DK167018B1 - 3-furylamino-1-benzazepiner samt fremgangsmaade til fremstillig deraf - Google Patents

3-furylamino-1-benzazepiner samt fremgangsmaade til fremstillig deraf Download PDF

Info

Publication number: DK167018B1
Authority: DK; Denmark
Prior art keywords: formula; compound; carboxy; furylamino; preparation
Prior art date: 1986-05-28

Application number

DK271087A

Other languages

Danish (da)

English (en)

Other versions

DK271087D0 (da

DK271087A (da

Inventor

Stephen K Boyer

Original Assignee

Ciba Geigy Ag

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.)

1986-05-28

Filing date

1987-05-27

Publication date

1993-08-16

1987-05-27 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1987-05-27 Publication of DK271087D0 publication Critical patent/DK271087D0/da

1987-11-29 Publication of DK271087A publication Critical patent/DK271087A/da

1993-08-16 Application granted granted Critical

1993-08-16 Publication of DK167018B1 publication Critical patent/DK167018B1/da

Links

238000000034 method Methods 0.000 title claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 27
150000001875 compounds Chemical class 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
YNVWHVWDCJOFHH-UHFFFAOYSA-N O1C=C(C=C1)NC=1NC2=C(C=CC1)C=CC=C2 Chemical class O1C=C(C=C1)NC=1NC2=C(C=CC1)C=CC=C2 YNVWHVWDCJOFHH-UHFFFAOYSA-N 0.000 claims description 6
YQOUMBVFEWZLME-VOTSOKGWSA-N (e)-2-oxo-4-phenylbut-3-enoic acid Chemical compound OC(=O)C(=O)\C=C\C1=CC=CC=C1 YQOUMBVFEWZLME-VOTSOKGWSA-N 0.000 claims description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
239000000047 product Substances 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 10
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
239000005541 ACE inhibitor Substances 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 6
239000012043 crude product Substances 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
238000005984 hydrogenation reaction Methods 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
150000005690 diesters Chemical class 0.000 description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
239000002002 slurry Substances 0.000 description 2
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ZRVKEVKIXFZQMC-UHFFFAOYSA-N 2-(azepin-1-yl)acetic acid Chemical compound OC(=O)CN1C=CC=CC=C1 ZRVKEVKIXFZQMC-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
-1 benzyl hydroxy function Chemical group 0.000 description 1
125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
CRPCSEZDTZRRFH-NSHDSACASA-N ethyl 2-[(3s)-3-amino-2-oxo-4,5-dihydro-3h-1-benzazepin-1-yl]acetate Chemical compound C1C[C@H](N)C(=O)N(CC(=O)OCC)C2=CC=CC=C21 CRPCSEZDTZRRFH-NSHDSACASA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
239000012535 impurity Substances 0.000 description 1
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000009738 saturating Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 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 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000007306 turnover Effects 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

DK271087A 1986-05-28 1987-05-27 3-furylamino-1-benzazepiner samt fremgangsmaade til fremstillig deraf DK167018B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86822786A	1986-05-28	1986-05-28
US86822786		1986-05-28

Publications (3)

Publication Number	Publication Date
DK271087D0 DK271087D0 (da)	1987-05-27
DK271087A DK271087A (da)	1987-11-29
DK167018B1 true DK167018B1 (da)	1993-08-16

Family

ID=25351280

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DK271087A DK167018B1 (da)	1986-05-28	1987-05-27	3-furylamino-1-benzazepiner samt fremgangsmaade til fremstillig deraf
DK130992A DK169322B1 (da)	1986-05-28	1992-10-27	Fremgangsmåde til fremstilling af 1-carboxymethyl-3-amino-2,3,4,5-tetrahydro-1H-(1)-benzazepin-2-oner eller salte deraf med syrer eller baser

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DK130992A DK169322B1 (da)	1986-05-28	1992-10-27	Fremgangsmåde til fremstilling af 1-carboxymethyl-3-amino-2,3,4,5-tetrahydro-1H-(1)-benzazepin-2-oner eller salte deraf med syrer eller baser

Country Status (10)

Country	Link
AT (1)	AT395008B (el)
CA (1)	CA1284499C (el)
DD (2)	DD263771A5 (el)
DK (2)	DK167018B1 (el)
ES (1)	ES2005880A6 (el)
FI (1)	FI88723C (el)
GR (1)	GR870819B (el)
HU (2)	HU199832B (el)
NO (1)	NO170489C (el)
PT (1)	PT84947B (el)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
KR20010043558A (ko) *	1998-05-13	2001-05-25	한센 핀 베네드, 안네 제헤르, 웨이콥 마리안느	감수분열 조절 화합물

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4410520A (en) *	1981-11-09	1983-10-18	Ciba-Geigy Corporation	3-Amino-[1]-benzazepin-2-one-1-alkanoic acids
US4473575A (en) *	1982-07-19	1984-09-25	Ciba-Geigy Corporation	3-Amino-(1)-benzazepin-2-one-1-alkanoic acids

1987
- 1987-05-25 FI FI872306A patent/FI88723C/fi not_active IP Right Cessation
- 1987-05-25 GR GR870819A patent/GR870819B/el unknown
- 1987-05-26 DD DD30316087A patent/DD263771A5/de not_active IP Right Cessation
- 1987-05-26 CA CA000537949A patent/CA1284499C/en not_active Expired - Lifetime
- 1987-05-26 DD DD32522387A patent/DD278787A5/de not_active IP Right Cessation
- 1987-05-26 PT PT8494787A patent/PT84947B/pt unknown
- 1987-05-27 DK DK271087A patent/DK167018B1/da active IP Right Grant
- 1987-05-27 HU HU244487A patent/HU199832B/hu unknown
- 1987-05-27 NO NO872226A patent/NO170489C/no unknown
- 1987-05-27 AT AT135787A patent/AT395008B/de not_active IP Right Cessation
- 1987-05-27 HU HU657987A patent/HU199807B/hu unknown
- 1987-05-28 ES ES8701572A patent/ES2005880A6/es not_active Expired
1992
- 1992-10-27 DK DK130992A patent/DK169322B1/da active IP Right Grant

Also Published As

Publication number	Publication date
PT84947A (en)	1987-06-01
FI872306A0 (fi)	1987-05-25
NO170489C (no)	1992-10-21
FI872306L (fi)	1987-11-29
HU199832B (en)	1990-03-28
NO872226D0 (no)	1987-05-27
DK271087D0 (da)	1987-05-27
ATA135787A (de)	1992-01-15
PT84947B (pt)	1990-02-08
GR870819B (en)	1987-09-25
NO170489B (no)	1992-07-13
DK130992D0 (da)	1992-10-27
FI88723C (fi)	1993-06-28
FI88723B (fi)	1993-03-15
DK130992A (da)	1992-10-27
DK271087A (da)	1987-11-29
DD263771A5 (de)	1989-01-11
DD278787A5 (de)	1990-05-16
HUT44534A (en)	1988-03-28
AT395008B (de)	1992-08-25
DK169322B1 (da)	1994-10-10
ES2005880A6 (es)	1989-04-01
NO872226L (no)	1987-11-30
HU199807B (en)	1990-03-28
CA1284499C (en)	1991-05-28

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Legal Events

Date	Code	Title	Description
1993-08-16	B1	Patent granted (law 1993)