IE46932B1 - -halomethyl amino acids - Google Patents
-halomethyl amino acidsInfo
- Publication number
- IE46932B1 IE46932B1 IE1167/78A IE116778A IE46932B1 IE 46932 B1 IE46932 B1 IE 46932B1 IE 1167/78 A IE1167/78 A IE 1167/78A IE 116778 A IE116778 A IE 116778A IE 46932 B1 IE46932 B1 IE 46932B1
- Authority
- IE
- Ireland
- Prior art keywords
- och
- hydrogen
- carbon atoms
- compound
- acid
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 57
- 239000001257 hydrogen Substances 0.000 claims abstract description 51
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 51
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 40
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 10
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims abstract description 6
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 22
- 235000019260 propionic acid Nutrition 0.000 claims description 20
- 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 20
- 238000000034 method Methods 0.000 claims description 16
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 230000002152 alkylating effect Effects 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 239000003153 chemical reaction reagent Substances 0.000 claims description 7
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 6
- 239000000010 aprotic solvent Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
- 125000004970 halomethyl group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- XZVHHLNLLVICFA-UHFFFAOYSA-N 2-amino-2-[(3,4-dihydroxyphenyl)methyl]-3,3-difluoropropanoic acid Chemical compound FC(F)C(C(O)=O)(N)CC1=CC=C(O)C(O)=C1 XZVHHLNLLVICFA-UHFFFAOYSA-N 0.000 claims 1
- MFBHBQUFNAJYHN-UHFFFAOYSA-N 2-amino-3,3-difluoro-2-[(4-hydroxyphenyl)methyl]propanoic acid Chemical compound FC(F)C(C(O)=O)(N)CC1=CC=C(O)C=C1 MFBHBQUFNAJYHN-UHFFFAOYSA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- -1 methylenedioxy Chemical group 0.000 abstract description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 6
- 230000003287 optical effect Effects 0.000 abstract description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 55
- 239000002253 acid Substances 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 40
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 38
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 37
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 30
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000460 chlorine Substances 0.000 description 25
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 23
- 102000003823 Aromatic-L-amino-acid decarboxylases Human genes 0.000 description 23
- 108090000121 Aromatic-L-amino-acid decarboxylases Proteins 0.000 description 23
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 229940095574 propionic acid Drugs 0.000 description 20
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
- 229940000681 5-hydroxytryptophan Drugs 0.000 description 17
- 238000011282 treatment Methods 0.000 description 17
- 239000002585 base Substances 0.000 description 16
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 229960004502 levodopa Drugs 0.000 description 14
- 229940073584 methylene chloride Drugs 0.000 description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
- 238000007792 addition Methods 0.000 description 13
- 235000001014 amino acid Nutrition 0.000 description 13
- 229960003638 dopamine Drugs 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000003112 inhibitor Substances 0.000 description 12
- APJYDQYYACXCRM-UHFFFAOYSA-N tryptamine Chemical compound C1=CC=C2C(CCN)=CNC2=C1 APJYDQYYACXCRM-UHFFFAOYSA-N 0.000 description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 238000006114 decarboxylation reaction Methods 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 230000002093 peripheral effect Effects 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000006239 protecting group Chemical group 0.000 description 8
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- DZGWFCGJZKJUFP-UHFFFAOYSA-N tyramine Chemical compound NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 150000002500 ions Chemical class 0.000 description 7
- 230000002427 irreversible effect Effects 0.000 description 7
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 102000004031 Carboxy-Lyases Human genes 0.000 description 6
- 108090000489 Carboxy-Lyases Proteins 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- 208000027089 Parkinsonian disease Diseases 0.000 description 6
- 206010034010 Parkinsonism Diseases 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 6
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 229960001701 chloroform Drugs 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 150000004820 halides Chemical class 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 229930186147 Cephalosporin Natural products 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 241000282414 Homo sapiens Species 0.000 description 5
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 5
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 125000003277 amino group Chemical group 0.000 description 5
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- 150000001780 cephalosporins Chemical class 0.000 description 5
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
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- 239000008101 lactose Substances 0.000 description 5
- 229910052744 lithium Inorganic materials 0.000 description 5
- ARNWQMJQALNBBV-UHFFFAOYSA-N lithium carbide Chemical compound [Li+].[Li+].[C-]#[C-] ARNWQMJQALNBBV-UHFFFAOYSA-N 0.000 description 5
- 150000007530 organic bases Chemical class 0.000 description 5
- 229960002888 oxitriptan Drugs 0.000 description 5
- 239000002831 pharmacologic agent Substances 0.000 description 5
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 5
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- 239000007858 starting material Substances 0.000 description 5
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
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- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- 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
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81424377A | 1977-07-11 | 1977-07-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE781167L IE781167L (en) | 1979-01-11 |
| IE46932B1 true IE46932B1 (en) | 1983-11-02 |
Family
ID=25214519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1167/78A IE46932B1 (en) | 1977-07-11 | 1978-06-08 | -halomethyl amino acids |
Country Status (16)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL59481A0 (en) * | 1977-07-11 | 1980-05-30 | Merrell Toraude & Co | -halomethyl amino acids |
| EP0007600B1 (en) * | 1978-07-24 | 1983-05-11 | Merck & Co. Inc. | Alpha-difluoromethyl amino acids and pharmaceutical composition containing the same |
| FR2450247A1 (fr) * | 1979-02-28 | 1980-09-26 | Tamsir Ndike Wade | Esters et acides aliphatiques a-amines b,b-difluores |
| IE49522B1 (en) * | 1979-04-26 | 1985-10-16 | Merrell Toraude & Co | Alpha-halomethylaminoacids |
| ZA813018B (en) * | 1980-05-09 | 1982-05-26 | Merrell Toraude & Co | Fluoromethylated tyrosine methyl ester |
| ZA815807B (en) * | 1980-08-23 | 1982-08-25 | Merrell Toraude & Co | Preparation of aminoacetonitrile derivatives |
| CA3121517A1 (en) * | 2018-12-06 | 2020-06-11 | Senda Biosciences, Inc. | Quaternary ammonium salts as inhibitors of trimethylamine production |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3046300A (en) * | 1960-10-21 | 1962-07-24 | Merck & Co Inc | alpha-trifluoromethyloxyphenylalanines |
| FR2392958A1 (fr) * | 1977-06-01 | 1978-12-29 | Merck & Co Inc | Nouveaux amino-acides fluores utiles comme medicament |
| IE47542B1 (en) * | 1977-06-01 | 1984-04-18 | Merck & Co Inc | Di-and tri-fluoromethyl amino acids and amines,compositions and processes for preparing said compounds |
-
1978
- 1978-06-07 ZA ZA00783273A patent/ZA783273B/xx unknown
- 1978-06-08 IE IE1167/78A patent/IE46932B1/en not_active IP Right Cessation
- 1978-06-13 NZ NZ187538A patent/NZ187538A/en unknown
- 1978-06-15 IL IL7854913A patent/IL54913A0/xx not_active IP Right Cessation
- 1978-06-21 AU AU37312/78A patent/AU525684B2/en not_active Expired
- 1978-06-27 GB GB7827966A patent/GB2005659B/en not_active Expired
- 1978-06-30 DE DE19782828738 patent/DE2828738A1/de not_active Withdrawn
- 1978-07-07 CH CH742978A patent/CH636846A5/de not_active IP Right Cessation
- 1978-07-08 JP JP8253178A patent/JPS5484544A/ja active Granted
- 1978-07-10 SE SE7807690A patent/SE7807690L/xx unknown
- 1978-07-10 FR FR7820516A patent/FR2397391A1/fr active Granted
- 1978-07-10 ES ES471595A patent/ES471595A1/es not_active Expired
- 1978-07-10 IT IT50230/78A patent/IT1105534B/it active
- 1978-07-10 DK DK783093A patent/DK309378A/da unknown
- 1978-07-10 BE BE189190A patent/BE868881A/xx not_active IP Right Cessation
- 1978-07-11 NL NL7807454A patent/NL7807454A/xx not_active Application Discontinuation
-
1979
- 1979-03-12 ES ES478517A patent/ES478517A1/es not_active Expired
- 1979-03-12 ES ES478516A patent/ES478516A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| ES471595A1 (es) | 1979-10-01 |
| DK309378A (da) | 1979-01-12 |
| GB2005659A (en) | 1979-04-25 |
| DE2828738A1 (de) | 1979-02-01 |
| NZ187538A (en) | 1982-08-17 |
| IE781167L (en) | 1979-01-11 |
| GB2005659B (en) | 1982-02-17 |
| IT7850230A0 (it) | 1978-07-10 |
| NL7807454A (nl) | 1979-01-15 |
| FR2397391A1 (fr) | 1979-02-09 |
| AU3731278A (en) | 1980-01-03 |
| JPS5484544A (en) | 1979-07-05 |
| ZA783273B (en) | 1979-06-27 |
| IL54913A0 (en) | 1978-08-31 |
| SE7807690L (sv) | 1979-01-12 |
| FR2397391B1 (enrdf_load_html_response) | 1981-02-20 |
| ES478516A1 (es) | 1979-07-16 |
| CH636846A5 (de) | 1983-06-30 |
| AU525684B2 (en) | 1982-11-25 |
| BE868881A (fr) | 1978-11-03 |
| ES478517A1 (es) | 1979-07-16 |
| JPS6326101B2 (enrdf_load_html_response) | 1988-05-27 |
| IT1105534B (it) | 1985-11-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Patent lapsed |