HUE029988T2 - Diaminopyrimidine derivatives and processes for their preparation - Google Patents

Info

Publication number

HUE029988T2

HUE029988T2 HUE12750114A HUE12750114A HUE029988T2 HU E029988 T2 HUE029988 T2 HU E029988T2 HU E12750114 A HUE12750114 A HU E12750114A HU E12750114 A HUE12750114 A HU E12750114A HU E029988 T2 HUE029988 T2 HU E029988T2

Authority

HU

Hungary

Prior art keywords

group

pyrrolidin

amino

propylpyrimidin

optionally substituted

Prior art date

2011-02-25

Links

• Espacenet
• Global Dossier
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• 238000000034 method Methods 0.000 title claims description 152
• 238000002360 preparation method Methods 0.000 title claims description 146
• 230000008569 process Effects 0.000 title claims description 6
• MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 title description 9
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 378
• -1 alkylcarbonyl amine Chemical class 0.000 claims description 308
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 263
• 150000001875 compounds Chemical class 0.000 claims description 256
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 234
• 229910052736 halogen Inorganic materials 0.000 claims description 217
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 216
• 150000002367 halogens Chemical class 0.000 claims description 211
• 125000000217 alkyl group Chemical group 0.000 claims description 204
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 191
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 173
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 161
• YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 154
• 125000001424 substituent group Chemical group 0.000 claims description 130
• 229910052739 hydrogen Inorganic materials 0.000 claims description 87
• 239000001257 hydrogen Substances 0.000 claims description 87
• 238000006243 chemical reaction Methods 0.000 claims description 66
• 150000003839 salts Chemical class 0.000 claims description 62
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
• 230000002829 reductive effect Effects 0.000 claims description 60
• 125000002541 furyl group Chemical group 0.000 claims description 58
• 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 55
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 48
• 125000003545 alkoxy group Chemical group 0.000 claims description 47
• 125000004076 pyridyl group Chemical group 0.000 claims description 47
• 125000001544 thienyl group Chemical group 0.000 claims description 47
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 44
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 43
• 239000000203 mixture Substances 0.000 claims description 43
• 125000003386 piperidinyl group Chemical group 0.000 claims description 43
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 42
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 42
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 42
• 125000004193 piperazinyl group Chemical group 0.000 claims description 40
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 39
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 39
• 125000001041 indolyl group Chemical group 0.000 claims description 38
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 35
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 35
• 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 33
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 33
• 125000000335 thiazolyl group Chemical group 0.000 claims description 32
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 31
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
• 125000002971 oxazolyl group Chemical group 0.000 claims description 30
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 30
• 125000002883 imidazolyl group Chemical group 0.000 claims description 29
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 29
• 125000001425 triazolyl group Chemical group 0.000 claims description 29
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
• 206010010774 Constipation Diseases 0.000 claims description 24
• 125000001072 heteroaryl group Chemical group 0.000 claims description 23
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 23
• 230000005176 gastrointestinal motility Effects 0.000 claims description 21
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 20
• 125000003282 alkyl amino group Chemical group 0.000 claims description 19
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 19
• 208000021302 gastroesophageal reflux disease Diseases 0.000 claims description 19
• 208000002551 irritable bowel syndrome Diseases 0.000 claims description 19
• 238000004519 manufacturing process Methods 0.000 claims description 19
• 241001024304 Mino Species 0.000 claims description 18
• 230000004064 dysfunction Effects 0.000 claims description 17
• 206010021518 Impaired gastric emptying Diseases 0.000 claims description 16
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
• 239000003814 drug Substances 0.000 claims description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims description 15
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
• 150000001412 amines Chemical class 0.000 claims description 14
• 239000002253 acid Substances 0.000 claims description 13
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 13
• 125000002393 azetidinyl group Chemical group 0.000 claims description 13
• 150000002431 hydrogen Chemical class 0.000 claims description 13
• 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 13
• 125000006242 amine protecting group Chemical group 0.000 claims description 12
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 11
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 11
• 150000007524 organic acids Chemical class 0.000 claims description 11
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 10
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
• 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 10
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
• 206010052105 Gastrointestinal hypomotility Diseases 0.000 claims description 9
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 9
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 8
• 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 8
• 206010012601 diabetes mellitus Diseases 0.000 claims description 8
• 229940079593 drug Drugs 0.000 claims description 8
• 201000005081 Intestinal Pseudo-Obstruction Diseases 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 7
• 230000003111 delayed effect Effects 0.000 claims description 7
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 5
• 150000001408 amides Chemical class 0.000 claims description 5
• 239000003795 chemical substances by application Substances 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000000843 powder Substances 0.000 claims description 5
• 208000011580 syndromic disease Diseases 0.000 claims description 5
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 210000004556 brain Anatomy 0.000 claims description 4
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 4
• FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
• 230000002159 abnormal effect Effects 0.000 claims description 3
• 230000000968 intestinal effect Effects 0.000 claims description 3
• 150000002576 ketones Chemical class 0.000 claims description 3
• HDCCJUCOIKLZNM-UHFFFAOYSA-N n-pyrrolidin-3-ylacetamide Chemical compound CC(=O)NC1CCNC1 HDCCJUCOIKLZNM-UHFFFAOYSA-N 0.000 claims description 3
• 238000010992 reflux Methods 0.000 claims description 3
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
• 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 2
• 125000004432 carbon atom Chemical group C* 0.000 claims description 2
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
• 210000001035 gastrointestinal tract Anatomy 0.000 claims description 2
• 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
• HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 2
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 9
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 6
• 125000004429 atom Chemical group 0.000 claims 6
• ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 5
• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 4
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
• PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 4
• 150000003573 thiols Chemical class 0.000 claims 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 3
• 125000003118 aryl group Chemical group 0.000 claims 3
• PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 3
• JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 3
• 239000001294 propane Substances 0.000 claims 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
• BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims 2
• FSCNUJMKSQHQSY-UHFFFAOYSA-N Gein Chemical compound COC1=CC(CC=C)=CC=C1OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)CO2)O)O1 FSCNUJMKSQHQSY-UHFFFAOYSA-N 0.000 claims 2
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
• 229920006328 Styrofoam Polymers 0.000 claims 2
• 241000009298 Trigla lyra Species 0.000 claims 2
• 150000001298 alcohols Chemical class 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 150000004665 fatty acids Chemical group 0.000 claims 2
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
• MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 2
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
• 229920000889 poly(m-phenylene isophthalamide) Polymers 0.000 claims 2
• 239000002244 precipitate Substances 0.000 claims 2
• VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical group OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 claims 2
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims 2
• 229930185107 quinolinone Natural products 0.000 claims 2
• 210000002784 stomach Anatomy 0.000 claims 2
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• 239000000126 substance Substances 0.000 claims 2
• 229910052717 sulfur Inorganic materials 0.000 claims 2
• 210000002435 tendon Anatomy 0.000 claims 2
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
• 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
• ONQBOTKLCMXPOF-UHFFFAOYSA-N 1-ethylpyrrolidine Chemical compound CCN1CCCC1 ONQBOTKLCMXPOF-UHFFFAOYSA-N 0.000 claims 1
• JKTCBAGSMQIFNL-UHFFFAOYSA-N 2,3-dihydrofuran Chemical compound C1CC=CO1 JKTCBAGSMQIFNL-UHFFFAOYSA-N 0.000 claims 1
• TVCXVUHHCUYLGX-UHFFFAOYSA-N 2-Methylpyrrole Chemical compound CC1=CC=CN1 TVCXVUHHCUYLGX-UHFFFAOYSA-N 0.000 claims 1
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical compound NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims 1
• OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 claims 1
• 101710111653 2-methylisocitrate lyase Proteins 0.000 claims 1
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
• AVFNKJKCERQPJI-UHFFFAOYSA-N 5-(2-imidazol-1-ylethyl)quinoline Chemical compound C=1C=CC2=NC=CC=C2C=1CCN1C=CN=C1 AVFNKJKCERQPJI-UHFFFAOYSA-N 0.000 claims 1
• 102100035767 Adrenocortical dysplasia protein homolog Human genes 0.000 claims 1
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• QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 claims 1
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
• FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims 1
• 102100026094 C-type lectin domain family 12 member A Human genes 0.000 claims 1
• 101710188619 C-type lectin domain family 12 member A Proteins 0.000 claims 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
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• 229910002553 FeIII Inorganic materials 0.000 claims 1
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• OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
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• APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 claims 1
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