/ja not_active Expired
-
1983
- 1983-11-09 SE SE8306145A patent/SE8306145L/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2632396A1 (de) | 1977-02-03 |
| DE2632396C2 (de) | 1982-11-25 |
| DK149110B (da) | 1986-01-27 |
| GB1510477A (en) | 1978-05-10 |
| CS201033B2 (en) | 1980-10-31 |
| AU506003B2 (en) | 1979-12-13 |
| SE452318B (sv) | 1987-11-23 |
| CH630892A5 (en) | 1982-07-15 |
| FR2318863B1 (cs) | 1980-10-31 |
| SE8306145D0 (sv) | 1983-11-09 |
| SE8306145L (sv) | 1983-11-09 |
| CA1104156A (en) | 1981-06-30 |
| FR2318863A1 (fr) | 1977-02-18 |
| DK331276A (da) | 1977-01-23 |
| JPS5758338B2 (cs) | 1982-12-09 |
| CS201034B2 (en) | 1980-10-31 |
| SE8001959L (sv) | 1980-03-13 |
| JPS5823654A (ja) | 1983-02-12 |
| JPS52136118A (en) | 1977-11-14 |
| DE2660626C2 (de) | 1985-07-11 |
| SE7606736L (sv) | 1977-01-23 |
| DK149110C (da) | 1986-09-08 |
| AU1591276A (en) | 1978-01-19 |
| JPS6050780B2 (ja) | 1985-11-11 |
| SE431642B (sv) | 1984-02-20 |
| NL7608064A (nl) | 1977-01-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU183048B (en) | Process for producing bracket-2s,3r-bracket closed-, bracket-2s,3s-bracket closed-, bracket-2rs,3r-bracket closed- or bracket-2rs,3rs-bracket closed-3-amino-2-hydroxy-propionyl-glycine derivatives | |
| US4202974A (en) | Process for preparing 3,4-dihydro-2(1H)-quinazolinone derivatives | |
| NO843909L (no) | Substituerte 2(1h)-kinazolinon-1-alkansyrer og -estere samt fremgangsmaate for deres fremstilling | |
| HU183018B (en) | Process for producing 4-aryl-quinazolin-2-bracket-1h-bracket closed-ones | |
| US4555571A (en) | Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters | |
| Khan et al. | Synthesis of 5H [l] benzopyrano [3, 4‐b] pyridin‐5‐one and its derivatives | |
| SU474985A3 (ru) | Способ получени 1-алкил-4-фенил-2(1н)хиназолинонов | |
| RU1838309C (ru) | Способ получени производных хиназолина или их формацевтически приемлемых кислотно-аддитивных солей | |
| KR100249637B1 (ko) | 신규플루오르-3-퀴놀린카르복시산 유도체 및 그의 제조방법 | |
| Elgemeie et al. | Activated nitriles in heterocyclic synthesis: A novel synthetic route to furyl-and thienyl-substituted pyridine derivatives | |
| KR100237142B1 (ko) | 벤조[b] 나프티리딘 제조방법 | |
| US4617392A (en) | 4-alkyl-5,6-methylenedioxy-2-1[H]-quinazolinones useful as cardiotonic agents | |
| NO853751L (no) | Fremgangsm¨te for fremstilling av 8-halogen-5,6-dialkoksyk inazolin-2,4-dioner og deres salter. | |
| CA1091229A (en) | Production of 4-phenyl-2(1h)-quinazolinones | |
| US4277607A (en) | Process for the preparation of 4-chloroquinolines | |
| US3316269A (en) | 2-pyridyl-2, 3-dihydro-4(1h)-quinazo-linones and derivatives thereof | |
| US4171441A (en) | Preparation of quinazolin-2(1H)-ones | |
| KR890004558B1 (ko) | 4-아미노-6,7-디 메톡시 퀴나졸린 유도체의 제조방법 | |
| Moriyama et al. | Synthesis of 8‐methylpyrido [2, 3‐d: 6, 5‐d'x] dipyrimidine‐2, 4, 6 (3H, 10H, 7H)‐triones and their use in the oxidation of alcohols | |
| US5223622A (en) | Quinazolin-2-ones | |
| US4731480A (en) | Process for preparing 2-acyl-3,4-dialkoxyanilines | |
| DK141502B (da) | Fremgangsmåde til fremstilling af en 7-acylamido-3-methyl-3-cephem-4-carboxylsyreester. | |
| US4804756A (en) | Process for preparing 5,6-dialkoxy-4-alkyl-2(1H)-quinazolinones | |
| DE2335760A1 (de) | 1,4-dihydro-4-oxo-chinolincarbonsaeure-derivate, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneipraeparate | |
| KR820001716B1 (ko) | 4-아릴-퀴나졸린-2(1h)-온류의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 |