SK4282000A3 - Pharmaceutical combinations - Google Patents

Pharmaceutical combinations Download PDF

Info

Publication number: SK4282000A3
Authority: SK; Slovakia
Prior art keywords: amino; alkyl; phenyl; dihydroisoquinoline; hydrogen
Prior art date: 1997-10-10

Application number

SK428-2000A

Other languages

English (en)

Slovak (sk)

Inventor

Peter Hamley

Alan Tinker

Original Assignee

Astrazeneca Uk 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.)

1997-10-10

Filing date

1998-10-05

Publication date

2001-01-18

1998-10-05 Application filed by Astrazeneca Uk Ltd filed Critical Astrazeneca Uk Ltd

2001-01-18 Publication of SK4282000A3 publication Critical patent/SK4282000A3/sk

Links

239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims description 20
-1 benzyloxyphenyl Chemical group 0.000 claims description 19
229940111134 coxibs Drugs 0.000 claims description 19
150000001875 compounds Chemical class 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 14
239000001257 hydrogen Substances 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 6
125000005936 piperidyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 4
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000003884 phenylalkyl group Chemical group 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000000068 chlorophenyl group Chemical group 0.000 claims description 2
125000001207 fluorophenyl group Chemical group 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000004464 hydroxyphenyl group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000002757 morpholinyl group Chemical group 0.000 claims description 2
DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims 1
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims 1
239000003112 inhibitor Substances 0.000 abstract description 26
206010061218 Inflammation Diseases 0.000 abstract description 15
230000004054 inflammatory process Effects 0.000 abstract description 15
238000011282 treatment Methods 0.000 abstract description 13
208000027866 inflammatory disease Diseases 0.000 abstract description 8
102000008299 Nitric Oxide Synthase Human genes 0.000 abstract description 3
108010021487 Nitric Oxide Synthase Proteins 0.000 abstract description 3
238000011260 co-administration Methods 0.000 abstract description 2
102000010907 Cyclooxygenase 2 Human genes 0.000 abstract 1
108010037462 Cyclooxygenase 2 Proteins 0.000 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 34
108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 32
102100029438 Nitric oxide synthase, inducible Human genes 0.000 description 32
MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 31
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
210000002683 foot Anatomy 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 10
VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical compound C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 description 9
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 9
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 9
239000000679 carrageenan Substances 0.000 description 8
235000010418 carrageenan Nutrition 0.000 description 8
229920001525 carrageenan Polymers 0.000 description 8
229940113118 carrageenan Drugs 0.000 description 8
201000010099 disease Diseases 0.000 description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 8
241000700159 Rattus Species 0.000 description 7
206010003246 arthritis Diseases 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
230000005764 inhibitory process Effects 0.000 description 6
150000003180 prostaglandins Chemical class 0.000 description 6
230000003110 anti-inflammatory effect Effects 0.000 description 5
239000003814 drug Substances 0.000 description 5
230000006698 induction Effects 0.000 description 5
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 5
208000022559 Inflammatory bowel disease Diseases 0.000 description 4
102100028452 Nitric oxide synthase, endothelial Human genes 0.000 description 4
101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
230000004968 inflammatory condition Effects 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
238000011321 prophylaxis Methods 0.000 description 4
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
206010030113 Oedema Diseases 0.000 description 3
102000001708 Protein Isoforms Human genes 0.000 description 3
108010029485 Protein Isoforms Proteins 0.000 description 3
229960000590 celecoxib Drugs 0.000 description 3
RZEKVGVHFLEQIL-UHFFFAOYSA-N celecoxib Chemical compound C1=CC(C)=CC=C1C1=CC(C(F)(F)F)=NN1C1=CC=C(S(N)(=O)=O)C=C1 RZEKVGVHFLEQIL-UHFFFAOYSA-N 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
208000037976 chronic inflammation Diseases 0.000 description 3
208000037893 chronic inflammatory disorder Diseases 0.000 description 3
230000000694 effects Effects 0.000 description 3
230000002757 inflammatory effect Effects 0.000 description 3
238000000034 method Methods 0.000 description 3
229940094443 oxytocics prostaglandins Drugs 0.000 description 3
230000001575 pathological effect Effects 0.000 description 3
230000035479 physiological effects, processes and functions Effects 0.000 description 3
230000008961 swelling Effects 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
MHTRUYAUQNWPBC-UHFFFAOYSA-N 3-(furan-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CO1 MHTRUYAUQNWPBC-UHFFFAOYSA-N 0.000 description 2
HWMWUMMILIHFLR-UHFFFAOYSA-N 3-(furan-3-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C=1C=COC=1 HWMWUMMILIHFLR-UHFFFAOYSA-N 0.000 description 2
SJEMPPKPSKQEHA-UHFFFAOYSA-N 3-cyclopropyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1CC1 SJEMPPKPSKQEHA-UHFFFAOYSA-N 0.000 description 2
SGASAPRGFSSJCC-UHFFFAOYSA-N 3-ethynyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC(C#C)CC2=C1 SGASAPRGFSSJCC-UHFFFAOYSA-N 0.000 description 2
GWZRFZUSUXYFLO-UHFFFAOYSA-N 5-cyclobutyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1CCC1 GWZRFZUSUXYFLO-UHFFFAOYSA-N 0.000 description 2
OTLLMGWJZKFCGF-UHFFFAOYSA-N 8-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1 OTLLMGWJZKFCGF-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
201000004624 Dermatitis Diseases 0.000 description 2
101000998969 Homo sapiens Inositol-3-phosphate synthase 1 Proteins 0.000 description 2
102100036881 Inositol-3-phosphate synthase 1 Human genes 0.000 description 2
102000000589 Interleukin-1 Human genes 0.000 description 2
108010002352 Interleukin-1 Proteins 0.000 description 2
208000002193 Pain Diseases 0.000 description 2
201000004681 Psoriasis Diseases 0.000 description 2
241000219061 Rheum Species 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
108060008682 Tumor Necrosis Factor Proteins 0.000 description 2
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 2
230000000202 analgesic effect Effects 0.000 description 2
238000010171 animal model Methods 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
239000002158 endotoxin Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
239000008103 glucose Substances 0.000 description 2
230000028709 inflammatory response Effects 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000001537 neural effect Effects 0.000 description 2
201000008482 osteoarthritis Diseases 0.000 description 2
230000007170 pathology Effects 0.000 description 2
230000004962 physiological condition Effects 0.000 description 2
206010039073 rheumatoid arthritis Diseases 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
208000011580 syndromic disease Diseases 0.000 description 2
125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
LQFVSORCQXDNCM-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2SC(C3N=C(C4=CC=CC=C4C3)N)=NC2=C1 LQFVSORCQXDNCM-UHFFFAOYSA-N 0.000 description 1
RDKMXFCWQURSLL-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=NC=CS1 RDKMXFCWQURSLL-UHFFFAOYSA-N 0.000 description 1
ILKAQXSEIAZAGJ-UHFFFAOYSA-N 3-(2-methylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound CC1=CC=CC=C1C1N=C(N)C2=CC=CC=C2C1 ILKAQXSEIAZAGJ-UHFFFAOYSA-N 0.000 description 1
LCHNDJWNIUCWAD-UHFFFAOYSA-N 3-(2-phenylethynyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C#CC1=CC=CC=C1 LCHNDJWNIUCWAD-UHFFFAOYSA-N 0.000 description 1
SIMLDIDAIWXGPT-UHFFFAOYSA-N 3-(3-chlorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(Cl)=C1 SIMLDIDAIWXGPT-UHFFFAOYSA-N 0.000 description 1
KLWZVSPGLUAFIN-UHFFFAOYSA-N 3-(3-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CC(F)=C1 KLWZVSPGLUAFIN-UHFFFAOYSA-N 0.000 description 1
OCUUMDCHFDZDDK-UHFFFAOYSA-N 3-(4-chlorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(Cl)C=C1 OCUUMDCHFDZDDK-UHFFFAOYSA-N 0.000 description 1
YHPUTQLDLSONET-UHFFFAOYSA-N 3-(4-methoxyphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(OC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 YHPUTQLDLSONET-UHFFFAOYSA-N 0.000 description 1
RTTZUQZPBRNFLW-UHFFFAOYSA-N 3-(4-methylsulfanylphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(SC)=CC=C1C1N=C(N)C2=CC=CC=C2C1 RTTZUQZPBRNFLW-UHFFFAOYSA-N 0.000 description 1
FHPIUNZZJDTGSZ-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C(C=C1)=CC=C1OCC1=CC=CC=C1 FHPIUNZZJDTGSZ-UHFFFAOYSA-N 0.000 description 1
WINWLXDDIRSNDM-UHFFFAOYSA-N 3-[3-(2-aminoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound NCCC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 WINWLXDDIRSNDM-UHFFFAOYSA-N 0.000 description 1
VYLJBFNFOKMCLB-UHFFFAOYSA-N 3-[3-(3-aminopropyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound NCCCC1=CC=CC(C2N=C(N)C3=CC=CC=C3C2)=C1 VYLJBFNFOKMCLB-UHFFFAOYSA-N 0.000 description 1
WBCQLYANPBVSJJ-UHFFFAOYSA-N 3-[4-(2-aminoethyl)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(CCN)=CC=C1C1N=C(N)C2=CC=CC=C2C1 WBCQLYANPBVSJJ-UHFFFAOYSA-N 0.000 description 1
BSBNVHHDNQPTMV-UHFFFAOYSA-N 3-[4-(3-aminopropoxy)phenyl]-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC(OCCCN)=CC=C1C1N=C(N)C2=CC=CC=C2C1 BSBNVHHDNQPTMV-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
FWLROWLVILMULO-UHFFFAOYSA-N 3-methyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC(C)CC2=C1 FWLROWLVILMULO-UHFFFAOYSA-N 0.000 description 1
AQZWYRYKUGMBEY-UHFFFAOYSA-N 3-pyridin-3-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CN=C1 AQZWYRYKUGMBEY-UHFFFAOYSA-N 0.000 description 1
YVJMJORBDKLUPO-UHFFFAOYSA-N 3-pyridin-4-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=NC=C1 YVJMJORBDKLUPO-UHFFFAOYSA-N 0.000 description 1
CDRBKBGYXOOEBB-UHFFFAOYSA-N 3-thiophen-2-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=CS1 CDRBKBGYXOOEBB-UHFFFAOYSA-N 0.000 description 1
MGJCYGSDDRNTQF-UHFFFAOYSA-N 3-thiophen-3-yl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC=CC=C2C(N)=NC1C=1C=CSC=1 MGJCYGSDDRNTQF-UHFFFAOYSA-N 0.000 description 1
PYRGEFPIYBRXKZ-UHFFFAOYSA-N 4-(1-amino-3,4-dihydroisoquinolin-3-yl)phenol Chemical compound C1C2=CC=CC=C2C(N)=NC1C1=CC=C(O)C=C1 PYRGEFPIYBRXKZ-UHFFFAOYSA-N 0.000 description 1
JDTOGSNUBVOBFU-UHFFFAOYSA-N 5,8-difluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 JDTOGSNUBVOBFU-UHFFFAOYSA-N 0.000 description 1
IUXBWVFFYMDQRD-UHFFFAOYSA-N 5-(1-methylpyrrol-2-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound CN1C=CC=C1C1N=C(N)C(SC=C2)=C2C1 IUXBWVFFYMDQRD-UHFFFAOYSA-N 0.000 description 1
FJFMOBYDHGJDGV-UHFFFAOYSA-N 5-(4-amino-5,8-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)pyridine-2-carbonitrile;hydrochloride Chemical compound Cl.N1C2=C(F)C=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)N=C1 FJFMOBYDHGJDGV-UHFFFAOYSA-N 0.000 description 1
OXLOREYBGOXXEV-UHFFFAOYSA-N 5-(furan-3-yl)-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C=1C=COC=1 OXLOREYBGOXXEV-UHFFFAOYSA-N 0.000 description 1
KBBLLKUZTNRELO-UHFFFAOYSA-N 5-chloro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(Cl)C=CC=C2C(N)=NC1C1=CC=CC=C1 KBBLLKUZTNRELO-UHFFFAOYSA-N 0.000 description 1
VNHBYKHXBCYPBJ-UHFFFAOYSA-N 5-ethynylimidazo[1,2-a]pyridine Chemical compound C#CC1=CC=CC2=NC=CN12 VNHBYKHXBCYPBJ-UHFFFAOYSA-N 0.000 description 1
KEASVJPWDYZLCE-UHFFFAOYSA-N 5-fluoro-3-(4-fluorophenyl)-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=C(F)C=C1 KEASVJPWDYZLCE-UHFFFAOYSA-N 0.000 description 1
CQCMHFYGKBQABE-UHFFFAOYSA-N 5-fluoro-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=C(F)C=CC=C2C(N)=NC1C1=CC=CC=C1 CQCMHFYGKBQABE-UHFFFAOYSA-N 0.000 description 1
NVANRLMNXVPARO-UHFFFAOYSA-N 5-methoxy-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C=2C(OC)=CC=CC=2C(N)=NC1C1=CC=CC=C1 NVANRLMNXVPARO-UHFFFAOYSA-N 0.000 description 1
BZMKAOPCFNDOAZ-UHFFFAOYSA-N 5-methyl-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C=2C(C)=CC=CC=2C(N)=NC1C1=CC=CC=C1 BZMKAOPCFNDOAZ-UHFFFAOYSA-N 0.000 description 1
OJTGYEZYCLLMBZ-UHFFFAOYSA-N 5-phenyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CC=C1 OJTGYEZYCLLMBZ-UHFFFAOYSA-N 0.000 description 1
FPIJYFMUGDPADO-UHFFFAOYSA-N 5-prop-1-ynyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(C#CC)CC2=C1SC=C2 FPIJYFMUGDPADO-UHFFFAOYSA-N 0.000 description 1
WCMXTLROFWDEOH-UHFFFAOYSA-N 5-propyl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound NC1=NC(CCC)CC2=C1SC=C2 WCMXTLROFWDEOH-UHFFFAOYSA-N 0.000 description 1
DQFBGLAGAZYBJX-UHFFFAOYSA-N 5-pyridin-3-yl-4,5-dihydrothieno[2,3-c]pyridin-7-amine Chemical compound C1C=2C=CSC=2C(N)=NC1C1=CC=CN=C1 DQFBGLAGAZYBJX-UHFFFAOYSA-N 0.000 description 1
NVWLCUBMMDJESN-UHFFFAOYSA-N 6,7-dihydrothieno[3,2-c]pyridine Chemical compound C1=NCCC2=C1C=CS2 NVWLCUBMMDJESN-UHFFFAOYSA-N 0.000 description 1
ISNQNGVISJCDEL-UHFFFAOYSA-N 6-bromo-3-phenyl-3,4-dihydroisoquinolin-1-amine Chemical compound C1C2=CC(Br)=CC=C2C(N)=NC1C1=CC=CC=C1 ISNQNGVISJCDEL-UHFFFAOYSA-N 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- 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
- A61K31/47—Quinolines; Isoquinolines
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

Landscapes

Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Organic Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Rheumatology (AREA)
General Chemical & Material Sciences (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

SK428-2000A 1997-10-10 1998-10-05 Pharmaceutical combinations SK4282000A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
SE9703693A SE9703693D0 (sv)	1997-10-10	1997-10-10	Novel combination
PCT/SE1998/001792 WO1999018960A1 (en)	1997-10-10	1998-10-05	Novel combination

Publications (1)

Publication Number	Publication Date
SK4282000A3 true SK4282000A3 (en)	2001-01-18

Family

ID=20408563

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK428-2000A SK4282000A3 (en)	1997-10-10	1998-10-05	Pharmaceutical combinations

Country Status (20)

Country	Link
US (1)	US6046191A (tr)
EP (1)	EP1027052A1 (tr)
JP (1)	JP2001519391A (tr)
KR (1)	KR20010031017A (tr)
CN (1)	CN1281362A (tr)
AU (1)	AU9469398A (tr)
BR (1)	BR9812753A (tr)
CA (1)	CA2305141A1 (tr)
CZ (1)	CZ20001272A3 (tr)
EE (1)	EE200000192A (tr)
HU (1)	HUP0003874A2 (tr)
IL (1)	IL135248A0 (tr)
IS (1)	IS5430A (tr)
MX (1)	MXPA00003445A (tr)
NO (1)	NO20001830L (tr)
PL (1)	PL339769A1 (tr)
SE (1)	SE9703693D0 (tr)
SK (1)	SK4282000A3 (tr)
TR (1)	TR200000928T2 (tr)
WO (1)	WO1999018960A1 (tr)

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KR20050005410A (ko) *	2002-02-19	2005-01-13	파마시아 코포레이션	요실금 치료용으로서의 시클로옥시게나제 저해제 및항무스카린제의 용도
US7220749B2 (en) *	2002-06-11	2007-05-22	Nitromed, Inc.	Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
AU2003261281A1 (en) *	2002-07-29	2004-02-16	Nicox S.A.	Cyclooxygenase- 2 selective inhibitors, compositions and methods of use
US8992980B2 (en) *	2002-10-25	2015-03-31	Boehringer Ingelheim Vetmedica Gmbh	Water-soluble meloxicam granules
ES2275218T3 (es) *	2003-05-07	2007-06-01	Osteologix A/S	Sales de estroncio hidrosolubles para el tratamiento de afecciones de cartilagos y/o huesos.
SI1622630T1 (sl) *	2003-05-07	2012-12-31	Osteologix A/S	Stroncijeva kombinacije za profilakso/zdravljenje patologij hrustanca in/ali kosti
EP1568369A1 (en)	2004-02-23	2005-08-31	Boehringer Ingelheim Vetmedica Gmbh	Use of meloxicam for the treatment of respiratory diseases in pigs
DE102004021281A1 (de) *	2004-04-29	2005-11-24	Boehringer Ingelheim Vetmedica Gmbh	Verwendung von Meloxicam-Formulierungen in der Veterinärmedizin
AU2005254154A1 (en) *	2004-06-17	2005-12-29	Osteologix A/S	Improving pain treatment with strontium combinations
DE102004030409A1 (de) *	2004-06-23	2006-01-26	Boehringer Ingelheim Vetmedica Gmbh	Neue Verwendung von Meloxicam in der Veterinärmedizin
NZ567627A (en) *	2005-09-30	2011-08-26	Boehringer Ingelheim Vetmed	Granulation process for making a divisible tablet containing meloxicam
EP2612854B1 (en)	2005-10-25	2015-04-29	Shionogi&Co., Ltd.	Aminothiazolidine and aminotetrahydrothiazepine derivatives as BACE 1 inhibitors
JP2007275193A (ja) *	2006-04-04	2007-10-25	Fujifilm Corp	光プローブおよび光断層画像化装置
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1997
- 1997-10-10 SE SE9703693A patent/SE9703693D0/xx unknown
1998
- 1998-10-05 CN CN98812081A patent/CN1281362A/zh active Pending
- 1998-10-05 HU HU0003874A patent/HUP0003874A2/hu unknown
- 1998-10-05 JP JP2000515595A patent/JP2001519391A/ja active Pending
- 1998-10-05 US US09/171,801 patent/US6046191A/en not_active Expired - Fee Related
- 1998-10-05 WO PCT/SE1998/001792 patent/WO1999018960A1/en not_active Ceased
- 1998-10-05 PL PL98339769A patent/PL339769A1/xx unknown
- 1998-10-05 EP EP98948031A patent/EP1027052A1/en not_active Withdrawn
- 1998-10-05 KR KR1020007003824A patent/KR20010031017A/ko not_active Withdrawn
- 1998-10-05 EE EEP200000192A patent/EE200000192A/xx unknown
- 1998-10-05 CZ CZ20001272A patent/CZ20001272A3/cs unknown
- 1998-10-05 TR TR2000/00928T patent/TR200000928T2/tr unknown
- 1998-10-05 AU AU94693/98A patent/AU9469398A/en not_active Abandoned
- 1998-10-05 SK SK428-2000A patent/SK4282000A3/sk unknown
- 1998-10-05 IL IL13524898A patent/IL135248A0/xx unknown
- 1998-10-05 MX MXPA00003445 patent/MXPA00003445A/es unknown
- 1998-10-05 BR BR9812753-5A patent/BR9812753A/pt not_active IP Right Cessation
- 1998-10-05 CA CA002305141A patent/CA2305141A1/en not_active Abandoned
2000
- 2000-04-06 IS IS5430A patent/IS5430A/is unknown
- 2000-04-07 NO NO20001830A patent/NO20001830L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IS5430A (is)	2000-04-06
EP1027052A1 (en)	2000-08-16
TR200000928T2 (tr)	2000-11-21
IL135248A0 (en)	2001-05-20
SE9703693D0 (sv)	1997-10-10
NO20001830L (no)	2000-05-10
EE200000192A (et)	2001-04-16
KR20010031017A (ko)	2001-04-16
PL339769A1 (en)	2001-01-02
AU9469398A (en)	1999-05-03
HUP0003874A2 (hu)	2001-05-28
US6046191A (en)	2000-04-04
CZ20001272A3 (cs)	2000-09-13
JP2001519391A (ja)	2001-10-23
MXPA00003445A (es)	2001-06-01
BR9812753A (pt)	2000-08-29
CN1281362A (zh)	2001-01-24
CA2305141A1 (en)	1999-04-22
NO20001830D0 (no)	2000-04-07
WO1999018960A1 (en)	1999-04-22

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