NL7908618A - Pyrrolo- en pyrido/2,1-c/(1,4)thiazinen en -thiazepinen. - Google Patents

Pyrrolo- en pyrido/2,1-c/(1,4)thiazinen en -thiazepinen. Download PDF

Info

Publication number: NL7908618A
Authority: NL; Netherlands
Prior art keywords: formula; compound; methyl; compounds; acid
Prior art date: 1978-12-07

Application number

NL7908618A

Other languages

English (en)

Dutch (nl)

Original Assignee

Squibb & Sons Inc

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.)

1978-12-07

Filing date

1979-11-28

Publication date

1980-06-10

1979-11-28 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-06-10 Publication of NL7908618A publication Critical patent/NL7908618A/nl

Links

150000004912 thiazepines Chemical class 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 44
238000000034 method Methods 0.000 claims description 13
-1 3-mercapto-2-methyl-propanoyl Chemical group 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 15
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
239000000203 mixture Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
229910052786 argon Inorganic materials 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
238000002360 preparation method Methods 0.000 description 5
229960002429 proline Drugs 0.000 description 5
102000005862 Angiotensin II Human genes 0.000 description 4
101800000733 Angiotensin-2 Proteins 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
206010020772 Hypertension Diseases 0.000 description 4
CZGUSIXMZVURDU-JZXHSEFVSA-N Ile(5)-angiotensin II Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C([O-])=O)NC(=O)[C@@H](NC(=O)[C@H](CCCNC(N)=[NH2+])NC(=O)[C@@H]([NH3+])CC([O-])=O)C(C)C)C1=CC=C(O)C=C1 CZGUSIXMZVURDU-JZXHSEFVSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
229950006323 angiotensin ii Drugs 0.000 description 4
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
UUUHXMGGBIUAPW-UHFFFAOYSA-N 1-[1-[2-[[5-amino-2-[[1-[5-(diaminomethylideneamino)-2-[[1-[3-(1h-indol-3-yl)-2-[(5-oxopyrrolidine-2-carbonyl)amino]propanoyl]pyrrolidine-2-carbonyl]amino]pentanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-methylpentanoyl]pyrrolidine-2-carbon Chemical compound C1CCC(C(=O)N2C(CCC2)C(O)=O)N1C(=O)C(C(C)CC)NC(=O)C(CCC(N)=O)NC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C1CCCN1C(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C1CCC(=O)N1 UUUHXMGGBIUAPW-UHFFFAOYSA-N 0.000 description 3
MHRDCHHESNJQIS-UHFFFAOYSA-N 2-methyl-3-sulfanylpropanoic acid Chemical compound SCC(C)C(O)=O MHRDCHHESNJQIS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
108010064733 Angiotensins Proteins 0.000 description 3
102000015427 Angiotensins Human genes 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
102000004270 Peptidyl-Dipeptidase A Human genes 0.000 description 3
108090000882 Peptidyl-Dipeptidase A Proteins 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
230000036772 blood pressure Effects 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
150000003566 thiocarboxylic acids Chemical class 0.000 description 3
PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
101800000734 Angiotensin-1 Proteins 0.000 description 2
102400000344 Angiotensin-1 Human genes 0.000 description 2
102000004881 Angiotensinogen Human genes 0.000 description 2
108090001067 Angiotensinogen Proteins 0.000 description 2
CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
ORWYRWWVDCYOMK-HBZPZAIKSA-N angiotensin I Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC(C)C)C(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C1=CC=C(O)C=C1 ORWYRWWVDCYOMK-HBZPZAIKSA-N 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
125000006239 protecting group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000006798 ring closing metathesis reaction Methods 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000002904 solvent Substances 0.000 description 2
FAKRSMQSSFJEIM-MLWJPKLSSA-N (2s)-1-(2-methyl-3-sulfanylpropanoyl)pyrrolidine-2-carboxylic acid Chemical compound SCC(C)C(=O)N1CCC[C@H]1C(O)=O FAKRSMQSSFJEIM-MLWJPKLSSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZAISDHPZTZIFQF-UHFFFAOYSA-N 2h-1,4-thiazine Chemical class C1SC=CN=C1 ZAISDHPZTZIFQF-UHFFFAOYSA-N 0.000 description 1
LZTCBZBNEBUGFG-UHFFFAOYSA-N 3,3,3-trifluoro-2-(sulfanylmethyl)propanoic acid Chemical compound OC(=O)C(CS)C(F)(F)F LZTCBZBNEBUGFG-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
108090000783 Renin Proteins 0.000 description 1
FSLLKNMCGHWMKU-UHFFFAOYSA-N S1(NCC(C=C1)=O)=O Chemical compound S1(NCC(C=C1)=O)=O FSLLKNMCGHWMKU-UHFFFAOYSA-N 0.000 description 1
102000005686 Serum Globulins Human genes 0.000 description 1
108010045362 Serum Globulins Proteins 0.000 description 1
SORGEQQSQGNZFI-UHFFFAOYSA-N [azido(phenoxy)phosphoryl]oxybenzene Chemical compound C=1C=CC=CC=1OP(=O)(N=[N+]=[N-])OC1=CC=CC=C1 SORGEQQSQGNZFI-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000012267 brine Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
150000005826 halohydrocarbons Chemical class 0.000 description 1
150000007928 imidazolide derivatives Chemical class 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000007788 liquid Substances 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
210000002381 plasma Anatomy 0.000 description 1
CHKVPAROMQMJNQ-UHFFFAOYSA-M potassium bisulfate Chemical compound [K+].OS([O-])(=O)=O CHKVPAROMQMJNQ-UHFFFAOYSA-M 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
230000007017 scission Effects 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Heart & Thoracic Surgery (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Peptides Or Proteins (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Hydrogenated Pyridines (AREA)
Pyrrole Compounds (AREA)

NL7908618A 1978-12-07 1979-11-28 Pyrrolo- en pyrido/2,1-c/(1,4)thiazinen en -thiazepinen. NL7908618A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US96733578		1978-12-07
US05/967,335 US4225495A (en)	1978-12-07	1978-12-07	Pyrrolo or pyrido [2,1-c][1,4] thiazines or thiazepines

Publications (1)

Publication Number	Publication Date
NL7908618A true NL7908618A (nl)	1980-06-10

Family

ID=25512648

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL7908618A NL7908618A (nl)	1978-12-07	1979-11-28	Pyrrolo- en pyrido/2,1-c/(1,4)thiazinen en -thiazepinen.

Country Status (18)

Country	Link
US (1)	US4225495A (fr)
JP (1)	JPS5581886A (fr)
AU (1)	AU532228B2 (fr)
BE (1)	BE880480A (fr)
CA (1)	CA1126728A (fr)
CH (1)	CH643268A5 (fr)
DE (1)	DE2949179A1 (fr)
DK (1)	DK520279A (fr)
FR (2)	FR2443468A1 (fr)
GB (1)	GB2036743B (fr)
HU (2)	HU182755B (fr)
IE (1)	IE49123B1 (fr)
IT (1)	IT1127282B (fr)
LU (1)	LU81956A1 (fr)
NL (1)	NL7908618A (fr)
NO (1)	NO793983L (fr)
SE (2)	SE446737B (fr)
ZA (1)	ZA796288B (fr)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4692458A (en) *	1980-03-05	1987-09-08	University Of Miami	Anti-hypertensive agents
US4385180A (en) *	1980-07-01	1983-05-24	American Home Products Corporation	10,10a-Dihydro-1H-thiozino[4,3-a,]-indole-1,4(3H)-diones
US4352753A (en) *	1980-08-11	1982-10-05	American Home Products Corporation	3-[[(2,3-Dihydro-1H-indol-2-yl)carbonyl]thio]propanoic (and acetic) acids as intermediates
US4415496A (en) *	1981-03-23	1983-11-15	Merck & Co., Inc.	Bicyclic lactams
US4661479A (en) *	1982-02-19	1987-04-28	Merck And Co., Inc.	Bicyclic lactams as antihypertensives
US4617301A (en) *	1983-06-22	1986-10-14	Merck & Co., Inc.	Sulfoxide and sulfone derivatives of bicyclic lactams as antihypertensives
US5508272A (en) *	1993-06-15	1996-04-16	Bristol-Myers Squibb Company	Compounds containing a fused bicycle ring and processes therefor
US5616775A (en) *	1994-05-05	1997-04-01	Bristol-Myers Squibb Co.	Process for preparing homocystein analogs useful as intermediates for compounds containing a fused bicyclic ring
US5587375A (en) *	1995-02-17	1996-12-24	Bristol-Myers Squibb Company	Azepinone compounds useful in the inhibition of ACE and NEP
US5877313A (en)	1995-05-17	1999-03-02	Bristol-Myers Squibb	Benzo-fused azepinone and piperidinone compounds useful in the inhibition of ACE and NEP
US5650408A (en) *	1995-06-07	1997-07-22	Karanewsky; Donald S.	Thiazolo benzazepine containing dual action inhibitors
US5635504A (en) *	1995-06-07	1997-06-03	Bristol-Myers Squibb Co.	Diazepine containing dual action inhibitors

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2891000A (en) *	1953-09-23	1959-06-16	Exxon Research Engineering Co	Process for feeding heavy oils into conversion systems
US4105776A (en) *	1976-06-21	1978-08-08	E. R. Squibb & Sons, Inc.	Proline derivatives and related compounds
US4046889A (en) *	1976-02-13	1977-09-06	E. R. Squibb & Sons, Inc.	Azetidine-2-carboxylic acid derivatives
US4154935A (en) *	1978-02-21	1979-05-15	E. R. Squibb & Sons, Inc.	Halogen substituted mercaptoacylamino acids
JPS5576888A (en) *	1978-12-04	1980-06-10	Yoshitomi Pharmaceut Ind Ltd	Bicyclic hetero compound and its preparation

1978
- 1978-12-07 US US05/967,335 patent/US4225495A/en not_active Expired - Lifetime
1979
- 1979-11-20 CA CA340,201A patent/CA1126728A/fr not_active Expired
- 1979-11-20 ZA ZA00796288A patent/ZA796288B/xx unknown
- 1979-11-23 AU AU53144/79A patent/AU532228B2/en not_active Expired
- 1979-11-28 NL NL7908618A patent/NL7908618A/nl not_active Application Discontinuation
- 1979-11-28 FR FR7929249A patent/FR2443468A1/fr active Granted
- 1979-11-29 GB GB7941320A patent/GB2036743B/en not_active Expired
- 1979-12-04 IE IE2329/79A patent/IE49123B1/en not_active IP Right Cessation
- 1979-12-04 IT IT27856/79A patent/IT1127282B/it active
- 1979-12-05 LU LU81956A patent/LU81956A1/fr unknown
- 1979-12-06 DE DE19792949179 patent/DE2949179A1/de not_active Ceased
- 1979-12-06 BE BE0/198464A patent/BE880480A/fr not_active IP Right Cessation
- 1979-12-06 CH CH1083879A patent/CH643268A5/de not_active IP Right Cessation
- 1979-12-06 HU HU812891A patent/HU182755B/hu unknown
- 1979-12-06 HU HU79SU1042A patent/HU179342B/hu unknown
- 1979-12-06 SE SE7910072A patent/SE446737B/sv not_active IP Right Cessation
- 1979-12-06 NO NO793983A patent/NO793983L/no unknown
- 1979-12-06 DK DK520279A patent/DK520279A/da not_active Application Discontinuation
- 1979-12-07 JP JP15971079A patent/JPS5581886A/ja active Pending
1980
- 1980-03-19 FR FR8006146A patent/FR2445318A1/fr active Granted
1984
- 1984-10-12 SE SE8405123A patent/SE452458B/sv not_active IP Right Cessation

Also Published As

Publication number	Publication date
FR2443468B1 (fr)	1983-04-22
DK520279A (da)	1980-06-08
US4225495A (en)	1980-09-30
JPS5581886A (en)	1980-06-20
FR2445318B1 (fr)	1983-04-22
DE2949179A1 (de)	1980-06-26
IT7927856A0 (it)	1979-12-04
HU179342B (en)	1982-10-28
GB2036743A (en)	1980-07-02
IE792329L (en)	1980-06-07
IE49123B1 (en)	1985-08-07
AU5314479A (en)	1980-06-12
FR2445318A1 (fr)	1980-07-25
BE880480A (fr)	1980-06-06
GB2036743B (en)	1982-11-24
SE452458B (sv)	1987-11-30
SE8405123D0 (sv)	1984-10-12
SE7910072L (sv)	1980-06-08
IT1127282B (it)	1986-05-21
LU81956A1 (fr)	1980-04-22
ZA796288B (en)	1980-11-26
SE446737B (sv)	1986-10-06
HU182755B (en)	1984-03-28
NO793983L (no)	1980-06-10
CH643268A5 (de)	1984-05-30
FR2443468A1 (fr)	1980-07-04
CA1126728A (fr)	1982-06-29
AU532228B2 (en)	1983-09-22
SE8405123L (sv)	1984-10-12

Legal Events

Date	Code	Title
1985-01-01	A85	Still pending on 85-01-01
1986-11-03	BA	A request for search or an international-type search has been filed
1987-02-02	BB	A search report has been drawn up
1987-07-01	BC	A request for examination has been filed
1999-08-02	BV	The patent application has lapsed

Publication	Publication Date	Title
US4192945A (en)	1980-03-11	Process for preparing proline and homoproline derivatives
KR830002450B1 (ko)	1983-10-26	치환 프로린의 메르캅토아실 유도체의 제조방법
FI76559C (fi)	1988-11-10	Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara hexahydroindol-2-karboxylsyraderivat och nya mellanprodukter.
EP0635003A1 (fr)	1995-01-25	Derives de perhydroisoindole comme antagonistes de la substance p
DK159419B (da)	1990-10-15	Analogifremgangsmaade til fremstilling af substituerede acylderivater af octahydro-1h-indol-2-carboxylsyrer
NL7908618A (nl)	1980-06-10	Pyrrolo- en pyrido/2,1-c/(1,4)thiazinen en -thiazepinen.
US4296113A (en)	1981-10-20	Mercaptoacyl derivatives of keto substituted proline and pipecolic acid
IE50839B1 (en)	1986-07-23	Novel processes for preparing proline derivatives and analogous compounds
EP0125056B1 (fr)	1991-01-16	Composés contenant des cycles à sept chaînons condensés, leur préparation et leur utilisation
US4647561A (en)	1987-03-03	1,5-benzodiazepine compounds
US4296033A (en)	1981-10-20	4-Azido-1-mercaptoacyl proline
FR2539417A1 (fr)	1984-07-20	Nouveaux pyrrolo-1, 2 heterocycles, leur preparation et les medicaments qui les contiennent
CZ280776B6 (cs)	1996-04-17	Derivát tripeptidu, způsob jeho přípravy a farmaceutický prostředek, který ho obsahuje
FR2689889A1 (fr)	1993-10-15	Nouveaux dérivés de perhydroisoindole, et leur préparation.
JPH0247480B2 (fr)	1990-10-19
FR2468589A1 (fr)	1981-05-08	Derives aminoacyles de mercaptoacyl amino-acides, a action antihypertensive
IMAKI et al.	1981	Potent orally active inhibitors of angiotensin-converting enzyme (ACE)
US4396773A (en)	1983-08-02	1,1'-[Dithiobis(2-alkyl-1-oxo-3,1-propanediyl)]-bis[2,3-dihydro-1H-indole-2-carboxylic acids and derivatives
GB1561704A (en)	1980-02-27	Azetidione derivatives
US4307110A (en)	1981-12-22	Mercaptoacyl derivatives of 3-substituted proline derivatives
GB2196958A (en)	1988-05-11	Halo-homostatin peptide derivatives, their preparation and pharmaceutical compositions containing them
US4352753A (en)	1982-10-05	3-[[(2,3-Dihydro-1H-indol-2-yl)carbonyl]thio]propanoic (and acetic) acids as intermediates
US4454292A (en)	1984-06-12	N-[2-Substituted-1-oxoalkyl]-2,3-dihydro-1H-indole-2-carboxylic acid derivatives
EP0132964A2 (fr)	1985-02-13	Dérivés de 2-azabicyclo[2,2,2]-octane
US4308388A (en)	1981-12-29	4-Azido-1-mercaptoacyl pipecolic acid