US3769317A - Novel ester derivatives of phenylpropanolamine - Google Patents
Novel ester derivatives of phenylpropanolamine Download PDFInfo
- Publication number
- US3769317A US3769317A US00118159A US3769317DA US3769317A US 3769317 A US3769317 A US 3769317A US 00118159 A US00118159 A US 00118159A US 3769317D A US3769317D A US 3769317DA US 3769317 A US3769317 A US 3769317A
- Authority
- US
- United States
- Prior art keywords
- phenylpropanolamine
- ester derivatives
- compounds
- novel ester
- derivatives
- 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 - Lifetime
Links
- -1 ester derivatives of phenylpropanolamine Chemical class 0.000 title description 6
- DLNKOYKMWOXYQA-APPZFPTMSA-N phenylpropanolamine Chemical class C[C@@H](N)[C@H](O)C1=CC=CC=C1 DLNKOYKMWOXYQA-APPZFPTMSA-N 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000000954 anitussive effect Effects 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- WDJHALXBUFZDSR-UHFFFAOYSA-N Acetoacetic acid Natural products CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001408 amides Chemical class 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 3
- WOWBFOBYOAGEEA-UHFFFAOYSA-N diafenthiuron Chemical compound CC(C)C1=C(NC(=S)NC(C)(C)C)C(C(C)C)=CC(OC=2C=CC=CC=2)=C1 WOWBFOBYOAGEEA-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 description 14
- DLNKOYKMWOXYQA-UHFFFAOYSA-N dl-pseudophenylpropanolamine Natural products CC(N)C(O)C1=CC=CC=C1 DLNKOYKMWOXYQA-UHFFFAOYSA-N 0.000 description 8
- 229960000395 phenylpropanolamine Drugs 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- PAWSVPVNIXFKOS-IHWYPQMZSA-N (Z)-2-aminobutenoic acid Chemical compound C\C=C(/N)C(O)=O PAWSVPVNIXFKOS-IHWYPQMZSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- PEOHLVWFSVQRLK-UHFFFAOYSA-N ethenylcarbamic acid Chemical class OC(=O)NC=C PEOHLVWFSVQRLK-UHFFFAOYSA-N 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
- IZHVBANLECCAGF-UHFFFAOYSA-N 2-hydroxy-3-(octadecanoyloxy)propyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)COC(=O)CCCCCCCCCCCCCCCCC IZHVBANLECCAGF-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 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 2
- 235000019483 Peanut oil Nutrition 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 239000003434 antitussive agent Substances 0.000 description 2
- 229940124584 antitussives Drugs 0.000 description 2
- 229940124630 bronchodilator Drugs 0.000 description 2
- 239000000168 bronchodilator agent Substances 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 239000000312 peanut oil Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 229940093858 ethyl acetoacetate Drugs 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 229940074045 glyceryl distearate Drugs 0.000 description 1
- 229940075507 glyceryl monostearate Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- NTMXFHGYWJIAAE-UHFFFAOYSA-N n,n-diethyl-3-oxobutanamide Chemical compound CCN(CC)C(=O)CC(C)=O NTMXFHGYWJIAAE-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 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
- A61K31/21—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
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
Definitions
- This invention relates to new organic compounds having valuable pharmacodynamic properties. More specifically this invention relates to vinylcarbamate derivatives of phenylpropanolamine having the following structural formula:
- the preferred and most advantageous compounds of this invention are the compounds wherein R is ethoxy, tertiarybutoxy and diethylamino.
- novel compounds of this invention are particularly useful as bronchodilator and antitussive agents.
- the similarity in therapeutic activity of phenylpropanolamine and the compounds of this invention may be explained by the occurrence of an in vivo hydrolysis of the vinylcarbamates to the phenylpropanolamine after administration.
- the compounds of this invention are therefore particularly advantageous as antitussives and bronchodilators because the hydrolysis results in a slower onset of action with a delayed time of peak effect.
- novel compounds of this invention as set forth in Formula I are prepared by reacting molar equivalents of phenylpropanolamine and the appropriate ester or amide of acetoacetic acid in an organic solvent according to the following synthetic procedure:
- the phenylpropanolamine derivatives as represented by Formula I are preferably employed in combination with either a liquid or solid nontoxic pharmaceutical carrier.
- a liquid or solid nontoxic pharmaceutical carrier A wide variety of pharmaceutical forms useful for oral ingestion may be employed.
- the preparation may take the form of tablets, capsules, powders, troches or lozenges.
- the pharmaceutical carrier may be, for example, lactose, magnesium stearate, starch, gums, such as acacia, terra alba, stearic acid, sorbitol, mannitol, ethyl cellulose or gelatin.
- the amount of solid carrier will vary widely but preferably is from 25 mg. to about 1 gm. If a liquid carrier is used, the preparation can be in the form of a syrup, elixir, liquid suspension, ampule, or soft gelatin capsule.
- the carrier or diluent can include any time delay material well known to the art, such as glyceryl monostearate or glyceryl distearate alone or with a wax.
- the pharmaceutical forms comprising the above novel phenylpropanolamine compounds are administered in dosage units internally, preferably orally.
- Advantageously equal daily doses are administered to provide a daily dosage regimen which produces antitussive activity.
- Each dosage unit Will contain the active medicament in an amount of about 10 mg. to about mg. preferably from about 25 mg. to about 50 mg.
- Advantageously equal doses will be administered 2 to 4 times daily with the daily dosage regimen being about 20 mg. to about 400 mg. preferably from about 50 mg. to about 200 mg.
- EXAMPLE 1 A mixture of 15.1 g. of phenylpropanolamine and 13.0 g. of ethylacetoacetate in 50 ml. of benzene is heated at reflux for about 3 hours until the calculated amount of water is collected. The warm mixture is treated with charcoal and cooled to yield 3-(fl-hydroxy-a-methylphenethyl)aminocrotonic acid, ethyl ester as a white solid having a melting point of 92.5-93.5 C.
- EXAMPLE 2 A mixture of 30.2 g. of phenylpropanolamine and 31.4 g. of N,N-diethyl acetoacetamide in ml. of benzene is heated at reflux for about two hours until 0.2 mole of water is collected. The mixture is decolorized with charcoal and diluted with hexane. The precipitate formed on cooling is N,N-diethyl-3-(fl-hydroxy-a-methylphenethylamino) crotonamide having a melting point of 86-87" C.
- EXAMPLE 4 Ingredients: Mg./ capsule 3 (13-hydroxy-ot-methylphenethyl)aminocrotonic acid, t-butyl ester Peanut oil Disperse the peanut oil in the ester and place in a soft gelatin capsule.
- One capsule is administered orally four times a day.
- One capsule is administered three times a day.
- R is a lower alkoxy group containing from 1 to 4 carbon atoms or a di-loweralkylamino group in which the loweralkyl group contains from 1 to carbon atoms.
- R is t-butoxy, being the compound S-(B-hydrOXy-amethylphenethyl)aminocrotonic acid, t-butyl ester.
- a chemical compound according to claim 1 in which R is ethoxy being the compound 3-(B-hydroxy-a-methylphenethyl)aminocrotonic acid, ethyl ester.
- the loi'reralkyl group contains from 1 to 4 carbon atoms.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Emergency Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
VINYLCARBMATE DERIVATIVES OF PHENYLPROPANOLAMINE HAVING ANTITUSSIVE ACTIVITY. METHOD OF PREPARATION COMPRISES REACTING PHENYPROPANOLAMINE WITH THE APPROPRIATE ACETOACETIC ACID ESTER OR AMIDE IN ANY SUITABLE ORGANIC SOLVENT.
Description
United States Patent Office 3,769,317 Patented Oct. 30, 1973 3,769,317 NOVEL ESTER DERIVATIVES OF PHENYLPROPANOLAMINE Henry Cecil Caldwell, Ambler, Pa., assignor to Smith Kline & French Laboratories, Philadelphia, Pa. No Drawing. Filed Feb. 23, 1971, Ser. No. 118,159 Int. Cl. C07c 103/30 US. Cl. 260-471 A 4 Claims ABSTRACT OF THE DISCLOSURE Vinylcarbamate derivatives of phenylpropanolamine having antitussive activity. Method of preparation comprises reacting phenylpropanolamine with the appropriate acetoacetic acid ester or amide in any suitable organic solvent.
This invention relates to new organic compounds having valuable pharmacodynamic properties. More specifically this invention relates to vinylcarbamate derivatives of phenylpropanolamine having the following structural formula:
FORMULA I -CH-OHCH3 H NC=CH III (3H3 wherein: R is a lower alkoxy or a di-loweralkylamino group. The term lower alkoxy and loweralkyl is here and elsewhere employed to designate a chain containing from one to four carbon atoms.
The preferred and most advantageous compounds of this invention are the compounds wherein R is ethoxy, tertiarybutoxy and diethylamino.
The novel compounds of this invention are particularly useful as bronchodilator and antitussive agents. The similarity in therapeutic activity of phenylpropanolamine and the compounds of this invention may be explained by the occurrence of an in vivo hydrolysis of the vinylcarbamates to the phenylpropanolamine after administration. The compounds of this invention are therefore particularly advantageous as antitussives and bronchodilators because the hydrolysis results in a slower onset of action with a delayed time of peak effect.
The novel compounds of this invention as set forth in Formula I are prepared by reacting molar equivalents of phenylpropanolamine and the appropriate ester or amide of acetoacetic acid in an organic solvent according to the following synthetic procedure:
CH-CH-CH:
CHaCOCI-IzCOR H NHz CH-CH 0 The phenylpropanolamine derivatives as represented by Formula I are preferably employed in combination with either a liquid or solid nontoxic pharmaceutical carrier. A wide variety of pharmaceutical forms useful for oral ingestion may be employed. Advantageously the preparation may take the form of tablets, capsules, powders, troches or lozenges. When a solid form is employed the pharmaceutical carrier may be, for example, lactose, magnesium stearate, starch, gums, such as acacia, terra alba, stearic acid, sorbitol, mannitol, ethyl cellulose or gelatin. The amount of solid carrier will vary widely but preferably is from 25 mg. to about 1 gm. If a liquid carrier is used, the preparation can be in the form of a syrup, elixir, liquid suspension, ampule, or soft gelatin capsule.
Similarly the carrier or diluent can include any time delay material well known to the art, such as glyceryl monostearate or glyceryl distearate alone or with a wax.
The pharmaceutical forms comprising the above novel phenylpropanolamine compounds are administered in dosage units internally, preferably orally. Advantageously equal daily doses are administered to provide a daily dosage regimen which produces antitussive activity. Each dosage unit Will contain the active medicament in an amount of about 10 mg. to about mg. preferably from about 25 mg. to about 50 mg. Advantageously equal doses will be administered 2 to 4 times daily with the daily dosage regimen being about 20 mg. to about 400 mg. preferably from about 50 mg. to about 200 mg.
The following examples are not limiting but are illustrative of compounds of this invention and the procedures for their preparation.
EXAMPLE 1 A mixture of 15.1 g. of phenylpropanolamine and 13.0 g. of ethylacetoacetate in 50 ml. of benzene is heated at reflux for about 3 hours until the calculated amount of water is collected. The warm mixture is treated with charcoal and cooled to yield 3-(fl-hydroxy-a-methylphenethyl)aminocrotonic acid, ethyl ester as a white solid having a melting point of 92.5-93.5 C.
EXAMPLE 2 EXAMPLE 3 A mixture of 30.2 g. of phenylpropanolamine and 31.4 g. of N,N-diethyl acetoacetamide in ml. of benzene is heated at reflux for about two hours until 0.2 mole of water is collected. The mixture is decolorized with charcoal and diluted with hexane. The precipitate formed on cooling is N,N-diethyl-3-(fl-hydroxy-a-methylphenethylamino) crotonamide having a melting point of 86-87" C.
EXAMPLE 4 Ingredients: Mg./ capsule 3 (13-hydroxy-ot-methylphenethyl)aminocrotonic acid, t-butyl ester Peanut oil Disperse the peanut oil in the ester and place in a soft gelatin capsule.
One capsule is administered orally four times a day.
EXAMPLE 5 Ingredients:
3 (,B-hydroxy-a-methylphenethyl)aminocrotonic acid, ethyl ester 50 Calcium sulfate dihydrate 100 Sucrose 25 Starch l5 Talc 5 Stearic acid 3 The sucrose, calcium sulfate and ethyl ester are thoroughly mixed and granulated with hot 10% gelatin solu- Mg./tablet EXAMPLE 6 Ingredients: Mg./capsule N,N diethyl 3 (B-hydroxy-a-methylphenethylamino)crotonamide 75 Lactose 125 The ingredients are thoroughly mixed and filled into a hard gelatin capsule.
One capsule is administered three times a day.
What is claimed is:
1. A chemical compound of the formula:
wherein: R is a lower alkoxy group containing from 1 to 4 carbon atoms or a di-loweralkylamino group in which the loweralkyl group contains from 1 to carbon atoms.
2. A chemical compound according to claim 1 in which R is t-butoxy, being the compound S-(B-hydrOXy-amethylphenethyl)aminocrotonic acid, t-butyl ester.
3. A chemical compound according to claim 1 in which R is diethylamino, being the compound N,N-diethyl-3-(flhydroxy-a-methylphenethylamino crotonamide.
4. A chemical compound according to claim 1 in which R is ethoxy, being the compound 3-(B-hydroxy-a-methylphenethyl)aminocrotonic acid, ethyl ester.
LORRAINE A. WEINBERGER, Primary Examiner L. A. THAXT ON, Assistant Examiner US. Cl. X.R.
mg UNITED STATES PATENT OFFICE v CERTIFICATE OF CORRECTION Patent No. 3,152,317 I mm October 30, 1973 Inventofls) Henry Cecil Caldwell It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
(l olunm 4, line 3 reading "the loweralkyl group contains from .1
1 to carbon atoms." shouldread:
"the loi'reralkyl group contains from 1 to 4 carbon atoms.'
Signed and sealed this 14th Gay-of'May 197b,;
Attestz" ..v 4
EDWARD I-LFLETCHEH, JR. 7 C. MARSHALL DANN I At'testing Officer I I Commissioner of Patents
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11815971A | 1971-02-23 | 1971-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3769317A true US3769317A (en) | 1973-10-30 |
Family
ID=22376830
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00118159A Expired - Lifetime US3769317A (en) | 1971-02-23 | 1971-02-23 | Novel ester derivatives of phenylpropanolamine |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3769317A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933911A (en) * | 1973-07-19 | 1976-01-20 | Imperial Chemical Industries Limited | 1-Aryl-2-amidoalkylaminoethanol derivatives |
| US4041074A (en) * | 1973-07-19 | 1977-08-09 | Imperial Chemical Industries Limited | 1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives |
| JP2763676B2 (en) | 1988-12-12 | 1998-06-11 | イーストマン ケミカル カンパニー | Functionalization of nucleophiles |
-
1971
- 1971-02-23 US US00118159A patent/US3769317A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933911A (en) * | 1973-07-19 | 1976-01-20 | Imperial Chemical Industries Limited | 1-Aryl-2-amidoalkylaminoethanol derivatives |
| US4041074A (en) * | 1973-07-19 | 1977-08-09 | Imperial Chemical Industries Limited | 1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives |
| JP2763676B2 (en) | 1988-12-12 | 1998-06-11 | イーストマン ケミカル カンパニー | Functionalization of nucleophiles |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| AS | Assignment |
Owner name: SMITHKLINE BECKMAN CORPORATION, PENNSYLVANIA Free format text: CHANGE OF NAME;ASSIGNOR:SMITHKLINE CORPORATION;REEL/FRAME:004080/0769 Effective date: 19820304 Owner name: SMITHKLINE BECKMAN CORPORATION Free format text: CHANGE OF NAME;ASSIGNOR:SMITHKLINE CORPORATION;REEL/FRAME:004080/0769 Effective date: 19820304 |