NO332265B1 - Pyrrolopyridin-2-karboksylsyreamidinhibitorer, fremstilling av og mellomprodukter ved fremstilling av slike, preparater og kombinasjoner omfattende slike, slike forbindelser og preparater som medikament samt slike forbindelser for behandling av sykdom - Google Patents

Pyrrolopyridin-2-karboksylsyreamidinhibitorer, fremstilling av og mellomprodukter ved fremstilling av slike, preparater og kombinasjoner omfattende slike, slike forbindelser og preparater som medikament samt slike forbindelser for behandling av sykdom Download PDF

Info

Publication number: NO332265B1
Authority: NO; Norway
Prior art keywords: alkyl; mmol; carboxylic acid; pyrrolo; pyridine
Prior art date: 2003-05-21

Application number

NO20055305A

Other languages

English (en)

Norwegian (no)

Other versions

NO20055305L (no

NO20055305D0 (no

Inventor

Karen Lesley Schofield

Stuart Edward Bradley

Thomas Martin Krulle

Peter John Murray

Martin James Procter

Robert John Rowley

Colin Peter Sambrook Smith

Gerard Hugh Thomas

Original Assignee

Prosidion Ltd

Priority date (The priority date 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 date listed.)

2003-05-21

Filing date

2005-11-10

Publication date

2012-08-13

2005-11-10 Application filed by Prosidion Ltd filed Critical Prosidion Ltd

2005-11-10 Publication of NO20055305D0 publication Critical patent/NO20055305D0/no

2005-12-15 Publication of NO20055305L publication Critical patent/NO20055305L/no

2012-08-13 Publication of NO332265B1 publication Critical patent/NO332265B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 476
239000003112 inhibitor Substances 0.000 title claims abstract description 24
238000011282 treatment Methods 0.000 title claims abstract description 19
238000002360 preparation method Methods 0.000 title claims description 322
239000003814 drug Substances 0.000 title claims description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 18
201000010099 disease Diseases 0.000 title description 9
239000000543 intermediate Substances 0.000 title description 5
YWHNNPXTZCBOJQ-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxamide Chemical compound C1=CC=C2NC(C(=O)N)=CC2=N1 YWHNNPXTZCBOJQ-UHFFFAOYSA-N 0.000 title description 2
150000003839 salts Chemical class 0.000 claims abstract description 64
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 10
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 7
208000035150 Hypercholesterolemia Diseases 0.000 claims abstract description 7
208000031226 Hyperlipidaemia Diseases 0.000 claims abstract description 7
201000001421 hyperglycemia Diseases 0.000 claims abstract description 7
201000008980 hyperinsulinism Diseases 0.000 claims abstract description 7
208000031225 myocardial ischemia Diseases 0.000 claims abstract description 7
230000001225 therapeutic effect Effects 0.000 claims abstract description 6
230000000069 prophylactic effect Effects 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 112
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 86
125000000623 heterocyclic group Chemical group 0.000 claims description 43
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 41
229910052736 halogen Inorganic materials 0.000 claims description 39
MIJRRMLODIKPEA-UHFFFAOYSA-N 5-chloro-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound ClC1=NC=C2NC(C(=O)O)=CC2=C1 MIJRRMLODIKPEA-UHFFFAOYSA-N 0.000 claims description 37
-1 hydroxy, fluoromethyl Chemical group 0.000 claims description 37
150000002367 halogens Chemical class 0.000 claims description 35
229910052757 nitrogen Inorganic materials 0.000 claims description 34
125000004093 cyano group Chemical group *C#N 0.000 claims description 32
125000001072 heteroaryl group Chemical group 0.000 claims description 28
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 24
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 24
125000003545 alkoxy group Chemical group 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 22
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 20
150000001412 amines Chemical class 0.000 claims description 18
NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 18
229920006395 saturated elastomer Polymers 0.000 claims description 18
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 17
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
125000001424 substituent group Chemical group 0.000 claims description 17
229910052717 sulfur Inorganic materials 0.000 claims description 17
239000011593 sulfur Chemical group 0.000 claims description 17
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
229910052799 carbon Inorganic materials 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
230000008878 coupling Effects 0.000 claims description 14
238000010168 coupling process Methods 0.000 claims description 14
238000005859 coupling reaction Methods 0.000 claims description 14
239000002253 acid Substances 0.000 claims description 13
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
125000002837 carbocyclic group Chemical group 0.000 claims description 12
229910052727 yttrium Inorganic materials 0.000 claims description 12
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 10
125000005842 heteroatom Chemical group 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 8
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 8
PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 8
KBHQUFPZXCNYKN-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=N1 KBHQUFPZXCNYKN-UHFFFAOYSA-N 0.000 claims description 8
YMSGAOPCRLRFMT-UHFFFAOYSA-N 5-chloro-1h-pyrrolo[2,3-b]pyridine-2-carboxylic acid Chemical compound ClC1=CN=C2NC(C(=O)O)=CC2=C1 YMSGAOPCRLRFMT-UHFFFAOYSA-N 0.000 claims description 8
102000004877 Insulin Human genes 0.000 claims description 8
108090001061 Insulin Proteins 0.000 claims description 8
WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 claims description 8
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 8
IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 8
125000004122 cyclic group Chemical group 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
229940125396 insulin Drugs 0.000 claims description 8
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 8
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
239000005557 antagonist Substances 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims description 6
MFMDNNLHOKXYLL-UHFFFAOYSA-N 6-chloro-1h-pyrrolo[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=C(Cl)N=C2NC(C(=O)O)=CC2=C1 MFMDNNLHOKXYLL-UHFFFAOYSA-N 0.000 claims description 6
IZFVERBPAPUYEK-UHFFFAOYSA-N 6-chloro-1h-pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=C(Cl)C=C2NC(C(=O)O)=CC2=C1 IZFVERBPAPUYEK-UHFFFAOYSA-N 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
LTAXMSVURJPVQV-UHFFFAOYSA-N 5-chloro-1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound ClC1=CC=C2NC(C(=O)O)=CC2=N1 LTAXMSVURJPVQV-UHFFFAOYSA-N 0.000 claims description 5
DXYLYCVOQBQXJU-UHFFFAOYSA-N 5-cyano-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound N#CC1=NC=C2NC(C(=O)O)=CC2=C1 DXYLYCVOQBQXJU-UHFFFAOYSA-N 0.000 claims description 5
239000000556 agonist Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 5
FUXSSMSAWSOUSN-QMMMGPOBSA-N (4s)-4-[(4-fluorophenyl)methyl]-1,3-oxazolidine-2,5-dione Chemical compound C1=CC(F)=CC=C1C[C@H]1C(=O)OC(=O)N1 FUXSSMSAWSOUSN-QMMMGPOBSA-N 0.000 claims description 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 4
CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 claims description 4
CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 claims description 4
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims description 4
VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 4
OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 claims description 4
HEAHLTGDUHXTTO-UHFFFAOYSA-N 1,3-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNC1 HEAHLTGDUHXTTO-UHFFFAOYSA-N 0.000 claims description 4
KZPUZEPLLNUDDZ-UHFFFAOYSA-N 1,3-thiazolidine 1-oxide Chemical compound O=S1CCNC1 KZPUZEPLLNUDDZ-UHFFFAOYSA-N 0.000 claims description 4
FQUYSHZXSKYCSY-UHFFFAOYSA-N 1,4-diazepane Chemical compound C1CNCCNC1 FQUYSHZXSKYCSY-UHFFFAOYSA-N 0.000 claims description 4
YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical compound O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 4
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
ANFOMGVCGLRXAC-UHFFFAOYSA-N 1h-pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=CC=C2NC(C(=O)O)=CC2=C1 ANFOMGVCGLRXAC-UHFFFAOYSA-N 0.000 claims description 4
FTAHXMZRJCZXDL-UHFFFAOYSA-N 3-piperideine Chemical compound C1CC=CCN1 FTAHXMZRJCZXDL-UHFFFAOYSA-N 0.000 claims description 4
NNWNNQTUZYVQRK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound BrC1=NC=C2NC(C(=O)O)=CC2=C1 NNWNNQTUZYVQRK-UHFFFAOYSA-N 0.000 claims description 4
BGRTVRRVFGHABF-UHFFFAOYSA-N 5-methoxy-1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound COC1=CC=C2NC(C(O)=O)=CC2=N1 BGRTVRRVFGHABF-UHFFFAOYSA-N 0.000 claims description 4
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 4
YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 claims description 4
XKMRRTOUMJRJIA-UHFFFAOYSA-N ammonia nh3 Chemical compound N.N XKMRRTOUMJRJIA-UHFFFAOYSA-N 0.000 claims description 4
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 4
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 claims description 4
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 4
BNBQRQQYDMDJAH-UHFFFAOYSA-N benzodioxan Chemical compound C1=CC=C2OCCOC2=C1 BNBQRQQYDMDJAH-UHFFFAOYSA-N 0.000 claims description 4
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000001786 isothiazolyl group Chemical group 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
XHWNEBDUPVMPKI-UHFFFAOYSA-N oxazetidine Chemical compound C1CON1 XHWNEBDUPVMPKI-UHFFFAOYSA-N 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
UHHKSVZZTYJVEG-UHFFFAOYSA-N oxepane Chemical compound C1CCCOCC1 UHHKSVZZTYJVEG-UHFFFAOYSA-N 0.000 claims description 4
AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 4
HZIVRQOIUMAXID-UHFFFAOYSA-N oxocane Chemical compound C1CCCOCCC1 HZIVRQOIUMAXID-UHFFFAOYSA-N 0.000 claims description 4
125000003373 pyrazinyl group Chemical group 0.000 claims description 4
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 claims description 4
125000003226 pyrazolyl group Chemical group 0.000 claims description 4
125000002098 pyridazinyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
125000000168 pyrrolyl group Chemical group 0.000 claims description 4
229940044601 receptor agonist Drugs 0.000 claims description 4
239000000018 receptor agonist Substances 0.000 claims description 4
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 claims description 4
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
BUGOPWGPQGYYGR-UHFFFAOYSA-N thiane 1,1-dioxide Chemical compound O=S1(=O)CCCCC1 BUGOPWGPQGYYGR-UHFFFAOYSA-N 0.000 claims description 4
NNLBRYQGMOYARS-UHFFFAOYSA-N thiane 1-oxide Chemical compound O=S1CCCCC1 NNLBRYQGMOYARS-UHFFFAOYSA-N 0.000 claims description 4
125000000335 thiazolyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
AMIGYDGSJCJWSD-UHFFFAOYSA-N thiocane Chemical compound C1CCCSCCC1 AMIGYDGSJCJWSD-UHFFFAOYSA-N 0.000 claims description 4
125000004306 triazinyl group Chemical group 0.000 claims description 4
125000001425 triazolyl group Chemical group 0.000 claims description 4
125000006661 (C4-C6) heterocyclic group Chemical group 0.000 claims description 3
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
VMJNTFXCTXAXTC-UHFFFAOYSA-N 2,2-difluoro-1,3-benzodioxole-5-carbonitrile Chemical group C1=C(C#N)C=C2OC(F)(F)OC2=C1 VMJNTFXCTXAXTC-UHFFFAOYSA-N 0.000 claims description 3
JCKFLPZVWFBDQZ-UHFFFAOYSA-N 5-ethynyl-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C#CC1=NC=C2NC(C(=O)O)=CC2=C1 JCKFLPZVWFBDQZ-UHFFFAOYSA-N 0.000 claims description 3
NBCQHRXBLPIFNR-UHFFFAOYSA-N 5-methyl-1h-pyrrolo[2,3-c]pyridine-2-carboxylic acid Chemical compound C1=NC(C)=CC2=C1NC(C(O)=O)=C2 NBCQHRXBLPIFNR-UHFFFAOYSA-N 0.000 claims description 3
125000005907 alkyl ester group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
238000010931 ester hydrolysis Methods 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
JWCVYQRPINPYQJ-UHFFFAOYSA-N thiepane Chemical compound C1CCCSCC1 JWCVYQRPINPYQJ-UHFFFAOYSA-N 0.000 claims description 3
XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims description 3
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
CZMLLVBNKAZHMK-UHFFFAOYSA-N 5-bromo-1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound BrC1=CC=C2NC(C(=O)O)=CC2=N1 CZMLLVBNKAZHMK-UHFFFAOYSA-N 0.000 claims description 2
FYMNETUBQDEDKO-UHFFFAOYSA-N 5-cyano-1h-pyrrolo[3,2-b]pyridine-2-carboxylic acid Chemical compound N#CC1=CC=C2NC(C(=O)O)=CC2=N1 FYMNETUBQDEDKO-UHFFFAOYSA-N 0.000 claims description 2
JRUYFJROYXAOAW-UHFFFAOYSA-N 6-cyano-1h-pyrrolo[2,3-b]pyridine-2-carboxylic acid Chemical compound C1=C(C#N)N=C2NC(C(=O)O)=CC2=C1 JRUYFJROYXAOAW-UHFFFAOYSA-N 0.000 claims description 2
AWYNTOXANZBHFJ-UHFFFAOYSA-N 6-cyano-1h-pyrrolo[3,2-c]pyridine-2-carboxylic acid Chemical compound N1=C(C#N)C=C2NC(C(=O)O)=CC2=C1 AWYNTOXANZBHFJ-UHFFFAOYSA-N 0.000 claims description 2
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DDSWCDPYKYPBBQ-UHFFFAOYSA-N [2-(4-methoxyphenyl)-1,3-dioxolan-2-yl]methanamine Chemical compound C1=CC(OC)=CC=C1C1(CN)OCCO1 DDSWCDPYKYPBBQ-UHFFFAOYSA-N 0.000 description 2
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VHYXAWLOJGIJPC-UHFFFAOYSA-N tert-butyl n-(piperidin-4-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNCC1 VHYXAWLOJGIJPC-UHFFFAOYSA-N 0.000 description 1
ZJTYRNPLVNMVPQ-LBPRGKRZSA-N tert-butyl n-[(2s)-1-oxo-3-phenylpropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](C=O)CC1=CC=CC=C1 ZJTYRNPLVNMVPQ-LBPRGKRZSA-N 0.000 description 1
QWYIDHJMNFKZQY-GJZGRUSLSA-N tert-butyl n-[(2s)-3-(4-fluorophenyl)-1-[(3s)-3-hydroxypyrrolidin-1-yl]-1-oxopropan-2-yl]carbamate Chemical compound C([C@H](NC(=O)OC(C)(C)C)C(=O)N1C[C@@H](O)CC1)C1=CC=C(F)C=C1 QWYIDHJMNFKZQY-GJZGRUSLSA-N 0.000 description 1
WCUFJYYHGYCNNS-NRFANRHFSA-N tert-butyl n-[1-[(2s)-2-[(5-chloro-1h-pyrrolo[2,3-c]pyridine-2-carbonyl)amino]-3-(4-fluorophenyl)propanoyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C(=O)[C@@H](NC(=O)C=1NC2=CN=C(Cl)C=C2C=1)CC1=CC=C(F)C=C1 WCUFJYYHGYCNNS-NRFANRHFSA-N 0.000 description 1
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VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000004571 thiomorpholin-4-yl group Chemical group N1(CCSCC1)* 0.000 description 1
FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Bioinformatics & Cheminformatics (AREA)
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Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Hematology (AREA)
Cardiology (AREA)
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Urology & Nephrology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pyrrole Compounds (AREA)
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NO20055305A 2003-05-21 2005-11-10 Pyrrolopyridin-2-karboksylsyreamidinhibitorer, fremstilling av og mellomprodukter ved fremstilling av slike, preparater og kombinasjoner omfattende slike, slike forbindelser og preparater som medikament samt slike forbindelser for behandling av sykdom NO332265B1 (no)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US47237503P	2003-05-21	2003-05-21
US55125604P	2004-03-08	2004-03-08
PCT/US2004/016243 WO2004104001A2 (en)	2003-05-21	2004-05-20	Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phoshorylase

Publications (3)

Publication Number	Publication Date
NO20055305D0 NO20055305D0 (no)	2005-11-10
NO20055305L NO20055305L (no)	2005-12-15
NO332265B1 true NO332265B1 (no)	2012-08-13

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Application Number	Title	Priority Date	Filing Date
NO20055305A NO332265B1 (no)	2003-05-21	2005-11-10	Pyrrolopyridin-2-karboksylsyreamidinhibitorer, fremstilling av og mellomprodukter ved fremstilling av slike, preparater og kombinasjoner omfattende slike, slike forbindelser og preparater som medikament samt slike forbindelser for behandling av sykdom

Country Status (16)

Country	Link
EP (1)	EP1636224B1 (uk)
JP (2)	JP2006528702A (uk)
KR (1)	KR101120935B1 (uk)
AT (1)	ATE473974T1 (uk)
AU (1)	AU2004240946B8 (uk)
BR (1)	BRPI0410445B1 (uk)
CA (1)	CA2525502C (uk)
DE (1)	DE602004028122D1 (uk)
EA (1)	EA009215B1 (uk)
IL (1)	IL171851A (uk)
MA (1)	MA27809A1 (uk)
MX (1)	MXPA05012547A (uk)
NO (1)	NO332265B1 (uk)
NZ (1)	NZ543482A (uk)
UA (1)	UA84146C2 (uk)
WO (1)	WO2004104001A2 (uk)

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CN103748070B (zh)	2011-05-31	2015-06-24	施万生物制药研发Ip有限责任公司	脑啡肽酶抑制剂
US9345247B2 (en)	2012-08-17	2016-05-24	Bayer Cropscience Ag	Azaindole carboxylic acid amides and azaindole thiocarboxylic acid amides for use as insecticides and acaricides
CN103626825B (zh) *	2013-09-30	2015-10-07	承德医学院	靶向肝脏的糖原磷酸化酶抑制剂胆酸类衍生物、其制备方法及医药用途
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2004
- 2004-05-20 AT AT04753127T patent/ATE473974T1/de not_active IP Right Cessation
- 2004-05-20 CA CA2525502A patent/CA2525502C/en not_active Expired - Fee Related
- 2004-05-20 NZ NZ543482A patent/NZ543482A/en not_active IP Right Cessation
- 2004-05-20 DE DE602004028122T patent/DE602004028122D1/de not_active Expired - Lifetime
- 2004-05-20 EA EA200501645A patent/EA009215B1/ru not_active IP Right Cessation
- 2004-05-20 BR BRPI0410445-5A patent/BRPI0410445B1/pt not_active IP Right Cessation
- 2004-05-20 WO PCT/US2004/016243 patent/WO2004104001A2/en not_active Ceased
- 2004-05-20 AU AU2004240946A patent/AU2004240946B8/en not_active Ceased
- 2004-05-20 EP EP04753127A patent/EP1636224B1/en not_active Expired - Lifetime
- 2004-05-20 JP JP2006533345A patent/JP2006528702A/ja not_active Withdrawn
- 2004-05-20 UA UAA200510756A patent/UA84146C2/uk unknown
- 2004-05-20 MX MXPA05012547A patent/MXPA05012547A/es active IP Right Grant
2005
- 2005-11-09 IL IL171851A patent/IL171851A/en active IP Right Grant
- 2005-11-10 NO NO20055305A patent/NO332265B1/no not_active IP Right Cessation
- 2005-11-21 MA MA28613A patent/MA27809A1/fr unknown
- 2005-11-21 KR KR1020057022252A patent/KR101120935B1/ko not_active Expired - Fee Related
2011
- 2011-08-09 JP JP2011174163A patent/JP5669691B2/ja not_active Expired - Fee Related

Also Published As

Publication number	Publication date
MA27809A1 (fr)	2006-03-01
JP5669691B2 (ja)	2015-02-12
DE602004028122D1 (de)	2010-08-26
EP1636224B1 (en)	2010-07-14
NO20055305L (no)	2005-12-15
EA009215B1 (ru)	2007-12-28
IL171851A (en)	2011-08-31
AU2004240946B2 (en)	2011-09-08
JP2011252005A (ja)	2011-12-15
JP2006528702A (ja)	2006-12-21
AU2004240946A1 (en)	2004-12-02
BRPI0410445A (pt)	2006-05-30
WO2004104001A2 (en)	2004-12-02
AU2004240946B8 (en)	2012-01-12
NZ543482A (en)	2009-02-28
KR101120935B1 (ko)	2012-03-05
MXPA05012547A (es)	2006-05-25
WO2004104001A3 (en)	2005-03-03
KR20060069792A (ko)	2006-06-22
UA84146C2 (uk)	2008-09-25
EP1636224A2 (en)	2006-03-22
ATE473974T1 (de)	2010-07-15
NO20055305D0 (no)	2005-11-10
BRPI0410445B1 (pt)	2017-11-28
CA2525502C (en)	2012-12-18
EA200501645A1 (ru)	2006-06-30
CA2525502A1 (en)	2004-12-02

Publication	Publication Date	Title
NO332265B1 (no)	2012-08-13	Pyrrolopyridin-2-karboksylsyreamidinhibitorer, fremstilling av og mellomprodukter ved fremstilling av slike, preparater og kombinasjoner omfattende slike, slike forbindelser og preparater som medikament samt slike forbindelser for behandling av sykdom
KR102642203B1 (ko)	2024-03-04	급속 진행형 섬유육종 폴리펩티드의 표적화 분해를 위한 다중 고리 화합물 및 방법
KR102564201B1 (ko)	2023-08-07	급속 진행성 섬유육종 폴리펩티드의 표적화 분해를 위한 화합물 및 방법
US8158622B2 (en)	2012-04-17	Pyrrolopyridine-2-carboxylic acid amide inhibitors of glycogen phosphorylase
TW202216679A (zh)	2022-05-01	抗病毒化合物
IL275058B1 (en)	2024-09-01	Sulphonyl urea derivatives as nlrp3 inflammasome modulators
KR20240095318A (ko)	2024-06-25	단백질분해 조절제 및 연관된 사용 방법
CA2608072A1 (en)	2006-11-30	Aminopiperidine quinolines and their azaisosteric analogues with antibacterial activity
EP1819332B1 (en)	2009-03-11	Pyrrolopyridine-2-carboxylic acid amides
ES2348702T3 (es)	2010-12-10	Amidas de acidos pirrolopiridina-2-carboxilicos inhibidores de la glucogeno-fosforilasa.
US20240156780A1 (en)	2024-05-16	Tlr2 modulator compounds, pharmaceutical compositions and uses thereof

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