TW449584B - Tricyclic Benzazepine, their perparation and the pharmaceutical composition containing them - Google Patents

Tricyclic Benzazepine, their perparation and the pharmaceutical composition containing them Download PDF

Info

Publication number: TW449584B
Authority: TW; Taiwan
Prior art keywords: cage; ministry; cns; page; please read
Prior art date: 1995-01-17

Application number

TW085100462A

Other languages

English (en)

Chinese (zh)

Inventor

Jay D Albright

Aranapakam M Venkatesan

Santos Efren G Delos

Original Assignee

American Cyanamid Co

Priority date (The priority date 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 date listed.)

1995-01-17

Filing date

1996-01-16

Publication date

2001-08-11

1995-12-22 Priority claimed from US08/548,805 external-priority patent/US5849735A/en

1996-01-16 Application filed by American Cyanamid Co filed Critical American Cyanamid Co

2001-08-11 Application granted granted Critical

2001-08-11 Publication of TW449584B publication Critical patent/TW449584B/zh

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DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 title claims description 31
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
229910001868 water Inorganic materials 0.000 claims abstract description 140
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 133
150000001875 compounds Chemical class 0.000 claims abstract description 83
238000000034 method Methods 0.000 claims abstract description 16
230000000694 effects Effects 0.000 claims abstract description 11
239000003038 vasopressin antagonist Substances 0.000 claims abstract description 11
229940116211 Vasopressin antagonist Drugs 0.000 claims abstract description 10
238000004519 manufacturing process Methods 0.000 claims abstract description 8
239000005557 antagonist Substances 0.000 claims abstract description 7
102000004136 Vasopressin Receptors Human genes 0.000 claims abstract description 5
108090000643 Vasopressin Receptors Proteins 0.000 claims abstract description 5
230000008060 renal absorption Effects 0.000 claims abstract description 3
201000010099 disease Diseases 0.000 claims abstract 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 201
239000007787 solid Substances 0.000 claims description 185
238000011049 filling Methods 0.000 claims description 147
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 137
239000000243 solution Substances 0.000 claims description 137
-1 benzyl Fluorenyl Chemical group 0.000 claims description 135
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 128
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 127
239000000047 product Substances 0.000 claims description 101
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 100
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 90
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 80
230000002079 cooperative effect Effects 0.000 claims description 78
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 77
235000000346 sugar Nutrition 0.000 claims description 77
150000001412 amines Chemical class 0.000 claims description 76
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 75
229910052786 argon Inorganic materials 0.000 claims description 69
239000002904 solvent Substances 0.000 claims description 68
239000007789 gas Chemical group 0.000 claims description 55
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 54
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 53
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 53
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 52
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 52
239000000706 filtrate Substances 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 47
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 45
239000013078 crystal Substances 0.000 claims description 40
239000000284 extract Substances 0.000 claims description 37
239000000391 magnesium silicate Substances 0.000 claims description 37
229910052919 magnesium silicate Inorganic materials 0.000 claims description 37
235000019792 magnesium silicate Nutrition 0.000 claims description 37
239000012267 brine Substances 0.000 claims description 35
238000006243 chemical reaction Methods 0.000 claims description 35
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 35
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 31
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
239000012265 solid product Substances 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 26
235000010290 biphenyl Nutrition 0.000 claims description 25
238000002309 gasification Methods 0.000 claims description 25
230000002265 prevention Effects 0.000 claims description 25
239000004305 biphenyl Substances 0.000 claims description 24
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
KBZOIRJILGZLEJ-LGYYRGKSSA-N argipressin Chemical compound C([C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@@H](C(N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N1)=O)N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(N)=O)C1=CC=CC=C1 KBZOIRJILGZLEJ-LGYYRGKSSA-N 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
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239000000741 silica gel Substances 0.000 claims description 23
229910002027 silica gel Inorganic materials 0.000 claims description 23
PXXJHWLDUBFPOL-UHFFFAOYSA-N benzamidine Chemical compound NC(=N)C1=CC=CC=C1 PXXJHWLDUBFPOL-UHFFFAOYSA-N 0.000 claims description 22
125000005605 benzo group Chemical group 0.000 claims description 22
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 claims description 22
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
239000000126 substance Substances 0.000 claims description 22
238000012360 testing method Methods 0.000 claims description 21
238000004458 analytical method Methods 0.000 claims description 19
239000007788 liquid Substances 0.000 claims description 19
229960003726 vasopressin Drugs 0.000 claims description 18
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 17
GXBMIBRIOWHPDT-UHFFFAOYSA-N Vasopressin Natural products N1C(=O)C(CC=2C=C(O)C=CC=2)NC(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CCCN=C(N)N)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C1CC1=CC=CC=C1 GXBMIBRIOWHPDT-UHFFFAOYSA-N 0.000 claims description 16
102000002852 Vasopressins Human genes 0.000 claims description 16
108010004977 Vasopressins Proteins 0.000 claims description 16
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 16
238000003756 stirring Methods 0.000 claims description 16
238000009739 binding Methods 0.000 claims description 15
102000005962 receptors Human genes 0.000 claims description 15
108020003175 receptors Proteins 0.000 claims description 15
230000027455 binding Effects 0.000 claims description 14
210000004369 blood Anatomy 0.000 claims description 14
239000008280 blood Substances 0.000 claims description 14
238000002474 experimental method Methods 0.000 claims description 14
230000003042 antagnostic effect Effects 0.000 claims description 12
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
239000012280 lithium aluminium hydride Substances 0.000 claims description 12
239000000463 material Substances 0.000 claims description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 11
229910052770 Uranium Inorganic materials 0.000 claims description 11
238000001819 mass spectrum Methods 0.000 claims description 11
LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical compound N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 claims description 10
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 claims description 10
239000000872 buffer Substances 0.000 claims description 10
238000007639 printing Methods 0.000 claims description 10
238000011282 treatment Methods 0.000 claims description 10
ZVAPWJGRRUHKGP-UHFFFAOYSA-N 1h-1,5-benzodiazepine Chemical compound N1C=CC=NC2=CC=CC=C12 ZVAPWJGRRUHKGP-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
230000002792 vascular Effects 0.000 claims description 8
239000012141 concentrate Substances 0.000 claims description 7
238000004949 mass spectrometry Methods 0.000 claims description 7
102000004169 proteins and genes Human genes 0.000 claims description 7
108090000623 proteins and genes Proteins 0.000 claims description 7
150000003839 salts Chemical class 0.000 claims description 7
108010039627 Aprotinin Proteins 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 6
239000008186 active pharmaceutical agent Substances 0.000 claims description 6
229960004405 aprotinin Drugs 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
ZPNFWUPYTFPOJU-LPYSRVMUSA-N iniprol Chemical compound C([C@H]1C(=O)NCC(=O)NCC(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@H](C(N[C@H](C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC=4C=CC=CC=4)C(=O)N[C@@H](CC=4C=CC(O)=CC=4)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC=4C=CC=CC=4)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CCCCN)NC(=O)[C@H](C)NC(=O)[C@H](CCCNC(N)=N)NC2=O)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CSSC[C@H](NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]2N(CCC2)C(=O)[C@@H](N)CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N2[C@@H](CCC2)C(=O)N2[C@@H](CCC2)C(=O)N[C@@H](CC=2C=CC(O)=CC=2)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N2[C@@H](CCC2)C(=O)N3)C(=O)NCC(=O)NCC(=O)N[C@@H](C)C(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@H](C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@H](C(=O)N1)C(C)C)[C@@H](C)O)[C@@H](C)CC)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 ZPNFWUPYTFPOJU-LPYSRVMUSA-N 0.000 claims description 6
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 claims description 6
VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims description 6
DHARILAASAAGJJ-UHFFFAOYSA-N 4-benzylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1CC1=CC=CC=C1 DHARILAASAAGJJ-UHFFFAOYSA-N 0.000 claims description 5
GDBQQVLCIARPGH-UHFFFAOYSA-N Leupeptin Natural products CC(C)CC(NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(C=O)CCCN=C(N)N GDBQQVLCIARPGH-UHFFFAOYSA-N 0.000 claims description 5
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239000003112 inhibitor Substances 0.000 claims description 5
GDBQQVLCIARPGH-ULQDDVLXSA-N leupeptin Chemical compound CC(C)C[C@H](NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](C=O)CCCN=C(N)N GDBQQVLCIARPGH-ULQDDVLXSA-N 0.000 claims description 5
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PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
239000012530 fluid Substances 0.000 claims description 4
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125000003147 glycosyl group Chemical group 0.000 claims description 4
230000009871 nonspecific binding Effects 0.000 claims description 4
YBYRMVIVWMBXKQ-UHFFFAOYSA-N phenylmethanesulfonyl fluoride Chemical compound FS(=O)(=O)CC1=CC=CC=C1 YBYRMVIVWMBXKQ-UHFFFAOYSA-N 0.000 claims description 4
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 claims description 4
KYVHGCKMVJDCNV-UHFFFAOYSA-N 1,4-benzothiazepine Chemical compound S1C=CN=CC2=CC=CC=C12 KYVHGCKMVJDCNV-UHFFFAOYSA-N 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 3
BOUPBBUTPAIGOX-UHFFFAOYSA-N C1=CC=CC2=NC3=CC=CC=C3C=C12.[Ar] Chemical compound C1=CC=CC2=NC3=CC=CC=C3C=C12.[Ar] BOUPBBUTPAIGOX-UHFFFAOYSA-N 0.000 claims description 3
239000007832 Na2SO4 Substances 0.000 claims description 3
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150000004985 diamines Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 3
238000005086 pumping Methods 0.000 claims description 3
229910052938 sodium sulfate Inorganic materials 0.000 claims description 3
235000011152 sodium sulphate Nutrition 0.000 claims description 3
229910052714 tellurium Inorganic materials 0.000 claims description 3
PORWMNRCUJJQNO-UHFFFAOYSA-N tellurium atom Chemical compound [Te] PORWMNRCUJJQNO-UHFFFAOYSA-N 0.000 claims description 3
QPPOMEOQNLTFRU-UHFFFAOYSA-N 1,4-thiazepine Chemical compound S1C=CC=NC=C1 QPPOMEOQNLTFRU-UHFFFAOYSA-N 0.000 claims description 2
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150000001409 amidines Chemical class 0.000 claims description 2
DATSOCBXQNFJEM-UHFFFAOYSA-N antimony neodymium Chemical compound [Sb].[Nd] DATSOCBXQNFJEM-UHFFFAOYSA-N 0.000 claims description 2
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ASTGEVIQIQQVKN-UHFFFAOYSA-N diazomethane oxolane Chemical compound O1CCCC1.[N+](=[N-])=C ASTGEVIQIQQVKN-UHFFFAOYSA-N 0.000 claims description 2
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LWJROJCJINYWOX-UHFFFAOYSA-L mercury dichloride Chemical compound Cl[Hg]Cl LWJROJCJINYWOX-UHFFFAOYSA-L 0.000 claims description 2
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HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 claims 4
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UDJFFSGCRRMVFH-UHFFFAOYSA-N pyrido[2,3-d]pyrimidine Chemical compound N1=CN=CC2=CC=CN=C21 UDJFFSGCRRMVFH-UHFFFAOYSA-N 0.000 description 1
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LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
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150000003377 silicon compounds Chemical class 0.000 description 1
235000020374 simple syrup Nutrition 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000342 sodium bisulfate Inorganic materials 0.000 description 1
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
AGOFQOOAJAPLDU-UHFFFAOYSA-N sodium;1,3,5-triazine-2,4,6-triamine Chemical compound [Na].NC1=NC(N)=NC(N)=N1 AGOFQOOAJAPLDU-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
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238000012453 sprague-dawley rat model Methods 0.000 description 1
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230000003068 static effect Effects 0.000 description 1
238000010025 steaming Methods 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
FHADSKGDQLZUIT-UHFFFAOYSA-N stilbene hydrochloride Chemical compound Cl.C1(=CC=CC=C1)C=CC1=CC=CC=C1 FHADSKGDQLZUIT-UHFFFAOYSA-N 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
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150000008163 sugars Chemical class 0.000 description 1
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150000003512 tertiary amines Chemical class 0.000 description 1
AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical class CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
150000000000 tetracarboxylic acids Chemical class 0.000 description 1
229910052716 thallium Inorganic materials 0.000 description 1
BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
230000004797 therapeutic response Effects 0.000 description 1
150000003553 thiiranes Chemical class 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
NBOMNTLFRHMDEZ-UHFFFAOYSA-N thiosalicylic acid Chemical compound OC(=O)C1=CC=CC=C1S NBOMNTLFRHMDEZ-UHFFFAOYSA-N 0.000 description 1
229940104230 thymidine Drugs 0.000 description 1
XPDWGBQVDMORPB-UHFFFAOYSA-N trifluoromethane acid Natural products FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-O triphenylphosphanium Chemical compound C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-O 0.000 description 1
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229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- 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
- 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
- A61P15/06—Antiabortive agents; Labour repressants
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/20—Dibenz [b, e] azepines; Hydrogenated dibenz [b, e] azepines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
- C07D223/24—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom
- C07D223/28—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines with hydrocarbon radicals, substituted by nitrogen atoms, attached to the ring nitrogen atom having a single bond between positions 10 and 11
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/38—[b, e]- or [b, f]-condensed with six-membered rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/12—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D267/16—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with two six-membered rings
- C07D267/20—[b, f]-condensed
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Engineering & Computer Science (AREA)
Reproductive Health (AREA)
Endocrinology (AREA)
Heart & Thoracic Surgery (AREA)
Pregnancy & Childbirth (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Urology & Nephrology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

TW085100462A 1995-01-17 1996-01-16 Tricyclic Benzazepine, their perparation and the pharmaceutical composition containing them TW449584B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US37316995A	1995-01-17	1995-01-17
US08/548,805 US5849735A (en)	1995-01-17	1995-12-22	Tricyclic benzazepine vasopressin antagonists

Publications (1)

Publication Number	Publication Date
TW449584B true TW449584B (en)	2001-08-11

Family

ID=27006077

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
TW085100462A TW449584B (en)	1995-01-17	1996-01-16	Tricyclic Benzazepine, their perparation and the pharmaceutical composition containing them

Country Status (14)

Country	Link
EP (1)	EP0804420A1 (de)
JP (1)	JPH10512865A (de)
CN (1)	CN1190391A (de)
AR (1)	AR002459A1 (de)
AU (1)	AU4904296A (de)
BR (1)	BR9606977A (de)
CA (1)	CA2210688A1 (de)
CZ (1)	CZ224597A3 (de)
EA (1)	EA000752B1 (de)
HU (1)	HUP9801219A3 (de)
IL (1)	IL116777A (de)
NZ (1)	NZ302881A (de)
TW (1)	TW449584B (de)
WO (1)	WO1996022282A1 (de)

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* Cited by examiner, † Cited by third party
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US5693635A (en) *	1993-07-29	1997-12-02	American Cyanamid Company	Tricyclic benzazepine vasopressin antagonists
AU3296497A (en) *	1996-06-13	1998-01-07	American Cyanamid Company	Tricyclic benzazepine vasopressin antagonists
AU8592598A (en) *	1997-07-30	1999-02-22	Wyeth	Tricyclic vasopressin agonists
US6194407B1 (en)	1997-07-30	2001-02-27	American Home Products Corporation	Tricyclic pyrido vasopressin agonists
AR018818A1 (es) *	1998-04-03	2001-12-12	Yamano Masaki	Una composicion farmaceutica para la terapia de un edema.
US6090803A (en) *	1998-07-24	2000-07-18	American Home Products Corporation	Tricyclic vasopressin agonists
US7138393B2 (en)	1998-07-24	2006-11-21	Wyeth	Biologically active vasopressin agonist metabolites
US6297234B1 (en)	1999-02-04	2001-10-02	American Home Products Corporation	Arylthiophene vasopressin agonists
AU6870500A (en) *	1999-09-06	2001-04-10	Takeda Chemical Industries Ltd.	Process for the preparation of 2,3-dihydroazepine derivatives
US7202239B2 (en)	2001-04-12	2007-04-10	Wyeth	Cyclohexylphenyl carboxamides tocolytic oxytocin receptor antagonists
US6977254B2 (en)	2001-04-12	2005-12-20	Wyeth	Hydroxy cyclohexenyl phenyl carboxamides tocolytic oxytocin receptor antagonists
US7064120B2 (en) *	2001-04-12	2006-06-20	Wyeth	Tricyclic pyridyl carboxamides and derivatives thereof tocolytic oxytocin receptor antagonists
EP1381370B1 (de)	2001-04-12	2007-03-07	Wyeth	N-biphenylcarbonyl- und n-phenylpyridylcarbonyl substituierte bi- and tricyclische azepine und diazepine als vasopressin-agonisten
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
US7022699B2 (en)	2001-04-12	2006-04-04	Wyeth	Cyclohexenyl phenyl diazepines vasopressin and oxytocin receptor modulators
US7109193B2 (en)	2001-04-12	2006-09-19	Wyeth	Tricyclic diazepines tocolytic oxytocin receptor antagonists
CN1294134C (zh)	2001-04-12	2007-01-10	惠氏公司	环己基苯基血管升压素激动剂
SE0102299D0 (sv) *	2001-06-26	2001-06-26	Astrazeneca Ab	Compounds
SE0102764D0 (sv)	2001-08-17	2001-08-17	Astrazeneca Ab	Compounds
RU2266906C1 (ru) *	2004-04-29	2005-12-27	Общество с ограниченной ответственностью "Исследовательский Институт Химического Разнообразия" (ООО "Исследовательский Институт Химического Разнообразия")	Анелированные карбамоилазагетероциклы, способы их получения (варианты), фармацевтическая композиция, фокусированная библиотека
KR101346902B1 (ko)	2005-07-09	2014-01-02	아스트라제네카 아베	당뇨병 치료에 있어 ｇｌｋ 활성화제로서 사용하기 위한헤테로아릴 벤즈아미드 유도체
PE20080145A1 (es)	2006-03-21	2008-02-11	Janssen Pharmaceutica Nv	Tetrahidro-pirimidoazepinas como moduladores de trpv1
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1996
- 1996-01-15 AR ARP960101027A patent/AR002459A1/es unknown
- 1996-01-16 CZ CZ972245A patent/CZ224597A3/cs unknown
- 1996-01-16 HU HU9801219A patent/HUP9801219A3/hu unknown
- 1996-01-16 BR BR9606977A patent/BR9606977A/pt not_active Application Discontinuation
- 1996-01-16 EP EP96905227A patent/EP0804420A1/de not_active Withdrawn
- 1996-01-16 CA CA002210688A patent/CA2210688A1/en not_active Abandoned
- 1996-01-16 CN CN96192568A patent/CN1190391A/zh active Pending
- 1996-01-16 WO PCT/US1996/001051 patent/WO1996022282A1/en not_active Ceased
- 1996-01-16 IL IL11677796A patent/IL116777A/xx not_active IP Right Cessation
- 1996-01-16 AU AU49042/96A patent/AU4904296A/en not_active Abandoned
- 1996-01-16 EA EA199700116A patent/EA000752B1/ru not_active IP Right Cessation
- 1996-01-16 NZ NZ302881A patent/NZ302881A/xx unknown
- 1996-01-16 JP JP8522448A patent/JPH10512865A/ja not_active Ceased
- 1996-01-16 TW TW085100462A patent/TW449584B/zh not_active IP Right Cessation

Also Published As

Publication number	Publication date
AU4904296A (en)	1996-08-07
IL116777A0 (en)	1996-05-14
JPH10512865A (ja)	1998-12-08
CA2210688A1 (en)	1996-07-25
CN1190391A (zh)	1998-08-12
CZ224597A3 (en)	1997-12-17
BR9606977A (pt)	1997-11-04
HUP9801219A2 (hu)	1998-10-28
NZ302881A (en)	1999-03-29
AR002459A1 (es)	1998-03-25
EP0804420A1 (de)	1997-11-05
EA199700116A1 (ru)	1997-12-30
IL116777A (en)	2000-11-21
EA000752B1 (ru)	2000-04-24
WO1996022282A1 (en)	1996-07-25
HUP9801219A3 (en)	2000-07-28

Legal Events

Date	Code	Title	Description
2001-12-27	GD4A	Issue of patent certificate for granted invention patent
2004-11-11	MM4A	Annulment or lapse of patent due to non-payment of fees

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