SK286759B6 - Tetrahydrochinolínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie - Google Patents
Tetrahydrochinolínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie Download PDFInfo
- Publication number
- SK286759B6 SK286759B6 SK1634-2003A SK16342003A SK286759B6 SK 286759 B6 SK286759 B6 SK 286759B6 SK 16342003 A SK16342003 A SK 16342003A SK 286759 B6 SK286759 B6 SK 286759B6
- Authority
- SK
- Slovakia
- Prior art keywords
- alkyl
- phenyl
- acetyl
- tetrahydro
- amino
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 10
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title description 80
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 189
- -1 nitro hydroxyl Chemical group 0.000 claims abstract description 69
- 125000003118 aryl group Chemical group 0.000 claims abstract description 58
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 39
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 33
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 32
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 23
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 18
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 17
- 150000002367 halogens Chemical class 0.000 claims abstract description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims abstract description 11
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 10
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 230000035558 fertility Effects 0.000 claims abstract description 6
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 claims abstract description 4
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims abstract description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 4
- RTWPATFTOPMBPW-UHFFFAOYSA-N 1-(6-amino-2,2,4-trimethyl-4-phenyl-3h-quinolin-1-yl)ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(N)C=C2C1(C)C1=CC=CC=C1 RTWPATFTOPMBPW-UHFFFAOYSA-N 0.000 claims description 38
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 19
- 150000003530 tetrahydroquinolines Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 6
- 125000001769 aryl amino group Chemical group 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000005116 aryl carbamoyl group Chemical group 0.000 claims description 5
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- VMFDEEWJXWIULP-UHFFFAOYSA-N 1-(6-methoxy-2,2,4-trimethyl-4-phenyl-3h-quinolin-1-yl)ethanone Chemical compound C12=CC(OC)=CC=C2N(C(C)=O)C(C)(C)CC1(C)C1=CC=CC=C1 VMFDEEWJXWIULP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- IBPJOBWPZTZRQS-UHFFFAOYSA-N 1-(2,2,4,6,8-pentamethyl-4-phenyl-3h-quinolin-1-yl)ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=C(C)C=C(C)C=C2C1(C)C1=CC=CC=C1 IBPJOBWPZTZRQS-UHFFFAOYSA-N 0.000 claims description 3
- ZHNPUEPFTRRAJP-UHFFFAOYSA-N 1-[4-(4-chlorophenyl)-2,2,4,6-tetramethyl-3h-quinolin-1-yl]ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(C)C=C2C1(C)C1=CC=C(Cl)C=C1 ZHNPUEPFTRRAJP-UHFFFAOYSA-N 0.000 claims description 3
- ARWKEHPZVPYGDT-UHFFFAOYSA-N n-(1-acetyl-2,2,4-trimethyl-4-phenyl-3h-quinolin-6-yl)-2,2,2-trifluoroacetamide Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(NC(=O)C(F)(F)F)C=C2C1(C)C1=CC=CC=C1 ARWKEHPZVPYGDT-UHFFFAOYSA-N 0.000 claims description 3
- QWLACKLMUBWFKR-UHFFFAOYSA-N n-[1-acetyl-2,2,4-trimethyl-4-(4-methylphenyl)-3h-quinolin-6-yl]benzamide Chemical compound C1=C2C(C)(C=3C=CC(C)=CC=3)CC(C)(C)N(C(=O)C)C2=CC=C1NC(=O)C1=CC=CC=C1 QWLACKLMUBWFKR-UHFFFAOYSA-N 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- WVAXDHRFGWSJSE-UHFFFAOYSA-N 1-[4-(4-bromophenyl)-2,2,4,6-tetramethyl-3h-quinolin-1-yl]ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(C)C=C2C1(C)C1=CC=C(Br)C=C1 WVAXDHRFGWSJSE-UHFFFAOYSA-N 0.000 claims description 2
- IUBSOZIHVZOVRB-UHFFFAOYSA-N 1-[6-amino-4-(4-aminophenyl)-2,2,4-trimethyl-3h-quinolin-1-yl]ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(N)C=C2C1(C)C1=CC=C(N)C=C1 IUBSOZIHVZOVRB-UHFFFAOYSA-N 0.000 claims description 2
- BMJCSYBLFOGGIA-UHFFFAOYSA-N n-[1-acetyl-2,2,4-trimethyl-4-(4-methylphenyl)-3h-quinolin-6-yl]-2,2,2-trifluoroacetamide Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(NC(=O)C(F)(F)F)C=C2C1(C)C1=CC=C(C)C=C1 BMJCSYBLFOGGIA-UHFFFAOYSA-N 0.000 claims description 2
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 3
- ZXGXGZGKWSUMJK-UHFFFAOYSA-N 2,4,6-trimethylquinoline Chemical compound N1=C(C)C=C(C)C2=CC(C)=CC=C21 ZXGXGZGKWSUMJK-UHFFFAOYSA-N 0.000 claims 2
- UHWQFJIDBCYRIB-UHFFFAOYSA-N 1-(2,2,4,6-tetramethyl-4-phenyl-3h-quinolin-1-yl)ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(C)C=C2C1(C)C1=CC=CC=C1 UHWQFJIDBCYRIB-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 abstract description 9
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 238000000034 method Methods 0.000 description 155
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 102
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 98
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 84
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 238000004128 high performance liquid chromatography Methods 0.000 description 70
- 125000004432 carbon atom Chemical group C* 0.000 description 59
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 46
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 239000000203 mixture Substances 0.000 description 34
- 238000005917 acylation reaction Methods 0.000 description 29
- 230000010933 acylation Effects 0.000 description 27
- 239000011541 reaction mixture Substances 0.000 description 26
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- 238000009833 condensation Methods 0.000 description 24
- 230000005494 condensation Effects 0.000 description 24
- 239000012044 organic layer Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000003480 eluent Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 description 17
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
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- 229940028334 follicle stimulating hormone Drugs 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
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- 238000003756 stirring Methods 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
- DKUNOXZTJNCJDK-UHFFFAOYSA-N 2,2,4-trimethyl-4-phenyl-3H-quinolin-1-amine Chemical compound CC1(C)CC(C)(c2ccccc2)c2ccccc2N1N DKUNOXZTJNCJDK-UHFFFAOYSA-N 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
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- 108010060374 FSH Receptors Proteins 0.000 description 10
- 238000003547 Friedel-Crafts alkylation reaction Methods 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 10
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 9
- 102000008175 FSH Receptors Human genes 0.000 description 9
- 239000011630 iodine Substances 0.000 description 9
- 229910052740 iodine Inorganic materials 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 8
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- 230000001404 mediated effect Effects 0.000 description 7
- BALPUPABKHYFCR-UHFFFAOYSA-N n-(1-acetyl-2,2,4-trimethyl-4-phenyl-3h-quinolin-6-yl)-2-hydroxybenzamide Chemical compound C1=C2C(C)(C=3C=CC=CC=3)CC(C)(C)N(C(=O)C)C2=CC=C1NC(=O)C1=CC=CC=C1O BALPUPABKHYFCR-UHFFFAOYSA-N 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- WVUMXBUVLLSUMD-UHFFFAOYSA-N 3-[(1-acetyl-2,2,4-trimethyl-4-phenyl-3h-quinolin-6-yl)amino]-3-oxopropanoic acid Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(NC(=O)CC(O)=O)C=C2C1(C)C1=CC=CC=C1 WVUMXBUVLLSUMD-UHFFFAOYSA-N 0.000 description 6
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 6
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- 239000012442 inert solvent Substances 0.000 description 6
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 5
- YIPDIHSVBRGRSA-UHFFFAOYSA-N 1-(6-hydroxy-2,2,4-trimethyl-4-phenyl-3h-quinolin-1-yl)ethanone Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(O)C=C2C1(C)C1=CC=CC=C1 YIPDIHSVBRGRSA-UHFFFAOYSA-N 0.000 description 5
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- 230000028327 secretion Effects 0.000 description 1
- 210000000717 sertoli cell Anatomy 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000002741 site-directed mutagenesis Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 230000021595 spermatogenesis Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000010009 steroidogenesis Effects 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- KNWMPOSCNXKJAJ-UHFFFAOYSA-N tert-butyl 1-acetyl-3-amino-2,2,4-trimethylquinoline-6-carboxylate Chemical compound C(C)(=O)N1C(C(=C(C2=CC(=CC=C12)C(=O)OC(C)(C)C)C)N)(C)C KNWMPOSCNXKJAJ-UHFFFAOYSA-N 0.000 description 1
- DGEHMLFUFOWHAF-UHFFFAOYSA-N tert-butyl 1-amino-2,2,4,7-tetramethylquinoline-6-carboxylate Chemical compound C(C)(C)(C)OC(=O)C=1C=C2C(=CC(N(C2=CC=1C)N)(C)C)C DGEHMLFUFOWHAF-UHFFFAOYSA-N 0.000 description 1
- XMCISUHCJIBPQC-UHFFFAOYSA-N tert-butyl 3-amino-1-butanoyl-2,2,4-trimethylquinoline-6-carboxylate Chemical compound C(C)(C)(C)OC(=O)C=1C=C2C(=C(C(N(C2=CC=1)C(CCC)=O)(C)C)N)C XMCISUHCJIBPQC-UHFFFAOYSA-N 0.000 description 1
- WMVAEBXGXONFMN-UHFFFAOYSA-N tert-butyl n-(1-butanoyl-2,2,4-trimethylquinolin-6-yl)carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=C2C(C)=CC(C)(C)N(C(=O)CCC)C2=C1 WMVAEBXGXONFMN-UHFFFAOYSA-N 0.000 description 1
- HSZKDVSZYCRBEC-UHFFFAOYSA-N tert-butyl n-(4-amino-2-methylphenyl)carbamate Chemical compound CC1=CC(N)=CC=C1NC(=O)OC(C)(C)C HSZKDVSZYCRBEC-UHFFFAOYSA-N 0.000 description 1
- 230000002381 testicular Effects 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- 238000013519 translation Methods 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
-
- 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
- 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
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/16—Masculine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A61P5/08—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
- C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Reproductive Health (AREA)
- Epidemiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01202531 | 2001-07-02 | ||
| PCT/EP2002/007053 WO2003004028A1 (en) | 2001-07-02 | 2002-06-25 | Tetrahydroquinoline derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK16342003A3 SK16342003A3 (sk) | 2004-07-07 |
| SK286759B6 true SK286759B6 (sk) | 2009-05-07 |
Family
ID=8180574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1634-2003A SK286759B6 (sk) | 2001-07-02 | 2002-06-25 | Tetrahydrochinolínové deriváty, farmaceutický prostriedok s ich obsahom a ich použitie |
Country Status (31)
| Country | Link |
|---|---|
| US (2) | US8058441B2 (enExample) |
| EP (1) | EP1406628B1 (enExample) |
| JP (1) | JP4523273B2 (enExample) |
| KR (1) | KR100908468B1 (enExample) |
| CN (1) | CN1261099C (enExample) |
| AR (1) | AR034669A1 (enExample) |
| AT (1) | ATE319451T1 (enExample) |
| AU (1) | AU2002317848B2 (enExample) |
| BR (1) | BR0210645A (enExample) |
| CA (1) | CA2452606C (enExample) |
| CY (1) | CY1106087T1 (enExample) |
| CZ (1) | CZ20042A3 (enExample) |
| DE (1) | DE60209734T2 (enExample) |
| DK (1) | DK1406628T3 (enExample) |
| EC (1) | ECSP034932A (enExample) |
| ES (1) | ES2260458T3 (enExample) |
| HR (1) | HRP20031080A2 (enExample) |
| HU (1) | HUP0400390A2 (enExample) |
| IL (1) | IL159288A0 (enExample) |
| IS (1) | IS2418B (enExample) |
| MX (1) | MXPA03011908A (enExample) |
| NO (1) | NO325516B1 (enExample) |
| NZ (1) | NZ530198A (enExample) |
| PE (1) | PE20030273A1 (enExample) |
| PL (1) | PL367638A1 (enExample) |
| PT (1) | PT1406628E (enExample) |
| RU (1) | RU2347570C2 (enExample) |
| SA (1) | SA02230260B1 (enExample) |
| SK (1) | SK286759B6 (enExample) |
| WO (1) | WO2003004028A1 (enExample) |
| ZA (1) | ZA200309921B (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUP0400390A2 (hu) * | 2001-07-02 | 2004-09-28 | Akzo Nobel N.V. | Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények |
| AU2003245773A1 (en) * | 2002-02-15 | 2003-09-04 | Glaxo Group Limited | Vanilloid receptor modulators |
| FR2836620B1 (fr) * | 2002-02-28 | 2004-04-16 | Snecma Services | Instrument de projection thermique |
| SE0200920D0 (sv) * | 2002-03-25 | 2002-03-25 | Astrazeneca Ab | Novel compounds |
| TWI306855B (en) * | 2002-12-20 | 2009-03-01 | Organon Nv | Tetrahydroquinoline derivatives |
| TWI322012B (en) * | 2002-12-20 | 2010-03-21 | Organon Nv | Tetrahydroquinoline derivatives |
| SE0300480D0 (sv) * | 2003-02-21 | 2003-02-21 | Astrazeneca Ab | Novel compounds |
| EP1644041A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| US20070281931A1 (en) * | 2003-05-29 | 2007-12-06 | Nigel Boughton-Smith | Pharmaceutical Composition Containing a P2x7 Receptor Antagonist and Methotrexate |
| EP1633401A1 (en) * | 2003-05-29 | 2006-03-15 | AstraZeneca AB | A pharmaceutical composition comprising a p2x7-receptor antagonist and a tumour necrosis factor alpha |
| GB0312609D0 (en) * | 2003-06-02 | 2003-07-09 | Astrazeneca Ab | Novel compounds |
| KR100554155B1 (ko) * | 2003-06-09 | 2006-02-22 | 학교법인 포항공과대학교 | 금속/반도체 나노막대 이종구조를 이용한 전극 구조물 및그 제조 방법 |
| SE0302139D0 (sv) * | 2003-07-28 | 2003-07-28 | Astrazeneca Ab | Novel compounds |
| SE0302192D0 (sv) * | 2003-08-08 | 2003-08-08 | Astrazeneca Ab | Novel compounds |
| SE0302488D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | New combination |
| SA05260265A (ar) * | 2004-08-30 | 2005-12-03 | استرازينيكا ايه بي | مركبات جديدة |
| SE0402925D0 (sv) * | 2004-11-30 | 2004-11-30 | Astrazeneca Ab | Novel Compounds |
| US7691848B2 (en) | 2005-03-02 | 2010-04-06 | Wyeth | Pyrrolobenzodiazepine arylcarboxamides and derivatives thereof as follicle-stimulating hormone receptor antagonists |
| UA92009C2 (ru) | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодия |
| UA92007C2 (ru) * | 2005-05-04 | 2010-09-27 | Н.В. Органон | Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодности |
| NZ562541A (en) | 2005-05-04 | 2009-02-28 | Organon Nv | Dihydropyridine derivatives |
| UA92008C2 (en) * | 2005-05-04 | 2010-09-27 | Н.В. Органон | 4-PHENYL-5-OXO-l,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES AS MEDICAMENTS FOR THE TREATMENT OF INFERTILITY |
| AU2006247601A1 (en) | 2005-05-12 | 2006-11-23 | Wyeth | Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (FSH-R) antagonists |
| CN101208342A (zh) | 2005-06-09 | 2008-06-25 | 惠氏公司 | 作为促卵泡激素受体拮抗剂的吡咯并苯并二氮杂䓬吡啶羧酰胺和衍生物 |
| US20070060573A1 (en) * | 2005-08-10 | 2007-03-15 | Lars Wortmann | Acyltryptophanols |
| CA2618888A1 (en) * | 2005-08-10 | 2007-02-15 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols for fertility control |
| WO2008071453A1 (en) * | 2006-12-13 | 2008-06-19 | Bayer Schering Pharma Aktiengesellschaft | 1,2-diarylacetylene derivatives of acyltryptophanols |
| EP1932831A1 (en) * | 2006-12-13 | 2008-06-18 | Bayer Schering Pharma Aktiengesellschaft | 1,2-Diarylacetylene Derivatives of Acyltryptophanols |
| TWI410422B (zh) | 2007-01-15 | 2013-10-01 | Mitsubishi Tanabe Pharma Corp | 縮合四氫喹啉衍生物及其醫藥用途 |
| TW200848021A (en) | 2007-03-06 | 2008-12-16 | Wyeth Corp | Sulfonylated heterocycles useful for modulation of the progesterone receptor |
| RU2460727C2 (ru) * | 2007-03-22 | 2012-09-10 | Астразенека Аб | Хинолиновые производные для лечения воспалительных заболеваний |
| TW200918058A (en) * | 2007-08-31 | 2009-05-01 | Organon Nv | TSH receptor antagonizing tetrahydroquinoline compounds |
| US8106073B2 (en) | 2007-11-30 | 2012-01-31 | Astrazeneca Ab | Quinoline derivatives 057 |
| RU2359684C1 (ru) * | 2008-01-23 | 2009-06-27 | Закрытое акционерное общество "СКАЙ ЛТД" | Способ лечения эндометриоза |
| TW200944523A (en) | 2008-02-08 | 2009-11-01 | Organon Nv | (Dihydro)pyrrolo[2,1-a]isoquinolines |
| US20100061976A1 (en) * | 2008-07-24 | 2010-03-11 | Searete Llc, A Limited Liability Corporation Of The State Of Delaware | Method for treating or preventing osteoporosis by reducing follicle stimulating hormone to cyclic physiological levels in a mammalian subject |
| TWI461426B (zh) * | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| US8071587B2 (en) | 2009-05-27 | 2011-12-06 | N. V. Organon | (Dihydro)imidazoiso[5,1-A]quinolines |
| US8431564B2 (en) | 2009-07-29 | 2013-04-30 | Merck Sharp & Dohme B.V. | Ring-annulated dihydropyrrolo[2,1-α]isoquinolines |
| TW201116531A (en) | 2009-07-29 | 2011-05-16 | Organon Nv | Ring-annulated dihydropyrrolo[2,1-a]isoquinolines |
| TW201116515A (en) | 2009-07-31 | 2011-05-16 | Organon Nv | Dihydrobenzoindazoles |
| BR112013007907A2 (pt) * | 2010-10-08 | 2016-06-14 | N30 Pharmaceuticals Inc | novos compostos de quinolina substituída como inibidores de s-nitrosoglutationa reductase |
| US8546427B2 (en) * | 2010-10-20 | 2013-10-01 | Hoffmann-La Roche Inc. | Tetrahydroquinoline derivatives |
| WO2016018553A1 (en) * | 2014-07-30 | 2016-02-04 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
| WO2019089412A1 (en) * | 2017-11-01 | 2019-05-09 | Merck Sharp & Dohme Corp. | Novel substituted tetrahydroquinolin compounds as indoleamine 2,3-dioxygenase (ido) inhibitors |
| CN119954701A (zh) * | 2024-06-18 | 2025-05-09 | 青岛润农化工有限公司 | 一种丁醚脲的合成方法 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686182A (en) * | 1950-12-07 | 1954-08-10 | Basf Ag | O-hydroxy-dihydro-quinoline carboxylic acids |
| EP0303306B1 (en) | 1987-08-08 | 1993-03-10 | Akzo N.V. | Contraceptive implant |
| CZ176197A3 (cs) * | 1994-12-22 | 1998-09-16 | Ligand Pharmaceuticals Incorporated | Modulátory steroidových receptorů a způsoby jejich přípravy a použití |
| JP4511042B2 (ja) * | 1998-08-07 | 2010-07-28 | メルク セローノ ソシエテ アノニム | 不妊症の治療のためのｆｓｈ模倣物 |
| JP2000143636A (ja) * | 1998-09-02 | 2000-05-26 | Sumitomo Pharmaceut Co Ltd | アミノ誘導体 |
| US6200963B1 (en) * | 1999-03-31 | 2001-03-13 | American Home Products Corporation | Aryl sulfonic acids as FSH antagonists |
| HUP0400390A2 (hu) | 2001-07-02 | 2004-09-28 | Akzo Nobel N.V. | Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények |
| TWI322012B (en) * | 2002-12-20 | 2010-03-21 | Organon Nv | Tetrahydroquinoline derivatives |
| TWI306855B (en) * | 2002-12-20 | 2009-03-01 | Organon Nv | Tetrahydroquinoline derivatives |
-
2002
- 2002-06-25 HU HU0400390A patent/HUP0400390A2/hu unknown
- 2002-06-25 BR BR0210645-0A patent/BR0210645A/pt not_active IP Right Cessation
- 2002-06-25 DK DK02747437T patent/DK1406628T3/da active
- 2002-06-25 HR HR20031080A patent/HRP20031080A2/hr not_active Application Discontinuation
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| Date | Code | Title | Description |
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| MM4A | Patent lapsed due to non-payment of maintenance fees |
Effective date: 20100625 |