SK285818B6 - Spôsob prípravy N-(1,1-dimetyletyl)-4-[[5'-etoxy-4-cis-[2-(4- morfolino)etoxy]-2'-oxospiro[cyklohexán-1,3'[3H]indol]-1'(2'H)- yl]-sulfonyl]-3-metoxybenzamidu a jeho solí - Google Patents

Spôsob prípravy N-(1,1-dimetyletyl)-4-[[5'-etoxy-4-cis-[2-(4- morfolino)etoxy]-2'-oxospiro[cyklohexán-1,3'[3H]indol]-1'(2'H)- yl]-sulfonyl]-3-metoxybenzamidu a jeho solí Download PDF

Info

Publication number: SK285818B6
Authority: SK; Slovakia
Prior art keywords: ethoxy; formula; compound; preparation; salts
Prior art date: 1999-07-15

Application number

SK46-2002A

Other languages

English (en)

Slovak (sk)

Other versions

SK462002A3 (en

Inventor

Gergely H�Ja

�Va Csik�S

Tak�Csy T�Nde Er�Sn�

Csaba G�Nczi

Judit Hal�Sz

Istv�N Hermecz

Csilla Majl�Th

Lajos Nagy

Csutor Andrea S�Nt�N�

P�Ter S�Rosi

K�Lm�N Simon

Tiborn Szomor

Gy�Rgyn� Szvoboda

Original Assignee

Sanofi-Aventis

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.)

1999-07-15

Filing date

2000-07-13

Publication date

2007-09-06

2000-07-13 Application filed by Sanofi-Aventis filed Critical Sanofi-Aventis

2003-03-04 Publication of SK462002A3 publication Critical patent/SK462002A3/sk

2007-09-06 Publication of SK285818B6 publication Critical patent/SK285818B6/sk

Links

150000003839 salts Chemical class 0.000 title claims abstract description 11
238000000034 method Methods 0.000 title claims abstract description 9
238000002360 preparation method Methods 0.000 title claims abstract description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 14
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 10
230000001131 transforming effect Effects 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
238000004090 dissolution Methods 0.000 description 2
239000000203 mixture Substances 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
FQBFGERKZZFZNX-UHFFFAOYSA-N 4-(tert-butylcarbamoyl)-2-methoxybenzenesulfonyl chloride Chemical compound COC1=CC(C(=O)NC(C)(C)C)=CC=C1S(Cl)(=O)=O FQBFGERKZZFZNX-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
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 description 1
102000002852 Vasopressins Human genes 0.000 description 1
108010004977 Vasopressins Proteins 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
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 description 1
-1 beta-morpholinoethoxy Chemical group 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
JXDYKVIHCLTXOP-UHFFFAOYSA-N isatin Chemical compound C1=CC=C2C(=O)C(=O)NC2=C1 JXDYKVIHCLTXOP-UHFFFAOYSA-N 0.000 description 1
TWHXWYVOWJCXSI-UHFFFAOYSA-N phosphoric acid;hydrate Chemical compound O.OP(O)(O)=O TWHXWYVOWJCXSI-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000002904 solvent Substances 0.000 description 1
125000003003 spiro group Chemical group 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
239000000725 suspension Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
229960003726 vasopressin Drugs 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/96—Spiro-condensed ring systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Diabetes (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Endocrinology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Indole Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

SK46-2002A 1999-07-15 2000-07-13 Spôsob prípravy N-(1,1-dimetyletyl)-4-[[5'-etoxy-4-cis-[2-(4- morfolino)etoxy]-2'-oxospiro[cyklohexán-1,3'[3H]indol]-1'(2'H)- yl]-sulfonyl]-3-metoxybenzamidu a jeho solí SK285818B6 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
HU9902376A HUP9902376A3 (en)	1999-07-15	1999-07-15	Process for producing n-(1,1-dimethyl)-4-[[s'-ethoxi-4-cis-[2-(4-morpholino)-ethoxi]-2'-oxospiro[cyclohexane-1,3'-[3h]indole]-1'(2'h)yl]-sulfonyl]-3-methoxybenzamide and its salts
PCT/HU2000/000078 WO2001005791A2 (en)	1999-07-15	2000-07-13	NEW PROCESS FOR THE PREPARATION OF N-(1,1-DIMETHYLETHYL)-4-[[5'-ETHOXY-4-cis-[2-(4-MORFOLINO)ETHOXY]-2'-OXOSPIRO[CYCLOHEXAN-1,3'-[H]INDOL]-1'(2'H)-yl]-SULFONYL]-3-METHOXYBENZAMIDE AND ITS SALTS

Publications (2)

Publication Number	Publication Date
SK462002A3 SK462002A3 (en)	2003-03-04
SK285818B6 true SK285818B6 (sk)	2007-09-06

Family

ID=89998742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK46-2002A SK285818B6 (sk)	1999-07-15	2000-07-13	Spôsob prípravy N-(1,1-dimetyletyl)-4-[[5'-etoxy-4-cis-[2-(4- morfolino)etoxy]-2'-oxospiro[cyklohexán-1,3'[3H]indol]-1'(2'H)- yl]-sulfonyl]-3-metoxybenzamidu a jeho solí

Country Status (17)

Country	Link
US (1)	US6600039B1 (cs)
EP (1)	EP1196381B1 (cs)
JP (1)	JP2003505389A (cs)
CN (1)	CN1174969C (cs)
AT (1)	ATE264842T1 (cs)
AU (1)	AU6308100A (cs)
BR (1)	BR0012425A (cs)
CA (1)	CA2378087C (cs)
CZ (1)	CZ2002145A3 (cs)
DE (1)	DE60010083T2 (cs)
ES (1)	ES2216927T3 (cs)
HR (1)	HRP20020142B1 (cs)
HU (1)	HUP9902376A3 (cs)
MX (1)	MXPA01013344A (cs)
PL (1)	PL195787B1 (cs)
SK (1)	SK285818B6 (cs)
WO (1)	WO2001005791A2 (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4823614A (en) *	1986-04-28	1989-04-25	Dahlin Erik B	Coriolis-type mass flowmeter
ATE295350T1 (de) *	2001-07-31	2005-05-15	Sanofi Aventis	Verfahren zur herstellung von 3 spiro'cyclohexan- 1,3'-'3höindolin-2'-onöderivaten

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2740136B1 (fr)	1995-10-24	1998-01-09	Sanofi Sa	Derives d'indolin-2-one, procede pour leur preparation et les compositions pharmaceutiques les contenant
FR2757157B1 (fr) *	1996-12-13	1999-12-31	Sanofi Sa	Derives d'indolin-2-one, procede pour leur preparation et compositions pharmaceutiques les contenant

1999
- 1999-07-15 HU HU9902376A patent/HUP9902376A3/hu unknown
2000
- 2000-07-13 HR HR20020142A patent/HRP20020142B1/xx not_active IP Right Cessation
- 2000-07-13 CA CA002378087A patent/CA2378087C/en not_active Expired - Fee Related
- 2000-07-13 CZ CZ2002145A patent/CZ2002145A3/cs unknown
- 2000-07-13 DE DE60010083T patent/DE60010083T2/de not_active Expired - Lifetime
- 2000-07-13 AU AU63081/00A patent/AU6308100A/en not_active Abandoned
- 2000-07-13 PL PL00352465A patent/PL195787B1/pl not_active IP Right Cessation
- 2000-07-13 BR BR0012425-7A patent/BR0012425A/pt not_active IP Right Cessation
- 2000-07-13 US US10/030,647 patent/US6600039B1/en not_active Expired - Fee Related
- 2000-07-13 MX MXPA01013344A patent/MXPA01013344A/es active IP Right Grant
- 2000-07-13 JP JP2001511450A patent/JP2003505389A/ja not_active Ceased
- 2000-07-13 AT AT00949822T patent/ATE264842T1/de not_active IP Right Cessation
- 2000-07-13 CN CNB008103143A patent/CN1174969C/zh not_active Expired - Fee Related
- 2000-07-13 SK SK46-2002A patent/SK285818B6/sk not_active IP Right Cessation
- 2000-07-13 EP EP00949822A patent/EP1196381B1/en not_active Expired - Lifetime
- 2000-07-13 ES ES00949822T patent/ES2216927T3/es not_active Expired - Lifetime
- 2000-07-13 WO PCT/HU2000/000078 patent/WO2001005791A2/en not_active Ceased

Also Published As

Publication number	Publication date
CN1420868A (zh)	2003-05-28
HU9902376D0 (en)	1999-10-28
JP2003505389A (ja)	2003-02-12
HRP20020142A2 (en)	2003-12-31
CA2378087A1 (en)	2001-01-25
AU6308100A (en)	2001-02-05
PL195787B1 (pl)	2007-10-31
EP1196381B1 (en)	2004-04-21
EP1196381A2 (en)	2002-04-17
US6600039B1 (en)	2003-07-29
BR0012425A (pt)	2002-06-11
CZ2002145A3 (cs)	2002-11-13
ATE264842T1 (de)	2004-05-15
HUP9902376A2 (hu)	2001-05-28
PL352465A1 (en)	2003-08-25
MXPA01013344A (es)	2002-08-20
HRP20020142B1 (en)	2010-09-30
DE60010083T2 (de)	2005-03-31
CN1174969C (zh)	2004-11-10
DE60010083D1 (de)	2004-05-27
HUP9902376A3 (en)	2002-11-28
SK462002A3 (en)	2003-03-04
CA2378087C (en)	2007-12-18
ES2216927T3 (es)	2004-11-01
WO2001005791A2 (en)	2001-01-25
WO2001005791A3 (en)	2001-07-19

Legal Events

Date	Code	Title	Description
2012-04-03	MM4A	Patent lapsed due to non-payment of maintenance fees	Effective date: 20110713

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