ZA200007076B - A pharmaceutical combination comprising a COX-2 inhibitor and iNOS inhibitor. - Google Patents
A pharmaceutical combination comprising a COX-2 inhibitor and iNOS inhibitor. Download PDFInfo
- Publication number
- ZA200007076B ZA200007076B ZA200007076A ZA200007076A ZA200007076B ZA 200007076 B ZA200007076 B ZA 200007076B ZA 200007076 A ZA200007076 A ZA 200007076A ZA 200007076 A ZA200007076 A ZA 200007076A ZA 200007076 B ZA200007076 B ZA 200007076B
- Authority
- ZA
- South Africa
- Prior art keywords
- quinazoline
- piperidine
- amine
- spiro
- fluorospiro
- Prior art date
Links
- 229940111134 coxibs Drugs 0.000 title claims description 12
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 title claims description 12
- 102100029438 Nitric oxide synthase, inducible Human genes 0.000 title description 28
- 239000003112 inhibitor Substances 0.000 title description 17
- 101710089543 Nitric oxide synthase, inducible Proteins 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 39
- -1 nitro, hydroxymethyl Chemical group 0.000 claims description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 20
- 229910052717 sulfur Inorganic materials 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 3
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000003386 piperidinyl group Chemical group 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000003003 spiro group Chemical group 0.000 claims 27
- 239000000203 mixture Substances 0.000 claims 7
- 239000000126 substance Substances 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- MGZQYLPBDWRLRS-UHFFFAOYSA-N 4-amino-5-fluorospiro[1H-quinazoline-2,4'-piperidine]-1'-carboxylic acid Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(O)=O)CC2 MGZQYLPBDWRLRS-UHFFFAOYSA-N 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 150000001412 amines Chemical class 0.000 claims 2
- 229960000590 celecoxib Drugs 0.000 claims 2
- 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 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- APKOMINTFZCZFO-UHFFFAOYSA-N (2-phenylmethoxyphenyl) 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OC1=CC=CC=C1OCC1=CC=CC=C1 APKOMINTFZCZFO-UHFFFAOYSA-N 0.000 claims 1
- AKWKXFUXQQNUGE-UHFFFAOYSA-N (3-amino-4-chlorophenyl)-(4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)C(N)=C1 AKWKXFUXQQNUGE-UHFFFAOYSA-N 0.000 claims 1
- KOCBGBJUDZNSJE-UHFFFAOYSA-N (4-amino-5,7-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=CC(F)=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CS1 KOCBGBJUDZNSJE-UHFFFAOYSA-N 0.000 claims 1
- UBKOYBCYKOMMLX-UHFFFAOYSA-N (4-amino-5,8-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyrazin-2-ylmethanone Chemical compound N1C2=C(F)C=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CN=CC=N1 UBKOYBCYKOMMLX-UHFFFAOYSA-N 0.000 claims 1
- RSWKKGGFYGUXKX-UHFFFAOYSA-N (4-amino-5,8-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=C(F)C=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CS1 RSWKKGGFYGUXKX-UHFFFAOYSA-N 0.000 claims 1
- XYVHDOIVLBKYSN-UHFFFAOYSA-N (4-amino-5-chlorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(furan-2-yl)methanone Chemical compound N1C2=CC=CC(Cl)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CO1 XYVHDOIVLBKYSN-UHFFFAOYSA-N 0.000 claims 1
- DIHJYVUOGXNGAH-UHFFFAOYSA-N (4-amino-5-chlorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=CC=CC(Cl)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CS1 DIHJYVUOGXNGAH-UHFFFAOYSA-N 0.000 claims 1
- VDHKOWHUJJLOJT-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,3'-azetidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(C1)CN1C(=O)C1=CC=CS1 VDHKOWHUJJLOJT-UHFFFAOYSA-N 0.000 claims 1
- KFHRZNJUQDYBJY-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(1,2-oxazol-3-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C=1C=CON=1 KFHRZNJUQDYBJY-UHFFFAOYSA-N 0.000 claims 1
- NZWAXDZRCSMJBT-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(1,2-oxazol-5-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=NO1 NZWAXDZRCSMJBT-UHFFFAOYSA-N 0.000 claims 1
- DNFWRSPJYBBOPI-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(1,2-thiazol-4-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C=1C=NSC=1 DNFWRSPJYBBOPI-UHFFFAOYSA-N 0.000 claims 1
- XIWOHKSOWPQQKR-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(1,3-benzodioxol-5-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC11CCN(C(=O)C=2C=C3OCOC3=CC=2)CC1 XIWOHKSOWPQQKR-UHFFFAOYSA-N 0.000 claims 1
- PDAROESMVYZUME-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(1-benzothiophen-2-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC11CCN(C(=O)C=2SC3=CC=CC=C3C=2)CC1 PDAROESMVYZUME-UHFFFAOYSA-N 0.000 claims 1
- ILCKXLSZAQDUQA-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(2-fluorophenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC=C1F ILCKXLSZAQDUQA-UHFFFAOYSA-N 0.000 claims 1
- VIMLGTXWXHFWLU-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3,4-dichlorophenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)C(Cl)=C1 VIMLGTXWXHFWLU-UHFFFAOYSA-N 0.000 claims 1
- HKGKHOSURFYMEX-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-bromophenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Br)C=C1 HKGKHOSURFYMEX-UHFFFAOYSA-N 0.000 claims 1
- LPHXOGYMVXBMGV-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-bromothiophen-2-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC(Br)=CS1 LPHXOGYMVXBMGV-UHFFFAOYSA-N 0.000 claims 1
- WQDRNIPMIVSODU-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-butylphenyl)methanone Chemical compound C1=CC(CCCC)=CC=C1C(=O)N1CCC2(N=C(N)C3=C(F)C=CC=C3N2)CC1 WQDRNIPMIVSODU-UHFFFAOYSA-N 0.000 claims 1
- QHHPFGJIVBDRLM-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCC2(N=C(N)C3=C(F)C=CC=C3N2)CC1 QHHPFGJIVBDRLM-UHFFFAOYSA-N 0.000 claims 1
- HYADBWLWDQEHQC-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-ethynylphenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#C)C=C1 HYADBWLWDQEHQC-UHFFFAOYSA-N 0.000 claims 1
- PBLLMEQBUDSAQC-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-iodophenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(I)C=C1 PBLLMEQBUDSAQC-UHFFFAOYSA-N 0.000 claims 1
- ZCOOYDCGKLWSOO-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-nitrophenyl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C([N+]([O-])=O)C=C1 ZCOOYDCGKLWSOO-UHFFFAOYSA-N 0.000 claims 1
- ISYQOHGPHWEVDP-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(5-chlorothiophen-2-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)S1 ISYQOHGPHWEVDP-UHFFFAOYSA-N 0.000 claims 1
- PSSXHJXRSQJUCU-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(5-ethylthiophen-2-yl)methanone Chemical compound S1C(CC)=CC=C1C(=O)N1CCC2(N=C(N)C3=C(F)C=CC=C3N2)CC1 PSSXHJXRSQJUCU-UHFFFAOYSA-N 0.000 claims 1
- MLJJWPOBARCEED-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(5-methylthiophen-2-yl)methanone Chemical compound S1C(C)=CC=C1C(=O)N1CCC2(N=C(N)C3=C(F)C=CC=C3N2)CC1 MLJJWPOBARCEED-UHFFFAOYSA-N 0.000 claims 1
- IZTDKOVHEGYKPL-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(6-chloropyridin-3-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)N=C1 IZTDKOVHEGYKPL-UHFFFAOYSA-N 0.000 claims 1
- MPTWCHUKDCSDPV-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(furan-2-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CO1 MPTWCHUKDCSDPV-UHFFFAOYSA-N 0.000 claims 1
- XGEBICJDODHDSM-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(thiadiazol-4-yl)methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CSN=N1 XGEBICJDODHDSM-UHFFFAOYSA-N 0.000 claims 1
- WFHLOVTZLHSUJR-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-[4-(1,3-thiazol-2-yl)phenyl]methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C1=NC=CS1 WFHLOVTZLHSUJR-UHFFFAOYSA-N 0.000 claims 1
- HVSJYCHNWXEDQS-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-[4-(trifluoromethoxy)phenyl]methanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(OC(F)(F)F)C=C1 HVSJYCHNWXEDQS-UHFFFAOYSA-N 0.000 claims 1
- OAPJJODFZBWXIT-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-naphthalen-2-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC11CCN(C(=O)C=2C=C3C=CC=CC3=CC=2)CC1 OAPJJODFZBWXIT-UHFFFAOYSA-N 0.000 claims 1
- AKYCWDWVZKGLHK-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-phenylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC=C1 AKYCWDWVZKGLHK-UHFFFAOYSA-N 0.000 claims 1
- FROYHFANPQGWHV-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyrazin-2-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CN=CC=N1 FROYHFANPQGWHV-UHFFFAOYSA-N 0.000 claims 1
- FDXOJIRLSDHJRM-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridin-3-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CN=C1 FDXOJIRLSDHJRM-UHFFFAOYSA-N 0.000 claims 1
- PSDMUSHNLOWHJY-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridin-4-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=NC=C1 PSDMUSHNLOWHJY-UHFFFAOYSA-N 0.000 claims 1
- WGEOFKYJXAQYMS-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-quinolin-6-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC11CCN(C(=O)C=2C=C3C=CC=NC3=CC=2)CC1 WGEOFKYJXAQYMS-UHFFFAOYSA-N 0.000 claims 1
- NYAHZYJRMJHXNX-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CS1 NYAHZYJRMJHXNX-UHFFFAOYSA-N 0.000 claims 1
- FHRCQQIVIJAXMW-UHFFFAOYSA-N (4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-3-ylmethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C=1C=CSC=1 FHRCQQIVIJAXMW-UHFFFAOYSA-N 0.000 claims 1
- YOGMHFXUEGAVGP-UHFFFAOYSA-N (4-amino-5-hydroxyspiro[1H-quinazoline-2,4'-piperidine]-1'-yl)-(4-bromophenyl)methanone Chemical compound BrC1=CC=C(C(=O)N2CCC3(CC2)NC2=CC=CC(=C2C(=N3)N)O)C=C1 YOGMHFXUEGAVGP-UHFFFAOYSA-N 0.000 claims 1
- YSLVFEKXFLRWJB-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 YSLVFEKXFLRWJB-UHFFFAOYSA-N 0.000 claims 1
- YTFXUYQLAYFSDK-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(2-nitrophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC=C1[N+]([O-])=O YTFXUYQLAYFSDK-UHFFFAOYSA-N 0.000 claims 1
- LYWXRZJLZASXOX-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3,5-difluorophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC(F)=CC(F)=C1 LYWXRZJLZASXOX-UHFFFAOYSA-N 0.000 claims 1
- UGIRRFQSYPWTIV-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3,5-dimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C(=O)N2CCC3(CC2)N=C(N)C2=CC=CC=C2N3)=C1 UGIRRFQSYPWTIV-UHFFFAOYSA-N 0.000 claims 1
- PQURLOMPBCHPGL-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=C(F)C(C)=CC=C1C(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 PQURLOMPBCHPGL-UHFFFAOYSA-N 0.000 claims 1
- SXVBQTLINWTTDH-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3-hydroxyphenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC(O)=C1 SXVBQTLINWTTDH-UHFFFAOYSA-N 0.000 claims 1
- CCBWQNZCZLKXGW-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(3-nitrophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC([N+]([O-])=O)=C1 CCBWQNZCZLKXGW-UHFFFAOYSA-N 0.000 claims 1
- VNWSZDTZAXJWTA-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-bromophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Br)C=C1 VNWSZDTZAXJWTA-UHFFFAOYSA-N 0.000 claims 1
- RSHKJRVJSVODHV-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-chlorophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 RSHKJRVJSVODHV-UHFFFAOYSA-N 0.000 claims 1
- ZHMUHIIKTOAYBJ-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-ethylphenyl)methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 ZHMUHIIKTOAYBJ-UHFFFAOYSA-N 0.000 claims 1
- ZYTYCDYFRYWVRC-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-fluorophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(F)C=C1 ZYTYCDYFRYWVRC-UHFFFAOYSA-N 0.000 claims 1
- OHNSXMZWFQQTCM-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 OHNSXMZWFQQTCM-UHFFFAOYSA-N 0.000 claims 1
- WVIIEGBETUCHMM-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-methylphenyl)methanone Chemical compound C1=CC(C)=CC=C1C(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 WVIIEGBETUCHMM-UHFFFAOYSA-N 0.000 claims 1
- NJTHXCSIFDORLB-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-nitrophenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C([N+]([O-])=O)C=C1 NJTHXCSIFDORLB-UHFFFAOYSA-N 0.000 claims 1
- STMUJZVGRUGXPP-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-phenylmethoxyphenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C(C=C1)=CC=C1OCC1=CC=CC=C1 STMUJZVGRUGXPP-UHFFFAOYSA-N 0.000 claims 1
- BKEHWSDXDOKAKY-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(4-pyrrol-1-ylphenyl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C(C=C1)=CC=C1N1C=CC=C1 BKEHWSDXDOKAKY-UHFFFAOYSA-N 0.000 claims 1
- JLSNBSZYVMRYPE-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(5-bromofuran-2-yl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Br)O1 JLSNBSZYVMRYPE-UHFFFAOYSA-N 0.000 claims 1
- OPTLWKIMIHXNQP-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(5-chlorothiophen-2-yl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(Cl)S1 OPTLWKIMIHXNQP-UHFFFAOYSA-N 0.000 claims 1
- CDTAQGVWXTWJSL-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-(furan-2-yl)methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CO1 CDTAQGVWXTWJSL-UHFFFAOYSA-N 0.000 claims 1
- JHWGWJFIJZBUBO-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-[4-(thiadiazol-4-yl)phenyl]methanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C(C=C1)=CC=C1C1=CSN=N1 JHWGWJFIJZBUBO-UHFFFAOYSA-N 0.000 claims 1
- CDMGWLJJDGVEHM-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-phenylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC=C1 CDMGWLJJDGVEHM-UHFFFAOYSA-N 0.000 claims 1
- QASSGVAMNALSJW-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridazin-3-ylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CN=N1 QASSGVAMNALSJW-UHFFFAOYSA-N 0.000 claims 1
- IZBCDOMUJBDFRK-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridin-2-ylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CC=N1 IZBCDOMUJBDFRK-UHFFFAOYSA-N 0.000 claims 1
- RZQBITLJVDCTCQ-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridin-3-ylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CN=C1 RZQBITLJVDCTCQ-UHFFFAOYSA-N 0.000 claims 1
- QPQYFHNRSWYIRL-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-pyridin-4-ylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=NC=C1 QPQYFHNRSWYIRL-UHFFFAOYSA-N 0.000 claims 1
- YCPVARZUSFKJFC-UHFFFAOYSA-N (4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-thiophen-2-ylmethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=CS1 YCPVARZUSFKJFC-UHFFFAOYSA-N 0.000 claims 1
- BANAKXZRCPMACJ-UHFFFAOYSA-N 1'-(1,3-thiazol-2-yl)spiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C1=NC=CS1 BANAKXZRCPMACJ-UHFFFAOYSA-N 0.000 claims 1
- JNFOYDZTLHMDOI-UHFFFAOYSA-N 1'-(4-methoxyphenyl)sulfonylspiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC2(N=C(N)C3=CC=CC=C3N2)CC1 JNFOYDZTLHMDOI-UHFFFAOYSA-N 0.000 claims 1
- YLRPEOQFDFJODI-UHFFFAOYSA-N 1'-(4-nitrophenyl)sulfonylspiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1S(=O)(=O)C1=CC=C([N+]([O-])=O)C=C1 YLRPEOQFDFJODI-UHFFFAOYSA-N 0.000 claims 1
- POJUMRIPMRZFND-UHFFFAOYSA-N 1'-benzyl-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1CC1=CC=CC=C1 POJUMRIPMRZFND-UHFFFAOYSA-N 0.000 claims 1
- PLVDEUNFGOERLC-UHFFFAOYSA-N 1'-benzylspiro[1h-quinazoline-2,3'-piperidine]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1(C1)CCCN1CC1=CC=CC=C1 PLVDEUNFGOERLC-UHFFFAOYSA-N 0.000 claims 1
- GHNOXODQBPONQP-UHFFFAOYSA-N 1'-benzylspiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1CC1=CC=CC=C1 GHNOXODQBPONQP-UHFFFAOYSA-N 0.000 claims 1
- ICXFAHOEALHNMX-UHFFFAOYSA-N 1'-methylsulfonylspiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound C1CN(S(=O)(=O)C)CCC21N=C(N)C1=CC=CC=C1N2 ICXFAHOEALHNMX-UHFFFAOYSA-N 0.000 claims 1
- LIWDTGMJUGTXEP-UHFFFAOYSA-N 1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NCNC2=C1 LIWDTGMJUGTXEP-UHFFFAOYSA-N 0.000 claims 1
- FIAREUUBRWXZPN-UHFFFAOYSA-N 1-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-2,2,2-trifluoroethanone Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)C(F)(F)F)CC2 FIAREUUBRWXZPN-UHFFFAOYSA-N 0.000 claims 1
- OGXGDEWNXVPOSL-UHFFFAOYSA-N 1-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-4-phenoxybutan-1-one Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)CCCOC1=CC=CC=C1 OGXGDEWNXVPOSL-UHFFFAOYSA-N 0.000 claims 1
- WOWHOIWNMKITEP-UHFFFAOYSA-N 1-(4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-yl)-2-[2-(trifluoromethyl)phenyl]ethanone Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)CC1=CC=CC=C1C(F)(F)F WOWHOIWNMKITEP-UHFFFAOYSA-N 0.000 claims 1
- ZCULUGBJSMGCDG-UHFFFAOYSA-N 1-methyl-2-phenyl-2h-quinazolin-4-amine Chemical compound N1=C(N)C2=CC=CC=C2N(C)C1C1=CC=CC=C1 ZCULUGBJSMGCDG-UHFFFAOYSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- GOAQIFIXXGXKFF-UHFFFAOYSA-N 2,2-dimethyl-1h-quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(C)(C)NC2=C1 GOAQIFIXXGXKFF-UHFFFAOYSA-N 0.000 claims 1
- OESYASHKFVCSTL-UHFFFAOYSA-N 2-(1,3-thiazol-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=NC=CS1 OESYASHKFVCSTL-UHFFFAOYSA-N 0.000 claims 1
- WPMXZRLXEGVIHU-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=NC=CN1 WPMXZRLXEGVIHU-UHFFFAOYSA-N 0.000 claims 1
- OSFDRCPUKQFYBL-UHFFFAOYSA-N 2-(2-aminoethyl)-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(CCN)NC2=C1 OSFDRCPUKQFYBL-UHFFFAOYSA-N 0.000 claims 1
- SRZVHVKEKUVWKE-UHFFFAOYSA-N 2-(2-nitrophenyl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1[N+]([O-])=O SRZVHVKEKUVWKE-UHFFFAOYSA-N 0.000 claims 1
- PZFBPUAOCMMRLZ-UHFFFAOYSA-N 2-(2-trimethylsilylethynyl)-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(C#C[Si](C)(C)C)NC2=C1 PZFBPUAOCMMRLZ-UHFFFAOYSA-N 0.000 claims 1
- DRBTXTOYZCLBJI-UHFFFAOYSA-N 2-(3-aminopropyl)-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(CCCN)NC2=C1 DRBTXTOYZCLBJI-UHFFFAOYSA-N 0.000 claims 1
- WKAUNVBOSOJUSS-UHFFFAOYSA-N 2-(4-amino-5-fluoro-1,2-dihydroquinazolin-2-yl)phenol Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1O WKAUNVBOSOJUSS-UHFFFAOYSA-N 0.000 claims 1
- QFSLLBYFMDJKDY-UHFFFAOYSA-N 2-(4-nitrophenyl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=C([N+]([O-])=O)C=C1 QFSLLBYFMDJKDY-UHFFFAOYSA-N 0.000 claims 1
- HLWCINSTSGDTIB-UHFFFAOYSA-N 2-(5-nitrothiophen-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=C([N+]([O-])=O)S1 HLWCINSTSGDTIB-UHFFFAOYSA-N 0.000 claims 1
- RIOVUWRMOKFDQS-UHFFFAOYSA-N 2-(furan-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=CO1 RIOVUWRMOKFDQS-UHFFFAOYSA-N 0.000 claims 1
- GUQOCUFCTACPTQ-UHFFFAOYSA-N 2-(furan-2-yl)-5-methylsulfanyl-1,2-dihydroquinazolin-4-amine Chemical compound N1=C(N)C=2C(SC)=CC=CC=2NC1C1=CC=CO1 GUQOCUFCTACPTQ-UHFFFAOYSA-N 0.000 claims 1
- KCGIUYAUVHLJJL-UHFFFAOYSA-N 2-[2-(2-aminoethyl)phenyl]-1,2-dihydroquinazolin-4-amine Chemical compound NCCC1=CC=CC=C1C1N=C(N)C2=CC=CC=C2N1 KCGIUYAUVHLJJL-UHFFFAOYSA-N 0.000 claims 1
- DZJUSQRIYRWFKW-UHFFFAOYSA-N 2-[2-(2-azidoethyl)phenyl]-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=CC=C1CCN=[N+]=[N-] DZJUSQRIYRWFKW-UHFFFAOYSA-N 0.000 claims 1
- PFKHXJPYRVMZLW-UHFFFAOYSA-N 2-[4-(dimethylamino)phenyl]-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC(N(C)C)=CC=C1C1N=C(N)C2=CC=CC=C2N1 PFKHXJPYRVMZLW-UHFFFAOYSA-N 0.000 claims 1
- UIIANCNAHLNGKW-UHFFFAOYSA-N 2-anthracen-9-yl-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(C3N=C(C4=CC=CC=C4N3)N)=C(C=CC=C3)C3=CC2=C1 UIIANCNAHLNGKW-UHFFFAOYSA-N 0.000 claims 1
- REDQGPXPTDODAT-UHFFFAOYSA-N 2-cyanoethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)OCCC#N)CC2 REDQGPXPTDODAT-UHFFFAOYSA-N 0.000 claims 1
- YQSLFNIIJBAELO-UHFFFAOYSA-N 2-cyclobutyl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1CCC1 YQSLFNIIJBAELO-UHFFFAOYSA-N 0.000 claims 1
- TWDKMKHCHFFGDT-UHFFFAOYSA-N 2-cyclobutyl-5-fluoro-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1CCC1 TWDKMKHCHFFGDT-UHFFFAOYSA-N 0.000 claims 1
- CODFUQOUEHCCNF-UHFFFAOYSA-N 2-cyclopentyl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1CCCC1 CODFUQOUEHCCNF-UHFFFAOYSA-N 0.000 claims 1
- MXQUJZRTIGEIOF-UHFFFAOYSA-N 2-cyclopropyl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1CC1 MXQUJZRTIGEIOF-UHFFFAOYSA-N 0.000 claims 1
- YFDYGSPBBLYHLX-UHFFFAOYSA-N 2-cyclopropyl-1-methyl-2h-quinazolin-4-amine Chemical compound N1=C(N)C2=CC=CC=C2N(C)C1C1CC1 YFDYGSPBBLYHLX-UHFFFAOYSA-N 0.000 claims 1
- MFRCBOKLESMGRI-UHFFFAOYSA-N 2-ethyl-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(CC)NC2=C1 MFRCBOKLESMGRI-UHFFFAOYSA-N 0.000 claims 1
- REYBEBUFZZALFV-UHFFFAOYSA-N 2-ethyl-2-methyl-1h-quinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(CC)(C)NC2=C1 REYBEBUFZZALFV-UHFFFAOYSA-N 0.000 claims 1
- KKIKPJKOGYZZHP-UHFFFAOYSA-N 2-ethynyl-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(C#C)NC2=C1 KKIKPJKOGYZZHP-UHFFFAOYSA-N 0.000 claims 1
- CLTSEWJWIDOHJZ-UHFFFAOYSA-N 2-methoxyethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCCOC)CCC21N=C(N)C1=C(F)C=CC=C1N2 CLTSEWJWIDOHJZ-UHFFFAOYSA-N 0.000 claims 1
- BFASSLCZFJPKRD-UHFFFAOYSA-N 2-methyl-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC=C2C(N)=NC(C)NC2=C1 BFASSLCZFJPKRD-UHFFFAOYSA-N 0.000 claims 1
- YVXJSSLNOVOYBG-UHFFFAOYSA-N 2-methyl-2-phenyl-1h-quinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1(C)C1=CC=CC=C1 YVXJSSLNOVOYBG-UHFFFAOYSA-N 0.000 claims 1
- FUCNABOVCYXQIG-UHFFFAOYSA-N 2-methylpropyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC(C)C)CCC21N=C(N)C1=C(F)C=CC=C1N2 FUCNABOVCYXQIG-UHFFFAOYSA-N 0.000 claims 1
- XNWAEPWOAAIYIV-UHFFFAOYSA-N 2-phenoxyethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OCCOC1=CC=CC=C1 XNWAEPWOAAIYIV-UHFFFAOYSA-N 0.000 claims 1
- HRFIDKBTEAWKLR-UHFFFAOYSA-N 2-pyridin-4-yl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=NC=C1 HRFIDKBTEAWKLR-UHFFFAOYSA-N 0.000 claims 1
- BANNSJWZPQEZDG-UHFFFAOYSA-N 3-(1,3-dioxoisoindol-2-yl)propyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC11CCN(C(=O)OCCCN2C(C3=CC=CC=C3C2=O)=O)CC1 BANNSJWZPQEZDG-UHFFFAOYSA-N 0.000 claims 1
- FBZPVUKOYWWJBN-UHFFFAOYSA-N 3-(4-amino-5-fluoro-1,2-dihydroquinazolin-2-yl)phenol Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC(O)=C1 FBZPVUKOYWWJBN-UHFFFAOYSA-N 0.000 claims 1
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims 1
- ASRPSFSSAFCIJP-UHFFFAOYSA-N 3-phenoxypropyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OCCCOC1=CC=CC=C1 ASRPSFSSAFCIJP-UHFFFAOYSA-N 0.000 claims 1
- JREYTKUJENPMHF-UHFFFAOYSA-N 4-(4-amino-1,2-dihydroquinazolin-2-yl)benzonitrile Chemical compound N1C2=CC=CC=C2C(N)=NC1C1=CC=C(C#N)C=C1 JREYTKUJENPMHF-UHFFFAOYSA-N 0.000 claims 1
- ZOOSQLBAMVUYMU-UHFFFAOYSA-N 4-(4-amino-5,7-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzonitrile Chemical compound N1C2=CC(F)=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 ZOOSQLBAMVUYMU-UHFFFAOYSA-N 0.000 claims 1
- QBEPROIELNJTPN-UHFFFAOYSA-N 4-(4-amino-5-chlorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzonitrile Chemical compound N1C2=CC=CC(Cl)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 QBEPROIELNJTPN-UHFFFAOYSA-N 0.000 claims 1
- SJUUAYNNEIVONX-UHFFFAOYSA-N 4-(4-amino-5-fluoro-1,2-dihydroquinazolin-2-yl)phenol Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=C(O)C=C1 SJUUAYNNEIVONX-UHFFFAOYSA-N 0.000 claims 1
- VXTIJEHJPZTWSC-UHFFFAOYSA-N 4-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)-2-fluorobenzonitrile Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C(F)=C1 VXTIJEHJPZTWSC-UHFFFAOYSA-N 0.000 claims 1
- MUXAPSCMXSGRMK-UHFFFAOYSA-N 4-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)-2-methylbenzonitrile Chemical compound C1=C(C#N)C(C)=CC(C(=O)N2CCC3(CC2)N=C(N)C2=C(F)C=CC=C2N3)=C1 MUXAPSCMXSGRMK-UHFFFAOYSA-N 0.000 claims 1
- GROLIDJOEMLLED-UHFFFAOYSA-N 4-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzonitrile Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 GROLIDJOEMLLED-UHFFFAOYSA-N 0.000 claims 1
- RYUPRRZQWHRNKD-UHFFFAOYSA-N 4-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbothioyl)benzonitrile Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=S)C1=CC=C(C#N)C=C1 RYUPRRZQWHRNKD-UHFFFAOYSA-N 0.000 claims 1
- OGFYIRCPFJGCPD-UHFFFAOYSA-N 4-(4-amino-5-methoxyspiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzonitrile Chemical compound N1=C(N)C=2C(OC)=CC=CC=2NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 OGFYIRCPFJGCPD-UHFFFAOYSA-N 0.000 claims 1
- REINVSVZVLMNRB-UHFFFAOYSA-N 4-(4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzenesulfonamide Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(S(N)(=O)=O)C=C1 REINVSVZVLMNRB-UHFFFAOYSA-N 0.000 claims 1
- LAHZEKUNLGBBCY-UHFFFAOYSA-N 4-(4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)benzonitrile Chemical compound N1C2=CC=CC=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)C=C1 LAHZEKUNLGBBCY-UHFFFAOYSA-N 0.000 claims 1
- FALRGMYMKLFBCW-UHFFFAOYSA-N 4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxamide Chemical compound C1CN(C(=O)N)CCC21N=C(N)C1=CC=CC=C1N2 FALRGMYMKLFBCW-UHFFFAOYSA-N 0.000 claims 1
- TWEHLZWFXKAKJA-UHFFFAOYSA-N 4-chlorobutyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)OCCCCCl)CC2 TWEHLZWFXKAKJA-UHFFFAOYSA-N 0.000 claims 1
- PAMAGZZQYDQEPT-UHFFFAOYSA-N 4-phenylbutyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OCCCCC1=CC=CC=C1 PAMAGZZQYDQEPT-UHFFFAOYSA-N 0.000 claims 1
- MPIJKWLZLLAICB-UHFFFAOYSA-N 5-(4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbonyl)pyridine-2-carbonitrile Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)C1=CC=C(C#N)N=C1 MPIJKWLZLLAICB-UHFFFAOYSA-N 0.000 claims 1
- ZBZXORNPMDSVBO-UHFFFAOYSA-N 5-chloro-2-(furan-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CO1 ZBZXORNPMDSVBO-UHFFFAOYSA-N 0.000 claims 1
- KZMMWKJKRXYXRH-UHFFFAOYSA-N 5-chloro-2-thiophen-2-yl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(Cl)=C2C(N)=NC1C1=CC=CS1 KZMMWKJKRXYXRH-UHFFFAOYSA-N 0.000 claims 1
- SVLIWQZMYTWKEX-UHFFFAOYSA-N 5-chloropentyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)OCCCCCCl)CC2 SVLIWQZMYTWKEX-UHFFFAOYSA-N 0.000 claims 1
- BFDAIAGGTOZVEA-UHFFFAOYSA-N 5-fluoro-1'-(thiophen-2-yliminomethyl)spiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C=NC1=CC=CS1 BFDAIAGGTOZVEA-UHFFFAOYSA-N 0.000 claims 1
- NGFFAUZBTWFKRY-UHFFFAOYSA-N 5-fluoro-2-(1,3-thiazol-2-yl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=NC=CS1 NGFFAUZBTWFKRY-UHFFFAOYSA-N 0.000 claims 1
- AKOSZLBIPKPADG-UHFFFAOYSA-N 5-fluoro-2-(4-fluorophenyl)-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=C(F)C=C1 AKOSZLBIPKPADG-UHFFFAOYSA-N 0.000 claims 1
- ADVXVBOVHBALNY-UHFFFAOYSA-N 5-fluoro-2-(4-methoxyphenyl)-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC(OC)=CC=C1C1N=C(N)C2=C(F)C=CC=C2N1 ADVXVBOVHBALNY-UHFFFAOYSA-N 0.000 claims 1
- UYXRIQUZSCKEBY-UHFFFAOYSA-N 5-fluoro-2-(4-methylsulfanylphenyl)-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC(SC)=CC=C1C1N=C(N)C2=C(F)C=CC=C2N1 UYXRIQUZSCKEBY-UHFFFAOYSA-N 0.000 claims 1
- PIVPSBNKQBZPLC-UHFFFAOYSA-N 5-fluoro-2-(furan-2-yl)-2-methyl-1h-quinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(C)C1=CC=CO1 PIVPSBNKQBZPLC-UHFFFAOYSA-N 0.000 claims 1
- WHZFSGZHOACEEC-UHFFFAOYSA-N 5-fluoro-2-[2-(trifluoromethyl)phenyl]-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1C(F)(F)F WHZFSGZHOACEEC-UHFFFAOYSA-N 0.000 claims 1
- IABLTGUVVWICLB-UHFFFAOYSA-N 5-fluoro-2-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=C(C(F)(F)F)C=C1 IABLTGUVVWICLB-UHFFFAOYSA-N 0.000 claims 1
- QFNLYCUBYXJYKQ-UHFFFAOYSA-N 5-fluoro-2-phenyl-1,2-dihydroquinazolin-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1C1=CC=CC=C1 QFNLYCUBYXJYKQ-UHFFFAOYSA-N 0.000 claims 1
- VAKMJMYAYACJOE-UHFFFAOYSA-N 5-fluoro-2-propan-2-yl-1,2-dihydroquinazolin-4-amine Chemical compound C1=CC(F)=C2C(N)=NC(C(C)C)NC2=C1 VAKMJMYAYACJOE-UHFFFAOYSA-N 0.000 claims 1
- BWQKVQOXURJROY-UHFFFAOYSA-N 5-fluorospiro[1h-quinazoline-2,3'-azetidine]-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CNC2 BWQKVQOXURJROY-UHFFFAOYSA-N 0.000 claims 1
- RUZOQNAMPCLLFI-UHFFFAOYSA-N 5-fluorospiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCNCC2 RUZOQNAMPCLLFI-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- ZRVUJXDFFKFLMG-UHFFFAOYSA-N Meloxicam Chemical compound OC=1C2=CC=CC=C2S(=O)(=O)N(C)C=1C(=O)NC1=NC=C(C)S1 ZRVUJXDFFKFLMG-UHFFFAOYSA-N 0.000 claims 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 235000010233 benzoic acid Nutrition 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 235000010290 biphenyl Nutrition 0.000 claims 1
- NPMHFMGHDIJHHJ-UHFFFAOYSA-N butyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCCCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 NPMHFMGHDIJHHJ-UHFFFAOYSA-N 0.000 claims 1
- 229920005556 chlorobutyl Polymers 0.000 claims 1
- ORJHMHMKBAQVNZ-UHFFFAOYSA-N cyclobutyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OC1CCC1 ORJHMHMKBAQVNZ-UHFFFAOYSA-N 0.000 claims 1
- QKANJNYYDUTJOD-UHFFFAOYSA-N cyclopentyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC1(CC1)CCN1C(=O)OC1CCCC1 QKANJNYYDUTJOD-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- PQJLAHMCHXZENU-UHFFFAOYSA-N ethyl 2-(4-amino-1,2-dihydroquinazolin-2-yl)pyrrole-1-carboxylate Chemical compound CCOC(=O)N1C=CC=C1C1N=C(N)C2=CC=CC=C2N1 PQJLAHMCHXZENU-UHFFFAOYSA-N 0.000 claims 1
- XDBCJNIYUIEEBA-UHFFFAOYSA-N ethyl 4'-amino-5'-fluoro-1'-methylspiro[piperidine-4,2'-quinazoline]-1-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N(C)C1=CC=CC(F)=C1C(N)=N2 XDBCJNIYUIEEBA-UHFFFAOYSA-N 0.000 claims 1
- VEZHBHLPCUVXSO-UHFFFAOYSA-N ethyl 4-amino-5,7-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=C(F)C=C(F)C=C1N2 VEZHBHLPCUVXSO-UHFFFAOYSA-N 0.000 claims 1
- NCBXOVPEHJFJMA-UHFFFAOYSA-N ethyl 4-amino-5,8-difluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=C(F)C=CC(F)=C1N2 NCBXOVPEHJFJMA-UHFFFAOYSA-N 0.000 claims 1
- UTCXKRXHURSMMU-UHFFFAOYSA-N ethyl 4-amino-5-chlorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=C(Cl)C=CC=C1N2 UTCXKRXHURSMMU-UHFFFAOYSA-N 0.000 claims 1
- GMSQWLPSYYHCMA-UHFFFAOYSA-N ethyl 4-amino-5-fluorospiro[1h-quinazoline-2,3'-azetidine]-1'-carboxylate Chemical compound C1N(C(=O)OCC)CC21N=C(N)C1=C(F)C=CC=C1N2 GMSQWLPSYYHCMA-UHFFFAOYSA-N 0.000 claims 1
- FTNKTGJCALFVLR-UHFFFAOYSA-N ethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 FTNKTGJCALFVLR-UHFFFAOYSA-N 0.000 claims 1
- HZNFNPNOLANCRF-UHFFFAOYSA-N ethyl 4-amino-5-hydroxyspiro[1H-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound CCOC(=O)N1CCC2(CC1)Nc1cccc(O)c1C(N)=N2 HZNFNPNOLANCRF-UHFFFAOYSA-N 0.000 claims 1
- WDEUWHGHBDLQLS-UHFFFAOYSA-N ethyl 4-amino-5-methoxyspiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=C(OC)C=CC=C1N2 WDEUWHGHBDLQLS-UHFFFAOYSA-N 0.000 claims 1
- VOVKMYMVOKLCKB-UHFFFAOYSA-N ethyl 4-aminospiro[1h-quinazoline-2,3'-piperidine]-1'-carboxylate Chemical compound C1N(C(=O)OCC)CCCC21N=C(N)C1=CC=CC=C1N2 VOVKMYMVOKLCKB-UHFFFAOYSA-N 0.000 claims 1
- AHHOSQDBUVVJMC-UHFFFAOYSA-N ethyl 4-aminospiro[1h-quinazoline-2,3'-pyrrolidine]-1'-carboxylate Chemical compound C1N(C(=O)OCC)CCC21N=C(N)C1=CC=CC=C1N2 AHHOSQDBUVVJMC-UHFFFAOYSA-N 0.000 claims 1
- JRIQJZQEZRAXTQ-UHFFFAOYSA-N ethyl 4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCC)CCC21N=C(N)C1=CC=CC=C1N2 JRIQJZQEZRAXTQ-UHFFFAOYSA-N 0.000 claims 1
- KKKPZBPTHCMOLC-UHFFFAOYSA-N ethyl n-[(4-amino-1,2-dihydroquinazolin-2-yl)methyl]carbamate Chemical compound C1=CC=C2C(N)=NC(CNC(=O)OCC)NC2=C1 KKKPZBPTHCMOLC-UHFFFAOYSA-N 0.000 claims 1
- HWWPBSFOVZSOIV-UHFFFAOYSA-N ethyl n-[2-(4-amino-1,2-dihydroquinazolin-2-yl)ethyl]carbamate Chemical compound C1=CC=C2C(N)=NC(CCNC(=O)OCC)NC2=C1 HWWPBSFOVZSOIV-UHFFFAOYSA-N 0.000 claims 1
- OASZGLQDCWJTPG-UHFFFAOYSA-N ethyl n-[3-(4-amino-1,2-dihydroquinazolin-2-yl)propyl]carbamate Chemical compound C1=CC=C2C(N)=NC(CCCNC(=O)OCC)NC2=C1 OASZGLQDCWJTPG-UHFFFAOYSA-N 0.000 claims 1
- 229950005722 flosulide Drugs 0.000 claims 1
- WKGGTZIYFSQLEF-UHFFFAOYSA-N hexyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCCCCCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 WKGGTZIYFSQLEF-UHFFFAOYSA-N 0.000 claims 1
- 229960001929 meloxicam Drugs 0.000 claims 1
- JWJJTPJYDSDVPZ-UHFFFAOYSA-N methyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OC)CCC21N=C(N)C1=C(F)C=CC=C1N2 JWJJTPJYDSDVPZ-UHFFFAOYSA-N 0.000 claims 1
- KVJOEMOOQPMHPU-UHFFFAOYSA-N methyl 4-aminospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OC)CCC21N=C(N)C1=CC=CC=C1N2 KVJOEMOOQPMHPU-UHFFFAOYSA-N 0.000 claims 1
- CXJONBHNIJFARE-UHFFFAOYSA-N n-[6-(2,4-difluorophenoxy)-1-oxo-2,3-dihydroinden-5-yl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=2CCC(=O)C=2C=C1OC1=CC=C(F)C=C1F CXJONBHNIJFARE-UHFFFAOYSA-N 0.000 claims 1
- HRJPPZFUNGWEBZ-UHFFFAOYSA-N o-ethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbothioate Chemical compound C1CN(C(=S)OCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 HRJPPZFUNGWEBZ-UHFFFAOYSA-N 0.000 claims 1
- RGMIHKSHJVEMLI-UHFFFAOYSA-N pent-4-ynyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)OCCCC#C)CC2 RGMIHKSHJVEMLI-UHFFFAOYSA-N 0.000 claims 1
- ZTBGTUKEGXERBI-UHFFFAOYSA-N pentyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCCCCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 ZTBGTUKEGXERBI-UHFFFAOYSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- CAKJPNLHAYGOIZ-UHFFFAOYSA-N prop-2-ynyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound N1C2=CC=CC(F)=C2C(N)=NC21CCN(C(=O)OCC#C)CC2 CAKJPNLHAYGOIZ-UHFFFAOYSA-N 0.000 claims 1
- GYQIFXOUPFHASL-UHFFFAOYSA-N propan-2-yl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OC(C)C)CCC21N=C(N)C1=C(F)C=CC=C1N2 GYQIFXOUPFHASL-UHFFFAOYSA-N 0.000 claims 1
- QUEZQVVHMOJXGT-UHFFFAOYSA-N propan-2-yl 4-aminospiro[1H-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound NC1=NC2(NC3=CC=CC=C13)CCN(CC2)C(=O)OC(C)C QUEZQVVHMOJXGT-UHFFFAOYSA-N 0.000 claims 1
- ZHEWFGMBRWXYEV-UHFFFAOYSA-N propyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carboxylate Chemical compound C1CN(C(=O)OCCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 ZHEWFGMBRWXYEV-UHFFFAOYSA-N 0.000 claims 1
- QBJQGVHAJXIHGL-UHFFFAOYSA-N s-ethyl 4-amino-5-fluorospiro[1h-quinazoline-2,4'-piperidine]-1'-carbothioate Chemical compound C1CN(C(=O)SCC)CCC21N=C(N)C1=C(F)C=CC=C1N2 QBJQGVHAJXIHGL-UHFFFAOYSA-N 0.000 claims 1
- 239000004576 sand Substances 0.000 claims 1
- YAGBUQONHWCOLW-UHFFFAOYSA-N spiro[1h-quinazoline-2,1'-cyclopentane]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC21CCCC2 YAGBUQONHWCOLW-UHFFFAOYSA-N 0.000 claims 1
- YSIFOLULMFTZKL-UHFFFAOYSA-N spiro[1h-quinazoline-2,4'-piperidine]-4-amine Chemical compound N1C2=CC=CC=C2C(N)=NC21CCNCC2 YSIFOLULMFTZKL-UHFFFAOYSA-N 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- MIMJSJSRRDZIPW-UHFFFAOYSA-N tilmacoxib Chemical compound C=1C=C(S(N)(=O)=O)C(F)=CC=1C=1OC(C)=NC=1C1CCCCC1 MIMJSJSRRDZIPW-UHFFFAOYSA-N 0.000 claims 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 32
- 108010076864 Nitric Oxide Synthase Type II Proteins 0.000 description 27
- 206010061218 Inflammation Diseases 0.000 description 7
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 7
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 7
- 230000004054 inflammatory process Effects 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 102100028452 Nitric oxide synthase, endothelial Human genes 0.000 description 4
- 101710090055 Nitric oxide synthase, endothelial Proteins 0.000 description 4
- 102000001708 Protein Isoforms Human genes 0.000 description 4
- 108010029485 Protein Isoforms Proteins 0.000 description 4
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 206010003246 arthritis Diseases 0.000 description 4
- 230000006698 induction Effects 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 150000003180 prostaglandins Chemical class 0.000 description 4
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 3
- 102100022397 Nitric oxide synthase, brain Human genes 0.000 description 3
- 101710111444 Nitric oxide synthase, brain Proteins 0.000 description 3
- 208000037976 chronic inflammation Diseases 0.000 description 3
- 208000037893 chronic inflammatory disorder Diseases 0.000 description 3
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 230000035479 physiological effects, processes and functions Effects 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000008299 Nitric Oxide Synthase Human genes 0.000 description 2
- 108010021487 Nitric Oxide Synthase Proteins 0.000 description 2
- 241000219061 Rheum Species 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 239000002158 endotoxin Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229940094443 oxytocics prostaglandins Drugs 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
- 229940124638 COX inhibitor Drugs 0.000 description 1
- 102000010907 Cyclooxygenase 2 Human genes 0.000 description 1
- 108010037462 Cyclooxygenase 2 Proteins 0.000 description 1
- 208000009386 Experimental Arthritis Diseases 0.000 description 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 description 1
- 102000008070 Interferon-gamma Human genes 0.000 description 1
- 108010074328 Interferon-gamma Proteins 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KCWZGJVSDFYRIX-YFKPBYRVSA-N N(gamma)-nitro-L-arginine methyl ester Chemical compound COC(=O)[C@@H](N)CCCN=C(N)N[N+]([O-])=O KCWZGJVSDFYRIX-YFKPBYRVSA-N 0.000 description 1
- NTNWOCRCBQPEKQ-YFKPBYRVSA-N N(omega)-methyl-L-arginine Chemical compound CN=C(N)NCCC[C@H](N)C(O)=O NTNWOCRCBQPEKQ-YFKPBYRVSA-N 0.000 description 1
- NTNWOCRCBQPEKQ-UHFFFAOYSA-N NG-mono-methyl-L-arginine Natural products CN=C(N)NCCCC(N)C(O)=O NTNWOCRCBQPEKQ-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 108700012920 TNF Proteins 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 206010054094 Tumour necrosis Diseases 0.000 description 1
- 229920000392 Zymosan Polymers 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229920001525 carrageenan Polymers 0.000 description 1
- 229940113118 carrageenan Drugs 0.000 description 1
- 235000010418 carrageenan Nutrition 0.000 description 1
- 239000000679 carrageenan Substances 0.000 description 1
- 230000008355 cartilage degradation Effects 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- HUPFGZXOMWLGNK-UHFFFAOYSA-N diflunisal Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C(=CC(F)=CC=2)F)=C1 HUPFGZXOMWLGNK-UHFFFAOYSA-N 0.000 description 1
- 229960000616 diflunisal Drugs 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 239000003797 essential amino acid Substances 0.000 description 1
- 229960002390 flurbiprofen Drugs 0.000 description 1
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 238000011554 guinea pig model Methods 0.000 description 1
- 229960001680 ibuprofen Drugs 0.000 description 1
- 208000009326 ileitis Diseases 0.000 description 1
- 230000028993 immune response Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 229960003130 interferon gamma Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000002540 macrophage Anatomy 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- 230000001129 nonadrenergic effect Effects 0.000 description 1
- 230000002536 noncholinergic effect Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 210000003024 peritoneal macrophage Anatomy 0.000 description 1
- 206010034674 peritonitis Diseases 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000008409 synovial inflammation Effects 0.000 description 1
- 210000005222 synovial tissue Anatomy 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 230000008728 vascular permeability Effects 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 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 1
Classifications
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE9802333A SE9802333D0 (sv) | 1998-06-29 | 1998-06-29 | Novel combination |
Publications (1)
Publication Number | Publication Date |
---|---|
ZA200007076B true ZA200007076B (en) | 2002-02-28 |
Family
ID=20411898
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ZA200007076A ZA200007076B (en) | 1998-06-29 | 2000-11-30 | A pharmaceutical combination comprising a COX-2 inhibitor and iNOS inhibitor. |
Country Status (22)
Country | Link |
---|---|
US (1) | US6248745B1 (ja) |
EP (1) | EP1100505A1 (ja) |
JP (1) | JP2002519324A (ja) |
KR (1) | KR20010053252A (ja) |
CN (1) | CN1313769A (ja) |
AU (1) | AU4944799A (ja) |
BR (1) | BR9911666A (ja) |
CA (1) | CA2334515A1 (ja) |
CZ (1) | CZ20004896A3 (ja) |
EE (1) | EE200000766A (ja) |
ID (1) | ID27394A (ja) |
IL (1) | IL140022A0 (ja) |
IN (1) | IN2000MU00721A (ja) |
IS (1) | IS5794A (ja) |
MX (1) | MXPA00012162A (ja) |
NO (1) | NO20006559L (ja) |
PL (1) | PL345028A1 (ja) |
SE (1) | SE9802333D0 (ja) |
SK (1) | SK18482000A3 (ja) |
TR (1) | TR200003808T2 (ja) |
WO (1) | WO2000000200A1 (ja) |
ZA (1) | ZA200007076B (ja) |
Families Citing this family (75)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE60038162T2 (de) * | 1999-12-08 | 2009-02-26 | Pharmacia Corp. | Celecoxib in festkörperform mit erhöhter bioverfügbarkeit |
JP2003523958A (ja) * | 1999-12-23 | 2003-08-12 | ニトロメド インコーポレーテッド | ニトロソ化およびニトロシル化されたシクロオキシゲナーゼ−2の阻害剤、組成物ならびに使用法 |
JP4092203B2 (ja) * | 2000-12-21 | 2008-05-28 | ニトロメッド,インク. | 新規のシクロオキシゲナーゼ2選択的阻害剤としての置換アリール化合物、組成物、および使用方法 |
US7012098B2 (en) * | 2001-03-23 | 2006-03-14 | Pharmacia Corporation | Inhibitors of inducible nitric oxide synthase for chemoprevention and treatment of cancers |
WO2003057196A1 (en) * | 2002-01-07 | 2003-07-17 | Pharmacia Corporation | Drug mixture with enhanced dissolution rate |
AU2003248642A1 (en) | 2002-06-11 | 2003-12-22 | Nitromed, Inc. | Nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use |
US20040077691A1 (en) * | 2002-06-21 | 2004-04-22 | Medinox, Inc. | Hydroxamate derivatives of non-steroidal anti-inflammatory drugs |
WO2004004648A2 (en) | 2002-07-03 | 2004-01-15 | Nitromed, Inc. | Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use |
EP1542972A4 (en) * | 2002-07-29 | 2008-01-23 | Nitromed Inc | CYCLOOXYGENASE-2 SELECTIVE INHIBITORS, COMPOSITION AND METHOD OF USE |
WO2004019986A1 (en) * | 2002-08-29 | 2004-03-11 | Schering Aktiengesellschaft | Methods of treating acute respiratory distress syndrome |
PL1534305T3 (pl) | 2003-05-07 | 2007-03-30 | Osteologix As | Leczenie zaburzeń chrząstek i kości solami strontu rozpuszczalnymi w wodzie |
ES2476027T3 (es) | 2005-10-25 | 2014-07-11 | Shionogi & Co., Ltd. | Derivados de aminodihidrotriazina |
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 |
EP2083579B1 (en) | 2006-10-25 | 2014-02-12 | Huawei Technologies Co., Ltd. | Processing location update request method, network entity, congestion control method and apparatus |
CA2676413A1 (en) * | 2007-01-19 | 2008-07-31 | Mallinckrodt Inc. | Diagnostic and therapeutic cyclooxygenase-2 binding ligands |
ES2476605T3 (es) | 2007-04-24 | 2014-07-15 | Shionogi & Co., Ltd. | Derivados de aminohidrotiazina sustituidos con grupos cíclicos |
WO2008133273A1 (ja) | 2007-04-24 | 2008-11-06 | Shionogi & Co., Ltd. | アルツハイマー症治療用医薬組成物 |
WO2009120186A1 (en) * | 2008-03-24 | 2009-10-01 | Carolus Therapeutics, Inc. | Methods and compositions for treating atherosclerosis and related conditions |
AU2009258496B8 (en) | 2008-06-13 | 2014-06-26 | Shionogi & Co., Ltd. | Sulfur-containing heterocyclic derivative having beta-secretase-inhibiting activity |
JPWO2010047372A1 (ja) | 2008-10-22 | 2012-03-22 | 塩野義製薬株式会社 | Bace1阻害活性を有する2−アミノピリミジン−4−オンおよび2−アミノピリジン誘導体 |
US8453441B2 (en) | 2008-11-06 | 2013-06-04 | Purdue Research Foundation | System and method for pump-controlled cylinder cushioning |
MY145791A (en) * | 2009-05-25 | 2012-04-30 | Liang Woon San | A method for producing a nutraceutical composition and the nutraceutical produced by the method |
US8999980B2 (en) | 2009-12-11 | 2015-04-07 | Shionogi & Co., Ltd. | Oxazine derivatives |
EP2518059A4 (en) * | 2009-12-24 | 2013-05-29 | Shionogi & Co | 4-AMINO-1,3-THIAZINE OR OXAZINE DERIVATIVE |
CA2786201C (en) | 2010-01-13 | 2017-01-17 | Basf Se | Novel mannanase variants |
EP2545181B1 (en) | 2010-03-12 | 2014-11-12 | Council Of Scientific & Industrial Research | Process for the production of violacein and its derivative deoxyviolacein containing bioactive pigment from chromobacterium sp. (mtcc 5522) |
DE102010030500A1 (de) | 2010-06-24 | 2011-12-29 | Heliatek Gmbh | Verdampfbares organisch halbleitendes Material und dessen Verwendung in einem optoelektronischen Bauelement |
EP2634188A4 (en) | 2010-10-29 | 2014-05-07 | Shionogi & Co | FUSIONED AMINODIHYDROPYRIMIDINE DERIVATIVE |
EP2634186A4 (en) | 2010-10-29 | 2014-03-26 | Shionogi & Co | naphthyridine |
WO2012163466A1 (de) | 2011-06-01 | 2012-12-06 | Josef Schweiger | Verbundkrone/verbundbrücke und verfahren zu deren herstellung |
DE102011018604A1 (de) | 2011-04-25 | 2014-02-13 | Michael Friebe | Medikamenteninfusor für die Anwendung in stark magnetischen Umgebungen |
TW201247635A (en) | 2011-04-26 | 2012-12-01 | Shionogi & Co | Oxazine derivatives and a pharmaceutical composition for inhibiting BAC1 containing them |
KR102128957B1 (ko) | 2011-10-07 | 2020-07-02 | 론자 리미티드 | 조절가능한 프로모터 |
DE102012201426A1 (de) | 2012-02-01 | 2013-08-01 | Leibniz-Institut Für Polymerforschung Dresden E.V. | Verfahren zum verbinden von kunststoffen und verfahren zum lösen einer verbindung im kunststoffverbund und kunststoffverbund |
DE102012007141A1 (de) | 2012-04-10 | 2013-10-10 | Bernhard Spindler | Jalousierbarer Rollladenpanzer |
DE102012106428A1 (de) | 2012-07-17 | 2014-01-23 | Reha Technology GmbH | Vorrichtung zur therapeutischen Behandlung, System zur gerätegestützten Lokomotionstherapie und Verfahren zur Steuerung der Vorrichtung |
WO2014024034A1 (es) | 2012-08-08 | 2014-02-13 | Choque Alberto Pati | Compostaje de residuos sólidos, liquidos y lodos biodegradables mediante humus de lombriz (eisenia foetida y especies similares) y mezclas de humus de lombriz y material estomacal con alto contenido de microrganismos |
DE102012214452B4 (de) | 2012-08-14 | 2019-08-01 | Henkel Ag & Co. Kgaa | Vorrichtung zum Auftragen einer fadenförmigen Masse |
DE102012016116A1 (de) | 2012-08-15 | 2014-02-20 | Josip Fellner | 360° Bag ln Box Spendersystem |
DE102012214554A1 (de) | 2012-08-16 | 2014-02-20 | Robert Bosch Gmbh | Verfahren zur Überführung von Batterien in einen entladenen Zustand, Batteriemanagementsystem, Inverter, System zur Erzeugung einer Wechselspannung, Ladestromquelle und Kraftfahrzeug |
DE102012108153A1 (de) | 2012-09-03 | 2014-03-06 | Ludwig-Maximilians-Universität München | Rohling und Verfahren zur Herstellung einer Dentalrestauration durch substraktive Bearbeitung |
WO2014065434A1 (en) | 2012-10-24 | 2014-05-01 | Shionogi & Co., Ltd. | Dihydrooxazine or oxazepine derivatives having bace1 inhibitory activity |
DE102012112186A1 (de) | 2012-12-12 | 2014-06-26 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Materialverbund, Verfahren zu dessen Herstellung, daraus hergestelltes System und Anwendung desselben |
WO2014135249A2 (de) | 2013-02-15 | 2014-09-12 | Jochen Mertens | Mixer mit massnahmen zur reduzierung des eintrages von luftsauerstoff in den mixer-inhalt |
DE102013101712B4 (de) | 2013-02-21 | 2020-05-28 | Heliatek Gmbh | Photoaktives organisches Material für optoelektronische Bauelemente |
DE102013101713B4 (de) | 2013-02-21 | 2020-10-01 | Heliatek Gmbh | Photoaktives, organisches Material für optoelektronische Bauelemente |
DE102013102364A1 (de) | 2013-03-10 | 2014-09-11 | Informium Ag | Verfahren zur Herstellung eines Identifikationsmerkmals mit integriertem Kopierschutz |
DE102013102366A1 (de) | 2013-03-10 | 2014-09-11 | Informium Ag | Vorrichtungen zur Herstellung und zum Auslesen eines Identifikationsmerkmals mit integriertem Kopierschutz |
DE102013102365A1 (de) | 2013-03-10 | 2014-09-11 | Informium Ag | Identifikationsmerkmal mit integriertem Kopierschutz |
DE102013004288A1 (de) | 2013-03-13 | 2014-09-18 | Matthias Lietzau | Fahrzeug Verbindungsfolie |
DE202013002767U1 (de) | 2013-03-22 | 2013-05-28 | Lorenz-Montagesysteme Gmbh | Ausgleichende Seitverbindung von Solarmodulen |
DE102013005741B3 (de) | 2013-04-05 | 2014-05-22 | IOT - Innovative Oberflächentechnologien GmbH | Vorrichtung zur Inertisierung bei UV-Bestrahlung in offenen Durchlaufanlagen |
EP2792394B1 (de) | 2013-04-16 | 2016-07-27 | Jörg Beutler | Interaktive Geschwindigkeitssteuerung |
DE102013104501A1 (de) | 2013-05-02 | 2014-11-06 | B. Braun Avitum Ag | Vorrichtung zur extrakorporalen Blutbehandlung |
DE102013008359A1 (de) | 2013-05-16 | 2014-11-20 | Sew-Eurodrive Gmbh & Co Kg | Energiespeicher, der aus in Reihe geschalten Energiespeicherzellen aufgebaut ist, und Schaltungsanordnung zur passiven Symmetrierung einer Reihenschaltung von Kondensatoren |
DE102013008919B4 (de) | 2013-05-24 | 2017-12-07 | Magdeburger Windkraftanlagen GmbH | Rotorsystem für die Energiewandlung von kinetischer Energie in Fluiden und Massenströmen |
DE202013006258U1 (de) | 2013-07-11 | 2013-10-11 | IMM Ingenieurbüro GmbH | Vorrichtung zum Erzeugen von heizbaren Flächen mit homogener Wärmeverteilung |
DE102013110693B4 (de) | 2013-09-27 | 2024-04-25 | Heliatek Gmbh | Photoaktives, organisches Material für optoelektronische Bauelemente |
EP2873807A1 (de) | 2013-11-18 | 2015-05-20 | Siemens Aktiengesellschaft | Abdeckplatte, Laufschaufel, Radscheibe, Bolzen und Gasturbine |
WO2015075040A1 (de) | 2013-11-19 | 2015-05-28 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verfahren zum verbinden von silikongummi mit einem substrat |
EP2902692B1 (de) | 2013-12-06 | 2017-10-25 | MAGNA STEYR Engineering AG & Co KG | Bauteil eines Tanksystems |
DE202014100570U1 (de) | 2014-02-10 | 2014-03-10 | Schlaadt Plastics Gmbh | Klappsystem zur Verbindung von Partikelschaumbauteilen mittels eines gegen Verlust gesicherten Steckelements |
DE102014004280A1 (de) | 2014-03-26 | 2015-10-01 | Florian M. König | Impulssignal-Erzeugungsvorrichtung für Zwecke der autonomen Batterieaufladung oder 120-/230-Volt-Lampenversorgung |
DE202014003299U1 (de) | 2014-04-14 | 2014-08-25 | Antje Koss | Stollenschuh mit Wechselstollensystem |
DE202014004532U1 (de) | 2014-05-28 | 2014-08-05 | Hans-Dieter Cornelius | Hygienevorlage |
DE102015214641A1 (de) | 2014-11-10 | 2016-05-12 | Hermann Roth | Zusammensetzung mit Säure und Isochinolinalkaloid |
DE102014017938A1 (de) | 2014-12-05 | 2016-06-09 | Florian M. König | Trichter-turbinenartige Vorrichtung mit elektromagnetischer Rotationssteuerung von Flüssigkeits-Mischvorgängen |
DE102015000003A1 (de) | 2015-01-02 | 2016-07-07 | Solukon Ingenieure GbR (vertretungsberechtigte Gesellschafter: Andreas Hartmann, 86391 Stadtbergen und Dominik Schmid, 86165 Augsburg) | Baubehälter für Produktionsanlagen zur Herstellung von Bauteilen in Schichtbauverfahren |
DE102015008129A1 (de) | 2015-01-22 | 2016-07-28 | Liebherr-Hausgeräte Lienz Gmbh | Verfahren zur Bestimmung der Dämmeigenschaft einer Wandung eines wärmeisolierten Behältnisses |
DE102015000887A1 (de) | 2015-01-23 | 2016-07-28 | Arnulf Deinzer | Zahnreinigungsgerät mit ausfahrbaren Borsten |
DE102015015877A1 (de) | 2015-12-09 | 2017-06-14 | Bayerisches Zentrum für angewandte Energieforschung, e.V. (ZAE Bayern) | Optisch schaltendes Element |
DE102016006696A1 (de) | 2016-05-27 | 2017-11-30 | Christoph Jaeger | Flugautosystem |
DE202016004226U1 (de) | 2016-07-06 | 2016-11-11 | Helmut Senkel | Schienensystem mit verfahrbaren Verbrauchern |
CN106279585A (zh) * | 2016-08-26 | 2017-01-04 | 宁波圣达精工智能科技有限公司 | 一种阻燃智能密集书架的制备方法 |
CN108832306B (zh) * | 2018-06-13 | 2023-11-03 | 中国科学院国家天文台 | 一种fast反射面中心孔柔性封堵结构 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA2235304A1 (en) | 1995-10-17 | 1997-04-24 | Thomas Mcinally | Pharmaceutically active quinazoline compounds |
-
1998
- 1998-06-29 SE SE9802333A patent/SE9802333D0/xx unknown
-
1999
- 1999-06-23 SK SK1848-2000A patent/SK18482000A3/sk unknown
- 1999-06-23 EP EP99933384A patent/EP1100505A1/en not_active Withdrawn
- 1999-06-23 US US09/380,379 patent/US6248745B1/en not_active Expired - Fee Related
- 1999-06-23 MX MXPA00012162 patent/MXPA00012162A/es unknown
- 1999-06-23 CA CA002334515A patent/CA2334515A1/en not_active Abandoned
- 1999-06-23 KR KR1020007014933A patent/KR20010053252A/ko not_active Application Discontinuation
- 1999-06-23 ID IDW20002691A patent/ID27394A/id unknown
- 1999-06-23 EE EEP200000766A patent/EE200000766A/xx unknown
- 1999-06-23 TR TR2000/03808T patent/TR200003808T2/xx unknown
- 1999-06-23 AU AU49447/99A patent/AU4944799A/en not_active Abandoned
- 1999-06-23 BR BR9911666-9A patent/BR9911666A/pt not_active Application Discontinuation
- 1999-06-23 PL PL99345028A patent/PL345028A1/xx not_active Application Discontinuation
- 1999-06-23 JP JP2000556785A patent/JP2002519324A/ja active Pending
- 1999-06-23 WO PCT/SE1999/001144 patent/WO2000000200A1/en not_active Application Discontinuation
- 1999-06-23 CN CN99810007A patent/CN1313769A/zh active Pending
- 1999-06-23 IL IL14002299A patent/IL140022A0/xx unknown
- 1999-06-23 CZ CZ20004896A patent/CZ20004896A3/cs unknown
-
2000
- 2000-08-01 IN IN721MU2000 patent/IN2000MU00721A/en unknown
- 2000-11-30 ZA ZA200007076A patent/ZA200007076B/en unknown
- 2000-12-21 NO NO20006559A patent/NO20006559L/no not_active Application Discontinuation
- 2000-12-27 IS IS5794A patent/IS5794A/is unknown
Also Published As
Publication number | Publication date |
---|---|
ID27394A (id) | 2001-04-05 |
NO20006559L (no) | 2001-02-28 |
CN1313769A (zh) | 2001-09-19 |
SK18482000A3 (sk) | 2001-07-10 |
NO20006559D0 (no) | 2000-12-21 |
JP2002519324A (ja) | 2002-07-02 |
EP1100505A1 (en) | 2001-05-23 |
CZ20004896A3 (en) | 2001-06-13 |
EE200000766A (et) | 2002-06-17 |
MXPA00012162A (es) | 2001-05-01 |
US6248745B1 (en) | 2001-06-19 |
IL140022A0 (en) | 2002-02-10 |
IN2000MU00721A (ja) | 2005-03-18 |
BR9911666A (pt) | 2001-03-20 |
WO2000000200A1 (en) | 2000-01-06 |
CA2334515A1 (en) | 2000-01-06 |
IS5794A (is) | 2000-12-27 |
PL345028A1 (en) | 2001-11-19 |
SE9802333D0 (sv) | 1998-06-29 |
AU4944799A (en) | 2000-01-17 |
TR200003808T2 (tr) | 2001-06-21 |
KR20010053252A (ko) | 2001-06-25 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
ZA200007076B (en) | A pharmaceutical combination comprising a COX-2 inhibitor and iNOS inhibitor. | |
US6046191A (en) | Combination | |
JP6532878B2 (ja) | 組合せ医薬 | |
WO2001074771A1 (en) | Pyrrole-2,5-dione derivatives for the treatment of diabetes | |
JP2008542219A (ja) | 疼痛処置法 | |
RU2008152180A (ru) | ПРОИЗВОДНЫЕ ПИРРОЛА, МОДУЛИРУЮЩИЕ АКТИВНОСТЬ CRTh2 РЕЦЕПТОРА | |
CA2526908A1 (en) | Combination of histone deacetylase inhibitors with chemotherapeutic agents | |
ATE357453T1 (de) | Comt-inhibitoren | |
JP2004510705A5 (ja) | ||
JP2008519080A5 (ja) | ||
CA2514373A1 (en) | N-phenylbenzamide derivatives as drugs for the treatment of copd | |
JP5487107B2 (ja) | 疼痛の処置におけるスルホニル置換2−スルホニルアミノ安息香酸n−フェニルアミドの使用 | |
Saini et al. | Recent advances in anti-inflammatory potential of pyridazinone derivatives | |
WO2013170757A1 (zh) | 4-氨基喹唑啉异羟肟酸类化合物及作为抗肿瘤药物应用 | |
EA200800071A1 (ru) | Производные бензофуранила как ингибиторы 5-нт6-рецептора | |
ES2230171T3 (es) | Compuestos 3,4-dihidro-(1h)quinazolin-2-ona como inhibidores de csbp/p38 quinasa. | |
JPWO2008001929A1 (ja) | 炎症性腸疾患の処置剤 | |
US20080125442A1 (en) | Cathepsin K Inhibitors and Atherosclerosis | |
WO2007103427A3 (en) | Medical use of bilirubin and its structural analogues | |
US10894038B2 (en) | Indolizine derivatives, composition and methods of use | |
BRPI0612582A2 (pt) | combinação de compostos orgánicos | |
EP1864663A1 (en) | Preventive and/or therapeutic agent for rheumatoid arthritis | |
RU2001102505A (ru) | Фармацевтическая комбинация, включающая в себя ингибитор цог-2 и ингибитор иc-no |