SYNTHESIS OF PHARMACEUTICAL

DRUGS
.
PHARMACEUTICAL DRUGS
 Pharmaceutical drugs are chemicals that are designed to prevent,
diagnose, treat, or cure a disorder. In layman terms, we simply call
them medicines.

IMPORTANCE OF PHARMACEUTICAL DRUGS

 The purpose of the pharmaceutical industry is to bring patients

innovative new therapies that help them to live longer, healthier
lives. ... Over the course of the past 50 years, this industry has tackled
some of the leading causes of disease and life-threatening illnesses
LIST OF COMPOUNDS
MALONYL UREA
PHENACETIN
ISONIAZID
TRYPTOPHAN
ISOPENTAQUINE
CHLOROQUINE
SULPHANILAMID
E
SULPHAPYRIDINE
Malonyl Urea

It is also called Barbituric Acid

INTRODUCTION
 Barbituric acid or malonylurea or
 6-hydroxyuracil is an organic compound based on
a pyrimidine heterocyclic skeleton. It is an odorless powder soluble in
water. Barbituric acid is the parent compound
of barbiturate drugs, although barbituric acid itself is not
pharmacologically active. The compound was first synthesized by Adolf
von Baeyer.
 Molecular Formula:C 4H4N2O3
SYNTHESI
S
1.The synthesis of barbituric
acid is effected by
condensation of diethyl
malonate with urea in the
presence of sodium ethoxide
which may be prepared by
reacting Na metal with
ethanol and it undergo
cyclization reaction with
diethyl malonate.
2. Barbituric acid prepared from malonic acid, urea, and
phosphorus oxychloride (POCl3)
USES

 Using the Knoevenagel condensation reaction, barbituric acid can

form a large variety of barbiturate drugs that behave as central nervous
system depressants. It used as hypnotics, sedatives, anticonvulsants and
anesthetics, although they are probably most familiar as 'sleeping
pills‘.
 Barbituric acid is a chemical building block in a laboratory synthesis
riboflavin (vitamin B2) and in a method of producing the
pharmaceutical drug minoxidil.
 PHENACETIN

[Acetophenetidin, N-(4-ethoxyphenyl)acetamide]
INTRODUCTION
 Phenacetin is a synthetic, white crystalline solid that is slightly soluble
in water and benzene, soluble in acetone and very soluble in
pyrimidine.
 Phenacetin is a member of the class of acetamides that is acetamide in
which one of the hydrogens attached to the nitrogen is substituted by a
4-ethoxyphenyl group.
 It is a member of acetamides and an aromatic ether.
SYNTHESI
S
SIDE EFFECTS
 Nausea
 Vomiting
 Allergic reactions
 Interstitial nephritis
 Tumorigenicity
 Bladder cancer
 Colon cancer
USE
S
 Phenacetin was used as an analgesic and fever-reducing drug in
both human and veterinary medicine for many years.
 It was withdrawn from medicinal use as dangerous from the
1970s
 Phenacetin also was once used as a stabilizer for hydrogen
peroxide in hair-bleaching preparations.
ISONIAZID
Isonicotinic acid
hydrazide.
ISONIAZID
• Isoniazid(INH), also known as isonicotinic acid hydrazide. It is used as
an antibiotic for the treatment of tuberculosis. For active tuberculosis it
is often used together with rifampicin, pyrazinamide, and either
streptomycin or ethambutol. For latent tuberculosis it is often used by
itself.
• Formula: C6H7N3O
• Molar mass: 137.139 g/mol
• Other names: isonicotinic acid hydrazide, isonicotinyl hydrazine,
INHA
ISONIAZID STRUCTURE

ISONIAZID: 2D STRUCTURE ISONIAZID: 3D STRUCTURE

PROPERTIES
• A carbohydrazide obtained by formal condensation between
pyridine-4-carboxylic acid and hydrazine.
• Isoniazid appears as odorless colorless or white crystals or white
crystals.
• Isoniazid is a synthetic derivative of nicotinic acid with anti-
mycobacterial properties.
• When isoniazid is heated to decomposition it emits toxic fumes of
nitrogen oxides.
• Boiling Point: 329.79° C
• Melting Point: 171-173° C
SYNTHESI
S
4-methyl pyridine on
oxidation forms isonicotinic
acid which on addition of
hydrazine and removal of
H2O results in the formation
of isoniazid.
CHEMICAL
SYNTHESIS
Basic hydrolysis of 4-cyano
pyridine converts
cyano/nitrile group to an
amide- isonicotinamide,
which then reacts with
hydrazine to produce
isoniazid
USE
S
 Isoniazid is used with other medications to treat active tuberculosis(TB)
infections.
 Isoniazid is also used alone to prevent active TB infections in people
who may be infected with bacteria (people with positive TB skin test).
 Isoniazid is an antibiotic and works by stopping the growth of bacteria.
SIDE EFFECTS
• sudden weakness or ill feeling, or fever for 3
days or longer;
• your back), nausea, loss of appetite; pain in
your upper stomach (may spread to
• vision changes, pain behind your eyes;
• confusion, memory problems, unusual
thoughts or behavior;
• pale skin, easy bruising or bleeding
(nosebleeds, bleeding gums).
PARA AMINO BENZOIC ACID

4-amino Benzoic Acid

PARA AMINO BENZOIC
ACID
 Para amino benzoic acid is commonly known as PABA.
 It is a white solid but can be grey in colour in commercial
samples.
 It is an intermediate in the synthesis of folate.
 It is slightly soluble in water and benzene and insoluble in
petroleum ether.
 PABA is commonly found in milk, eggs, grains and meat.
SYNTHESIS: FROM TOLUENE
• Toluene is nitrated to
produce o-nitrotoluene and
p-nitrotoluene and then
oxidised to p- nitrobenzoic
acid. Finally the nitro
group of p-nitrobenzoic
acid is reduced with
hydrogenation catalyst such
as hydrochloric acid - tin
mixture or platinum.
USE
S
 PABA is best known as the active ingredient of sunscreen. It can block
UV radiations from the skin.
 It has been used to improve discoloration in skin and hair.
 It is taken by mouth to treat skin conditions like vitiligo, morphia,
lymph blastoma cutis and dermatomyositis.
 It is used to cure other diseases like anaemia (tired blood), arthritis,
rheumatic fever and conspiration.
 It is used in the production of azo dyes and cross linking agents.
 It is also used as a biodegradable pesticide.
TRYPTOPHAN
It is an amino
acid
INTRODUCTION

 Tryptophan is a α-amino acid used in the

biosynthesis of proteins. It contains an α-
amino group, an α- carboxylic acid group
and a side chain indole making
it non polar aromatic amino acid. It is
essential in humans and body cannot
synthesize it and it must be obtained via
diet.
SYNTHESI
S
•
HOH2-CH-COOH
| NH2
-H2 O

Indole 2–
hydroxyl
aniline Tryptophan
USE
S
 Severe PMS symptoms (premenstrual dysphoric disorder or
PMDD). Taking 6 grams of tryptophan per day seems to decrease
mood swings, tension, and irritability in women with PMDD.
 It helps to quit smoking.
 Depression: Early research suggests that tryptophan might
improve the effectiveness of common medications for depression.
• It helps in treating digestive tract infection that can lead to
ulcers (Helicobacter pylori or H. pylori).
• Helps to come out of Insomnia.
FOODS WITH
TRYPTOPHAN
Tryptophan can be found in some foods, especially those high in
protein.
Foods known to be high in tryptophan include:
 chicken
 eggs
 cheese
 fish
 peanuts
 pumpkin and sesame seeds
 milk
 ISOPENTAQUIN
.E
INTRODUCTION AND
USES
 It is a heterocyclic compound having molecular
formula C18H27N3O
 It is also considered as a anti malarial drug
 Used in treatment of pneumonia
SYNTHESI
S
By the condensation of 8-amino 6-methoxy quinolone with 2-
bromo 5-isopropyl amino pentane
CHLOROQUINE
Properties
Preparation

• Three Steps:
•
•
Preparation of Dichloroquiline
•
Preparation of Novaldiamine
•
Condensation of Dichloroquiline and
Novaldiamine
Preparation of Dichloroquiline
Preparation of Novaldiamine

Novaldiamine (1-diethylamino-4-aminopentane)
is prepared by reaction of Ethyleneoxide and
Diethylamine
Condensation
Uses

• It is mostly used to treat Malaria

• It also for Hepatic Amoebiasis
• Researchers at Brigham Hospital in Boston published the results of
a study of 96,032 hospitalized COVID-19 patients, evaluating
whether the use of antimalarial drugs chloroquine or
hydroxychloroquine (HCQ), with or without an antibiotic, were
helpful in battling the disease. They found that of the 15,000 patients
who received either of the drugs were almost twice as likely to die
compared to the patients who did not receive them.
SULPHANILAMIDE

Molecular Formula: C6H8N2O2S

Molecular Weight: 172.208 g/mol
INTRODUCTION
 Sulphanilamide is an organic compound consisting of an Aniline
derivatized with a Sulphonamide group.
 White coloured, crystalline solid or powdery, Odourless.
 Melting point: 164⁰ – 166⁰ C
 Boiling Point: 400.5 ± 47.0 °C
 Density: 1.08 (at 25⁰C)
USE
S
 Powdered sulphanilamide was used by the Allies in World War II to
reduce infection rates.
 Sulphanilamide is primarily used for the treatment of Fungal
Infections.
 Sulphanilamide is also used in the manufacture of azo dyes.
SYNTHESI
S
 Aniline to Acetanilide
Acetanilide to
Sulphanilamide
.
SULPHANILAMIDE FROM
CHLOROBENZENE
• Chlorobenzene reacts with hydrogen chlorosulphide to give p-
Chlorobenzene sulfonyl chloride.

• p-Chlorobenzene sulfonyl chloride reacts with Ammonia inpresence

of Na-OH gives Sulfanilamide.
SULPHANILAMIDE FROM P-TOLUENE
SULPHONAMIDE
PARA TOULENE SULPHONAMIDE

Sulfonamide functional group (also

spelled sulphonamide) is
R-S(=O)2-NH2, a sulfonyl group connected to
an amine group. Relatively speaking this group
is unreactive. The amine center is no longer
basic.

Molecular Weight: 171.22 g/mol

Molecular Formula: C7H9NO2S
SYNTHESIS

P-toluene sulphonamide
on undergoing oxidation
gives acid derivative,
chlorinated by PCl5, by
treating with NH3 at last
by
undergoing Hoffmann
degradation gives
sulphanilamide.
SULPHAPYRIDIN
E
C11H11N3O2S
INTRODUCTION
Sulfapyridine (INN; also known as sulphapyridine) is a
sulfanilamide antibacterial medication. Sulfapyridine is no longer
prescribed as treatment for infections.
• Formula: C11H11N3O2S
• Molar mass: 249.29 g·mol −1
• Melting point: 192℃
SYNTHESIS: FROM N-acetylsulfalinyl
chloride
PREPERATION:

 2-amino pyridine(C5H6N2) an colorless solid reacts with N- acetyl

sulfanyl chloride and the mixture in heated on a steam bath
resulting an intermediate.
 The intermediate is now hydrolysed by boiling with Sodium
Hydroxide.
 Which will now result in the removal of sodium acetate and
formation of Sulfapyridine.
USE
S
• used to treat linear IgA disease and has use in veterinary medicine.
• It is no longer prescribed for humans because of its solubility in
water is pH dependent.
• It may also crystallize in urinary bladder or urethra and cause
blockage or pain.
• It is a good anti bacterial drug.
• It is used to help control dermatitis herpetiformis a skin disease.
THANK
YOU
GROUP MEMBERS
Varun Adithya Suraj
Smithi Rakshana
Suvitha Velushree
Swathi Priya Yeshwanth
Swetha Vishnu Shree
Tamizmaran Yogeshwaran
Vasantha Kumar
Yeshwanth
Yogeshwara
n