IE32928L - Amino bicyclo carboxylic acids - Google Patents
Amino bicyclo carboxylic acidsInfo
- Publication number
- IE32928L IE32928L IE681465A IE146568A IE32928L IE 32928 L IE32928 L IE 32928L IE 681465 A IE681465 A IE 681465A IE 146568 A IE146568 A IE 146568A IE 32928 L IE32928 L IE 32928L
- Authority
- IE
- Ireland
- Prior art keywords
- reaction
- steps
- followed
- acid
- base
- Prior art date
Links
- 150000001735 carboxylic acids Chemical class 0.000 title 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 abstract 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 abstract 1
- 238000003512 Claisen condensation reaction Methods 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 229960000583 acetic acid Drugs 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000010933 acylation Effects 0.000 abstract 1
- 238000005917 acylation reaction Methods 0.000 abstract 1
- 230000001476 alcoholic effect Effects 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 230000001567 anti-fibrinolytic effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000002615 fibrolytic effect Effects 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 230000001575 pathological effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
Classifications
-
- 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
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1,209,799. Aminomethylbicyclocarboxylic acids. MERCK & CO. Inc. 9 Dec., 1968 [14 Dec., 1967], No. 58306/68. Heading C2C. Novel compounds of formula wherein n is 2 or 3, X is H 2 or O, R<SP>1</SP> is H or alkanoyl and R‹ is H, a non-toxic esterifying group or a cation, and acid addition salts thereof, are prepared as in steps 9 and 11 of the reaction schemes below, optionally followed by acylation, esterification and/or salt formation where appropriate. Intermediates are prepared as in steps 1 to 8 and 10 of the reaction schemes below, wherein R is ethyl. The numbered reaction steps are as follows:- (1) Claisen condensation with NaOC 2 H 5 , (2) Reaction with NaH or other strong base followed by Br(CH 2 ) n Br, (3) Reaction with HS(CH 2 ) 2 SH in presence of BF 3 etherate in glacial acetic acid, (4) Reduction with Raney nickel, (5) Gentle saponification with a base such as NaOH in aqueous alcohol, (6) Reaction with triethylamine and chloroformic ester, followed by ammonia to convert the anhydride to the amide, (7) Dehydration with POCl 3 in 1,2-dichloroethane or pyridine, (8) Heat with base such as NaOH in aqueous alcohol, (9) Catalytic reduction, such as over Pt in aqueous alcoholic HCl solution, (10) Reaction with 1,2-ethylene glycol in presence of toluene sulfonic acid in benzene and (11) Heating with acid. Pharmaceutical compositions having antifibrinolytic activity being in conventional forms for oral and parenteral administration comprise an above novel compound and a carrier therefor. A method for treating disorders resulting from a pathological fibrolytic state using the novel compounds is also claimed for non-humans.
[GB1209799A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69040467A | 1967-12-14 | 1967-12-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32928L true IE32928L (en) | 1969-06-14 |
| IE32928B1 IE32928B1 (en) | 1974-01-23 |
Family
ID=24772307
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1465/68A IE32928B1 (en) | 1967-12-14 | 1968-12-02 | Aminoalkylbicyclocarboxylic acids |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | AT289752B (en) |
| BE (1) | BE725459A (en) |
| BR (1) | BR6804856D0 (en) |
| CH (1) | CH518262A (en) |
| DE (1) | DE1812979A1 (en) |
| DK (1) | DK122809B (en) |
| ES (1) | ES361113A1 (en) |
| FI (1) | FI50970C (en) |
| FR (2) | FR8218M (en) |
| GB (1) | GB1209799A (en) |
| IE (1) | IE32928B1 (en) |
| IL (1) | IL31192A (en) |
| NL (1) | NL6817950A (en) |
| NO (1) | NO125182B (en) |
| SE (1) | SE357196B (en) |
| YU (2) | YU33008B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3641128A (en) * | 1969-06-17 | 1972-02-08 | Merck & Co Inc | Antifibrinolytic compounds |
| JPS4910951B1 (en) * | 1970-03-25 | 1974-03-13 | ||
| IE47589B1 (en) * | 1978-01-20 | 1984-05-02 | Daiichi Seiyaku Co | Process for producing 4-amino-methylbicyclo (2,2,2)octane-1-carboxylic acid and intermediate compound therefor |
| DE3336678A1 (en) * | 1983-10-08 | 1985-04-25 | Rudolf Wanzl Kg, 8874 Leipheim | Stackable shopping trolley with brake device |
| DE19917999B4 (en) * | 1999-04-21 | 2007-01-11 | Brand Gülletechnik GmbH | Automatically releasing brake device for a mobile transport device |
-
1968
- 1968-12-01 IL IL31192A patent/IL31192A/en unknown
- 1968-12-02 YU YU2827/68A patent/YU33008B/en unknown
- 1968-12-02 IE IE1465/68A patent/IE32928B1/en unknown
- 1968-12-04 SE SE16572/68A patent/SE357196B/xx unknown
- 1968-12-05 DE DE19681812979 patent/DE1812979A1/en not_active Withdrawn
- 1968-12-05 ES ES361113A patent/ES361113A1/en not_active Expired
- 1968-12-09 GB GB58306/68A patent/GB1209799A/en not_active Expired
- 1968-12-09 FI FI683518A patent/FI50970C/en active
- 1968-12-13 BE BE725459D patent/BE725459A/xx unknown
- 1968-12-13 BR BR204856/68A patent/BR6804856D0/en unknown
- 1968-12-13 DK DK611768AA patent/DK122809B/en not_active IP Right Cessation
- 1968-12-13 FR FR178115A patent/FR8218M/fr not_active Expired
- 1968-12-13 FR FR178116A patent/FR1605239A/fr not_active Expired
- 1968-12-13 AT AT1216768A patent/AT289752B/en not_active IP Right Cessation
- 1968-12-13 NL NL6817950A patent/NL6817950A/xx unknown
- 1968-12-13 NO NO4991/68A patent/NO125182B/no unknown
- 1968-12-13 CH CH1867168A patent/CH518262A/en not_active IP Right Cessation
-
1973
- 1973-08-23 YU YU2271/73A patent/YU34393B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI50970B (en) | 1976-05-31 |
| GB1209799A (en) | 1970-10-21 |
| IL31192A (en) | 1972-03-28 |
| NL6817950A (en) | 1969-06-17 |
| YU33008B (en) | 1976-03-31 |
| BE725459A (en) | 1969-06-13 |
| SE357196B (en) | 1973-06-18 |
| FI50970C (en) | 1976-09-10 |
| YU282768A (en) | 1975-08-31 |
| CH518262A (en) | 1972-01-31 |
| IL31192A0 (en) | 1969-02-27 |
| DE1812979A1 (en) | 1969-07-24 |
| IE32928B1 (en) | 1974-01-23 |
| YU34393B (en) | 1979-07-10 |
| FR1605239A (en) | 1973-08-31 |
| AT289752B (en) | 1971-05-10 |
| ES361113A1 (en) | 1970-08-01 |
| DK122809B (en) | 1972-04-17 |
| NO125182B (en) | 1972-07-31 |
| BR6804856D0 (en) | 1973-03-20 |
| YU227173A (en) | 1978-12-31 |
| FR8218M (en) | 1970-09-21 |
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