KR830009105A - 이미다조 디아제핀의 제조방법 - Google Patents
이미다조 디아제핀의 제조방법 Download PDFInfo
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- KR830009105A KR830009105A KR1019820000862A KR820000862A KR830009105A KR 830009105 A KR830009105 A KR 830009105A KR 1019820000862 A KR1019820000862 A KR 1019820000862A KR 820000862 A KR820000862 A KR 820000862A KR 830009105 A KR830009105 A KR 830009105A
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- halogen
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- trifluoromethyl
- cyano
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- 238000000034 method Methods 0.000 title claims 6
- BMGXAZCDDYTVFV-UHFFFAOYSA-N imidazo[4,5-c]diazepine Chemical compound C1=CN=NC2=NC=NC2=C1 BMGXAZCDDYTVFV-UHFFFAOYSA-N 0.000 title claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 20
- 239000001257 hydrogen Substances 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 18
- 150000002367 halogens Chemical class 0.000 claims 18
- 150000002431 hydrogen Chemical class 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- -1 dimethylene, trimethylene Chemical group 0.000 claims 6
- 125000006410 propenylene group Chemical group 0.000 claims 6
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 5
- 125000004414 alkyl thio group Chemical group 0.000 claims 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 3
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 3
- CEHKKWWXELBNPS-UHFFFAOYSA-N 1,4-benzodiazepine-1-carboxylic acid Chemical compound OC(=O)N1C=CN=CC2=CC=CC=C12 CEHKKWWXELBNPS-UHFFFAOYSA-N 0.000 claims 2
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003277 amino group Chemical group 0.000 claims 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- WXBBGXSCFXZZSI-UHFFFAOYSA-N 1h-imidazo[1,5-a][1,4]benzodiazepine-1-carboxylic acid Chemical compound N1=CC2=CC=CC=C2N2C(C(=O)O)N=CC2=C1 WXBBGXSCFXZZSI-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- LWUDDYHYYNNIQI-ZDUSSCGKSA-N bretazenil Chemical compound O=C1C2=C(Br)C=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCCN21 LWUDDYHYYNNIQI-ZDUSSCGKSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- ZXQYGBMAQZUVMI-GCMPRSNUSA-N gamma-cyhalothrin Chemical compound CC1(C)[C@@H](\C=C(/Cl)C(F)(F)F)[C@H]1C(=O)O[C@H](C#N)C1=CC=CC(OC=2C=CC=CC=2)=C1 ZXQYGBMAQZUVMI-GCMPRSNUSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- NEOSNTOOTGEEQK-LBPRGKRZSA-N tert-butyl (7S)-11-oxo-13-(trifluoromethyl)-2,4,10-triazatetracyclo[10.4.0.02,6.07,10]hexadeca-1(16),3,5,12,14-pentaene-5-carboxylate Chemical compound C([C@H]1C=2N3C=NC=2C(=O)OC(C)(C)C)CN1C(=O)C1=C3C=CC=C1C(F)(F)F NEOSNTOOTGEEQK-LBPRGKRZSA-N 0.000 claims 1
- WNNMAVYBIDQVON-ZDUSSCGKSA-N tert-butyl (7S)-12-oxo-14-(trifluoromethyl)-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate Chemical compound C([C@H]1C=2N3C=NC=2C(=O)OC(C)(C)C)CCN1C(=O)C1=C3C=CC=C1C(F)(F)F WNNMAVYBIDQVON-ZDUSSCGKSA-N 0.000 claims 1
- NPRHJHZWJXUBAC-ZDUSSCGKSA-N tert-butyl (7S)-14-chloro-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate Chemical compound O=C1C2=C(Cl)C=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCCN21 NPRHJHZWJXUBAC-ZDUSSCGKSA-N 0.000 claims 1
- KWYPSUSXIWCZBB-AWEZNQCLSA-N tert-butyl (7S)-14-methyl-12-oxo-2,4,11-triazatetracyclo[11.4.0.02,6.07,11]heptadeca-1(17),3,5,13,15-pentaene-5-carboxylate Chemical compound O=C1N2CCC[C@H]2C2=C(C(=O)OC(C)(C)C)N=CN2C2=C1C(C)=CC=C2 KWYPSUSXIWCZBB-AWEZNQCLSA-N 0.000 claims 1
- IQSYKHVFMYGJER-UHFFFAOYSA-N tert-butyl 2-isocyanoacetate Chemical compound CC(C)(C)OC(=O)C[N+]#[C-] IQSYKHVFMYGJER-UHFFFAOYSA-N 0.000 claims 1
- BWVJHTLMZSXUFK-LBPRGKRZSA-N tert.butyl (s)-8-chloro-12,12a-dihydro-9-oxo-9h,11h-azeto[2,1-c]imidazo[1,5-a][1,4]benzodiazepine-1-carboxylate Chemical compound O=C1C2=C(Cl)C=CC=C2N2C=NC(C(=O)OC(C)(C)C)=C2[C@@H]2CCN21 BWVJHTLMZSXUFK-LBPRGKRZSA-N 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
- C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
-
- 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
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/38—Oxygen atoms in positions 2 and 3, e.g. isatin
-
- 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
- C07D471/12—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 three hetero rings
- C07D471/14—Ortho-condensed systems
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- 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
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- 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
- C07D487/12—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 three hetero rings
- C07D487/14—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
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- 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
- C07D495/12—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 three hetero rings
- C07D495/14—Ortho-condensed systems
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (21)
- a) 염기의 존재하에서 일반식 II의 화합물을 3급-부틸이소시아노아세테이트와 반응시키거나 b) 일반식 III의 카복실산을 상응하는 3급-부틸에스테르로 전환시키거나 c) 일반식 Ia 화합물에서 할로겐원자를 시아노기로 치환하거나 R21이 할로겐을 나타내면 이를 저급알킬티오기로 치환시키거나 d) 일반식 b 화합물에서 아미노기를 수소, 할로겐원자, 시아노 또는 니트로기로 치환시키거나 e) 일반식 Ic 화합물을 아미노기에 대해 α-위치에서 할로겐화 시키거나 f) 일반식 Id 화합물에서 저급알킬티오기를 저급알킬설피닐 또는 저급알킬설포닐기로 산화시키거나 저급알킬설피닐기를 저급알킬설포닐기로 산화시키고 g) 경우에 따라 수득한 일반식 I화합물을 약제학적으로 허용할 수 있는 산부가염으로 전환시킴을 특징으로 하여 일반식 I의 이미다조디아제핀 및 그의 약제학적으로 허용할 수 있는 산부가염을 제조하는 방법.상기식에서, A는 α 및 β로서 나타낸 두 탄소원자와 함께 하기그룹을 나타내며B는 디메틸렌, 트리메틸렌 또는 프로페닐렌을 나타내고, R1은 수소, 할로겐, 트리플루오로메틸, 아미노, 니트로, 시아노 또는 저급알킬을 나타내며, R2는 수소, 할로겐, 트리플루오메틸, 아미노, 니트로, 시아노, 저급알킬, 저급알콕시, 저급알킬티오, 저급알킬설피닐, 또는 저급알킬설포닐을 나타내며(단 일반식 III 화합물에서 A가 (a)그룹이면 R1및/또는 R2은아미노를 나타내지 않는다), γ로서 나타낸 탄소원자는 (S) 또는 (R,S)-배위를 가니며, X는 이탈기를 나타내며, R11은 할로겐 이고 R21은 수소, 트리플루오로메틸, 아미노, 니트로, 시아노 또는 저급알킬을 나타내거나 또는 R11이 수소, 트리플루오로메틸, 아미노, 니트로, 시아노 또는 저급알킬을 나타내고 R21은 할로겐을 나타내며 R12가 아미노를 나타내고 R22는 수소, 할로겐트리플루오로메틸, 니트로, 시아노 또는 저급알킬을 나타내거나 또는 R12가 수소, 할로겐, 트리플루오로메틸, 니트로, 시아노 또는 저급알킬을 나타내고 R22는 아미노를 나타내고, R13와 R23중의 하나가 아미노를 나타내면 다른 하나는 수소를 나타내며, R14는 수소, 할로겐, 트리플루오로메틸, 니트로, 시아노 또는 저급알킬을 나타내고, R24는 저급알킬티오 또는 저급알킬설피닐을 나타낸다.
- 제1항중의 a),b) 또는 c)에 있어서, A가 제1항에서 정의된 (a)그룹을 나타내고, R1및 R2중의 하나가 수소를 나타내고 다른하나는 니트로 또는 시아노를 나타내며, B는 디메틸렌, 트리메틸렌 또는 프로페닐렌을 나타내고 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항중의 a),b) 또는 g)에 있어서, A가 제1항에서 정의된 (a)그룹 또는 (d)그룹을 나타내고, B는 디메틸렌을 나타내며 R1은 수소, 할로겐, 트리플루오로메틸 나타내고 R2는 수소, 할로겐, 트리플루오로메틸 또는 저급알킬을 나타내며 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항 a)에 있어서, A가 제1항에서 정의된 (a)또는 (d)그룹을 나타내며 B는 트리메틸렌 또는 프로페닐렌을 나타내고 R1은 수소, 할로겐 또는 트리플루오로메틸을 나타내며 R2는 수소, 할로겐 트리플루오로메틸 또는 저급알킬을 나타내고 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항중의 a),b) 또는 g)에 있어서, A가 제1항에서 정의된 (b)그룹 또는 (c)그룹을 나타내고 B가 디메틸렌, 트리메틸렌 또는 프로페닐렌을 나타내며 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항중의 a),b),c) 또는 (b)에 있어서, A가 제1항에서 정의된 (a)그룹을 나타내고 B는 디메틸렌트리메틸렌 또는 프로페닐렌을 나타내며, R1이 저급알킬을 나타내고, R2가 수소, 할로겐, 트리플루오로메틸, 니트로, 시아노, 또는 저급알킬을 나타내거나 또는 R1및 R2중의 하나가 니트로 또는 시아노를 나타내고 다른 하나는 할로겐, 트리플루오로메틸, 니트로, 시아노 또는 저급알킬을 나타내며 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항중의 b) 또는 (g)에 있어서, A가 제1항에서 정의된 (a)그룹 또는 (d)그룹을 나타내며 B는 트리메틸렌 또는 프로페닐렌을 나타내고 R1은 수소, 할로겐 또는 트리플루오로메틸을 나타내며 R2는 수소, 할로겐 트리플루오로메틸 또는 저급알킬을 나타내고 γ로서 나타낸 탄소원자는 (S)-또는 (R,S)-배위를 가짐이 특징인 방법.
- 제1항에 있어서, A가 제1항에서 정의된 (a),(b),(c) 또는 (d)그룹을 나타내고, R1은 수소, 아미노 또는 할로겐을 나타내며 R2는 수소, 할로겐, 트리플루오로메틸, 저급알킬, 시아노, 니트로, 아미노, 저급알콕시, 저급알킬티오, 저급알킬설피닐 또는 저급알킬설포닐을 나타냄이 특징인 방법.
- 제8항에서 있어서, A가 제1항에서 정의된 (a)그룹을 나타내고 R1은 수소 또는 할로겐을 나타내며 R2는 할로겐, 트리플루오로메틸 또는 저급알킬을 나타냄이 특징인 방법.
- 제1항, 제8항 및 제9항중의 어느하나에 있어서, B가 디메틸렌 또는 트리메틸렌을 나타냄이 특징인 방법.
- 제1항 및 제8항 내지 제10항중의 어느 하나에 있어서, γ로서 나타낸 탄소원자가 (S)-배위를 가짐이 특징인 방법.
- 제1항에 있어서, 3급-부틸(S)-12,12a-디하이드로-9-옥소-8-트리플루오로메틸-9H,11H-아제토[2,1-c]이미다조[1,5-a][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-12,12a-디하이드로-9-메틸-9-옥소-9H,11H-아제토[2,1-c]이미다조[1,5-a][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-8-클로로-8-플루오로-11,12,13,13a-테트라하이드로-9-옥소-9H-이미다조[1,5-a]피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-8-클로로-11,12,13,13a-테트라하이드로-9-옥소-9H-이미다조[1,5-a]피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-8-에틸-11,12,13,13a-테트라하이드로-9-옥소-9H-이미다조[1,5-a]피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-11,12,13,13a-테트라하이드로-9-옥소-8-트리플루오로메틸-9H-이미다조[1,5-a]피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-8-브로모-11,12,13,13a-테트라하이드로-9-옥소-9H-이미다조[1,5-a]피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-11,12,13,13a-테트라하이드로-8-요도-9-옥소-9H-이미다조[1,5-a]-피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-8-클로로-12,12a-디하이드로-9-옥소-9H,11H-아제토[2,1-c]이미다조[1,5-a][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.
- 제1항에 있어서, 3급-부틸(S)-11,12,13,13a-테트라하이드로-8-메틸-9-옥소-9H-이미다조[1,5-a]-피롤로[2,1-c][1,4]벤조디아제핀-1-카복실레이트가 제조되는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH133981 | 1981-02-27 | ||
| CH134181 | 1981-02-27 | ||
| CH134281 | 1981-02-27 | ||
| CH133881 | 1981-02-27 | ||
| CH1341 | 1981-02-27 | ||
| CH1342 | 1981-02-27 | ||
| CH1339 | 1981-02-27 | ||
| CH1338 | 1981-02-27 | ||
| CH3675 | 1981-06-04 | ||
| CH367581 | 1981-06-04 | ||
| CH7934 | 1981-12-11 | ||
| CH793481 | 1981-12-11 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR830009105A true KR830009105A (ko) | 1983-12-17 |
| KR890002624B1 KR890002624B1 (ko) | 1989-07-20 |
Family
ID=27543637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR8200862A KR890002624B1 (ko) | 1981-02-27 | 1982-02-26 | 이미다조 디아제핀의 제조방법 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4353827A (ko) |
| EP (1) | EP0059391B1 (ko) |
| KR (1) | KR890002624B1 (ko) |
| AU (1) | AU551891B2 (ko) |
| BR (1) | BR8201024A (ko) |
| CA (1) | CA1185602A (ko) |
| CS (1) | CS247064B2 (ko) |
| DE (1) | DE3263633D1 (ko) |
| DK (1) | DK168073B1 (ko) |
| FI (1) | FI73430C (ko) |
| HK (1) | HK23288A (ko) |
| IE (1) | IE52543B1 (ko) |
| IL (1) | IL65056A0 (ko) |
| MC (1) | MC1442A1 (ko) |
| NO (1) | NO157620C (ko) |
| NZ (1) | NZ199793A (ko) |
| PH (1) | PH19881A (ko) |
| PT (1) | PT74504B (ko) |
| YU (1) | YU45860B (ko) |
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| MC1528A1 (fr) * | 1982-07-21 | 1984-04-13 | Hoffmann La Roche | Imidazobenzodiazepines |
| CS249146B2 (en) * | 1984-01-19 | 1987-03-12 | Hoffmann La Roche | Method of new imidazodiazepine's derivatives production |
| DK174086D0 (da) * | 1986-04-16 | 1986-04-16 | Ferrosan As | Nye benzodiazepinderivater samt fremgangsmaade til fremstilling af samme |
| CA1327008C (en) * | 1988-01-15 | 1994-02-15 | Walter Merz | Anti-psychotic imidazobenzodiazepine |
| CA1312825C (en) * | 1988-01-27 | 1993-01-19 | F. Hoffmann-La Roche Ag | Prevention or interruption of panic states with an imidazobenzodiazepine |
| CA2015336A1 (en) * | 1989-05-19 | 1990-11-19 | F. Hoffmann-La Roche Ag | Imidazodiazepines for the treatment of neurological symptoms |
| CA2055308A1 (en) * | 1990-11-29 | 1992-05-30 | Roman Amrein | Imidazobenzodiazepine for the treatment of sleep disorders |
| JO2259B1 (en) * | 1999-05-12 | 2004-10-07 | اف. هوفمان- لاروش أيه جي | Method for the manufacture of diazapine derivatives |
| US7678818B2 (en) * | 2006-02-07 | 2010-03-16 | Hoffmann-La Roche Inc. | Anthranilamide and 2-amino-heteroarene-carboxamide compounds |
| US20090054412A1 (en) * | 2007-08-20 | 2009-02-26 | John Alan Kemp | Treatment of Sleep Disorders |
| BRPI0815579A2 (pt) | 2007-08-20 | 2015-02-18 | Evotec Neurosciences Gmbh | Tratamento de distúrbio do sono |
| JP5870400B2 (ja) | 2010-04-15 | 2016-03-01 | シアトル ジェネティクス，インコーポレーテッド | 標的化ピロロベンゾジアゼピンコンジュゲート |
| EP2558475A1 (en) | 2010-04-15 | 2013-02-20 | Spirogen Sàrl | Pyrrolobenzodiazepines used to treat proliferative diseases |
| AU2012311505B2 (en) | 2011-09-20 | 2016-09-29 | Medimmune Limited | Pyrrolobenzodiazepines as unsymmetrical dimeric PBD compounds for inclusion in targeted conjugates |
| CN103997893B (zh) | 2011-10-14 | 2019-04-12 | 西雅图基因公司 | 吡咯并苯并二氮杂卓和靶向结合物 |
| KR101891859B1 (ko) | 2011-10-14 | 2018-08-24 | 메디뮨 리미티드 | 피롤로벤조디아제핀 |
| WO2013055990A1 (en) | 2011-10-14 | 2013-04-18 | Seattle Genetics, Inc. | Pyrrolobenzodiazepines and targeted conjugates |
| CN110183470A (zh) | 2011-10-14 | 2019-08-30 | 麦迪穆有限责任公司 | 吡咯并苯并二氮杂卓 |
| CN103374000B (zh) * | 2012-04-13 | 2015-11-11 | 中国科学院广州生物医药与健康研究院 | 嘧啶并二氮杂卓类化合物及其药用组合物和应用 |
| EP2906249B1 (en) | 2012-10-12 | 2018-06-27 | MedImmune Limited | Synthesis and intermediates of pyrrolobenzodiazepine derivatives for conjugation |
| EP2906298B1 (en) | 2012-10-12 | 2018-10-03 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| PT2906296T (pt) | 2012-10-12 | 2018-06-01 | Medimmune Ltd | Conjugados de pirrolobenzodiazepina-anticorpo |
| EP2906297B1 (en) | 2012-10-12 | 2017-12-06 | ADC Therapeutics SA | Pyrrolobenzodiazepine-antibody conjugates |
| LT2906253T (lt) | 2012-10-12 | 2018-10-10 | Adc Therapeutics Sa | Pirolobenzodiazepino-anti-psma antikūno konjugatas |
| CA2887899C (en) | 2012-10-12 | 2020-03-31 | Adc Therapeutics Sarl | Pyrrolobenzodiazepine-anti-cd22 antibody conjugates |
| ME03486B (me) | 2012-10-12 | 2020-01-20 | Medimmune Ltd | Pirolobenzodiazepini i njihovi konjugati |
| CA3060520C (en) | 2012-10-12 | 2022-05-17 | Medimmune Limited | Pyrrolobenzodiazepines and conjugates thereof |
| ES2680153T3 (es) | 2012-10-12 | 2018-09-04 | Adc Therapeutics Sa | Conjugados de anticuerpos anti-PSMA-pirrolobenzodiazepinas |
| GB201317982D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| GB201317981D0 (en) | 2013-10-11 | 2013-11-27 | Spirogen Sarl | Pyrrolobenzodiazepines and conjugates thereof |
| EP3054986B1 (en) | 2013-10-11 | 2019-03-20 | Medimmune Limited | Pyrrolobenzodiazepine-antibody conjugates |
| WO2015052534A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| WO2015052532A1 (en) | 2013-10-11 | 2015-04-16 | Spirogen Sàrl | Pyrrolobenzodiazepine-antibody conjugates |
| GB201416112D0 (en) | 2014-09-12 | 2014-10-29 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| CA2968447A1 (en) | 2014-11-25 | 2016-06-02 | Adc Therapeutics Sa | Pyrrolobenzodiazepine-antibody conjugates and their use to treat neoplasms |
| GB201506411D0 (en) | 2015-04-15 | 2015-05-27 | Bergenbio As | Humanized anti-axl antibodies |
| GB201506402D0 (en) | 2015-04-15 | 2015-05-27 | Berkel Patricius H C Van And Howard Philip W | Site-specific antibody-drug conjugates |
| GB201601431D0 (en) | 2016-01-26 | 2016-03-09 | Medimmune Ltd | Pyrrolobenzodiazepines |
| GB201602359D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201602356D0 (en) | 2016-02-10 | 2016-03-23 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201607478D0 (en) | 2016-04-29 | 2016-06-15 | Medimmune Ltd | Pyrrolobenzodiazepine Conjugates |
| GB201617466D0 (en) | 2016-10-14 | 2016-11-30 | Medimmune Ltd | Pyrrolobenzodiazepine conjugates |
| GB201702031D0 (en) | 2017-02-08 | 2017-03-22 | Medlmmune Ltd | Pyrrolobenzodiazepine-antibody conjugates |
| KR20200032243A (ko) | 2017-02-08 | 2020-03-25 | 에이디씨 테라퓨틱스 에스에이 | 피롤로벤조디아제핀-항체 컨주게이트 |
| PT3612537T (pt) | 2017-04-18 | 2022-08-29 | Medimmune Ltd | Conjugados de pirrolobenzodiazepina |
| EP3612234B1 (en) | 2017-04-20 | 2024-03-13 | ADC Therapeutics SA | Combination therapy with an anti-axl antibody-drug conjugate |
| UA127900C2 (uk) | 2017-06-14 | 2024-02-07 | Ейдісі Терапьютікс Са | Схема дозування для введення adc до cd19 |
| DK3668874T3 (da) | 2017-08-18 | 2022-02-14 | Medimmune Ltd | Pyrrolobenzodiazepin-konjugater |
| GB201803342D0 (en) | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| GB201806022D0 (en) | 2018-04-12 | 2018-05-30 | Medimmune Ltd | Pyrrolobenzodiazepines and conjugates thereof |
| EP4069369A4 (en) * | 2019-12-06 | 2024-02-14 | Schroedinger Inc | CYCLIC COMPOUNDS AND METHODS OF USE THEREOF |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3933794A (en) * | 1971-08-04 | 1976-01-20 | The Upjohn Company | 2-(2-Alkynylamino)-3H-1,4-benzodiazepines |
| GB1600600A (en) * | 1977-03-10 | 1981-10-21 | Diamond Shamrock Chem | Plasticiser compositions for use with synthetic resin polymers |
| US4118386A (en) * | 1977-04-04 | 1978-10-03 | Hoffmann-La Roche Inc. | Synthesis of imidazo[1,5-a]diazepine-3-carboxylates |
| CA1143728A (en) * | 1979-10-04 | 1983-03-29 | Max Gerecke | Imidazodiazepine derivatives |
-
1982
- 1982-01-21 CA CA000394685A patent/CA1185602A/en not_active Expired
- 1982-02-10 PH PH26851A patent/PH19881A/en unknown
- 1982-02-17 CS CS821081A patent/CS247064B2/cs unknown
- 1982-02-18 US US06/349,801 patent/US4353827A/en not_active Expired - Lifetime
- 1982-02-19 DK DK074282A patent/DK168073B1/da not_active IP Right Cessation
- 1982-02-19 IL IL65056A patent/IL65056A0/xx not_active IP Right Cessation
- 1982-02-19 EP EP82101273A patent/EP0059391B1/de not_active Expired
- 1982-02-19 DE DE8282101273T patent/DE3263633D1/de not_active Expired
- 1982-02-22 AU AU80669/82A patent/AU551891B2/en not_active Expired
- 1982-02-22 NZ NZ199793A patent/NZ199793A/en unknown
- 1982-02-25 FI FI820647A patent/FI73430C/fi not_active IP Right Cessation
- 1982-02-25 MC MC821577A patent/MC1442A1/xx unknown
- 1982-02-26 BR BR8201024A patent/BR8201024A/pt unknown
- 1982-02-26 IE IE421/82A patent/IE52543B1/en not_active IP Right Cessation
- 1982-02-26 PT PT74504A patent/PT74504B/pt unknown
- 1982-02-26 KR KR8200862A patent/KR890002624B1/ko not_active IP Right Cessation
- 1982-02-26 YU YU43682A patent/YU45860B/sh unknown
- 1982-02-26 NO NO820622A patent/NO157620C/no unknown
-
1988
- 1988-03-30 HK HK232/88A patent/HK23288A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| MC1442A1 (fr) | 1982-12-06 |
| NO157620C (no) | 1988-04-20 |
| YU45860B (sh) | 1992-09-07 |
| AU551891B2 (en) | 1986-05-15 |
| PH19881A (en) | 1986-08-13 |
| NO157620B (no) | 1988-01-11 |
| YU43682A (en) | 1988-08-31 |
| NZ199793A (en) | 1985-08-30 |
| FI73430C (fi) | 1987-10-09 |
| EP0059391B1 (de) | 1985-05-08 |
| IL65056A0 (en) | 1982-04-30 |
| DK168073B1 (da) | 1994-01-31 |
| CA1185602A (en) | 1985-04-16 |
| US4353827A (en) | 1982-10-12 |
| EP0059391A1 (de) | 1982-09-08 |
| DE3263633D1 (en) | 1985-06-13 |
| FI820647L (fi) | 1982-08-28 |
| NO820622L (no) | 1982-08-30 |
| BR8201024A (pt) | 1983-01-04 |
| PT74504A (en) | 1982-03-01 |
| CS247064B2 (en) | 1986-11-13 |
| FI73430B (fi) | 1987-06-30 |
| HK23288A (en) | 1988-04-08 |
| KR890002624B1 (ko) | 1989-07-20 |
| AU8066982A (en) | 1982-09-02 |
| IE52543B1 (en) | 1987-12-09 |
| DK74282A (da) | 1982-08-28 |
| IE820421L (en) | 1982-08-27 |
| PT74504B (en) | 1984-11-26 |
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