import os
import re
import numpy as np
from scipy.sparse.csgraph import shortest_path
import pandas as pd
pd.options.display.max_colwidth=500
ent_pattern = re.compile('T(\d+)\t([A-Z_]+) (\d+ \d+(;\d+ \d+)*)\t(.+)')
rel_pattern = re.compile('R(\d+)\t([A-Z_]+) Arg1:T(\d+) Arg2:T(\d+)')
ref_pattern = re.compile('R(\d+)\tCOREFERENCE Arg1:T(\d+) Arg2:T(\d+)')
folder = './test/sample/'
for filename in os.listdir(folder):
if filename.endswith('.ann'):
with open(folder + filename, 'r', encoding='utf8') as fin:
text = fin.read()
rels = rel_pattern.findall(text)
if len(rels) == 0:
continue
assert len(rels) == int(rels[-1][0])
df_ent = pd.DataFrame([(e[0], e[1], e[2], e[4]) for e in ent_pattern.findall(text)],
columns=['id', 'type', 'range', 'text']).set_index('id')
df_ref = pd.DataFrame(ref_pattern.findall(text), columns=['id', 'ent1', 'ent2'])
df = df_ref.join(df_ent, on='ent1', rsuffix='1').join(df_ent, on='ent2', rsuffix='2')
common_span = set(df['range']) & set(df['range2'])
if len(common_span) != 0:
print(filename)
display(df)
coref_dict = {r:e for e, r in zip(df['ent1'], df['range'])}
ent_dict = {r:e for e, r in zip(df['ent2'], df['range2'])}
all_spans = sorted(set(df['range']) | set(df['range2']))
num_spans = len(all_spans)
df_graph = pd.DataFrame(np.zeros((num_spans, num_spans), dtype=int), index=all_spans, columns=all_spans)
for r1, r2 in zip(df['range'], df['range2']):
df_graph.loc[r1, r2] = 1
d = shortest_path(df_graph.values, directed=True)
print('new rels')
new_rels = []
for e1, e2 in zip(*np.where(((~np.isinf(d)) & (d>1)))):
r1 = all_spans[e1]
r2 = all_spans[e2]
new_rels.append((coref_dict[r1], ent_dict[r2]))
with open(folder + filename, 'a', encoding='utf8') as fout:
for i, (e1, e2) in enumerate(new_rels, start=len(rels)+1):
rel_str = 'R%d\tCOREFERENCE Arg1:T%s Arg2:T%s'%(i, e1, e2)
print(rel_str)
fout.write(rel_str + '\n')
0001.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 11 | 18 | 1 | COREFERENCE | 701 802 | 400 mg (88%) of [5-(2,3-difluorophenyl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-acetic acid | ENTITY | 6 91 | [5-(2,3-difluorophenyl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-acetic acid |
1 | 12 | 13 | 12 | COREFERENCE | 830 843 | a white solid | ENTITY | 701 802 | 400 mg (88%) of [5-(2,3-difluorophenyl)-3-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-acetic acid |
new rels R13 COREFERENCE Arg1:T13 Arg2:T1 0002.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 7 | 4 | COREFERENCE | 601 612 | the solvent | ENTITY | 367 395 | ethanol (20 mL)/water (5 mL) |
1 | 7 | 9 | 8 | COREFERENCE | 691 703 | yellow solid | ENTITY | 614 632;671 687 | The title compound (1.180 g, 95.2%) |
2 | 8 | 13 | 1 | COREFERENCE | 614 632;671 687 | The title compound (1.180 g, 95.2%) | ENTITY | 22 139 | N-(3-chloro-4-fluorophenyl)-N-(2-fluoro-4-(hydrazinecarbonyl)benzyl)tetrahydro-2H-thiopyran-4-carboxamide 1,1-dioxide |
new rels R9 COREFERENCE Arg1:T9 Arg2:T1 0003.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 6 | 15 | 8 | COREFERENCE | 451 460 | The solid | ENTITY | 442 449 | a solid |
1 | 9 | 16 | 2 | COREFERENCE | 518 550 | the title compound (72 mg, 62 %) | ENTITY | 111 116 | LXXVI |
2 | 10 | 17 | 1 | COREFERENCE | 111 116 | LXXVI | ENTITY | 30 109 | 2'-amino-6-(2-amino-6-morpholinopyrimidin-4-yl)-3'-fluoro-[2,4'-bipyridin]-5-ol |
new rels R11 COREFERENCE Arg1:T16 Arg2:T1 0006.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 7 | 4 | COREFERENCE | 520 531 | the solvent | ENTITY | 294 309 | ethanol (10 mL) |
1 | 10 | 12 | 11 | COREFERENCE | 720 732 | a foam solid | ENTITY | 681 716 | the title compound (0.115 g, 95.8%) |
2 | 11 | 17 | 1 | COREFERENCE | 681 716 | the title compound (0.115 g, 95.8%) | ENTITY | 22 109 | N-((5-(hydrazinecarbonyl)pyridin-2-yl)methyl)-1-methyl-N-phenylpiperidine-4-carboxamide |
new rels R12 COREFERENCE Arg1:T12 Arg2:T1 0007.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 19 | 33 | 20 | COREFERENCE | 1268 1293 | the compound of Example 8 | ENTITY | 1126 1239 | 1-(4-(dimethylamino)piperidin-1-yl)-3-(1-ethyl-1H-imidazol-2-yl)-3-hydroxypropan-1-one (0.221 g, 0.751 mmol, 43%) |
1 | 20 | 22 | 21 | COREFERENCE | 1298 1313 | a colorless oil | ENTITY | 1268 1293 | the compound of Example 8 |
2 | 21 | 32 | 1 | COREFERENCE | 1126 1239 | 1-(4-(dimethylamino)piperidin-1-yl)-3-(1-ethyl-1H-imidazol-2-yl)-3-hydroxypropan-1-one (0.221 g, 0.751 mmol, 43%) | ENTITY | 25 111 | 1-(4-(dimethylamino)piperidin-1-yl)-3-(1-ethyl-1H-imidazol-2-yl)-3-hydroxypropan-1-one |
new rels R22 COREFERENCE Arg1:T33 Arg2:T1 R23 COREFERENCE Arg1:T22 Arg2:T20 R24 COREFERENCE Arg1:T22 Arg2:T1 0008.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 3 | 6 | 2 | COREFERENCE | 229 232 | 87% | ENTITY | 48 69 | 12.12 g of Compound 7 |
1 | 4 | 7 | 1 | COREFERENCE | 48 69 | 12.12 g of Compound 7 | ENTITY | 37 47 | Compound 7 |
new rels R5 COREFERENCE Arg1:T6 Arg2:T1 0009.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 7 | 5 | COREFERENCE | 251 262 | the solvent | ENTITY | 149 160 | DMF (14 mL) |
1 | 7 | 15 | 9 | COREFERENCE | 382 388 | eluent | ENTITY | 360 378 | CH2Cl2/MeOH (10:1) |
2 | 10 | 12 | 11 | COREFERENCE | 415 434 | a light brown solid | ENTITY | 397 411;435 450 | the product 34 (273 mg, 76.4%) |
3 | 11 | 17 | 1 | COREFERENCE | 397 411;435 450 | the product 34 (273 mg, 76.4%) | ENTITY | 13 24 | Compound 34 |
new rels R12 COREFERENCE Arg1:T12 Arg2:T1 0010.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 18 | 1 | COREFERENCE | 114 124 | compound 7 | ENTITY | 10 112 | N-(2-Methoxy-4-(piperidin-4-yl)phenyl)-3-(2-methoxyphenyl)-3H-[1,2,3]tria zolo[4,5-d]pyrimidin-5-amine |
1 | 4 | 19 | 6 | COREFERENCE | 398 410 | the solution | ENTITY | 259 280 | the reaction solution |
2 | 14 | 17 | 16 | COREFERENCE | 814 826 | This product | ENTITY | 774 812 | a yellow solid 7-c (6.9 g, yield: 82%) |
3 | 15 | 24 | 3 | COREFERENCE | 774 812 | a yellow solid 7-c (6.9 g, yield: 82%) | ENTITY | 141 153 | compound 7-c |
new rels R16 COREFERENCE Arg1:T17 Arg2:T3 0011.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 15 | 1 | COREFERENCE | 16 85 | 7-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indolin-2-one | ENTITY | 0 14 | Intermediate 5 |
1 | 4 | 7 | 16 | COREFERENCE | 328 339 | The solvent | ENTITY | 200 211 | TFA (11 mL) |
2 | 11 | 14 | 13 | COREFERENCE | 529 556 | a white solid (861 mg, 58%) | ENTITY | 507 525 | the title compound |
3 | 12 | 20 | 3 | COREFERENCE | 507 525 | the title compound | ENTITY | 94 123 | 5-Bromo-7-chloroindolin-2-one |
new rels R13 COREFERENCE Arg1:T14 Arg2:T3 0012.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 17 | 16 | COREFERENCE | 601 639 | a light yellow oil (105 mg, 74% yield) | ENTITY | 579 597 | the title compound |
1 | 2 | 18 | 2 | COREFERENCE | 579 597 | the title compound | ENTITY | 17 70 | 8-Bromo-2-(tert-butyl)-7-methylimidazo[1,2-a]pyridine |
2 | 3 | 19 | 1 | COREFERENCE | 17 70 | 8-Bromo-2-(tert-butyl)-7-methylimidazo[1,2-a]pyridine | ENTITY | 0 15 | Intermediate 41 |
3 | 4 | 20 | 21 | COREFERENCE | 279 287 | The vial | ENTITY | 74 90 | a microwave vial |
new rels R18 COREFERENCE Arg1:T18 Arg2:T1 R19 COREFERENCE Arg1:T17 Arg2:T1 R20 COREFERENCE Arg1:T17 Arg2:T2 0013.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 3 | 2 | COREFERENCE | 331 334 | 76e | ENTITY | 179 330;335 355 | (E)-methyl 3-(4-((1R,3R/1S,3S)-6-bromo-2-(2-fluoro-2-methylpropyl)-3-methyl-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridin-1-yl)-3,5-difluorophenyl)acrylate (200 mg, 0.373 mmol) |
1 | 2 | 5 | 4 | COREFERENCE | 425 428 | 17a | ENTITY | 357 424;429 449 | 1-ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (166 mg, 0.746 mmol) |
2 | 14 | 23 | 1 | COREFERENCE | 1167 1186;971 1162 | (110 mg, yield 53%) the title compound (E)-methyl 3-(4-((1R,3R/1S,3S)-6-(1-ethyl-1H-pyrazol-4-yl)-2-(2-fluoro-2-methylpropyl)-3-methyl-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridin-1-yl)-3,5-difluoroph enyl)acrylate | ENTITY | 7 178 | (E)-methyl3-(4-((1R,3R/1S,3S)-6-(1-ethyl-1H-pyrazol-4-yl)-2-(2-fluoro-2-methylpropyl)-3-methyl-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridin-1-yl)-3,5-difluoroph enyl)acrylate |
3 | 15 | 16 | 15 | COREFERENCE | 1163 1166 | 76f | ENTITY | 1167 1186;971 1162 | (110 mg, yield 53%) the title compound (E)-methyl 3-(4-((1R,3R/1S,3S)-6-(1-ethyl-1H-pyrazol-4-yl)-2-(2-fluoro-2-methylpropyl)-3-methyl-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridin-1-yl)-3,5-difluoroph enyl)acrylate |
4 | 16 | 17 | 15 | COREFERENCE | 1190 1202 | a yellow oil | ENTITY | 1167 1186;971 1162 | (110 mg, yield 53%) the title compound (E)-methyl 3-(4-((1R,3R/1S,3S)-6-(1-ethyl-1H-pyrazol-4-yl)-2-(2-fluoro-2-methylpropyl)-3-methyl-1,2,3,4-tetrahydrobenzofuro[2,3-c]pyridin-1-yl)-3,5-difluoroph enyl)acrylate |
new rels R17 COREFERENCE Arg1:T16 Arg2:T1 R18 COREFERENCE Arg1:T17 Arg2:T1 0014.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 11 | 1 | COREFERENCE | 242 273 | compound 50-e (1.6g, yield 64%) | ENTITY | 13 26 | compound 50-e |
1 | 6 | 7 | 6 | COREFERENCE | 275 286 | The product | ENTITY | 242 273 | compound 50-e (1.6g, yield 64%) |
new rels R7 COREFERENCE Arg1:T7 Arg2:T1 0016.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 11 | 13 | 12 | COREFERENCE | 570 582 | a yellow oil | ENTITY | 502 566 | methyl 2-(2,3-dihydrobenzofuran-5-yl)acetate (4.0 g, yield: 93%) |
1 | 12 | 20 | 1 | COREFERENCE | 502 566 | methyl 2-(2,3-dihydrobenzofuran-5-yl)acetate (4.0 g, yield: 93%) | ENTITY | 5 53 | 2-(7-bromo-2,3-dihydrobenzofuran-5-yl)ethan-1-ol |
new rels R13 COREFERENCE Arg1:T13 Arg2:T1 0020.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 11 | 14 | 13 | COREFERENCE | 699 712 | colorless oil | ENTITY | 679 695 | (0.150 g, 94.9%) |
1 | 12 | 19 | 12 | COREFERENCE | 679 695 | (0.150 g, 94.9%) | ENTITY | 622 640 | The title compound |
2 | 13 | 20 | 1 | COREFERENCE | 622 640 | The title compound | ENTITY | 22 80 | N-(2-fluoro-4-(hydrazinecarbonyl)benzyl)-N-phenylacetamide |
new rels R14 COREFERENCE Arg1:T19 Arg2:T1 R15 COREFERENCE Arg1:T14 Arg2:T1 R16 COREFERENCE Arg1:T14 Arg2:T12 0021.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 10 | 13 | 11 | COREFERENCE | 784 815 | the title compound (33 mg, 53%) | ENTITY | 682 693 | The product |
1 | 11 | 18 | 1 | COREFERENCE | 682 693 | The product | ENTITY | 10 201 | 1,1-Dioxo-3,3-dibutyl-5-phenyl-7-methylthio-8-[N-((R)-α-{N-[1-(R)-2-(R)-1-(t-butoxycarbonyl)-1-hydroxy-prop-2-yl]carbamoyl}benzyl)carbamoylmethoxy]-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine |
new rels R12 COREFERENCE Arg1:T13 Arg2:T1 0023.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 14 | 17 | 15 | COREFERENCE | 834 847 | a brown solid | ENTITY | 736 830 | 1.1 g (48%) of 6-[(3-chloro-4-fluorophenyl)carbonyl]-1-oxa-6-azaspiro[2.5]octane-2-carbonitril |
1 | 15 | 23 | 1 | COREFERENCE | 736 830 | 1.1 g (48%) of 6-[(3-chloro-4-fluorophenyl)carbonyl]-1-oxa-6-azaspiro[2.5]octane-2-carbonitril | ENTITY | 8 87 | 6-[(3-chloro-4-fluorophenyl)carbonyl]-1-oxa-6-azaspiro[2.5]octane-2-carbonitril |
new rels R16 COREFERENCE Arg1:T17 Arg2:T1 0024.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 4 | 3 | COREFERENCE | 279 281 | 6a | ENTITY | 239 278;282 301;374 375 | 1-(benzo[b]thiophen-2-yl)propan-2-amine (155 mg, 0.811 mmol ) |
1 | 2 | 6 | 5 | COREFERENCE | 430 432 | 1b | ENTITY | 380 429;433 452 | 2-fluoro-2-methylpropyl trifluoromethanesulfonate (545 mg, 2.43 mmol) |
2 | 10 | 14 | 12 | COREFERENCE | 882 894 | a yellow oil | ENTITY | 765 856;860 878 | the title compound N-(1-(benzo[b]thiophen-2-yl)propan-2-yl)-2-fluoro-2-methylpropan-1-amine (75 mg, yield 35%) |
3 | 11 | 13 | 12 | COREFERENCE | 857 859 | 6b | ENTITY | 765 856;860 878 | the title compound N-(1-(benzo[b]thiophen-2-yl)propan-2-yl)-2-fluoro-2-methylpropan-1-amine (75 mg, yield 35%) |
4 | 12 | 18 | 2 | COREFERENCE | 765 856;860 878 | the title compound N-(1-(benzo[b]thiophen-2-yl)propan-2-yl)-2-fluoro-2-methylpropan-1-amine (75 mg, yield 35%) | ENTITY | 166 238 | N-(1-(benzo[b]thiophen-2-yl)propan-2-yl)-2-fluoro-2-methylpropan-1-amine |
new rels R13 COREFERENCE Arg1:T13 Arg2:T2 R14 COREFERENCE Arg1:T14 Arg2:T2 0025.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 12 | 14 | 13 | COREFERENCE | 993 1008 | a colorless gum | ENTITY | 805 989 | N,N'-(((((((2,2'-dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(methylene))bis(oxy))bis(2-methoxypyridine-6,3-diyl))bis(methylene))bis(azanediyl))bis(ethane-2,1-diyl))diacetamide (230 mg, 33%) |
1 | 13 | 15 | 1 | COREFERENCE | 805 989 | N,N'-(((((((2,2'-dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(methylene))bis(oxy))bis(2-methoxypyridine-6,3-diyl))bis(methylene))bis(azanediyl))bis(ethane-2,1-diyl))diacetamide (230 mg, 33%) | ENTITY | 7 177 | N,N'-(((((((2,2'-Dimethyl-[1,1'-biphenyl]-3,3'-diyl)bis(methylene))bis(oxy))bis(2-methoxypyridine-6,3-diyl))bis(methylene))bis(azanediyl))bis(ethane-2,1-diyl))diacetamide |
new rels R14 COREFERENCE Arg1:T14 Arg2:T1 0028.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 6 | 8 | 7 | COREFERENCE | 492 507 | a white crystal | ENTITY | 422 488 | (R)-3-aminoquinuclidine.monosulfate (4.85 g: 21.6 mmol, yield=78%) |
1 | 7 | 12 | 1 | COREFERENCE | 422 488 | (R)-3-aminoquinuclidine.monosulfate (4.85 g: 21.6 mmol, yield=78%) | ENTITY | 24 59 | (R)-3-aminoquinuclidine.monosulfate |
new rels R8 COREFERENCE Arg1:T8 Arg2:T1 0032.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 10 | 2 | COREFERENCE | 200 202 | 3b | ENTITY | 149 199;203 221 | 3-(2-((2-fluoro-2-methylpropyl)amino)propyl)phenol (113 mg, 0.5 mmol) |
1 | 2 | 15 | 5 | COREFERENCE | 314 316 | 1e | ENTITY | 262 313;317 335 | (E)-methyl 3-(3,5-difluoro-4-formylphenyl) acrylate (113 mg, 0.5 mmol) |
2 | 9 | 19 | 14 | COREFERENCE | 570 712;716 733 | (E)-methyl 3-(3,5-difluoro-4-((1S,3R/1R,3S)-2-(2-fluoro-2-methylpropyl)-6-hydroxy-3-methyl-1,2, 3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylate (15 mg, yield 7%) | ENTITY | 551 569 | the title compound |
3 | 10 | 20 | 11 | COREFERENCE | 713 715 | 3c | ENTITY | 570 712;716 733 | (E)-methyl 3-(3,5-difluoro-4-((1S,3R/1R,3S)-2-(2-fluoro-2-methylpropyl)-6-hydroxy-3-methyl-1,2, 3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylate (15 mg, yield 7%) |
4 | 11 | 21 | 12 | COREFERENCE | 737 751 | a yellow solid | ENTITY | 713 715 | 3c |
5 | 12 | 13 | 1 | COREFERENCE | 551 569 | the title compound | ENTITY | 7 148 | (E)-methyl 3-(3,5-difluoro-4-((1S,3R/1R,3S)-2-(2-fluoro-2-methylpropyl)-6-hydroxy-3-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl)acrylate |
new rels R13 COREFERENCE Arg1:T19 Arg2:T1 R14 COREFERENCE Arg1:T20 Arg2:T14 R15 COREFERENCE Arg1:T20 Arg2:T1 R16 COREFERENCE Arg1:T21 Arg2:T14 R17 COREFERENCE Arg1:T21 Arg2:T11 R18 COREFERENCE Arg1:T21 Arg2:T1 0033.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 9 | 1 | COREFERENCE | 257 268 | COMPOUND 14 | ENTITY | 18 255 | (S)-3-(3,5-DIFLUOROPHENYL)-N-((2R,6S,8AS,14AS,20S,23AS)-2,6-DIMETHYL-5,8,14,19,23-PENTAOXOOCTADECAHYDRO-1H,5H,14H,19H-PYRIDO[2,1-I]DIPYRROLO[2,1-C:2',1'-L]OXA[4,7,10,13]TETRAAZACYCLOHEXADECIN-20-YL)-2-(3-(4-ETHYLPHENYL)UREIDO)PROPANAMIDE |
1 | 2 | 10 | 2 | COREFERENCE | 271 282 | Compound 14 | ENTITY | 257 268 | COMPOUND 14 |
2 | 6 | 12 | 3 | COREFERENCE | 489 500 | Compound 14 | ENTITY | 271 282 | Compound 14 |
3 | 7 | 8 | 7 | COREFERENCE | 517 551 | a ligh yellow solid (35.7 mg, 44%) | ENTITY | 489 500 | Compound 14 |
new rels R8 COREFERENCE Arg1:T10 Arg2:T1 R9 COREFERENCE Arg1:T12 Arg2:T1 R10 COREFERENCE Arg1:T12 Arg2:T2 R11 COREFERENCE Arg1:T8 Arg2:T1 R12 COREFERENCE Arg1:T8 Arg2:T2 R13 COREFERENCE Arg1:T8 Arg2:T3 0034.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 13 | 1 | COREFERENCE | 126 233 | 1-(Cyclopropylmethyl)-6-(2-(2,4-dimethylthiazol-5-yl)ethyl)-4-methyl-pyrazolo [4,3 - d]pyrimidine-5,7-dione | ENTITY | 11 118 | 1-(Cyclopropylmethyl)-6-(2-(2,4-dimethylthiazol-5-yl)ethyl)-4-methyl-pyrazolo [4,3 - d]pyrimidine-5,7-dione |
1 | 11 | 12 | 2 | COREFERENCE | 762 896 | 1-(cyclopropylmethyl)-6-(2-(2,4-dimethylthiazol-5-yl)ethyl)-4-methyl-pyrazolo[4,3-d]pyrimidine-5,7-dione (20.0 mg) with a yield of 25% | ENTITY | 126 233 | 1-(Cyclopropylmethyl)-6-(2-(2,4-dimethylthiazol-5-yl)ethyl)-4-methyl-pyrazolo [4,3 - d]pyrimidine-5,7-dione |
new rels R12 COREFERENCE Arg1:T12 Arg2:T1 0035.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 12 | 6 | COREFERENCE | 670 695 | the compound of Example 7 | ENTITY | 511 641 | 1-(4-(dimethylamino)piperidin-1-yl)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)propan-1-one hydrochloride (0.0220 g, 0.0623 mmol, 79%) |
1 | 6 | 13 | 1 | COREFERENCE | 511 641 | 1-(4-(dimethylamino)piperidin-1-yl)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)propan-1-one hydrochloride (0.0220 g, 0.0623 mmol, 79%) | ENTITY | 25 126 | 1-(4-(dimethylamino)piperidin-1-yl)-3-hydroxy-3-(1-methyl-1H-imidazol-2-yl)propan-1-one hydrochloride |
2 | 7 | 8 | 7 | COREFERENCE | 700 713 | a white solid | ENTITY | 670 695 | the compound of Example 7 |
new rels R8 COREFERENCE Arg1:T12 Arg2:T1 R9 COREFERENCE Arg1:T8 Arg2:T1 R10 COREFERENCE Arg1:T8 Arg2:T6 0036.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 16 | 1 | COREFERENCE | 16 82 | 5-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-methoxypyridine | ENTITY | 0 15 | Intermediate 6B |
1 | 14 | 15 | 2 | COREFERENCE | 631 736 | the title compound 5-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-methoxypyridine (2.71 g, 95% yield) | ENTITY | 16 82 | 5-bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-2-methoxypyridine |
new rels R15 COREFERENCE Arg1:T15 Arg2:T1 0038.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 15 | 23 | 1 | COREFERENCE | 629 660 | Compound 132 (64 mg, 66% yield) | ENTITY | 20 32 | Compound 132 |
1 | 16 | 17 | 16 | COREFERENCE | 664 686 | a yellow oily material | ENTITY | 629 660 | Compound 132 (64 mg, 66% yield) |
new rels R17 COREFERENCE Arg1:T17 Arg2:T1 0042.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 14 | 18 | 17 | COREFERENCE | 1058 1074 | a colourless gum | ENTITY | 916 1054 | (1S,3R)-1-(5-bromo-3-fluoropyridin-2-yl)-2-((1-fluorocyclopropyl)methyl)-3,5-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-amine (0.672 g, 63%) |
1 | 15 | 23 | 1 | COREFERENCE | 916 1054 | (1S,3R)-1-(5-bromo-3-fluoropyridin-2-yl)-2-((1-fluorocyclopropyl)methyl)-3,5-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-amine (0.672 g, 63%) | ENTITY | 15 138 | (1S,3R)-1-(5-bromo-3-fluoropyridin-2-yl)-2-((1-fluorocyclopropyl)methyl)-3,5-dimethyl-1,2,3,4-tetrahydroisoquinolin-6-amine |
new rels R16 COREFERENCE Arg1:T18 Arg2:T1 0043.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 6 | 15 | 8 | COREFERENCE | 760 786 | the compound of Example 14 | ENTITY | 609 732 | (S)-1-(3-(dimethylamino)piperidin-1-yl)-3-(1-methyl-1H-imidazol-2-yl)propan-1-one hydrochloride (0.0576 g, 0.171 mmol, 53%) |
1 | 7 | 10 | 9 | COREFERENCE | 791 804 | a white solid | ENTITY | 760 786 | the compound of Example 14 |
2 | 8 | 16 | 2 | COREFERENCE | 609 732 | (S)-1-(3-(dimethylamino)piperidin-1-yl)-3-(1-methyl-1H-imidazol-2-yl)propan-1-one hydrochloride (0.0576 g, 0.171 mmol, 53%) | ENTITY | 24 119 | (S)-1-(3-(dimethylamino)piperidin-1-yl)-3-(1-methyl-1H-imidazol-2-yl)propan-1-one Hydrochloride |
new rels R9 COREFERENCE Arg1:T15 Arg2:T2 R10 COREFERENCE Arg1:T10 Arg2:T2 R11 COREFERENCE Arg1:T10 Arg2:T8 0044.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 20 | 1 | COREFERENCE | 41 135 | 1-ethyl-N-phenyl-N-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)azetidine-3-carboxamide | ENTITY | 25 39 | compound 11139 |
1 | 2 | 21 | 2 | COREFERENCE | 158 172 | compound 11139 | ENTITY | 41 135 | 1-ethyl-N-phenyl-N-(4-(5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)azetidine-3-carboxamide |
2 | 17 | 19 | 18 | COREFERENCE | 1009 1022 | a white solid | ENTITY | 970 1005 | the title compound (0.042 g, 42.8%) |
3 | 18 | 27 | 3 | COREFERENCE | 970 1005 | the title compound (0.042 g, 42.8%) | ENTITY | 158 172 | compound 11139 |
new rels R19 COREFERENCE Arg1:T19 Arg2:T3 R20 COREFERENCE Arg1:T19 Arg2:T1 R21 COREFERENCE Arg1:T19 Arg2:T2 R22 COREFERENCE Arg1:T21 Arg2:T1 R23 COREFERENCE Arg1:T27 Arg2:T1 R24 COREFERENCE Arg1:T27 Arg2:T2 0045.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 12 | 14 | 13 | COREFERENCE | 948 967 | a light brown solid | ENTITY | 818 944 | (6S,8R)-6-(5-bromopyridin-2-yl)-7-(2,2-difluoroethyl)-8-methyl-6,7,8,9-tetrahydro-3H-pyrazolo[4,3-f]isoquinoline (438 mg, 60%) |
1 | 13 | 21 | 1 | COREFERENCE | 818 944 | (6S,8R)-6-(5-bromopyridin-2-yl)-7-(2,2-difluoroethyl)-8-methyl-6,7,8,9-tetrahydro-3H-pyrazolo[4,3-f]isoquinoline (438 mg, 60%) | ENTITY | 15 127 | (6S,8R)-6-(5-bromopyridin-2-yl)-7-(2,2-difluoroethyl)-8-methyl-6,7,8,9-tetrahydro-3H-pyrazolo[4,3-f]isoquinoline |
new rels R14 COREFERENCE Arg1:T14 Arg2:T1 0046.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 5 | 7 | 6 | COREFERENCE | 521 536 | a white crystal | ENTITY | 449 517 | racemic 3-aminoquinuclidine.diacetate (4.41 g: 39.0 mmol, yield=89%) |
1 | 6 | 11 | 1 | COREFERENCE | 449 517 | racemic 3-aminoquinuclidine.diacetate (4.41 g: 39.0 mmol, yield=89%) | ENTITY | 36 73 | racemic 3-aminoquinuclidine.diacetate |
new rels R7 COREFERENCE Arg1:T7 Arg2:T1 0049.ann
id | ent1 | ent2 | type | range | text | type2 | range2 | text2 | |
---|---|---|---|---|---|---|---|---|---|
0 | 1 | 11 | 1 | COREFERENCE | 112 205 | 7-(Cyclopropylmethyl)-1-(5-isopropylisoxazol-4-yl)methyl)-3-methyl-1H-purine-2,6(3H,7H)-dione | ENTITY | 11 104 | 7-(Cyclopropylmethyl)-1-(5-isopropylisoxazol-4-yl)methyl)-3-methyl-1H-purine-2,6(3H,7H)-dione |
1 | 9 | 10 | 2 | COREFERENCE | 638 761 | 7-(cyclopropylmethyl)-1-(5-isopropylisoxazol-4-yl)methyl)-3-methyl-1H-purine-2,6(3H,7H)-dione (80.0 mg) with a yield of 37% | ENTITY | 112 205 | 7-(Cyclopropylmethyl)-1-(5-isopropylisoxazol-4-yl)methyl)-3-methyl-1H-purine-2,6(3H,7H)-dione |
new rels R10 COREFERENCE Arg1:T10 Arg2:T1