HUP0400390A2 - Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények - Google Patents
Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények Download PDFInfo
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- HUP0400390A2 HUP0400390A2 HU0400390A HUP0400390A HUP0400390A2 HU P0400390 A2 HUP0400390 A2 HU P0400390A2 HU 0400390 A HU0400390 A HU 0400390A HU P0400390 A HUP0400390 A HU P0400390A HU P0400390 A2 HUP0400390 A2 HU P0400390A2
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- Hungary
- Prior art keywords
- alkyl
- group
- amino
- acetyl
- aryl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 230000001225 therapeutic effect Effects 0.000 claims abstract description 6
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 86
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 47
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 125000001072 heteroaryl group Chemical group 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 21
- 150000003530 tetrahydroquinolines Chemical class 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 8
- 125000005199 aryl carbonyloxy group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000005201 cycloalkylcarbonyloxy group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 5
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 4
- 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 description 4
- 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
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 230000035558 fertility Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000002485 formyl group Chemical group [H]C(*)=O 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
- 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
- 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
- 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 2
- 125000003277 amino group Chemical group 0.000 claims 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 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- -1 C(O)-NH Inorganic materials 0.000 abstract description 23
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- 206010006187 Breast cancer Diseases 0.000 abstract description 3
- 208000026310 Breast neoplasm Diseases 0.000 abstract description 3
- 201000009273 Endometriosis Diseases 0.000 abstract description 3
- 206010060862 Prostate cancer Diseases 0.000 abstract description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 abstract description 3
- 229940124558 contraceptive agent Drugs 0.000 abstract description 3
- 239000003433 contraceptive agent Substances 0.000 abstract description 3
- 230000001419 dependent effect Effects 0.000 abstract description 3
- 125000000962 organic group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 42
- 239000000203 mixture Substances 0.000 description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 26
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 15
- 125000005842 heteroatom Chemical group 0.000 description 15
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- 229940028334 follicle stimulating hormone Drugs 0.000 description 14
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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- 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 1
- JAKLNDLCOLMARD-UHFFFAOYSA-N n-(1-acetyl-2,2,4-trimethyl-4-phenyl-3h-quinolin-6-yl)-4-pyridin-3-ylbenzamide Chemical compound C1=C2C(C)(C=3C=CC=CC=3)CC(C)(C)N(C(=O)C)C2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CN=C1 JAKLNDLCOLMARD-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000027758 ovulation cycle Effects 0.000 description 1
- 125000005429 oxyalkyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 1
- 230000001817 pituitary effect Effects 0.000 description 1
- 210000002826 placenta Anatomy 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
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- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000001850 reproductive effect Effects 0.000 description 1
- 230000027272 reproductive process Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002863 seminiferous tubule Anatomy 0.000 description 1
- 210000000717 sertoli cell Anatomy 0.000 description 1
- 230000011664 signaling Effects 0.000 description 1
- 238000010898 silica gel chromatography Methods 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
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 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
- 238000003756 stirring Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 238000005694 sulfonylation reaction Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- WWEJANUNXGNDAC-UHFFFAOYSA-N tert-butyl n-(1-acetyl-2,2,4-trimethyl-4-phenyl-3h-quinolin-6-yl)carbamate Chemical compound C1C(C)(C)N(C(=O)C)C2=CC=C(NC(=O)OC(C)(C)C)C=C2C1(C)C1=CC=CC=C1 WWEJANUNXGNDAC-UHFFFAOYSA-N 0.000 description 1
- YECLJUVQMVUOHY-UHFFFAOYSA-N tert-butyl n-(2,2,4,7-tetramethyl-1h-quinolin-6-yl)carbamate Chemical compound CC1=C(NC(=O)OC(C)(C)C)C=C2C(C)=CC(C)(C)NC2=C1 YECLJUVQMVUOHY-UHFFFAOYSA-N 0.000 description 1
- TXFUWJLANVJXMK-UHFFFAOYSA-N tert-butyl n-(2,2,4-trimethyl-1h-quinolin-6-yl)carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C=C2C(C)=CC(C)(C)NC2=C1 TXFUWJLANVJXMK-UHFFFAOYSA-N 0.000 description 1
- WIVYTYZCVWHWSH-UHFFFAOYSA-N tert-butyl n-(4-aminophenyl)carbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=C(N)C=C1 WIVYTYZCVWHWSH-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
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000013518 transcription 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Endocrinology (AREA)
- Diabetes (AREA)
- Epidemiology (AREA)
- Reproductive Health (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 (1)
| Publication Number | Publication Date |
|---|---|
| HUP0400390A2 true HUP0400390A2 (hu) | 2004-09-28 |
Family
ID=8180574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU0400390A HUP0400390A2 (hu) | 2001-07-02 | 2002-06-25 | Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények |
Country Status (31)
| Country | Link |
|---|---|
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| 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) |
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| ES2260458T3 (es) | 2001-07-02 | 2006-11-01 | Akzo Nobel N.V. | Derivados de tetrahidroquinolina. |
| TW200403223A (en) * | 2002-02-15 | 2004-03-01 | Glaxo Group Ltd | Novel compounds |
| 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 |
| WO2004105798A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A PHARMACEUTICAL COMPOSITION COMPRISING A P2X7-RECEPTOR ANTAGONIST AND A TUMOUR NECROSIS FACTOR α |
| WO2004105796A1 (en) * | 2003-05-29 | 2004-12-09 | Astrazeneca Ab | A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate |
| EP1644041A1 (en) * | 2003-05-29 | 2006-04-12 | AstraZeneca AB | A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine |
| 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 |
| EP1879866B1 (en) | 2005-05-04 | 2011-03-16 | N.V. Organon | 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 |
| 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 |
| AU2006247601A1 (en) | 2005-05-12 | 2006-11-23 | Wyeth | Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (FSH-R) antagonists |
| WO2006135687A1 (en) | 2005-06-09 | 2006-12-21 | Wyeth | Pyrrolobenzodiazepine pyridine carboxamides and derivatives as follicle-stimulating hormone receptor antagonists |
| WO2007017289A2 (en) * | 2005-08-10 | 2007-02-15 | Bayer Schering Pharma Aktiengesellschaft | Acyltryptophanols for fertility control |
| US20070060573A1 (en) * | 2005-08-10 | 2007-03-15 | Lars Wortmann | Acyltryptophanols |
| EP1932831A1 (en) * | 2006-12-13 | 2008-06-18 | Bayer Schering Pharma Aktiengesellschaft | 1,2-Diarylacetylene Derivatives of Acyltryptophanols |
| US20080221195A1 (en) * | 2006-12-13 | 2008-09-11 | Lars Wortmann | 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 |
| AU2008228067B2 (en) * | 2007-03-22 | 2011-12-08 | Astrazeneca Ab | Quinoline derivatives for the treatment of inflammatory diseases |
| TW200918058A (en) | 2007-08-31 | 2009-05-01 | Organon Nv | TSH receptor antagonizing tetrahydroquinoline compounds |
| PE20091036A1 (es) | 2007-11-30 | 2009-08-15 | Astrazeneca Ab | Derivado de quinolina como antagonista del receptor p2x7 |
| 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 |
| US8071587B2 (en) | 2009-05-27 | 2011-12-06 | N. V. Organon | (Dihydro)imidazoiso[5,1-A]quinolines |
| TWI461426B (zh) * | 2009-05-27 | 2014-11-21 | Merck Sharp & Dohme | （二氫）咪唑並異〔５，１－ａ〕喹啉類 |
| 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 |
| EP3174932B1 (en) * | 2014-07-30 | 2021-06-09 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
| US12275729B2 (en) | 2017-11-01 | 2025-04-15 | Merck Sharp & Dohme Llc | 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2686182A (en) | 1950-12-07 | 1954-08-10 | Basf Ag | O-hydroxy-dihydro-quinoline carboxylic acids |
| ATE86484T1 (de) | 1987-08-08 | 1993-03-15 | Akzo Nv | Kontrazeptives implantat. |
| RU2191774C2 (ru) | 1994-12-22 | 2002-10-27 | Лайджэнд Фармасьютикалз Инкорпорейтед | Соединения-модуляторы стероидных рецепторов и способы |
| IL141063A (en) * | 1998-08-07 | 2005-06-19 | Applied Research Systems | Derivatives of pyrrolidine-2-carboxylic acid and piperidine-2-carboxylic acids and pharmaceutical compositions comprising said derivatives for treating infertility |
| 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 |
| ES2260458T3 (es) | 2001-07-02 | 2006-11-01 | Akzo Nobel N.V. | Derivados de tetrahidroquinolina. |
| TWI322012B (en) | 2002-12-20 | 2010-03-21 | Organon Nv | Tetrahydroquinoline derivatives |
| TWI306855B (en) | 2002-12-20 | 2009-03-01 | Organon Nv | Tetrahydroquinoline derivatives |
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2002
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| Date | Code | Title | Description |
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| GB9A | Succession in title |
Owner name: N.V. ORGANON, NL Free format text: FORMER OWNER(S): AKZO NOBEL N.V., NL |
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| FD9A | Lapse of provisional protection due to non-payment of fees |