SK21993A3 - (r)-4-nitro-alfa-methyl-benzenemethanamine salts - Google Patents
(r)-4-nitro-alfa-methyl-benzenemethanamine salts Download PDFInfo
- Publication number
- SK21993A3 SK21993A3 SK21993A SK21993A SK21993A3 SK 21993 A3 SK21993 A3 SK 21993A3 SK 21993 A SK21993 A SK 21993A SK 21993 A SK21993 A SK 21993A SK 21993 A3 SK21993 A3 SK 21993A3
- Authority
- SK
- Slovakia
- Prior art keywords
- carbon atoms
- salt
- alkyl
- alpha
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims abstract description 46
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- -1 10-undecynyloxy, 11-dodecynyl Chemical group 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims abstract description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- RAEVOBPXEHVUFY-ZCFIWIBFSA-N 22038-87-5 Chemical class C[C@@H](N)C1=CC=C([N+]([O-])=O)C=C1 RAEVOBPXEHVUFY-ZCFIWIBFSA-N 0.000 claims description 10
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- QTZPRMCKSZATQD-DEOSSOPVSA-N (3s)-3-(2-carboxyethylsulfanyl)-3-[2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC(=O)CCS[C@@H](CC(O)=O)C1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 QTZPRMCKSZATQD-DEOSSOPVSA-N 0.000 claims description 3
- SQMPIRKQQGDPQX-JOCHJYFZSA-N 3-[(r)-carboxy-(2-dodecylphenyl)methyl]sulfanylpropanoic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[C@@H](SCCC(O)=O)C(O)=O SQMPIRKQQGDPQX-JOCHJYFZSA-N 0.000 claims description 3
- BYOIQSZYXCRWNY-XMMPIXPASA-N 3-[(r)-carboxy-[2-(8-phenyloctyl)phenyl]methyl]sulfanylpropanoic acid Chemical compound OC(=O)CCS[C@@H](C(O)=O)C1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 BYOIQSZYXCRWNY-XMMPIXPASA-N 0.000 claims description 3
- 101100440696 Caenorhabditis elegans cor-1 gene Proteins 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 150000002617 leukotrienes Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000002071 phenylalkoxy group Chemical group 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- VLLVTLIDDQVAMQ-QFIPXVFZSA-N (3s)-3-(2-carboxyethylsulfanyl)-3-(2-dodecylphenyl)propanoic acid Chemical compound CCCCCCCCCCCCC1=CC=CC=C1[C@H](CC(O)=O)SCCC(O)=O VLLVTLIDDQVAMQ-QFIPXVFZSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 230000003042 antagnostic effect Effects 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 229910052796 boron Inorganic materials 0.000 claims 2
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 claims 1
- APBLOMTYFBATOG-UHFFFAOYSA-N OC(C(=O)O)CC1=C(C=CC=C1)CCCCCCCCC1=CC=CC=C1 Chemical compound OC(C(=O)O)CC1=C(C=CC=C1)CCCCCCCCC1=CC=CC=C1 APBLOMTYFBATOG-UHFFFAOYSA-N 0.000 claims 1
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 125000004001 thioalkyl group Chemical group 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 3
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 239000003199 leukotriene receptor blocking agent Substances 0.000 abstract 1
- 125000001400 nonyl 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])C([H])([H])[H] 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000004296 chiral HPLC Methods 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 230000008602 contraction Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WNAHEVXTGAEKIY-ZDUSSCGKSA-N tert-butyl n-[(2r)-1-phenylbut-3-en-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@@H](C=C)CC1=CC=CC=C1 WNAHEVXTGAEKIY-ZDUSSCGKSA-N 0.000 description 2
- 238000000825 ultraviolet detection Methods 0.000 description 2
- HLCLTOJXMUXWQW-ZCFIWIBFSA-N (1r)-1-(4-iodophenyl)ethanamine Chemical compound C[C@@H](N)C1=CC=C(I)C=C1 HLCLTOJXMUXWQW-ZCFIWIBFSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 description 1
- QTZPRMCKSZATQD-UHFFFAOYSA-N 3-(2-carboxyethylsulfanyl)-3-[2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC(=O)CCSC(CC(O)=O)C1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 QTZPRMCKSZATQD-UHFFFAOYSA-N 0.000 description 1
- YDQKVWHMLNHSII-UHFFFAOYSA-N 3-[2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC=C1CCCCCCCCC1=CC=CC=C1 YDQKVWHMLNHSII-UHFFFAOYSA-N 0.000 description 1
- QNSOTAZGCLSTMN-UHFFFAOYSA-N 3-[3-hydroxy-2-(8-phenyloctyl)phenyl]propanoic acid Chemical compound OC=1C(=C(C=CC1)CCC(=O)O)CCCCCCCCC1=CC=CC=C1 QNSOTAZGCLSTMN-UHFFFAOYSA-N 0.000 description 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 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 241001227713 Chiron Species 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 238000006217 Nerdel homologation reaction Methods 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000000172 allergic effect Effects 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 210000003651 basophil Anatomy 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229960001340 histamine Drugs 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 231100000245 skin permeability Toxicity 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/56—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- 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
- A61P37/08—Antiallergic agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58612490A | 1990-09-21 | 1990-09-21 | |
| PCT/US1991/006862 WO1992005151A1 (en) | 1990-09-21 | 1991-09-20 | Crystallization of optical isomers of leukotriene antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK21993A3 true SK21993A3 (en) | 1993-10-06 |
Family
ID=24344408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK21993A SK21993A3 (en) | 1990-09-21 | 1991-09-20 | (r)-4-nitro-alfa-methyl-benzenemethanamine salts |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US5288900A (xx) |
| EP (1) | EP0552254A1 (xx) |
| JP (1) | JPH06501269A (xx) |
| KR (1) | KR930702284A (xx) |
| CN (1) | CN1060653A (xx) |
| AU (1) | AU662299B2 (xx) |
| CA (1) | CA2091245A1 (xx) |
| CZ (1) | CZ45193A3 (xx) |
| IE (1) | IE913308A1 (xx) |
| IL (1) | IL99578A0 (xx) |
| MX (1) | MX9101206A (xx) |
| MY (1) | MY131049A (xx) |
| NZ (1) | NZ239875A (xx) |
| PL (1) | PL296247A1 (xx) |
| PT (1) | PT99021A (xx) |
| SK (1) | SK21993A3 (xx) |
| TW (1) | TW221805B (xx) |
| WO (1) | WO1992005151A1 (xx) |
| YU (1) | YU157091A (xx) |
| ZA (1) | ZA917560B (xx) |
| ZW (1) | ZW13191A1 (xx) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10336185A1 (de) * | 2003-08-07 | 2005-02-24 | Bayer Chemicals Ag | Enantiomerenangereicherte 1-Phenylethylamine |
| AU2006207461A1 (en) * | 2005-01-24 | 2006-07-27 | Cinvention Ag | Metal containing composite materials |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4874792A (en) * | 1985-04-19 | 1989-10-17 | Smithkline Beckman Corporation | Thiophenyl Alkanoic acids useful as leukotriene antagonists |
| US4937253A (en) * | 1985-04-19 | 1990-06-26 | Smithkline Beecham Corporation | Ester prodrugs |
| US4845272A (en) * | 1987-07-10 | 1989-07-04 | Kuraray Co., Ltd. | Process for the optical resolution of (±)-cis or (±)-trans-permethric acid |
| AU610528B2 (en) * | 1987-10-29 | 1991-05-23 | Smithkline Beckman Corporation | Leukotriene antagonists |
| IT1217988B (it) * | 1988-01-28 | 1990-03-30 | Ind Chimica Profarmaco Spa | Procedimento per la risoluzione ottica di un pacemo |
| US4904822A (en) * | 1988-02-19 | 1990-02-27 | Kuraray Co., Ltd. | Process for the optical resolution of (+)-2-hydroxy-4-phenylbutanoic acid |
| IT1226300B (it) * | 1988-07-26 | 1990-12-27 | Zambon Spa | Processo per la preparazione di intermedi per la sintesi del diltiazem. |
| EP0365189B1 (en) * | 1988-10-21 | 1995-06-14 | Kabushiki Kaisha Kosmek | Quick-acting coupling |
-
1991
- 1991-09-20 AU AU87675/91A patent/AU662299B2/en not_active Ceased
- 1991-09-20 EP EP91918951A patent/EP0552254A1/en not_active Withdrawn
- 1991-09-20 US US08/030,076 patent/US5288900A/en not_active Expired - Fee Related
- 1991-09-20 CZ CS93451A patent/CZ45193A3/cs unknown
- 1991-09-20 ZW ZW131/91A patent/ZW13191A1/xx unknown
- 1991-09-20 CA CA002091245A patent/CA2091245A1/en not_active Abandoned
- 1991-09-20 IE IE330891A patent/IE913308A1/en unknown
- 1991-09-20 SK SK21993A patent/SK21993A3/sk unknown
- 1991-09-20 JP JP3517260A patent/JPH06501269A/ja active Pending
- 1991-09-20 PL PL29624791A patent/PL296247A1/xx unknown
- 1991-09-20 WO PCT/US1991/006862 patent/WO1992005151A1/en not_active Application Discontinuation
- 1991-09-20 MX MX9101206A patent/MX9101206A/es not_active IP Right Cessation
- 1991-09-20 PT PT99021A patent/PT99021A/pt not_active Application Discontinuation
- 1991-09-20 NZ NZ239875A patent/NZ239875A/en unknown
- 1991-09-21 CN CN91108031A patent/CN1060653A/zh active Pending
- 1991-09-21 MY MYPI91001722A patent/MY131049A/en unknown
- 1991-09-23 ZA ZA917560A patent/ZA917560B/xx unknown
- 1991-09-23 YU YU157091A patent/YU157091A/sh unknown
- 1991-09-26 IL IL99578A patent/IL99578A0/xx unknown
- 1991-10-22 TW TW080108332A patent/TW221805B/zh active
-
1993
- 1993-03-17 KR KR1019930700813A patent/KR930702284A/ko not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO1992005151A1 (en) | 1992-04-02 |
| CZ45193A3 (en) | 1994-02-16 |
| IL99578A0 (en) | 1992-08-18 |
| PT99021A (pt) | 1992-12-31 |
| AU662299B2 (en) | 1995-08-31 |
| EP0552254A1 (en) | 1993-07-28 |
| ZA917560B (en) | 1992-09-30 |
| JPH06501269A (ja) | 1994-02-10 |
| TW221805B (xx) | 1994-03-21 |
| NZ239875A (en) | 1994-06-27 |
| US5288900A (en) | 1994-02-22 |
| CA2091245A1 (en) | 1992-03-22 |
| PL296247A1 (en) | 1993-09-06 |
| KR930702284A (ko) | 1993-09-08 |
| MY131049A (en) | 2007-07-31 |
| YU157091A (sh) | 1994-01-20 |
| AU8767591A (en) | 1992-04-15 |
| ZW13191A1 (en) | 1992-02-05 |
| IE913308A1 (en) | 1992-02-25 |
| CN1060653A (zh) | 1992-04-29 |
| MX9101206A (es) | 1992-05-04 |
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