UA64690C2 - A condensed benzadepine derivative, an intermediate compound for preparing thereof and a pharmaceutical composition - Google Patents

A condensed benzadepine derivative, an intermediate compound for preparing thereof and a pharmaceutical composition Download PDF

Info

Publication number: UA64690C2
Authority: UA; Ukraine
Prior art keywords: group; lower alkyl; substituted; ring; resulting
Prior art date: 1993-07-21

Application number

UA96010145A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Yamanouty Farmaceutical Co Ltd

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.)

1993-07-21

Filing date

1994-07-19

Publication date

2004-03-15

1994-07-19 Application filed by Yamanouty Farmaceutical Co Ltd filed Critical Yamanouty Farmaceutical Co Ltd

2004-03-15 Publication of UA64690C2 publication Critical patent/UA64690C2/uk

Links

239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 5
150000001875 compounds Chemical class 0.000 title claims description 133
125000000217 alkyl group Chemical group 0.000 claims abstract description 97
150000003839 salts Chemical class 0.000 claims abstract description 34
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 abstract description 22
150000008038 benzoazepines Chemical class 0.000 claims abstract description 20
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 20
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 19
101800001144 Arg-vasopressin Proteins 0.000 claims abstract description 18
102100026383 Vasopressin-neurophysin 2-copeptin Human genes 0.000 claims abstract description 18
125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
125000002947 alkylene group Chemical group 0.000 claims abstract description 7
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 6
-1 1-piperazinyl group Chemical group 0.000 claims description 147
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 93
125000003277 amino group Chemical group 0.000 claims description 62
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 36
125000002252 acyl group Chemical group 0.000 claims description 32
125000003282 alkyl amino group Chemical group 0.000 claims description 26
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
125000005843 halogen group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 20
125000003118 aryl group Chemical group 0.000 claims description 16
125000000753 cycloalkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 15
125000002883 imidazolyl group Chemical group 0.000 claims description 13
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 12
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 10
239000005557 antagonist Substances 0.000 claims description 9
125000005236 alkanoylamino group Chemical group 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 8
239000005711 Benzoic acid Substances 0.000 claims description 7
235000010233 benzoic acid Nutrition 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
230000003042 antagnostic effect Effects 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 abstract description 9
239000001257 hydrogen Substances 0.000 abstract description 6
229910052739 hydrogen Inorganic materials 0.000 abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 4
229910052760 oxygen Inorganic materials 0.000 abstract description 4
239000001301 oxygen Substances 0.000 abstract description 4
125000004434 sulfur atom Chemical group 0.000 abstract description 4
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 3
229910052736 halogen Inorganic materials 0.000 abstract description 3
150000002367 halogens Chemical class 0.000 abstract description 3
239000004480 active ingredient Substances 0.000 abstract description 2
229940116211 Vasopressin antagonist Drugs 0.000 abstract 1
150000001555 benzenes Chemical group 0.000 abstract 1
150000002431 hydrogen Chemical class 0.000 abstract 1
239000003038 vasopressin antagonist Substances 0.000 abstract 1
239000000243 solution Substances 0.000 description 141
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 100
238000006243 chemical reaction Methods 0.000 description 90
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
238000000034 method Methods 0.000 description 62
239000000203 mixture Substances 0.000 description 62
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
239000002904 solvent Substances 0.000 description 52
ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 50
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
239000007864 aqueous solution Substances 0.000 description 47
229920006395 saturated elastomer Polymers 0.000 description 47
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 36
125000006239 protecting group Chemical group 0.000 description 36
238000002844 melting Methods 0.000 description 34
230000008018 melting Effects 0.000 description 34
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
238000010992 reflux Methods 0.000 description 33
239000012044 organic layer Substances 0.000 description 32
235000019441 ethanol Nutrition 0.000 description 31
239000013078 crystal Substances 0.000 description 28
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
229910000030 sodium bicarbonate Inorganic materials 0.000 description 27
235000017557 sodium bicarbonate Nutrition 0.000 description 27
238000003756 stirring Methods 0.000 description 25
238000004821 distillation Methods 0.000 description 24
125000003342 alkenyl group Chemical group 0.000 description 23
239000007787 solid Substances 0.000 description 23
239000000126 substance Substances 0.000 description 23
238000001816 cooling Methods 0.000 description 22
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 22
238000010438 heat treatment Methods 0.000 description 22
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
125000000304 alkynyl group Chemical group 0.000 description 19
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 19
239000000706 filtrate Substances 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
239000002198 insoluble material Substances 0.000 description 18
239000002253 acid Substances 0.000 description 17
238000000921 elemental analysis Methods 0.000 description 17
239000012046 mixed solvent Substances 0.000 description 17
229910000027 potassium carbonate Inorganic materials 0.000 description 17
235000011181 potassium carbonates Nutrition 0.000 description 17
239000007858 starting material Substances 0.000 description 17
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
238000004440 column chromatography Methods 0.000 description 15
238000001914 filtration Methods 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 13
239000011780 sodium chloride Substances 0.000 description 13
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
125000004423 acyloxy group Chemical group 0.000 description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 12
MVEAAGBEUOMFRX-UHFFFAOYSA-N ethyl acetate;hydrochloride Chemical compound Cl.CCOC(C)=O MVEAAGBEUOMFRX-UHFFFAOYSA-N 0.000 description 12
238000012360 testing method Methods 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 11
125000004453 alkoxycarbonyl group Chemical group 0.000 description 11
238000007112 amidation reaction Methods 0.000 description 11
230000008485 antagonism Effects 0.000 description 11
239000003795 chemical substances by application Substances 0.000 description 11
239000007924 injection Substances 0.000 description 11
238000002347 injection Methods 0.000 description 11
239000010410 layer Substances 0.000 description 11
DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical group N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 10
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
235000011167 hydrochloric acid Nutrition 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
238000005191 phase separation Methods 0.000 description 10
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
229910052794 bromium Inorganic materials 0.000 description 9
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 9
239000012528 membrane Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
125000001425 triazolyl group Chemical group 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
AXJDEHNQPMZKOS-UHFFFAOYSA-N acetylazanium;chloride Chemical compound [Cl-].CC([NH3+])=O AXJDEHNQPMZKOS-UHFFFAOYSA-N 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
230000015572 biosynthetic process Effects 0.000 description 8
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 8
125000000623 heterocyclic group Chemical group 0.000 description 8
230000003993 interaction Effects 0.000 description 8
125000000168 pyrrolyl group Chemical group 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
125000003396 thiol group Chemical group [H]S* 0.000 description 8
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 7
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 7
125000004457 alkyl amino carbonyl group Chemical group 0.000 description 7
125000004093 cyano group Chemical group *C#N 0.000 description 7
230000000694 effects Effects 0.000 description 7
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 7
239000008101 lactose Substances 0.000 description 7
239000000843 powder Substances 0.000 description 7
239000003826 tablet Substances 0.000 description 7
229960003726 vasopressin Drugs 0.000 description 7
229910021590 Copper(II) bromide Inorganic materials 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 6
239000012153 distilled water Substances 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000002140 halogenating effect Effects 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
125000003373 pyrazinyl group Chemical group 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
125000000714 pyrimidinyl group Chemical group 0.000 description 6
230000007958 sleep Effects 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
125000003831 tetrazolyl group Chemical group 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
210000002700 urine Anatomy 0.000 description 6
VWFZSVSAZLYSFX-UHFFFAOYSA-N 1-(4-aminobenzoyl)-3,4-dihydro-2h-1-benzazepin-5-one Chemical compound C1=CC(N)=CC=C1C(=O)N1C2=CC=CC=C2C(=O)CCC1 VWFZSVSAZLYSFX-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
229920002153 Hydroxypropyl cellulose Polymers 0.000 description 5
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 5
235000011054 acetic acid Nutrition 0.000 description 5
150000001412 amines Chemical class 0.000 description 5
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 5
230000027455 binding Effects 0.000 description 5
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 5
125000000392 cycloalkenyl group Chemical group 0.000 description 5
239000001863 hydroxypropyl cellulose Substances 0.000 description 5
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
239000012907 medicinal substance Substances 0.000 description 5
WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 5
125000004043 oxo group Chemical group O=* 0.000 description 5
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
239000000047 product Substances 0.000 description 5
125000003226 pyrazolyl group Chemical group 0.000 description 5
239000011593 sulfur Substances 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 4
ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 description 4
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
208000004880 Polyuria Diseases 0.000 description 4
241000700159 Rattus Species 0.000 description 4
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
125000001931 aliphatic group Chemical group 0.000 description 4
125000003302 alkenyloxy group Chemical group 0.000 description 4
125000005092 alkenyloxycarbonyl group Chemical group 0.000 description 4
230000009435 amidation Effects 0.000 description 4
150000008064 anhydrides Chemical class 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
125000000524 functional group Chemical group 0.000 description 4
239000008187 granular material Substances 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
150000008282 halocarbons Chemical class 0.000 description 4
150000007529 inorganic bases Chemical class 0.000 description 4
229910052740 iodine Inorganic materials 0.000 description 4
239000003446 ligand Substances 0.000 description 4
KYPIASPTMDEDQB-UHFFFAOYSA-N n,2-diphenylacetamide Chemical compound C=1C=CC=CC=1NC(=O)CC1=CC=CC=C1 KYPIASPTMDEDQB-UHFFFAOYSA-N 0.000 description 4
125000002971 oxazolyl group Chemical group 0.000 description 4
125000005544 phthalimido group Chemical group 0.000 description 4
125000002098 pyridazinyl group Chemical group 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
230000028327 secretion Effects 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
239000000725 suspension Substances 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
NKRKBYFBKLDCFB-UHFFFAOYSA-N 1,2,3,4-tetrahydro-1-benzazepin-5-one Chemical compound O=C1CCCNC2=CC=CC=C12 NKRKBYFBKLDCFB-UHFFFAOYSA-N 0.000 description 3
KUCBNTWUKOGPPC-UHFFFAOYSA-N 1-(4-nitrobenzoyl)-3,4-dihydro-2h-1-benzazepin-5-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)N1C2=CC=CC=C2C(=O)CCC1 KUCBNTWUKOGPPC-UHFFFAOYSA-N 0.000 description 3
ILYSAKHOYBPSPC-UHFFFAOYSA-N 2-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=CC=CC=C1 ILYSAKHOYBPSPC-UHFFFAOYSA-N 0.000 description 3
SFWWGMKXCYLZEG-UHFFFAOYSA-N 3-methylmorpholine Chemical compound CC1COCCN1 SFWWGMKXCYLZEG-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
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RIGIWEGXTTUCIQ-UHFFFAOYSA-N hydroxy-imino-diphenyl-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1P(=O)(N)C1=CC=CC=C1 RIGIWEGXTTUCIQ-UHFFFAOYSA-N 0.000 description 1
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
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238000011534 incubation Methods 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000005929 isobutyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])OC(*)=O 0.000 description 1
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238000002955 isolation Methods 0.000 description 1
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
125000005932 isopentyloxycarbonyl group Chemical group 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
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239000004571 lime Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
235000001055 magnesium Nutrition 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052748 manganese Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
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230000002503 metabolic effect Effects 0.000 description 1
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125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
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125000002757 morpholinyl group Chemical group 0.000 description 1
JVRMUFJCFLXSMJ-UHFFFAOYSA-N n,2-diphenylbenzamide Chemical compound C=1C=CC=C(C=2C=CC=CC=2)C=1C(=O)NC1=CC=CC=C1 JVRMUFJCFLXSMJ-UHFFFAOYSA-N 0.000 description 1
125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
230000008693 nausea Effects 0.000 description 1
230000032393 negative regulation of gluconeogenesis Effects 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005933 neopentyloxycarbonyl group Chemical group 0.000 description 1
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208000009928 nephrosis Diseases 0.000 description 1
231100001027 nephrosis Toxicity 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
229960003104 ornithine Drugs 0.000 description 1
150000002916 oxazoles Chemical class 0.000 description 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001148 pentyloxycarbonyl group Chemical group 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000005561 phenanthryl group Chemical group 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000005936 piperidyl group Chemical group 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 1
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
229920000053 polysorbate 80 Polymers 0.000 description 1
229940068968 polysorbate 80 Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
208000024896 potassium deficiency disease Diseases 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000011118 potassium hydroxide Nutrition 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
238000000746 purification Methods 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000029865 regulation of blood pressure Effects 0.000 description 1
JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
125000005415 substituted alkoxy group Chemical group 0.000 description 1
125000004426 substituted alkynyl group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003464 sulfur compounds Chemical class 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
206010042772 syncope Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000001308 synthesis method Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000028016 temperature homeostasis Effects 0.000 description 1
125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005934 tert-pentyloxycarbonyl group Chemical group 0.000 description 1
VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
150000004867 thiadiazoles Chemical group 0.000 description 1
230000001256 tonic effect Effects 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
231100000397 ulcer Toxicity 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
229940124549 vasodilator Drugs 0.000 description 1
239000003071 vasodilator agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- 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
- A61P9/08—Vasodilators for multiple indications
- 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
- C07D223/16—Benzazepines; Hydrogenated benzazepines
- 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
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Hematology (AREA)
Gastroenterology & Hepatology (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Obesity (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Output Control And Ontrol Of Special Type Engine (AREA)

UA96010145A 1993-07-21 1994-07-19 A condensed benzadepine derivative, an intermediate compound for preparing thereof and a pharmaceutical composition UA64690C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP18043593		1993-07-21
PCT/JP1994/001183 WO1995003305A1 (en)	1993-07-21	1994-07-19	Fused benzazepine derivative and pharmaceutical composition containing the same

Publications (1)

Publication Number	Publication Date
UA64690C2 true UA64690C2 (en)	2004-03-15

Family

ID=16083198

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
UA96010145A UA64690C2 (en)	1993-07-21	1994-07-19	A condensed benzadepine derivative, an intermediate compound for preparing thereof and a pharmaceutical composition

Country Status (18)

Country	Link
US (2)	US5723606A (de)
EP (2)	EP0709386B1 (de)
KR (1)	KR100304331B1 (de)
CN (1)	CN1040210C (de)
AT (2)	ATE239726T1 (de)
AU (2)	AU683483B2 (de)
CA (1)	CA2167673C (de)
DE (2)	DE69432632T2 (de)
ES (2)	ES2198418T3 (de)
FI (1)	FI113178B (de)
HU (1)	HUT74582A (de)
NO (1)	NO306303B1 (de)
NZ (1)	NZ268671A (de)
PL (1)	PL177738B1 (de)
RU (1)	RU2129123C1 (de)
TW (1)	TW279163B (de)
UA (1)	UA64690C2 (de)
WO (1)	WO1995003305A1 (de)

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AU779929B2 (en) *	2000-10-04	2005-02-17	Warner-Lambert Company	Treatment of pulmonary hypertension
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US20080221084A1 (en) *	2006-10-30	2008-09-11	Otsuka Pharmaceutical Co., Ltd.	Method for reducing infarction using vasopressin antagonist compounds, and compositions and combinations therefor
US20090069295A1 (en) *	2007-09-09	2009-03-12	Protia, Llc	Deuterium-enriched conivaptan
EP2240029A4 (de) *	2008-01-07	2012-08-22	Synta Pharmaceuticals Corp	Verbindungen zur verwendung gegen entzündungs- und immunspezifische erkrankungen
WO2009102761A1 (en) *	2008-02-12	2009-08-20	Bristol-Myers Squibb Company	1,2,3-triazoles as 11-beta hydroxysteroid dehydrogenase type i inhibitors
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1994
- 1994-07-19 CN CN94192831A patent/CN1040210C/zh not_active Expired - Fee Related
- 1994-07-19 US US08/586,686 patent/US5723606A/en not_active Expired - Lifetime
- 1994-07-19 PL PL94312654A patent/PL177738B1/pl not_active IP Right Cessation
- 1994-07-19 NZ NZ268671A patent/NZ268671A/en not_active IP Right Cessation
- 1994-07-19 HU HU9600102A patent/HUT74582A/hu unknown
- 1994-07-19 AT AT94921117T patent/ATE239726T1/de not_active IP Right Cessation
- 1994-07-19 AT AT00204704T patent/ATE277003T1/de not_active IP Right Cessation
- 1994-07-19 DE DE69432632T patent/DE69432632T2/de not_active Expired - Lifetime
- 1994-07-19 ES ES94921117T patent/ES2198418T3/es not_active Expired - Lifetime
- 1994-07-19 ES ES00204704T patent/ES2228405T3/es not_active Expired - Lifetime
- 1994-07-19 DE DE69434032T patent/DE69434032T2/de not_active Expired - Lifetime
- 1994-07-19 CA CA002167673A patent/CA2167673C/en not_active Expired - Lifetime
- 1994-07-19 RU RU96105390/04A patent/RU2129123C1/ru not_active IP Right Cessation
- 1994-07-19 UA UA96010145A patent/UA64690C2/uk unknown
- 1994-07-19 EP EP94921117A patent/EP0709386B1/de not_active Expired - Lifetime
- 1994-07-19 KR KR1019960700265A patent/KR100304331B1/ko not_active Expired - Fee Related
- 1994-07-19 EP EP00204704A patent/EP1097920B1/de not_active Expired - Lifetime
- 1994-07-19 AU AU71957/94A patent/AU683483B2/en not_active Ceased
- 1994-07-19 WO PCT/JP1994/001183 patent/WO1995003305A1/ja not_active Ceased
- 1994-07-20 TW TW083106656A patent/TW279163B/zh not_active IP Right Cessation
1996
- 1996-01-19 NO NO960231A patent/NO306303B1/no not_active IP Right Cessation
- 1996-01-19 FI FI960260A patent/FI113178B/fi active
1997
- 1997-10-02 AU AU39906/97A patent/AU3990697A/en not_active Abandoned
- 1997-11-18 US US08/972,271 patent/US5856564A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
AU3990697A (en)	1997-12-18
NO960231L (no)	1996-03-21
FI113178B (fi)	2004-03-15
HUT74582A (en)	1997-01-28
EP0709386A4 (de)	1997-06-25
NO960231D0 (no)	1996-01-19
DE69434032T2 (de)	2005-09-22
EP1097920B1 (de)	2004-09-22
DE69432632T2 (de)	2004-02-19
AU7195794A (en)	1995-02-20
FI960260A0 (fi)	1996-01-19
CA2167673A1 (en)	1995-02-02
KR100304331B1 (ko)	2001-11-22
RU2129123C1 (ru)	1999-04-20
EP1097920A1 (de)	2001-05-09
AU683483B2 (en)	1997-11-13
CA2167673C (en)	2004-09-21
CN1127508A (zh)	1996-07-24
CN1040210C (zh)	1998-10-14
ATE239726T1 (de)	2003-05-15
EP0709386A1 (de)	1996-05-01
PL177738B1 (pl)	2000-01-31
NO306303B1 (no)	1999-10-18
PL312654A1 (en)	1996-04-29
DE69434032D1 (de)	2004-10-28
DE69432632D1 (de)	2003-06-12
EP0709386B1 (de)	2003-05-07
TW279163B (de)	1996-06-21
KR960703917A (ko)	1996-08-31
WO1995003305A1 (en)	1995-02-02
ATE277003T1 (de)	2004-10-15
ES2198418T3 (es)	2004-02-01
NZ268671A (en)	1997-09-22
US5723606A (en)	1998-03-03
ES2228405T3 (es)	2005-04-16
HU9600102D0 (en)	1996-03-28
US5856564A (en)	1999-01-05
FI960260A7 (fi)	1996-01-19

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