NO325516B1 - Tetrahydrokinolinderivater, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikament for kontroll av fruktbarhet. - Google Patents
Tetrahydrokinolinderivater, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikament for kontroll av fruktbarhet. Download PDFInfo
- Publication number
- NO325516B1 NO325516B1 NO20035763A NO20035763A NO325516B1 NO 325516 B1 NO325516 B1 NO 325516B1 NO 20035763 A NO20035763 A NO 20035763A NO 20035763 A NO20035763 A NO 20035763A NO 325516 B1 NO325516 B1 NO 325516B1
- Authority
- NO
- Norway
- Prior art keywords
- alkyl
- phenyl
- tetrahydro
- acetyl
- trimethylquinoline
- Prior art date
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- 239000003814 drug Substances 0.000 title claims description 11
- 230000035558 fertility Effects 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title description 8
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims description 127
- 150000001875 compounds Chemical class 0.000 claims description 74
- -1 Tetrahydroquinoline derivative compound Chemical class 0.000 claims description 50
- 125000005842 heteroatom Chemical group 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 20
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 7
- 150000003839 salts Chemical class 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
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000005204 heteroarylcarbonyloxy group Chemical group 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 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 description 3
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 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 2
- CRXJHMATYNYLBQ-UHFFFAOYSA-N 1-(6-amino-2,2,4-trimethyl-4-phenyl-3h-quinolin-1-yl)propan-1-one Chemical compound C1C(C)(C)N(C(=O)CC)C2=CC=C(N)C=C2C1(C)C1=CC=CC=C1 CRXJHMATYNYLBQ-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
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 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
- 238000000034 method Methods 0.000 description 157
- 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
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 73
- 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
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- 239000000203 mixture Substances 0.000 description 30
- 238000005917 acylation reaction Methods 0.000 description 27
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- 239000012044 organic layer Substances 0.000 description 24
- 239000000243 solution Substances 0.000 description 23
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- 239000003480 eluent Substances 0.000 description 22
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
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- 229910002027 silica gel Inorganic materials 0.000 description 17
- 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 description 16
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- 210000004027 cell Anatomy 0.000 description 16
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- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- 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 14
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 229940028334 follicle stimulating hormone Drugs 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- 108010060374 FSH Receptors Proteins 0.000 description 11
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- 102000008175 FSH Receptors Human genes 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000012267 brine Substances 0.000 description 10
- 230000000694 effects Effects 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
- 238000003547 Friedel-Crafts alkylation reaction Methods 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
- 230000014509 gene expression Effects 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- 238000006069 Suzuki reaction reaction Methods 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- 150000003530 tetrahydroquinolines Chemical class 0.000 description 7
- 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
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- 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 6
- 238000012360 testing method Methods 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
- ZNRLMGFXSPUZNR-UHFFFAOYSA-N 2,2,4-trimethyl-1h-quinoline Chemical class C1=CC=C2C(C)=CC(C)(C)NC2=C1 ZNRLMGFXSPUZNR-UHFFFAOYSA-N 0.000 description 5
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- 125000003342 alkenyl group Chemical group 0.000 description 5
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- 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
- 238000002560 therapeutic procedure Methods 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
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 238000001890 transfection Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 210000002700 urine Anatomy 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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)
- 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 (2)
| Publication Number | Publication Date |
|---|---|
| NO20035763L NO20035763L (no) | 2003-12-29 |
| NO325516B1 true NO325516B1 (no) | 2008-06-02 |
Family
ID=8180574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20035763A NO325516B1 (no) | 2001-07-02 | 2003-12-22 | Tetrahydrokinolinderivater, farmasoytiske preparater omfattende slike samt anvendelse av slike for fremstilling av medikament for kontroll av fruktbarhet. |
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 |
|---|---|---|---|---|
| NZ530198A (en) * | 2001-07-02 | 2005-11-25 | Akzo Nobel Nv | Tetrahydroquinoline derivatives |
| JP2005526723A (ja) * | 2002-02-15 | 2005-09-08 | グラクソ グループ リミテッド | バニロイド受容体モジュレーター |
| 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 |
| US20070281931A1 (en) * | 2003-05-29 | 2007-12-06 | Nigel Boughton-Smith | Pharmaceutical Composition Containing a P2x7 Receptor Antagonist and Methotrexate |
| RU2350354C2 (ru) * | 2003-05-29 | 2009-03-27 | Астразенека Аб | ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ, СОДЕРЖАЩАЯ АНТАГОНИСТ Р2Х7 РЕЦЕПТОРА И ФАКТОР НЕКРОЗА ОПУХОЛИ α |
| 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 |
| 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 |
| CN101171234B (zh) | 2005-05-04 | 2011-11-16 | 欧加农股份有限公司 | 二氢吡啶衍生物 |
| 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 |
| CA2607882A1 (en) | 2005-05-12 | 2006-11-23 | Wyeth | Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (fsh-r) antagonists |
| CA2609714A1 (en) | 2005-06-09 | 2006-12-21 | Wyeth | Pyrrolobenzodiazepine pyridine carboxamides and derivatives as follicle-stimulating hormone receptor antagonists |
| US20070060573A1 (en) * | 2005-08-10 | 2007-03-15 | Lars Wortmann | Acyltryptophanols |
| JP2009504597A (ja) * | 2005-08-10 | 2009-02-05 | バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト | アシルトリプトファノール |
| US20080221195A1 (en) * | 2006-12-13 | 2008-09-11 | Lars Wortmann | 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 |
| ES2388454T3 (es) * | 2007-03-22 | 2012-10-15 | Astrazeneca Ab | Derivados de quinolina para el tratamiento de enfermedades inflamatorias |
| 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 |
| SI2624695T1 (sl) * | 2010-10-08 | 2016-01-29 | Nivalis Therapeutics, Inc. | Nove substituirane kinolinske spojine kot inhibitorji S-nitrozoglutation reduktaze |
| 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 |
| 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 |
| DE3879031T2 (de) | 1987-08-08 | 1993-06-24 | Akzo Nv | Kontrazeptives implantat. |
| EP1043326A1 (en) * | 1994-12-22 | 2000-10-11 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| PT1102763E (pt) * | 1998-08-07 | 2005-01-31 | Applied Research Systems | Mimeticos fsh para o tratamento da infertilidade |
| 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 |
| NZ530198A (en) | 2001-07-02 | 2005-11-25 | Akzo Nobel Nv | Tetrahydroquinoline derivatives |
| 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 NZ NZ530198A patent/NZ530198A/en not_active IP Right Cessation
- 2002-06-25 EP EP02747437A patent/EP1406628B1/en not_active Expired - Lifetime
- 2002-06-25 PT PT02747437T patent/PT1406628E/pt unknown
- 2002-06-25 IL IL15928802A patent/IL159288A0/xx not_active IP Right Cessation
- 2002-06-25 US US10/482,707 patent/US8058441B2/en not_active Expired - Fee Related
- 2002-06-25 MX MXPA03011908A patent/MXPA03011908A/es active IP Right Grant
- 2002-06-25 CA CA2452606A patent/CA2452606C/en not_active Expired - Fee Related
- 2002-06-25 DE DE60209734T patent/DE60209734T2/de not_active Expired - Lifetime
- 2002-06-25 BR BR0210645-0A patent/BR0210645A/pt not_active IP Right Cessation
- 2002-06-25 RU RU2004102693/15A patent/RU2347570C2/ru not_active IP Right Cessation
- 2002-06-25 PL PL02367638A patent/PL367638A1/xx unknown
- 2002-06-25 HU HU0400390A patent/HUP0400390A2/hu unknown
- 2002-06-25 CN CNB02813334XA patent/CN1261099C/zh not_active Expired - Fee Related
- 2002-06-25 ES ES02747437T patent/ES2260458T3/es not_active Expired - Lifetime
- 2002-06-25 JP JP2003510039A patent/JP4523273B2/ja not_active Expired - Fee Related
- 2002-06-25 AU AU2002317848A patent/AU2002317848B2/en not_active Ceased
- 2002-06-25 DK DK02747437T patent/DK1406628T3/da active
- 2002-06-25 CZ CZ20042A patent/CZ20042A3/cs unknown
- 2002-06-25 KR KR1020037017088A patent/KR100908468B1/ko not_active Expired - Fee Related
- 2002-06-25 WO PCT/EP2002/007053 patent/WO2003004028A1/en not_active Ceased
- 2002-06-25 AT AT02747437T patent/ATE319451T1/de not_active IP Right Cessation
- 2002-06-25 SK SK1634-2003A patent/SK286759B6/sk not_active IP Right Cessation
- 2002-06-25 HR HR20031080A patent/HRP20031080A2/hr not_active Application Discontinuation
- 2002-06-27 PE PE2002000581A patent/PE20030273A1/es not_active Application Discontinuation
- 2002-07-01 AR ARP020102468A patent/AR034669A1/es unknown
- 2002-08-26 SA SA02230260A patent/SA02230260B1/ar unknown
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2003
- 2003-12-11 IS IS7071A patent/IS2418B/is unknown
- 2003-12-22 ZA ZA200309921A patent/ZA200309921B/en unknown
- 2003-12-22 NO NO20035763A patent/NO325516B1/no not_active IP Right Cessation
- 2003-12-30 EC EC2003004932A patent/ECSP034932A/es unknown
-
2006
- 2006-05-16 CY CY20061100628T patent/CY1106087T1/el unknown
-
2011
- 2011-10-07 US US13/268,214 patent/US8258293B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
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