CA2116334A1 - Oxytocin antagonist - Google Patents
Oxytocin antagonistInfo
- Publication number
- CA2116334A1 CA2116334A1 CA 2116334 CA2116334A CA2116334A1 CA 2116334 A1 CA2116334 A1 CA 2116334A1 CA 2116334 CA2116334 CA 2116334 CA 2116334 A CA2116334 A CA 2116334A CA 2116334 A1 CA2116334 A1 CA 2116334A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally
- substituted
- alkyl
- alkoxy
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003336 oxytocin antagonist Substances 0.000 title claims abstract description 59
- 229940121361 oxytocin antagonists Drugs 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229960001723 oxytocin Drugs 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 claims abstract description 12
- 101800000989 Oxytocin Proteins 0.000 claims abstract description 12
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 claims abstract description 12
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 claims abstract description 12
- 239000004480 active ingredient Substances 0.000 claims abstract description 11
- 208000005171 Dysmenorrhea Diseases 0.000 claims abstract description 9
- 206010013935 Dysmenorrhoea Diseases 0.000 claims abstract description 9
- 208000004145 Endometritis Diseases 0.000 claims abstract description 7
- 206010036595 Premature delivery Diseases 0.000 claims abstract description 7
- -1 hydrazinocarbonyl Chemical group 0.000 claims description 1805
- 125000000217 alkyl group Chemical group 0.000 claims description 477
- 125000003545 alkoxy group Chemical group 0.000 claims description 316
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 313
- 125000004432 carbon atom Chemical group C* 0.000 claims description 248
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 231
- 125000001424 substituent group Chemical group 0.000 claims description 215
- 125000001589 carboacyl group Chemical group 0.000 claims description 188
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 139
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 90
- 125000000623 heterocyclic group Chemical group 0.000 claims description 79
- 125000005843 halogen group Chemical group 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
- 125000003386 piperidinyl group Chemical group 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 56
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 54
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 51
- 125000002915 carbonyl group Chemical class [*:2]C([*:1])=O 0.000 claims description 44
- 229910052799 carbon Inorganic materials 0.000 claims description 41
- 125000004423 acyloxy group Chemical group 0.000 claims description 38
- 125000003342 alkenyl group Chemical group 0.000 claims description 35
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 34
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 31
- 229910052717 sulfur Inorganic materials 0.000 claims description 30
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000004434 sulfur atom Chemical group 0.000 claims description 27
- 125000003277 amino group Chemical group 0.000 claims description 26
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 24
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000004193 piperazinyl group Chemical group 0.000 claims description 20
- 125000004076 pyridyl group Chemical group 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000002883 imidazolyl group Chemical group 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 17
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 17
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 16
- 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 125000002947 alkylene group Chemical group 0.000 claims description 14
- 125000003368 amide group Chemical group 0.000 claims description 14
- MZBVNYACSSGXID-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-1-benzazepine Chemical compound N1CCCCC2=CC=CC=C21 MZBVNYACSSGXID-UHFFFAOYSA-N 0.000 claims description 13
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 7
- 125000005400 pyridylcarbonyl group Chemical group N1=C(C=CC=C1)C(=O)* 0.000 claims description 7
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 7
- 125000005185 naphthylcarbonyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 5
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001984 thiazolidinyl group Chemical group 0.000 claims description 5
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 5
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 4
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000004628 isothiazolidinyl group Chemical group S1N(CCC1)* 0.000 claims description 4
- 125000005969 isothiazolinyl group Chemical group 0.000 claims description 4
- 125000003971 isoxazolinyl group Chemical group 0.000 claims description 4
- 125000005968 oxazolinyl group Chemical group 0.000 claims description 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 4
- 125000002755 pyrazolinyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 230000003042 antagnostic effect Effects 0.000 claims description 3
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 3
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 3
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 3
- 125000002636 imidazolinyl group Chemical group 0.000 claims description 3
- 125000003965 isoxazolidinyl group Chemical group 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 210000002460 smooth muscle Anatomy 0.000 claims description 3
- DIYUNWKOPDPZCZ-UHFFFAOYSA-N 1-[1-[4-[6-(diethylamino)-5-hydroxyhexoxy]benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C1=CC(OCCCCC(O)CN(CC)CC)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 DIYUNWKOPDPZCZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000539 amino acid group Chemical group 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000000160 oxazolidinyl group Chemical group 0.000 claims description 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims 6
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims 1
- OMNAFXFVUZGVDO-UHFFFAOYSA-N 1-[1-[4-(5-hydroxy-6-pyrrolidin-1-ylhexoxy)benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C=1C=C(C(=O)N2CCC(CC2)N2C3=CC=CC=C3CCC2=O)C=CC=1OCCCCC(O)CN1CCCC1 OMNAFXFVUZGVDO-UHFFFAOYSA-N 0.000 claims 1
- MQDVJDNIGVXBPZ-UHFFFAOYSA-N 1-[1-[4-(5-pyrrolidin-1-ylpentoxy)benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C1CC(N2C3=CC=CC=C3CCC2=O)CCN1C(=O)C(C=C1)=CC=C1OCCCCCN1CCCC1 MQDVJDNIGVXBPZ-UHFFFAOYSA-N 0.000 claims 1
- VEHRBOROUDEXHX-UHFFFAOYSA-N 1-[1-[4-[5-(diethylamino)pentoxy]benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C1=CC(OCCCCCN(CC)CC)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 VEHRBOROUDEXHX-UHFFFAOYSA-N 0.000 claims 1
- KAJKHTRVDYCYSO-UHFFFAOYSA-N 1-[1-[4-[5-(dimethylamino)-4-hydroxypentoxy]benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C1=CC(OCCCC(O)CN(C)C)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 KAJKHTRVDYCYSO-UHFFFAOYSA-N 0.000 claims 1
- DUELXLLYXQPHON-UHFFFAOYSA-N 1-[1-[4-[8-(diethylamino)-7-hydroxyoctoxy]benzoyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one Chemical compound C1=CC(OCCCCCCC(O)CN(CC)CC)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 DUELXLLYXQPHON-UHFFFAOYSA-N 0.000 claims 1
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- MSHPYKGWAKAPLI-UHFFFAOYSA-N 3-[4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]propyl carbamate Chemical compound C1=CC(OCCCOC(=O)N)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 MSHPYKGWAKAPLI-UHFFFAOYSA-N 0.000 claims 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims 1
- 125000005210 alkyl ammonium group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- WRNXUQJJCIZICJ-UHFFFAOYSA-N mozavaptan Chemical compound C12=CC=CC=C2C(N(C)C)CCCN1C(=O)C(C=C1)=CC=C1NC(=O)C1=CC=CC=C1C WRNXUQJJCIZICJ-UHFFFAOYSA-N 0.000 claims 1
- KSNUCNRMDYJBKT-UHFFFAOYSA-N n-[3-[4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]propyl]acetamide Chemical compound C1=CC(OCCCNC(=O)C)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 KSNUCNRMDYJBKT-UHFFFAOYSA-N 0.000 claims 1
- ZNKOUFFBKXUPAW-UHFFFAOYSA-N n-[3-[4-[4-(7-fluoro-2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]propyl]acetamide Chemical compound C1=CC(OCCCNC(=O)C)=CC=C1C(=O)N1CCC(N2C3=CC(F)=CC=C3CCC2=O)CC1 ZNKOUFFBKXUPAW-UHFFFAOYSA-N 0.000 claims 1
- IHFUGFLYZAVAOH-UHFFFAOYSA-N n-[3-chloro-4-(7-fluoro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)phenyl]-2-methylbenzamide Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1Cl)=CC=C1C(=O)N1C2=CC=C(F)C=C2C(O)CCC1 IHFUGFLYZAVAOH-UHFFFAOYSA-N 0.000 claims 1
- ZATPFKWGNKFRHK-UHFFFAOYSA-N n-[4-(7-chloro-5-hydroxy-2,3,4,5-tetrahydro-1-benzazepine-1-carbonyl)-3-methoxyphenyl]-2-methylbenzamide Chemical compound C=1C=C(C(=O)N2C3=CC=C(Cl)C=C3C(O)CCC2)C(OC)=CC=1NC(=O)C1=CC=CC=C1C ZATPFKWGNKFRHK-UHFFFAOYSA-N 0.000 claims 1
- DVMXTWCHCARTQS-UHFFFAOYSA-N n-[4-[4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]butyl]acetamide Chemical compound C1=CC(OCCCCNC(=O)C)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 DVMXTWCHCARTQS-UHFFFAOYSA-N 0.000 claims 1
- KKBXHTGRDPDXTC-UHFFFAOYSA-N n-[5-[4-[4-(2-oxo-3,4-dihydroquinolin-1-yl)piperidine-1-carbonyl]phenoxy]pentyl]acetamide Chemical compound C1=CC(OCCCCCNC(=O)C)=CC=C1C(=O)N1CCC(N2C3=CC=CC=C3CCC2=O)CC1 KKBXHTGRDPDXTC-UHFFFAOYSA-N 0.000 claims 1
- GYHCTFXIZSNGJT-UHFFFAOYSA-N tolvaptan Chemical compound CC1=CC=CC=C1C(=O)NC(C=C1C)=CC=C1C(=O)N1C2=CC=C(Cl)C=C2C(O)CCC1 GYHCTFXIZSNGJT-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 5
- 201000010099 disease Diseases 0.000 abstract description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 4
- 125000004429 atom Chemical group 0.000 description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 35
- 125000002252 acyl group Chemical group 0.000 description 34
- DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 32
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 32
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- 239000003826 tablet Substances 0.000 description 31
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 30
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 29
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 29
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 28
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 27
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 27
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 24
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 21
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- 238000002360 preparation method Methods 0.000 description 16
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 235000019441 ethanol Nutrition 0.000 description 15
- 229920001223 polyethylene glycol Polymers 0.000 description 15
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- 230000002401 inhibitory effect Effects 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 12
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 11
- 125000003884 phenylalkyl group Chemical group 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000002202 Polyethylene glycol Substances 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 10
- 125000004487 4-tetrahydropyranyl group Chemical group [H]C1([H])OC([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 238000002347 injection Methods 0.000 description 9
- 239000007924 injection Substances 0.000 description 9
- 125000005505 thiomorpholino group Chemical group 0.000 description 9
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 229920002261 Corn starch Polymers 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000008120 corn starch Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 7
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 7
- 235000019359 magnesium stearate Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 6
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 125000006308 propyl amino group Chemical group 0.000 description 6
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 241000282320 Panthera leo Species 0.000 description 5
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 150000001721 carbon Chemical group 0.000 description 5
- 235000015165 citric acid Nutrition 0.000 description 5
- 229960004106 citric acid Drugs 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
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- YFGAFXCSLUUJRG-WCCKRBBISA-M sodium;(2s)-2-amino-5-(diaminomethylideneamino)pentanoate Chemical compound [Na+].[O-]C(=O)[C@@H](N)CCCN=C(N)N YFGAFXCSLUUJRG-WCCKRBBISA-M 0.000 description 1
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- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000000196 tragacanth Substances 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-O tributylazanium Chemical compound CCCC[NH+](CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-O 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000430 tryptophan group Chemical group [H]N([H])C(C(=O)O*)C([H])([H])C1=C([H])N([H])C2=C([H])C([H])=C([H])C([H])=C12 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002987 valine group Chemical group [H]N([H])C([H])(C(*)=O)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17556392 | 1992-07-02 | ||
| JP175563/1992 | 1992-07-02 | ||
| JP17556692 | 1992-07-02 | ||
| JP175566/1992 | 1992-07-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2116334A1 true CA2116334A1 (en) | 1994-01-20 |
Family
ID=26496804
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2116334 Abandoned CA2116334A1 (en) | 1992-07-02 | 1993-06-22 | Oxytocin antagonist |
Country Status (8)
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5356904A (en) * | 1992-10-07 | 1994-10-18 | Merck & Co., Inc. | Carbostyril oxytocin receptor antagonists |
| GB9307527D0 (en) * | 1993-04-13 | 1993-06-02 | Fujisawa Pharmaceutical Co | New venzamide derivatives,processes for the preparation thereof and pharmaceutical composition comprising the same |
| WO1995002405A1 (en) * | 1993-07-16 | 1995-01-26 | Merck & Co., Inc. | Benzoxazinone and benzopyrimidinone piperidinyl tocolytic oxytocin receptor antagonists |
| EP0805681A4 (en) * | 1995-01-24 | 1998-05-06 | Merck & Co Inc | TOCOLYTIC ANTAGONISTS OF OXYTOCIN RECEPTORS |
| TW359669B (en) * | 1995-12-15 | 1999-06-01 | Otsuka Pharma Co Ltd | Benzazepine derivatives |
| US5726172A (en) * | 1996-01-16 | 1998-03-10 | Merck & Co., Inc. | Tocolytic oxytocin receptor antagonists |
| AR011913A1 (es) | 1997-03-06 | 2000-09-13 | Yamano Masaki | Derivados de 4,4-difluoro-2,3,4,5-tetrahidro-1h-1-benzoazepina y composiciones farmaceuticas de los mismos. |
| US7109193B2 (en) | 2001-04-12 | 2006-09-19 | Wyeth | Tricyclic diazepines tocolytic oxytocin receptor antagonists |
| US7022699B2 (en) | 2001-04-12 | 2006-04-04 | Wyeth | Cyclohexenyl phenyl diazepines vasopressin and oxytocin receptor modulators |
| US6977254B2 (en) | 2001-04-12 | 2005-12-20 | Wyeth | Hydroxy cyclohexenyl phenyl carboxamides tocolytic oxytocin receptor antagonists |
| US7202239B2 (en) | 2001-04-12 | 2007-04-10 | Wyeth | Cyclohexylphenyl carboxamides tocolytic oxytocin receptor antagonists |
| US7064120B2 (en) | 2001-04-12 | 2006-06-20 | Wyeth | Tricyclic pyridyl carboxamides and derivatives thereof tocolytic oxytocin receptor antagonists |
| US7326700B2 (en) | 2001-04-12 | 2008-02-05 | Wyeth | Cyclohexenyl phenyl carboxamides tocolytic oxytocin receptor antagonists |
| US6900200B2 (en) | 2001-04-12 | 2005-05-31 | Wyeth | Tricyclic hydroxy carboxamides and derivatives thereof tocolytic oxytocin receptor antagonists |
| GB0120051D0 (en) * | 2001-08-16 | 2001-10-10 | Ferring Bv | Oxytocin agonists |
| US20050228016A1 (en) * | 2002-06-13 | 2005-10-13 | Enrique Michelotti | Tetrahydroquinolines for modulating the expression of exogenous genes via an ecdysone receptor complex |
| NZ537858A (en) | 2002-07-15 | 2008-04-30 | Myriad Genetics Inc | Compounds, compositions, and methods employing same |
| US7504508B2 (en) | 2002-10-04 | 2009-03-17 | Millennium Pharmaceuticals, Inc. | PGD2 receptor antagonists for the treatment of inflammatory diseases |
| JP2006508077A (ja) | 2002-10-04 | 2006-03-09 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症疾患を治療するためのｐｇｄ２レセプタアンタゴニスト |
| EP1554260A1 (en) * | 2002-10-22 | 2005-07-20 | Glaxo Group Limited | Aryloxyalkylamine derivatives as h3 receptor ligands |
| TW200503994A (en) * | 2003-01-24 | 2005-02-01 | Novartis Ag | Organic compounds |
| TWI322689B (en) | 2003-02-24 | 2010-04-01 | Otsuka Pharma Co Ltd | Method for treating severe heart failure and medicament therefor |
| JP2008543726A (ja) | 2005-02-24 | 2008-12-04 | ミレニアム・ファーマシューティカルズ・インコーポレイテッド | 炎症性疾患の処置のためのｐｇｄ２受容体アンタゴニスト |
| US7671058B2 (en) | 2006-06-21 | 2010-03-02 | Institute Of Medicinal Molecular Design, Inc. | N-(3,4-disubstituted phenyl) salicylamide derivatives |
| CN101686983A (zh) | 2007-05-10 | 2010-03-31 | Amr科技公司 | 芳基和杂芳基取代的四氢苯并-1,4-二氮杂䓬及其阻断去甲肾上腺素、多巴胺和5-羟色胺重摄取的用途 |
| TWI459947B (zh) | 2007-06-26 | 2014-11-11 | Otsuka Pharma Co Ltd | 苯并氮呯化合物及藥學製劑 |
| CN102030709B (zh) * | 2009-09-25 | 2013-10-16 | 江苏豪森医药集团有限公司 | 用作加压素受体拮抗剂的苯并氮杂卓类化合物 |
| US9102669B2 (en) | 2011-12-06 | 2015-08-11 | Janssen Pharmaceutica Nv | Substituted piperidinyl-pyridazinyl derivatives useful as SCD 1 inhibitors |
| WO2013085954A1 (en) | 2011-12-06 | 2013-06-13 | Janssen Pharmaceutica Nv | Substituted piperidinyl-carboxamide derivatives useful as scd 1 inhibitors |
| WO2017156164A1 (en) | 2016-03-09 | 2017-09-14 | Board Of Regents, The University Of Texas System | 20-hete receptor (gpr75) antagonists and methods of use |
| WO2019003433A1 (ja) | 2017-06-30 | 2019-01-03 | 大塚製薬株式会社 | ベンゾアゼピン誘導体 |
| KR20210040368A (ko) * | 2018-06-29 | 2021-04-13 | 킨네이트 바이오파마 인크. | 사이클린 의존성 키나제의 억제제 |
| US20240101568A1 (en) * | 2020-11-26 | 2024-03-28 | Shanghai Jemincare Pharmaceutical Co., Ltd | Novel benzazepine spiro derivative |
| CN112851583B (zh) * | 2021-01-19 | 2023-09-08 | 徐州医科大学 | 新型苯并氮杂䓬类化合物、组合物及其用途 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK0382185T3 (da) * | 1989-02-10 | 1994-07-04 | Otsuka Pharma Co Ltd | Carbostyrilderivater |
| CA2026856A1 (en) * | 1989-10-05 | 1991-04-06 | Mark G. Bock | 3-substituted-1,4-benzodiazepines useful as oxytocin |
| DE69026708T2 (de) * | 1989-10-20 | 1997-04-03 | Otsuka Pharma Co Ltd | Benzoheterozyklische verbindungen |
| TW199153B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1990-08-07 | 1993-02-01 | Dtsuka Seiyaku Kk |
-
1993
- 1993-06-22 TW TW82104913A patent/TW249201B/zh active
- 1993-06-22 CA CA 2116334 patent/CA2116334A1/en not_active Abandoned
- 1993-06-22 EP EP93913553A patent/EP0602209A1/en not_active Withdrawn
- 1993-06-22 WO PCT/JP1993/000835 patent/WO1994001113A1/en not_active Application Discontinuation
- 1993-06-22 AU AU43569/93A patent/AU657424B2/en not_active Ceased
- 1993-07-02 CN CN 93109876 patent/CN1091288A/zh active Pending
- 1993-07-02 MX MX9304015A patent/MX9304015A/es unknown
-
1997
- 1997-03-11 ID IDP970772A patent/ID15999A/id unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU4356993A (en) | 1994-01-31 |
| ID15999A (id) | 1997-08-21 |
| TW249201B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-06-11 |
| MX9304015A (es) | 1994-02-28 |
| EP0602209A1 (en) | 1994-06-22 |
| CN1091288A (zh) | 1994-08-31 |
| AU657424B2 (en) | 1995-03-09 |
| WO1994001113A1 (en) | 1994-01-20 |
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