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-Chemistry for Humanity- DOC NO-Sym imp-001/0416 Page 1 of 25 Symphony Pharma Life Sciences Pvt. Ltd. Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323 S. No Impurity chemical name/ code CAS No/ Structure API 1 4-{1-[4-(2-Azepan-1-yl-ethoxy)-benzyl-5- benzyloxy-3-methyl-1 H-indole-2-yl}-phenol 328933-58-0 Bazedoxifene acetate 2 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol 91444-54-1 Bazedoxifene acetate 3 1-(4-Hydroxy-benzyl)-2-(4-hydroxy-phenyl)- 3-methyl-1H-indole-5-ol 104599-10-2 Bazedoxifene acetate 4 1-(4-(2-(Azepan-1-yl)ethoxy)benzyl)-5- (benzyloxy)-2-(4-benzyloxy)phenyl)-3-methyl-1H- indole 198480-21-6 Bazedoxifene acetate 5 2-(4-Hydroxy-phenyl)-3-methyl-1-{4-[2-(1-oxy-azepan- 1-yl)- ethoxy]-benzyl}-1H-indol-5-ol 1174289-22-5 Bazedoxifene acetate 6 1-(4-(benzyloxy)phenyl)-2-(4-benzyloxy)phenylamino- propan-1-one 1048697-94-4 Bazedoxifene acetate 7 (R)-2-(4-Aminophenethylamino)-1-phenylethanol hydrochloride 391901-45-4 Mirabegron 8 N-(2-{4-[2-(2-Amino-thiozol-4-yl)acetyl amino]- phenyl}-ethyl-2-hydroxy-2-phenyl-acetamide Mirabegron 9 2-(2-Amino-thiozol-4-yl)- N[4-(2-phenethyl amino-ethyl)-phenyl]-acetamide 1581284-82-3 Mirabegron H N N H O N S NH2 OH O
Transcript
Page 1: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 1 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

S.No

Impurity chemical name/ code

CAS No/ Structure

API

1 4-{1-[4-(2-Azepan-1-yl-ethoxy)-benzyl-5- benzyloxy-3-methyl-1 H-indole-2-yl}-phenol

328933-58-0

Bazedoxifene acetate

2 2-(4-hydroxyphenyl)-3-methyl-1H-indol-5-ol 91444-54-1 Bazedoxifene

acetate

3 1-(4-Hydroxy-benzyl)-2-(4-hydroxy-phenyl)- 3-methyl-1H-indole-5-ol

104599-10-2 Bazedoxifene

acetate

4 1-(4-(2-(Azepan-1-yl)ethoxy)benzyl)-5- (benzyloxy)-2-(4-benzyloxy)phenyl)-3-methyl-1H-indole

198480-21-6 Bazedoxifene

acetate

5 2-(4-Hydroxy-phenyl)-3-methyl-1-{4-[2-(1-oxy-azepan-1-yl)- ethoxy]-benzyl}-1H-indol-5-ol

1174289-22-5 Bazedoxifene

acetate

6 1-(4-(benzyloxy)phenyl)-2-(4-benzyloxy)phenylamino-propan-1-one

1048697-94-4 Bazedoxifene

acetate

7 (R)-2-(4-Aminophenethylamino)-1-phenylethanol hydrochloride

391901-45-4 Mirabegron

8 N-(2-{4-[2-(2-Amino-thiozol-4-yl)acetyl amino]-phenyl}-ethyl-2-hydroxy-2-phenyl-acetamide

Mirabegron

9 2-(2-Amino-thiozol-4-yl)- N[4-(2-phenethyl amino-ethyl)-phenyl]-acetamide

1581284-82-3 Mirabegron

HN

NH

O

N

S

NH2

OH

O

Page 2: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 2 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

10 (S) -2-(2-amino thiozol-4-yl)-4-[2-[(2-hydroxy-2-phenyl ethyl) amino] ethyl] acetamide

1796931-48-0

Mirabegron

11

2-(2-Amino-thiozol-4-yl)-N-(4-{2-[[2-(2-amino-thiazol-4-yl)-acetyl] -(2-hydroxy-2-phenyl-ethyl)-amino}-ethyl}-phenyl)-acetamide

1684452-83-2 Mirabegron

12 ((S)-2-((4-nitrophenethyl) amino)-1-phenylethanol hydrochloride

Mirabegron

13 4-(2-(phenethylamino)ethyl)aniline hydrochloride 1581285-26-8 Mirabegron

14 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl) benzofuran derivative

Dronedarone Hydrochloride

15 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl) benzofuran derivative

Dronedarone Hydrochloride

16 N-(2-butyl-3-(4-(3-(dibutylamino)propoxy)benzoyl)benzofuran-5-yl)- N-(methylsulfonyl)methane sulfonamide

Dronedarone Hydrochloride

17 N-[2-n-Butyl-3-[4-[3-(di-n-butylamino)propoxy]benzoyl] benzofuran-5-yl]methanesulfonamid -N-oxide

1638586-56-7 Dronedarone Hydrochloride

18 ( R)-(+)-1-(2-Naphthyl)ethylamine Hydrochloride

3906-16-9 Cinacalcet

Hydrochloride

NH

N+O

-O

OH

H Cl

O

NH O

O HN

S

O

O

O

H2N O

O

N

O

N O

O

N

S

O

O

SO

O

Page 3: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 3 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

19 ( R)-a-methyl-N-[3-[3-(trifluoromethyl)phenyl]methyl] -1-naphtalenemethane amine

Cinacalcet Hydrochloride

20 (1-Napthalen-1-yl-ethyl)-bis- [3-(3-triflurometyhl-phenyl]-propyl)-amine

1271930-15-4 Cinacalcet

Hydrochloride

21 ( R)-a-methyl-N-[3-[3-(trifluoromethyl) phenyl]methyl]-1-naphtalenemethane amine-N-oxide

1229224-94-5 Cinacalcet

Hydrochloride

22 (S)-N-[1-(1-naphthyl)ethyl]- 3-[3-(trifluoromethyl)phenyl]propan-1-aminehydrochloride

226256-56-0 Cinacalcet

Hydrochloride

23 (S)-N-((R)-1-(naphthalen-1-yl)ethyl)-2-(3-(trifluoromethyl)phenyl) propan-1-amine

Cinacalcet Hydrochloride

24 3-(3-(trifluoromethyl)phenyl)propyl 1-(naphthalen-5-yl)ethylcarbamate

Cinacalcet Hydrochloride

25 (R)-N-((R)-1-(naphthalen-1-yl)ethyl)-2-(3-(trifluoromethyl)phenyl)propan-1-amine

Cinacalcet Hydrochloride

26 (SR)-N-1-(naphthalen-1-yl)ethyl)-2-(3-(trifluoromethyl)phenyl) propan-1-amine

Cinacalcet Hydrochloride

27

2-(3-(trifluoromethyl)phenyl) propanalCinacalcet 2-(3-(trifluoromethyl)phenyl) propanal sodium bisulphate adduct

1034094-54-6

OH

SO3Na

F

FF

Cinacalcet Hydrochloride

HNF

F

F

CH3

F

F

FO

HN

O CH3

(R)NH

F

F F

(R)

NHF

F F

Page 4: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 4 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

28 (R)-N-(1-(naphthalen-2-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine

Cinacalcet Hydrochloride

29 Benzyl-carbamic acid isobutyl ester

Lacosamide

30 (R)-2-Acetamido-N-benzyl- -3-hydroxy propanamide 175481-38-6 Lacosamide

31 (R) -2-(benzylcarbamoyl)- 2-acetamidoethyl isobutyl carbonate

Lacosamide

32 (R)-2-Acetamido-3-benzylamino -3-oxopropyl acetate

Lacosamide

33 N-Benzylacetamide impurity

Lacosamide

34 (R)-2-Amino-N-benzyl-3- Methoxypropanamide 1322062-76-9 Lacosamide

35 ( R)-2-[(R)-2-acetamido-3-methoxy propanamido]- N-benzyl-3-methoxy propanamide

Lacosamide

36 (S)-2-acetamido-N-benzyl-3-hydroxypropanamide 171623-03-03 Lacosamide

37 (R)-2-acetamodo-N-benzyl-3-methoxy-N-methylpropanamide

Lacosamide

NH

O

O

O NH

O

NH

O

O

O

O NH

O

NH

O

O

NH

O

H3CO N

H

O

NHO

OCH3N

HH3C

O

O

N

OO

NH

HN

FF

F(R)

Page 5: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 5 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

38 (S)-2-acetamido-N-benzyl-3-methoxypropanamide 175481-37-5 Lacosamide

39 N-Benzyl-2-acetamido-2-propene acid amide impurity 86921-49-5 Lacosamide

40 2-Amino-N-benzyl-3-hydroxy-propionamide

Lacosamide

41 N-Benzyl-3-methoxy-2-propionylamino-propionamide 1318777-56-8 Lacosamide

42 Methyll 2-{[(4-N-hexyloxy carbonyl carbmimidaoyl phenyl)amino]methyl} -1-methyl-1H-benzimidazole-5-carboxylate

Dabigatran Etexilate Mesylate

43 Ethyl 2-{[(4-N-hexyloxy carbonyl carbmimidaoyl phenyl)amino]methyl} -1-methyl-1H-benzimidazole-5-carboxylate

Dabigatran Etexilate Mesylate

44 Ethyl 2-{[(4-carbamimidoylphenyl)amino]methyl}-1-methyl -1H-benzimidazole-5-carboxylate hydrochloride

Dabigatran Etexilate Mesylate

45 (E)-2-(((4-(N’-((hexyloxy )carbonyl) carbamimidoyl) phenyl) amino)methyl)-1-methyl-1H-benzo[d]imidazole-5-carboxylic acid

Dabigatran

NH

OH

H2N

O

N

O

N

N

HNNH

NHN

O

O

O

O

O

O

N

N

HNNH2

NH .HCl

HO

O

N

N

HNNH2

NH

N

N

O

OHHN

NH2

N

OO

Page 6: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 6 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

46 trans-(3aRS,12bRS)-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

129385-59-7 Asenapine

47 trans-(3aRS,12bRS)-11-chloro-2,3,3a,12b-tetrahydro-2-methyl-1H-dibenz [2,3:6,7]oxepino[4,5-c]pyrrol-1-one

129385-59-8 Asenapine

48 cis-(3aRS,12bRS)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1H-dibenz[2,3:6,7]oxepino[4,5-c]pyrrol-1-one

912356-09-3 Asenapine

49 8-Bromo-11- (1-methyl-4- piperidinylidene)-6,11-dihydro-5H- Benzo [5,6] cyclohepta [1,2-b] pyridine

130642-57-8 Desloratadine

50 3-[2-(3-chlorophenyl)ethyl] pyridine-2-carbonitrile 31255-57-9 Desloratadine

51 4-(8-Bromo-5,6-dihydro-benzo[5,6]cycloheptal[1,2b]pyridin-11-ylidene)-piperdine-1-carboxylic acid ethyl ester

Desloratadine

52 (1-methyl-4-piperidinyl)-3-[2-(3-chlorophenyl) ethyl]-2-pyridinyl-methanone

130642-50-1 Desloratadine.

53 8-bromo-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

117796-50-6

Desloratadine

N

N

Br

O O

Page 7: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 7 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

54 Isoleucine impurity of CBM 137863-88-8 Valsartan

55 (S)-N-butyryl-N-{[2’-(1H-tetrazole-5-yl) -biphenyl-4-yl]-methyl}valine

952652-79-8 Valsartan

56 Calcium (3R,5R)-3,5-dihydroxy-7-(2-isopropyl-4.5-diphenyl-3-(phenylcarbamoyl)-1H-pyrool-1-yl)heptanoate

433289-83-9 Atorvastatin

57 N-(1-cyanocyclopentyl)pentanamide 194984-24-2 Irbesartan

58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan

59

1,3-bis-(2-methoxyphenoxy)propane-2-ol 16929-60-5 Ranolazine

60 2, 2-Dichloro-N-(2, 6-dimethylphenyl) acetamide 39084-88-3 Ranolazine

61 1, 4-Bis-[(2, 6-dimethylphenyl)-aminocarbonylmethyl]piperazine

380204-72-8 Ranolazine

62

(3aR,4S,7R,7aS)-2-(((1S,2S)-2-((4-(benzo[d]isothiazol-3-yl) piperazin-1-yl)methyl)cyclohexyl)methyl)hexahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

1448443-35-3 Lurasidone

63 (E)-1-(3-trifluoromethyl-5,6-dihydro-[1,2,4]triazolo[4,3,a]pyrazin -7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-one

1253056-18-6 Sitagliptin

Page 8: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 8 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

64

(E)-1-(3-trifluoromethyl-5,6-dihydro-[1,2,4]triazolo[4,3,a]pyrazin -7(8H)-yl)-4-(2,4,5-trifluorophenyl)but-2-en-1-oneSitagliptin

OF

F F

N

NN

N

FFF

HN

Sitagliptin

65 (3R,4S)-1-(4-chlorophenyl)-3-((S)-3-(4-fluorophenyl)- 3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one

1700622-08-7 Ezetimibe

66 (3S,4S)-1-(4-fluorophenyl)-3-((S)-3-(4-fluorophenyl) -3-hydroxypropyl)-4-(4-hydroxyphenyl)azetidin-2-one

1593543-07-7 Ezetimibe

67

(4S)-3-((2R)-5-(4-fluorophenyl)-2-((S)-((4-fluorophenyl)amino)(4-hydroxyphenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one

Ezetimibe

68

(S)-3-((2R,5S)-5-(4-fluorophenyl)-2-((R)-((4-fluorophenyl)amino)(4-((trimethylsilyl)oxy)phenyl)methyl)-5-((trimethylsilyl)oxy)pentanoyl)-4-phenyloxazolidin-2-one

Ezetimibe

69 8-Bromo-3-methyl-1,7-bis((4methylquinazolin-2-yl) methyl)-1H-purine- 2,6(3H,7H)-dione

N

N

N

NO

O

N

N

N

N

Br

Linagliptin

70 8-Bromo-3-methyl-1,7-bis((4methylquinazolin-2-yl) methyl)-1H-purine- 2,6(3H,7H)-dione

N

N

N

NH

O

O

N

N

Br

Linagliptin

71 (Z)-8-bromo-7-(3-bromobut-2-en-1-yl) -3-methyl-1H-purine-2,6(3H,7H)-dione

N

N N

NH

O

O

Br

Br

Linagliptin

72

(R)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-8-(piperidin-3-ylamino)-1H-purine-2,6(3H,7H)-dione

1446263-38-2 Linagliptin

ONO

O

O Si

HO

N

FF

H

O

N

(S)

O

(R)

(S)

O

OSi

(R)

O Si

HN F

F

Page 9: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 9 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

73 (R)-8-(3-aminopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-6-((4-methylquinazolin-2-yl)methoxy)-3,7-dihydro-2H-purin-2-one

Linagliptin

74 (S)-8-(3-aminopiperidin-1-yl)-7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

668270-11-9 Linagliptin

75 7-(but-2-yn-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

Linagliptin

76 (R,E)-8-(3-aminopiperidin-1-yl)-7-(3-bromobut-2-en-1-yl)-3-methyl-1-((4-methylquinazolin-2-yl)methyl)-1H-purine-2,6(3H,7H)-dione

1638744-06-5 Linagliptin

77 8-bromo-1,7-di(but-2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Linagliptin

78 bromo-6-(1-bromoeth-5-fluoropyrimidine 1307315-02-1 Voriconazole

79 2-(4-Amino-1H-1,2,4-triazol-1-yl)- 1-(2,4-difluorophenyl)ethanone bromide

Voriconazole

80 (2R,3R/2S,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

239807-04-6 Voriconazole

81 (2R,3R/2S,3S)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol

137234-76-5 Voriconazole

82 (2R,3S/2S,3R)-3-(4-chloro-5-fluoropyrimidin-6-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl) butan-2-ol

137234-75-4 Voriconazole

NN

N

N OON

N

NH2N

.hemi tartrate

N

NN

N

O

O

N

N

F F

NN

N+ NH2

O .Br

Page 10: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

-Chemistry for Humanity- DOC NO-Sym imp-001/0416

Page 10 of 25 Symphony Pharma Life Sciences Pvt. Ltd.

Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

83 2S,3R-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol

137234-63-0 Voriconazole

84

(S)-2-((1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl)-1-((1R,3R,5R,7S)-3-hydroxyadamantan-1-yl)-2-oxoethan-1-aminium chloride

Saxagliptin

85

(S)-2-((1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl)-1-((1R,3R,5R,7S)-3-hydroxyadamantan-1-yl)-2-oxoethan-1-aminium chloride

1194836-77-5 Saxagliptin

86 1S,3S,5S)-2-((S)-2-(adamantan-1-yl)-2-aminoacetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Saxagliptin

87

tert-butyl ((S)-2-((1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl) -1-((1R,3R,5R,7S)-3-hydroxyadamantan-1-yl)-2-oxoethyl)carbamate

709031-43-6 Saxagliptin

88 tert-butyl((S)-2-((1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl)-1-((1R,3R,5S,7S)-3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate

Saxagliptin

89 (S)-2-((tert-butoxycarbonyl)amino)-2-((1r,3R,5S,7S)-3,5-dihydroxyadamantan-1-yl)acetic acid

681282-72-4 Saxagliptin

90 1S,3S,5S)-2-((S)-2-(adamantan-1-yl)-2-aminoacetyl)-2-azabicyclo[3.1.0]hexane-3-carbonitrile

Saxagliptin

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91 tert-butyl((S)-2-((1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-((1r,3R,5S,7S)-3,5-dihydroxyadamantan-1-yl)-2-oxoethyl)carbamate

862590-99-6 Saxagliptin

92 tert-butyl((R-)-2-((1S,3S,5S)-3-cyano-2-azabicyclo[3.1.0]hexan-2-yl)-1-((1R,3S,5R,7S)-3-hydroxyadamantan-1-yl)-2-oxoethyl)carbamate

1564266-92-7 Saxagliptin

93 7-methoxy-1-vinylnaphthalene 1095930-99-6 Agomelatine

94 2-(7-methoxy-1-naphthyl)ethyl formate

Agomelatine

95 N-[2-(7-hydroxy-1-naphthyl)ethyl]acetamide 152302-45-9 Agomelatine

96 2-(7-methoxy-1-naphthyl)ethanol 99416-99-6 Agomelatine

97 6-methyl-4-phenylchroman-2-ol 209747-04-6 Tolterodine

98 Bis{4-methyl-2-(3-phenylpropyl)phenol} 854306-72-2 Tolterodine

99 4-[Bis-(5-amino-1-methyl indol-3-yl) methyl]-3-methoxy benzoic acid methyl ester

Zafirlukast

100 4-[Bis-(5-cyclopentyloxycarbonylamino-l-methyl indol-3-y1)-methyl] - 3-methoxy-benzoic acid

Zafirlukast

O

O

O

H

O

O

O

N

H2N

N

NH2

O

OHO

NH

HN

O

O

HN

NH

O O

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101 4-[[5-Cyclopentyloxy carbonyl amino-2- [(3-methoxy benzoic acid-4-y1)-methyl]-1-methyl indol-3-yl] - methyl] - 3-methoxy- benzoic acid.

Zafirlukast

102 Dimethyl 4,4'-((5-amino-1-methyl-1H-indole-2,3-diyl)bis(methylene))bis(3-methoxybenzoate)

Zafirlukast

103 4-(bis(5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid methyl ester

Zafirlukast

104

4-(bis(5-(((cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acid

Zafirlukast

105 dicyclopentyl (((2-methoxy-4-((o-tolylsulfonyl)carbamoyl)phenyl)methylene)bis(1methyl-1H-indole-3,5-diyl))dicarbamate

Zafirlukast

106

4-[[5-Cyclopentyloxy carbonyl amino-2- [(3-methoxy benzoic acid methyl ester-4-yl)-methyl]-1-methyl indol-3-yl] - methyl] - 3-methoxy- benzoic acid methyl ester

Zafirlukast

107 Methyl 4-(5-nitro-1-methyl indol-3-yl methyl)-3-methoxy benzoate

Zafirlukast

108 (2S)-2-[[(4S)-4-[[4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]-4-carboxybutanoyl]amino]pentanedioic acid.

144051-68-3 Pemetrexed

O

OH

O

N

O

HO

O

HN

O

O

N

O

O

H2N

O

O

OO

O

OCH3

O

N

HN

O

O

N

NH

O O

O

OHO

N

HN

O

O

N

NH

O O

O

O

N

HN

O

O

N

NH

O O

HN S

OO

O

O

O

N

O

O

O

HN

O

O

O

O

O

N

N+O

O-

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109 (2R)-2-[[4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]-pentanedioic acid

182009-04-7 Pemetrexed

110

(S)-4-(4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)-5-methoxy-5-oxopentanoic acid

1265908-63-1 Pemetrexed

111 sodium (S)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)-5-methoxy-5-oxopentanoate

1265908-60-8 Pemetrexed

112 4-amino-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

19171-19-8 Lenalidomide

113 methyl ((1R,4S)-4-isopropylcyclohexane-1-carbonyl)-L-phenylalaninate

958230-63-2 Nateglinide

114 (R)-3-(aminomethyl)-5-methylhexanoic acid 148553-51-9 Pregabalin

115 ((S)-4-cyclohexyl-1-ethoxy-1-oxobutan-2-yl)-L-alanine

Enalapril

116 ((S)-4-cyclohexyl-1-ethoxy-1-oxobutan-2-yl)-L-alanyl-L-proline

Enalapril

117 2-methyl-N-[4-cyano-3-(trifluoromethyl)phenyl]-2-propenamideimpurity-B

90357-53-2 Bicalutamide

118 N-[4-cyano-3-(trifluoromethyl)phenyl]-3-[(2-fluorophenyl)-sulfonyl]-2-hydroxy-2-methyl-propanamide

1159977-36-2 Bicalutamide

119 (+)N-[4-nitro-3-(trifluoromethyl) phenyl]-3-[(4-fluorophenyl)-sulfonyl]-2-hydroxy-2-methyl-propanamide

90357-00-9 Bicalutamide

HO

O

NH

O

O

N

OOH

O

NH

O

O

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120 (S,E)-1-(2-(3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)-3-hydroxypropyl)phenyl)ethan-1-one

184764-13-4 Montelukast

121 [[(1H-benzimidazole-2-yl)sulfinyl]methyl]-3-methyl-4- (2,2,2-trifluoroethoxy)-pyridine 1-oxide

213476-12-1 Lansoprazole

122 1-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-yl)ethan-1-one

58905-16-1 Fluconazole

123 2-(4-fluorophenyl)-1,3-bis (1H-1, 2,4-triazol-1-yl)- propan-2-ol

81886-51-3 Fluconazole

124

(2S,3aS,6aS)-1-(((S)-1-isopropoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

295328-72-2 Ramipril

125 (S)-10-hydroxy-10,11-dihydro-5H-dibenz[b,f]azepine 1431547-14-6 Eslicarbazepine

126 1-(9H-carbazol-4-yloxy)-3-(benzyl(2-(2-methoxy phenoxy)ethyl)amino)propan-2-ol

Carvedilol

127 (3R,5R,E)-7-(4-(4-Fluorophenyl)-6-isopropyl-2-[methylsulfonamido)pyrimidin-5-yl]-3-,5-dihydroxyhept-6-enoate

1422515-55-6 Rosuvastatin

128 6-(5-Chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-oneImpurity C

148891-53-6 Eszopiclone

129 2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)-3-hydroxypropyl propionate

194159-18-7 Valganciclovir

OH

NH

O

O

O

NH

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130 2-((2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)-3-hydroxypropyl ((benzyloxy)carbonyl)-D-valinate

Valganciclovir

131 2-((2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)-3-hydroxypropyl D-valinate

1394000-00-0 Valganciclovir

132 2-((2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy)propane-1,3-diyl (2R,2'R)-bis(2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate)

Valganciclovir

133 4,5-diphenyl-2-oxazole propionamide

Oxaprozin

134 Methyl-4,5-diphenyl-2-oxazole propionate

Oxaprozin

135 Ethyl methyl 2,6-bis[(2-aminoethoxy)methyl]-4-(2- chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

721958-74-3 Amlodipine

136 2,2'-((3-fluoro-4-morpholinophenyl)azanediyl)bis(2-hydroxypropane-3,1-diyl))bis(isoindoline-1,3-dione

Linezolid

137 (R)-N-[[3-{3-Fluoro-4-(4-morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl]-acetamide

872992-20-6 Linezolid

HN

N

N

O

H2N N

O

OH

O CH3

CH3

HN

O

O

O

HN

N

N

O

H2N N

O

O

O CH3

CH3

HN

O

CH3H3C

NH

OO

O

O

O

O

NO

NH2

O

N

O

O

N

O

O

N

OH

O

O

F

N

O

OH

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138 4-(4-(dimethylamino)butanoyl)-3-(hydroxylmethyl)benzonitrile

1433278-33-1 Escitalopram

Oxalate

139 N-cyano-3-(((2-((diaminomethylene)amino)thiazol-4-yl)methyl)thio)propanimidamide

76823-97-7 Famotidine

140 ethyl (R)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

180468-41-1 Solifenacin

141 3-(4-chlorobutanoyl)-1H-indole-5-carbonitrile 276863-95-7 Vilazodone

142

5-(4-(4-(5-cyano-1-(4-(5-cyano-1H-indol-3-yl)butyl)-1H-indol-3-yl)butyl)piperazin-1-yl)benzofuran-2-carboxamide

Vilazodone

143 2-(2,3-Dichlorophenyl)-2-(guanidinylimino)acetonitrile 84689-20-3 Lamotrigine

144 6-(2,4-dichloro-phenyl)-[1,2,4]triazine-3,5-diyldiamine 38943-76-9 Lamotrigine

145 4'-[[7-Methyl-5-(1-Methyl-1H-benzimidazol-2-yl)-2-propyl-1H benzimidazol-1-yl] methyl] biphenyl-2-carboxylic acid

1026353-20-7 Telmisartan

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146 (Z)-2-(2-oxopyrrolidin-1-yl)but-2-enamide 358629-47-7 Levetiracetam

147 5-chloro-N-(4-(3-oxo-4-morpholino)phenyl)-N-((2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide

Rivaroxaban

148 6,7-dihydrothieno[3,2-c]pyridin-4(5H)-one 68559-60-4 Clopidogrel

149 (5S)-2-Amino-5-(N,N-dibenzylamino)-4-oxo-1,6-diphenylhex-2-ene

156732-13-7 Ritonavir

150 (6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3,7-diyl)bis((4-(2-(piperidin-1-yl)ethoxy)phenyl)methanone)

1159977-58-8 Raloxifene

151 Methyl-4-(cyclopropyl-oxo-methyl)-a,a-dimethyl phenyl acetate.

Fexofenadine

152 (2R,3R)-3-(3-hydroxyphenyl)-N,N,2-trimethylpentan-1-amine oxide

Tapentadol

153 3-((2R,3R)-1-(diMethylaMino)-2-Methylpentan-3-yl)phenol hydrochloride

Tapentadol

S

O

N O

NHO

O

NO

Cl

O

O

O

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154 (2S,3aS,6aS)-1-(((S)-4-cyclohexyl-1-ethoxy-1-oxobutan-2-yl)-L-alanyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid

99742-35-5 Ramipril

155 [2S,3S,5S]-2-N,N-Dibenzylamino-3-hydroxy-5-(t-butyloxycarbonylamino)-1,6-diphenylhexane

162849-93-6 Ritonavir

156 Ethyl(2-amino-4-((2-fluorobenzyl)amino)phenyl) carbamate

1476737-81-1 Retigabine

157 [2,4-Bis-(2-fluoro-benzylamino)-phenyl]-carbamic acid ethyl ester

Retigabine

158 2-vinylbenzaldehyde 28272-96-0 Lacidipine

159 4-Fluoro-a-cyclopropylcarbonylbenzyl bromide 1359829-52-9 Prasugrel

160 3-Fluoro-a-cyclopropylcarbonylbenzyl bromide 1359829-72-3

Prasugrel

161 5-(2-cyclopropyl-1-(4-fluorophenyl)-2-oxoethyl)-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

1618107-98-4 Prasugrel

HN

NHNH

F

O

O

F

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162 5-(2-cyclopropyl-1-(3-fluorophenyl)-2-oxoethyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridin-2-yl acetate

1391194-39-0 Prasugrel

163 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen-1-amine

1450657-31-4 Apremilast

164 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-one

1450657-28-9 Apremilast

165 3-(4-acetamido-1,3-dioxoisoindolin-2-yl)phthalic acid

Apremilast

166 (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl) ethan-1-amine

608142-27-4 Apremilast

167 (R)-N-(2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methyl sulfonyl)ethyl)-1,3-dioxoisoindolin-4-yl) acetamide

608141-44-2 Apremilast

168 (S)-4-amino-2-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)isoindolin-1,3-dione

635705-72-5 Apremilast

169 2-(5-iodo-2-methylbenzyl)-5-phenylthiophene

Canagliflozin S

I

NH

O

O

O

N

HO

O

OH

O

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170 (2R,3S,4R,5R)-1-(3-(5-(4-fluorophenyl)thiophene-2-carbonyl)-4-methylphenyl)-2,3,4,5,6-pentahydroxyhexan-1-one

Canagliflozin

171 (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxy-1-(4-methyl-3-((5-phenylthiophen-2yl)methyl)phenyl)hexan-1-one

Canagliflozin

172 (2S,3R,4S,5S,6R)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

1030825-21-8 Canagliflozin

173

(2R,3R,4R,5R)-2-((R)-1,2-dihydroxyethyl)-5-(3-((5-(4-

fluorophenyl)thiophen-2-yl)methyl)-4-

methylphenyl)tetrahydrofuran-3,4-diol

Canagliflozin

174 (2R,3S,4R,5R,6S)-2-(hydroxymethyl)-6-(4-methyl-3-((5-phenylthiophen-2-yl)methyl)phenyl)tetrahydro-2H-pyran-3,4,5-triol

842133-16-8 Canagliflozin

175 (2R,3R,4R,5S)-2-((R)-1,2-dihydroxyethyl)-5-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)tetrahydrofuran-3,4-diol

Canagliflozin

176

1-((2S,3S)-2-(benzyloxy)pentan-3-yl)-2-formyl-N-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)hydrazine-1-carboxamide

Posaconazole

177

2-((2S,3R)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Posaconazole

O

S OH

OH

OH

OH

OH

N

NH

O

HN

N

N

HO

O

O

N

NN

O

NNHO

O

O

HOOH

SF

HO

HO

O

HOOH

SF

HO

HO

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178 N'-((2S,3S)-2-(benzyloxy)pentan-3-yl)formohydrazide 170985-85-0 Posaconazole

179 2-((2R,3R)-2-(benzyloxy)pentan-3-yl)-4-(4-(4-(4-hydroxyphenyl)piperazin-1-yl)phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Posaconazole

180

4-(4-(4-(4-(((3R,5R)-5-((1H-1,2,4-triazol-1-yl)methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methoxy)phenyl) piperazin-1-yl)phenyl)-2-((2S,3S)-2-hydroxy hexan-3-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one

Posaconazole

181 (S)-4-Isobutylpyrrolidin-2-one 181289-23-6 Pregabalin

182 4-isobutylpiperidone-2,6-dione 916982-10-0 Pregabalin

183 [2-[(2-aminophenyl)thio]phenyl]-[4-[2-(2-hydroxy-ethoxy)ethyl]piperazin-1-yl]methanone

848814-27-7 Quetiapine

184 N-(2-[[2-([4-[2-(2-hydroxyethoxy)ethyl]piperazin-1- yl] carbonyl)phenyl]thio]phenyl)acetamide

1371638-10-6 Quetiapine

N

NN

O

NN

HOO

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185 (S)-3-((R)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one

528565-93-7 Ezetimibe

186 (5R)-5-Phenyl morpholin-3-one 192815-71-7 Eliglustat

187 (5S)-5-Phenyl morpholin-3-one 1052209-96-7 Eliglustat

188 (5R)-N-Tert-Butyloxycarbonyl -3,4,5,6-Tetrahydro-5-Phenyl-4(H)-1,4-Oxazin-2-One

119878-90-9 Eliglustat

189 (5S)-N-Tert-Butyloxycarbonyl -3,4,5,6-Tetrahydro-5-Phenyl-4(H)-1,4-Oxazin-2-One

220077-24-7 Eliglustat

190 (2-Hydroxy-(1R)-phenyl ethyl amino)-acetic acid

Eliglustat

191 (2-Hydroxy-(1S)-phenyl ethyl amino)-acetic acid

Eliglustat

192 2-((1-benzylpiperidin-4-yl)methyl)-3-hydroxy-5,6-dimethoxy-2,3-dihydro-1H-inden-1-one

Donepezil

OO

O

NOH

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193 2-(2,6-dioxopiperidin-3-yl)-4-(hydroxyamino) isoindoline-1,3-dione

497147-11-2 Pomalidomide

194 2-(4-Chlorophenoxy)aniline (2770-11-8 Amoxapine

195 11-(piperazin-1-yl) dibenzo[b,f][1,4]oxazepin 21636-40-8 Amoxapine

196 Ethyl [2-(4-Chlorophenoxy)phenyl]carbamate 31879-60-4 Amoxapine

197 4-chloro-2(imino(phenyl)methyl)aniline 5606-39-3 Amoxapine

198 diethyl 2-aminomalonate 13433-00-6 Amoxapine

199 N-[2-(4-Chlorophenoxy)phenyl]piperazine-1-

carboxamide

Amoxapine

HN

O

Cl

N

O

NH

Page 24: -Chemistry for Humanity- DOC NO-Sym imp-001/0416sympharma.com/downloads/api-impurities-product-list.pdf58 4-chloro-4-methyl-5-methylene-1,3-dioxolan-2-one 95579-71-8 Olmesartan 59

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Plot.#7/A, Biotech Park, Phase-II, Genome Valley, Kolthur (V), Shameerpet (M), Medchal(Dist.), 500101,Telangana,India Website: www.sympharma.com Email: [email protected] Tel: +91- 9550352323

200 1,4-Bis(2-chlorodibenzo[b,f][1,4]oxazepine-11-

yl)piperazine

Amoxapine

201 11H-10λ2-dibenzo[b,f][1,4]oxazepin-11-one

Amoxapine

202 4-(2-Chlorodibenzo[b,f][1,4]oxazepin-11-yl)-N-[2-(4-

chlorophenoxy)phenyl] piperazine-1-carboxamide

Amoxapine

203 (2,8-dichloro-11-(piperazin-1-yl)

dibenzo[b,f][1,4]oxazepin-10-um-10-yl)methanide

Amoxapine

204 Ethyl 4-(2-chlorodibenzo[b,f][1,4]oxazepin-11-

yl)piperazine-1-carboxylate

Amoxapine

N

O Cl

N

N

NO

Cl

HN

O

O

HN

O

Cl

N

O

N N

O

Cl

N

O Cl

N

NH

Cl

N

O Cl

N

N

O

OEt

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205 (S)-6-fluoro-2-((R)-oxiran-2-yl)chromane 197706-51-7 Nebivolol

206 (R)-6-fluoro-2-((S)-oxiran-2-yl)chromane 129050-26-6 Nebivolol

207

(S)-2-(benzyl((R)-2-((R)-6-fluorochroman-2-yl)-2-

hydroxyethyl)amino)-1-((R)-6-fluorochroman-2-

yl)ethan-1-ol

1421916-53-1 Nebivolol

208 (R,1S,1'S)-2,2'-azanediylbis(1-((R)-6-fluorochroman-2-

yl)ethanol)hydrochloride 920275-23-6 Nebivolol

209

(S,1R,1'R)-2,2'-azanediylbis(1-((S)-6-fluorochroman-2-

yl)ethanol) hydrochloride 920275-19-0 Nebivolol

210 (R)-2-amino-1-((S)-6-fluorochroman-2-yl)ethan-1-ol 303176-42-3 Nebivolol

211 (S)-2-amino-1-((R)-6-fluorochroman-2-yl)ethan-1-ol 905454-41-3 Nebivolol


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