GB1374294A - 2-amino-methylphenols - Google Patents
2-amino-methylphenolsInfo
- Publication number
- GB1374294A GB1374294A GB5904971A GB5904971A GB1374294A GB 1374294 A GB1374294 A GB 1374294A GB 5904971 A GB5904971 A GB 5904971A GB 5904971 A GB5904971 A GB 5904971A GB 1374294 A GB1374294 A GB 1374294A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- general formula
- butyl
- chloro
- pharmaceutically acceptable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- FEDLEBCVFZMHBP-UHFFFAOYSA-N 2-amino-3-methylphenol Chemical class CC1=CC=CC(O)=C1N FEDLEBCVFZMHBP-UHFFFAOYSA-N 0.000 title 1
- KPRZOPQOBJRYSW-UHFFFAOYSA-N 2-(aminomethyl)phenol Chemical class NCC1=CC=CC=C1O KPRZOPQOBJRYSW-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- YWJUSEYMIHBBMO-UHFFFAOYSA-N 2-chloro-3,5-dimethoxy-4-methylphenol Chemical compound COC1=CC(O)=C(Cl)C(OC)=C1C YWJUSEYMIHBBMO-UHFFFAOYSA-N 0.000 abstract 1
- VUGCKXJUVZGJRZ-UHFFFAOYSA-N 2-chloro-4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C(Cl)=C1 VUGCKXJUVZGJRZ-UHFFFAOYSA-N 0.000 abstract 1
- KULSVCANYQIOFD-UHFFFAOYSA-N 2-chloro-5-methoxyphenol Chemical compound COC1=CC=C(Cl)C(O)=C1 KULSVCANYQIOFD-UHFFFAOYSA-N 0.000 abstract 1
- GDEHXPCZWFXRKC-UHFFFAOYSA-N 4-(2-methylpropyl)phenol Chemical compound CC(C)CC1=CC=C(O)C=C1 GDEHXPCZWFXRKC-UHFFFAOYSA-N 0.000 abstract 1
- MEPLZFDVWVPBCJ-UHFFFAOYSA-N 4-tert-butyl-2-chloro-5-methoxyphenol Chemical compound COC1=CC(O)=C(Cl)C=C1C(C)(C)C MEPLZFDVWVPBCJ-UHFFFAOYSA-N 0.000 abstract 1
- ORLJSROIQHIMQM-UHFFFAOYSA-N 4-tert-butyl-2-fluorophenol Chemical compound CC(C)(C)C1=CC=C(O)C(F)=C1 ORLJSROIQHIMQM-UHFFFAOYSA-N 0.000 abstract 1
- DTNQNHHVSJPDSG-UHFFFAOYSA-N 4-tert-butyl-2-iodophenol Chemical compound CC(C)(C)C1=CC=C(O)C(I)=C1 DTNQNHHVSJPDSG-UHFFFAOYSA-N 0.000 abstract 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002934 diuretic Substances 0.000 abstract 1
- 230000001882 diuretic effect Effects 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- MNQOPPDTVHYCEZ-UHFFFAOYSA-N n-(hydroxymethyl)formamide Chemical compound OCNC=O MNQOPPDTVHYCEZ-UHFFFAOYSA-N 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 230000000894 saliuretic effect Effects 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 239000003981 vehicle Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/46—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C215/48—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups
- C07C215/50—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by hydroxy groups with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
- C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
- C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- 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
- C07C233/16—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 singly-bound oxygen atoms
- C07C233/17—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 singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—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 singly-bound oxygen atoms 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
- C07F3/12—Aromatic substances containing mercury
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1374294 2 - Aminomethylphenols; organomercury compound MERCK & CO Inc 20 Dec 1971 [23 Dec 1970] 59049/71 Headings C2C and C2J Novel 2-aminomethylphenols of the general formula wherein each of X<SP>1</SP> and X<SP>3</SP> is a hydrogen or halogen atom or an alkyl or alkoxy group, X<SP>2</SP> is an alkyl group and X<SP>4</SP> is a halogen atom, and non- toxic, pharmaceutically acceptable salts thereof are prepared by treating a 2-acylaminomethylphenol of the general formula wherein R is an acyl group and R<SP>2</SP> is a hydrogen atom or C 1-4 alkyl group, with an aqueous solution in the presence of an acid or base, followed optionally by neutralization of the resulting salt. 2-Acylaminomethylphenols of the second general formula above are prepared (a) by treating a phenol of the general formula with an N-hydroxymethyl-carboxamide of the general formula HOCH 2 NHR in the presence of a strong mineral acid or (b) by halogenating the corresponding compound in which X<SP>4</SP> or X<SP>3</SP> is a hydrogen atom (itself prepared analogously to (a)). Phenols of the third general formula above wherein R<SP>2</SP> is a methoxy group may be prepared by reaction of the corresponding compound wherein R<SP>2</SP> is a hydrogen atom with dimethyl sulphate. 2-Chloro-4-t-butyl-5-methoxyphenol is prepared by reaction of 2-chloro-5-methoxyphenol with isobutylene in the presence of concentrated R 2 SO 4 ; and 4-t-butyl-2-fluorophenol is prepared analogously. 4-iso-Butyl-2- chlorophenol is prepared by treatment of 4-isobutylphenol with sulphuryl chloride; and 2 - chloro - 3,5 - dimethoxy - 4 - methylphenol is prepared analogously. 4-t-Butyl-2-iodophenol is prepared by treatment of 4-t-butylphenol with mercuric acetate and sodium chloride, and reaction of the resulting 4-t-butyl-2-chloromercuriphenol with iodine. Pharmaceutical compositions having diuretic and saluretic activity comprise, as active ingredient, a 2-aminomethylphenol of the first general formula above or a non-toxic, pharmaceutically acceptable salt thereof, together with a pharmaceutically acceptable carrier or vehicle, and may be administered orally.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10117870A | 1970-12-23 | 1970-12-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1374294A true GB1374294A (en) | 1974-11-20 |
Family
ID=22283384
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5904971A Expired GB1374294A (en) | 1970-12-23 | 1971-12-20 | 2-amino-methylphenols |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS547780B1 (en) |
| AU (1) | AU470485B2 (en) |
| CA (1) | CA1006542A (en) |
| CH (1) | CH566964A5 (en) |
| FR (1) | FR2119066B1 (en) |
| GB (1) | GB1374294A (en) |
| NL (1) | NL149783B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070464A (en) * | 1976-02-19 | 1978-01-24 | Merck & Co., Inc. | Method of treating autoimmune diseases |
| FR2466495A1 (en) * | 1979-10-02 | 1981-04-10 | United Kingdom Government | INTERMEDIATE COMPOUNDS FOR THE PRODUCTION OF LIQUID CRYSTALS AND APPLICATION THEREOF |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996279A (en) | 1973-01-02 | 1976-12-07 | Gerot-Pharmazeutika Dr. Walter Otto K.G. | Novel 2-amino methyl-4,6-dihalogenphenol derivatives and methods for the preparation thereof |
| US4159279A (en) * | 1977-11-23 | 1979-06-26 | Merck & Co., Inc. | Nuclear substituted 2-hydroxyphenylmethanesulfamic acids |
| DE2934508A1 (en) * | 1978-09-06 | 1980-03-20 | Sandoz Ag | ALPHA -ALKYL-O-OXYBENZYLAMINE DERIVATIVES, THEIR PRODUCTION AND REMEDIES CONTAINING THEM |
| EP0020300A1 (en) * | 1979-05-28 | 1980-12-10 | Ciba-Geigy Ag | Aromatic hydroxy compounds, process for their preparation, pharmaceutical compositions containing such compounds, and use of the latter |
| FR2621590B1 (en) * | 1987-10-08 | 1990-05-25 | Inst Textile De France | NEW MERCUROBUTOL DERIVATIVES |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3321518A (en) * | 1961-06-27 | 1967-05-23 | Rohm & Haas | N-substituted poly(thiocarbamyl) phenols |
-
1971
- 1971-12-09 NL NL7116915A patent/NL149783B/en not_active IP Right Cessation
- 1971-12-14 CA CA130,145A patent/CA1006542A/en not_active Expired
- 1971-12-14 AU AU36844/71A patent/AU470485B2/en not_active Expired
- 1971-12-16 CH CH1837871A patent/CH566964A5/xx not_active IP Right Cessation
- 1971-12-17 JP JP10200171A patent/JPS547780B1/ja active Pending
- 1971-12-20 GB GB5904971A patent/GB1374294A/en not_active Expired
- 1971-12-23 FR FR7146444A patent/FR2119066B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4070464A (en) * | 1976-02-19 | 1978-01-24 | Merck & Co., Inc. | Method of treating autoimmune diseases |
| FR2466495A1 (en) * | 1979-10-02 | 1981-04-10 | United Kingdom Government | INTERMEDIATE COMPOUNDS FOR THE PRODUCTION OF LIQUID CRYSTALS AND APPLICATION THEREOF |
Also Published As
| Publication number | Publication date |
|---|---|
| AU470485B2 (en) | 1976-03-18 |
| CA1006542A (en) | 1977-03-08 |
| DE2163908A1 (en) | 1972-07-06 |
| CH566964A5 (en) | 1975-09-30 |
| JPS547780B1 (en) | 1979-04-10 |
| NL149783B (en) | 1976-06-15 |
| AU3684471A (en) | 1973-06-21 |
| FR2119066B1 (en) | 1974-10-18 |
| FR2119066A1 (en) | 1972-08-04 |
| NL7116915A (en) | 1972-06-27 |
| DE2163908B2 (en) | 1976-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SPA | Amended specification published | ||
| PE20 | Patent expired after termination of 20 years |