SE8003116L - ALFA-halomethyl-amino acids - Google Patents
ALFA-halomethyl-amino acidsInfo
- Publication number
- SE8003116L SE8003116L SE8003116A SE8003116A SE8003116L SE 8003116 L SE8003116 L SE 8003116L SE 8003116 A SE8003116 A SE 8003116A SE 8003116 A SE8003116 A SE 8003116A SE 8003116 L SE8003116 L SE 8003116L
- Authority
- SE
- Sweden
- Prior art keywords
- hydroxy
- hydrogen
- formula
- ch2f
- hydrolysing
- Prior art date
Links
- 229910052739 hydrogen Inorganic materials 0.000 abstract 4
- 239000001257 hydrogen Substances 0.000 abstract 4
- 150000002431 hydrogen Chemical group 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- -1 hydroxy, methyl Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 230000003301 hydrolyzing effect Effects 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- GNFVFPBRMLIKIM-UHFFFAOYSA-N 2-fluoroacetonitrile Chemical compound FCC#N GNFVFPBRMLIKIM-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
- 125000005122 aminoalkylamino group Chemical group 0.000 abstract 1
- 125000005219 aminonitrile group Chemical group 0.000 abstract 1
- 150000003863 ammonium salts Chemical class 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000004658 ketimines Chemical class 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/12—Ketones
- A61K31/122—Ketones having the oxygen directly attached to a ring, e.g. quinones, vitamin K1, anthralin
- A61K31/125—Camphor; Nuclear substituted derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
- C07C229/36—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings with at least one amino group and one carboxyl group bound to the same carbon atom of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- C07C233/45—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 carboxyl groups
- C07C233/46—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—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 carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
- C07C237/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide 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
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
- C07C49/163—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/175—Saturated compounds containing keto groups bound to acyclic carbon atoms containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/24—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups
- C07C49/245—Unsaturated compounds containing keto groups bound to acyclic carbon atoms containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
-
- 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
Abstract
Compounds of formula I <IMAGE> wherein Y is -CH2F, -CHF2, -CH2Cl or -CHCl2; R is hydroxy, alkoxy, amino alkylamino, dialkylamino or carboxyalkylamino, R1 is hydrogen, alkylcarbonyl, alkoxycarbonyl or aminoalkylcarbonyl, and three of R2, R3, R4, R5 and R6 are hydrogen and the other two are selected from hydroxy, methyl and methoxy, and salts thereof. Also disclosed is a process of preparing compounds of formula I in which R is hydroxy, R1 is hydrogen, Y is -CH2F and R2, R3, R4, R5 and R6 are various combinations of hydrogen, methyl, ethyl, halogen, trifluoromethyl, hydroxy, methoxy and methylenedioxy by reacting a novel ketone of formula III <IMAGE> wherein R12 to R16 correspond to R2 to R6 provided that hydroxy groups are protected, with sodium cyanide and an ammonium salt, and hydrolysing the resulting aminonitrile. The novel ketones are prepared by reacting a suitable benzyl Grignard with fluoroacetonitrile and hydrolysing the resulting ketimine.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3371979A | 1979-04-26 | 1979-04-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
SE8003116L true SE8003116L (en) | 1980-10-27 |
Family
ID=21872052
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SE8003116A SE8003116L (en) | 1979-04-26 | 1980-04-24 | ALFA-halomethyl-amino acids |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS55145647A (en) |
AU (1) | AU5774180A (en) |
BE (1) | BE882105R (en) |
CH (1) | CH646939A5 (en) |
DE (3) | DE3012602A1 (en) |
DK (1) | DK180880A (en) |
ES (2) | ES8201534A1 (en) |
GB (1) | GB2050356B (en) |
IE (1) | IE49522B1 (en) |
IT (1) | IT1143940B (en) |
NL (1) | NL8002417A (en) |
NO (1) | NO801209L (en) |
SE (1) | SE8003116L (en) |
ZA (1) | ZA801118B (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4101873C2 (en) | 1991-01-23 | 1993-12-09 | Isis Pharma Gmbh | Orally administrable drug form for the treatment of central dopamine deficiency states |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
FR2392958A1 (en) * | 1977-06-01 | 1978-12-29 | Merck & Co Inc | NEW FLUORINE AMINO ACIDS USEFUL AS A MEDICINAL PRODUCT |
ZA783273B (en) * | 1977-07-11 | 1979-06-27 | Merrell Toraude & Co | A-halomethyl amino acids |
AU3872678A (en) * | 1977-09-01 | 1980-02-14 | Merrell Toraude & Co | Alpha-halomethyl amines |
ATE3282T1 (en) * | 1978-07-24 | 1983-05-15 | Merck & Co. Inc. | ALPHA-DIFLUOROMETHYL-ALPHA-AMINO ACIDS AND PHARMACEUTICAL COMPOSITION CONTAINING THEM. |
-
1980
- 1980-02-26 IE IE382/80A patent/IE49522B1/en not_active IP Right Cessation
- 1980-02-27 ZA ZA00801118A patent/ZA801118B/en unknown
- 1980-03-06 BE BE0/199691A patent/BE882105R/en not_active IP Right Cessation
- 1980-03-18 CH CH213680A patent/CH646939A5/en not_active IP Right Cessation
- 1980-04-01 DE DE19803012602 patent/DE3012602A1/en not_active Withdrawn
- 1980-04-01 DE DE19803012641 patent/DE3012641A1/en not_active Withdrawn
- 1980-04-01 DE DE19803012581 patent/DE3012581A1/en not_active Withdrawn
- 1980-04-10 ES ES490442A patent/ES8201534A1/en not_active Expired
- 1980-04-10 ES ES490441A patent/ES490441A0/en active Granted
- 1980-04-22 IT IT48484/80A patent/IT1143940B/en active
- 1980-04-23 AU AU57741/80A patent/AU5774180A/en not_active Abandoned
- 1980-04-24 SE SE8003116A patent/SE8003116L/en not_active Application Discontinuation
- 1980-04-25 NO NO801209A patent/NO801209L/en unknown
- 1980-04-25 DK DK180880A patent/DK180880A/en unknown
- 1980-04-25 NL NL8002417A patent/NL8002417A/en not_active Application Discontinuation
- 1980-04-25 JP JP5442780A patent/JPS55145647A/en active Pending
- 1980-04-25 GB GB8013819A patent/GB2050356B/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
DE3012602A1 (en) | 1980-11-06 |
IE49522B1 (en) | 1985-10-16 |
DK180880A (en) | 1980-10-27 |
NO801209L (en) | 1980-10-27 |
JPS55145647A (en) | 1980-11-13 |
DE3012641A1 (en) | 1980-11-06 |
IT1143940B (en) | 1986-10-29 |
GB2050356A (en) | 1981-01-07 |
ES490442A0 (en) | 1982-01-01 |
IE800382L (en) | 1980-10-26 |
NL8002417A (en) | 1980-10-28 |
ES8201533A1 (en) | 1982-01-01 |
AU5774180A (en) | 1980-10-30 |
CH646939A5 (en) | 1984-12-28 |
GB2050356B (en) | 1983-05-18 |
ZA801118B (en) | 1981-02-25 |
DE3012581A1 (en) | 1980-11-13 |
IT8048484A0 (en) | 1980-04-22 |
ES490441A0 (en) | 1982-01-01 |
BE882105R (en) | 1980-07-01 |
ES8201534A1 (en) | 1982-01-01 |
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