NO321370B1 - Cyklotiokarbamatderivater som progesteronreseptormodulatorer, farmasoytisk preparat omfattende disse, deres anvendelse for fremstilling av medikamenter samt derivater for bruk som medikament. - Google Patents

Info

Publication number

NO321370B1

NO321370B1 NO20015381A NO20015381A NO321370B1 NO 321370 B1 NO321370 B1 NO 321370B1 NO 20015381 A NO20015381 A NO 20015381A NO 20015381 A NO20015381 A NO 20015381A NO 321370 B1 NO321370 B1 NO 321370B1

Authority

NO

Norway

Prior art keywords

dihydro

dimethyl

benzoxazin

alkyl

thioxo

Prior art date

1999-05-04

Links

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• 239000003814 drug Substances 0.000 title claims description 14
• 238000004519 manufacturing process Methods 0.000 title claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 239000002379 progesterone receptor modulator Substances 0.000 title 1
• 229940095745 sex hormone and modulator of the genital system progesterone receptor modulator Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 142
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 47
• 150000003839 salts Chemical class 0.000 claims abstract description 19
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 17
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
• 125000001424 substituent group Chemical group 0.000 claims abstract description 16
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 14
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 7
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
• 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 3
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 3
• 239000003433 contraceptive agent Substances 0.000 claims abstract description 3
• 230000002254 contraceptive effect Effects 0.000 claims abstract description 3
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 64
• 229910052799 carbon Inorganic materials 0.000 claims description 33
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 28
• 229920006395 saturated elastomer Polymers 0.000 claims description 20
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
• 229910052739 hydrogen Inorganic materials 0.000 claims description 18
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
• -1 [ 1,3]oxazin-6-yl Chemical group 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 8
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• 210000001072 colon Anatomy 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
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• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 3
• 125000004637 2-oxopiperidinyl group Chemical group O=C1N(CCCC1)* 0.000 claims description 3
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• NAQUDAIOMWNXJF-UHFFFAOYSA-N 6-(3-fluorophenyl)-4-methyl-1,4-dihydro-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)OC(=S)NC2=CC=C1C1=CC=CC(F)=C1 NAQUDAIOMWNXJF-UHFFFAOYSA-N 0.000 claims description 3
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 3
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• 230000015572 biosynthetic process Effects 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
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• 125000003386 piperidinyl group Chemical group 0.000 claims description 3
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
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• 125000001544 thienyl group Chemical group 0.000 claims description 3
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• JXEZBFHBHFDRCM-UHFFFAOYSA-N 5-(4,4-dimethyl-2-sulfanylidene-1h-3,1-benzoxazin-6-yl)-4-methylthiophene-2-carbonitrile Chemical compound C1=C(C#N)SC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1C JXEZBFHBHFDRCM-UHFFFAOYSA-N 0.000 claims description 2
• XCHOFVZQFUVVEB-UHFFFAOYSA-N 6-(3-chlorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical group C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(Cl)=C1 XCHOFVZQFUVVEB-UHFFFAOYSA-N 0.000 claims description 2
• YBBTTYFZWTXGQD-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-methyl-4-phenyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C=3C=CC=CC=3)OC(=S)NC2=CC=C1C1=CC=CC(Cl)=C1 YBBTTYFZWTXGQD-UHFFFAOYSA-N 0.000 claims description 2
• JKKKYMAGXVPMSE-UHFFFAOYSA-N 6-(3-fluorophenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound C1=C2C(C)(C)OC(=S)NC2=CC=C1C1=CC=CC(F)=C1 JKKKYMAGXVPMSE-UHFFFAOYSA-N 0.000 claims description 2
• UMQGDADSFKJZKD-UHFFFAOYSA-N 6-(3-methoxyphenyl)-4,4-dimethyl-1h-3,1-benzoxazine-2-thione Chemical compound COC1=CC=CC(C=2C=C3C(C)(C)OC(=S)NC3=CC=2)=C1 UMQGDADSFKJZKD-UHFFFAOYSA-N 0.000 claims description 2
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
• 229910020008 S(O) Inorganic materials 0.000 claims description 2
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 2
• 239000003974 emollient agent Substances 0.000 claims description 2
• LAQPNDIUHRHNCV-UHFFFAOYSA-N isophthalonitrile Chemical compound N#CC1=CC=CC(C#N)=C1 LAQPNDIUHRHNCV-UHFFFAOYSA-N 0.000 claims description 2
• 229930192474 thiophene Natural products 0.000 claims description 2
• 125000005843 halogen group Chemical group 0.000 claims 4
• LAWUZBKFMNSOGG-UHFFFAOYSA-N thiophene-2-carbonitrile Chemical compound N#CC1=CC=[C]S1 LAWUZBKFMNSOGG-UHFFFAOYSA-N 0.000 claims 2
• WGSXKYXKAARAKD-UHFFFAOYSA-N 1-fluoro-3-isocyanato-5-(trifluoromethyl)benzene Chemical group FC1=CC(N=C=O)=CC(C(F)(F)F)=C1 WGSXKYXKAARAKD-UHFFFAOYSA-N 0.000 claims 1
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